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Premnoside E

Family: Plantae - Lamiaceae
Kingdom: Plantae
Class: Terpenoid
- Subclass: Iridoid Glycoside

Canonical Smiles	OC[C@H]1O[C@@H](O[C@@H]2OC=CC3C2[C@@]2(CO)O[C@H]2[C@H]3O[C@H]2O[C@H](C)[C@H]([C@@H]([C@@H]2O)OC(=O)/C=C/c2ccc(cc2)OC)OC(=O)/C=C/c2ccc(cc2)OC)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C41H48O18/c1-20-34(55-27(44)14-8-21-4-10-23(50-2)11-5-21)36(56-28(45)15-9-22-6-12-24(51-3)13-7-22)33(49)40(53-20)57-35-25-16-17-52-38(29(25)41(19-43)37(35)59-41)58-39-32(48)31(47)30(46)26(18-42)54-39/h4-17,20,25-26,29-40,42-43,46-49H,18-19H2,1-3H3/b14-8+,15-9+/t20-,25?,26-,29?,30-,31+,32-,33+,34-,35+,36-,37+,38+,39+,40-,41-/m1/s1
InChIKey	FMRHDGCSVPKQPN-OXRCYREBSA-N
Formula	C₄₁H₄₈O₁₈
HBA	18
HBD	6
MW	828.82
Rotatable Bonds	14
TPSA	251.12
LogP	-0.19
Number Rings	7
Number Aromatic Rings	2
Heavy Atom Count	59
Formal Charge	0
Fraction CSP3	0.51
Exact Mass	828.28
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Premna odorata	Lamiaceae	Plantae	1037421
2	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]
Elmaidomy A.H, Mohammed R, et al. (2019). Metabolomic Profiling and Cytotoxic Tetrahydrofurofuran Lignans Investigations from Premna odorata Blanco. Metabolites, 2019, 9(10), 223. [View] [PubMed]

No compound-protein relationship available.

SMILES: c1ccccc1C=CC(=O)OC2C(OC(=O)C=Cc3ccccc3)COC(C2)OC(C(O4)C45)C6C5C(OC=C6)OC7CCCCO7

Level: 4

Mol. Weight: 828.82 g/mol

SMILES: c1ccccc1C=CC(=O)OC2C(OC(=O)C=Cc3ccccc3)COC(C2)OC(C(O4)C45)C6C5COC=C6

Level: 3

Mol. Weight: 828.82 g/mol

SMILES: c1ccccc1C=CC(=O)OC2CCC(OC2)OC(C(O3)C34)C5C4C(OC=C5)OC6CCCCO6

Level: 3

Mol. Weight: 828.82 g/mol

SMILES: c1ccccc1C=CC(=O)OC2CC(OCC2)OC(C(O3)C34)C5C4C(OC=C5)OC6CCCCO6

Level: 3

Mol. Weight: 828.82 g/mol

SMILES: c1ccccc1C=CC(=O)OC2CCC(OC2)OC(C(O3)C34)C5C4COC=C5

Level: 2

Mol. Weight: 828.82 g/mol

SMILES: c1ccccc1C=CC(=O)OC2CC(OCC2)OC(C(O3)C34)C5C4COC=C5

Level: 2

Mol. Weight: 828.82 g/mol

SMILES: c1ccccc1C=CC(=O)OC2C(COCC2)OC(=O)C=Cc3ccccc3

Level: 2

Mol. Weight: 828.82 g/mol

SMILES: O1CCCCC1OC(C(O2)C23)C4C3C(OC=C4)OC5CCCCO5

Level: 2

Mol. Weight: 828.82 g/mol

SMILES: C1=COCC2C1C(C(O3)C23)OC4CCCCO4

Level: 1

Mol. Weight: 828.82 g/mol

SMILES: C12C(O2)CC3C1C(OC=C3)OC4CCCCO4

Level: 1

Mol. Weight: 828.82 g/mol

SMILES: C1OCCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 828.82 g/mol

SMILES: C1COCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 828.82 g/mol

SMILES: C12C(O2)CC3C1COC=C3

Level: 0

Mol. Weight: 828.82 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 828.82 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 828.82 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.65
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: 373.100
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 49482.69

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.740
Plasma Protein Binding: 50.56
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: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Inhibitor

Excretion

Clearance: 5.570
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Toxic
Bioconcentration Factor: -1149.110
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.510
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 4.160
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: -89811762.390
Rat (Acute): 3.340
Rat (Chronic Oral): 4.710
Fathead Minnow: 113375.980
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Toxic
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 10096292.740
Hydration Free Energy: -2.920
Log(D) at pH=7.4: 2.020
Log(P): 1.89
Log S: -3.45
Log(Vapor Pressure): -332384.26
Melting Point: 155.99
pKa Acid: -2357.94
pKa Basic: -2.47

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8837
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8772
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	2	0.8529
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8381
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7752
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7696
Orf1ab polyprotein	Q6T1E9	Q6T1E9_CVHSA	SARS coronavirus CUHK-L2	3	0.7663
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7621
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7620
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7535
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7520
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7514
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7462
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	2	0.7441
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7428
Bifunctional protein GlmU	P43889	GLMU_HAEIN	Haemophilus influenzae	3	0.7427
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	2	0.7414
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7404
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	2	0.7399
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7399
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7388
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7385
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7380
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7378
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7369
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	2	0.7367
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	2	0.7360
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7354
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7353
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7352
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	2	0.7351
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7322
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7311
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7311
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7309
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7302
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7301
Pantothenate synthetase	P9WIL4	PANC_MYCTO	Mycobacterium tuberculosis	2	0.7301
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	2	0.7295
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7276
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	2	0.7273
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7273
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	2	0.7246
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7243
Ribosome-inactivating protein 3	P25891	RIP3_MAIZE	Zea mays	2	0.7243
Albumin	P02768	ALBU_HUMAN	Homo sapiens	2	0.7242
RIO-type serine/threonine-protein kinase Rio1	O28471	RIO1_ARCFU	Archaeoglobus fulgidus	2	0.7239
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	2	0.7225
Myosin heavy chain kinase A	P42527	MHCKA_DICDI	Dictyostelium discoideum	2	0.7217
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7215
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7211
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	2	0.7209
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7204
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	2	0.7197
Protein kinase C iota type	Q62074	KPCI_MOUSE	Mus musculus	2	0.7194
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7188
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7187
Serine/threonine-protein kinase toxin HipA	P23874	HIPA_ECOLI	Escherichia coli	2	0.7165
Biotin carboxylase	P24182	ACCC_ECOLI	Escherichia coli	2	0.7164
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	2	0.7158
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	2	0.7150
Aminoglycoside N(3)-acetyltransferase	A0A3P1UCA6	Q81P86_BACAN	Bacillus anthracis	2	0.7145
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7135
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	2	0.7134
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7133
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	2	0.7128
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	2	0.7123
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	2	0.7112
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	2	0.7103
Pantothenate synthetase	P9WIL4	PANC_MYCTO	Mycobacterium tuberculosis	2	0.7097
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	2	0.7095
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	2	0.7092
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	2	0.7090
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7087
Focal adhesion kinase 1	Q05397	FAK1_HUMAN	Homo sapiens	2	0.7085
Glycogen phosphorylase, liver form	P06737	PYGL_HUMAN	Homo sapiens	3	0.7070
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	2	0.7068
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	2	0.7066
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate hydrolase	P47229	BPHD_PARXL	Paraburkholderia xenovorans	2	0.7061
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	2	0.7040
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	2	0.7037
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	2	0.7028
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	2	0.7002

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