NP-MRD: Showing NP-Card for 5-(propan-2-ylidene)-3-[(1r,3s,6r,7s,10r,11r,16s)-10,11,15,15-tetramethyl-19-oxapentacyclo[14.2.1.0²,¹⁴.0³,¹¹.0⁶,¹⁰]nonadec-2(14)-en-7-yl]cyclopent-2-en-1-one (NP0170139)

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Record Information

Version

2.0

Created at

2022-09-03 06:13:48 UTC

Updated at

2022-09-03 06:13:48 UTC

NP-MRD ID

NP0170139

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-(propan-2-ylidene)-3-[(1r,3s,6r,7s,10r,11r,16s)-10,11,15,15-tetramethyl-19-oxapentacyclo[14.2.1.0²,¹⁴.0³,¹¹.0⁶,¹⁰]nonadec-2(14)-en-7-yl]cyclopent-2-en-1-one

Description

Gypensapogenin B belongs to the class of organic compounds known as oxasteroids and derivatives. These are steroid derivatives where a carbon atom of the steroid is replaced by an oxygen atom. 5-(propan-2-ylidene)-3-[(1r,3s,6r,7s,10r,11r,16s)-10,11,15,15-tetramethyl-19-oxapentacyclo[14.2.1.0²,¹⁴.0³,¹¹.0⁶,¹⁰]nonadec-2(14)-en-7-yl]cyclopent-2-en-1-one is found in Gynostemma pentaphyllum. 5-(propan-2-ylidene)-3-[(1r,3s,6r,7s,10r,11r,16s)-10,11,15,15-tetramethyl-19-oxapentacyclo[14.2.1.0²,¹⁴.0³,¹¹.0⁶,¹⁰]nonadec-2(14)-en-7-yl]cyclopent-2-en-1-one was first documented in 2012 (PMID: 22342101). Based on a literature review very few articles have been published on Gypensapogenin B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032208132D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309032208132D          

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 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 16 28  1  0  0  0  0
 28 29  1  6  0  0  0
 25 29  1  6  0  0  0
  6 30  2  0  0  0  0
 30 31  1  0  0  0  0
  4 31  1  0  0  0  0
 31 32  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0170139

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=C1CC(=CC1=O)[C@H]1CC[C@]2(C)[C@@H]1CC[C@@H]1C3=C(CC[C@@]21C)C(C)(C)[C@@H]1CC[C@H]3O1

> <INCHI_IDENTIFIER>
InChI=1S/C30H42O2/c1-17(2)20-15-18(16-24(20)31)19-11-13-29(5)21(19)7-8-23-27-22(12-14-30(23,29)6)28(3,4)26-10-9-25(27)32-26/h16,19,21,23,25-26H,7-15H2,1-6H3/t19-,21-,23-,25-,26+,29-,30-/m1/s1

> <INCHI_KEY>
NNUMQZNZQGQGCN-AGHUFMIKSA-N

> <FORMULA>
C30H42O2

> <MOLECULAR_WEIGHT>
434.664

> <EXACT_MASS>
434.318480592

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
52.85337938002946

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-(propan-2-ylidene)-3-[(1R,3S,6R,7S,10R,11R,16S)-10,11,15,15-tetramethyl-19-oxapentacyclo[14.2.1.0^{2,14}.0^{3,11}.0^{6,10}]nonadec-2(14)-en-7-yl]cyclopent-2-en-1-one

> <ALOGPS_LOGP>
6.32

> <JCHEM_LOGP>
6.404035578999999

> <ALOGPS_LOGS>
-5.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.644705084540153

