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Showing NP-Card for 1-Methoxy-4,5-dihydroniveusin A (NP0336520)

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Record Information
Version2.0
Created at2024-09-11 06:39:32 UTC
Updated at2024-09-11 06:39:32 UTC
NP-MRD IDNP0336520
Secondary Accession NumbersNone
Natural Product Identification
Common Name1-Methoxy-4,5-dihydroniveusin A
Description1-Methoxy-4,5-dihydroniveusin A belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. 1-Methoxy-4,5-dihydroniveusin A was first documented in 2006 (PMID: 16724843). Based on a literature review very few articles have been published on 1-Methoxy-4,5-dihydroniveusin A.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0336520 (1-Methoxy-4,5-dihydroniveusin A)


  Mrv2104 05262309112D          

 29 31  0  0  0  0            999 V2000
    2.3512    3.5652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7281    4.3207    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3933    4.3207    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2593    3.5946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2593    2.7402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3512    2.7107    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6482    5.1052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4732    5.1052    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1078    3.9082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0607    0.8873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3933    1.3722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6482    2.1568    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4732    2.1568    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7281    1.3722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0607    0.0623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5128    1.1173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4514    4.7176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3214    4.7328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0296    3.8900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6705    3.3705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2171    1.0748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5025    1.4873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5025    2.3123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2170    2.7248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7881    2.7248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7881    3.5498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0736    2.3123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9581    5.7726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7786    5.6864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  6  1  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5 12  1  0  0  0  0
 13  6  1  0  0  0  0
  3  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  2  1  0  0  0  0
  3  9  1  1  0  0  0
  2  9  1  1  0  0  0
 10 11  1  0  0  0  0
 10 14  1  0  0  0  0
 13 14  1  1  0  0  0
 12 13  1  0  0  0  0
 10 15  2  0  0  0  0
 14 16  2  0  0  0  0
  6 27  1  1  0  0  0
  2 17  1  6  0  0  0
  3 18  1  6  0  0  0
  4 19  1  0  0  0  0
 19 20  1  0  0  0  0
 12 11  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
  8 28  1  6  0  0  0
 28 29  1  0  0  0  0
M  END
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3D MOL for NP0336520 (1-Methoxy-4,5-dihydroniveusin A)

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3D SDF for NP0336520 (1-Methoxy-4,5-dihydroniveusin A)

  Mrv2104 05262309112D          

 29 31  0  0  0  0            999 V2000
    2.3512    3.5652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7281    4.3207    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3933    4.3207    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2593    3.5946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2593    2.7402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3512    2.7107    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6482    5.1052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4732    5.1052    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1078    3.9082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0607    0.8873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3933    1.3722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6482    2.1568    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4732    2.1568    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7281    1.3722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0607    0.0623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5128    1.1173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4514    4.7176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3214    4.7328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0296    3.8900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6705    3.3705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2171    1.0748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5025    1.4873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5025    2.3123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2170    2.7248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7881    2.7248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7881    3.5498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0736    2.3123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9581    5.7726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7786    5.6864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  6  1  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5 12  1  0  0  0  0
 13  6  1  0  0  0  0
  3  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  2  1  0  0  0  0
  3  9  1  1  0  0  0
  2  9  1  1  0  0  0
 10 11  1  0  0  0  0
 10 14  1  0  0  0  0
 13 14  1  1  0  0  0
 12 13  1  0  0  0  0
 10 15  2  0  0  0  0
 14 16  2  0  0  0  0
  6 27  1  1  0  0  0
  2 17  1  6  0  0  0
  3 18  1  6  0  0  0
  4 19  1  0  0  0  0
 19 20  1  0  0  0  0
 12 11  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
  8 28  1  6  0  0  0
 28 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0336520

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H]1C[C@@]2(O)O[C@]1(C)C[C@@H](OC(=O)C(\C)=C\C)[C@@H]1[C@H](OC(=O)C1=C)\C=C2\CO

> <INCHI_IDENTIFIER>
InChI=1/C21H28O8/c1-6-11(2)18(23)28-15-8-20(4)16(26-5)9-21(25,29-20)13(10-22)7-14-17(15)12(3)19(24)27-14/h6-7,14-17,22,25H,3,8-10H2,1-2,4-5H3/b11-6+,13-7-/t14-,15-,16+,17+,20?,21?/s2

> <INCHI_KEY>
HLEQIALHIWJEKM-JFRSSCDXNA-N

> <FORMULA>
C21H28O8

> <MOLECULAR_WEIGHT>
408.447

> <EXACT_MASS>
408.178417862

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
42.13405059616551

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2Z,4R,8R,9R,11R,12S)-1-hydroxy-2-(hydroxymethyl)-12-methoxy-11-methyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.0^{4,8}]tetradec-2-en-9-yl (2E)-2-methylbut-2-enoate

> <JCHEM_LOGP>
1.789776181333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.091686994785192

