dihydropyranocoumarin D2

ID: ALA1098736

Chembl Id: CHEMBL1098736

PubChem CID: 46832811

Max Phase: Preclinical

Molecular Formula: C23H20O5

Molecular Weight: 376.41

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Dihydropyranocoumarin D2 | dihydropyranocoumarin D2|CHEMBL1098736|SCHEMBL14105795

Canonical SMILES:  CC1(C)Oc2cc3oc(=O)ccc3cc2C[C@@H]1OC(=O)/C=C/c1ccccc1

Standard InChI:  InChI=1S/C23H20O5/c1-23(2)20(27-22(25)10-8-15-6-4-3-5-7-15)13-17-12-16-9-11-21(24)26-18(16)14-19(17)28-23/h3-12,14,20H,13H2,1-2H3/b10-8+/t20-/m0/s1

Standard InChI Key:  MPIAWVNZVMGWII-MFUYTVRRSA-N

Alternative Forms

1. Parent:

   

   ALA1098736

   DIHYDROPYRANOCOUMARIN D2

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: 376.41

Molecular Weight (Monoisotopic): 376.1311

AlogP: 4.13

#Rotatable Bonds: 3

Polar Surface Area: 65.74

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.77

CX LogD: 4.77

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.39

Np Likeness Score: 1.68

References

1. Kim DS, Park SH, Lee HK, Choo SJ, Lee JH, Song GY, Yoo ID, Kwon SB, Na JI, Park KC..  (2010)  Hypopigmentary action of dihydropyranocoumarin D2, a decursin derivative, as a MITF-degrading agent.,  73  (5): [PMID:20392068] [10.1021/np900455j]

2. Lee K, Lee JH, Boovanahalli SK, Choi Y, Choo SJ, Yoo ID, Kim DH, Yun MY, Lee GW, Song GY..  (2010)  Synthesis of (S)-(+)-decursin and its analogues as potent inhibitors of melanin formation in B16 murine melanoma cells.,  45  (12): [PMID:20884093] [10.1016/j.ejmech.2010.09.006]

3. Lee JH, Kim MA, Park S, Cho SH, Yun E, O YS, Kim J, Goo JI, Yun MY, Choi Y, Oh S, Song GY..  (2016)  Synthesis and evaluation of (+)-decursin derivatives as inhibitors of the Wnt/β-catenin pathway.,  26  (15): [PMID:27329797] [10.1016/j.bmcl.2016.06.029]

Source

Source(1):

• Scientific Literature