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8-benzylthio-paenimetabolin-I

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)CSCc1ccccc1
InChI	InChI=1S/C17H20O4S/c1-16-8-14(18)12-7-17(16,19)21-15(20-16)13(12)10-22-9-11-5-3-2-4-6-11/h2-6,12-13,15,19H,7-10H2,1H3/t12-,13?,15+,16+,17-/m1/s1
InChIKey	HVCAYESIEMOOBK-GHHJJDSHSA-N
Formula	C₁₇H₂₀O₄S
HBA	5
HBD	1
MW	320.41
Rotatable Bonds	4
TPSA	55.76
LogP	2.35
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: 100969045

No compound-protein relationship available.

SMILES: c1ccccc1CSCC(C(O2)O3)C(C(=O)C4)CC3C24

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): -4.75
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.540
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.15

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.160
Plasma Protein Binding: 65.02
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: Substrate
CYP 2C19 Inhibitor: 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: 14.980
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.750
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.810
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.120
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: -0.800
Rat (Acute): 2.630
Rat (Chronic Oral): 1.430
Fathead Minnow: 3.950
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: 382.270
Hydration Free Energy: -8.120
Log(D) at pH=7.4: 2.140
Log(P): 2.0
Log S: -2.98
Log(Vapor Pressure): -7.24
Melting Point: 106.45
pKa Acid: 6.49
pKa Basic: 3.62

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9353
HTH-type transcriptional regulator EthR	P9WMC1	ETHR_MYCTU	Mycobacterium tuberculosis	3	0.9105
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.9066
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	3	0.8976
Disintegrin and metalloproteinase domain-containing protein 17	P78536	ADA17_HUMAN	Homo sapiens	3	0.8605
Cytochrome P450	S6BVH1	S6BVH1_RHOER	Rhodococcus erythropolis	3	0.8542
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.8542
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.8466
5-methylthioadenosine/S-adenosylhomocysteine deaminase	Q7NZ90	Q7NZ90_CHRVO	Chromobacterium violaceum	3	0.8261
Reaction center protein L chain	P0C0Y7	RCEH_RHOSH	Rhodobacter sphaeroides	3	0.8178
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.8104
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.8077
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.8017
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	2	0.7890
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7855
Gastrotropin	P51161	FABP6_HUMAN	Homo sapiens	3	0.7851
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7770
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7650
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	2	0.7648
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase	O67060	ISPE_AQUAE	Aquifex aeolicus	3	0.7647
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	2	0.7632
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7626
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.7602
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7577
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7556
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	2	0.7527
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7526
M17 leucyl aminopeptidase	Q8IL11	Q8IL11_PLAF7	Plasmodium falciparum	3	0.7513
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	2	0.7482
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	2	0.7459
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7422
DNA-binding transcriptional dual regulator CRP	P0ACJ8	CRP_ECOLI	Escherichia coli	3	0.7413
Adenosine 5'-monophosphoramidase HINT1	P49773	HINT1_HUMAN	Homo sapiens	3	0.7407
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	3	0.7362
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7336
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	2	0.7333
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7326
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	2	0.7296
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7292
Cyclic AMP receptor protein	Q5SID7	CRP_THET8	Thermus thermophilus	3	0.7284
ADP-ribosylation factor 1	P84077	ARF1_HUMAN	Homo sapiens	2	0.7282
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7281
cGMP-dependent protein kinase 2	Q13237	KGP2_HUMAN	Homo sapiens	3	0.7269
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	2	0.7247
Single-stranded-DNA-specific exonuclease RecJ	D0EM60	D0EM60_DEIRD	Deinococcus radiodurans	2	0.7241
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7231
Nucleoside diphosphate kinase	P15266	NDK_MYXXA	Myxococcus xanthus	2	0.7220
F420-dependent methylenetetrahydromethanopterin dehydrogenase	P94951	MTD_METKA	Methanopyrus kandleri	2	0.7195
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	2	0.7192
Phosphotriesterase	Q5KZU5	Q5KZU5_GEOKA	Geobacillus kaustophilus	2	0.7180
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	2	0.7161
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7150
Polymerase basic protein 2	P31345	PB2_I75A3	Influenza A virus	2	0.7139
Albumin	P02768	ALBU_HUMAN	Homo sapiens	2	0.7136
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7135
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	2	0.7121
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7121
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7095
Epothilone C/D epoxidase	Q9KIZ4	C167_SORCE	Sorangium cellulosum	2	0.7089
Histone deacetylase 8	Q9BY41	HDAC8_HUMAN	Homo sapiens	2	0.7067
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	2	0.7066
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	2	0.7053
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	2	0.7050
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7049
Collagenase 3	P45452	MMP13_HUMAN	Homo sapiens	3	0.7044
Nitric oxide synthase, inducible	P35228	NOS2_HUMAN	Homo sapiens	2	0.7042
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	2	0.7027
Methionine aminopeptidase 2	P9WK19	MAP12_MYCTU	Mycobacterium tuberculosis	3	0.7024
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7020
Plasma membrane ATPase	Q42932	Q42932_NICPL	Nicotiana plumbaginifolia	2	0.7013
Streptavidin	P22629	SAV_STRAV	Streptomyces avidinii	3	0.7003
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7000

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