NP-MRD: Showing NP-Card for 14,15-Dihydro-15beta-methoxy-3-epicaryoptin (NP0074180)

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Record Information

Version

2.0

Created at

2022-04-28 19:20:57 UTC

Updated at

2022-04-28 19:20:57 UTC

NP-MRD ID

NP0074180

Secondary Accession Numbers

None

Natural Product Identification

Common Name

14,15-Dihydro-15beta-methoxy-3-epicaryoptin

Description

[(1R,2S,4aS,5R,7R,8S,8aR)-5-[(2R,3aR,5R,6aS)-5-methoxy-hexahydrofuro[2,3-b]furan-2-yl]-2,8-bis(acetyloxy)-5,7-dimethyl-octahydro-2H-spiro[naphthalene-1,2'-oxirane]-8a-yl]methyl acetate belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. 14,15-Dihydro-15beta-methoxy-3-epicaryoptin is found in Clerodendrum inerme . Based on a literature review very few articles have been published on [(1R,2S,4aS,5R,7R,8S,8aR)-5-[(2R,3aR,5R,6aS)-5-methoxy-hexahydrofuro[2,3-b]furan-2-yl]-2,8-bis(acetyloxy)-5,7-dimethyl-octahydro-2H-spiro[naphthalene-1,2'-oxirane]-8a-yl]methyl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282221202D          

 37 41  0  0  1  0            999 V2000
   -4.6622   -2.1560    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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  1 10  1  0  0  0  0
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  9 13  1  6  0  0  0
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  1 33  1  1  0  0  0
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 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304282221202D          

 37 41  0  0  1  0            999 V2000
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   -6.1766    0.2676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7486    0.3174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0238   -1.4145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8468   -1.3570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2085   -0.6155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4907    0.1598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0315   -0.5579    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  1 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 12  1  1  0  0  0
  9 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
  5 17  1  1  0  0  0
 17 18  1  0  0  0  0
 19 18  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 17 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 19 24  1  0  0  0  0
 23 25  1  6  0  0  0
 25 26  1  0  0  0  0
  5 27  1  6  0  0  0
  3 28  1  6  0  0  0
  2 29  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
  1 33  1  1  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0074180

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H]1C[C@H]2C[C@@H](O[C@H]2O1)[C@]1(C)C[C@@H](C)[C@H](OC(C)=O)[C@]2(COC(C)=O)[C@H]1CC[C@H](OC(C)=O)[C@]21CO1

> <INCHI_IDENTIFIER>
InChI=1S/C27H40O10/c1-14-11-25(5,21-9-18-10-22(31-6)37-24(18)36-21)19-7-8-20(34-16(3)29)27(13-33-27)26(19,12-32-15(2)28)23(14)35-17(4)30/h14,18-24H,7-13H2,1-6H3/t14-,18-,19+,20+,21-,22-,23+,24+,25-,26+,27-/m1/s1

> <INCHI_KEY>
JXFGBIHSAQWMCE-PAMZQGRGSA-N

> <FORMULA>
C27H40O10

> <MOLECULAR_WEIGHT>
524.607

> <EXACT_MASS>
524.262147488

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
55.29116003712019

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1R,2S,4aS,5R,7R,8S,8aR)-5-[(2R,3aR,5R,6aS)-5-methoxy-hexahydrofuro[2,3-b]furan-2-yl]-2,8-bis(acetyloxy)-5,7-dimethyl-octahydro-2H-spiro[naphthalene-1,2'-oxirane]-8a-yl]methyl acetate

