Cerulenin

Details

• Internal ID: 354a0ed8-1e18-4cde-99c0-bf387b3db3e6
• Taxonomy: Organoheterocyclic compounds > Epoxides > Oxirane carboxylic acids and derivatives
• IUPAC Name: (2R,3S)-3-[(4E,7E)-nona-4,7-dienoyl]oxirane-2-carboxamide
• InChI: InChI=1S/C12H17NO3/c1-2-3-4-5-6-7-8-9(14)10-11(16-10)12(13)15/h2-3,5-6,10-11H,4,7-8H2,1H3,(H2,13,15)/b3-2+,6-5+/t10-,11-/m1/s1
• InChI Key: GVEZIHKRYBHEFX-NQQPLRFYSA-N
• Popularity: 1,310 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₁₇NO₃
• Molecular Weight: 223.27 g/mol
• Exact Mass: 223.12084340 g/mol
• Topological Polar Surface Area (TPSA): 72.70 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 1.11
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 7

Synonyms

• 17397-89-6
• Helicocerin
• (2R,3S)-3-((4E,7E)-nona-4,7-dienoyl)oxirane-2-carboxamide
• 2,3-Epoxy-4-oxo-7,10-dodecadienamide
• (2R,3S)-3-[(4E,7E)-nona-4,7-dienoyl]oxirane-2-carboxamide
• (2R,3S)-2,3-Epoxy-4-oxo-7E,10E-dodecadienamide
• CHEMBL45627
• CHEBI:171741
• MF286Y830Q
• (2R,3S)-3-((4E,7E)-Nona-4,7-dienoyl)-oxirane-2-carboxylic acid amide
• (+)-Cerulenin
• SR-05000002362
• EINECS 241-424-8
• NSC 116069
• UNII-MF286Y830Q
• 3-(1-Oxo-4,7-nonadienyl)oxiranecarboxamide
• 2-Oxiranecarboxamide, 3-[(4E,7E)-1-oxo-4,7-nonadien-1-yl]-, (2R,3S)-
• NSC-116069
• 2-OXIRANECARBOXAMIDE, 3-((4E,7E)-1-OXO-4,7-NONADIEN-1-YL)-, (2R,3S)-
• 7,10-DODECADIENAMIDE, 2,3-EPOXY-4-OXO-
• Oxiranecarboxamide, 3-(1-oxo-4,7-nonadienyl)-, (2R-(2alpha,3alpha(4E,7E)))-
• (2S)(3R)-2,3-Epoxy-4-oxo-7,10-dodecadienoylamide
• CERULENIN [MI]
• SCHEMBL41207
• BSPBio_001276
• MLS006010821
• (2r,3s)-3-(nona-4,7-dienoyl)oxirane-2-carboxamide
• DTXSID2040995
• CHEBI:94649
• HMS1362P17
• HMS1792P17
• HMS1990P17
• HMS3403P17
• HMS3649F20
• HY-A0210
• BDBM50009248
• MFCD00083595
• NSC764755
• (2R,3S)-3-[(4E,7E)-1-Oxo-4,7-nonadien-1-yl]-2-oxiranecarboxamide
• (2R-(2alpha,3alpha(4E,7E)))-3-(1-Oxonona-4,7-dienyl)oxirane-2-carboxamide
• Oxiranecarboxamide, 3-(1-oxo-4,7-nonadienyl)-, [2R-[2a,3a(4E,7E)]]-
• CCG-208171
• CS-6992
• DB01034
• NSC-764755
• IDI1_002233
• Oxiranecarboxamide, 3-(1-oxo-4,7-nonadienyl)-, (2R-(2-alpha,3-alpha(4E,7E)))-
• NCGC00163492-01
• NCGC00163492-02
• G237
• SMR000058786
• F85539
• 3-Nona-4,7-dienoyl-oxirane-2-carboxylic acid amide
• J-010957
• Q5065296
• SR-05000002362-2
• SR-05000002362-3
• BRD-K52075040-001-02-2
• BRD-K52075040-001-03-0
• BRD-K52075040-001-04-8
• Cerulenin, >=98% (HPLC), from Cephalosporium caerulens
• Cerulenin, Cephalosporium caerulens - CAS 17397-89-6
• Z2311575475
• 3-Nona-4,7-dienoyl-oxirane-2-carboxylic acid amide(Cerulenin)
• Oxiranecarboxamide, 3-[(4E,7E)-1-Oxo-4,7-nonadienyl]-, (2R,3S)-
• (2R-(2.ALPHA.,3.ALPHA.(4E,7E)))-3-(1-OXONONA-4,7-DIENYL)OXIRANE- 2-CARBOXAMIDE
• 1X9
• OXIRANECARBOXAMIDE, 3-(1-OXO-4,7-NONADIENYL)-, (2R-(2- .ALPHA.,3-.ALPHA.(4E,7E)))-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9777	97.77%
Caco-2	-	0.9373	93.73%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.6342	63.42%
OATP2B1 inhibitior	-	0.8619	86.19%
OATP1B1 inhibitior	+	0.7558	75.58%
OATP1B3 inhibitior	+	0.9447	94.47%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.8587	85.87%
P-glycoprotein inhibitior	-	0.9490	94.90%
P-glycoprotein substrate	-	0.9179	91.79%
CYP3A4 substrate	-	0.5816	58.16%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8569	85.69%
CYP3A4 inhibition	-	0.9438	94.38%
CYP2C9 inhibition	-	0.7838	78.38%
CYP2C19 inhibition	-	0.6400	64.00%
CYP2D6 inhibition	-	0.9346	93.46%
CYP1A2 inhibition	-	0.6305	63.05%
CYP2C8 inhibition	-	0.9027	90.27%
CYP inhibitory promiscuity	-	0.8871	88.71%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8000	80.00%
Carcinogenicity (trinary)	Non-required	0.6137	61.37%
Eye corrosion	-	0.9515	95.15%
Eye irritation	-	0.8860	88.60%
Skin irritation	-	0.6670	66.70%
Skin corrosion	-	0.9032	90.32%
Ames mutagenesis	-	0.5347	53.47%
Human Ether-a-go-go-Related Gene inhibition	-	0.7148	71.48%
Micronuclear	+	0.5600	56.00%
Hepatotoxicity	-	0.6324	63.24%
skin sensitisation	-	0.8457	84.57%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	-	0.5164	51.64%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.6531	65.31%
Acute Oral Toxicity (c)	III	0.7030	70.30%
Estrogen receptor binding	-	0.7114	71.14%
Androgen receptor binding	-	0.8242	82.42%
Thyroid receptor binding	-	0.7083	70.83%
Glucocorticoid receptor binding	-	0.4730	47.30%
Aromatase binding	-	0.6693	66.93%
PPAR gamma	-	0.7084	70.84%
Honey bee toxicity	-	0.9488	94.88%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	-	0.6362	63.62%

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	94.26%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.80%	99.17%
CHEMBL2730	P21980	Protein-glutamine gamma-glutamyltransferase	91.20%	92.38%
CHEMBL3401	O75469	Pregnane X receptor	85.39%	94.73%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	84.72%	89.34%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.02%	91.11%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.87%	96.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.87%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.62%	97.25%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 5282054
• LOTUS: LTS0055318
• wikiData: Q5065296