Dasyscyphin D

ID: ALA505417

PubChem CID: 25058111

Max Phase: Preclinical

Molecular Formula: C22H32O2

Molecular Weight: 328.50

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Dasyscyphin D | Dasyscyphin D|CHEMBL505417|CHEBI:202838|(3S,4aR,6aS,11aR,11bR)-4,4,6a,8,11b-pentamethyl-1,2,3,4a,5,6,11,11a-octahydrobenzo[a]fluorene-3,7-diol|(3S,4aR,6aS,11aR,11bR)-4,4,6a,8,11b-pentamethyl-1,2,3,4a,5,6,11,11a-octahydrobenzo[a]luorene-3,7-diol

Canonical SMILES:  Cc1ccc2c(c1O)[C@@]1(C)CC[C@H]3C(C)(C)[C@@H](O)CC[C@]3(C)[C@H]1C2

Standard InChI:  InChI=1S/C22H32O2/c1-13-6-7-14-12-16-21(4)11-9-17(23)20(2,3)15(21)8-10-22(16,5)18(14)19(13)24/h6-7,15-17,23-24H,8-12H2,1-5H3/t15-,16+,17-,21-,22-/m0/s1

Standard InChI Key:  BOKAOWALBQCATC-AWTYYCOISA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   -3.1485    1.5736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1497    0.7511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4397    0.3387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4415    1.9818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7309    1.5773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7307    0.7511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9455    1.8298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4572    1.1624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9510    0.4943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6174   -0.2613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2068   -0.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3660    1.0753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6957    0.3117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5188    0.2174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0183    0.8845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6844    1.6522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8552    1.7447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3580    1.8983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8329    0.7942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2272   -0.1873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5111   -0.5995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4621    1.9857    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4395   -0.4815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8597    0.3396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1032   -0.3954    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1697   -0.2997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  6  2  0
  6  9  1  0
  8  7  1  0
  7  5  1  0
 12 17  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
  8  9  1  0
 12 18  1  6
  1  2  2  0
 15 19  1  6
  5  4  2  0
 14 20  1  0
  4  1  1  0
 14 21  1  0
  5  6  1  0
  8 12  1  0
  8 22  1  1
  9 10  1  0
  3 23  1  0
 10 11  1  0
  2 24  1  0
 11 13  1  0
 13 25  1  1
 12 13  1  0
  9 26  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA505417

   DASYSCYPHIN D

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: 328.50

Molecular Weight (Monoisotopic): 328.2402

AlogP: 4.73

#Rotatable Bonds: ┄

Polar Surface Area: 40.46

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.00

CX Basic pKa: ┄

CX LogP: 5.15

CX LogD: 5.15

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.72

Np Likeness Score: 2.60

References

1. Liermann JC, Kolshorn H, Anke H, Thines E, Opatz T..  (2008)  Tetracyclic terpenoids from Dasyscyphus niveus, dasyscyphins D and E.,  71  (9): [PMID:18771321] [10.1021/np800355a]

Source

Source(1):

• Scientific Literature