NP-MRD: Showing NP-Card for (+)-Amotsangin D (NP0076158)

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Record Information

Version

2.0

Created at

2022-04-28 21:19:16 UTC

Updated at

2022-04-28 21:19:16 UTC

NP-MRD ID

NP0076158

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Amotsangin D

Description

(R,1bR,2R,3R,4R,5aS,5bR)-3-(acetyloxy)--(furan-3-yl)-4-[(3R,4S)-3-(2-methoxy-2-oxoethyl)-2,2,4-trimethyl-7-oxo-2,3,4,7-tetrahydrooxepin-4-yl]-1b-methyl-5-methylidene-octahydroindeno[1,7a-b]oxiren-2-yl propanoate belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups. (+)-Amotsangin D is found in Amoora tsangii. Based on a literature review very few articles have been published on (R,1bR,2R,3R,4R,5aS,5bR)-3-(acetyloxy)--(furan-3-yl)-4-[(3R,4S)-3-(2-methoxy-2-oxoethyl)-2,2,4-trimethyl-7-oxo-2,3,4,7-tetrahydrooxepin-4-yl]-1b-methyl-5-methylidene-octahydroindeno[1,7a-b]oxiren-2-yl propanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282223192D          

 42 46  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652304282223192D          

 42 46  0  0  1  0            999 V2000
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    3.7828    2.6290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6254    2.9382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8341    0.5042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8359    0.7399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4001    1.3892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6727    0.4538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7044   -1.1015    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3284   -1.6411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2955   -2.4655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6305   -2.9537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8442   -3.7921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8341   -2.7382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5061   -1.9813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8934   -1.2528    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2330   -0.6348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6052   -0.9246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7616   -1.7346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2286   -0.3841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0083   -0.6537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1140   -2.6928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4450   -1.8760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6094   -1.0045    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  2  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 11 15  2  0  0  0  0
  8 16  1  6  0  0  0
  5 16  1  6  0  0  0
  4 17  1  1  0  0  0
  3 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
  2 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
  1 27  1  6  0  0  0
 27 28  1  6  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 27 34  1  0  0  0  0
 34 35  1  6  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 33 40  1  0  0  0  0
 33 41  1  0  0  0  0
 27 42  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0076158

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(=O)O[C@H]1[C@H](OC(C)=O)[C@@H](C(=C)[C@@]23O[C@@H]2C[C@@H](C2=COC=C2)[C@]13C)[C@]1(C)C=CC(=O)OC(C)(C)[C@@H]1CC(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C32H40O10/c1-9-23(34)40-28-27(39-18(3)33)26(30(6)12-10-24(35)42-29(4,5)21(30)15-25(36)37-8)17(2)32-22(41-32)14-20(31(28,32)7)19-11-13-38-16-19/h10-13,16,20-22,26-28H,2,9,14-15H2,1,3-8H3/t20-,21-,22+,26+,27+,28-,30+,31+,32+/m0/s1

> <INCHI_KEY>
GSUKMHXCYNYYGR-YRRDFDOLSA-N

> <FORMULA>
C32H40O10

> <MOLECULAR_WEIGHT>
584.662

> <EXACT_MASS>
584.262147488

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
59.71697626965855

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(R,1bR,2R,3R,4R,5aS,5bR)-3-(acetyloxy)--(furan-3-yl)-4-[(3R,4S)-3-(2-methoxy-2-oxoethyl)-2,2,4-trimethyl-7-oxo-2,3,4,7-tetrahydrooxepin-4-yl]-1b-methyl-5-methylidene-octahydroindeno[1,7a-b]oxiren-2-yl propanoate

> <ALOGPS_LOGP>
4.83

> <JCHEM_LOGP>
3.5846283376666683

> <ALOGPS_LOGS>
-4.55

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8598624535109276

> <JCHEM_POLAR_SURFACE_AREA>
130.87

> <JCHEM_REFRACTIVITY>
148.1512

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.64e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(R,1bR,2R,3R,4R,5aS,5bR)-3-(acetyloxy)--(furan-3-yl)-4-[(3R,4S)-3-(2-methoxy-2-oxoethyl)-2,2,4-trimethyl-7-oxo-3H-oxepin-4-yl]-1b-methyl-5-methylidene-hexahydroindeno[1,7a-b]oxiren-2-yl propanoate

