Ursolic acid






Names

    • NSC 167406
    • Urs-12-en-28-oic acid, 3-hydroxy-, (3.beta.)-
    • (1S,2R,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid
    • 77-52-1
    • 6Q5
    • 3.beta.-hydroxy-Urs-12-en-28-oate
    • AB00513802
    • HY-N0140
    • SR-01000779684
    • Urs-12-en-28-oic acid, 3-hydroxy-, (3beta)-
    • 3beta-Hydroxyurs-12-en-28-oic acid
    • ursolic-acid
    • 3beta-Hydroxyurs-12-en-28-oate
    • 3beta-hydroxy-Urs-12-en-28-oic acid
    • NCGC00017223-06
    • (3beta)-3-hydroxy-Urs-12-en-28-oate
    • EINECS 201-034-0
    • 3beta-hydroxy-Urs-12-en-28-oate
    • Ursolic acidMalol; Urson; 3beta-Hydroxyurs-12-en-28-oic acid
    • Malol
    • URSOLIC ACID (USP-RS)
    • 3beta-Hydroxy-12-ursen-28-ic acid
    • BRD-K68185022-001-14-8
    • AI3-03109
    • Ursolic acid, analytical standard
    • SMR000445681
    • (3.BETA.)-3-HYDROXYURS-12-EN-28-OIC ACID
    • (3beta)-3-Hydroxyurs-12-en-28-oate
    • SCHEMBL70205
    • URSOLIC ACID [USP-RS]
    • Prunol
    • HSDB 7685
    • URSOLIC ACID [MI]
    • URSOLIC ACID [HSDB]
    • (3beta,5beta,18alpha,20beta)-3-hydroxyurs-12-en-28-oic acid
    • HY-N0140R
    • 3beta-Hydroxy-12-ursen-28-oic Acid
    • NSC-4060
    • BDBM50148911
    • Ursolic acid
    • Ursolic acid (Standard)
    • MLS002207073
    • AKOS005228010
    • C08988
    • Ursolic acid, primary pharmaceutical reference standard
    • .beta.-Ursolic acid
    • URSOLIC ACID (CONSTITUENT OF HOLY BASIL LEAF)
    • Ursolic acid, European Pharmacopoeia (EP) Reference Standard
    • NSC4060
    • BRD-K68185022-001-02-3
    • 3B-HYDROXYURS-12-EN-28-OIC ACID
    • (3beta)-3-Hydroxyurs-12-en-28-oic acid
    • Ursolicacid
    • URSOLIC ACID (CONSTITUENT OF HOLY BASIL LEAF) [DSC]
    • Ursolic acid, United States Pharmacopeia (USP) Reference Standard
    • P3M2575F3F
    • (+)-Ursolic acid
    • U0065
    • SR-01000779684-5
    • NSC-167406
    • Q416260
    • AS-35119
    • Prestwick3_000089
    • CS-3799
    • Urson
    • Q-201916
    • AF479D19-631E-48F1-8ABA-FB2A806046FA
    • MFCD00009621
    • CHEMBL169
    • Prunol;Urson;Malol
    • NSC 4060
    • Bungeolic acid
    • SR-01000779684-4
    • Micromerol
    • 1ST001599
    • BPBio1_000020
    • TNP00103
    • DB15588
    • (3 beta)-3-hydroxyurs-12-en-28-oic acid
    • CCRIS 7123
    • DTXSID70883221
    • CCG-208282
    • MLS002154196
    • 3.beta.-hydroxy-Urs-12-en-28-oic acid
    • Ursolic acid, >=90%
    • UNII-P3M2575F3F
    • Urs-12-en-28-oic acid, 3beta-hydroxy-
    • HMS2231P19
    • AKOS016023773
    • NS00006443
    • CHEBI:9908
    • BRD-K68185022-001-12-2
    • (3beta)-3-hydroxy-Urs-12-en-28-oic acid
    • BSPBio_000018
    • MLS000728569
    • HMS2095A20
    • URSOLIC ACID [WHO-DD]
    • LMPR0106180007
    • (1S,2R,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylicacid

