5-(3,4,5-Trimethoxy-phenyl)-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxole

ID: ALA2115046

Chembl Id: CHEMBL2115046

PubChem CID: 9908081

Max Phase: Preclinical

Molecular Formula: C22H24O6

Molecular Weight: 384.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc([C@H]2c3cc4c(cc3C[C@H]3COC[C@@H]32)OCO4)cc(OC)c1OC

Standard InChI:  InChI=1S/C22H24O6/c1-23-19-6-13(7-20(24-2)22(19)25-3)21-15-8-18-17(27-11-28-18)5-12(15)4-14-9-26-10-16(14)21/h5-8,14,16,21H,4,9-11H2,1-3H3/t14-,16-,21-/m0/s1

Standard InChI Key:  CKUGPDQJERTFDI-HTZUNMPGSA-N

Alternative Forms

1. Parent:

   

   ALA2115046

   (5S,5aR,8aR)-5-(3,4,5-trimethoxyphenyl)-5,5a,6,8,8a,9-hexahydro-[2]benzofuro[5,6-f][1,3]benzodioxole

Molecule Features

Natural Product: Yes

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: 384.43

Molecular Weight (Monoisotopic): 384.1573

AlogP: 3.39

#Rotatable Bonds: 4

Polar Surface Area: 55.38

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.01

CX LogD: 3.01

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.81

Np Likeness Score: 1.26

References

1. Dantzig A, LaLonde RT, Ramdayal F, Shepard RL, Yanai K, Zhang M..  (2001)  Cytotoxic responses to aromatic ring and configurational variations in alpha-conidendrin, podophyllotoxin, and sikkimotoxin derivatives.,  44  (2): [PMID:11170627] [10.1021/jm990563p]

2. Gensler WJ, Murthy CD, Trammell MH..  (1977)  Nonenolizable podophyllotoxin derivatives.,  20  (5): [PMID:853503] [10.1021/jm00215a004]

Source

Source(1):

• Scientific Literature