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6 ́ ́ ́-feruloylspinosin

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

Canonical Smiles	COC1=C(C=CC(=C1)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)O
InChI	InChI=1S/C38H40O18/c1-50-22-11-16(3-9-19(22)41)4-10-27(43)52-15-26-31(45)33(47)35(49)38(55-26)56-37-34(48)30(44)25(14-39)54-36(37)29-23(51-2)13-24-28(32(29)46)20(42)12-21(53-24)17-5-7-18(40)8-6-17/h3-13,25-26,30-31,33-41,44-49H,14-15H2,1-2H3
InChIKey	WZAXZHIVHPRTIU-UHFFFAOYSA-N
Formula	C₃₈H₄₀O₁₈
HBA	18
HBD	9
MW	784.72
Rotatable Bonds	11
TPSA	284.73
LogP	0.2
Number Rings	6
Number Aromatic Rings	4
Heavy Atom Count	56
Formal Charge	0
Fraction CSP3	0.37
Exact Mass	784.22
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: 21597353

Cas: 77690-92-7

Zinc: ZINC000095627961

Nmrshiftdb2: 60028674

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: 784.72 g/mol

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

Level: 3

Mol. Weight: 784.72 g/mol

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

Level: 3

Mol. Weight: 784.72 g/mol

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

Level: 2

Mol. Weight: 784.72 g/mol

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

Level: 2

Mol. Weight: 784.72 g/mol

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

Level: 2

Mol. Weight: 784.72 g/mol

SMILES: O1CCCCC1COC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 784.72 g/mol

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

Level: 1

Mol. Weight: 784.72 g/mol

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

Level: 1

Mol. Weight: 784.72 g/mol

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 784.72 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 784.72 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 784.72 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 784.72 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.57
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 34.460
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 5305.96

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.870
Plasma Protein Binding: -9.46
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: 7.840
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -123.420
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.980
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 7.510
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: -9626375.050
Rat (Acute): 2.270
Rat (Chronic Oral): 4.340
Fathead Minnow: 12160.100
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: 1075799.420
Hydration Free Energy: -2.920
Log(D) at pH=7.4: 1.030
Log(P): 2.09
Log S: -6.17
Log(Vapor Pressure): -35400.04
Melting Point: 220.9
pKa Acid: -220.53
pKa Basic: 5.5

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9563
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9524
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.9504
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9459
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.9315
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.9161
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.9067
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9063
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9047
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.8964
Trichothecene 15-O-acetyltransferase TRI3	Q9C1B7	TRI3_FUSSP	Fusarium sporotrichioides	3	0.8906
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	3	0.8892
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.8886
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.8846
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.8843
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8814
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8811
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8774
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8735
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8696
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8660
Caffeic acid O-methyltransferase	Q9ZTU2	Q9ZTU2_LOLPR	Lolium perenne	4	0.8641
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8607
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.8568
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8549
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8329
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	3	0.8270
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.8263
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8233
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	3	0.8217
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8214
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8173
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8170
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.8157
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.8111
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.8082
4,4'-diapophytoene synthase	A9JQL9	CRTM_STAAU	Staphylococcus aureus	3	0.8048
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.8048
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.8028
ADP-ribosylation factor 1	P84077	ARF1_HUMAN	Homo sapiens	2	0.8021
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7921
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7867
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	3	0.7838
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7831
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7819
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7762
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	3	0.7704
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7701
Tubulin--tyrosine ligase	F6Z895	A9ULH4_XENTR	Xenopus tropicalis	4	0.7698
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7669
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7659
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7648
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7635
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	4	0.7635
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7634
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	4	0.7620
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7600
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7589
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7552
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7537
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7531
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7525
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7507
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	4	0.7499
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7461
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7457
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.7457
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7428
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7402
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7402
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7384
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7375
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7365
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7358
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7347
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7336
Interleukin-2	P60568	IL2_HUMAN	Homo sapiens	3	0.7329
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7326
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	3	0.7325
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	3	0.7314
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7314
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7313
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7309
Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4	Q8GZB6	SUVH4_ARATH	Arabidopsis thaliana	3	0.7306
Histone-lysine N-methyltransferase EHMT2	Q96KQ7	EHMT2_HUMAN	Homo sapiens	3	0.7303
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	3	0.7293
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7283
Mitogen-activated protein kinase kinase kinase 7	O43318	M3K7_HUMAN	Homo sapiens	3	0.7270
Histone-lysine N-methyltransferase 2A	Q03164	KMT2A_HUMAN	Homo sapiens	3	0.7259
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7253
Streptavidin	P22629	SAV_STRAV	Streptomyces avidinii	3	0.7251
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7245
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7240
SKP1-like protein 1A	Q39255	SKP1A_ARATH	Arabidopsis thaliana	3	0.7222
Phenolphthiocerol/phthiocerol polyketide synthase subunit C	P96202	PPSC_MYCTU	Mycobacterium tuberculosis	3	0.7220
Histone deacetylase 7	Q8WUI4	HDAC7_HUMAN	Homo sapiens	3	0.7212
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7212
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7212
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	2	0.7202
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.7187
Caffeoyl-CoA O-methyltransferase	Q40313	CAMT_MEDSA	Medicago sativa	3	0.7179
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	4	0.7170
14-3-3 protein gamma	P61981	1433G_HUMAN	Homo sapiens	3	0.7169
Chorismate mutase AroH	P19080	AROH_BACSU	Bacillus subtilis	2	0.7153
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7148
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7144
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	4	0.7143
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	2	0.7138
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7130
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7120
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7118
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7114
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7108
Histone-lysine N-methyltransferase 2A	Q03164	KMT2A_HUMAN	Homo sapiens	3	0.7096
Single-strand selective monofunctional uracil DNA glycosylase	Q9YGN6	SMUG1_XENLA	Xenopus laevis	3	0.7096
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	4	0.7091
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7084
Transitional endoplasmic reticulum ATPase	Q01853	TERA_MOUSE	Mus musculus	3	0.7081
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.7081
Neutrophil gelatinase-associated lipocalin	P80188	NGAL_HUMAN	Homo sapiens	2	0.7078
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7074
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7074
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	3	0.7073
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7069
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.7060
Streptavidin	P22629	SAV_STRAV	Streptomyces avidinii	3	0.7056
Aspartate aminotransferase	P00509	AAT_ECOLI	Escherichia coli	2	0.7050
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7050
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7048
Uracil-DNA glycosylase	P20536	UNG_VACCC	Vaccinia virus	3	0.7046
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	2	0.7043
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	3	0.7042
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7040
Purine nucleoside phosphorylase	B9JYS2	B9JYS2_AGRVS	Agrobacterium vitis	3	0.7024
Protease	O38896	O38896_9HIV1	Human immunodeficiency virus 1	3	0.7013
Histone-lysine N-methyltransferase 2C	Q8NEZ4	KMT2C_HUMAN	Homo sapiens	3	0.7011
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	3	0.7010
Kynurenine--oxoglutarate transaminase 1	Q16773	KAT1_HUMAN	Homo sapiens	2	0.7008
Fructose-1,6-bisphosphatase 1	P09467	F16P1_HUMAN	Homo sapiens	2	0.7008
Uridine phosphorylase	Q9KT71	Q9KT71_VIBCH	Vibrio cholerae serotype O1	3	0.7004
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate hydrolase	P47229	BPHD_PARXL	Paraburkholderia xenovorans	2	0.7004
Uracil-DNA glycosylase	P13051	UNG_HUMAN	Homo sapiens	3	0.7001

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