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2-(3’,4’-dihydroxyphenyl) ethyl-3-O-alpha-L-rhamnopyranosyl-4-O-p-hydroxyphenylacetyl-6-O-caffeoyl-beta-D-glucopyranoside

Family: Plantae - Bignoniaceae
Kingdom: Plantae
Class: Phenolic
- Subclass: Caffeic Acid Derivative

Canonical Smiles	O=C(OCC1O[C@@H](OCCc2ccc(c(c2)O)O)[C@H](C([C@@H]1OC(=O)Cc1ccc(cc1)O)O[C@@H]1OC(C)[C@H](C([C@@H]1O)O)O)O)/C=C/c1ccc(c(c1)O)O
InChI	InChI=1S/C37H42O17/c1-18-30(45)31(46)32(47)37(51-18)54-35-33(48)36(49-13-12-21-5-10-24(40)26(42)15-21)52-27(34(35)53-29(44)16-20-2-7-22(38)8-3-20)17-50-28(43)11-6-19-4-9-23(39)25(41)14-19/h2-11,14-15,18,27,30-42,45-48H,12-13,16-17H2,1H3/b11-6+/t18?,27?,30-,31?,32+,33+,34-,35?,36-,37+/m1/s1
InChIKey	BXZRZXGIZDTSFV-JEYGFGRRSA-N
Formula	C₃₇H₄₂O₁₇
HBA	17
HBD	9
MW	758.73
Rotatable Bonds	13
TPSA	271.59
LogP	0.48
Number Rings	5
Number Aromatic Rings	3
Heavy Atom Count	54
Formal Charge	0
Fraction CSP3	0.41
Exact Mass	758.24
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Jacaranda mimosaefolia	Bignoniaceae	Plantae	185774

Showing of synonyms

Zaghloul AM, Gohar AA, et al. (2011). Phenylpropanoids from the stem bark of Jacaranda mimosaefolia. Natural Product Research,2011,25(1),68-76. [View] [PubMed]

Pubchem: 162951213

No compound-protein relationship available.

SMILES: c1ccccc1C=CC(=O)OCC2C(OC(=O)Cc3ccccc3)C(OC4CCCCO4)CC(O2)OCCc5ccccc5

Level: 4

Mol. Weight: 758.73 g/mol

SMILES: c1ccccc1C=CC(=O)OCC2C(OC(=O)Cc3ccccc3)CCC(O2)OCCc4ccccc4

Level: 3

Mol. Weight: 758.73 g/mol

SMILES: c1ccccc1C=CC(=O)OCC2C(C(CCO2)OC3CCCCO3)OC(=O)Cc4ccccc4

Level: 3

Mol. Weight: 758.73 g/mol

SMILES: c1ccccc1C=CC(=O)OCC2CC(OC3CCCCO3)CC(O2)OCCc4ccccc4

Level: 3

Mol. Weight: 758.73 g/mol

SMILES: c1ccccc1CC(=O)OC(C2OC3CCCCO3)COC(C2)OCCc4ccccc4

Level: 3

Mol. Weight: 758.73 g/mol

SMILES: c1ccccc1C=CC(=O)OCC2C(CCCO2)OC(=O)Cc3ccccc3

Level: 2

Mol. Weight: 758.73 g/mol

SMILES: c1ccccc1C=CC(=O)OCC2CCCC(O2)OCCc3ccccc3

Level: 2

Mol. Weight: 758.73 g/mol

SMILES: c1ccccc1C=CC(=O)OCC2CC(CCO2)OC3CCCCO3

Level: 2

Mol. Weight: 758.73 g/mol

SMILES: c1ccccc1CC(=O)OC2CCC(OC2)OCCc3ccccc3

Level: 2

Mol. Weight: 758.73 g/mol

SMILES: c1ccccc1CC(=O)OC(COCC2)C2OC3CCCCO3

Level: 2

Mol. Weight: 758.73 g/mol

SMILES: c1ccccc1CCOC(OCC2)CC2OC3CCCCO3

Level: 2

Mol. Weight: 758.73 g/mol

SMILES: O1CCCCC1COC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 758.73 g/mol