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.32661870942134

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8000269666114335

> <JCHEM_POLAR_SURFACE_AREA>
111.52000000000001

> <JCHEM_REFRACTIVITY>
103.11529999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2Z,4R,8R,9R,11R,12S)-1-hydroxy-2-(hydroxymethyl)-12-methoxy-11-methyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.0^{4,8}]tetradec-2-en-9-yl (2E)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0336520 (1-Methoxy-4,5-dihydroniveusin A)
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PDB for NP0336520 (1-Methoxy-4,5-dihydroniveusin A)
HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0       4.389   6.655   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.226   8.065   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.734   8.065   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.484   6.710   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.484   5.115   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.389   5.060   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.210   9.530   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.750   9.530   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.068   7.295   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.980   1.656   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.734   2.561   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.210   4.026   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.750   4.026   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.226   2.561   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.980   0.116   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.691   2.086   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.576   8.806   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.600   8.835   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -1.922   7.261   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -3.118   6.292   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       9.739   2.006   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.405   2.776   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.405   4.316   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.738   5.086   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.071   5.086   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       7.071   6.626   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       5.737   4.316   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       3.655  10.776   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       5.187  10.615   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    8    9   17                                             
CONECT    3    4    7    9   18                                             
CONECT    4    3    5   19                                                  
CONECT    5    4   12                                                       
CONECT    6    1   13   27                                                  
CONECT    7    3    8                                                       
CONECT    8    7    2   28                                                  
CONECT    9    3    2                                                       
CONECT   10   11   14   15                                                  
CONECT   11   10   12                                                       
CONECT   12    5   13   11                                                  
CONECT   13    6   14   12                                                  
CONECT   14   10   13   16                                                  
CONECT   15   10                                                            
CONECT   16   14                                                            
CONECT   17    2                                                            
CONECT   18    3                                                            
CONECT   19    4   20                                                       
CONECT   20   19                                                            
CONECT   21   22                                                            
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27    6   25                                                       
CONECT   28    8   29                                                       
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   62    0
END

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3D PDB for NP0336520 (1-Methoxy-4,5-dihydroniveusin A)
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SMILES for NP0336520 (1-Methoxy-4,5-dihydroniveusin A)
CO[C@H]1C[C@@]2(O)O[C@]1(C)C[C@@H](OC(=O)C(\C)=C\C)[C@@H]1[C@H](OC(=O)C1=C)\C=C2\CO
Download
INCHI for NP0336520 (1-Methoxy-4,5-dihydroniveusin A)
InChI=1/C21H28O8/c1-6-11(2)18(23)28-15-8-20(4)16(26-5)9-21(25,29-20)13(10-22)7-14-17(15)12(3)19(24)27-14/h6-7,14-17,22,25H,3,8-10H2,1-2,4-5H3/b11-6+,13-7-/t14-,15-,16+,17+,20?,21?/s2
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View in JSmol
SynonymsNot Available
Chemical FormulaC21H28O8
Average Mass408.4470 Da
Monoisotopic Mass408.17842 Da
IUPAC Name(1R,2Z,4R,8R,9R,11R,12S)-1-hydroxy-2-(hydroxymethyl)-12-methoxy-11-methyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.0^{4,8}]tetradec-2-en-9-yl (2E)-2-methylbut-2-enoate
Traditional Name(1R,2Z,4R,8R,9R,11R,12S)-1-hydroxy-2-(hydroxymethyl)-12-methoxy-11-methyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.0^{4,8}]tetradec-2-en-9-yl (2E)-2-methylbut-2-enoate
CAS Registry NumberNot Available
SMILES
CO[C@H]1C[C@@]2(O)O[C@]1(C)C[C@@H](OC(=O)C(\C)=C\C)[C@@H]1[C@H](OC(=O)C1=C)\C=C2\CO
InChI Identifier
InChI=1/C21H28O8/c1-6-11(2)18(23)28-15-8-20(4)16(26-5)9-21(25,29-20)13(10-22)7-14-17(15)12(3)19(24)27-14/h6-7,14-17,22,25H,3,8-10H2,1-2,4-5H3/b11-6+,13-7-/t14-,15-,16+,17+,20?,21?/s2
InChI KeyHLEQIALHIWJEKM-JFRSSCDXNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassTerpene lactones  
Direct ParentTerpene lactones  
Alternative Parents
Substituents
  • Terpene lactone
    • 

  • Sesquiterpenoid
    • 

  • Fatty acid ester
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Gamma butyrolactone
    • 

  • Monosaccharide
    • 

  • Fatty acyl
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Tetrahydrofuran
    • 

  • Enoate ester
    • 

  • Lactone
    • 

  • Hemiacetal
    • 

  • Carboxylic acid ester
    • 

  • Organoheterocyclic compound
    • 

  • Oxacycle
    • 

  • Ether
    • 

  • Dialkyl ether
    • 

  • Carboxylic acid derivative
    • 

  • Primary alcohol
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Alcohol
    • 

  • Carbonyl group
    • 

  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.79ChemAxon
pKa (Strongest Acidic)11.33ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area111.52 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity103.12 m³·mol⁻¹ChemAxon
Polarizability42.13 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Macias FA, Fernandez A, Varela RM, Molinillo JM, Torres A, Alves PL: Sesquiterpene lactones as allelochemicals. J Nat Prod. 2006 May;69(5):795-800. doi: 10.1021/np060056s. [PubMed:16724843  ]