ANPDB

Select a section from the left sidebar

Tomenin

Family: Plantae - Asteraceae
Kingdom: Plantae
Class: Coumarin
- Subclass: Coumarin Glucoside

Canonical Smiles	OC[C@H]1O[C@@H](Oc2c(OC)c(OC)cc3c2ccc(=O)o3)[C@@H]([C@H]([C@@H]1O)O)O
InChI	InChI=1S/C17H20O10/c1-23-9-5-8-7(3-4-11(19)25-8)15(16(9)24-2)27-17-14(22)13(21)12(20)10(6-18)26-17/h3-5,10,12-14,17-18,20-22H,6H2,1-2H3/t10-,12-,13+,14-,17+/m1/s1
InChIKey	DHNNEMKGTXETQO-HFVZKWEFSA-N
Formula	C₁₇H₂₀O₁₀
HBA	10
HBD	4
MW	384.34
Rotatable Bonds	5
TPSA	148.05
LogP	-1.01
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	27
Formal Charge	0
Fraction CSP3	0.47
Exact Mass	384.11
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Artemisia herba-alba	Asteraceae	Plantae	72329

Showing of synonyms

Mohamed T.A, Abd El Aty A.A, et al. (2021). New antimicrobial metabolites from the medicinal herb Artemisia herba-Alba. Natural product research, 2021, 35(12), 1959-1967. [View] [PubMed]

Pubchem: 5321970

Cas: 28446-08-4

Zinc: ZINC000033834024

Chebi: 191610

No compound-protein relationship available.

SMILES: c1cc(=O)oc(c12)cccc2OC3CCCCO3

Level: 1

Mol. Weight: 384.34 g/mol

SMILES: c1cccc(c12)oc(=O)cc2

Level: 0

Mol. Weight: 384.34 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 384.34 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.75
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -4.950
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -1.34

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.890
Plasma Protein Binding: 69.79
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: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 5.850
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.840
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.070
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.030
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: -6.710
Rat (Acute): 2.320
Rat (Chronic Oral): 3.540
Fathead Minnow: 4.110
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 490.350
Hydration Free Energy: -13.010
Log(D) at pH=7.4: -0.370
Log(P): -1.45
Log S: -2.44
Log(Vapor Pressure): -10.43
Melting Point: 177.39
pKa Acid: 5.44
pKa Basic: 3.69

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.9061
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8908
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.8176
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.8051
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7849
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7817
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7527
beta-glucosidase	Q92AS9	Q92AS9_LISIN	Listeria innocua serovar 6a	3	0.7457
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7433
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7345
Adenosine 5'-monophosphoramidase HINT1	P80912	HINT1_RABIT	Oryctolagus cuniculus	3	0.7343
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7325
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7323
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7269
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7216
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7173
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7171
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7160
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7142
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7138
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	2	0.7088
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	2	0.7085
Metallo-beta-lactamase type 2	C7C422	BLAN1_KLEPN	Klebsiella pneumoniae	2	0.7066
Riboflavin synthase	Q58584	RISC_METJA	Methanocaldococcus jannaschii	4	0.7025
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	2	0.7015

Download SDF