NP-MRD: Showing NP-Card for 2-imino-5-[(3z)-indol-3-ylidenemethyl]-1,3-dimethylimidazol-4-ol (NP0319174)

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Record Information

Version

2.0

Created at

2022-09-11 20:04:41 UTC

Updated at

2022-09-11 20:04:41 UTC

NP-MRD ID

NP0319174

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-imino-5-[(3z)-indol-3-ylidenemethyl]-1,3-dimethylimidazol-4-ol

Description

Aplysinopsin 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. 2-imino-5-[(3z)-indol-3-ylidenemethyl]-1,3-dimethylimidazol-4-ol is found in Astroides calycularis and Verongula rigida. 2-imino-5-[(3z)-indol-3-ylidenemethyl]-1,3-dimethylimidazol-4-ol was first documented in 2020 (PMID: 33348536). Based on a literature review a small amount of articles have been published on Aplysinopsin (PMID: 33572064) (PMID: 34779368) (PMID: 34063867) (PMID: 33418314).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 35  0  0  0  0  0  0  0  0999 V2000
   -5.0680   -1.2576   -0.0185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0955   -1.4562   -0.2754 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1686   -0.5848   -0.1326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3653    0.6658    0.3612 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6599    1.1860    0.7967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1669    1.2475    0.3445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9021    2.5391    0.7649 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1974    0.3706   -0.1601 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2180    0.6664   -0.2955 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1343   -0.0983    0.2428 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0087   -1.3047    1.0340 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1992   -1.7015    1.3124 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2043   -0.8744    0.7848 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5988   -0.9130    0.8319 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3702    0.0461    0.2138 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7385    1.0651   -0.4650 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3578    1.0898   -0.5022 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5833    0.1405    0.1089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8638   -0.7569   -0.4450 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3620   -1.9941   -1.0258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5055    2.1487    1.2887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1877    0.4303    1.4099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2315    1.4111   -0.1507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2778    3.1222    0.2251 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5554    1.5535   -0.8623 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0784   -1.7502    1.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1269   -1.6975    1.3553 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4629    0.0113    0.2544 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3504    1.8174   -0.9492 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8331    1.8793   -1.0292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3682   -1.8302   -1.4604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3776   -2.8115   -0.2700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0225   -2.3599   -1.8555 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0
  4  3  1  0
  3  2  2  0
  3 19  1  0
 19 20  1  0
 19  8  1  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  2  0
 16 17  1  0
 17 18  2  0
  8  6  2  0
  6  7  1  0
  6  4  1  0
 18 10  1  0
 18 13  1  0
  5 21  1  0
  5 22  1  0
  5 23  1  0
  2  1  1  0
 20 31  1  0
 20 32  1  0
 20 33  1  0
  9 25  1  0
 11 26  1  0
 14 27  1  0
 15 28  1  0
 16 29  1  0
 17 30  1  0
  7 24  1  0
M  END


  Mrv1652309112222042D          

 19 21  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
    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  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
  7 15  1  0  0  0  0
  5 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
  2 18  1  0  0  0  0
 18 19  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0319174

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C(=N)N(C)C(\C=C2/C=NC3=CC=CC=C23)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C14H14N4O/c1-17-12(13(19)18(2)14(17)15)7-9-8-16-11-6-4-3-5-10(9)11/h3-8,15,19H,1-2H3/b9-7+,15-14?

> <INCHI_KEY>
CYKDGQFRORUDQP-YHUDWFPJSA-N

> <FORMULA>
C14H14N4O

> <MOLECULAR_WEIGHT>
254.293

> <EXACT_MASS>
254.116761087

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
27.631157981101417

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
1.8656906146666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.946808460694701

> <JCHEM_PKA_STRONGEST_BASIC>
5.387353758196394

> <JCHEM_POLAR_SURFACE_AREA>
62.92

> <JCHEM_REFRACTIVITY>
98.44760000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2-imino-5-[(3Z)-indol-3-ylidenemethyl]-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  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      -0.483  -5.740   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       0.287  -7.074   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.015  -5.579   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0      -3.045  -6.724   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3   18                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   16                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   15                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10    7                                                  
CONECT   16    5   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    2   19                                                  
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₄H₁₄N₄O

Average Mass

254.2930 Da

Monoisotopic Mass

254.11676 Da

IUPAC Name

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

Traditional Name

2-imino-5-[(3Z)-indol-3-ylidenemethyl]-1,3-dimethylimidazol-4-ol

CAS Registry Number

Not Available

SMILES

CN1C(=N)N(C)C(\C=C2/C=NC3=CC=CC=C23)=C1O

InChI Identifier

InChI=1S/C14H14N4O/c1-17-12(13(19)18(2)14(17)15)7-9-8-16-11-6-4-3-5-10(9)11/h3-8,15,19H,1-2H3/b9-7+,15-14?

