Berkeleyamide A

Details

• Internal ID: 8ecf3b28-3554-4cfe-82fc-6fa0bd001bf6
• Taxonomy: Benzenoids > Benzene and substituted derivatives
• IUPAC Name: (3R,5S)-3-[(1S)-1-hydroxy-3-oxo-4-phenylbutyl]-5-(2-methylpropyl)pyrrolidin-2-one
• SMILES (Canonical): CC(C)CC1CC(C(=O)N1)C(CC(=O)CC2=CC=CC=C2)O
• SMILES (Isomeric): CC(C)C[C@H]1C[C@@H](C(=O)N1)[C@H](CC(=O)CC2=CC=CC=C2)O
• InChI: InChI=1S/C18H25NO3/c1-12(2)8-14-10-16(18(22)19-14)17(21)11-15(20)9-13-6-4-3-5-7-13/h3-7,12,14,16-17,21H,8-11H2,1-2H3,(H,19,22)/t14-,16+,17-/m0/s1
• InChI Key: KACACYYTPVUKSL-UAGQMJEPSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₅NO₃
• Molecular Weight: 303.40 g/mol
• Exact Mass: 303.18344366 g/mol
• Topological Polar Surface Area (TPSA): 66.40 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.10
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 7

Synonyms

• CHEMBL466565
• Berkeleamide A
• BDBM50261541

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9756	97.56%
Caco-2	+	0.6818	68.18%
Blood Brain Barrier	+	0.6080	60.80%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.8107	81.07%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9289	92.89%
OATP1B3 inhibitior	+	0.9406	94.06%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.5844	58.44%
P-glycoprotein inhibitior	-	0.8547	85.47%
P-glycoprotein substrate	+	0.6128	61.28%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	0.5975	59.75%
CYP2D6 substrate	-	0.7988	79.88%
CYP3A4 inhibition	-	0.9372	93.72%
CYP2C9 inhibition	-	0.8597	85.97%
CYP2C19 inhibition	-	0.8834	88.34%
CYP2D6 inhibition	-	0.8935	89.35%
CYP1A2 inhibition	-	0.9339	93.39%
CYP2C8 inhibition	-	0.7964	79.64%
CYP inhibitory promiscuity	-	0.8119	81.19%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.6286	62.86%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.9745	97.45%
Skin irritation	-	0.7918	79.18%
Skin corrosion	-	0.9348	93.48%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4352	43.52%
Micronuclear	+	0.6500	65.00%
Hepatotoxicity	+	0.6067	60.67%
skin sensitisation	-	0.8794	87.94%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.6521	65.21%
Acute Oral Toxicity (c)	III	0.5817	58.17%
Estrogen receptor binding	+	0.6678	66.78%
Androgen receptor binding	+	0.5280	52.80%
Thyroid receptor binding	-	0.5988	59.88%
Glucocorticoid receptor binding	-	0.5450	54.50%
Aromatase binding	-	0.5732	57.32%
PPAR gamma	+	0.6819	68.19%
Honey bee toxicity	-	0.9464	94.64%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	-	0.3908	39.08%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4801	P29466	Caspase-1	330 nM	IC50	PMID: 18330993
CHEMBL283	P08254	Matrix metalloproteinase 3	330 nM	IC50	PMID: 18330993

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.82%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.28%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.37%	85.14%
CHEMBL221	P23219	Cyclooxygenase-1	96.36%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.83%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.84%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	86.14%	83.82%
CHEMBL4208	P20618	Proteasome component C5	86.08%	90.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.90%	90.71%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.85%	93.00%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	82.66%	97.64%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.70%	97.09%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.29%	93.03%

Plants that contains it

• Clibadium microcephalum
• Globularia nudicaulis
• Helianthus pumilus
• Leucas aspera
• Stemona parviflora

Cross-Links

• PubChem: 44577362
• NPASS: NPC188010
• ChEMBL: CHEMBL466565
• LOTUS: LTS0175608
• wikiData: Q77369672