NP-MRD: Showing NP-Card for (+)-Leuzeasterone (NP0081853)

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Record Information

Version

2.0

Created at

2022-04-29 02:55:21 UTC

Updated at

2022-04-29 02:55:21 UTC

NP-MRD ID

NP0081853

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Leuzeasterone

Description

(6S)-6-[(1R)-1-hydroxy-1-[(1R,2R,4S,5R,7R,11S,14S,15R)-4,5,11-trihydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-9-en-14-yl]ethyl]-4-(2-hydroxypropan-2-yl)-5,6-dihydro-2H-pyran-2-one belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (+)-Leuzeasterone is found in Rhaponticum carthamoides . Based on a literature review very few articles have been published on (6S)-6-[(1R)-1-hydroxy-1-[(1R,2R,4S,5R,7R,11S,14S,15R)-4,5,11-trihydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-9-en-14-yl]ethyl]-4-(2-hydroxypropan-2-yl)-5,6-dihydro-2H-pyran-2-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292204552D          

 37 41  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652304292204552D          

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   -5.6543    0.3469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4716    0.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7672    1.1641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5415   -0.4703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3558   -0.2237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6585   -1.2364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0361   -0.6122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1983   -2.9315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  7  5  1  1  0  0  0
  7  8  1  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  7 12  1  0  0  0  0
 11 13  1  6  0  0  0
 10 14  1  6  0  0  0
  8 15  1  6  0  0  0
  3 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  1 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 16 21  1  0  0  0  0
 19 22  1  6  0  0  0
 23 22  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 23 29  1  0  0  0  0
 25 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 30 33  1  0  0  0  0
 22 34  1  6  0  0  0
 22 35  1  6  0  0  0
 17 36  1  6  0  0  0
 16 37  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0081853

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(O)C1=CC(=O)O[C@@H](C1)[C@](C)(O)[C@H]1CC[C@@]2(O)C3=CC(=O)[C@@H]4C[C@@H](O)[C@@H](O)C[C@]4(C)[C@H]3CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C29H42O8/c1-25(2,34)15-10-23(37-24(33)11-15)28(5,35)22-7-9-29(36)17-12-19(30)18-13-20(31)21(32)14-26(18,3)16(17)6-8-27(22,29)4/h11-12,16,18,20-23,31-32,34-36H,6-10,13-14H2,1-5H3/t16-,18-,20+,21-,22-,23-,26+,27+,28+,29+/m0/s1

> <INCHI_KEY>
MUCBZHHNTRNVMC-WNOPJWQXSA-N

> <FORMULA>
C29H42O8

> <MOLECULAR_WEIGHT>
518.647

> <EXACT_MASS>
518.287968312

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
56.76034217236898

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6S)-6-[(1R)-1-hydroxy-1-[(1R,2R,4S,5R,7R,11S,14S,15R)-4,5,11-trihydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-14-yl]ethyl]-4-(2-hydroxypropan-2-yl)-5,6-dihydro-2H-pyran-2-one

> <ALOGPS_LOGP>
1.68

> <JCHEM_LOGP>
1.0290857840000007

> <ALOGPS_LOGS>
-3.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.678156954909998

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.191142169312979

> <JCHEM_PKA_STRONGEST_BASIC>
-2.945925007121666

> <JCHEM_POLAR_SURFACE_AREA>
144.52

> <JCHEM_REFRACTIVITY>
136.87130000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.87e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6S)-6-[(1R)-1-hydroxy-1-[(1R,2R,4S,5R,7R,11S,14S,15R)-4,5,11-trihydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-14-yl]ethyl]-4-(2-hydroxypropan-2-yl)-5,6-dihydropyran-2-one

