14-Deoxylactucin

Details

• Internal ID: bd9b47af-5b74-48ac-a4f3-9ca95243c3ce
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: (3aR,4S,9aS,9bR)-4-hydroxy-6,9-dimethyl-3-methylidene-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-2,7-dione
• SMILES (Canonical): CC1=C2C(C3C(C(C1)O)C(=C)C(=O)O3)C(=CC2=O)C
• SMILES (Isomeric): CC1=C2[C@@H]([C@@H]3[C@@H]([C@H](C1)O)C(=C)C(=O)O3)C(=CC2=O)C
• InChI: InChI=1S/C15H16O4/c1-6-4-10(17)13-8(3)15(18)19-14(13)12-7(2)5-9(16)11(6)12/h5,10,12-14,17H,3-4H2,1-2H3/t10-,12-,13+,14+/m0/s1
• InChI Key: LLUKLZVIROBDGI-SCUASFONSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₆O₄
• Molecular Weight: 260.28 g/mol
• Exact Mass: 260.10485899 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 1.31
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• 74635-52-2
• 11,13-Dehydrodesacetylmatricarin
• (3aR,4S,9aS,9bR)-4-hydroxy-6,9-dimethyl-3-methylidene-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-2,7-dione
• 14-deoxy-lactucin
• CHEMBL4099705
• DTXSID20225617
• 11,13-dehydrodesacetyl-matricarin
• 14-Deoxylactucin (Dehydrodesacetylmatricarin)
• (3aR)-3,3abeta,4,5,9abeta,9balpha-Hexahydro-4beta-hydroxy-6,9-dimethyl-3-methyleneazuleno[4,5-b]furan-2,7-dione
• Azuleno(4,5-b)furan-2,7-dione, 3,3a,4,5,9a,9b-hexahydro-4-hydroxy-6,9-dimethyl-3-methylene-, (3aR-(3aalpha,4alpha,9aalpha,9bbeta))-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9893	98.93%
Caco-2	-	0.5852	58.52%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.6714	67.14%
Subcellular localzation	Mitochondria	0.5244	52.44%
OATP2B1 inhibitior	-	0.8592	85.92%
OATP1B1 inhibitior	+	0.9293	92.93%
OATP1B3 inhibitior	+	0.9470	94.70%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9673	96.73%
P-glycoprotein inhibitior	-	0.8852	88.52%
P-glycoprotein substrate	-	0.8217	82.17%
CYP3A4 substrate	+	0.5140	51.40%
CYP2C9 substrate	-	0.7859	78.59%
CYP2D6 substrate	-	0.8901	89.01%
CYP3A4 inhibition	-	0.8402	84.02%
CYP2C9 inhibition	-	0.9107	91.07%
CYP2C19 inhibition	-	0.8993	89.93%
CYP2D6 inhibition	-	0.9383	93.83%
CYP1A2 inhibition	-	0.7882	78.82%
CYP2C8 inhibition	-	0.9065	90.65%
CYP inhibitory promiscuity	-	0.9627	96.27%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.4674	46.74%
Eye corrosion	-	0.9209	92.09%
Eye irritation	-	0.5469	54.69%
Skin irritation	-	0.5489	54.89%
Skin corrosion	-	0.8579	85.79%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6569	65.69%
Micronuclear	-	0.5200	52.00%
Hepatotoxicity	+	0.7995	79.95%
skin sensitisation	-	0.6890	68.90%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.7918	79.18%
Acute Oral Toxicity (c)	II	0.4377	43.77%
Estrogen receptor binding	-	0.6976	69.76%
Androgen receptor binding	+	0.5287	52.87%
Thyroid receptor binding	-	0.6460	64.60%
Glucocorticoid receptor binding	-	0.5608	56.08%
Aromatase binding	-	0.8165	81.65%
PPAR gamma	-	0.7659	76.59%
Honey bee toxicity	-	0.8384	83.84%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9367	93.67%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.45%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.62%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.57%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.41%	99.23%
CHEMBL2581	P07339	Cathepsin D	86.85%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	86.30%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.66%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	83.78%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.69%	86.33%
CHEMBL4523377	Q86WV6	Stimulator of interferon genes protein	80.68%	95.48%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.26%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.11%	89.00%

Plants that contains it

• Achillea collina
• Ajania fruticulosa
• Annona rensoniana
• Archidendron clypearia
• Aristolochia maxima
• Artemisia ludoviciana
• Artemisia xerophytica
• Bergenia purpurascens
• Betula pendula subsp. mandshurica
• Bischofia javanica
• Caragana tibetica
• Crataegus sinaica
• Discaria chacaye
• Euphorbia ferganensis
• Gardenia jasminoides
• Isodon rubescens
• Jasminum officinale
• Lasiocephalus ovatus
• Ligularia platyglossa
• Macrotyloma axillare
• Malus asiatica
• Mikania obtusata
• Montrouziera sphaeroidea
• Pimpinella saxifraga
• Polygala myrtifolia
• Polystichum deltodon
• Rhodiola stephani
• Sarcomelicope argyrophylla
• Scrophularia wattii
• Seriphidium vachanicum
• Solanum bahamense
• Tanacetum cilicicum
• Tinospora smilacina
• Trigonostemon reidioides
• Tropaeolum speciosum
• Vatica diospyroides

Cross-Links

• PubChem: 156302
• NPASS: NPC287387
• LOTUS: LTS0252949
• wikiData: Q83104661