NP-MRD: Showing NP-Card for (7z)-14-[5-(3-heptyloxiran-2-yl)penta-1,3-diyn-1-yl]-1,5,5,8-tetramethyl-15-oxatricyclo[9.4.0.0⁴,⁷]pentadeca-7,13-diene (NP0269416)

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Record Information

Version

2.0

Created at

2022-09-08 14:53:28 UTC

Updated at

2022-09-08 14:53:28 UTC

NP-MRD ID

NP0269416

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(7z)-14-[5-(3-heptyloxiran-2-yl)penta-1,3-diyn-1-yl]-1,5,5,8-tetramethyl-15-oxatricyclo[9.4.0.0⁴,⁷]pentadeca-7,13-diene

Description

Glycyrrhizaisoflavone C belongs to the class of organic compounds known as pyranoisoflavonoids. These are isoflavonoids that contain a pyran ring fused to either of the A, B, or C ring of the isoflavonoid skeleton. Glycyrrhizaisoflavone C is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Glycyrrhizaisoflavone C has been detected, but not quantified in, herbs and spices and tea. (7z)-14-[5-(3-heptyloxiran-2-yl)penta-1,3-diyn-1-yl]-1,5,5,8-tetramethyl-15-oxatricyclo[9.4.0.0⁴,⁷]pentadeca-7,13-diene is found in Panax ginseng. This could make glycyrrhizaisoflavone C a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241217372D          

 34 37  0  0  0  0            999 V2000
    2.5548   -1.2399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5548   -0.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2691   -0.0014    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9819   -0.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9819   -1.2399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2691   -1.6501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6948   -0.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4091   -0.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.1219   -0.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.8362   -1.2399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.4260    1.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.9819    0.4115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  4 19  1  0  0  0  0
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 21 22  1  0  0  0  0
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 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv0541 02241217372D          

 34 37  0  0  0  0            999 V2000
    2.5548   -1.2399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5548   -0.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.8375    1.2372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5517    1.6501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  2 20  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  4 19  1  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  7  8  1  0  0  0  0
  8 10  1  0  0  0  0
  9 13  1  0  0  0  0
 10 11  1  0  0  0  0
 10 15  1  0  0  0  0
 11 12  2  0  0  0  0
 11 14  1  0  0  0  0
 12 13  1  0  0  0  0
 12 18  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 20 21  3  0  0  0  0
 21 22  1  0  0  0  0
 22 23  3  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0269416

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCC1OC1CC#CC#CC1=CCC2CC\C(C)=C3\CC(C)(C)C3CCC2(C)O1

> <INCHI_IDENTIFIER>
InChI=1S/C32H46O2/c1-6-7-8-9-12-15-29-30(33-29)16-13-10-11-14-26-20-19-25-18-17-24(2)27-23-31(3,4)28(27)21-22-32(25,5)34-26/h20,25,28-30H,6-9,12,15-19,21-23H2,1-5H3/b27-24-

> <INCHI_KEY>
UZINSQVBXBQDEQ-PNHLSOANSA-N

> <FORMULA>
C32H46O2

> <MOLECULAR_WEIGHT>
462.7064

> <EXACT_MASS>
462.349780716

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
60.205106515558136

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(7Z)-14-[5-(3-heptyloxiran-2-yl)penta-1,3-diyn-1-yl]-1,5,5,8-tetramethyl-15-oxatricyclo[9.4.0.0⁴,⁷]pentadeca-7,13-diene

> <ALOGPS_LOGP>
8.30

> <JCHEM_LOGP>
8.376338559333334

> <ALOGPS_LOGS>
-5.59

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.631011415406157

> <JCHEM_PKA_STRONGEST_BASIC>
-4.133338508050395

> <JCHEM_POLAR_SURFACE_AREA>
21.759999999999998

> <JCHEM_REFRACTIVITY>
144.99749999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.20e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(7Z)-14-[5-(3-heptyloxiran-2-yl)penta-1,3-diyn-1-yl]-1,5,5,8-tetramethyl-15-oxatricyclo[9.4.0.0⁴,⁷]pentadeca-7,13-diene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       4.769  -2.315   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.769  -0.773   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       6.102  -0.003   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       7.433  -0.773   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.433  -2.315   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.102  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.764  -0.003   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.097  -0.773   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.097  -2.315   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.428  -0.003   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.761  -0.773   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.761  -2.315   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.428  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.097  -0.003   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.761   0.768   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.995   2.104   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.536   2.104   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.097  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.433   0.768   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.431  -0.003   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.095   0.768   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.757   1.539   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.582   2.309   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.920   3.080   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.925   2.309   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.774   2.309   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -3.849   0.681   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -6.105   3.080   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -7.438   2.309   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -8.769   3.080   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -10.102   2.309   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0     -11.433   3.080   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -12.763   2.309   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0     -14.097   3.080   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7   19                                             
CONECT    5    4    6    9                                                  
CONECT    6    1    5                                                       
CONECT    7    4    8                                                       
CONECT    8    7   10                                                       
CONECT    9    5   13                                                       
CONECT   10    8   11   15                                                  
CONECT   11   10   12   14                                                  
CONECT   12   11   13   18                                                  
CONECT   13    9   12                                                       
CONECT   14   11   15                                                       
CONECT   15   10   14   16   17                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   12                                                            
CONECT   19    4                                                            
CONECT   20    2   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25   27   28                                                  
CONECT   27   25   26                                                       
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₄₆O₂