> <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       2.569  -0.643   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.487   0.594   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.874   2.007   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.344   2.183   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.427   0.946   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.039  -0.467   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.633  -0.936   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.033   1.437   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.018   2.977   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.452   3.438   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.942   4.898   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.411   5.359   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.427   6.899   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.967   7.389   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.049   6.152   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.728  -0.073   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.067   3.622   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.554   2.596   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.878   3.672   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.171   2.108   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       7.061   4.907   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.634   5.485   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.290   0.941   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       7.160   1.381   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       8.214   2.593   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       8.722   0.847   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.182  -2.056   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.346  -3.063   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.285  -4.602   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.044  -5.514   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       3.443  -7.079   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       1.557  -5.111   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       0.945  -3.698   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.668  -2.339   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       0.435  -1.185   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -1.130  -1.726   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -1.422  -3.238   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -2.293  -0.717   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -3.749  -1.220   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -0.213  -5.027   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -0.831  -3.502   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       4.871  -1.875   0.000  0.00  0.00           C+0
CONECT    1    2    6   27                                                  
CONECT    2    1    3   23                                                  
CONECT    3    2    4   18                                                  
CONECT    4    3    5   10   17                                             
CONECT    5    4    6    8   16                                             
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9   16                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4   11                                                  
CONECT   11   10   12   15                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   11                                                       
CONECT   16    8    5                                                       
CONECT   17    4                                                            
CONECT   18    3   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21                                                            
CONECT   23    2   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27    1   28   34   42                                             
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34   40   41                                             
CONECT   34   33   27   35                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38                                                            
CONECT   40   33                                                            
CONECT   41   33                                                            
CONECT   42   27                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   92    0
END

View in JSmol

Synonyms

Value	Source
(R,1BR,2R,3R,4R,5AS,5BR)-3-(acetyloxy)--(furan-3-yl)-4-[(3R,4S)-3-(2-methoxy-2-oxoethyl)-2,2,4-trimethyl-7-oxo-2,3,4,7-tetrahydrooxepin-4-yl]-1b-methyl-5-methylidene-octahydroindeno[1,7a-b]oxiren-2-yl propanoic acid	Generator

Chemical Formula

C₃₂H₄₀O₁₀

Average Mass

584.6620 Da

Monoisotopic Mass

584.26215 Da

IUPAC Name

Traditional Name

(R,1bR,2R,3R,4R,5aS,5bR)-3-(acetyloxy)--(furan-3-yl)-4-[(3R,4S)-3-(2-methoxy-2-oxoethyl)-2,2,4-trimethyl-7-oxo-3H-oxepin-4-yl]-1b-methyl-5-methylidene-hexahydroindeno[1,7a-b]oxiren-2-yl propanoate

CAS Registry Number

Not Available

SMILES

CCC(=O)O[C@H]1[C@H](OC(C)=O)[C@@H](C(=C)[C@@]23O[C@@H]2C[C@@H](C2=COC=C2)[C@]13C)[C@]1(C)C=CC(=O)OC(C)(C)[C@@H]1CC(=O)OC

InChI Identifier

InChI=1S/C32H40O10/c1-9-23(34)40-28-27(39-18(3)33)26(30(6)12-10-24(35)42-29(4,5)21(30)15-25(36)37-8)17(2)32-22(41-32)14-20(31(28,32)7)19-11-13-38-16-19/h10-13,16,20-22,26-28H,2,9,14-15H2,1,3-8H3/t20-,21-,22+,26+,27+,28-,30+,31+,32+/m0/s1

InChI Key

GSUKMHXCYNYYGR-YRRDFDOLSA-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
Amoora tsangii	Plant	KNApSAcK

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
Oxane
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Furan
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	4.83	ALOGPS
logP	3.58	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	130.87 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	148.15 m³·mol⁻¹	ChemAxon
Polarizability	59.72 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

163049802

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Amotsangin D (NP0076158)

MOL for NP0076158 ((+)-Amotsangin D)

3D MOL for NP0076158 ((+)-Amotsangin D)

3D SDF for NP0076158 ((+)-Amotsangin D)

3D-SDF for NP0076158 ((+)-Amotsangin D)

PDB for NP0076158 ((+)-Amotsangin D)

3D PDB for NP0076158 ((+)-Amotsangin D)

SMILES for NP0076158 ((+)-Amotsangin D)

INCHI for NP0076158 ((+)-Amotsangin D)

Structure for NP0076158 ((+)-Amotsangin D)

3D Structure for NP0076158 ((+)-Amotsangin D)