NP-MRD: Showing NP-Card for Ormosianine O (NP0331873)

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Record Information

Version

2.0

Created at

2023-09-27 00:31:26 UTC

Updated at

2024-09-03 04:17:16 UTC

NP-MRD ID

NP0331873

Natural Product DOI

https://doi.org/10.57994/0979

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ormosianine O

Description

Ormosianine O 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. Based on a literature review very few articles have been published on Ormosianine O.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 09272300312D          

 22 25  0  0  1  0            999 V2000
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5834   -0.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4084   -0.5834    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7469    0.3094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5834    1.4084    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4084    1.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9917    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9917   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7062   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4207   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4207    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7062    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7062    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1351    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2295    0.3157    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 H   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
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  0  0  0  0
  5  6  1  6  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  0  0  0  0
 14  9  1  0  0  0  0
 14 15  1  6  0  0  0
 13 16  2  0  0  0  0
 10 17  1  6  0  0  0
 18  3  1  0  0  0  0
  7 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  2 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331873

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CCC[C@H](O)N1C[C@H]1C[C@@H]2CN2[C@H](O)C(=O)CC[C@@]12[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H24N2O3/c18-13-5-4-12-9-6-10(8-17(12)15(13)20)11-2-1-3-14(19)16(11)7-9/h9-12,14-15,19-20H,1-8H2/t9-,10-,11+,12+,14+,15-/m1/s1

> <INCHI_KEY>
CQBHGAVZKXNVJM-BBEFNTSISA-N

> <FORMULA>
C15H24N2O3

> <MOLECULAR_WEIGHT>
280.368

> <EXACT_MASS>
280.178692641

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
29.71852154846227

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,6R,9R,10S,14S)-6,14-dihydroxy-7,15-diazatetracyclo[7.7.1.0^{2,7}.0^{10,15}]heptadecan-5-one

> <JCHEM_LOGP>
0.3304080456666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.598534403498283

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.797181486197035

> <JCHEM_PKA_STRONGEST_BASIC>
8.409974306512137

> <JCHEM_POLAR_SURFACE_AREA>
64.00999999999999

> <JCHEM_REFRACTIVITY>
74.55069999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,6R,9R,10S,14S)-6,14-dihydroxy-7,15-diazatetracyclo[7.7.1.0^{2,7}.0^{10,15}]heptadecan-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-SEP-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-23         0                                  
HETATM    1  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       1.089  -1.089   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.629  -1.089   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.394   0.578   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.089   2.629   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.629   2.629   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       3.718   1.540   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       3.718  -0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.052  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.385  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.385   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.052   2.310   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.052   3.850   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       7.719   2.310   0.000  0.00  0.00           O+0
HETATM   17  H   UNK     0       2.295   0.589   0.000  0.00  0.00           H+0
HETATM   18  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM   19  H   UNK     0      -1.334   0.770   0.000  0.00  0.00           H+0
HETATM   20  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   22                                                  
CONECT    3    2    4   18                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   18                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9    5   11   17                                             
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13    9   15                                                  
CONECT   15   14                                                            
CONECT   16   13                                                            
CONECT   17   10                                                            
CONECT   18    3    7   19   20                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21    2                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₄N₂O₃

Average Mass

280.3680 Da

Monoisotopic Mass

280.17869 Da

IUPAC Name

(1R,2S,6R,9R,10S,14S)-6,14-dihydroxy-7,15-diazatetracyclo[7.7.1.0^{2,7}.0^{10,15}]heptadecan-5-one

Traditional Name

(1R,2S,6R,9R,10S,14S)-6,14-dihydroxy-7,15-diazatetracyclo[7.7.1.0^{2,7}.0^{10,15}]heptadecan-5-one

CAS Registry Number

Not Available

SMILES

[H][C@@]12CCC[C@H](O)N1C[C@H]1C[C@@H]2CN2[C@H](O)C(=O)CC[C@@]12[H]

InChI Identifier

InChI=1S/C15H24N2O3/c18-13-5-4-12-9-6-10(8-17(12)15(13)20)11-2-1-3-14(19)16(11)7-9/h9-12,14-15,19-20H,1-8H2/t9-,10-,11+,12+,14+,15-/m1/s1

InChI Key

CQBHGAVZKXNVJM-BBEFNTSISA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, CDCl3, experimental)	[email protected]	Not Available	Not Available	2023-09-27	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	[email protected]	Not Available	Not Available	2023-09-27	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, CDCl3, experimental)	[email protected]	Not Available	Not Available	2023-09-27	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, CDCl3, experimental)	[email protected]	Not Available	Not Available	2023-09-27	View Spectrum
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	[email protected]	Not Available	Not Available	2023-09-27	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	[email protected]	Not Available	Not Available	2023-09-27	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)	[email protected]	Not Available	Not Available	2023-09-27	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	[email protected]	Not Available	Not Available	2023-09-27	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)	[email protected]	Not Available	Not Available	2023-09-27	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ormosia yunnanensis		Not Available

Chemical Taxonomy

Description

This compound 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
Piperidinone
Piperidine
Monosaccharide
Alpha-hydroxy ketone
Cyclic ketone
Ketone
Azacycle
Organoheterocyclic compound
Alkanolamine
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen 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
logP	0.33	ChemAxon
pKa (Strongest Acidic)	11.8	ChemAxon
pKa (Strongest Basic)	8.41	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	64.01 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	74.55 m³·mol⁻¹	ChemAxon
Polarizability	29.72 Å³	ChemAxon
Number of Rings	4	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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

DOI: 10.1021/acs.jnatprod.3c00493

Showing NP-Card for Ormosianine O (NP0331873)

MOL for NP0331873 (Ormosianine O)

3D MOL for NP0331873 (Ormosianine O)

3D SDF for NP0331873 (Ormosianine O)

3D-SDF for NP0331873 (Ormosianine O)

PDB for NP0331873 (Ormosianine O)

3D PDB for NP0331873 (Ormosianine O)

SMILES for NP0331873 (Ormosianine O)

INCHI for NP0331873 (Ormosianine O)

Structure for NP0331873 (Ormosianine O)

3D Structure for NP0331873 (Ormosianine O)