NP-MRD: Showing NP-Card for Lupeolic acid (NP0139984)

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Record Information

Version

2.0

Created at

2022-06-29 20:19:44 UTC

Updated at

2022-06-29 20:19:44 UTC

NP-MRD ID

NP0139984

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lupeolic acid

Description

Lupeolic acid, also known as lupeolate, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Lupeolic acid was first documented in 2012 (PMID: 22732453). Based on a literature review a small amount of articles have been published on lupeolic acid (PMID: 29232585) (PMID: 31581678) (PMID: 31181656) (PMID: 28903409).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652306292222192D          

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M  END


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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  1  0  0  0
 17 28  1  6  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 16 31  1  1  0  0  0
 13 32  1  6  0  0  0
  7 33  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0139984

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C30H48O3/c1-18(2)19-10-13-26(3)16-17-28(5)20(24(19)26)8-9-21-27(4)14-12-23(31)30(7,25(32)33)22(27)11-15-29(21,28)6/h19-24,31H,1,8-17H2,2-7H3,(H,32,33)/t19-,20+,21+,22+,23+,24+,26+,27+,28+,29+,30+/m0/s1

> <INCHI_KEY>
NYJYXELDYSTZFI-XSDHLHMPSA-N

> <FORMULA>
C30H48O3

> <MOLECULAR_WEIGHT>
456.711

> <EXACT_MASS>
456.360345406

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
54.57616499452306

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
5.46

> <JCHEM_LOGP>
6.639739080000002

> <ALOGPS_LOGS>
-6.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.7171099791673

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.595807206647877

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0375459266020215

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
132.6255

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.64e-04 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

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       0.977  -4.407   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       3.577  -5.001   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      11.254 -11.118   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.518 -10.414   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      12.440 -11.952   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      13.888  -9.712   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      13.554  -8.280   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       8.185  -6.864   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.061 -10.670   0.000  0.00  0.00           C+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   33                                             
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   32                                             
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   31                                                  
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   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   16                                                            
CONECT   32   13                                                            
CONECT   33    7                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Value	Source
Lupeolate	Generator

Chemical Formula

C₃₀H₄₈O₃

Average Mass

456.7110 Da

Monoisotopic Mass

456.36035 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C30H48O3/c1-18(2)19-10-13-26(3)16-17-28(5)20(24(19)26)8-9-21-27(4)14-12-23(31)30(7,25(32)33)22(27)11-15-29(21,28)6/h19-24,31H,1,8-17H2,2-7H3,(H,32,33)/t19-,20+,21+,22+,23+,24+,26+,27+,28+,29+,30+/m0/s1

InChI Key

NYJYXELDYSTZFI-XSDHLHMPSA-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

Not Available

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
15-hydroxysteroid
Hydroxysteroid
Steroid
Beta-hydroxy acid
Hydroxy acid
Cyclic alcohol
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Alcohol
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
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

Not Available

Chemspider ID

20120049

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12111950

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Saeed A, Hussain H, Shamraiz U, Rehman NU, Khan HY, Badshah A, Heller L, Csuk R, Ali M, Khan A, Al-Harrasi A: Synthesis of new triterpenic monomers and dimers as potential antiproliferative agents and their molecular docking studies. Eur J Med Chem. 2018 Jan 1;143:948-957. doi: 10.1016/j.ejmech.2017.10.079. [PubMed:29232585 ]
Schmiech M, Lang SJ, Ulrich J, Werner K, Rashan LJ, Syrovets T, Simmet T: Comparative Investigation of Frankincense Nutraceuticals: Correlation of Boswellic and Lupeolic Acid Contents with Cytokine Release Inhibition and Toxicity against Triple-Negative Breast Cancer Cells. Nutrients. 2019 Oct 2;11(10):2341. doi: 10.3390/nu11102341. [PubMed:31581678 ]
Schmiech M, Lang SJ, Werner K, Rashan LJ, Syrovets T, Simmet T: Comparative Analysis of Pentacyclic Triterpenic Acid Compositions in Oleogum Resins of Different Boswellia Species and Their In Vitro Cytotoxicity against Treatment-Resistant Human Breast Cancer Cells. Molecules. 2019 Jun 7;24(11):2153. doi: 10.3390/molecules24112153. [PubMed:31181656 ]
Schmidt C, Loos C, Jin L, Schmiech M, Schmidt CQ, Gaafary ME, Syrovets T, Simmet T: Acetyl-lupeolic acid inhibits Akt signaling and induces apoptosis in chemoresistant prostate cancer cells in vitro and in vivo. Oncotarget. 2017 Jul 8;8(33):55147-55161. doi: 10.18632/oncotarget.19101. eCollection 2017 Aug 15. [PubMed:28903409 ]
Verhoff M, Seitz S, Northoff H, Jauch J, Schaible AM, Werz O: A novel C(28)-hydroxylated lupeolic acid suppresses the biosynthesis of eicosanoids through inhibition of cytosolic phospholipase A(2). Biochem Pharmacol. 2012 Sep 1;84(5):681-91. doi: 10.1016/j.bcp.2012.06.016. Epub 2012 Jun 23. [PubMed:22732453 ]

Showing NP-Card for Lupeolic acid (NP0139984)

MOL for NP0139984 (Lupeolic acid)

3D MOL for NP0139984 (Lupeolic acid)

3D SDF for NP0139984 (Lupeolic acid)

3D-SDF for NP0139984 (Lupeolic acid)

PDB for NP0139984 (Lupeolic acid)

3D PDB for NP0139984 (Lupeolic acid)

SMILES for NP0139984 (Lupeolic acid)

INCHI for NP0139984 (Lupeolic acid)

Structure for NP0139984 (Lupeolic acid)

3D Structure for NP0139984 (Lupeolic acid)