Artocarpin

Details

• Internal ID: fdfb1ec8-9885-401b-a808-0dbe37856223
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavones > 3-prenylated flavones
• IUPAC Name: 2-(2,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-6-[(E)-3-methylbut-1-enyl]-3-(3-methylbut-2-enyl)chromen-4-one
• SMILES (Canonical): CC(C)C=CC1=C(C=C2C(=C1O)C(=O)C(=C(O2)C3=C(C=C(C=C3)O)O)CC=C(C)C)OC
• SMILES (Isomeric): CC(C)/C=C/C1=C(C=C2C(=C1O)C(=O)C(=C(O2)C3=C(C=C(C=C3)O)O)CC=C(C)C)OC
• InChI: InChI=1S/C26H28O6/c1-14(2)6-9-18-21(31-5)13-22-23(24(18)29)25(30)19(10-7-15(3)4)26(32-22)17-11-8-16(27)12-20(17)28/h6-9,11-14,27-29H,10H2,1-5H3/b9-6+
• InChI Key: KRGDFVQWQJIMEK-RMKNXTFCSA-N
• Popularity: 53 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₂₈O₆
• Molecular Weight: 436.50 g/mol
• Exact Mass: 436.18858861 g/mol
• Topological Polar Surface Area (TPSA): 96.20 Ų
• XlogP: 5.70
• Atomic LogP (AlogP): 5.76
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 6

Synonyms

• 7608-44-8
• NSC241010
• CHEMBL72617
• 2-(2,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-6-[(E)-3-methylbut-1-enyl]-3-(3-methylbut-2-enyl)chromen-4-one
• CHEBI:65439
• Artocarpin Lectin
• 2-(2,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-6-[(1E)-3-methylbut-1-en-1-yl]-3-(3-methylbut-2-en-1-yl)-4H-chromen-4-one
• Artocaprin
• SCHEMBL374230
• BDBM50051348
• AKOS040760278
• NSC-241010
• Q27133884
• 2-(2,4-Dihydroxy-phenyl)-5-hydroxy-7-methoxy-6-((E)-3-methyl-but-1-enyl)-3-(3-methyl-but-2-enyl)-chromen-4-one
• 2-(2,4-Dihydroxyphenyl)-5-hydroxy-7-methoxy-6-(3-methyl-1-butenyl)-3-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one, 9CI
• 2-(2,4-Dihydroxyphenyl)-5-hydroxy-7-methoxy-6-(3-methyl-1-butenyl)-3-(3-methyl-2-butenyl)-4H-chromen-4-one
• 5-hydroxy-7-methoxy-3-(3-methyl-2-butenyl)-6-(3-methyl-1-butenyl)-2-(2,4-dihydroxyphenyl)-4H-1-benzopyran-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9881	98.81%
Caco-2	+	0.4911	49.11%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7207	72.07%
OATP2B1 inhibitior	-	0.5693	56.93%
OATP1B1 inhibitior	+	0.7815	78.15%
OATP1B3 inhibitior	+	0.8347	83.47%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9085	90.85%
P-glycoprotein inhibitior	+	0.8517	85.17%
P-glycoprotein substrate	+	0.6409	64.09%
CYP3A4 substrate	+	0.6182	61.82%
CYP2C9 substrate	-	0.5773	57.73%
CYP2D6 substrate	-	0.8161	81.61%
CYP3A4 inhibition	-	0.5253	52.53%
CYP2C9 inhibition	+	0.8720	87.20%
CYP2C19 inhibition	+	0.9528	95.28%
CYP2D6 inhibition	-	0.5522	55.22%
CYP1A2 inhibition	+	0.8834	88.34%
CYP2C8 inhibition	+	0.7135	71.35%
CYP inhibitory promiscuity	+	0.9669	96.69%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6401	64.01%
Eye corrosion	-	0.9883	98.83%
Eye irritation	-	0.6400	64.00%
Skin irritation	-	0.7643	76.43%
Skin corrosion	-	0.9555	95.55%
Ames mutagenesis	+	0.5563	55.63%
Human Ether-a-go-go-Related Gene inhibition	-	0.6107	61.07%
Micronuclear	+	0.5500	55.00%
Hepatotoxicity	-	0.5000	50.00%
skin sensitisation	-	0.8395	83.95%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.8817	88.17%
Acute Oral Toxicity (c)	III	0.7260	72.60%
Estrogen receptor binding	+	0.8966	89.66%
Androgen receptor binding	+	0.8798	87.98%
Thyroid receptor binding	+	0.6050	60.50%
Glucocorticoid receptor binding	+	0.8584	85.84%
Aromatase binding	+	0.5566	55.66%
PPAR gamma	+	0.8468	84.68%
Honey bee toxicity	-	0.6993	69.93%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9894	98.94%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL256	P0DMS8	Adenosine A3 receptor	4590 nM	Ki	PMID: 8691424

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.23%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.83%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	93.47%	94.73%
CHEMBL1951	P21397	Monoamine oxidase A	93.40%	91.49%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.03%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.90%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.62%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.26%	95.56%
CHEMBL3194	P02766	Transthyretin	92.24%	90.71%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.70%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.17%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.33%	99.17%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.33%	99.15%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	88.46%	89.62%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	87.13%	90.71%
CHEMBL1937	Q92769	Histone deacetylase 2	86.75%	94.75%
CHEMBL2413	P32246	C-C chemokine receptor type 1	84.60%	89.50%
CHEMBL2535	P11166	Glucose transporter	83.64%	98.75%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.61%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.31%	96.09%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	80.98%	95.64%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	80.60%	83.10%

Plants that contains it

• Artocarpus altilis
• Artocarpus gomezianus
• Artocarpus heterophyllus
• Broussonetia papyrifera

Cross-Links

• PubChem: 5458461
• NPASS: NPC282300
• ChEMBL: CHEMBL72617
• LOTUS: LTS0018720
• wikiData: Q27133884