2-hydroxy-5-isopropyl-2,4,6-cycloheptatrien-1-one

ID: ALA1275999

Chembl Id: CHEMBL1275999

Cas Number: 672-76-4

PubChem CID: 12649

Max Phase: Preclinical

Molecular Formula: C10H12O2

Molecular Weight: 164.20

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)c1ccc(O)c(=O)cc1

Standard InChI:  InChI=1S/C10H12O2/c1-7(2)8-3-5-9(11)10(12)6-4-8/h3-7H,1-2H3,(H,11,12)

Standard InChI Key:  WKEWHSLZDDZONF-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA1275999

   GAMMA-THUJAPLICIN

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: 164.20

Molecular Weight (Monoisotopic): 164.0837

AlogP: 1.88

#Rotatable Bonds: 1

Polar Surface Area: 37.30

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.43

CX Basic pKa: ┄

CX LogP: 2.06

CX LogD: 2.06

Aromatic Rings: 1

Heavy Atoms: 12

QED Weighted: 0.69

Np Likeness Score: 0.49

References

1. Takahashi S, Kamiya T, Saeki K, Nezu T, Takeuchi S, Takasawa R, Sunaga S, Yoshimori A, Ebizuka S, Abe T, Tanuma S..  (2010)  Structural insights into the hot spot amino acid residues of mushroom tyrosinase for the bindings of thujaplicins.,  18  (22): [PMID:20947360] [10.1016/j.bmc.2010.08.056]

2. PubChem BioAssay data set, 

3. Inamori Y, Sakagami Y, Morita Y, Shibata M, Sugiura M, Kumeda Y, Okabe T, Tsujibo H, Ishida N..  (2000)  Antifungal activity of Hinokitiol-related compounds on wood-rotting fungi and their insecticidal activities.,  23  (8): [PMID:10963310] [10.1248/bpb.23.995]

4. Yoshimori A, Oyama T, Takahashi S, Abe H, Kamiya T, Abe T, Tanuma S..  (2014)  Structure-activity relationships of the thujaplicins for inhibition of human tyrosinase.,  22  (21): [PMID:25288494] [10.1016/j.bmc.2014.08.027]

5. Meck C, D'Erasmo MP, Hirsch DR, Murelli RP..  (2014)  The biology and synthesis of α-hydroxytropolones.,  5  (7): [PMID:25089179] [10.1039/c4md00055b]

6. Pillaiyar T, Namasivayam V, Manickam M, Jung SH..  (2018)  Inhibitors of Melanogenesis: An Updated Review.,  61  (17): [PMID:29763564] [10.1021/acs.jmedchem.7b00967]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays