Metabolite Dapagliflozin 3-O-glucuronide

Name

Dapagliflozin 3-O-glucuronide

Description

Not Available

Structure

Similar Structures

Synonyms

Dapagliflozin M-15 metabolite

UNII

X42P3B148J

CAS number

1351438-75-9

Weight

Average: 585.0
Monoisotopic: 584.1660542

Chemical Formula

C₂₇H₃₃ClO₁₂

InChI Key

ZYZULHSUKTZGTR-PTNNFGGUSA-N

InChI

InChI=1S/C27H33ClO12/c1-2-37-15-6-3-12(4-7-15)9-14-10-13(5-8-16(14)28)23-22(34)24(18(30)17(11-29)38-23)39-27-21(33)19(31)20(32)25(40-27)26(35)36/h3-8,10,17-25,27,29-34H,2,9,11H2,1H3,(H,35,36)/t17-,18-,19+,20+,21-,22+,23+,24+,25+,27-/m1/s1

IUPAC Name

(2S,3S,4S,5R,6R)-6-{[(2S,3S,4R,5R,6R)-2-{4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

SMILES

CCOC1=CC=C(CC2=CC(=CC=C2Cl)[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O[C@@H]3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)C(O)=O)[C@H]2O)C=C1

Reactions

Dapagliflozin

Dapagliflozin 3-O-glucuronide

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0a4r-0113970000-0a7f3948e0fc9d614320
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-001i-1001090000-f31869d04bc18b7089f3
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-054o-0239310000-7d2e877c62f12b34dbf4
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-001i-9003460000-692bec305e7aade2420f
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-004u-2937680000-e5de2c55ac141512318d
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-003u-7268960000-8a8578246a6b34769894

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	221.76343	predicted	DeepCCS 1.0 (2019)
[M+H]+	223.41663	predicted	DeepCCS 1.0 (2019)
[M+Na]+	229.57347	predicted	DeepCCS 1.0 (2019)

External Links

ChemSpider: 34995189

Predicted Properties

Property	Value	Source
Water Solubility	0.388 mg/mL	ALOGPS
logP	1.24	ALOGPS
logP	0.66	Chemaxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	3.2	Chemaxon
pKa (Strongest Basic)	-3	Chemaxon
Physiological Charge	-1	Chemaxon
Hydrogen Acceptor Count	12	Chemaxon
Hydrogen Donor Count	7	Chemaxon
Polar Surface Area	195.6 Å²	Chemaxon
Rotatable Bond Count	9	Chemaxon
Refractivity	137.21 m³·mol^-1	Chemaxon
Polarizability	57.93 Å³	Chemaxon
Number of Rings	4	Chemaxon
Bioavailability	0	Chemaxon
Rule of Five	No	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	Yes	Chemaxon

Metabolite Dapagliflozin 3-O-glucuronide

Structure for Dapagliflozin 3-O-glucuronide

Collision Cross Sections (CCS)