(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{2-[(1S,2S,5R,7R,10R,11S,14S,15S)-5-hydroxy-2,15-dimethyl(4,4,5,6,6-2H5)tetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]-2-oxoethoxy}oxane-2-carboxylic acid

• ChemBase ID: 178323
• Molecular Formular: C27H42O9
• Molecular Mass: 510.61698
• Monoisotopic Mass: 510.28288292
• SMILES: C1[C@H](C[C@@H]2[C@](C1)([C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@H](CC2)C(=O)CO[C@H]1[C@@H]([C@@H]([C@@H]([C@H](O1)C(=O)O)O)O)O)C)C)O
• Canonical SMILES: O[C@@H]1CC[C@]2([C@@H](C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2C(=O)CO[C@@H]1O[C@H](C(=O)O)[C@H]([C@H]([C@H]1O)O)O)C)C
• InChI: InChI=1S/C27H42O9/c1-26-9-7-14(28)11-13(26)3-4-15-16-5-6-18(27(16,2)10-8-17(15)26)19(29)12-35-25-22(32)20(30)21(31)23(36-25)24(33)34/h13-18,20-23,25,28,30-32H,3-12H2,1-2H3,(H,33,34)/t13-,14-,15+,16+,17+,18-,20+,21+,22-,23+,25-,26+,27+/m1/s1
• InChIKey: GSKNTGPRELRWGP-RVBRMEHISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{2-[(1S,2S,5R,7R,10R,11S,14S,15S)-5-hydroxy-2,15-dimethyl(4,4,5,6,6-^2H₅)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]-2-oxoethoxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{2-[(1S,2S,5R,7R,10R,11S,14S,15S)-5-hydroxy-2,15-dimethyl(4,4,5,6,6-^2H₅)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]-2-oxoethoxy}oxane-2-carboxylic acid
• Synonyms: (3α,5β)-3-Hydroxy-20-oxopregnan-21-yl-d5 β-D-Glucopyranosiduronic Acid; Tetrahydro 11-Deoxycorticosterone-d5 21-β-D-Glucuronide

Database IDs

• PubChem SID: 164234233
• PubChem CID: 71752438

CALCULATED PROPERTIES

• Acid pKa: 3.1883285
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -0.569132
• LogD (pH = 7.4): -1.7283531
• Log P: 1.7191287
• Molar Refractivity: 126.8896 cm^3
• Polarizability: 51.404594 Å^3
• Polar Surface Area: 153.75 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - T293282

Labelled Tetrahydro 11-Deoxycorticosterone 3α-β-D-Glucuronide (T293275). Tetrahydro 11-Deoxycorticosterone 3α-β-D-Glucuronide is a glucuronide metabolite of 11-Deoxycorticosterone (DOC) (D232590).

REFERENCES

• Mattox, V.R., et al.: Steroids, 42, 349 (1983)