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3,6-di-O-caffeoyl-(alpha/beta)-glucose

Family: Plantae - Rosaceae
Kingdom: Plantae
Class: Phenolic
- Subclass: Caffeoyl Ester

Canonical Smiles	O=C(OCC1OC(O)[C@H](C([C@@H]1O)OC(=O)/C=C/c1ccc(c(c1)O)O)O)CCc1ccc(c(c1)O)O
InChI	InChI=1S/C24H26O12/c25-14-5-1-12(9-16(14)27)3-7-19(29)34-11-18-21(31)23(22(32)24(33)35-18)36-20(30)8-4-13-2-6-15(26)17(28)10-13/h1-2,4-6,8-10,18,21-28,31-33H,3,7,11H2/b8-4+/t18?,21-,22+,23?,24?/m1/s1
InChIKey	ZJNXCKPIUZHIBZ-KBAGINIPSA-N
Formula	C₂₄H₂₆O₁₂
HBA	12
HBD	7
MW	506.46
Rotatable Bonds	8
TPSA	203.44
LogP	0.05
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	36
Formal Charge	0
Fraction CSP3	0.33
Exact Mass	506.14
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Rubus sanctus	Rosaceae	Plantae	75089

Showing of synonyms

Hussein S.A, Ayoub N.A, et al. (2003). Caffeoyl sugar esters and an ellagitannin from Rubus sanctus. Phytochemistry, 2003, 63(8), 905-11. [View] [PubMed]

No compound-protein relationship available.

SMILES: c1ccccc1C=CC(=O)OC(CCO2)CC2COC(=O)CCc3ccccc3

Level: 2

Mol. Weight: 506.46 g/mol

SMILES: O1CCCCC1COC(=O)CCc2ccccc2

Level: 1

Mol. Weight: 506.46 g/mol

SMILES: C1COCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 506.46 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 506.46 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 506.46 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -7.16
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -5.08
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -1.33

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.82
Plasma Protein Binding: 37.24
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: 15.29
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: -2.34
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.94
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.56
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: -355.19
Rat (Acute): 2.13
Rat (Chronic Oral): 3.78
Fathead Minnow: 4.39
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 605.58
Hydration Free Energy: -3.3
Log(D) at pH=7.4: 0.97
Log(P): 0.4
Log S: -3.29
Log(Vapor Pressure): -12.11
Melting Point: 187.28
pKa Acid: 6.35
pKa Basic: 5.23

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9354
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9075
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.9037
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	4	0.9027
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.8817
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8743
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	3	0.8689
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8679
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8502
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8440
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8345
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8288
Aminoglycoside N(3)-acetyltransferase	A0A3P1UCA6	Q81P86_BACAN	Bacillus anthracis	3	0.8264
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.8145
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8123
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8118
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8075
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.8045
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8014
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8004
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7962
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.7900
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7888
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7873
Avidin	P02701	AVID_CHICK	Gallus gallus	3	0.7818
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	3	0.7774
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7760
Caffeic acid O-methyltransferase	Q9ZTU2	Q9ZTU2_LOLPR	Lolium perenne	4	0.7757
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7707
Cytochrome P450	Q93H81	Q93H81_STRAX	Streptomyces avermitilis	3	0.7688
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.7674
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7670
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7637
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7629
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7584
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7583
Ribosomal RNA small subunit methyltransferase NEP1	Q06287	NEP1_YEAST	Saccharomyces cerevisiae	4	0.7579
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7530
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.7510
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7505
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	3	0.7504
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7499
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7466
Threonine--tRNA ligase	P0A8M3	SYT_ECOLI	Escherichia coli	3	0.7414
Eukaryotic translation initiation factor 4E-1	P29557	IF4E1_WHEAT	Triticum aestivum	4	0.7376
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7353
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7309
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7302
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.7297
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	3	0.7278
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7277
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	3	0.7268
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7239
Eukaryotic translation initiation factor 4E type 3	Q9DBB5	IF4E3_MOUSE	Mus musculus	3	0.7231
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7210
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7198
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7187
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7186
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7179
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7177
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7168
ATP-dependent protease subunit HslV	P0A7B8	HSLV_ECOLI	Escherichia coli	3	0.7155
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7155
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	3	0.7154
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.7149
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7148
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7148
Uncharacterized protein YML079W	Q03629	YMH9_YEAST	Saccharomyces cerevisiae	2	0.7120
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7118
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7106
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7103
Ethylene receptor 1	P49333	ETR1_ARATH	Arabidopsis thaliana	3	0.7096
Dihydropteroate synthase	Q81VW8	Q81VW8_BACAN	Bacillus anthracis	2	0.7081
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7075
Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4	Q8GZB6	SUVH4_ARATH	Arabidopsis thaliana	3	0.7075
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	2	0.7067
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7066
Histone-lysine N-methyltransferase EHMT2	Q96KQ7	EHMT2_HUMAN	Homo sapiens	3	0.7065
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7064
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	3	0.7059
Elongation factor Tu 1	P0CE47	EFTU1_ECOLI	Escherichia coli	3	0.7052
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7049
Protocatechuate 3,4-dioxygenase beta chain	P00437	PCXB_PSEPU	Pseudomonas putida	2	0.7048
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	2	0.7046
Anthranilate phosphoribosyltransferase	P00500	TRPD_ACIAD	Acinetobacter baylyi	2	0.7038
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7037
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7036
Tryptophan--tRNA ligase	Q9PIB4	SYW_CAMJE	Campylobacter jejuni subsp. jejuni serotype O:2	4	0.7028
DNA polymerase theta	O75417	DPOLQ_HUMAN	Homo sapiens	4	0.7018
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	2	0.7017

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