NP-MRD: Showing NP-Card for (+)-Isogosterone C (NP0082794)

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Record Information

Version

2.0

Created at

2022-04-29 03:52:54 UTC

Updated at

2022-04-29 03:52:54 UTC

NP-MRD ID

NP0082794

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Isogosterone C

Description

(2R,3S)-2-[(2R,2'S,3'S,4'aS,4'bS,5S,10'aR)-3'-(acetyloxy)-2',5-dihydroxy-2',4'b-dimethyl-7'-oxo-3',4',4'a,4'b,7',9',10',10'a-octahydro-2'H-spiro[oxolane-2,1'-phenanthrene]-5-yl]-6-methylheptan-3-yl acetate belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene. (+)-Isogosterone C is found in Dendronephythya sp. Based on a literature review very few articles have been published on (2R,3S)-2-[(2R,2'S,3'S,4'aS,4'bS,5S,10'aR)-3'-(acetyloxy)-2',5-dihydroxy-2',4'b-dimethyl-7'-oxo-3',4',4'a,4'b,7',9',10',10'a-octahydro-2'H-spiro[oxolane-2,1'-phenanthrene]-5-yl]-6-methylheptan-3-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292205522D          

 39 42  0  0  1  0            999 V2000
    1.8426   -8.2797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1672   -7.2960    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    1.7477   -7.4602    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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  2  1  1  1  0  0  0
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  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  5 11  1  1  0  0  0
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  4 13  1  0  0  0  0
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  4 16  1  6  0  0  0
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 17 28  1  1  0  0  0
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  3 30  1  6  0  0  0
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 37 38  1  0  0  0  0
  2 38  1  0  0  0  0
 32 38  1  0  0  0  0
 38 39  1  6  0  0  0
M  END

     RDKit          3D

 85 88  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652304292205522D          

 39 42  0  0  1  0            999 V2000
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    4.4324   -4.3952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7179   -3.9827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7179   -3.1577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0034   -4.3952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8613   -5.2202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8613   -4.3952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1468   -3.9827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5758   -3.9827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8613   -6.8702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1553   -7.2676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0192   -8.4432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1140   -9.2627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4517   -9.7546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5465  -10.5741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8842  -11.0660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9790  -11.8855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1270  -10.7383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0322   -9.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6945   -9.4269    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9374   -9.0993    0.0000 C   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  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  5 11  1  1  0  0  0
  5 12  1  6  0  0  0
  4 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  4 16  1  6  0  0  0
 15 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 18 24  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 17 28  1  1  0  0  0
 15 29  1  6  0  0  0
  3 30  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
  2 38  1  0  0  0  0
 32 38  1  0  0  0  0
 38 39  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0082794

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CC[C@H](OC(C)=O)[C@@H](C)[C@]1(O)CC[C@@]2(O1)[C@@H]1CCC3=CC(=O)C=C[C@@]3(C)[C@H]1C[C@H](OC(C)=O)[C@]2(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C31H46O8/c1-18(2)8-11-26(37-20(4)32)19(3)31(36)15-14-30(39-31)24-10-9-22-16-23(34)12-13-28(22,6)25(24)17-27(29(30,7)35)38-21(5)33/h12-13,16,18-19,24-27,35-36H,8-11,14-15,17H2,1-7H3/t19-,24-,25+,26+,27+,28-,29+,30-,31+/m1/s1

> <INCHI_KEY>
PVZHSMTYGAKBDL-OMEQVKFISA-N

> <FORMULA>
C31H46O8

> <MOLECULAR_WEIGHT>
546.701

> <EXACT_MASS>
546.319268441

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
85

> <JCHEM_AVERAGE_POLARIZABILITY>
59.67054942927525

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S)-2-[(2R,2'S,3'S,4'aS,4'bS,5S,10'aR)-3'-(acetyloxy)-2',5-dihydroxy-2',4'b-dimethyl-7'-oxo-3',4',4'a,4'b,7',9',10',10'a-octahydro-2'H-spiro[oxolane-2,1'-phenanthrene]-5-yl]-6-methylheptan-3-yl acetate

