chempirical

Shikonin

C16H16O5CAS 517-89-5288.30 g/mol

Open in Covalent MOL file
HOOOHHOO
AlcoholAlkeneKetonePhenol

Properties

Molecular formula
C16H16O5
Molar mass
288.30 g/mol
Exact mass
288.0998 Da
Density
1.373 g/mL
Melting point
147 °C
logP
2.12Crippen estimate
Polar surface area
94.8 Ų
H-bond donors / acceptors
3 / 5
Rotatable bonds
3
Stereocentres
Rin SMILES atom order

Hazards

Warning
Irritant (GHS07)

Aggregated from 2 ECHA notifications, via PubChem; a share says how many notifiers assign that statement.

Precautionary statements

P261, P264, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, P501

Identifiers

CAS number
517-89-5
SMILES
CC(C)=CC[C@@H](O)C1=CC(=O)c2c(O)ccc(O)c2C1=O
InChIKey
NEZONWMXZKDMKF-SNVBAGLBSA-N
InChI
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

Weigh it out

Type any one amount. The others follow from the molar mass and density.

Names and synonyms

14 names · show all
  • 1,4-Naphthalenedione, 5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methyl-3-penten-1-yl]-
  • 1,4-Naphthoquinone, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-, (+)-
  • 1,4-Naphthalenedione, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-, (R)-
  • 1,4-Naphthalenedione, 5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methyl-3-pentenyl]-
  • 5,8-Dihydroxy-2-[(1R)-1-hydroxy-4-methyl-3-penten-1-yl]-1,4-naphthalenedione
  • C.I. 75535
  • Tokyo violet
  • (+)-Shikonin
  • Isoarnebin 4
  • NSC 252844
  • Shikonin S
  • Shikonine
  • (R)-(+)-Shikonin
  • 1,4-Naphthalenedione 5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methyl-3-penten-1-yl]-

Work with Shikonin

Predict the NMR spectrum1H and 13C shifts with multiplicities Make a solutionWhat to weigh for any molarity and volume Check drug-likenessLipinski, Veber and lead-likeness Isotope patternExact mass and the mass spectrum pattern

Stereoisomers, salts and isotopologues

The same compound in another form: other stereochemistry, a salt or hydrate, the free acid or base, or an isotope-labelled version.

Alkannin517-88-4Enantiomer

Similar compounds

Acetylshikonin24502-78-171 % similar Beta,beta-Dimethylacrylshikonin24502-79-269 % similar Deoxyshikonin43043-74-958 % similar Plumbagin481-42-540 % similar Naphthazarin475-38-739 % similar Isobavachalcone20784-50-335 % similar 2,3-Dichloro-5,8-dihydroxy-1,4-naphthoquinone14918-69-534 % similar Demethylsuberosin21422-04-833 % similar

Tanimoto similarity of circular fingerprints over the whole catalogue. All similar compounds

Same formula

Columbianetin acetate23180-65-6

Elsewhere

PubChem CAS Common Chemistry NIST WebBook