NP-MRD: Showing NP-Card for Pennogenin (NP0140882)

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Record Information

Version

2.0

Created at

2022-06-29 21:56:39 UTC

Updated at

2022-06-29 21:56:39 UTC

NP-MRD ID

NP0140882

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Pennogenin

Description

Pennogenin belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Thus, pennogenin is considered to be a sterol. Pennogenin is found in Dioscorea bulbifera, Dioscorea composita, Dracaena cambodiana, Paris polyphylla and Polygonatum stenophyllum. Pennogenin was first documented in 2020 (PMID: 32488904). Based on a literature review a significant number of articles have been published on pennogenin (PMID: 32378425) (PMID: 33460752) (PMID: 32315895) (PMID: 34279421) (PMID: 35610010) (PMID: 35335224).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652306292223562D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306292223562D          

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M  END
> <DATABASE_ID>
NP0140882

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1[C@@]2(CC[C@@H](C)CO2)O[C@H]2C[C@H]3[C@@H]4CC=C5C[C@@H](O)CC[C@]5(C)[C@H]4CC[C@]3(C)[C@@]12O

> <INCHI_IDENTIFIER>
InChI=1S/C27H42O4/c1-16-7-12-26(30-15-16)17(2)27(29)23(31-26)14-22-20-6-5-18-13-19(28)8-10-24(18,3)21(20)9-11-25(22,27)4/h5,16-17,19-23,28-29H,6-15H2,1-4H3/t16-,17-,19+,20-,21+,22+,23+,24+,25+,26-,27-/m1/s1

> <INCHI_KEY>
SYYHBUHOUUETMI-WJOMMTHPSA-N

> <FORMULA>
C27H42O4

> <MOLECULAR_WEIGHT>
430.629

> <EXACT_MASS>
430.308309832

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0      16.028   0.271   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.508   0.520   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.532  -0.671   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.013  -0.421   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.469   1.020   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.374  -0.063   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.006   0.644   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.255   2.164   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      10.778   2.396   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       7.887   2.871   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.792   1.788   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.483   0.412   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.637  -0.875   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.100  -0.785   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.408   0.591   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.255   1.878   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.563   3.254   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.026   3.343   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.180   2.057   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.871   0.681   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.025  -0.606   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.487  -0.517   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.204   0.859   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.642   2.146   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -1.741   0.949   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       3.562  -0.696   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.315  -0.884   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       9.238  -0.878   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      10.606  -1.585   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      12.445   2.211   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      13.965   1.961   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   31                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    9   30                                             
CONECT    6    5    7   29                                                  
CONECT    7    6    8   12   28                                             
CONECT    8    7    9   10                                                  
CONECT    9    8    5                                                       
CONECT   10    8   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11    7   13   27                                             
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   11   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   15   21   26                                             
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23   19                                                       
CONECT   25   23                                                            
CONECT   26   20                                                            
CONECT   27   12                                                            
CONECT   28    7                                                            
CONECT   29    6                                                            
CONECT   30    5   31                                                       
CONECT   31   30    2                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   72    0
END

View in JSmol

Synonyms

Value	Source
(25R)-Spirost-5-ene-3beta,17-diol	ChEBI
(25R)-Spirost-5-ene-3b,17-diol	Generator
(25R)-Spirost-5-ene-3β,17-diol	Generator

Chemical Formula

C₂₇H₄₂O₄

Average Mass

430.6290 Da

Monoisotopic Mass

430.30831 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@@H]1[C@@]2(CC[C@@H](C)CO2)O[C@H]2C[C@H]3[C@@H]4CC=C5C[C@@H](O)CC[C@]5(C)[C@H]4CC[C@]3(C)[C@@]12O

InChI Identifier

InChI=1S/C27H42O4/c1-16-7-12-26(30-15-16)17(2)27(29)23(31-26)14-22-20-6-5-18-13-19(28)8-10-24(18,3)21(20)9-11-25(22,27)4/h5,16-17,19-23,28-29H,6-15H2,1-4H3/t16-,17-,19+,20-,21+,22+,23+,24+,25+,26-,27-/m1/s1

InChI Key

SYYHBUHOUUETMI-WJOMMTHPSA-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
Dioscorea bulbifera	LOTUS Database	35616633
Dioscorea composita	LOTUS Database	35616633
Dracaena cambodiana	LOTUS Database	35616633
Paris polyphylla	LOTUS Database	35616633
Polygonatum stenophyllum	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
Spirostane skeleton
3-hydroxy-delta-5-steroid
3-hydroxysteroid
Hydroxysteroid
3-beta-hydroxy-delta-5-steroid
3-beta-hydroxysteroid
17-hydroxysteroid
Steroid
Delta-5-steroid
Ketal
Oxane
Monosaccharide
Tetrahydrofuran
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Acetal
Hydrocarbon derivative
Alcohol
Organooxygen compound
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

3beta-hydroxy steroid (CHEBI:71824 )
organic heterohexacyclic compound (CHEBI:71824 )
17alpha-hydroxy steroid (CHEBI:71824 )
oxaspiro compound (CHEBI:71824 )
sapogenin (CHEBI:71824 )
Spirostanols and derivatives (LMST01080041 )

