1-(5,8-Dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl acetate

HCID 32464
NotesReactions
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Basic information

CAS
106295-33-4
Standard SMILES
CC(=O)OC(CC=C(C)C)C1=CC(=O)c2c(O)ccc(O)c2C1=O
InChIKey
WNFXUXZJJKTDOZ-UHFFFAOYSA-N
Molecular formula
C18H18O6
Average molar mass
330.3 g/mol
Monoisotopic mass
330.1103383

Overview

Acetylshikonin is a hydroxy-1,4-naphthoquinone and an acetate ester.

Names & identifiers

Preferred name
1-(5,8-Dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl acetate
IUPAC
[1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] acetate
English name
acetylshikonin
Molecular formula
C18H18O6
Molecular weight
330.33

Names & synonyms

1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl acetateDTXSID30909976RefChem:1054489DTXCID80133903454984-93-9DL-Acetylshikoninacetyl shikoninAlkannin, monoacetateNSC 291844NSC-291844ARNEBIN 3ARNEBIN-3
Show more names
1,4-Naphthalenedione, 2-(1-(acetyloxy)-4-methyl-3-pentenyl)-5,8-dihydroxy-1,4-Naphthalenedione, 2-[1-(acetyloxy)-4-methyl-3-penten-1-yl]-5,8-dihydroxy-
ALKANNIN MONOACETATEAcetylshikoninShikonin, acetylCHEMBL28569orb1222466orb1680290SCHEMBL1240671CHEBI:81069HY-N2181A

Database identifiers

CAS
106295-33-4、23444-71-5、24502-78-1、54984-93-9
PubChem CID
32464
DTXSID
DTXSID30909976
ChEMBL
CHEMBL28569
ChEBI
CHEBI:81069
Nikkaji
J1.354.872B

Properties

Computed structural properties

XLogP
3.5
Topological polar surface area
101 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
6
Rotatable bonds
5
Heavy atoms
24

Physicochemical properties

Boiling point
553.2 · 553.2±50.0 °C(Predicted)
Density
1.326 · 1.326±0.06 g/cm3(Predicted)
solubility
Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
form
Powder
pka
7.12 · 7.12±0.20(Predicted)
LogP
2.7 · 2.700 (est)

Chemistry & industry

Applications

UsesDL-Acetylshikonin is a non-selective, reversible cytochrome P450 inhibitor with IC50 values of 1.4-4.0 μM. DL-Acetylshikonin has anti-cancer and anti-inflammatory activities[1].

Suppliers9 total

杭州摩库生物医药科技有限公司+86-057181025280; +8617767106207 · [email protected]
武汉众志诚生物技术有限公司13628624121 13628604890 · [email protected]
武汉天植生物技术有限公司18607101326 15172504745 · [email protected]
EMMX Biotechnology LLC888-539-0666 · [email protected]
南京狄尔格医药科技有限公司025-025-51191215 18013836722 · [email protected]

Additional notes

DefinitionChEBI: Acetylshikonin is an acetate ester and a hydroxy-1,4-naphthoquinone.

Related reactions

1 records
New reaction record

Compound notes

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