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Premnoside F

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]2OC(=O)/C=C/c2ccc(cc2)OC)OC(=O)/C=C/c2ccc(cc2)OC)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C41H48O18/c1-20-30(46)35(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)40(53-20)57-34-25-16-17-52-38(29(25)41(19-43)37(34)59-41)58-39-33(49)32(48)31(47)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	HNDCCLJCIPXDSQ-LUUYTIGFSA-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)CCOC2OC(C(O4)C45)C6C5C(OC=C6)OC7CCCCO7

Level: 4

Mol. Weight: 828.82 g/mol

SMILES: c1ccccc1C=CC(=O)OC2C(OC(=O)C=Cc3ccccc3)CCOC2OC(C(O4)C45)C6C5COC=C6

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)OC2C(OCCC2)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)C5C4COC=C5

Level: 2

Mol. Weight: 828.82 g/mol

SMILES: c1ccccc1C=CC(=O)OC2C(OCCC2)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): -5.63
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: 373.890
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 49583.15

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.740
Plasma Protein Binding: 50.35
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: 5.620
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Toxic
Bioconcentration Factor: -1151.090
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.530
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 4.210
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: -89993954.530
Rat (Acute): 3.330
Rat (Chronic Oral): 4.610
Fathead Minnow: 113605.790
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: 10116778.240
Hydration Free Energy: -2.920
Log(D) at pH=7.4: 1.880
Log(P): 1.72
Log S: -3.47
Log(Vapor Pressure): -333058.71
Melting Point: 154.59
pKa Acid: -2363.5
pKa Basic: -2.78

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8837
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	2	0.8541
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.8228
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8121
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7943
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7894
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9QYJ6	PDE10_RAT	Rattus norvegicus	3	0.7747
Phosphoenolpyruvate carboxykinase [GTP]	A5TYT6	PCKG_MYCTA	Mycobacterium tuberculosis	3	0.7744
Phosphoenolpyruvate carboxykinase [GTP]	P9WIH3	PCKG_MYCTU	Mycobacterium tuberculosis	3	0.7713
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7621
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7557
Insulin-degrading enzyme	P14735	IDE_HUMAN	Homo sapiens	2	0.7545
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7532
Bifunctional protein GlmU	P43889	GLMU_HAEIN	Haemophilus influenzae	3	0.7495
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	2	0.7494
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	4	0.7490
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7487
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7472
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7469
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.7456
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7452
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	2	0.7440
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7410
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7403
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	2	0.7389
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7385
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7383
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	2	0.7381
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7378
Non-receptor tyrosine-protein kinase TYK2	P29597	TYK2_HUMAN	Homo sapiens	3	0.7375
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7375
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7370
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7365
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	2	0.7362
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	2	0.7361
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7358
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7355
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	2	0.7355
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7352
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7327
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7322
Antitumor antibiotic C-1027 apoprotein	Q06110	CAGA_STRGL	Streptomyces globisporus	3	0.7321
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7321
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7314
Albumin	P02768	ALBU_HUMAN	Homo sapiens	2	0.7301
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7299
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7291
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	2	0.7287
Myosin heavy chain kinase A	P42527	MHCKA_DICDI	Dictyostelium discoideum	2	0.7285
Glutathione S-transferase F2	P46422	GSTF2_ARATH	Arabidopsis thaliana	2	0.7259
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	2	0.7255
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7242
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7240
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	2	0.7223
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7222
Pantothenate synthetase	P9WIL4	PANC_MYCTO	Mycobacterium tuberculosis	2	0.7221
Secoisolariciresinol dehydrogenase	Q94KL8	SILD_PODPE	Podophyllum peltatum	3	0.7217
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7213
Ribosome-inactivating protein 3	P25891	RIP3_MAIZE	Zea mays	2	0.7212
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7212
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7210
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7208
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	2	0.7196
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	2	0.7175
Protein kinase C iota type	Q62074	KPCI_MOUSE	Mus musculus	2	0.7171
RIO-type serine/threonine-protein kinase Rio1	O28471	RIO1_ARCFU	Archaeoglobus fulgidus	2	0.7157
Biotin carboxylase	P24182	ACCC_ECOLI	Escherichia coli	2	0.7154
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	2	0.7153
Pantothenate synthetase	P9WIL4	PANC_MYCTO	Mycobacterium tuberculosis	2	0.7137
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	2	0.7134
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	2	0.7133
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7130
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7127
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	2	0.7123
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7120
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	2	0.7105
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	2	0.7097
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7085
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	2	0.7083
Focal adhesion kinase 1	Q05397	FAK1_HUMAN	Homo sapiens	2	0.7081
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	2	0.7080
Aminoglycoside N(3)-acetyltransferase	A0A3P1UCA6	Q81P86_BACAN	Bacillus anthracis	2	0.7078
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate hydrolase	P47229	BPHD_PARXL	Paraburkholderia xenovorans	2	0.7078
Serine/threonine-protein kinase toxin HipA	P23874	HIPA_ECOLI	Escherichia coli	2	0.7073
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	2	0.7070
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	2	0.7069
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	2	0.7060
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7054
Phosphoenolpyruvate carboxykinase [GTP]	A5TYT6	PCKG_MYCTA	Mycobacterium tuberculosis	3	0.7043
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7032
tyrosine--tRNA ligase	Q4QFJ7	Q4QFJ7_LEIMA	Leishmania major	3	0.7026
Copper-transporting ATPase	Q97UU7	Q97UU7_SACS2	Saccharolobus solfataricus	3	0.7019
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	2	0.7019
3-hydroxybenzoate 4-monooxygenase	Q6SSJ6	MOBA_COMTE	Comamonas testosteroni	2	0.7014
Chorismate mutase AroH	P19080	AROH_BACSU	Bacillus subtilis	2	0.7012
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7008
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	2	0.7008
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	P49354	FNTA_HUMAN	Homo sapiens	3	0.7007
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	2	0.7000

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