ID: ALA565966

Max Phase: Preclinical

Molecular Formula: C29H30O9

Molecular Weight: 522.55

Molecule Type: Small molecule

Representations

Canonical SMILES:  COc1cc2c(c(OC)c1OC)-c1c(cc3c(c1O)OCO3)C[C@H](C)[C@](C)(O)[C@H]2OC(=O)c1ccccc1

Standard InChI:  InChI=1S/C29H30O9/c1-15-11-17-12-20-24(37-14-36-20)23(30)21(17)22-18(13-19(33-3)25(34-4)26(22)35-5)27(29(15,2)32)38-28(31)16-9-7-6-8-10-16/h6-10,12-13,15,27,30,32H,11,14H2,1-5H3/t15-,27-,29-/m0/s1

Standard InChI Key:  VJGNXZQPNWMFAQ-SSEZWIOCSA-N

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

Properties

Molecular Weight: 522.55

Molecular Weight (Monoisotopic): 522.1890

AlogP: 4.66

#Rotatable Bonds: 5

Polar Surface Area: 112.91

Molecular Species: NEUTRAL

HBA: 9

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.39

CX Basic pKa:

CX LogP: 4.75

CX LogD: 4.75

Aromatic Rings: 3

Heavy Atoms: 38

QED Weighted: 0.46

Np Likeness Score: 1.76

References

1. Ma WH, Lu Y, Huang H, Zhou P, Chen DF..  (2009)  Schisanwilsonins A-G and related anti-HBV lignans from the fruits of Schisandra wilsoniana.,  19  (17): [PMID:19640714] [10.1016/j.bmcl.2009.07.078]

2. Li L, Pan Q, Sun M, Lu Q, Hu X..  (2006)  Dibenzocyclooctadiene lignans: a class of novel inhibitors of multidrug resistance-associated protein 1.,  80  (1): [PMID:17129588] [10.1016/j.lfs.2006.11.002]

3. Brunhofer G, Fallarero A, Karlsson D, Batista-Gonzalez A, Shinde P, Gopi Mohan C, Vuorela P..  (2012)  Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.,  20  (22): [PMID:23062825] [10.1016/j.bmc.2012.09.040]

4. Liu HW, Yu XZ, Padula D, Pescitelli G, Lin ZW, Wang F, Ding K, Lei M, Gao JM..  (2013)  Lignans from Schisandra sphenathera Rehd. et Wils. and semisynthetic schisantherin A analogues: absolute configuration, and their estrogenic and anti-proliferative activity.,  59  [PMID:23237974] [10.1016/j.ejmech.2012.11.003]

5. Lee MA, Kim WK, Park HJ, Kang SS, Lee SK..  (2013)  Anti-proliferative activity of hydnocarpin, a natural lignan, is associated with the suppression of Wnt/β-catenin signaling pathway in colon cancer cells.,  23  (20): [PMID:24018191] [10.1016/j.bmcl.2013.08.065]

Source

Source(2):

• Scientific Literature
• TP-search Transporter Database