NP-MRD: Showing NP-Card for Betulinaldehyde (NP0139988)

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Record Information

Version

2.0

Created at

2022-06-29 20:19:56 UTC

Updated at

2022-06-29 20:19:56 UTC

NP-MRD ID

NP0139988

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Betulinaldehyde

Description

BETULINALDEHYDE belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Betulinaldehyde is found in Bersama swinnyi, Ceriops decandra, Cichorium intybus, Cornus kousa, Coussarea paniculata, Dillenia papuana, Diospyros eriantha, Diospyros maritima, Diospyros virginiana, Diospyros wallichii, Doliocarpus dentatus, Lawsonia inermis, Melaleuca ericifolia, Melaleuca leucadendra, Melilotus messanensis, Paliurus hemsleyanus, Phoradendron reichenbachianum, Prunus dulcis and Sarracenia flava. Betulinaldehyde was first documented in 2019 (PMID: 31195082). Based on a literature review a small amount of articles have been published on BETULINALDEHYDE (PMID: 34365946) (PMID: 34570641) (PMID: 32779093) (PMID: 35511385).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652306292222192D          

 32 36  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306292222192D          

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 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 12 21  1  0  0  0  0
 21 22  1  0  0  0  0
  9 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  7 24  1  0  0  0  0
 22 25  1  1  0  0  0
 21 26  1  6  0  0  0
 17 27  1  0  0  0  0
 17 28  1  0  0  0  0
 16 29  1  6  0  0  0
 13 30  1  6  0  0  0
  7 31  1  6  0  0  0
 31 32  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0139988

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)[C@@H]1CC[C@@]2(CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]12)C=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H48O2/c1-19(2)20-10-15-30(18-31)17-16-28(6)21(25(20)30)8-9-23-27(5)13-12-24(32)26(3,4)22(27)11-14-29(23,28)7/h18,20-25,32H,1,8-17H2,2-7H3/t20-,21+,22-,23+,24-,25+,27-,28+,29+,30+/m0/s1

> <INCHI_KEY>
FELCJAPFJOPHSD-ROUWMTJPSA-N

> <FORMULA>
C30H48O2

> <MOLECULAR_WEIGHT>
440.712

> <EXACT_MASS>
440.365430786

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
53.761467640017294

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,5S,8R,9R,10R,13R,14R,17S,19R)-17-hydroxy-1,2,14,18,18-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosane-5-carbaldehyde

> <ALOGPS_LOGP>
5.35

> <JCHEM_LOGP>
6.481122827666669

> <ALOGPS_LOGS>
-6.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.48943339017772

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8351216011238239

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
131.7001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.59e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5S,8R,9R,10R,13R,14R,17S,19R)-17-hydroxy-1,2,14,18,18-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosane-5-carbaldehyde

> <JCHEM_VEBER_RULE>
1

$$$$

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       3.577  -5.001   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.105  -5.454   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.977  -4.407   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.762  -6.956   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.346  -7.561   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.484  -9.094   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.985  -9.438   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.775  -8.116   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.315  -8.139   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.105  -6.817   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.645  -6.841   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.395  -8.186   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.935  -8.209   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.725  -6.888   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.265  -6.911   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.014  -8.256   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.224  -9.578   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.684  -9.555   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.894 -10.876   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.354 -10.853   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.605  -9.508   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.065  -9.484   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.275 -10.806   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.735 -10.783   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.814 -10.830   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.742 -11.042   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.518 -10.414   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.254 -11.118   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      13.554  -8.280   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       8.185  -6.864   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.061 -10.670   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -0.468 -10.485   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   24   31                                             
CONECT    8    7    4    9                                                  
CONECT    9    8   10   22                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   21                                                  
CONECT   13   12   14   18   30                                             
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   29                                                  
CONECT   17   16   18   27   28                                             
CONECT   18   17   13   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   12   22   26                                             
CONECT   22   21    9   23   25                                             
CONECT   23   22   24                                                       
CONECT   24   23    7                                                       
CONECT   25   22                                                            
CONECT   26   21                                                            
CONECT   27   17                                                            
CONECT   28   17                                                            
CONECT   29   16                                                            
CONECT   30   13                                                            
CONECT   31    7   32                                                       
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₈O₂

