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4-[(6-O-(5-O-(3,4-dimethoxybenzoyl)-beta-apiofuranosyl)-beta-glucopyranoside)oxy]-5-methoxycoumarin

Family: Plantae - Ebenaceae
Kingdom: Plantae
Class: Coumarin
- Subclass: Coumarin Glycoside Derivative

Canonical Smiles	COc1cc(ccc1OC)C(=O)OCC1(O)CO[C@@H]([C@H]1O)OC[C@@H]1OC(Oc2cc(=O)oc3c2c(C)ccc3)[C@H]([C@@H]([C@H]1O)O)O
InChI	InChI=1S/C30H34O15/c1-14-5-4-6-17-22(14)19(10-21(31)43-17)44-28-25(34)24(33)23(32)20(45-28)11-40-29-26(35)30(37,13-42-29)12-41-27(36)15-7-8-16(38-2)18(9-15)39-3/h4-10,20,23-26,28-29,32-35,37H,11-13H2,1-3H3/t20-,23-,24+,25-,26+,28?,29-,30?/m0/s1
InChIKey	KBPMNLSIDNWHGY-UABMZYDQSA-N
Formula	C₃₀H₃₄O₁₅
HBA	15
HBD	5
MW	634.59
Rotatable Bonds	10
TPSA	213.04
LogP	-0.37
Number Rings	5
Number Aromatic Rings	3
Heavy Atom Count	45
Formal Charge	0
Fraction CSP3	0.47
Exact Mass	634.19
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Diospyros bipindensis	Ebenaceae	Plantae	413723

Showing of synonyms

Cesari I, Queiroz EF, et al. (2013). Extensive phytochemical investigation of the polar constituents of Diospyros bipindensis Gürke traditionally used by Baka pygmies.. Phytochemistry,2013, 96, 279-287. [View] [PubMed]

No compound-protein relationship available.

SMILES: c1ccccc1C(=O)OCC2CC(OC2)OCC3CCCC(O3)Oc4cc(=O)oc(c45)cccc5

Level: 3

Mol. Weight: 634.59 g/mol

SMILES: O1CCCC1OCC2CCCC(O2)Oc3cc(=O)oc(c34)cccc4

Level: 2

Mol. Weight: 634.59 g/mol

SMILES: c1ccccc1C(=O)OCC2CC(OC2)OCC3CCCCO3

Level: 2

Mol. Weight: 634.59 g/mol

SMILES: c1cccc(c12)oc(=O)cc2OC3CCCCO3

Level: 1

Mol. Weight: 634.59 g/mol

SMILES: c1ccccc1C(=O)OCC2CCOC2

Level: 1

Mol. Weight: 634.59 g/mol

SMILES: O1CCCCC1COC2CCCO2

Level: 1

Mol. Weight: 634.59 g/mol

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

Level: 0

Mol. Weight: 634.59 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 634.59 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 634.59 g/mol

SMILES: C1CCOC1

Level: 0

Mol. Weight: 634.59 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.27
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -4.930
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 25.78

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.030
Plasma Protein Binding: 75.95
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: Non-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: 4.600
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -1.740
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.870
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.620
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -49081.380
Rat (Acute): 2.460
Rat (Chronic Oral): 4.000
Fathead Minnow: 77.990
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 681.740
Hydration Free Energy: -2.920
Log(D) at pH=7.4: 1.210
Log(P): 0.42
Log S: -3.67
Log(Vapor Pressure): -50.27
Melting Point: 197.42
pKa Acid: 5.22
pKa Basic: 1.19

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	0.9675
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.9114
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.9022
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8982
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8937
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8567
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.8063
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.8012
Bifunctional dihydrofolate reductase-thymidylate synthase	P13922	DRTS_PLAFK	Plasmodium falciparum	3	0.7933
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.7927
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	3	0.7894
histidine kinase	O32393	O32393_ARTPT	Arthrospira platensis	3	0.7753
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7739
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	3	0.7657
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.7652
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7548
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.7490
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7486
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	3	0.7471
Glutathione S-transferase P	P09211	GSTP1_HUMAN	Homo sapiens	2	0.7428
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7412
Uncharacterized protein	Q3F0V8	Q3F0V8_BACTI	Bacillus thuringiensis serovar israelensis ATCC 35646	3	0.7389
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7310
Elongation factor Tu 1	P0CE47	EFTU1_ECOLI	Escherichia coli	3	0.7292
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7288
Ephrin type-A receptor 2	P29317	EPHA2_HUMAN	Homo sapiens	3	0.7284
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7283
Ribonuclease TTHA0252	Q5SLP1	RNSE_THET8	Thermus thermophilus	3	0.7282
Caffeoyl-CoA O-methyltransferase	Q40313	CAMT_MEDSA	Medicago sativa	3	0.7276
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7264
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	3	0.7260
Nuclear receptor subfamily 1 group I member 3	O35627	NR1I3_MOUSE	Mus musculus	3	0.7257
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7248
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7222
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	2	0.7218
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7212
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7210
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7194
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7182
Phenolphthiocerol/phthiocerol polyketide synthase subunit C	P96202	PPSC_MYCTU	Mycobacterium tuberculosis	3	0.7159
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	2	0.7150
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	2	0.7148
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.7131
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7130
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7082
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7080
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7077
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7058
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.7052
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	3	0.7043
Orotidine 5'-phosphate decarboxylase	O26232	PYRF_METTH	Methanothermobacter thermautotrophicus	3	0.7038
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	3	0.7036
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7024

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