ID: ALA293914

Max Phase: Preclinical

Molecular Formula: C44H26O12

Molecular Weight: 746.68

Molecule Type: Small molecule

Representations

Synonyms (1): NSC-158393
Synonyms from Alternative Forms(1):

Canonical SMILES:  O=c1c(C(c2ccc(C(c3c(O)oc4ccccc4c3=O)c3c(O)oc4ccccc4c3=O)cc2)c2c(O)oc3ccccc3c2=O)c(O)oc2ccccc12

Standard InChI:  InChI=1S/C44H26O12/c45-37-23-9-1-5-13-27(23)53-41(49)33(37)31(34-38(46)24-10-2-6-14-28(24)54-42(34)50)21-17-19-22(20-18-21)32(35-39(47)25-11-3-7-15-29(25)55-43(35)51)36-40(48)26-12-4-8-16-30(26)56-44(36)52/h1-20,31-32,49-52H

Standard InChI Key:  GSKXJQZBERQLFV-UHFFFAOYSA-N

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

Properties

Molecular Weight: 746.68

Molecular Weight (Monoisotopic): 746.1424

AlogP: 7.30

#Rotatable Bonds: 6

Polar Surface Area: 201.76

Molecular Species: ACID

HBA: 12

HBD: 4

#RO5 Violations: 3

HBA (Lipinski): 12

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 4.72

CX Basic pKa:

CX LogP: 7.86

CX LogD: -0.11

Aromatic Rings: 9

Heavy Atoms: 56

QED Weighted: 0.13

Np Likeness Score: 0.03

References

1. Wang S, Milne GW, Yan X, Posey IJ, Nicklaus MC, Graham L, Rice WG..  (1996)  Discovery of novel, non-peptide HIV-1 protease inhibitors by pharmacophore searching.,  39  (10): [PMID:8642563] [10.1021/jm950874+]

2. Mazumder A, Wang S, Neamati N, Nicklaus M, Sunder S, Chen J, Milne GW, Rice WG, Burke TR, Pommier Y..  (1996)  Antiretroviral agents as inhibitors of both human immunodeficiency virus type 1 integrase and protease.,  39  (13): [PMID:8691444] [10.1021/jm960074e]

3. Zhao H, Neamati N, Hong H, Mazumder A, Wang S, Sunder S, Milne GW, Pommier Y, Burke TR..  (1997)  Coumarin-based inhibitors of HIV integrase.,  40  (2): [PMID:9003523] [10.1021/jm960450v]

4. Hong H, Neamati N, Wang S, Nicklaus MC, Mazumder A, Zhao H, Burke TR, Pommier Y, Milne GW..  (1997)  Discovery of HIV-1 integrase inhibitors by pharmacophore searching.,  40  (6): [PMID:9083481] [10.1021/jm960754h]

5. Nolan KA, Zhao H, Faulder PF, Frenkel AD, Timson DJ, Siegel D, Ross D, Burke TR, Stratford IJ, Bryce RA..  (2007)  Coumarin-based inhibitors of human NAD(P)H:quinone oxidoreductase-1. Identification, structure-activity, off-target effects and in vitro human pancreatic cancer toxicity.,  50  (25): [PMID:17999461] [10.1021/jm070472p]

6. Hamdi N, Puerta MC, Valerga P..  (2008)  Synthesis, structure, antimicrobial and antioxidant investigations of dicoumarol and related compounds.,  43  (11): [PMID:18485537] [10.1016/j.ejmech.2008.03.038]

Source

Source(1):

• Scientific Literature