NP-MRD: Showing NP-Card for 2-(3-{2,4,5,6,8,10-hexamethyltricyclo[6.3.1.0⁴,¹¹]dodeca-2,6,9-trien-12-yl}-1-hydroxyprop-2-en-1-ylidene)-tetrahydropyrrolizine-1,3-dione (NP0181799)

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Record Information

Version

2.0

Created at

2022-09-03 20:22:55 UTC

Updated at

2022-09-03 20:22:55 UTC

NP-MRD ID

NP0181799

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(3-{2,4,5,6,8,10-hexamethyltricyclo[6.3.1.0⁴,¹¹]dodeca-2,6,9-trien-12-yl}-1-hydroxyprop-2-en-1-ylidene)-tetrahydropyrrolizine-1,3-dione

Description

2-(3-{2,4,5,6,8,10-Hexamethyltricyclo[6.3.1.0⁴,¹¹]Dodeca-2,6,9-trien-12-yl}-1-hydroxyprop-2-en-1-ylidene)-hexahydro-1H-pyrrolizine-1,3-dione belongs to the class of organic compounds known as pyrrolizidinones. Pyrrolizidinones are compounds containing a pyrrolizidine moiety which bears a ketone. Pyrrolizidine is a bicyclic ring system made up of two fused pyrrolidine ring sharing a nitrogen atom. 2-(3-{2,4,5,6,8,10-Hexamethyltricyclo[6.3.1.0⁴,¹¹]Dodeca-2,6,9-trien-12-yl}-1-hydroxyprop-2-en-1-ylidene)-hexahydro-1H-pyrrolizine-1,3-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241504412D          

 32 36  0  0  0  0            999 V2000
    2.7294    1.7922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7510    0.8110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5959    0.6791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9372   -0.1064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5767   -0.8909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3076   -1.4021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3332   -1.7211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4900   -1.5351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1325   -2.3318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2803   -0.5966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7984   -1.1789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7270   -0.9853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2597   -0.3794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1908    0.4186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9919    1.3089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7485    1.6838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7890    2.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.5852    2.7239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0367    2.0335    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    5.1922    0.6434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1574   -0.6198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3681   -0.9700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5153    0.8709    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
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  5  6  1  0  0  0  0
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  8 10  1  0  0  0  0
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  5 12  1  0  0  0  0
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  3 32  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1533004241504412D          

 32 36  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0181799

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C(C)=CC2(C)C=C(C)C3C(C2C=CC(O)=C2C(=O)C4CCCN4C2=O)C(C)=CC13C

> <INCHI_IDENTIFIER>
InChI=1S/C28H35NO3/c1-15-12-27(5)13-17(3)24-22(16(2)14-28(24,6)18(15)4)19(27)9-10-21(30)23-25(31)20-8-7-11-29(20)26(23)32/h9-10,12-14,18-20,22,24,30H,7-8,11H2,1-6H3

> <INCHI_KEY>
WDPIULZTNJKEMP-UHFFFAOYSA-N

> <FORMULA>
C28H35NO3

> <MOLECULAR_WEIGHT>
433.592

> <EXACT_MASS>
433.261693991

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
49.555992404802296

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(3-{2,4,5,6,8,10-hexamethyltricyclo[6.3.1.0⁴,¹¹]dodeca-2,6,9-trien-12-yl}-1-hydroxyprop-2-en-1-ylidene)-hexahydro-1H-pyrrolizine-1,3-dione

> <ALOGPS_LOGP>
4.71

> <JCHEM_LOGP>
3.8950739123333347

> <ALOGPS_LOGS>
-4.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.3988867054627

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.849518137477587

> <JCHEM_PKA_STRONGEST_BASIC>
-1.0582931195774923

> <JCHEM_POLAR_SURFACE_AREA>
57.61

> <JCHEM_REFRACTIVITY>
131.78099999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.10e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(3-{2,4,5,6,8,10-hexamethyltricyclo[6.3.1.0⁴,¹¹]dodeca-2,6,9-trien-12-yl}-1-hydroxyprop-2-en-1-ylidene)-tetrahydropyrrolizine-1,3-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       5.095   3.346   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.135   1.514   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.712   1.268   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.349  -0.199   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.677  -1.663   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.041  -2.617   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.222  -3.213   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.648  -2.866   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.981  -4.353   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.257  -1.114   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.357  -2.201   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.090  -1.839   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.085  -0.708   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.956   0.781   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.585   2.443   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.997   3.143   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.073   4.681   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.383   6.155   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.559   5.085   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.524   6.285   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.964   5.737   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.888   4.199   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0       9.402   3.796   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0       8.642   2.668   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       9.692   1.201   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       3.964   3.150   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.160  -1.157   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.357   0.382   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.939   0.451   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.836   1.723   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.687  -1.811   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.429   1.626   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   29                                                  
CONECT    3    2    4   32                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7   12                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   29                                                  
CONECT   11   10   12   27                                                  
CONECT   12   11    5   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   26                                                  
CONECT   16   15   17   24                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   23                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   19   24                                                  
CONECT   24   23   16   25                                                  
CONECT   25   24                                                            
CONECT   26   15                                                            
CONECT   27   11   28   31                                                  
CONECT   28   27   29                                                       
CONECT   29   28    2   10   30                                             
CONECT   30   29                                                            
CONECT   31   27                                                            
CONECT   32    3                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₅NO₃

