ANPDB

Select a section from the left sidebar

6 ́ ́ ́-sinapoylspinosin

Family: Plantae - Rhamnaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavone Glycoside

Canonical Smiles	COC1=CC(=CC(=C1O)OC)C=CC(=O)OCC2C(C(C(C(O2)OC3C(C(C(OC3C4=C(C=C5C(=C4O)C(=O)C=C(O5)C6=CC=C(C=C6)O)OC)CO)O)O)O)O)O
InChI	InChI=1S/C39H42O19/c1-51-21-13-22-28(19(42)12-20(55-22)17-5-7-18(41)8-6-17)33(47)29(21)37-38(35(49)31(45)25(14-40)56-37)58-39-36(50)34(48)32(46)26(57-39)15-54-27(43)9-4-16-10-23(52-2)30(44)24(11-16)53-3/h4-13,25-26,31-32,34-41,44-50H,14-15H2,1-3H3
InChIKey	BFWPTYMTWQBGHH-UHFFFAOYSA-N
Formula	C₃₉H₄₂O₁₉
HBA	19
HBD	9
MW	814.75
Rotatable Bonds	12
TPSA	293.96
LogP	0.21
Number Rings	6
Number Aromatic Rings	4
Heavy Atom Count	58
Formal Charge	0
Fraction CSP3	0.38
Exact Mass	814.23
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Ziziphus spina-christi	Rhamnaceae	Plantae	264981

Showing of synonyms

Kadioglu O, Jacob S, et al. (2016). Evaluating ancient Egyptian prescriptions today: Anti-inflammatory activity of Ziziphus spina-christi. Phytomedicine : international journal of phytotherapy and phytopharmacology,2016, 23(3), 293-306. [View] [PubMed]

Pubchem: 101616450

Zinc: ZINC000255198721

No compound-protein relationship available.

SMILES: c1ccccc1C=CC(=O)OCC2CCCC(O2)OC(CCCO3)C3c(c4)ccc(c45)oc(cc5=O)-c6ccccc6

Level: 4

Mol. Weight: 814.75 g/mol

SMILES: c1ccccc1C=CC(=O)OCC2CCCC(O2)OC(CCCO3)C3c(c4)ccc(c45)occc5=O

Level: 3

Mol. Weight: 814.75 g/mol

SMILES: c1ccccc1-c(cc2=O)oc(c23)ccc(c3)C4C(CCCO4)OC5CCCCO5

Level: 3

Mol. Weight: 814.75 g/mol

SMILES: c1ccccc1C=CC(=O)OCC2CCCC(O2)OC3CCCOC3

Level: 2

Mol. Weight: 814.75 g/mol

SMILES: O=c1ccoc(c12)ccc(c2)C3C(CCCO3)OC4CCCCO4

Level: 2

Mol. Weight: 814.75 g/mol

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

Level: 2

Mol. Weight: 814.75 g/mol

SMILES: O1CCCCC1COC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 814.75 g/mol

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

Level: 1

Mol. Weight: 814.75 g/mol

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

Level: 1

Mol. Weight: 814.75 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 814.75 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 814.75 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 814.75 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 814.75 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.59
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 94.250
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 13129.31

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.850
Plasma Protein Binding: -11.03
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: 7.430
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Toxic
Bee: Toxic
Bioconcentration Factor: -302.980
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.940
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.310
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: -23825257.640
Rat (Acute): 2.230
Rat (Chronic Oral): 4.420
Fathead Minnow: 30083.420
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Toxic

General Properties

Boiling Point: 2672586.380
Hydration Free Energy: -2.920
Log(D) at pH=7.4: 1.080
Log(P): 1.66
Log S: -6.23
Log(Vapor Pressure): -87979.69
Melting Point: 219.72
pKa Acid: -593.45
pKa Basic: 5.26

