(2S,3S,4S,5R,6R)-6-{[(2S,3R,4S,5S,6S)-2-{[(3S,6aR,6bS,8aS,11S,12aR,14aR,14bS)-11-carboxy-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-6-carboxy-4,5-dihydroxyoxan-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid amine

• ChemBase ID: 104805
• Molecular Formular: C42H65NO16
• Molecular Mass: 839.9626
• Monoisotopic Mass: 839.43033501
• SMILES: CC1(C)C2CC[C@]3(C)[C@H](C(=O)C=C4[C@@H]5C[C@](C)(CC[C@]5(C)CC[C@@]34C)C(=O)O)[C@@]2(C)CC[C@@H]1O[C@@H]1[C@@H]([C@H]([C@@H]([C@@H](C(=O)O)O1)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](C(=O)O)O1)O)O)O.N
• Canonical SMILES: O[C@@H]1[C@@H](O[C@@H]2O[C@H](C(=O)O)[C@H]([C@@H]([C@H]2O)O)O)[C@H](O[C@@H]([C@H]1O)C(=O)O)O[C@H]1CC[C@]2(C(C1(C)C)CC[C@@]1([C@@H]2C(=O)C=C2[C@@]1(C)CC[C@@]1([C@H]2C[C@](C)(CC1)C(=O)O)C)C)C.N
• InChI: InChI=1S/C42H62O16.H3N/c1-37(2)21-8-11-42(7)31(20(43)16-18-19-17-39(4,36(53)54)13-12-38(19,3)14-15-41(18,42)6)40(21,5)10-9-22(37)55-35-30(26(47)25(46)29(57-35)33(51)52)58-34-27(48)23(44)24(45)28(56-34)32(49)50;/h16,19,21-31,34-35,44-48H,8-15,17H2,1-7H3,(H,49,50)(H,51,52)(H,53,54);1H3/t19-,21?,22-,23-,24-,25-,26-,27+,28-,29-,30+,31+,34-,35-,38+,39-,40-,41+,42+;/m0./s1
• InChIKey: ILRKKHJEINIICQ-UIAZACTHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-6-{[(2S,3R,4S,5S,6S)-2-{[(3S,6aR,6bS,8aS,11S,12aR,14aR,14bS)-11-carboxy-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-6-carboxy-4,5-dihydroxyoxan-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid amine
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-6-{[(2S,3R,4S,5S,6S)-2-{[(3S,6aR,6bS,8aS,11S,12aR,14aR,14bS)-11-carboxy-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-2,3,4a,5,6,7,8,9,10,12,12a,14a-dodecahydro-1H-picen-3-yl]oxy}-6-carboxy-4,5-dihydroxyoxan-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid amine
• Synonyms: Glycyrrhizin; GLYCYRRHIZIC ACID AMMONIUM SALT TRIHYDRATE

Database IDs

• CAS Number: 53956-04-0
• EC Number: 258-887-7
• PubChem SID: 162091968
• PubChem CID: 16213697

CALCULATED PROPERTIES

• Acid pKa: 2.961005
• H Acceptors: 16
• H Donor: 8
• LogD (pH = 5.5): -2.329018
• LogD (pH = 7.4): -6.5692225
• Log P: 3.1302059
• Molar Refractivity: 198.8299 cm^3
• Polarizability: 80.55014 Å^3
• Polar Surface Area: 267.04 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 209°C
• Density: 0.919 g/ml

Safety Information

• Storage Condition: Room Temperature (15-30°C), Desiccate
• RTECS: LZ6500000

DETAILS

MP Biomedicals - 02157249

Ammonium Salt

REFERENCES

• Cinatl, J., et al., The Lancet, 361 : 2045-2046 (2003).