NP-MRD: Showing NP-Card for Cucurbitadienol (NP0140720)

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Record Information

Version

2.0

Created at

2022-06-29 21:48:34 UTC

Updated at

2022-06-29 21:48:34 UTC

NP-MRD ID

NP0140720

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cucurbitadienol

Description

Cucurbitadienol belongs to the class of organic compounds known as cucurbitacins. These are polycyclic compounds containing the tetracyclic cucurbitane nucleus skeleton, 19-(10->9b)-abeo-10alanost-5-ene (also known as 9b-methyl-19-nor lanosta-5-ene), with a variety of oxygenation functionalities at different positions. Cucurbitadienol is found in Toxicodendron sylvestre. Cucurbitadienol was first documented in 2021 (PMID: 34228189). Based on a literature review a small amount of articles have been published on cucurbitadienol (PMID: 35305722) (PMID: 35049440) (PMID: 34264303).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652306292223482D          

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 25 27  1  0  0  0  0
 24 28  1  6  0  0  0
 16 29  1  6  0  0  0
 13 30  1  6  0  0  0
 12 31  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0140720

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](CCC=C(C)C)[C@H]1CC[C@@]2(C)[C@@H]3CC=C4[C@@H](CC[C@H](O)C4(C)C)[C@]3(C)CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C30H50O/c1-20(2)10-9-11-21(3)22-16-17-30(8)25-14-12-23-24(13-15-26(31)27(23,4)5)28(25,6)18-19-29(22,30)7/h10,12,21-22,24-26,31H,9,11,13-19H2,1-8H3/t21-,22-,24-,25-,26+,28+,29-,30+/m1/s1

> <INCHI_KEY>
WSPRAEIJBDUDRX-FBJXRMALSA-N

> <FORMULA>
C30H50O

> <MOLECULAR_WEIGHT>
426.729

> <EXACT_MASS>
426.38616623

$$$$

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       9.302  -2.907   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.882  -1.480   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.407  -1.269   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.353  -2.485   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.878  -2.275   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.823  -3.490   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      16.349  -3.280   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.243  -4.917   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.937  -0.264   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.365   1.215   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.090   2.079   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.874   1.134   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.398  -0.314   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.405  -1.492   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.889  -1.221   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.366   0.228   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.358   1.405   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.835   2.854   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.319   3.125   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.326   1.947   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.850   0.499   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.857  -0.678   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.341  -0.407   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.182   1.041   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.810   2.218   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.332   3.252   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.028   3.743   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -1.698   1.312   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       3.373  -0.949   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.069  -1.700   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.505   2.629   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    2   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   17   31                                             
CONECT   13   12    9   14   30                                             
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   21   29                                             
CONECT   17   16   12   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   25                                                  
CONECT   21   20   16   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   28                                                  
CONECT   25   24   20   26   27                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   24                                                            
CONECT   29   16                                                            
CONECT   30   13                                                            
CONECT   31   12                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Value	Source
(1S,4S,9beta)-9,10,14-Trimethyl-4,9-cyclo-9,10-secocholesta-5,24-dien-1-ol	ChEBI
10alpha-Cucurbita-5,24-diene-3beta-ol	ChEBI
Cucurbita-5,24-dien-3-ol	ChEBI
(1S,4S,9b)-9,10,14-Trimethyl-4,9-cyclo-9,10-secocholesta-5,24-dien-1-ol	Generator
(1S,4S,9Β)-9,10,14-trimethyl-4,9-cyclo-9,10-secocholesta-5,24-dien-1-ol	Generator
10a-Cucurbita-5,24-diene-3b-ol	Generator
10Α-cucurbita-5,24-diene-3β-ol	Generator
19(10--9 beta)Abeo-lanosta-5(6),24-dien-3 beta-ol	MeSH

Chemical Formula

C₃₀H₅₀O

Average Mass

426.7290 Da

Monoisotopic Mass

426.38617 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@H](CCC=C(C)C)[C@H]1CC[C@@]2(C)[C@@H]3CC=C4[C@@H](CC[C@H](O)C4(C)C)[C@]3(C)CC[C@]12C

