NP-MRD: Showing NP-Card for 3beta-Acetoxy-28,13-ursanolide. (NP0084649)

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Record Information

Version

2.0

Created at

2022-04-29 05:19:43 UTC

Updated at

2022-04-29 05:19:43 UTC

NP-MRD ID

NP0084649

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3beta-Acetoxy-28,13-ursanolide.

Description

Ursolic acid lactone acetate belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. 3beta-Acetoxy-28,13-ursanolide. is found in Eucalyptus camaldulensis and Helichrysum italicum . Based on a literature review very few articles have been published on ursolic acid lactone acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292207192D          

 39 44  0  0  1  0            999 V2000
    3.1500   -1.2759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652304292207192D          

 39 44  0  0  1  0            999 V2000
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    9.2418   -1.0991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0048   -1.8145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7668   -1.1009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9418   -1.1015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5288   -0.3873    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1168   -1.1020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7038   -0.3879    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8788   -0.3939    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2984   -1.1131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4643   -1.1184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9789   -0.4170    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2267   -0.9096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5173   -0.3992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7337   -0.6573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4809   -0.0133    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9607    0.6579    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 16 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 12 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 10 34  1  0  0  0  0
 34 35  1  1  0  0  0
 35 36  1  0  0  0  0
  7 36  1  1  0  0  0
 36 37  2  0  0  0  0
 34 38  1  0  0  0  0
  7 38  1  0  0  0  0
  2 38  1  0  0  0  0
 38 39  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0084649

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12[C@@H](C)[C@H](C)CC[C@]11CC[C@]3(C)[C@@]2(CC[C@]2([H])[C@@]4(C)CC[C@H](OC(C)=O)C(C)(C)[C@]4([H])CC[C@@]32C)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C32H50O4/c1-19-9-15-31-18-17-30(8)29(7)14-10-22-27(4,5)24(35-21(3)33)12-13-28(22,6)23(29)11-16-32(30,36-26(31)34)25(31)20(19)2/h19-20,22-25H,9-18H2,1-8H3/t19-,20+,22+,23-,24+,25-,28+,29-,30+,31+,32+/m1/s1

> <INCHI_KEY>
NJLCBLDWBHWOFU-NOAGMNDJSA-N

> <FORMULA>
C32H50O4

> <MOLECULAR_WEIGHT>
498.748

> <EXACT_MASS>
498.37091009

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
86

> <JCHEM_AVERAGE_POLARIZABILITY>
59.39054184927646

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4S,5R,8R,10S,13R,14R,17S,18R,19S,20R)-4,5,9,9,13,19,20-heptamethyl-23-oxo-24-oxahexacyclo[15.5.2.0^{1,18}.0^{4,17}.0^{5,14}.0^{8,13}]tetracosan-10-yl acetate

> <ALOGPS_LOGP>
6.41

> <JCHEM_LOGP>
7.0116353909999996

> <ALOGPS_LOGS>
-7.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.763190644516497

> <JCHEM_POLAR_SURFACE_AREA>
52.6

> <JCHEM_REFRACTIVITY>
139.95839999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.92e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4S,5R,8R,10S,13R,14R,17S,18R,19S,20R)-4,5,9,9,13,19,20-heptamethyl-23-oxo-24-oxahexacyclo[15.5.2.0^{1,18}.0^{4,17}.0^{5,14}.0^{8,13}]tetracosan-10-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       5.880  -2.382   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.738  -1.420   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.214  -2.285   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.159  -3.824   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.910  -1.467   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.965   0.072   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.326   0.793   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.204   2.154   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.800   2.091   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.453   0.605   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.293   1.896   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.010   0.609   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.168   2.141   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.779   1.943   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.319   1.944   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.089   0.611   0.000  0.00  0.00           C+0
HETATM   17  H   UNK     0      11.860  -0.722   0.000  0.00  0.00           H+0
HETATM   18  C   UNK     0      12.629   0.612   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.361   2.129   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.076   1.140   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.400  -0.721   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      14.940  -0.720   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      15.711  -2.053   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      17.251  -2.052   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      14.942  -3.387   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      12.631  -2.055   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.091  -2.056   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.320  -0.723   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.551  -2.057   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.780  -0.724   0.000  0.00  0.00           C+0
HETATM   31  H   UNK     0       7.240  -0.735   0.000  0.00  0.00           H+0
HETATM   32  C   UNK     0       8.024  -2.078   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.467  -2.088   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.561  -0.778   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       4.157  -1.698   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       2.832  -0.745   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       1.370  -1.227   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       4.631  -0.025   0.000  0.00  0.00           C+0
HETATM   39  H   UNK     0       5.527   1.228   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   38                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   36   38                                             
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   34                                             
CONECT   11   10                                                            
CONECT   12   10   13   14   30                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   28                                             
CONECT   17   16                                                            
CONECT   18   16   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   21   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   16   29   30                                             
CONECT   29   28                                                            
CONECT   30   28   12   31   32                                             
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   10   35   38                                             
CONECT   35   34   36                                                       
CONECT   36   35    7   37                                                  
CONECT   37   36                                                            
CONECT   38   34    7    2   39                                             
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   88    0
END

