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Stynophyllanin A

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

Canonical Smiles	OC1Cc2c(O)cc(c(c2OC1c1ccc(c(c1)O)O)[C@@H]1[C@H]2OC(=O)c3c1c(O)c(O)c(c3c1c(C(=O)O[C@H]2[C@@H]2OC(=O)c3cc(O)c(c(c3c3cc(C(=O)OC[C@@H]2OC(=O)c2cc(O)c(c(c2)O)O)c(c(c3O)O)O)O)O)cc(c(c1O)O)O)O)O
InChI	InChI=1S/C56H40O31/c57-19-2-1-12(3-21(19)59)47-27(65)7-14-20(58)10-22(60)31(48(14)84-47)34-33-35-32(43(73)46(76)44(33)74)30-17(9-26(64)40(70)42(30)72)55(80)87-51(50(34)86-56(35)81)49-28(83-52(77)13-4-23(61)38(68)24(62)5-13)11-82-53(78)18-6-15(36(66)45(75)37(18)67)29-16(54(79)85-49)8-25(63)39(69)41(29)71/h1-6,8-10,27-28,34,47,49-51,57-76H,7,11H2/t27?,28-,34-,47?,49+,50+,51-/m0/s1
InChIKey	PWRHEVDCZFUGDE-ZVMOZOGRSA-N
Formula	C₅₆H₄₀O₃₁
HBA	31
HBD	20
MW	1208.91
Rotatable Bonds	5
TPSA	545.33
LogP	3.3
Number Rings	12
Number Aromatic Rings	7
Heavy Atom Count	87
Formal Charge	0
Fraction CSP3	0.16
Exact Mass	1208.16
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Eucalyptus citriodora	Myrtaceae	Plantae	34329

Showing of synonyms

Al-Sayed E, El-Naga R.N. (2015). Protective role of ellagitannins from Eucalyptus citriodora against ethanol-induced gastriculcerinrats: Impact on oxidative stress, inflammation and calcitonin-generelated peptide.. Phytomedicine : international journal of phytotherapy and phytopharmacology,2015, 22(1), 5-15. [View] [PubMed]

No compound-protein relationship available.

SMILES: c1ccccc1C(=O)OC(COC(=O)c(cc2c34)ccc2)C(OC(=O)c3cccc4)C(OC(=O)c(c5c6c78)cccc5)C(OC8=O)C(c7ccc6)c9cccc(c19)CCC(O1)c1ccccc1

Level: 4

Mol. Weight: 1208.91 g/mol

SMILES: c1ccccc1C(=O)OC(COC(=O)c(cc2c34)ccc2)C(OC(=O)c3cccc4)C(OC(=O)c(c5c6c78)cccc5)C(OC8=O)C(c7ccc6)c9cccc(c19)CCCO1

Level: 3

Mol. Weight: 1208.91 g/mol

SMILES: c12c3cc(ccc3)C(=O)OCCC(OC(=O)c1cccc2)C(OC(=O)c(c4c5c67)cccc4)C(OC7=O)C(c6ccc5)c8cccc(c89)CCC(O9)c1ccccc1

Level: 3

Mol. Weight: 1208.91 g/mol

SMILES: c12c3cc(ccc3)C(=O)OCCC(OC(=O)c1cccc2)C(OC(=O)c(c4c5c67)cccc4)C(OC7=O)C(c6ccc5)c8cccc(c89)CCCO9

Level: 2

Mol. Weight: 1208.91 g/mol

SMILES: c1ccccc1C(=O)OC(COC(=O)c(cc2c34)ccc2)C(OC(=O)c3cccc4)C(C(OC5=O)Cc6ccc7)OC(=O)c(c8c7c56)cccc8

Level: 2

Mol. Weight: 1208.91 g/mol

SMILES: c1cccc(c1c2c34)C(=O)OCC(OC4=O)C(c3ccc2)c5cccc(c56)CCC(O6)c7ccccc7

Level: 2

Mol. Weight: 1208.91 g/mol

SMILES: c1cccc(c1c2c34)C(=O)OC(C(OC4=O)Cc3ccc2)C(OC(=O)c5cccc6)CCOC(=O)c(cc7c56)ccc7

Level: 1

Mol. Weight: 1208.91 g/mol

SMILES: c1cccc(c1c2c34)C(=O)OCC(OC4=O)C(c3ccc2)c5cccc(c56)CCCO6

Level: 1

Mol. Weight: 1208.91 g/mol

SMILES: c1ccccc1C(=O)OC(COC(=O)c(cc2c34)ccc2)COC(=O)c3cccc4

Level: 1

Mol. Weight: 1208.91 g/mol

SMILES: c1cccc(c12)OC(CC2)c3ccccc3

Level: 1

Mol. Weight: 1208.91 g/mol

SMILES: c12c3cc(ccc3)C(=O)OCCCOC(=O)c1cccc2

Level: 0

Mol. Weight: 1208.91 g/mol

SMILES: c1cccc(c1c2c34)C(=O)OCC(OC4=O)Cc3ccc2

Level: 0

Mol. Weight: 1208.91 g/mol

SMILES: C1CCOc(c12)cccc2

Level: 0

Mol. Weight: 1208.91 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 1208.91 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.14
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 10705117413.400
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 1399034668078.75

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.110
Plasma Protein Binding: 17.08
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: Inhibitor

Excretion

Clearance: 10.350
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Safe
Bioconcentration Factor: -32538368248.390
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -13287.240
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 4.050
Micronucleos: Toxic
NR-AhR: Toxic
NR-AR: Safe
NR-AR-LBD: Toxic
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -2539180372191019.000
Rat (Acute): 2.520
Rat (Chronic Oral): 5446316.020
Fathead Minnow: 3205175306491.110
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 285587417949444.312
Hydration Free Energy: -2.920
Log(D) at pH=7.4: -158758103.360
Log(P): -18480.38
Log S: -8.17
Log(Vapor Pressure): -9404250275548.1
Melting Point: -2852571.2
pKa Acid: -68524785966.51
pKa Basic: -551279744.63

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	0.8979
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.8555
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	4	0.8268
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8041
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7726
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q4WP27	Q4WP27_ASPFU	Aspergillus fumigatus	3	0.7211
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7211

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