(2E,4S,5S,6R)-4,5,6-Trihydroxy-2-methyl-6-[(7R)-10-methylcyclohex-10-en-7-yl]hept-2-enoic acid; Elgonene F

ID: ALA4551243

PubChem CID: 155555004

Max Phase: Preclinical

Molecular Formula: C15H24O5

Molecular Weight: 284.35

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC1=CC[C@H]([C@@](C)(O)[C@@H](O)[C@@H](O)/C=C(\C)C(=O)O)CC1

Standard InChI:  InChI=1S/C15H24O5/c1-9-4-6-11(7-5-9)15(3,20)13(17)12(16)8-10(2)14(18)19/h4,8,11-13,16-17,20H,5-7H2,1-3H3,(H,18,19)/b10-8+/t11-,12-,13-,15+/m0/s1

Standard InChI Key:  XXNHEUYPKWZRDU-KVXDWFHTSA-N

Molfile:  

 
     RDKit          2D

 21 21  0  0  0  0  0  0  0  0999 V2000
   20.9663   -2.4144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9663   -3.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6716   -3.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3810   -3.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3810   -2.4144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6716   -1.9976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0940   -2.0038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8047   -2.4186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5177   -2.0079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2283   -2.4227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9414   -2.0121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6520   -2.4269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3609   -2.0162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.6496   -3.2482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.9438   -1.1908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2551   -3.6454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8023   -3.2399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6791   -1.2918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.4963   -1.2918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0836   -2.8230    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   24.5201   -1.1907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 11 15  1  0
  2 16  1  0
  8 17  1  6
  7 18  1  0
  7 19  1  6
  5 20  1  6
  9 21  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4551243

   ---

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: 284.35

Molecular Weight (Monoisotopic): 284.1624

AlogP: 1.24

#Rotatable Bonds: 5

Polar Surface Area: 97.99

Molecular Species: ACID

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.39

CX Basic pKa: ┄

CX LogP: 1.11

CX LogD: -1.79

Aromatic Rings: ┄

Heavy Atoms: 20

QED Weighted: 0.45

Np Likeness Score: 2.41

References

1. Cheng T, Chepkirui C, Decock C, Matasyoh JC, Stadler M..  (2019)  Sesquiterpenes from an Eastern African Medicinal Mushroom Belonging to the Genus Sanghuangporus.,  82  (5): [PMID:31001977] [10.1021/acs.jnatprod.8b01086]

Source

Source(1):

• Scientific Literature