Caesalpinista B

ID: ALA4079488

PubChem CID: 137652177

Max Phase: Preclinical

Molecular Formula: C23H32O6

Molecular Weight: 404.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)[C@]1(C)CCC[C@@]2(COC(C)=O)[C@H]1[C@H](O)C[C@H]1[C@@H](C)c3ccoc3C[C@@H]12

Standard InChI:  InChI=1S/C23H32O6/c1-13-15-6-9-28-19(15)11-17-16(13)10-18(25)20-22(3,21(26)27-4)7-5-8-23(17,20)12-29-14(2)24/h6,9,13,16-18,20,25H,5,7-8,10-12H2,1-4H3/t13-,16-,17-,18+,20-,22+,23-/m0/s1

Standard InChI Key:  CNRDGMAZSRXKTL-FQJGYRCVSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   30.0751  -12.4477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6706  -11.7420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2617  -12.4451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9690  -10.5203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9690  -11.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6743  -10.1076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3796  -10.5203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3761  -11.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0782  -11.7468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7882  -11.3435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0851  -10.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7878  -10.5288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4958  -10.1306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0904   -9.2979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8045   -8.8982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5080   -9.3106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1176   -8.7690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7909   -8.0218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9794   -8.1017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.1981  -10.5484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4445  -12.4425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.6680  -13.1541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.2572  -13.8605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5828  -12.1217    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   31.0736  -12.5640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.3723   -9.7031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6609   -9.3009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.6536   -8.4837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9423   -8.0814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3577   -8.0688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.0780  -10.9289    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   31.7797   -9.7114    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  6
  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 11  1  0
  8  9  1  0
  9 10  1  0
 10 12  1  0
 11 12  1  0
 11 14  1  0
 12 13  1  0
 13 16  1  0
 15 14  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 15  1  0
 13 20  1  6
  3 21  2  0
  3 22  1  0
 22 23  1  0
  8 24  1  6
  9 25  1  1
  7 26  1  1
 26 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  2  0
 11 31  1  6
 12 32  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4079488

   ---

Molecule Features

Natural Product: Yes

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: 404.50

Molecular Weight (Monoisotopic): 404.2199

AlogP: 3.47

#Rotatable Bonds: 3

Polar Surface Area: 85.97

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.69

CX LogD: 2.69

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.78

Np Likeness Score: 2.84

References

1. Qiao Y, Xu Q, Hu Z, Li XN, Xiang M, Liu J, Huang J, Zhu H, Wang J, Luo Z, Xue Y, Zhang Y..  (2016)  Diterpenoids of the Cassane Type from Caesalpinia decapetala.,  79  (12): [PMID:27966950] [10.1021/acs.jnatprod.6b00910]

Source

Source(1):

• Scientific Literature