NP-MRD: Showing NP-Card for Cyclooroidin (NP0069764)

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Record Information

Version

2.0

Created at

2022-04-28 15:06:29 UTC

Updated at

2022-04-28 15:06:30 UTC

NP-MRD ID

NP0069764

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cyclooroidin

Description

Cyclooroidin belongs to the class of organic compounds known as 2-heteroaryl carboxamides. 2-Heteroaryl carboxamides are compounds containing a heteroaromatic ring that carries a carboxamide group. Cyclooroidin is found in Agelas oroides. Cyclooroidin was first documented in 2010 (PMID: 20949972). Based on a literature review a small amount of articles have been published on Cyclooroidin (PMID: 28212701) (PMID: 24555471) (PMID: 21338082) (PMID: 20929213).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 32  0  0  0  0  0  0  0  0999 V2000
    3.9608    0.3177    1.8715 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1909    0.2035    0.6821 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5372    0.6749   -0.5514 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5722    0.3880   -1.4374 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5606   -0.2947   -0.7577 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3058   -0.7978   -1.3617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8361    0.1990   -1.3039 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0331   -0.4724   -1.9680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5011   -1.5778   -1.1264 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7948   -1.2947    0.2556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6117   -1.9710    0.9036 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0525   -0.1604    0.8025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1168    0.4133    2.0680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2635    1.4851    2.1008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9073    2.6776    3.5557 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.6962    1.5321    0.8348 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5735    2.8188    0.2513 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -1.1842    0.5255    0.0576 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9891   -0.3750    0.5100 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0424    1.1940    2.4161 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4650   -0.5236    2.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5538    0.6291   -2.4925 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4602   -1.1189   -2.4099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0695   -1.7126   -0.8215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6154    1.1140   -1.8864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7707   -0.8540   -2.9728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8609    0.2572   -2.0318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6067   -2.5020   -1.5360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7358    0.0612    2.8684 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4450   -0.8364    1.2724 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 16 18  1  0
  5 19  1  0
 19  2  1  0
 18  7  1  0
 18 12  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  6 23  1  0
  6 24  1  0
  7 25  1  6
  8 26  1  0
  8 27  1  0
  9 28  1  0
 13 29  1  0
 19 30  1  0
M  END


  Mrv1652304282217062D          

 19 21  0  0  1  0            999 V2000
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1060    3.2499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6580    3.8630    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2455    4.5775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4385    4.4059    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5811    5.3311    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    2.9750    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
  9 13  1  0  0  0  0
 12 14  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
  5 17  2  0  0  0  0
 16 18  1  0  0  0  0
 15 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0069764

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1=NC=C(C[C@H]2CNC(=O)C3=CC(Br)=C(Br)N23)N1

> <INCHI_IDENTIFIER>
InChI=1S/C11H11Br2N5O/c12-7-2-8-10(19)15-4-6(18(8)9(7)13)1-5-3-16-11(14)17-5/h2-3,6H,1,4H2,(H,15,19)(H3,14,16,17)/t6-/m0/s1

> <INCHI_KEY>
TWKBAJGOPXDKMJ-LURJTMIESA-N

> <FORMULA>
C11H11Br2N5O

> <MOLECULAR_WEIGHT>
389.051

> <EXACT_MASS>
386.933036

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
30.699767126432114

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4S)-4-[(2-amino-1H-imidazol-5-yl)methyl]-6,7-dibromo-1H,2H,3H,4H-pyrrolo[1,2-a]pyrazin-1-one

> <ALOGPS_LOGP>
1.60

> <JCHEM_LOGP>
0.8385143563333334

> <ALOGPS_LOGS>
-3.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.772293249184852

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.450419061449491

> <JCHEM_PKA_STRONGEST_BASIC>
9.091775880567491

> <JCHEM_POLAR_SURFACE_AREA>
88.73

> <JCHEM_REFRACTIVITY>
78.77890000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.26e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4S)-4-[(2-amino-3H-imidazol-4-yl)methyl]-6,7-dibromo-2H,3H,4H-pyrrolo[1,2-a]pyrazin-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       6.258   2.073   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.924  -0.237   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       3.590   3.613   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.924   5.923   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.258   6.693   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.664   6.066   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       8.695   7.211   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       7.925   8.545   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       6.419   8.224   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0       8.551   9.951   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   18 Br   UNK     0      -0.320   2.843   0.000  0.00  0.00          Br+0
HETATM   19 Br   UNK     0       1.650   5.553   0.000  0.00  0.00          Br+0
CONECT    1    2    7                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   17                                                  
CONECT    6    5    7   15                                                  
CONECT    7    6    1    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12    9                                                       
CONECT   14   12                                                            
CONECT   15    6   16   19                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16    5                                                       
CONECT   18   16                                                            
CONECT   19   15                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₁H₁₁Br₂N₅O

