NP-MRD: Showing NP-Card for 2-[(2e,5e,7e,11e,13e)-10-hydroxy-3,7,9,11,13-pentamethylpentadeca-2,5,7,11,13-pentaen-1-yl]-6-methoxy-3-methylpyridin-4-ol (NP0281661)

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Record Information

Version

2.0

Created at

2022-09-09 08:08:40 UTC

Updated at

2022-09-09 08:08:40 UTC

NP-MRD ID

NP0281661

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[(2e,5e,7e,11e,13e)-10-hydroxy-3,7,9,11,13-pentamethylpentadeca-2,5,7,11,13-pentaen-1-yl]-6-methoxy-3-methylpyridin-4-ol

Description

JBIR-02 belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. 2-[(2e,5e,7e,11e,13e)-10-hydroxy-3,7,9,11,13-pentamethylpentadeca-2,5,7,11,13-pentaen-1-yl]-6-methoxy-3-methylpyridin-4-ol was first documented in 2007 (PMID: 17721005). Based on a literature review a small amount of articles have been published on JBIR-02 (PMID: 23330661) (PMID: 21561424).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092210082D          

 31 31  0  0  0  0            999 V2000
    2.8579   10.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
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  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
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 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
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 28 30  2  0  0  0  0
 22 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END

     RDKit          3D

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   -7.0528    0.6685    0.9948 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0220    0.2649    0.1624 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.8055    0.2672   -1.1989 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309092210082D          

 31 31  0  0  0  0            999 V2000
    2.8579   10.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0281661

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C(C)C(C\C=C(/C)C\C=C\C(\C)=C\C(C)C(O)C(\C)=C\C(\C)=C\C)=N1

> <INCHI_IDENTIFIER>
InChI=1S/C27H39NO3/c1-9-18(2)15-21(5)27(30)22(6)16-20(4)12-10-11-19(3)13-14-24-23(7)25(29)17-26(28-24)31-8/h9-10,12-13,15-17,22,27,30H,11,14H2,1-8H3,(H,28,29)/b12-10+,18-9+,19-13+,20-16+,21-15+

> <INCHI_KEY>
AIDLWDQRTGLLNU-RLAGNCKMSA-N

> <FORMULA>
C27H39NO3

> <MOLECULAR_WEIGHT>
425.613

> <EXACT_MASS>
425.29299412

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
51.41019648702073

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(2E,5E,7E,11E,13E)-10-hydroxy-3,7,9,11,13-pentamethylpentadeca-2,5,7,11,13-pentaen-1-yl]-6-methoxy-3-methylpyridin-4-ol

> <JCHEM_LOGP>
6.311512944666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.921195059267216

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.34159320118666

> <JCHEM_PKA_STRONGEST_BASIC>
1.8045560752551206

> <JCHEM_POLAR_SURFACE_AREA>
62.58000000000001

> <JCHEM_REFRACTIVITY>
135.42940000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2-[(2E,5E,7E,11E,13E)-10-hydroxy-3,7,9,11,13-pentamethylpentadeca-2,5,7,11,13-pentaen-1-yl]-6-methoxy-3-methylpyridin-4-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       5.335  20.020   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335  18.480   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  17.710   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  18.480   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  16.170   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  15.400   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  16.170   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  13.860   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.001  13.090   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.334  13.090   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000  13.860   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  11.550   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000  10.780   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334  11.550   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0       2.667   1.540   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   30                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   22   31                                                  
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₉NO₃

Average Mass

425.6130 Da

Monoisotopic Mass

425.29299 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C(C)C(C\C=C(/C)C\C=C\C(\C)=C\C(C)C(O)C(\C)=C\C(\C)=C\C)=N1

InChI Identifier

InChI=1S/C27H39NO3/c1-9-18(2)15-21(5)27(30)22(6)16-20(4)12-10-11-19(3)13-14-24-23(7)25(29)17-26(28-24)31-8/h9-10,12-13,15-17,22,27,30H,11,14H2,1-8H3,(H,28,29)/b12-10+,18-9+,19-13+,20-16+,21-15+

