NP-MRD: Showing NP-Card for (1s,2r,7r,9r,11r)-2-({[(2e)-5-hydroxy-3-methylpent-2-enoyl]oxy}methyl)-1,5-dimethyl-12-methylidene-8-oxatricyclo[7.2.1.0²,⁷]dodec-5-en-11-yl (2e,4e,6r,7r)-6,7-dihydroxyocta-2,4-dienoate (NP0253394)

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Record Information

Version

2.0

Created at

2022-09-07 17:15:16 UTC

Updated at

2022-09-07 17:15:16 UTC

NP-MRD ID

NP0253394

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,7r,9r,11r)-2-({[(2e)-5-hydroxy-3-methylpent-2-enoyl]oxy}methyl)-1,5-dimethyl-12-methylidene-8-oxatricyclo[7.2.1.0²,⁷]dodec-5-en-11-yl (2e,4e,6r,7r)-6,7-dihydroxyocta-2,4-dienoate

Description

12,13-Deoxytrichoverrin B belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms. (1s,2r,7r,9r,11r)-2-({[(2e)-5-hydroxy-3-methylpent-2-enoyl]oxy}methyl)-1,5-dimethyl-12-methylidene-8-oxatricyclo[7.2.1.0²,⁷]dodec-5-en-11-yl (2e,4e,6r,7r)-6,7-dihydroxyocta-2,4-dienoate is found in Albifimbria verrucaria. Based on a literature review very few articles have been published on 12,13-Deoxytrichoverrin B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072219152D          

 37 39  0  0  1  0            999 V2000
    2.1043    1.2782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7514    1.7900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2908    1.0015    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7168    1.7080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4300    2.4816    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0026    3.0756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8033    2.8768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0314    2.0839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3758    3.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1765    3.2720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7490    3.8660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  3 37  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309072219152D          

 37 39  0  0  1  0            999 V2000
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    0.4562    1.6004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2938    1.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1289    1.1228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8789    1.4666    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4729    0.8940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  1  0  0  0
  5 18  1  0  0  0  0
  2 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 20 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
 35 36  1  0  0  0  0
 20 36  1  0  0  0  0
 36 37  1  6  0  0  0
  3 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0253394

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H](O)[C@H](O)\C=C\C=C\C(=O)O[C@@H]1C[C@H]2O[C@@H]3C=C(C)CC[C@]3(COC(=O)\C=C(/C)CCO)[C@]1(C)C2=C

> <INCHI_IDENTIFIER>
InChI=1S/C29H40O8/c1-18-10-12-29(17-35-27(34)15-19(2)11-13-30)25(14-18)36-23-16-24(28(29,5)20(23)3)37-26(33)9-7-6-8-22(32)21(4)31/h6-9,14-15,21-25,30-32H,3,10-13,16-17H2,1-2,4-5H3/b8-6+,9-7+,19-15+/t21-,22-,23-,24-,25-,28-,29-/m1/s1

> <INCHI_KEY>
DQMXCXZEZVSOMG-DMELOKKLSA-N

> <FORMULA>
C29H40O8

> <MOLECULAR_WEIGHT>
516.631

> <EXACT_MASS>
516.272318248

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
55.815412021308624

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,7R,9R,11R)-2-({[(2E)-5-hydroxy-3-methylpent-2-enoyl]oxy}methyl)-1,5-dimethyl-12-methylidene-8-oxatricyclo[7.2.1.0^{2,7}]dodec-5-en-11-yl (2E,4E,6R,7R)-6,7-dihydroxyocta-2,4-dienoate

> <JCHEM_LOGP>
2.722659493999999

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.406924140131157

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.743006304847125

> <JCHEM_PKA_STRONGEST_BASIC>
-1.8750005698696115

> <JCHEM_POLAR_SURFACE_AREA>
122.52

> <JCHEM_REFRACTIVITY>
142.2241

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,7R,9R,11R)-2-({[(2E)-5-hydroxy-3-methylpent-2-enoyl]oxy}methyl)-1,5-dimethyl-12-methylidene-8-oxatricyclo[7.2.1.0^{2,7}]dodec-5-en-11-yl (2E,4E,6R,7R)-6,7-dihydroxyocta-2,4-dienoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       3.928   2.386   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.136   3.341   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.143   1.869   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.938   3.188   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.403   4.632   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       7.471   5.741   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       8.966   5.370   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       9.392   3.890   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      10.035   6.479   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.529   6.108   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.598   7.216   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.093   6.845   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      15.161   7.954   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      14.735   9.434   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      16.656   7.583   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      17.725   8.692   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      17.082   6.103   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.940   5.114   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.739   6.641   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.651   4.271   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.681   5.811   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.362   6.606   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.391   8.145   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.739   8.890   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.072   8.941   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.101  10.480   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.449  11.225   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.217  11.275   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.188  12.815   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.507  13.610   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.396   5.162   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.996   4.521   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.852   2.987   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.548   2.346   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.107   2.096   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.507   2.738   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       4.616   1.669   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   18                                                  
CONECT    3    2    4   37                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   18                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18    5    2   19   20                                             
CONECT   19   18                                                            
CONECT   20   18   21   31   36                                             
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29                                                            
CONECT   31   20   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35   20   37                                                  
CONECT   37   36    3                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₄₀O₈