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9568
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.9568
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.9504
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9476
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9442
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.9295
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.9218
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	4	0.9083
Uracil-DNA glycosylase	P20536	UNG_VACCC	Vaccinia virus	4	0.9054
Single-strand selective monofunctional uracil DNA glycosylase	Q9YGN6	SMUG1_XENLA	Xenopus laevis	4	0.8994
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8984
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.8925
Uridine phosphorylase	Q9KT71	Q9KT71_VIBCH	Vibrio cholerae serotype O1	4	0.8906
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8884
Caffeic acid O-methyltransferase	Q9ZTU2	Q9ZTU2_LOLPR	Lolium perenne	4	0.8881
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8879
Uridine phosphorylase	P0A1F6	UDP_SALTY	Salmonella typhimurium	4	0.8866
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8800
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8789
Uridine phosphorylase	Q5XA29	Q5XA29_STRP6	Streptococcus pyogenes serotype M6	4	0.8773
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8764
Uridine phosphorylase 2	O95045	UPP2_HUMAN	Homo sapiens	4	0.8741
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8724
Uracil-DNA glycosylase	P13051	UNG_HUMAN	Homo sapiens	4	0.8723
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8714
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8711
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8709
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8700
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	3	0.8699
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.8696
Uridine phosphorylase	Q9KT71	Q9KT71_VIBCH	Vibrio cholerae serotype O1	4	0.8684
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8680
Nucleoside phosphorylase, putative	Q57VZ2	Q57VZ2_TRYB2	Trypanosoma brucei brucei	4	0.8674
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8635
Insulin-degrading enzyme	P14735	IDE_HUMAN	Homo sapiens	3	0.8631
Uracil-DNA glycosylase	P9WFQ9	UNG_MYCTU	Mycobacterium tuberculosis	4	0.8570
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.8534
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.8502
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8487
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8465
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8435
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.8414
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8367
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	4	0.8243
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.8223
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.8189
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8172
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.8156
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.8140
Trichothecene 15-O-acetyltransferase TRI3	Q9C1B7	TRI3_FUSSP	Fusarium sporotrichioides	3	0.8125
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	4	0.8117
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	3	0.8086
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	4	0.8084
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.8059
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.8042
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7998
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	3	0.7970
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7969
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7963
Thymidylate kinase	Q9KQI2	KTHY_VIBCH	Vibrio cholerae serotype O1	4	0.7948
Interleukin-2	P60568	IL2_HUMAN	Homo sapiens	3	0.7920
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7891
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7842
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.7819
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7744
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	4	0.7702
4,4'-diapophytoene synthase	A9JQL9	CRTM_STAAU	Staphylococcus aureus	3	0.7690
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase	Q8DNV6	Q8DNV6_STRR6	Streptococcus pneumoniae	3	0.7687
Beta sliding clamp	P0A988	DPO3B_ECOLI	Escherichia coli	3	0.7682
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	4	0.7659
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7648
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7640
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7631
Glucose-1-phosphate thymidylyltransferase	Q9AGY4	Q9AGY4_ANETH	Aneurinibacillus thermoaerophilus	4	0.7620
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7618
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7617
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	4	0.7609
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7601
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7573
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7561
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7550
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7538
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7519
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7516
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7490
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7480
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7478
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7468
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7453
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	4	0.7445
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7424
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7421
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7414
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7392
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7372
Cholinesterase	P06276	CHLE_HUMAN	Homo sapiens	3	0.7369
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7365
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7365
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7326
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7320
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7308
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7290
Histone deacetylase 7	Q8WUI4	HDAC7_HUMAN	Homo sapiens	3	0.7255
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7234
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7233
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7225
14-3-3 protein gamma	P61981	1433G_HUMAN	Homo sapiens	3	0.7218
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7215
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	3	0.7212
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7185
Eukaryotic translation initiation factor 4E-1	P29557	IF4E1_WHEAT	Triticum aestivum	4	0.7179
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	4	0.7168
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.7165
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	3	0.7152
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7143
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7126
Phenolphthiocerol/phthiocerol polyketide synthase subunit C	P96202	PPSC_MYCTU	Mycobacterium tuberculosis	3	0.7126
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7125
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7125
Ephrin type-A receptor 2	P29317	EPHA2_HUMAN	Homo sapiens	3	0.7118
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7118
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7118
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	4	0.7116
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	3	0.7082
Transthyretin	P02767	TTHY_RAT	Rattus norvegicus	2	0.7081
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	4	0.7077
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7074
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.7072
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7069
KLTH0G14146p	C5DN49	C5DN49_LACTC	Lachancea thermotolerans	4	0.7064
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7051
dTDP-4-dehydrorhamnose 3,5-epimerase	A0A6L7H6N0	A0A1S0QLH9_BACAN	Bacillus anthracis	3	0.7048
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7046
ADP-ribosylation factor 1	P84077	ARF1_HUMAN	Homo sapiens	2	0.7043
Formylmethanofuran--tetrahydromethanopterin formyltransferase	Q49610	FTR_METKA	Methanopyrus kandleri	3	0.7041
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7033
Single-stranded-DNA-specific exonuclease RecJ	D0EM60	D0EM60_DEIRD	Deinococcus radiodurans	2	0.7032
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	3	0.7032
DNA mismatch repair protein Msh2	P43246	MSH2_HUMAN	Homo sapiens	3	0.7012
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7009
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	4	0.7009
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	3	0.7003

Download SDF