ID: ALA2021442

Max Phase: Preclinical

Molecular Formula: C41H50O11

Molecular Weight: 718.84

Molecule Type: Small molecule

Representations

Synonyms (2): Manassantin A | Manassantin B1
Synonyms from Alternative Forms(2):

Canonical SMILES:  COc1ccc([C@@H](O)[C@@H](C)Oc2ccc([C@H]3O[C@H](c4ccc(O[C@H](C)[C@H](O)c5ccc(OC)c(OC)c5)c(OC)c4)[C@H](C)[C@H]3C)cc2O)cc1OC

Standard InChI:  InChI=1S/C41H50O11/c1-22-23(2)41(29-13-17-34(37(21-29)49-9)51-25(4)39(44)27-11-16-33(46-6)36(20-27)48-8)52-40(22)28-12-14-31(30(42)18-28)50-24(3)38(43)26-10-15-32(45-5)35(19-26)47-7/h10-25,38-44H,1-9H3/t22-,23-,24-,25-,38+,39+,40+,41+/m1/s1

Standard InChI Key:  BHSIFEWQADUTCG-FZBBBUCASA-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: 718.84

Molecular Weight (Monoisotopic): 718.3353

AlogP: 7.52

#Rotatable Bonds: 15

Polar Surface Area: 134.53

Molecular Species: NEUTRAL

HBA: 11

HBD: 3

#RO5 Violations: 3

HBA (Lipinski): 11

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 9.76

CX Basic pKa:

CX LogP: 6.44

CX LogD: 6.44

Aromatic Rings: 4

Heavy Atoms: 52

QED Weighted: 0.11

Np Likeness Score: 0.75

References

1. Kasper AC, Moon EJ, Hu X, Park Y, Wooten CM, Kim H, Yang W, Dewhirst MW, Hong J..  (2009)  Analysis of HIF-1 inhibition by manassantin A and analogues with modified tetrahydrofuran configurations.,  19  (14): [PMID:19423348] [10.1016/j.bmcl.2009.04.071]

2. Minegishi H, Fukashiro S, Ban HS, Nakamura H..  (2013)  Discovery of Indenopyrazoles as a New Class of Hypoxia Inducible Factor (HIF)-1 Inhibitors.,  4  (2): [PMID:24900662] [10.1021/ml3004632]

3. Minegishi H, Fukashiro S, Ban HS, Nakamura H..  (2013)  Discovery of Indenopyrazoles as a New Class of Hypoxia Inducible Factor (HIF)-1 Inhibitors.,  4  (2): [PMID:24900662] [10.1021/ml3004632]

4. Cui H, Xu B, Wu T, Xu J, Yuan Y, Gu Q..  (2014)  Potential antiviral lignans from the roots of Saururus chinensis with activity against Epstein-Barr virus lytic replication.,  77  (1): [PMID:24359277] [10.1021/np400757k]

5. Yap JL, Chauhan J, Jung K, Chen L, Prochownik EV, Fletcher S.  (2012)  Small-molecule inhibitors of dimeric transcription factors: Antagonism of proteinprotein and proteinDNA interactions,  3  (5): [10.1039/C2MD00289B]

6. Kwon DY, Lee HE, Weitzel DH, Park K, Lee SH, Lee CT, Stephenson TN, Park H, Fitzgerald MC, Chi JT, Mook RA, Dewhirst MW, Lee YM, Hong J..  (2015)  Synthesis and Biological Evaluation of Manassantin Analogues for Hypoxia-Inducible Factor 1α Inhibition.,  58  (19): [PMID:26394152] [10.1021/acs.jmedchem.5b01220]

Source

Source(1):

• Scientific Literature