NP-MRD: Showing NP-Card for Deoxynupharidine (NP0051071)

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Record Information

Version

2.0

Created at

2022-04-27 22:30:39 UTC

Updated at

2022-04-27 22:30:39 UTC

NP-MRD ID

NP0051071

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Deoxynupharidine

Description

Deoxynupharidine belongs to the class of organic compounds known as quinolizines. Quinolizines are compounds containing a quinolizine moiety, which consists of two fused pyridine rings sharing a nitrogen atom. Deoxynupharidine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Deoxynupharidine is found in Nuphar japonicum , Nuphar luteum , Nuphar microphylla and Nymphaea spp.. Deoxynupharidine was first documented in 2003 (PMID: 14643343). Based on a literature review a small amount of articles have been published on Deoxynupharidine (PMID: 26493620) (PMID: 15624924) (PMID: 12967291).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 42  0  0  0  0  0  0  0  0999 V2000
   -2.4039   -2.7108   -0.5296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6322   -1.4095   -0.7917 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6379   -0.2978   -0.7382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2451    0.7589    0.3042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8060    1.0894    0.0606 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3102    2.2823    0.8037 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6292    3.5888    0.1152 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1470    2.1095    1.0958 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9053    1.4020    0.0089 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2458    0.1053   -0.4055 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1400   -1.0480   -0.3399 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5383   -1.7731    0.7542 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3861   -2.7669    0.3141 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4828   -2.6321   -0.9862 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7706   -1.6375   -1.4207 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0416   -0.0343    0.3776 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5899   -1.3018    0.2718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0527   -2.5747    0.3606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6787   -3.5331   -0.3481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0406   -2.9552   -1.3921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1258   -1.4950   -1.7760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5762    0.2364   -1.7288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6737   -0.6199   -0.6322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8724    1.6381    0.0822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4287    0.3436    1.3204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7033    1.3118   -1.0340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8455    2.3067    1.7897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0335    3.6709   -0.8059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3977    4.4160    0.8305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7177    3.6068   -0.0778 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2491    1.4756    2.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6492    3.0803    1.2707 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8980    1.1168    0.4452 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0964    2.0803   -0.8389 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9026    0.2666   -1.4698 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2348   -1.5856    1.7587 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8918   -3.5265    0.8924 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7000   -1.3415   -2.4588 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1787   -2.0829    0.1022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0573   -1.5597    1.2660 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  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 16  1  0
 16 17  1  0
 10 11  1  0
 11 15  2  0
 15 14  1  0
 14 13  1  0
 13 12  2  0
 17  2  1  0
 12 11  1  0
 16  5  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  6
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  6
  6 27  1  1
  7 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  6
 17 39  1  0
 17 40  1  0
 15 38  1  0
 13 37  1  0
 12 36  1  0
M  END


  Mrv1652304282200302D          

 17 19  0  0  1  0            999 V2000
   -0.7145   -0.4125    0.0000 C   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
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    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
    1.4289   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0964   -2.9599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -3.7445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -3.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7615   -2.9599    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   -1.6500    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
  3  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  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
  4 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 11 15  1  0  0  0  0
  7 16  1  6  0  0  0
  2 17  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0051071

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CC[C@H]2[C@H](C)CC[C@H](N2C1)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H23NO/c1-11-3-5-14-12(2)4-6-15(16(14)9-11)13-7-8-17-10-13/h7-8,10-12,14-15H,3-6,9H2,1-2H3/t11-,12+,14-,15-/m0/s1

> <INCHI_KEY>
VACYOTYBTLYIEB-NEBZKDRISA-N

> <FORMULA>
C15H23NO

> <MOLECULAR_WEIGHT>
233.355

> <EXACT_MASS>
233.177964365

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
27.065951337829297

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,4S,7S,9aS)-4-(furan-3-yl)-1,7-dimethyl-octahydro-1H-quinolizine

> <ALOGPS_LOGP>
4.45

> <JCHEM_LOGP>
3.6051001593333325

> <ALOGPS_LOGS>
-3.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.524301422384548

> <JCHEM_POLAR_SURFACE_AREA>
16.380000000000003

> <JCHEM_REFRACTIVITY>
69.6817

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.54e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
deoxynupharidine

> <JCHEM_VEBER_RULE>
1

$$$$

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  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -0.770   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  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.913  -5.525   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.437  -6.990   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.897  -6.990   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.421  -5.525   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   16                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    4   11                                                  
CONECT   11   10   12   15                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   11                                                       
CONECT   16    7                                                            
CONECT   17    2                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

