NP-MRD: Showing NP-Card for 3-angeloyloxy-5-isobutanoyloxy-7-hydroxycarvotacetone (NP0332281)

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Record Information

Version

2.0

Created at

2023-12-22 12:00:44 UTC

Updated at

2024-09-03 04:18:42 UTC

NP-MRD ID

NP0332281

Natural Product DOI

https://doi.org/10.57994/1482

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-angeloyloxy-5-isobutanoyloxy-7-hydroxycarvotacetone

Description

3-Angeloyloxy-5-isobutanoyloxy-7-hydroxycarvotacetone belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol. 3-angeloyloxy-5-isobutanoyloxy-7-hydroxycarvotacetone was first documented in 2024 (PMID: 38061483). Based on a literature review very few articles have been published on 3-angeloyloxy-5-isobutanoyloxy-7-hydroxycarvotacetone.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 12222312002D          

 27 27  0  0  1  0            999 V2000
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  0  0  0  0
  3  4  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  5  9  2  0  0  0  0
 10  3  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 17 23  2  0  0  0  0
 15 24  1  0  0  0  0
 24 25  2  0  0  0  0
  2 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END


  Mrv2104 12222312002D          

 27 27  0  0  1  0            999 V2000
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  0  0  0  0
  3  4  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  5  9  2  0  0  0  0
 10  3  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 17 23  2  0  0  0  0
 15 24  1  0  0  0  0
 24 25  2  0  0  0  0
  2 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0332281

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(C)=C(/C)C(=O)O[C@@H]1C=C(CO)C(=O)[C@@H](OC(=O)C(C)C)[C@@H]1C([H])(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C19H28O6/c1-7-12(6)19(23)24-14-8-13(9-20)16(21)17(15(14)10(2)3)25-18(22)11(4)5/h7-8,10-11,14-15,17,20H,9H2,1-6H3/b12-7-/t14-,15-,17+/m1/s1

> <INCHI_KEY>
RRQFGVFSJAMXBA-UVDMBJKLSA-N

> <FORMULA>
C19H28O6

> <MOLECULAR_WEIGHT>
352.427

> <EXACT_MASS>
352.188588622

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
38.14243306848525

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,5S,6R)-3-(hydroxymethyl)-5-[(2-methylpropanoyl)oxy]-4-oxo-6-(propan-2-yl)cyclohex-2-en-1-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_LOGP>
3.534622184333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.73662573618039

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.947006894624376

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8215531892938204

> <JCHEM_POLAR_SURFACE_AREA>
89.90000000000002

> <JCHEM_REFRACTIVITY>
94.1853

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,5S,6R)-3-(hydroxymethyl)-6-isopropyl-5-[(2-methylpropanoyl)oxy]-4-oxocyclohex-2-en-1-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-DEC-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-DEC-23         0                                  
HETATM    1  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   14  H   UNK     0       2.667  -1.540   0.000  0.00  0.00           H+0
HETATM   15  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   21  H   UNK     0      -4.001  -2.310   0.000  0.00  0.00           H+0
HETATM   22  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   25                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    5                                                            
CONECT   10    3   11   15                                                  
CONECT   11   10   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11                                                            
CONECT   15   10   16   24                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   23                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   17                                                            
CONECT   24   15   25                                                       
CONECT   25   24    2   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₈O₆

Average Mass

352.4270 Da

Monoisotopic Mass

352.18859 Da

IUPAC Name

(1R,5S,6R)-3-(hydroxymethyl)-5-[(2-methylpropanoyl)oxy]-4-oxo-6-(propan-2-yl)cyclohex-2-en-1-yl (2Z)-2-methylbut-2-enoate

Traditional Name

(1R,5S,6R)-3-(hydroxymethyl)-6-isopropyl-5-[(2-methylpropanoyl)oxy]-4-oxocyclohex-2-en-1-yl (2Z)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

