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Swertiajaponin

Family: Plantae - Caprifoliaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavone Glucoside

Canonical Smiles	OC[C@H]1O[C@H]([C@@H]([C@H]([C@@H]1O)O)O)c1c(OC)cc2c(c1O)c(=O)cc(o2)c1ccc(c(c1)O)O
InChI	InChI=1S/C22H22O11/c1-31-13-6-14-16(11(26)5-12(32-14)8-2-3-9(24)10(25)4-8)19(28)17(13)22-21(30)20(29)18(27)15(7-23)33-22/h2-6,15,18,20-25,27-30H,7H2,1H3/t15-,18-,20+,21-,22+/m1/s1
InChIKey	DLVLXOYLQKCAME-DGHBBABESA-N
Formula	C₂₂H₂₂O₁₁
HBA	11
HBD	7
MW	462.41
Rotatable Bonds	4
TPSA	190.28
LogP	0.1
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	33
Formal Charge	0
Fraction CSP3	0.32
Exact Mass	462.12
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Scabiosa stellata	Caprifoliaceae	Plantae	596806

Showing of synonyms

Lehbili M, Alabdul Magid A, et al. (2018). Two new bis-iridoids isolated from Scabiosa stellata and their antibacterial, antioxidant, anti-tyrosinase and cytotoxic activities. Fitoterapia, 2018, 125, 41-48. [View] [PubMed]

Pubchem: 442659

Cas: 6980-25-2

Gnps: CCMSLIB00006482309

Zinc: ZINC000004098603

Kegg Ligand: C10187

Nmrshiftdb2: 60023014

Chembl: CHEMBL4160301

No compound-protein relationship available.

SMILES: c1ccccc1-c(cc2=O)oc(c23)ccc(c3)C4CCCCO4

Level: 2

Mol. Weight: 462.41 g/mol

SMILES: O=c1ccoc(c12)ccc(c2)C3CCCCO3

Level: 1

Mol. Weight: 462.41 g/mol

SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3

Level: 1

Mol. Weight: 462.41 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 462.41 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 462.41 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 462.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.69
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.400
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 1.38

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.880
Plasma Protein Binding: 83.84
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Non-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: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 14.030
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -1.550
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.140
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.400
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: Safe
T. Pyriformis: -117.780
Rat (Acute): 2.360
Rat (Chronic Oral): 4.240
Fathead Minnow: 3.950
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: 637.340
Hydration Free Energy: -3.890
Log(D) at pH=7.4: 0.600
Log(P): 0.59
Log S: -4.72
Log(Vapor Pressure): -13.29
Melting Point: 227.07
pKa Acid: 4.79
pKa Basic: 7.31

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	4	0.9643
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.9389
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9381
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.9201
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.9065
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9055
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8952
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8859
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.8821
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8771
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8708
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8661
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.8530
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8506
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.8447
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8362
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.8327
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.8265
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8249
Putative b-glycan phosphorylase	Q21MB1	Q21MB1_SACD2	Saccharophagus degradans	4	0.8216
Squalene synthase	P37268	FDFT_HUMAN	Homo sapiens	3	0.8187
GTP 3',8-cyclase	P69848	MOAA_STAA8	Staphylococcus aureus	4	0.8184
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8169
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8168
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.8043
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.8038
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8009
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7949
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7828
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7773
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7696
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7695
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.7673
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7655
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.7644
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7597
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	3	0.7592
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	3	0.7575
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.7513
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7502
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7496
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	P0AF12	MTNN_ECOLI	Escherichia coli	3	0.7475
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7448
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7445
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	4	0.7402
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7392
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7389
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7381
Histone deacetylase 7	Q8WUI4	HDAC7_HUMAN	Homo sapiens	3	0.7367
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7329
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	4	0.7313
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.7284
Beta-galactosidase	P00722	BGAL_ECOLI	Escherichia coli	3	0.7275
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7267
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7223
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7205
Ribosomal RNA large subunit methyltransferase J	P37634	RLMJ_ECOLI	Escherichia coli	4	0.7185
Cytosine-specific methyltransferase	Q8EVR5	Q8EVR5_MYCPE	Mycoplasma penetrans	4	0.7158
UDP-N-acetylmuramoyl-L-alanyl-D-glutamate--LD-lysine ligase	Q9WY79	MURE_THEMA	Thermotoga maritima	3	0.7154
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7153
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7137
Beta sliding clamp	P0A988	DPO3B_ECOLI	Escherichia coli	3	0.7136
Gag-Pol polyprotein	P0C6F2	POL_HV1LW	Human immunodeficiency virus type 1 group M subtype B	3	0.7116
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7098
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.7092
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7091
Fructose-1,6-bisphosphatase 1	P09467	F16P1_HUMAN	Homo sapiens	3	0.7090
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	4	0.7087
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7087
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7085
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	4	0.7079
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7057
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7042
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	3	0.7042
Acetylcholinesterase	P22303	ACES_HUMAN	Homo sapiens	3	0.7039
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7016
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7015
Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4	Q8GZB6	SUVH4_ARATH	Arabidopsis thaliana	3	0.7007

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