NP-MRD: Showing NP-Card for (1r,2s,4s,4as,5s,5's,6r,8as)-4,6-bis(acetyloxy)-5'-(2-hydroxyethyl)-2,5,5',8a-tetramethyl-3-oxo-hexahydrospiro[naphthalene-1,2'-oxolan]-5-ylmethyl acetate (NP0220211)

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Record Information

Version

2.0

Created at

2022-09-05 21:27:38 UTC

Updated at

2022-09-05 21:27:38 UTC

NP-MRD ID

NP0220211

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2s,4s,4as,5s,5's,6r,8as)-4,6-bis(acetyloxy)-5'-(2-hydroxyethyl)-2,5,5',8a-tetramethyl-3-oxo-hexahydrospiro[naphthalene-1,2'-oxolan]-5-ylmethyl acetate

Description

CHEMBL3608483 belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. (1r,2s,4s,4as,5s,5's,6r,8as)-4,6-bis(acetyloxy)-5'-(2-hydroxyethyl)-2,5,5',8a-tetramethyl-3-oxo-hexahydrospiro[naphthalene-1,2'-oxolan]-5-ylmethyl acetate is found in Leonurus macranthus. Based on a literature review very few articles have been published on CHEMBL3608483.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052223272D          

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 16 17  1  1  0  0  0
 16 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  6  0  0  0
 21 23  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 21 26  1  0  0  0  0
 18 26  1  1  0  0  0
 18 27  1  0  0  0  0
  8 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
  6 31  1  0  0  0  0
 31 32  1  1  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0220211

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C(=O)[C@@H](OC(C)=O)[C@H]2[C@@](C)(COC(C)=O)[C@@H](CC[C@]2(C)[C@@]11CC[C@@](C)(CCO)O1)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H40O9/c1-15-20(31)21(34-18(4)30)22-24(6,14-32-16(2)28)19(33-17(3)29)8-9-25(22,7)26(15)11-10-23(5,35-26)12-13-27/h15,19,21-22,27H,8-14H2,1-7H3/t15-,19-,21-,22+,23+,24+,25+,26-/m1/s1

> <INCHI_KEY>
BTOUAJKAVXLICM-GCDFGGQNSA-N

> <FORMULA>
C26H40O9

> <MOLECULAR_WEIGHT>
496.597

> <EXACT_MASS>
496.267232868

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
52.45566333755321

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1R,2S,4S,4aS,5S,5'S,6R,8aS)-4,6-bis(acetyloxy)-5'-(2-hydroxyethyl)-2,5,5',8a-tetramethyl-3-oxo-octahydro-2H-spiro[naphthalene-1,2'-oxolane]-5-yl]methyl acetate

> <JCHEM_LOGP>
1.5444158583333327

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.367223311631577

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.709622479740506

> <JCHEM_PKA_STRONGEST_BASIC>
-2.4132504240147945

> <JCHEM_POLAR_SURFACE_AREA>
125.43

> <JCHEM_REFRACTIVITY>
123.98699999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,4S,4aS,5S,5'S,6R,8aS)-4,6-bis(acetyloxy)-5'-(2-hydroxyethyl)-2,5,5',8a-tetramethyl-3-oxo-hexahydrospiro[naphthalene-1,2'-oxolane]-5-ylmethyl acetate

> <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      -2.926   2.426   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.229   1.053   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -3.070  -0.238   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -0.691   0.969   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.005  -0.404   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.543  -0.488   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.358   1.041   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.017  -0.040   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.366   1.460   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.241   2.512   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.590   4.012   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.466   5.064   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.064   4.460   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.839   1.907   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.188   3.407   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.964   0.855   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.437   1.303   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.614  -0.645   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.127  -0.354   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.871  -1.702   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.818  -2.826   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.023  -4.145   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.047  -3.755   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.856  -5.284   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       9.084  -6.213   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       5.424  -2.173   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.141  -1.092   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.885  -2.441   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.792  -2.592   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.318  -3.040   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.194  -1.988   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -0.280  -2.435   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -0.629  -3.935   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.496  -4.987   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -2.102  -4.383   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                                                       
CONECT    6    5    7    8   31                                             
CONECT    7    6                                                            
CONECT    8    6    9   27                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    9   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   26   27                                             
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23   26                                             
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   21   18                                                       
CONECT   27   18    8   28   29                                             
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30    6   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₄₀O₉

Average Mass

496.5970 Da

Monoisotopic Mass

496.26723 Da

IUPAC Name

[(1R,2S,4S,4aS,5S,5'S,6R,8aS)-4,6-bis(acetyloxy)-5'-(2-hydroxyethyl)-2,5,5',8a-tetramethyl-3-oxo-octahydro-2H-spiro[naphthalene-1,2'-oxolane]-5-yl]methyl acetate

Traditional Name

(1R,2S,4S,4aS,5S,5'S,6R,8aS)-4,6-bis(acetyloxy)-5'-(2-hydroxyethyl)-2,5,5',8a-tetramethyl-3-oxo-hexahydrospiro[naphthalene-1,2'-oxolane]-5-ylmethyl acetate

