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6'-caffeoyl-(1-1') beta-D-glucopyranosyl-catechol

Family: Plantae - Salicaceae
Kingdom: Plantae
Class: Phenolic

Canonical Smiles	O=C(/C=C/c1ccc(c(c1)O)O)OC[C@H]1O[C@@H](Oc2ccccc2O)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C21H22O10/c22-12-7-5-11(9-14(12)24)6-8-17(25)29-10-16-18(26)19(27)20(28)21(31-16)30-15-4-2-1-3-13(15)23/h1-9,16,18-24,26-28H,10H2/b8-6+/t16-,18-,19+,20-,21-/m1/s1
InChIKey	ZFMCQFCMYAUUBO-KLEREXGMSA-N
Formula	C₂₁H₂₂O₁₀
HBA	10
HBD	6
MW	434.4
Rotatable Bonds	6
TPSA	166.14
LogP	0.25
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	31
Formal Charge	0
Fraction CSP3	0.29
Exact Mass	434.12
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Flacourtia rukam	Salicaceae	Plantae	1085434

Showing of synonyms

Afifi N.I, Moawad A.S, et al. (2022). Four new phenolics and antiparasitic secondary metabolites from Flacourtia rukam Zoll. & Mortizi. Natural product research, 2022, 36(14), 3626-3637. [View] [PubMed]

Pubchem: 44513070

Zinc: ZINC000141684000

Nmrshiftdb2: 70061537

No compound-protein relationship available.

SMILES: c1ccccc1C=CC(=O)OCC2CCCC(O2)Oc3ccccc3

Level: 2

Mol. Weight: 434.4 g/mol

SMILES: O1CCCCC1COC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 434.4 g/mol

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 434.4 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 434.4 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 434.4 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.83
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.96
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.24

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.99
Plasma Protein Binding: 78.77
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: 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: 13.73
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: -1.87
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.09
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.85
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: -37.86
Rat (Acute): 2.06
Rat (Chronic Oral): 3.9
Fathead Minnow: 4.15
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: 538.68
Hydration Free Energy: -6.07
Log(D) at pH=7.4: 1.27
Log(P): 1.14
Log S: -3.81
Log(Vapor Pressure): -12.23
Melting Point: 199.19
pKa Acid: 5.65
pKa Basic: 5.28

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	0.9346
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9083
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8948
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.8942
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.8781
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8713
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	3	0.8710
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8686
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8588
Carnitine O-palmitoyltransferase 2, mitochondrial	P18886	CPT2_RAT	Rattus norvegicus	3	0.8500
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.8449
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8372
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8357
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8347
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8315
Bifunctional protein GlmU	P43889	GLMU_HAEIN	Haemophilus influenzae	3	0.8254
Aminoglycoside N(3)-acetyltransferase	A0A3P1UCA6	Q81P86_BACAN	Bacillus anthracis	3	0.8254
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.8168
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8131
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8117
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8060
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8016
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7992
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.7942
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.7893
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7881
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7861
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.7844
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	3	0.7826
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7788
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7748
5-methylthioadenosine/S-adenosylhomocysteine deaminase	Q7NZ90	Q7NZ90_CHRVO	Chromobacterium violaceum	3	0.7725
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7710
Stimulator of interferon genes protein	Q86WV6	STING_HUMAN	Homo sapiens	3	0.7684
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7673
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7643
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7624
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7600
Caffeic acid O-methyltransferase	Q9ZTU2	Q9ZTU2_LOLPR	Lolium perenne	4	0.7553
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7536
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7531
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7502
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7492
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	4	0.7473
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7471
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7438
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7426
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.7414
Insulin-degrading enzyme	P14735	IDE_HUMAN	Homo sapiens	2	0.7410
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7409
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7373
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7362
Multidrug efflux pump subunit AcrB	P31224	ACRB_ECOLI	Escherichia coli	3	0.7360
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.7357
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7353
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7342
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7339
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7331
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	4	0.7317
Avidin	P02701	AVID_CHICK	Gallus gallus	3	0.7312
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7306
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7275
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7261
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7251
DNA polymerase theta	O75417	DPOLQ_HUMAN	Homo sapiens	4	0.7248
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7244
Beta-galactoside-specific lectin 1	P81446	ML1_VISAL	Viscum album	3	0.7238
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7221
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7216
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7215
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7200
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	2	0.7183
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7174
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	2	0.7167
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7161
Casein kinase I isoform gamma-3	Q9Y6M4	KC1G3_HUMAN	Homo sapiens	4	0.7143
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7137
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7125
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	3	0.7117
Tryptophan--tRNA ligase	Q9PIB4	SYW_CAMJE	Campylobacter jejuni subsp. jejuni serotype O:2	4	0.7115
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7114
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7110
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7105
Anthranilate phosphoribosyltransferase	P00500	TRPD_ACIAD	Acinetobacter baylyi	2	0.7091
Uncharacterized protein YML079W	Q03629	YMH9_YEAST	Saccharomyces cerevisiae	2	0.7090
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7085
Dihydropteroate synthase	Q81VW8	Q81VW8_BACAN	Bacillus anthracis	2	0.7078
Camphor 5-monooxygenase	P00183	CPXA_PSEPU	Pseudomonas putida	3	0.7074
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7074
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	2	0.7069
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7064
DNA ligase	P43813	DNLJ_HAEIN	Haemophilus influenzae	3	0.7051
Chorismate mutase AroH	P19080	AROH_BACSU	Bacillus subtilis	2	0.7051
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7044
Protocatechuate 3,4-dioxygenase beta chain	P00437	PCXB_PSEPU	Pseudomonas putida	2	0.7038
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7038
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7037
Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4	Q8GZB6	SUVH4_ARATH	Arabidopsis thaliana	3	0.7035
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7025
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	2	0.7020
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7017
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	2	0.7017
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7015
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7013

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