NP-MRD: Showing NP-Card for N-Formylcytisine (NP0140255)

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Record Information

Version

2.0

Created at

2022-06-29 21:16:32 UTC

Updated at

2022-06-29 21:16:32 UTC

NP-MRD ID

NP0140255

Secondary Accession Numbers

None

Natural Product Identification

Common Name

N-Formylcytisine

Description

N-Formylcytisine belongs to the class of organic compounds known as cytisine and derivatives. These are lupin alkaloids with a structure based on the cytisine skeleton, which is a tetracyclic ketone containing fused pyridine and piperidine rings that form pyrido[1,2a][1,5]diazocin-8-one. N-Formylcytisine is found in Echinosophora koreensis, Maackia amurensis, Maackia hupehensis, Maackia tenuifolia, Petteria ramentacea, Sophora chrysophylla, Sophora tonkinensis, Spartium junceum and Ulex europaeus. N-Formylcytisine was first documented in 2003 (PMID: 14713148). Based on a literature review a small amount of articles have been published on N-Formylcytisine (PMID: 16876210) (PMID: 16042152) (PMID: 20835948).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 32  0  0  0  0  0  0  0  0999 V2000
    1.9871    1.7883    2.3831 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1061    0.6227    1.9460 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8342    0.3616    0.5836 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9814   -1.0017    0.1064 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9643   -1.3909   -0.9112 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7872   -0.2495   -1.9081 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2938    0.9542   -1.1531 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4269    1.4352   -0.2770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8941    0.5680   -0.3664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7849    1.5817    0.0251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9147    1.3008    0.7621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1901    0.0019    1.1305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3049   -0.9689    0.7358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5427   -2.1781    1.0674 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1771   -0.6817   -0.0010 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3412   -1.8128   -0.3430 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4154   -0.1450    2.6361 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9872   -1.0359   -0.4039 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0397   -1.6979    0.9526 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3773   -2.2603   -1.4975 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1119   -0.5638   -2.7281 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8073   -0.0227   -2.3012 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0137    1.7706   -1.8508 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1423    2.3190    0.3204 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2568    1.7188   -0.9671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5537    2.5982   -0.2728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6046    2.0694    1.0679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0718   -0.2586    1.7121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2148   -2.3929    0.6154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9379   -2.4296   -1.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
  8  3  1  0
 15  9  1  0
 16  5  1  0
  2 17  1  0
  4 18  1  0
  4 19  1  0
  5 20  1  6
  6 21  1  0
  6 22  1  0
  7 23  1  6
  8 24  1  0
  8 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 16 29  1  0
 16 30  1  0
M  END


  Mrv1652306292223162D          

 16 18  0  0  1  0            999 V2000
    2.9569    2.0595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0266    0.9506    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6573    1.4824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7273    2.3044    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1955    2.9351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3735    3.0051    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7427    2.4733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0658    2.9449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3189    2.5944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2490    1.7724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9259    1.3008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8560    0.4788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6728    1.6512    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2046    1.0205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5135    2.5544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6902    3.3602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  1  1  6  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  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  0  0  0  0
  2 14  1  0  0  0  0
  4 15  1  0  0  0  0
 15 16  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0140255

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=CN1C[C@@H]2C[C@H](C1)C1=CC=CC(=O)N1C2

> <INCHI_IDENTIFIER>
InChI=1S/C12H14N2O2/c15-8-13-5-9-4-10(7-13)11-2-1-3-12(16)14(11)6-9/h1-3,8-10H,4-7H2/t9-,10+/m0/s1

> <INCHI_KEY>
PCYQRXYBKKZUSR-VHSXEESVSA-N

> <FORMULA>
C12H14N2O2

> <MOLECULAR_WEIGHT>
218.256

> <EXACT_MASS>
218.105527699

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
22.146625845992183

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,9S)-6-oxo-7,11-diazatricyclo[7.3.1.0^{2,7}]trideca-2,4-diene-11-carbaldehyde

> <ALOGPS_LOGP>
0.67

> <JCHEM_LOGP>
-0.7186100400000001

> <ALOGPS_LOGS>
-0.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8024730449376712

