(3aR,4aS,8aR,8bS)-4a-[2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethyl]-3-[4-[2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethyl]phenyl]-1,2,3a,8,8a,8b-hexahydro-[1]benzofuro[2,3-b]pyrrol-7-one

Details

• Internal ID: d11ef749-af62-4cee-81ae-c8c7c592b79f
• Taxonomy: Organoheterocyclic compounds > Pyrrolidines > Phenylpyrrolidines
• IUPAC Name: (3aR,4aS,8aR,8bS)-4a-[2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethyl]-3-[4-[2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethyl]phenyl]-1,2,3a,8,8a,8b-hexahydro-[1]benzofuro[2,3-b]pyrrol-7-one
• SMILES (Canonical): C1CN(C2C1C3CC(=O)C=CC3(O2)CCOC4C(C(C(C(O4)CO)O)O)O)C5=CC=C(C=C5)CCOC6C(C(C(C(O6)CO)O)O)O
• SMILES (Isomeric): C1CN([C@H]2[C@@H]1[C@H]3CC(=O)C=C[C@@]3(O2)CCO[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)C5=CC=C(C=C5)CCO[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O
• InChI: InChI=1S/C32H45NO14/c34-14-21-23(37)25(39)27(41)30(45-21)43-11-7-16-1-3-17(4-2-16)33-10-6-19-20-13-18(36)5-8-32(20,47-29(19)33)9-12-44-31-28(42)26(40)24(38)22(15-35)46-31/h1-5,8,19-31,34-35,37-42H,6-7,9-15H2/t19-,20+,21+,22+,23+,24+,25-,26-,27+,28+,29+,30+,31+,32+/m0/s1
• InChI Key: QCBWMDCBFUJLKV-PBKFSEAISA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₄₅NO₁₄
• Molecular Weight: 667.70 g/mol
• Exact Mass: 667.28400511 g/mol
• Topological Polar Surface Area (TPSA): 228.00 Ų
• XlogP: -1.80
• Atomic LogP (AlogP): -2.68
• H-Bond Acceptor: 15
• H-Bond Donor: 8
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6934	69.34%
Caco-2	-	0.8751	87.51%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.5601	56.01%
OATP2B1 inhibitior	-	0.8616	86.16%
OATP1B1 inhibitior	+	0.8638	86.38%
OATP1B3 inhibitior	+	0.9422	94.22%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9037	90.37%
BSEP inhibitior	+	0.9000	90.00%
P-glycoprotein inhibitior	+	0.6651	66.51%
P-glycoprotein substrate	+	0.5224	52.24%
CYP3A4 substrate	+	0.6986	69.86%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8502	85.02%
CYP3A4 inhibition	-	0.9209	92.09%
CYP2C9 inhibition	-	0.8580	85.80%
CYP2C19 inhibition	-	0.8445	84.45%
CYP2D6 inhibition	-	0.8817	88.17%
CYP1A2 inhibition	-	0.8858	88.58%
CYP2C8 inhibition	+	0.6276	62.76%
CYP inhibitory promiscuity	-	0.8037	80.37%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5559	55.59%
Eye corrosion	-	0.9870	98.70%
Eye irritation	-	0.9250	92.50%
Skin irritation	-	0.7644	76.44%
Skin corrosion	-	0.9322	93.22%
Ames mutagenesis	-	0.7154	71.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.8298	82.98%
Micronuclear	+	0.8400	84.00%
Hepatotoxicity	-	0.5500	55.00%
skin sensitisation	-	0.8561	85.61%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.6566	65.66%
Acute Oral Toxicity (c)	III	0.5433	54.33%
Estrogen receptor binding	+	0.7890	78.90%
Androgen receptor binding	+	0.6642	66.42%
Thyroid receptor binding	-	0.5527	55.27%
Glucocorticoid receptor binding	+	0.5680	56.80%
Aromatase binding	-	0.4904	49.04%
PPAR gamma	+	0.6468	64.68%
Honey bee toxicity	-	0.7209	72.09%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.8394	83.94%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.74%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.99%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.42%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.49%	97.25%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.36%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.26%	97.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.96%	94.00%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	91.11%	94.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.50%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.85%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.68%	94.45%
CHEMBL218	P21554	Cannabinoid CB1 receptor	88.56%	96.61%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.91%	95.56%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	84.76%	95.83%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.65%	86.92%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.00%	93.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.55%	89.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.81%	100.00%

Plants that contains it

• Millingtonia hortensis

Cross-Links

• PubChem: 162996641
• LOTUS: LTS0181758
• wikiData: Q105218142