4-(6,7-dihydroxy-3,7-dimethyloct-2-enyloxy)-7H-furo[3,2-g]chromen-7-one

ID: ALA513494

Chembl Id: CHEMBL513494

Cas Number: 145414-76-2

PubChem CID: 6440498

Product Number: D131746

Max Phase: Preclinical

Molecular Formula: C21H24O6

Molecular Weight: 372.42

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 6',7'-Dihydroxy-Bergamottin | 6',7'-dihydroxybergamottin|145414-76-2|6',7'-dihydroxy Bergamottin|71339-34-9|6,7-dihydroxybergamottin|4-[(E)-6,7-dihydroxy-3,7-dimethyloct-2-enoxy]furo[3,2-g]chromen-7-one|7H-Furo[3,2-g][1]benzopyran-7-one, 4-[[(2E)-6,7-dihydroxy-3,7-dimethyl-2-octen-1-yl]oxy]-|4-[[(2E)-6,7-Dihydroxy-3,7-dimethyl-2-octenyl]oxy]-7H-fuoro[3,2-g][1]benzopyran-7-one|7H-Furo[3,2-g][1]benzopyran-7-one, 4-[(6,7-dihydroxy-3,7-dimethyl-2-octen-1-yl)oxy]-|6',7'-Dihydroxy-Bergamottin|CHEMBL51Show More⌵

Canonical SMILES:  C/C(=C\COc1c2ccoc2cc2oc(=O)ccc12)CCC(O)C(C)(C)O

Standard InChI:  InChI=1S/C21H24O6/c1-13(4-6-18(22)21(2,3)24)8-10-26-20-14-5-7-19(23)27-17(14)12-16-15(20)9-11-25-16/h5,7-9,11-12,18,22,24H,4,6,10H2,1-3H3/b13-8+

Standard InChI Key:  IXZUPBUEKFXTSD-MDWZMJQESA-N

Alternative Forms

1. Parent:

   

   ALA513494

   DIHYDROXYBERGAMOTTIN

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 372.42

Molecular Weight (Monoisotopic): 372.1573

AlogP: 3.78

#Rotatable Bonds: 7

Polar Surface Area: 93.04

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.84

CX Basic pKa: ┄

CX LogP: 2.67

CX LogD: 2.67

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.48

Np Likeness Score: 1.90

References

1. Hirata T, Fujii M, Akita K, Yanaka N, Ogawa K, Kuroyanagi M, Hongo D..  (2009)  Identification and physiological evaluation of the components from citrus fruits as potential drugs for anti-corpulence and anticancer.,  17  (1): [PMID:19054677] [10.1016/j.bmc.2008.11.039]

2. PubChem BioAssay data set, 

3. Fontana E, Dansette PM, Poli SM..  (2005)  Cytochrome p450 enzymes mechanism based inhibitors: common sub-structures and reactivity.,  6  (1): [PMID:16248836] [10.2174/138920005774330639]

4. Satoh H, Yamashita F, Tsujimoto M, Murakami H, Koyabu N, Ohtani H, Sawada Y..  (2005)  Citrus juices inhibit the function of human organic anion-transporting polypeptide OATP-B.,  33  (1): [PMID:15640378] [10.1124/dmd.104.002337]

5. Li P, Lu C, Balani SK, Gan LS..  (2011)  A refined cytochrome P540 IC₅₀ shift assay for reliably identifying CYP3A time-dependent inhibitors.,  39  (6): [PMID:21393461] [10.1124/dmd.111.038208]

6. Chen J, Lu Y, Ye X, Emam M, Zhang H, Wang H..  (2020)  Current advances in Vibrio harveyi quorum sensing as drug discovery targets.,  207  [PMID:32871343] [10.1016/j.ejmech.2020.112741]

Source

Source(3):

• Scientific Literature
• PubChem BioAssays
• TP-search Transporter Database