ANPDB

Select a section from the left sidebar

3-O-methyl-4-(alpha-L-rhamnopyranosyl)ellagic acid

Family: Plantae - Combretaceae
Kingdom: Plantae
Class: Phenolic
- Subclass: Ellagic Acid Derivative

Canonical Smiles	COc1c(O[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O)O)cc2c3c1oc(=O)c1c3c(oc2=O)c(c(c1)O)O
InChI	InChI=1S/C21H18O12/c1-5-12(23)14(25)15(26)21(30-5)31-9-4-7-11-10-6(19(27)33-18(11)16(9)29-2)3-8(22)13(24)17(10)32-20(7)28/h3-5,12,14-15,21-26H,1-2H3/t5-,12-,14+,15+,21-/m0/s1
InChIKey	LPXGCZRQLILWOH-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	Terminalia brownii	Combretaceae	Plantae	1548809

Showing of synonyms

Machumi F, Midiwo JO, et al. (2013). Phytochemical, antimicrobial and antiplasmodial investigations of Terminalia brownii. Natural Product Communications,2013,8(6),761-764. [View] [PubMed]

Pubchem: 16720461

Cas: 639089-97-7

Zinc: ZINC000095913628

Nmrshiftdb2: 60026128

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

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.29
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -4.990
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -0.79

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.400
Plasma Protein Binding: 81.63
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: 9.590
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -1.010
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.030
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.590
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: -140.240
Rat (Acute): 2.410
Rat (Chronic Oral): 3.420
Fathead Minnow: 4.560
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: 586.370
Hydration Free Energy: -3.430
Log(D) at pH=7.4: 1.870
Log(P): 0.15
Log S: -4.4
Log(Vapor Pressure): -10.83
Melting Point: 206.75
pKa Acid: 6.81
pKa Basic: 2.41

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	0.9268
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.9268
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.8580
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.8580
Lysozyme C II	P11941	LYSC2_ONCMY	Oncorhynchus mykiss	3	0.8546
Lysozyme C II	P11941	LYSC2_ONCMY	Oncorhynchus mykiss	3	0.8546
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.8498
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.8498
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	3	0.8446
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	3	0.8446
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8416
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8416
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8398
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8398
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8220
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8220
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.8179
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.8179
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8174
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8174
Tetracycline repressor protein class B from transposon Tn10	P04483	TETR2_ECOLX	Escherichia coli	3	0.8033
Tetracycline repressor protein class B from transposon Tn10	P04483	TETR2_ECOLX	Escherichia coli	3	0.8033
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8026
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8026
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7971
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7971
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.7829
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.7829
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7827
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7827
Non-receptor tyrosine-protein kinase TYK2	P29597	TYK2_HUMAN	Homo sapiens	5	0.7633
Non-receptor tyrosine-protein kinase TYK2	P29597	TYK2_HUMAN	Homo sapiens	5	0.7633
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7576
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7576
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7508
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7508
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7496
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7496
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7481
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7481
IAG-nucleoside hydrolase	Q9GPQ4	Q9GPQ4_TRYVI	Trypanosoma vivax	4	0.7463
IAG-nucleoside hydrolase	Q9GPQ4	Q9GPQ4_TRYVI	Trypanosoma vivax	4	0.7463
Nucleoprotein	P33469	NCAP_CVHOC	Human coronavirus OC43	3	0.7440
Nucleoprotein	P33469	NCAP_CVHOC	Human coronavirus OC43	3	0.7440
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7437
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7437
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7389
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7389
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	4	0.7388
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	4	0.7388
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.7283
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.7283
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	4	0.7262
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	4	0.7262
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7227
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7227
Fructose-1,6-bisphosphatase 1	P09467	F16P1_HUMAN	Homo sapiens	3	0.7187
Fructose-1,6-bisphosphatase 1	P09467	F16P1_HUMAN	Homo sapiens	3	0.7187
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7178
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7178
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7161
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7161
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7152
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7152
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7150
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7150
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7082
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7082
Purine nucleoside phosphorylase DeoD-type	O34925	DEOD_BACSU	Bacillus subtilis	3	0.7072
Purine nucleoside phosphorylase DeoD-type	O34925	DEOD_BACSU	Bacillus subtilis	3	0.7072
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7044
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7044
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7043
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7043
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7038
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7038

Download SDF