NP-MRD: Showing NP-Card for (3s,4ar,6br,8ar,12s,12ar,12br,14ar,14br)-4,4,6a,6b,8a,12,14b-heptamethyl-11-methylidene-hexadecahydropicen-3-yl acetate (NP0202729)

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Record Information

Version

2.0

Created at

2022-09-04 22:00:16 UTC

Updated at

2022-09-04 22:00:16 UTC

NP-MRD ID

NP0202729

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,4ar,6br,8ar,12s,12ar,12br,14ar,14br)-4,4,6a,6b,8a,12,14b-heptamethyl-11-methylidene-hexadecahydropicen-3-yl acetate

Description

Taraxasteryl acetate belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (3s,4ar,6br,8ar,12s,12ar,12br,14ar,14br)-4,4,6a,6b,8a,12,14b-heptamethyl-11-methylidene-hexadecahydropicen-3-yl acetate is found in Brickellia veronicifolia and Pleocarphus revolutus. (3s,4ar,6br,8ar,12s,12ar,12br,14ar,14br)-4,4,6a,6b,8a,12,14b-heptamethyl-11-methylidene-hexadecahydropicen-3-yl acetate was first documented in 2016 (PMID: 28036090). Based on a literature review a small amount of articles have been published on Taraxasteryl acetate (PMID: 32841700) (PMID: 33968579) (PMID: 30037105) (PMID: 28902635).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052200002D          

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M  END

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M  END


  Mrv1652309052200002D          

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   11.6013   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0138   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8388   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6013   -3.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3638   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5388   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1263   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.7138   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8263   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4138   -2.7770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8263   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 14 13  1  1  0  0  0
 14 15  1  0  0  0  0
  9 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 19 18  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 19 30  1  0  0  0  0
 14 30  1  0  0  0  0
 30 31  1  1  0  0  0
 32 11  1  1  0  0  0
  5 32  1  0  0  0  0
 32 33  1  0  0  0  0
  2 33  1  0  0  0  0
 33 34  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0202729

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1[C@@H]2[C@H]3CC[C@@H]4[C@@]5(C)CC[C@H](OC(C)=O)C(C)(C)[C@@H]5CCC4(C)[C@]3(C)CC[C@@]2(C)CCC1=C

> <INCHI_IDENTIFIER>
InChI=1S/C32H52O2/c1-20-12-15-29(6)18-19-31(8)23(27(29)21(20)2)10-11-25-30(7)16-14-26(34-22(3)33)28(4,5)24(30)13-17-32(25,31)9/h21,23-27H,1,10-19H2,2-9H3/t21-,23-,24+,25-,26+,27-,29-,30+,31-,32?/m1/s1

> <INCHI_KEY>
SFEUTIOWNUGQMZ-VDJWUHLSSA-N

> <FORMULA>
C32H52O2

> <MOLECULAR_WEIGHT>
468.766

> <EXACT_MASS>
468.396730914

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
86

> <JCHEM_AVERAGE_POLARIZABILITY>
58.55710300220139

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,4aR,6bR,8aR,12S,12aR,12bR,14aR,14bR)-4,4,6a,6b,8a,12,14b-heptamethyl-11-methylidene-docosahydropicen-3-yl acetate

> <JCHEM_LOGP>
7.889171891333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.00377816438925

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
140.0598

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3S,4aR,6bR,8aR,12S,12aR,12bR,14aR,14bR)-4,4,6a,6b,8a,12,14b-heptamethyl-11-methylidene-hexadecahydropicen-3-yl acetate

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       7.796  -6.517   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.566  -5.184   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.796  -3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.566  -2.516   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.106  -2.516   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.336  -1.183   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.876  -1.183   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.416  -1.183   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.186  -2.516   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.956  -1.183   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.416  -3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.186  -5.184   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.726  -5.184   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.496  -3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.726  -2.516   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.887  -0.985   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      15.496  -1.183   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.036  -1.183   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      17.806  -2.516   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      19.346  -2.516   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      19.078  -1.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      20.793  -1.990   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      20.116  -3.850   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      21.656  -3.850   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      22.426  -5.184   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      23.966  -5.184   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      21.656  -6.517   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      19.346  -5.184   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      17.806  -5.184   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      17.036  -3.850   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      16.266  -5.184   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.876  -3.850   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.106  -5.184   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.876  -6.517   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   33                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7   32                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   15                                             
CONECT   10    9                                                            
CONECT   11    9   12   32                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   30                                                  
CONECT   15   14    9   16   17                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   30                                                  
CONECT   20   19   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   20   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   23   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   19   14   31                                             
CONECT   31   30                                                            
CONECT   32   11    5   33                                                  
CONECT   33   32    2   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Value	Source
Taraxasteryl acetic acid	Generator
Urs-20(30)-en-3-ol acetate	MeSH
Taraxasterol acetate	MeSH

Chemical Formula

C₃₂H₅₂O₂

Average Mass

468.7660 Da

Monoisotopic Mass

468.39673 Da

IUPAC Name

(3S,4aR,6bR,8aR,12S,12aR,12bR,14aR,14bR)-4,4,6a,6b,8a,12,14b-heptamethyl-11-methylidene-docosahydropicen-3-yl acetate

Traditional Name

(3S,4aR,6bR,8aR,12S,12aR,12bR,14aR,14bR)-4,4,6a,6b,8a,12,14b-heptamethyl-11-methylidene-hexadecahydropicen-3-yl acetate