View in JSmol

Synonyms

Value	Source
Deoxynupharidine hydrochloride, (1alpha,4beta,7beta,9aalpha,1R)-isomer	MeSH
Deoxynupharidine, (1alpha,4alpha,7alpha,9abeta,1S)-isomer	MeSH
Deoxynupharidine, (1alpha,4alpha,7beta,9abeta,1S)-isomer	MeSH
Deoxynupharidine, (1alpha,4beta,7alpha,9aalpha,1R)-isomer	MeSH
Desoxynupharidine	MeSH

Chemical Formula

C₁₅H₂₃NO

Average Mass

233.3550 Da

Monoisotopic Mass

233.17796 Da

IUPAC Name

(1R,4S,7S,9aS)-4-(furan-3-yl)-1,7-dimethyl-octahydro-1H-quinolizine

Traditional Name

deoxynupharidine

CAS Registry Number

Not Available

SMILES

C[C@H]1CC[C@H]2[C@H](C)CC[C@H](N2C1)C1=COC=C1

InChI Identifier

InChI=1S/C15H23NO/c1-11-3-5-14-12(2)4-6-15(16(14)9-11)13-7-8-17-10-13/h7-8,10-12,14-15H,3-6,9H2,1-2H3/t11-,12+,14-,15-/m0/s1

InChI Key

VACYOTYBTLYIEB-NEBZKDRISA-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
Nuphar japonicum	Plant	KNApSAcK
Nuphar lutea	Plant	KNApSAcK
Nuphar microphylla	LOTUS Database	35616633
Nymphaea spp.	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinolizines. Quinolizines are compounds containing a quinolizine moiety, which consists of two fused pyridine rings sharing a nitrogen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolizines

Sub Class

Not Available

Direct Parent

Quinolizines

Alternative Parents

Substituents

Quinolizidine
Quinolizine
Aralkylamine
Piperidine
Furan
Heteroaromatic compound
Tertiary amine
Tertiary aliphatic amine
Oxacycle
Azacycle
Amine
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

quinolizines (CHEBI:4427 )
Quinolizidine alkaloids (C09945 )

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	4.45	ALOGPS
logP	3.61	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Basic)	9.52	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	16.38 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	69.68 m³·mol⁻¹	ChemAxon
Polarizability	27.07 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

C00001971

Chemspider ID

390950

KEGG Compound ID

C09945

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442525

PDB ID

Not Available

ChEBI ID

4427

Good Scents ID

rw1541651

References

General References

Li H, Wu J: Vinylogous Mukaiyama-Michael Reactions of Dihydropyridinones. Org Lett. 2015 Nov 6;17(21):5424-7. doi: 10.1021/acs.orglett.5b02778. Epub 2015 Oct 23. [PubMed:26493620 ]
Goodenough KM, Moran WJ, Raubo P, Harrity JP: Development of a flexible approach to Nuphar alkaloids via two enantiospecific piperidine-forming reactions. J Org Chem. 2005 Jan 7;70(1):207-13. doi: 10.1021/jo048455k. [PubMed:15624924 ]
Matsuda H, Morikawa T, Oda M, Asao Y, Yoshikawa M: Potent anti-metastatic activity of dimeric sesquiterpene thioalkaloids from the rhizome of Nuphar pumilum. Bioorg Med Chem Lett. 2003 Dec 15;13(24):4445-9. doi: 10.1016/j.bmcl.2003.09.019. [PubMed:14643343 ]
Moran WJ, Goodenough KM, Raubo P, Harrity JP: A concise asymmetric route to Nuphar alkaloids. A formal synthesis of (-)-deoxynupharidine. Org Lett. 2003 Sep 18;5(19):3427-9. doi: 10.1021/ol035156t. [PubMed:12967291 ]

Showing NP-Card for Deoxynupharidine (NP0051071)

MOL for NP0051071 (Deoxynupharidine)

3D MOL for NP0051071 (Deoxynupharidine)

3D SDF for NP0051071 (Deoxynupharidine)

3D-SDF for NP0051071 (Deoxynupharidine)

PDB for NP0051071 (Deoxynupharidine)

3D PDB for NP0051071 (Deoxynupharidine)

SMILES for NP0051071 (Deoxynupharidine)

INCHI for NP0051071 (Deoxynupharidine)

Structure for NP0051071 (Deoxynupharidine)

3D Structure for NP0051071 (Deoxynupharidine)