NP-MRD: Showing NP-Card for methyl (4ar,4br,7r,7ar,10ar,11s,12r,12as)-12-(acetyloxy)-11-(butanoyloxy)-1,1,4a-trimethyl-8-oxo-dodecahydrophenanthro[1,10a-c]furan-7-carboxylate (NP0159784)

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Record Information

Version

2.0

Created at

2022-09-02 17:35:38 UTC

Updated at

2022-09-02 17:35:38 UTC

NP-MRD ID

NP0159784

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (4ar,4br,7r,7ar,10ar,11s,12r,12as)-12-(acetyloxy)-11-(butanoyloxy)-1,1,4a-trimethyl-8-oxo-dodecahydrophenanthro[1,10a-c]furan-7-carboxylate

Description

Methyl (1R,2S,3R,4S,9R,10R,13R,14R)-3-(acetyloxy)-2-(butanoyloxy)-5,5,9-trimethyl-15-oxo-16-oxatetracyclo[8.7.0.0¹,¹⁴.0⁴,⁹]Heptadecane-13-carboxylate belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups. methyl (4ar,4br,7r,7ar,10ar,11s,12r,12as)-12-(acetyloxy)-11-(butanoyloxy)-1,1,4a-trimethyl-8-oxo-dodecahydrophenanthro[1,10a-c]furan-7-carboxylate is found in Aplysilla rosea. Based on a literature review very few articles have been published on methyl (1R,2S,3R,4S,9R,10R,13R,14R)-3-(acetyloxy)-2-(butanoyloxy)-5,5,9-trimethyl-15-oxo-16-oxatetracyclo[8.7.0.0¹,¹⁴.0⁴,⁹]Heptadecane-13-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022219352D          

 35 38  0  0  1  0            999 V2000
    0.6522    3.9045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3471    3.4598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3095    2.6357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0044    2.1911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7370    2.5706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9668    1.3669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7729    0.8870    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3943    1.3018    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4319    2.1259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1644    2.5054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.3803    1.8438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.4896    0.9121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6241    0.0981    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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 18 19  1  0  0  0  0
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 35 34  1  1  0  0  0
  7 35  1  0  0  0  0
 30 35  1  0  0  0  0
 22 35  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309022219352D          

 35 38  0  0  1  0            999 V2000
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  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 13  8  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 13 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 25 30  1  0  0  0  0
 30 31  1  1  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 35 34  1  1  0  0  0
  7 35  1  0  0  0  0
 30 35  1  0  0  0  0
 22 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0159784

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC(=O)O[C@@H]1[C@H](OC(C)=O)[C@H]2C(C)(C)CCC[C@]2(C)[C@H]2CC[C@H]([C@H]3C(=O)OC[C@@]123)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C27H40O8/c1-7-9-18(29)35-22-20(34-15(2)28)21-25(3,4)12-8-13-26(21,5)17-11-10-16(23(30)32-6)19-24(31)33-14-27(17,19)22/h16-17,19-22H,7-14H2,1-6H3/t16-,17-,19+,20-,21+,22-,26-,27-/m1/s1

> <INCHI_KEY>
HSNFEZIDNHOEMW-UEZFYZMHSA-N

> <FORMULA>
C27H40O8

> <MOLECULAR_WEIGHT>
492.609

> <EXACT_MASS>
492.272318248

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
52.45865925630689

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1R,2S,3R,4S,9R,10R,13R,14R)-3-(acetyloxy)-2-(butanoyloxy)-5,5,9-trimethyl-15-oxo-16-oxatetracyclo[8.7.0.0^{1,14}.0^{4,9}]heptadecane-13-carboxylate

> <ALOGPS_LOGP>
2.45

> <JCHEM_LOGP>
3.628149125666667

> <ALOGPS_LOGS>
-5.19

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.935170604547142

> <JCHEM_PKA_STRONGEST_BASIC>
-6.45190429601766

> <JCHEM_POLAR_SURFACE_AREA>
105.2

> <JCHEM_REFRACTIVITY>
124.43619999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.19e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,2S,3R,4S,9R,10R,13R,14R)-3-(acetyloxy)-2-(butanoyloxy)-5,5,9-trimethyl-15-oxo-16-oxatetracyclo[8.7.0.0^{1,14}.0^{4,9}]heptadecane-13-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       1.217   7.288   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.515   6.458   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.444   4.920   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.742   4.090   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.109   4.798   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       3.671   2.552   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       5.176   1.656   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.336   2.430   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.406   3.968   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       7.774   4.677   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.844   6.215   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       9.071   3.847   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       7.633   1.600   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.001   2.308   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.065   3.532   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.043   3.442   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.298   1.478   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.228  -0.060   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.860  -0.768   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.563   0.062   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.493  -1.477   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.196  -0.647   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.125  -2.185   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.758  -2.894   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.461  -2.064   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.093  -2.772   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.796  -1.942   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       2.023  -4.310   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.656  -5.019   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.531  -0.525   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.435   0.556   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.915   0.305   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       3.125   1.933   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       4.647   1.703   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.898   0.183   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   35                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    8   14   20                                                  
CONECT   14   13   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   13   21   22                                             
CONECT   21   20                                                            
CONECT   22   20   23   35                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28                                                            
CONECT   30   25   31   35                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34    7   30   22                                             
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Value	Source
Methyl (1R,2S,3R,4S,9R,10R,13R,14R)-3-(acetyloxy)-2-(butanoyloxy)-5,5,9-trimethyl-15-oxo-16-oxatetracyclo[8.7.0.0,.0,]heptadecane-13-carboxylic acid	Generator

