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Record Information
Version2.0
Created at2021-01-05 20:38:18 UTC
Updated at2024-09-12 20:07:40 UTC
NP-MRD IDNP0010798
Secondary Accession NumbersNone
Natural Product Identification
Common NameBahamaolide A
Provided ByNPAtlasNPAtlas Logo
DescriptionBahamaolide A belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. Bahamaolide A is found in Streptomyces sp. Bahamaolide A was first documented in 2012 (PMID: 22574670). Based on a literature review a small amount of articles have been published on Bahamaolide A (PMID: 36424454) (PMID: 25052426).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC39H64O11
Average Mass708.9300 Da
Monoisotopic Mass708.44486 Da
IUPAC Name(3E,5E,7E,9E,11E,13E,16R,18S,20S,22S,24S,26R,28S,30S,32S,35S,36S)-16,18,20,22,24,26,28,30,32-nonahydroxy-35-methyl-36-(propan-2-yl)-1-oxacyclohexatriaconta-3,5,7,9,11,13-hexaen-2-one
Traditional Name(3E,5E,7E,9E,11E,13E,16R,18S,20S,22S,24S,26R,28S,30S,32S,35S,36S)-16,18,20,22,24,26,28,30,32-nonahydroxy-36-isopropyl-35-methyl-1-oxacyclohexatriaconta-3,5,7,9,11,13-hexaen-2-one
CAS Registry NumberNot Available
SMILES
[H]O[C@]1([H])C([H])([H])\C([H])=C(/[H])\C(\[H])=C(/[H])\C(\[H])=C(/[H])\C(\[H])=C(/[H])\C(\[H])=C(/[H])\C(\[H])=C([H])\C(=O)O[C@@]([H])(C([H])(C([H])([H])[H])C([H])([H])[H])[C@@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[C@]([H])(O[H])C([H])([H])[C@]([H])(O[H])C([H])([H])[C@]([H])(O[H])C([H])([H])[C@@]([H])(O[H])C([H])([H])[C@]([H])(O[H])C([H])([H])[C@@]([H])(O[H])C([H])([H])[C@@]([H])(O[H])C([H])([H])[C@@]([H])(O[H])C1([H])[H]
InChI Identifier
InChI=1/C39H64O11/c1-27(2)39-28(3)17-18-30(41)20-32(43)22-34(45)24-36(47)26-37(48)25-35(46)23-33(44)21-31(42)19-29(40)15-13-11-9-7-5-4-6-8-10-12-14-16-38(49)50-39/h4-14,16,27-37,39-48H,15,17-26H2,1-3H3/b5-4+,8-6+,9-7+,12-10+,13-11+,16-14+/t28-,29+,30-,31-,32-,33-,34-,35-,36+,37+,39-/s2
InChI KeyOLPMWTXTIALTJI-AVURYLKENA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Streptomyces sp.NPAtlas
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassMacrolides and analogues
Sub ClassNot Available
Direct ParentMacrolides and analogues
Alternative Parents
Substituents
  • Macrolide
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Carboxylic acid ester
  • Lactone
  • Secondary alcohol
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Polyol
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Organic oxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
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
logP0.96ChemAxon
pKa (Strongest Acidic)14.19ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area208.37 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity202.18 m³·mol⁻¹ChemAxon
Polarizability80.98 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
NPAtlas IDNPA002760
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Kim DG, Moon K, Kim SH, Park SH, Park S, Lee SK, Oh KB, Shin J, Oh DC: Bahamaolides A and B, antifungal polyene polyol macrolides from the marine actinomycete Streptomyces sp. J Nat Prod. 2012 May 25;75(5):959-67. doi: 10.1021/np3001915. Epub 2012 May 10. [PubMed:22574670 ]
  2. Aiken SG, Bateman JM, Liao HH, Fawcett A, Bootwicha T, Vincetti P, Myers EL, Noble A, Aggarwal VK: Iterative synthesis of 1,3-polyboronic esters with high stereocontrol and application to the synthesis of bahamaolide A. Nat Chem. 2023 Feb;15(2):248-256. doi: 10.1038/s41557-022-01087-9. Epub 2022 Nov 24. [PubMed:36424454 ]
  3. Lee SH, Moon K, Kim H, Shin J, Oh DC, Oh KB: Bahamaolide A from the marine-derived Streptomyces sp. CNQ343 inhibits isocitrate lyase in Candida albicans. Bioorg Med Chem Lett. 2014 Sep 1;24(17):4291-3. doi: 10.1016/j.bmcl.2014.07.021. Epub 2014 Jul 15. [PubMed:25052426 ]