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8-(2-naphthyl)thio-paenimetabolin-I

Family: 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)CSc1ccc2c(c1)cccc2
InChI	InChI=1S/C20H20O4S/c1-19-10-17(21)15-9-20(19,22)24-18(23-19)16(15)11-25-14-7-6-12-4-2-3-5-13(12)8-14/h2-8,15-16,18,22H,9-11H2,1H3/t15-,16?,18+,19+,20-/m1/s1
InChIKey	FWDWOOQUVYRKDJ-XEUDDIOWSA-N
Formula	C₂₀H₂₀O₄S
HBA	5
HBD	1
MW	356.44
Rotatable Bonds	3
TPSA	55.76
LogP	3.36
Number Rings	5
Number Aromatic Rings	2
Heavy Atom Count	25
Formal Charge	0
Fraction CSP3	0.45
Exact Mass	356.11
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: 100969044

No compound-protein relationship available.

SMILES: C12C3CC(C(=O)C1)C(C(O2)O3)CSc(c4)ccc(c45)cccc5

Level: 1

Mol. Weight: 326.42 g/mol

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

Level: 0

Mol. Weight: 154.16 g/mol

SMILES: c1cccc(c12)cccc2

Level: 0

Mol. Weight: 128.17 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.0
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.540
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.7

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.510
Plasma Protein Binding: 86.39
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: 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: 9.360
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.540
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.340
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 5.960
Micronucleos: Toxic
NR-AhR: Toxic
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: -3.600
Rat (Acute): 3.120
Rat (Chronic Oral): 1.470
Fathead Minnow: 4.290
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: 440.010
Hydration Free Energy: -7.090
Log(D) at pH=7.4: 3.320
Log(P): 3.26
Log S: -4.37
Log(Vapor Pressure): -8.52
Melting Point: 131.96
pKa Acid: 7.01
pKa Basic: 3.24

