NP-MRD: Showing NP-Card for Poricoic acid F (NP0066503)

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Record Information

Version

1.0

Created at

2022-04-28 10:45:42 UTC

Updated at

2022-04-28 10:45:42 UTC

NP-MRD ID

NP0066503

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Poricoic acid F

Description

Poricoic acid A, also known as poricoate a, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Poricoic acid F is found in Poria cocos WOLF . It was first documented in 2021 (PMID: 34976099). Based on a literature review a significant number of articles have been published on poricoic acid A (PMID: 34945705) (PMID: 34621284) (PMID: 35397422) (PMID: 34669780).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282212452D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304282212452D          

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  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  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
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 11 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
  9 22  1  6  0  0  0
  7 23  1  6  0  0  0
  6 24  1  1  0  0  0
  3 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
  1 27  1  0  0  0  0
 26 28  1  1  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 25 31  1  1  0  0  0
 25 32  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0066503

> <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](C(C)=C)[C@](C)(CCC(O)=O)C3=CC[C@]12C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C31H46O5/c1-18(2)20(5)9-10-21(28(35)36)27-25(32)17-31(8)24-12-11-22(19(3)4)29(6,15-14-26(33)34)23(24)13-16-30(27,31)7/h12-13,18,21-22,25,27,32H,3,5,9-11,14-17H2,1-2,4,6-8H3,(H,33,34)(H,35,36)/t21-,22+,25-,27+,29+,30-,31+/m1/s1

> <INCHI_KEY>
KVAQLXUMUVEKGR-SMFZDKLCSA-N

> <FORMULA>
C31H46O5

> <MOLECULAR_WEIGHT>
498.704

> <EXACT_MASS>
498.334524581

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
57.66237307205854

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
5.32

> <JCHEM_LOGP>
5.487835189666667

> <ALOGPS_LOGS>
-5.13

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.060179307652644

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.457536116366582

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8546782916907754

> <JCHEM_POLAR_SURFACE_AREA>
94.83

> <JCHEM_REFRACTIVITY>
144.2767

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.66e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-[(2R,3R,3aR,6S,7S,9bR)-6-(2-carboxyethyl)-2-hydroxy-3a,6,9b-trimethyl-7-(prop-1-en-2-yl)-1H,2H,3H,4H,7H,8H-cyclopenta[a]naphthalen-3-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      16.353  11.902   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      16.033  10.396   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      17.177   9.366   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      16.857   7.859   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.392   7.383   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.248   8.414   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.568   9.920   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.235  10.690   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.090   9.660   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.716   8.253   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.946   6.919   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.406   6.919   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.636   5.586   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.096   5.586   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.326   6.919   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.326   4.252   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.786   4.252   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.096   2.918   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.716   5.586   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      14.256   5.586   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      11.946   4.252   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      10.584   9.980   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      14.729  11.452   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.772   6.949   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      18.642   9.841   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      18.962  11.348   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      17.818  12.378   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      20.427  11.824   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      20.747  13.330   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      21.571  10.793   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      19.169   8.394   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      20.136   9.469   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      20.561   7.989   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      19.491   6.881   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      19.915   5.400   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      17.997   7.253   0.000  0.00  0.00           O+0
CONECT    1    2   27                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4   25                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   10   24                                             
CONECT    7    6    2    8   23                                             
CONECT    8    7    9                                                       
CONECT    9    8   10   22                                                  
CONECT   10    9    6   11                                                  
CONECT   11   10   12   19                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   11   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22    9                                                            
CONECT   23    7                                                            
CONECT   24    6                                                            
CONECT   25    3   26   31   32                                             
CONECT   26   25   27   28                                                  
CONECT   27   26    1                                                       
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   25                                                            
CONECT   32   25   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

