Blephariside B - Compound Card

Blephariside B

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Blephariside B

Structure
Zoomed Structure
  • Family: Plantae - Acanthaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavonol Glycoside
Canonical Smiles OCC1O[C@@H](Oc2c(oc3c(c2=O)c(O)cc(c3)O)c2ccc(c(c2)O[C@@H]2OC(COC(=O)/C=C/Cc3ccc(c(c3)O)O)[C@H]([C@@H](C2O)O)O)O)C([C@H]([C@@H]1O)O)O
InChI InChI=1S/C37H38O20/c38-12-23-27(45)30(48)33(51)37(55-23)57-35-29(47)26-20(43)10-16(39)11-22(26)53-34(35)15-5-7-18(41)21(9-15)54-36-32(50)31(49)28(46)24(56-36)13-52-25(44)3-1-2-14-4-6-17(40)19(42)8-14/h1,3-11,23-24,27-28,30-33,36-43,45-46,48-51H,2,12-13H2/b3-1+/t23?,24?,27-,28-,30+,31+,32?,33?,36-,37+/m1/s1
InChIKey JWPKIAYHWVEGAD-LTDSZXQWSA-N
Formula C37H38O20
HBA 20
HBD 12
MW 802.69
Rotatable Bonds 11
TPSA 336.19
LogP -1.3
Number Rings 6
Number Aromatic Rings 4
Heavy Atom Count 57
Formal Charge 0
Fraction CSP3 0.35
Exact Mass 802.2
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: 162951757
Nmrshiftdb2: 70098929

No compound-protein relationship available.

Structure

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

Level: 4

Mol. Weight: 802.69 g/mol

Structure

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

Level: 3

Mol. Weight: 802.69 g/mol

Structure

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

Level: 3

Mol. Weight: 802.69 g/mol

Structure

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

Level: 2

Mol. Weight: 802.69 g/mol

Structure

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

Level: 2

Mol. Weight: 802.69 g/mol

Structure

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

Level: 2

Mol. Weight: 802.69 g/mol

Structure

SMILES: O1CCCCC1COC(=O)C=CCc2ccccc2

Level: 1

Mol. Weight: 802.69 g/mol

Structure

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

Level: 1

Mol. Weight: 802.69 g/mol

Structure

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

Level: 1

Mol. Weight: 802.69 g/mol

Structure

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 802.69 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 802.69 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 802.69 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 802.69 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
46.23
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
6869.29

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.71
Plasma Protein Binding
46.14
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
10.63
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-161.06
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.02
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
8.28
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
-12463505.31
Rat (Acute)
2.32
Rat (Chronic Oral)
5.03
Fathead Minnow
15741.1
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
1393781.07
Hydration Free Energy
-2.92
Log(D) at pH=7.4
-0.39
Log(P)
0.06
Log S
-5.23
Log(Vapor Pressure)
-45869.68
Melting Point
255.95
pKa Acid
-292.21
pKa Basic
8.52
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 0.9271
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9271
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9126
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9126
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.9027
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.9027
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8935
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8935
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8873
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8873
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8849
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8849
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8790
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8790
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8698
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8698
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8645
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8645
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8571
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8571
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.8557
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.8557
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.8438
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.8438
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8398
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8398
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8309
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8309
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8273
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8273
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8265
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8265
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8217
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8217
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8190
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8190
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.7993
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.7993
Aminoglycoside N(3)-acetyltransferase A0A3P1UCA6 Q81P86_BACAN Bacillus anthracis 3 0.7895
Aminoglycoside N(3)-acetyltransferase A0A3P1UCA6 Q81P86_BACAN Bacillus anthracis 3 0.7895
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.7884
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.7884
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7835
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7835
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7783
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7783
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7754
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7754
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7746
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7746
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7731
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7731
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7700
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7700
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7696
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7696
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7676
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7676
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7468
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7468
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7405
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7405
Caffeoyl-CoA O-methyltransferase Q40313 CAMT_MEDSA Medicago sativa 3 0.7376
Caffeoyl-CoA O-methyltransferase Q40313 CAMT_MEDSA Medicago sativa 3 0.7376
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7365
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7365
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7314
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7314
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7290
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7290
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7280
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7280
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7247
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7247
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.7217
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.7217
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7204
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7204
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 4 0.7188
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 4 0.7188
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7182
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7182
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7159
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7159
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 2 0.7131
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 2 0.7131
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7115
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7115
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 3 0.7115
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 3 0.7115
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 2 0.7108
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 2 0.7108
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7101
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7101
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7100
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7100
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7100
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7100
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7096
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7096
Periplasmic pH-dependent serine endoprotease DegQ P39099 DEGQ_ECOLI Escherichia coli 4 0.7070
Periplasmic pH-dependent serine endoprotease DegQ P39099 DEGQ_ECOLI Escherichia coli 4 0.7070
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7066
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7066
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7059
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7059
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7058
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7058
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7043
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7043
Acyl-CoA:acyl-CoA alkyltransferase Q8PDX2 OLEA_XANCP Xanthomonas campestris pv. campestris 3 0.7037
Acyl-CoA:acyl-CoA alkyltransferase Q8PDX2 OLEA_XANCP Xanthomonas campestris pv. campestris 3 0.7037
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7028
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7028
Neopullulanase 2 Q08751 NEPU2_THEVU Thermoactinomyces vulgaris 3 0.7022
Neopullulanase 2 Q08751 NEPU2_THEVU Thermoactinomyces vulgaris 3 0.7022
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7021
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7021
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7021
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7021
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7013
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7013
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7011
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7011
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7009
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7009
3',5'-cyclic-AMP phosphodiesterase 4B Q07343 PDE4B_HUMAN Homo sapiens 3 0.7006
3',5'-cyclic-AMP phosphodiesterase 4B Q07343 PDE4B_HUMAN Homo sapiens 3 0.7006
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7001
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7001

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