ZARAGOZIC ACID A

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C35H46O14
Molecular Weight	690.7313
Optical Activity	UNSPECIFIED
Defined Stereocenters	10 / 10
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC[C@H](C)C[C@H](C)\C=C\C(=O)O[C@@H]1[C@@H](O)[C@]3(CCC(=C)[C@@H](OC(C)=O)[C@H](C)CC2=CC=CC=C2)O[C@@]1(C(O)=O)[C@@](O)([C@H](O3)C(O)=O)C(O)=O

InChI

InChIKey=DFKDOZMCHOGOBR-NCSQYGPNSA-N

InChI=1S/C35H46O14/c1-7-19(2)17-20(3)13-14-25(37)47-28-27(38)33(48-29(30(39)40)34(45,31(41)42)35(28,49-33)32(43)44)16-15-21(4)26(46-23(6)36)22(5)18-24-11-9-8-10-12-24/h8-14,19-20,22,26-29,38,45H,4,7,15-18H2,1-3,5-6H3,(H,39,40)(H,41,42)(H,43,44)/b14-13+/t19-,20+,22+,26+,27+,28+,29+,33-,34+,35-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C35H46O14
Molecular Weight	690.7313
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	10 / 10
E/Z Centers	1
Optical Activity	UNSPECIFIED

Approval Year

Targets

Primary Target	Pharmacology	Potency
Squalene synthetase 1 Target ID: CHEMBL3815 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8419946 \| https://www.ncbi.nlm.nih.gov/pubmed/1601846	Inhibitor 8297	78.0 pM [Ki]
Protein farnesyltransferase 13 Target ID: CHEMBL2095178 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8463291	Inhibitor 8297	216.0 nM [IC50]
Geranylgeranyl transferase type I 7 Target ID: CHEMBL2096987 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8463291	Inhibitor 8297	620.0 nM [IC50]

PubMed

Title	Date	PubMed
Zaragozic acids: a family of fungal metabolites that are picomolar competitive inhibitors of squalene synthase.	1993 Jan 1	8419946
Expression, purification, and characterization of the human squalene synthase: use of yeast and baculoviral systems.	1995 Feb 1	7864626
Truncation of human squalene synthase yields active, crystallizable protein.	1998 Feb 15	9473303
Inhibitors of sterol biosynthesis and amphotericin B reduce the viability of pneumocystis carinii f. sp. carinii.	2000 Jun	10817720
Regulation of oxysterol 7alpha-hydroxylase (CYP7B1) in primary cultures of rat hepatocytes.	2002 Jun	12029625
Species-specific mechanisms for cholesterol 7alpha-hydroxylase (CYP7A1) regulation by drugs and bile acids.	2005 Feb 1	15629111
Squalene synthase, a determinant of Raft-associated cholesterol and modulator of cancer cell proliferation.	2007 Jun 29	17483544

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 19:52:47 GMT 2023` Edited by `admin` on `Fri Dec 15 19:52:47 GMT 2023`
Record UNII	1117HVX02L
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ZARAGOZIC ACID A

Common Name

English

GR-105155X

Code

English

L-ERYTHRO-L-GLYCERO-D-ALTRO-7-TRIDECULO-7,4-FURANOSONIC ACID, 2,7-ANHYDRO-3,4-DI-C-CARBOXY-8,9,10,12,13-PENTADEOXY-10-METHYLENE-12-(PHENYLMETHYL)-, 11-ACETATE 5-((2E,4S,6S)-4,6-DIMETHYL-2-OCTENOATE), (7S)-

Systematic Name

English

SQUALESTATIN 1

Common Name

English

SQUALESTATIN I

Common Name

English

L-694599

Code

English

ZARAGOZIC ACID A [MI]

Common Name

English

SQUALESTATIN

Common Name

English

SQUALESTATIN S1

Common Name

English

Code System Code Type Description

CAS

142561-96-4