InChI Key

CYKDGQFRORUDQP-YHUDWFPJSA-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
Verongula rigida	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
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
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	1.87	ChemAxon
pKa (Strongest Acidic)	9.95	ChemAxon
pKa (Strongest Basic)	5.39	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	98.45 m³·mol⁻¹	ChemAxon
Polarizability	27.63 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

C00042029

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

135476741

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Riyanti, Marner M, Hartwig C, Patras MA, Wodi SIM, Rieuwpassa FJ, Ijong FG, Balansa W, Schaberle TF: Sustainable Low-Volume Analysis of Environmental Samples by Semi-Automated Prioritization of Extracts for Natural Product Research (SeaPEPR). Mar Drugs. 2020 Dec 17;18(12):649. doi: 10.3390/md18120649. [PubMed:33348536 ]
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 ]
Singla RK, Ashraf GM, Ganash M, G VB, Shen B: Physicochemical, Interaction & Topological Descriptors vs. hMAO-A Inhibition of Aplysinopsin Analogs: A Boulevard to the Discovery of Semi-synthetic Antidepression Agents. Curr Drug Metab. 2021;22(11):905-915. doi: 10.2174/1389200222666211015155014. [PubMed:34779368 ]
Song S, Kim S, El-Sawy ER, Cerella C, Orlikova-Boyer B, Kirsch G, Christov C, Dicato M, Diederich M: Anti-Leukemic Properties of Aplysinopsin Derivative EE-84 Alone and Combined to BH3 Mimetic A-1210477. Mar Drugs. 2021 May 21;19(6):285. doi: 10.3390/md19060285. [PubMed:34063867 ]
Nuthakki VK, Yadav Bheemanaboina RR, Bharate SB: Identification of aplysinopsin as a blood-brain barrier permeable scaffold for anti-cholinesterase and anti-BACE-1 activity. Bioorg Chem. 2021 Feb;107:104568. doi: 10.1016/j.bioorg.2020.104568. Epub 2020 Dec 19. [PubMed:33418314 ]
LOTUS database [Link]

Showing NP-Card for 2-imino-5-[(3z)-indol-3-ylidenemethyl]-1,3-dimethylimidazol-4-ol (NP0319174)

MOL for NP0319174 (2-imino-5-[(3z)-indol-3-ylidenemethyl]-1,3-dimethylimidazol-4-ol)

3D MOL for NP0319174 (2-imino-5-[(3z)-indol-3-ylidenemethyl]-1,3-dimethylimidazol-4-ol)

3D SDF for NP0319174 (2-imino-5-[(3z)-indol-3-ylidenemethyl]-1,3-dimethylimidazol-4-ol)

3D-SDF for NP0319174 (2-imino-5-[(3z)-indol-3-ylidenemethyl]-1,3-dimethylimidazol-4-ol)

PDB for NP0319174 (2-imino-5-[(3z)-indol-3-ylidenemethyl]-1,3-dimethylimidazol-4-ol)

3D PDB for NP0319174 (2-imino-5-[(3z)-indol-3-ylidenemethyl]-1,3-dimethylimidazol-4-ol)

SMILES for NP0319174 (2-imino-5-[(3z)-indol-3-ylidenemethyl]-1,3-dimethylimidazol-4-ol)

INCHI for NP0319174 (2-imino-5-[(3z)-indol-3-ylidenemethyl]-1,3-dimethylimidazol-4-ol)

Structure for NP0319174 (2-imino-5-[(3z)-indol-3-ylidenemethyl]-1,3-dimethylimidazol-4-ol)

3D Structure for NP0319174 (2-imino-5-[(3z)-indol-3-ylidenemethyl]-1,3-dimethylimidazol-4-ol)