Average Mass

433.5920 Da

Monoisotopic Mass

433.26169 Da

IUPAC Name

2-(3-{2,4,5,6,8,10-hexamethyltricyclo[6.3.1.0⁴,¹¹]dodeca-2,6,9-trien-12-yl}-1-hydroxyprop-2-en-1-ylidene)-hexahydro-1H-pyrrolizine-1,3-dione

Traditional Name

2-(3-{2,4,5,6,8,10-hexamethyltricyclo[6.3.1.0⁴,¹¹]dodeca-2,6,9-trien-12-yl}-1-hydroxyprop-2-en-1-ylidene)-tetrahydropyrrolizine-1,3-dione

CAS Registry Number

Not Available

SMILES

CC1C(C)=CC2(C)C=C(C)C3C(C2C=CC(O)=C2C(=O)C4CCCN4C2=O)C(C)=CC13C

InChI Identifier

InChI=1S/C28H35NO3/c1-15-12-27(5)13-17(3)24-22(16(2)14-28(24,6)18(15)4)19(27)9-10-21(30)23-25(31)20-8-7-11-29(20)26(23)32/h9-10,12-14,18-20,22,24,30H,7-8,11H2,1-6H3

InChI Key

WDPIULZTNJKEMP-UHFFFAOYSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrrolizidinones. Pyrrolizidinones are compounds containing a pyrrolizidine moiety which bears a ketone. Pyrrolizidine is a bicyclic ring system made up of two fused pyrrolidine ring sharing a nitrogen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolizidines

Sub Class

Pyrrolizidinones

Direct Parent

Pyrrolizidinones

Alternative Parents

Substituents

Pyrrolizidinone
Pyrrolidone
2-pyrrolidone
3-pyrrolidone
N-alkylpyrrolidine
Pyrrolidine
Tertiary carboxylic acid amide
Vinylogous acid
Lactam
Ketone
Carboxamide group
Enol
Carboxylic acid derivative
Azacycle
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
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	4.71	ALOGPS
logP	3.9	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	5.85	ChemAxon
pKa (Strongest Basic)	-1.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	57.61 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	131.78 m³·mol⁻¹	ChemAxon
Polarizability	49.56 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

76181106

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-(3-{2,4,5,6,8,10-hexamethyltricyclo[6.3.1.0⁴,¹¹]dodeca-2,6,9-trien-12-yl}-1-hydroxyprop-2-en-1-ylidene)-tetrahydropyrrolizine-1,3-dione (NP0181799)

MOL for NP0181799 (2-(3-{2,4,5,6,8,10-hexamethyltricyclo[6.3.1.0⁴,¹¹]dodeca-2,6,9-trien-12-yl}-1-hydroxyprop-2-en-1-ylidene)-tetrahydropyrrolizine-1,3-dione)

3D MOL for NP0181799 (2-(3-{2,4,5,6,8,10-hexamethyltricyclo[6.3.1.0⁴,¹¹]dodeca-2,6,9-trien-12-yl}-1-hydroxyprop-2-en-1-ylidene)-tetrahydropyrrolizine-1,3-dione)

3D SDF for NP0181799 (2-(3-{2,4,5,6,8,10-hexamethyltricyclo[6.3.1.0⁴,¹¹]dodeca-2,6,9-trien-12-yl}-1-hydroxyprop-2-en-1-ylidene)-tetrahydropyrrolizine-1,3-dione)

3D-SDF for NP0181799 (2-(3-{2,4,5,6,8,10-hexamethyltricyclo[6.3.1.0⁴,¹¹]dodeca-2,6,9-trien-12-yl}-1-hydroxyprop-2-en-1-ylidene)-tetrahydropyrrolizine-1,3-dione)

PDB for NP0181799 (2-(3-{2,4,5,6,8,10-hexamethyltricyclo[6.3.1.0⁴,¹¹]dodeca-2,6,9-trien-12-yl}-1-hydroxyprop-2-en-1-ylidene)-tetrahydropyrrolizine-1,3-dione)

3D PDB for NP0181799 (2-(3-{2,4,5,6,8,10-hexamethyltricyclo[6.3.1.0⁴,¹¹]dodeca-2,6,9-trien-12-yl}-1-hydroxyprop-2-en-1-ylidene)-tetrahydropyrrolizine-1,3-dione)

SMILES for NP0181799 (2-(3-{2,4,5,6,8,10-hexamethyltricyclo[6.3.1.0⁴,¹¹]dodeca-2,6,9-trien-12-yl}-1-hydroxyprop-2-en-1-ylidene)-tetrahydropyrrolizine-1,3-dione)

INCHI for NP0181799 (2-(3-{2,4,5,6,8,10-hexamethyltricyclo[6.3.1.0⁴,¹¹]dodeca-2,6,9-trien-12-yl}-1-hydroxyprop-2-en-1-ylidene)-tetrahydropyrrolizine-1,3-dione)

Structure for NP0181799 (2-(3-{2,4,5,6,8,10-hexamethyltricyclo[6.3.1.0⁴,¹¹]dodeca-2,6,9-trien-12-yl}-1-hydroxyprop-2-en-1-ylidene)-tetrahydropyrrolizine-1,3-dione)

3D Structure for NP0181799 (2-(3-{2,4,5,6,8,10-hexamethyltricyclo[6.3.1.0⁴,¹¹]dodeca-2,6,9-trien-12-yl}-1-hydroxyprop-2-en-1-ylidene)-tetrahydropyrrolizine-1,3-dione)