Pentalenolactone O

Details

• Internal ID: 88ea7873-dc43-4ec8-af7c-d9444bc440db
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (1R,4aR,6aR,7S)-1-hydroxy-1-(hydroxymethyl)-7,8-dimethyl-2-oxo-4,4a,6a,7-tetrahydropentaleno[1,6a-c]pyran-5-carboxylic acid
• InChI: InChI=1S/C15H18O6/c1-7-4-14-10(8(7)2)3-9(12(17)18)11(14)5-21-13(19)15(14,20)6-16/h3-4,8,10-11,16,20H,5-6H2,1-2H3,(H,17,18)/t8-,10-,11+,14?,15-/m1/s1
• InChI Key: FWDDYLWFBHUEKH-QXGHTHNXSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₆
• Molecular Weight: 294.30 g/mol
• Exact Mass: 294.11033829 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): 0.11
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

• (1R,4aR,6aR,7S)-1-hydroxy-1-(hydroxymethyl)-7,8-dimethyl-2-oxo-4,4a,6a,7-tetrahydropentaleno[1,6a-c]pyran-5-carboxylic acid
• 93361-64-9
• (1R,4aR,6aR,7S)-1-hydroxy-1-(hydroxymethyl)-7,8-dimethyl-2-oxo-4,4a,6a,7-tetrahydropentaleno(1,6a-c)pyran-5-carboxylic acid
• RefChem:928787
• orb1992635
• CHEBI:182050
• AKOS040734075
• NCGC00380353-01

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7401	74.01%
Caco-2	-	0.7145	71.45%
Blood Brain Barrier	+	0.5428	54.28%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7401	74.01%
OATP2B1 inhibitior	-	0.8552	85.52%
OATP1B1 inhibitior	+	0.8923	89.23%
OATP1B3 inhibitior	+	0.9655	96.55%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9164	91.64%
P-glycoprotein inhibitior	-	0.9437	94.37%
P-glycoprotein substrate	-	0.7491	74.91%
CYP3A4 substrate	+	0.5384	53.84%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9086	90.86%
CYP3A4 inhibition	-	0.9392	93.92%
CYP2C9 inhibition	-	0.9046	90.46%
CYP2C19 inhibition	-	0.8609	86.09%
CYP2D6 inhibition	-	0.9165	91.65%
CYP1A2 inhibition	-	0.8707	87.07%
CYP2C8 inhibition	-	0.8631	86.31%
CYP inhibitory promiscuity	-	0.9649	96.49%
UGT catelyzed	+	0.6362	63.62%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6474	64.74%
Eye corrosion	-	0.9854	98.54%
Eye irritation	-	0.6128	61.28%
Skin irritation	-	0.6684	66.84%
Skin corrosion	-	0.9322	93.22%
Ames mutagenesis	+	0.5377	53.77%
Human Ether-a-go-go-Related Gene inhibition	-	0.8217	82.17%
Micronuclear	-	0.6600	66.00%
Hepatotoxicity	+	0.5711	57.11%
skin sensitisation	-	0.8346	83.46%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	-	0.7231	72.31%
Acute Oral Toxicity (c)	III	0.3843	38.43%
Estrogen receptor binding	+	0.6464	64.64%
Androgen receptor binding	+	0.7034	70.34%
Thyroid receptor binding	+	0.5671	56.71%
Glucocorticoid receptor binding	+	0.6689	66.89%
Aromatase binding	-	0.6417	64.17%
PPAR gamma	-	0.7128	71.28%
Honey bee toxicity	-	0.8881	88.81%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.7400	74.00%
Fish aquatic toxicity	-	0.4138	41.38%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.43%	96.09%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	89.40%	94.80%
CHEMBL2581	P07339	Cathepsin D	87.96%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	84.87%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.87%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	84.07%	91.19%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.03%	86.33%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	82.34%	93.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.85%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.20%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.09%	97.09%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 10357087
• LOTUS: LTS0235484
• wikiData: Q75062715