NP-MRD: Showing NP-Card for (4r)-4-[(3r,3ar,6s,7s,9s,9br)-6-(2-carboxyethyl)-9-hydroxy-3a,6,9b-trimethyl-5-oxo-7-(prop-1-en-2-yl)-1h,2h,3h,4h,7h,8h,9h-cyclopenta[a]naphthalen-3-yl]pentanoic acid (NP0267030)

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Record Information

Version

2.0

Created at

2022-09-08 11:40:36 UTC

Updated at

2022-09-08 11:40:36 UTC

NP-MRD ID

NP0267030

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4r)-4-[(3r,3ar,6s,7s,9s,9br)-6-(2-carboxyethyl)-9-hydroxy-3a,6,9b-trimethyl-5-oxo-7-(prop-1-en-2-yl)-1h,2h,3h,4h,7h,8h,9h-cyclopenta[a]naphthalen-3-yl]pentanoic acid

Description

Fornicatin B belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. (4r)-4-[(3r,3ar,6s,7s,9s,9br)-6-(2-carboxyethyl)-9-hydroxy-3a,6,9b-trimethyl-5-oxo-7-(prop-1-en-2-yl)-1h,2h,3h,4h,7h,8h,9h-cyclopenta[a]naphthalen-3-yl]pentanoic acid is found in Ganoderma fornicatum. Based on a literature review very few articles have been published on Fornicatin B.

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652309082213402D          

 33 35  0  0  1  0            999 V2000
    4.6296    7.2656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8226    7.4371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2706    6.8240    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4636    6.9955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1665    5.5978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END

  Mrv1652309082213402D          

 33 35  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0267030

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](CCC(O)=O)[C@H]1CC[C@@]2(C)C3=C(C(=O)C[C@]12C)[C@@](C)(CCC(O)=O)[C@@H](C[C@@H]3O)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C27H40O6/c1-15(2)18-13-19(28)24-23(25(18,4)11-10-22(32)33)20(29)14-27(6)17(9-12-26(24,27)5)16(3)7-8-21(30)31/h16-19,28H,1,7-14H2,2-6H3,(H,30,31)(H,32,33)/t16-,17-,18+,19+,25+,26+,27-/m1/s1

> <INCHI_KEY>
YXVYBSGFMJBSQD-YDTNFRICSA-N

> <FORMULA>
C27H40O6

> <MOLECULAR_WEIGHT>
460.611

> <EXACT_MASS>
460.282489008

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
51.90749847131523

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4R)-4-[(3R,3aR,6S,7S,9S,9bR)-6-(2-carboxyethyl)-9-hydroxy-3a,6,9b-trimethyl-5-oxo-7-(prop-1-en-2-yl)-1H,2H,3H,3aH,4H,5H,6H,7H,8H,9H,9bH-cyclopenta[a]naphthalen-3-yl]pentanoic acid

> <JCHEM_LOGP>
3.888930321333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.835684114931365

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.203063353001113

> <JCHEM_PKA_STRONGEST_BASIC>
-3.009277955506402

> <JCHEM_POLAR_SURFACE_AREA>
111.89999999999999

> <JCHEM_REFRACTIVITY>
125.67369999999991

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4R)-4-[(3R,3aR,6S,7S,9S,9bR)-6-(2-carboxyethyl)-9-hydroxy-3a,6,9b-trimethyl-5-oxo-7-(prop-1-en-2-yl)-1H,2H,3H,4H,7H,8H,9H-cyclopenta[a]naphthalen-3-yl]pentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       8.642  13.562   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.136  13.883   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.660  15.347   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.105  12.738   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.599  13.058   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.568  11.914   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.062  12.234   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.044  10.449   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.551  10.129   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.026   8.664   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       7.533   8.344   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.996   7.520   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.490   7.840   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.810   6.334   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.244   6.935   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.244   5.395   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.910   4.625   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.577   4.625   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.911   5.395   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.245   4.625   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.578   5.395   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       6.245   3.085   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.998   7.840   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.474   9.305   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.014   9.305   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.387  10.712   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.581  11.273   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.761  10.284   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.061  11.698   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.169  10.628   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.649  11.053   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      11.757   9.983   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      11.022  12.547   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   27                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   25                                                  
CONECT    9    8   10   27                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15   25                                             
CONECT   14   13                                                            
CONECT   15   13   16   23                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   15   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24    8   13   26                                             
CONECT   26   25                                                            
CONECT   27    9    4   28   29                                             
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₀O₆

Average Mass

460.6110 Da

Monoisotopic Mass

460.28249 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@H](CCC(O)=O)[C@H]1CC[C@@]2(C)C3=C(C(=O)C[C@]12C)[C@@](C)(CCC(O)=O)[C@@H](C[C@@H]3O)C(C)=C

