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3-O-methylellagic acid-4′-O-alpha-L-rhamnopyranoside

Family: Plantae - Dipterocarpaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavone Glycoside

Canonical Smiles	COc1c(O)cc2c3c1oc(=O)c1c3c(oc2=O)c(c(c1)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)O
InChI	InChI=1S/C21H18O12/c1-5-12(23)14(25)15(26)21(30-5)31-9-4-7-10-11-6(19(27)32-17(10)13(9)24)3-8(22)16(29-2)18(11)33-20(7)28/h3-5,12,14-15,21-26H,1-2H3/t5-,12-,14+,15+,21-/m0/s1
InChIKey	IAYGIELPGJHKME-UKZWKHHHSA-N
Formula	C₂₁H₁₈O₁₂
HBA	12
HBD	5
MW	462.36
Rotatable Bonds	3
TPSA	189.26
LogP	0.12
Number Rings	5
Number Aromatic Rings	4
Heavy Atom Count	33
Formal Charge	0
Fraction CSP3	0.33
Exact Mass	462.08
Number of Lipinski Rule Violations	1

#	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]

Pubchem: 44560360

Cas: 51768-39-9

Zinc: ZINC000040864091

Nmrshiftdb2: 60081436

Chembl: CHEMBL460463

No compound-protein relationship available.

SMILES: c12c3c4c(=O)oc2cc(OC5CCCCO5)cc1c(=O)oc3ccc4

Level: 1

Mol. Weight: 462.36 g/mol

SMILES: c12c3c4c(=O)oc2cccc1c(=O)oc3ccc4

Level: 0

Mol. Weight: 462.36 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 462.36 g/mol

Antibacterial

Absorption

Caco-2 (logPapp): -6.42
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.080
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -0.98

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.390
Plasma Protein Binding: 81.22
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: Non-Inhibitor
CYP 2C9 Substrate: Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 9.490
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -1.070
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.910
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.820
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: -140.060
Rat (Acute): 2.450
Rat (Chronic Oral): 3.550
Fathead Minnow: 4.480
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 584.910
Hydration Free Energy: -3.360
Log(D) at pH=7.4: 2.050
Log(P): 0.26
Log S: -4.27
Log(Vapor Pressure): -10.66
Melting Point: 204.91
pKa Acid: 6.85
pKa Basic: 2.29

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.9449
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.9139
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.8950
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	5	0.8799
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8734
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.8636
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8580
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8490
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8477
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	3	0.8474
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.8416
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8378
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8279
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	3	0.8279
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.8252
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.8204
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.8172
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.8148
NAD(P)H dehydrogenase [quinone] 1	P15559	NQO1_HUMAN	Homo sapiens	4	0.8028
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8026
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	4	0.8001
Mitogen-activated protein kinase kinase kinase 5	Q99683	M3K5_HUMAN	Homo sapiens	3	0.7965
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	4	0.7878
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7841
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7827
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	3	0.7797
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.7748
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7741
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7713
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7689
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7685
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7682
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7653
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7620
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7619
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7530
Diphtheria toxin	P00588	DTX_CORBE	Corynephage beta	3	0.7457
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7431
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7429
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7422
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7415
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7398
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7386
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	4	0.7378
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7363
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	2	0.7341
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.7327
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7320
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7294
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7280
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7278
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7261
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.7255
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7249
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7241
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.7232
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7214
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7195
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	4	0.7179
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7177
Metallo-beta-lactamase type 2	C7C422	BLAN1_KLEPN	Klebsiella pneumoniae	2	0.7162
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7150
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7111
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7101
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	3	0.7074
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7031
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7028
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7026
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7009
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7002

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