Beta-Hydroxyisovalerylshikonin

HCID 479502

Substructure search Find similar structures

Basic information

CAS: 7415-78-3
Standard SMILES: CC(C)=CC[C@@H](OC(=O)CC(C)(C)O)C1=CC(=O)c2c(O)ccc(O)c2C1=O
InChIKey: MXANJRGHSFELEJ-MRXNPFEDSA-N
Molecular formula: C21H24O7
Average molar mass: 388.4 g/mol
Monoisotopic mass: 388.1522031

Overview

beta-Hydroxyisovalerylshikonin has been reported in Onosma paniculata, Lithospermum erythrorhizon, and Echium plantagineum with data available.

Names & identifiers

Preferred name: Beta-Hydroxyisovalerylshikonin
IUPAC: [(1R)-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

beta-Hydroxyisovalerylshikoninbeta-HIVS7415-78-3[(1R)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] 3-hydroxy-3-methylbutanoate((1R)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl) 3-hydroxy-3-methylbutanoateRefChem:119397Beta-Hydroxylsovalerylshikonin(R)-1-(5,8-Dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl 3-hydroxy-3-methylbutanoate-Hydroxyisovalerylshikonin3'-HydroxyisovalerylshikoninNSC110263NSC-110263

Show more names

β-Hydroxyisovalerylshikoninβ-Hydroxyisovalerylshikoninβ-HIVSAlkannin Impurity 1β-hydroxylsovalerylshikoninβ-hydroxylsovalerylshikoninBETA-HYDROXYISOVALERYSHIKONIN5,8-Dihydroxy-2-[(R)-1-[(3-hydroxy-3-methylbutanoyl)oxy]-4-methyl-3-pentenyl]-1,4-naphthalenedione

MFCD04038036|?-Hydroxyisovalerylshikoninbeta-Hydroxyisovalerylshikoni(1r)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl 3-hydroxy-3-methylbutanoateSCHEMBL842120orb1297444SCHEMBL29378718(c)micro-Hydroxyisovalerylshikonin

Database identifiers

CAS: 7415-78-3
PubChem CID: 479502
ChEMBL: CHEMBL397309
Nikkaji: J392.400I

Properties

Computed structural properties

XLogP: 3.4
Topological polar surface area: 121 Å²
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 · 1 item

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].

Suppliers49 total

南京世洲生物科技有限公司025-85560043 15850508050 · [email protected]

成都普瑞法科技开发有限公司+86-028-82633397 18982077548 · [email protected]

成都乐美天医药科技有限公司17308096051 17308096051 · [email protected]

Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]

上海纯优生物科技有限公司15921393123 18302135232 · [email protected]

Related reactions

0 records

New reaction record

No reaction records under the current filter.

Compound notes

Loading…