2,3-Dihydroxy-1-(hydroxymethyl)-1,7,7a-trimethyl-1a,2,3,6,7,7b-hexahydrocyclopropa[a]naphthalen-5-one

Details

• Internal ID: e1500ba3-0198-4607-a7b9-a76cc298bf6f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Aristolane sesquiterpenoids
• IUPAC Name: 2,3-dihydroxy-1-(hydroxymethyl)-1,7,7a-trimethyl-1a,2,3,6,7,7b-hexahydrocyclopropa[a]naphthalen-5-one
• SMILES (Canonical): CC1CC(=O)C=C2C1(C3C(C3(C)CO)C(C2O)O)C
• SMILES (Isomeric): CC1CC(=O)C=C2C1(C3C(C3(C)CO)C(C2O)O)C
• InChI: InChI=1S/C15H22O4/c1-7-4-8(17)5-9-11(18)12(19)10-13(15(7,9)3)14(10,2)6-16/h5,7,10-13,16,18-19H,4,6H2,1-3H3
• InChI Key: DNDJVLRCUVQAAL-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₄
• Molecular Weight: 266.33 g/mol
• Exact Mass: 266.15180918 g/mol
• Topological Polar Surface Area (TPSA): 77.80 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): 0.51
• H-Bond Acceptor: 4
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9843	98.43%
Caco-2	+	0.5223	52.23%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6919	69.19%
OATP2B1 inhibitior	-	0.8576	85.76%
OATP1B1 inhibitior	+	0.8930	89.30%
OATP1B3 inhibitior	+	0.9344	93.44%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.9504	95.04%
P-glycoprotein inhibitior	-	0.9029	90.29%
P-glycoprotein substrate	-	0.7135	71.35%
CYP3A4 substrate	+	0.5456	54.56%
CYP2C9 substrate	-	0.8057	80.57%
CYP2D6 substrate	-	0.8762	87.62%
CYP3A4 inhibition	-	0.7765	77.65%
CYP2C9 inhibition	-	0.8066	80.66%
CYP2C19 inhibition	-	0.8233	82.33%
CYP2D6 inhibition	-	0.8816	88.16%
CYP1A2 inhibition	-	0.6649	66.49%
CYP2C8 inhibition	-	0.9280	92.80%
CYP inhibitory promiscuity	-	0.7529	75.29%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6585	65.85%
Eye corrosion	-	0.9894	98.94%
Eye irritation	-	0.9566	95.66%
Skin irritation	-	0.6300	63.00%
Skin corrosion	-	0.9393	93.93%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7809	78.09%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	+	0.5268	52.68%
skin sensitisation	-	0.7550	75.50%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	+	0.7318	73.18%
Acute Oral Toxicity (c)	III	0.6960	69.60%
Estrogen receptor binding	+	0.5362	53.62%
Androgen receptor binding	+	0.5783	57.83%
Thyroid receptor binding	+	0.5523	55.23%
Glucocorticoid receptor binding	+	0.5661	56.61%
Aromatase binding	-	0.5760	57.60%
PPAR gamma	-	0.6250	62.50%
Honey bee toxicity	-	0.9110	91.10%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9549	95.49%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	95.66%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.45%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.28%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.77%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.79%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.24%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.96%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.15%	97.09%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.81%	90.71%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	80.76%	86.00%

Plants that contains it

• Lythrum salicaria

Cross-Links

• PubChem: 78384717
• LOTUS: LTS0188379
• wikiData: Q81986620