NP-MRD: Showing NP-Card for 2-(2-isopropylazirin-1-yl)-1-methyl-9h-purin-6-one (NP0304825)

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Record Information

Version

2.0

Created at

2022-09-10 20:11:42 UTC

Updated at

2022-09-10 20:11:42 UTC

NP-MRD ID

NP0304825

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(2-isopropylazirin-1-yl)-1-methyl-9h-purin-6-one

Description

Acremolin belongs to the class of organic compounds known as hypoxanthines. Hypoxanthines are compounds containing the purine derivative 1H-purin-6(9H)-one. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring. 2-(2-isopropylazirin-1-yl)-1-methyl-9h-purin-6-one is found in Sarocladium strictum. 2-(2-isopropylazirin-1-yl)-1-methyl-9h-purin-6-one was first documented in 2013 (PMID: 23635003). Based on a literature review a small amount of articles have been published on Acremolin (PMID: 25944530) (PMID: 28602098) (PMID: 33977846) (PMID: 30445873).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 32  0  0  0  0  0  0  0  0999 V2000
    3.3773   -0.9349    0.7345 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1960   -0.0414   -0.4663 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3347    1.4256   -0.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8882   -0.2862   -1.1062 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1926   -0.7090   -2.1958 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4666   -0.2618   -1.0585 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8124   -0.0318   -0.4831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4385    1.1528   -0.6180 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6652    1.3390   -0.0529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4927    2.4009   -0.0355 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5901    2.0684    0.6640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4658    0.7975    1.0932 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2820    0.3303    0.6596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6209   -0.8791    0.7860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1735   -1.8090    1.4345 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4051   -1.0211    0.2093 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7268   -2.2716    0.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0421   -1.7911    0.5253 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4384   -1.3350    1.1275 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8163   -0.3056    1.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0156   -0.2750   -1.1788 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3299    1.6211    0.3155 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2804    1.9931   -1.0665 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5103    1.7743    0.5340 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2379   -1.1089   -3.2189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3098    3.3220   -0.4885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4214    2.7270    0.8401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9564   -2.6769    1.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1383   -3.0140   -0.3738 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3726   -2.1996    0.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 13  2  0
 13 12  1  0
 12 11  2  0
 11 10  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
  6  4  1  0
 16  7  1  0
 10  9  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  5 25  1  0
 11 27  1  0
 10 26  1  0
 17 28  1  0
 17 29  1  0
 17 30  1  0
M  END


  Mrv1652309102222112D          

 17 19  0  0  0  0            999 V2000
    5.0385    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3240    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3240    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6095    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1970   -0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.6979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    0.0000 C   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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  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  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
  7 16  1  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0304825

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1=CN1C1=NC2=C(N=CN2)C(=O)N1C

> <INCHI_IDENTIFIER>
InChI=1S/C11H13N5O/c1-6(2)7-4-16(7)11-14-9-8(12-5-13-9)10(17)15(11)3/h4-6H,1-3H3,(H,12,13)

> <INCHI_KEY>
JHSAOVNIXNGOCW-UHFFFAOYSA-N

> <FORMULA>
C11H13N5O

> <MOLECULAR_WEIGHT>
231.259

> <EXACT_MASS>
231.112010059

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
23.744503979608822

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-methyl-2-[2-(propan-2-yl)-1H-azirin-1-yl]-6,9-dihydro-1H-purin-6-one

> <JCHEM_LOGP>
0.4793689573333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.370973226577673

> <JCHEM_PKA_STRONGEST_BASIC>
1.832842141417345

> <JCHEM_POLAR_SURFACE_AREA>
64.36

> <JCHEM_REFRACTIVITY>
65.21409999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2-(2-isopropylazirin-1-yl)-1-methyl-9H-purin-6-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       9.405   1.303   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.071   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.071   3.613   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.738   1.303   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.968  -0.031   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       5.198   1.303   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       2.530   1.303   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      -0.268   1.597   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      -0.268   4.089   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.530   5.923   0.000  0.00  0.00           O+0
HETATM   16  N   UNK     0       3.864   3.613   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       5.198   4.383   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4    6                                                       
CONECT    6    5    4    7                                                  
CONECT    7    6    8   16                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    9   14                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    7   17                                                  
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₁H₁₃N₅O

