(7S,8S,8aS)-7-hydroxy-3-[(1E)-3-hydroxyprop-1-en-1-yl]-7-methyl-6-oxo-6,7,8,8a-tetrahydro-1H-isochromen-8-yl 2,4-dihydroxy-6-methylbenzoate

ID: ALA2011647

Chembl Id: CHEMBL2011647

PubChem CID: 57333718

Max Phase: Preclinical

Molecular Formula: C21H22O8

Molecular Weight: 402.40

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Pinophilin B | Pinophilin B|CHEMBL2011647|CHEBI:202740|BDBM50379294|[(7S,8S,8aS)-7-hydroxy-3-[(E)-3-hydroxyprop-1-enyl]-7-methyl-6-oxo-8,8a-dihydro-1H-isochromen-8-yl] 2,4-dihydroxy-6-methylbenzoate

Canonical SMILES:  Cc1cc(O)cc(O)c1C(=O)O[C@H]1[C@@H]2COC(/C=C/CO)=CC2=CC(=O)[C@@]1(C)O

Standard InChI:  InChI=1S/C21H22O8/c1-11-6-13(23)9-16(24)18(11)20(26)29-19-15-10-28-14(4-3-5-22)7-12(15)8-17(25)21(19,2)27/h3-4,6-9,15,19,22-24,27H,5,10H2,1-2H3/b4-3+/t15-,19+,21-/m1/s1

Standard InChI Key:  KKSKNERURMTALE-XWEVTOJWSA-N

Alternative Forms

1. Parent:

   

   ALA2011647

   PINOPHILIN B

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: 402.40

Molecular Weight (Monoisotopic): 402.1315

AlogP: 1.27

#Rotatable Bonds: 4

Polar Surface Area: 133.52

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.70

CX Basic pKa: ┄

CX LogP: 1.97

CX LogD: 1.95

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.55

Np Likeness Score: 2.67

References

1. Myobatake Y, Takeuchi T, Kuramochi K, Kuriyama I, Ishido T, Hirano K, Sugawara F, Yoshida H, Mizushina Y..  (2012)  Pinophilins A and B, inhibitors of mammalian A-, B-, and Y-family DNA polymerases and human cancer cell proliferation.,  75  (2): [PMID:22264170] [10.1021/np200523b]

2. Zhao DL, Shao CL, Zhang Q, Wang KL, Guan FF, Shi T, Wang CY..  (2015)  Azaphilone and Diphenyl Ether Derivatives from a Gorgonian-Derived Strain of the Fungus Penicillium pinophilum.,  78  (9): [PMID:26291474] [10.1021/acs.jnatprod.5b00575]

3. Ren J, Ding SS, Zhu A, Cao F, Zhu HJ..  (2017)  Bioactive Azaphilone Derivatives from the Fungus Talaromyces aculeatus.,  80  (8): [PMID:28749670] [10.1021/acs.jnatprod.7b00032]

4. Cao F, Meng ZH, Wang P, Luo DQ, Zhu HJ..  (2020)  Dipleosporalones A and B, Dimeric Azaphilones from a Marine-Derived Pleosporales sp. Fungus.,  83  (4): [PMID:32243144] [10.1021/acs.jnatprod.0c00132]

Source

Source(1):

• Scientific Literature