Ferroheme C

Identification

Generic Name

Ferroheme C

DrugBank Accession Number

DB03317

Background

Not Available

Type

Small Molecule

Groups

Experimental

Structure

Similar Structures

Weight: Average: 684.65
Monoisotopic: 684.152734
Chemical Formula: C₃₄H₃₆FeN₄O₄S₂

Synonyms

Heme C

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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings

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Pharmacodynamics

Not Available

Mechanism of action

Target	Actions	Organism
UNitrite reductase	Not Available	Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
UHigh-molecular-weight cytochrome c	Not Available	Desulfovibrio vulgaris (strain Hildenborough / ATCC 29579 / NCIMB 8303)
UCytochrome c''	Not Available	Methylophilus methylotrophus
UQuinohemoprotein ethanol dehydrogenase type-1	Not Available	Comamonas testosteroni
UNitrite reductase	Not Available	Paracoccus pantotrophus
UCytochrome c4	Not Available	Pseudomonas stutzeri
UCytochrome c	Not Available	Humans
UCytochrome c-552	Not Available	Escherichia coli (strain K12)
UCytochrome c2	Not Available	Rhodopseudomonas palustris (strain ATCC BAA-98 / CGA009)
UCytochrome c-550	Not Available	Synechocystis sp. (strain PCC 6803 / Kazusa)
UCytochrome c-552	Not Available	Paracoccus denitrificans
UCytochrome c-551	Not Available	Pseudomonas stutzeri
UCytochrome c3	Not Available	Desulfuromonas acetoxidans
USplit-Soret cytochrome c	Not Available	Desulfovibrio desulfuricans (strain ATCC 27774 / DSM 6949)
UGroup 1 truncated hemoglobin GlbN	Not Available	Mycobacterium tuberculosis
UCytochrome c-553	Not Available	Bacillus pasteurii
UCytochrome P450 2C9	Not Available	Humans
UNine-heme cytochrome c	Not Available	Desulfovibrio desulfuricans (strain ATCC 27774 / DSM 6949)
UCytochrome c3, 13 kDa	Not Available	Desulfovibrio baculatus (strain Norway 4)
UCytochrome c551 peroxidase	Not Available	Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
UCytochrome c3	Not Available	Desulfovibrio vulgaris (strain Miyazaki F / DSM 19637)
UCytochrome c'	Not Available	Rhodobacter sphaeroides (strain ATCC 17023 / 2.4.1 / NCIB 8253 / DSM 158)
UCytochrome c3	Not Available	Desulfovibrio desulfuricans

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Not Available

Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects

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Toxicity

Not Available

Pathways

Not Available

Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">

Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">: This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions: Not Available

Chemical Identifiers

UNII: Not Available
CAS number: 26598-29-8
InChI Key: XSWPXBWSKQRBRZ-IDTMDVKXSA-L
InChI: InChI=1S/C34H38N4O4S2.Fe/c1-15-21(7-9-31(39)40)27-14-28-22(8-10-32(41)42)16(2)24(36-28)12-29-34(20(6)44)18(4)26(38-29)13-30-33(19(5)43)17(3)25(37-30)11-23(15)35-27;/h11-14,19-20H,7-10H2,1-6H3,(H6,35,36,37,38,39,40,41,42,43,44);/q;+2/p-2/b23-11-,24-12-,25-11-,26-13-,27-14-,28-14-,29-12-,30-13-;
IUPAC Name: 4,20-bis(2-carboxyethyl)-5,9,14,19-tetramethyl-10,15-bis(1-sulfanylethyl)-2lambda5,22,23lambda5,25-tetraaza-1-ferraoctacyclo[11.9.1.1^{1,8}.1^{3,21}.0^{2,6}.0^{16,23}.0^{18,22}.0^{11,25}]pentacosa-2,4,6,8,10,12,14,16(23),17,19,21(24)-undecaene-2,23-bis(ylium)-1,1-diuide
SMILES: CC(S)C1=C2C=C3C(C)=C(C(C)S)C4=[N+]3[Fe--]35N6C(=C4)C(C)=C(CCC(O)=O)C6=CC4=[N+]3C(=CC(N25)=C1C)C(C)=C4CCC(O)=O

References

General References

Not Available

External Links

PubChem Compound: 51351657
PubChem Substance: 46508322
ChemSpider: 392105
ChEBI: 60562
PDBe Ligand: HEC
Wikipedia: Heme_C

