(1S,4S,5S,6R,9S,10R,13S)-9-hydroxy-5,6,14-trimethyl-3,16-dioxapentacyclo[8.7.1.01,13.04,13.05,10]octadec-14-ene-12,17-dione

Details

• Internal ID: deaddb62-3648-42f2-8f8f-c1a925235ab7
• Taxonomy: Organoheterocyclic compounds > Naphthopyrans > Naphthopyranones
• IUPAC Name: (1S,4S,5S,6R,9S,10R,13S)-9-hydroxy-5,6,14-trimethyl-3,16-dioxapentacyclo[8.7.1.01,13.04,13.05,10]octadec-14-ene-12,17-dione
• SMILES (Canonical): CC1CCC(C23C1(C4C5(C(=COC(=O)C5(C2)CO4)C)C(=O)C3)C)O
• SMILES (Isomeric): C[C@@H]1CC[C@@H]([C@]23[C@]1([C@H]4[C@@]5(C(=COC(=O)[C@]5(C2)CO4)C)C(=O)C3)C)O
• InChI: InChI=1S/C19H24O5/c1-10-4-5-12(20)17-6-13(21)19-11(2)7-23-15(22)18(19,8-17)9-24-14(19)16(10,17)3/h7,10,12,14,20H,4-6,8-9H2,1-3H3/t10-,12+,14+,16-,17-,18+,19-/m1/s1
• InChI Key: BAJOUHGLCVMCDJ-GXIBURAJSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₄O₅
• Molecular Weight: 332.40 g/mol
• Exact Mass: 332.16237386 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 1.98
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9895	98.95%
Caco-2	+	0.7633	76.33%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.8114	81.14%
OATP2B1 inhibitior	-	0.8633	86.33%
OATP1B1 inhibitior	+	0.8875	88.75%
OATP1B3 inhibitior	+	0.9516	95.16%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6020	60.20%
BSEP inhibitior	-	0.7581	75.81%
P-glycoprotein inhibitior	-	0.8530	85.30%
P-glycoprotein substrate	-	0.6619	66.19%
CYP3A4 substrate	+	0.6515	65.15%
CYP2C9 substrate	-	0.8133	81.33%
CYP2D6 substrate	-	0.8308	83.08%
CYP3A4 inhibition	-	0.7847	78.47%
CYP2C9 inhibition	-	0.8800	88.00%
CYP2C19 inhibition	-	0.9539	95.39%
CYP2D6 inhibition	-	0.9599	95.99%
CYP1A2 inhibition	-	0.8607	86.07%
CYP2C8 inhibition	-	0.7960	79.60%
CYP inhibitory promiscuity	-	0.9796	97.96%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5550	55.50%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9344	93.44%
Skin irritation	+	0.5299	52.99%
Skin corrosion	-	0.9134	91.34%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6581	65.81%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	+	0.5285	52.85%
skin sensitisation	-	0.8595	85.95%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.5728	57.28%
Acute Oral Toxicity (c)	I	0.3821	38.21%
Estrogen receptor binding	+	0.7875	78.75%
Androgen receptor binding	+	0.7499	74.99%
Thyroid receptor binding	+	0.5971	59.71%
Glucocorticoid receptor binding	+	0.7540	75.40%
Aromatase binding	+	0.7012	70.12%
PPAR gamma	+	0.5356	53.56%
Honey bee toxicity	-	0.9234	92.34%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9815	98.15%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	92.45%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.01%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.22%	99.23%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.70%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.37%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.08%	100.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.68%	92.94%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	86.93%	86.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.49%	86.33%
CHEMBL1871	P10275	Androgen Receptor	85.33%	96.43%

Plants that contains it

• Ligularia sagitta

Cross-Links

• PubChem: 163190875
• LOTUS: LTS0096065
• wikiData: Q104922251