CAS Registry Number

Not Available

SMILES

C[C@H]1[C@@H]2[C@H]3CC[C@@H]4[C@@]5(C)CC[C@H](OC(C)=O)C(C)(C)[C@@H]5CCC4(C)[C@]3(C)CC[C@@]2(C)CCC1=C

InChI Identifier

InChI=1S/C32H52O2/c1-20-12-15-29(6)18-19-31(8)23(27(29)21(20)2)10-11-25-30(7)16-14-26(34-22(3)33)28(4,5)24(30)13-17-32(25,31)9/h21,23-27H,1,10-19H2,2-9H3/t21-,23-,24+,25-,26+,27-,29-,30+,31-,32?/m1/s1

InChI Key

SFEUTIOWNUGQMZ-VDJWUHLSSA-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
Brickellia veronicifolia	LOTUS Database	35616633
Pleocarphus revolutus	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
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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
logP	7.89	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	140.06 m³·mol⁻¹	ChemAxon
Polarizability	58.56 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00022684

Chemspider ID

91462

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101225

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Bihani T: Plumeria rubra L.- A review on its ethnopharmacological, morphological, phytochemical, pharmacological and toxicological studies. J Ethnopharmacol. 2021 Jan 10;264:113291. doi: 10.1016/j.jep.2020.113291. Epub 2020 Aug 22. [PubMed:32841700 ]
Bansod AA, Ramasamy G, Nathan B, Kandhasamy R, Palaniappan M, Vichangal Pridiuldi S: Exploring the endogenous potential of Hemidesmus indicus against breast cancer using in silico studies and quantification of 2-hydroxy-4-methoxy benzaldehyde through RP-HPLC. 3 Biotech. 2021 May;11(5):235. doi: 10.1007/s13205-021-02768-x. Epub 2021 Apr 24. [PubMed:33968579 ]
Bahadir-Acikara O, Ozbilgin S, Saltan-Iscan G, Dall'Acqua S, Rjaskova V, Ozgokce F, Suchy V, Smejkal K: Phytochemical Analysis of Podospermum and Scorzonera n-Hexane Extracts and the HPLC Quantitation of Triterpenes. Molecules. 2018 Jul 21;23(7):1813. doi: 10.3390/molecules23071813. [PubMed:30037105 ]
Ivanov I, Petkova N, Tumbarski J, Dincheva I, Badjakov I, Denev P, Pavlov A: GC-MS characterization of n-hexane soluble fraction from dandelion (Taraxacum officinale Weber ex F.H. Wigg.) aerial parts and its antioxidant and antimicrobial properties. Z Naturforsch C J Biosci. 2018 Jan 26;73(1-2):41-47. doi: 10.1515/znc-2017-0107. [PubMed:28902635 ]
Ramos PA, Guerra AR, Guerreiro O, Santos SA, Oliveira H, Freire CS, Silvestre AJ, Duarte MF: Antiproliferative Effects of Cynara cardunculus L. var. altilis (DC) Lipophilic Extracts. Int J Mol Sci. 2016 Dec 29;18(1):63. doi: 10.3390/ijms18010063. [PubMed:28036090 ]
LOTUS database [Link]

Showing NP-Card for (3s,4ar,6br,8ar,12s,12ar,12br,14ar,14br)-4,4,6a,6b,8a,12,14b-heptamethyl-11-methylidene-hexadecahydropicen-3-yl acetate (NP0202729)

MOL for NP0202729 ((3s,4ar,6br,8ar,12s,12ar,12br,14ar,14br)-4,4,6a,6b,8a,12,14b-heptamethyl-11-methylidene-hexadecahydropicen-3-yl acetate)

3D MOL for NP0202729 ((3s,4ar,6br,8ar,12s,12ar,12br,14ar,14br)-4,4,6a,6b,8a,12,14b-heptamethyl-11-methylidene-hexadecahydropicen-3-yl acetate)

3D SDF for NP0202729 ((3s,4ar,6br,8ar,12s,12ar,12br,14ar,14br)-4,4,6a,6b,8a,12,14b-heptamethyl-11-methylidene-hexadecahydropicen-3-yl acetate)

3D-SDF for NP0202729 ((3s,4ar,6br,8ar,12s,12ar,12br,14ar,14br)-4,4,6a,6b,8a,12,14b-heptamethyl-11-methylidene-hexadecahydropicen-3-yl acetate)

PDB for NP0202729 ((3s,4ar,6br,8ar,12s,12ar,12br,14ar,14br)-4,4,6a,6b,8a,12,14b-heptamethyl-11-methylidene-hexadecahydropicen-3-yl acetate)

3D PDB for NP0202729 ((3s,4ar,6br,8ar,12s,12ar,12br,14ar,14br)-4,4,6a,6b,8a,12,14b-heptamethyl-11-methylidene-hexadecahydropicen-3-yl acetate)

SMILES for NP0202729 ((3s,4ar,6br,8ar,12s,12ar,12br,14ar,14br)-4,4,6a,6b,8a,12,14b-heptamethyl-11-methylidene-hexadecahydropicen-3-yl acetate)

INCHI for NP0202729 ((3s,4ar,6br,8ar,12s,12ar,12br,14ar,14br)-4,4,6a,6b,8a,12,14b-heptamethyl-11-methylidene-hexadecahydropicen-3-yl acetate)

Structure for NP0202729 ((3s,4ar,6br,8ar,12s,12ar,12br,14ar,14br)-4,4,6a,6b,8a,12,14b-heptamethyl-11-methylidene-hexadecahydropicen-3-yl acetate)

3D Structure for NP0202729 ((3s,4ar,6br,8ar,12s,12ar,12br,14ar,14br)-4,4,6a,6b,8a,12,14b-heptamethyl-11-methylidene-hexadecahydropicen-3-yl acetate)