InChI Key

AIDLWDQRTGLLNU-RLAGNCKMSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Alkyl aryl ether
Dihydropyridine
Methylpyridine
Hydropyridine
Pyridine
Heteroaromatic compound
Vinylogous amide
Vinylogous ester
Secondary alcohol
Cyclic ketone
Azacycle
Ether
Organoheterocyclic compound
Alcohol
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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

28284366

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

17755099

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ueda JY, Togashi T, Matukura S, Nagai A, Nakashima T, Komaki H, Anzai K, Harayama S, Doi T, Takahashi T, Natsume T, Kisu Y, Goshima N, Nomura N, Takagi M, Shin-Ya K: A novel nuclear export inhibitor JBIR-02, a new piericidin discovered from Streptomyces sp. ML55. J Antibiot (Tokyo). 2007 Jul;60(7):459-62. doi: 10.1038/ja.2007.59. [PubMed:17721005 ]
Hoecker J, Gademann K: Enantioselective total syntheses and absolute configuration of JBIR-02 and Mer-A2026B. Org Lett. 2013 Feb 1;15(3):670-3. doi: 10.1021/ol303502a. Epub 2013 Jan 18. [PubMed:23330661 ]
Gademann K: Controlling protein transport by small molecules. Curr Drug Targets. 2011 Oct;12(11):1574-80. doi: 10.2174/138945011798109446. [PubMed:21561424 ]
LOTUS database [Link]

Showing NP-Card for 2-[(2e,5e,7e,11e,13e)-10-hydroxy-3,7,9,11,13-pentamethylpentadeca-2,5,7,11,13-pentaen-1-yl]-6-methoxy-3-methylpyridin-4-ol (NP0281661)

MOL for NP0281661 (2-[(2e,5e,7e,11e,13e)-10-hydroxy-3,7,9,11,13-pentamethylpentadeca-2,5,7,11,13-pentaen-1-yl]-6-methoxy-3-methylpyridin-4-ol)

3D MOL for NP0281661 (2-[(2e,5e,7e,11e,13e)-10-hydroxy-3,7,9,11,13-pentamethylpentadeca-2,5,7,11,13-pentaen-1-yl]-6-methoxy-3-methylpyridin-4-ol)

3D SDF for NP0281661 (2-[(2e,5e,7e,11e,13e)-10-hydroxy-3,7,9,11,13-pentamethylpentadeca-2,5,7,11,13-pentaen-1-yl]-6-methoxy-3-methylpyridin-4-ol)

3D-SDF for NP0281661 (2-[(2e,5e,7e,11e,13e)-10-hydroxy-3,7,9,11,13-pentamethylpentadeca-2,5,7,11,13-pentaen-1-yl]-6-methoxy-3-methylpyridin-4-ol)

PDB for NP0281661 (2-[(2e,5e,7e,11e,13e)-10-hydroxy-3,7,9,11,13-pentamethylpentadeca-2,5,7,11,13-pentaen-1-yl]-6-methoxy-3-methylpyridin-4-ol)

3D PDB for NP0281661 (2-[(2e,5e,7e,11e,13e)-10-hydroxy-3,7,9,11,13-pentamethylpentadeca-2,5,7,11,13-pentaen-1-yl]-6-methoxy-3-methylpyridin-4-ol)

SMILES for NP0281661 (2-[(2e,5e,7e,11e,13e)-10-hydroxy-3,7,9,11,13-pentamethylpentadeca-2,5,7,11,13-pentaen-1-yl]-6-methoxy-3-methylpyridin-4-ol)

INCHI for NP0281661 (2-[(2e,5e,7e,11e,13e)-10-hydroxy-3,7,9,11,13-pentamethylpentadeca-2,5,7,11,13-pentaen-1-yl]-6-methoxy-3-methylpyridin-4-ol)

Structure for NP0281661 (2-[(2e,5e,7e,11e,13e)-10-hydroxy-3,7,9,11,13-pentamethylpentadeca-2,5,7,11,13-pentaen-1-yl]-6-methoxy-3-methylpyridin-4-ol)

3D Structure for NP0281661 (2-[(2e,5e,7e,11e,13e)-10-hydroxy-3,7,9,11,13-pentamethylpentadeca-2,5,7,11,13-pentaen-1-yl]-6-methoxy-3-methylpyridin-4-ol)