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5-[(1E)-2-(4-beta-D-galactopyranosyloxyphenyl) ethenyl]-4, 7-dimethoxy-3-2H-1-benzopyran-2-one

Family: Plantae - Dipterocarpaceae
Kingdom: Plantae
Class: Coumarin
- Subclass: Stilbene-Coumarin Derivative

Canonical Smiles	COc1cc(/C=C/c2ccc(cc2)O[C@@H]2O[C@H](CO)[C@@H]([C@@H]([C@H]2O)O)O)c2c(c1)oc(=O)cc2OC
InChI	InChI=1S/C25H26O10/c1-31-16-9-14(21-17(32-2)11-20(27)34-18(21)10-16)6-3-13-4-7-15(8-5-13)33-25-24(30)23(29)22(28)19(12-26)35-25/h3-11,19,22-26,28-30H,12H2,1-2H3/b6-3+/t19-,22+,23+,24-,25-/m1/s1
InChIKey	BSVOIIIUBIWNCA-QGGZOQPNSA-N
Formula	C₂₅H₂₆O₁₀
HBA	10
HBD	4
MW	486.47
Rotatable Bonds	7
TPSA	148.05
LogP	1.16
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	35
Formal Charge	0
Fraction CSP3	0.32
Exact Mass	486.15
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Monotes kerstingii	Dipterocarpaceae	Plantae	2029430

Showing of synonyms

Fotso GW, Mogue Kamdem L, et al. (2019). Antimicrobial secondary metabolites from the stem barks and leaves of Monotes kerstingii Gilg (Dipterocarpaceae).. Fitoterapia,2019, 137, 104239. [View] [PubMed]

No compound-protein relationship available.

SMILES: c1cc(=O)oc(c12)cccc2C=Cc3ccc(cc3)OC4CCCCO4

Level: 2

Mol. Weight: 486.47 g/mol

SMILES: c1ccccc1C=Cc2cccc(c23)oc(=O)cc3

Level: 1

Mol. Weight: 486.47 g/mol

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 486.47 g/mol

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

Level: 0

Mol. Weight: 486.47 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 486.47 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 486.47 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.13
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.820
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -0.95

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.310
Plasma Protein Binding: 92.92
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 0.790
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.420
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.510
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.950
Micronucleos: Toxic
NR-AhR: Toxic
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -386.670
Rat (Acute): 2.710
Rat (Chronic Oral): 3.620
Fathead Minnow: 4.740
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Toxic
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Toxic

General Properties

Boiling Point: 554.840
Hydration Free Energy: -3.090
Log(D) at pH=7.4: 2.170
Log(P): 1.43
Log S: -3.85
Log(Vapor Pressure): -11.68
Melting Point: 198.63
pKa Acid: 6.67
pKa Basic: 3.4

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.9782
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.9619
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.9578
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.9417
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9297
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.9265
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.9225
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.9007
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.9004
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.8905
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.8796
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.8773
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8684
ALK tyrosine kinase receptor	Q9UM73	ALK_HUMAN	Homo sapiens	3	0.8628
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.8488
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8481
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.8405
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8311
Achbp	I6L8L2	I6L8L2_CAPTE	Capitella teleta	3	0.8310
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	3	0.8079
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8072
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.8063
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.8018
Caspase-3	P42574	CASP3_HUMAN	Homo sapiens	3	0.7931
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7925
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.7876
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7841
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7805
ADP-ribosylation factor 1	P84077	ARF1_HUMAN	Homo sapiens	2	0.7797
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7791
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7771
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.7747
cGMP-dependent protein kinase 1	P00516	KGP1_BOVIN	Bos taurus	3	0.7716
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.7660
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	Q0QF01	SDHA_PIG	Sus scrofa	3	0.7637
Polymerase basic protein 2	Q2LG68	Q2LG68_9INFA	Influenza A virus)	4	0.7629
HTH-type transcriptional regulator EthR	P9WMC1	ETHR_MYCTU	Mycobacterium tuberculosis	3	0.7621
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7580
Prenyltransferase	Q4R2T2	Q4R2T2_STRC1	Streptomyces sp	2	0.7551
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	2	0.7550
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7534
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7533
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.7517
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7517
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7473
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7467
Nucleoside 2-deoxyribosyltransferase	Q8RLY5	Q8RLY5_LACHE	Lactobacillus helveticus	3	0.7449
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7435
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7406
AGAP003309-PA	A0A1U7F4W2	A0A1U7F4W2_ANOGA	Anopheles gambiae	3	0.7346
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7326
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	4	0.7322
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7320
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.7316
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7314
Cytochrome P450 2E1	P05181	CP2E1_HUMAN	Homo sapiens	3	0.7286
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7284
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7280
Mitogen-activated protein kinase kinase kinase 5	Q99683	M3K5_HUMAN	Homo sapiens	3	0.7276
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.7258
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7252
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	2	0.7232
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	2	0.7218
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7209
Protein UshA	P07024	USHA_ECOLI	Escherichia coli	3	0.7200
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	4	0.7199
Glycogen synthase	P0A6U8	GLGA_ECOLI	Escherichia coli	3	0.7191
6-phosphogluconate dehydrogenase, decarboxylating	P96789	6PGD_LACLM	Lactococcus lactis subsp. cremoris	3	0.7188
Eugenol synthase 1	Q15GI4	EGS1_OCIBA	Ocimum basilicum	3	0.7187
Bifunctional dihydrofolate reductase-thymidylate synthase	P13922	DRTS_PLAFK	Plasmodium falciparum	2	0.7187
ALK tyrosine kinase receptor	Q9UM73	ALK_HUMAN	Homo sapiens	3	0.7183
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7177
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7172
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.7171
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7170
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.7170
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7162
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7162
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7161
FMN-dependent NAD(P)H:quinone oxidoreductase 1	Q9I5F3	AZOR1_PSEAE	Pseudomonas aeruginosa	2	0.7160
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7129
Elongation factor Tu 1	P0CE47	EFTU1_ECOLI	Escherichia coli	3	0.7128
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	P49354	FNTA_HUMAN	Homo sapiens	3	0.7124
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7121
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	2	0.7115
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7110
Pteridine reductase, putative	Q581W1	Q581W1_TRYB2	Trypanosoma brucei brucei	2	0.7106
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7078
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7077
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7075
3',5'-cyclic-AMP phosphodiesterase 4A	P27815	PDE4A_HUMAN	Homo sapiens	3	0.7072
Metallo-beta-lactamase type 2	C7C422	BLAN1_KLEPN	Klebsiella pneumoniae	2	0.7072
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7060
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7044
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	2	0.7040
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.7034
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7029
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7019
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7017
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7014
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7006
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7005
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7003
Beta-galactosidase	P00722	BGAL_ECOLI	Escherichia coli	3	0.7001

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