[(1S,2S,3R,4S,5S,7S,9R,10R,12R,15S,16S,17S)-4,9-diacetyloxy-3-benzoyloxy-5,10,15-trihydroxy-2,6,6,12-tetramethyl-11,13-dioxatetracyclo[8.7.0.02,7.012,16]heptadecan-17-yl] benzoate

Details

• Internal ID: 188b2460-d343-4cc1-87ae-2896590cfeaf
• Taxonomy: Organoheterocyclic compounds > Naphthopyrans
• IUPAC Name: [(1S,2S,3R,4S,5S,7S,9R,10R,12R,15S,16S,17S)-4,9-diacetyloxy-3-benzoyloxy-5,10,15-trihydroxy-2,6,6,12-tetramethyl-11,13-dioxatetracyclo[8.7.0.02,7.012,16]heptadecan-17-yl] benzoate
• SMILES (Canonical): CC(=O)OC1CC2C(C(C(C(C2(C3C1(OC4(C(C3OC(=O)C5=CC=CC=C5)C(CO4)O)C)O)C)OC(=O)C6=CC=CC=C6)OC(=O)C)O)(C)C
• SMILES (Isomeric): CC(=O)O[C@@H]1C[C@@H]2[C@@]([C@@H]3[C@]1(O[C@@]4([C@H]([C@H]3OC(=O)C5=CC=CC=C5)[C@@H](CO4)O)C)O)([C@H]([C@H]([C@H](C2(C)C)O)OC(=O)C)OC(=O)C6=CC=CC=C6)C
• InChI: InChI=1S/C37H44O13/c1-19(38)46-25-17-24-34(3,4)30(41)28(47-20(2)39)31(49-33(43)22-15-11-8-12-16-22)35(24,5)29-27(48-32(42)21-13-9-7-10-14-21)26-23(40)18-45-36(26,6)50-37(25,29)44/h7-16,23-31,40-41,44H,17-18H2,1-6H3/t23-,24+,25-,26+,27-,28+,29-,30-,31+,35+,36-,37+/m1/s1
• InChI Key: GXKFNMIKBKSMLQ-UPAQOOKSSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₇H₄₄O₁₃
• Molecular Weight: 696.70 g/mol
• Exact Mass: 696.27819145 g/mol
• Topological Polar Surface Area (TPSA): 184.00 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 2.79
• H-Bond Acceptor: 13
• H-Bond Donor: 3
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9345	93.45%
Caco-2	-	0.8200	82.00%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7421	74.21%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8392	83.92%
OATP1B3 inhibitior	+	0.8726	87.26%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9823	98.23%
P-glycoprotein inhibitior	+	0.8339	83.39%
P-glycoprotein substrate	-	0.5420	54.20%
CYP3A4 substrate	+	0.6715	67.15%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8662	86.62%
CYP3A4 inhibition	-	0.8680	86.80%
CYP2C9 inhibition	-	0.8726	87.26%
CYP2C19 inhibition	-	0.9155	91.55%
CYP2D6 inhibition	-	0.9376	93.76%
CYP1A2 inhibition	-	0.8331	83.31%
CYP2C8 inhibition	+	0.6873	68.73%
CYP inhibitory promiscuity	-	0.9211	92.11%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5180	51.80%
Eye corrosion	-	0.9918	99.18%
Eye irritation	-	0.9039	90.39%
Skin irritation	-	0.7803	78.03%
Skin corrosion	-	0.9321	93.21%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7289	72.89%
Micronuclear	-	0.5500	55.00%
Hepatotoxicity	-	0.6319	63.19%
skin sensitisation	-	0.8589	85.89%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.4721	47.21%
Estrogen receptor binding	+	0.7830	78.30%
Androgen receptor binding	+	0.6487	64.87%
Thyroid receptor binding	+	0.5874	58.74%
Glucocorticoid receptor binding	+	0.6465	64.65%
Aromatase binding	+	0.6142	61.42%
PPAR gamma	+	0.7560	75.60%
Honey bee toxicity	-	0.6791	67.91%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9472	94.72%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.93%	86.33%
CHEMBL221	P23219	Cyclooxygenase-1	95.44%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.90%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.12%	91.11%
CHEMBL2581	P07339	Cathepsin D	92.75%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.67%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.03%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.84%	95.56%
CHEMBL5028	O14672	ADAM10	87.60%	97.50%
CHEMBL340	P08684	Cytochrome P450 3A4	87.25%	91.19%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.33%	89.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	85.78%	82.69%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.82%	95.50%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.18%	97.14%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	83.82%	83.00%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	83.41%	94.08%
CHEMBL1951	P21397	Monoamine oxidase A	81.80%	91.49%
CHEMBL2996	Q05655	Protein kinase C delta	81.25%	97.79%
CHEMBL4208	P20618	Proteasome component C5	81.10%	90.00%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	81.00%	94.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.99%	95.89%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	80.48%	81.11%

Plants that contains it

• Angelica ursina
• Ardisia macrocarpa
• Cenchrus americanus
• Chlorophytum malayense
• Clausena indica
• Empetrum nigrum
• Ephedra lomatolepis
• Euonymus maackii
• Gentiana olivieri
• Jateorhiza palmata
• Lindera umbellata
• Morus notabilis
• Nicotiana gossei
• Orthosiphon aristatus var. aristatus
• Picradeniopsis oppositifolia
• Pinus halepensis
• Pinus thunbergii
• Pterocaulon rugosum
• Rauvolfia tetraphylla
• Salvia prionitis
• Satureja montana
• Saussurea triangulata
• Senecio grandiflorus
• Stephania succifera
• Stevia salicifolia
• Tetraria capillaris
• Teucrium alyssifolium
• Vernonanthura serratuloides
• Zephyranthes carinata

Cross-Links

• PubChem: 10963538
• NPASS: NPC89880
• LOTUS: LTS0031051
• wikiData: Q105023134