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Kaempferol-3-glucoside-2''-p-coumaroyl

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

Canonical Smiles	OC[C@H]1O[C@@H](Oc2c(oc3c(c2=O)c(O)cc(c3)O)c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)OC(=O)/C=C/c1ccc(cc1)O
InChI	InChI=1S/C30H26O13/c31-13-21-24(37)26(39)29(42-22(36)10-3-14-1-6-16(32)7-2-14)30(41-21)43-28-25(38)23-19(35)11-18(34)12-20(23)40-27(28)15-4-8-17(33)9-5-15/h1-12,21,24,26,29-35,37,39H,13H2/b10-3+/t21-,24-,26+,29-,30+/m1/s1
InChIKey	IKONEAPXVKTZFF-NLGJGAJZSA-N
Formula	C₃₀H₂₆O₁₃
HBA	13
HBD	7
MW	594.53
Rotatable Bonds	7
TPSA	216.58
LogP	1.73
Number Rings	5
Number Aromatic Rings	4
Heavy Atom Count	43
Formal Charge	0
Fraction CSP3	0.2
Exact Mass	594.14
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Rosa canina	Rosaceae	Plantae	74635

Showing of synonyms

Fetni S, Bertella N, et al. (2020). Composition and biological activity of the Algerian plant Rosa canina L by HPLC-UV-MS. Arabian Journal of Chemistry, 2020, 13(1), 1105-1119. [View]

Pubchem: 6442291

Cas: 137018-32-7

Gnps: CCMSLIB00000218650

Chebi: 192429

Nmrshiftdb2: 60031666

No compound-protein relationship available.

SMILES: c1ccccc1C=CC(=O)OC2C(OCCC2)Oc(c3=O)c(-c4ccccc4)oc(c35)cccc5

Level: 3

Mol. Weight: 594.53 g/mol

SMILES: c1ccccc1C=CC(=O)OC2C(OCCC2)Oc(c3=O)coc(c34)cccc4

Level: 2

Mol. Weight: 594.53 g/mol

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

Level: 2

Mol. Weight: 594.53 g/mol

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

Level: 1

Mol. Weight: 594.53 g/mol

SMILES: C1OCCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 594.53 g/mol

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

Level: 1

Mol. Weight: 594.53 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 594.53 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 594.53 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 594.53 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.98
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.040
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 10.17

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.990
Plasma Protein Binding: 85.09
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: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 10.880
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.750
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.190
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.260
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: Safe
T. Pyriformis: -17739.470
Rat (Acute): 2.380
Rat (Chronic Oral): 3.450
Fathead Minnow: 42.790
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Toxic
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 443.730
Hydration Free Energy: -3.150
Log(D) at pH=7.4: 1.800
Log(P): 2.93
Log S: -5.11
Log(Vapor Pressure): -17.13
Melting Point: 237.77
pKa Acid: 6.05
pKa Basic: 5.58

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9766
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9432
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.9095
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.9032
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8986
Botulinum neurotoxin type A	P0DPI0	BXA1_CLOBO	Clostridium botulinum	3	0.8850
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8832
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.8812
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	3	0.8805
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8678
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8657
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8640
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8602
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.8505
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8475
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8456
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.8409
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8381
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8380
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8338
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.8217
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8133
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.8114
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	6	0.8113
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.8094
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.8019
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8016
Prostaglandin reductase 1	Q14914	PTGR1_HUMAN	Homo sapiens	4	0.8015
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.8002
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7962
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7962
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7949
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.7898
Cytochrome P450 1A1	P04798	CP1A1_HUMAN	Homo sapiens	3	0.7874
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7854
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	4	0.7834
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.7811
Seed lectin subunit I	P05045	LEC1_VIGUC	Vigna unguiculata subsp. cylindrica	3	0.7791
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.7785
UDP-galactopyranose mutase	Q48485	GLF1_KLEPN	Klebsiella pneumoniae	4	0.7779
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7768
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7766
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7728
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7720
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7718
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.7676
Isoflavone 4'-O-methyltransferase	Q29U70	I4OMT_MEDTR	Medicago truncatula	3	0.7665
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.7663
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7636
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	5	0.7591
Multidrug-efflux transporter 1 regulator	P39075	BMRR_BACSU	Bacillus subtilis	3	0.7576
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7573
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7549
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7516
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7508
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7472
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7441
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7404
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	4	0.7367
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7352
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7349
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7347
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	2	0.7283
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.7266
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7251
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7244
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	2	0.7212
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.7209
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7188
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7173
Antitumor antibiotic C-1027 apoprotein	Q06110	CAGA_STRGL	Streptomyces globisporus	3	0.7173
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7165
Beta-lactamase	P00811	AMPC_ECOLI	Escherichia coli	3	0.7156
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7127
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7125
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7105
Anthranilate phosphoribosyltransferase	P00500	TRPD_ACIAD	Acinetobacter baylyi	2	0.7095
Pteridine reductase	O76290	O76290_TRYBB	Trypanosoma brucei brucei	3	0.7095
Fructose-1,6-bisphosphatase 1	P09467	F16P1_HUMAN	Homo sapiens	2	0.7053
Oxygenase	Q194P4	Q194P4_STRAA	Streptomyces argillaceus	3	0.7044
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7041
Angiotensin-converting enzyme 2	Q9BYF1	ACE2_HUMAN	Homo sapiens	2	0.7034
Geranylgeranyl transferase type-2 subunit alpha	Q08602	PGTA_RAT	Rattus norvegicus	3	0.7030
Orf1a polyprotein	Q692E5	Q692E5_CVHSA	SARS coronavirus TJF	3	0.7016
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7012
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7010
Formate--tetrahydrofolate ligase	P21164	FTHS_MOOTH	Moorella thermoacetica	2	0.7006
Flavin reductase (NADPH)	P30043	BLVRB_HUMAN	Homo sapiens	3	0.7004

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