[H]\C(C)=C(/C)C(=O)O[C@@H]1C=C(CO)C(=O)[C@@H](OC(=O)C(C)C)[C@@H]1C([H])(C)C

InChI Identifier

InChI=1S/C19H28O6/c1-7-12(6)19(23)24-14-8-13(9-20)16(21)17(15(14)10(2)3)25-18(22)11(4)5/h7-8,10-11,14-15,17,20H,9H2,1-6H3/b12-7-/t14-,15-,17+/m1/s1

InChI Key

RRQFGVFSJAMXBA-UVDMBJKLSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, CD3OD, experimental)	olaf.kunert@uni-graz.at	University of Graz - Institute of Pharmaceutical Sciences	Olaf Kunert	2023-12-22	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, CD3OD, experimental)	olaf.kunert@uni-graz.at	University of Graz - Institute of Pharmaceutical Sciences	Olaf Kunert	2023-12-22	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, CD3OD, experimental)	olaf.kunert@uni-graz.at	University of Graz - Institute of Pharmaceutical Sciences	Olaf Kunert	2023-12-22	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, CD3OD, experimental)	olaf.kunert@uni-graz.at	University of Graz - Institute of Pharmaceutical Sciences	Olaf Kunert	2023-12-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD3OD, experimental)	olaf.kunert@uni-graz.at	University of Graz - Institute of Pharmaceutical Sciences	Olaf Kunert	2023-12-22	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohol esters

Direct Parent

Fatty alcohol esters

Alternative Parents

Substituents

Fatty alcohol ester
P-menthane monoterpenoid
Monoterpenoid
Monocyclic monoterpenoid
Fatty alcohol
Cyclohexenone
Alpha-acyloxy ketone
Fatty acid ester
Alpha-branched alpha,beta-unsaturated-ketone
Monosaccharide
Dicarboxylic acid or derivatives
Beta-hydroxy ketone
Alpha,beta-unsaturated ketone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Enone
Acryloyl-group
Cyclic ketone
Ketone
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic 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	3.53	ChemAxon
pKa (Strongest Acidic)	14.95	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	89.9 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	94.19 m³·mol⁻¹	ChemAxon
Polarizability	38.14 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Tran HT, Pirker T, Pferschy-Wenzig EM, Kunert O, Huynh L, Bauer R: Structures and bioactivities of monomeric and dimeric carvotacetones from Sphaeranthus africanus. Phytochemistry. 2024 Feb;218:113938. doi: 10.1016/j.phytochem.2023.113938. Epub 2023 Dec 5. [PubMed:38061483 ]

Showing NP-Card for 3-angeloyloxy-5-isobutanoyloxy-7-hydroxycarvotacetone (NP0332281)

MOL for NP0332281 (3-angeloyloxy-5-isobutanoyloxy-7-hydroxycarvotacetone)

3D MOL for NP0332281 (3-angeloyloxy-5-isobutanoyloxy-7-hydroxycarvotacetone)

3D SDF for NP0332281 (3-angeloyloxy-5-isobutanoyloxy-7-hydroxycarvotacetone)

3D-SDF for NP0332281 (3-angeloyloxy-5-isobutanoyloxy-7-hydroxycarvotacetone)

PDB for NP0332281 (3-angeloyloxy-5-isobutanoyloxy-7-hydroxycarvotacetone)

3D PDB for NP0332281 (3-angeloyloxy-5-isobutanoyloxy-7-hydroxycarvotacetone)

SMILES for NP0332281 (3-angeloyloxy-5-isobutanoyloxy-7-hydroxycarvotacetone)

INCHI for NP0332281 (3-angeloyloxy-5-isobutanoyloxy-7-hydroxycarvotacetone)

Structure for NP0332281 (3-angeloyloxy-5-isobutanoyloxy-7-hydroxycarvotacetone)

3D Structure for NP0332281 (3-angeloyloxy-5-isobutanoyloxy-7-hydroxycarvotacetone)