C.I. Natural Red 20

Details

• Internal ID: 812e8e3f-9661-4615-ba05-4cb4d94c55fc
• Taxonomy: Benzenoids > Naphthalenes > Naphthoquinones
• IUPAC Name: 5,8-dihydroxy-2-(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(=CCC(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
• InChI Key: NEZONWMXZKDMKF-UHFFFAOYSA-N
• Popularity: 723 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
• Atomic LogP (AlogP): 2.12
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

• SHIKALKIN
• C.I. Natural Red 20
• (+-)-Shikonin
• Anchusin
• (+/-)-Alkannin
• ARNEBIN-4
• (Rac)-Shikonin
• 5,8-dihydroxy-2-(1-hydroxy-4-methylpent-3-enyl)naphthalene-1,4-dione
• (+-)-Alkannin
• Shikonine
• Alkanna Red
• C.I. 75530
• NSC94524
• (+)-Shikonin
• NSC252844
• NSC407295
• NSC 291845
• (+/-)-Shikonin
• C16H16O5
• 1,4-Naphthalenedione, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-
• 5,8-Dihydroxy-6-(1-hydroxy-4-methylpent-3-en-1-yl)naphthalene-1,4-dione
• 1,4-Naphthalenedione, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)- (9CI)
• shikonin, (+)-isomer
• C.I. 75535
• C.I. 75535;Isoarnebin 4
• Gromwell
• 1, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-, (S)-
• 1, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-, (-)-
• 1, 5,8-dihydroxy-6-(1-hydroxy-4-methyl-3-pentenyl)-, (-)-
• NSC-94524
• NSC-252844
• natural red 20
• Shikonin (7b)
• (+-)-Shikalkin
• ALKANNIN, 1-
• KBioGR_000610
• KBioSS_000610
• CHEMBL29285
• SCHEMBL3182028
• Shikonin, >=98% (HPLC)
• SCHEMBL14305203
• KBio2_000610
• KBio2_003178
• KBio2_005746
• KBio3_001079
• KBio3_001080
• NEZONWMXZKDMKF-UHFFFAOYSA-
• DTXSID00862100
• 1,4-Naphthalenedione, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-, (R)-
• 1,4-NAPHTHOQUINONE, 5,8-DIHYDROXY-2-(1-HYDROXY-4-METHYL-3-PENTENYL)-, (+)-
• 5,8-dihydroxy-2-[(1S)-1-hydroxy-4-methylpent-3-enyl]naphthalene-1,4-dione
• CHEBI:174748
• BDBM178090
• Bio2_000475
• Bio2_000955
• HMS1362P11
• BCP29329
• BCP34282
• HY-N6004
• NSC291845
• 5,8-dihydroxy-2-(1-hydroxy-4-methyl-pent-3-enyl)naphthalene-1,4-dione
• AKOS016034343
• ( inverted exclamation markA)-Shikonin
• NSC-291845
• NSC-407295
• IDI1_002230
• QTL1_000075
• SMP2_000188
• LS-95639
• LS-95640
• NCI60_002031
• CS-0032051
• FT-0651798
• FT-0746742
• FT-0774471
• H1780
• (-)-Shikonin;C.I. 75535; Isoarnebin 4
• 3-(2,2-Dimethylpropionylamino)isonicotinicacid
• Q-100621
• 1, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-
• 1, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-, (R)-
• 1, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-, (+)-
• 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-1,4-naphthoquinone
• 5,8-DIHYDROXY-2-(1-HYDROXY-4-METHYLPENT-3-EN-1-YL)NAPHTHALENE-1,4-DIONE
• 11019-15-1
• 8001-98-7
• 85921-41-1
• InChI=1/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

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	-	0.6593	65.93%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.8243	82.43%
OATP2B1 inhibitior	-	0.7124	71.24%
OATP1B1 inhibitior	+	0.9391	93.91%
OATP1B3 inhibitior	+	0.9560	95.60%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.8073	80.73%
P-glycoprotein inhibitior	-	0.9107	91.07%
P-glycoprotein substrate	-	0.9172	91.72%
CYP3A4 substrate	-	0.5793	57.93%
CYP2C9 substrate	-	0.6023	60.23%
CYP2D6 substrate	-	0.8340	83.40%
CYP3A4 inhibition	-	0.6708	67.08%
CYP2C9 inhibition	+	0.8714	87.14%
CYP2C19 inhibition	+	0.7648	76.48%
CYP2D6 inhibition	+	0.6042	60.42%
CYP1A2 inhibition	+	0.8668	86.68%
CYP2C8 inhibition	-	0.9263	92.63%
CYP inhibitory promiscuity	+	0.7179	71.79%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8363	83.63%
Carcinogenicity (trinary)	Non-required	0.6524	65.24%
Eye corrosion	-	0.9906	99.06%
Eye irritation	+	0.5265	52.65%
Skin irritation	-	0.6365	63.65%
Skin corrosion	-	0.9118	91.18%
Ames mutagenesis	+	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7431	74.31%
Micronuclear	-	0.5141	51.41%
Hepatotoxicity	+	0.6375	63.75%
skin sensitisation	+	0.6001	60.01%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	+	0.5668	56.68%
Acute Oral Toxicity (c)	III	0.7812	78.12%
Estrogen receptor binding	+	0.5593	55.93%
Androgen receptor binding	+	0.5547	55.47%
Thyroid receptor binding	-	0.5853	58.53%
Glucocorticoid receptor binding	+	0.8022	80.22%
Aromatase binding	+	0.6380	63.80%
PPAR gamma	+	0.8189	81.89%
Honey bee toxicity	-	0.9113	91.13%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.7700	77.00%
Fish aquatic toxicity	+	0.9940	99.40%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
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
CHEMBL1075189	P14618	Pyruvate kinase isozymes M1/M2	500 nM	IC50	via Super-PRED

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

• Alkanna cappadocica
• Alkanna tinctoria
• Arnebia decumbens
• Arnebia euchroma
• Arnebia guttata
• Arnebia hispidissima
• Echium plantagineum
• Echium rubrum
• Lithospermum erythrorhizon
• Lithospermum officinale

Cross-Links

• PubChem: 5208
• NPASS: NPC242358
• LOTUS: LTS0253004
• wikiData: Q105198603