(1S,4aR)-5-(carboxymethyl)-7-hydroxy-1,4a-dimethyl-6-methylenedecahydronaphthalene-1-carboxylic acid

ID: ALA1077022

PubChem CID: 46881228

Max Phase: Preclinical

Molecular Formula: C16H24O5

Molecular Weight: 296.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1C(O)CC2[C@](C)(CCC[C@]2(C)C(=O)O)C1CC(=O)O

Standard InChI:  InChI=1S/C16H24O5/c1-9-10(7-13(18)19)15(2)5-4-6-16(3,14(20)21)12(15)8-11(9)17/h10-12,17H,1,4-8H2,2-3H3,(H,18,19)(H,20,21)/t10?,11?,12?,15-,16+/m1/s1

Standard InChI Key:  ZVBBGMJUCZRFPO-RFVWGAHZSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
    2.9979  -17.3409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9979  -18.1659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7099  -18.5742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7099  -16.9242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4220  -17.3409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4230  -18.1659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1341  -18.5752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1319  -16.9252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5632  -16.9358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5703  -16.1078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8551  -15.6893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1328  -16.0988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9625  -19.3584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875  -19.3584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4767  -20.0252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8472  -17.3437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8503  -18.1610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8607  -14.8643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9917  -18.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4167  -16.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5657  -18.5719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  0
  8 12  1  0
 16  9  2  0
 10 11  1  0
 11 12  1  0
 13 14  1  0
  1  2  1  0
  1  4  1  0
  3 13  1  0
  5  8  1  0
 13 15  2  0
 17 16  1  0
  6  7  1  0
  7 17  1  0
  8 16  1  0
 11 18  2  0
  2  3  1  0
  3 19  1  6
  3  6  1  0
  5 20  1  1
  5  4  1  0
 17 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1077022

   (1S,4aR)-5-(carboxymethyl)-7-hydroxy-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic 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: 296.36

Molecular Weight (Monoisotopic): 296.1624

AlogP: 2.30

#Rotatable Bonds: 3

Polar Surface Area: 94.83

Molecular Species: ACID

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.15

CX Basic pKa: ┄

CX LogP: 1.87

CX LogD: -3.75

Aromatic Rings: ┄

Heavy Atoms: 21

QED Weighted: 0.69

Np Likeness Score: 2.87

References

1. Herath HM, Herath WH, Carvalho P, Khan SI, Tekwani BL, Duke SO, Tomaso-Peterson M, Nanayakkara NP..  (2009)  Biologically active tetranorditerpenoids from the fungus Sclerotinia homoeocarpa causal agent of dollar spot in turfgrass.,  72  (12): [PMID:19928902] [10.1021/np900334k]

Source

Source(1):

• Scientific Literature