Euphorhelipane A

ID: ALA4476668

PubChem CID: 155538543

Max Phase: Preclinical

Molecular Formula: C20H30O4

Molecular Weight: 334.46

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H30O4/c1-11-7-8-15-13(3)17(22)20(24,18(23)16(11)15)12(2)9-10-19(5,6)14(4)21/h7-13,15-17,22,24H,1-6H3/b10-9+/t11-,12+,13-,15-,16+,17-,20-/m0/s1

Standard InChI Key:  VBBUAGFTVXZMSN-PTVWPMOQSA-N

Molfile:  

 
     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
    7.0782   -8.6754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8995   -8.6754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4868   -7.9636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7611  -12.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4705  -11.9566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4705  -11.1353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7611  -10.7184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0517  -11.9566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0472  -11.1353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2646  -10.8871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7837  -11.5508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2718  -12.2133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1836  -10.7246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8901  -11.1394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1860   -9.9033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8990   -9.4968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6103   -8.2648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6127   -7.4435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3209   -8.6796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7611  -13.1824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1818  -12.3662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0476  -12.7779    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0393  -10.3139    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0078  -10.1071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7622   -9.8971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1773  -11.5439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  9  7  1  0
  8  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12  8  1  0
  6 13  1  0
 13 14  1  1
 13 15  1  0
 15 16  2  0
 16  2  1  0
  2 17  1  0
 17 18  2  0
 17 19  1  0
  4 20  1  1
  5 21  1  1
  8 22  1  1
  9 23  1  6
 10 24  1  6
  7 25  2  0
  6 26  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4476668

   ---

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: 334.46

Molecular Weight (Monoisotopic): 334.2144

AlogP: 2.54

#Rotatable Bonds: 4

Polar Surface Area: 74.60

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.90

CX Basic pKa: ┄

CX LogP: 3.04

CX LogD: 3.04

Aromatic Rings: ┄

Heavy Atoms: 24

QED Weighted: 0.77

Np Likeness Score: 1.49

References

1. Li W, Tang YQ, Chen SX, Tang GH, Gan LS, Li C, Rao Y, Huang ZS, Yin S..  (2019)  Euphorhelipanes A and B, Triglyceride-Lowering Euphorbia Diterpenoids with a Bicyclo[4.3.0]nonane Core from Euphorbia helioscopia.,  82  (2): [PMID:30724086] [10.1021/acs.jnatprod.8b00780]

Source

Source(1):

• Scientific Literature