NP-MRD: Showing NP-Card for (+)-Cerulenin (NP0062256)

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Record Information

Version

2.0

Created at

2022-04-28 06:55:55 UTC

Updated at

2022-04-28 06:55:55 UTC

NP-MRD ID

NP0062256

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Cerulenin

Description

Cerulenin belongs to the class of organic compounds known as oxirane carboxylic acids and derivatives. Oxirane carboxylic acids and derivatives are compounds containing an oxirane ring bearing a carboxylic acid group (or a derivative thereof). Cerulenin is a very strong basic compound (based on its pKa). (+)-Cerulenin is found in Cephalosporium caerulens. An epoxydodecadienamide isolated from several species, including Acremonium, Acrocylindrum and Helicoceras.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 33  0  0  0  0  0  0  0  0999 V2000
   -2.6526   -1.4726   -2.1833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2694   -0.6375   -2.1488 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7405   -0.2643   -1.0183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5614    0.8474   -0.9761 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3978   -1.0241    0.1970 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0003   -0.6605    1.4027 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5852   -0.4181    1.2230 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2763    1.0249    1.2976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9219    1.8565    0.7162 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1230    1.4689    2.1223 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0496    1.6526    1.1639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3744    0.3764    0.4722 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5436   -0.2248    0.5589 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9046   -1.5005   -0.1174 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0698   -1.3008   -1.0461 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6607   -0.1417   -1.2100 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8164    0.1015   -2.1177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3640    0.9648   -1.5988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3442   -2.1368    0.0944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9308   -1.1164    1.8135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8967    0.7031    2.8720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3698    2.4241    2.6168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2095    2.3918    0.3789 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8852    2.0534    1.7418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3817   -0.0991   -0.1419 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3110    0.2377    1.1683 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0937   -1.9564   -0.6820 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2110   -2.2542    0.6631 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4296   -2.1510   -1.5991 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2743    0.7159   -0.6350 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4273    0.9142   -1.6754 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4934    0.4195   -3.1334 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4802   -0.7937   -2.1492 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  1  0
 16 15  2  0
 15 14  1  0
 14 13  1  0
 13 12  2  0
 12 11  1  0
 11 10  1  0
 10  8  1  0
  8  9  2  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  1  0
  3  2  2  0
  5  7  1  0
 16 30  1  0
 17 31  1  0
 17 32  1  0
 17 33  1  0
 15 29  1  0
 14 27  1  0
 14 28  1  0
 13 26  1  0
 12 25  1  0
 11 23  1  0
 11 24  1  0
 10 21  1  0
 10 22  1  0
  7 20  1  1
  5 19  1  6
  4 18  1  0
  2  1  1  0
M  END


  Mrv1572004161622382D          

 22 22  0  0  1  0            999 V2000
   -0.7783   -3.9507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0638   -3.5382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6507   -3.9507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3651   -3.5382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3651   -2.7132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0796   -2.3007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0796   -1.4757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3651   -1.0632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3651   -0.2382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6507    0.1743    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2382    0.8888    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2382    1.7138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4763    2.1263    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0796    0.1743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9526    2.1263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1743    0.1743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0638   -2.7132    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6507   -4.7757    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6507   -2.3007    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7941   -2.7132    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2340    0.7577    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5587    1.1023    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  2  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  2  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  1  0  0  0
 11 10  1  0  0  0  0
 11 12  1  1  0  0  0
 13 12  2  0  0  0  0
 14  9  2  0  0  0  0
 15 12  1  0  0  0  0
 16 10  1  0  0  0  0
 16 11  1  0  0  0  0
 17  2  1  0  0  0  0
 18  3  1  0  0  0  0
 19  5  1  0  0  0  0
 20  6  1  0  0  0  0
 10 21  1  6  0  0  0
 11 22  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0062256

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(C)=C(\[H])C\C([H])=C(/[H])CCC(=O)[C@@]1([H])O[C@@]1([H])C(O)=N

> <INCHI_IDENTIFIER>
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

> <FORMULA>
C12H17NO3

> <MOLECULAR_WEIGHT>
223.272

> <EXACT_MASS>
223.120843411

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
23.62124170880265

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3S)-3-[(4E,7E)-nona-4,7-dienoyl]oxirane-2-carboximidic acid

> <ALOGPS_LOGP>
1.83

> <JCHEM_LOGP>
-0.32563105486201427

> <ALOGPS_LOGS>
-3.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.79833469137565

