Epicochlioquinone A

CAT: 0931-TN10442-02Size: 50 mgDry Ice: NoHazardous: No

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CAT#:0931-TN10442-02Size:50 mg

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CAS Number

147384-57-4

Target

Acyltransferase

Related Pathways

Metabolism

Bioactivity

Epicochlioquinone A inhibits rat liver microsomal ACAT with an IC50 of 1.7 μM and inhibits plasma lecithin-cholesterol acyltransferase (LCAT) with an IC50 of 15.8 μM. At a dosage of 75 mg/kg, it can reduce cholesterol absorption in rats by 50%.

Smiles

C[C@@]12[C@@]3([C@@](C)(OC4=C([C@H]3O)C(=O)C=C([C@@H]([C@@H]([C@H](CC)C)OC(C)=O)C)C4=O)CC[C@]1(O[C@@H](C(C)(C)O)CC2)[H])[H]

Molecular Formula

C30H44O8

Molecular Weight

532.666

Shipping Conditions

Ice Packs

Storage Temperature

-20°C

Chemical Information

epi-cochlioquinone A

Epi-cochlioquinone A is an organic heterotetracyclic that is 1,2,3,4a,5,6,6a,12,12a,12b-decahydropyrano[3,2-a]xanthene-8,11-dione substituted by a 2-hydroxypropan-2-yl group at position 3, hydroxy group at position 12, methyl groups at positions 6a and 12b and a 3-(acetyloxy)-4-methylhexan-2-yl moiety at position 9. Isolated from the fermentation broth of Stachybotrys bisbyi SANK 17777, it acts as an inhibitor of acyl-CoA:cholesterol acyltransferase. It has a role as a metabolite and an EC 2.3.1.26 (sterol O-acyltransferase) inhibitor. It is a member of p-quinones, a tertiary alcohol, a secondary alcohol, a cyclic ether, an organic heterotetracyclic compound and an acetate ester.

CAS Number	147384-57-4
PubChem CID	3073217
IUPAC Name	[(2S,3R,4S)-2-[(3R,4aR,6aS,12S,12aS,12bR)-12-hydroxy-3-(2-hydroxypropan-2-yl)-6a,12b-dimethyl-8,11-dioxo-1,2,3,4a,5,6,12,12a-octahydropyrano[3,2-a]xanthen-9-yl]-4-methylhexan-3-yl] acetate
Molecular Formula	C30H44O8
Molecular Weight	532.7
XLogP	3.4
Topological Polar Surface Area	119
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	7
Heavy Atom Count	38
Formal Charge	0
Complexity	1070

SMILES

CC[C@H](C)[C@H]([C@@H](C)C1=CC(=O)C2=C(C1=O)O[C@]3(CC[C@@H]4[C@@]([C@H]3[C@@H]2O)(CC[C@@H](O4)C(C)(C)O)C)C)OC(=O)C

InChI

InChI=1S/C30H44O8/c1-9-15(2)25(36-17(4)31)16(3)18-14-19(32)22-24(34)27-29(7)12-10-20(28(5,6)35)37-21(29)11-13-30(27,8)38-26(22)23(18)33/h14-16,20-21,24-25,27,34-35H,9-13H2,1-8H3/t15-,16-,20+,21+,24+,25+,27+,29-,30-/m0/s1

InChIKey

UWSYUCZPPVXEKW-UDLMDNSSSA-N

Chemical Structure

2D Structure

CAS: 147384-57-4

CID: 3073217

Formula: C30H44O8

MW: 532.7

Interactive 3D Structure

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View on PubChem Raw 3D data

Computed Properties

Property	Value
Molecular Weight	532.7
XLogP3	3.4
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	7
Exact Mass	532.30361836
Monoisotopic Mass	532.30361836
Topological Polar Surface Area	119 Å²
Heavy Atom Count	38
Formal Charge	0
Complexity	1070
Isotope Atom Count	0
Defined Atom Stereocenter Count	9
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently-Bonded Unit Count	1
Compound Is Canonicalized	Yes

Alternative Products

Catalog	Name
HY-16197	Epicochlioquinone A

Epicochlioquinone A

Chemical Information

Alternative Products

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