5-Hydroxylapachol

Details

• Internal ID: 60442756-2fcc-4251-ae74-66631964971f
• Taxonomy: Benzenoids > Naphthalenes > Naphthoquinones
• IUPAC Name: 4,5-dihydroxy-3-(3-methylbut-2-enyl)naphthalene-1,2-dione
• SMILES (Canonical): CC(=CCC1=C(C2=C(C=CC=C2O)C(=O)C1=O)O)C
• SMILES (Isomeric): CC(=CCC1=C(C2=C(C=CC=C2O)C(=O)C1=O)O)C
• InChI: InChI=1S/C15H14O4/c1-8(2)6-7-10-13(17)12-9(14(18)15(10)19)4-3-5-11(12)16/h3-6,16-17H,7H2,1-2H3
• InChI Key: ZDNKGOAYDCAKCR-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₄O₄
• Molecular Weight: 258.27 g/mol
• Exact Mass: 258.08920892 g/mol
• Topological Polar Surface Area (TPSA): 74.60 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 2.78
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• Hydroxylapachol
• CHEMBL1089642
• 4,5-dihydroxy-3-(3-methylbut-2-enyl)naphthalene-1,2-dione

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9943	99.43%
Caco-2	+	0.7756	77.56%
Blood Brain Barrier	+	0.5121	51.21%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6527	65.27%
OATP2B1 inhibitior	-	0.7144	71.44%
OATP1B1 inhibitior	+	0.9209	92.09%
OATP1B3 inhibitior	+	0.9225	92.25%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8588	85.88%
BSEP inhibitior	-	0.8425	84.25%
P-glycoprotein inhibitior	-	0.8970	89.70%
P-glycoprotein substrate	-	0.8449	84.49%
CYP3A4 substrate	-	0.5470	54.70%
CYP2C9 substrate	-	0.8037	80.37%
CYP2D6 substrate	-	0.8510	85.10%
CYP3A4 inhibition	-	0.7681	76.81%
CYP2C9 inhibition	+	0.9365	93.65%
CYP2C19 inhibition	+	0.6413	64.13%
CYP2D6 inhibition	-	0.5415	54.15%
CYP1A2 inhibition	+	0.8784	87.84%
CYP2C8 inhibition	-	0.9066	90.66%
CYP inhibitory promiscuity	+	0.8149	81.49%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9328	93.28%
Carcinogenicity (trinary)	Non-required	0.7049	70.49%
Eye corrosion	-	0.9855	98.55%
Eye irritation	+	0.9637	96.37%
Skin irritation	-	0.5960	59.60%
Skin corrosion	-	0.8313	83.13%
Ames mutagenesis	+	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8255	82.55%
Micronuclear	+	0.5100	51.00%
Hepatotoxicity	+	0.7000	70.00%
skin sensitisation	+	0.6076	60.76%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	+	0.8273	82.73%
Acute Oral Toxicity (c)	III	0.6663	66.63%
Estrogen receptor binding	+	0.8213	82.13%
Androgen receptor binding	+	0.5498	54.98%
Thyroid receptor binding	-	0.6111	61.11%
Glucocorticoid receptor binding	+	0.8817	88.17%
Aromatase binding	-	0.6569	65.69%
PPAR gamma	+	0.7646	76.46%
Honey bee toxicity	-	0.9146	91.46%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9968	99.68%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.80%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	95.25%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.27%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.23%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	92.24%	94.73%
CHEMBL1937	Q92769	Histone deacetylase 2	89.22%	94.75%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.61%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.69%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.29%	96.09%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	81.00%	93.03%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	80.84%	82.69%

Plants that contains it

• Tectona grandis

Cross-Links

• PubChem: 5318245
• NPASS: NPC131592
• LOTUS: LTS0148666
• wikiData: Q105372431