NP-MRD: Showing NP-Card for (1s,2s,4r,6r,8s,9s,10r,13r,14r,17s)-8,17-dihydroxy-2,8,10,13,18,18-hexamethyl-6-(2-methylprop-1-en-1-yl)-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicos-19-ene-12,16-dione (NP0178095)

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Record Information

Version

1.0

Created at

2022-09-03 16:01:50 UTC

Updated at

2022-09-03 16:01:50 UTC

NP-MRD ID

NP0178095

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s,4r,6r,8s,9s,10r,13r,14r,17s)-8,17-dihydroxy-2,8,10,13,18,18-hexamethyl-6-(2-methylprop-1-en-1-yl)-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicos-19-ene-12,16-dione

Description

(1S,2S,4R,6R,8S,9S,10R,13R,14R,17S)-8,17-dihydroxy-2,8,10,13,18,18-hexamethyl-6-(2-methylprop-1-en-1-yl)-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]Henicos-19-ene-12,16-dione belongs to the class of organic compounds known as 11-oxosteroids. These are steroid derivatives carrying a C=O group at the 11-position of the steroid skeleton. (1s,2s,4r,6r,8s,9s,10r,13r,14r,17s)-8,17-dihydroxy-2,8,10,13,18,18-hexamethyl-6-(2-methylprop-1-en-1-yl)-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicos-19-ene-12,16-dione is found in Ecballium elaterium. Based on a literature review very few articles have been published on (1S,2S,4R,6R,8S,9S,10R,13R,14R,17S)-8,17-dihydroxy-2,8,10,13,18,18-hexamethyl-6-(2-methylprop-1-en-1-yl)-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]Henicos-19-ene-12,16-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032218012D          

 35 39  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309032218012D          

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    1.9817   -3.2104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6322   -3.7178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9248   -4.0334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0045   -2.2858    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4889   -1.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3316   -1.5323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1528   -0.8645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1522   -1.4467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6366   -2.1146    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0496   -1.4004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4123   -3.2641    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  0  0  0  0
  2  4  2  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  6  0  0  0
  7 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 19 18  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 18 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 19 28  1  0  0  0  0
 15 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 10 33  1  0  0  0  0
 13 33  1  0  0  0  0
 33 34  1  6  0  0  0
 11 35  1  0  0  0  0
  5 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0178095

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=C[C@H]1C[C@](C)(O)[C@@H]2[C@@H](C[C@@]3(C)[C@@H]4CC=C5[C@@H](CC(=O)[C@@H](O)C5(C)C)[C@]4(C)C(=O)C[C@]23C)O1

> <INCHI_IDENTIFIER>
InChI=1S/C30H44O5/c1-16(2)11-17-13-29(7,34)24-21(35-17)14-27(5)22-10-9-18-19(12-20(31)25(33)26(18,3)4)30(22,8)23(32)15-28(24,27)6/h9,11,17,19,21-22,24-25,33-34H,10,12-15H2,1-8H3/t17-,19+,21+,22-,24+,25+,27-,28+,29-,30-/m0/s1

> <INCHI_KEY>
MTVYZEDBHRQICX-YZXIXWLISA-N

> <FORMULA>
C30H44O5

> <MOLECULAR_WEIGHT>
484.677

> <EXACT_MASS>
484.318874517

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
55.38633910160491

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,4R,6R,8S,9S,10R,13R,14R,17S)-8,17-dihydroxy-2,8,10,13,18,18-hexamethyl-6-(2-methylprop-1-en-1-yl)-5-oxapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{14,19}]henicos-19-ene-12,16-dione

> <JCHEM_LOGP>
3.6172113396666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.603699728940654

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.910368611317121

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9760429684313703

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
137.1832

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,4R,6R,8S,9S,10R,13R,14R,17S)-8,17-dihydroxy-2,8,10,13,18,18-hexamethyl-6-(2-methylprop-1-en-1-yl)-5-oxapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{14,19}]henicos-19-ene-12,16-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0     -11.589  -4.988   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -10.124  -4.511   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -9.805  -3.004   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.979  -5.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.515  -5.063   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -7.196  -3.557   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.732  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.456  -1.721   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -4.519  -2.131   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -4.586  -4.109   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.905  -5.616   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.571  -6.385   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.428  -5.354   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.950  -6.818   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.896  -5.513   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.268  -6.920   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.263  -7.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.168  -5.833   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.540  -4.427   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.444  -3.180   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.976  -3.340   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.880  -2.093   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.603  -4.746   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.135  -4.906   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.699  -5.993   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.914  -6.940   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.593  -7.529   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.008  -4.267   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.913  -3.020   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.619  -2.860   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       0.285  -1.614   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -2.151  -2.701   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -3.055  -3.947   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -3.826  -2.614   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -6.370  -6.093   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   35                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11   33                                                  
CONECT   11   10   12   35                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15   33                                             
CONECT   14   13                                                            
CONECT   15   13   16   28                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   25                                                  
CONECT   19   18   20   28                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   18   26   27                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   19   15   29   30                                             
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   10   13   34                                             
CONECT   34   33                                                            
CONECT   35   11    5                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₄O₅

