NP-MRD: Showing NP-Card for 4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadeca-11,13-diene-2,6,10-trione (NP0146856)

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Record Information

Version

2.0

Created at

2022-09-02 02:20:22 UTC

Updated at

2022-09-02 02:20:22 UTC

NP-MRD ID

NP0146856

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadeca-11,13-diene-2,6,10-trione

Description

4,8-Dihydroxy-5,5,7,9,13-pentamethyl-16-[1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadeca-11,13-diene-2,6,10-trione 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-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadeca-11,13-diene-2,6,10-trione is found in Myxococcus xanthus. Based on a literature review very few articles have been published on 4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadeca-11,13-diene-2,6,10-trione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022204202D          

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  Mrv1652309022204202D          

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 21 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 34 32  1  4  0  0  0
 34 35  2  0  0  0  0
  2 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0146856

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C(O)C(C)C(=O)C(C)(C)C(O)CC(=O)OC(CC=C(C)C=CC1=O)C(C)=CC1=CSC(C)=N1

> <INCHI_IDENTIFIER>
InChI=1S/C27H37NO6S/c1-15-8-10-21(29)17(3)25(32)18(4)26(33)27(6,7)23(30)13-24(31)34-22(11-9-15)16(2)12-20-14-35-19(5)28-20/h8-10,12,14,17-18,22-23,25,30,32H,11,13H2,1-7H3

> <INCHI_KEY>
VARJYEHLJSMYQM-UHFFFAOYSA-N

> <FORMULA>
C27H37NO6S

> <MOLECULAR_WEIGHT>
503.65

> <EXACT_MASS>
503.234159089

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
54.66291434264807

> <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-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadeca-11,13-diene-2,6,10-trione

> <ALOGPS_LOGP>
3.60

> <JCHEM_LOGP>
4.248835949

> <ALOGPS_LOGS>
-5.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.615326895108037

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.999881603186719

> <JCHEM_PKA_STRONGEST_BASIC>
2.726300026492813

> <JCHEM_POLAR_SURFACE_AREA>
113.79000000000002

> <JCHEM_REFRACTIVITY>
137.72669999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.46e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadeca-11,13-diene-2,6,10-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       2.667  14.940   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  15.710   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335  14.940   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  13.400   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  12.630   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  11.090   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335  10.320   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  10.320   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   8.780   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.913   7.875   0.000  0.00  0.00           C+0
HETATM   11  S   UNK     0       3.437   6.410   0.000  0.00  0.00           S+0
HETATM   12  C   UNK     0       1.897   6.410   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.992   5.164   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       1.421   7.875   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0       2.667  13.400   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.334  12.630   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.334  11.090   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.000  13.400   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.334  12.630   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.334  11.090   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.667  13.400   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.194  11.953   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.184  13.667   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.667  14.940   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -4.001  15.710   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -1.334  15.710   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.000  14.940   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.334  17.250   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -2.667  18.020   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.000  18.020   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.000  19.560   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.334  17.250   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       1.334  15.710   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       2.667  18.020   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.001  17.250   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   35                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   15                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    9                                                       
CONECT   15    5   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23   24                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   21   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34    2                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₇NO₆S

Average Mass

503.6500 Da

Monoisotopic Mass

503.23416 Da

IUPAC Name

4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadeca-11,13-diene-2,6,10-trione

Traditional Name

4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadeca-11,13-diene-2,6,10-trione

CAS Registry Number

Not Available

SMILES

CC1C(O)C(C)C(=O)C(C)(C)C(O)CC(=O)OC(CC=C(C)C=CC1=O)C(C)=CC1=CSC(C)=N1

InChI Identifier

InChI=1S/C27H37NO6S/c1-15-8-10-21(29)17(3)25(32)18(4)26(33)27(6,7)23(30)13-24(31)34-22(11-9-15)16(2)12-20-14-35-19(5)28-20/h8-10,12,14,17-18,22-23,25,30,32H,11,13H2,1-7H3

InChI Key

VARJYEHLJSMYQM-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
Myxococcus xanthus	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-thiazole
Azole
Heteroaromatic compound
Thiazole
Carboxylic acid ester
Ketone
Lactone
Secondary alcohol
Cyclic ketone
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Azacycle
Organoheterocyclic compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organic oxygen 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	3.6	ALOGPS
logP	4.25	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	14	ChemAxon
pKa (Strongest Basic)	2.73	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	113.79 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	137.73 m³·mol⁻¹	ChemAxon
Polarizability	54.66 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

72968003

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-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadeca-11,13-diene-2,6,10-trione (NP0146856)

MOL for NP0146856 (4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadeca-11,13-diene-2,6,10-trione)

3D MOL for NP0146856 (4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadeca-11,13-diene-2,6,10-trione)

3D SDF for NP0146856 (4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadeca-11,13-diene-2,6,10-trione)

3D-SDF for NP0146856 (4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadeca-11,13-diene-2,6,10-trione)

PDB for NP0146856 (4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadeca-11,13-diene-2,6,10-trione)

3D PDB for NP0146856 (4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadeca-11,13-diene-2,6,10-trione)

SMILES for NP0146856 (4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadeca-11,13-diene-2,6,10-trione)

INCHI for NP0146856 (4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadeca-11,13-diene-2,6,10-trione)

Structure for NP0146856 (4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadeca-11,13-diene-2,6,10-trione)

3D Structure for NP0146856 (4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadeca-11,13-diene-2,6,10-trione)