NP-MRD: Showing NP-Card for (2z,6r)-6-[(5ar,7as,7bs,10r,11as,12bs)-5,5,7b,12b-tetramethyl-11-methylidene-3-oxo-1h,2h,5ah,6h,7h,7ah,8h,9h,10h,11ah-fluoreno[2,1-c]oxepin-10-yl]-2-methylhept-2-enoic acid (NP0250659)

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Record Information

Version

2.0

Created at

2022-09-07 13:33:44 UTC

Updated at

2022-09-07 13:33:45 UTC

NP-MRD ID

NP0250659

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2z,6r)-6-[(5ar,7as,7bs,10r,11as,12bs)-5,5,7b,12b-tetramethyl-11-methylidene-3-oxo-1h,2h,5ah,6h,7h,7ah,8h,9h,10h,11ah-fluoreno[2,1-c]oxepin-10-yl]-2-methylhept-2-enoic acid

Description

Kadcoccinic acid C, also known as kadcoccinate C, belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. (2z,6r)-6-[(5ar,7as,7bs,10r,11as,12bs)-5,5,7b,12b-tetramethyl-11-methylidene-3-oxo-1h,2h,5ah,6h,7h,7ah,8h,9h,10h,11ah-fluoreno[2,1-c]oxepin-10-yl]-2-methylhept-2-enoic acid is found in Kadsura coccinea. Based on a literature review very few articles have been published on Kadcoccinic acid C.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072215332D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309072215332D          

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  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  3 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 20  1  1  0  0  0
 21 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  2  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
 21 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 18 32  1  6  0  0  0
 32 33  2  0  0  0  0
 34 33  1  1  0  0  0
  2 34  1  0  0  0  0
 16 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0250659

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](CC\C=C(\C)C(O)=O)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@@H]4[C@](C)(CCC(=O)OC4(C)C)C3=C[C@H]2C1=C

> <INCHI_IDENTIFIER>
InChI=1S/C30H44O4/c1-18(9-8-10-19(2)27(32)33)21-13-15-29(6)22-11-12-25-28(4,5)34-26(31)14-16-30(25,7)24(22)17-23(29)20(21)3/h10,17-18,21-23,25H,3,8-9,11-16H2,1-2,4-7H3,(H,32,33)/b19-10-/t18-,21-,22-,23+,25+,29+,30-/m1/s1

> <INCHI_KEY>
ZMWGNOQGBYBGGS-HGIOFNIASA-N

> <FORMULA>
C30H44O4

> <MOLECULAR_WEIGHT>
468.678

> <EXACT_MASS>
468.323959897

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
55.43014030324173

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2Z,6R)-2-methyl-6-[(2S,8R,11S,12S,15R,17S)-2,7,7,12-tetramethyl-16-methylidene-5-oxo-6-oxatetracyclo[9.7.0.0^{2,8}.0^{12,17}]octadec-1(18)-en-15-yl]hept-2-enoic acid

> <JCHEM_LOGP>
6.3714760293333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.938206079802285

> <JCHEM_PKA_STRONGEST_BASIC>
-7.050084288039019

> <JCHEM_POLAR_SURFACE_AREA>
63.6

> <JCHEM_REFRACTIVITY>
136.7244

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2Z,6R)-2-methyl-6-[(2S,8R,11S,12S,15R,17S)-2,7,7,12-tetramethyl-16-methylidene-5-oxo-6-oxatetracyclo[9.7.0.0^{2,8}.0^{12,17}]octadec-1(18)-en-15-yl]hept-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       5.880  -7.788   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.927  -6.249   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.618  -5.439   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.261  -6.168   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.214  -7.707   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.952  -5.357   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.595  -6.086   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.714  -5.276   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.071  -6.005   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.381  -5.194   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.118  -7.544   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -3.475  -8.273   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -0.809  -8.354   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.665  -3.899   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.021  -3.170   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.331  -3.981   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.539  -2.455   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.809  -3.550   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.478  -2.163   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.014  -2.049   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.881  -3.322   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.382  -2.980   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.715  -1.592   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.587  -2.020   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      14.586  -3.941   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      14.585  -5.481   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      15.972  -6.150   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      13.380  -6.440   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.879  -6.096   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.212  -4.709   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.441  -6.042   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.676  -4.823   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.733  -6.040   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.284  -5.520   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   34                                                  
CONECT    3    2    4   14                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    3   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   34                                             
CONECT   17   16                                                            
CONECT   18   16   19   32                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   30                                                  
CONECT   22   21   23   24   25                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   22   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   21   31   32                                             
CONECT   31   30                                                            
CONECT   32   30   18   33                                                  
CONECT   33   32   34                                                       
CONECT   34   33    2   16                                                  
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
Kadcoccinate C	Generator

Chemical Formula

C₃₀H₄₄O₄

Average Mass

468.6780 Da

Monoisotopic Mass

468.32396 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@H](CC\C=C(\C)C(O)=O)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@@H]4[C@](C)(CCC(=O)OC4(C)C)C3=C[C@H]2C1=C

