(1S,9R,12R,15R,16S)-8-hydroxy-1,12-dimethyl-6-propan-2-yl-15-[(2R,4S,5S,6S)-3,4,5-trihydroxy-6-[[(2R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-5,10-dioxatetracyclo[7.6.1.02,7.012,16]hexadeca-2,6-diene-4,11-dione

Details

• Internal ID: a1694c7d-3a0c-4e09-85a5-31a708aec591
• Taxonomy: Organoheterocyclic compounds > Naphthopyrans
• IUPAC Name: (1S,9R,12R,15R,16S)-8-hydroxy-1,12-dimethyl-6-propan-2-yl-15-[(2R,4S,5S,6S)-3,4,5-trihydroxy-6-[[(2R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-5,10-dioxatetracyclo[7.6.1.02,7.012,16]hexadeca-2,6-diene-4,11-dione
• SMILES (Canonical): CC(C)C1=C2C(C3C4C(CCC(C4(C2=CC(=O)O1)C)OC5C(C(C(C(O5)COC6C(C(C(C(O6)CO)O)O)O)O)O)O)(C(=O)O3)C)O
• SMILES (Isomeric): CC(C)C1=C2C([C@H]3[C@@H]4[C@@](CC[C@H]([C@@]4(C2=CC(=O)O1)C)O[C@H]5C([C@H]([C@@H]([C@@H](O5)CO[C@H]6C([C@H]([C@@H]([C@@H](O6)CO)O)O)O)O)O)O)(C(=O)O3)C)O
• InChI: InChI=1S/C31H44O16/c1-10(2)24-16-11(7-15(33)46-24)31(4)14(5-6-30(3)26(31)25(19(16)36)47-29(30)41)45-28-23(40)21(38)18(35)13(44-28)9-42-27-22(39)20(37)17(34)12(8-32)43-27/h7,10,12-14,17-23,25-28,32,34-40H,5-6,8-9H2,1-4H3/t12-,13-,14+,17+,18+,19?,20-,21-,22?,23?,25-,26+,27+,28-,30+,31-/m0/s1
• InChI Key: HLCQNKQLAGJUPK-KAHMRSRISA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₄₄O₁₆
• Molecular Weight: 672.70 g/mol
• Exact Mass: 672.26293531 g/mol
• Topological Polar Surface Area (TPSA): 251.00 Ų
• XlogP: -3.00
• Atomic LogP (AlogP): -2.58
• H-Bond Acceptor: 16
• H-Bond Donor: 8
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6811	68.11%
Caco-2	-	0.8809	88.09%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.7706	77.06%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8538	85.38%
OATP1B3 inhibitior	+	0.8933	89.33%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	-	0.8125	81.25%
P-glycoprotein inhibitior	+	0.6074	60.74%
P-glycoprotein substrate	-	0.5298	52.98%
CYP3A4 substrate	+	0.6823	68.23%
CYP2C9 substrate	-	0.6086	60.86%
CYP2D6 substrate	-	0.8673	86.73%
CYP3A4 inhibition	-	0.8861	88.61%
CYP2C9 inhibition	-	0.7563	75.63%
CYP2C19 inhibition	-	0.8302	83.02%
CYP2D6 inhibition	-	0.9409	94.09%
CYP1A2 inhibition	-	0.7126	71.26%
CYP2C8 inhibition	+	0.5312	53.12%
CYP inhibitory promiscuity	-	0.8599	85.99%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5838	58.38%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.9264	92.64%
Skin irritation	-	0.7699	76.99%
Skin corrosion	-	0.9276	92.76%
Ames mutagenesis	-	0.5801	58.01%
Human Ether-a-go-go-Related Gene inhibition	-	0.4156	41.56%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.6267	62.67%
skin sensitisation	-	0.9071	90.71%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	+	0.4549	45.49%
Acute Oral Toxicity (c)	III	0.5970	59.70%
Estrogen receptor binding	+	0.7709	77.09%
Androgen receptor binding	+	0.7092	70.92%
Thyroid receptor binding	-	0.5663	56.63%
Glucocorticoid receptor binding	+	0.6359	63.59%
Aromatase binding	+	0.6655	66.55%
PPAR gamma	+	0.7227	72.27%
Honey bee toxicity	-	0.7468	74.68%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.9339	93.39%

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	97.74%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.00%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.96%	97.09%
CHEMBL2581	P07339	Cathepsin D	92.67%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.84%	89.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.34%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.43%	94.45%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	88.34%	96.21%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.07%	86.33%
CHEMBL220	P22303	Acetylcholinesterase	86.48%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.42%	95.56%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.19%	92.62%
CHEMBL1937	Q92769	Histone deacetylase 2	85.87%	94.75%
CHEMBL226	P30542	Adenosine A1 receptor	85.73%	95.93%
CHEMBL5255	O00206	Toll-like receptor 4	85.29%	92.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.24%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.96%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.98%	94.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.18%	91.07%
CHEMBL4581	P52732	Kinesin-like protein 1	82.59%	93.18%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.25%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.76%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.49%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	81.19%	94.73%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.91%	93.04%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	80.64%	95.71%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.43%	97.14%

Plants that contains it

• Nageia nagi

Cross-Links

• PubChem: 101927624
• LOTUS: LTS0055293
• wikiData: Q105030084