NP-MRD: Showing NP-Card for (1s,3r,5s,6r,8r,10s,15s,16s)-10-hydroxy-3-isopropyl-14,14,17-trimethyl-6-(2-methylprop-1-en-1-yl)-4-oxahexacyclo[14.3.1.1⁵,⁸.0¹,⁸.0³,⁵.0¹⁰,¹⁵]henicos-17-ene-2,21-dione (NP0202788)

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Record Information

Version

2.0

Created at

2022-09-04 22:04:45 UTC

Updated at

2022-09-04 22:04:46 UTC

NP-MRD ID

NP0202788

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3r,5s,6r,8r,10s,15s,16s)-10-hydroxy-3-isopropyl-14,14,17-trimethyl-6-(2-methylprop-1-en-1-yl)-4-oxahexacyclo[14.3.1.1⁵,⁸.0¹,⁸.0³,⁵.0¹⁰,¹⁵]henicos-17-ene-2,21-dione

Description

Isoperadione belongs to the class of organic compounds known as monoterpenoids. Monoterpenoids are compounds containing a chain of two isoprene units. (1s,3r,5s,6r,8r,10s,15s,16s)-10-hydroxy-3-isopropyl-14,14,17-trimethyl-6-(2-methylprop-1-en-1-yl)-4-oxahexacyclo[14.3.1.1⁵,⁸.0¹,⁸.0³,⁵.0¹⁰,¹⁵]henicos-17-ene-2,21-dione is found in Salvia bucharica. Based on a literature review very few articles have been published on Isoperadione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052200042D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309052200042D          

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  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 17 14  1  6  0  0  0
  9 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 20 19  1  6  0  0  0
  7 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  0  0  0  0
 20 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  1  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 27 31  1  0  0  0  0
 31 32  1  0  0  0  0
  5 32  1  0  0  0  0
 27 32  1  0  0  0  0
 32 33  1  6  0  0  0
  7 33  1  6  0  0  0
 33 34  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0202788

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@@]12O[C@@]11[C@H](C[C@]3(C[C@@]4(O)CCCC(C)(C)[C@@H]4[C@@H]4C[C@]3(CC=C4C)C2=O)C1=O)C=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C30H42O4/c1-17(2)13-20-14-27-16-28(33)11-8-10-25(6,7)22(28)21-15-26(27,12-9-19(21)5)23(31)29(18(3)4)30(20,34-29)24(27)32/h9,13,18,20-22,33H,8,10-12,14-16H2,1-7H3/t20-,21+,22-,26+,27-,28-,29-,30+/m0/s1

> <INCHI_KEY>
YNOSWMBOMJTLHL-YSYMETDRSA-N

> <FORMULA>
C30H42O4

> <MOLECULAR_WEIGHT>
466.662

> <EXACT_MASS>
466.308309832

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
53.61504833299748

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3R,5S,6R,8R,10S,15S,16S)-10-hydroxy-14,14,17-trimethyl-6-(2-methylprop-1-en-1-yl)-3-(propan-2-yl)-4-oxahexacyclo[14.3.1.1^{5,8}.0^{1,8}.0^{3,5}.0^{10,15}]henicos-17-ene-2,21-dione

> <JCHEM_LOGP>
6.109712850333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.480512457934953

> <JCHEM_PKA_STRONGEST_BASIC>
-3.026023850899251

> <JCHEM_POLAR_SURFACE_AREA>
66.9

> <JCHEM_REFRACTIVITY>
133.69389999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3R,5S,6R,8R,10S,15S,16S)-10-hydroxy-3-isopropyl-14,14,17-trimethyl-6-(2-methylprop-1-en-1-yl)-4-oxahexacyclo[14.3.1.1^{5,8}.0^{1,8}.0^{3,5}.0^{10,15}]henicos-17-ene-2,21-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       1.008   7.110   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.661   5.715   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.781   4.452   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.196   5.584   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.850   4.190   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.434   3.907   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.691   2.253   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.074   3.103   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.531   2.552   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.216   4.060   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       9.633   3.627   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.116   3.210   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.495   1.717   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.393   0.642   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.643  -0.257   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.724  -0.745   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.910   1.060   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.008  -0.335   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.669   0.221   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.333   0.535   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.946  -1.100   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.003  -2.286   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.536  -1.884   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.604  -2.994   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.725   0.118   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       3.326  -1.369   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.579   1.247   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.477   0.172   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.005   0.589   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.857  -1.320   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       1.513   2.385   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       3.043   2.772   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.407   2.391   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       4.117   0.878   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   32                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   20   33                                             
CONECT    8    7    9                                                       
CONECT    9    8   10   11   17                                             
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14    9   18                                                  
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19    7   21   25                                             
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   18   24                                                  
CONECT   24   23                                                            
CONECT   25   20   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   31   32                                             
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   27   32                                                       
CONECT   32   31    5   27   33                                             
CONECT   33   32    7   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₂O₄

Average Mass

466.6620 Da

Monoisotopic Mass

466.30831 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(C)[C@@]12O[C@@]11[C@H](C[C@]3(C[C@@]4(O)CCCC(C)(C)[C@@H]4[C@@H]4C[C@]3(CC=C4C)C2=O)C1=O)C=C(C)C

