Betulinic acid






Names

    • Lup-20(29)-en-28-oic acid, 3beta -hydroxy-
    • beta-betulinic acid
    • C30H48O3
    • HMS1791P09
    • SCHEMBL61767
    • Prestwick3_000417
    • NSC-677578
    • NSC-113090
    • MFCD00009619
    • NSC113090
    • Lup-20(29)-en-28-oic acid, 3-hydroxy-, (3.beta.)-
    • Mairin
    • HMS2232K03
    • als-357
    • CCG-208159
    • 3-Hydroxy-(3beta)-Lup-20(29)-en-28-oic acid
    • (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid
    • Betulinic Acid, 24
    • .beta.-betulinic acid
    • BDBM23208
    • 472-15-1
    • Betulinic acid (Standard)
    • betulinic-acid
    • s3603
    • Betulic acid
    • Lup-20(29)-en-28-oic acid, 3-hydroxy-, (3beta)-
    • cid_64971
    • HMS2096C16
    • NCGC00163409-09
    • DS-15257
    • Betulinic acid, >=98% (HPLC)
    • STL570261
    • 3-Hydroxylup-20(29)-en-28-oic acid
    • NSC 113090
    • HB3799
    • Betulinic acid, technical grade, 90%
    • NCGC00163409-02
    • BSPBio_001587
    • BRD-K45401373-001-05-0
    • RL9-080
    • betulinic acid
    • 3beta-Hydroxy-20(29)-lupaene-28-oic acid
    • C08619
    • Betulinic acid, analytical standard
    • SMR000445624
    • MLS006011257
    • Lupatic acid;Betulic acid
    • HY-10529
    • (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysene-3a-carboxylic acid
    • CHEMBL269277
    • NSC677578
    • EINECS 207-448-8
    • 3beta-Hydroxy-lup-20(29)-en-28-oic acid
    • (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylicacid
    • BRD-K45401373-001-20-9
    • HY-10529R
    • 06L
    • AKOS015920276
    • BP-25391
    • SPBio_002313
    • CCRIS 6748
    • Prestwick1_000417
    • MLS000728510
    • GTPL3945
    • LMPR0106140004
    • SR-01000779609-3
    • Betulinic acid?
    • NCGC00163409-12
    • Q-100500
    • (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysene-3a-carboxylicacid
    • (3.BETA.)-3-HYDROXYLUP-20(29)-EN-28-OIC ACID
    • Q384111
    • (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-Hydroxy-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-eicosahydro-cyclopenta[a]chrysene-3a-carboxylic acid
    • BSPBio_000374
    • HMS1569C16
    • Prestwick0_000417
    • NCGC00163409-03
    • SMP2_000205
    • BETULINIC ACID [MI]
    • HMS1989P09
    • (1R,2R,5S,8R,9R,10R,13R,14R,17S,19R)-17-hydroxy-1,2,14,18,18-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosane-5-carboxylic acid
    • UNII-4G6A18707N
    • CHEBI:3087
    • Betulinicacid
    • DB12480
    • Lup-20(29)-en-28-oic acid, 3beta-hydroxy-
    • HMS3402P09
    • 4G6A18707N
    • (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid
    • (3beta)-3-hydroxylup-20(29)-en-28-oic acid
    • Prestwick_95
    • Betulinic acid
    • NSC 677578
    • Prestwick2_000417
    • SR-01000779609
    • 3beta-hydroxylup-20(29)-en-28-oic acid
    • (3beta)-3-Hydroxy-lup-20(29)-en-28-oic Acid
    • Lupatic Acid
    • DTXSID80861974
    • (1R,3 aS,5aR,5bR,7aR,9S,11aR,11bR,13 aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysene-3a-carboxylic acid
    • NS00042781
    • CS-1216
    • BPBio1_000412
    • BRD-K45401373-001-22-5

Attributes

  • Canonical SMILES

    CC(=C)[C@@H]1CC[C@]2([C@H]1[C@H]3CC[C@@H]4[C@]5(CC[C@@H](C([C@@H]5CC[C@]4([C@@]3(CC2)C)C)(C)C)O)C)C(=O)O

  • InChI

    InChI=1S/C30H48O3/c1-18(2)19-10-15-30(25(32)33)17-16-28(6)20(24(19)30)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h19-24,31H,1,8-17H2,2-7H3,(H,32,33)/t19-,20+,21-,22+,23-,24+,27-,28+,29+,30-/m0/s1

  • Molecule Class: Terpenoids
  • TPSA: 57.53
  • #RotBonds: 2
  • MW: 456.7110000000003
  • HBD: 2
  • HBA: 2
  • logP: 7.089500000000008
  • Chemical Formula: C30H48O3


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. contorta Cameroon 761060 N43440/HNC
    T. inconspicua Cameroon 761075 NHC61026

External Databases


References

  • A New Antimicrobial Phenylpropanol from the Leaves of Tabernaemontana inconspicua Stapf. (Apocynaceae) Inhibits Pathogenic Gram-Negative Bacteria. Antibiotics (Basel), 2022 (PMID 35052998).
  • Contortamide, a new anti-colon cancer cerebroside and other constituents from Tabernaemontana contorta Stapf (Apocynaceae). Nat Prod Res, 2021 (PMID 31274013).

Compound-Protein Relationships

Compound Activities

    • Anticolon cancer
    • Antimicrobial

Predicted NMR Spectral Data


Predicted MS Fragmentation Pattern

    N.B.: It is recommended to zoom in on a specific area of an MS plot before hovering on a peak.


Predicted ADMET Properties

    Property Model Name Predicted Value

    Absorption Caco-2 (logPaap) -5.47
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.67
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Non-Substrate
    Skin Permeability -1.89

    Distribution Blood-Brain Barrier (Central Nervous System) -1.92
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 2.02
    Plasma Protein Binding 94.58
    Steady State Volume of Distribution 0.48

    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 2.99
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs

    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -0.8
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Safe
    Liver Injury I Toxic
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose 1.95
    Liver Injury II Safe
    hERG Blockers Toxic
    Daphnia Maga 3.7
    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 Safe
    T. Pyriformis -111.09
    Rat (Acute) 2.48
    Rat (Chronic Oral) 2.11
    Fathead Minnow 3.86
    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 460.53
    Hydration Free Energy -2.54
    Log(D) at pH=7.4 5.26
    Log(P) 6.74
    Log S -6.44
    Log(Vapor Pressure) -9.54
    Melting Point 263.8
    pKa Acid 5.99
    pKa Basic 8.38