Stachyonic acid A

ID: ALA4537884

PubChem CID: 155548783

Max Phase: Preclinical

Molecular Formula: C20H30O2

Molecular Weight: 302.46

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=C/C(C)=C/C[C@H]1C(C)=CC[C@@H]2[C@]1(C)CCC[C@@]2(C)C(=O)O

Standard InChI:  InChI=1S/C20H30O2/c1-6-14(2)8-10-16-15(3)9-11-17-19(16,4)12-7-13-20(17,5)18(21)22/h6,8-9,16-17H,1,7,10-13H2,2-5H3,(H,21,22)/b14-8+/t16-,17+,19+,20+/m0/s1

Standard InChI Key:  SKEMYAAMDHTYBL-ONIUZDBUSA-N

Molfile:  

 
     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
    4.5977   -8.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1914   -7.2925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7764   -8.0030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4825   -6.0612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4825   -6.8862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1951   -5.6425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9036   -6.0612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9001   -6.8862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6095   -7.2973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3268   -6.8922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3303   -6.0672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6164   -5.6473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0475   -5.6564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1850   -8.7193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4227   -8.0082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8963   -5.2362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6093   -4.8216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3207   -4.4051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3136   -3.5801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0251   -3.1593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0180   -2.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5951   -3.1716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3126   -7.6007    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  1
  4  5  1  0
  4  6  1  0
  5  2  1  0
  2  8  1  0
  7  6  1  0
  7  8  1  0
  7 12  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
  1 14  1  0
  1 15  2  0
  7 16  1  1
 12 17  1  1
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 19 22  1  0
  8 23  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4537884

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 302.46

Molecular Weight (Monoisotopic): 302.2246

AlogP: 5.37

#Rotatable Bonds: 4

Polar Surface Area: 37.30

Molecular Species: ACID

HBA: 1

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.88

CX Basic pKa: ┄

CX LogP: 5.27

CX LogD: 2.79

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.56

Np Likeness Score: 3.24

References

1. Tan YP, Xue Y, Savchenko AI, Houston SD, Modhiran N, McMillan CLD, Boyle GM, Bernhardt PV, Young PR, Watterson D, Williams CM..  (2019)  Basimarols A, B, and C, Highly Oxygenated Pimarane Diterpenoids from Basilicum polystachyon.,  82  (10): [PMID:31553187] [10.1021/acs.jnatprod.9b00522]

Source

Source(1):

• Scientific Literature