thorectandrol C

ID: ALA463450

PubChem CID: 636729

Max Phase: Preclinical

Molecular Formula: C27H40O5

Molecular Weight: 444.61

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Thorectandrol C | CHEMBL463450

Canonical SMILES:  C=C1CCC[C@H]2[C@](C)(CC/C(C)=C/C[C@@H](O)C3=CC(=O)OC3)[C@@H](C)[C@H](OC(C)=O)C[C@]12C

Standard InChI:  InChI=1S/C27H40O5/c1-17(10-11-22(29)21-14-25(30)31-16-21)12-13-26(5)19(3)23(32-20(4)28)15-27(6)18(2)8-7-9-24(26)27/h10,14,19,22-24,29H,2,7-9,11-13,15-16H2,1,3-6H3/b17-10+/t19-,22+,23+,24-,26+,27+/m0/s1

Standard InChI Key:  DHZHHHTYJVQJEJ-VIYFSLSRSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
    4.5083   -9.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5083  -10.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2204  -10.4208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2204   -8.7708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9324   -9.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9334  -10.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6445  -10.4218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3590  -10.0107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3580   -9.1857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6424   -8.7718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9292  -10.8333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9250   -8.3625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2250   -8.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0500   -8.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8750   -8.0484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2824   -7.3310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1074   -7.3252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8649   -6.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5149   -6.6079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2201  -11.2458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0723   -8.7730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0735  -10.4233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0734  -11.2483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7878  -11.6608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3589  -11.6607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3399   -6.6021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7471   -5.8849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7574   -7.3136    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5702   -5.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8446   -5.1259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1894   -4.6244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5102   -5.0927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6354   -4.8906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  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
  3 20  2  0
  8  9  1  0
  9 21  1  1
  9 10  1  0
  8 22  1  6
  5  6  1  0
 22 23  1  0
  6 11  1  1
 23 24  1  0
 23 25  2  0
  5 12  1  6
 19 26  1  0
  1  2  1  0
 26 27  1  0
 10 13  1  1
 26 28  1  6
 27 29  2  0
  1  4  1  0
 10 14  1  0
  2  3  1  0
 14 15  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 27  1  0
  3  6  1  0
 30 33  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA463450

   THORECTANDROL C

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: 444.61

Molecular Weight (Monoisotopic): 444.2876

AlogP: 5.29

#Rotatable Bonds: 7

Polar Surface Area: 72.83

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 5.73

CX Basic pKa: ┄

CX LogP: 4.66

CX LogD: 3.00

Aromatic Rings: ┄

Heavy Atoms: 32

QED Weighted: 0.43

Np Likeness Score: 3.46

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]

Source

Source(1):

• Scientific Literature