NP-MRD: Showing NP-Card for Dehydropachymic acid (NP0071121)

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Record Information

Version

2.0

Created at

2022-04-28 16:31:34 UTC

Updated at

2022-04-28 16:31:34 UTC

NP-MRD ID

NP0071121

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Dehydropachymic acid

Description

Dehydropachymic acid belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Dehydropachymic acid is found in Poria cocos . Dehydropachymic acid was first documented in 2020 (PMID: 32489056). Based on a literature review a small amount of articles have been published on dehydropachymic acid (PMID: 34242946) (PMID: 33166752) (PMID: 34621284) (PMID: 31605966).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282218312D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304282218312D          

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   -0.9457    4.1254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2918    3.4110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7668    4.8399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5918    4.8399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3543    4.1254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6243    7.1940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8451    7.9825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3324    5.5705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7696    6.3129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4276    8.8138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6699    8.9749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2950    7.8847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9081    7.3327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6927    7.5876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7366    6.5257    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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
  4 14  1  1  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 18 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 16 29  1  6  0  0  0
 11 30  1  6  0  0  0
 10 31  1  1  0  0  0
  5 32  1  1  0  0  0
  3 33  1  0  0  0  0
  3 34  1  0  0  0  0
  2 35  1  1  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0071121

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(=C)CC[C@H]([C@H]1[C@H](O)C[C@@]2(C)C3=CC[C@H]4C(C)(C)[C@H](CC[C@]4(C)C3=CC[C@]12C)OC(C)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C33H50O5/c1-19(2)20(3)10-11-22(29(36)37)28-25(35)18-33(9)24-12-13-26-30(5,6)27(38-21(4)34)15-16-31(26,7)23(24)14-17-32(28,33)8/h12,14,19,22,25-28,35H,3,10-11,13,15-18H2,1-2,4-9H3,(H,36,37)/t22-,25-,26+,27+,28+,31-,32-,33+/m1/s1

> <INCHI_KEY>
RWIALJIVPUCERT-DRCQUEPLSA-N

> <FORMULA>
C33H50O5

> <MOLECULAR_WEIGHT>
526.758

> <EXACT_MASS>
526.36582471

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
88

> <JCHEM_AVERAGE_POLARIZABILITY>
62.22161289843285

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-[(2S,5S,7R,11R,13R,14R,15R)-5-(acetyloxy)-13-hydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(17),9-dien-14-yl]-6-methyl-5-methylideneheptanoic acid

> <ALOGPS_LOGP>
6.44

> <JCHEM_LOGP>
5.757789661333334

> <ALOGPS_LOGS>
-5.46

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.900497413856183

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.749322250484615

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8546782903250003

> <JCHEM_POLAR_SURFACE_AREA>
83.83000000000001

> <JCHEM_REFRACTIVITY>
151.57270000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.84e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-[(2S,5S,7R,11R,13R,14R,15R)-5-(acetyloxy)-13-hydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(17),9-dien-14-yl]-6-methyl-5-methylideneheptanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      13.699  12.736   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.019  14.242   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.875  15.273   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.410  14.797   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.090  13.290   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.235  12.260   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.626  12.815   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.305  11.308   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.841  10.832   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.696  11.863   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.016  13.369   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.481  13.845   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.801  15.351   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.266  15.827   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.683  14.139   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.538  13.109   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.165  11.702   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.395  10.368   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.855  10.368   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.085   9.034   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.545   9.034   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.225  10.368   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.225   7.701   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.765   7.701   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.545   6.367   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.165   9.034   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.705   9.034   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       4.395   7.701   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       3.032  13.429   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       7.177  14.901   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.220  10.398   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.770  11.784   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      13.865  16.452   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      12.450  16.753   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      15.484  14.718   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      16.628  13.688   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      18.093  14.164   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      16.308  12.181   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   35                                                  
CONECT    3    2    4   33   34                                             
CONECT    4    3    5   14                                                  
CONECT    5    4    6    7   32                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   17   31                                             
CONECT   11   10   12   15   30                                             
CONECT   12   11    7   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13    4                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17   29                                                  
CONECT   17   16   10   18                                                  
CONECT   18   17   19   26                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   18   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   16                                                            
CONECT   30   11                                                            
CONECT   31   10                                                            
CONECT   32    5                                                            
CONECT   33    3                                                            
CONECT   34    3                                                            
CONECT   35    2   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Value	Source
Dehydropachymate	Generator

Chemical Formula

C₃₃H₅₀O₅

Average Mass

526.7580 Da

Monoisotopic Mass

526.36582 Da

IUPAC Name

(2R)-2-[(2S,5S,7R,11R,13R,14R,15R)-5-(acetyloxy)-13-hydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(17),9-dien-14-yl]-6-methyl-5-methylideneheptanoic acid