Attributes

  • Canonical SMILES

    C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)O)C)C)[C@@H]2[C@H]1C)C)C(=O)O

  • InChI

    InChI=1S/C30H48O3/c1-18-10-15-30(25(32)33)17-16-28(6)20(24(30)19(18)2)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h8,18-19,21-24,31H,9-17H2,1-7H3,(H,32,33)/t18-,19+,21+,22-,23+,24+,27+,28-,29-,30+/m1/s1

  • Molecule Class: Terpenoids
  • TPSA: 57.53
  • #RotBonds: 1
  • MW: 456.7110000000002
  • HBD: 2
  • HBA: 2
  • logP: 7.089500000000008
  • Chemical Formula: C30H48O3


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. africana - 761050 -
    T. chippii Ivory Coast - Lg12291
    T. contorta Cameroon 761060 N43440/HNC
    T. divaricata China, Japan, Thailand, Bangladesh, Vienna 52861 BBP0671
    T. elegans Mozambique, South Africa, Indonesia 761068 23/SM
    T. lonciflora Mozambique, South Africa, Indonesia - -
    T. orientalis Mozambique, South Africa, Indonesia 715769 -
    T. ventricosa Kenya 761103 AM2017/04

External Databases


References

  • Antileishmanial and cytotoxic activity of secondary metabolites from Taberneamontana ventricosa and two aloe species. Nat Prod Res, 2022 (PMID 33459049).
  • Contortamide, a new anti-colon cancer cerebroside and other constituents from Tabernaemontana contorta Stapf (Apocynaceae). Nat Prod Res, 2021 (PMID 31274013).
  • Induction of triterpene biosynthesis by elicitors in suspension cultures of Tabernaemontana species. Plant Cell Rep, 1988 (PMID 24241415).

Compound-Protein Relationships


Compound Activities

    • Cytotoxicity
    • Antimicrobial
    • Anticolon cancer
    • Antileishmanial

Predicted NMR Spectral Data


Predicted MS Fragmentation Patternn


Predicted ADMET Properties

    Category Property Name Predicted Value
    Absorption Caco-2 (logPaap) -5.38
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.69
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Non-Substrate
    Skin Permeability -1.83
    Distribution Blood-Brain Barrier (Central Nervous System) -2.0
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.9
    Plasma Protein Binding 91.77
    Steady State Volume of Distribution 0.55
    Metabolism Breast Cancer Resistance Protein Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate Non-Substrate
    CYP 2C19 Inhibitor Non-Inhibitor
    CYP 2C19 substrate Non-Substrate
    CYP 2C9 Inhibitor Non-Inhibitor
    CYP 2C9 Substrate Non-Substrate
    CYP 2D6 Inhibitor Non-Inhibitor
    CYP 2D6 Substrate Non-Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Inhibitor
    OATP1B3 Inhibitor
    Excretion Clearance 2.98
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -0.57
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Safe
    Liver Injury I Toxic
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose 1.98
    Liver Injury II Safe
    hERG Blockers Toxic
    Daphnia Maga 3.3
    Micronucleos Safe
    NR-AhR Safe
    NR-AR Toxic
    NR-AR-LBD Safe
    NR-Aromatase Safe
    NR-ER Safe
    NR-ER-LBD Safe
    NR-GR Toxic
    NR-PPAR-gamma Safe
    NR-TR Toxic
    T. Pyriformis -94.72
    Rat (Acute) 2.37
    Rat (Chronic Oral) 2.05
    Fathead Minnow 3.89
    Respiratory Disease Toxic
    Skin Sensitisation Toxic
    SR-ATAD5 Safe
    SR-ARE Toxic
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 464.92
    Hydration Free Energy -2.94
    Log(D) at pH=7.4 5.25
    Log(P) 7.02
    Log S -6.45
    Log(Vapor Pressure) -9.16
    Melting Point 246.4
    pKa Acid 6.08
    pKa Basic 8.54