thorectandrol A

ID: ALA446595

PubChem CID: 5352106

Max Phase: Preclinical

Molecular Formula: C25H38O3

Molecular Weight: 386.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1CCC[C@H]2[C@](C)(CC/C(C)=C/C[C@H]3OC(=O)C=C3CO)[C@@H](C)CC[C@]12C

Standard InChI:  InChI=1S/C25H38O3/c1-17(9-10-21-20(16-26)15-23(27)28-21)11-13-24(4)19(3)12-14-25(5)18(2)7-6-8-22(24)25/h9,15,19,21-22,26H,2,6-8,10-14,16H2,1,3-5H3/b17-9+/t19-,21+,22-,24+,25+/m0/s1

Standard InChI Key:  QQKDQHJTKIBERS-OGXBFCNVSA-N

Molfile:  

     RDKit          2D

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   -4.6083   -1.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6083   -2.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8963   -2.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8963   -1.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1843   -1.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1832   -2.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4722   -2.7760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7576   -2.3648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7587   -1.5398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4743   -1.1260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1875   -3.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1917   -0.7167    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8917   -0.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0667   -0.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2417   -0.4025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8342    0.3148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0092    0.3206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2517    1.0264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3982    1.0380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2232    1.0438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7094    0.3805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4922    0.6410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4864    1.4660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7000    1.7153    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2917   -0.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6982   -1.0471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1504    1.9557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8966   -3.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0443   -1.1272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 10 14  1  0
  2  3  1  0
 14 15  1  0
  3  6  1  0
 15 16  1  0
  5  4  1  0
 16 17  2  0
  5 10  1  0
 16 18  1  0
  6  7  1  0
 17 19  1  0
  7  8  1  0
 20 19  1  1
 20 21  1  0
  8  9  1  0
  9 10  1  0
  5  6  1  0
  6 11  1  1
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 20  1  0
 21 25  1  0
  5 12  1  6
 25 26  1  0
  1  2  1  0
 23 27  2  0
 10 13  1  1
  3 28  2  0
  1  4  1  0
  9 29  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA446595

   THORECTANDROL A

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: 386.58

Molecular Weight (Monoisotopic): 386.2821

AlogP: 5.75

#Rotatable Bonds: 6

Polar Surface Area: 46.53

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.82

CX Basic pKa: ┄

CX LogP: 5.53

CX LogD: 5.52

Aromatic Rings: ┄

Heavy Atoms: 28

QED Weighted: 0.47

Np Likeness Score: 3.66

References

1. Charan RD, McKee TC, Boyd MR..  (2002)  Thorectandrols C, D, and E, new sesterterpenes from the marine sponge Thorectandra sp.,  65  (4): [PMID:11975486] [10.1021/np010439k]

2. Charan RD, McKee TC, Boyd MR..  (2001)  Thorectandrols A and B, new cytotoxic sesterterpenes from the marine sponge Thorectandra species.,  64  (5): [PMID:11374971] [10.1021/np000544e]

Source

Source(1):

• Scientific Literature