Antroquinonol

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Also known as: Hocena, Antroquinonol a, (+)-antroquinonol a, 1010081-09-0, (+)-antroquinonol, Ax9p92t7jz

Molecular Formula

C₂₄H₃₈O₄

Molecular Weight

390.6 g/mol

InChI Key

LJTSIMVOOOLKOL-FNRDIUJOSA-N

FDA UNII

AX9P92T7JZ

Antroquinonol Capsule is an orally available capsule containing antroquinonol, a farnesylated quinone derivative isolated from the mycelium of Antrodia camphorata, with potential antineoplastic activity. Upon oral administration, antroquinonol binds to and inhibits protein prenylation mediated by the enzymes farnesyltransferase (FTase) and geranylgeranyltransferase 1 (GGTase-1). This prevents both post-translational prenylation and signaling activity of a number of Ras superfamily proteins, such as Ras and Rho. This results in the inhibition of downstream signaling, such as the PI3K/mTOR signaling pathway, and induces apoptosis in susceptible tumor cells. Ras superfamily proteins are overexpressed in numerous cancer cell types, and play a key role in tumor cell proliferation and survival.

1 2D Structure

Antroquinonol

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(4R,5R,6R)-4-hydroxy-2,3-dimethoxy-6-methyl-5-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl]cyclohex-2-en-1-one

2.1.2 InChI

InChI=1S/C24H38O4/c1-16(2)10-8-11-17(3)12-9-13-18(4)14-15-20-19(5)21(25)23(27-6)24(28-7)22(20)26/h10,12,14,19-20,22,26H,8-9,11,13,15H2,1-7H3/b17-12+,18-14+/t19-,20-,22-/m1/s1

2.1.3 InChI Key

LJTSIMVOOOLKOL-FNRDIUJOSA-N

2.1.4 Canonical SMILES

CC1C(C(C(=C(C1=O)OC)OC)O)CC=C(C)CCC=C(C)CCC=C(C)C

2.1.5 Isomeric SMILES

C[C@@H]1[C@H]([C@H](C(=C(C1=O)OC)OC)O)C/C=C(\C)/CC/C=C(\C)/CCC=C(C)C

2.2 Other Identifiers

2.2.1 UNII

AX9P92T7JZ

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (+)-antroquinonol A

2. Antroquinonol A

3. Antroquinonol D

2.3.2 Depositor-Supplied Synonyms

1. Hocena

2. Antroquinonol A

3. (+)-antroquinonol A

4. 1010081-09-0

5. (+)-antroquinonol

6. Ax9p92t7jz

7. Chebi:65415

8. J3.387.174k

9. Antroquinonol D

10. (4r,5r,6r)-4-hydroxy-2,3-dimethoxy-6-methyl-5-((2e,6e)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)cyclohex-2-en-1-one

11. (4r,5r,6r)-4-hydroxy-2,3-dimethoxy-6-methyl-5-((2e,6e)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)cyclohex-2-enone

12. (4r,5r,6r)-4-hydroxy-2,3-dimethoxy-6-methyl-5-[(2e,6e)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]cyclohex-2-en-1-one

13. 2-cyclohexen-1-one, 4-hydroxy-2,3-dimethoxy-6-methyl-5-((2e,6e)-3,7,11-trimethyl-2,6,10-dodecatrien-1-yl)-, (4r,5r,6r)-

14. Unii-ax9p92t7jz

15. Antroquinonol [who-dd]

16. Chembl3235620

17. Schembl16919581

18. Db12326

19. Hy-19893

20. Cs-0016956

21. Q27133859

22. (4r)-2,3-dimethoxy-4.alpha.-hydroxy-5.alpha.-((2e,6e)-3,7,11-trimethyl-2,6,10-dodecatrienyl)-6.beta.-methyl-2-cyclohexene-1-one

23. (4r)-2,3-dimethoxy-4alpha-hydroxy-5alpha-((2e,6e)-3,7,11-trimethyl-2,6,10-dodecatrienyl)-6beta-methyl-2-cyclohexene-1-one

24. (4r,5r,6r)-4-hydroxy-2,3-dimethoxy-6-methyl-5-[(2e,6e)-3,7,11-trimethyldodeca-2,6,10-trienyl]cyclohex-2-en-1-one

2.4 Create Date

2008-08-18

3 Chemical and Physical Properties

Molecular Formula	C₂₄H₃₈O₄
Molecular Weight	390.6 g/mol
XLogP3	5.8
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	10
Exact Mass	390.27700969 g/mol
Monoisotopic Mass	390.27700969 g/mol
Topological Polar Surface Area	55.8 Å²
Heavy Atom Count	28
Formal Charge	0
Complexity	648
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	2
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1