(1R,4S,5R,9S,10R,13S)-13-hydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylic acid hydrate

• ChemBase ID: 154077
• Molecular Formular: C20H32O4
• Molecular Mass: 336.46568
• Monoisotopic Mass: 336.2300595
• SMILES: C[C@@]12CCC[C@@]([C@H]1CC[C@]13[C@H]2CC[C@](C1)(C(=C)C3)O)(C)C(=O)O.O
• Canonical SMILES: OC(=O)[C@]1(C)CCC[C@@]2([C@@H]1CC[C@@]13[C@H]2CC[C@](C3)(C(=C)C1)O)C.O
• InChI: InChI=1S/C20H30O3.H2O/c1-13-11-19-9-5-14-17(2,7-4-8-18(14,3)16(21)22)15(19)6-10-20(13,23)12-19;/h14-15,23H,1,4-12H2,2-3H3,(H,21,22);1H2/t14-,15-,17+,18+,19+,20-;/m0./s1
• InChIKey: SGPAFVVDOPSBEU-CRRYNOPCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,4S,5R,9S,10R,13S)-13-hydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^1,^1^0.0^4,^9]hexadecane-5-carboxylic acid hydrate
• IUPAC Traditional name: steviol hydrate
• Synonyms: (4α)-13-hydroxykaur-16-en-18-oic acid; (4α)-13-Hydroxykaur-16-en-18-oic acid hydrate; Steviol hydrate; Steviol

Database IDs

• CAS Number: 471-80-7(anhydrous)
• MDL Number: MFCD20441965
• PubChem SID: 162248216
• PubChem CID: 71311788

CALCULATED PROPERTIES

• Acid pKa: 4.704006
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.7888951
• LogD (pH = 7.4): 1.0111245
• Log P: 3.648531
• Molar Refractivity: 88.8917 cm^3
• Polarizability: 35.538048 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL
• Apperance: white to tan powder

Safety Information

• German water hazard class: 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C20H30O3 · xH2O

DETAILS

Sigma Aldrich - H8664

Biochem/physiol Actions
Steviol is an inhibitor of hOAT1 and hOAT3 organic anion transporters. Human organic anion transporter hOAT1 belongs to a superfamily of organic anion transporters, which play critical roles in the body disposition of clinically important drugs including anti-HIV therapeutics, anti-tumor drugs, antibiotics, anti-hypertensives, and anti-inflammatories. Steviol is a useful tool for studying renal drug clearance.