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Artocarpesin

Family: Plantae - Moraceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Prenylated Flavone

Canonical Smiles	CC(=CCc1c(O)cc2c(c1O)c(=O)cc(o2)c1ccc(cc1O)O)C
InChI	InChI=1S/C20H18O6/c1-10(2)3-5-13-15(23)8-18-19(20(13)25)16(24)9-17(26-18)12-6-4-11(21)7-14(12)22/h3-4,6-9,21-23,25H,5H2,1-2H3
InChIKey	YWUVFGZTDLJVCR-UHFFFAOYSA-N
Formula	C₂₀H₁₈O₆
HBA	6
HBD	4
MW	354.36
Rotatable Bonds	3
TPSA	111.13
LogP	3.79
Number Rings	3
Number Aromatic Rings	3
Heavy Atom Count	26
Formal Charge	0
Fraction CSP3	0.15
Exact Mass	354.11
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Morus mesozygia	Moraceae	Plantae	3054370

Showing of synonyms

Fozing CDA (2009). Prenylated arylbenzofuran derivatives from Morus mesozygia with antioxidant activity.. Phytochemistry,2009, 70(2), 216-221. [View] [PubMed]

Pubchem: 399491

Cas: 3162-09-2

Zinc: ZINC000001658458

Chebi: 175537

Nmrshiftdb2: 60025907

Chembl: CHEMBL1915458

Comptox: DTXSID30327994

Bindingdb: 50358100

No compound-protein relationship available.

SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3

Level: 1

Mol. Weight: 354.36 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 354.36 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 354.36 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.44
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -5.01
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -0.23

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.94
Plasma Protein Binding: 85.05
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Inhibitor
CYP 2C9 Substrate: Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 4.81
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.6
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.51
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.08
Micronucleos: Toxic
NR-AhR: Toxic
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Toxic
NR-ER: Toxic
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: 1.74
Rat (Acute): 2.36
Rat (Chronic Oral): 3.04
Fathead Minnow: 4.79
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 508.04
Hydration Free Energy: -11.88
Log(D) at pH=7.4: 3.65
Log(P): 5.01
Log S: -5.81
Log(Vapor Pressure): -9.16
Melting Point: 242.15
pKa Acid: 6.03
pKa Basic: 6.99

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.9555
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9451
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.9366
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.9208
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.9106
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.9083
IOMT 3	Q06YR3	Q06YR3_MEDTR	Medicago truncatula	4	0.9013
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	4	0.8965
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8941
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8905
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8869
Biotin carboxylase	P24182	ACCC_ECOLI	Escherichia coli	4	0.8808
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	4	0.8776
4,4'-diapophytoene synthase	A9JQL9	CRTM_STAAU	Staphylococcus aureus	3	0.8775
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.8767
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8730
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	3	0.8690
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8668
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8644
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.8632
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8592
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8552
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8552
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.8530
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	4	0.8517
Nucleoside diphosphate kinase A 2	P52175	NDKA2_BOVIN	Bos taurus	4	0.8457
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.8450
17beta-hydroxysteroid dehydrogenase	O93874	O93874_COCLU	Cochliobolus lunatus	4	0.8386
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.8354
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8330
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8306
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial	Q15119	PDK2_HUMAN	Homo sapiens	3	0.8234
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.8233
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8231
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8229
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	4	0.8196
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8180
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8156
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.8133
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase	Q46381	BPHB_COMTE	Comamonas testosteroni	3	0.8125
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.8058
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8039
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.8023
Histamine N-methyltransferase	P50135	HNMT_HUMAN	Homo sapiens	4	0.7995
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.7987
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7975
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7915
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.7913
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7905
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7885
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7860
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	4	0.7853
Chalcone synthase 2	P30074	CHS2_MEDSA	Medicago sativa	5	0.7849
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	4	0.7835
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7818
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7818
Isoleucine--tRNA ligase	P56690	SYI_THET8	Thermus thermophilus	3	0.7789
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7778
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7775
F420-dependent NADP reductase	O29370	FNO_ARCFU	Archaeoglobus fulgidus	4	0.7770
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7762
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	4	0.7756
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7754
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.7747
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.7702
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.7697
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7689
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7676
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.7670
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	3	0.7626
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7620
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	3	0.7620
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7600
Tau-tubulin kinase 1	Q5TCY1	TTBK1_HUMAN	Homo sapiens	4	0.7595
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7592
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7557
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	4	0.7554
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7542
Nucleoside diphosphate kinase	P15266	NDK_MYXXA	Myxococcus xanthus	3	0.7523
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7505
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.7497
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.7494
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7493
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7489
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	4	0.7481
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7462
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7461
Cyclic dipeptide N-prenyltransferase	D1D8L6	D1D8L6_ASPFM	Neosartorya fumigata	3	0.7456
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7453
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7447
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	3	0.7397
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7392
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7390
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	3	0.7381
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7377
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.7372
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7353
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7347
17beta-hydroxysteroid dehydrogenase	O93874	O93874_COCLU	Cochliobolus lunatus	4	0.7326
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7326
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7319
17beta-hydroxysteroid dehydrogenase	O93874	O93874_COCLU	Cochliobolus lunatus	3	0.7307
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7297
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.7284
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7270
Pteridine reductase, putative	Q581W1	Q581W1_TRYB2	Trypanosoma brucei brucei	4	0.7247
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7244
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.7239
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7237
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7236
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	3	0.7213
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7208
Dihydroflavonol 4-reductase	P51110	DFRA_VITVI	Vitis vinifera	3	0.7206
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.7202
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7202
Phosphodiesterase	Q8WQX9	Q8WQX9_9TRYP	Trypanosoma brucei	3	0.7201
Renin	P00797	RENI_HUMAN	Homo sapiens	3	0.7193
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	4	0.7191
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7177
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	5	0.7176
Genome polyprotein	Q2YHF0	POLG_DEN4T	Dengue virus type 4	3	0.7160
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.7142
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7132
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7132
Camphor 5-monooxygenase	P00183	CPXA_PSEPU	Pseudomonas putida	4	0.7120
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7119
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	2	0.7115
Dihydroflavonol 4-reductase	P51110	DFRA_VITVI	Vitis vinifera	3	0.7061
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.7061
Biphenyl-2,3-diol 1,2-dioxygenase	P17297	BPHC_PSES1	Pseudomonas sp	3	0.7060
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.7059
Cytochrome P450 1A1	P04798	CP1A1_HUMAN	Homo sapiens	3	0.7057
Cyclic AMP receptor protein	Q5SID7	CRP_THET8	Thermus thermophilus	3	0.7047
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7040
Avidin	P02701	AVID_CHICK	Gallus gallus	3	0.7034
Glycylpeptide N-tetradecanoyltransferase	A5K1A2	A5K1A2_PLAVS	Plasmodium vivax	3	0.7022
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7019
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7016

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