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Premnoside C

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(c(c2)OC)O)OC(=O)/C=C/c2ccc(c(c2)O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C40H46O20/c1-17-29(48)34(56-26(46)9-5-18-3-7-21(43)23(45)13-18)35(57-27(47)10-6-19-4-8-22(44)24(14-19)52-2)39(54-17)58-33-20-11-12-53-37(28(20)40(16-42)36(33)60-40)59-38-32(51)31(50)30(49)25(15-41)55-38/h3-14,17,20,25,28-39,41-45,48-51H,15-16H2,1-2H3/b9-5+,10-6+/t17-,20?,25-,28?,29-,30-,31+,32-,33+,34+,35+,36+,37+,38+,39-,40-/m1/s1
InChIKey	FOZKHCMNOIXOHB-GHCJPZGZSA-N
Formula	C₄₀H₄₆O₂₀
HBA	20
HBD	9
MW	846.79
Rotatable Bonds	13
TPSA	302.58
LogP	-1.08
Number Rings	7
Number Aromatic Rings	2
Heavy Atom Count	60
Formal Charge	0
Fraction CSP3	0.5
Exact Mass	846.26
Number of Lipinski Rule Violations	3

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

Showing of synonyms

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: 846.79 g/mol

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

Level: 3

Mol. Weight: 846.79 g/mol

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

Level: 3

Mol. Weight: 846.79 g/mol

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

Level: 3

Mol. Weight: 846.79 g/mol

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

Level: 2

Mol. Weight: 846.79 g/mol

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

Level: 2

Mol. Weight: 846.79 g/mol

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

Level: 2

Mol. Weight: 846.79 g/mol

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

Level: 2

Mol. Weight: 846.79 g/mol

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

Level: 1

Mol. Weight: 846.79 g/mol

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

Level: 1

Mol. Weight: 846.79 g/mol

SMILES: C1OCCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 846.79 g/mol

SMILES: C1COCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 846.79 g/mol

SMILES: C12C(O2)CC3C1COC=C3

Level: 0

Mol. Weight: 846.79 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 846.79 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 846.79 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.02
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: 458.620
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 60691.95

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.600
Plasma Protein Binding: 44.55
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: 10.490
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Toxic
Bee: Toxic
Bioconcentration Factor: -1407.600
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.620
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.110
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: -110154956.250
Rat (Acute): 2.740
Rat (Chronic Oral): 4.950
Fathead Minnow: 139055.120
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Toxic

General Properties

Boiling Point: 12383315.840
Hydration Free Energy: -2.920
Log(D) at pH=7.4: 0.040
Log(P): 0.11
Log S: -3.51
Log(Vapor Pressure): -407701.93
Melting Point: 189.81
pKa Acid: -2909.0
pKa Basic: -1.8

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	0.9501
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9018
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.8981
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8738
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	3	0.8613
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8600
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	3	0.8503
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.8498
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.8415
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8377
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8235
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.8215
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8211
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8132
Aminoglycoside N(3)-acetyltransferase	A0A3P1UCA6	Q81P86_BACAN	Bacillus anthracis	3	0.8128
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8110
histidine kinase	O32393	O32393_ARTPT	Arthrospira platensis	3	0.7946
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7937
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7891
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	3	0.7887
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7786
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7751
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.7631
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7629
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7618
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7587
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7543
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7501
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7447
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.7443
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7357
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	3	0.7330
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	3	0.7295
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7288
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7286
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7281
Purine nucleoside phosphorylase DeoD-type	O34925	DEOD_BACSU	Bacillus subtilis	2	0.7272
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7267
Insulin-degrading enzyme	P14735	IDE_HUMAN	Homo sapiens	2	0.7249
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.7240
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7229
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	4	0.7220
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7218
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	3	0.7211
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7208
Histone-lysine N-methyltransferase 2C	Q8NEZ4	KMT2C_HUMAN	Homo sapiens	3	0.7192
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7175
Histone-lysine N-methyltransferase EHMT2	Q96KQ7	EHMT2_HUMAN	Homo sapiens	3	0.7170
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7166
Peroxidase C1A	P00433	PER1A_ARMRU	Armoracia rusticana	2	0.7159
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7144
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7134
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7118
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7091
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.7073
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7066
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	2	0.7063
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	2	0.7060
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	2	0.7053
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	3	0.7051
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7047
Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4	Q8GZB6	SUVH4_ARATH	Arabidopsis thaliana	3	0.7046
DNA ligase	P43813	DNLJ_HAEIN	Haemophilus influenzae	3	0.7038
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	3	0.7022
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	2	0.7016
Anthranilate phosphoribosyltransferase	P00500	TRPD_ACIAD	Acinetobacter baylyi	2	0.7012
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7011
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7004

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