Average Mass

516.6310 Da

Monoisotopic Mass

516.27232 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@@H](O)[C@H](O)\C=C\C=C\C(=O)O[C@@H]1C[C@H]2O[C@@H]3C=C(C)CC[C@]3(COC(=O)\C=C(/C)CCO)[C@]1(C)C2=C

InChI Identifier

InChI=1S/C29H40O8/c1-18-10-12-29(17-35-27(34)15-19(2)11-13-30)25(14-18)36-23-16-24(28(29,5)20(23)3)37-26(33)9-7-6-8-22(32)21(4)31/h6-9,14-15,21-25,30-32H,3,10-13,16-17H2,1-2,4-5H3/b8-6+,9-7+,19-15+/t21-,22-,23-,24-,25-,28-,29-/m1/s1

InChI Key

DQMXCXZEZVSOMG-DMELOKKLSA-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
Albifimbria verrucaria	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohols

Direct Parent

Fatty alcohols

Alternative Parents

Substituents

Fatty alcohol
Fatty acid ester
Oxepane
Dicarboxylic acid or derivatives
Oxane
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Ether
Dialkyl ether
Carboxylic acid derivative
Primary alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
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

78441540

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139588574

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2r,7r,9r,11r)-2-({[(2e)-5-hydroxy-3-methylpent-2-enoyl]oxy}methyl)-1,5-dimethyl-12-methylidene-8-oxatricyclo[7.2.1.0²,⁷]dodec-5-en-11-yl (2e,4e,6r,7r)-6,7-dihydroxyocta-2,4-dienoate (NP0253394)

MOL for NP0253394 ((1s,2r,7r,9r,11r)-2-({[(2e)-5-hydroxy-3-methylpent-2-enoyl]oxy}methyl)-1,5-dimethyl-12-methylidene-8-oxatricyclo[7.2.1.0²,⁷]dodec-5-en-11-yl (2e,4e,6r,7r)-6,7-dihydroxyocta-2,4-dienoate)

3D MOL for NP0253394 ((1s,2r,7r,9r,11r)-2-({[(2e)-5-hydroxy-3-methylpent-2-enoyl]oxy}methyl)-1,5-dimethyl-12-methylidene-8-oxatricyclo[7.2.1.0²,⁷]dodec-5-en-11-yl (2e,4e,6r,7r)-6,7-dihydroxyocta-2,4-dienoate)

3D SDF for NP0253394 ((1s,2r,7r,9r,11r)-2-({[(2e)-5-hydroxy-3-methylpent-2-enoyl]oxy}methyl)-1,5-dimethyl-12-methylidene-8-oxatricyclo[7.2.1.0²,⁷]dodec-5-en-11-yl (2e,4e,6r,7r)-6,7-dihydroxyocta-2,4-dienoate)

3D-SDF for NP0253394 ((1s,2r,7r,9r,11r)-2-({[(2e)-5-hydroxy-3-methylpent-2-enoyl]oxy}methyl)-1,5-dimethyl-12-methylidene-8-oxatricyclo[7.2.1.0²,⁷]dodec-5-en-11-yl (2e,4e,6r,7r)-6,7-dihydroxyocta-2,4-dienoate)

PDB for NP0253394 ((1s,2r,7r,9r,11r)-2-({[(2e)-5-hydroxy-3-methylpent-2-enoyl]oxy}methyl)-1,5-dimethyl-12-methylidene-8-oxatricyclo[7.2.1.0²,⁷]dodec-5-en-11-yl (2e,4e,6r,7r)-6,7-dihydroxyocta-2,4-dienoate)

3D PDB for NP0253394 ((1s,2r,7r,9r,11r)-2-({[(2e)-5-hydroxy-3-methylpent-2-enoyl]oxy}methyl)-1,5-dimethyl-12-methylidene-8-oxatricyclo[7.2.1.0²,⁷]dodec-5-en-11-yl (2e,4e,6r,7r)-6,7-dihydroxyocta-2,4-dienoate)

SMILES for NP0253394 ((1s,2r,7r,9r,11r)-2-({[(2e)-5-hydroxy-3-methylpent-2-enoyl]oxy}methyl)-1,5-dimethyl-12-methylidene-8-oxatricyclo[7.2.1.0²,⁷]dodec-5-en-11-yl (2e,4e,6r,7r)-6,7-dihydroxyocta-2,4-dienoate)

INCHI for NP0253394 ((1s,2r,7r,9r,11r)-2-({[(2e)-5-hydroxy-3-methylpent-2-enoyl]oxy}methyl)-1,5-dimethyl-12-methylidene-8-oxatricyclo[7.2.1.0²,⁷]dodec-5-en-11-yl (2e,4e,6r,7r)-6,7-dihydroxyocta-2,4-dienoate)

Structure for NP0253394 ((1s,2r,7r,9r,11r)-2-({[(2e)-5-hydroxy-3-methylpent-2-enoyl]oxy}methyl)-1,5-dimethyl-12-methylidene-8-oxatricyclo[7.2.1.0²,⁷]dodec-5-en-11-yl (2e,4e,6r,7r)-6,7-dihydroxyocta-2,4-dienoate)

3D Structure for NP0253394 ((1s,2r,7r,9r,11r)-2-({[(2e)-5-hydroxy-3-methylpent-2-enoyl]oxy}methyl)-1,5-dimethyl-12-methylidene-8-oxatricyclo[7.2.1.0²,⁷]dodec-5-en-11-yl (2e,4e,6r,7r)-6,7-dihydroxyocta-2,4-dienoate)