NP-MRD: Showing NP-Card for (+)-Carthamoleusterone (NP0081786)

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Record Information

Version

2.0

Created at

2022-04-29 02:52:04 UTC

Updated at

2022-04-29 02:52:04 UTC

NP-MRD ID

NP0081786

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Carthamoleusterone

Description

Carthamoleusterone belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. (+)-Carthamoleusterone is found in Rhaponticum carthamoides . (+)-Carthamoleusterone was first documented in 2008 (PMID: 18243263). Based on a literature review very few articles have been published on Carthamoleusterone.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292204522D          

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M  END

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M  END


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   -1.1983   -2.9315    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1995   -0.2384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  6  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
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 22 26  1  0  0  0  0
 26 27  1  1  0  0  0
 24 28  1  1  0  0  0
 28 29  1  0  0  0  0
 24 30  1  6  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 22 33  1  1  0  0  0
 17 34  1  6  0  0  0
 16 35  1  1  0  0  0
  1 36  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0081786

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@@]1(CO)C[C@H](O)[C@](C)(O1)[C@H]1CC[C@@]2(O)C3=CC(=O)[C@@H]4C[C@@H](O)[C@@H](O)C[C@]4(C)[C@H]3[C@H](O)C[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C28H44O8/c1-14(2)27(13-29)12-22(34)26(5,36-27)21-6-7-28(35)16-9-17(30)15-8-18(31)19(32)10-24(15,3)23(16)20(33)11-25(21,28)4/h9,14-15,18-23,29,31-35H,6-8,10-13H2,1-5H3/t15-,18+,19-,20+,21-,22-,23+,24-,25+,26+,27-,28+/m0/s1

> <INCHI_KEY>
KFWPEZQKCIZSHF-VGKHSYQCSA-N

> <FORMULA>
C28H44O8

> <MOLECULAR_WEIGHT>
508.652

> <EXACT_MASS>
508.303618377

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
55.77482186160934

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,4S,5R,7R,11S,14S,15R,17R)-4,5,11,17-tetrahydroxy-14-[(2R,3S,5R)-3-hydroxy-5-(hydroxymethyl)-2-methyl-5-(propan-2-yl)oxolan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-one

> <ALOGPS_LOGP>
0.48

> <JCHEM_LOGP>
-0.21397643633333374

> <ALOGPS_LOGS>
-2.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.74790052716466

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.311106491226571

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8691977341890693

> <JCHEM_POLAR_SURFACE_AREA>
147.68

> <JCHEM_REFRACTIVITY>
132.8529

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.89e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,4S,5R,7R,11S,14S,15R,17R)-4,5,11,17-tetrahydroxy-14-[(2R,3S,5R)-3-hydroxy-5-(hydroxymethyl)-5-isopropyl-2-methyloxolan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-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  O   UNK     0      -6.285   0.023   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -7.811  -0.188   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -8.082  -1.704   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -6.724  -2.430   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -6.513  -3.955   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -8.195   1.304   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -7.096   2.382   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -9.285   0.256   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -10.407  -0.800   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -9.639   1.755   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -4.305  -0.550   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -3.801  -1.143   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -2.237  -5.472   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       0.372  -0.445   0.000  0.00  0.00           O+0
CONECT    1    2   18   36                                                  
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   35                                             
CONECT   17   16   18   19   34                                             
CONECT   18   17    1                                                       
CONECT   19   17   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
CONECT   22   19   23   26   33                                             
CONECT   23   22   24                                                       
CONECT   24   23   25   28   30                                             
CONECT   25   24   26                                                       
CONECT   26   25   22   27                                                  
CONECT   27   26                                                            
CONECT   28   24   29                                                       
CONECT   29   28                                                            
CONECT   30   24   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   22                                                            
CONECT   34   17                                                            
CONECT   35   16                                                            
CONECT   36    1                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₄O₈

Average Mass

508.6520 Da

Monoisotopic Mass

508.30362 Da

IUPAC Name

(1R,2R,4S,5R,7R,11S,14S,15R,17R)-4,5,11,17-tetrahydroxy-14-[(2R,3S,5R)-3-hydroxy-5-(hydroxymethyl)-2-methyl-5-(propan-2-yl)oxolan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-one

Traditional Name

(1R,2R,4S,5R,7R,11S,14S,15R,17R)-4,5,11,17-tetrahydroxy-14-[(2R,3S,5R)-3-hydroxy-5-(hydroxymethyl)-5-isopropyl-2-methyloxolan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-one

CAS Registry Number

Not Available

SMILES

CC(C)[C@@]1(CO)C[C@H](O)[C@](C)(O1)[C@H]1CC[C@@]2(O)C3=CC(=O)[C@@H]4C[C@@H](O)[C@@H](O)C[C@]4(C)[C@H]3[C@H](O)C[C@]12C

InChI Identifier

InChI=1S/C28H44O8/c1-14(2)27(13-29)12-22(34)26(5,36-27)21-6-7-28(35)16-9-17(30)15-8-18(31)19(32)10-24(15,3)23(16)20(33)11-25(21,28)4/h9,14-15,18-23,29,31-35H,6-8,10-13H2,1-5H3/t15-,18+,19-,20+,21-,22-,23+,24-,25+,26+,27-,28+/m0/s1

InChI Key

KFWPEZQKCIZSHF-VGKHSYQCSA-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 cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cholestane steroids

Direct Parent

Cholesterols and derivatives

Alternative Parents

Substituents

Cholesterol-skeleton
Ecdysteroid
22-hydroxysteroid
6-oxosteroid
3-beta-hydroxysteroid
11-hydroxysteroid
11-alpha-hydroxysteroid
Oxosteroid
Hydroxysteroid
14-hydroxysteroid
2-hydroxysteroid
3-hydroxysteroid
3-hydroxy-delta-7-steroid
Delta-7-steroid
Cyclohexenone
Monosaccharide
Tetrahydrofuran
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Ketone
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Dialkyl ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
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	0.48	ALOGPS
logP	-0.21	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	13.31	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	147.68 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	132.85 m³·mol⁻¹	ChemAxon
Polarizability	55.77 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	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

C00048346

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

101851588

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Budesinsky M, Vokac K, Harmatha J, Cvacka J: Additional minor ecdysteroid components of Leuzea carthamoides. Steroids. 2008 May;73(5):502-14. doi: 10.1016/j.steroids.2007.12.021. Epub 2007 Dec 28. [PubMed:18243263 ]

Showing NP-Card for (+)-Carthamoleusterone (NP0081786)

MOL for NP0081786 ((+)-Carthamoleusterone)

3D MOL for NP0081786 ((+)-Carthamoleusterone)

3D SDF for NP0081786 ((+)-Carthamoleusterone)

3D-SDF for NP0081786 ((+)-Carthamoleusterone)

PDB for NP0081786 ((+)-Carthamoleusterone)

3D PDB for NP0081786 ((+)-Carthamoleusterone)

SMILES for NP0081786 ((+)-Carthamoleusterone)

INCHI for NP0081786 ((+)-Carthamoleusterone)

Structure for NP0081786 ((+)-Carthamoleusterone)

3D Structure for NP0081786 ((+)-Carthamoleusterone)