rocagloic acid

ID: ALA518601

Chembl Id: CHEMBL518601

Cas Number: 190385-15-0

PubChem CID: 10322821

Max Phase: Preclinical

Molecular Formula: C27H26O8

Molecular Weight: 478.50

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Rocagloic Acid | Rocagloic Acid|190385-15-0|SCHEMBL750035|CHEMBL518601|HY-19355|MS-28886|CS-0015423|F82075|(1R,2R,3S,3aR,8bS)-1,8b-dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxylic acid

Canonical SMILES:  COc1ccc([C@@]23Oc4cc(OC)cc(OC)c4[C@]2(O)[C@H](O)[C@H](C(=O)O)[C@H]3c2ccccc2)cc1

Standard InChI:  InChI=1S/C27H26O8/c1-32-17-11-9-16(10-12-17)27-22(15-7-5-4-6-8-15)21(25(29)30)24(28)26(27,31)23-19(34-3)13-18(33-2)14-20(23)35-27/h4-14,21-22,24,28,31H,1-3H3,(H,29,30)/t21-,22-,24-,26+,27+/m1/s1

Standard InChI Key:  HLORMQRMDNZHJH-PXIJUOARSA-N

Alternative Forms

1. Parent:

   

   ALA518601

   ROCAGLOIC ACID

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: 478.50

Molecular Weight (Monoisotopic): 478.1628

AlogP: 3.05

#Rotatable Bonds: 6

Polar Surface Area: 114.68

Molecular Species: ACID

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.57

CX Basic pKa: ┄

CX LogP: 2.75

CX LogD: -0.61

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.50

Np Likeness Score: 1.45

References

1. Rivero-Cruz JF, Chai HB, Kardono LB, Setyowati FM, Afriatini JJ, Riswan S, Farnsworth NR, Cordell GA, Pezzuto JM, Swanson SM, Kinghorn AD..  (2004)  Cytotoxic constituents of the twigs and leaves of Aglaia rubiginosa.,  67  (3): [PMID:15043407] [10.1021/np0304417]

2. Wang SK, Cheng YJ, Duh CY..  (2001)  Cytotoxic constituents from leaves of Aglaia elliptifolia.,  64  (1): [PMID:11170675] [10.1021/np000341q]

3. Chambers JM, Lindqvist LM, Savage GP, Rizzacasa MA..  (2016)  Total synthesis of a biotinylated rocaglate: Selective targeting of the translation factors eIF4AI/II.,  26  (2): [PMID:26718843] [10.1016/j.bmcl.2015.12.045]

Source

Source(1):

• Scientific Literature