NP-MRD: Showing NP-Card for 5-{[(3z)-6-bromoindol-3-ylidene]methyl}-2-imino-1,3-dimethylimidazol-4-ol (NP0307271)

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Record Information

Version

2.0

Created at

2022-09-11 00:17:08 UTC

Updated at

2022-09-11 00:17:08 UTC

NP-MRD ID

NP0307271

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-{[(3z)-6-bromoindol-3-ylidene]methyl}-2-imino-1,3-dimethylimidazol-4-ol

Description

6-Bromoaplysinopsin belongs to the class of organic compounds known as indoles and derivatives. These are organic compounds containing an indole, which is a bicyclic ring system made up of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. 5-{[(3z)-6-bromoindol-3-ylidene]methyl}-2-imino-1,3-dimethylimidazol-4-ol is found in Astroides calycularis and Smenospongia aurea. 5-{[(3z)-6-bromoindol-3-ylidene]methyl}-2-imino-1,3-dimethylimidazol-4-ol was first documented in 2021 (PMID: 33572064). Based on a literature review very few articles have been published on 6-bromoaplysinopsin.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 35  0  0  0  0  0  0  0  0999 V2000
   -3.8901   -0.8672    2.4395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1886   -0.6199    1.4675 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2517   -0.2029    0.6680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4534    0.1572   -0.6115 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7419    0.1258   -1.2812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2638    0.5287   -1.1152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0475    0.9726   -2.4224 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2693    0.4068   -0.1416 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1369    0.7531   -0.3024 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1096   -0.0986   -0.0571 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9908   -1.4588    0.3849 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1594   -1.9581    0.5288 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1653   -1.0154    0.2084 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5370   -1.0592    0.2045 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2807    0.0296   -0.1563 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1915    0.0043   -0.1734 Br  0  0  0  0  0  0  0  0  0  0  0  0
    4.6499    1.1996   -0.5251 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2629    1.2848   -0.5345 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5625    0.1724   -0.1667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9273   -0.0466    0.9401 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3597   -0.3171    2.2385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5516    0.0274   -0.5310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8064   -0.7125   -2.0065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8743    1.1157   -1.7683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3149    0.6256   -3.0121 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4606    1.7515   -0.6402 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0929   -2.0207    0.5662 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0480   -1.9607    0.4894 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1856    2.0918   -0.8173 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7784    2.2076   -0.8258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3662    0.1642    2.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0066    0.1215    3.0368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2987   -1.4025    2.4436 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0
  4  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
  8 20  1  0
 20 21  1  0
 20  3  1  0
  3  2  2  0
  3  4  1  0
 19 10  1  0
 19 13  1  0
  5 22  1  0
  5 23  1  0
  5 24  1  0
  7 25  1  0
  9 26  1  0
 11 27  1  0
 14 28  1  0
 17 29  1  0
 18 30  1  0
 21 31  1  0
 21 32  1  0
 21 33  1  0
  2  1  1  0
M  END


  Mrv1652309112202172D          

 20 22  0  0  0  0            999 V2000
   -2.0044   -1.8464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2508   -2.1820    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5363   -1.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4500   -0.9490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -2.3215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.1271    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   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
   -0.2587   -3.0752    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1538   -3.7897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0792   -2.9890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6313   -3.6021    0.0000 N   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  1  0  0  0  0
  3  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  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  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 10 16  1  0  0  0  0
  7 16  1  0  0  0  0
  5 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
  2 19  1  0  0  0  0
 19 20  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0307271

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C(O)=C(\C=C2/C=NC3=CC(Br)=CC=C23)N(C)C1=N

> <INCHI_IDENTIFIER>
InChI=1S/C14H13BrN4O/c1-18-12(13(20)19(2)14(18)16)5-8-7-17-11-6-9(15)3-4-10(8)11/h3-7,16,20H,1-2H3/b8-5+,16-14?

