SCS-C005195
(Z)-6-hydroxy-7-methoxy-2-(4-methoxybenzylidene)-1-benzofuran-3(2H)-one 4-O-尾-D-glucopyranoside
Pathway: Shikimates and Phenylpropanoids
Superclass: Flavonoids
Class: Aurones
Glycoside
Chemical Structure
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3D conformers are computationally generated from SMILES by RDKit for visualization and download; they are not experimental crystal or NMR structures.
Source Information
Penicillium citrinum
(NA)
Kingdom
Fungi
Phylum
Ascomycota
Class
Eurotiomycetes
Order
Eurotiales
Family
Aspergillaceae
Genus
Penicillium
Species
Penicillium citrinum
Zhangzhou
Records of Natural Products, 2015, 9, 271-275. || Natural Product Communications, 2013, 8, 67-68. || Chemistry of Natural Compounds, 2013, 49, 653-656. || Natural Product Communications, 2013, 8, 1069-1070. || Acta Chimica Sinica / Acta Chim. Sin, 2001. || Natural Product Communications, 2013, 8, 1127-1128. || Chemical Journal of Chinese Universities, 2007. || Acta Chimica Sinica, 2002. || Turkish Journal of Chemistry, 1999, 23(3), 339-344. || Chinese Journal of Organic Chemistry, 2002. || Chinese Journal of Chemistry, 2013, 31, 100-104. || Marine Drugs, 2068. || Helvetica Chimica Acta, 2013, 96, 1188-1196. || Liu Qing || Li Ruisheng. Study on chemical constituents of Chinese soft coral. (37) Structure of a novel polyhydroxylated steroid / 《() --》. || The Journal of Antibiotics, 2013, 66, 327-331. || Indian Journal of Chemistry, Section B, 2002. || Acta Scientiarum Naturalium Universitatis Sunyatseni, 2002. || Acta Scientiarum Naturalium Universitatis Sunyatseni, 1999. || Acta Scientiarum Naturalium Universitatis Sunyatseni, 1998, 37(3), 82-85. || Acta Scientiarum Naturalium Universitatis Sunyatseni, 1987. || Chinese Journal of Organic Chemistry, 2007. || Natural Product Communications, 2015, 10, 1033-1037. || Acta Scientiarum Naturalium Universitatis Sunyatseni, 2001. || Chemical Research in Chinese Universities, 1998, 14(4), 426-427. || Acta Scientiarum Naturalium Universitatis Sunyatseni, 1986. || Phytochemistry Letters, 2013, 6, 392-396. || Natural Product Reports, 1997. || Chinese Journal of Organic Chemistry, 2001. || Journal of Natural Products, 2013. || Chinese Journal of Marine Drugs, 1998, 17(1), 1-3. || Chemical Journal of Chinese Universities, 2021. || Chinese Journal of Marine Drugs, 2003, 22, 28-30. || Natural Product Communications, 2015, 10, 1203-1208. || Archives of Pharmacal Research, 2013, 36, 739-744. || Steroids, 2013, 78, 396-400.
Drug-likeness (Lipinski Ro5)
Molecular Weight
476.4 Da
Threshold ≤ 500
ALogP
0.20
Threshold ≤ 5
H-Bond Donors
5
Threshold ≤ 5
H-Bond Acceptors
11
Threshold ≤ 10
1 violation (HBA) — borderline drug-like
Chemical Properties
Molecular Formula:
C23H24O11
Molecular Weight:
476.4300 Da
SMILES:
COc1ccc(/C=C2\Oc3c(OC)c(O)cc(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)c3C2=O)cc1
InChIKey:
XHFZRZHUGLAKRG-CPYCMRKHSA-N
InChI:
InChI=1S/C23H24O11/c1-30-11-5-3-10(4-6-11)7-14-17(26)16-13(8-12(25)21(31-2)22(16)32-14)33-23-20(29)19(28)18(27)15(9-24)34-23/h3-8,15,18-20,23-25,27-29H,9H2,1-2H3/b14-7-/t15-,18-,19+,20-,23-/m1/s1
Calculated Properties
ALogP:
0.204 lipophilicity
TPSA:
164.37 Ų polar surface area
H-Bond Donors:
5
H-Bond Acceptors:
11
Rotatable Bonds:
6
Ring Count:
4
(2 aromatic)
Chiral Centers:
5
Fsp³:
0.3478 fraction sp³ carbon
Database Information
Compound ID:
SCS-C005195
NPClassifier Pathway:
Shikimates and Phenylpropanoids
NPClassifier Superclass:
Flavonoids
NPClassifier Class:
Aurones
Glycoside:
Yes
NPClassifier Status:
Classified
External Links:
General chemistry
Natural product databases
Biological Activity Data
No bioactivity data available for this compound.