(1S,2R,4S,5R,10S,11S,13R,14R,15R,18R)-5-[(1R)-1,2-dihydroxyethyl]-14-hydroxy-10,15-dimethyl-3,6,12,17-tetraoxahexacyclo[8.7.1.02,4.04,9.011,13.015,18]octadec-8-ene-7,16-dione

Details

• Internal ID: a4809c8d-26a6-4bb6-b51d-2ac9cf1b8674
• Taxonomy: Organoheterocyclic compounds > Naphthopyrans
• IUPAC Name: (1S,2R,4S,5R,10S,11S,13R,14R,15R,18R)-5-[(1R)-1,2-dihydroxyethyl]-14-hydroxy-10,15-dimethyl-3,6,12,17-tetraoxahexacyclo[8.7.1.02,4.04,9.011,13.015,18]octadec-8-ene-7,16-dione
• SMILES (Canonical): CC12C3C(C4C5(O4)C(OC(=O)C=C5C3(C6C(C1O)O6)C)C(CO)O)OC2=O
• SMILES (Isomeric): C[C@@]12[C@@H]3[C@@H]([C@@H]4[C@]5(O4)[C@H](OC(=O)C=C5[C@]3([C@H]6[C@@H]([C@@H]1O)O6)C)[C@@H](CO)O)OC2=O
• InChI: InChI=1S/C18H20O9/c1-16-6-3-7(21)24-12(5(20)4-19)18(6)14(27-18)8-10(16)17(2,15(23)26-8)11(22)9-13(16)25-9/h3,5,8-14,19-20,22H,4H2,1-2H3/t5-,8+,9-,10-,11+,12-,13-,14-,16-,17-,18-/m1/s1
• InChI Key: QXERJFRPZQVUJS-CRAPDYCYSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₀O₉
• Molecular Weight: 380.30 g/mol
• Exact Mass: 380.11073221 g/mol
• Topological Polar Surface Area (TPSA): 138.00 Ų
• XlogP: -2.30
• Atomic LogP (AlogP): -1.96
• H-Bond Acceptor: 9
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9337	93.37%
Caco-2	-	0.8261	82.61%
Blood Brain Barrier	-	0.5661	56.61%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7422	74.22%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8803	88.03%
OATP1B3 inhibitior	+	0.9596	95.96%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.8604	86.04%
P-glycoprotein inhibitior	-	0.6941	69.41%
P-glycoprotein substrate	-	0.5497	54.97%
CYP3A4 substrate	+	0.6069	60.69%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8796	87.96%
CYP3A4 inhibition	-	0.7608	76.08%
CYP2C9 inhibition	-	0.8700	87.00%
CYP2C19 inhibition	-	0.8778	87.78%
CYP2D6 inhibition	-	0.9104	91.04%
CYP1A2 inhibition	-	0.8886	88.86%
CYP2C8 inhibition	-	0.8297	82.97%
CYP inhibitory promiscuity	-	0.9131	91.31%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4882	48.82%
Eye corrosion	-	0.9826	98.26%
Eye irritation	-	0.9602	96.02%
Skin irritation	-	0.6500	65.00%
Skin corrosion	-	0.9093	90.93%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7895	78.95%
Micronuclear	-	0.5341	53.41%
Hepatotoxicity	-	0.5176	51.76%
skin sensitisation	-	0.7891	78.91%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.5912	59.12%
Acute Oral Toxicity (c)	III	0.3811	38.11%
Estrogen receptor binding	+	0.6553	65.53%
Androgen receptor binding	+	0.6128	61.28%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.4892	48.92%
Aromatase binding	+	0.5672	56.72%
PPAR gamma	+	0.6503	65.03%
Honey bee toxicity	-	0.8522	85.22%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.7400	74.00%
Fish aquatic toxicity	+	0.7076	70.76%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	93.46%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.73%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.32%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.86%	85.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.27%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.41%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	85.80%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.98%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.31%	86.33%

Plants that contains it

• Podocarpus macrophyllus

Cross-Links

• PubChem: 44179219
• LOTUS: LTS0099440
• wikiData: Q105229563