Floridolide A

ID: ALA4251191

PubChem CID: 101321350

Max Phase: Preclinical

Molecular Formula: C20H28O4

Molecular Weight: 332.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H]1CC[C@@]2(C)C(C(=O)O)=CCC[C@H]2[C@]1(C)CCC1=CCOC1=O

Standard InChI:  InChI=1S/C20H28O4/c1-13-7-10-20(3)15(17(21)22)5-4-6-16(20)19(13,2)11-8-14-9-12-24-18(14)23/h5,9,13,16H,4,6-8,10-12H2,1-3H3,(H,21,22)/t13-,16-,19+,20-/m0/s1

Standard InChI Key:  WUUOACSBQPHDQM-NCJOTSGUSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   28.9470   -6.5623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9458   -7.3818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6539   -7.7908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6521   -6.1534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3607   -6.5587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3595   -7.3793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0657   -7.7883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7776   -7.3813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7788   -6.5607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0680   -6.1471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3558   -5.7410    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   30.3516   -8.1925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6555   -8.6079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9487   -9.0180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.3641   -9.0151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.0681   -5.3299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7758   -4.9213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7758   -4.1041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7714   -5.7327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4875   -6.1538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4383   -3.6262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1858   -2.8490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3685   -2.8490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.1161   -3.6262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3391   -3.8793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  6  1  0
  5  4  1  0
  4  1  1  0
  5  6  1  0
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  5 11  1  6
  6 12  1  6
  3 13  1  0
 13 14  1  0
 13 15  2  0
 10 16  1  0
 16 17  1  0
 17 18  1  0
 10 19  1  1
  9 20  1  1
 18 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 18  1  0
 24 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4251191

   (4aS,5R,6S,8aR)-5,6,8a-trimethyl-5-[2-(5-oxo-2H-furan-4-yl)ethyl]-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylic acid

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: 332.44

Molecular Weight (Monoisotopic): 332.1988

AlogP: 4.11

#Rotatable Bonds: 4

Polar Surface Area: 63.60

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.42

CX Basic pKa: ┄

CX LogP: 4.38

CX LogD: 1.51

Aromatic Rings: ┄

Heavy Atoms: 24

QED Weighted: 0.79

Np Likeness Score: 3.51

References

1. Qiao Y, Zheng H, Li L, Zhang J, Li Y, Li S, Zhu R, Zhou J, Zhao S, Jiang Y, Lou H..  (2018)  Terpenoids with vasorelaxant effects from the Chinese liverwort Scapania carinthiaca.,  26  (14): [PMID:30049584] [10.1016/j.bmc.2018.07.035]

Source

Source(1):

• Scientific Literature