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count

Pharmacoeconomics

Manufacturers: Not Available
Packagers: Not Available
Dosage Forms: Not Available
Prices: Not Available
Patents: Not Available

Properties

State

Solid

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.00697 mg/mL	ALOGPS
logP	-0.06	ALOGPS
logP	1.54	Chemaxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	3.35	Chemaxon
Physiological Charge	-2	Chemaxon
Hydrogen Acceptor Count	4	Chemaxon
Hydrogen Donor Count	4	Chemaxon
Polar Surface Area	92.22 Å²	Chemaxon
Rotatable Bond Count	8	Chemaxon
Refractivity	185.02 m³·mol^-1	Chemaxon
Polarizability	77.1 Å³	Chemaxon
Number of Rings	8	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	No	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	Yes	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.9637
Blood Brain Barrier	+	0.6117
Caco-2 permeable	-	0.5851
P-glycoprotein substrate	Substrate	0.6791
P-glycoprotein inhibitor I	Non-inhibitor	0.6149
P-glycoprotein inhibitor II	Non-inhibitor	0.8075
Renal organic cation transporter	Non-inhibitor	0.8816
CYP450 2C9 substrate	Non-substrate	0.7234
CYP450 2D6 substrate	Non-substrate	0.8258
CYP450 3A4 substrate	Substrate	0.5911
CYP450 1A2 substrate	Inhibitor	0.5213
CYP450 2C9 inhibitor	Non-inhibitor	0.6976
CYP450 2D6 inhibitor	Non-inhibitor	0.7239
CYP450 2C19 inhibitor	Non-inhibitor	0.7656
CYP450 3A4 inhibitor	Non-inhibitor	0.7545
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.6522
Ames test	Non AMES toxic	0.6283
Carcinogenicity	Non-carcinogens	0.9233
Biodegradation	Not ready biodegradable	0.9928
Rat acute toxicity	2.6478 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9199
hERG inhibition (predictor II)	Non-inhibitor	0.8916

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST): Not Available
Spectra: Not Available
Chromatographic Properties: Collision Cross Sections (CCS)
Not Available

Targets

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Details1. Nitrite reductase

Kind: Protein
Organism: Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
Pharmacological action: Unknown

General Function: Nitrite reductase (no-forming) activity
Specific Function: Not Available
Gene Name: nirS
Uniprot ID: P24474
Uniprot Name: Nitrite reductase
Molecular Weight: 62652.855 Da

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]

Details2. High-molecular-weight cytochrome c

Kind: Protein
Organism: Desulfovibrio vulgaris (strain Hildenborough / ATCC 29579 / NCIMB 8303)
Pharmacological action: Unknown

General Function: Metal ion binding
Specific Function: HMWC (high-molecular-weight cytochrome c), ORF2, ORF3, ORF4, ORF5 and ORF6 in the HMC operon form a transmembrane protein complex that allows electron flow from the periplasmic hydrogenase to the c...
Gene Name: hmcA
Uniprot ID: P24092
Uniprot Name: High-molecular-weight cytochrome c
Molecular Weight: 58901.06 Da

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]

Details3. Cytochrome c''

Kind: Protein
Organism: Methylophilus methylotrophus
Pharmacological action: Unknown

General Function: Metal ion binding
Specific Function: Not Available
Gene Name: cycA
Uniprot ID: Q9RQB9
Uniprot Name: Cytochrome c''
Molecular Weight: 15791.975 Da

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]

Details4. Quinohemoprotein ethanol dehydrogenase type-1

Kind: Protein
Organism: Comamonas testosteroni
Pharmacological action: Unknown

General Function: Oxidoreductase activity, acting on ch-oh group of donors
Specific Function: Catalyzes the dye-linked oxidation of primary alcohols to the corresponding aldehydes and the (subsequent) oxidation of the aldehydes to carboxylic acids.
Gene Name: qheDH
Uniprot ID: Q46444
Uniprot Name: Quinohemoprotein ethanol dehydrogenase type-1
Molecular Weight: 76822.435 Da

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]

Details5. Nitrite reductase

Kind: Protein
Organism: Paracoccus pantotrophus
Pharmacological action: Unknown

General Function: Nitrite reductase (no-forming) activity
Specific Function: Not Available
Gene Name: nirS
Uniprot ID: P72181
Uniprot Name: Nitrite reductase
Molecular Weight: 65382.815 Da

