Alkannin-beta-hydroxyisovalerate
Basic information
- CAS
7415-78-3- Standard SMILES
CC(C)=CCC(OC(=O)CC(C)(C)O)C1=CC(=O)c2c(O)ccc(O)c2C1=O- InChIKey
MXANJRGHSFELEJ-UHFFFAOYSA-N- Molecular formula
- C21H24O7
- Average molar mass
- 388.4 g/mol
- Monoisotopic mass
- 388.1522031
Names & identifiers
- Preferred name
- Alkannin-beta-hydroxyisovalerate
- IUPAC
- [1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] 3-hydroxy-3-methylbutanoate
- English name
- beta-Hydroxyisovalerylshikonin
- Molecular formula
- C21H24O7
- Molecular weight
- 388.41
Names & synonyms
Alkannin-beta-hydroxyisovalerate[1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] 3-hydroxy-3-methylbutanoate87798-74-1Beta-HydroxylsovalerylshikoninNSC110263NSC-110263NSC 373954?-Hydroxyisovalerylshikonin|A-hydroxylsovalerylshikoninSCHEMBL28984891MXANJRGHSFELEJ-UHFFFAOYSA-Alkannin-.beta.-hydroxyisovalerate
Show more names
β-Hydroxyisovalerylshikoninβ-Hydroxyisovalerylshikoninβ-HIVSAlkannin Impurity 1β-hydroxylsovalerylshikoninβ-hydroxylsovalerylshikoninBETA-HYDROXYISOVALERYSHIKONINbeta-Hydroxyisovalerylshikonin5,8-Dihydroxy-2-[(R)-1-[(3-hydroxy-3-methylbutanoyl)oxy]-4-methyl-3-pentenyl]-1,4-naphthalenedione
HAA41578NSC373954AKOS037515319NSC-373954
Database identifiers
- CAS
7415-78-3、87798-74-1- PubChem CID
- 100203
Properties
Computed structural properties
- XLogP
- 3.4
- Topological polar surface area
- 121 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 7
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 700
Physicochemical properties
- Melting point
- 90 · 90-92 °C
- Boiling point
- 616.9 · 616.9±55.0 °C(Predicted)
- Density
- 1.312 · 1.312±0.06 g/cm3(Predicted)
- storage temp.
- 4 °C, · 4°C, protect from light
- solubility
- Soluble in DMSO
- pka
- 7.08 · 7.08±0.20(Predicted)
- form
- Solid
- color
- Brown to black
- LogP
- 2.424 · 2.424 (est)
Chemistry & industry
Applications
UsesBeta-hydroxyisovalerylshikonin is a natural product isolated from Lithospermum erythrorhizon, acts as a potent inhibitor of protein tyrosine kinases (PTK), with IC50s of 0.7μM and 1μM for EGFR and v-Src receptor, respectively. Beta-hydroxyisovalerylshikonin is effective against a wide variety of tumor cell lines, and most efficiently induces cell-death in NCI-H522 and DMS114 cells[1].
Related reactions
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Compound notes
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