cis-(+/-)-2-(8-Methoxy-1-methyl-5,10-dioxo-3,4,5,10-tetrahydro-1H-naphtho[2,3-c]pyran-3-yl)acetic acid

ID: ALA608117

Chembl Id: CHEMBL608117

PubChem CID: 45257209

Max Phase: Preclinical

Molecular Formula: C17H16O6

Molecular Weight: 316.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc2c(c1)C(=O)C1=C(C[C@H](CC(=O)O)O[C@@H]1C)C2=O

Standard InChI:  InChI=1S/C17H16O6/c1-8-15-13(6-10(23-8)7-14(18)19)16(20)11-4-3-9(22-2)5-12(11)17(15)21/h3-5,8,10H,6-7H2,1-2H3,(H,18,19)/t8-,10-/m1/s1

Standard InChI Key:  YOYHYPFUGDLGQZ-PSASIEDQSA-N

Alternative Forms

1. Parent:

   

   ALA608117

   2-[(1R,3R)-8-methoxy-1-methyl-5,10-dioxo-3,4-dihydro-1H-benzo[g]isochromen-3-yl]acetic acid

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: 316.31

Molecular Weight (Monoisotopic): 316.0947

AlogP: 2.02

#Rotatable Bonds: 3

Polar Surface Area: 89.90

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.57

CX Basic pKa: ┄

CX LogP: 1.21

CX LogD: -2.14

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.92

Np Likeness Score: 1.19

References

1. Sperry J, Lorenzo-Castrillejo I, Brimble MA, Machín F..  (2009)  Pyranonaphthoquinone derivatives of eleutherin, ventiloquinone L, thysanone and nanaomycin A possessing a diverse topoisomerase II inhibition and cytotoxicity spectrum.,  17  (20): [PMID:19783445] [10.1016/j.bmc.2009.08.064]

2. Heapy AM, Patterson AV, Smaill JB, Jamieson SM, Guise CP, Sperry J, Hume PA, Rathwell K, Brimble MA..  (2013)  Synthesis and cytotoxicity of pyranonaphthoquinone natural product analogues under bioreductive conditions.,  21  (24): [PMID:24436995] [10.1016/j.bmc.2013.09.052]

Source

Source(1):

• Scientific Literature