Average Mass

484.6770 Da

Monoisotopic Mass

484.31887 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(C)=C[C@H]1C[C@](C)(O)[C@@H]2[C@@H](C[C@@]3(C)[C@@H]4CC=C5[C@@H](CC(=O)[C@@H](O)C5(C)C)[C@]4(C)C(=O)C[C@]23C)O1

InChI Identifier

InChI=1S/C30H44O5/c1-16(2)11-17-13-29(7,34)24-21(35-17)14-27(5)22-10-9-18-19(12-20(31)25(33)26(18,3)4)30(22,8)23(32)15-28(24,27)6/h9,11,17,19,21-22,24-25,33-34H,10,12-15H2,1-8H3/t17-,19+,21+,22-,24+,25+,27-,28+,29-,30-/m0/s1

InChI Key

MTVYZEDBHRQICX-YZXIXWLISA-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
Ecballium elaterium	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 11-oxosteroids. These are steroid derivatives carrying a C=O group at the 11-position of the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Oxosteroids

Direct Parent

11-oxosteroids

Alternative Parents

Substituents

20-hydroxysteroid
3-hydroxy-delta-5-steroid
3-hydroxysteroid
14-alpha-methylsteroid
Hydroxysteroid
3-alpha-hydroxysteroid
11-oxosteroid
Delta-5-steroid
Oxane
Cyclic alcohol
Tertiary alcohol
Cyclic ketone
Ketone
Secondary alcohol
Organoheterocyclic compound
Ether
Dialkyl ether
Oxacycle
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organooxygen compound
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

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

162847483

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2s,4r,6r,8s,9s,10r,13r,14r,17s)-8,17-dihydroxy-2,8,10,13,18,18-hexamethyl-6-(2-methylprop-1-en-1-yl)-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicos-19-ene-12,16-dione (NP0178095)

MOL for NP0178095 ((1s,2s,4r,6r,8s,9s,10r,13r,14r,17s)-8,17-dihydroxy-2,8,10,13,18,18-hexamethyl-6-(2-methylprop-1-en-1-yl)-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicos-19-ene-12,16-dione)

3D MOL for NP0178095 ((1s,2s,4r,6r,8s,9s,10r,13r,14r,17s)-8,17-dihydroxy-2,8,10,13,18,18-hexamethyl-6-(2-methylprop-1-en-1-yl)-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicos-19-ene-12,16-dione)

3D SDF for NP0178095 ((1s,2s,4r,6r,8s,9s,10r,13r,14r,17s)-8,17-dihydroxy-2,8,10,13,18,18-hexamethyl-6-(2-methylprop-1-en-1-yl)-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicos-19-ene-12,16-dione)

3D-SDF for NP0178095 ((1s,2s,4r,6r,8s,9s,10r,13r,14r,17s)-8,17-dihydroxy-2,8,10,13,18,18-hexamethyl-6-(2-methylprop-1-en-1-yl)-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicos-19-ene-12,16-dione)

PDB for NP0178095 ((1s,2s,4r,6r,8s,9s,10r,13r,14r,17s)-8,17-dihydroxy-2,8,10,13,18,18-hexamethyl-6-(2-methylprop-1-en-1-yl)-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicos-19-ene-12,16-dione)

3D PDB for NP0178095 ((1s,2s,4r,6r,8s,9s,10r,13r,14r,17s)-8,17-dihydroxy-2,8,10,13,18,18-hexamethyl-6-(2-methylprop-1-en-1-yl)-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicos-19-ene-12,16-dione)

SMILES for NP0178095 ((1s,2s,4r,6r,8s,9s,10r,13r,14r,17s)-8,17-dihydroxy-2,8,10,13,18,18-hexamethyl-6-(2-methylprop-1-en-1-yl)-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicos-19-ene-12,16-dione)

INCHI for NP0178095 ((1s,2s,4r,6r,8s,9s,10r,13r,14r,17s)-8,17-dihydroxy-2,8,10,13,18,18-hexamethyl-6-(2-methylprop-1-en-1-yl)-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicos-19-ene-12,16-dione)

Structure for NP0178095 ((1s,2s,4r,6r,8s,9s,10r,13r,14r,17s)-8,17-dihydroxy-2,8,10,13,18,18-hexamethyl-6-(2-methylprop-1-en-1-yl)-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicos-19-ene-12,16-dione)

3D Structure for NP0178095 ((1s,2s,4r,6r,8s,9s,10r,13r,14r,17s)-8,17-dihydroxy-2,8,10,13,18,18-hexamethyl-6-(2-methylprop-1-en-1-yl)-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicos-19-ene-12,16-dione)