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4-methoxylonchocarpin

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

Canonical Smiles	COc1ccc(cc1)/C=C/C(=O)c1ccc2c(c1O)C=CC(O2)(C)C
InChI	InChI=1S/C21H20O4/c1-21(2)13-12-17-19(25-21)11-9-16(20(17)23)18(22)10-6-14-4-7-15(24-3)8-5-14/h4-13,23H,1-3H3/b10-6+
InChIKey	XEVCTBKORYCFCZ-UXBLZVDNSA-N
Formula	C₂₁H₂₀O₄
HBA	4
HBD	1
MW	336.39
Rotatable Bonds	4
TPSA	55.76
LogP	4.48
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	25
Formal Charge	0
Fraction CSP3	0.19
Exact Mass	336.14
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Dorstenia mannii	Moraceae	Plantae	194258
2	Dorstenia poinsettiifolia	Moraceae	Plantae	2605000

Showing of synonyms

Ngadjui BT, Kapche GW, et al. (1999). Prenylated flavonoids and a dihydro-4-phenylcoumarinfrom Dorstenia poinsettifolia. Phytochemistry, 1999, 51(1), 119-123. [View]
Ngadjui BT, Kouam SF, et al. (2000). Prenylated flavonoids from the aerial parts of Dorstenia mannii.. Phytochemistry,2000, 55(8), 915-919. [View] [PubMed]

Pubchem: 10472189

Cas: 51589-67-4

Zinc: ZINC000014557839

Chebi: 180251

Nmrshiftdb2: 70009519

Chembl: CHEMBL369768

Bindingdb: 50505207

No compound-protein relationship available.

SMILES: C1=CCOc(c12)ccc(c2)C(=O)C=Cc3ccccc3

Level: 1

Mol. Weight: 336.39 g/mol

SMILES: C1=CCOc(c12)cccc2

Level: 0

Mol. Weight: 336.39 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 336.39 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.76
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.460
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.01

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.150
Plasma Protein Binding: 56.52
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 4.330
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.690
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.090
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.450
Micronucleos: Toxic
NR-AhR: Toxic
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Toxic
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: 3.030
Rat (Acute): 2.370
Rat (Chronic Oral): 2.510
Fathead Minnow: 5.010
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: 430.720
Hydration Free Energy: -8.720
Log(D) at pH=7.4: 4.740
Log(P): 5.28
Log S: -6.57
Log(Vapor Pressure): -7.32
Melting Point: 138.32
pKa Acid: 8.82
pKa Basic: 5.21