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]

Details6. Cytochrome c4

Kind: Protein
Organism: Pseudomonas stutzeri
Pharmacological action: Unknown

General Function: Iron ion binding
Specific Function: Diheme, high potential cytochrome c believed to be an intermediate electron donor to terminal oxidation systems.
Gene Name: cc4
Uniprot ID: Q52369
Uniprot Name: Cytochrome c4
Molecular Weight: 21741.505 Da

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]

Details7. Cytochrome c

Kind: Protein
Organism: Humans
Pharmacological action: Unknown

General Function: Metal ion binding
Specific Function: Electron carrier protein. The oxidized form of the cytochrome c heme group can accept an electron from the heme group of the cytochrome c1 subunit of cytochrome reductase. Cytochrome c then transfe...
Gene Name: CYCS
Uniprot ID: P99999
Uniprot Name: Cytochrome c
Molecular Weight: 11748.69 Da

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Details8. Cytochrome c-552

Kind: Protein
Organism: Escherichia coli (strain K12)
Pharmacological action: Unknown

General Function: Nitrite reductase (cytochrome, ammonia-forming) activity
Specific Function: Catalyzes the reduction of nitrite to ammonia, consuming six electrons in the process (PubMed:9593308, PubMed:11863430, PubMed:18311941, PubMed:20629638). Has very low activity toward hydroxylamine...
Gene Name: nrfA
Uniprot ID: P0ABK9
Uniprot Name: Cytochrome c-552
Molecular Weight: 53702.545 Da

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]

Details9. Cytochrome c2

Kind: Protein
Organism: Rhodopseudomonas palustris (strain ATCC BAA-98 / CGA009)
Pharmacological action: Unknown

General Function: Metal ion binding
Specific Function: Cytochrome c2 is found mainly in purple, non-sulfur, photosynthetic bacteria where it functions as the electron donor to the oxidized bacteriochlorophyll in the photophosphorylation pathway. Howeve...
Gene Name: cycA
Uniprot ID: P00091
Uniprot Name: Cytochrome c2
Molecular Weight: 14632.81 Da

Details10. Cytochrome c-550

Kind: Protein
Organism: Synechocystis sp. (strain PCC 6803 / Kazusa)
Pharmacological action: Unknown

General Function: Iron ion binding
Specific Function: Low-potential cytochrome c that plays a role in the oxygen-evolving complex of photosystem II (PSII). Required for normal function or stabilization of PSII. Extrinsic protein associated with PSII t...
Gene Name: psbV
Uniprot ID: Q55013
Uniprot Name: Cytochrome c-550
Molecular Weight: 17883.935 Da

Details11. Cytochrome c-552

Kind: Protein
Organism: Paracoccus denitrificans
Pharmacological action: Unknown

General Function: Metal ion binding
Specific Function: Mediates the electron transport between the cytochrome bc1 complex and cytochrome-c oxidase.
Gene Name: cycM
Uniprot ID: P54820
Uniprot Name: Cytochrome c-552
Molecular Weight: 18209.365 Da

Details12. Cytochrome c-551

Kind: Protein
Organism: Pseudomonas stutzeri
Pharmacological action: Unknown

General Function: Iron ion binding
Specific Function: Electron donor for cytochrome cd1 in nitrite and nitrate respiration.
Gene Name: nirM
Uniprot ID: P00101
Uniprot Name: Cytochrome c-551
Molecular Weight: 10796.685 Da

Details13. Cytochrome c3

Kind: Protein
Organism: Desulfuromonas acetoxidans
Pharmacological action: Unknown

General Function: Metal ion binding
Specific Function: Participates in sulfate respiration coupled with phosphorylation by transferring electrons from the enzyme dehydrogenase to ferredoxin.
Gene Name: cyd
Uniprot ID: P00137
Uniprot Name: Cytochrome c3
Molecular Weight: 7262.195 Da

Details14. Split-Soret cytochrome c

Kind: Protein
Organism: Desulfovibrio desulfuricans (strain ATCC 27774 / DSM 6949)
Pharmacological action: Unknown

General Function: Metal ion binding
Specific Function: Diheme cytochrome c which may be involved in sulfate reduction.
Gene Name: Not Available
Uniprot ID: P81040
Uniprot Name: Split-Soret cytochrome c
Molecular Weight: 29988.94 Da

