(6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-4,6,7-trihydroxy-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid

ID: ALA307753

Chembl Id: CHEMBL307753

PubChem CID: 44308533

Max Phase: Preclinical

Molecular Formula: C25H30O13

Molecular Weight: 538.50

Molecule Type: Small molecule

Names and Identifiers

Synonyms: L-731078 | CHEMBL307753|BDBM50038118|(6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-4,6,7-trihydroxy-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid

Canonical SMILES:  C=C(CCC12OC(C(=O)O)C(O)(C(=O)O)C(C(=O)O)(O1)[C@H](O)[C@H]2O)[C@@H](OC(C)=O)[C@H](C)Cc1ccccc1

Standard InChI:  InChI=1S/C25H30O13/c1-12(16(36-14(3)26)13(2)11-15-7-5-4-6-8-15)9-10-23-17(27)18(28)25(38-23,22(33)34)24(35,21(31)32)19(37-23)20(29)30/h4-8,13,16-19,27-28,35H,1,9-11H2,2-3H3,(H,29,30)(H,31,32)(H,33,34)/t13-,16-,17-,18-,19?,23?,24?,25?/m1/s1

Standard InChI Key:  RUIMBWGGEYKRPS-RFYBCTDESA-N

Alternative Forms

1. Parent:

   

   ALA307753

   (6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-4,6,7-trihydroxy-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic 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: 538.50

Molecular Weight (Monoisotopic): 538.1686

AlogP: -0.30

#Rotatable Bonds: 11

Polar Surface Area: 217.35

Molecular Species: ACID

HBA: 10

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 2.72

CX Basic pKa:

CX LogP: 1.09

CX LogD: -7.93

Aromatic Rings: 1

Heavy Atoms: 38

QED Weighted: 0.16

Np Likeness Score: 1.82

References

1. Shaw RE, Burgess C, Cousins RP, Giblin GM, Livermore DG, Shingler AH, Smith C, Youds PM.  (1994)  Synthesis of novel monocyclic squalestatin analogues as potential inhibitors of squalene synthase,  4  (18): [10.1016/S0960-894X(00)80062-1]

2. Harris GH, Dufresne C, Joshua H, Koch LA, Zink DL, Salmon PM, Goklen KE, Kurtz MM, Rew DJ, Bergstrom JD, Wilson KE.  (1995)  Isolation, structure determination and squalene synthase activity of L-731,120 and L-731,128, alkyl citrate analogs of zaragozic acids A and B,  5  (20): [10.1016/0960-894X(95)00419-T]

3. Ponpipom MM, Girotra NN, Bugianesi RL, Roberts CD, Berger GD, Burk RM, Marquis RW, Parsons WH, Bartizal KF, Bergstom JD..  (1994)  Structure-activity relationships of C1 and C6 side chains of zaragozic acid A derivatives.,  37  (23): [PMID:7966163] [10.1021/jm00049a022]

Source

Source(1):

• Scientific Literature