InChI Identifier

InChI=1S/C30H44O4/c1-18(9-8-10-19(2)27(32)33)21-13-15-29(6)22-11-12-25-28(4,5)34-26(31)14-16-30(25,7)24(22)17-23(29)20(21)3/h10,17-18,21-23,25H,3,8-9,11-16H2,1-2,4-7H3,(H,32,33)/b19-10-/t18-,21-,22-,23+,25+,29+,30-/m1/s1

InChI Key

ZMWGNOQGBYBGGS-HGIOFNIASA-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
Kadsura coccinea	LOTUS Database	35616633

Chemical Taxonomy

Description

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
Bisabolane sesquiterpenoid
Sesquiterpenoid
Caprolactone
Medium-chain fatty acid
Branched fatty acid
Heterocyclic fatty acid
Methyl-branched fatty acid
Oxepane
Dicarboxylic acid or derivatives
Fatty acyl
Fatty acid
Unsaturated fatty acid
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Carbonyl group
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

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

59000158

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

122181858

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2z,6r)-6-[(5ar,7as,7bs,10r,11as,12bs)-5,5,7b,12b-tetramethyl-11-methylidene-3-oxo-1h,2h,5ah,6h,7h,7ah,8h,9h,10h,11ah-fluoreno[2,1-c]oxepin-10-yl]-2-methylhept-2-enoic acid (NP0250659)

MOL for NP0250659 ((2z,6r)-6-[(5ar,7as,7bs,10r,11as,12bs)-5,5,7b,12b-tetramethyl-11-methylidene-3-oxo-1h,2h,5ah,6h,7h,7ah,8h,9h,10h,11ah-fluoreno[2,1-c]oxepin-10-yl]-2-methylhept-2-enoic acid)

3D MOL for NP0250659 ((2z,6r)-6-[(5ar,7as,7bs,10r,11as,12bs)-5,5,7b,12b-tetramethyl-11-methylidene-3-oxo-1h,2h,5ah,6h,7h,7ah,8h,9h,10h,11ah-fluoreno[2,1-c]oxepin-10-yl]-2-methylhept-2-enoic acid)

3D SDF for NP0250659 ((2z,6r)-6-[(5ar,7as,7bs,10r,11as,12bs)-5,5,7b,12b-tetramethyl-11-methylidene-3-oxo-1h,2h,5ah,6h,7h,7ah,8h,9h,10h,11ah-fluoreno[2,1-c]oxepin-10-yl]-2-methylhept-2-enoic acid)

3D-SDF for NP0250659 ((2z,6r)-6-[(5ar,7as,7bs,10r,11as,12bs)-5,5,7b,12b-tetramethyl-11-methylidene-3-oxo-1h,2h,5ah,6h,7h,7ah,8h,9h,10h,11ah-fluoreno[2,1-c]oxepin-10-yl]-2-methylhept-2-enoic acid)

PDB for NP0250659 ((2z,6r)-6-[(5ar,7as,7bs,10r,11as,12bs)-5,5,7b,12b-tetramethyl-11-methylidene-3-oxo-1h,2h,5ah,6h,7h,7ah,8h,9h,10h,11ah-fluoreno[2,1-c]oxepin-10-yl]-2-methylhept-2-enoic acid)

3D PDB for NP0250659 ((2z,6r)-6-[(5ar,7as,7bs,10r,11as,12bs)-5,5,7b,12b-tetramethyl-11-methylidene-3-oxo-1h,2h,5ah,6h,7h,7ah,8h,9h,10h,11ah-fluoreno[2,1-c]oxepin-10-yl]-2-methylhept-2-enoic acid)

SMILES for NP0250659 ((2z,6r)-6-[(5ar,7as,7bs,10r,11as,12bs)-5,5,7b,12b-tetramethyl-11-methylidene-3-oxo-1h,2h,5ah,6h,7h,7ah,8h,9h,10h,11ah-fluoreno[2,1-c]oxepin-10-yl]-2-methylhept-2-enoic acid)

INCHI for NP0250659 ((2z,6r)-6-[(5ar,7as,7bs,10r,11as,12bs)-5,5,7b,12b-tetramethyl-11-methylidene-3-oxo-1h,2h,5ah,6h,7h,7ah,8h,9h,10h,11ah-fluoreno[2,1-c]oxepin-10-yl]-2-methylhept-2-enoic acid)

Structure for NP0250659 ((2z,6r)-6-[(5ar,7as,7bs,10r,11as,12bs)-5,5,7b,12b-tetramethyl-11-methylidene-3-oxo-1h,2h,5ah,6h,7h,7ah,8h,9h,10h,11ah-fluoreno[2,1-c]oxepin-10-yl]-2-methylhept-2-enoic acid)

3D Structure for NP0250659 ((2z,6r)-6-[(5ar,7as,7bs,10r,11as,12bs)-5,5,7b,12b-tetramethyl-11-methylidene-3-oxo-1h,2h,5ah,6h,7h,7ah,8h,9h,10h,11ah-fluoreno[2,1-c]oxepin-10-yl]-2-methylhept-2-enoic acid)