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	0.9520
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.9512
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.9276
Tetracycline repressor protein class B from transposon Tn10	P04483	TETR2_ECOLX	Escherichia coli	3	0.9129
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase	Q84HC8	NCSB1_STRCZ	Streptomyces carzinostaticus	3	0.9078
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	3	0.8928
Carminomycin 4-O-methyltransferase DnrK	Q06528	DNRK_STRPE	Streptomyces peucetius	3	0.8830
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.8710
Thymidine kinase	P0DTH5	KITH_HHV11	Human herpesvirus 1	3	0.8592
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8469
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.8397
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.8286
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.8173
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	3	0.8120
Enoyl-[acyl-carrier-protein] reductase [NADH]	P9WGR1	INHA_MYCTU	Mycobacterium tuberculosis	3	0.8110
Disintegrin and metalloproteinase domain-containing protein 17	P78536	ADA17_HUMAN	Homo sapiens	3	0.8031
Enoyl-[acyl-carrier-protein] reductase [NADH]	P9WGR1	INHA_MYCTU	Mycobacterium tuberculosis	3	0.8026
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7956
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7931
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7870
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	2	0.7825
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7824
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7815
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	2	0.7718
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7706
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7669
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7665
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	2	0.7661
Class B acid phosphatase	Q540U1	APHA_SALTM	Salmonella typhimurium	2	0.7661
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	2	0.7657
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	F6MZ55	F6MZ55_9FIRM	Sporomusa ovata	2	0.7643
Glutathione S-transferase P	P09211	GSTP1_HUMAN	Homo sapiens	2	0.7642
Cyclic AMP receptor protein	Q5SID7	CRP_THET8	Thermus thermophilus	3	0.7628
DNA-binding transcriptional dual regulator CRP	P0ACJ8	CRP_ECOLI	Escherichia coli	3	0.7615
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase	Q84HC8	NCSB1_STRCZ	Streptomyces carzinostaticus	3	0.7602
Reaction center protein L chain	P0C0Y7	RCEH_RHOSH	Rhodobacter sphaeroides	3	0.7583
Thiamine-phosphate synthase	P39594	THIE_BACSU	Bacillus subtilis	2	0.7581
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7580
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7574
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7560
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	F6MZ55	F6MZ55_9FIRM	Sporomusa ovata	2	0.7535
prolyl oligopeptidase	Q9X6R4	Q9X6R4_AERCA	Aeromonas caviae	3	0.7527
Gag-Pol polyprotein	P03366	POL_HV1B1	Human immunodeficiency virus type 1 group M subtype B	2	0.7522
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7514
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	2	0.7505
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.7495
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7494
Aromatic-amino-acid aminotransferase	P95468	TYRB_PARDE	Paracoccus denitrificans	2	0.7485
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7455
Glutathione S-transferase A1	P08263	GSTA1_HUMAN	Homo sapiens	2	0.7447
Albumin	P14639	ALBU_SHEEP	Ovis aries	2	0.7436
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7432
Thiamine-phosphate synthase	P39594	THIE_BACSU	Bacillus subtilis	2	0.7429
Thiamine-phosphate synthase	P39594	THIE_BACSU	Bacillus subtilis	2	0.7417
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7416
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7406
Kynurenine 3-monooxygenase	P38169	KMO_YEAST	Saccharomyces cerevisiae	2	0.7394
Casein kinase II subunit alpha'	P19784	CSK22_HUMAN	Homo sapiens	2	0.7389
4-chlorobenzoyl CoA ligase	Q8GN86	Q8GN86_9BURK	Alcaligenes sp. AL3007	2	0.7384
Beta-2 adrenergic receptor	P07550	ADRB2_HUMAN	Homo sapiens	2	0.7383
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	2	0.7381
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	2	0.7377
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7333
4-chlorobenzoyl CoA ligase	Q8GN86	Q8GN86_9BURK	Alcaligenes sp. AL3007	2	0.7322
Albumin	P02768	ALBU_HUMAN	Homo sapiens	2	0.7320
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	4	0.7313
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7313
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	2	0.7313
Cytochrome P450 2E1	P05181	CP2E1_HUMAN	Homo sapiens	2	0.7291
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7284
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7282
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	2	0.7272
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7245
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7240
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7236
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	2	0.7232
Pteridine reductase, putative	Q581W1	Q581W1_TRYB2	Trypanosoma brucei brucei	2	0.7229
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	2	0.7228
Multidrug transporter MdfA	P0AEY8	MDFA_ECOLI	Escherichia coli	3	0.7224
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7218
Ribosomal protein S6 kinase beta-1	P23443	KS6B1_HUMAN	Homo sapiens	3	0.7208
Naphthalene 1,2-dioxygenase system, large oxygenase component	P0A110	NDOB_PSEPU	Pseudomonas putida	2	0.7208
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7206
Aromatic-amino-acid aminotransferase	P95468	TYRB_PARDE	Paracoccus denitrificans	2	0.7200
4-chlorobenzoyl CoA ligase	Q8GN86	Q8GN86_9BURK	Alcaligenes sp. AL3007	2	0.7193
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7188
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7188
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7187
5-methylthioadenosine/S-adenosylhomocysteine deaminase	Q7NZ90	Q7NZ90_CHRVO	Chromobacterium violaceum	3	0.7185
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	2	0.7179
4-chlorobenzoyl CoA ligase	Q8GN86	Q8GN86_9BURK	Alcaligenes sp. AL3007	2	0.7161
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	2	0.7149
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7149
Troponin C, slow skeletal and cardiac muscles	P63316	TNNC1_HUMAN	Homo sapiens	2	0.7147
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	2	0.7145
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4	Q9Y3Q4	HCN4_HUMAN	Homo sapiens	3	0.7137
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7134
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	2	0.7131
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7123
prolyl oligopeptidase	Q9X6R4	Q9X6R4_AERCA	Aeromonas caviae	2	0.7104
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7103
Gag-Pol polyprotein	P03366	POL_HV1B1	Human immunodeficiency virus type 1 group M subtype B	2	0.7070
Prolyl endopeptidase	P23687	PPCE_PIG	Sus scrofa	3	0.7044
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	2	0.7010
Methionine aminopeptidase 2	P50579	MAP2_HUMAN	Homo sapiens	2	0.7010
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7002
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7001
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4	Q9Y3Q4	HCN4_HUMAN	Homo sapiens	3	0.7001

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