2-hydroxy-3-isopropyl-2,4,6-cycloheptatrien-1-one

ID: ALA1275969

Chembl Id: CHEMBL1275969

Cas Number: 1946-74-3

PubChem CID: 80297

Max Phase: Preclinical

Molecular Formula: C10H12O2

Molecular Weight: 164.20

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)c1ccccc(=O)c1O

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

Standard InChI Key:  TUFYVOCKVJOUIR-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA1275969

   ALPHA-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: 11.26

CX Basic pKa: ┄

CX LogP: 2.06

CX LogD: 2.06

Aromatic Rings: 1

Heavy Atoms: 12

QED Weighted: 0.69

Np Likeness Score: 0.60

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. Morita Y, Matsumura E, Okabe T, Fukui T, Shibata M, Sugiura M, Ohe T, Tsujibo H, Ishida N, Inamori Y..  (2004)  Biological activity of alpha-thujaplicin, the isomer of hinokitiol.,  27  (6): [PMID:15187442] [10.1248/bpb.27.899]

3. 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]

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

5. 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(1):

• Scientific Literature