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Guajavin A

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

Canonical Smiles	OC1Cc2c(O)cc(c(c2OC1c1cc(O)c(c(c1)O)O)C1C2OC(=O)c3c1c(O)c(O)c(c3c1c(C(=O)OC2C2OC(=O)c3cc(O)c(c(c3c3c(C(=O)OCC2OC(=O)c2cc(O)c(c(c2)O)O)cc(c(c3O)O)O)O)O)cc(c(c1O)O)O)O)O
InChI	InChI=1S/C56H40O32/c57-17-9-18(58)31(48-13(17)5-26(66)47(85-48)11-1-19(59)36(67)20(60)2-11)34-33-35-32(44(75)46(77)45(33)76)30-16(8-25(65)40(71)43(30)74)55(81)88-51(50(34)87-56(35)82)49-27(84-52(78)12-3-21(61)37(68)22(62)4-12)10-83-53(79)14-6-23(63)38(69)41(72)28(14)29-15(54(80)86-49)7-24(64)39(70)42(29)73/h1-4,6-9,26-27,34,47,49-51,57-77H,5,10H2
InChIKey	QJOSZTCZZUNIRY-UHFFFAOYSA-N
Formula	C₅₆H₄₀O₃₂
HBA	32
HBD	21
MW	1224.9
Rotatable Bonds	5
TPSA	565.56
LogP	3.0
Number Rings	12
Number Aromatic Rings	7
Heavy Atom Count	88
Formal Charge	0
Fraction CSP3	0.16
Exact Mass	1224.15
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]

Pubchem: 131752682

Cas: 145826-24-0

No compound-protein relationship available.

SMILES: c1cccc(c1c23)C(=O)OCC(OC(=O)c4ccccc4)C(OC(=O)c2cccc3)C(OC(=O)c(c5c6c78)cccc5)C(OC8=O)C(c7ccc6)c9cccc(c19)CCC(O1)c1ccccc1

Level: 4

Mol. Weight: 1224.9 g/mol

SMILES: c1cccc(c1c23)C(=O)OCC(OC(=O)c4ccccc4)C(OC(=O)c2cccc3)C(OC(=O)c(c5c6c78)cccc5)C(OC8=O)C(c7ccc6)c9cccc(c19)CCCO1

Level: 3

Mol. Weight: 1224.9 g/mol

SMILES: c1cccc(c1c23)C(=O)OCCC(OC(=O)c2cccc3)C(OC(=O)c(c4c5c67)cccc4)C(OC7=O)C(c6ccc5)c8cccc(c89)CCC(O9)c1ccccc1

Level: 3

Mol. Weight: 1224.9 g/mol

SMILES: c1cccc(c1c23)C(=O)OCCC(OC(=O)c2cccc3)C(OC(=O)c(c4c5c67)cccc4)C(OC7=O)C(c6ccc5)c8cccc(c89)CCCO9

Level: 2

Mol. Weight: 1224.9 g/mol

SMILES: c1cccc(c1c23)C(=O)OCC(OC(=O)c4ccccc4)C(OC(=O)c2cccc3)C(C(OC5=O)Cc6ccc7)OC(=O)c(c8c7c56)cccc8

Level: 2

Mol. Weight: 1224.9 g/mol

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

Level: 2

Mol. Weight: 1224.9 g/mol

SMILES: c1cccc(c1c2c34)C(=O)OC(C(OC4=O)Cc3ccc2)C(OC(=O)c5cccc6)CCOC(=O)c(c7c56)cccc7

Level: 1

Mol. Weight: 1224.9 g/mol

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

Level: 1

Mol. Weight: 1224.9 g/mol

SMILES: c1cccc(c1c23)C(=O)OCC(COC(=O)c2cccc3)OC(=O)c4ccccc4

Level: 1

Mol. Weight: 1224.9 g/mol

SMILES: c1cccc(c12)OC(CC2)c3ccccc3

Level: 1

Mol. Weight: 1224.9 g/mol

SMILES: c1cccc(c1c23)C(=O)OCCCOC(=O)c2cccc3

Level: 0

Mol. Weight: 1224.9 g/mol

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

Level: 0

Mol. Weight: 1224.9 g/mol

SMILES: C1CCOc(c12)cccc2

Level: 0

Mol. Weight: 1224.9 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 1224.9 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.19
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 64186305892.280
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 8388403105627.89

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): -0.030
Plasma Protein Binding: 9.89
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: 10.450
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Safe
Bioconcentration Factor: -195095267386.620
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -79661.120
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: -15224548460206642.000
Rat (Acute): 2.630
Rat (Chronic Oral): 32655318.180
Fathead Minnow: 19217741298737.930
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: 1712339446040526.000
Hydration Free Energy: -2.920
Log(D) at pH=7.4: -951889887.670
Log(P): -110811.4
Log S: -8.19
Log(Vapor Pressure): -56386468082989.65
Melting Point: -17128780.41
pKa Acid: -410864435370.3
pKa Basic: -3305391663.41

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	0.8815
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.7851
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.7699
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7677
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7625
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7553
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7287
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7282
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.7217
Polymerase acidic protein	Q5EP34	Q5EP34_9INFA	Influenza A virus	3	0.7176
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	4	0.7066

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