NP-MRD: Showing NP-Card for 21-nor-4-ene-chaxine A (NP0332769)

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Record Information

Version

2.0

Created at

2024-04-19 23:45:25 UTC

Updated at

2024-09-03 04:20:15 UTC

NP-MRD ID

NP0332769

Natural Product DOI

https://doi.org/10.57994/2040

Secondary Accession Numbers

None

Natural Product Identification

Common Name

21-nor-4-ene-chaxine A

Description

21-Nor-4-ene-chaxine A belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. 21-nor-4-ene-chaxine A was first documented in 2024 (PMID: 38576052). Based on a literature review very few articles have been published on 21-nor-4-ene-chaxine A.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01022302222D          

 24 26  0  0  1  0            999 V2000
   -2.8092    6.5548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1961    6.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3891    6.1743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9766    5.4598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1696    5.2883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0853    4.5036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4667    3.8905    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3179    3.6356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2737    4.0621    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6862    3.3476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1342    2.7345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3805    3.0701    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4237    2.2462    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3340    2.6576    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0484    3.0701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7629    2.6576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4774    3.0701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1918    2.6576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9063    3.0701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1918    1.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3340    1.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7217    4.6752    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5287    4.8467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2823    5.1823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 14 21  1  1  0  0  0
  9 22  1  6  0  0  0
  9 23  1  0  0  0  0
  4 23  1  0  0  0  0
 23 24  2  0  0  0  0
  2 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0332769

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(CC[C@@]2([H])C3=CC(=O)OC3=CC[C@]12C)[C@H](C)CCCC(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O2/c1-13(2)6-5-7-14(3)16-8-9-17-15-12-19(21)22-18(15)10-11-20(16,17)4/h10,12-14,16-17H,5-9,11H2,1-4H3/t14-,16-,17+,20-/m1/s1

> <INCHI_KEY>
AUKVBHBQATUCDB-DFYYWFRZSA-N

> <FORMULA>
C20H30O2

> <MOLECULAR_WEIGHT>
302.458

> <EXACT_MASS>
302.224580206

$$$$

HEADER    PROTEIN                                 02-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-JAN-23         0                                  
HETATM    1  O   UNK     0      -5.244  12.236   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -4.099  11.205   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.593  11.525   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -1.823  10.192   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.317   9.871   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.159   8.407   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.871   7.262   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.593   6.786   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.378   7.583   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.148   6.249   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.117   5.104   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.710   5.731   0.000  0.00  0.00           C+0
HETATM   13  H   UNK     0      -0.791   4.193   0.000  0.00  0.00           H+0
HETATM   14  C   UNK     0       0.623   4.961   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.957   5.731   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.291   4.961   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.624   5.731   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.958   4.961   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.292   5.731   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.958   3.421   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.623   3.421   0.000  0.00  0.00           C+0
HETATM   22  H   UNK     0      -1.347   8.727   0.000  0.00  0.00           H+0
HETATM   23  C   UNK     0      -2.853   9.047   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.260   9.674   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   24                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   23                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   12                                             
CONECT    8    7                                                            
CONECT    9    7   10   22   23                                             
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7   13   14                                             
CONECT   13   12                                                            
CONECT   14   12   15   21                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   14                                                            
CONECT   22    9                                                            
CONECT   23    9    4   24                                                  
CONECT   24   23    2                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₀O₂

Average Mass

302.4580 Da

Monoisotopic Mass

302.22458 Da

IUPAC Name

(5aR,6R,8aR)-5a-methyl-6-[(2R)-6-methylheptan-2-yl]-2H,5H,5aH,6H,7H,8H,8aH-indeno[5,4-b]furan-2-one

Traditional Name

(5aR,6R,8aR)-5a-methyl-6-[(2R)-6-methylheptan-2-yl]-5H,6H,7H,8H,8aH-indeno[5,4-b]furan-2-one

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CC[C@@]2([H])C3=CC(=O)OC3=CC[C@]12C)[C@H](C)CCCC(C)C

InChI Identifier

InChI=1S/C20H30O2/c1-13(2)6-5-7-14(3)16-8-9-17-15-12-19(21)22-18(15)10-11-20(16,17)4/h10,12-14,16-17H,5-9,11H2,1-4H3/t14-,16-,17+,20-/m1/s1

InChI Key

AUKVBHBQATUCDB-DFYYWFRZSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	simmswli@163.com	School of Medicine Shanghai University	Song-Wei Li	2024-04-19	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	simmswli@163.com	School of Medicine Shanghai University	Song-Wei Li	2024-04-19	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	simmswli@163.com	School of Medicine Shanghai University	Song-Wei Li	2024-04-19	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	simmswli@163.com	School of Medicine Shanghai University	Song-Wei Li	2024-04-19	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)	simmswli@163.com	School of Medicine Shanghai University	Song-Wei Li	2024-04-19	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, CDCl3, experimental)	simmswli@163.com	School of Medicine Shanghai University	Song-Wei Li	2024-04-19	View Spectrum
1D_DEPT NMR	¹³C NMR Spectrum (1D, 126 MHz, CDCl3, experimental)	simmswli@163.com	School of Medicine Shanghai University	Song-Wei Li	2024-04-19	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600.17360102, CDCl₃, simulated)	simmswli@163.com	School of Medicine Shanghai University	Song-Wei Li	2024-04-19	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
officinalis		Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Farsesane sesquiterpenoid
Sesquiterpenoid
Fatty acid ester
Fatty acyl
2-furanone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Enol ester
Dihydrofuran
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
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	5.31	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	91.79 m³·mol⁻¹	ChemAxon
Polarizability	37.11 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 21-nor-4-ene-chaxine A (NP0332769)

MOL for NP0332769 (21-nor-4-ene-chaxine A)

3D MOL for NP0332769 (21-nor-4-ene-chaxine A)

3D SDF for NP0332769 (21-nor-4-ene-chaxine A)

3D-SDF for NP0332769 (21-nor-4-ene-chaxine A)

PDB for NP0332769 (21-nor-4-ene-chaxine A)

3D PDB for NP0332769 (21-nor-4-ene-chaxine A)

SMILES for NP0332769 (21-nor-4-ene-chaxine A)

INCHI for NP0332769 (21-nor-4-ene-chaxine A)

Structure for NP0332769 (21-nor-4-ene-chaxine A)

3D Structure for NP0332769 (21-nor-4-ene-chaxine A)