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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00048504

Chemspider ID

23253323

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12314056

PDB ID

Not Available

ChEBI ID

71824

Good Scents ID

Not Available

References

General References

Singh PP, Bora PS, Suresh PS, Bhatt V, Sharma U: Qualitative and quantitative determination of steroidal saponins in Trillium govanianum by UHPLC-QTOF-MS/MS and UHPLC-ELSD. Phytochem Anal. 2020 Nov;31(6):861-873. doi: 10.1002/pca.2951. Epub 2020 Jun 3. [PubMed:32488904 ]
Singh PP, Suresh PS, Bora PS, Bhatt V, Sharma U: Govanoside B, a new steroidal saponin from rhizomes of Trillium govanianum. Nat Prod Res. 2020 May 6:1-9. doi: 10.1080/14786419.2020.1761360. [PubMed:32378425 ]
Gupta DD, Mishra S, Verma SS, Shekher A, Rai V, Awasthee N, Das TJ, Paul D, Das SK, Tag H, Chandra Gupta S, Hui PK: Evaluation of antioxidant, anti-inflammatory and anticancer activities of diosgenin enriched Paris polyphylla rhizome extract of Indian Himalayan landraces. J Ethnopharmacol. 2021 Apr 24;270:113842. doi: 10.1016/j.jep.2021.113842. Epub 2021 Jan 16. [PubMed:33460752 ]
Wang W, Wang W, Ge H, Li G, Shen P, Xu S, Yu B, Zhang J: Biocatalytic allylic hydroxylation of unsaturated triterpenes and steroids by Bacillus megaterium CGMCC 1.1741. Bioorg Chem. 2020 Jun;99:103826. doi: 10.1016/j.bioorg.2020.103826. Epub 2020 Apr 6. [PubMed:32315895 ]
Lin LT, Shi YC, Choong CY, Tai CJ: The Fruits of Paris polyphylla Inhibit Colorectal Cancer Cell Migration Induced by Fusobacterium nucleatum-Derived Extracellular Vesicles. Molecules. 2021 Jul 4;26(13). pii: molecules26134081. doi: 10.3390/molecules26134081. [PubMed:34279421 ]
Zhiyong LI, Na Z, Jianliang LI, Liang F, Yanyan J, Caifeng LI, Ling L, Xiulan H: Effcacy-oriented compatibility for Tianma (), Yanlingcao () and Bingpian () on improving cerebral ischemia stroke by network pharmacology and serum pharmacological methods. J Tradit Chin Med. 2022 Jun;42(3):408-416. doi: 10.19852/j.cnki.jtcm.2022.03.007. [PubMed:35610010 ]
Valencia-Mejia E, Leon-Wilchez YY, Monribot-Villanueva JL, Ramirez-Vazquez M, Bonilla-Landa I, Guerrero-Analco JA: Isolation and Identification of Pennogenin Tetraglycoside from Cestrum nocturnum (Solanaceae) and Its Antifungal Activity against Fusarium kuroshium, Causal Agent of Fusarium Dieback. Molecules. 2022 Mar 13;27(6):1860. doi: 10.3390/molecules27061860. [PubMed:35335224 ]
Hua X, Song W, Wang K, Yin X, Hao C, Duan B, Xu Z, Su T, Xue Z: Effective prediction of biosynthetic pathway genes involved in bioactive polyphyllins in Paris polyphylla. Commun Biol. 2022 Jan 13;5(1):50. doi: 10.1038/s42003-022-03000-z. [PubMed:35027659 ]
Li Z, Tang Y, Liu Z, Fan Q, Chen M, Lin Z, Zhao C, Lin R: Hepatotoxicity induced by PPⅥ and PPⅦ in zebrafish were related to the Cholesterol disorder. Phytomedicine. 2022 Jan;95:153787. doi: 10.1016/j.phymed.2021.153787. Epub 2021 Oct 11. [PubMed:34782205 ]
Bian Y, Zeng H, Tao H, Huang L, Du Z, Wang J, Ding K: A pectin-like polysaccharide from Polygala tenuifolia inhibits pancreatic cancer cell growth in vitro and in vivo by inducing apoptosis and suppressing autophagy. Int J Biol Macromol. 2020 Nov 1;162:107-115. doi: 10.1016/j.ijbiomac.2020.06.054. Epub 2020 Jun 9. [PubMed:32531363 ]

Showing NP-Card for Pennogenin (NP0140882)

MOL for NP0140882 (Pennogenin)

3D MOL for NP0140882 (Pennogenin)

3D SDF for NP0140882 (Pennogenin)

3D-SDF for NP0140882 (Pennogenin)

PDB for NP0140882 (Pennogenin)

3D PDB for NP0140882 (Pennogenin)

SMILES for NP0140882 (Pennogenin)

INCHI for NP0140882 (Pennogenin)

Structure for NP0140882 (Pennogenin)

3D Structure for NP0140882 (Pennogenin)