> <ALOGPS_LOGP>
3.49

> <JCHEM_LOGP>
4.127066326999997

> <ALOGPS_LOGS>
-5.18

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.960514860784418

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.729459403695191

> <JCHEM_PKA_STRONGEST_BASIC>
-3.706886032908508

> <JCHEM_POLAR_SURFACE_AREA>
119.36000000000001

> <JCHEM_REFRACTIVITY>
146.3836

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.57e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S)-2-[(2R,2'S,3'S,4'aS,4'bS,5S,10'aR)-3'-(acetyloxy)-2',5-dihydroxy-2',4'b-dimethyl-7'-oxo-3',4',4'a,9',10',10'a-hexahydrospiro[oxolane-2,1'-phenanthrene]-5-yl]-6-methylheptan-3-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       3.439 -15.456   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.853 -16.067   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.089 -15.149   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.912 -13.619   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.499 -13.008   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.262 -13.926   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.849 -13.314   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.613 -14.232   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.790 -15.762   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.801 -13.621   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.061 -11.574   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.624 -11.740   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.896 -12.079   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.356 -11.588   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.274 -12.824   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       7.382 -14.080   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       9.607 -12.054   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.607 -10.514   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.274  -9.744   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.274  -8.204   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.940  -7.434   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.940  -5.894   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.606  -8.204   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      10.941  -9.744   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      10.941  -8.204   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       9.607  -7.434   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      12.275  -7.434   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.941 -12.824   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       9.623 -13.566   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       7.502 -15.761   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.679 -17.290   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.443 -18.209   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.620 -19.738   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.384 -20.657   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       5.561 -22.186   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       3.970 -20.045   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       3.793 -18.515   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       5.030 -17.597   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       3.616 -16.985   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   38                                                  
CONECT    3    2    4   30                                                  
CONECT    4    3    5   13   16                                             
CONECT    5    4    6   11   12                                             
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    5                                                            
CONECT   12    5                                                            
CONECT   13    4   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17   29                                             
CONECT   16   15    4                                                       
CONECT   17   15   18   28                                                  
CONECT   18   17   19   24                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   18   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   17                                                            
CONECT   29   15                                                            
CONECT   30    3   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   38                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37    2   32   39                                             
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

View in JSmol

Synonyms

Value	Source
(2R,3S)-2-[(2R,2's,3's,4'AS,4'BS,5S,10'ar)-3'-(acetyloxy)-2',5-dihydroxy-2',4'b-dimethyl-7'-oxo-3',4',4'a,4'b,7',9',10',10'a-octahydro-2'H-spiro[oxolane-2,1'-phenanthrene]-5-yl]-6-methylheptan-3-yl acetic acid	Generator

Chemical Formula

C₃₁H₄₆O₈

Average Mass

546.7010 Da

Monoisotopic Mass

546.31927 Da

IUPAC Name

Traditional Name

(2R,3S)-2-[(2R,2'S,3'S,4'aS,4'bS,5S,10'aR)-3'-(acetyloxy)-2',5-dihydroxy-2',4'b-dimethyl-7'-oxo-3',4',4'a,9',10',10'a-hexahydrospiro[oxolane-2,1'-phenanthrene]-5-yl]-6-methylheptan-3-yl acetate

CAS Registry Number

Not Available

SMILES

CC(C)CC[C@H](OC(C)=O)[C@@H](C)[C@]1(O)CC[C@@]2(O1)[C@@H]1CCC3=CC(=O)C=C[C@@]3(C)[C@H]1C[C@H](OC(C)=O)[C@]2(C)O

InChI Identifier

InChI=1S/C31H46O8/c1-18(2)8-11-26(37-20(4)32)19(3)31(36)15-14-30(39-31)24-10-9-22-16-23(34)12-13-28(22,6)25(24)17-27(29(30,7)35)38-21(5)33/h12-13,16,18-19,24-27,35-36H,8-11,14-15,17H2,1-7H3/t19-,24-,25+,26+,27+,28-,29+,30-,31+/m1/s1

InChI Key

PVZHSMTYGAKBDL-OMEQVKFISA-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
Dendronephythya sp.	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Not Available

Direct Parent

Phenanthrenes and derivatives

Alternative Parents

Substituents

Phenanthrene
Dicarboxylic acid or derivatives
Tetrahydrofuran
Tertiary alcohol
Cyclic alcohol
Cyclic ketone
Ketone
Hemiacetal
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
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	3.49	ALOGPS
logP	4.13	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	11.73	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	119.36 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	146.38 m³·mol⁻¹	ChemAxon
Polarizability	59.67 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

162980612

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Isogosterone C (NP0082794)

MOL for NP0082794 ((+)-Isogosterone C)

3D MOL for NP0082794 ((+)-Isogosterone C)

3D SDF for NP0082794 ((+)-Isogosterone C)

3D-SDF for NP0082794 ((+)-Isogosterone C)

PDB for NP0082794 ((+)-Isogosterone C)

3D PDB for NP0082794 ((+)-Isogosterone C)

SMILES for NP0082794 ((+)-Isogosterone C)

INCHI for NP0082794 ((+)-Isogosterone C)

Structure for NP0082794 ((+)-Isogosterone C)

3D Structure for NP0082794 ((+)-Isogosterone C)