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Stenopalustroside A

Family: Plantae - Thymelaeaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavonol Glycoside

Canonical Smiles	O=C(OCC1O[C@@H](Oc2c(oc3c(c2=O)c(O)cc(c3)O)c2ccc(cc2)O)C([C@H]([C@@H]1O)OC(=O)/C=C\c1ccc(cc1)O)O)/C=C\c1ccc(cc1)O
InChI	InChI=1S/C39H32O15/c40-23-9-1-20(2-10-23)5-15-30(45)50-19-29-33(47)37(53-31(46)16-6-21-3-11-24(41)12-4-21)35(49)39(52-29)54-38-34(48)32-27(44)17-26(43)18-28(32)51-36(38)22-7-13-25(42)14-8-22/h1-18,29,33,35,37,39-44,47,49H,19H2/b15-5-,16-6-/t29?,33-,35?,37+,39+/m1/s1
InChIKey	NFSCOXCDAAETPI-XPENEVEOSA-N
Formula	C₃₉H₃₂O₁₅
HBA	15
HBD	7
MW	740.67
Rotatable Bonds	10
TPSA	242.88
LogP	3.7
Number Rings	6
Number Aromatic Rings	5
Heavy Atom Count	54
Formal Charge	0
Fraction CSP3	0.15
Exact Mass	740.17
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Thymelaea microphylla	Thymelaeaceae	Plantae	224056

Showing of synonyms

Kerbab K, Mekhelfi T, et al. (2015). Chemical composition and antioxidant activity of a polar extract of Thymelaea microphylla Coss. Et Dur. Nat Prod Res,2015,29(7),671-5. [View] [PubMed]

Pubchem: 44259014

No compound-protein relationship available.

SMILES: c1ccccc1C=CC(=O)OCC2CC(OC(=O)C=Cc3ccccc3)CC(O2)Oc(c4=O)c(-c5ccccc5)oc(c46)cccc6

Level: 4

Mol. Weight: 740.67 g/mol

SMILES: c1ccccc1C=CC(=O)OCC2CC(OC(=O)C=Cc3ccccc3)CC(O2)Oc(c4=O)coc(c45)cccc5

Level: 3

Mol. Weight: 740.67 g/mol

SMILES: c1ccccc1C=CC(=O)OCC2CCCC(O2)Oc(c3=O)c(-c4ccccc4)oc(c35)cccc5

Level: 3

Mol. Weight: 740.67 g/mol

SMILES: c1ccccc1C=CC(=O)OC2CC(OCC2)Oc(c3=O)c(-c4ccccc4)oc(c35)cccc5

Level: 3

Mol. Weight: 740.67 g/mol

SMILES: c1ccccc1C=CC(=O)OCC2CCCC(O2)Oc(c3=O)coc(c34)cccc4

Level: 2

Mol. Weight: 740.67 g/mol

SMILES: c1ccccc1C=CC(=O)OCC2CC(CCO2)OC(=O)C=Cc3ccccc3

Level: 2

Mol. Weight: 740.67 g/mol

SMILES: c1ccccc1C=CC(=O)OC2CC(OCC2)Oc(c3=O)coc(c34)cccc4

Level: 2

Mol. Weight: 740.67 g/mol

SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC4CCCCO4

Level: 2

Mol. Weight: 740.67 g/mol

SMILES: O1CCCCC1COC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 740.67 g/mol

SMILES: c1cccc(c12)occ(c2=O)OC3CCCCO3

Level: 1

Mol. Weight: 740.67 g/mol

SMILES: C1COCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 740.67 g/mol

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

Level: 1

Mol. Weight: 740.67 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 740.67 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 740.67 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 740.67 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.58
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 11.42
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 2232.43

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.04
Plasma Protein Binding: 74.01
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: 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: Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Inhibitor
OATP1B3: Inhibitor

Excretion

Clearance: 9.96
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -53.75
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.24
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 8.28
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Toxic
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Toxic
T. Pyriformis: -4052041.35
Rat (Acute): 2.41
Rat (Chronic Oral): 3.89
Fathead Minnow: 5122.39
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 448217.01
Hydration Free Energy: -2.92
Log(D) at pH=7.4: 3.24
Log(P): 5.09
Log S: -6.56
Log(Vapor Pressure): -14761.27
Melting Point: 253.77
pKa Acid: -72.86
pKa Basic: 3.24