InChI Identifier

InChI=1S/C30H50O/c1-20(2)10-9-11-21(3)22-16-17-30(8)25-14-12-23-24(13-15-26(31)27(23,4)5)28(25,6)18-19-29(22,30)7/h10,12,21-22,24-26,31H,9,11,13-19H2,1-8H3/t21-,22-,24-,25-,26+,28+,29-,30+/m1/s1

InChI Key

WSPRAEIJBDUDRX-FBJXRMALSA-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
Rhus sylvestris	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cucurbitacins. These are polycyclic compounds containing the tetracyclic cucurbitane nucleus skeleton, 19-(10->9b)-abeo-10alanost-5-ene (also known as 9b-methyl-19-nor lanosta-5-ene), with a variety of oxygenation functionalities at different positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cucurbitacins

Direct Parent

Cucurbitacins

Alternative Parents

Substituents

Cucurbitacin skeleton
Triterpenoid
3-hydroxy-delta-5-steroid
3-hydroxysteroid
Hydroxysteroid
14-alpha-methylsteroid
3-beta-hydroxy-delta-5-steroid
3-beta-hydroxysteroid
Delta-5-steroid
Cyclic alcohol
Secondary alcohol
Alcohol
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

tetracyclic triterpenoid (CHEBI:62456 )

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

C00053063

Chemspider ID

20056514

KEGG Compound ID

Not Available

BioCyc ID

CPD-11541

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14543446

PDB ID

Not Available

ChEBI ID

62456

Good Scents ID

Not Available

References

General References

Lertphadungkit P, Qiao X, Sirikantaramas S, Satitpatipan V, Ye M, Bunsupa S: De novo transcriptome analysis and identification of candidate genes associated with triterpenoid biosynthesis in Trichosanthes cucumerina L. Plant Cell Rep. 2021 Oct;40(10):1845-1858. doi: 10.1007/s00299-021-02748-8. Epub 2021 Jul 6. [PubMed:34228189 ]
Thirumal Kumar D, Shree Devi MS, Udhaya Kumar S, Sherlin A, Mathew A, Lakshmipriya M, Sathiyarajeswaran P, Gnanasambandan R, Siva R, Magesh R, George Priya Doss C: Understanding the activating mechanism of the immune system against COVID-19 by Traditional Indian Medicine: Network pharmacology approach. Adv Protein Chem Struct Biol. 2022;129:275-379. doi: 10.1016/bs.apcsb.2021.11.007. Epub 2022 Jan 29. [PubMed:35305722 ]
Evary YM, Masyita A, Kurnianto AA, Asri RM, Rifai Y: Molecular Docking of Phytochemical Compounds of Momordica charantia as Potential Inhibitors against SARS-CoV-2. Infect Disord Drug Targets. 2022;22(3):e130122200221. doi: 10.2174/1871526522666220113143358. [PubMed:35049440 ]
Dong L, Almeida A, Pollier J, Khakimov B, Bassard JE, Miettinen K, Staerk D, Mehran R, Olsen CE, Motawia MS, Goossens A, Bak S: An Independent Evolutionary Origin for Insect Deterrent Cucurbitacins in Iberis amara. Mol Biol Evol. 2021 Oct 27;38(11):4659-4673. doi: 10.1093/molbev/msab213. [PubMed:34264303 ]

Showing NP-Card for Cucurbitadienol (NP0140720)

MOL for NP0140720 (Cucurbitadienol)

3D MOL for NP0140720 (Cucurbitadienol)

3D SDF for NP0140720 (Cucurbitadienol)

3D-SDF for NP0140720 (Cucurbitadienol)

PDB for NP0140720 (Cucurbitadienol)

3D PDB for NP0140720 (Cucurbitadienol)

SMILES for NP0140720 (Cucurbitadienol)

INCHI for NP0140720 (Cucurbitadienol)

Structure for NP0140720 (Cucurbitadienol)

3D Structure for NP0140720 (Cucurbitadienol)