NP-MRD: Showing NP-Card for 4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[1-(2-methyl-1,3-oxazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadec-13-ene-2,6-dione (NP0175475)

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Record Information

Version

2.0

Created at

2022-09-03 12:57:01 UTC

Updated at

2022-09-03 12:57:02 UTC

NP-MRD ID

NP0175475

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[1-(2-methyl-1,3-oxazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadec-13-ene-2,6-dione

Description

4,8-Dihydroxy-5,5,7,9,13-pentamethyl-16-[1-(2-methyl-1,3-oxazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadec-13-ene-2,6-dione belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. 4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[1-(2-methyl-1,3-oxazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadec-13-ene-2,6-dione is found in Sorangium cellulosum. 4,8-Dihydroxy-5,5,7,9,13-pentamethyl-16-[1-(2-methyl-1,3-oxazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadec-13-ene-2,6-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004261504092D          

 34 35  0  0  0  0            999 V2000
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  6 34  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1533004261504092D          

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 21 23  1  0  0  0  0
  2 23  1  0  0  0  0
 23 24  1  0  0  0  0
  9 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  4  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 27 32  1  0  0  0  0
 25 33  1  0  0  0  0
  6 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0175475

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CCCC(C)=CCC(OC(=O)CC(O)C(C)(C)C(=O)C(C)C1O)C(C)=CC1=COC(C)=N1

> <INCHI_IDENTIFIER>
InChI=1S/C27H41NO6/c1-16-9-8-10-17(2)25(31)19(4)26(32)27(6,7)23(29)14-24(30)34-22(12-11-16)18(3)13-21-15-33-20(5)28-21/h11,13,15,17,19,22-23,25,29,31H,8-10,12,14H2,1-7H3

> <INCHI_KEY>
QJBTYCVYJKZKMC-UHFFFAOYSA-N

> <FORMULA>
C27H41NO6

> <MOLECULAR_WEIGHT>
475.626

> <EXACT_MASS>
475.293388044

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
52.487951302596606

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[1-(2-methyl-1,3-oxazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadec-13-ene-2,6-dione

> <ALOGPS_LOGP>
4.00

> <JCHEM_LOGP>
4.379407876999999

> <ALOGPS_LOGS>
-4.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.727566724179379

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.086923380314165

> <JCHEM_PKA_STRONGEST_BASIC>
0.5848256165601162

> <JCHEM_POLAR_SURFACE_AREA>
109.86

> <JCHEM_REFRACTIVITY>
131.5441

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.43e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[1-(2-methyl-1,3-oxazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadec-13-ene-2,6-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0      13.337  14.940   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.670  15.710   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      16.004  14.940   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      16.004  13.400   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.670  12.630   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.337  13.400   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.003  12.630   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.669  13.400   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336  12.630   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.002  13.400   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       8.002  14.940   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.668  15.710   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       9.336  15.710   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336  17.250   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.002  18.020   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      10.669  18.020   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.680  19.200   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.659  19.200   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.003  17.250   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      12.003  15.710   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      13.337  18.020   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.337  19.560   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.670  17.250   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      16.004  18.020   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       9.336  11.090   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.002  10.320   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.002   8.780   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.248   7.875   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       8.772   6.410   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       7.232   6.410   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.327   5.164   0.000  0.00  0.00           C+0
HETATM   32  N   UNK     0       6.756   7.875   0.000  0.00  0.00           N+0
HETATM   33  C   UNK     0      10.669  10.320   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      12.432  14.646   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   23                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   34                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   25                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21    2   24                                                  
CONECT   24   23                                                            
CONECT   25    9   26   33                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   27                                                       
CONECT   33   25                                                            
CONECT   34    6                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₁NO₆

Average Mass

475.6260 Da

Monoisotopic Mass

475.29339 Da

IUPAC Name

4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[1-(2-methyl-1,3-oxazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadec-13-ene-2,6-dione

Traditional Name

4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[1-(2-methyl-1,3-oxazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadec-13-ene-2,6-dione

CAS Registry Number

Not Available

SMILES

CC1CCCC(C)=CCC(OC(=O)CC(O)C(C)(C)C(=O)C(C)C1O)C(C)=CC1=COC(C)=N1

InChI Identifier

InChI=1S/C27H41NO6/c1-16-9-8-10-17(2)25(31)19(4)26(32)27(6,7)23(29)14-24(30)34-22(12-11-16)18(3)13-21-15-33-20(5)28-21/h11,13,15,17,19,22-23,25,29,31H,8-10,12,14H2,1-7H3

InChI Key

QJBTYCVYJKZKMC-UHFFFAOYSA-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
Sorangium cellulosum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Not Available

Direct Parent

Macrolides and analogues

Alternative Parents

Substituents

Macrolide
2,4-disubstituted 1,3-oxazole
Azole
Heteroaromatic compound
Oxazole
Carboxylic acid ester
Ketone
Lactone
Cyclic ketone
Secondary alcohol
Carboxylic acid derivative
Oxacycle
Azacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Carbonyl group
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
logP	4	ALOGPS
logP	4.38	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	14.09	ChemAxon
pKa (Strongest Basic)	0.58	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	109.86 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	131.54 m³·mol⁻¹	ChemAxon
Polarizability	52.49 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

77490186

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[1-(2-methyl-1,3-oxazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadec-13-ene-2,6-dione (NP0175475)

MOL for NP0175475 (4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[1-(2-methyl-1,3-oxazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadec-13-ene-2,6-dione)

3D MOL for NP0175475 (4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[1-(2-methyl-1,3-oxazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadec-13-ene-2,6-dione)

3D SDF for NP0175475 (4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[1-(2-methyl-1,3-oxazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadec-13-ene-2,6-dione)

3D-SDF for NP0175475 (4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[1-(2-methyl-1,3-oxazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadec-13-ene-2,6-dione)

PDB for NP0175475 (4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[1-(2-methyl-1,3-oxazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadec-13-ene-2,6-dione)

3D PDB for NP0175475 (4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[1-(2-methyl-1,3-oxazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadec-13-ene-2,6-dione)

SMILES for NP0175475 (4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[1-(2-methyl-1,3-oxazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadec-13-ene-2,6-dione)

INCHI for NP0175475 (4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[1-(2-methyl-1,3-oxazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadec-13-ene-2,6-dione)

Structure for NP0175475 (4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[1-(2-methyl-1,3-oxazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadec-13-ene-2,6-dione)

3D Structure for NP0175475 (4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[1-(2-methyl-1,3-oxazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadec-13-ene-2,6-dione)