> <JCHEM_PKA_STRONGEST_BASIC>
-4.056236261396635

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
132.07469999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.41e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-(propan-2-ylidene)-3-[(1R,3S,6R,7S,10R,11R,16S)-10,11,15,15-tetramethyl-19-oxapentacyclo[14.2.1.0^{2,14}.0^{3,11}.0^{6,10}]nonadec-2(14)-en-7-yl]cyclopent-2-en-1-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      14.648  -4.402   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.431  -2.877   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.642  -1.927   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.002  -2.303   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.626  -0.810   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.090  -0.705   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.271   0.599   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.845   2.028   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.664   3.016   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.359   2.197   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.142   3.722   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.735   0.704   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.629  -0.368   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.148   0.053   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.772   1.547   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.291   1.969   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.916   3.462   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.022   4.534   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.503   4.112   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.878   2.619   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.598   3.980   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.514   4.100   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.448   5.325   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.528   5.283   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.141   3.402   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.832   1.893   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.818   0.710   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.358   0.744   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.917   1.796   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      10.516  -2.134   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      11.697  -3.122   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      11.593  -4.658   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   31                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   30                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   20                                             
CONECT   11   10                                                            
CONECT   12   10    7   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17   28                                                  
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   15   10   21                                             
CONECT   21   20                                                            
CONECT   22   17   23   24   25                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   22   26   29                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   16   29                                                  
CONECT   29   28   25                                                       
CONECT   30    6   31                                                       
CONECT   31   30    4   32                                                  
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₂O₂

Average Mass

434.6640 Da

Monoisotopic Mass

434.31848 Da

IUPAC Name

5-(propan-2-ylidene)-3-[(1R,3S,6R,7S,10R,11R,16S)-10,11,15,15-tetramethyl-19-oxapentacyclo[14.2.1.0^{2,14}.0^{3,11}.0^{6,10}]nonadec-2(14)-en-7-yl]cyclopent-2-en-1-one

Traditional Name

5-(propan-2-ylidene)-3-[(1R,3S,6R,7S,10R,11R,16S)-10,11,15,15-tetramethyl-19-oxapentacyclo[14.2.1.0^{2,14}.0^{3,11}.0^{6,10}]nonadec-2(14)-en-7-yl]cyclopent-2-en-1-one

CAS Registry Number

Not Available

SMILES

CC(C)=C1CC(=CC1=O)[C@H]1CC[C@]2(C)[C@@H]1CC[C@@H]1C3=C(CC[C@@]21C)C(C)(C)[C@@H]1CC[C@H]3O1

InChI Identifier

InChI=1S/C30H42O2/c1-17(2)20-15-18(16-24(20)31)19-11-13-29(5)21(19)7-8-23-27-22(12-14-30(23,29)6)28(3,4)26-10-9-25(27)32-26/h16,19,21,23,25-26H,7-15H2,1-6H3/t19-,21-,23-,25-,26+,29-,30-/m1/s1

InChI Key

NNUMQZNZQGQGCN-AGHUFMIKSA-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
Gynostemma pentaphyllum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxasteroids and derivatives. These are steroid derivatives where a carbon atom of the steroid is replaced by an oxygen atom.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Oxasteroids and derivatives

Direct Parent

Oxasteroids and derivatives

Alternative Parents

Substituents

2-oxasteroid
Sesquiterpenoid
Naphthopyran
Naphthalene
Pyran
Oxolane
Ketone
Cyclic ketone
Oxacycle
Ether
Dialkyl ether
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen 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	6.32	ALOGPS
logP	6.4	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	16.64	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	132.07 m³·mol⁻¹	ChemAxon
Polarizability	52.85 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

28494952

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

57400364

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Li N, Wu CF, Xu XY, Liu ZY, Li X, Zhao YQ: Triterpenes possessing an unprecedented skeleton isolated from hydrolyzate of total saponins from Gynostemma pentaphyllum. Eur J Med Chem. 2012 Apr;50:173-8. doi: 10.1016/j.ejmech.2012.01.052. Epub 2012 Feb 3. [PubMed:22342101 ]
LOTUS database [Link]

