Desacetoxymatricarin

Details

• Internal ID: a2bbbed5-06be-44de-9d1c-fb413f8eabce
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: (3S,3aS,9aS,9bS)-3,6,9-trimethyl-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-2,7-dione
• SMILES (Canonical): CC1C2CCC(=C3C(C2OC1=O)C(=CC3=O)C)C
• SMILES (Isomeric): C[C@H]1[C@@H]2CCC(=C3[C@@H]([C@H]2OC1=O)C(=CC3=O)C)C
• InChI: InChI=1S/C15H18O3/c1-7-4-5-10-9(3)15(17)18-14(10)13-8(2)6-11(16)12(7)13/h6,9-10,13-14H,4-5H2,1-3H3/t9-,10-,13-,14-/m0/s1
• InChI Key: BJPSSVHNEGMBDQ-NUZBWSBOSA-N
• Popularity: 22 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₃
• Molecular Weight: 246.30 g/mol
• Exact Mass: 246.125594432 g/mol
• Topological Polar Surface Area (TPSA): 43.40 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 2.42
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• Desacetoxymatricarin
• Leucomisine
• 17946-87-1
• Deacetoxymatricarin
• Leukodin
• Leukomisin
• Axillin
• Leucodine
• Leukodin, (+)-
• Desacetoxymatricarine
• (+)-Leukodin
• Matricarin, deacetoxy-
• (3s,3as,9as,9bs)-3,6,9-trimethyl-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-2,7-dione
• UNII-1G2W00IRUI
• 1G2W00IRUI
• CHEBI:4441
• Deacetoxy matricarin
• Guaia-1(10),3-dien-12-oic acid, 6-alpha-hydroxy-2-oxo-, gamma-lactone, (11S)-
• Azuleno(4,5-b)furan-2,7-dione, 3,3a,4,5,9a,9b-hexahydro-3,6,9-trimethyl-, (3S,3aS,9aS,9bS)-
• Azuleno(4,5-b)furan-2,7-dione, 3,3a,4,5,9a,9b-hexahydro-3,6,9-trimethyl-, (3S-(3alpha,3aalpha,9aalpha,9bbeta))-
• Azuleno(4,5-b)furan-2,7-dione, 3,3a,4,5,9a,9b-hexahydro-3,6,9-trimethyl-,(3S,3aS,9aS,9bS)-
• SMR000445670
• (3aS,9aS,9bS)-3,6,9-trimethyl-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-2,7-dione
• Spectrum_001968
• SpecPlus_000876
• Prestwick0_001084
• Prestwick1_001084
• Prestwick2_001084
• Prestwick3_001084
• Spectrum2_001657
• Spectrum3_001631
• Spectrum4_001825
• Spectrum5_000589
• BSPBio_001128
• BSPBio_003321
• KBioGR_002495
• KBioSS_002530
• MLS000728557
• MLS002154146
• DivK1c_006972
• SPBio_001813
• SPBio_003024
• BPBio1_001242
• CHEMBL517040
• DESACETOXYMATRICARIN [MI]
• KBio1_001916
• KBio2_002522
• KBio2_005090
• KBio2_007658
• KBio3_002541
• DTXSID20170810
• BJPSSVHNEGMBDQ-NUZBWSBOSA-N
• HMS1571I10
• HMS2098I10
• HMS2221B10
• BBL036667
• CCG-38769
• STL559046
• AKOS015969701
• 11,13-DIHYDRO-DEHYDROLEUCODINE
• NCGC00163587-02
• NCGC00163587-03
• LS-73187
• AB00514036
• C09394
• J-011454
• BRD-K96119599-001-05-4
• Q27106383

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9957	99.57%
Caco-2	+	0.8423	84.23%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.5310	53.10%
OATP2B1 inhibitior	-	0.8556	85.56%
OATP1B1 inhibitior	+	0.9480	94.80%
OATP1B3 inhibitior	+	0.9621	96.21%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.8792	87.92%
P-glycoprotein inhibitior	-	0.8959	89.59%
P-glycoprotein substrate	-	0.8351	83.51%
CYP3A4 substrate	+	0.5118	51.18%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8968	89.68%
CYP3A4 inhibition	-	0.9333	93.33%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	+	0.9107	91.07%
CYP2C8 inhibition	-	0.8988	89.88%
CYP inhibitory promiscuity	-	0.8681	86.81%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5058	50.58%
Eye corrosion	-	0.9296	92.96%
Eye irritation	-	0.6098	60.98%
Skin irritation	+	0.5607	56.07%
Skin corrosion	-	0.8245	82.45%
Ames mutagenesis	-	0.7900	79.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4595	45.95%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	+	0.8125	81.25%
skin sensitisation	-	0.5816	58.16%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	-	0.6444	64.44%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	+	0.4943	49.43%
Acute Oral Toxicity (c)	III	0.5827	58.27%
Estrogen receptor binding	-	0.7429	74.29%
Androgen receptor binding	+	0.6935	69.35%
Thyroid receptor binding	-	0.6630	66.30%
Glucocorticoid receptor binding	-	0.6981	69.81%
Aromatase binding	-	0.9006	90.06%
PPAR gamma	-	0.7871	78.71%
Honey bee toxicity	-	0.8763	87.63%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.9713	97.13%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4481	P35228	Nitric oxide synthase, inducible	91.61%	94.80%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.68%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.19%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.60%	100.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.96%	91.11%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	84.95%	93.40%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.94%	97.09%
CHEMBL1978	P11511	Cytochrome P450 19A1	83.53%	91.76%
CHEMBL2581	P07339	Cathepsin D	83.38%	98.95%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	82.24%	94.78%
CHEMBL4072	P07858	Cathepsin B	82.10%	93.67%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	81.74%	86.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.40%	99.23%
CHEMBL1871	P10275	Androgen Receptor	81.15%	96.43%

Plants that contains it

• Achillea abrotanoides
• Achillea conferta
• Achillea millefolium
• Achillea sipikorensis
• Achillea vermicularis
• Aequatorium verrucosum
• Anthemis anthemiformis
• Anthemis pseudocotula
• Artemisia adamsii
• Artemisia cana
• Artemisia lucentica
• Artemisia princeps
• Artemisia reptans
• Brachypterum scandens
• Grosvenoria coelocaulis
• Lactuca serriola
• Oncosiphon suffruticosus
• Picris conyzoides
• Podachaenium eminens
• Stevia pilosa
• Tanacetum artemisioides

Cross-Links

• PubChem: 167683
• NPASS: NPC15975
• ChEMBL: CHEMBL517040
• LOTUS: LTS0136471
• wikiData: Q27106383