NP-MRD: Showing NP-Card for 3,4-Secocucurbita-4,24-diene-3,26,29-trioic acid (NP0139564)

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Record Information

Version

2.0

Created at

2022-06-29 20:00:15 UTC

Updated at

2022-06-29 20:00:15 UTC

NP-MRD ID

NP0139564

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,4-Secocucurbita-4,24-diene-3,26,29-trioic acid

Description

329975-47-5 Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. 3,4-Secocucurbita-4,24-diene-3,26,29-trioic acid is found in Russula rosea. 329975-47-5 Is a weakly acidic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241518192D          

 36 38  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004241518192D          

 36 38  0  0  0  0            999 V2000
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    2.2677   -3.3379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4431   -3.3122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0531   -2.5852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5476   -3.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  4  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 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
 19 20  2  0  0  0  0
 20 21  1  4  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 19 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 25 31  1  0  0  0  0
 16 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 11 35  1  0  0  0  0
 14 35  1  0  0  0  0
 35 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0139564

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CCC=C(C)C(O)=O)C1CCC2(C)C3CCC(C(CCC(O)=O)C3(C)CCC12C)=C(C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H46O6/c1-18(8-7-9-19(2)26(33)34)22-14-15-30(6)24-12-10-21(20(3)27(35)36)23(11-13-25(31)32)28(24,4)16-17-29(22,30)5/h9,18,22-24H,7-8,10-17H2,1-6H3,(H,31,32)(H,33,34)(H,35,36)

> <INCHI_KEY>
MLKGNOBMWJPGDM-UHFFFAOYSA-N

> <FORMULA>
C30H46O6

> <MOLECULAR_WEIGHT>
502.692

> <EXACT_MASS>
502.329439201

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
57.902988945105534

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-[6-(2-carboxyethyl)-7-(1-carboxyethylidene)-3a,5a,9b-trimethyl-dodecahydro-1H-cyclopenta[a]naphthalen-3-yl]-2-methylhept-2-enoic acid

> <ALOGPS_LOGP>
5.32

> <JCHEM_LOGP>
6.608874468666665

> <ALOGPS_LOGS>
-5.63

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
4.745555151407218

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.242376913189679

> <JCHEM_POLAR_SURFACE_AREA>
111.89999999999999

> <JCHEM_REFRACTIVITY>
140.0571

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.17e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-[6-(2-carboxyethyl)-7-(1-carboxyethylidene)-3a,5a,9b-trimethyl-octahydro-1H-cyclopenta[a]naphthalen-3-yl]-2-methylhept-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      -0.433  -6.968   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.706  -5.453   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.155  -4.931   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.331  -5.926   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.780  -5.404   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.053  -3.889   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.877  -2.894   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.502  -3.367   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -6.775  -1.852   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -7.678  -4.361   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.470  -4.459   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.357  -2.923   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.783  -2.341   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.777  -3.517   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.447  -2.130   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.316  -3.565   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.128  -2.256   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.667  -2.304   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.395  -3.661   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.934  -3.709   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.745  -2.400   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.662  -5.066   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      11.201  -5.114   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       8.851  -6.375   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.584  -4.970   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.312  -6.327   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.500  -7.636   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.228  -8.993   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       8.767  -9.041   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       6.417 -10.302   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       5.044  -4.922   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.772  -6.279   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.233  -6.231   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.694  -6.183   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.966  -4.826   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.022  -6.043   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    2   12   35                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   35                                             
CONECT   15   14                                                            
CONECT   16   14   17   31                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   25                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   19   26   31                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   25   16   32   33                                             
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   11   14   36                                             
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

View in JSmol

Synonyms

Value	Source
6-[6-(2-Carboxyethyl)-7-(1-carboxyethylidene)-3a,5a,9b-trimethyl-dodecahydro-1H-cyclopenta[a]naphthalen-3-yl]-2-methylhept-2-enoate	Generator

Chemical Formula

C₃₀H₄₆O₆

Average Mass

502.6920 Da

Monoisotopic Mass

502.32944 Da

IUPAC Name

6-[6-(2-carboxyethyl)-7-(1-carboxyethylidene)-3a,5a,9b-trimethyl-dodecahydro-1H-cyclopenta[a]naphthalen-3-yl]-2-methylhept-2-enoic acid

Traditional Name

6-[6-(2-carboxyethyl)-7-(1-carboxyethylidene)-3a,5a,9b-trimethyl-octahydro-1H-cyclopenta[a]naphthalen-3-yl]-2-methylhept-2-enoic acid

CAS Registry Number

Not Available

SMILES

CC(CCC=C(C)C(O)=O)C1CCC2(C)C3CCC(C(CCC(O)=O)C3(C)CCC12C)=C(C)C(O)=O

InChI Identifier

InChI=1S/C30H46O6/c1-18(8-7-9-19(2)26(33)34)22-14-15-30(6)24-12-10-21(20(3)27(35)36)23(11-13-25(31)32)28(24,4)16-17-29(22,30)5/h9,18,22-24H,7-8,10-17H2,1-6H3,(H,31,32)(H,33,34)(H,35,36)

InChI Key

MLKGNOBMWJPGDM-UHFFFAOYSA-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
Russula rosea	LOTUS Database	35616633

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
Tricarboxylic acid or derivatives
Carbocyclic fatty acid
Fatty acyl
Carboxylic acid
Carboxylic acid derivative
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	5.32	ALOGPS
logP	6.61	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	4.24	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	111.9 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	140.06 m³·mol⁻¹	ChemAxon
Polarizability	57.9 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	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

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

78384715

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 3,4-Secocucurbita-4,24-diene-3,26,29-trioic acid (NP0139564)

MOL for NP0139564 (3,4-Secocucurbita-4,24-diene-3,26,29-trioic acid)

3D MOL for NP0139564 (3,4-Secocucurbita-4,24-diene-3,26,29-trioic acid)

3D SDF for NP0139564 (3,4-Secocucurbita-4,24-diene-3,26,29-trioic acid)

3D-SDF for NP0139564 (3,4-Secocucurbita-4,24-diene-3,26,29-trioic acid)

PDB for NP0139564 (3,4-Secocucurbita-4,24-diene-3,26,29-trioic acid)

3D PDB for NP0139564 (3,4-Secocucurbita-4,24-diene-3,26,29-trioic acid)

SMILES for NP0139564 (3,4-Secocucurbita-4,24-diene-3,26,29-trioic acid)

INCHI for NP0139564 (3,4-Secocucurbita-4,24-diene-3,26,29-trioic acid)

Structure for NP0139564 (3,4-Secocucurbita-4,24-diene-3,26,29-trioic acid)

3D Structure for NP0139564 (3,4-Secocucurbita-4,24-diene-3,26,29-trioic acid)