Shikonin

Details

• Internal ID: fd3f3a1f-89a8-4a91-9817-941514f39282
• Taxonomy: Benzenoids > Naphthalenes > Naphthoquinones
• IUPAC Name: 5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methylpent-3-enyl]naphthalene-1,4-dione
• SMILES (Canonical): CC(=CCC(C1=CC(=O)C2=C(C=CC(=C2C1=O)O)O)O)C
• SMILES (Isomeric): CC(=CC[C@H](C1=CC(=O)C2=C(C=CC(=C2C1=O)O)O)O)C
• 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
• InChI Key: NEZONWMXZKDMKF-SNVBAGLBSA-N
• Popularity: 1,798 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₆O₅
• Molecular Weight: 288.29 g/mol
• Exact Mass: 288.09977361 g/mol
• Topological Polar Surface Area (TPSA): 94.80 Ų
• XlogP: 3.00

Synonyms

• 517-89-5
• Isoarnebin 4
• (R)-5,8-Dihydroxy-2-(1-hydroxy-4-methylpent-3-en-1-yl)naphthalene-1,4-dione
• Tokyo Violet
• Shikonin S
• (+)-Shikonin
• NSC 252844
• (R)-(+)-Shikonin
• UNII-3IK6592UBW
• Shikonine
• 5,8-Dihydroxy-2-[(1R)-1-hydroxy-4-methyl-pent-3-enyl]naphthalene-1,4-dione
• CCRIS 6492
• HSDB 8100
• BRN 2058010
• 3IK6592UBW
• Alkanna Red
• CHEBI:81068
• DTXSID30199653
• C.I. 75535
• 5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methylpent-3-enyl]naphthalene-1,4-dione
• (+)-5,8-Dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-1,4-naphthoquinone
• C17412
• C16H16O5
• 5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methylpent-3-en-1-yl]-1,4-dihydronaphthalene-1,4-dione
• shikonin, (+)-isomer
• 1,4-Naphthalenedione, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-, (R)-
• SR-05000001466
• C.I. 75535;Isoarnebin 4
• NSC-252844
• 1,4-naphthalenedione, 5,8-dihydroxy-2-((1r)-1-hydroxy-4-methyl-3-pentenyl)-
• 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
• 5,8-DIHYDROXY-2-((1R)-1-HYDROXY-4-METHYLPENT-3-ENYL)NAPHTHALENE-1,4-DIONE
• 5,8-Dihydroxy-2-[(1R)-1-hydroxy-4-methyl-3-penten-1-yl]-1,4-naphthalenedione
• 1,4-NAPHTHOQUINONE, 5,8-DIHYDROXY-2-(1-HYDROXY-4-METHYL-3-PENTENYL)-, (+)-
• (R)-Shikonin
• Shikonin,(S)
• SCHEMBL33969
• BSPBio_001270
• MLS006010149
• DTXCID90122144
• NEZONWMXZKDMKF-SNVBAGLBSA-N
• HMS1792P11
• HMS1990P11
• HMS2089L09
• HMS3403P11
• AMY39404
• HY-N0822
• MFCD00075680
• s8279
• AKOS015900416
• CCG-208272
• CS-5906
• NCGC00163489-01
• NCGC00163489-02
• NCGC00163489-04
• NCGC00163489-05
• AC-26871
• AS-13554
• BP-30212
• SMR002530673
• C15906
• J-502235
• SR-05000001466-1
• SR-05000001466-3
• Q27155024

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	15848.9 nM	Potency	via CMAUP
CHEMBL1293236	P46063	ATP-dependent DNA helicase Q1	10000 nM	Potency	via CMAUP
CHEMBL3775	P30304	Dual specificity phosphatase Cdc25A	220 nM	IC50	via Super-PRED
CHEMBL4804	P30305	Dual specificity phosphatase Cdc25B	400 nM	IC50	via Super-PRED
CHEMBL203	P00533	Epidermal growth factor receptor erbB1	139.2 nM	IC50	via Super-PRED
CHEMBL1293224	P10636	Microtubule-associated protein tau	4466.8 nM; 2238.7 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	25000 nM	IC50	PMID: 15050628
CHEMBL1075189	P14618	Pyruvate kinase isozymes M1/M2	500 nM	IC50	via Super-PRED
CHEMBL1293232	Q16637	Survival motor neuron protein	5623.4 nM	Potency	via CMAUP
CHEMBL1947	P10828	Thyroid hormone receptor beta-1	28183.8 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.86%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.35%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.70%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.35%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.03%	85.14%
CHEMBL3401	O75469	Pregnane X receptor	87.41%	94.73%
CHEMBL3038469	P24941	CDK2/Cyclin A	84.20%	91.38%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.05%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.96%	99.15%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	80.61%	96.67%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.49%	90.71%

Plants that contains it

• Arnebia decumbens
• Arnebia euchroma
• Arnebia guttata
• Arnebia hispidissima
• Echium plantagineum
• Echium rubrum
• Eucalyptus coccifera
• Lithospermum erythrorhizon
• Lithospermum officinale
• Onosma paniculata
• Rhizomnium magnifolium
• Strychnos usambarensis

Cross-Links

• PubChem: 479503
• NPASS: NPC246693
• ChEMBL: CHEMBL9470
• LOTUS: LTS0139652
• wikiData: Q27155024