Average Mass

389.0510 Da

Monoisotopic Mass

386.93304 Da

IUPAC Name

(4S)-4-[(2-amino-1H-imidazol-5-yl)methyl]-6,7-dibromo-1H,2H,3H,4H-pyrrolo[1,2-a]pyrazin-1-one

Traditional Name

(4S)-4-[(2-amino-3H-imidazol-4-yl)methyl]-6,7-dibromo-2H,3H,4H-pyrrolo[1,2-a]pyrazin-1-one

CAS Registry Number

Not Available

SMILES

NC1=NC=C(C[C@H]2CNC(=O)C3=CC(Br)=C(Br)N23)N1

InChI Identifier

InChI=1S/C11H11Br2N5O/c12-7-2-8-10(19)15-4-6(18(8)9(7)13)1-5-3-16-11(14)17-5/h2-3,6H,1,4H2,(H,15,19)(H3,14,16,17)/t6-/m0/s1

InChI Key

TWKBAJGOPXDKMJ-LURJTMIESA-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
Agelas oroides	Animalia	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-heteroaryl carboxamides. 2-Heteroaryl carboxamides are compounds containing a heteroaromatic ring that carries a carboxamide group.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acid derivatives

Direct Parent

2-heteroaryl carboxamides

Alternative Parents

Substituents

2-heteroaryl carboxamide
Aminoimidazole
Aryl bromide
Aryl halide
Substituted pyrrole
Heteroaromatic compound
Azole
Imidazole
Pyrrole
Amino acid or derivatives
Secondary carboxylic acid amide
Lactam
Azacycle
Organoheterocyclic compound
Organobromide
Organohalogen compound
Primary amine
Organic nitrogen compound
Amine
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	1.6	ALOGPS
logP	0.84	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	13.45	ChemAxon
pKa (Strongest Basic)	9.09	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	88.73 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	78.78 m³·mol⁻¹	ChemAxon
Polarizability	30.7 Å³	ChemAxon
Number of Rings	3	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

C00028118

Chemspider ID

8914393

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10739060

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lindel T: Chemistry and Biology of the Pyrrole-Imidazole Alkaloids. Alkaloids Chem Biol. 2017;77:117-219. doi: 10.1016/bs.alkal.2016.12.001. Epub 2017 Jan 20. [PubMed:28212701 ]
Mszar NW, Haeffner F, Hoveyda AH: NHC-Cu-catalyzed addition of propargylboron reagents to phosphinoylimines. Enantioselective synthesis of trimethylsilyl-substituted homoallenylamides and application to the synthesis of S-(-)-cyclooroidin. J Am Chem Soc. 2014 Mar 5;136(9):3362-5. doi: 10.1021/ja500373s. Epub 2014 Feb 20. [PubMed:24555471 ]
Bhandari MR, Yousufuddin M, Lovely CJ: Diversity-oriented approach to pyrrole-imidazole alkaloid frameworks. Org Lett. 2011 Mar 18;13(6):1382-5. doi: 10.1021/ol200067e. Epub 2011 Feb 21. [PubMed:21338082 ]
Trost BM, Osipov M, Dong G: Palladium-catalyzed dynamic kinetic asymmetric transformations of vinyl aziridines with nitrogen heterocycles: rapid access to biologically active pyrroles and indoles. J Am Chem Soc. 2010 Nov 10;132(44):15800-7. doi: 10.1021/ja1071509. [PubMed:20949972 ]
Mukherjee S, Sivappa R, Yousufuddin M, Lovely CJ: Asymmetric total synthesis of ent-cyclooroidin. Org Lett. 2010 Nov 5;12(21):4940-3. doi: 10.1021/ol1020916. [PubMed:20929213 ]

Showing NP-Card for Cyclooroidin (NP0069764)

MOL for NP0069764 (Cyclooroidin)

3D MOL for NP0069764 (Cyclooroidin)

3D SDF for NP0069764 (Cyclooroidin)

3D-SDF for NP0069764 (Cyclooroidin)

PDB for NP0069764 (Cyclooroidin)

3D PDB for NP0069764 (Cyclooroidin)

SMILES for NP0069764 (Cyclooroidin)

INCHI for NP0069764 (Cyclooroidin)

Structure for NP0069764 (Cyclooroidin)

3D Structure for NP0069764 (Cyclooroidin)