SCS-C005191

(-)-4-O-(4-O-beta-D-glucopyranosylcaffeoyl)quinic acid

Pathway: Shikimates and Phenylpropanoids Superclass: Phenylpropanoids (C6-C3) Class: Cinnamic acids and derivatives Glycoside

Back to List

Chemical Structure

Structure of (-)-4-O-(4-O-beta-D-glucopyranosylcaffeoyl)quinic acid

Loading 3D structure...

3D conformers are computationally generated from SMILES by RDKit for visualization and download; they are not experimental crystal or NMR structures.

Download: SDF SMILES

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

516.5 Da

Threshold ≤ 500

ALogP

-3.17

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

3 violations (MW, HBD, HBA) — not drug-like by Ro5

Chemical Properties

Molecular Formula:

C22H28O14

Molecular Weight:

516.4500 Da

SMILES:

O=C(/C=C/c1ccc(O[C@H]2O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]2O)c(O)c1)O[C@H]1[C@H](O)C[C@@](O)(C(=O)O)C[C@H]1O

InChIKey:

                        WFYFOXSDFJBMRW-PJBQEJTBSA-N
                        
                    

InChI:

InChI=1S/C22H28O14/c23-8-14-16(28)17(29)18(30)20(35-14)34-13-3-1-9(5-10(13)24)2-4-15(27)36-19-11(25)6-22(33,21(31)32)7-12(19)26/h1-5,11-12,14,16-20,23-26,28-30,33H,6-8H2,(H,31,32)/b4-2+/t11-,12-,14+,16+,17-,18+,19-,20+,22-/m1/s1

Calculated Properties

ALogP:

-3.173 lipophilicity

TPSA:

243.90 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

3 (1 aromatic)

Chiral Centers:

Fsp³:

0.5455 fraction sp³ carbon

Database Information

Compound ID:

SCS-C005191

NPClassifier Pathway:

Shikimates and Phenylpropanoids

NPClassifier Superclass:

Phenylpropanoids (C6-C3)

NPClassifier Class:

Cinnamic acids and derivatives

Glycoside:

Yes

NPClassifier Status:

Classified

External Links:

General chemistry

PubChem ChemSpider ChEMBL

Natural product databases

COCONUT NP Atlas CMNPD: CMNPD26350

Biological Activity Data

No bioactivity data available for this compound.

Back to Compounds