NP-MRD: Showing NP-Card for 13,14,15,16-tertranor-3-clerodene-12,18-dioic acid (NP0331424)

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Record Information

Version

2.0

Created at

2022-12-25 08:06:29 UTC

Updated at

2024-09-03 04:15:43 UTC

NP-MRD ID

NP0331424

Natural Product DOI

https://doi.org/10.57994/0373

Secondary Accession Numbers

None

Natural Product Identification

Common Name

13,14,15,16-tertranor-3-clerodene-12,18-dioic acid

Description

(4AR,5S,6R,8aR)-5-(carboxymethyl)-5,6,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylic acid belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. Based on a literature review very few articles have been published on (4aR,5S,6R,8aR)-5-(carboxymethyl)-5,6,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 44 45  0  0  0  0  0  0  0  0999 V2000
   -2.5290   -1.7720   -1.3769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1631   -1.1858   -1.1446 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3231   -2.2025   -0.4447 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8933   -1.7527    0.2435 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0648   -0.3216    0.5969 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8790   -0.0821    2.0742 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4837    0.0853    0.3206 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5448   -0.8281    0.8091 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7629   -0.5706    0.6268 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2376   -1.9792    1.4729 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8326    1.1802   -0.3103 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9136    2.1953   -0.8549 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5275    1.9668   -0.2030 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2060    0.5285   -0.2798 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2367    0.1147   -0.2930 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8528   -0.2825    0.9854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0618    1.0739   -1.0529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3605    2.3627   -0.4522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8797    3.2434   -1.1998 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1461    2.7562    0.8638 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7755   -1.6837   -2.4653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5298   -2.8846   -1.1968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3461   -1.3177   -0.8285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6736   -0.9231   -2.0999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9333   -2.8652    0.2274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0156   -2.9344   -1.2635 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9873   -2.3599    1.1860 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7935   -2.0505   -0.3810 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2478   -0.8270    2.5849 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8929   -0.2517    2.5512 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6249    0.9467    2.3120 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8312   -2.7790    1.5006 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9180    1.3257   -0.4280 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2483    3.2290   -0.7272 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7841    1.9484   -1.9480 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5839    2.4217    0.7828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1092    2.6133   -0.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5653    0.2346   -1.3299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6444    0.3895    1.8410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9773   -0.2314    0.8232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6928   -1.3318    1.2979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5681    1.3046   -2.0495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0500    0.6354   -1.3906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9546    2.8610    1.4725 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  1
  5 14  1  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11  7  2  0
  7  8  1  0
  8 10  1  0
  8  9  2  0
 14 15  1  0
 15 16  1  1
 15 17  1  0
 17 18  1  0
 18 20  1  0
 18 19  2  0
 15  2  1  0
  7  5  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  6
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  6 29  1  0
  6 30  1  0
  6 31  1  0
 14 38  1  6
 13 36  1  0
 13 37  1  0
 12 34  1  0
 12 35  1  0
 11 33  1  0
 10 32  1  0
 16 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
 17 43  1  0
 20 44  1  0
M  END


  Mrv1652309032220032D          

 20 21  0  0  1  0            999 V2000
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8163   -2.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0416   -2.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4788   -3.0781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3033   -3.0493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0915   -3.8065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  7 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  6  0  0  0
  5 14  1  0  0  0  0
 14 15  1  0  0  0  0
  2 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331424

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CC[C@]2(C)[C@H](CCC=C2C(O)=O)[C@@]1(C)CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H24O4/c1-10-7-8-15(2)11(14(19)20)5-4-6-12(15)16(10,3)9-13(17)18/h5,10,12H,4,6-9H2,1-3H3,(H,17,18)(H,19,20)/t10-,12+,15+,16+/m1/s1

> <INCHI_KEY>
HAIVIKUHMDNVLL-LPGAHRBXSA-N

> <FORMULA>
C16H24O4

> <MOLECULAR_WEIGHT>
280.364

> <EXACT_MASS>
280.167459253

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
30.329781108027635

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4aR,5S,6R,8aR)-5-(carboxymethyl)-5,6,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylic acid

> <JCHEM_LOGP>
3.038453156666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.047135028104905

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.352535714745661

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
75.53259999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4aR,5S,6R,8aR)-5-(carboxymethyl)-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.390  -4.440   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.944  -4.440   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.760  -5.746   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.300  -5.692   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.037  -7.105   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7   14                                             
CONECT    6    5                                                            
CONECT    7    5    8   11                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    7   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    5   15                                                  
CONECT   15   14    2   16   17                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Value	Source
(4AR,5S,6R,8ar)-5-(carboxymethyl)-5,6,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate	Generator

Chemical Formula

C₁₆H₂₄O₄

Average Mass

280.3640 Da

Monoisotopic Mass

280.16746 Da

IUPAC Name

(4aR,5S,6R,8aR)-5-(carboxymethyl)-5,6,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylic acid

Traditional Name

(4aR,5S,6R,8aR)-5-(carboxymethyl)-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

C[C@@H]1CC[C@]2(C)[C@H](CCC=C2C(O)=O)[C@@]1(C)CC(O)=O

InChI Identifier

InChI=1S/C16H24O4/c1-10-7-8-15(2)11(14(19)20)5-4-6-12(15)16(10,3)9-13(17)18/h5,10,12H,4,6-9H2,1-3H3,(H,17,18)(H,19,20)/t10-,12+,15+,16+/m1/s1

InChI Key

HAIVIKUHMDNVLL-LPGAHRBXSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, CD3OD, experimental)	wuaizhi@gzucm.edu.cn	Not Available	Not Available	2022-12-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD3OD, experimental)	wuaizhi@gzucm.edu.cn	Not Available	Not Available	2022-12-25	View Spectrum

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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Dicarboxylic acids and derivatives

Direct Parent

Dicarboxylic acids and derivatives

Alternative Parents

Substituents

Dicarboxylic acid or derivatives
Carboxylic acid
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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
logP	3.04	ChemAxon
pKa (Strongest Acidic)	4.35	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	75.53 m³·mol⁻¹	ChemAxon
Polarizability	30.33 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	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

51693746

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

DOI: 10.1016/j.fitote.2022.105394

Showing NP-Card for 13,14,15,16-tertranor-3-clerodene-12,18-dioic acid (NP0331424)

MOL for NP0331424 (13,14,15,16-tertranor-3-clerodene-12,18-dioic acid)

3D MOL for NP0331424 (13,14,15,16-tertranor-3-clerodene-12,18-dioic acid)

3D SDF for NP0331424 (13,14,15,16-tertranor-3-clerodene-12,18-dioic acid)

3D-SDF for NP0331424 (13,14,15,16-tertranor-3-clerodene-12,18-dioic acid)

PDB for NP0331424 (13,14,15,16-tertranor-3-clerodene-12,18-dioic acid)

3D PDB for NP0331424 (13,14,15,16-tertranor-3-clerodene-12,18-dioic acid)

SMILES for NP0331424 (13,14,15,16-tertranor-3-clerodene-12,18-dioic acid)

INCHI for NP0331424 (13,14,15,16-tertranor-3-clerodene-12,18-dioic acid)

Structure for NP0331424 (13,14,15,16-tertranor-3-clerodene-12,18-dioic acid)

3D Structure for NP0331424 (13,14,15,16-tertranor-3-clerodene-12,18-dioic acid)