NP-MRD: Showing NP-Card for 17-methoxy-16-hydroxyfarnesyl-triacetate lactone (NP0331889)

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Record Information

Version

1.0

Created at

2023-09-27 04:01:56 UTC

Updated at

2024-04-19 09:54:50 UTC

NP-MRD ID

NP0331889

Secondary Accession Numbers

None

Natural Product Identification

Common Name

17-methoxy-16-hydroxyfarnesyl-triacetate lactone

Description

Not Available

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 09272304012D          

 27 27  0  0  1  0            999 V2000
    0.7145    2.0625    0.0000 O   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 C   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
    0.7145   -0.4125    0.0000 O   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 C   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
    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
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    7.0125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868    7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1283    6.7105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3033    8.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  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
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  2  8  1  0  0  0  0
  4  9  2  0  0  0  0
  3 10  1  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
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 20  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 26  1  0  0  0  0
 23 27  1  0  0  0  0
M  END


  Mrv2104 09272304012D          

 27 27  0  0  1  0            999 V2000
    0.7145    2.0625    0.0000 O   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 C   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
    0.7145   -0.4125    0.0000 O   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 C   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
    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
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    7.0125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868    7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1283    6.7105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3033    8.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  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
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  2  8  1  0  0  0  0
  4  9  2  0  0  0  0
  3 10  1  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
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 20  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 26  1  0  0  0  0
 23 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331889

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(C)(C)[C@@H](O)CC\C(C)=C\CC\C(C)=C\CC1=C(O)C=C(C)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H34O5/c1-15(10-12-18-19(23)14-17(3)27-21(18)25)8-7-9-16(2)11-13-20(24)22(4,5)26-6/h9-10,14,20,23-24H,7-8,11-13H2,1-6H3/b15-10+,16-9+/t20-/m0/s1

> <INCHI_KEY>
DALFIYUVYJOQKJ-CGJANUHBSA-N

> <FORMULA>
C22H34O5

> <MOLECULAR_WEIGHT>
378.509

> <EXACT_MASS>
378.240624195

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
43.617461666535206

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-hydroxy-3-[(2E,6E,10S)-10-hydroxy-11-methoxy-3,7,11-trimethyldodeca-2,6-dien-1-yl]-6-methyl-2H-pyran-2-one

> <JCHEM_LOGP>
3.981893991999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.00199437546372

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.658026048798354

> <JCHEM_PKA_STRONGEST_BASIC>
-3.235327746205296

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
112.06960000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-3-[(2E,6E,10S)-10-hydroxy-11-methoxy-3,7,11-trimethyldodeca-2,6-dien-1-yl]-6-methylpyran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-SEP-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-23         0                                  
HETATM    1  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002   9.240   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.336   8.470   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.002  10.780   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.336  11.550   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.336  13.090   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       8.002  13.860   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      10.669  13.860   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      12.003  14.630   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      12.003  16.170   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.439  12.526   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.899  15.194   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    2                                                       
CONECT    9    4                                                            
CONECT   10    3   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   26   27                                             
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23                                                            
CONECT   27   23                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₄O₅

Average Mass

378.5090 Da

Monoisotopic Mass

378.24062 Da

IUPAC Name

4-hydroxy-3-[(2E,6E,10S)-10-hydroxy-11-methoxy-3,7,11-trimethyldodeca-2,6-dien-1-yl]-6-methyl-2H-pyran-2-one

Traditional Name

4-hydroxy-3-[(2E,6E,10S)-10-hydroxy-11-methoxy-3,7,11-trimethyldodeca-2,6-dien-1-yl]-6-methylpyran-2-one

CAS Registry Number

Not Available

SMILES

COC(C)(C)[C@@H](O)CC\C(C)=C\CC\C(C)=C\CC1=C(O)C=C(C)OC1=O

InChI Identifier

InChI=1S/C22H34O5/c1-15(10-12-18-19(23)14-17(3)27-21(18)25)8-7-9-16(2)11-13-20(24)22(4,5)26-6/h9-10,14,20,23-24H,7-8,11-13H2,1-6H3/b15-10+,16-9+/t20-/m0/s1

InChI Key

DALFIYUVYJOQKJ-CGJANUHBSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, C3D6O, experimental)	shuyilin@usc.edu	Not Available	Not Available	2023-09-27	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, C3D6O, experimental)	shuyilin@usc.edu	Not Available	Not Available	2023-09-27	View Spectrum
1D NMR	[¹³C, ] NMR Spectrum (2D, 101 MHz, C3D6O, experimental)	shuyilin@usc.edu	Not Available	Not Available	2023-09-27	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, C3D6O, experimental)	shuyilin@usc.edu	Not Available	Not Available	2023-09-27	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, C3D6O, experimental)	shuyilin@usc.edu	Not Available	Not Available	2023-09-27	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 400 MHz, C3D6O, experimental)	shuyilin@usc.edu	Not Available	Not Available	2023-09-27	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Classification

Not classified

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	3.98	ChemAxon
pKa (Strongest Acidic)	7.66	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	112.07 m³·mol⁻¹	ChemAxon
Polarizability	43.62 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

Not Available

References

General References

Not Available

Showing NP-Card for 17-methoxy-16-hydroxyfarnesyl-triacetate lactone (NP0331889)

MOL for NP0331889 (17-methoxy-16-hydroxyfarnesyl-triacetate lactone)

3D MOL for NP0331889 (17-methoxy-16-hydroxyfarnesyl-triacetate lactone)

3D SDF for NP0331889 (17-methoxy-16-hydroxyfarnesyl-triacetate lactone)

3D-SDF for NP0331889 (17-methoxy-16-hydroxyfarnesyl-triacetate lactone)

PDB for NP0331889 (17-methoxy-16-hydroxyfarnesyl-triacetate lactone)

3D PDB for NP0331889 (17-methoxy-16-hydroxyfarnesyl-triacetate lactone)

SMILES for NP0331889 (17-methoxy-16-hydroxyfarnesyl-triacetate lactone)

INCHI for NP0331889 (17-methoxy-16-hydroxyfarnesyl-triacetate lactone)

Structure for NP0331889 (17-methoxy-16-hydroxyfarnesyl-triacetate lactone)

3D Structure for NP0331889 (17-methoxy-16-hydroxyfarnesyl-triacetate lactone)