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Cycloartocarpesin

Family: Plantae - Moraceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Pyranoflavonoid

Canonical Smiles	Oc1ccc(c(c1)O)c1cc(=O)c2c(o1)cc1c(c2O)C=CC(O1)(C)C
InChI	InChI=1S/C20H16O6/c1-20(2)6-5-12-16(26-20)9-17-18(19(12)24)14(23)8-15(25-17)11-4-3-10(21)7-13(11)22/h3-9,21-22,24H,1-2H3
InChIKey	LXEJWVDCRDILQQ-UHFFFAOYSA-N
Formula	C₂₀H₁₆O₆
HBA	6
HBD	3
MW	352.34
Rotatable Bonds	1
TPSA	100.13
LogP	3.76
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	26
Formal Charge	0
Fraction CSP3	0.15
Exact Mass	352.09
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: 15224382

Cas: 23806-61-3

Zinc: ZINC000013414436

Chebi: 175502

Nmrshiftdb2: 60029420

Chembl: CHEMBL221908

Bindingdb: 50193721

No compound-protein relationship available.

SMILES: O1CC=Cc(c2)c1cc(c23)oc(cc3=O)-c4ccccc4

Level: 1

Mol. Weight: 352.34 g/mol

SMILES: O=c1ccoc(c12)cc3c(c2)C=CCO3

Level: 0

Mol. Weight: 352.34 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 352.34 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.95
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.950
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -0.01

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.000
Plasma Protein Binding: 76.03
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: 4.750
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.850
Biodegradation: Safe
Carcinogenesis: Toxic
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.660
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.310
Micronucleos: Toxic
NR-AhR: Toxic
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Toxic
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: 1.090
Rat (Acute): 2.510
Rat (Chronic Oral): 2.620
Fathead Minnow: 4.710
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Toxic
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 503.640
Hydration Free Energy: -11.770
Log(D) at pH=7.4: 4.350
Log(P): 4.41
Log S: -5.81
Log(Vapor Pressure): -9.5
Melting Point: 282.95
pKa Acid: 6.67
pKa Basic: 5.19

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	0.9549
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9477
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.9359
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.9184
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.8911
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.8893
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8790
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8685
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8656
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8596
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8535
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8533
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8325
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8275
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8226
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8224
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8181
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial	Q15119	PDK2_HUMAN	Homo sapiens	3	0.8091
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase	Q46381	BPHB_COMTE	Comamonas testosteroni	3	0.8056
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.8050
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.8019
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.8013
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.7913
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.7906
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7887
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7867
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7866
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7852
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7844
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7810
Isoleucine--tRNA ligase	P56690	SYI_THET8	Thermus thermophilus	3	0.7799
F420-dependent NADP reductase	O29370	FNO_ARCFU	Archaeoglobus fulgidus	4	0.7772
IOMT 3	Q06YR3	Q06YR3_MEDTR	Medicago truncatula	4	0.7769
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.7766
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7756
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7746
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7732
4,4'-diapophytoene synthase	A9JQL9	CRTM_STAAU	Staphylococcus aureus	3	0.7701
Nucleoside diphosphate kinase	P15266	NDK_MYXXA	Myxococcus xanthus	3	0.7645
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7620
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7613
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	4	0.7544
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7483
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7464
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7462
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.7455
Biotin carboxylase	P24182	ACCC_ECOLI	Escherichia coli	4	0.7441
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.7418
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7387
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7372
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7371
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.7358
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.7317
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7288
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7255
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.7249
Sulfotransferase 1E1	P49888	ST1E1_HUMAN	Homo sapiens	3	0.7238
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7226
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7214
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	4	0.7187
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7166
Beta-2-microglobulin	P61769	B2MG_HUMAN	Homo sapiens	3	0.7115
Peripheral plasma membrane protein CASK	O14936	CSKP_HUMAN	Homo sapiens	3	0.7087
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7079
Dihydroflavonol 4-reductase	P51110	DFRA_VITVI	Vitis vinifera	3	0.7074
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7069
Renin	P00797	RENI_HUMAN	Homo sapiens	3	0.7054
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7037
Glycylpeptide N-tetradecanoyltransferase	A5K1A2	A5K1A2_PLAVS	Plasmodium vivax	3	0.7028
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7014
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	4	0.7001

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