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

Family: Plantae - Lactobacillaceae
Kingdom: Plantae
Class: Terpenoid
- Subclass: Monoterpene Glycoside

Canonical Smiles	Cc1ccc(cc1)SCC1[C@H]2O[C@@]3([C@](O2)(C[C@H]1C(=O)C3)O)C
InChI	InChI=1S/C17H20O4S/c1-10-3-5-11(6-4-10)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	YYJOXYIBEPTHJT-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: 100969043

No compound-protein relationship available.

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

Level: 1

Mol. Weight: 320.41 g/mol

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

Level: 0

Mol. Weight: 320.41 g/mol

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: -4.64
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.18

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.33
Plasma Protein Binding: 61.02
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: 11.34
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.92
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.22
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.37
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: -0.48
Rat (Acute): 2.83
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: 375.39
Hydration Free Energy: -7.65
Log(D) at pH=7.4: 2.81
Log(P): 2.43
Log S: -3.61
Log(Vapor Pressure): -7.29
Melting Point: 112.49
pKa Acid: 6.82
pKa Basic: 3.38

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	0.9441
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.9272
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9223
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	3	0.8924
Disintegrin and metalloproteinase domain-containing protein 17	P78536	ADA17_HUMAN	Homo sapiens	3	0.8496
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.8267
Nitroreductase domain-containing protein	Q8DW21	Q8DW21_STRMU	Streptococcus mutans serotype c	3	0.8232
Carminomycin 4-O-methyltransferase DnrK	Q06528	DNRK_STRPE	Streptomyces peucetius	3	0.8159
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8152
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	3	0.8093
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.8019
DNA-binding transcriptional dual regulator CRP	P0ACJ8	CRP_ECOLI	Escherichia coli	3	0.7870
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7839
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7830
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7823
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7766
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7760
Cyclic AMP receptor protein	Q5SID7	CRP_THET8	Thermus thermophilus	3	0.7750
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	2	0.7725
Thiamine-phosphate synthase	P39594	THIE_BACSU	Bacillus subtilis	2	0.7721
Naphthalene 1,2-dioxygenase system, large oxygenase component	P0A110	NDOB_PSEPU	Pseudomonas putida	2	0.7693
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7674
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7660
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7651
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	2	0.7621
Aromatic-amino-acid aminotransferase	P95468	TYRB_PARDE	Paracoccus denitrificans	2	0.7585
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	2	0.7567
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	2	0.7560
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7559
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7555
Albumin	P14639	ALBU_SHEEP	Ovis aries	2	0.7543
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	F6MZ55	F6MZ55_9FIRM	Sporomusa ovata	2	0.7539
4-chlorobenzoyl CoA ligase	Q8GN86	Q8GN86_9BURK	Alcaligenes sp. AL3007	2	0.7497
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	2	0.7471
4-chlorobenzoyl CoA ligase	Q8GN86	Q8GN86_9BURK	Alcaligenes sp. AL3007	2	0.7433
Troponin C, slow skeletal and cardiac muscles	P63316	TNNC1_HUMAN	Homo sapiens	2	0.7432
4-chlorobenzoyl CoA ligase	Q8GN86	Q8GN86_9BURK	Alcaligenes sp. AL3007	2	0.7425
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7402
Glutathione S-transferase P	P09211	GSTP1_HUMAN	Homo sapiens	2	0.7399
Glutathione S-transferase A1	P08263	GSTA1_HUMAN	Homo sapiens	2	0.7371
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase	Q84HC8	NCSB1_STRCZ	Streptomyces carzinostaticus	2	0.7361
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	4	0.7345
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	3	0.7339
Thiamine-phosphate synthase	P39594	THIE_BACSU	Bacillus subtilis	2	0.7296
Achbp	I6L8L2	I6L8L2_CAPTE	Capitella teleta	2	0.7274
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7270
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7254
Ribosomal protein S6 kinase beta-1	P23443	KS6B1_HUMAN	Homo sapiens	3	0.7247
Gag-Pol polyprotein	P03366	POL_HV1B1	Human immunodeficiency virus type 1 group M subtype B	2	0.7237
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7197
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7189
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7183
Death-associated protein kinase 3	O43293	DAPK3_HUMAN	Homo sapiens	2	0.7176
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	F6MZ55	F6MZ55_9FIRM	Sporomusa ovata	2	0.7172
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7169
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	2	0.7167
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4	Q9Y3Q4	HCN4_HUMAN	Homo sapiens	3	0.7160
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	2	0.7159
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	2	0.7154
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7139
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7131
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7126
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	2	0.7118
3-hydroxydecanoyl-[acyl-carrier-protein] dehydratase	O33877	FABA_PSEAE	Pseudomonas aeruginosa	2	0.7105
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	2	0.7101
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2	O88703	HCN2_MOUSE	Mus musculus	3	0.7097
Metapyrocatechase	Q7WYF5	Q7WYF5_9PSED	Pseudomonas alkylphenolica	2	0.7092
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7091
Reaction center protein L chain	P0C0Y7	RCEH_RHOSH	Rhodobacter sphaeroides	3	0.7071
Albumin	P02768	ALBU_HUMAN	Homo sapiens	2	0.7059
Class B acid phosphatase	Q540U1	APHA_SALTM	Salmonella typhimurium	2	0.7057
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	2	0.7049
GCN5-related N-acetyltransferase	B1YEL6	B1YEL6_EXIS2	Exiguobacterium sibiricum	3	0.7028

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