CAS Registry Number

Not Available

SMILES

C[C@@H]1C(=O)[C@@H](OC(C)=O)[C@H]2[C@@](C)(COC(C)=O)[C@@H](CC[C@]2(C)[C@@]11CC[C@@](C)(CCO)O1)OC(C)=O

InChI Identifier

InChI=1S/C26H40O9/c1-15-20(31)21(34-18(4)30)22-24(6,14-32-16(2)28)19(33-17(3)29)8-9-25(22,7)26(15)11-10-23(5,35-26)12-13-27/h15,19,21-22,27H,8-14H2,1-7H3/t15-,19-,21-,22+,23+,24+,25+,26-/m1/s1

InChI Key

BTOUAJKAVXLICM-GCDFGGQNSA-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
Leonurus macranthus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Grindelane diterpenoid
Tricarboxylic acid or derivatives
Alpha-acyloxy ketone
Tetrahydrofuran
Carboxylic acid ester
Ketone
Cyclic ketone
Carboxylic acid derivative
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Alcohol
Organooxygen compound
Primary alcohol
Organic oxygen compound
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	1.54	ChemAxon
pKa (Strongest Acidic)	15.71	ChemAxon
pKa (Strongest Basic)	-2.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	125.43 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	123.99 m³·mol⁻¹	ChemAxon
Polarizability	52.46 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

59002216

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

122186910

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2s,4s,4as,5s,5's,6r,8as)-4,6-bis(acetyloxy)-5'-(2-hydroxyethyl)-2,5,5',8a-tetramethyl-3-oxo-hexahydrospiro[naphthalene-1,2'-oxolan]-5-ylmethyl acetate (NP0220211)

MOL for NP0220211 ((1r,2s,4s,4as,5s,5's,6r,8as)-4,6-bis(acetyloxy)-5'-(2-hydroxyethyl)-2,5,5',8a-tetramethyl-3-oxo-hexahydrospiro[naphthalene-1,2'-oxolan]-5-ylmethyl acetate)

3D MOL for NP0220211 ((1r,2s,4s,4as,5s,5's,6r,8as)-4,6-bis(acetyloxy)-5'-(2-hydroxyethyl)-2,5,5',8a-tetramethyl-3-oxo-hexahydrospiro[naphthalene-1,2'-oxolan]-5-ylmethyl acetate)

3D SDF for NP0220211 ((1r,2s,4s,4as,5s,5's,6r,8as)-4,6-bis(acetyloxy)-5'-(2-hydroxyethyl)-2,5,5',8a-tetramethyl-3-oxo-hexahydrospiro[naphthalene-1,2'-oxolan]-5-ylmethyl acetate)

3D-SDF for NP0220211 ((1r,2s,4s,4as,5s,5's,6r,8as)-4,6-bis(acetyloxy)-5'-(2-hydroxyethyl)-2,5,5',8a-tetramethyl-3-oxo-hexahydrospiro[naphthalene-1,2'-oxolan]-5-ylmethyl acetate)

PDB for NP0220211 ((1r,2s,4s,4as,5s,5's,6r,8as)-4,6-bis(acetyloxy)-5'-(2-hydroxyethyl)-2,5,5',8a-tetramethyl-3-oxo-hexahydrospiro[naphthalene-1,2'-oxolan]-5-ylmethyl acetate)

3D PDB for NP0220211 ((1r,2s,4s,4as,5s,5's,6r,8as)-4,6-bis(acetyloxy)-5'-(2-hydroxyethyl)-2,5,5',8a-tetramethyl-3-oxo-hexahydrospiro[naphthalene-1,2'-oxolan]-5-ylmethyl acetate)

SMILES for NP0220211 ((1r,2s,4s,4as,5s,5's,6r,8as)-4,6-bis(acetyloxy)-5'-(2-hydroxyethyl)-2,5,5',8a-tetramethyl-3-oxo-hexahydrospiro[naphthalene-1,2'-oxolan]-5-ylmethyl acetate)

INCHI for NP0220211 ((1r,2s,4s,4as,5s,5's,6r,8as)-4,6-bis(acetyloxy)-5'-(2-hydroxyethyl)-2,5,5',8a-tetramethyl-3-oxo-hexahydrospiro[naphthalene-1,2'-oxolan]-5-ylmethyl acetate)

Structure for NP0220211 ((1r,2s,4s,4as,5s,5's,6r,8as)-4,6-bis(acetyloxy)-5'-(2-hydroxyethyl)-2,5,5',8a-tetramethyl-3-oxo-hexahydrospiro[naphthalene-1,2'-oxolan]-5-ylmethyl acetate)

3D Structure for NP0220211 ((1r,2s,4s,4as,5s,5's,6r,8as)-4,6-bis(acetyloxy)-5'-(2-hydroxyethyl)-2,5,5',8a-tetramethyl-3-oxo-hexahydrospiro[naphthalene-1,2'-oxolan]-5-ylmethyl acetate)