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9761
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9403
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.9382
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.9364
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9007
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.8990
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8926
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8923
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8917
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8831
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.8801
Protease	O38896	O38896_9HIV1	Human immunodeficiency virus 1	3	0.8728
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.8693
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.8610
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8567
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8566
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8554
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8542
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	4	0.8519
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8519
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8518
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	4	0.8515
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8487
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8475
Cytochrome P450 1A1	P04798	CP1A1_HUMAN	Homo sapiens	3	0.8391
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.8322
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.8319
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.8312
Cyclic dipeptide N-prenyltransferase	D1D8L6	D1D8L6_ASPFM	Neosartorya fumigata	3	0.8266
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8243
Glutathione S-transferase F2	P46422	GSTF2_ARATH	Arabidopsis thaliana	3	0.8233
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8201
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.8192
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8163
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	4	0.8159
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8148
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8105
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8101
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8067
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.8052
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.8031
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.8027
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8003
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7978
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7954
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.7925
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7886
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.7880
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7880
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.7878
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7859
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7855
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7771
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7760
Avidin	P02701	AVID_CHICK	Gallus gallus	3	0.7760
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	4	0.7728
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7711
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.7701
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.7684
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7680
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7677
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7673
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7654
Iron-uptake system-binding protein	P40409	FEUA_BACSU	Bacillus subtilis	4	0.7651
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7633
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7629
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7624
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7624
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.7609
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.7593
Prolyl tripeptidyl peptidase	Q7MUW6	PTP_PORGI	Porphyromonas gingivalis	3	0.7583
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7570
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.7564
Precorrin-3 methylase	O68097	O68097_RHOCA	Rhodobacter capsulatus	4	0.7558
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7540
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7519
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7507
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7497
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7482
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7481
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.7476
Annexin A5	P08758	ANXA5_HUMAN	Homo sapiens	3	0.7472
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7462
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7450
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	2	0.7439
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	3	0.7423
Disintegrin and metalloproteinase domain-containing protein 17	P78536	ADA17_HUMAN	Homo sapiens	3	0.7411
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7409
Prolyl endopeptidase	P23687	PPCE_PIG	Sus scrofa	3	0.7406
Streptogramin A acetyltransferase	P50870	VATD_ENTFC	Enterococcus faecium	3	0.7406
Serine/threonine-protein kinase PLK1	P53350	PLK1_HUMAN	Homo sapiens	3	0.7335
Acetylglutamate kinase	Q0ASS9	Q0ASS9_MARMM	Maricaulis maris	3	0.7333
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7319
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7317
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	2	0.7306
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7304
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7295
Caffeoyl-CoA O-methyltransferase	Q40313	CAMT_MEDSA	Medicago sativa	3	0.7287
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7252
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7244
FMN-dependent NAD(P)H:quinone oxidoreductase 1	Q9I5F3	AZOR1_PSEAE	Pseudomonas aeruginosa	2	0.7241
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase	O67060	ISPE_AQUAE	Aquifex aeolicus	3	0.7232
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7222
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7220
Acyl-CoA:acyl-CoA alkyltransferase	Q8PDX2	OLEA_XANCP	Xanthomonas campestris pv. campestris	3	0.7219
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	P49354	FNTA_HUMAN	Homo sapiens	3	0.7213
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.7208
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.7197
Uncharacterized protein YML079W	Q03629	YMH9_YEAST	Saccharomyces cerevisiae	2	0.7192
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7189
Flavin reductase (NADPH)	P30043	BLVRB_HUMAN	Homo sapiens	3	0.7178
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.7164
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.7162
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	5	0.7150
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.7146
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7145
adenine phosphoribosyltransferase	Q967M2	Q967M2_GIAIN	Giardia intestinalis	2	0.7135
Anthranilate phosphoribosyltransferase	P00500	TRPD_ACIAD	Acinetobacter baylyi	2	0.7117
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7111
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7101
Protein RecA	Q59560	RECA_MYCS2	Mycolicibacterium smegmatis155)	3	0.7087
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7083
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7078
Beta-lactamase	Q9L5C8	Q9L5C8_ECOLX	Escherichia coli	3	0.7077
Glycogen phosphorylase, liver form	P06737	PYGL_HUMAN	Homo sapiens	3	0.7068
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7067
Thymidylate kinase	Q8I4S1	Q8I4S1_PLAF7	Plasmodium falciparum	5	0.7066
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.7065
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7049
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7036
Nitric oxide synthase 1	P29476	NOS1_RAT	Rattus norvegicus	3	0.7035
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	P49354	FNTA_HUMAN	Homo sapiens	4	0.7032
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.7030
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7029
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7028
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7017
Protein polybromo-1	Q86U86	PB1_HUMAN	Homo sapiens	5	0.7015
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	2	0.7013
Chaperone protein ClpB	Q9RA63	CLPB_THET8	Thermus thermophilus	4	0.7010
Mandelate racemase	P11444	MANR_PSEPU	Pseudomonas putida	2	0.7006
Formate--tetrahydrofolate ligase	P21164	FTHS_MOOTH	Moorella thermoacetica	2	0.7001
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	2	0.7000

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