NP-MRD: Showing NP-Card for nordinone (NP0153232)

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Record Information

Version

2.0

Created at

2022-09-02 09:51:32 UTC

Updated at

2022-09-02 09:51:32 UTC

NP-MRD ID

NP0153232

Secondary Accession Numbers

None

Natural Product Identification

Common Name

nordinone

Description

(1S,2R,10R,17R)-17-hydroxy-2,14,14-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-6,11(15)-dien-5-one belongs to the class of organic compounds known as oxosteroids. These are steroid derivatives carrying a C=O group attached to steroid skeleton. nordinone is found in Monocillium nordinii. Based on a literature review very few articles have been published on (1S,2R,10R,17R)-17-hydroxy-2,14,14-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-6,11(15)-dien-5-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 50 53  0  0  0  0  0  0  0  0999 V2000
    4.1545    0.4074    1.4532 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5673    0.0207    0.1145 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1899   -1.2872   -0.3148 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7397    1.1065   -0.8949 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3926    1.7981   -0.8795 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4822    0.6716   -0.5402 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0801   -0.2054    0.2345 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3865   -1.2171    1.0610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0137   -1.5208    0.5111 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6748   -2.1997    1.5232 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6444   -0.1475    0.2483 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0725    0.4226   -0.9374 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5838    1.6775   -1.4833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8990    1.1783   -2.0971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6778    0.6111   -0.9727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9713    0.9037   -0.9354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8623    0.4109    0.1198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0938    0.2916   -0.0139 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2427    0.0380    1.4140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7503    0.1839    1.4033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1298   -0.2377    0.0853 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5908   -1.6688   -0.2216 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2298    0.1469    1.4308 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6923   -0.1878    2.2830 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0766    1.4849    1.6674 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2828   -1.0766   -0.4663 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0157   -2.0151    0.4813 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7159   -1.5676   -1.2849 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5531    1.8130   -0.6326 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9351    0.6326   -1.8921 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4290    2.5748   -0.0968 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1466    2.2400   -1.8714 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9477   -2.1755    0.9979 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2833   -0.9145    2.1239 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1199   -2.0981   -0.4084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6325   -3.1670    1.3291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3504    0.4661    1.1319 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0312   -0.3426   -1.7579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8258    2.4095   -0.7135 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0559    2.0825   -2.2669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6341    0.4453   -2.8692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3675    2.0434   -2.5600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4473    1.5344   -1.6980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5375   -0.9847    1.7267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6481    0.7261    2.1842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3370   -0.4743    2.1949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4017    1.2112    1.6193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8587   -2.2176    0.6925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5414   -1.6304   -0.8324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8637   -2.1968   -0.8700 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  6
  7  2  1  0
 21 11  1  0
 12  6  1  0
 21 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  6
 10 36  1  0
 11 37  1  1
 12 38  1  6
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 16 43  1  0
 19 44  1  0
 19 45  1  0
 20 46  1  0
 20 47  1  0
 22 48  1  0
 22 49  1  0
 22 50  1  0
M  END


  Mrv1652309022211512D          

 22 25  0  0  1  0            999 V2000
    5.5996    1.1118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875    0.9666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7280    1.7894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168    0.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340   -0.2889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826    0.2174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629    0.9934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311    1.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6190    1.4789    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0872    2.1096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387    0.7029    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8705    0.0722    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5902   -0.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7781   -0.8489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4342   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976    0.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9098    0.1221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266    0.5577    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8069    1.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 11  9  1  1  0  0  0
 11 12  1  0  0  0  0
 12  6  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  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
 15 21  1  0  0  0  0
 11 21  1  0  0  0  0
 21 22  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0153232

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CCC2=C1C[C@@H](O)[C@H]1[C@H]2CCC2=CC(=O)CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O2/c1-19(2)8-7-14-15-5-4-12-10-13(21)6-9-20(12,3)18(15)17(22)11-16(14)19/h10,15,17-18,22H,4-9,11H2,1-3H3/t15-,17+,18+,20-/m0/s1

> <INCHI_KEY>
ALFAUJVLIRDQGD-MMTROXRISA-N

> <FORMULA>
C20H28O2

> <MOLECULAR_WEIGHT>
300.442

> <EXACT_MASS>
300.208930142

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
35.471300050282935

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,10R,17R)-17-hydroxy-2,14,14-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-6,11(15)-dien-5-one

> <ALOGPS_LOGP>
3.36

> <JCHEM_LOGP>
3.125251358000001

> <ALOGPS_LOGS>
-3.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.7759569375348

> <JCHEM_PKA_STRONGEST_BASIC>
-0.47828995071653246

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
89.63879999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.44e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,10R,17R)-17-hydroxy-2,14,14-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-6,11(15)-dien-5-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      10.453   2.075   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.937   1.804   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.826   3.340   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.365   0.325   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.090  -0.539   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.874   0.406   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.398   1.854   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.405   3.032   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.889   2.761   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.896   3.938   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.366   1.312   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.358   0.135   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.835  -1.314   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.319  -1.585   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.326  -0.407   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.810  -0.678   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.182   0.499   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.698   0.228   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.341   1.947   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.857   2.218   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.850   1.041   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.373   2.489   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4    7                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   21                                                  
CONECT   12   11    6   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   15   11   22                                             
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₈O₂

Average Mass

300.4420 Da

Monoisotopic Mass

300.20893 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC1(C)CCC2=C1C[C@@H](O)[C@H]1[C@H]2CCC2=CC(=O)CC[C@]12C

InChI Identifier

InChI=1S/C20H28O2/c1-19(2)8-7-14-15-5-4-12-10-13(21)6-9-20(12,3)18(15)17(22)11-16(14)19/h10,15,17-18,22H,4-9,11H2,1-3H3/t15-,17+,18+,20-/m0/s1

InChI Key

ALFAUJVLIRDQGD-MMTROXRISA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Monocillium nordinii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxosteroids. These are steroid derivatives carrying a C=O group attached to steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Oxosteroids

Direct Parent

Oxosteroids

Alternative Parents

Substituents

3-oxosteroid
Hydroxysteroid
Oxosteroid
11-alpha-hydroxysteroid
11-hydroxysteroid
Cyclohexenone
Cyclic alcohol
Secondary alcohol
Ketone
Cyclic ketone
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	3.36	ALOGPS
logP	3.13	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	18.78	ChemAxon
pKa (Strongest Basic)	-0.48	ChemAxon
Hydrogen Acceptor Count	2	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

2298522

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3033958

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for nordinone (NP0153232)

MOL for NP0153232 (nordinone)

3D MOL for NP0153232 (nordinone)

3D SDF for NP0153232 (nordinone)

3D-SDF for NP0153232 (nordinone)

PDB for NP0153232 (nordinone)

3D PDB for NP0153232 (nordinone)

SMILES for NP0153232 (nordinone)

INCHI for NP0153232 (nordinone)

Structure for NP0153232 (nordinone)

3D Structure for NP0153232 (nordinone)