Dmask

Details

• Internal ID: 3402c0a7-6376-4b5c-92fc-bbc38b2a4243
• Taxonomy: Benzenoids > Naphthalenes > Naphthoquinones
• IUPAC Name: [1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] 3-methylbut-2-enoate
• SMILES (Canonical): CC(=CCC(C1=CC(=O)C2=C(C=CC(=C2C1=O)O)O)OC(=O)C=C(C)C)C
• SMILES (Isomeric): CC(=CCC(C1=CC(=O)C2=C(C=CC(=C2C1=O)O)O)OC(=O)C=C(C)C)C
• InChI: InChI=1S/C21H22O6/c1-11(2)5-8-17(27-18(25)9-12(3)4)13-10-16(24)19-14(22)6-7-15(23)20(19)21(13)26/h5-7,9-10,17,22-23H,8H2,1-4H3
• InChI Key: BATBOVZTQBLKIL-UHFFFAOYSA-N
• Popularity: 25 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₂O₆
• Molecular Weight: 370.40 g/mol
• Exact Mass: 370.14163842 g/mol
• Topological Polar Surface Area (TPSA): 101.00 Ų
• XlogP: 5.00
• Atomic LogP (AlogP): 3.64
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

• Arnebin 1
• (Rac)-Arnebin 1
• Isoarnebin I
• NSC140377
• [1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] 3-methylbut-2-enoate
• 34539-65-6
• 5162-01-6
• (beta,beta-Dimethylacryl)shikonin
• Arnebin
• Arnebin I
• 2-Butenoic acid, 3-methyl-, 1-(1,4-dihydro-5,8-dihydroxy-1,4-dioxo-2-naphthalenyl)-4-methyl-3-pentenyl ester, (+)-
• Alkanin b,b-dimethylacrylate
• Alkanin,.beta.-dimethylacrylate
• SCHEMBL4279672
• CHEMBL2002642
• DTXSID10947396
• 2-Butenoic acid, 3-methyl-, (1R)-1-(1,4-dihydro-5,8-dihydroxy-1,4-dioxo-2-naphthalenyl)-4-methyl-3-pentenyl ester
• 2-Butenoic acid, 3-methyl-, 1-(1,4-dihydro-5,8-dihydroxy-1,4-dioxo-2-naphthalenyl)-4-methyl-3-pentenyl ester, (R)-
• BCP15526
• BCP31231
• HY-N5112
• .beta.,.beta.-Dimethylacrylshikonin
• AKOS037515608
• NSC-140377
• (c)micro,(c)micro-Dimethylacrylalkannin
• Shikonin .beta.,.beta.-dimethylacrylate
• LS-47172
• NCI60_000890
• CS-0032426
• D2118
• FT-0774263
• A874947
• Dimethylacrylshikonin;(Beta,beta-dimethylacryl)shikonin
• 1-(5,8-Dihydroxy-1,4-dioxo-1,4-dihydro-2-naphthalenyl)-4-methyl-3-pentenyl 3-methyl-2-butenoate #
• 1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl 3-methylbut-2-enoate
• 2-Butenoic acid, 1-(5,8-dihydro- 1,4-dihydroxy-5,8-dioxo-2-naphthalenyl)-4-methyl-3-pentenyl ester
• 2-Butenoic acid, 3-methyl-, 1-(1,4-dihydro-5,8-dihydroxy-1,4-dioxo-2-naphthalenyl)-4-methyl-3-pentenyl ester
• 23444-70-4
• 5,8-Dihydroxy-2-[1-(beta,beta-dimethylacryloyloxy)-4-methyl-3-pentenyl]-1,4-naphthalenedione
• Crotonic acid, 3-methyl-, ester with 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-1,4-naphthoquinone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9964	99.64%
Caco-2	+	0.5081	50.81%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.8530	85.30%
OATP2B1 inhibitior	-	0.7194	71.94%
OATP1B1 inhibitior	+	0.9318	93.18%
OATP1B3 inhibitior	+	0.8274	82.74%
MATE1 inhibitior	-	0.7000	70.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.6817	68.17%
P-glycoprotein inhibitior	-	0.6208	62.08%
P-glycoprotein substrate	-	0.8487	84.87%
CYP3A4 substrate	+	0.5255	52.55%
CYP2C9 substrate	-	0.7821	78.21%
CYP2D6 substrate	-	0.8836	88.36%
CYP3A4 inhibition	-	0.8636	86.36%
CYP2C9 inhibition	+	0.7122	71.22%
CYP2C19 inhibition	+	0.6642	66.42%
CYP2D6 inhibition	-	0.6033	60.33%
CYP1A2 inhibition	+	0.6975	69.75%
CYP2C8 inhibition	-	0.7792	77.92%
CYP inhibitory promiscuity	+	0.6420	64.20%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8733	87.33%
Carcinogenicity (trinary)	Non-required	0.6414	64.14%
Eye corrosion	-	0.9924	99.24%
Eye irritation	-	0.6144	61.44%
Skin irritation	-	0.7485	74.85%
Skin corrosion	-	0.9662	96.62%
Ames mutagenesis	+	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7148	71.48%
Micronuclear	+	0.5059	50.59%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.5755	57.55%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	+	0.6635	66.35%
Acute Oral Toxicity (c)	III	0.6456	64.56%
Estrogen receptor binding	+	0.6701	67.01%
Androgen receptor binding	+	0.6583	65.83%
Thyroid receptor binding	-	0.5515	55.15%
Glucocorticoid receptor binding	+	0.6954	69.54%
Aromatase binding	-	0.6526	65.26%
PPAR gamma	+	0.6937	69.37%
Honey bee toxicity	-	0.8648	86.48%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.31%	94.45%
CHEMBL2581	P07339	Cathepsin D	97.23%	98.95%
CHEMBL4040	P28482	MAP kinase ERK2	97.07%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.73%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.95%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	88.47%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.72%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.34%	99.15%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.90%	96.00%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	82.28%	85.30%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.56%	86.92%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	80.19%	96.67%

Plants that contains it

• Alkanna cappadocica
• Alkanna hirsutissima
• Alkanna tinctoria
• Arnebia euchroma
• Arnebia guttata
• Arnebia hispidissima
• Arnebia speciosa
• Jatropha glandulifera
• Lithospermum erythrorhizon

Cross-Links

• PubChem: 32465
• NPASS: NPC29649
• LOTUS: LTS0157046
• wikiData: Q104252786