View in JSmol

Synonyms

Value	Source
Poricoate a	Generator

Chemical Formula

C₃₁H₄₆O₅

Average Mass

498.7040 Da

Monoisotopic Mass

498.33452 Da

IUPAC Name

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

Traditional Name

(2R)-2-[(2R,3R,3aR,6S,7S,9bR)-6-(2-carboxyethyl)-2-hydroxy-3a,6,9b-trimethyl-7-(prop-1-en-2-yl)-1H,2H,3H,4H,7H,8H-cyclopenta[a]naphthalen-3-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](C(C)=C)[C@](C)(CCC(O)=O)C3=CC[C@]12C)C(O)=O

InChI Identifier

InChI=1S/C31H46O5/c1-18(2)20(5)9-10-21(28(35)36)27-25(32)17-31(8)24-12-11-22(19(3)4)29(6,15-14-26(33)34)23(24)13-16-30(27,31)7/h12-13,18,21-22,25,27,32H,3,5,9-11,14-17H2,1-2,4,6-8H3,(H,33,34)(H,35,36)/t21-,22+,25-,27+,29+,30-,31+/m1/s1

InChI Key

KVAQLXUMUVEKGR-SMFZDKLCSA-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
Poria cocos WOLF	-	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
Medium-chain fatty acid
Branched fatty acid
Methyl-branched fatty acid
Hydroxy fatty acid
Dicarboxylic acid or derivatives
Fatty acyl
Fatty acid
Unsaturated fatty acid
Cyclic alcohol
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

secondary alcohol (CHEBI:68353 )
dicarboxylic acid (CHEBI:68353 )
tricyclic triterpenoid (CHEBI:68353 )

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	5.49	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	4.46	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	144.28 m³·mol⁻¹	ChemAxon
Polarizability	57.66 Å³	ChemAxon
Number of Rings	3	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

C00040060

Chemspider ID

4581934

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5471851

PDB ID

Not Available

ChEBI ID

68353

Good Scents ID

Not Available

References

General References

Zhang L, Yin M, Feng X, Ibrahim SA, Liu Y, Huang W: Anti-Inflammatory Activity of Four Triterpenoids Isolated from Poriae Cutis. Foods. 2021 Dec 20;10(12). pii: foods10123155. doi: 10.3390/foods10123155. [PubMed:34945705 ]
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 ]
Chen L, Fang W, Liu J, Qi X, Zhao L, Wang Y, Liu Y, Kong D, Sun X, Li X, Sha Q, Sun G: Poricoic acid A (PAA) inhibits T-cell acute lymphoblastic leukemia through inducing autophagic cell death and ferroptosis. Biochem Biophys Res Commun. 2022 Jun 11;608:108-115. doi: 10.1016/j.bbrc.2022.03.105. Epub 2022 Mar 23. [PubMed:35397422 ]
Li B, Fan S, Hu J, Ma Y, Feng Y, Wang F, Wang X, Niu L: Phytochemical Analysis Using UPLC-MS/MS Combined with Network Pharmacology Methods to Explore the Biomarkers for the Quality Control of Lingguizhugan Decoction. Evid Based Complement Alternat Med. 2021 Dec 22;2021:7849032. doi: 10.1155/2021/7849032. eCollection 2021. [PubMed:34976099 ]
Ma R, Zhang Z, Xu J, Liang X, Zhao Q: Poricoic acid A induces apoptosis and autophagy in ovarian cancer via modulating the mTOR/p70s6k signaling axis. Braz J Med Biol Res. 2021 Oct 18;54(12):e11183. doi: 10.1590/1414-431X2021e11183. eCollection 2021. [PubMed:34669780 ]

Showing NP-Card for Poricoic acid F (NP0066503)

MOL for NP0066503 (Poricoic acid F)

3D MOL for NP0066503 (Poricoic acid F)

3D SDF for NP0066503 (Poricoic acid F)

3D-SDF for NP0066503 (Poricoic acid F)

PDB for NP0066503 (Poricoic acid F)

3D PDB for NP0066503 (Poricoic acid F)

SMILES for NP0066503 (Poricoic acid F)

INCHI for NP0066503 (Poricoic acid F)

Structure for NP0066503 (Poricoic acid F)

3D Structure for NP0066503 (Poricoic acid F)