Average Mass

231.2590 Da

Monoisotopic Mass

231.11201 Da

IUPAC Name

1-methyl-2-[2-(propan-2-yl)-1H-azirin-1-yl]-6,9-dihydro-1H-purin-6-one

Traditional Name

2-(2-isopropylazirin-1-yl)-1-methyl-9H-purin-6-one

CAS Registry Number

Not Available

SMILES

CC(C)C1=CN1C1=NC2=C(N=CN2)C(=O)N1C

InChI Identifier

InChI=1S/C11H13N5O/c1-6(2)7-4-16(7)11-14-9-8(12-5-13-9)10(17)15(11)3/h4-6H,1-3H3,(H,12,13)

InChI Key

JHSAOVNIXNGOCW-UHFFFAOYSA-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
Acremonium strictum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hypoxanthines. Hypoxanthines are compounds containing the purine derivative 1H-purin-6(9H)-one. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Imidazopyrimidines

Sub Class

Purines and purine derivatives

Direct Parent

Hypoxanthines

Alternative Parents

Substituents

6-oxopurine
Hypoxanthine
Aminopyrimidine
Pyrimidone
Pyrimidine
Azole
Imidazole
Heteroaromatic compound
Vinylogous amide
Lactam
Azirine
Enamine
Azacycle
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organopnictogen compound
Organic nitrogen 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	0.48	ChemAxon
pKa (Strongest Acidic)	10.37	ChemAxon
pKa (Strongest Basic)	1.83	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.36 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	65.21 m³·mol⁻¹	ChemAxon
Polarizability	23.74 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

Not Available

Chemspider ID

29394155

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

60144918

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Tian Y, Qin X, Lin X, Kaliyaperumal K, Zhou X, Liu J, Ju Z, Tu Z, Liu Y: Sydoxanthone C and acremolin B produced by deep-sea-derived fungus Aspergillus sp. SCSIO Ind09F01. J Antibiot (Tokyo). 2015 Nov;68(11):703-6. doi: 10.1038/ja.2015.55. Epub 2015 May 6. [PubMed:25944530 ]
Li WT, Luo D, Huang JN, Wang LL, Zhang FG, Xi T, Liao JM, Lu YY: Antibacterial constituents from Antarctic fungus, Aspergillus sydowii SP-1. Nat Prod Res. 2018 Mar;32(6):662-667. doi: 10.1080/14786419.2017.1335730. Epub 2017 Jun 12. [PubMed:28602098 ]
Niu S, Chen Z, Pei S, Shao Z, Zhang G, Hong B: Acremolin D, a new acremolin alkaloid from the deep-sea sediment derived Aspergillus sydowii fungus. Nat Prod Res. 2022 Oct;36(19):4936-4942. doi: 10.1080/14786419.2021.1913587. Epub 2021 May 12. [PubMed:33977846 ]
Banert K, Tantillo DJ: A problem in the structure assignment of acremolin C, which is most probably identical with acremolin B. Nat Prod Res. 2019 Oct;33(20):3011-3015. doi: 10.1080/14786419.2018.1509330. Epub 2018 Nov 16. [PubMed:30445873 ]
Januar LA, Molinski TF: Acremolin from Acremonium strictum is N(2),3-etheno-2'-isopropyl-1-methylguanine, not a 1H-azirine. Synthesis and structural revision. Org Lett. 2013 May 17;15(10):2370-3. doi: 10.1021/ol400752s. Epub 2013 May 1. [PubMed:23635003 ]
LOTUS database [Link]

Showing NP-Card for 2-(2-isopropylazirin-1-yl)-1-methyl-9h-purin-6-one (NP0304825)

MOL for NP0304825 (2-(2-isopropylazirin-1-yl)-1-methyl-9h-purin-6-one)

3D MOL for NP0304825 (2-(2-isopropylazirin-1-yl)-1-methyl-9h-purin-6-one)

3D SDF for NP0304825 (2-(2-isopropylazirin-1-yl)-1-methyl-9h-purin-6-one)

3D-SDF for NP0304825 (2-(2-isopropylazirin-1-yl)-1-methyl-9h-purin-6-one)

PDB for NP0304825 (2-(2-isopropylazirin-1-yl)-1-methyl-9h-purin-6-one)

3D PDB for NP0304825 (2-(2-isopropylazirin-1-yl)-1-methyl-9h-purin-6-one)

SMILES for NP0304825 (2-(2-isopropylazirin-1-yl)-1-methyl-9h-purin-6-one)

INCHI for NP0304825 (2-(2-isopropylazirin-1-yl)-1-methyl-9h-purin-6-one)

Structure for NP0304825 (2-(2-isopropylazirin-1-yl)-1-methyl-9h-purin-6-one)

3D Structure for NP0304825 (2-(2-isopropylazirin-1-yl)-1-methyl-9h-purin-6-one)