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Record Information
Version2.0
Created at2021-06-20 19:14:57 UTC
Updated at2021-06-30 00:07:19 UTC
NP-MRD IDNP0035943
Secondary Accession NumbersNone
Natural Product Identification
Common Namebreynceanothanolic acid
Provided ByJEOL DatabaseJEOL Logo
DescriptionBreynceanothanolic acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. breynceanothanolic acid is found in Breynia fruticosa. breynceanothanolic acid was first documented in 2011 (PMID: 21428418). Based on a literature review very few articles have been published on breynceanothanolic acid.
Structure
Thumb
Synonyms
ValueSource
5alpha,10alpha-Epoxy-9alpha,27alpha-lactone-25(10->2alpha)abeo-a(1)-norlup-20(29)-en-28-Oic acidChEBI
5a,10a-Epoxy-9a,27a-lactone-25(10->2a)abeo-a(1)-norlup-20(29)-en-28-OateGenerator
5a,10a-Epoxy-9a,27a-lactone-25(10->2a)abeo-a(1)-norlup-20(29)-en-28-Oic acidGenerator
5alpha,10alpha-Epoxy-9alpha,27alpha-lactone-25(10->2alpha)abeo-a(1)-norlup-20(29)-en-28-OateGenerator
5Α,10α-epoxy-9α,27α-lactone-25(10->2α)abeo-a(1)-norlup-20(29)-en-28-OateGenerator
5Α,10α-epoxy-9α,27α-lactone-25(10->2α)abeo-a(1)-norlup-20(29)-en-28-Oic acidGenerator
BreynceanothanolateGenerator
Chemical FormulaC29H40O5
Average Mass468.6340 Da
Monoisotopic Mass468.28757 Da
IUPAC Name(1R,4R,5R,6R,9S,12S,13S,16R,19S,20S)-13,17,17,19-tetramethyl-22-oxo-6-(prop-1-en-2-yl)-21,23-dioxaheptacyclo[10.8.2.1^{16,20}.0^{1,13}.0^{4,12}.0^{5,9}.0^{16,20}]tricosane-9-carboxylic acid
Traditional Name(1R,4R,5R,6R,9S,12S,13S,16R,19S,20S)-13,17,17,19-tetramethyl-22-oxo-6-(prop-1-en-2-yl)-21,23-dioxaheptacyclo[10.8.2.1^{16,20}.0^{1,13}.0^{4,12}.0^{5,9}.0^{16,20}]tricosane-9-carboxylic acid
CAS Registry NumberNot Available
SMILES
[H]OC(=O)[C@]12C([H])([H])C([H])([H])[C@@]([H])(C(=C([H])[H])C([H])([H])[H])[C@]1([H])[C@@]1([H])C([H])([H])C([H])([H])[C@@]34OC(=O)[C@]1(C([H])([H])C2([H])[H])[C@]3(C([H])([H])[H])C([H])([H])C([H])([H])[C@]12O[C@]41[C@@]([H])(C([H])([H])[H])C([H])([H])C2(C([H])([H])[H])C([H])([H])[H]
InChI Identifier
InChI=1S/C29H40O5/c1-16(2)18-7-9-25(21(30)31)12-13-26-19(20(18)25)8-10-28(33-22(26)32)24(26,6)11-14-27-23(4,5)15-17(3)29(27,28)34-27/h17-20H,1,7-15H2,2-6H3,(H,30,31)/t17-,18-,19+,20+,24-,25-,26+,27+,28+,29-/m0/s1
InChI KeySNCMVKNGLNUISS-GCWSBASFSA-N
Experimental Spectra
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Breynia fruticosaJEOL database
    • Liu, Y. -P., et al, J. Nat. Prod. 74, 1161 (2011)
Chemical Taxonomy
ClassificationNot classified
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
logP4.71ALOGPS
logP5.5ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)4.16ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area76.13 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity125.34 m³·mol⁻¹ChemAxon
Polarizability52.1 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID26343469
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID67583
Good Scents IDNot Available
References
General References
  1. Liu YP, Cai XH, Feng T, Li Y, Li XN, Luo XD: Triterpene and sterol derivatives from the roots of Breynia fruticosa. J Nat Prod. 2011 May 27;74(5):1161-8. doi: 10.1021/np2000914. Epub 2011 Mar 23. [PubMed:21428418 ]
  2. Liu, Y. -P., et al. (2011). Liu, Y. -P., et al, J. Nat. Prod. 74, 1161 (2011). J. Nat. Prod..