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Matricarin

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

Canonical Smiles	CC(=O)O[C@H]1C[C@@H]2[C@@H]([C@@H]3[C@H](C1=C)C[C@@H]([C@H]3C)OC(=O)C)OC(=O)[C@H]2C
InChI	InChI=1S/C19H26O6/c1-8-13-6-16(24-12(5)21)10(3)17(13)18-14(9(2)19(22)25-18)7-15(8)23-11(4)20/h9-10,13-18H,1,6-7H2,2-5H3/t9-,10+,13-,14-,15-,16-,17-,18-/m0/s1
InChIKey	LJYLKGAKLSAVRU-DHXXLEEMSA-N
Formula	C₁₉H₂₆O₆
HBA	6
HBD	0
MW	350.41
Rotatable Bonds	2
TPSA	78.9
LogP	2.26
Number Rings	3
Number Aromatic Rings	0
Heavy Atom Count	25
Formal Charge	0
Fraction CSP3	0.74
Exact Mass	350.17
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Arctotis grandis	Asteraceae	Plantae	41478
2	Achillea ligustica	Asteraceae	Plantae	282745

Showing of synonyms

Mahmoud AA, Al-Shihry SS, et al. (2012). A new epimeric sesquiterpene lactone from Achillea ligustica.. Records of Natural Products,2012,6(1),21-27. [View]
Halim AF, Zaghloul AM, et al. (1983). Further guaianolides from Arctotis grandis.. Phytochemistry,1983,22(6),1510-1512.. [View]

Pubchem: 3083923

Cas: 5989-43-5

Zinc: ZINC000006018862

Chebi: 174918

Nmrshiftdb2: 60058305

Chembl: CHEMBL2087220

Comptox: DTXSID60208606

CPRiL: 425898

SMILES: C1CCC2C(=C)CCC(C3C12)CC(=O)O3

Level: 0

Mol. Weight: 350.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.59
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.69
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.27

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.45
Plasma Protein Binding: 54.61
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: 11.79
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.08
Biodegradation: Safe
Carcinogenesis: Toxic
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.16
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 5.28
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: -3.28
Rat (Acute): 3.47
Rat (Chronic Oral): 2.05
Fathead Minnow: 3.92
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 371.14
Hydration Free Energy: -5.61
Log(D) at pH=7.4: 1.3
Log(P): 2.47
Log S: -3.45
Log(Vapor Pressure): -6.77
Melting Point: 123.67
pKa Acid: 10.25
pKa Basic: 5.16

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.9120
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.9120
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8979
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8979
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8706
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8706
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.8594
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.8594
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	4	0.8234
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	4	0.8234
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8090
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8090
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7978
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7978
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7748
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7748
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7668
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7668
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.7650
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.7650
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7531
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7531
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7245
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7245
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7237
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7237
Aromatase	P11511	CP19A_HUMAN	Homo sapiens	3	0.7190
Aromatase	P11511	CP19A_HUMAN	Homo sapiens	3	0.7190
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.7121
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.7121
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7089
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7089
Trichothecene 15-O-acetyltransferase TRI3	Q9C1B7	TRI3_FUSSP	Fusarium sporotrichioides	3	0.7041
Trichothecene 15-O-acetyltransferase TRI3	Q9C1B7	TRI3_FUSSP	Fusarium sporotrichioides	3	0.7041
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7026
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7026
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7025
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7025

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