NP-MRD: Showing NP-Card for Hanishin (NP0069932)

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Record Information

Version

2.0

Created at

2022-04-28 15:13:48 UTC

Updated at

2022-04-28 15:13:48 UTC

NP-MRD ID

NP0069932

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Hanishin

Description

(?)-Hanishin 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. Hanishin is found in Acanthella carterie and Stylissa carteri. Hanishin was first documented in 2012 (PMID: 22315925). Based on a literature review a small amount of articles have been published on (?)-Hanishin (PMID: 35427139) (PMID: 26615890) (PMID: 26176657).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 31  0  0  0  0  0  0  0  0999 V2000
    5.0924   -0.0024    0.9569 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9891    0.2105   -0.0559 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7216    0.1339    0.5195 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5628    0.3062   -0.2614 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7715    0.5263   -1.4761 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2232    0.2346    0.2989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8515    0.3655   -0.7281 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8313   -0.7035   -1.7582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3210   -1.9741   -1.2005 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5852   -1.8473   -0.5509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3590   -2.8165   -0.4372 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9683   -0.5487   -0.0115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1110   -0.0828    0.6398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9945    1.2599    0.9310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2347    2.4158    1.8054 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.7518    1.6039    0.4419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9742    3.3545    0.5297 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.1546    0.5040   -0.1179 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8541   -0.8842    1.5676 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2470    0.8760    1.6029 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0228   -0.2196    0.4014 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0953   -0.6306   -0.7998 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1339    1.1451   -0.6145 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1062   -0.7856    0.7550 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0474    0.9489    1.1303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6154    1.3280   -1.2906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5308   -0.3707   -2.5820 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1365   -0.8233   -2.2290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7704   -2.8217   -1.3019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9501   -0.7023    0.8708 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  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
 18  7  1  0
 18 12  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  6 24  1  0
  6 25  1  0
  7 26  1  6
  8 27  1  0
  8 28  1  0
  9 29  1  0
 13 30  1  0
M  END


  Mrv1652304282217132D          

 18 19  0  0  1  0            999 V2000
    0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1715   -0.0180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9920    0.0682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3276   -0.6855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4045    0.7827    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.3805    0.5951    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
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  6 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
  5 16  2  0  0  0  0
 15 17  1  0  0  0  0
 14 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0069932

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCOC(=O)C[C@H]1CNC(=O)C2=CC(Br)=C(Br)N12

> <INCHI_IDENTIFIER>
InChI=1S/C11H12Br2N2O3/c1-2-18-9(16)3-6-5-14-11(17)8-4-7(12)10(13)15(6)8/h4,6H,2-3,5H2,1H3,(H,14,17)/t6-/m0/s1

> <INCHI_KEY>
ZUYPAYZEOBAJDN-LURJTMIESA-N

> <FORMULA>
C11H12Br2N2O3

> <MOLECULAR_WEIGHT>
380.036

> <EXACT_MASS>
377.921468

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
29.570778307443256

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
ethyl 2-[(4S)-6,7-dibromo-1-oxo-1H,2H,3H,4H-pyrrolo[1,2-a]pyrazin-4-yl]acetate

> <ALOGPS_LOGP>
2.16

> <JCHEM_LOGP>
1.6149244036666666

> <ALOGPS_LOGS>
-3.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.748432740631394

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3933818785028338

> <JCHEM_POLAR_SURFACE_AREA>
60.33

> <JCHEM_REFRACTIVITY>
72.5966

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.36e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ethyl [(4S)-6,7-dibromo-1-oxo-2H,3H,4H-pyrrolo[1,2-a]pyrazin-4-yl]acetate

> <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       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       0.000  -4.620   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      -1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       0.000  -1.540   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.001  -3.850   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       5.335  -1.540   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002  -1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.320  -0.034   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.852   0.127   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.478  -1.280   0.000  0.00  0.00           C+0
HETATM   17 Br   UNK     0      -2.622   1.461   0.000  0.00  0.00          Br+0
HETATM   18 Br   UNK     0       0.710   1.111   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   16                                                  
CONECT    6    5    7   14                                                  
CONECT    7    6    1    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14    6   15   18                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15    5                                                       
CONECT   17   15                                                            
CONECT   18   14                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₁H₁₂Br₂N₂O₃

Average Mass

380.0360 Da

Monoisotopic Mass

377.92147 Da

IUPAC Name

ethyl 2-[(4S)-6,7-dibromo-1-oxo-1H,2H,3H,4H-pyrrolo[1,2-a]pyrazin-4-yl]acetate

Traditional Name

ethyl [(4S)-6,7-dibromo-1-oxo-2H,3H,4H-pyrrolo[1,2-a]pyrazin-4-yl]acetate

CAS Registry Number

Not Available

SMILES

CCOC(=O)C[C@H]1CNC(=O)C2=CC(Br)=C(Br)N12

InChI Identifier

InChI=1S/C11H12Br2N2O3/c1-2-18-9(16)3-6-5-14-11(17)8-4-7(12)10(13)15(6)8/h4,6H,2-3,5H2,1H3,(H,14,17)/t6-/m0/s1

InChI Key

ZUYPAYZEOBAJDN-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
Acanthella carterie	Plant	KNApSAcK
Axinella carteri	LOTUS Database	35616633

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
Aryl bromide
Aryl halide
Substituted pyrrole
Pyrrole
Heteroaromatic compound
Secondary carboxylic acid amide
Lactam
Carboxylic acid ester
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic oxide
Organooxygen compound
Organonitrogen compound
Organobromide
Organohalogen compound
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
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	2.16	ALOGPS
logP	1.61	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	14.75	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	60.33 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	72.6 m³·mol⁻¹	ChemAxon
Polarizability	29.57 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

Not Available

Chemspider ID

26608745

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bracket

METLIN ID

Not Available

PubChem Compound

57325869

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 ]
Zhao DG, Ma YY, Peng W, Zhou AY, Zhang Y, Ding L, Du Z, Zhang K: Total synthesis and cytotoxic activities of longamide B, longamide B methyl ester, hanishin, and their analogues. Bioorg Med Chem Lett. 2016 Jan 1;26(1):6-8. doi: 10.1016/j.bmcl.2015.11.069. Epub 2015 Nov 23. [PubMed:26615890 ]
Adhikary ND, Kwon S, Chung WJ, Koo S: One-Pot Conversion of Carbohydrates into Pyrrole-2-carbaldehydes as Sustainable Platform Chemicals. J Org Chem. 2015 Aug 7;80(15):7693-701. doi: 10.1021/acs.joc.5b01349. Epub 2015 Jul 27. [PubMed:26176657 ]
Cheng G, Wang X, Bao H, Cheng C, Liu N, Hu Y: Total syntheses of (-)-hanishin, (-)-longamide B, and (-)-longamide B methyl ester via a novel preparation of N-substituted pyrrole-2-carboxylates [corrected]. Org Lett. 2012 Feb 17;14(4):1062-5. doi: 10.1021/ol203433c. Epub 2012 Feb 8. [PubMed:22315925 ]

Showing NP-Card for Hanishin (NP0069932)

MOL for NP0069932 (Hanishin)

3D MOL for NP0069932 (Hanishin)

3D SDF for NP0069932 (Hanishin)

3D-SDF for NP0069932 (Hanishin)

PDB for NP0069932 (Hanishin)

3D PDB for NP0069932 (Hanishin)

SMILES for NP0069932 (Hanishin)

INCHI for NP0069932 (Hanishin)

Structure for NP0069932 (Hanishin)

3D Structure for NP0069932 (Hanishin)