Showing NP-Card for 5-(propan-2-ylidene)-3-[(1r,3s,6r,7s,10r,11r,16s)-10,11,15,15-tetramethyl-19-oxapentacyclo[14.2.1.0²,¹⁴.0³,¹¹.0⁶,¹⁰]nonadec-2(14)-en-7-yl]cyclopent-2-en-1-one (NP0170139)

MOL for NP0170139 (5-(propan-2-ylidene)-3-[(1r,3s,6r,7s,10r,11r,16s)-10,11,15,15-tetramethyl-19-oxapentacyclo[14.2.1.0²,¹⁴.0³,¹¹.0⁶,¹⁰]nonadec-2(14)-en-7-yl]cyclopent-2-en-1-one)

3D MOL for NP0170139 (5-(propan-2-ylidene)-3-[(1r,3s,6r,7s,10r,11r,16s)-10,11,15,15-tetramethyl-19-oxapentacyclo[14.2.1.0²,¹⁴.0³,¹¹.0⁶,¹⁰]nonadec-2(14)-en-7-yl]cyclopent-2-en-1-one)

3D SDF for NP0170139 (5-(propan-2-ylidene)-3-[(1r,3s,6r,7s,10r,11r,16s)-10,11,15,15-tetramethyl-19-oxapentacyclo[14.2.1.0²,¹⁴.0³,¹¹.0⁶,¹⁰]nonadec-2(14)-en-7-yl]cyclopent-2-en-1-one)

3D-SDF for NP0170139 (5-(propan-2-ylidene)-3-[(1r,3s,6r,7s,10r,11r,16s)-10,11,15,15-tetramethyl-19-oxapentacyclo[14.2.1.0²,¹⁴.0³,¹¹.0⁶,¹⁰]nonadec-2(14)-en-7-yl]cyclopent-2-en-1-one)

PDB for NP0170139 (5-(propan-2-ylidene)-3-[(1r,3s,6r,7s,10r,11r,16s)-10,11,15,15-tetramethyl-19-oxapentacyclo[14.2.1.0²,¹⁴.0³,¹¹.0⁶,¹⁰]nonadec-2(14)-en-7-yl]cyclopent-2-en-1-one)

3D PDB for NP0170139 (5-(propan-2-ylidene)-3-[(1r,3s,6r,7s,10r,11r,16s)-10,11,15,15-tetramethyl-19-oxapentacyclo[14.2.1.0²,¹⁴.0³,¹¹.0⁶,¹⁰]nonadec-2(14)-en-7-yl]cyclopent-2-en-1-one)

SMILES for NP0170139 (5-(propan-2-ylidene)-3-[(1r,3s,6r,7s,10r,11r,16s)-10,11,15,15-tetramethyl-19-oxapentacyclo[14.2.1.0²,¹⁴.0³,¹¹.0⁶,¹⁰]nonadec-2(14)-en-7-yl]cyclopent-2-en-1-one)

INCHI for NP0170139 (5-(propan-2-ylidene)-3-[(1r,3s,6r,7s,10r,11r,16s)-10,11,15,15-tetramethyl-19-oxapentacyclo[14.2.1.0²,¹⁴.0³,¹¹.0⁶,¹⁰]nonadec-2(14)-en-7-yl]cyclopent-2-en-1-one)

Structure for NP0170139 (5-(propan-2-ylidene)-3-[(1r,3s,6r,7s,10r,11r,16s)-10,11,15,15-tetramethyl-19-oxapentacyclo[14.2.1.0²,¹⁴.0³,¹¹.0⁶,¹⁰]nonadec-2(14)-en-7-yl]cyclopent-2-en-1-one)

3D Structure for NP0170139 (5-(propan-2-ylidene)-3-[(1r,3s,6r,7s,10r,11r,16s)-10,11,15,15-tetramethyl-19-oxapentacyclo[14.2.1.0²,¹⁴.0³,¹¹.0⁶,¹⁰]nonadec-2(14)-en-7-yl]cyclopent-2-en-1-one)