Jesterone

C15H20O4 — CID 10515747

IUPAC(1R,5S,6R)-5-hydroxy-4-(hydroxymethyl)-1-(3-methylbut-2-enyl)-3-[(E)-prop-1-enyl]-7-oxabicyclo[4.1.0]hept-3-en-2-one
SMILESC/C=C/C1=C([C@@H]([C@@H]2[C@](C1=O)(O2)CC=C(C)C)O)CO
InChIInChI=1S/C15H20O4/c1-4-5-10-11(8-16)12(17)14-15(19-14,13(10)18)7-6-9(2)3/h4-6,12,14,16-17H,7-8H2,1-3H3/b5-4+/t12-,14+,15-/m0/s1
InChIKeyIIGGBGHNVOFBQW-ZQUADUEKSA-N
MW264.32 g/mol
LogP1.30
Rot. Bonds4

About Jesterone

Jesterone (PubChem CID 10515747) has the molecular formula C15H20O4 and a molecular weight of 264.32 g/mol. Its IUPAC name is (1R,5S,6R)-5-hydroxy-4-(hydroxymethyl)-1-(3-methylbut-2-enyl)-3-[(E)-prop-1-enyl]-7-oxabicyclo[4.1.0]hept-3-en-2-one.

Molecular Properties

Compound NameJesterone
PubChem CID10515747
Molecular FormulaC15H20O4
Molecular Weight264.32 g/mol
Exact Mass264.14
IUPAC Name(1R,5S,6R)-5-hydroxy-4-(hydroxymethyl)-1-(3-methylbut-2-enyl)-3-[(E)-prop-1-enyl]-7-oxabicyclo[4.1.0]hept-3-en-2-one
SMILESC/C=C/C1=C([C@@H]([C@@H]2[C@](C1=O)(O2)CC=C(C)C)O)CO
InChIInChI=1S/C15H20O4/c1-4-5-10-11(8-16)12(17)14-15(19-14,13(10)18)7-6-9(2)3/h4-6,12,14,16-17H,7-8H2,1-3H3/b5-4+/t12-,14+,15-/m0/s1
InChIKeyIIGGBGHNVOFBQW-ZQUADUEKSA-N
XLogP1.30
TPSA70.10 Ų
H-Bond Donors2
H-Bond Acceptors4
Rotatable Bonds4
Heavy Atoms19
Complexity482

Lipinski Rule of Five

Passes Rule of Five

RuleValue
MW ≤ 500264.32
LogP ≤ 51.30
H-Bond Donors ≤ 52
H-Bond Acceptors ≤ 104

Computed Properties (RDKit)

Structural Alerts{'alert_name': 'isolated_alkene', 'substructure': 'N/A'}, {'alert_name': 'Three-membered_heterocycle', 'substructure': 'N/A'}

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Related Compounds

Parasitenone
CID 636767
(E)-4-[(1R,5S,6R)-3-[(E)-hept-1-enyl]-5-hydroxy-4-(hydroxymethyl)-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-1-yl]-2-methylbut-2-enoic acid
CID 637206
Ambuic Acid
CID 11152290
Panepoxydone
CID 11148494
(1s,5r,6s)-4-[(1e)-1-Hepten-1-yl]-5-hydroxy-3-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one
CID 11414080
Pestalic acid E
CID 139590833
(1S,6R)-3-(hydroxymethyl)-4-[(E)-prop-1-enyl]-7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione
CID 6917396
(1R,5S,6R)-5-hydroxy-4-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one
CID 10464548
7-Deacetoxyyanuthone
CID 10360155
(E)-4-[(1R,5R,6R)-4-(acetyloxymethyl)-3-[(E)-hept-1-enyl]-5-hydroxy-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-1-yl]-2-methylbut-2-enoic acid
CID 25195250
(E)-4-[(1R,5R,6R)-3-heptyl-5-hydroxy-4-(hydroxymethyl)-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-1-yl]-2-methylbut-2-enoic acid
CID 25207982
(E)-4-[(1R,5R,6R)-3-[(1E,3E)-hepta-1,3-dienyl]-5-hydroxy-4-(hydroxymethyl)-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-1-yl]-2-methylbut-2-enoic acid
CID 25207985

Frequently Asked Questions

What is the IUPAC name of Jesterone?
The IUPAC name of Jesterone (CID 10515747) is (1R,5S,6R)-5-hydroxy-4-(hydroxymethyl)-1-(3-methylbut-2-enyl)-3-[(E)-prop-1-enyl]-7-oxabicyclo[4.1.0]hept-3-en-2-one.
What is the SMILES notation for Jesterone?
The canonical SMILES for Jesterone is C/C=C/C1=C([C@@H]([C@@H]2[C@](C1=O)(O2)CC=C(C)C)O)CO.
What is the InChIKey of Jesterone?
The InChIKey is IIGGBGHNVOFBQW-ZQUADUEKSA-N. The full InChI is InChI=1S/C15H20O4/c1-4-5-10-11(8-16)12(17)14-15(19-14,13(10)18)7-6-9(2)3/h4-6,12,14,16-17H,7-8H2,1-3H3/b5-4+/t12-,14+,15-/m0/s1.
What are the key properties of Jesterone?
Jesterone has a molecular weight of 264.32 g/mol, XLogP of 1.30, 4 rotatable bonds, 2 hydrogen bond donors, and 4 hydrogen bond acceptors.
Where does this data come from?
All data for Jesterone is sourced from PubChem (CID 10515747), the world's largest open chemistry database maintained by the National Library of Medicine (NIH).