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Premnoside B

Family: Lamiaceae
Kingdom: Plantae
Class: Iridoid
- Subclass: Acylated 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)O)OC(=O)/C=C/c2ccc(c(c2)O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C39H44O19/c1-17-28(47)33(54-25(45)11-6-19-4-9-22(43)23(44)14-19)34(55-26(46)10-5-18-2-7-20(42)8-3-18)38(52-17)56-32-21-12-13-51-36(27(21)39(16-41)35(32)58-39)57-37-31(50)30(49)29(48)24(15-40)53-37/h2-14,17,21,24,27-38,40-44,47-50H,15-16H2,1H3/b10-5+,11-6+/t17-,21?,24-,27?,28-,29-,30+,31-,32+,33+,34+,35+,36+,37+,38-,39-/m1/s1
InChIKey	CWOWGVARVOJSSH-SAHHVHMBSA-N
Formula	C₃₉H₄₄O₁₉
HBA	19
HBD	9
MW	816.76
Rotatable Bonds	12
TPSA	293.35
LogP	-1.09
Number Rings	7
Number Aromatic Rings	2
Heavy Atom Count	58
Formal Charge	0
Fraction CSP3	0.49
Exact Mass	816.25
Number of Lipinski Rule Violations	3

#	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(OC(=O)C=Cc3ccccc3)CCOC2OC(C(O4)C45)C6C5C(OC=C6)OC7CCCCO7

Level: 4

Mol. Weight: 630.69 g/mol

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

Level: 3

Mol. Weight: 530.57 g/mol

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

Level: 3

Mol. Weight: 484.55 g/mol

SMILES: c1ccccc1C=CC(=O)OC2C(OCCC2)OC(C(O3)C34)C5C4C(OC=C5)OC6CCCCO6

Level: 3

Mol. Weight: 484.55 g/mol

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

Level: 2

Mol. Weight: 384.43 g/mol

SMILES: c1ccccc1C=CC(=O)OC2C(OCCC2)OC(C(O3)C34)C5C4COC=C5

Level: 2

Mol. Weight: 384.43 g/mol

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

Level: 2

Mol. Weight: 378.42 g/mol

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

Level: 2

Mol. Weight: 338.4 g/mol

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

Level: 1

Mol. Weight: 238.28 g/mol

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

Level: 1

Mol. Weight: 238.28 g/mol

SMILES: C1OCCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 232.28 g/mol

SMILES: C1COCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 232.28 g/mol

SMILES: C12C(O2)CC3C1COC=C3

Level: 0

Mol. Weight: 138.17 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 86.13 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.12
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 182.150
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 24554.82

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.640
Plasma Protein Binding: 47.61
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: 10.120
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Toxic
Bioconcentration Factor: -568.050
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.550
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.950
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: -44568492.520
Rat (Acute): 2.700
Rat (Chronic Oral): 5.040
Fathead Minnow: 56266.100
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: 5006700.810
Hydration Free Energy: -2.920
Log(D) at pH=7.4: -0.360
Log(P): 0.26
Log S: -3.3
Log(Vapor Pressure): -164795.38
Melting Point: 191.28
pKa Acid: -1145.28
pKa Basic: 1.25

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	0.9355
Thymidylate synthase	P0A886	TYSY_ECO57	Escherichia coli O157:H7	3	0.9175
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9073
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.8992
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8956
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8841
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8723
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8668
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.8579
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8574
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8502
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.8473
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	4	0.8399
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8311
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8300
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8265
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.8264
Aminoglycoside N(3)-acetyltransferase	A0A3P1UCA6	Q81P86_BACAN	Bacillus anthracis	3	0.8253
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8221
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.8192
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.8179
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8118
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	4	0.8107
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8099
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.8073
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	3	0.8037
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8018
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7972
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7925
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.7919
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7910
Secoisolariciresinol dehydrogenase	Q94KL8	SILD_PODPE	Podophyllum peltatum	4	0.7873
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	4	0.7872
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7856
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	3	0.7828
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.7824
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	3	0.7823
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.7805
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	3	0.7802
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7799
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7725
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7722
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7713
Avidin	P02701	AVID_CHICK	Gallus gallus	3	0.7703
Seminal ribonuclease	P00669	RNS_BOVIN	Bos taurus	3	0.7661
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7648
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	3	0.7618
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7602
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7601
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	4	0.7578
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7552
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7534
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7498
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7494
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7430
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7360
Genome polyprotein	C0LMU0	C0LMU0_9FLAV	dengue virus type 3	3	0.7358
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.7316
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7299
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7297
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	3	0.7283
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7275
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7270
Kinesin-like protein KIF11	P52732	KIF11_HUMAN	Homo sapiens	3	0.7253
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7248
Caffeic acid O-methyltransferase	Q9ZTU2	Q9ZTU2_LOLPR	Lolium perenne	4	0.7245
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7243
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7240
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7236
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	3	0.7236
Purine nucleoside phosphorylase DeoD-type	O34925	DEOD_BACSU	Bacillus subtilis	2	0.7228
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	3	0.7223
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7221
Casein kinase I isoform gamma-3	Q9Y6M4	KC1G3_HUMAN	Homo sapiens	4	0.7201
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7185
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7183
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.7180
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	3	0.7179
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	2	0.7179
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7163
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7162
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7160
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7154
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7152
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7150
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	4	0.7146
Uncharacterized protein YML079W	Q03629	YMH9_YEAST	Saccharomyces cerevisiae	2	0.7135
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7126
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7120
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	2	0.7103
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	2	0.7102
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7101
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7094
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7088
Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4	Q8GZB6	SUVH4_ARATH	Arabidopsis thaliana	3	0.7069
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7069
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	2	0.7047
Capsid protein VP1	O56137	O56137_9VIRU	Adeno-associated virus - 6	3	0.7046
DNA ligase	P43813	DNLJ_HAEIN	Haemophilus influenzae	3	0.7045
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	P0AF12	MTNN_ECOLI	Escherichia coli	2	0.7039
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7031
Protease	O38896	O38896_9HIV1	Human immunodeficiency virus 1	3	0.7020
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7018
Class 10 plant pathogenesis-related protein 2B	Q9LLQ2	P102B_LUPLU	Lupinus luteus	2	0.7001

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