Viburtinoside A - Compound Card

Viburtinoside A

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Viburtinoside A

Structure
Zoomed Structure
  • Family: Plantae - Adoxaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Acylated Iridoid Glucoside
Canonical Smiles CCOC(=O)O[C@H]1CC2C([C@@]1(O)OC(=O)OCC)[C@@](C)(OC=C2COC1OC(CO)C(C(C1OC(=O)/C=C/c1ccc(cc1)O)O)O)OC(=O)CC(C)C
InChI InChI=1S/C36H48O18/c1-6-46-33(43)51-25-15-23-21(18-49-35(5,53-27(40)14-19(3)4)31(23)36(25,45)54-34(44)47-7-2)17-48-32-30(29(42)28(41)24(16-37)50-32)52-26(39)13-10-20-8-11-22(38)12-9-20/h8-13,18-19,23-25,28-32,37-38,41-42,45H,6-7,14-17H2,1-5H3/b13-10+/t23?,24?,25-,28?,29?,30?,31?,32?,35-,36-/m0/s1
InChIKey TXBXKTCBHQVGDF-QNTHRGHTSA-N
Formula C36H48O18
HBA 18
HBD 5
MW 768.76
Rotatable Bonds 14
TPSA 252.5
LogP 2.03
Number Rings 4
Number Aromatic Rings 1
Heavy Atom Count 54
Formal Charge 0
Fraction CSP3 0.61
Exact Mass 768.28
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Viburnum tinus Adoxaceae Plantae 237959

Showing of synonyms

  • Mohamed MA, Marzouk MSA, et al. (2005). Phytochemical constituents and hepatoprotective activity of Viburnum tinus. Phytochemistry,2005,66,2780-2786. [View] [PubMed]
Pubchem: 162817622
Nmrshiftdb2: 60072671

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C=CC(=O)OC2C(OCCC2)OCC3=COCC(C34)CCC4

Level: 2

Mol. Weight: 768.76 g/mol

Structure

SMILES: O1CCCCC1OCC2=COCC(C23)CCC3

Level: 1

Mol. Weight: 768.76 g/mol

Structure

SMILES: C1OCCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 768.76 g/mol

Structure

SMILES: C1CCC(C12)COC=C2

Level: 0

Mol. Weight: 768.76 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 768.76 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 768.76 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.69
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
1.53
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
899.93

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.75
Plasma Protein Binding
43.84
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
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
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
7.84
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-22.4
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.01
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.71
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-1637274.87
Rat (Acute)
2.92
Rat (Chronic Oral)
4.09
Fathead Minnow
2073.68
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
178239.86
Hydration Free Energy
-2.92
Log(D) at pH=7.4
1.65
Log(P)
3.2
Log S
-3.53
Log(Vapor Pressure)
-5869.24
Melting Point
121.9
pKa Acid
-11.11
pKa Basic
-1.11
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.9082
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.9082
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8603
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8603
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.8528
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.8528
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.8491
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.8491
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8240
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8240
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8206
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8206
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.8163
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.8163
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7955
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7955
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7900
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7900
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7804
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7804
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7750
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7750
Glucosidase II subunit alpha Q9STC1 Q9STC1_GRALE Gracilariopsis lemaneiformis 3 0.7674
Glucosidase II subunit alpha Q9STC1 Q9STC1_GRALE Gracilariopsis lemaneiformis 3 0.7674
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7632
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7632
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7598
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7598
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7563
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7563
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7524
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7524
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7513
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7513
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7442
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7442
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7402
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7402
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7384
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7384
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7382
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7382
Casein kinase I isoform gamma-2 P78368 KC1G2_HUMAN Homo sapiens 3 0.7354
Casein kinase I isoform gamma-2 P78368 KC1G2_HUMAN Homo sapiens 3 0.7354
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7330
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7330
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7324
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7324
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 4 0.7310
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 4 0.7310
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7289
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7289
Threonine--tRNA ligase P0A8M3 SYT_ECOLI Escherichia coli 3 0.7282
Threonine--tRNA ligase P0A8M3 SYT_ECOLI Escherichia coli 3 0.7282
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7277
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7277
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7259
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7259
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 2 0.7253
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 2 0.7253
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7242
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7242
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7217
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7217
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7212
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7212
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7207
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7207
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7173
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7173
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7159
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7159
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7133
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7133
Myosin heavy chain kinase A P42527 MHCKA_DICDI Dictyostelium discoideum 2 0.7132
Myosin heavy chain kinase A P42527 MHCKA_DICDI Dictyostelium discoideum 2 0.7132
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7126
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7126
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7125
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7125
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7118
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7118
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7109
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7109
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7104
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7104
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7094
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7094
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 2 0.7085
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 2 0.7085
Protein kinase C iota type Q62074 KPCI_MOUSE Mus musculus 2 0.7079
Protein kinase C iota type Q62074 KPCI_MOUSE Mus musculus 2 0.7079
Anthranilate phosphoribosyltransferase P00500 TRPD_ACIAD Acinetobacter baylyi 2 0.7074
Anthranilate phosphoribosyltransferase P00500 TRPD_ACIAD Acinetobacter baylyi 2 0.7074
Purine nucleoside phosphorylase DeoD-type B1JL34 DEOD_YERPY Yersinia pseudotuberculosis serotype O:3 2 0.7067
Purine nucleoside phosphorylase DeoD-type B1JL34 DEOD_YERPY Yersinia pseudotuberculosis serotype O:3 2 0.7067
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 2 0.7062
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 2 0.7062
Kynurenine--oxoglutarate transaminase 1 Q16773 KAT1_HUMAN Homo sapiens 2 0.7057
Kynurenine--oxoglutarate transaminase 1 Q16773 KAT1_HUMAN Homo sapiens 2 0.7057
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7053
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7053
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7052
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7052
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7047
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7047
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7046
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7046
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 2 0.7040
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 2 0.7040
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7032
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7032
RIO-type serine/threonine-protein kinase Rio1 O28471 RIO1_ARCFU Archaeoglobus fulgidus 2 0.7028
RIO-type serine/threonine-protein kinase Rio1 O28471 RIO1_ARCFU Archaeoglobus fulgidus 2 0.7028
Succinyl-CoA:acetate CoA-transferase B3EY95 SCACT_ACEAC Acetobacter aceti 2 0.7024
Succinyl-CoA:acetate CoA-transferase B3EY95 SCACT_ACEAC Acetobacter aceti 2 0.7024
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7017
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7017
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 2 0.7016
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 2 0.7016
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7015
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7015
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7015
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7015
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 2 0.7011
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 2 0.7011
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7010
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7010
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 2 0.7008
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 2 0.7008
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7005
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7005

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