Chemical Formula

C₂₇H₄₀O₈

Average Mass

492.6090 Da

Monoisotopic Mass

492.27232 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CCCC(=O)O[C@@H]1[C@H](OC(C)=O)[C@H]2C(C)(C)CCC[C@]2(C)[C@H]2CC[C@H]([C@H]3C(=O)OC[C@@]123)C(=O)OC

InChI Identifier

InChI=1S/C27H40O8/c1-7-9-18(29)35-22-20(34-15(2)28)21-25(3,4)12-8-13-26(21,5)17-11-10-16(23(30)32-6)19-24(31)33-14-27(17,19)22/h16-17,19-22H,7-14H2,1-6H3/t16-,17-,19+,20-,21+,22-,26-,27-/m1/s1

InChI Key

HSNFEZIDNHOEMW-UEZFYZMHSA-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
Aplysilla rosea	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tetracarboxylic acids and derivatives

Direct Parent

Tetracarboxylic acids and derivatives

Alternative Parents

Substituents

Tetracarboxylic acid or derivatives
Fatty acid ester
Gamma butyrolactone
Fatty acyl
Tetrahydrofuran
Methyl ester
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Organic oxide
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	2.45	ALOGPS
logS	-5.2	ALOGPS

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

10476905

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15818339

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (4ar,4br,7r,7ar,10ar,11s,12r,12as)-12-(acetyloxy)-11-(butanoyloxy)-1,1,4a-trimethyl-8-oxo-dodecahydrophenanthro[1,10a-c]furan-7-carboxylate (NP0159784)

MOL for NP0159784 (methyl (4ar,4br,7r,7ar,10ar,11s,12r,12as)-12-(acetyloxy)-11-(butanoyloxy)-1,1,4a-trimethyl-8-oxo-dodecahydrophenanthro[1,10a-c]furan-7-carboxylate)

3D MOL for NP0159784 (methyl (4ar,4br,7r,7ar,10ar,11s,12r,12as)-12-(acetyloxy)-11-(butanoyloxy)-1,1,4a-trimethyl-8-oxo-dodecahydrophenanthro[1,10a-c]furan-7-carboxylate)

3D SDF for NP0159784 (methyl (4ar,4br,7r,7ar,10ar,11s,12r,12as)-12-(acetyloxy)-11-(butanoyloxy)-1,1,4a-trimethyl-8-oxo-dodecahydrophenanthro[1,10a-c]furan-7-carboxylate)

3D-SDF for NP0159784 (methyl (4ar,4br,7r,7ar,10ar,11s,12r,12as)-12-(acetyloxy)-11-(butanoyloxy)-1,1,4a-trimethyl-8-oxo-dodecahydrophenanthro[1,10a-c]furan-7-carboxylate)

PDB for NP0159784 (methyl (4ar,4br,7r,7ar,10ar,11s,12r,12as)-12-(acetyloxy)-11-(butanoyloxy)-1,1,4a-trimethyl-8-oxo-dodecahydrophenanthro[1,10a-c]furan-7-carboxylate)

3D PDB for NP0159784 (methyl (4ar,4br,7r,7ar,10ar,11s,12r,12as)-12-(acetyloxy)-11-(butanoyloxy)-1,1,4a-trimethyl-8-oxo-dodecahydrophenanthro[1,10a-c]furan-7-carboxylate)

SMILES for NP0159784 (methyl (4ar,4br,7r,7ar,10ar,11s,12r,12as)-12-(acetyloxy)-11-(butanoyloxy)-1,1,4a-trimethyl-8-oxo-dodecahydrophenanthro[1,10a-c]furan-7-carboxylate)

INCHI for NP0159784 (methyl (4ar,4br,7r,7ar,10ar,11s,12r,12as)-12-(acetyloxy)-11-(butanoyloxy)-1,1,4a-trimethyl-8-oxo-dodecahydrophenanthro[1,10a-c]furan-7-carboxylate)

Structure for NP0159784 (methyl (4ar,4br,7r,7ar,10ar,11s,12r,12as)-12-(acetyloxy)-11-(butanoyloxy)-1,1,4a-trimethyl-8-oxo-dodecahydrophenanthro[1,10a-c]furan-7-carboxylate)

3D Structure for NP0159784 (methyl (4ar,4br,7r,7ar,10ar,11s,12r,12as)-12-(acetyloxy)-11-(butanoyloxy)-1,1,4a-trimethyl-8-oxo-dodecahydrophenanthro[1,10a-c]furan-7-carboxylate)