1-((5aR,8aS)-2,2,5a,8a-tetramethyl-5,5a,6,7,8,8a-hexahydro-2H-indeno[4,5-b]furan-4(3H)-ylidene)propan-2-one

ID: ALA582882

PubChem CID: 25156429

Max Phase: Preclinical

Molecular Formula: C18H26O2

Molecular Weight: 274.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)/C=C1\C[C@@]2(C)CCC[C@]2(C)C2=C1CC(C)(C)O2

Standard InChI:  InChI=1S/C18H26O2/c1-12(19)9-13-10-17(4)7-6-8-18(17,5)15-14(13)11-16(2,3)20-15/h9H,6-8,10-11H2,1-5H3/b13-9+/t17-,18-/m1/s1

Standard InChI Key:  XHMJUNQEHUQUOV-LJXZRRFRSA-N

Molfile:  

     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
    2.9799  -12.4912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6958  -12.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4078  -11.6671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4029  -12.4898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1838  -12.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6713  -12.0859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1916  -11.4176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4000  -10.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3958  -13.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2668  -12.9060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9749  -11.6685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6911  -11.2544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5186  -10.4452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6957  -10.3592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3597  -11.1152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1000   -9.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9750   -9.9458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2695  -13.7310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5564  -14.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9853  -14.1412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  9  1  1
  1 10  2  0
 11 12  2  0
  1 11  1  0
  2  4  1  0
  3 12  1  0
  4  5  1  0
  5  6  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 11  1  0
  6  7  1  0
 14 16  1  0
  7  3  1  0
 14 17  1  0
  3  4  1  0
 10 18  1  0
  3  8  1  6
 18 19  1  0
  1  2  1  0
 18 20  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA582882

   (1E)-1-[(5aR,8aS)-2,2,5a,8a-tetramethyl-5,6,7,8-tetrahydro-3H-cyclopenta[g][1]benzofuran-4-ylidene]propan-2-one

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: 274.40

Molecular Weight (Monoisotopic): 274.1933

AlogP: 4.56

#Rotatable Bonds: 1

Polar Surface Area: 26.30

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.06

CX LogD: 3.06

Aromatic Rings: ┄

Heavy Atoms: 20

QED Weighted: 0.66

Np Likeness Score: 2.18

References

1. Mokrini R, Mesaoud MB, Daoudi M, Hellio C, Maréchal JP, El Hattab M, Ortalo-Magné A, Piovetti L, Culioli G..  (2008)  Meroditerpenoids and derivatives from the brown alga Cystoseira baccata and their antifouling properties.,  71  (11): [PMID:18980381] [10.1021/np8004216]

Source

Source(1):

• Scientific Literature