[(1S,2S,4Z,8Z,12R,13S)-12-hydroxy-4,8,12-trimethyl-16-methylidene-15-oxo-14-oxabicyclo[11.3.1]heptadeca-4,8-dien-2-yl] acetate

C22H32O5 — CID 100921072

IUPAC[(1S,2S,4Z,8Z,12R,13S)-12-hydroxy-4,8,12-trimethyl-16-methylidene-15-oxo-14-oxabicyclo[11.3.1]heptadeca-4,8-dien-2-yl] acetate
SMILESC=C1C(=O)O[C@H]2C[C@@H]1[C@@H](OC(C)=O)C/C(C)=C\CC/C(C)=C\CC[C@@]2(C)O
InChIInChI=1S/C22H32O5/c1-14-8-6-9-15(2)12-19(26-17(4)23)18-13-20(27-21(24)16(18)3)22(5,25)11-7-10-14/h9-10,18-20,25H,3,6-8,11-13H2,1-2,4-5H3/b14-10-,15-9-/t18-,19-,20-,22+/m0/s1
InChIKeyWMGWWFHPPNGBBT-XLQUWDFMSA-N
MW376.49 g/mol
LogP4.01
Rot. Bonds1

About [(1S,2S,4Z,8Z,12R,13S)-12-hydroxy-4,8,12-trimethyl-16-methylidene-15-oxo-14-oxabicyclo[11.3.1]heptadeca-4,8-dien-2-yl] acetate

[(1S,2S,4Z,8Z,12R,13S)-12-hydroxy-4,8,12-trimethyl-16-methylidene-15-oxo-14-oxabicyclo[11.3.1]heptadeca-4,8-dien-2-yl] acetate (PubChem CID 100921072) has the molecular formula C22H32O5 and a molecular weight of 376.49 g/mol. Its IUPAC name is [(1S,2S,4Z,8Z,12R,13S)-12-hydroxy-4,8,12-trimethyl-16-methylidene-15-oxo-14-oxabicyclo[11.3.1]heptadeca-4,8-dien-2-yl] acetate.

Molecular Properties

Compound Name[(1S,2S,4Z,8Z,12R,13S)-12-hydroxy-4,8,12-trimethyl-16-methylidene-15-oxo-14-oxabicyclo[11.3.1]heptadeca-4,8-dien-2-yl] acetate
PubChem CID100921072
Molecular FormulaC22H32O5
Molecular Weight376.49 g/mol
Exact Mass376.22
IUPAC Name[(1S,2S,4Z,8Z,12R,13S)-12-hydroxy-4,8,12-trimethyl-16-methylidene-15-oxo-14-oxabicyclo[11.3.1]heptadeca-4,8-dien-2-yl] acetate
SMILESC=C1C(=O)O[C@H]2C[C@@H]1[C@@H](OC(C)=O)C/C(C)=C\CC/C(C)=C\CC[C@@]2(C)O
InChIInChI=1S/C22H32O5/c1-14-8-6-9-15(2)12-19(26-17(4)23)18-13-20(27-21(24)16(18)3)22(5,25)11-7-10-14/h9-10,18-20,25H,3,6-8,11-13H2,1-2,4-5H3/b14-10-,15-9-/t18-,19-,20-,22+/m0/s1
InChIKeyWMGWWFHPPNGBBT-XLQUWDFMSA-N
XLogP4.01
TPSA72.83 Ų
H-Bond Donors1
H-Bond Acceptors5
Rotatable Bonds1
Heavy Atoms27
Complexity—

Lipinski Rule of Five

Passes Rule of Five

RuleValue
MW ≤ 500376.49
LogP ≤ 54.01
H-Bond Donors ≤ 51
H-Bond Acceptors ≤ 105

Computed Properties (RDKit)

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

Analyze [(1S,2S,4Z,8Z,12R,13S)-12-hydroxy-4,8,12-trimethyl-16-methylidene-15-oxo-14-oxabicyclo[11.3.1]heptadeca-4,8-dien-2-yl] acetate with MolForge