Details15. Group 1 truncated hemoglobin GlbN

Kind: Protein
Organism: Mycobacterium tuberculosis
Pharmacological action: Unknown

General Function: Binds oxygen cooperatively with very high affinity (P(50) = 0.013 mmHg at 20 degrees Celsius) because of a fast combination (25 microM(-1).s(-1)) and a slow dissociation (0.2 s(-1)) rate.
Specific Function: Heme binding
Gene Name: glbN
Uniprot ID: P9WN25
Uniprot Name: Group 1 truncated hemoglobin GlbN
Molecular Weight: 14448.445 Da

Details16. Cytochrome c-553

Kind: Protein
Organism: Bacillus pasteurii
Pharmacological action: Unknown

General Function: Iron ion binding
Specific Function: Natural electron acceptor for a formate dehydrogenase.
Gene Name: Not Available
Uniprot ID: P82599
Uniprot Name: Cytochrome c-553
Molecular Weight: 8990.665 Da

Details17. Cytochrome P450 2C9

Kind: Protein
Organism: Humans
Pharmacological action: Unknown

General Function: Steroid hydroxylase activity
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name: CYP2C9
Uniprot ID: P11712
Uniprot Name: Cytochrome P450 2C9
Molecular Weight: 55627.365 Da

Details18. Nine-heme cytochrome c

Kind: Protein
Organism: Desulfovibrio desulfuricans (strain ATCC 27774 / DSM 6949)
Pharmacological action: Unknown

General Function: Metal ion binding
Specific Function: May form part of a transmembrane redox complex through which electrons are transferred to the cytoplasm for reduction of sulfate.
Gene Name: Not Available
Uniprot ID: Q9RN68
Uniprot Name: Nine-heme cytochrome c
Molecular Weight: 35024.955 Da

Details19. Cytochrome c3, 13 kDa

Kind: Protein
Organism: Desulfovibrio baculatus (strain Norway 4)
Pharmacological action: Unknown

General Function: Metal ion binding
Specific Function: Participates in sulfate respiration coupled with phosphorylation by transferring electrons from the enzyme dehydrogenase to ferredoxin.
Gene Name: Not Available
Uniprot ID: P00136
Uniprot Name: Cytochrome c3, 13 kDa
Molecular Weight: 12622.275 Da

Details20. Cytochrome c551 peroxidase

Kind: Protein
Organism: Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
Pharmacological action: Unknown

General Function: Metal ion binding
Specific Function: Catalyzes the peroxidative oxidation of azurin and cytochrome c551. Likely to provide protection against toxic peroxides.
Gene Name: ccpA
Uniprot ID: P14532
Uniprot Name: Cytochrome c551 peroxidase
Molecular Weight: 37403.035 Da

Details21. Cytochrome c3

Kind: Protein
Organism: Desulfovibrio vulgaris (strain Miyazaki F / DSM 19637)
Pharmacological action: Unknown

General Function: Metal ion binding
Specific Function: Participates in sulfate respiration coupled with phosphorylation by transferring electrons from the enzyme dehydrogenase to ferredoxin.
Gene Name: Not Available
Uniprot ID: P00132
Uniprot Name: Cytochrome c3
Molecular Weight: 13843.065 Da

Details22. Cytochrome c'

Kind: Protein
Organism: Rhodobacter sphaeroides (strain ATCC 17023 / 2.4.1 / NCIB 8253 / DSM 158)
Pharmacological action: Unknown

General Function: Iron ion binding
Specific Function: Cytochrome c' is the most widely occurring bacterial c-type cytochrome. Cytochromes c' are high-spin proteins and the heme has no sixth ligand. Their exact function is not known.
Gene Name: cycP
Uniprot ID: P00148
Uniprot Name: Cytochrome c'
Molecular Weight: 15362.42 Da

Details23. Cytochrome c3

Kind: Protein
Organism: Desulfovibrio desulfuricans
Pharmacological action: Unknown

General Function: Metal ion binding
Specific Function: Not Available
Gene Name: cytc3
Uniprot ID: Q9L915
Uniprot Name: Cytochrome c3
Molecular Weight: 13795.125 Da

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52

Ferroheme C

Identification

Structure for Ferroheme C (DB03317)

Pharmacology

Interactions

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Collision Cross Sections (CCS)

Targets

References

References

References

References

References

References

References

References