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Record Information
Version1.0
Created at2021-01-06 07:00:30 UTC
Updated at2021-07-15 17:37:07 UTC
NP-MRD IDNP0021733
Secondary Accession NumbersNone
Natural Product Identification
Common NameSangivamycin
Provided ByNPAtlasNPAtlas Logo
DescriptionSangivamycin belongs to the class of organic compounds known as pyrrolopyrimidine nucleosides and nucleotides. These are nucleoside derivatives containing a ribose derivative which is n-glycosylated to a pyrrolopyrimidine. Also called deazapurine nucleosides, they are analogs of purine nucleosides with the N atom of the purine being replaced by a C atom at position 7. Sangivamycin is found in Streptomyces sp. It was first documented in 1968 (PMID: 5748694). Based on a literature review very few articles have been published on sangivamycin (PMID: 26024233) (PMID: 3338987).
Structure
Data?1624506920
Synonyms
ValueSource
7-Deaza-7-carbamoyladenosineChEBI
7-Deazaadenosine-7-carboxamideChEBI
4-amino-5-carboxamido-7-(D-Ribofuranosyl)-pyrrolo-(2,3-D)pyrimidineMeSH
Sangivamycin monohydrochlorideMeSH
Chemical FormulaC12H15N5O5
Average Mass309.2780 Da
Monoisotopic Mass309.10732 Da
IUPAC Name4-amino-7-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide
Traditional Name4-amino-7-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrrolo[2,3-d]pyrimidine-5-carboxamide
CAS Registry NumberNot Available
SMILES
NC(=O)C1=CN([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C2=C1C(N)=NC=N2
InChI Identifier
InChI=1S/C12H15N5O5/c13-9-6-4(10(14)21)1-17(11(6)16-3-15-9)12-8(20)7(19)5(2-18)22-12/h1,3,5,7-8,12,18-20H,2H2,(H2,14,21)(H2,13,15,16)/t5-,7-,8-,12-/m1/s1
InChI KeyOBZJZDHRXBKKTJ-JTFADIMSSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Streptomyces sp.NPAtlas
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrrolopyrimidine nucleosides and nucleotides. These are nucleoside derivatives containing a ribose derivative which is n-glycosylated to a pyrrolopyrimidine. Also called deazapurine nucleosides, they are analogs of purine nucleosides with the N atom of the purine being replaced by a C atom at position 7.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPyrrolopyrimidine nucleosides and nucleotides
Sub ClassNot Available
Direct ParentPyrrolopyrimidine nucleosides and nucleotides
Alternative Parents
Substituents
  • Pyrrolopyrimidine ribonucleoside
  • Glycosyl compound
  • N-glycosyl compound
  • Pentose monosaccharide
  • Pyrrolo[2,3-d]pyrimidine
  • Pyrimidinecarboxamide
  • Pyrrolopyrimidine
  • Pyrrole-3-carboxamide
  • Pyrrole-3-carboxylic acid or derivatives
  • Aminopyrimidine
  • Monosaccharide
  • Pyrimidine
  • Substituted pyrrole
  • Imidolactam
  • Vinylogous amide
  • Pyrrole
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Secondary alcohol
  • Carboxamide group
  • Primary carboxylic acid amide
  • Azacycle
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Organic oxide
  • Primary alcohol
  • Primary amine
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.4ALOGPS
logP-2.4ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)12.45ChemAxon
pKa (Strongest Basic)5.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area169.74 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity74.45 m³·mol⁻¹ChemAxon
Polarizability29.36 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
NPAtlas IDNPA005297
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID14261
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSangivamycin
METLIN IDNot Available
PubChem Compound14978
PDB IDNot Available
ChEBI ID85997
Good Scents IDNot Available
References
General References
  1. Rao KV: Structure of sangivamycin. J Med Chem. 1968 Sep;11(5):939-41. doi: 10.1021/jm00311a005. [PubMed:5748694 ]
  2. Metushi IG, Wriston A, Banerjee P, Gohlke BO, English AM, Lucas A, Moore C, Sidney J, Buus S, Ostrov DA, Mallal S, Phillips E, Shabanowitz J, Hunt DF, Preissner R, Peters B: Acyclovir Has Low but Detectable Influence on HLA-B*57:01 Specificity without Inducing Hypersensitivity. PLoS One. 2015 May 29;10(5):e0124878. doi: 10.1371/journal.pone.0124878. eCollection 2015. [PubMed:26024233 ]
  3. Loomis CR, Bell RM: Sangivamycin, a nucleoside analogue, is a potent inhibitor of protein kinase C. J Biol Chem. 1988 Feb 5;263(4):1682-92. [PubMed:3338987 ]