NP-MRD: Showing NP-Card for (2r,2's,4'ar,4'bs,7's,8'ar,10'ar)-3a-hydroperoxy-2',7'-dihydroxy-5-methoxy-4'b,7,8',8',10'a-pentamethyl-2',3',4',4'a,5',6',7',8'a,9',10'-decahydro-3h-spiro[1-benzofuran-2,1'-phenanthren]-4-one (NP0319226)

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Record Information

Version

2.0

Created at

2022-09-11 20:09:04 UTC

Updated at

2022-09-11 20:09:04 UTC

NP-MRD ID

NP0319226

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,2's,4'ar,4'bs,7's,8'ar,10'ar)-3a-hydroperoxy-2',7'-dihydroxy-5-methoxy-4'b,7,8',8',10'a-pentamethyl-2',3',4',4'a,5',6',7',8'a,9',10'-decahydro-3h-spiro[1-benzofuran-2,1'-phenanthren]-4-one

Description

CHEMBL511980 belongs to the class of organic compounds known as isocopalane and spongiane diterpenoids. These are diterpenoids with a structure based on the isocopalane (Tetradecahydro-1,1,4a,7,8,8a-hexamethylphenanthrene) or the 15,16-epoxyisocopalane skeleton. (2r,2's,4'ar,4'bs,7's,8'ar,10'ar)-3a-hydroperoxy-2',7'-dihydroxy-5-methoxy-4'b,7,8',8',10'a-pentamethyl-2',3',4',4'a,5',6',7',8'a,9',10'-decahydro-3h-spiro[1-benzofuran-2,1'-phenanthren]-4-one is found in Stypopodium flabelliforme. Based on a literature review very few articles have been published on CHEMBL511980.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112222092D          

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 14 15  2  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 19  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 27 30  1  0  0  0  0
 21 30  1  0  0  0  0
 30 31  1  6  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 20 33  1  0  0  0  0
  9 33  1  0  0  0  0
 33 34  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0319226

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(C)=C2O[C@@]3(CC2(OO)C1=O)[C@@H](O)CC[C@@H]1[C@@]2(C)CC[C@H](O)C(C)(C)[C@@H]2CC[C@@]31C

> <INCHI_IDENTIFIER>
InChI=1S/C27H40O7/c1-15-13-16(32-6)21(30)26(34-31)14-27(33-22(15)26)20(29)8-7-18-24(4)11-10-19(28)23(2,3)17(24)9-12-25(18,27)5/h13,17-20,28-29,31H,7-12,14H2,1-6H3/t17-,18+,19-,20-,24-,25+,26?,27-/m0/s1

> <INCHI_KEY>
YSWYEMBQVGXRLL-RBVSQCECSA-N

> <FORMULA>
C27H40O7

> <MOLECULAR_WEIGHT>
476.61

> <EXACT_MASS>
476.277403628

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
51.70323850827416

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,2'S,4'aR,4'bS,7'S,8'aR,10'aR)-3a-hydroperoxy-2',7'-dihydroxy-5-methoxy-4'b,7,8',8',10'a-pentamethyl-3',3a,4,4',4'a,4'b,5',6',7',8',8'a,9',10',10'a-tetradecahydro-2'H,3H-spiro[1-benzofuran-2,1'-phenanthrene]-4-one

> <JCHEM_LOGP>
2.8614689389999985

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.959032492403534

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.648256767988002

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8350296819839412

> <JCHEM_POLAR_SURFACE_AREA>
105.45000000000002

> <JCHEM_REFRACTIVITY>
128.24560000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,2'S,4'aR,4'bS,7'S,8'aR,10'aR)-3a-hydroperoxy-2',7'-dihydroxy-5-methoxy-4'b,7,8',8',10'a-pentamethyl-2',3',4',4'a,5',6',7',8'a,9',10'-decahydro-3H-spiro[1-benzofuran-2,1'-phenanthrene]-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      13.057   3.323   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      11.518   3.379   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      10.700   2.075   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.420   0.714   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.602  -0.591   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.323  -1.952   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.063  -0.535   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       7.992  -1.641   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.609  -0.964   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.825   0.561   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.342   0.826   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       7.483   2.104   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       5.947   1.999   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       9.161   2.131   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.440   3.492   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.553  -2.503   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       7.857  -3.321   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.192  -3.223   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.887  -2.405   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.943  -0.866   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.638  -0.048   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.582  -1.587   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.278  -0.769   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.027   0.049   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.029   1.588   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.276   2.406   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.390   2.309   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.444   3.524   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.422   3.452   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.695   1.491   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.055   2.212   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.360   1.394   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.304  -0.145   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.375   0.961   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   14                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   16   33                                             
CONECT   10    9   11                                                       
CONECT   11   10    7   12   14                                             
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11    3   15                                                  
CONECT   15   14                                                            
CONECT   16    9   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   33                                                  
CONECT   21   20   22   23   30                                             
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29   30                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   27   21   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   20    9   34                                             
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₀O₇

Average Mass

476.6100 Da

Monoisotopic Mass

476.27740 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC1=CC(C)=C2O[C@@]3(CC2(OO)C1=O)[C@@H](O)CC[C@@H]1[C@@]2(C)CC[C@H](O)C(C)(C)[C@@H]2CC[C@@]31C

