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Valoneic dilactone acid

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

Canonical Smiles	OC(=O)c1cc(O)c(c(c1Oc1cc2c(=O)oc3c4c2c(c1O)oc(=O)c4cc(c3O)O)O)O
InChI	InChI=1S/C21H10O13/c22-7-2-6(19(28)29)16(15(27)12(7)24)32-9-3-5-11-10-4(20(30)34-18(11)14(9)26)1-8(23)13(25)17(10)33-21(5)31/h1-3,22-27H,(H,28,29)
InChIKey	BPAOAXAAABIQKR-UHFFFAOYSA-N
Formula	C₂₁H₁₀O₁₃
HBA	12
HBD	7
MW	470.3
Rotatable Bonds	3
TPSA	228.33
LogP	2.21
Number Rings	5
Number Aromatic Rings	5
Heavy Atom Count	34
Formal Charge	0
Fraction CSP3	0.0
Exact Mass	470.01
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Epilobium hirsutum	Onagraceae	Plantae	210355
2	Eucalyptus camaledulensis	Myrtaceae	Plantae	34316

Showing of synonyms

Singab A-N, Ayoub N, et al. (2011). Phenolic Constituents of Eucalyptus camaldulensis Dehnh, with Potential Antioxidant and Cytotoxic Activities. Records of Natural Products,2011,5(4),271-280. [View]
Barakat HH, Hussein SAM, et al. (1997). Polyphenolic metabolites of Epilobium hirsutum. Phytochemistry,1997,46(5),935-941. [View]

Pubchem: 10151874

Cas: 60202-70-2

Zinc: ZINC000014827345

Nmrshiftdb2: 60025161

Chembl: CHEMBL5079864

Comptox: DTXSID60436184

CPRiL: 411900

SMILES: c12c3c4c(=O)oc2cc(Oc5ccccc5)cc1c(=O)oc3ccc4

Level: 1

Mol. Weight: 470.3 g/mol

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

Level: 0

Mol. Weight: 470.3 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 470.3 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.45
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.64
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 1.2

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.4
Plasma Protein Binding: 88.14
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: 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: 9.68
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: -2.17
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.25
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.35
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: -196.38
Rat (Acute): 2.36
Rat (Chronic Oral): 4.3
Fathead Minnow: 4.42
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: 675.04
Hydration Free Energy: -3.48
Log(D) at pH=7.4: -0.28
Log(P): 1.79
Log S: -4.0
Log(Vapor Pressure): -10.2
Melting Point: 327.39
pKa Acid: 10.17
pKa Basic: 3.03

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Protocatechuate 3,4-dioxygenase beta chain	P00437	PCXB_PSEPU	Pseudomonas putida	3	0.9201
Protocatechuate 3,4-dioxygenase beta chain	P00437	PCXB_PSEPU	Pseudomonas putida	3	0.9201
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.9054
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.9054
Protocatechuate 3,4-dioxygenase beta chain	P00437	PCXB_PSEPU	Pseudomonas putida	3	0.9028
Protocatechuate 3,4-dioxygenase beta chain	P00437	PCXB_PSEPU	Pseudomonas putida	3	0.9028
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.8735
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.8735
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.8503
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.8503
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8332
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8332
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.8167
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.8167
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8133
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8133
Vanillate porin OpdK	Q9HUR5	Q9HUR5_PSEAE	Pseudomonas aeruginosa	3	0.8076
Vanillate porin OpdK	Q9HUR5	Q9HUR5_PSEAE	Pseudomonas aeruginosa	3	0.8076
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	3	0.7987
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	3	0.7987
SRSF protein kinase 1	Q96SB4	SRPK1_HUMAN	Homo sapiens	4	0.7858
SRSF protein kinase 1	Q96SB4	SRPK1_HUMAN	Homo sapiens	4	0.7858
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7848
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7848
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.7818
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.7818
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7800
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7800
Ectonucleoside triphosphate diphosphohydrolase I	Q5ZUA2	Q5ZUA2_LEGPH	Legionella pneumophila subsp. pneumophila	3	0.7766
Ectonucleoside triphosphate diphosphohydrolase I	Q5ZUA2	Q5ZUA2_LEGPH	Legionella pneumophila subsp. pneumophila	3	0.7766
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7740
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7740
Dihydropteroate synthase	Q81VW8	Q81VW8_BACAN	Bacillus anthracis	3	0.7669
Dihydropteroate synthase	Q81VW8	Q81VW8_BACAN	Bacillus anthracis	3	0.7669
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7662
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7662
Hygromycin-B 4-O-kinase	P00557	KHYB_ECOLX	Escherichia coli	4	0.7653
Hygromycin-B 4-O-kinase	P00557	KHYB_ECOLX	Escherichia coli	4	0.7653
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7645
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7645
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.7635
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.7635
Vanillate porin OpdK	Q9HUR5	Q9HUR5_PSEAE	Pseudomonas aeruginosa	3	0.7586
Vanillate porin OpdK	Q9HUR5	Q9HUR5_PSEAE	Pseudomonas aeruginosa	3	0.7586
Seminal ribonuclease	P00669	RNS_BOVIN	Bos taurus	3	0.7552
Seminal ribonuclease	P00669	RNS_BOVIN	Bos taurus	3	0.7552
Polymerase acidic protein	Q5EP34	Q5EP34_9INFA	Influenza A virus	3	0.7518
Polymerase acidic protein	Q5EP34	Q5EP34_9INFA	Influenza A virus	3	0.7518
Shikimate dehydrogenase (NADP(+))	P56119	AROE_HELPY	Helicobacter pylori	3	0.7447
Shikimate dehydrogenase (NADP(+))	P56119	AROE_HELPY	Helicobacter pylori	3	0.7447
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7440
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7440
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7417
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7417
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7374
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7374
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	5	0.7354
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	5	0.7354
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7335
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7335
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7331
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7331
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.7327
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.7327
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	4	0.7282
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	4	0.7282
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	3	0.7259
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	3	0.7259
UDP-galactopyranose mutase	Q48485	GLF1_KLEPN	Klebsiella pneumoniae	3	0.7246
UDP-galactopyranose mutase	Q48485	GLF1_KLEPN	Klebsiella pneumoniae	3	0.7246
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7224
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7224
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7218
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7218
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7191
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7191
Serine/threonine-protein kinase receptor R3	P37023	ACVL1_HUMAN	Homo sapiens	4	0.7178
Serine/threonine-protein kinase receptor R3	P37023	ACVL1_HUMAN	Homo sapiens	4	0.7178
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.7168
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.7168
Aspartate carbamoyltransferase catalytic subunit	P0A786	PYRB_ECOLI	Escherichia coli	3	0.7137
Aspartate carbamoyltransferase catalytic subunit	P0A786	PYRB_ECOLI	Escherichia coli	3	0.7137
Thymidylate synthase	P04818	TYSY_HUMAN	Homo sapiens	3	0.7133
Thymidylate synthase	P04818	TYSY_HUMAN	Homo sapiens	3	0.7133
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7121
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7121
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7069
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7069
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.7066
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.7066
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7013
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7013

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