> <INCHI_KEY>
RZEXTWCYINCKES-JENRKBSESA-N

> <FORMULA>
C14H13BrN4O

> <MOLECULAR_WEIGHT>
333.189

> <EXACT_MASS>
332.027274

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
31.499194125756322

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-{[(3Z)-6-bromo-3H-indol-3-ylidene]methyl}-2-imino-1,3-dimethyl-2,3-dihydro-1H-imidazol-4-ol

> <JCHEM_LOGP>
2.6344432400000004

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.396599750458366

> <JCHEM_PKA_STRONGEST_BASIC>
4.919894251597867

> <JCHEM_POLAR_SURFACE_AREA>
62.92

> <JCHEM_REFRACTIVITY>
106.0704

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
5-{[(3Z)-6-bromoindol-3-ylidene]methyl}-2-imino-1,3-dimethylimidazol-4-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      -3.742  -3.447   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -2.335  -4.073   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      -1.001  -3.303   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.840  -1.771   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.143  -4.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   13 Br   UNK     0       7.591   0.237   0.000  0.00  0.00          Br+0
HETATM   14  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      -0.483  -5.740   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       0.287  -7.074   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.015  -5.579   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0      -3.045  -6.724   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3   19                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   17                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   16                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   10    7                                                  
CONECT   17    5   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17    2   20                                                  
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₄H₁₃BrN₄O

Average Mass

333.1890 Da

Monoisotopic Mass

332.02727 Da

IUPAC Name

5-{[(3Z)-6-bromo-3H-indol-3-ylidene]methyl}-2-imino-1,3-dimethyl-2,3-dihydro-1H-imidazol-4-ol

Traditional Name

5-{[(3Z)-6-bromoindol-3-ylidene]methyl}-2-imino-1,3-dimethylimidazol-4-ol

CAS Registry Number

Not Available

SMILES

CN1C(O)=C(\C=C2/C=NC3=CC(Br)=CC=C23)N(C)C1=N

InChI Identifier

InChI=1S/C14H13BrN4O/c1-18-12(13(20)19(2)14(18)16)5-8-7-17-11-6-9(15)3-4-10(8)11/h3-7,16,20H,1-2H3/b8-5+,16-14?

InChI Key

RZEXTWCYINCKES-JENRKBSESA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Astroides calycularis	LOTUS Database	35616633
Smenospongia aurea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indoles and derivatives. These are organic compounds containing an indole, which is a bicyclic ring system made up of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Not Available

Direct Parent

Indoles and derivatives

Alternative Parents

Substituents

Indole or derivatives
Benzenoid
N-substituted imidazole
Aryl halide
Aryl bromide
Heteroaromatic compound
Imidazole
Azole
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organobromide
Organohalogen compound
Imine
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	2.63	ChemAxon
pKa (Strongest Acidic)	9.4	ChemAxon
pKa (Strongest Basic)	4.92	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	62.92 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	106.07 m³·mol⁻¹	ChemAxon
Polarizability	31.5 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

C00045187

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

135433933

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Khushi S, Salim AA, Elbanna AH, Nahar L, Capon RJ: New from Old: Thorectandrin Alkaloids in a Southern Australian Marine Sponge, Thorectandra choanoides (CMB-01889). Mar Drugs. 2021 Feb 9;19(2):97. doi: 10.3390/md19020097. [PubMed:33572064 ]
LOTUS database [Link]

Showing NP-Card for 5-{[(3z)-6-bromoindol-3-ylidene]methyl}-2-imino-1,3-dimethylimidazol-4-ol (NP0307271)

MOL for NP0307271 (5-{[(3z)-6-bromoindol-3-ylidene]methyl}-2-imino-1,3-dimethylimidazol-4-ol)

3D MOL for NP0307271 (5-{[(3z)-6-bromoindol-3-ylidene]methyl}-2-imino-1,3-dimethylimidazol-4-ol)

3D SDF for NP0307271 (5-{[(3z)-6-bromoindol-3-ylidene]methyl}-2-imino-1,3-dimethylimidazol-4-ol)

3D-SDF for NP0307271 (5-{[(3z)-6-bromoindol-3-ylidene]methyl}-2-imino-1,3-dimethylimidazol-4-ol)

PDB for NP0307271 (5-{[(3z)-6-bromoindol-3-ylidene]methyl}-2-imino-1,3-dimethylimidazol-4-ol)

3D PDB for NP0307271 (5-{[(3z)-6-bromoindol-3-ylidene]methyl}-2-imino-1,3-dimethylimidazol-4-ol)

SMILES for NP0307271 (5-{[(3z)-6-bromoindol-3-ylidene]methyl}-2-imino-1,3-dimethylimidazol-4-ol)

INCHI for NP0307271 (5-{[(3z)-6-bromoindol-3-ylidene]methyl}-2-imino-1,3-dimethylimidazol-4-ol)

Structure for NP0307271 (5-{[(3z)-6-bromoindol-3-ylidene]methyl}-2-imino-1,3-dimethylimidazol-4-ol)

3D Structure for NP0307271 (5-{[(3z)-6-bromoindol-3-ylidene]methyl}-2-imino-1,3-dimethylimidazol-4-ol)