8-(m-tolyl)thio-paenimetabolin-I - Compound Card

8-(m-tolyl)thio-paenimetabolin-I

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8-(m-tolyl)thio-paenimetabolin-I

Structure
Zoomed Structure
  • Family: Plantae - Lactobacillaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Monoterpene Glycoside
Canonical Smiles Cc1cccc(c1)SCC1[C@H]2O[C@@]3([C@](O2)(C[C@H]1C(=O)C3)O)C
InChI InChI=1S/C17H20O4S/c1-10-4-3-5-11(6-10)22-9-13-12-7-17(19)16(2,8-14(12)18)20-15(13)21-17/h3-6,12-13,15,19H,7-9H2,1-2H3/t12-,13?,15+,16+,17-/m1/s1
InChIKey FCDORSAYLUXVBH-GHHJJDSHSA-N
Formula C17H20O4S
HBA 5
HBD 1
MW 320.41
Rotatable Bonds 3
TPSA 55.76
LogP 2.52
Number Rings 4
Number Aromatic Rings 1
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.59
Exact Mass 320.11
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Lactobacillus brevis Lactobacillaceae Plantae 1580

Showing of synonyms

  • Abdel-Hafez A.A, Meselhy M.R, et al. (1998). Potent Anticonvulsant Paeonimetabolin-I Derivatives Obtained by Incubation of Paeoniflorin and Thiol Compounds with Lactobacillus brevis.. Chemical & pharmaceutical bulletin, 1998, 46(9), 1486-7. [View] [PubMed]
Pubchem: 100969042

No compound-protein relationship available.

Structure

SMILES: C12C3CC(C(=O)C1)C(C(O2)O3)CSc4ccccc4

Level: 1

Mol. Weight: 320.41 g/mol

Structure

SMILES: C12C3CC(C(=O)C1)CC(O2)O3

Level: 0

Mol. Weight: 320.41 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 320.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.86
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.66
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.21

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.37
Plasma Protein Binding
61.07
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
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
11.2
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.97
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.27
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.41
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
Toxic
T. Pyriformis
-0.51
Rat (Acute)
2.92
Rat (Chronic Oral)
1.2
Fathead Minnow
3.92
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
374.6
Hydration Free Energy
-7.54
Log(D) at pH=7.4
2.86
Log(P)
2.42
Log S
-3.49
Log(Vapor Pressure)
-7.35
Melting Point
105.71
pKa Acid
6.91
pKa Basic
3.26
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 3 0.9522
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.9371
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.9278
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9253
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.9228
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.8934
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.8853
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.8746
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.8461
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.8279
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 3 0.8122
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.8046
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8018
DNA-binding transcriptional dual regulator CRP P0ACJ8 CRP_ECOLI Escherichia coli 3 0.7969
Cytochrome b-c1 complex subunit 1, mitochondrial P31800 QCR1_BOVIN Bos taurus 3 0.7903
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7891
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7824
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7787
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 2 0.7744
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 2 0.7740
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7726
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7707
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7707
Achbp I6L8L2 I6L8L2_CAPTE Capitella teleta 2 0.7671
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 2 0.7670
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7649
Aromatic-amino-acid aminotransferase P95468 TYRB_PARDE Paracoccus denitrificans 2 0.7648
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7636
3-hydroxydecanoyl-[acyl-carrier-protein] dehydratase O33877 FABA_PSEAE Pseudomonas aeruginosa 2 0.7633
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 2 0.7623
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7622
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7613
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7607
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7597
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 2 0.7576
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 2 0.7569
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7557
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7536
Naphthalene 1,2-dioxygenase system, large oxygenase component P0A110 NDOB_PSEPU Pseudomonas putida 2 0.7526
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 2 0.7524
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7519
Albumin P14639 ALBU_SHEEP Ovis aries 2 0.7509
Cyclic AMP receptor protein Q5SID7 CRP_THET8 Thermus thermophilus 3 0.7509
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 2 0.7504
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7499
Dicamba O-demethylase, oxygenase component Q5S3I3 DDMC_STEMA Stenotrophomonas maltophilia 2 0.7495
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7490
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7489
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7475
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 2 0.7464
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7439
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7438
cAMP-dependent protein kinase catalytic subunit alpha P17612 KAPCA_HUMAN Homo sapiens 2 0.7419
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7415
Cytochrome P450 2E1 P05181 CP2E1_HUMAN Homo sapiens 2 0.7412
Troponin C, slow skeletal and cardiac muscles P63316 TNNC1_HUMAN Homo sapiens 2 0.7408
4-chlorobenzoyl CoA ligase Q8GN86 Q8GN86_9BURK Alcaligenes sp. AL3007 2 0.7395
Scytalone dehydratase P56221 SCYD_MAGO7 Pyricularia oryzae 3 0.7381
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 2 0.7358
4-chlorobenzoyl CoA ligase Q8GN86 Q8GN86_9BURK Alcaligenes sp. AL3007 2 0.7354
4-chlorobenzoyl CoA ligase Q8GN86 Q8GN86_9BURK Alcaligenes sp. AL3007 2 0.7351
glutaryl-CoA dehydrogenase (ETF) Q3JP94 Q3JP94_BURP1 Burkholderia pseudomallei 2 0.7346
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7343
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7337
Beta-2 adrenergic receptor P07550 ADRB2_HUMAN Homo sapiens 3 0.7320
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7320
Kynurenine 3-monooxygenase P38169 KMO_YEAST Saccharomyces cerevisiae 2 0.7320
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 2 0.7308
Trichosurin Q29147 TRIC_TRIVU Trichosurus vulpecula 2 0.7296
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7293
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7289
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7281
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7280
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7279
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 3 0.7277
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7273
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 3 0.7273
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7256
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7246
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7227
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7224
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7193
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2 O88703 HCN2_MOUSE Mus musculus 3 0.7192
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 2 0.7191
4-chlorobenzoyl CoA ligase Q8GN86 Q8GN86_9BURK Alcaligenes sp. AL3007 2 0.7189
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7187
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 2 0.7178
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7162
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7154
Scytalone dehydratase P56221 SCYD_MAGO7 Pyricularia oryzae 3 0.7134
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7127
Disintegrin and metalloproteinase domain-containing protein 17 P78536 ADA17_HUMAN Homo sapiens 3 0.7127
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7115
Nitroreductase domain-containing protein Q8DW21 Q8DW21_STRMU Streptococcus mutans serotype c 3 0.7109
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 2 0.7107
1-deoxy-D-xylulose 5-phosphate reductoisomerase P45568 DXR_ECOLI Escherichia coli 2 0.7104
AGAP003309-PA A0A1U7F4W2 A0A1U7F4W2_ANOGA Anopheles gambiae 2 0.7103
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.7101
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7094
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7085
Cytochrome P450 2E1 P05181 CP2E1_HUMAN Homo sapiens 2 0.7074
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7065
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7049
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7047
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7041
Metapyrocatechase Q7WYF5 Q7WYF5_9PSED Pseudomonas alkylphenolica 2 0.7037
Ribosomal protein S6 kinase beta-1 P23443 KS6B1_HUMAN Homo sapiens 3 0.7033
Histone deacetylase-like amidohydrolase Q70I53 HDAH_ALCSD Alcaligenes sp.) 2 0.7024
Class B acid phosphatase Q540U1 APHA_SALTM Salmonella typhimurium 2 0.7015

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