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Blephariside A

Family: Plantae - Acanthaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavonol Glycoside

Canonical Smiles	O=C(OCC1O[C@@H](Oc2cc(ccc2O)c2oc3cc(O)cc(c3c(=O)c2O[C@@H]2OC(C)[C@H]([C@@H](C2O)O)O)O)C([C@H]([C@@H]1O)O)O)/C=C/Cc1ccc(c(c1)O)O
InChI	InChI=1S/C37H38O19/c1-14-27(44)30(47)32(49)36(52-14)56-35-29(46)26-21(42)11-17(38)12-23(26)53-34(35)16-6-8-19(40)22(10-16)54-37-33(50)31(48)28(45)24(55-37)13-51-25(43)4-2-3-15-5-7-18(39)20(41)9-15/h2,4-12,14,24,27-28,30-33,36-42,44-45,47-50H,3,13H2,1H3/b4-2+/t14?,24?,27-,28-,30+,31+,32?,33?,36+,37-/m1/s1
InChIKey	XHXVLRZUTJFZBB-FVSJBEQDSA-N
Formula	C₃₇H₃₈O₁₉
HBA	19
HBD	11
MW	786.69
Rotatable Bonds	10
TPSA	315.96
LogP	-0.28
Number Rings	6
Number Aromatic Rings	4
Heavy Atom Count	56
Formal Charge	0
Fraction CSP3	0.35
Exact Mass	786.2
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Blepharis ciliaris	Acanthaceae	Plantae	1569713

Showing of synonyms

Mohamed GA, Ibrahim SRM, et al. (2015). Blepharisides A and B, new flavonol glycosides from Blepharis ciliaris growing in Saudi Arabia. Phytochemistry Letters,2015,11,177-182. [View]

Pubchem: 163054860

Nmrshiftdb2: 70098930

No compound-protein relationship available.

SMILES: c1ccccc1CC=CC(=O)OCC2CCCC(O2)Oc(ccc3)cc3-c(oc(c45)cccc5)c(c4=O)OC6CCCCO6

Level: 4

Mol. Weight: 786.69 g/mol

SMILES: c1ccccc1CC=CC(=O)OCC2CCCC(O2)Oc(ccc3)cc3-c(cc4=O)oc(c45)cccc5

Level: 3

Mol. Weight: 786.69 g/mol

SMILES: O1CCCCC1Oc(c2=O)c(oc(c23)cccc3)-c4cc(ccc4)OC5CCCCO5

Level: 3

Mol. Weight: 786.69 g/mol

SMILES: c1ccccc1CC=CC(=O)OCC2CCCC(O2)Oc3ccccc3

Level: 2

Mol. Weight: 786.69 g/mol

SMILES: c1cccc(c12)oc(cc2=O)-c3cc(ccc3)OC4CCCCO4

Level: 2

Mol. Weight: 786.69 g/mol

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

Level: 2

Mol. Weight: 786.69 g/mol

SMILES: O1CCCCC1COC(=O)C=CCc2ccccc2

Level: 1

Mol. Weight: 786.69 g/mol

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

Level: 1

Mol. Weight: 786.69 g/mol

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

Level: 1

Mol. Weight: 786.69 g/mol

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 786.69 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 786.69 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 786.69 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 786.69 g/mol

Anti-inflammatory

Antioxidant

Absorption

Caco-2 (logPapp): -6.64
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 24.94
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 4059.59

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.77
Plasma Protein Binding: 49.02
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: 11.21
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -95.49
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.1
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 8.33
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: -7365156.42
Rat (Acute): 2.32
Rat (Chronic Oral): 4.75
Fathead Minnow: 9305.37
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: 820647.96
Hydration Free Energy: -2.92
Log(D) at pH=7.4: 0.1
Log(P): 1.14
Log S: -5.82
Log(Vapor Pressure): -27002.63
Melting Point: 249.25
pKa Acid: -163.03
pKa Basic: 6.23

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	0.9155
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9155
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8965
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8965
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8792
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8792
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8706
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8706
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8475
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8475
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8362
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8362
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8331
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8331
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7994
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7994
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7847
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7847
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7807
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7807
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7661
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7661
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	6	0.7654
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	6	0.7654
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7621
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7621
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7421
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7421
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7397
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7397
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7379
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7379
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7317
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7317
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7137
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7137
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7082
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7082
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7053
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7053
Acyl-CoA:acyl-CoA alkyltransferase	Q8PDX2	OLEA_XANCP	Xanthomonas campestris pv. campestris	3	0.7039
Acyl-CoA:acyl-CoA alkyltransferase	Q8PDX2	OLEA_XANCP	Xanthomonas campestris pv. campestris	3	0.7039
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7013
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7013

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