> <JCHEM_PKA_STRONGEST_ACIDIC>
-3.383222626551974

> <JCHEM_PKA_STRONGEST_BASIC>
12.56245441151201

> <JCHEM_POLAR_SURFACE_AREA>
73.68

> <JCHEM_REFRACTIVITY>
73.47930000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.22e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cerulenin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-16         0                                  
HETATM    1  C   UNK     0      -1.453  -7.375   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.119  -6.605   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.215  -7.375   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.548  -6.605   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.548  -5.065   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.882  -4.295   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.882  -2.755   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.548  -1.985   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.548  -0.445   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.215   0.325   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.445   1.659   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.445   3.199   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      -0.889   3.969   0.000  0.00  0.00           N+0
HETATM   14  O   UNK     0       3.882   0.325   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       1.778   3.969   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -0.325   0.325   0.000  0.00  0.00           O+0
HETATM   17  H   UNK     0      -0.119  -5.065   0.000  0.00  0.00           H+0
HETATM   18  H   UNK     0       1.215  -8.915   0.000  0.00  0.00           H+0
HETATM   19  H   UNK     0       1.215  -4.295   0.000  0.00  0.00           H+0
HETATM   20  H   UNK     0       5.216  -5.065   0.000  0.00  0.00           H+0
HETATM   21  H   UNK     0       2.304   1.414   0.000  0.00  0.00           H+0
HETATM   22  H   UNK     0      -1.043   2.058   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4   18                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   19                                                  
CONECT    6    5    7   20                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11   16   21                                             
CONECT   11   10   12   16   22                                             
CONECT   12   11   13   15                                                  
CONECT   13   12                                                            
CONECT   14    9                                                            
CONECT   15   12                                                            
CONECT   16   10   11                                                       
CONECT   17    2                                                            
CONECT   18    3                                                            
CONECT   19    5                                                            
CONECT   20    6                                                            
CONECT   21   10                                                            
CONECT   22   11                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

View in JSmol

Synonyms

Value	Source
(2R,3S)-3-((4E,7E)-Nona-4,7-dienoyl)-oxirane-2-carboxylic acid amide	ChEBI
(2R,3S)-3-((4E,7E)-Nona-4,7-dienoyl)oxirane-2-carboxamide	ChEBI
(2R,3S)-3-((4E,7E)-Nona-4,7-dienoyl)-oxirane-2-carboxylate amide	Generator
Cerulenin	MeSH
2,3-Epoxy-4-oxo-7,10-dodecadienoylamide	MeSH

Chemical Formula

C₁₂H₁₇NO₃

Average Mass

223.2720 Da

Monoisotopic Mass

223.12084 Da

IUPAC Name

(2R,3S)-3-[(4E,7E)-nona-4,7-dienoyl]oxirane-2-carboximidic acid

Traditional Name

cerulenin

CAS Registry Number

Not Available

SMILES

[H]\C(C)=C(\[H])C\C([H])=C(/[H])CCC(=O)[C@@]1([H])O[C@@]1([H])C(O)=N

InChI Identifier

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

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cephalosporium caerulens	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxirane carboxylic acids and derivatives. Oxirane carboxylic acids and derivatives are compounds containing an oxirane ring bearing a carboxylic acid group (or a derivative thereof).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Epoxides

Sub Class

Oxirane carboxylic acids and derivatives

Direct Parent

Oxirane carboxylic acids and derivatives

Alternative Parents

Substituents

Oxirane carboxylic acid or derivatives
Monosaccharide
Carboxamide group
Ketone
Primary carboxylic acid amide
Carboxylic acid derivative
Dialkyl ether
Ether
Oxacycle
Carbonyl group
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

monocarboxylic acid amide (CHEBI:171741 )
epoxide (CHEBI:171741 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.83	ALOGPS
logP	-0.33	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	-3.4	ChemAxon
pKa (Strongest Basic)	12.56	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	73.68 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	73.48 m³·mol⁻¹	ChemAxon
Polarizability	23.62 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00018711

Chemspider ID

Not Available

KEGG Compound ID

C12058

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cerulenin

METLIN ID

Not Available

PubChem Compound

5282054

PDB ID

Not Available

ChEBI ID

171741

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Cerulenin (NP0062256)

MOL for NP0062256 ((+)-Cerulenin)

3D MOL for NP0062256 ((+)-Cerulenin)

3D SDF for NP0062256 ((+)-Cerulenin)

3D-SDF for NP0062256 ((+)-Cerulenin)

PDB for NP0062256 ((+)-Cerulenin)

3D PDB for NP0062256 ((+)-Cerulenin)

SMILES for NP0062256 ((+)-Cerulenin)

INCHI for NP0062256 ((+)-Cerulenin)

Structure for NP0062256 ((+)-Cerulenin)

3D Structure for NP0062256 ((+)-Cerulenin)