Details of the Drug

General Information of Drug (ID: DM4JZPT)

Drug Name

Squalestatin 1

Synonyms

Zaragozic acid A; squalestatin 1; Squalestatin; 142561-96-4; ZARAGOZIC ACIDS A; UNII-1117HVX02L; CHEMBL280978; CHEBI:75170; 1117HVX02L; 1S-((4S-acetoxy-5R-methyl-3-methylene-6-phenylhexyl)-6-(E)-4S,6S-dimethyloct-2-enoyloxy)-4,7S-dihydroxy-2,8-dioxabicyclo[321]octane-3S,4S,5R-tricarboxylic acid; 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-(4,6-dimethyl-2-octenoate), (5(2E,4S,6S),7S)-; Squalestatin 1, Glaxo; Zaragozic acid A, Glaxo

Indication

Disease Entry	ICD 11	Status	REF
Arteriosclerosis	BD40	Terminated	[1]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 3

Molecular Weight (mw)

690.7

Logarithm of the Partition Coefficient (xlogp)

4.9

Rotatable Bond Count (rotbonds)

19

Hydrogen Bond Donor Count (hbonddonor)

5

Hydrogen Bond Acceptor Count (hbondacc)

14

Chemical Identifiers

Formula: C35H46O14
IUPAC Name: (1S,3S,4S,5R,6R,7R)-1-[(4S,5R)-4-acetyloxy-5-methyl-3-methylidene-6-phenylhexyl]-6-[(E,4S,6S)-4,6-dimethyloct-2-enoyl]oxy-4,7-dihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid
Canonical SMILES: CC[C@H](C)C[C@H](C)/C=C/C(=O)O[C@@H]1[C@H]([C@]2(O[C@@H]([C@]([C@@]1(O2)C(=O)O)(C(=O)O)O)C(=O)O)CCC(=C)[C@H]([C@H](C)CC3=CC=CC=C3)OC(=O)C)O
InChI: 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
InChIKey: DFKDOZMCHOGOBR-NCSQYGPNSA-N

Cross-matching ID

PubChem CID: 6438355
ChEBI ID: CHEBI:75170
CAS Number: 142561-96-4
TTD ID: D0O1AV

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
RAC-alpha serine/threonine-protein kinase (AKT1)	TTWTSCV	AKT1_HUMAN	Inhibitor	[2]
Squalene synthetase (FDFT1)	TTFQEO5	FDFT_HUMAN	Modulator	[3]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease

Arteriosclerosis

ICD Disease Classification

BD40

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Squalene synthetase (FDFT1)	DTT	FDFT1	7.85E-01	-0.09	-0.38

Molecular Expression Atlas (MEA)

MEA Detail

Jump to Detail Molecular Expression Atlas of This Drug

References

1	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 3057).
2	Raft nanodomains contribute to Akt/PKB plasma membrane recruitment and activation. Nat Chem Biol. 2008 Sep;4(9):538-47.
3	Squalestatin 1, a potent inhibitor of squalene synthase, which lowers serum cholesterol in vivo. J Biol Chem. 1992 Jun 15;267(17):11705-8.