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Record Information
Version2.0
Created at2022-09-09 03:40:54 UTC
Updated at2022-09-09 03:40:54 UTC
NP-MRD IDNP0278594
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1s,2r,4as,6as,6br,10s,12ar,12br,14bs)-10-(acetyloxy)-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydro-1h-picene-4a-carboxylic acid
DescriptionUrsolic acid acetate, also known as ursolate acetate, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (1s,2r,4as,6as,6br,10s,12ar,12br,14bs)-10-(acetyloxy)-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydro-1h-picene-4a-carboxylic acid is found in Cynomorium songaricum, Desfontainia spinosa, Diospyros lotus, Ilex latifolia, Leucoblepharis subsessilis, Ligustrum obtusifolium, Pieris japonica, Rhododendron anthopogon, Scaevola floribunda and Tripterygium hypoglaucum. (1s,2r,4as,6as,6br,10s,12ar,12br,14bs)-10-(acetyloxy)-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydro-1h-picene-4a-carboxylic acid was first documented in 2019 (PMID: 31835879). Based on a literature review a small amount of articles have been published on Ursolic acid acetate (PMID: 32003062) (PMID: 29130365) (PMID: 35022913) (PMID: 34023985).
Structure
Thumb
Synonyms
ValueSource
Ursolate acetateGenerator
Ursolic acid acetic acidGenerator
Chemical FormulaC32H50O4
Average Mass498.7480 Da
Monoisotopic Mass498.37091 Da
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILES
C[C@@H]1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](OC(C)=O)C(C)(C)C5CC[C@@]34C)[C@@H]2[C@H]1C)C(O)=O
InChI Identifier
InChI=1S/C32H50O4/c1-19-11-16-32(27(34)35)18-17-30(7)22(26(32)20(19)2)9-10-24-29(6)14-13-25(36-21(3)33)28(4,5)23(29)12-15-31(24,30)8/h9,19-20,23-26H,10-18H2,1-8H3,(H,34,35)/t19-,20+,23?,24-,25+,26+,29+,30-,31-,32+/m1/s1
InChI KeyPHFUCJXOLZAQNH-ISPSOPIZSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Cynomorium songaricumLOTUS Database
Desfontainia spinosaLOTUS Database
Diospyros lotusLOTUS Database
Ilex latifoliaLOTUS Database
Leucoblepharis subsessilisLOTUS Database
Ligustrum obtusifoliumLOTUS Database
Pieris japonicaLOTUS Database
Rhododendron anthopogonLOTUS Database
Scaevola floribundaLOTUS Database
Tripterygium hypoglaucumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
Alternative Parents
Substituents
  • Triterpenoid
  • Dicarboxylic acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic 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
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID19270414
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound15917992
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Ali A, Ahmed Zaki M, Parveen A, Ali Z, Khan IA: Bioassay guided isolation of mosquito biting deterrent compounds from Strumpfia maritima. Pest Manag Sci. 2020 Jul;76(7):2342-2346. doi: 10.1002/ps.5769. Epub 2020 Feb 26. [PubMed:32003062 ]
  2. Opoku F, Govender PP, Pooe OJ, Simelane MBC: Evaluating Iso-Mukaadial Acetate and Ursolic Acid Acetate as Plasmodium falciparum Hypoxanthine-Guanine-Xanthine Phosphoribosyltransferase Inhibitors. Biomolecules. 2019 Dec 11;9(12). pii: biom9120861. doi: 10.3390/biom9120861. [PubMed:31835879 ]
  3. de Azevedo MML, Cascaes MM, Guilhon GMSP, Andrade EHA, Zoghbi MDGB, da Silva JKR, Santos LS, da Silva SHM: Lupane triterpenoids, antioxidant potential and antimicrobial activity of Myrciaria floribunda (H. West ex Willd.) O. Berg. Nat Prod Res. 2019 Feb;33(4):506-515. doi: 10.1080/14786419.2017.1402311. Epub 2017 Nov 13. [PubMed:29130365 ]
  4. Tembe N, Machaba KE, Ndagi U, Kumalo HM, Mhlongo NN: Ursolic acid as a potential inhibitor of Mycobacterium tuberculosis cytochrome bc1 oxidase-a molecular modelling perspective. J Mol Model. 2022 Jan 13;28(2):35. doi: 10.1007/s00894-021-04993-w. [PubMed:35022913 ]
  5. Salomane N, Pooe OJ, Simelane MBC: Iso-mukaadial acetate and ursolic acid acetate inhibit the chaperone activity of Plasmodium falciparum heat shock protein 70-1. Cell Stress Chaperones. 2021 Jul;26(4):685-693. doi: 10.1007/s12192-021-01212-6. Epub 2021 May 23. [PubMed:34023985 ]
  6. LOTUS database [Link]