Helioscopinin B - Compound Card

Helioscopinin B

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Helioscopinin B

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Tannin
Canonical Smiles O[C@@H]1C2COC(=O)c3cc(O)c(c(c3c3c(C(=O)O[C@H](O2)C([C@@H]1OC(=O)c1cc(O)c(c(c1)O)O)O)cc(c(c3O)O)O)O)O
InChI InChI=1S/C27H22O18/c28-9-1-6(2-10(29)16(9)32)24(39)44-23-19(35)13-5-42-25(40)7-3-11(30)17(33)20(36)14(7)15-8(4-12(31)18(34)21(15)37)26(41)45-27(43-13)22(23)38/h1-4,13,19,22-23,27-38H,5H2/t13?,19-,22?,23-,27+/m1/s1
InChIKey ISRNLRCYYLHRQD-ZHQJDPFESA-N
Formula C27H22O18
HBA 18
HBD 11
MW 634.46
Rotatable Bonds 2
TPSA 310.66
LogP -0.3
Number Rings 5
Number Aromatic Rings 3
Heavy Atom Count 45
Formal Charge 0
Fraction CSP3 0.22
Exact Mass 634.08
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Euphorbia helioscopia Euphorbiaceae Plantae 154990

Showing of synonyms

  • Mohamed AH, Hegazy MF, et al. (2012). Euphorbia helioscopia: Chemical constituents and biological activities. International Journal of Phytopharmacology,2012,3(1),78-90. [View]
Pubchem: 162888536

No compound-protein relationship available.

Structure

SMILES: c1cccc2C(=O)OC(O3)CC(OC(=O)c4ccccc4)CC3COC(=O)c(c5c12)cccc5

Level: 1

Mol. Weight: 634.46 g/mol

Structure

SMILES: c1cccc(c1c23)C(=O)OCC4CCCC(O4)OC(=O)c2cccc3

Level: 0

Mol. Weight: 634.46 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 634.46 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.58
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.5
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
18.32

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.49
Plasma Protein Binding
24.99
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
12.53
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-4.18
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.9
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.01
Micronucleos
Toxic
NR-AhR
Toxic
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
-28702.03
Rat (Acute)
2.44
Rat (Chronic Oral)
4.23
Fathead Minnow
55.99
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
403.2
Hydration Free Energy
-2.93
Log(D) at pH=7.4
-1.75
Log(P)
0.06
Log S
-4.53
Log(Vapor Pressure)
-19.05
Melting Point
277.89
pKa Acid
5.13
pKa Basic
7.23
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 0.9254
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9254
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.9138
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.9138
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8782
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8782
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8722
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8722
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8644
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8644
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8574
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8574
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8547
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8547
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8511
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8511
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8453
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8453
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8425
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8425
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8401
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8401
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.8398
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.8398
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8333
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8333
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8232
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8232
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8191
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8191
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8182
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8182
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8114
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8114
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 4 0.8046
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 4 0.8046
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8042
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8042
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 3 0.8039
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 3 0.8039
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8026
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8026
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7942
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7942
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7939
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7939
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7910
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7910
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 4 0.7841
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 4 0.7841
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7800
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7800
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7709
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7709
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7670
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7670
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7644
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7644
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7609
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7609
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7585
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7585
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7578
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7578
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7520
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7520
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7504
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7504
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7483
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7483
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7405
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7405
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7381
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7381
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7310
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7310
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7261
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7261
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7256
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7256
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7248
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7248
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7223
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7223
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7216
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7216
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7202
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7202
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7198
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7198
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7186
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7186
Mitogen-activated protein kinase FUS3 P16892 FUS3_YEAST Saccharomyces cerevisiae 4 0.7177
Mitogen-activated protein kinase FUS3 P16892 FUS3_YEAST Saccharomyces cerevisiae 4 0.7177
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7167
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7167
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7166
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7166
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7160
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7160
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7158
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7158
Single-strand selective monofunctional uracil DNA glycosylase Q9YGN6 SMUG1_XENLA Xenopus laevis 4 0.7118
Single-strand selective monofunctional uracil DNA glycosylase Q9YGN6 SMUG1_XENLA Xenopus laevis 4 0.7118
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7116
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7116
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7094
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7094
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7060
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7060
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7053
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.7053
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7038
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7038
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7029
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7029
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7004
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7004

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