ANPDB

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Parthenolide

Family: Plantae - Magnoliaceae
Kingdom: Plantae
Class: Terpenoid
- Subclass: Sesquiterpene Lactone

Canonical Smiles	C/C/1=C\CC[C@@]2(C)O[C@H]2[C@@H]2[C@@H](CC1)C(=C)C(=O)O2
InChI	InChI=1S/C15H20O3/c1-9-5-4-8-15(3)13(18-15)12-11(7-6-9)10(2)14(16)17-12/h5,11-13H,2,4,6-8H2,1,3H3/b9-5+/t11-,12-,13-,15+/m0/s1
InChIKey	KTEXNACQROZXEV-SLXBATTESA-N
Formula	C₁₅H₂₀O₃
HBA	3
HBD	0
MW	248.32
Rotatable Bonds	0
TPSA	38.83
LogP	2.76
Number Rings	3
Number Aromatic Rings	0
Heavy Atom Count	18
Formal Charge	0
Fraction CSP3	0.67
Exact Mass	248.14
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Magnolia grandiflora	Magnoliaceae	Plantae	3406

Showing of synonyms

Abdelgaleil SAM, Hashinaga F (2007). Allelopathic potential of two sesquiterpene lactones from Magnolia grandiflora L.. Biochemical Systematics and Ecology,2007,35(11),737-742. [View]

Pubchem: 6473881

Cas: 503551-53-9

Gnps: CCMSLIB00004692440

Zinc: ZINC000030726283

Kegg Ligand: C07609

Chebi: 181553

Nmrshiftdb2: 60059910

Chembl: CHEMBL540445

Drugbank: DB13063

Bindingdb: 50433441

CPRiL: 55487

SMILES: C=C1C(=O)OC2C1CCC=CCCC(O3)C23

Level: 0

Mol. Weight: 248.32 g/mol

Allelopathic

Absorption

Caco-2 (logPapp): -5.08
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.41
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.69

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.23
Plasma Protein Binding: 23.76
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: 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: 16.32
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.89
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: -0.47
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 4.85
Micronucleos: Safe
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: 1.99
Rat (Acute): 1.96
Rat (Chronic Oral): 1.63
Fathead Minnow: 4.03
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: 330.29
Hydration Free Energy: -4.54
Log(D) at pH=7.4: 2.34
Log(P): 2.86
Log S: -3.21
Log(Vapor Pressure): -3.99
Melting Point: 44.26
pKa Acid: 6.76
pKa Basic: 4.82

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	2	0.7706
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	2	0.7706
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	2	0.7680
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	2	0.7680
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7640
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7640
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	2	0.7572
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	2	0.7572
Alcohol dehydrogenase 1C	P00326	ADH1G_HUMAN	Homo sapiens	2	0.7403
Alcohol dehydrogenase 1C	P00326	ADH1G_HUMAN	Homo sapiens	2	0.7403
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	2	0.7314
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	2	0.7314
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7277
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7277
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	2	0.7251
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	2	0.7251
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	2	0.7248
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	2	0.7248
Steroid 17-alpha-hydroxylase/17,20 lyase	P05093	CP17A_HUMAN	Homo sapiens	2	0.7090
Steroid 17-alpha-hydroxylase/17,20 lyase	P05093	CP17A_HUMAN	Homo sapiens	2	0.7090
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7072
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7072
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7066
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7066
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7030
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7030
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	3	0.7009
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	3	0.7009

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