(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?,??.0?,?.0??,??]henicosane-5-carboxylic acid

• ChemBase ID: 106009
• Molecular Formular: C30H48O3
• Molecular Mass: 456.70032
• Monoisotopic Mass: 456.3603454
• SMILES: O=C(O)[C@]12[C@@H]([C@@H]3[C@@]([C@]4([C@@H]([C@]5(C)[C@@H](CC4)C(C)(C)[C@@H](O)CC5)CC3)C)(C)CC1)[C@H](C(=C)C)CC2
• Canonical SMILES: CC(=C)[C@@H]1CC[C@]2([C@H]1[C@H]1CC[C@H]3[C@@]([C@]1(C)CC2)(C)CC[C@@H]1[C@]3(C)CC[C@@H](C1(C)C)O)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
• InChIKey: QGJZLNKBHJESQX-FZFNOLFKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (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?,??.0?,?.0??,??]henicosane-5-carboxylic acid; (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,^1^0.0^5,^9.0^1^4,^1^9]henicosane-5-carboxylic acid
• IUPAC Traditional name: mairin
• Synonyms: 3β-Hydroxy-20(29)-lupaene-28-oic acid; Betulinic acid; 3β-Hydroxy-20(29)-lupaene-28-oic acid; BETULINIC ACID; Betulic acid; Mairin; 白桦脂酸; 桦木酸

Database IDs

• CAS Number: 472-15-1
• EC Number: 207-448-8
• MDL Number: MFCD00009619
• PubChem SID: 24888370; 162087270
• PubChem CID: 64971
• CHEBI ID: 3087
• CHEMBL: 269277
• Chemspider ID: 58496
• Wikipedia Title: Betulinic_acid

CALCULATED PROPERTIES

• Acid pKa: 4.7483134
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 5.817948
• LogD (pH = 7.4): 4.041123
• Log P: 6.639739
• Molar Refractivity: 132.6255 cm^3
• Polarizability: 53.23124 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 295-298 °C (dec.)(lit.); 295-298°C (dec); 316–318 °C
• Optical Rotation: [α]20/D +7.8°, c = 0.9 in pyridine

Safety Information

• Storage Condition: -20°C
• German water hazard class: 3
• Safety Statements: R
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97%; ≥97.0% (HPLC); ≥98% (HPLC); 90%
• Grade: analytical standard; technical grade
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C30H48O3

DETAILS

MP Biomedicals - 02195859

Purity: >97%
Selectively inhibits human melanoma in cell culture and in animal models and demonstrates antitumor properties by inducing apoptosis. Possess anti-HIV properties.

Sigma Aldrich - B8936

Biochem/physiol Actions
Betulinic acid, a pentacyclic triterpene, selectively induces apoptosis in tumor cells by directly activating the mitochondrial pathway of apoptosis through a p53- and CD95-independent mechanism.

Sigma Aldrich - 855057

Biochem/physiol Actions
Betulinic acid, a pentacyclic triterpene, selectively induces apoptosis in tumor cells by directly activating the mitochondrial pathway of apoptosis through a p53- and CD95-independent mechanism.
Packaging
100, 500 mg in glass bottle

Sigma Aldrich - 91466

Biochem/physiol Actions
Betulinic acid, a pentacyclic triterpene, selectively induces apoptosis in tumor cells by directly activating the mitochondrial pathway of apoptosis through a p53- and CD95-independent mechanism.