Traditional Name

(2R)-2-[(2S,5S,7R,11R,13R,14R,15R)-5-(acetyloxy)-13-hydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(17),9-dien-14-yl]-6-methyl-5-methylideneheptanoic acid

CAS Registry Number

Not Available

SMILES

CC(C)C(=C)CC[C@H]([C@H]1[C@H](O)C[C@@]2(C)C3=CC[C@H]4C(C)(C)[C@H](CC[C@]4(C)C3=CC[C@]12C)OC(C)=O)C(O)=O

InChI Identifier

InChI=1S/C33H50O5/c1-19(2)20(3)10-11-22(29(36)37)28-25(35)18-33(9)24-12-13-26-30(5,6)27(38-21(4)34)15-16-31(26,7)23(24)14-17-32(28,33)8/h12,14,19,22,25-28,35H,3,10-11,13,15-18H2,1-2,4-9H3,(H,36,37)/t22-,25-,26+,27+,28+,31-,32-,33+/m1/s1

InChI Key

RWIALJIVPUCERT-DRCQUEPLSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Wolfiporia cocos	-	KNApSAcK

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
Ergostane-skeleton
Hydroxy bile acid, alcohol, or derivatives
Monohydroxy bile acid, alcohol, or derivatives
Cholane-skeleton
Bile acid, alcohol, or derivatives
Steroid ester
Steroid acid
16-hydroxysteroid
16-alpha-hydroxysteroid
14-alpha-methylsteroid
Hydroxysteroid
Steroid
Delta-7-steroid
Medium-chain fatty acid
Hydroxy fatty acid
Fatty acyl
Unsaturated fatty acid
Fatty acid
Dicarboxylic acid or derivatives
Cyclic alcohol
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organooxygen compound
Organic oxide
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	6.44	ALOGPS
logP	5.76	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	4.75	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	151.57 m³·mol⁻¹	ChemAxon
Polarizability	62.22 Å³	ChemAxon
Number of Rings	4	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

C00024045

Chemspider ID

57256982

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15226717

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhang J, Guo H, Yan F, Yuan S, Li S, Zhu P, Chen W, Peng C, Peng D: An UPLC - Q - Orbitrap method for pharmacokinetics and tissue distribution of four triterpenoids in rats after oral administration of Poria cocos ethanol extracts. J Pharm Biomed Anal. 2021 Sep 5;203:114237. doi: 10.1016/j.jpba.2021.114237. Epub 2021 Jul 2. [PubMed:34242946 ]
Sofrenic I, Andelkovic B, Todorovic N, Stanojkovic T, Vujisic L, Novakovic M, Milosavljevic S, Tesevic V: Cytotoxic triterpenoids and triterpene sugar esters from the medicinal mushroom Fomitopsis betulina. Phytochemistry. 2021 Jan;181:112580. doi: 10.1016/j.phytochem.2020.112580. Epub 2020 Nov 6. [PubMed:33166752 ]
Yang M, Zhao Y, Qin Y, Xu R, Yang Z, Peng H: Untargeted Metabolomics and Targeted Quantitative Analysis of Temporal and Spatial Variations in Specialized Metabolites Accumulation in Poria cocos (Schw.) Wolf (Fushen). Front Plant Sci. 2021 Sep 21;12:713490. doi: 10.3389/fpls.2021.713490. eCollection 2021. [PubMed:34621284 ]
Tian SS, Zhao XM, Liu Y, Ge XH, Feng WH, Chen LM, Yan LH, Wang ZM: [Studies on quality standards of Poria]. Zhongguo Zhong Yao Za Zhi. 2020 Apr;45(8):1734-1744. doi: 10.19540/j.cnki.cjcmm.20200202.203. [PubMed:32489056 ]
Wang Q, Zuo Z, Huang H, Wang Y: Comparison and quantitative analysis of wild and cultivated Macrohyporia cocos using attenuated total refection-Fourier transform infrared spectroscopy combined with ultra-fast liquid chromatography. Spectrochim Acta A Mol Biomol Spectrosc. 2020 Feb 5;226:117633. doi: 10.1016/j.saa.2019.117633. Epub 2019 Oct 8. [PubMed:31605966 ]

Showing NP-Card for Dehydropachymic acid (NP0071121)

MOL for NP0071121 (Dehydropachymic acid)

3D MOL for NP0071121 (Dehydropachymic acid)

3D SDF for NP0071121 (Dehydropachymic acid)

3D-SDF for NP0071121 (Dehydropachymic acid)

PDB for NP0071121 (Dehydropachymic acid)

3D PDB for NP0071121 (Dehydropachymic acid)

SMILES for NP0071121 (Dehydropachymic acid)

INCHI for NP0071121 (Dehydropachymic acid)

Structure for NP0071121 (Dehydropachymic acid)

3D Structure for NP0071121 (Dehydropachymic acid)