> <ALOGPS_LOGP>
2.44

> <JCHEM_LOGP>
1.7545101319999974

> <ALOGPS_LOGS>
-4.19

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.730648564870146

> <JCHEM_POLAR_SURFACE_AREA>
119.12000000000003

> <JCHEM_REFRACTIVITY>
126.5718

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.39e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,4aS,5R,7R,8S,8aR)-5-[(2R,3aR,5R,6aS)-5-methoxy-hexahydrofuro[2,3-b]furan-2-yl]-2,8-bis(acetyloxy)-5,7-dimethyl-hexahydro-2H-spiro[naphthalene-1,2'-oxirane]-8a-ylmethyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -8.703  -4.025   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.756  -2.486   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.451  -1.669   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.091  -2.392   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.037  -3.932   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -7.343  -4.748   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -7.289  -6.287   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -8.595  -7.103   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -9.955  -6.380   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -10.009  -4.841   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -11.548  -4.894   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0     -10.825  -3.535   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0     -11.261  -7.196   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0     -11.207  -8.735   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -9.848  -9.458   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0     -12.513  -9.551   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.497  -3.932   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.592  -2.686   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.127  -3.162   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.127  -4.702   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -3.592  -5.177   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -0.663  -5.177   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.243  -3.932   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.663  -2.686   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.783  -3.932   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.553  -5.265   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -5.176  -5.208   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -7.504  -0.130   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0     -10.116  -1.763   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0     -10.170  -0.224   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0     -11.530   0.499   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -8.864   0.593   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -9.378  -2.640   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0     -10.914  -2.533   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0     -11.589  -1.149   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0     -12.116   0.298   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0     -13.125  -1.041   0.000  0.00  0.00           C+0
CONECT    1    2    6   10   33                                             
CONECT    2    1    3   29                                                  
CONECT    3    2    4   28                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   17   27                                             
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9    1   11   12                                             
CONECT   11   10   12                                                       
CONECT   12   11   10                                                       
CONECT   13    9   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17    5   18   21                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20   17                                                       
CONECT   22   20   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23   19                                                       
CONECT   25   23   26                                                       
CONECT   26   25                                                            
CONECT   27    5                                                            
CONECT   28    3                                                            
CONECT   29    2   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33    1   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

View in JSmol

Synonyms

Value	Source
[(1R,2S,4AS,5R,7R,8S,8ar)-5-[(2R,3ar,5R,6as)-5-methoxy-hexahydrofuro[2,3-b]furan-2-yl]-2,8-bis(acetyloxy)-5,7-dimethyl-octahydro-2H-spiro[naphthalene-1,2'-oxirane]-8a-yl]methyl acetic acid	Generator

Chemical Formula

C₂₇H₄₀O₁₀

Average Mass

524.6070 Da

Monoisotopic Mass

524.26215 Da

IUPAC Name

[(1R,2S,4aS,5R,7R,8S,8aR)-5-[(2R,3aR,5R,6aS)-5-methoxy-hexahydrofuro[2,3-b]furan-2-yl]-2,8-bis(acetyloxy)-5,7-dimethyl-octahydro-2H-spiro[naphthalene-1,2'-oxirane]-8a-yl]methyl acetate

Traditional Name

(1R,2S,4aS,5R,7R,8S,8aR)-5-[(2R,3aR,5R,6aS)-5-methoxy-hexahydrofuro[2,3-b]furan-2-yl]-2,8-bis(acetyloxy)-5,7-dimethyl-hexahydro-2H-spiro[naphthalene-1,2'-oxirane]-8a-ylmethyl acetate

CAS Registry Number

Not Available

SMILES

CO[C@H]1C[C@H]2C[C@@H](O[C@H]2O1)[C@]1(C)C[C@@H](C)[C@H](OC(C)=O)[C@]2(COC(C)=O)[C@H]1CC[C@H](OC(C)=O)[C@]21CO1

InChI Identifier

InChI=1S/C27H40O10/c1-14-11-25(5,21-9-18-10-22(31-6)37-24(18)36-21)19-7-8-20(34-16(3)29)27(13-33-27)26(19,12-32-15(2)28)23(14)35-17(4)30/h14,18-24H,7-13H2,1-6H3/t14-,18-,19+,20+,21-,22-,23+,24+,25-,26+,27-/m1/s1

InChI Key

JXFGBIHSAQWMCE-PAMZQGRGSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Volkameria inermis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic acids and derivatives

Alternative Parents

Substituents

Tricarboxylic acid or derivatives
Furofuran
Tetrahydrofuran
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen 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
logP	2.44	ALOGPS
logP	1.75	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	119.12 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	126.57 m³·mol⁻¹	ChemAxon
Polarizability	55.29 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

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

162821206

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 14,15-Dihydro-15beta-methoxy-3-epicaryoptin (NP0074180)

MOL for NP0074180 (14,15-Dihydro-15beta-methoxy-3-epicaryoptin)

3D MOL for NP0074180 (14,15-Dihydro-15beta-methoxy-3-epicaryoptin)

3D SDF for NP0074180 (14,15-Dihydro-15beta-methoxy-3-epicaryoptin)

3D-SDF for NP0074180 (14,15-Dihydro-15beta-methoxy-3-epicaryoptin)

PDB for NP0074180 (14,15-Dihydro-15beta-methoxy-3-epicaryoptin)

3D PDB for NP0074180 (14,15-Dihydro-15beta-methoxy-3-epicaryoptin)

SMILES for NP0074180 (14,15-Dihydro-15beta-methoxy-3-epicaryoptin)

INCHI for NP0074180 (14,15-Dihydro-15beta-methoxy-3-epicaryoptin)

Structure for NP0074180 (14,15-Dihydro-15beta-methoxy-3-epicaryoptin)

3D Structure for NP0074180 (14,15-Dihydro-15beta-methoxy-3-epicaryoptin)