View in JSmol

Synonyms

Value	Source
Ursolate lactone acetate	Generator
Ursolic acid lactone acetic acid	Generator

Chemical Formula

C₃₂H₅₀O₄

Average Mass

498.7480 Da

Monoisotopic Mass

498.37091 Da

IUPAC Name

(1S,4S,5R,8R,10S,13R,14R,17S,18R,19S,20R)-4,5,9,9,13,19,20-heptamethyl-23-oxo-24-oxahexacyclo[15.5.2.0^{1,18}.0^{4,17}.0^{5,14}.0^{8,13}]tetracosan-10-yl acetate

Traditional Name

(1S,4S,5R,8R,10S,13R,14R,17S,18R,19S,20R)-4,5,9,9,13,19,20-heptamethyl-23-oxo-24-oxahexacyclo[15.5.2.0^{1,18}.0^{4,17}.0^{5,14}.0^{8,13}]tetracosan-10-yl acetate

CAS Registry Number

Not Available

SMILES

[H][C@@]12[C@@H](C)[C@H](C)CC[C@]11CC[C@]3(C)[C@@]2(CC[C@]2([H])[C@@]4(C)CC[C@H](OC(C)=O)C(C)(C)[C@]4([H])CC[C@@]32C)OC1=O

InChI Identifier

InChI=1S/C32H50O4/c1-19-9-15-31-18-17-30(8)29(7)14-10-22-27(4,5)24(35-21(3)33)12-13-28(22,6)23(29)11-16-32(30,36-26(31)34)25(31)20(19)2/h19-20,22-25H,9-18H2,1-8H3/t19-,20+,22+,23-,24+,25-,28+,29-,30+,31+,32+/m1/s1

InChI Key

NJLCBLDWBHWOFU-NOAGMNDJSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Eucalyptus camaldulensis	LOTUS Database	35616633
Helichrysum italicum	Plant	KNApSAcK

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
Caprolactone
Oxepane
Dicarboxylic acid or derivatives
Gamma butyrolactone
Tetrahydrofuran
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	6.41	ALOGPS
logP	7.01	ChemAxon
logS	-7.2	ALOGPS
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	139.96 m³·mol⁻¹	ChemAxon
Polarizability	59.39 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

C00054172

Chemspider ID

10277039

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21669106

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 3beta-Acetoxy-28,13-ursanolide. (NP0084649)

MOL for NP0084649 (3beta-Acetoxy-28,13-ursanolide.)

3D MOL for NP0084649 (3beta-Acetoxy-28,13-ursanolide.)

3D SDF for NP0084649 (3beta-Acetoxy-28,13-ursanolide.)

3D-SDF for NP0084649 (3beta-Acetoxy-28,13-ursanolide.)

PDB for NP0084649 (3beta-Acetoxy-28,13-ursanolide.)

3D PDB for NP0084649 (3beta-Acetoxy-28,13-ursanolide.)

SMILES for NP0084649 (3beta-Acetoxy-28,13-ursanolide.)

INCHI for NP0084649 (3beta-Acetoxy-28,13-ursanolide.)

Structure for NP0084649 (3beta-Acetoxy-28,13-ursanolide.)

3D Structure for NP0084649 (3beta-Acetoxy-28,13-ursanolide.)