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.9468
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.9329
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.9022
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.9008
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8969
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.8667
Purine nucleoside phosphorylase	Q8I3X4	Q8I3X4_PLAF7	Plasmodium falciparum	3	0.8495
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	2	0.8462
HTH-type transcriptional regulator EthR	P9WMC1	ETHR_MYCTU	Mycobacterium tuberculosis	4	0.8408
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.8384
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8294
Matrilysin	P09237	MMP7_HUMAN	Homo sapiens	3	0.8221
Cholesterol side-chain cleavage enzyme, mitochondrial	P05108	CP11A_HUMAN	Homo sapiens	3	0.8203
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.8203
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8197
Beta-elicitin cinnamomin	P15569	ELIB_PHYCI	Phytophthora cinnamomi	3	0.8179
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.8135
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7981
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7921
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7915
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7900
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7879
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7876
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7836
Isoliquiritigenin 2'-O-methyltransferase	P93324	CHOMT_MEDSA	Medicago sativa	3	0.7832
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7816
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7813
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.7806
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.7786
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7781
Class B acid phosphatase	Q540U1	APHA_SALTM	Salmonella typhimurium	2	0.7774
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7764
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7762
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7751
Decaprenylphosphoryl-beta-D-ribose oxidase	I6X8C4	I6X8C4_MYCTU	Mycobacterium tuberculosis	3	0.7738
Cyclic dipeptide N-prenyltransferase	D1D8L6	D1D8L6_ASPFM	Neosartorya fumigata	2	0.7737
Histone deacetylase 8	Q9BY41	HDAC8_HUMAN	Homo sapiens	3	0.7713
Protein BRASSINOSTEROID INSENSITIVE 1	O22476	BRI1_ARATH	Arabidopsis thaliana	3	0.7708
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7697
Methionine aminopeptidase 2	P50579	MAP2_HUMAN	Homo sapiens	3	0.7696
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7685
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7675
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7671
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.7660
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7646
Nicotinamide phosphoribosyltransferase	P43490	NAMPT_HUMAN	Homo sapiens	3	0.7633
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7632
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7627
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7619
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7614
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7604
Protein BRASSINOSTEROID INSENSITIVE 1	O22476	BRI1_ARATH	Arabidopsis thaliana	3	0.7603
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7590
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7566
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7566
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7562
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7547
Ephrin type-A receptor 2	P29317	EPHA2_HUMAN	Homo sapiens	3	0.7538
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7537
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7535
Lanosterol 14-alpha-demethylase	Q385E8	Q385E8_TRYB2	Trypanosoma brucei brucei	3	0.7532
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.7530
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7527
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	2	0.7523
L-lactate dehydrogenase A chain	P13491	LDHA_RABIT	Oryctolagus cuniculus	2	0.7490
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	4	0.7484
Protein RecA	Q59560	RECA_MYCS2	Mycolicibacterium smegmatis155)	3	0.7471
Purine nucleoside phosphorylase DeoD-type	Q5EEL8	DEOD_BACCE	Bacillus cereus	3	0.7465
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7455
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7445
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7439
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7429
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	2	0.7428
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7425
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7421
Purine nucleoside phosphorylase DeoD-type	O34925	DEOD_BACSU	Bacillus subtilis	3	0.7419
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7418
Purine nucleoside phosphorylase DeoD-type	Q5EEL8	DEOD_BACCE	Bacillus cereus	3	0.7414
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7394
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7390
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7380
histone deacetylase	A5H660	A5H660_SCHMA	Schistosoma mansoni	3	0.7379
prolyl oligopeptidase	Q9X6R4	Q9X6R4_AERCA	Aeromonas caviae	3	0.7375
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7373
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7372
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7366
Protein BRASSINOSTEROID INSENSITIVE 1	O22476	BRI1_ARATH	Arabidopsis thaliana	3	0.7363
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7362
Methionine aminopeptidase 2	P9WK19	MAP12_MYCTU	Mycobacterium tuberculosis	3	0.7360
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7351
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7336
Caspase-3	P42574	CASP3_HUMAN	Homo sapiens	2	0.7330
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	2	0.7316
Acetylcholine-binding protein	P58154	ACHP_LYMST	Lymnaea stagnalis	3	0.7315
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	2	0.7312
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7295
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial	Q15119	PDK2_HUMAN	Homo sapiens	3	0.7292
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7283
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4	Q9Y3Q4	HCN4_HUMAN	Homo sapiens	3	0.7281
FMN-dependent NAD(P)H:quinone oxidoreductase 1	Q9I5F3	AZOR1_PSEAE	Pseudomonas aeruginosa	2	0.7274
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.7265
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7253
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7248
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	2	0.7237
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7236
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7236
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7235
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7235
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.7223
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7216
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	2	0.7196
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.7184
Single-stranded-DNA-specific exonuclease RecJ	D0EM60	D0EM60_DEIRD	Deinococcus radiodurans	2	0.7184
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7181
Phytohormone-binding protein CSBP	A0A1S3THR8	PHBP_VIGRR	Vigna radiata var. radiata	2	0.7181
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7179
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase	O67060	ISPE_AQUAE	Aquifex aeolicus	3	0.7176
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	2	0.7171
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7159
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	2	0.7157
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7155
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7141
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.7139
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7137
Phosphodiesterase	Q8WQX9	Q8WQX9_9TRYP	Trypanosoma brucei	3	0.7111
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7110
Caffeoyl-CoA O-methyltransferase	Q40313	CAMT_MEDSA	Medicago sativa	3	0.7098
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	3	0.7097
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7089
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.7083
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7081
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7081
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial	Q15119	PDK2_HUMAN	Homo sapiens	3	0.7080
L-seryl-tRNA(Sec) kinase	Q58933	PSTK_METJA	Methanocaldococcus jannaschii	2	0.7077
F420-dependent methylenetetrahydromethanopterin dehydrogenase	P94951	MTD_METKA	Methanopyrus kandleri	2	0.7076
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7059
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	2	0.7059
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7053
Abscisic acid receptor PYR1	O49686	PYR1_ARATH	Arabidopsis thaliana	3	0.7049
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.7043
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.7043
Ribonuclease TTHA0252	Q5SLP1	RNSE_THET8	Thermus thermophilus	3	0.7031
5-methylthioadenosine/S-adenosylhomocysteine deaminase	Q7NZ90	Q7NZ90_CHRVO	Chromobacterium violaceum	2	0.7023
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7014
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7012
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7011

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