NP-MRD: Showing NP-Card for (+)-Grandisine D (NP0077976)

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Record Information

Version

1.0

Created at

2022-04-28 23:07:34 UTC

Updated at

2022-04-28 23:07:34 UTC

NP-MRD ID

NP0077976

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Grandisine D

Description

(5S,6R)-6-[(8R,8aS)-octahydroindolizine-8-carbonyl]-5-methylcyclohex-2-en-1-one belongs to the class of organic compounds known as indolizidines. These are polycyclic compounds containing an indolizidine, which is a bicyclic heterocycle containing a saturated six-member ring fused to a saturated five-member ring, one of the bridging atoms being nitrogen. (+)-Grandisine D is found in Elaeocarpus angustifolius and Elaeocarpus grandis. Based on a literature review very few articles have been published on (5S,6R)-6-[(8R,8aS)-octahydroindolizine-8-carbonyl]-5-methylcyclohex-2-en-1-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 44  0  0  0  0  0  0  0  0999 V2000
    3.3319   -1.9935   -0.2146 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9841   -0.5748    0.1530 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1989    0.2756    0.0330 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8904    1.6889    0.3295 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8091    2.2159   -0.2255 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0149    1.3188   -1.0940 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5696    1.7662   -2.1980 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7841   -0.0656   -0.6200 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5347   -0.2540    0.1464 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6874   -0.7827    1.2702 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8257    0.1259   -0.3101 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9217    1.6094   -0.4850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1516    2.1782    0.2216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3190    1.2689   -0.1814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1485    0.0345    0.5008 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9246   -1.0557    0.0200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2320   -2.2702    0.6066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7823   -1.8947    0.6710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8147   -0.3836    0.7089 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9030   -1.9476   -1.1779 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4470   -2.6441   -0.3106 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0594   -2.3653    0.5432 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6876   -0.5901    1.2413 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9624   -0.1005    0.7305 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6192    0.1911   -0.9914 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4959    2.3132    0.9718 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4850    3.2401   -0.0864 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7527   -0.6978   -1.5562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0474   -0.3913   -1.2770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0674    2.1615   -0.0569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0702    1.8400   -1.5654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3126    3.2061   -0.1057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9899    2.0648    1.3085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3119    1.1746   -1.2867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2932    1.7175    0.1114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0519   -1.1057   -1.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9495   -1.0349    0.4910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3962   -3.1817    0.0199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5784   -2.4405    1.6503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3096   -2.3035    1.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2457   -2.2778   -0.2186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4732   -0.0358    1.7057 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  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
  8  2  1  0
 19 11  1  0
 19 15  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  1
  3 24  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  0
  8 28  1  6
 11 29  1  6
 12 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
 17 39  1  0
 18 40  1  0
 18 41  1  0
 19 42  1  1
M  END


  Mrv1652304292201072D          

 19 21  0  0  1  0            999 V2000
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    3.5854    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3523    4.4104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0668    4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    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
  6  7  1  6  0  0  0
  7  8  2  0  0  0  0
  9  7  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 16  1  1  0  0  0
  5 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  4 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0077976

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CC=CC(=O)[C@@H]1C(=O)[C@@H]1CCCN2CCC[C@@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C16H23NO2/c1-11-5-2-8-14(18)15(11)16(19)12-6-3-9-17-10-4-7-13(12)17/h2,8,11-13,15H,3-7,9-10H2,1H3/t11-,12+,13-,15+/m0/s1

> <INCHI_KEY>
PVKYIBHVAJSUIB-SFDCQRBFSA-N

> <FORMULA>
C16H23NO2

> <MOLECULAR_WEIGHT>
261.365

> <EXACT_MASS>
261.172878985

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
29.04322084227855

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5S,6R)-6-[(8R,8aS)-octahydroindolizine-8-carbonyl]-5-methylcyclohex-2-en-1-one

> <ALOGPS_LOGP>
2.71

> <JCHEM_LOGP>
2.2707859836963222

> <ALOGPS_LOGS>
-2.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.510354918081628

> <JCHEM_PKA_STRONGEST_BASIC>
9.92987153840319

> <JCHEM_POLAR_SURFACE_AREA>
37.38

> <JCHEM_REFRACTIVITY>
76.51559999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.99e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5S,6R)-6-[(8R,8aS)-octahydroindolizine-8-carbonyl]-5-methylcyclohex-2-en-1-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       3.590   2.073   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.924   5.923   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.590   6.693   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.258   6.693   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.258   8.233   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.591   9.003   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.925   8.233   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.925   6.693   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.591   5.923   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       7.591   4.383   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.924   9.003   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   19                                                  
CONECT    5    4    6   17                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   14                                                  
CONECT   10    9   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9   15                                                  
CONECT   15   14                                                            
CONECT   16   10                                                            
CONECT   17    5   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18    4                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₂₃NO₂

Average Mass

261.3650 Da

Monoisotopic Mass

261.17288 Da

IUPAC Name

(5S,6R)-6-[(8R,8aS)-octahydroindolizine-8-carbonyl]-5-methylcyclohex-2-en-1-one

Traditional Name

(5S,6R)-6-[(8R,8aS)-octahydroindolizine-8-carbonyl]-5-methylcyclohex-2-en-1-one

CAS Registry Number

Not Available

SMILES

C[C@H]1CC=CC(=O)[C@@H]1C(=O)[C@@H]1CCCN2CCC[C@@H]12

InChI Identifier

InChI=1S/C16H23NO2/c1-11-5-2-8-14(18)15(11)16(19)12-6-3-9-17-10-4-7-13(12)17/h2,8,11-13,15H,3-7,9-10H2,1H3/t11-,12+,13-,15+/m0/s1

InChI Key

PVKYIBHVAJSUIB-SFDCQRBFSA-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
Elaeocarpus angustifolius	LOTUS Database	35616633
Elaeocarpus grandis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolizidines. These are polycyclic compounds containing an indolizidine, which is a bicyclic heterocycle containing a saturated six-member ring fused to a saturated five-member ring, one of the bridging atoms being nitrogen.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indolizidines

Sub Class

Not Available

Direct Parent

Indolizidines

Alternative Parents

Substituents

Indolizidine
Cyclohexenone
1,3-diketone
N-alkylpyrrolidine
1,3-dicarbonyl compound
Piperidine
Beta-aminoketone
Pyrrolidine
Cyclic ketone
Tertiary aliphatic amine
Tertiary amine
Ketone
Azacycle
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
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	2.71	ALOGPS
logP	2.27	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	8.51	ChemAxon
pKa (Strongest Basic)	9.93	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	37.38 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	76.52 m³·mol⁻¹	ChemAxon
Polarizability	29.04 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

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

163105591

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Grandisine D (NP0077976)

MOL for NP0077976 ((+)-Grandisine D)

3D MOL for NP0077976 ((+)-Grandisine D)

3D SDF for NP0077976 ((+)-Grandisine D)

3D-SDF for NP0077976 ((+)-Grandisine D)

PDB for NP0077976 ((+)-Grandisine D)

3D PDB for NP0077976 ((+)-Grandisine D)

SMILES for NP0077976 ((+)-Grandisine D)

INCHI for NP0077976 ((+)-Grandisine D)

Structure for NP0077976 ((+)-Grandisine D)

3D Structure for NP0077976 ((+)-Grandisine D)