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(2S,3S,4S,5R,6S)-6-{[5,6-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
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ChemBase ID:
129421
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Molecular Formular:
C21H18O12
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Molecular Mass:
462.36042
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Monoisotopic Mass:
462.07982602
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SMILES and InChIs
SMILES:
O=c1cc(oc2cc(O[C@@H]3O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]3O)c(O)c(O)c12)c1ccc(O)cc1
Canonical SMILES:
OC(=O)[C@H]1O[C@@H](Oc2cc3oc(cc(=O)c3c(c2O)O)c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI:
InChI=1S/C21H18O12/c22-8-3-1-7(2-4-8)10-5-9(23)13-11(31-10)6-12(14(24)15(13)25)32-21-18(28)16(26)17(27)19(33-21)20(29)30/h1-6,16-19,21-22,24-28H,(H,29,30)/t16-,17-,18+,19-,21+/m0/s1
InChIKey:
DJSISFGPUUYILV-ZFORQUDYSA-N
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Cite this record
CBID:129421 http://www.chembase.cn/molecule-129421.html
NAMES AND DATABASE IDS
NAMES AND DATABASE IDS
Names Database IDs
IUPAC name
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(2S,3S,4S,5R,6S)-6-{[5,6-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
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IUPAC Traditional name
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Synonyms
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Breviscapine
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Breviscapin
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Scutellarein-7-glucuronide
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Scutellarein-7beta-D-glucuronide
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Scutellarein-7beta-D-glucuronoside
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Scutellarein-7-O-beta-D-glucuronide
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7-(β-D-glucopyranuronosyloxy)-5,6-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
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Scutellarin
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5,6-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl-β-D-glucopyranosiduronic acid hydrate
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7-(β-D-Glucopyranuronosyloxy)-5,6-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one hydrate
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Scutellarein-7-O-β-D-glucuronide
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Scutellarin hydrate
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5,6-Dihydroxy-2-(p-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl β-D-Glucopyranosiduronic Acid
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4',5,6,7-Tetrahydroxyflavone 7-β-D-Glucopyranuronoside
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Scutellarein 7-O-β-D-Glucuronide
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Scutellarein 7-β-D-Glucuronoside
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Scutellarin B
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5,6-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl-β-D-glucopyranosiduronic acid
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7-(β-D-Glucopyranuronosyloxy)-5,6-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
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Scutellarin
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CAS Number
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MDL Number
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Beilstein Number
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PubChem SID
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PubChem CID
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CHEMBL
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Chemspider ID
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Wikipedia Title
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DATA SOURCES
DATA SOURCES
All Sources Commercial Sources Non-commercial Sources
CALCULATED PROPERTIES
CALCULATED PROPERTIES
JChem
Acid pKa
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2.6182313
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H Acceptors
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12
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H Donor
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7
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LogD (pH = 5.5)
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-2.3393724
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LogD (pH = 7.4)
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-3.091061
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Log P
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0.45533025
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Molar Refractivity
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106.9066 cm3
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Polarizability
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41.499382 Å3
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Polar Surface Area
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203.44 Å2
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Rotatable Bonds
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4
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Lipinski's Rule of Five
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false
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DETAILS
DETAILS
Wikipedia
Sigma Aldrich
TRC
Sigma Aldrich -
SML0014
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Biochem/physiol Actions Scutellarin is a flavonoid that exhibits a number of cardio- and neuro-protective effects. Scutellarin inhibits p38 activity, ERK phosphorylation, and TGF-β expression and fibrosis in a rat myocardial infarct model. In a cerebral ischemia-reperfusion model, the compound reduced infarct volume and neurological deficits by increasing eNOS expression while inhibiting the induction of iNOS. |
Sigma Aldrich -
73577
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Biochem/physiol Actions Scutellarin is a flavonoid that exhibits a number of cardio- and neuro-protective effects. Scutellarin inhibits p38 activity, ERK phosphorylation, and TGF-β expression and fibrosis in a rat myocardial infarct model. In a cerebral ischemia-reperfusion model, the compound reduced infarct volume and neurological deficits by increasing eNOS expression while inhibiting the induction of iNOS. |
Toronto Research Chemicals -
S201900
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Scutellarin is an active flavonoid component from the medical plant Erigeron breviscapus (Vant) Hand-Mazz. Scutellarin is used as a micrpcirculation promoter for the treatment of cardio-cerebrovascular diseases. Studies suggest that Scutellarin has anti-c |
PATENTS
PATENTS
PubChem Patent
Google Patent