NP-MRD: Showing NP-Card for (1r,9r,10s)-6-hydroxy-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadec-2-en-8-one (NP0255520)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-07 20:03:16 UTC

Updated at

2022-09-07 20:03:16 UTC

NP-MRD ID

NP0255520

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,9r,10s)-6-hydroxy-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadec-2-en-8-one

Description

Argyrolobine belongs to the class of organic compounds known as sparteine, lupanine, and related alkaloids. These are alkaloids with a structure based on either sparteine, lupanine, or derivatives thereof. These are tetracyclic compounds made of two fused quinolizidine ring systems. (1r,9r,10s)-6-hydroxy-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadec-2-en-8-one is found in Lupinus argenteus. Based on a literature review very few articles have been published on Argyrolobine.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          2D

 41 44  0  0  0  0  0  0  0  0999 V2000
    3.0000    2.5981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5000    2.5981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7500    3.8971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7500    3.8971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5000    2.5981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2500    3.8971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5000    5.1962    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2500    6.4952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5000    7.7942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    7.7942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7500    6.4952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    5.1962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7500    1.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7500   -1.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7500   -1.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6491    0.9642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7500    1.2990    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7920    4.9761    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8057    4.6923    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9935    4.7360    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9888    2.4152    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5080    3.0802    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5080    4.7140    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5080    5.6783    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3991    7.4594    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9095    8.3073    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2395    9.2714    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2605    9.2714    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4095    8.3073    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8991    7.4594    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0982    5.8377    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5000    5.1962    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0000    0.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4895   -2.7762    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1595   -1.8121    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1595   -1.8121    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4895   -2.7762    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6491   -0.9642    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0586    0.4512    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 17  1  0
 17 16  1  0
 16 15  1  0
 15 14  1  0
 14 13  2  0
 13  5  1  0
  5  4  1  0
  4  3  1  0
  3 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  3  2  1  0
  2  1  2  0
  2 19  1  0
 19 17  1  0
 19 13  1  0
  6  5  1  0
  7 12  1  0
 18 41  1  0
 17 40  1  0
 16 38  1  0
 16 39  1  0
 15 36  1  0
 15 37  1  0
 14 35  1  0
  5 23  1  6
  4 21  1  0
  4 22  1  0
  3 20  1  1
 12 34  1  6
 11 32  1  0
 11 33  1  0
 10 30  1  0
 10 31  1  0
  9 28  1  0
  9 29  1  0
  8 26  1  0
  8 27  1  0
  6 24  1  0
  6 25  1  0
M  END


  Mrv1652309072222032D          

 19 22  0  0  1  0            999 V2000
    0.7686   -0.1362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0843    0.6260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9093    0.6260    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2478    1.5188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0843    2.6178    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9093    2.6178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4927    2.0344    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2071    2.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9216    2.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9216    1.2094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2071    0.7969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4927    1.2094    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5009    2.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2135    2.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9280    2.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9280    1.2094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2135    0.7969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2135   -0.0281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5009    1.2094    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  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  1  0  0  0  0
  3 12  1  0  0  0  0
 12  7  1  1  0  0  0
  5 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 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
 13 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0255520

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1CCC=C2[C@@H]3C[C@H]([C@@H]4CCCCN4C3)C(=O)N12

> <INCHI_IDENTIFIER>
InChI=1S/C15H22N2O2/c18-14-6-3-5-12-10-8-11(15(19)17(12)14)13-4-1-2-7-16(13)9-10/h5,10-11,13-14,18H,1-4,6-9H2/t10-,11-,13+,14?/m1/s1

> <INCHI_KEY>
JHXYFYGGFKMUPN-SOUXNPJUSA-N

> <FORMULA>
C15H22N2O2

> <MOLECULAR_WEIGHT>
262.353

> <EXACT_MASS>
262.168127956

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
65.66163799339611

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,9R,10S)-6-hydroxy-7,15-diazatetracyclo[7.7.1.0^{2,7}.0^{10,15}]heptadec-2-en-8-one

> <JCHEM_LOGP>
0.443109486333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.445443508123962

> <JCHEM_PKA_STRONGEST_BASIC>
8.69116302121166

> <JCHEM_POLAR_SURFACE_AREA>
43.78000000000001

> <JCHEM_REFRACTIVITY>
74.12989999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,9R,10S)-6-hydroxy-7,15-diazatetracyclo[7.7.1.0^{2,7}.0^{10,15}]heptadec-2-en-8-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  O   UNK     0       1.435  -0.254   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.024   1.169   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.564   1.169   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.329   2.835   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.024   4.886   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.564   4.886   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       4.653   3.798   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       5.987   4.568   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.320   3.798   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.320   2.258   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.987   1.488   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.653   2.258   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.935   3.798   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.399   4.568   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.732   3.798   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.732   2.258   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.399   1.488   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.399  -0.052   0.000  0.00  0.00           O+0
HETATM   19  N   UNK     0       0.935   2.258   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3   19                                                  
CONECT    3    2    4   12                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    3    7                                                  
CONECT   13    5   14   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17    2   13                                                  
MASTER        0    0    0    0    0    0    0    0   19    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₂N₂O₂

Average Mass

262.3530 Da

Monoisotopic Mass

262.16813 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

OC1CCC=C2[C@@H]3C[C@H]([C@@H]4CCCCN4C3)C(=O)N12

InChI Identifier

InChI=1S/C15H22N2O2/c18-14-6-3-5-12-10-8-11(15(19)17(12)14)13-4-1-2-7-16(13)9-10/h5,10-11,13-14,18H,1-4,6-9H2/t10-,11-,13+,14?/m1/s1

InChI Key

JHXYFYGGFKMUPN-SOUXNPJUSA-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
Lupinus argenteus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sparteine, lupanine, and related alkaloids. These are alkaloids with a structure based on either sparteine, lupanine, or derivatives thereof. These are tetracyclic compounds made of two fused quinolizidine ring systems.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Lupin alkaloids

Sub Class

Sparteine, lupanine, and related alkaloids

Direct Parent

Sparteine, lupanine, and related alkaloids

Alternative Parents

Substituents

Sparteine-lupanine skeleton
Quinolizidine
Delta-lactam
Piperidinone
Tetrahydropyridine
Piperidine
Tertiary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Lactam
Tertiary aliphatic amine
Tertiary amine
Alkanolamine
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Amine
Organic nitrogen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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

C00002211

Chemspider ID

391245

KEGG Compound ID

C10754

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442942

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,9r,10s)-6-hydroxy-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadec-2-en-8-one (NP0255520)

MOL for NP0255520 ((1r,9r,10s)-6-hydroxy-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadec-2-en-8-one)

3D MOL for NP0255520 ((1r,9r,10s)-6-hydroxy-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadec-2-en-8-one)

3D SDF for NP0255520 ((1r,9r,10s)-6-hydroxy-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadec-2-en-8-one)

3D-SDF for NP0255520 ((1r,9r,10s)-6-hydroxy-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadec-2-en-8-one)

PDB for NP0255520 ((1r,9r,10s)-6-hydroxy-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadec-2-en-8-one)

3D PDB for NP0255520 ((1r,9r,10s)-6-hydroxy-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadec-2-en-8-one)

SMILES for NP0255520 ((1r,9r,10s)-6-hydroxy-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadec-2-en-8-one)

INCHI for NP0255520 ((1r,9r,10s)-6-hydroxy-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadec-2-en-8-one)

Structure for NP0255520 ((1r,9r,10s)-6-hydroxy-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadec-2-en-8-one)

3D Structure for NP0255520 ((1r,9r,10s)-6-hydroxy-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadec-2-en-8-one)