Isogambogenic acid

ID: ALA4584357

Cas Number: 887923-47-9

PubChem CID: 101389903

Max Phase: Preclinical

Molecular Formula: C38H46O8

Molecular Weight: 630.78

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)=CCC/C(C)=C/Cc1c(O)c(CC=C(C)C)c2c(c1O)C(=O)C1=C[C@@H]3C[C@H]4C(C)(C)O[C@@](C/C=C(\C)C(=O)O)(C3=O)[C@@]14O2

Standard InChI:  InChI=1S/C38H46O8/c1-20(2)10-9-11-22(5)13-15-25-30(39)26(14-12-21(3)4)33-29(31(25)40)32(41)27-18-24-19-28-36(7,8)46-37(34(24)42,38(27,28)45-33)17-16-23(6)35(43)44/h10,12-13,16,18,24,28,39-40H,9,11,14-15,17,19H2,1-8H3,(H,43,44)/b22-13+,23-16+/t24-,28+,37+,38-/m1/s1

Standard InChI Key:  RCWNBHCZYXWDOV-SDNKGDDVSA-N

Molfile:  

 
     RDKit          2D

 48 52  0  0  0  0  0  0  0  0999 V2000
    7.5817  -27.1118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9007  -27.5162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5858  -26.3317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9131  -25.9314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2586  -27.5162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2668  -25.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2792  -25.1596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9643  -24.7592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9007  -28.3045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9643  -23.9668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2545  -28.3087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2792  -23.5789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6495  -23.5789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2239  -27.1118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8669  -26.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8669  -27.1118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5455  -27.5060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5455  -25.9377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2260  -26.3238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6890  -25.5993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3398  -25.0297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5607  -25.1743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8412  -25.5310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8407  -24.7221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1410  -24.3181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1405  -23.5091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4418  -24.7230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6675  -24.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7616  -24.4538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9597  -25.5971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1680  -25.9221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3292  -27.7194    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4942  -25.5216    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9520  -26.3400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9520  -27.1241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6580  -25.9284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6578  -27.5359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3674  -27.1305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0732  -27.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7828  -27.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0696  -28.3594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4886  -27.5486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1982  -27.1432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9040  -27.5549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6136  -27.1495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9004  -28.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4325  -23.1010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8480  -23.1001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  2  0
  2 14  1  0
  3  4  1  0
 19  4  1  1
 34  6  2  0
  5  1  1  0
  6  3  1  0
  7  6  1  0
  8  7  1  0
  9  2  2  0
 10  8  2  0
 11  5  1  0
 12 10  1  0
 13 10  1  0
  2  1  1  0
  5 35  2  0
 14 19  1  0
 14 17  2  0
 18 15  1  0
 15 16  1  0
 16 17  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 18  1  0
 18 23  1  1
 23 24  1  0
 24 25  2  0
 25 26  1  0
 25 27  1  0
 21 28  1  0
 21 29  1  0
 20 30  1  0
 30 16  1  0
 15 31  2  0
 16 32  1  6
 20 33  1  6
 34 35  1  0
 34 36  1  0
 35 37  1  0
 37 38  1  0
 38 39  2  0
 39 40  1  0
 39 41  1  0
 40 42  1  0
 42 43  1  0
 43 44  2  0
 44 45  1  0
 44 46  1  0
 26 47  2  0
 26 48  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4584357

   Isogambogenic acid

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: 630.78

Molecular Weight (Monoisotopic): 630.3193

AlogP: 7.27

#Rotatable Bonds: 10

Polar Surface Area: 130.36

Molecular Species: ACID

HBA: 7

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.56

CX Basic pKa: ┄

CX LogP: 8.23

CX LogD: 4.65

Aromatic Rings: 1

Heavy Atoms: 46

QED Weighted: 0.18

Np Likeness Score: 3.13

References

1. Ren Y, de Blanco EJC, Fuchs JR, Soejarto DD, Burdette JE, Swanson SM, Kinghorn AD..  (2019)  Potential Anticancer Agents Characterized from Selected Tropical Plants.,  82  (3): [PMID:30830783] [10.1021/acs.jnatprod.9b00018]

Source

Source(1):

• Scientific Literature