Neoclausenamide

Details

• Internal ID: 328d1586-e335-4708-a5ef-e670c43ed6cb
• Taxonomy: Organoheterocyclic compounds > Pyrrolidines > Phenylpyrrolidines
• IUPAC Name: (3R,4S,5R)-3-hydroxy-5-[(S)-hydroxy(phenyl)methyl]-1-methyl-4-phenylpyrrolidin-2-one
• SMILES (Canonical): CN1C(C(C(C1=O)O)C2=CC=CC=C2)C(C3=CC=CC=C3)O
• SMILES (Isomeric): CN1[C@H]([C@@H]([C@H](C1=O)O)C2=CC=CC=C2)[C@H](C3=CC=CC=C3)O
• InChI: InChI=1S/C18H19NO3/c1-19-15(16(20)13-10-6-3-7-11-13)14(17(21)18(19)22)12-8-4-2-5-9-12/h2-11,14-17,20-21H,1H3/t14-,15+,16-,17+/m0/s1
• InChI Key: WGYGSZOQGYRGIP-VVLHAWIVSA-N
• Popularity: 45 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₉NO₃
• Molecular Weight: 297.30 g/mol
• Exact Mass: 297.13649347 g/mol
• Topological Polar Surface Area (TPSA): 60.80 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 1.71
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• (+)-Neoclausenamide
• CHEMBL507740
• (3R,4S,5R)-3-hydroxy-5-[(S)-hydroxy(phenyl)methyl]-1-methyl-4-phenylpyrrolidin-2-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9506	95.06%
Caco-2	+	0.6654	66.54%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.8036	80.36%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9209	92.09%
OATP1B3 inhibitior	+	0.9353	93.53%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.5822	58.22%
P-glycoprotein inhibitior	-	0.7653	76.53%
P-glycoprotein substrate	-	0.8986	89.86%
CYP3A4 substrate	-	0.5885	58.85%
CYP2C9 substrate	-	0.6031	60.31%
CYP2D6 substrate	-	0.7982	79.82%
CYP3A4 inhibition	-	0.8761	87.61%
CYP2C9 inhibition	-	0.8291	82.91%
CYP2C19 inhibition	-	0.7356	73.56%
CYP2D6 inhibition	-	0.8700	87.00%
CYP1A2 inhibition	-	0.7638	76.38%
CYP2C8 inhibition	-	0.9820	98.20%
CYP inhibitory promiscuity	-	0.6998	69.98%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8500	85.00%
Carcinogenicity (trinary)	Non-required	0.5155	51.55%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.8594	85.94%
Skin irritation	-	0.7914	79.14%
Skin corrosion	-	0.9533	95.33%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6110	61.10%
Micronuclear	+	0.7300	73.00%
Hepatotoxicity	-	0.6718	67.18%
skin sensitisation	-	0.9039	90.39%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.6712	67.12%
Nephrotoxicity	-	0.5846	58.46%
Acute Oral Toxicity (c)	III	0.6539	65.39%
Estrogen receptor binding	+	0.5310	53.10%
Androgen receptor binding	-	0.5079	50.79%
Thyroid receptor binding	-	0.6765	67.65%
Glucocorticoid receptor binding	-	0.5931	59.31%
Aromatase binding	+	0.6188	61.88%
PPAR gamma	+	0.5237	52.37%
Honey bee toxicity	-	0.8991	89.91%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	-	0.5316	53.16%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	96.99%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.25%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.25%	95.56%
CHEMBL4040	P28482	MAP kinase ERK2	94.17%	83.82%
CHEMBL221	P23219	Cyclooxygenase-1	89.55%	90.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.97%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.65%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	84.18%	91.49%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.00%	99.23%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	81.76%	94.62%

Plants that contains it

• Clausena lansium
• Eleutherococcus senticosus

Cross-Links

• PubChem: 10149519
• NPASS: NPC293377
• LOTUS: LTS0000523
• wikiData: Q105305118