NP-MRD: Showing NP-Card for Oroidin (NP0070263)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 15:33:29 UTC

Updated at

2022-04-28 15:33:29 UTC

NP-MRD ID

NP0070263

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Oroidin

Description

Oroidin, also known as 7-(15)N-oroidin, 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. Oroidin is found in Agelas dispar, Agelas mauritiana, Agelas oroides, Agelas sceptrum, Agelas sventres, Agelas wiedenmayeri, Agelas wiedenmeyeri, Stylissa carteri, Stylissa caribica and Stylissa massa. Oroidin was first documented in 2020 (PMID: 32880173). Based on a literature review a small amount of articles have been published on Oroidin (PMID: 35427139) (PMID: 33901899) (PMID: 33683231) (PMID: 33417773).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 31  0  0  0  0  0  0  0  0999 V2000
    6.5307    1.1711    0.6350 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2382    0.8526    0.1491 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7084    1.3766   -0.9648 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4736    0.8659   -1.1405 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2216   -0.0059   -0.1039 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9953   -0.7773    0.0909 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9755   -0.7078   -0.7408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2599   -1.5252   -0.4884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4056   -0.6541   -0.3355 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6735   -1.2080   -0.0907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8065   -2.4448   -0.0062 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8240   -0.3423    0.0633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8553    1.0447   -0.0005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1519    1.4700    0.2004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7256    3.2861    0.2082 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -5.9101    0.3346    0.3870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8049    0.3400    0.7114 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -5.0991   -0.7340    0.3013 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3161    0.0015    0.6742 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2533    0.4454    0.8014 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7601    2.1542    0.8292 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7933    1.0873   -1.9399 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9298   -1.4235    0.9467 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0655   -0.0568   -1.5858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4267   -2.1261   -1.4007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0980   -2.2011    0.3544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3050    0.3902   -0.4048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9675    1.6368   -0.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4343   -1.7158    0.4077 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4865   -0.5342    1.5455 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 19  1  0
  5  6  1  0
  6  7  2  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
 19  2  1  0
 18 12  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
 19 30  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
 13 28  1  0
 18 29  1  0
M  END


  Mrv1652304282217332D          

 19 20  0  0  0  0            999 V2000
    3.2978   -3.0091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9652   -3.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7103   -4.2786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8853   -4.2786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6304   -3.4940    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4004   -4.9461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7359   -5.6997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5799   -4.8598    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0950   -5.5273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2745   -5.4410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0611   -4.6874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8815   -4.6011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4336   -5.2142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1873   -4.8787    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1010   -4.0582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2940   -3.8866    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7141   -3.5061    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7499   -3.2391    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.2978   -2.1841    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  1  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 12 16  1  0  0  0  0
 15 17  1  0  0  0  0
  2 18  1  0  0  0  0
  1 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0070263

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1=NC=C(N1)\C=C\CNC(=O)C1=CC(Br)=C(Br)N1

> <INCHI_IDENTIFIER>
InChI=1S/C11H11Br2N5O/c12-7-4-8(18-9(7)13)10(19)15-3-1-2-6-5-16-11(14)17-6/h1-2,4-5,18H,3H2,(H,15,19)(H3,14,16,17)/b2-1+

> <INCHI_KEY>
QKJAXHBFQSBDAR-OWOJBTEDSA-N

> <FORMULA>
C11H11Br2N5O

> <MOLECULAR_WEIGHT>
389.051

> <EXACT_MASS>
386.933036

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
31.434326892387134

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-[(2E)-3-(2-amino-1H-imidazol-5-yl)prop-2-en-1-yl]-4,5-dibromo-1H-pyrrole-2-carboxamide

> <ALOGPS_LOGP>
2.05

> <JCHEM_LOGP>
1.2765520983333334

> <ALOGPS_LOGS>
-3.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
12.971238812212082

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.975594438074685

> <JCHEM_PKA_STRONGEST_BASIC>
8.98032020444493

> <JCHEM_POLAR_SURFACE_AREA>
99.58999999999999

> <JCHEM_REFRACTIVITY>
81.6342

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.29e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
oroidin

> <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       6.156  -5.617   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.402  -6.522   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.926  -7.987   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.386  -7.987   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       4.910  -6.522   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       4.481  -9.233   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.107 -10.640   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0       2.949  -9.072   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       2.044 -10.318   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.512 -10.157   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.114  -8.750   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.646  -8.589   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.676  -9.733   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      -4.083  -9.107   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      -3.922  -7.575   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      -2.416  -7.255   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0      -5.066  -6.545   0.000  0.00  0.00           N+0
HETATM   18 Br   UNK     0       8.866  -6.046   0.000  0.00  0.00          Br+0
HETATM   19 Br   UNK     0       6.156  -4.077   0.000  0.00  0.00          Br+0
CONECT    1    2    5   19                                                  
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4    1                                                       
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15   12                                                       
CONECT   17   15                                                            
CONECT   18    2                                                            
CONECT   19    1                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Value	Source
7-(15)N-Oroidin	MeSH