SMILES: C1OCCCC1OC(=O)Cc2ccccc2

Level: 1

Mol. Weight: 758.73 g/mol

SMILES: c1ccccc1CCOC2CCCCO2

Level: 1

Mol. Weight: 758.73 g/mol

SMILES: C1COCCC1OC2CCCCO2

Level: 1

Mol. Weight: 758.73 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 758.73 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 758.73 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.79
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 5.54
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 1468.13

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.78
Plasma Protein Binding: 43.28
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: Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 12.63
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -33.77
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.9
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.62
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: -2666397.12
Rat (Acute): 2.21
Rat (Chronic Oral): 4.68
Fathead Minnow: 3373.95
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 293447.74
Hydration Free Energy: -2.92
Log(D) at pH=7.4: 1.04
Log(P): 1.49
Log S: -5.42
Log(Vapor Pressure): -9638.51
Melting Point: 212.88
pKa Acid: -37.02
pKa Basic: 3.18

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	0.9374
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9374
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9243
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9243
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.8992
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.8992
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8938
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8938
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.8867
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	3	0.8867
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.8659
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.8659
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8652
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8652
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	4	0.8640
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	4	0.8640
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8627
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8627
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8616
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8616
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8452
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8452
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8414
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8414
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.8401
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.8401
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8338
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8338
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8282
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8282
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8175
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8175
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8062
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8062
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.8030
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.8030
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.8026
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.8026
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7901
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7901
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7885
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7885
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.7740
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.7740
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7680
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7680
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7674
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7674
Aminoglycoside N(3)-acetyltransferase	A0A3P1UCA6	Q81P86_BACAN	Bacillus anthracis	3	0.7630
Aminoglycoside N(3)-acetyltransferase	A0A3P1UCA6	Q81P86_BACAN	Bacillus anthracis	3	0.7630
Caffeic acid O-methyltransferase	Q9ZTU2	Q9ZTU2_LOLPR	Lolium perenne	4	0.7606
Caffeic acid O-methyltransferase	Q9ZTU2	Q9ZTU2_LOLPR	Lolium perenne	4	0.7606
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7525
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7525
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7515
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7515
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7505
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7505
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7503
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7503
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7498
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7498
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7374
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7374
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	3	0.7353
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	3	0.7353
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7319
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7319
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7268
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7268
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7250
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7250
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7249
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7249
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7223
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7223
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7218
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7218
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	3	0.7203
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	3	0.7203
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7194
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7194
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7160
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.7160
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7160
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.7160
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7160
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7160
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7160
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7160
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7155
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7155
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7151
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7151
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7142
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7142
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7098
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7098
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7091
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7091
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	3	0.7084
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	3	0.7084
Gentisate 1,2-dioxygenase	Q67FT0	Q67FT0_PSESE	Pseudaminobacter salicylatoxidans	2	0.7083
Gentisate 1,2-dioxygenase	Q67FT0	Q67FT0_PSESE	Pseudaminobacter salicylatoxidans	2	0.7083
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7072
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7072
Small heat shock protein StHsp14.0	Q970D9	Q970D9_SULTO	Sulfurisphaera tokodaii	3	0.7045
Small heat shock protein StHsp14.0	Q970D9	Q970D9_SULTO	Sulfurisphaera tokodaii	3	0.7045
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7035
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7035
Uncharacterized protein YML079W	Q03629	YMH9_YEAST	Saccharomyces cerevisiae	2	0.7024
Uncharacterized protein YML079W	Q03629	YMH9_YEAST	Saccharomyces cerevisiae	2	0.7024
Protocatechuate 3,4-dioxygenase beta chain	P00437	PCXB_PSEPU	Pseudomonas putida	2	0.7019
Protocatechuate 3,4-dioxygenase beta chain	P00437	PCXB_PSEPU	Pseudomonas putida	2	0.7019
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7018
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7018
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7014
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7014

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