2-Methyl-butyric acid 8-[2-(4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester (5-epi-compactin)

ID: ALA3350220

PubChem CID: 118718801

Max Phase: Preclinical

Molecular Formula: C23H34O5

Molecular Weight: 390.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@H](C)C(=O)O[C@H]1CCC=C2C=C[C@H](C)[C@H](CC[C@H]3C[C@@H](O)CC(=O)O3)C21

Standard InChI:  InChI=1S/C23H34O5/c1-4-14(2)23(26)28-20-7-5-6-16-9-8-15(3)19(22(16)20)11-10-18-12-17(24)13-21(25)27-18/h6,8-9,14-15,17-20,22,24H,4-5,7,10-13H2,1-3H3/t14-,15-,17+,18-,19-,20-,22?/m0/s1

Standard InChI Key:  AJLFOPYRIVGYMJ-KDPPNUJGSA-N

Molfile:  

     RDKit          2D

 30 32  0  0  1  0  0  0  0  0999 V2000
    6.1137   -8.3376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3890   -7.9336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8508   -4.6019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6769   -6.7009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1137   -9.1580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3890   -7.1132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8216   -7.9253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8216   -9.5703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8383   -5.4265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5463   -9.1580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5713   -4.2021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8216   -7.0965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5463   -8.3251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5588   -5.8513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6769   -5.8471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2751   -4.6227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1387   -4.1896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2709   -5.4473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3890   -9.5745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9523   -7.1132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5463   -6.6884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6769   -8.3501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6769   -9.1622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9998   -4.2146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2584   -7.9211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2401   -6.7009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9523   -7.9461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5238   -7.1132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4630   -7.5588    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9873   -5.0350    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  9  1  0
  4  6  1  0
  5  1  1  0
  2  6  1  6
  7  1  1  0
  8  5  1  0
  9 14  1  0
 10 13  1  0
 11 16  1  0
  7 12  1  1
 13  7  1  0
 14 21  1  6
 15  4  2  0
 16 18  1  0
 17  3  2  0
 18 14  1  0
 19  5  2  0
 20  4  1  0
 21 12  1  0
 22  2  1  0
 23 19  1  0
 16 24  1  6
 13 25  1  1
 26 20  1  0
 20 27  1  1
 28 26  1  0
  7 29  1  6
 16 30  1  1
  8 10  2  0
 22 23  1  0
  3 11  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3350220

   ---

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: 390.52

Molecular Weight (Monoisotopic): 390.2406

AlogP: 3.95

#Rotatable Bonds: 6

Polar Surface Area: 72.83

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.62

CX LogD: 3.62

Aromatic Rings: ┄

Heavy Atoms: 28

QED Weighted: 0.70

Np Likeness Score: 2.47

References

1. Heathcock CH, Hadley CR, Rosen T, Theisen PD, Hecker SJ..  (1987)  Total synthesis and biological evaluation of structural analogues of compactin and dihydromevinolin.,  30  (10): [PMID:3656359] [10.1021/jm00393a030]

Source

Source(1):

• Scientific Literature