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

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

Select a section from the left sidebar

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

Structure
Zoomed Structure
  • Family: Plantae - Lactobacillaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Monoterpene Glycoside
Canonical Smiles O=C1C[C@]2(C)O[C@@H]3C([C@H]1C[C@@]2(O)O3)CSc1ccccc1C
InChI InChI=1S/C17H20O4S/c1-10-5-3-4-6-14(10)22-9-12-11-7-17(19)16(2,8-13(11)18)20-15(12)21-17/h3-6,11-12,15,19H,7-9H2,1-2H3/t11-,12?,15+,16+,17-/m1/s1
InChIKey HBUYIGGAUFFTKM-LKGUYIIYSA-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: 100969040

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)
-4.84
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.690
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.0

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.580
Plasma Protein Binding
64.21
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
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
11.210
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.070
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.070
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.540
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
Toxic
T. Pyriformis
-0.470
Rat (Acute)
3.050
Rat (Chronic Oral)
1.170
Fathead Minnow
3.920
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
376.840
Hydration Free Energy
-7.980
Log(D) at pH=7.4
2.820
Log(P)
2.51
Log S
-3.54
Log(Vapor Pressure)
-7.59
Melting Point
119.7
pKa Acid
7.08
pKa Basic
3.04
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.9268
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.9222
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.9144
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.9098
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.9091
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.9069
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8972
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.8936
Beta-2 adrenergic receptor P07550 ADRB2_HUMAN Homo sapiens 3 0.8846
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8652
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8624
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.8386
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.8257
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 3 0.8148
Class B acid phosphatase Q540U1 APHA_SALTM Salmonella typhimurium 2 0.8079
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8054
cAMP-dependent protein kinase catalytic subunit alpha P17612 KAPCA_HUMAN Homo sapiens 2 0.7938
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7932
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7932
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 2 0.7922
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR0 INHA_MYCTO Mycobacterium tuberculosis 3 0.7898
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7879
AGAP003309-PA A0A1U7F4W2 A0A1U7F4W2_ANOGA Anopheles gambiae 2 0.7854
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 2 0.7833
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7824
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7809
glutaryl-CoA dehydrogenase (ETF) Q3JP94 Q3JP94_BURP1 Burkholderia pseudomallei 2 0.7787
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7776
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7774
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7768
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7697
Cyclic AMP receptor protein Q5SID7 CRP_THET8 Thermus thermophilus 3 0.7694
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7667
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7648
Envelope glycoprotein gp160 C6G099 C6G099_9HIV1 Human immunodeficiency virus 1 2 0.7647
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7642
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7632
Albumin P14639 ALBU_SHEEP Ovis aries 2 0.7601
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7593
Metapyrocatechase Q7WYF5 Q7WYF5_9PSED Pseudomonas alkylphenolica 2 0.7589
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 2 0.7584
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7569
Aromatic-amino-acid aminotransferase P95468 TYRB_PARDE Paracoccus denitrificans 2 0.7552
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7549
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 2 0.7549
Cellular retinol-binding protein type II Q8UVG6 Q8UVG6_DANRE Danio rerio 3 0.7547
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7539
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 2 0.7521
4-chlorobenzoyl CoA ligase Q8GN86 Q8GN86_9BURK Alcaligenes sp. AL3007 2 0.7474
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7456
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7455
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 3 0.7441
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7434
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 2 0.7430
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7429
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7426
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7421
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7417
DNA-binding transcriptional dual regulator CRP P0ACJ8 CRP_ECOLI Escherichia coli 3 0.7416
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.7411
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7406
Cytochrome P450 2E1 P05181 CP2E1_HUMAN Homo sapiens 2 0.7400
Naphthalene 1,2-dioxygenase system, large oxygenase component P0A110 NDOB_PSEPU Pseudomonas putida 2 0.7396
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 2 0.7392
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7388
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7387
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7380
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7377
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7371
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 2 0.7363
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 2 0.7349
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7341
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7339
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 2 0.7338
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7331
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.7319
4-chlorobenzoyl CoA ligase Q8GN86 Q8GN86_9BURK Alcaligenes sp. AL3007 2 0.7313
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 3 0.7307
4-chlorobenzoyl CoA ligase Q8GN86 Q8GN86_9BURK Alcaligenes sp. AL3007 2 0.7302
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7298
Trichosurin Q29147 TRIC_TRIVU Trichosurus vulpecula 2 0.7291
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7280
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7279
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7275
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7269
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 2 0.7264
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7261
4-chlorobenzoyl CoA ligase Q8GN86 Q8GN86_9BURK Alcaligenes sp. AL3007 2 0.7260
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 2 0.7241
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7228
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7219
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7192
Dicamba O-demethylase, oxygenase component Q5S3I3 DDMC_STEMA Stenotrophomonas maltophilia 2 0.7179
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 2 0.7172
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 2 0.7169
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7167
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7164
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7158
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 2 0.7155
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7130
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7111
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7109
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 3 0.7105
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 2 0.7091
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7089
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7076
Nucleoside diphosphate kinase Q5UQL3 NDK_MIMIV Acanthamoeba polyphaga mimivirus 2 0.7067
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7062
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7059
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7057
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7057
Polymerase basic protein 2 P31345 PB2_I75A3 Influenza A virus 2 0.7051
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 2 0.7034
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7022
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7003
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 2 0.7001

Download SDF