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Kaempferol 3-O-robinobioside

Family: Plantae - Rubiaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavonoid Glycoside

Canonical Smiles	Oc1ccc(cc1)c1oc2cc(O)cc(c2c(=O)c1O[C@@H]1OC(CO[C@@H]2OC(C)[C@@H]([C@@H](C2O)O)O)[C@@H](C(C1O)O)O)O
InChI	InChI=1S/C27H30O15/c1-9-17(31)20(34)22(36)26(39-9)38-8-15-18(32)21(35)23(37)27(41-15)42-25-19(33)16-13(30)6-12(29)7-14(16)40-24(25)10-2-4-11(28)5-3-10/h2-7,9,15,17-18,20-23,26-32,34-37H,8H2,1H3/t9?,15?,17-,18-,20-,21?,22?,23?,26+,27-/m0/s1
InChIKey	RTATXGUCZHCSNG-VDQDLQOTSA-N
Formula	C₂₇H₃₀O₁₅
HBA	15
HBD	9
MW	594.52
Rotatable Bonds	6
TPSA	249.2
LogP	-1.39
Number Rings	5
Number Aromatic Rings	3
Heavy Atom Count	42
Formal Charge	0
Fraction CSP3	0.44
Exact Mass	594.16
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Ixora undulata	Rubiaceae	Plantae	1231253

Showing of synonyms

Sugimoto S, Wanas AS, et al. (2014). Structure elucidation of secondary metabolites isolated from the leaves of Ixora undulate and their inhibitory activity toward advanced glycation end-products formation. Phytochemistry,2014,108,189-195. [View] [PubMed]

Pubchem: 44258742

Nmrshiftdb2: 70038286

No compound-protein relationship available.

SMILES: O1CCCCC1OCC2CCCC(O2)Oc(c3=O)c(-c4ccccc4)oc(c35)cccc5

Level: 3

Mol. Weight: 594.52 g/mol

SMILES: O1CCCCC1OCC2CCCC(O2)Oc(c3=O)coc(c34)cccc4

Level: 2

Mol. Weight: 594.52 g/mol

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

Level: 2

Mol. Weight: 594.52 g/mol

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

Level: 1

Mol. Weight: 594.52 g/mol

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

Level: 1

Mol. Weight: 594.52 g/mol

SMILES: O1CCCCC1COC2CCCCO2

Level: 1

Mol. Weight: 594.52 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 594.52 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 594.52 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 594.52 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.64
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.400
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 6.15

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.830
Plasma Protein Binding: 44.49
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: 11.840
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -3.210
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: 5.400
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: -9037.390
Rat (Acute): 2.290
Rat (Chronic Oral): 4.550
Fathead Minnow: 19.950
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 533.240
Hydration Free Energy: -3.120
Log(D) at pH=7.4: -0.470
Log(P): 0.35
Log S: -4.3
Log(Vapor Pressure): -12.53
Melting Point: 209.8
pKa Acid: 3.93
pKa Basic: 7.12

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9763
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9763
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9446
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9446
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.9323
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.9323
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.8978
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.8978
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8918
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.8918
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8912
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8912
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.8600
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.8600
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.8508
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.8508
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8500
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8500
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8499
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8499
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	3	0.8405
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	3	0.8405
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8346
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8346
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8179
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8179
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.8124
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.8124
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.8063
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.8063
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8056
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8056
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8018
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8018
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.7996
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.7996
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7959
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7959
Prolyl tripeptidyl peptidase	Q7MUW6	PTP_PORGI	Porphyromonas gingivalis	3	0.7910
Prolyl tripeptidyl peptidase	Q7MUW6	PTP_PORGI	Porphyromonas gingivalis	3	0.7910
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7897
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7897
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.7869
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.7869
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7839
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7839
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	6	0.7813
Ribosomal protein S6 kinase alpha-3	P18654	KS6A3_MOUSE	Mus musculus	6	0.7813
Avidin	P02701	AVID_CHICK	Gallus gallus	3	0.7798
Avidin	P02701	AVID_CHICK	Gallus gallus	3	0.7798
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7786
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7786
Streptogramin A acetyltransferase	P50870	VATD_ENTFC	Enterococcus faecium	3	0.7766
Streptogramin A acetyltransferase	P50870	VATD_ENTFC	Enterococcus faecium	3	0.7766
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7760
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7760
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7731
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7731
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7700
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7700
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7686
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7686
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7648
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7648
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7620
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7620
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7582
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7582
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7542
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7542
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7529
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7529
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7524
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7524
Cytochrome P450 1A1	P04798	CP1A1_HUMAN	Homo sapiens	3	0.7495
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7495
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7495
Cytochrome P450 1A1	P04798	CP1A1_HUMAN	Homo sapiens	3	0.7495
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7494
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7494
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7478
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7478
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7450
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7450
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7407
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7407
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	5	0.7403
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	5	0.7403
Beta-glucuronidase	P05804	BGLR_ECOLI	Escherichia coli	3	0.7397
Beta-glucuronidase	P05804	BGLR_ECOLI	Escherichia coli	3	0.7397
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7394
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7394
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.7388
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.7388
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7325
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7325
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7297
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7297
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7264
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7264
Flavin reductase (NADPH)	P30043	BLVRB_HUMAN	Homo sapiens	3	0.7096
Flavin reductase (NADPH)	P30043	BLVRB_HUMAN	Homo sapiens	3	0.7096
Serine/threonine-protein kinase PLK1	P53350	PLK1_HUMAN	Homo sapiens	3	0.7050
Serine/threonine-protein kinase PLK1	P53350	PLK1_HUMAN	Homo sapiens	3	0.7050
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7036
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7036
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7006
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7006

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