(E)-5-[(1S,4aR,8aR)-2-(hydroxymethyl)-5,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-(acetyloxymethyl)pent-2-enoic acid

C22H34O5 — CID 38358916

IUPAC(E)-5-[(1S,4aR,8aR)-2-(hydroxymethyl)-5,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-(acetyloxymethyl)pent-2-enoic acid
SMILESCC(=O)OC/C(=C/C(=O)O)CC[C@@H]1C(CO)=CC[C@@H]2C(C)(C)CCC[C@@]12C
InChIInChI=1S/C22H34O5/c1-15(24)27-14-16(12-20(25)26)6-8-18-17(13-23)7-9-19-21(2,3)10-5-11-22(18,19)4/h7,12,18-19,23H,5-6,8-11,13-14H2,1-4H3,(H,25,26)/b16-12+/t18-,19-,22+/m1/s1
InChIKeyOEWYXUOBTOXNMX-VBIQWIQDSA-N
MW378.51 g/mol
LogP4.11
Rot. Bonds7

About (E)-5-[(1S,4aR,8aR)-2-(hydroxymethyl)-5,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-(acetyloxymethyl)pent-2-enoic acid

(E)-5-[(1S,4aR,8aR)-2-(hydroxymethyl)-5,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-(acetyloxymethyl)pent-2-enoic acid (PubChem CID 38358916) has the molecular formula C22H34O5 and a molecular weight of 378.51 g/mol. Its IUPAC name is (E)-5-[(1S,4aR,8aR)-2-(hydroxymethyl)-5,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-(acetyloxymethyl)pent-2-enoic acid.

Molecular Properties

Compound Name(E)-5-[(1S,4aR,8aR)-2-(hydroxymethyl)-5,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-(acetyloxymethyl)pent-2-enoic acid
PubChem CID38358916
Molecular FormulaC22H34O5
Molecular Weight378.51 g/mol
Exact Mass378.24
IUPAC Name(E)-5-[(1S,4aR,8aR)-2-(hydroxymethyl)-5,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-(acetyloxymethyl)pent-2-enoic acid
SMILESCC(=O)OC/C(=C/C(=O)O)CC[C@@H]1C(CO)=CC[C@@H]2C(C)(C)CCC[C@@]12C
InChIInChI=1S/C22H34O5/c1-15(24)27-14-16(12-20(25)26)6-8-18-17(13-23)7-9-19-21(2,3)10-5-11-22(18,19)4/h7,12,18-19,23H,5-6,8-11,13-14H2,1-4H3,(H,25,26)/b16-12+/t18-,19-,22+/m1/s1
InChIKeyOEWYXUOBTOXNMX-VBIQWIQDSA-N
XLogP4.11
TPSA83.83 Ų
H-Bond Donors2
H-Bond Acceptors4
Rotatable Bonds7
Heavy Atoms27
Complexity—

Lipinski Rule of Five

Passes Rule of Five

RuleValue
MW ≤ 500378.51
LogP ≤ 54.11
H-Bond Donors ≤ 52
H-Bond Acceptors ≤ 104

Computed Properties (RDKit)

Structural Alerts{'alert_name': 'isolated_alkene', 'substructure': 'N/A'}, {'alert_name': 'Michael_acceptor_1', 'substructure': 'N/A'}

Analyze (E)-5-[(1S,4aR,8aR)-2-(hydroxymethyl)-5,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-(acetyloxymethyl)pent-2-enoic acid with MolForge

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Related Compounds

Cacospongionolide B
CID 10386285
Cacospongionolide E
CID 23243376
16-Acetoxy-6-oxo-7,13-labdadien-15-oic acid
CID 45359949
(E)-5-[(1S,4aR,8aR)-2-formyl-5,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-(acetyloxymethyl)pent-2-enoic acid
CID 45359950
1,4a-dimethyl-6-methylidene-5-[2-(5-oxo-2H-furan-4-yl)ethyl]-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
CID 14806212
Pinusolidic Acid
CID 25880646
(2S)-3-[2-[(1S,2R,4aR,8aR)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]ethyl]-2-hydroxy-2H-furan-5-one
CID 44224156
10beta-Hydroxytaxa-4(20),11-dien-5alpha-yl acetate
CID 443488
(2E)-5-[(1R,2R,4aR,5R,8aS)-2-hydroxy-5-(hydroxymethyl)-2,5,8a-trimethyldecahydronaphthalen-1-yl]-3-methylpent-2-enoic acid
CID 24899923
(1S,4aR,5S)-5-[(E)-5-methoxy-3-methyl-5-oxopent-3-enyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
CID 23928101
(4aR,5S,8R,9aR)-8-hydroxy-9a-methoxy-3,4a,5-trimethyl-5,6,7,8-tetrahydro-4H-benzo[f][1]benzofuran-2-one
CID 11185028
1beta,8alpha-Dihydroxyeremophila-7(11),9-dien-12,8-olide
CID 11357536

Frequently Asked Questions

What is the IUPAC name of (E)-5-[(1S,4aR,8aR)-2-(hydroxymethyl)-5,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-(acetyloxymethyl)pent-2-enoic acid?
The IUPAC name of (E)-5-[(1S,4aR,8aR)-2-(hydroxymethyl)-5,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-(acetyloxymethyl)pent-2-enoic acid (CID 38358916) is (E)-5-[(1S,4aR,8aR)-2-(hydroxymethyl)-5,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-(acetyloxymethyl)pent-2-enoic acid.
What is the SMILES notation for (E)-5-[(1S,4aR,8aR)-2-(hydroxymethyl)-5,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-(acetyloxymethyl)pent-2-enoic acid?
The canonical SMILES for (E)-5-[(1S,4aR,8aR)-2-(hydroxymethyl)-5,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-(acetyloxymethyl)pent-2-enoic acid is CC(=O)OC/C(=C/C(=O)O)CC[C@@H]1C(CO)=CC[C@@H]2C(C)(C)CCC[C@@]12C.
What is the InChIKey of (E)-5-[(1S,4aR,8aR)-2-(hydroxymethyl)-5,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-(acetyloxymethyl)pent-2-enoic acid?
The InChIKey is OEWYXUOBTOXNMX-VBIQWIQDSA-N. The full InChI is InChI=1S/C22H34O5/c1-15(24)27-14-16(12-20(25)26)6-8-18-17(13-23)7-9-19-21(2,3)10-5-11-22(18,19)4/h7,12,18-19,23H,5-6,8-11,13-14H2,1-4H3,(H,25,26)/b16-12+/t18-,19-,22+/m1/s1.
What are the key properties of (E)-5-[(1S,4aR,8aR)-2-(hydroxymethyl)-5,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-(acetyloxymethyl)pent-2-enoic acid?
(E)-5-[(1S,4aR,8aR)-2-(hydroxymethyl)-5,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-(acetyloxymethyl)pent-2-enoic acid has a molecular weight of 378.51 g/mol, XLogP of 4.11, 7 rotatable bonds, 2 hydrogen bond donors, and 4 hydrogen bond acceptors.
Where does this data come from?
All data for (E)-5-[(1S,4aR,8aR)-2-(hydroxymethyl)-5,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-(acetyloxymethyl)pent-2-enoic acid is sourced from PubChem (CID 38358916), the world's largest open chemistry database maintained by the National Library of Medicine (NIH).