(1R,2S,6R,7S,10S,12R,14S)-7,10-dihydroxy-9,14-dimethyl-5-methylidene-3,13-dioxatetracyclo[8.4.0.02,6.012,14]tetradec-8-en-4-one

Details

• Internal ID: 7c99c3e0-c45f-4a2c-bb70-bbea9b82bef5
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (1R,2S,6R,7S,10S,12R,14S)-7,10-dihydroxy-9,14-dimethyl-5-methylidene-3,13-dioxatetracyclo[8.4.0.02,6.012,14]tetradec-8-en-4-one
• SMILES (Canonical): CC1=CC(C2C(C3C1(CC4C3(O4)C)O)OC(=O)C2=C)O
• SMILES (Isomeric): CC1=C[C@@H]([C@@H]2[C@@H]([C@@H]3[C@]1(C[C@@H]4[C@]3(O4)C)O)OC(=O)C2=C)O
• InChI: InChI=1S/C15H18O5/c1-6-4-8(16)10-7(2)13(17)19-11(10)12-14(3)9(20-14)5-15(6,12)18/h4,8-12,16,18H,2,5H2,1,3H3/t8-,9+,10+,11-,12-,14+,15+/m0/s1
• InChI Key: PZDRZDGLTHNUDS-LMGGXVIJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₅
• Molecular Weight: 278.30 g/mol
• Exact Mass: 278.11542367 g/mol
• Topological Polar Surface Area (TPSA): 79.30 Ų
• XlogP: -0.40
• Atomic LogP (AlogP): 0.31
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9780	97.80%
Caco-2	-	0.7421	74.21%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.5335	53.35%
OATP2B1 inhibitior	-	0.8595	85.95%
OATP1B1 inhibitior	+	0.9149	91.49%
OATP1B3 inhibitior	+	0.9555	95.55%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9681	96.81%
P-glycoprotein inhibitior	-	0.8871	88.71%
P-glycoprotein substrate	-	0.7364	73.64%
CYP3A4 substrate	+	0.5814	58.14%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8491	84.91%
CYP3A4 inhibition	-	0.5781	57.81%
CYP2C9 inhibition	-	0.9133	91.33%
CYP2C19 inhibition	-	0.8872	88.72%
CYP2D6 inhibition	-	0.9404	94.04%
CYP1A2 inhibition	-	0.8116	81.16%
CYP2C8 inhibition	-	0.8559	85.59%
CYP inhibitory promiscuity	-	0.9377	93.77%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9525	95.25%
Carcinogenicity (trinary)	Non-required	0.5173	51.73%
Eye corrosion	-	0.9788	97.88%
Eye irritation	-	0.9305	93.05%
Skin irritation	-	0.5520	55.20%
Skin corrosion	-	0.8323	83.23%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6457	64.57%
Micronuclear	+	0.5100	51.00%
Hepatotoxicity	+	0.8125	81.25%
skin sensitisation	-	0.6555	65.55%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.6767	67.67%
Acute Oral Toxicity (c)	III	0.3229	32.29%
Estrogen receptor binding	+	0.7079	70.79%
Androgen receptor binding	+	0.5728	57.28%
Thyroid receptor binding	+	0.5459	54.59%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	+	0.5639	56.39%
PPAR gamma	-	0.5583	55.83%
Honey bee toxicity	-	0.8040	80.40%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.8754	87.54%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.60%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.57%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.35%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.88%	85.14%
CHEMBL218	P21554	Cannabinoid CB1 receptor	86.95%	96.61%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.79%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.51%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.49%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	83.11%	94.73%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.42%	100.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.28%	94.00%

Plants that contains it

• Achillea clypeolata

Cross-Links

• PubChem: 100955712
• LOTUS: LTS0062695
• wikiData: Q105216923