Identification

Generic Name
Siroheme
DrugBank Accession Number
DB02832
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 914.645
Monoisotopic: 914.194523449
Chemical Formula
C42H42FeN4O16
Synonyms
Not Available

Pharmacology

Indication

Not Available

Reduce drug development failure rates
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Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug events
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
USulfite reductase [NADPH] hemoprotein beta-componentNot AvailableEscherichia coli (strain K12)
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
Not Available

Interactions

Drug Interactions
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

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as metallotetrapyrroles. These are polycyclic compounds containing a tetrapyrrole skeleton combined with a metal atom.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Tetrapyrroles and derivatives
Sub Class
Metallotetrapyrroles
Direct Parent
Metallotetrapyrroles
Alternative Parents
Substituted pyrroles / Heteroaromatic compounds / Organic transition metal salts / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic zwitterions / Organic oxides / Hydrocarbon derivatives
show 1 more
Substituents
Aromatic heteropolycyclic compound / Azacycle / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Heteroaromatic compound / Hydrocarbon derivative / Metallotetrapyrrole skeleton / Organic nitrogen compound / Organic oxide
show 9 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
52553-42-1
InChI Key
PGYXHNRRBJLFEV-NBUGCWMUSA-N
InChI
InChI=1S/C42H42N4O16.Fe/c1-41(17-39(59)60)23(5-9-35(51)52)29-14-27-21(11-37(55)56)19(3-7-33(47)48)25(43-27)13-26-20(4-8-34(49)50)22(12-38(57)58)28(44-26)15-31-42(2,18-40(61)62)24(6-10-36(53)54)30(46-31)16-32(41)45-29;/h13-16H,3-12,17-18H2,1-2H3,(H,47,48)(H,49,50)(H,51,52)(H,53,54)(H,55,56)(H,57,58)(H,59,60)(H,61,62);/q-4;+4/b25-13-,27-14-,31-15-,32-16-;/t41-,42-;/m0./s1
IUPAC Name
3-[(1R,5S,10S)-9,15,19-tris(2-carboxyethyl)-5,10,14,20-tetrakis(carboxymethyl)-5,10-dimethyl-2,22,23,25-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-3,6,8,11,13,15,17,19,21(24)-nonaen-4-yl]propanoic acid
SMILES
C[C@@]1(CC(O)=O)C2=CC3=C(CC(O)=O)C(CCC(O)=O)=C4C=C5N6C(=CC7=C(CCC(O)=O)[C@](C)(CC(O)=O)C8=CC(N2[Fe@]6(N34)N78)=C1CCC(O)=O)C(CC(O)=O)=C5CCC(O)=O

References

General References
Not Available
KEGG Compound
C00748
PubChem Compound
11968291
PubChem Substance
46507092
ChemSpider
26328986
ChEBI
28599
PDBe Ligand
SRM
Wikipedia
Siroheme
PDB Entries
1aop / 1zj8 / 1zj9 / 2akj / 2aop / 2gep / 2v4j / 2xsj / 3aop / 3b0g
show 45 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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 Solubility0.296 mg/mLALOGPS
logP1.54ALOGPS
logP-0.61ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)2.62ChemAxon
Physiological Charge-7ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area313.05 Å2ChemAxon
Rotatable Bond Count20ChemAxon
Refractivity218.95 m3·mol-1ChemAxon
Polarizability91.46 Å3ChemAxon
Number of Rings8ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9835
Blood Brain Barrier+0.6498
Caco-2 permeable-0.5802
P-glycoprotein substrateSubstrate0.7518
P-glycoprotein inhibitor INon-inhibitor0.5483
P-glycoprotein inhibitor IINon-inhibitor0.8378
Renal organic cation transporterNon-inhibitor0.8638
CYP450 2C9 substrateNon-substrate0.7768
CYP450 2D6 substrateNon-substrate0.8338
CYP450 3A4 substrateSubstrate0.5827
CYP450 1A2 substrateNon-inhibitor0.5863
CYP450 2C9 inhibitorNon-inhibitor0.7171
CYP450 2D6 inhibitorNon-inhibitor0.8055
CYP450 2C19 inhibitorNon-inhibitor0.7777
CYP450 3A4 inhibitorInhibitor0.5405
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6481
Ames testNon AMES toxic0.6343
CarcinogenicityNon-carcinogens0.9238
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.6887 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8394
hERG inhibition (predictor II)Non-inhibitor0.8744
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Targets

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Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Sulfite reductase (nadph) activity
Specific Function
Component of the sulfite reductase complex that catalyzes the 6-electron reduction of sulfite to sulfide. This is one of several activities required for the biosynthesis of L-cysteine from sulfate.
Gene Name
cysI
Uniprot ID
P17846
Uniprot Name
Sulfite reductase [NADPH] hemoprotein beta-component
Molecular Weight
63997.615 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. [Article]
  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. [Article]

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