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Ericoside

Family: Plantae - Ericaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Biflavonoid

Canonical Smiles	C1([C@@H](O[C@H]2O[C@H](C([C@H]([C@H]2O)O)O)C)C(=O)c2c(O)cc(O)cc2O1)c1ccc(Oc2cc(c3c(O[C@@H]4O[C@@H](C([C@@H]([C@@H]4O)O)O)C)c(=O)c4c(O)cc(O)cc4o3)ccc2)cc1
InChI	InChI=1S/C42H40O19/c1-15-29(47)33(51)35(53)41(55-15)60-39-31(49)27-23(45)11-19(43)13-25(27)58-37(39)17-6-8-21(9-7-17)57-22-5-3-4-18(10-22)38-40(61-42-36(54)34(52)30(48)16(2)56-42)32(50)28-24(46)12-20(44)14-26(28)59-38/h3-16,29-30,33-37,39,41-48,51-54H,1-2H3/t15-,16+,29?,30?,33+,34-,35+,36-,37?,39-,41+,42-/m0/s1
InChIKey	OZPCKTMNVPTKAJ-VYGFWKHPSA-N
Formula	C₄₂H₄₀O₁₉
HBA	19
HBD	10
MW	848.76
Rotatable Bonds	8
TPSA	304.96
LogP	1.81
Number Rings	8
Number Aromatic Rings	5
Heavy Atom Count	61
Formal Charge	0
Fraction CSP3	0.33
Exact Mass	848.22
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Erica mannii	Ericaceae	Plantae	2984617

Showing of synonyms

Bitchagno GT, Tankeo SB, et al. (2016). Ericoside, a new antibacterial biflavonoid from Erica mannii (Ericaceae).. Fitoterapia,2016, 109, 206-211. [View] [PubMed]

No compound-protein relationship available.

SMILES: O1CCCCC1Oc(c2=O)c(oc(c23)cccc3)-c4cc(ccc4)Oc(cc5)ccc5C(Oc(c67)cccc7)C(C6=O)OC8CCCCO8

Level: 5

Mol. Weight: 848.76 g/mol

SMILES: c1cccc(c12)oc(cc2=O)-c3cc(ccc3)Oc(cc4)ccc4C(Oc(c56)cccc6)C(C5=O)OC7CCCCO7

Level: 4

Mol. Weight: 848.76 g/mol

SMILES: O1CCCCC1Oc(c2=O)c(oc(c23)cccc3)-c4cc(ccc4)Oc(cc5)ccc5C(CC6=O)Oc(c67)cccc7

Level: 4

Mol. Weight: 848.76 g/mol

SMILES: c1cccc(c12)oc(cc2=O)-c3cc(ccc3)Oc(cc4)ccc4C(CC5=O)Oc(c56)cccc6

Level: 3

Mol. Weight: 848.76 g/mol

SMILES: O1CCCCC1OC(C2=O)C(Oc(c23)cccc3)c4ccc(cc4)Oc5ccccc5

Level: 3

Mol. Weight: 848.76 g/mol

SMILES: O1CCCCC1Oc(c2=O)c(oc(c23)cccc3)-c4cc(ccc4)Oc5ccccc5

Level: 3

Mol. Weight: 848.76 g/mol

SMILES: c1cccc(c12)OC(c3ccccc3)C(C2=O)OC4CCCCO4

Level: 2

Mol. Weight: 848.76 g/mol

SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC4CCCCO4

Level: 2

Mol. Weight: 848.76 g/mol

SMILES: c1cccc(c12)OC(CC2=O)c3ccc(cc3)Oc4ccccc4

Level: 2

Mol. Weight: 848.76 g/mol

SMILES: c1cccc(c12)oc(cc2=O)-c3cc(ccc3)Oc4ccccc4

Level: 2

Mol. Weight: 848.76 g/mol

SMILES: c1cccc(c12)OCC(C2=O)OC3CCCCO3

Level: 1

Mol. Weight: 848.76 g/mol

SMILES: c1cccc(c12)occ(c2=O)OC3CCCCO3

Level: 1

Mol. Weight: 848.76 g/mol

SMILES: c1cccc(c12)OC(CC2=O)c3ccccc3

Level: 1

Mol. Weight: 848.76 g/mol

SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3

Level: 1

Mol. Weight: 848.76 g/mol

SMILES: c1ccccc1Oc2ccccc2

Level: 1

Mol. Weight: 848.76 g/mol

SMILES: c1cccc(c12)OCCC2=O

Level: 0

Mol. Weight: 848.76 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 848.76 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 848.76 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 848.76 g/mol

Antibacterial

Absorption

Caco-2 (logPapp): -6.55
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 549.03
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 72554.58

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.88
Plasma Protein Binding: 75.58
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: 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: 7.46
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Toxic
Bee: Toxic
Bioconcentration Factor: -1685.13
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.89
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.62
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: -131681004.76
Rat (Acute): 2.6
Rat (Chronic Oral): 5.06
Fathead Minnow: 166228.18
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: 14802901.83
Hydration Free Energy: -2.92
Log(D) at pH=7.4: 1.99
Log(P): 3.06
Log S: -6.61
Log(Vapor Pressure): -487394.71
Melting Point: 265.22
pKa Acid: -3496.95
pKa Basic: -1.33

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.9029
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8866
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8766
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.8423
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.8380
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8285
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8242
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.8224
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.8134
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.8083
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.8028
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8025
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.8007
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7981
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7971
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7970
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	3	0.7926
Lysozyme C II	P11941	LYSC2_ONCMY	Oncorhynchus mykiss	3	0.7833
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.7798
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7795
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7728
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7712
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.7491
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7464
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	Q0QF01	SDHA_PIG	Sus scrofa	3	0.7383
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7334
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7323
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7308
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7285
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	4	0.7223
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7219
Dihydrofolate reductase	P0A017	DYR_STAAU	Staphylococcus aureus	4	0.7213
Periplasmic pH-dependent serine endoprotease DegQ	P39099	DEGQ_ECOLI	Escherichia coli	4	0.7150
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.7147
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7143
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7107
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7101
O-methyltransferase family 2	D5STZ7	D5STZ7_PLAL2	Planctopirus limnophila	4	0.7099
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7098
Serine/threonine-protein kinase PLK1	P53350	PLK1_HUMAN	Homo sapiens	3	0.7091
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7088
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7021

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