6-O-[(2''-O-p-methoxy-cis-cinnamoyl-3''-O-acetyl)-alpha-L-rhamnopyranosyl]-catalpol - Compound Card

6-O-[(2''-O-p-methoxy-cis-cinnamoyl-3''-O-acetyl)-alpha-L-rhamnopyranosyl]-catalpol

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6-O-[(2''-O-p-methoxy-cis-cinnamoyl-3''-O-acetyl)-alpha-L-rhamnopyranosyl]-catalpol

Structure
Zoomed Structure
  • Family: Plantae - Scrophulariaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Iridoid Glycoside
Canonical Smiles COc1cc(ccc1O)C(=O)OC[C@H]1OC(O[C@@H]2OC=C[C@@H]3[C@H]2[C@H](C)[C@H]([C@H]3O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C23H30O12/c1-9-15-11(17(26)16(9)25)5-6-32-22(15)35-23-20(29)19(28)18(27)14(34-23)8-33-21(30)10-3-4-12(24)13(7-10)31-2/h3-7,9,11,14-20,22-29H,8H2,1-2H3/t9-,11+,14+,15+,16+,17-,18+,19-,20+,22-,23?/m0/s1
InChIKey KRBXVXVIFDREQY-YDDPPXOHSA-N
Formula C23H30O12
HBA 12
HBD 6
MW 498.48
Rotatable Bonds 6
TPSA 184.6
LogP -1.14
Number Rings 4
Number Aromatic Rings 1
Heavy Atom Count 35
Formal Charge 0
Fraction CSP3 0.61
Exact Mass 498.17
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Verbascum dentifolium Scrophulariaceae Plantae 512637

Showing of synonyms

  • Arrif S, Lavaud C, et al. (2008). Iridoids from Verbascum dentifolium. Biochemical Systematics and Ecology,2008,36(8),669-673. [View]
Pubchem: 162817087
Nmrshiftdb2: 70024412

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(=O)OCC2CCCC(O2)OC(OC=C3)C(C34)CCC4

Level: 2

Mol. Weight: 498.48 g/mol

Structure

SMILES: C1CCC(C12)C(OC=C2)OC3CCCCO3

Level: 1

Mol. Weight: 498.48 g/mol

Structure

SMILES: c1ccccc1C(=O)OCC2CCCCO2

Level: 1

Mol. Weight: 498.48 g/mol

Structure

SMILES: C1CCC(C12)COC=C2

Level: 0

Mol. Weight: 498.48 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 498.48 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 498.48 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.03
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.090
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.48

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.780
Plasma Protein Binding
57.79
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
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
6.560
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-3.170
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.980
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
4.730
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
-354.990
Rat (Acute)
2.400
Rat (Chronic Oral)
3.770
Fathead Minnow
4.210
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
528.550
Hydration Free Energy
-3.230
Log(D) at pH=7.4
0.780
Log(P)
0.12
Log S
-1.87
Log(Vapor Pressure)
-12.57
Melting Point
172.49
pKa Acid
4.52
pKa Basic
2.78
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9420
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9420
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.9266
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.9266
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
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8997
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8997
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8901
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8901
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8839
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8839
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8762
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8762
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8760
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8760
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8514
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8514
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8454
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8454
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8353
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8353
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8266
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8266
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.8235
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.8235
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8207
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8207
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.8082
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.8082
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8049
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8049
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7971
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7971
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7940
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7940
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7868
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7868
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7753
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7753
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7706
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7706
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7662
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7662
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7616
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7616
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7538
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7538
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7516
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7516
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7483
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7483
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7404
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7404
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7364
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7364
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7348
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7348
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7323
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7323
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7321
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7321
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7317
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7317
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7305
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7305
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7299
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7299
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 3 0.7297
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 3 0.7297
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7262
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7262
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7258
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7258
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7241
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7241
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7228
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7228
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7221
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7221
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7218
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7218
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7213
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7213
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7194
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7194
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7184
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7184
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7183
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7183
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7169
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7169
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 2 0.7167
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 2 0.7167
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 2 0.7150
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 2 0.7150
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7137
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7137
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7132
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7132
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7129
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7129
Histone-lysine N-methyltransferase 2A Q03164 KMT2A_HUMAN Homo sapiens 3 0.7128
Histone-lysine N-methyltransferase 2A Q03164 KMT2A_HUMAN Homo sapiens 3 0.7128
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7121
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7121
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7115
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7115
Maltose/maltodextrin-binding periplasmic protein P0AEX9 MALE_ECOLI Escherichia coli 3 0.7110
Maltose/maltodextrin-binding periplasmic protein P0AEX9 MALE_ECOLI Escherichia coli 3 0.7110
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.7108
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.7108
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7105
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7105
Oxygenase Q194P4 Q194P4_STRAA Streptomyces argillaceus 3 0.7096
Oxygenase Q194P4 Q194P4_STRAA Streptomyces argillaceus 3 0.7096
ATP-dependent protease subunit HslV P0A7B8 HSLV_ECOLI Escherichia coli 3 0.7088
ATP-dependent protease subunit HslV P0A7B8 HSLV_ECOLI Escherichia coli 3 0.7088
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 3 0.7074
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 3 0.7074
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7068
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7068
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7064
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7064
Histone-lysine N-methyltransferase 2C Q8NEZ4 KMT2C_HUMAN Homo sapiens 3 0.7054
Histone-lysine N-methyltransferase 2C Q8NEZ4 KMT2C_HUMAN Homo sapiens 3 0.7054
Neopullulanase 2 Q08751 NEPU2_THEVU Thermoactinomyces vulgaris 3 0.7046
Neopullulanase 2 Q08751 NEPU2_THEVU Thermoactinomyces vulgaris 3 0.7046
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7034
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7034
Elongation factor Tu 1 P0CE47 EFTU1_ECOLI Escherichia coli 3 0.7029
Elongation factor Tu 1 P0CE47 EFTU1_ECOLI Escherichia coli 3 0.7029
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7026
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7026
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7009
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7009

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