InChI Identifier

InChI=1S/C27H40O6/c1-15(2)18-13-19(28)24-23(25(18,4)11-10-22(32)33)20(29)14-27(6)17(9-12-26(24,27)5)16(3)7-8-21(30)31/h16-19,28H,1,7-14H2,2-6H3,(H,30,31)(H,32,33)/t16-,17-,18+,19+,25+,26+,27-/m1/s1

InChI Key

YXVYBSGFMJBSQD-YDTNFRICSA-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
Ganoderma fornicatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Seco-podocarpan diterpenoid
Carbocyclic fatty acid
Branched fatty acid
Cyclohexenone
Methyl-branched fatty acid
Hydroxy fatty acid
Dicarboxylic acid or derivatives
Fatty acyl
Secondary alcohol
Ketone
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxide
Organic oxygen compound
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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

9388404

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11213342

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (4r)-4-[(3r,3ar,6s,7s,9s,9br)-6-(2-carboxyethyl)-9-hydroxy-3a,6,9b-trimethyl-5-oxo-7-(prop-1-en-2-yl)-1h,2h,3h,4h,7h,8h,9h-cyclopenta[a]naphthalen-3-yl]pentanoic acid (NP0267030)

MOL for NP0267030 ((4r)-4-[(3r,3ar,6s,7s,9s,9br)-6-(2-carboxyethyl)-9-hydroxy-3a,6,9b-trimethyl-5-oxo-7-(prop-1-en-2-yl)-1h,2h,3h,4h,7h,8h,9h-cyclopenta[a]naphthalen-3-yl]pentanoic acid)

3D MOL for NP0267030 ((4r)-4-[(3r,3ar,6s,7s,9s,9br)-6-(2-carboxyethyl)-9-hydroxy-3a,6,9b-trimethyl-5-oxo-7-(prop-1-en-2-yl)-1h,2h,3h,4h,7h,8h,9h-cyclopenta[a]naphthalen-3-yl]pentanoic acid)

3D SDF for NP0267030 ((4r)-4-[(3r,3ar,6s,7s,9s,9br)-6-(2-carboxyethyl)-9-hydroxy-3a,6,9b-trimethyl-5-oxo-7-(prop-1-en-2-yl)-1h,2h,3h,4h,7h,8h,9h-cyclopenta[a]naphthalen-3-yl]pentanoic acid)

3D-SDF for NP0267030 ((4r)-4-[(3r,3ar,6s,7s,9s,9br)-6-(2-carboxyethyl)-9-hydroxy-3a,6,9b-trimethyl-5-oxo-7-(prop-1-en-2-yl)-1h,2h,3h,4h,7h,8h,9h-cyclopenta[a]naphthalen-3-yl]pentanoic acid)

PDB for NP0267030 ((4r)-4-[(3r,3ar,6s,7s,9s,9br)-6-(2-carboxyethyl)-9-hydroxy-3a,6,9b-trimethyl-5-oxo-7-(prop-1-en-2-yl)-1h,2h,3h,4h,7h,8h,9h-cyclopenta[a]naphthalen-3-yl]pentanoic acid)

3D PDB for NP0267030 ((4r)-4-[(3r,3ar,6s,7s,9s,9br)-6-(2-carboxyethyl)-9-hydroxy-3a,6,9b-trimethyl-5-oxo-7-(prop-1-en-2-yl)-1h,2h,3h,4h,7h,8h,9h-cyclopenta[a]naphthalen-3-yl]pentanoic acid)

SMILES for NP0267030 ((4r)-4-[(3r,3ar,6s,7s,9s,9br)-6-(2-carboxyethyl)-9-hydroxy-3a,6,9b-trimethyl-5-oxo-7-(prop-1-en-2-yl)-1h,2h,3h,4h,7h,8h,9h-cyclopenta[a]naphthalen-3-yl]pentanoic acid)

INCHI for NP0267030 ((4r)-4-[(3r,3ar,6s,7s,9s,9br)-6-(2-carboxyethyl)-9-hydroxy-3a,6,9b-trimethyl-5-oxo-7-(prop-1-en-2-yl)-1h,2h,3h,4h,7h,8h,9h-cyclopenta[a]naphthalen-3-yl]pentanoic acid)

Structure for NP0267030 ((4r)-4-[(3r,3ar,6s,7s,9s,9br)-6-(2-carboxyethyl)-9-hydroxy-3a,6,9b-trimethyl-5-oxo-7-(prop-1-en-2-yl)-1h,2h,3h,4h,7h,8h,9h-cyclopenta[a]naphthalen-3-yl]pentanoic acid)

3D Structure for NP0267030 ((4r)-4-[(3r,3ar,6s,7s,9s,9br)-6-(2-carboxyethyl)-9-hydroxy-3a,6,9b-trimethyl-5-oxo-7-(prop-1-en-2-yl)-1h,2h,3h,4h,7h,8h,9h-cyclopenta[a]naphthalen-3-yl]pentanoic acid)