Average Mass

462.7064 Da

Monoisotopic Mass

462.34978 Da

IUPAC Name

(7Z)-14-[5-(3-heptyloxiran-2-yl)penta-1,3-diyn-1-yl]-1,5,5,8-tetramethyl-15-oxatricyclo[9.4.0.0⁴,⁷]pentadeca-7,13-diene

Traditional Name

(7Z)-14-[5-(3-heptyloxiran-2-yl)penta-1,3-diyn-1-yl]-1,5,5,8-tetramethyl-15-oxatricyclo[9.4.0.0⁴,⁷]pentadeca-7,13-diene

CAS Registry Number

Not Available

SMILES

CCCCCCCC1OC1CC#CC#CC1=CCC2CC\C(C)=C3\CC(C)(C)C3CCC2(C)O1

InChI Identifier

InChI=1S/C32H46O2/c1-6-7-8-9-12-15-29-30(33-29)16-13-10-11-14-26-20-19-25-18-17-24(2)27-23-31(3,4)28(27)21-22-32(25,5)34-26/h20,25,28-30H,6-9,12,15-19,21-23H2,1-5H3/b27-24-

InChI Key

UZINSQVBXBQDEQ-PNHLSOANSA-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
Panax ginseng	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranoisoflavonoids. These are isoflavonoids that contain a pyran ring fused to either of the A, B, or C ring of the isoflavonoid skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Pyranoisoflavonoids

Direct Parent

Pyranoisoflavonoids

Alternative Parents

Substituents

Pyranoisoflavonoid
Isoflavone
Hydroxyisoflavonoid
2,2-dimethyl-1-benzopyran
Chromone
Chromane
Benzopyran
1-benzopyran
Anisole
Pyranone
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Pyran
Heteroaromatic compound
Ether
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	8.3	ALOGPS
logP	8.38	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	18.63	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	21.76 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	145 m³·mol⁻¹	ChemAxon
Polarizability	60.21 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0035526

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB014218

KNApSAcK ID

Not Available

Chemspider ID

8770552

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10595178

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (7z)-14-[5-(3-heptyloxiran-2-yl)penta-1,3-diyn-1-yl]-1,5,5,8-tetramethyl-15-oxatricyclo[9.4.0.0⁴,⁷]pentadeca-7,13-diene (NP0269416)

MOL for NP0269416 ((7z)-14-[5-(3-heptyloxiran-2-yl)penta-1,3-diyn-1-yl]-1,5,5,8-tetramethyl-15-oxatricyclo[9.4.0.0⁴,⁷]pentadeca-7,13-diene)

3D MOL for NP0269416 ((7z)-14-[5-(3-heptyloxiran-2-yl)penta-1,3-diyn-1-yl]-1,5,5,8-tetramethyl-15-oxatricyclo[9.4.0.0⁴,⁷]pentadeca-7,13-diene)

3D SDF for NP0269416 ((7z)-14-[5-(3-heptyloxiran-2-yl)penta-1,3-diyn-1-yl]-1,5,5,8-tetramethyl-15-oxatricyclo[9.4.0.0⁴,⁷]pentadeca-7,13-diene)

3D-SDF for NP0269416 ((7z)-14-[5-(3-heptyloxiran-2-yl)penta-1,3-diyn-1-yl]-1,5,5,8-tetramethyl-15-oxatricyclo[9.4.0.0⁴,⁷]pentadeca-7,13-diene)

PDB for NP0269416 ((7z)-14-[5-(3-heptyloxiran-2-yl)penta-1,3-diyn-1-yl]-1,5,5,8-tetramethyl-15-oxatricyclo[9.4.0.0⁴,⁷]pentadeca-7,13-diene)

3D PDB for NP0269416 ((7z)-14-[5-(3-heptyloxiran-2-yl)penta-1,3-diyn-1-yl]-1,5,5,8-tetramethyl-15-oxatricyclo[9.4.0.0⁴,⁷]pentadeca-7,13-diene)

SMILES for NP0269416 ((7z)-14-[5-(3-heptyloxiran-2-yl)penta-1,3-diyn-1-yl]-1,5,5,8-tetramethyl-15-oxatricyclo[9.4.0.0⁴,⁷]pentadeca-7,13-diene)

INCHI for NP0269416 ((7z)-14-[5-(3-heptyloxiran-2-yl)penta-1,3-diyn-1-yl]-1,5,5,8-tetramethyl-15-oxatricyclo[9.4.0.0⁴,⁷]pentadeca-7,13-diene)

Structure for NP0269416 ((7z)-14-[5-(3-heptyloxiran-2-yl)penta-1,3-diyn-1-yl]-1,5,5,8-tetramethyl-15-oxatricyclo[9.4.0.0⁴,⁷]pentadeca-7,13-diene)

3D Structure for NP0269416 ((7z)-14-[5-(3-heptyloxiran-2-yl)penta-1,3-diyn-1-yl]-1,5,5,8-tetramethyl-15-oxatricyclo[9.4.0.0⁴,⁷]pentadeca-7,13-diene)