5,6,8-trihydroxy-7-(5-methylhex-4-en-2-yl)naphthalene-1,4-dione

Details

• Internal ID: 34efd951-491f-4158-aa44-0b7c1552e23f
• Taxonomy: Benzenoids > Naphthalenes > Naphthoquinones
• IUPAC Name: 5,6,8-trihydroxy-7-(5-methylhex-4-en-2-yl)naphthalene-1,4-dione
• SMILES (Canonical): CC(CC=C(C)C)C1=C(C2=C(C(=O)C=CC2=O)C(=C1O)O)O
• SMILES (Isomeric): CC(CC=C(C)C)C1=C(C2=C(C(=O)C=CC2=O)C(=C1O)O)O
• InChI: InChI=1S/C17H18O5/c1-8(2)4-5-9(3)12-15(20)13-10(18)6-7-11(19)14(13)17(22)16(12)21/h4,6-7,9,20-22H,5H2,1-3H3
• InChI Key: IHBGVXPGDZCHRJ-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₈O₅
• Molecular Weight: 302.32 g/mol
• Exact Mass: 302.11542367 g/mol
• Topological Polar Surface Area (TPSA): 94.80 Ų
• XlogP: 4.00
• Atomic LogP (AlogP): 3.20
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9823	98.23%
Caco-2	+	0.8059	80.59%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.5980	59.80%
OATP2B1 inhibitior	-	0.7132	71.32%
OATP1B1 inhibitior	+	0.8741	87.41%
OATP1B3 inhibitior	+	0.9277	92.77%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.6882	68.82%
P-glycoprotein inhibitior	-	0.8129	81.29%
P-glycoprotein substrate	-	0.9333	93.33%
CYP3A4 substrate	-	0.5966	59.66%
CYP2C9 substrate	-	0.8004	80.04%
CYP2D6 substrate	-	0.8599	85.99%
CYP3A4 inhibition	-	0.7568	75.68%
CYP2C9 inhibition	+	0.7965	79.65%
CYP2C19 inhibition	-	0.5000	50.00%
CYP2D6 inhibition	-	0.5634	56.34%
CYP1A2 inhibition	+	0.8543	85.43%
CYP2C8 inhibition	-	0.9818	98.18%
CYP inhibitory promiscuity	+	0.7067	70.67%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9411	94.11%
Carcinogenicity (trinary)	Non-required	0.6583	65.83%
Eye corrosion	-	0.9899	98.99%
Eye irritation	-	0.6529	65.29%
Skin irritation	-	0.6502	65.02%
Skin corrosion	-	0.8611	86.11%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4652	46.52%
Micronuclear	-	0.5600	56.00%
Hepatotoxicity	+	0.6448	64.48%
skin sensitisation	-	0.5291	52.91%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	-	0.6510	65.10%
Acute Oral Toxicity (c)	III	0.6049	60.49%
Estrogen receptor binding	-	0.4933	49.33%
Androgen receptor binding	-	0.5807	58.07%
Thyroid receptor binding	-	0.7479	74.79%
Glucocorticoid receptor binding	+	0.6201	62.01%
Aromatase binding	-	0.5969	59.69%
PPAR gamma	+	0.6344	63.44%
Honey bee toxicity	-	0.9498	94.98%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.8100	81.00%
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
CHEMBL2581	P07339	Cathepsin D	97.08%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.02%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.38%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.04%	95.56%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	87.17%	89.34%
CHEMBL3401	O75469	Pregnane X receptor	85.74%	94.73%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.10%	90.71%
CHEMBL4208	P20618	Proteasome component C5	83.50%	90.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.65%	85.14%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	80.37%	83.10%
CHEMBL1937	Q92769	Histone deacetylase 2	80.03%	94.75%

Plants that contains it

• Lithospermum erythrorhizon

Cross-Links

• PubChem: 5321285
• NPASS: NPC35351