Average Mass

440.7120 Da

Monoisotopic Mass

440.36543 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(=C)[C@@H]1CC[C@@]2(CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]12)C=O

InChI Identifier

InChI=1S/C30H48O2/c1-19(2)20-10-15-30(18-31)17-16-28(6)21(25(20)30)8-9-23-27(5)13-12-24(32)26(3,4)22(27)11-14-29(23,28)7/h18,20-25,32H,1,8-17H2,2-7H3/t20-,21+,22-,23+,24-,25+,27-,28+,29+,30+/m0/s1

InChI Key

FELCJAPFJOPHSD-ROUWMTJPSA-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
Bersama swinnyi	LOTUS Database	35616633
Ceriops decandra	LOTUS Database	35616633
Cichorium intybus	LOTUS Database	35616633
Cornus kousa	LOTUS Database	35616633
Coussarea paniculata	LOTUS Database	35616633
Dillenia papuana	LOTUS Database	35616633
Diospyros eriantha	LOTUS Database	35616633
Diospyros maritima	LOTUS Database	35616633
Diospyros virginiana	LOTUS Database	35616633
Diospyros wallichii	LOTUS Database	35616633
Doliocarpus dentatus	LOTUS Database	35616633
Lawsonia inermis	LOTUS Database	35616633
Melaleuca ericifolia	LOTUS Database	35616633
Melaleuca leucadendra	LOTUS Database	35616633
Melilotus messanensis	LOTUS Database	35616633
Paliurus hemsleyanus	LOTUS Database	35616633
Phoradendron reichenbachianum	LOTUS Database	35616633
Prunus dulcis	LOTUS Database	35616633
Sarracenia flava	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
18-oxosteroid
Oxosteroid
Steroid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Alcohol
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00021224

Chemspider ID

89999

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

99615

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Chung PY, Gan MY, Chin BY: Pentacyclic triterpenoids as antibiofilm agents against methicillin-resistant and biofilm-forming Staphylococcus aureus (MRSA). Curr Pharm Biotechnol. 2021 Aug 5. pii: CPB-EPUB-117113. doi: 10.2174/1389201022666210806092643. [PubMed:34365946 ]
Missi MB, Evina JN, Zintchem AAA, October N, Bona A, Moela P, Betote Diboue PH, Ngono Bikobo DS, Pegnyemb DE: Antibacterial and cytotoxic activities of undescribed cassiaric acid and other constituents from Cassia arereh stem barks. Nat Prod Res. 2021 Sep 27:1-10. doi: 10.1080/14786419.2021.1981313. [PubMed:34570641 ]
Vu TO, Tran PT, Seo W, Lee JH, Min BS, Kim JA: Triterpenoids from Celastrus orbiculatus Thunb. inhibit RANKL-induced osteoclast formation and bone resorption via c-Fos signaling. J Nat Med. 2021 Jan;75(1):56-65. doi: 10.1007/s11418-020-01444-3. Epub 2020 Aug 10. [PubMed:32779093 ]
Purohit S, Bohra MK, Jain R: Identification of Bioactive Pentacyclic Triterpenoids and Fatty Acid Derivatives from Cissus quadrangularis and C. rotundifolia Through Untargeted Metabolite Profiling. Appl Biochem Biotechnol. 2022 May 5. pii: 10.1007/s12010-022-03940-6. doi: 10.1007/s12010-022-03940-6. [PubMed:35511385 ]
Yang F, Zhang R, Ni D, Luo X, Chen S, Luo C, Xiao W: Discovery of betulinaldehyde as a natural RORgammat agonist. Fitoterapia. 2019 Sep;137:104200. doi: 10.1016/j.fitote.2019.104200. Epub 2019 Jun 10. [PubMed:31195082 ]

Showing NP-Card for Betulinaldehyde (NP0139988)

MOL for NP0139988 (Betulinaldehyde)

3D MOL for NP0139988 (Betulinaldehyde)

3D SDF for NP0139988 (Betulinaldehyde)

3D-SDF for NP0139988 (Betulinaldehyde)

PDB for NP0139988 (Betulinaldehyde)

3D PDB for NP0139988 (Betulinaldehyde)

SMILES for NP0139988 (Betulinaldehyde)

INCHI for NP0139988 (Betulinaldehyde)

Structure for NP0139988 (Betulinaldehyde)

3D Structure for NP0139988 (Betulinaldehyde)