InChI Identifier

InChI=1S/C30H42O4/c1-17(2)13-20-14-27-16-28(33)11-8-10-25(6,7)22(28)21-15-26(27,12-9-19(21)5)23(31)29(18(3)4)30(20,34-29)24(27)32/h9,13,18,20-22,33H,8,10-12,14-16H2,1-7H3/t20-,21+,22-,26+,27-,28-,29-,30+/m0/s1

InChI Key

YNOSWMBOMJTLHL-YSYMETDRSA-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
Salvia bucharica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as monoterpenoids. Monoterpenoids are compounds containing a chain of two isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Monoterpenoids

Alternative Parents

Substituents

Monoterpenoid
Oxepane
Tertiary alcohol
Cyclic alcohol
Ketone
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
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

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

100970221

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,3r,5s,6r,8r,10s,15s,16s)-10-hydroxy-3-isopropyl-14,14,17-trimethyl-6-(2-methylprop-1-en-1-yl)-4-oxahexacyclo[14.3.1.1⁵,⁸.0¹,⁸.0³,⁵.0¹⁰,¹⁵]henicos-17-ene-2,21-dione (NP0202788)

MOL for NP0202788 ((1s,3r,5s,6r,8r,10s,15s,16s)-10-hydroxy-3-isopropyl-14,14,17-trimethyl-6-(2-methylprop-1-en-1-yl)-4-oxahexacyclo[14.3.1.1⁵,⁸.0¹,⁸.0³,⁵.0¹⁰,¹⁵]henicos-17-ene-2,21-dione)

3D MOL for NP0202788 ((1s,3r,5s,6r,8r,10s,15s,16s)-10-hydroxy-3-isopropyl-14,14,17-trimethyl-6-(2-methylprop-1-en-1-yl)-4-oxahexacyclo[14.3.1.1⁵,⁸.0¹,⁸.0³,⁵.0¹⁰,¹⁵]henicos-17-ene-2,21-dione)

3D SDF for NP0202788 ((1s,3r,5s,6r,8r,10s,15s,16s)-10-hydroxy-3-isopropyl-14,14,17-trimethyl-6-(2-methylprop-1-en-1-yl)-4-oxahexacyclo[14.3.1.1⁵,⁸.0¹,⁸.0³,⁵.0¹⁰,¹⁵]henicos-17-ene-2,21-dione)

3D-SDF for NP0202788 ((1s,3r,5s,6r,8r,10s,15s,16s)-10-hydroxy-3-isopropyl-14,14,17-trimethyl-6-(2-methylprop-1-en-1-yl)-4-oxahexacyclo[14.3.1.1⁵,⁸.0¹,⁸.0³,⁵.0¹⁰,¹⁵]henicos-17-ene-2,21-dione)

PDB for NP0202788 ((1s,3r,5s,6r,8r,10s,15s,16s)-10-hydroxy-3-isopropyl-14,14,17-trimethyl-6-(2-methylprop-1-en-1-yl)-4-oxahexacyclo[14.3.1.1⁵,⁸.0¹,⁸.0³,⁵.0¹⁰,¹⁵]henicos-17-ene-2,21-dione)

3D PDB for NP0202788 ((1s,3r,5s,6r,8r,10s,15s,16s)-10-hydroxy-3-isopropyl-14,14,17-trimethyl-6-(2-methylprop-1-en-1-yl)-4-oxahexacyclo[14.3.1.1⁵,⁸.0¹,⁸.0³,⁵.0¹⁰,¹⁵]henicos-17-ene-2,21-dione)

SMILES for NP0202788 ((1s,3r,5s,6r,8r,10s,15s,16s)-10-hydroxy-3-isopropyl-14,14,17-trimethyl-6-(2-methylprop-1-en-1-yl)-4-oxahexacyclo[14.3.1.1⁵,⁸.0¹,⁸.0³,⁵.0¹⁰,¹⁵]henicos-17-ene-2,21-dione)

INCHI for NP0202788 ((1s,3r,5s,6r,8r,10s,15s,16s)-10-hydroxy-3-isopropyl-14,14,17-trimethyl-6-(2-methylprop-1-en-1-yl)-4-oxahexacyclo[14.3.1.1⁵,⁸.0¹,⁸.0³,⁵.0¹⁰,¹⁵]henicos-17-ene-2,21-dione)

Structure for NP0202788 ((1s,3r,5s,6r,8r,10s,15s,16s)-10-hydroxy-3-isopropyl-14,14,17-trimethyl-6-(2-methylprop-1-en-1-yl)-4-oxahexacyclo[14.3.1.1⁵,⁸.0¹,⁸.0³,⁵.0¹⁰,¹⁵]henicos-17-ene-2,21-dione)

3D Structure for NP0202788 ((1s,3r,5s,6r,8r,10s,15s,16s)-10-hydroxy-3-isopropyl-14,14,17-trimethyl-6-(2-methylprop-1-en-1-yl)-4-oxahexacyclo[14.3.1.1⁵,⁸.0¹,⁸.0³,⁵.0¹⁰,¹⁵]henicos-17-ene-2,21-dione)