Chemical Formula

C₁₁H₁₁Br₂N₅O

Average Mass

389.0510 Da

Monoisotopic Mass

386.93304 Da

IUPAC Name

N-[(2E)-3-(2-amino-1H-imidazol-5-yl)prop-2-en-1-yl]-4,5-dibromo-1H-pyrrole-2-carboxamide

Traditional Name

oroidin

CAS Registry Number

Not Available

SMILES

NC1=NC=C(N1)\C=C\CNC(=O)C1=CC(Br)=C(Br)N1

InChI Identifier

InChI=1S/C11H11Br2N5O/c12-7-4-8(18-9(7)13)10(19)15-3-1-2-6-5-16-11(14)17-6/h1-2,4-5,18H,3H2,(H,15,19)(H3,14,16,17)/b2-1+

InChI Key

QKJAXHBFQSBDAR-OWOJBTEDSA-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 dispar	LOTUS Database	35616633
Agelas mauritiana	LOTUS Database	35616633
Agelas oroides	LOTUS Database	35616633
Agelas sceptrum	LOTUS Database	35616633
Agelas sventres	Animalia	KNApSAcK
Agelas wiedenmayeri	LOTUS Database	35616633
Agelas wiedenmeyeri	Animalia	KNApSAcK
Axinella carteri	-	KNApSAcK
Stylissa caribica	-	KNApSAcK
Stylissa massa	-	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
Pyrrole-2-carboxamide
Pyrrole-2-carboxylic acid or derivatives
Aminoimidazole
Aryl bromide
Aryl halide
Substituted pyrrole
Azole
Imidazole
Pyrrole
Heteroaromatic compound
Amino acid or derivatives
Secondary carboxylic acid amide
Organoheterocyclic compound
Azacycle
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Primary amine
Organooxygen compound
Organonitrogen compound
Organobromide
Organohalogen compound
Amine
Organopnictogen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyrroles (CHEBI:70037 )
carboxamide (CHEBI:70037 )

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	2.05	ALOGPS
logP	1.28	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	11.98	ChemAxon
pKa (Strongest Basic)	8.98	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	99.59 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	81.63 m³·mol⁻¹	ChemAxon
Polarizability	31.43 Å³	ChemAxon
Number of Rings	2	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

C00028776

Chemspider ID

4880362

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Oroidin

METLIN ID

Not Available

PubChem Compound

6312649

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Freire VF, Gubiani JR, Spencer TM, Hajdu E, Ferreira AG, Ferreira DAS, de Castro Levatti EV, Burdette JE, Camargo CH, Tempone AG, Berlinck RGS: Feature-Based Molecular Networking Discovery of Bromopyrrole Alkaloids from the Marine Sponge Agelas dispar. J Nat Prod. 2022 May 27;85(5):1340-1350. doi: 10.1021/acs.jnatprod.2c00094. Epub 2022 Apr 15. [PubMed:35427139 ]
Akunuri R, Vadakattu M, Bujji S, Veerareddy V, Madhavi YV, Nanduri S: Fused-azepinones: Emerging scaffolds of medicinal importance. Eur J Med Chem. 2021 Aug 5;220:113445. doi: 10.1016/j.ejmech.2021.113445. Epub 2021 Apr 20. [PubMed:33901899 ]
Herath AK, Lovely CJ: Pyrrole carboxamide introduction in the total synthesis of pyrrole-imidazole alkaloids. Org Biomol Chem. 2021 Mar 28;19(12):2603-2621. doi: 10.1039/d0ob02052d. Epub 2021 Mar 8. [PubMed:33683231 ]
Juillet C, Ermolenko L, Boyarskaya D, Baratte B, Josselin B, Nedev H, Bach S, Iorga BI, Bignon J, Ruchaud S, Al-Mourabit A: From Synthetic Simplified Marine Metabolite Analogues to New Selective Allosteric Inhibitor of Aurora B Kinase. J Med Chem. 2021 Jan 28;64(2):1197-1219. doi: 10.1021/acs.jmedchem.0c02064. Epub 2021 Jan 8. [PubMed:33417773 ]
Bhandari MR, Herath AK, Rasapalli S, Yousufuddin M, Lovely CJ: Total Synthesis of the Nagelamides - Synthetic Studies toward the Reported Structure of Nagelamide D and Nagelamide E Framework. J Org Chem. 2020 Oct 16;85(20):12971-12987. doi: 10.1021/acs.joc.0c01617. Epub 2020 Sep 30. [PubMed:32880173 ]

Showing NP-Card for Oroidin (NP0070263)

MOL for NP0070263 (Oroidin)

3D MOL for NP0070263 (Oroidin)

3D SDF for NP0070263 (Oroidin)

3D-SDF for NP0070263 (Oroidin)

PDB for NP0070263 (Oroidin)

3D PDB for NP0070263 (Oroidin)

SMILES for NP0070263 (Oroidin)

INCHI for NP0070263 (Oroidin)

Structure for NP0070263 (Oroidin)

3D Structure for NP0070263 (Oroidin)