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Related Compounds

Mupirocin
CID 446596
[(1S,2S,4R,7E,10S,11R)-8-(hydroxymethyl)-4-methyl-12-methylidene-13-oxo-3,14-dioxatricyclo[9.3.0.02,4]tetradec-7-en-10-yl] 2-methylprop-2-enoate
CID 156017709
[(3aR,4R,5Z,10R,11R,11aS)-6-formyl-11-hydroxy-3-methylidene-2-oxospiro[4,7,8,9,11,11a-hexahydro-3aH-cyclodeca[b]furan-10,2'-oxirane]-4-yl] 2-methylprop-2-enoate
CID 44409577
Flexibilide
CID 5458571
Altamisic acid
CID 15143694
Sinulaflexiolide F
CID 24970446
Psilostachyin B
CID 5320768
3beta-Hydroxyparthenolide
CID 138911145
[(3aR,4R,5E,10R,11R,11aS)-6-formyl-11-hydroxy-3-methylidene-2-oxospiro[4,7,8,9,11,11a-hexahydro-3aH-cyclodeca[b]furan-10,2'-oxirane]-4-yl] 2-methylprop-2-enoate
CID 44398301
[(1S,2R,4R,7E,11E,14S,15R)-4,8,12-trimethyl-16-methylidene-17-oxo-3,18-dioxatricyclo[13.3.0.02,4]octadeca-7,11-dien-14-yl] acetate
CID 44383511
(1R,4E,8E,12S,13S)-12-hydroxy-4,8,12-trimethyl-16-methylidene-14-oxabicyclo[11.3.1]heptadeca-4,8-dien-15-one
CID 155532095
[(1S,2S,4E,8Z,12R,13S)-12-hydroxy-4,8,12-trimethyl-16-methylidene-15-oxo-14-oxabicyclo[11.3.1]heptadeca-4,8-dien-2-yl] acetate
CID 16215733

Frequently Asked Questions

What is the IUPAC name of [(1S,2S,4Z,8Z,12R,13S)-12-hydroxy-4,8,12-trimethyl-16-methylidene-15-oxo-14-oxabicyclo[11.3.1]heptadeca-4,8-dien-2-yl] acetate?
The IUPAC name of [(1S,2S,4Z,8Z,12R,13S)-12-hydroxy-4,8,12-trimethyl-16-methylidene-15-oxo-14-oxabicyclo[11.3.1]heptadeca-4,8-dien-2-yl] acetate (CID 100921072) is [(1S,2S,4Z,8Z,12R,13S)-12-hydroxy-4,8,12-trimethyl-16-methylidene-15-oxo-14-oxabicyclo[11.3.1]heptadeca-4,8-dien-2-yl] acetate.
What is the SMILES notation for [(1S,2S,4Z,8Z,12R,13S)-12-hydroxy-4,8,12-trimethyl-16-methylidene-15-oxo-14-oxabicyclo[11.3.1]heptadeca-4,8-dien-2-yl] acetate?
The canonical SMILES for [(1S,2S,4Z,8Z,12R,13S)-12-hydroxy-4,8,12-trimethyl-16-methylidene-15-oxo-14-oxabicyclo[11.3.1]heptadeca-4,8-dien-2-yl] acetate is C=C1C(=O)O[C@H]2C[C@@H]1[C@@H](OC(C)=O)C/C(C)=C\CC/C(C)=C\CC[C@@]2(C)O.
What is the InChIKey of [(1S,2S,4Z,8Z,12R,13S)-12-hydroxy-4,8,12-trimethyl-16-methylidene-15-oxo-14-oxabicyclo[11.3.1]heptadeca-4,8-dien-2-yl] acetate?
The InChIKey is WMGWWFHPPNGBBT-XLQUWDFMSA-N. The full InChI is InChI=1S/C22H32O5/c1-14-8-6-9-15(2)12-19(26-17(4)23)18-13-20(27-21(24)16(18)3)22(5,25)11-7-10-14/h9-10,18-20,25H,3,6-8,11-13H2,1-2,4-5H3/b14-10-,15-9-/t18-,19-,20-,22+/m0/s1.
What are the key properties of [(1S,2S,4Z,8Z,12R,13S)-12-hydroxy-4,8,12-trimethyl-16-methylidene-15-oxo-14-oxabicyclo[11.3.1]heptadeca-4,8-dien-2-yl] acetate?
[(1S,2S,4Z,8Z,12R,13S)-12-hydroxy-4,8,12-trimethyl-16-methylidene-15-oxo-14-oxabicyclo[11.3.1]heptadeca-4,8-dien-2-yl] acetate has a molecular weight of 376.49 g/mol, XLogP of 4.01, 1 rotatable bonds, 1 hydrogen bond donors, and 5 hydrogen bond acceptors.
Where does this data come from?
All data for [(1S,2S,4Z,8Z,12R,13S)-12-hydroxy-4,8,12-trimethyl-16-methylidene-15-oxo-14-oxabicyclo[11.3.1]heptadeca-4,8-dien-2-yl] acetate is sourced from PubChem (CID 100921072), the world's largest open chemistry database maintained by the National Library of Medicine (NIH).