4,5-Dihydro-4-hydroxy-5-S-glutathionyl-benzo[a]pyrene (PAMDB000944)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000944
Identification
Name: 4,5-Dihydro-4-hydroxy-5-S-glutathionyl-benzo[a]pyrene
Description:4,5-dihydro-4-hydroxy-5-s-glutathionyl-benzo[a]pyrene is a member of the chemical class known as Peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another. 3-amino-2-propanol is invovled in L-threonine metabolism. D-1-Amino-2-propanol:NAD+ oxidoreductase activity, which catalyzes the second step in a pathway wherein L-threonine is converted to D-1-amino-2-propanol via the intermediate formation of aminoacetone, has been purified 500-fold from Pseudomonas aeruginosa.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • (R)-1-aminopropan-2-ol
  • 1-Amino-2-propanol
  • 3-Amino-2-propanol
  • Aminopropanol
  • D-1-Amino-2-propanol
  • D-1-Aminopropan-2-ol
  • DL-1-amino-2-propanol
Chemical Formula: C30H29N3O7S
Average Molecular Weight: 575.632
Monoisotopic Molecular Weight: 575.172620987
InChI Key: PZXCOGFLSNREMF-SUZCJKPRSA-N
InChI:InChI=1S/C30H29N3O7S/c31-21(30(39)40)10-11-23(34)33-22(29(38)32-13-24(35)36)14-41-28-20-12-16-4-1-2-6-17(16)18-9-8-15-5-3-7-19(27(28)37)25(15)26(18)20/h1-9,12,21-22,27-28,37H,10-11,13-14,31H2,(H,32,38)(H,33,34)(H,35,36)(H,39,40)/t21-,22-,27?,28?/m0/s1
CAS number: Not Available
IUPAC Name:(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)-C-hydroxycarbonimidoyl]-2-({11-hydroxypentacyclo[10.6.2.0?,??0?????0??????icosa-1(19),2,4,6,8,12,14,16(20),17-nonaen-10-yl}sulfanyl)ethyl]-C-hydroxycarbonimidoyl}butanoic acid
Traditional IUPAC Name: (2S)-2-amino-4-{[(1R)-1-(carboxymethyl-C-hydroxycarbonimidoyl)-2-({11-hydroxypentacyclo[10.6.2.0?,??0?????0??????icosa-1(19),2,4,6,8,12,14,16(20),17-nonaen-10-yl}sulfanyl)ethyl]-C-hydroxycarbonimidoyl}butanoic acid
SMILES:[H][C@](N)(CCC(O)=N[C@@]([H])(CSC1([H])C2=CC3=CC=CC=C3C3=C2C2=C(C=CC=C2C1([H])O)C=C3)C(O)=NCC(O)=O)C(O)=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.
Kingdom Organic compounds
Super ClassOrganic acids and derivatives
Class Carboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct Parent Peptides
Alternative Parents
Substituents
  • Alpha peptide
  • Chrysene
  • Phenanthrene
  • N-acyl-aliphatic-alpha amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • D-alpha-amino acid
  • Naphthalene
  • Alpha-amino acid or derivatives
  • Alpha-amino acid
  • Amino fatty acid
  • Fatty acyl
  • Benzenoid
  • Dicarboxylic acid or derivatives
  • Secondary alcohol
  • Dialkylthioether
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Sulfenyl compound
  • Thioether
  • Carboxylic acid
  • Carboximidic acid derivative
  • Carboximidic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic homopolycyclic compound
Molecular Framework Aromatic homopolycyclic compounds
External Descriptors Not Available
Physical Properties
State: Not Available
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.00342 mg/mLALOGPS
logP0.19ALOGPS
logP0.68ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)2.07ChemAxon
pKa (Strongest Basic)9.54ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area186.03 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity153.14 m3·mol-1ChemAxon
Polarizability59.66 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Benzo[a]pyrene-4,5-oxide + Glutathione <> 4,5-Dihydro-4-hydroxy-5-S-glutathionyl-benzo[a]pyrene
1-Amino-2-propanol + NAD + 4,5-Dihydro-4-hydroxy-5-S-glutathionyl-benzo[a]pyrene < NADH + Hydrogen ion + Aminoacetone
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0adj-2011390000-7a7dbf308ba61fa538f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9103720000-1eef252466caae626959View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9142100000-aa9f26588448cdcc954cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0kn9-0133090000-45cda9ad0c81d7f90fd3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f89-0196010000-141a30f61669cde8948aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udl-2942000000-afdbd3b8e287537675d8View in MoNA
References
References:
  • Campbell, R. L., Swain, R. R., Dekker, E. E. (1978). "Purification, separation, and characterization of two molecular forms of D-1-amino-2-propanol:NAD+ oxidoreductase activity from extracts of Escherichia coli K-12." J Biol Chem 253:7282-7288. Pubmed: 359547
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDHMDB60391
Pubchem Compound ID11954068
Kegg IDC14855
ChemSpider ID10128363
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
• GSH-dependent disulfide bond oxidoreductase
General function:
Not Available
Specific function:
Not Available
Gene Name:
yfcG
Locus Tag:
PA1033
Molecular weight:
24.5 kDa