InChI Identifier

InChI=1S/C27H40O7/c1-15-13-16(32-6)21(30)26(34-31)14-27(33-22(15)26)20(29)8-7-18-24(4)11-10-19(28)23(2,3)17(24)9-12-25(18,27)5/h13,17-20,28-29,31H,7-12,14H2,1-6H3/t17-,18+,19-,20-,24-,25+,26?,27-/m0/s1

InChI Key

YSWYEMBQVGXRLL-RBVSQCECSA-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
Stypopodium flabelliforme	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isocopalane and spongiane diterpenoids. These are diterpenoids with a structure based on the isocopalane (Tetradecahydro-1,1,4a,7,8,8a-hexamethylphenanthrene) or the 15,16-epoxyisocopalane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Isocopalane and spongiane diterpenoids

Alternative Parents

Substituents

Spongiane diterpenoid
Phenanthrene
Benzofuran
Cyclic alcohol
Tetrahydrofuran
Ketone
Hydroperoxide
Secondary alcohol
Alkyl hydroperoxide
Oxacycle
Peroxol
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Alcohol
Organooxygen compound
Organic oxygen compound
Carbonyl group
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

23326725

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44559224

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,2's,4'ar,4'bs,7's,8'ar,10'ar)-3a-hydroperoxy-2',7'-dihydroxy-5-methoxy-4'b,7,8',8',10'a-pentamethyl-2',3',4',4'a,5',6',7',8'a,9',10'-decahydro-3h-spiro[1-benzofuran-2,1'-phenanthren]-4-one (NP0319226)

MOL for NP0319226 ((2r,2's,4'ar,4'bs,7's,8'ar,10'ar)-3a-hydroperoxy-2',7'-dihydroxy-5-methoxy-4'b,7,8',8',10'a-pentamethyl-2',3',4',4'a,5',6',7',8'a,9',10'-decahydro-3h-spiro[1-benzofuran-2,1'-phenanthren]-4-one)

3D MOL for NP0319226 ((2r,2's,4'ar,4'bs,7's,8'ar,10'ar)-3a-hydroperoxy-2',7'-dihydroxy-5-methoxy-4'b,7,8',8',10'a-pentamethyl-2',3',4',4'a,5',6',7',8'a,9',10'-decahydro-3h-spiro[1-benzofuran-2,1'-phenanthren]-4-one)

3D SDF for NP0319226 ((2r,2's,4'ar,4'bs,7's,8'ar,10'ar)-3a-hydroperoxy-2',7'-dihydroxy-5-methoxy-4'b,7,8',8',10'a-pentamethyl-2',3',4',4'a,5',6',7',8'a,9',10'-decahydro-3h-spiro[1-benzofuran-2,1'-phenanthren]-4-one)

3D-SDF for NP0319226 ((2r,2's,4'ar,4'bs,7's,8'ar,10'ar)-3a-hydroperoxy-2',7'-dihydroxy-5-methoxy-4'b,7,8',8',10'a-pentamethyl-2',3',4',4'a,5',6',7',8'a,9',10'-decahydro-3h-spiro[1-benzofuran-2,1'-phenanthren]-4-one)

PDB for NP0319226 ((2r,2's,4'ar,4'bs,7's,8'ar,10'ar)-3a-hydroperoxy-2',7'-dihydroxy-5-methoxy-4'b,7,8',8',10'a-pentamethyl-2',3',4',4'a,5',6',7',8'a,9',10'-decahydro-3h-spiro[1-benzofuran-2,1'-phenanthren]-4-one)

3D PDB for NP0319226 ((2r,2's,4'ar,4'bs,7's,8'ar,10'ar)-3a-hydroperoxy-2',7'-dihydroxy-5-methoxy-4'b,7,8',8',10'a-pentamethyl-2',3',4',4'a,5',6',7',8'a,9',10'-decahydro-3h-spiro[1-benzofuran-2,1'-phenanthren]-4-one)

SMILES for NP0319226 ((2r,2's,4'ar,4'bs,7's,8'ar,10'ar)-3a-hydroperoxy-2',7'-dihydroxy-5-methoxy-4'b,7,8',8',10'a-pentamethyl-2',3',4',4'a,5',6',7',8'a,9',10'-decahydro-3h-spiro[1-benzofuran-2,1'-phenanthren]-4-one)

INCHI for NP0319226 ((2r,2's,4'ar,4'bs,7's,8'ar,10'ar)-3a-hydroperoxy-2',7'-dihydroxy-5-methoxy-4'b,7,8',8',10'a-pentamethyl-2',3',4',4'a,5',6',7',8'a,9',10'-decahydro-3h-spiro[1-benzofuran-2,1'-phenanthren]-4-one)

Structure for NP0319226 ((2r,2's,4'ar,4'bs,7's,8'ar,10'ar)-3a-hydroperoxy-2',7'-dihydroxy-5-methoxy-4'b,7,8',8',10'a-pentamethyl-2',3',4',4'a,5',6',7',8'a,9',10'-decahydro-3h-spiro[1-benzofuran-2,1'-phenanthren]-4-one)

3D Structure for NP0319226 ((2r,2's,4'ar,4'bs,7's,8'ar,10'ar)-3a-hydroperoxy-2',7'-dihydroxy-5-methoxy-4'b,7,8',8',10'a-pentamethyl-2',3',4',4'a,5',6',7',8'a,9',10'-decahydro-3h-spiro[1-benzofuran-2,1'-phenanthren]-4-one)