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4-(alpha-L-rhamnopyranosyl)ellagic acid

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

Canonical Smiles	O[C@H]1[C@@H](O[C@H]([C@@H]([C@H]1O)O)C)Oc1cc2c(=O)oc3c4c2c(c1O)oc(=O)c4cc(c3O)O
InChI	InChI=1S/C20H16O12/c1-4-11(22)14(25)15(26)20(29-4)30-8-3-6-10-9-5(18(27)32-17(10)13(8)24)2-7(21)12(23)16(9)31-19(6)28/h2-4,11,14-15,20-26H,1H3/t4-,11-,14+,15+,20-/m0/s1
InChIKey	NLOYJHDXNPMFKW-RGYXEVLJSA-N
Formula	C₂₀H₁₆O₁₂
HBA	12
HBD	6
MW	448.34
Rotatable Bonds	2
TPSA	200.26
LogP	-0.19
Number Rings	5
Number Aromatic Rings	4
Heavy Atom Count	32
Formal Charge	0
Fraction CSP3	0.3
Exact Mass	448.06
Number of Lipinski Rule Violations	2

#	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: 10026656

Cas: 211371-02-7

Zinc: ZINC000040395475

Chebi: 167701

Nmrshiftdb2: 60022822

Chembl: CHEMBL516559

Bindingdb: 50478560

CPRiL: 102806

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

Level: 1

Mol. Weight: 448.34 g/mol

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

Level: 0

Mol. Weight: 448.34 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 448.34 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.61
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.39
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 0.03

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.19
Plasma Protein Binding: 82.69
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Inhibitor
CYP 1A2 Inhibitor: 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: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 12.37
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -1.75
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.13
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.6
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: -82.99
Rat (Acute): 2.4
Rat (Chronic Oral): 4.07
Fathead Minnow: 3.99
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: 627.89
Hydration Free Energy: -4.51
Log(D) at pH=7.4: 1.22
Log(P): -0.28
Log S: -4.32
Log(Vapor Pressure): -11.31
Melting Point: 225.86
pKa Acid: 4.67
pKa Basic: 4.63

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	0.9229
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.9229
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.8535
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.8535
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8394
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8394
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.8189
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.8189
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8002
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8002
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.7992
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.7992
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7856
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7856
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.7634
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.7634
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7574
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7574
Non-receptor tyrosine-protein kinase TYK2	P29597	TYK2_HUMAN	Homo sapiens	5	0.7529
Non-receptor tyrosine-protein kinase TYK2	P29597	TYK2_HUMAN	Homo sapiens	5	0.7529
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7524
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7524
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	4	0.7498
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	4	0.7498
IAG-nucleoside hydrolase	Q9GPQ4	Q9GPQ4_TRYVI	Trypanosoma vivax	4	0.7461
IAG-nucleoside hydrolase	Q9GPQ4	Q9GPQ4_TRYVI	Trypanosoma vivax	4	0.7461
Nucleoprotein	P33469	NCAP_CVHOC	Human coronavirus OC43	3	0.7398
Nucleoprotein	P33469	NCAP_CVHOC	Human coronavirus OC43	3	0.7398
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7397
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7397
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7390
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7390
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7389
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7389
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7388
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7388
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7379
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7379
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7360
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7360
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7316
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7316
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	4	0.7224
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	4	0.7224
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7204
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7204
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7193
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7193
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7173
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7173
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7160
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7160
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7078
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7078
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7071
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7071
Diphtheria toxin	P00588	DTX_CORBE	Corynephage beta	3	0.7060
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7060
Diphtheria toxin	P00588	DTX_CORBE	Corynephage beta	3	0.7060
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7060
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7026
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7026
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7022
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7022

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