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Nilocitin

Family: Plantae - Tamaricaceae
Kingdom: Plantae
Class: Tannin
- Subclass: Ellagitannin

Canonical Smiles	OCC1OC(O)C(C(C1O)OC(=O)c1cc(O)c(c(c1)O)O)OC(=O)c1cc(O)c(c(c1)O)O
InChI	InChI=1S/C20H20O14/c21-5-12-15(28)16(33-18(29)6-1-8(22)13(26)9(23)2-6)17(20(31)32-12)34-19(30)7-3-10(24)14(27)11(25)4-7/h1-4,12,15-17,20-28,31H,5H2
InChIKey	LRRLFFLVWQTQGZ-UHFFFAOYSA-N
Formula	C₂₀H₂₀O₁₄
HBA	14
HBD	9
MW	484.37
Rotatable Bonds	5
TPSA	243.9
LogP	-1.26
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	34
Formal Charge	0
Fraction CSP3	0.3
Exact Mass	484.09
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Reaumuria vermiculata	Tamaricaceae	Plantae	1518163

Showing of synonyms

Nawwar MA, Ayoub NA, et al. (2012). Cytotoxic ellagitannins from Reaumuria vermiculata. Fitoterapia,2012,83(7),1256-1266. [View] [PubMed]

Pubchem: 14213991

Nmrshiftdb2: 60033267

No compound-protein relationship available.

SMILES: c1ccccc1C(=O)OC2C(COCC2)OC(=O)c3ccccc3

Level: 2

Mol. Weight: 484.37 g/mol

SMILES: c1ccccc1C(=O)OC2CCOCC2

Level: 1

Mol. Weight: 484.37 g/mol

SMILES: c1ccccc1C(=O)OC2CCCOC2

Level: 1

Mol. Weight: 484.37 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 484.37 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 484.37 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.72
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.8
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -0.19

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.47
Plasma Protein Binding: 0.94
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: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 13.42
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: -2.59
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.75
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 5.8
Micronucleos: Toxic
NR-AhR: Toxic
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: -110.54
Rat (Acute): 2.31
Rat (Chronic Oral): 3.8
Fathead Minnow: 3.69
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Toxic

General Properties

Boiling Point: 634.73
Hydration Free Energy: -4.06
Log(D) at pH=7.4: -0.51
Log(P): -1.05
Log S: -3.88
Log(Vapor Pressure): -11.16
Melting Point: 194.56
pKa Acid: 6.22
pKa Basic: 5.96

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9149
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9149
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8669
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8669
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8413
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8413
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	4	0.8357
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	4	0.8357
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8328
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8328
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8328
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8328
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8287
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8287
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8256
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8256
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8123
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8123
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8064
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8064
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9QYJ6	PDE10_RAT	Rattus norvegicus	3	0.8049
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9QYJ6	PDE10_RAT	Rattus norvegicus	3	0.8049
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8041
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8041
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7946
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7946
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7946
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7946
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7841
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7841
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7677
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7677
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.7593
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.7593
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.7582
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.7582
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.7530
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.7530
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7530
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7530
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7468
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7468
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7430
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7430
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7387
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7387
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7346
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7346
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7331
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7331
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.7308
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.7308
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	4	0.7293
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	4	0.7293
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7205
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7205
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.7193
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.7193
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	4	0.7181
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	4	0.7181
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7167
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7167
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4	Q9Y3Q4	HCN4_HUMAN	Homo sapiens	4	0.7146
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4	Q9Y3Q4	HCN4_HUMAN	Homo sapiens	4	0.7146
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	2	0.7088
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	2	0.7088
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7085
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7085
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	4	0.7070
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	4	0.7070
Thymidylate synthase	P0A886	TYSY_ECO57	Escherichia coli O157:H7	3	0.7017
Thymidylate synthase	P0A886	TYSY_ECO57	Escherichia coli O157:H7	3	0.7017

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