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CHEMISTRY
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ACTIVE PHARMA INGREDIENTS

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Chemistry

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Also known as: Tiaprost, 71116-82-0, (e)-7-[3,5-dihydroxy-2-[(e)-3-hydroxy-4-thiophen-3-yloxybut-1-enyl]cyclopentyl]hept-5-enoic acid, 5-heptenoic acid,7-[3,5-dihydroxy-2-[3-hydroxy-4-(3-thienyloxy)-1-butenyl]cyclopentyl]-, 7-[3,5-dihydroxy-2-[3-hydroxy-4-(3-thienyloxy)-1-butenyl]cyclopentyl]-5-heptenoic acid, Schembl12495592

Molecular Formula

C₂₀H₂₈O₆S

Molecular Weight

396.5 g/mol

InChI Key

FYBFDIIAPRHIQS-SYJKBYRUSA-N

1 2D Structure

Tiaprost

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(E)-7-[3,5-dihydroxy-2-[(E)-3-hydroxy-4-thiophen-3-yloxybut-1-enyl]cyclopentyl]hept-5-enoic acid

2.1.2 InChI

InChI=1S/C20H28O6S/c21-14(12-26-15-9-10-27-13-15)7-8-17-16(18(22)11-19(17)23)5-3-1-2-4-6-20(24)25/h1,3,7-10,13-14,16-19,21-23H,2,4-6,11-12H2,(H,24,25)/b3-1+,8-7+

2.1.3 InChI Key

FYBFDIIAPRHIQS-SYJKBYRUSA-N

2.1.4 Canonical SMILES

C1C(C(C(C1O)C=CC(COC2=CSC=C2)O)CC=CCCCC(=O)O)O

2.1.5 Isomeric SMILES

C1C(C(C(C1O)/C=C/C(COC2=CSC=C2)O)C/C=C/CCCC(=O)O)O

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Tiaprost

2. Tiaprost, (1r-(1alpha(z),2beta(1e,3r*),3alpha,5alpha))-isomer

3. Tiaprost, (1r-(1alpha(z),2beta(1e,3s*),3alpha,5alpha))-isomer

2.2.2 Depositor-Supplied Synonyms

1. Tiaprost

2. 71116-82-0

3. (e)-7-[3,5-dihydroxy-2-[(e)-3-hydroxy-4-thiophen-3-yloxybut-1-enyl]cyclopentyl]hept-5-enoic Acid

4. 5-heptenoic Acid,7-[3,5-dihydroxy-2-[3-hydroxy-4-(3-thienyloxy)-1-butenyl]cyclopentyl]-

5. 7-[3,5-dihydroxy-2-[3-hydroxy-4-(3-thienyloxy)-1-butenyl]cyclopentyl]-5-heptenoic Acid

6. Schembl12495592

7. Schembl12495595

8. Dtxsid901021711

9. Bcp30311

10. Akos015896642

11. Hy-111478

12. Cs-0041593

13. A850966

2.3 Create Date

2006-04-28

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₂₈O₆S
Molecular Weight	396.5 g/mol
XLogP3	1.7
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	11
Exact Mass	396.16065978 g/mol
Monoisotopic Mass	396.16065978 g/mol
Topological Polar Surface Area	136 Å²
Heavy Atom Count	27
Formal Charge	0
Complexity	509
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	5
Defined Bond Stereocenter Count	2
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1