> <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      -0.620  -1.622   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.097  -3.071   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.090  -4.248   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.567  -5.696   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.949  -5.967   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.473  -7.416   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.942  -4.790   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.419  -3.342   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.412  -2.164   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.928  -2.436   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.451  -3.884   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.458  -5.061   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.967  -4.155   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       4.920  -1.258   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.896  -1.893   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.606  -3.977   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.129  -2.529   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.136  -1.351   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.668  -2.579   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.096  -4.058   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.822  -4.922   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.613  -1.363   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -6.559  -0.147   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -8.084  -0.358   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -9.029   0.858   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -8.449   2.285   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -6.923   2.495   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -6.343   3.922   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -5.978   1.280   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0     -10.555   0.648   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -12.080   0.437   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0     -10.765   2.173   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0     -10.344  -0.878   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -4.398  -0.418   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -6.829  -2.308   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -3.801  -1.143   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -2.237  -5.472   0.000  0.00  0.00           O+0
CONECT    1    2   18                                                       
CONECT    2    1    3    8                                                  
CONECT    3    2    4   16                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   12                                                  
CONECT    8    7    2    9   15                                             
CONECT    9    8   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11    7                                                       
CONECT   13   11                                                            
CONECT   14   10                                                            
CONECT   15    8                                                            
CONECT   16    3   17   21   37                                             
CONECT   17   16   18   19   36                                             
CONECT   18   17    1                                                       
CONECT   19   17   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
CONECT   22   19   23   34   35                                             
CONECT   23   22   24   29                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   23                                                       
CONECT   30   25   31   32   33                                             
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   30                                                            
CONECT   34   22                                                            
CONECT   35   22                                                            
CONECT   36   17                                                            
CONECT   37   16                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₄₂O₈

Average Mass

518.6470 Da

Monoisotopic Mass

518.28797 Da

IUPAC Name

(6S)-6-[(1R)-1-hydroxy-1-[(1R,2R,4S,5R,7R,11S,14S,15R)-4,5,11-trihydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-14-yl]ethyl]-4-(2-hydroxypropan-2-yl)-5,6-dihydro-2H-pyran-2-one

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(C)(O)C1=CC(=O)O[C@@H](C1)[C@](C)(O)[C@H]1CC[C@@]2(O)C3=CC(=O)[C@@H]4C[C@@H](O)[C@@H](O)C[C@]4(C)[C@H]3CC[C@]12C

InChI Identifier

InChI=1S/C29H42O8/c1-25(2,34)15-10-23(37-24(33)11-15)28(5,35)22-7-9-29(36)17-12-19(30)18-13-20(31)21(32)14-26(18,3)16(17)6-8-27(22,29)4/h11-12,16,18,20-23,31-32,34-36H,6-10,13-14H2,1-5H3/t16-,18-,20+,21-,22-,23-,26+,27+,28+,29+/m0/s1

InChI Key

MUCBZHHNTRNVMC-WNOPJWQXSA-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
Rhaponticum carthamoides	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
Cholesterol-skeleton
Cholestane-skeleton
Ecdysteroid
Steroid lactone
20-hydroxysteroid
6-oxosteroid
3-beta-hydroxysteroid
Oxosteroid
Hydroxysteroid
14-hydroxysteroid
2-hydroxysteroid
3-hydroxysteroid
3-hydroxy-delta-7-steroid
Steroid
Delta-7-steroid
Cyclohexenone
Dihydropyranone
Pyran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	1.68	ALOGPS
logP	1.03	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	13.19	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	144.52 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	136.87 m³·mol⁻¹	ChemAxon
Polarizability	56.76 Å³	ChemAxon
Number of Rings	5	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

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

162868258

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Leuzeasterone (NP0081853)

MOL for NP0081853 ((+)-Leuzeasterone)

3D MOL for NP0081853 ((+)-Leuzeasterone)

3D SDF for NP0081853 ((+)-Leuzeasterone)

3D-SDF for NP0081853 ((+)-Leuzeasterone)

PDB for NP0081853 ((+)-Leuzeasterone)

3D PDB for NP0081853 ((+)-Leuzeasterone)

SMILES for NP0081853 ((+)-Leuzeasterone)

INCHI for NP0081853 ((+)-Leuzeasterone)

Structure for NP0081853 ((+)-Leuzeasterone)

3D Structure for NP0081853 ((+)-Leuzeasterone)