(4aS,6aR,6bR,8aR,10S,12aR,12bR,14bS,E)-10-hydroxy-6a-(4-(4-hydroxy-3-methoxyphenyl)-2-oxobut-3-enyl)-2,2,6b,9,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid

ID: ALA503336

PubChem CID: 44583700

Max Phase: Preclinical

Molecular Formula: C40H56O6

Molecular Weight: 632.88

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(/C=C/C(=O)C[C@@]23CC[C@@]4(C(=O)O)CCC(C)(C)C[C@H]4C2=CC[C@@H]2[C@@]4(C)CC[C@H](O)C(C)(C)[C@@H]4CC[C@]23C)ccc1O

Standard InChI:  InChI=1S/C40H56O6/c1-35(2)18-19-39(34(44)45)20-21-40(23-26(41)10-8-25-9-12-29(42)30(22-25)46-7)27(28(39)24-35)11-13-32-37(5)16-15-33(43)36(3,4)31(37)14-17-38(32,40)6/h8-12,22,28,31-33,42-43H,13-21,23-24H2,1-7H3,(H,44,45)/b10-8+/t28-,31-,32+,33-,37-,38+,39-,40-/m0/s1

Standard InChI Key:  VFJODNONXFOWFG-IWFHGSTGSA-N

Molfile:  

     RDKit          2D

 49 54  0  0  0  0  0  0  0  0999 V2000
   -1.7399  -18.1717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0251  -18.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0266  -19.4101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3117  -19.8237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3132  -20.6485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3974  -21.0621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1138  -20.6512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0297  -21.0595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0312  -21.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7445  -20.6459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7429  -19.8211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7390  -17.3471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0244  -16.9353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0146  -16.5111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0146  -17.3400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3028  -17.7523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3028  -16.0946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5869  -16.5111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5858  -17.3400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8709  -17.7533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8730  -16.0956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1577  -16.5115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1499  -14.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8722  -15.2698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4347  -15.2787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4453  -16.1026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7403  -16.5192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0205  -16.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7193  -14.8715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0131  -15.2978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3004  -14.8990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2835  -14.0763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9856  -13.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7086  -14.0504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7244  -15.6988    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1656  -15.6821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5942  -15.6821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7380  -17.7575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8938  -18.3354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7192  -18.3354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4534  -16.9275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1757  -17.3330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3041  -15.7071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3019  -16.5288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4113  -15.2966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3024  -16.9234    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8779  -16.9192    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5745  -13.0664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4040  -13.0664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 22 26  1  0
 25 23  2  0
 23 24  1  0
 25 26  1  0
  1 12  1  0
  1  2  2  0
 12 13  2  0
 14 15  1  0
 25 29  1  0
 26 27  1  0
 27 28  1  0
 28 30  1  0
 29 30  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
 14 17  1  0
 15 16  1  0
 29 34  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 16 19  1  0
 29 35  1  1
 18 17  1  0
 22 36  1  1
 18 19  1  0
 18 37  1  1
  6  7  1  0
 15 38  1  1
  5  8  1  0
 16 39  1  0
  8  9  1  0
 16 40  1  0
 18 21  1  0
 26 41  1  6
 19 20  1  0
 41 12  1  0
 20 42  1  0
 30 43  1  1
 42 22  1  0
 21 22  1  0
 43 44  1  0
 43 45  2  0
  8 10  2  0
 10 11  1  0
 19 46  1  6
  3 11  2  0
 21 47  1  6
 33 48  1  0
 21 24  1  0
 33 49  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA503336

   (4aS,6aR,6bR,8aR,10S,12aR,12bR,14bS,E)-10-hydroxy-6a-(4-(4-hydroxy-3-methoxyphenyl)-2-oxobut-3-enyl)-2,2,6b,9,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid

Molecule Features

Natural Product: No

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: 632.88

Molecular Weight (Monoisotopic): 632.4077

AlogP: 8.60

#Rotatable Bonds: 6

Polar Surface Area: 104.06

Molecular Species: ACID

HBA: 5

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 4.57

CX Basic pKa: ┄

CX LogP: 7.95

CX LogD: 5.19

Aromatic Rings: 1

Heavy Atoms: 46

QED Weighted: 0.21

Np Likeness Score: 2.69

References

1. Lee JS, Kim J, Kim BY, Lee HS, Ahn JS, Chang YS..  (2000)  Inhibition of phospholipase cgamma1 and cancer cell proliferation by triterpene esters from Uncaria rhynchophylla.,  63  (6): [PMID:10869194] [10.1021/np990478k]

Source

Source(1):

• Scientific Literature