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Chemistry

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Also known as: Cicloxolone, 52247-86-6, Bx 363a [as disodium salt], Chembl2106051, Zinc8214526, (2s,4as,6ar,6as,6br,8ar,10s,12as,14br)-10-[(1s,2r)-2-carboxycyclohexanecarbonyl]oxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1h-picene-2-carboxylic acid
Molecular Formula
C38H56O7
Molecular Weight
624.8  g/mol
InChI Key
IPIHZIYZLLMCRF-APMXPKBPSA-N

Cicloxolone
Cicloxolone is a broad spectrum antiviral agent with a largely non-specific and complex mode of antiviral action. Cicloxolone has been shown to impair Golgi apparatus functions related to transport of glycoproteins of vesicular stomatitis virus.
1 2D Structure

Cicloxolone

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2S,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bR)-10-[(1S,2R)-2-carboxycyclohexanecarbonyl]oxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylic acid
2.1.2 InChI
InChI=1S/C38H56O7/c1-33(2)27-12-15-38(7)29(36(27,5)14-13-28(33)45-31(42)23-11-9-8-10-22(23)30(40)41)26(39)20-24-25-21-35(4,32(43)44)17-16-34(25,3)18-19-37(24,38)6/h20,22-23,25,27-29H,8-19,21H2,1-7H3,(H,40,41)(H,43,44)/t22-,23+,25+,27+,28+,29-,34-,35+,36+,37-,38-/m1/s1
2.1.3 InChI Key
IPIHZIYZLLMCRF-APMXPKBPSA-N
2.1.4 Canonical SMILES
CC1(C2CCC3(C(C2(CCC1OC(=O)C4CCCCC4C(=O)O)C)C(=O)C=C5C3(CCC6(C5CC(CC6)(C)C(=O)O)C)C)C)C
2.1.5 Isomeric SMILES
C[C@]12CC[C@](C[C@H]1C3=CC(=O)[C@@H]4[C@]5(CC[C@@H](C([C@@H]5CC[C@]4([C@@]3(CC2)C)C)(C)C)OC(=O)[C@H]6CCCC[C@H]6C(=O)O)C)(C)C(=O)O
2.2 Synonyms
2.2.1 MeSH Synonyms

1. 3-hydroxy-11-oxoolean-12-en-30-oic Acid 1,2-cyclohexanedicarboxylate

2. Cicloxolone

3. Cicloxolone Sodium

4. Cicloxolone, (3beta(cis),20beta)-isomer, Disodium Salt

2.2.2 Depositor-Supplied Synonyms

1. Cicloxolone

2. 52247-86-6

3. Bx 363a [as Disodium Salt]

4. Chembl2106051

5. Zinc8214526

6. (2s,4as,6ar,6as,6br,8ar,10s,12as,14br)-10-[(1s,2r)-2-carboxycyclohexanecarbonyl]oxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1h-picene-2-carboxylic Acid

2.3 Create Date
2013-02-04
3 Chemical and Physical Properties
Molecular Weight 624.8 g/mol
Molecular Formula C38H56O7
XLogP38.1
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count7
Rotatable Bond Count5
Exact Mass624.40260412 g/mol
Monoisotopic Mass624.40260412 g/mol
Topological Polar Surface Area118 Ų
Heavy Atom Count45
Formal Charge0
Complexity1330
Isotope Atom Count0
Defined Atom Stereocenter Count11
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1

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