Shikonin

C16H16O5 — CID 479503

IUPAC5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methylpent-3-enyl]naphthalene-1,4-dione
SMILESCC(=CC[C@H](C1=CC(=O)C2=C(C=CC(=C2C1=O)O)O)O)C
InChIInChI=1S/C16H16O5/c1-8(2)3-4-10(17)9-7-13(20)14-11(18)5-6-12(19)15(14)16(9)21/h3,5-7,10,17-19H,4H2,1-2H3/t10-/m1/s1
InChIKeyNEZONWMXZKDMKF-SNVBAGLBSA-N
MW288.29 g/mol
LogP3.00
Rot. Bonds3

About Shikonin

Shikonin (PubChem CID 479503) has the molecular formula C16H16O5 and a molecular weight of 288.29 g/mol. Its IUPAC name is 5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methylpent-3-enyl]naphthalene-1,4-dione.

Molecular Properties

Compound NameShikonin
PubChem CID479503
Molecular FormulaC16H16O5
Molecular Weight288.29 g/mol
Exact Mass288.10
IUPAC Name5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methylpent-3-enyl]naphthalene-1,4-dione
SMILESCC(=CC[C@H](C1=CC(=O)C2=C(C=CC(=C2C1=O)O)O)O)C
InChIInChI=1S/C16H16O5/c1-8(2)3-4-10(17)9-7-13(20)14-11(18)5-6-12(19)15(14)16(9)21/h3,5-7,10,17-19H,4H2,1-2H3/t10-/m1/s1
InChIKeyNEZONWMXZKDMKF-SNVBAGLBSA-N
XLogP3.00
TPSA94.80 Ų
H-Bond Donors3
H-Bond Acceptors5
Rotatable Bonds3
Heavy Atoms21
Complexity501

Lipinski Rule of Five

Passes Rule of Five

RuleValue
MW ≤ 500288.29
LogP ≤ 53.00
H-Bond Donors ≤ 53
H-Bond Acceptors ≤ 105

Computed Properties (RDKit)

Structural Alerts{'alert_name': 'quinone_A(370)', 'substructure': 'N/A'}, {'alert_name': 'ene_one_D(1)', 'substructure': 'N/A'}, {'alert_name': 'hydroquinone', 'substructure': 'N/A'}, {'alert_name': 'isolated_alkene', 'substructure': 'N/A'}

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Related Compounds

Chrysophanol
CID 10208
1,8-Dihydroxyanthraquinone
CID 2950
Plumbagin
CID 10205
Juglone
CID 3806
Quinizarin
CID 6688
Aloe emodin
CID 10207
Naphthazarin
CID 10141
Alkannin
CID 72521
(+-)-Shikonin
CID 5208
2-Acetylhydroquinone
CID 10279
Nanaomycin A
CID 442757
Anthrarufin
CID 8328

Frequently Asked Questions

What is the IUPAC name of Shikonin?
The IUPAC name of Shikonin (CID 479503) is 5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methylpent-3-enyl]naphthalene-1,4-dione.
What is the SMILES notation for Shikonin?
The canonical SMILES for Shikonin is CC(=CC[C@H](C1=CC(=O)C2=C(C=CC(=C2C1=O)O)O)O)C.
What is the InChIKey of Shikonin?
The InChIKey is NEZONWMXZKDMKF-SNVBAGLBSA-N. The full InChI is InChI=1S/C16H16O5/c1-8(2)3-4-10(17)9-7-13(20)14-11(18)5-6-12(19)15(14)16(9)21/h3,5-7,10,17-19H,4H2,1-2H3/t10-/m1/s1.
What are the key properties of Shikonin?
Shikonin has a molecular weight of 288.29 g/mol, XLogP of 3.00, 3 rotatable bonds, 3 hydrogen bond donors, and 5 hydrogen bond acceptors.
Where does this data come from?
All data for Shikonin is sourced from PubChem (CID 479503), the world's largest open chemistry database maintained by the National Library of Medicine (NIH).