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Identification
NameHeme C
Accession NumberDB03317  (EXPT01722)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIINot Available
CAS numberNot Available
WeightAverage: 618.503
Monoisotopic: 618.192947729
Chemical FormulaC34H34FeN4O4
InChI KeyInChIKey=HXQIYSLZKNYNMH-STIJKOADSA-N
InChI
InChI=1S/C34H34N4O4.Fe/c1-7-21-17(3)25-13-26-19(5)23(9-11-33(39)40)31(37-26)16-32-24(10-12-34(41)42)20(6)28(38-32)15-30-22(8-2)18(4)27(36-30)14-29(21)35-25;/h7-8,13-16H,9-12H2,1-6H3,(H,39,40)(H,41,42);/q-4;+4/b21-7-,22-8-,26-13-,29-14-,30-15-,31-16-;
IUPAC Name
3-[(1S,10Z,15Z)-20-(2-carboxyethyl)-10,15-diethylidene-5,9,14,19-tetramethyl-2,22,23,25-tetraaza-1-ferraoctacyclo[11.9.1.1¹,⁸.1³,²¹.0²,⁶.0¹⁶,²³.0¹⁸,²².0¹¹,²⁵]pentacosa-3(24),4,6,8,11,13,16,18,20-nonaen-4-yl]propanoic acid
SMILES
C\C=C1\C(C)=C2C=C3N4C(=CC5=C(CCC(O)=O)C(C)=C6C=C7N8C(C=C1N2[Fe@]48N56)=C(C)\C7=C\C)C(CCC(O)=O)=C3C
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as metallotetrapyrroles. These are polycyclic compounds containing a tetrapyrrole skeleton combined with a metal atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassTetrapyrroles and derivatives
Sub ClassMetallotetrapyrroles
Direct ParentMetallotetrapyrroles
Alternative Parents
Substituents
  • Metallotetrapyrrole skeleton
  • Substituted pyrrole
  • Dicarboxylic acid or derivatives
  • Heteroaromatic compound
  • Pyrrole
  • Azacycle
  • Organic metal salt
  • Metalloheterocycle
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic transition metal salt
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.94 mg/mLALOGPS
logP4.28ALOGPS
logP0.19ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)3.17ChemAxon
pKa (Strongest Basic)9.05ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area89.25 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity174.1 m3·mol-1ChemAxon
Polarizability70.53 Å3ChemAxon
Number of Rings8ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

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
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 cytoplasmic enzymes that catalyze reduction of sulfates.
Gene Name:
hmcA
Uniprot ID:
P24092
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
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
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
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
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 transfers this electron to the cytochrome oxidase complex, the final protein carrier in the mitochondrial electron-transport chain.Plays a role in apoptosis. Suppression of the anti-apoptotic members or acti...
Gene Name:
CYCS
Uniprot ID:
P99999
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 (PubMed:11863430). Has even lower activity toward sulfite (PubMed:20629638). Sulfite reductase activity is maximal at neutral pH (By similarity).
Gene Name:
nrfA
Uniprot ID:
P0ABK9
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. However, it may also have a role in the respiratory chain and is found in some non-photosynthetic bacteria.
Gene Name:
cycA
Uniprot ID:
P00091
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 that enhances oxygen evolution.
Gene Name:
psbV
Uniprot ID:
Q55013
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
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
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
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
Molecular Weight:
29988.94 Da
Kind
Protein
Organism
Mycobacterium tuberculosis
Pharmacological action
unknown
General Function:
Involved in oxygen binding
Specific 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
Gene Name:
glbN
Uniprot ID:
P0A592
Molecular Weight:
14449.0 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
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
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
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
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
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
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
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
Molecular Weight:
13795.125 Da
Comments
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:21