> <JCHEM_POLAR_SURFACE_AREA>
40.620000000000005

> <JCHEM_REFRACTIVITY>
62.003700000000016

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.38e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,9S)-6-oxo-7,11-diazatricyclo[7.3.1.0^{2,7}]trideca-2,4-diene-11-carbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0       5.519   3.844   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.650   1.774   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.827   2.767   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       6.958   4.302   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       5.965   5.479   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.430   5.609   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.253   4.617   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.990   5.497   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.595   4.843   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.465   3.308   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.728   2.428   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.598   0.894   0.000  0.00  0.00           O+0
HETATM   13  N   UNK     0       3.123   3.082   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       4.115   1.905   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.425   4.768   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.755   6.272   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   14                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   15                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    7   14                                                  
CONECT   14   13    2                                                       
CONECT   15    4   16                                                       
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₂H₁₄N₂O₂

Average Mass

218.2560 Da

Monoisotopic Mass

218.10553 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

O=CN1C[C@@H]2C[C@H](C1)C1=CC=CC(=O)N1C2

InChI Identifier

InChI=1S/C12H14N2O2/c15-8-13-5-9-4-10(7-13)11-2-1-3-12(16)14(11)6-9/h1-3,8-10H,4-7H2/t9-,10+/m0/s1

InChI Key

PCYQRXYBKKZUSR-VHSXEESVSA-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
Echinosophora koreensis	LOTUS Database	35616633
Maackia amurensis	LOTUS Database	35616633
Maackia hupehensis	LOTUS Database	35616633
Maackia tenuifolia	LOTUS Database	35616633
Petteria ramentacea	LOTUS Database	35616633
Sophora chrysophylla	LOTUS Database	35616633
Sophora tonkinensis	LOTUS Database	35616633
Spartium junceum	LOTUS Database	35616633
Ulex europaeus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cytisine and derivatives. These are lupin alkaloids with a structure based on the cytisine skeleton, which is a tetracyclic ketone containing fused pyridine and piperidine rings that form pyrido[1,2a][1,5]diazocin-8-one.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Lupin alkaloids

Sub Class

Cytisine and derivatives

Direct Parent

Cytisine and derivatives

Alternative Parents

Substituents

Cytisine
Pyridinone
Piperidine
Pyridine
Tertiary carboxylic acid amide
Heteroaromatic compound
Carboxamide group
Lactam
Carboxylic acid derivative
Organoheterocyclic compound
Azacycle
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organic nitrogen 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00007735

Chemspider ID

156343

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

179619

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Maximo P, Lourenco A, Tei A, Wink M: Chemotaxonomy of Portuguese Ulex: quinolizidine alkaloids as taxonomical markers. Phytochemistry. 2006 Sep;67(17):1943-9. doi: 10.1016/j.phytochem.2006.05.037. Epub 2006 Jul 28. [PubMed:16876210 ]
Martins A, Wink M, Tei A, Brum-Bousquet M, Tillequin F, Rauter AP: A phytochemical study of the quinolizidine alkaloids from Genista tenera by gas chromatography-mass spectrometry. Phytochem Anal. 2005 Jul-Aug;16(4):264-6. doi: 10.1002/pca.832. [PubMed:16042152 ]
Li X, Wang D, Cui Z: A new cytisine-type alkaloid from the stem bark of Maackia amurensis. Nat Prod Res. 2010 Oct;24(16):1499-502. doi: 10.1080/14786410903265561. [PubMed:20835948 ]
Martins A, Wink M, Tei A, Rauter AP: Quinolizidine alkaloid profiles of two taxa of Teline maderensis. Z Naturforsch C J Biosci. 2003 Nov-Dec;58(11-12):776-8. doi: 10.1515/znc-2003-11-1203. [PubMed:14713148 ]

Showing NP-Card for N-Formylcytisine (NP0140255)

MOL for NP0140255 (N-Formylcytisine)

3D MOL for NP0140255 (N-Formylcytisine)

3D SDF for NP0140255 (N-Formylcytisine)

3D-SDF for NP0140255 (N-Formylcytisine)

PDB for NP0140255 (N-Formylcytisine)

3D PDB for NP0140255 (N-Formylcytisine)

SMILES for NP0140255 (N-Formylcytisine)

INCHI for NP0140255 (N-Formylcytisine)

Structure for NP0140255 (N-Formylcytisine)

3D Structure for NP0140255 (N-Formylcytisine)