(1S,2R,4S,5R,10S,11R,13S,14R,15R,18R)-14-hydroxy-10,15-dimethyl-5-[1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethyl]-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: b599ca90-4e41-484d-b615-8fe042e8f99d
• Taxonomy: Organoheterocyclic compounds > Naphthopyrans
• IUPAC Name: (1S,2R,4S,5R,10S,11R,13S,14R,15R,18R)-14-hydroxy-10,15-dimethyl-5-[1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethyl]-3,6,12,17-tetraoxahexacyclo[8.7.1.02,4.04,9.011,13.015,18]octadec-8-ene-7,16-dione
• SMILES (Canonical): CC(C1C23C(O2)C4C5C(C(C6C(C5(C3=CC(=O)O1)C)O6)O)(C(=O)O4)C)OC7C(C(C(C(O7)CO)O)O)O
• SMILES (Isomeric): CC([C@@H]1[C@]23[C@H](O2)[C@@H]4[C@H]5[C@]([C@H]([C@H]6[C@@H]([C@@]5(C3=CC(=O)O1)C)O6)O)(C(=O)O4)C)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O
• InChI: InChI=1S/C24H30O13/c1-6(32-20-12(29)11(28)10(27)7(5-25)33-20)17-24-8(4-9(26)34-17)22(2)15-13(19(24)37-24)36-21(31)23(15,3)16(30)14-18(22)35-14/h4,6-7,10-20,25,27-30H,5H2,1-3H3/t6?,7-,10-,11+,12-,13+,14+,15-,16+,17-,18+,19-,20-,22-,23-,24-/m1/s1
• InChI Key: QGWDZDZECYBAPW-QXHHVATHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₃₀O₁₃
• Molecular Weight: 526.50 g/mol
• Exact Mass: 526.16864101 g/mol
• Topological Polar Surface Area (TPSA): 197.00 Ų
• XlogP: -2.90
• Atomic LogP (AlogP): -3.11
• H-Bond Acceptor: 13
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7554	75.54%
Caco-2	-	0.8775	87.75%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.7449	74.49%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8440	84.40%
OATP1B3 inhibitior	+	0.9300	93.00%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.8115	81.15%
P-glycoprotein inhibitior	-	0.5134	51.34%
P-glycoprotein substrate	-	0.5233	52.33%
CYP3A4 substrate	+	0.6550	65.50%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8855	88.55%
CYP3A4 inhibition	-	0.8564	85.64%
CYP2C9 inhibition	-	0.8443	84.43%
CYP2C19 inhibition	-	0.8678	86.78%
CYP2D6 inhibition	-	0.9273	92.73%
CYP1A2 inhibition	-	0.8763	87.63%
CYP2C8 inhibition	-	0.6615	66.15%
CYP inhibitory promiscuity	-	0.7789	77.89%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5818	58.18%
Eye corrosion	-	0.9842	98.42%
Eye irritation	-	0.9383	93.83%
Skin irritation	-	0.6921	69.21%
Skin corrosion	-	0.9314	93.14%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5522	55.22%
Micronuclear	-	0.5641	56.41%
Hepatotoxicity	-	0.5625	56.25%
skin sensitisation	-	0.8330	83.30%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.5975	59.75%
Acute Oral Toxicity (c)	I	0.3932	39.32%
Estrogen receptor binding	+	0.6529	65.29%
Androgen receptor binding	+	0.6777	67.77%
Thyroid receptor binding	+	0.5184	51.84%
Glucocorticoid receptor binding	+	0.5545	55.45%
Aromatase binding	+	0.5690	56.90%
PPAR gamma	+	0.6660	66.60%
Honey bee toxicity	-	0.7228	72.28%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.7650	76.50%
Fish aquatic toxicity	+	0.8124	81.24%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.72%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.05%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.73%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.25%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	90.33%	94.73%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.14%	97.25%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.58%	96.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.47%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.02%	95.56%
CHEMBL4072	P07858	Cathepsin B	85.29%	93.67%
CHEMBL218	P21554	Cannabinoid CB1 receptor	82.50%	96.61%
CHEMBL1937	Q92769	Histone deacetylase 2	82.49%	94.75%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.25%	86.92%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.93%	97.09%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.27%	93.56%

Plants that contains it

• Podocarpus macrophyllus

Cross-Links

• PubChem: 101600200
• NPASS: NPC175532