NP-MRD: Showing NP-Card for 3,4-Secolupa-4(23),20(29)-diene-3,28-dioic acid (NP0137684)

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Record Information

Version

2.0

Created at

2022-05-31 16:03:21 UTC

Updated at

2022-05-31 16:03:21 UTC

NP-MRD ID

NP0137684

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,4-Secolupa-4(23),20(29)-diene-3,28-dioic acid

Description

36138-41-7 Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Based on a literature review very few articles have been published on 36138-41-7.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652305312218032D          

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M  END

     RDKit          3D

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M  END


  Mrv1652305312218032D          

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    4.7050   -2.3711    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5330   -3.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9959   -3.9415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7101   -3.3182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5486   -0.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2761   -0.0204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8479    0.0260    0.0000 C   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  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 16 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
  8 27  1  0  0  0  0
 14 27  1  0  0  0  0
 27 28  1  6  0  0  0
 23 29  1  6  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 10 32  1  0  0  0  0
  2 32  1  0  0  0  0
  5 32  1  0  0  0  0
 32 33  1  1  0  0  0
  5 34  1  6  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
  2 37  1  1  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0137684

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]1(CC[C@@]2(CC[C@]3(C)[C@]([H])(CC[C@]4([H])[C@@](C)(CCC(O)=O)[C@@]([H])(CC[C@@]34C)C(C)=C)[C@@]12[H])C(O)=O)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C30H46O4/c1-18(2)20-10-15-30(26(33)34)17-16-28(6)22(25(20)30)8-9-23-27(5,13-12-24(31)32)21(19(3)4)11-14-29(23,28)7/h20-23,25H,1,3,8-17H2,2,4-7H3,(H,31,32)(H,33,34)/t20-,21-,22+,23+,25+,27-,28+,29+,30-/m0/s1

> <INCHI_KEY>
OCFWERYSZNWGQD-RGAAFHQASA-N

> <FORMULA>
C30H46O4

> <MOLECULAR_WEIGHT>
470.694

> <EXACT_MASS>
470.339609961

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
55.11311966319008

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,5S,6S,7R,10R,11R,12R,15S)-6-(2-carboxyethyl)-1,2,6-trimethyl-5,12-bis(prop-1-en-2-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-15-carboxylic acid

> <JCHEM_LOGP>
6.810910018666666

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.143317281907648

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.532382330862476

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
134.48099999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5S,6S,7R,10R,11R,12R,15S)-6-(2-carboxyethyl)-1,2,6-trimethyl-5,12-bis(prop-1-en-2-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-15-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 31-MAY-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   31-MAY-22         0                                  
HETATM    1  H   UNK     0       7.968  -1.649   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   11  H   UNK     0       8.313  -1.800   0.000  0.00  0.00           H+0
HETATM   12  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   15  H   UNK     0      13.330  -3.613   0.000  0.00  0.00           H+0
HETATM   16  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      15.185  -1.391   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.323  -0.719   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.311   0.464   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.780   1.909   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      14.767   3.091   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      12.263   2.173   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   24  H   UNK     0      15.839  -4.519   0.000  0.00  0.00           H+0
HETATM   25  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.243  -5.363   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      16.362  -3.071   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      17.355  -4.248   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      16.886  -1.622   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   33  H   UNK     0       8.783  -4.426   0.000  0.00  0.00           H+0
HETATM   34  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       7.459  -7.358   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       5.059  -6.194   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       6.624  -0.764   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       7.982  -0.038   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       5.316   0.049   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   32   37                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   32   34                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   27                                             
CONECT    9    8                                                            
CONECT   10    8   11   12   32                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   27                                             
CONECT   15   14                                                            
CONECT   16   14   17   18   23                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   16   24   25   29                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26    8   14   28                                             
CONECT   28   27                                                            
CONECT   29   23   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   10    2    5   33                                             
CONECT   33   32                                                            
CONECT   34    5   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37    2   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₆O₄

Average Mass

470.6940 Da

Monoisotopic Mass

470.33961 Da

IUPAC Name

(1R,2R,5S,6S,7R,10R,11R,12R,15S)-6-(2-carboxyethyl)-1,2,6-trimethyl-5,12-bis(prop-1-en-2-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-15-carboxylic acid

Traditional Name

(1R,2R,5S,6S,7R,10R,11R,12R,15S)-6-(2-carboxyethyl)-1,2,6-trimethyl-5,12-bis(prop-1-en-2-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-15-carboxylic acid

CAS Registry Number

36138-41-7

SMILES

[H][C@]1(CC[C@@]2(CC[C@]3(C)[C@]([H])(CC[C@]4([H])[C@@](C)(CCC(O)=O)[C@@]([H])(CC[C@@]34C)C(C)=C)[C@@]12[H])C(O)=O)C(C)=C

InChI Identifier

InChI=1S/C30H46O4/c1-18(2)20-10-15-30(26(33)34)17-16-28(6)22(25(20)30)8-9-23-27(5,13-12-24(31)32)21(19(3)4)11-14-29(23,28)7/h20-23,25H,1,3,8-17H2,2,4-7H3,(H,31,32)(H,33,34)/t20-,21-,22+,23+,25+,27-,28+,29+,30-/m0/s1

InChI Key

OCFWERYSZNWGQD-RGAAFHQASA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
3-carboxy steroid
Steroid acid
Androstane-skeleton
18-hydroxysteroid
18-oxosteroid
Hydroxysteroid
Oxosteroid
Steroid
Carbocyclic fatty acid
Dicarboxylic acid or derivatives
Fatty acyl
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organooxygen compound
Organic oxygen 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
logP	6.81	ChemAxon
pKa (Strongest Acidic)	4.53	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	6	ChemAxon
Refractivity	134.48 m³·mol⁻¹	ChemAxon
Polarizability	55.11 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

53608316

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

91302444

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 3,4-Secolupa-4(23),20(29)-diene-3,28-dioic acid (NP0137684)

MOL for NP0137684 (3,4-Secolupa-4(23),20(29)-diene-3,28-dioic acid)

3D MOL for NP0137684 (3,4-Secolupa-4(23),20(29)-diene-3,28-dioic acid)

3D SDF for NP0137684 (3,4-Secolupa-4(23),20(29)-diene-3,28-dioic acid)

3D-SDF for NP0137684 (3,4-Secolupa-4(23),20(29)-diene-3,28-dioic acid)

PDB for NP0137684 (3,4-Secolupa-4(23),20(29)-diene-3,28-dioic acid)

3D PDB for NP0137684 (3,4-Secolupa-4(23),20(29)-diene-3,28-dioic acid)

SMILES for NP0137684 (3,4-Secolupa-4(23),20(29)-diene-3,28-dioic acid)

INCHI for NP0137684 (3,4-Secolupa-4(23),20(29)-diene-3,28-dioic acid)

Structure for NP0137684 (3,4-Secolupa-4(23),20(29)-diene-3,28-dioic acid)

3D Structure for NP0137684 (3,4-Secolupa-4(23),20(29)-diene-3,28-dioic acid)