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2-(3’,4’-dihydroxyphenyl) ethyl-3-O-alpha-L-rhamnopyranosyl-4-O-piperidine- 3-carboxylic acid-6-O-caffeoyl-alpha-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)C1CCCNC1)O[C@@H]1OC(C)[C@H](C([C@@H]1O)O)O)O)/C=C/c1ccc(c(c1)O)O
InChI	InChI=1S/C35H45NO16/c1-17-27(42)28(43)29(44)35(49-17)52-32-30(45)34(47-12-10-19-5-8-22(38)24(40)14-19)50-25(31(32)51-33(46)20-3-2-11-36-15-20)16-48-26(41)9-6-18-4-7-21(37)23(39)13-18/h4-9,13-14,17,20,25,27-32,34-40,42-45H,2-3,10-12,15-16H2,1H3/b9-6+/t17?,20?,25?,27-,28?,29+,30+,31-,32?,34-,35+/m1/s1
InChIKey	FZOLEWCEXHBQLU-HWMDIFDBSA-N
Formula	C₃₅H₄₅NO₁₆
HBA	17
HBD	9
MW	735.74
Rotatable Bonds	12
TPSA	263.39
LogP	-0.47
Number Rings	5
Number Aromatic Rings	2
Heavy Atom Count	52
Formal Charge	0
Fraction CSP3	0.54
Exact Mass	735.27
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: 162920035

No compound-protein relationship available.

SMILES: c1ccccc1C=CC(=O)OCC2C(OC(=O)C3CCCNC3)C(OC4CCCCO4)CC(O2)OCCc5ccccc5

Level: 4

Mol. Weight: 735.74 g/mol

SMILES: c1ccccc1C=CC(=O)OCC2C(OC(=O)C3CCCNC3)CCC(O2)OCCc4ccccc4

Level: 3

Mol. Weight: 735.74 g/mol

SMILES: c1ccccc1C=CC(=O)OCC2C(C(CCO2)OC3CCCCO3)OC(=O)C4CCCNC4

Level: 3

Mol. Weight: 735.74 g/mol

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

Level: 3

Mol. Weight: 735.74 g/mol

SMILES: C1NCCCC1C(=O)OC(C2OC3CCCCO3)COC(C2)OCCc4ccccc4

Level: 3

Mol. Weight: 735.74 g/mol

SMILES: c1ccccc1C=CC(=O)OCC2C(CCCO2)OC(=O)C3CCCNC3

Level: 2

Mol. Weight: 735.74 g/mol

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

Level: 2

Mol. Weight: 735.74 g/mol

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

Level: 2

Mol. Weight: 735.74 g/mol

SMILES: C1NCCCC1C(=O)OC2CCC(OC2)OCCc3ccccc3

Level: 2

Mol. Weight: 735.74 g/mol

SMILES: C1NCCCC1C(=O)OC(COCC2)C2OC3CCCCO3

Level: 2

Mol. Weight: 735.74 g/mol

SMILES: c1ccccc1CCOC(OCC2)CC2OC3CCCCO3

Level: 2

Mol. Weight: 735.74 g/mol

SMILES: O1CCCCC1COC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 735.74 g/mol

SMILES: C1NCCCC1C(=O)OC2CCCOC2

Level: 1

Mol. Weight: 735.74 g/mol

SMILES: c1ccccc1CCOC2CCCCO2

Level: 1

Mol. Weight: 735.74 g/mol

SMILES: C1COCCC1OC2CCCCO2

Level: 1

Mol. Weight: 735.74 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 735.74 g/mol

SMILES: C1CCNCC1

Level: 0

Mol. Weight: 735.74 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 735.74 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.76
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -0.63
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 666.53

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.72
Plasma Protein Binding: 37.45
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: 9.39
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -14.51
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.53
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.34
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: -1211701.9
Rat (Acute): 2.26
Rat (Chronic Oral): 3.79
Fathead Minnow: 1537.92
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: 130132.31
Hydration Free Energy: -2.92
Log(D) at pH=7.4: 0.6
Log(P): -0.12
Log S: -4.39
Log(Vapor Pressure): -4278.52
Melting Point: 224.99
pKa Acid: -5.56
pKa Basic: 6.05

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	0.9366
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9366
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8952
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8952
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8665
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8665
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.8660
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.8660
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8625
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8625
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8596
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8596
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8306
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8306
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8270
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8270
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8214
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8214
Prolyl tripeptidyl peptidase	Q7MUW6	PTP_PORGI	Porphyromonas gingivalis	3	0.7745
Prolyl tripeptidyl peptidase	Q7MUW6	PTP_PORGI	Porphyromonas gingivalis	3	0.7745
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7742
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7742
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7664
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7664
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7569
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7569
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7499
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7499
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7489
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7489
Tubulin--tyrosine ligase	F6Z895	A9ULH4_XENTR	Xenopus tropicalis	4	0.7419
Tubulin--tyrosine ligase	F6Z895	A9ULH4_XENTR	Xenopus tropicalis	4	0.7419
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.7332
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.7332
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7180
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7180
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7167
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7167
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7136
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7136
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7135
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7135
Uncharacterized protein YML079W	Q03629	YMH9_YEAST	Saccharomyces cerevisiae	2	0.7131
Uncharacterized protein YML079W	Q03629	YMH9_YEAST	Saccharomyces cerevisiae	2	0.7131
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7080
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7080
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7079
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7079
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	2	0.7067
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	2	0.7067
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7063
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7063
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7046
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7046
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7028
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7028
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7014
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7014

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