NP-MRD: Showing NP-Card for Nectrianolin B (NP0044196)

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Record Information

Version

1.0

Created at

2021-11-12 23:56:28 UTC

Updated at

2021-11-26 17:46:30 UTC

NP-MRD ID

NP0044196

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Nectrianolin B

Description

Nectrianolin 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. Nectrianolin B is found in Nectria pseudotrichia. It was first documented in 2017 (Nanang Rudianto Ariefta et al.). Based on a literature review very few articles have been published on Nectrianolin B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652311262118462D          

 33 35  0  0  1  0            999 V2000
   -3.4237    5.6605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3949    6.4850    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0945    6.9222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0657    7.7467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3373    8.1340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6376    7.6969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6664    6.8724    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8435    6.8148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2539    6.1579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6664    5.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6664    4.0145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2539    3.3000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -0.7145    3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  6 33  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652311262118462D          

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M  END
> <DATABASE_ID>
NP0044196

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H](O)CC(=O)OCC1=CC(=O)[C@]2(O[C@H]2[C@@H]1O)[C@@H](O)\C=C(/C)CC[C@@]1(C)[C@H](C)CCC=C1C

> <INCHI_IDENTIFIER>
InChI=1S/C26H38O7/c1-15(9-10-25(5)16(2)7-6-8-17(25)3)11-20(28)26-21(29)13-19(23(31)24(26)33-26)14-32-22(30)12-18(4)27/h7,11,13,17-18,20,23-24,27-28,31H,6,8-10,12,14H2,1-5H3/b15-11+/t17-,18-,20+,23-,24+,25-,26-/m1/s1

> <INCHI_KEY>
OFSSRZNLGJTEKA-WMQOLYJXSA-N

> <FORMULA>
C26H38O7

> <MOLECULAR_WEIGHT>
462.583

> <EXACT_MASS>
462.261753564

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
51.13023163918815

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1S,2R,6S)-2-hydroxy-6-[(1S,2E)-1-hydroxy-3-methyl-5-[(1S,6R)-1,2,6-trimethylcyclohex-2-en-1-yl]pent-2-en-1-yl]-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]methyl (3R)-3-hydroxybutanoate

> <ALOGPS_LOGP>
2.88

> <JCHEM_LOGP>
2.7888909863333318

> <ALOGPS_LOGS>
-4.38

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.748081866384663

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.69644404989345

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6206840788444623

> <JCHEM_POLAR_SURFACE_AREA>
116.59

> <JCHEM_REFRACTIVITY>
125.74049999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.91e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1S,2R,6S)-2-hydroxy-6-[(1S,2E)-1-hydroxy-3-methyl-5-[(1S,6R)-1,2,6-trimethylcyclohex-2-en-1-yl]pent-2-en-1-yl]-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]methyl (3R)-3-hydroxybutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-NOV-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-NOV-21         0                                  
HETATM    1  C   UNK     0      -6.391  10.566   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.337  12.105   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.643  12.921   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.589  14.461   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.230  15.184   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.924  14.367   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.977  12.828   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.441  12.721   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.207  11.495   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.977  10.161   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.207   8.827   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.977   7.494   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.207   6.160   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.667   7.700   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -4.001   3.850   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -4.977   4.826   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -2.667   8.827   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -3.564  15.090   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   33                                                  
CONECT    7    6    2    8    9                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   32                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   31                                                  
CONECT   14   13   15   16   20                                             
CONECT   15   14   16   17                                                  
CONECT   16   15   14                                                       
CONECT   17   15   18   30                                                  
CONECT   18   17   19   22                                                  
CONECT   19   18   20                                                       
CONECT   20   19   14   21                                                  
CONECT   21   20                                                            
CONECT   22   18   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   17                                                            
CONECT   31   13                                                            
CONECT   32   11                                                            
CONECT   33    6                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₈O₇

Average Mass

462.5830 Da

Monoisotopic Mass

462.26175 Da

IUPAC Name

[(1S,2R,6S)-2-hydroxy-6-[(1S,2E)-1-hydroxy-3-methyl-5-[(1S,6R)-1,2,6-trimethylcyclohex-2-en-1-yl]pent-2-en-1-yl]-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]methyl (3R)-3-hydroxybutanoate

Traditional Name

[(1S,2R,6S)-2-hydroxy-6-[(1S,2E)-1-hydroxy-3-methyl-5-[(1S,6R)-1,2,6-trimethylcyclohex-2-en-1-yl]pent-2-en-1-yl]-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]methyl (3R)-3-hydroxybutanoate

CAS Registry Number

Not Available

SMILES

C[C@@H](O)CC(=O)OCC1=CC(=O)[C@]2(O[C@H]2[C@@H]1O)[C@@H](O)\C=C(/C)CC[C@@]1(C)[C@H](C)CCC=C1C

InChI Identifier

InChI=1S/C26H38O7/c1-15(9-10-25(5)16(2)7-6-8-17(25)3)11-20(28)26-21(29)13-19(23(31)24(26)33-26)14-32-22(30)12-18(4)27/h7,11,13,17-18,20,23-24,27-28,31H,6,8-10,12,14H2,1-5H3/b15-11+/t17-,18-,20+,23-,24+,25-,26-/m1/s1

InChI Key

OFSSRZNLGJTEKA-WMQOLYJXSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Pyridine-d5, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Nectria pseudotrichia	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
Cyclohexenone
Fatty acid ester
Beta-hydroxy acid
Hydroxy acid
Secondary alcohol
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen 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
logP	2.88	ALOGPS
logP	2.79	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	12.7	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	116.59 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	125.74 m³·mol⁻¹	ChemAxon
Polarizability	51.13 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

78439398

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139591224

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Nanang Rudianto Ariefta et al. (2017). Nectrianolins A, B, and C, new metabolites produced by endophytic fungus Nectria pseudotrichia 120-1NP. Tetrahedron Letters, Volume 58, Issue 43, 25 October 2017, Pages 4082-4086. DOI: 10.1016/j.tetlet.2017.09.032. Tetrahedron Letters.

Showing NP-Card for Nectrianolin B (NP0044196)

MOL for NP0044196 (Nectrianolin B)

3D MOL for NP0044196 (Nectrianolin B)

3D SDF for NP0044196 (Nectrianolin B)

3D-SDF for NP0044196 (Nectrianolin B)

PDB for NP0044196 (Nectrianolin B)

3D PDB for NP0044196 (Nectrianolin B)

SMILES for NP0044196 (Nectrianolin B)

INCHI for NP0044196 (Nectrianolin B)

Structure for NP0044196 (Nectrianolin B)

3D Structure for NP0044196 (Nectrianolin B)