Identification

Name
Heme C
Accession Number
DB03317  (EXPT01722)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
UNII
Not Available
CAS number
Not Available
Weight
Average: 684.65
Monoisotopic: 684.152734
Chemical Formula
C34H36FeN4O4S2
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

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UNitrite reductaseNot AvailablePseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
UHigh-molecular-weight cytochrome cNot AvailableDesulfovibrio vulgaris (strain Hildenborough / ATCC 29579 / NCIMB 8303)
UCytochrome c''Not AvailableMethylophilus methylotrophus
UQuinohemoprotein ethanol dehydrogenase type-1Not AvailableComamonas testosteroni
UNitrite reductaseNot AvailableParacoccus pantotrophus
UCytochrome c4Not AvailablePseudomonas stutzeri
UCytochrome cNot AvailableHuman
UCytochrome c-552Not AvailableEscherichia coli (strain K12)
UCytochrome c2Not AvailableRhodopseudomonas palustris (strain ATCC BAA-98 / CGA009)
UCytochrome c-550Not AvailableSynechocystis sp. (strain PCC 6803 / Kazusa)
UCytochrome c-552Not AvailableParacoccus denitrificans
UCytochrome c-551Not AvailablePseudomonas stutzeri
UCytochrome c3Not AvailableDesulfuromonas acetoxidans
USplit-Soret cytochrome cNot AvailableDesulfovibrio desulfuricans (strain ATCC 27774 / DSM 6949)
UGroup 1 truncated hemoglobin GlbNNot AvailableMycobacterium tuberculosis
UCytochrome c-553Not AvailableBacillus pasteurii
UCytochrome P450 2C9Not AvailableHuman
UNine-heme cytochrome cNot AvailableDesulfovibrio desulfuricans (strain ATCC 27774 / DSM 6949)
UCytochrome c3, 13 kDaNot AvailableDesulfovibrio baculatus (strain Norway 4)
UCytochrome c551 peroxidaseNot AvailablePseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
UCytochrome c3Not AvailableDesulfovibrio vulgaris (strain Miyazaki F / DSM 19637)
UCytochrome c'Not AvailableRhodobacter sphaeroides (strain ATCC 17023 / 2.4.1 / NCIB 8253 / DSM 158)
UCytochrome c3Not AvailableDesulfovibrio 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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
51351657
PubChem Substance
46508322
ChemSpider
392105
ChEBI
60562
HET
HEC

Clinical Trials

Clinical Trials
Not Available

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
PropertyValueSource
Water Solubility0.00697 mg/mLALOGPS
logP-0.06ALOGPS
logP1.54ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)3.35ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area92.22 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity185.02 m3·mol-1ChemAxon
Polarizability77.1 Å3ChemAxon
Number of Rings8ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9637
Blood Brain Barrier+0.6117
Caco-2 permeable-0.5851
P-glycoprotein substrateSubstrate0.6791
P-glycoprotein inhibitor INon-inhibitor0.6149
P-glycoprotein inhibitor IINon-inhibitor0.8075
Renal organic cation transporterNon-inhibitor0.8816
CYP450 2C9 substrateNon-substrate0.7234
CYP450 2D6 substrateNon-substrate0.8258
CYP450 3A4 substrateSubstrate0.5911
CYP450 1A2 substrateInhibitor0.5213
CYP450 2C9 inhibitorNon-inhibitor0.6976
CYP450 2D6 inhibitorNon-inhibitor0.7239
CYP450 2C19 inhibitorNon-inhibitor0.7656
CYP450 3A4 inhibitorNon-inhibitor0.7545
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6522
Ames testNon AMES toxic0.6283
CarcinogenicityNon-carcinogens0.9233
BiodegradationNot ready biodegradable0.9928
Rat acute toxicity2.6478 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9199
hERG inhibition (predictor II)Non-inhibitor0.8916
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Taxonomy

Classification
Not classified

Targets

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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. 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. [PubMed:17016423]
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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. 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. [PubMed:17016423]
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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. 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. [PubMed:17016423]
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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. 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. [PubMed:17016423]
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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. 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. [PubMed:17016423]
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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. 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. [PubMed:17016423]
Kind
Protein
Organism
Human
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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. 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. [PubMed:17016423]
  3. 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. [PubMed:10592235]
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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. 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. [PubMed:17016423]
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
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
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
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
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
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
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
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
Kind
Protein
Organism
Human
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
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
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
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
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
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
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 on June 13, 2005 07:24 / Updated on November 09, 2017 03:26