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Rhamnocitrin-3-O-beta-(6''-O-E-p-coumaroyl)-glucopyranoside

Family: Plantae - Capparaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavone

Canonical Smiles	COc1cc(O)c2c(c1)oc(c(c2=O)OC1O[C@H](COC(=O)/C=C/c2ccc(cc2)O)[C@H]([C@@H]([C@H]1O)O)O)c1ccc(cc1)O
InChI	InChI=1S/C31H28O13/c1-40-19-12-20(34)24-21(13-19)42-29(16-5-9-18(33)10-6-16)30(26(24)37)44-31-28(39)27(38)25(36)22(43-31)14-41-23(35)11-4-15-2-7-17(32)8-3-15/h2-13,22,25,27-28,31-34,36,38-39H,14H2,1H3/b11-4+/t22-,25-,27+,28-,31?/m1/s1
InChIKey	FRZQTGONAKOMSV-IPCDYBEYSA-N
Formula	C₃₁H₂₈O₁₃
HBA	13
HBD	6
MW	608.55
Rotatable Bonds	8
TPSA	205.58
LogP	2.03
Number Rings	5
Number Aromatic Rings	4
Heavy Atom Count	44
Formal Charge	0
Fraction CSP3	0.23
Exact Mass	608.15
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Boscia angustifolia	Capparaceae	Plantae	511493

Showing of synonyms

Salem M, Hussein S, et al. (2016). Phytochemical investigation of Boscia angustifolia A. Rich. (Capparaceae). Biochemical Systematics and Ecology, 2016, 65, 202-204. [View]

No compound-protein relationship available.

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

Level: 3

Mol. Weight: 608.55 g/mol

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

Level: 2

Mol. Weight: 608.55 g/mol

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

Level: 2

Mol. Weight: 608.55 g/mol

SMILES: O1CCCCC1COC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 608.55 g/mol

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

Level: 1

Mol. Weight: 608.55 g/mol

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

Level: 1

Mol. Weight: 608.55 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 608.55 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 608.55 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 608.55 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.46
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -4.870
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 16.94

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.120
Plasma Protein Binding: 71.75
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: 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: 7.920
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.040
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.170
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.900
Micronucleos: Toxic
NR-AhR: Toxic
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: -30273.050
Rat (Acute): 2.480
Rat (Chronic Oral): 3.970
Fathead Minnow: 59.110
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Toxic

General Properties

Boiling Point: 401.820
Hydration Free Energy: -2.920
Log(D) at pH=7.4: 2.990
Log(P): 3.26
Log S: -5.72
Log(Vapor Pressure): -15.11
Melting Point: 212.91
pKa Acid: 6.89
pKa Basic: 2.4

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9800
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9463
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.9402
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.9139
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.9013
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8998
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8881
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8803
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	3	0.8763
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.8712
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.8708
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8601
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.8486
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8483
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.8476
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.8337
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.8302
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8242
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8203
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.8153
Flavin reductase (NADPH)	P30043	BLVRB_HUMAN	Homo sapiens	3	0.8134
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	4	0.8123
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.8047
Insulin-degrading enzyme	P14735	IDE_HUMAN	Homo sapiens	3	0.8043
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	4	0.8025
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.8014
Glutathione S-transferase F2	P46422	GSTF2_ARATH	Arabidopsis thaliana	3	0.8006
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7948
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7915
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7915
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7903
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7902
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase	O67060	ISPE_AQUAE	Aquifex aeolicus	3	0.7879
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.7864
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7849
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7848
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7838
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7807
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7798
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7768
Chloramphenicol 3-O phosphotransferase	Q56148	CPT_STRVP	Streptomyces venezuelae	4	0.7753
Botulinum neurotoxin type A	P0DPI0	BXA1_CLOBO	Clostridium botulinum	3	0.7734
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7698
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7688
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7652
Protein polybromo-1	Q86U86	PB1_HUMAN	Homo sapiens	5	0.7646
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7644
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7639
Cyclin-dependent kinase 5	Q00535	CDK5_HUMAN	Homo sapiens	4	0.7630
Orf1a polyprotein	Q692E5	Q692E5_CVHSA	SARS coronavirus TJF	3	0.7612
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7597
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.7588
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	4	0.7574
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7570
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7558
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	3	0.7521
Streptogramin A acetyltransferase	P50870	VATD_ENTFC	Enterococcus faecium	3	0.7493
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7491
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7481
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.7475
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7455
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7454
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7444
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7421
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7420
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.7407
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7398
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7359
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.7358
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7328
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7326
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7307
17beta-hydroxysteroid dehydrogenase	O93874	O93874_COCLU	Cochliobolus lunatus	3	0.7304
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7290
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7283
Nitric oxide synthase 1	P29476	NOS1_RAT	Rattus norvegicus	3	0.7269
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7266
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	3	0.7264
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	4	0.7260
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7253
Threonine--tRNA ligase	P0A8M3	SYT_ECOLI	Escherichia coli	3	0.7250
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7234
Cytochrome P450 1A1	P04798	CP1A1_HUMAN	Homo sapiens	3	0.7224
Basic phospholipase A2 homolog piratoxin-1	P58399	PA2H1_BOTPI	Bothrops pirajai	4	0.7206
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7206
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	3	0.7205
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7196
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.7194
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7178
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7157
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7134
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7124
17beta-hydroxysteroid dehydrogenase	O93874	O93874_COCLU	Cochliobolus lunatus	3	0.7120
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7118
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	2	0.7102
Serine/threonine-protein kinase PLK1	P53350	PLK1_HUMAN	Homo sapiens	3	0.7096
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7092
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.7076
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	5	0.7069
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7064
Ethylene receptor 1	P49333	ETR1_ARATH	Arabidopsis thaliana	3	0.7060
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7052
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7038
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7032
3-hydroxyisobutyryl-CoA hydrolase, mitochondrial	Q6NVY1	HIBCH_HUMAN	Homo sapiens	3	0.7029
Aminoglycoside N(3)-acetyltransferase	A0A3P1UCA6	Q81P86_BACAN	Bacillus anthracis	3	0.7026
Beta-lactamase	Q9L5C8	Q9L5C8_ECOLX	Escherichia coli	3	0.7001

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