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1-O-trans-p-coumaroyl-2-O-trans-caffeoyl-alpha-L-rhamnopyranoside

Family: Plantae - Lamiaceae
Kingdom: Plantae
Class: Rhamnose
- Subclass: Acylated Rhamnopyranose

Canonical Smiles	Oc1ccc(cc1)/C=C/C(=O)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1OC(=O)/C=C/c1ccc(c(c1)O)O)O)O
InChI	InChI=1S/C24H24O10/c1-13-21(30)22(31)23(33-19(28)11-6-15-4-9-17(26)18(27)12-15)24(32-13)34-20(29)10-5-14-2-7-16(25)8-3-14/h2-13,21-27,30-31H,1H3/b10-5+,11-6+/t13-,21-,22+,23+,24-/m0/s1
InChIKey	WEOINEOAKSIIEZ-XNBRKEAASA-N
Formula	C₂₄H₂₄O₁₀
HBA	10
HBD	5
MW	472.45
Rotatable Bonds	6
TPSA	162.98
LogP	1.45
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	34
Formal Charge	0
Fraction CSP3	0.25
Exact Mass	472.14
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Premna odorata	Lamiaceae	Plantae	1037421

Showing of synonyms

Elmaidomy A.H, Mohyeldin M.M, et al. (2017). Acylated Iridoids and Rhamnopyranoses from Premna odorata (Lamiaceae) as Novel Mesenchymal–Epithelial Transition Factor Receptor Inhibitors for the Control of Breast Cancer.. Phytotherapy research : PTR, 2017, 31(10), 1546-1556. [View] [PubMed]

No compound-protein relationship available.

SMILES: c1ccccc1C=CC(=O)OC2C(OCCC2)OC(=O)C=Cc3ccccc3

Level: 2

Mol. Weight: 472.45 g/mol

SMILES: O1CCCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 472.45 g/mol

SMILES: C1OCCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 472.45 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 472.45 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 472.45 g/mol

Anticancer

Absorption

Caco-2 (logPapp): -6.73
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.870
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -2.27

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.930
Plasma Protein Binding: 81.2
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: Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 13.350
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: -0.870
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.040
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.470
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Toxic
T. Pyriformis: -144.210
Rat (Acute): 2.150
Rat (Chronic Oral): 3.980
Fathead Minnow: 4.250
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Toxic
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 544.460
Hydration Free Energy: -3.230
Log(D) at pH=7.4: 2.030
Log(P): 2.45
Log S: -4.66
Log(Vapor Pressure): -10.68
Melting Point: 193.81
pKa Acid: 6.61
pKa Basic: 2.33

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	0.9368
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.9148
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9117
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8732
Thymidylate synthase	P0A886	TYSY_ECO57	Escherichia coli O157:H7	3	0.8703
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8639
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	3	0.8637
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8621
Streptogramin A acetyltransferase	P50870	VATD_ENTFC	Enterococcus faecium	3	0.8510
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8418
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8365
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8352
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8313
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8307
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.8224
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8224
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.8212
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.8207
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	3	0.8164
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	2	0.8128
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.8081
Copper-transporting ATPase	Q97UU7	Q97UU7_SACS2	Saccharolobus solfataricus	4	0.8066
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8047
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8007
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7953
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7928
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7885
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7840
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.7819
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	3	0.7812
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7795
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7778
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7772
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7757
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7725
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7724
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7695
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7692
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7681
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7636
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	3	0.7625
Caffeic acid O-methyltransferase	Q9ZTU2	Q9ZTU2_LOLPR	Lolium perenne	4	0.7612
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7564
Seminal ribonuclease	P00669	RNS_BOVIN	Bos taurus	3	0.7556
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7533
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7513
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7507
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7505
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7487
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7443
Eukaryotic translation initiation factor 4E-1	P29557	IF4E1_WHEAT	Triticum aestivum	4	0.7422
Kinesin-like protein KIF11	P52732	KIF11_HUMAN	Homo sapiens	3	0.7410
Tubulin--tyrosine ligase	F6Z895	A9ULH4_XENTR	Xenopus tropicalis	4	0.7407
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.7406
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7392
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7383
Basic phospholipase A2 homolog piratoxin-1	P58399	PA2H1_BOTPI	Bothrops pirajai	4	0.7378
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7365
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7359
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7350
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7339
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7335
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7328
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7328
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7328
Albumin	P02768	ALBU_HUMAN	Homo sapiens	2	0.7251
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.7241
Kinesin heavy chain	Q41460	Q41460_SOLTU	Solanum tuberosum	3	0.7238
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7237
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	3	0.7236
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7223
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7214
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7202
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7202
Reaction center protein L chain	P0C0Y7	RCEH_RHOSH	Rhodobacter sphaeroides	3	0.7197
Insulin-degrading enzyme	P14735	IDE_HUMAN	Homo sapiens	2	0.7183
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7178
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7163
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7162
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7154
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	2	0.7151
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7147
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7135
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7128
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.7101
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7094
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7081
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7079
Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4	Q8GZB6	SUVH4_ARATH	Arabidopsis thaliana	3	0.7071
Purine nucleoside phosphorylase DeoD-type	B1JL34	DEOD_YERPY	Yersinia pseudotuberculosis serotype O:3	2	0.7059
Anthranilate phosphoribosyltransferase	P00500	TRPD_ACIAD	Acinetobacter baylyi	2	0.7057
Fructose-1,6-bisphosphatase 1	P09467	F16P1_HUMAN	Homo sapiens	2	0.7055
DNA ligase	P43813	DNLJ_HAEIN	Haemophilus influenzae	3	0.7052
Kynurenine--oxoglutarate transaminase 1	Q16773	KAT1_HUMAN	Homo sapiens	2	0.7050
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7043
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7041
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7040
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7038
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7029
Tryptophan--tRNA ligase	Q9PIB4	SYW_CAMJE	Campylobacter jejuni subsp. jejuni serotype O:2	4	0.7025
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	4	0.7023
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	2	0.7015
Chromosome partitioning protein ParA	B0ZE06	B0ZE06_ECOLX	Escherichia coli	3	0.7013
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7013
Formate--tetrahydrofolate ligase	P21164	FTHS_MOOTH	Moorella thermoacetica	2	0.7008
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7004

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