NP-MRD: Showing NP-Card for 7,11-dihydroxy-3-{1-[2-(hydroxymethyl)-1,3-thiazol-4-yl]prop-1-en-2-yl}-8,8,10,12,16-pentamethyl-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione (NP0226514)

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Record Information

Version

2.0

Created at

2022-09-06 05:34:59 UTC

Updated at

2022-09-06 05:34:59 UTC

NP-MRD ID

NP0226514

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7,11-dihydroxy-3-{1-[2-(hydroxymethyl)-1,3-thiazol-4-yl]prop-1-en-2-yl}-8,8,10,12,16-pentamethyl-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione

Description

7,11-Dihydroxy-3-{1-[2-(hydroxymethyl)-1,3-thiazol-4-yl]prop-1-en-2-yl}-8,8,10,12,16-pentamethyl-4,17-dioxabicyclo[14.1.0]Heptadecane-5,9-dione belongs to the class of organic compounds known as epothilones and analogues. These are macrolides consisting of a 16-member lactone ring conjugated at the carbon 16 with a 1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl group. Some epothilone analogues containing a lactam ring instead of the lactone ring. 7,11-dihydroxy-3-{1-[2-(hydroxymethyl)-1,3-thiazol-4-yl]prop-1-en-2-yl}-8,8,10,12,16-pentamethyl-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione is found in Sorangium cellulosum. 7,11-Dihydroxy-3-{1-[2-(hydroxymethyl)-1,3-thiazol-4-yl]prop-1-en-2-yl}-8,8,10,12,16-pentamethyl-4,17-dioxabicyclo[14.1.0]Heptadecane-5,9-dione is a moderately basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231517282D          

 36 38  0  0  0  0            999 V2000
    3.3048   -1.1701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2721    0.7624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4112    0.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1902    1.4457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

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M  END


  Mrv1533004231517282D          

 36 38  0  0  0  0            999 V2000
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    0.8824    5.6964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9100    6.5209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2097    6.9571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5332    5.1894    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5310    2.9297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  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  1  0  0  0  0
  8  9  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
  2 25  1  0  0  0  0
 25 26  1  0  0  0  0
 11 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  4  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 32 35  2  0  0  0  0
 29 35  1  0  0  0  0
 27 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0226514

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CCCC2(C)OC2CC(OC(=O)CC(O)C(C)(C)C(=O)C(C)C1O)C(C)=CC1=CSC(CO)=N1

> <INCHI_IDENTIFIER>
InChI=1S/C27H41NO7S/c1-15-8-7-9-27(6)21(35-27)11-19(16(2)10-18-14-36-22(13-29)28-18)34-23(31)12-20(30)26(4,5)25(33)17(3)24(15)32/h10,14-15,17,19-21,24,29-30,32H,7-9,11-13H2,1-6H3

> <INCHI_KEY>
UKIMCRYGLFQEOE-UHFFFAOYSA-N

> <FORMULA>
C27H41NO7S

> <MOLECULAR_WEIGHT>
523.69

> <EXACT_MASS>
523.260373838

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
56.73759063611543

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7,11-dihydroxy-3-{1-[2-(hydroxymethyl)-1,3-thiazol-4-yl]prop-1-en-2-yl}-8,8,10,12,16-pentamethyl-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione

> <ALOGPS_LOGP>
2.87

> <JCHEM_LOGP>
3.3054857123333328

> <ALOGPS_LOGS>
-4.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.185907718825288

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.508939660738935

> <JCHEM_PKA_STRONGEST_BASIC>
1.071502859178128

> <JCHEM_POLAR_SURFACE_AREA>
129.48000000000002

> <JCHEM_REFRACTIVITY>
136.4622

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.51e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7,11-dihydroxy-3-{1-[2-(hydroxymethyl)-1,3-thiazol-4-yl]prop-1-en-2-yl}-8,8,10,12,16-pentamethyl-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0       6.169  -2.184   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.306  -0.909   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.770  -1.018   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.907   0.257   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.371   0.148   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.508   1.423   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.768   0.560   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.355   2.699   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.181   2.808   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.717   2.918   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.390   4.303   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.926   4.413   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.599   5.798   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.736   7.073   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       7.135   5.907   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.998   4.632   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       9.535   4.741   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       7.325   3.247   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.731   3.875   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.806   2.824   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.188   1.971   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       9.724   2.081   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.515   0.586   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.378  -0.689   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.979   0.476   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.842  -0.799   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.527   5.578   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.200   6.964   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.337   8.239   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.798   8.291   0.000  0.00  0.00           C+0
HETATM   31  S   UNK     0       0.372   9.770   0.000  0.00  0.00           S+0
HETATM   32  C   UNK     0       1.647  10.633   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.699  12.172   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       0.392  12.987   0.000  0.00  0.00           O+0
HETATM   35  N   UNK     0       2.862   9.687   0.000  0.00  0.00           N+0
HETATM   36  C   UNK     0       0.991   5.469   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   25                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8    6   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   27                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23    2   26                                                  
CONECT   26   25                                                            
CONECT   27   11   28   36                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   35                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   35                                                  
CONECT   33   32   34                                                       
CONECT   34   33                                                            
CONECT   35   32   29                                                       
CONECT   36   27                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₁NO₇S

Average Mass

523.6900 Da

Monoisotopic Mass

523.26037 Da

IUPAC Name

7,11-dihydroxy-3-{1-[2-(hydroxymethyl)-1,3-thiazol-4-yl]prop-1-en-2-yl}-8,8,10,12,16-pentamethyl-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione

Traditional Name

7,11-dihydroxy-3-{1-[2-(hydroxymethyl)-1,3-thiazol-4-yl]prop-1-en-2-yl}-8,8,10,12,16-pentamethyl-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione

CAS Registry Number

Not Available

SMILES

CC1CCCC2(C)OC2CC(OC(=O)CC(O)C(C)(C)C(=O)C(C)C1O)C(C)=CC1=CSC(CO)=N1

InChI Identifier

InChI=1S/C27H41NO7S/c1-15-8-7-9-27(6)21(35-27)11-19(16(2)10-18-14-36-22(13-29)28-18)34-23(31)12-20(30)26(4,5)25(33)17(3)24(15)32/h10,14-15,17,19-21,24,29-30,32H,7-9,11-13H2,1-6H3

InChI Key

UKIMCRYGLFQEOE-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 epothilones and analogues. These are macrolides consisting of a 16-member lactone ring conjugated at the carbon 16 with a 1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl group. Some epothilone analogues containing a lactam ring instead of the lactone ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Epothilones and analogues

Direct Parent

Epothilones and analogues

Alternative Parents

Substituents

Epothilone
2,4-disubstituted 1,3-thiazole
Azole
Heteroaromatic compound
Thiazole
Carboxylic acid ester
Ketone
Lactone
Secondary alcohol
Cyclic ketone
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Azacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organic nitrogen compound
Organic oxide
Organonitrogen compound
Organooxygen compound
Primary alcohol
Alcohol
Aromatic alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	2.87	ALOGPS
logP	3.31	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	13.51	ChemAxon
pKa (Strongest Basic)	1.07	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	129.48 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	136.46 m³·mol⁻¹	ChemAxon
Polarizability	56.74 Å³	ChemAxon
Number of Rings	3	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

72808432

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 7,11-dihydroxy-3-{1-[2-(hydroxymethyl)-1,3-thiazol-4-yl]prop-1-en-2-yl}-8,8,10,12,16-pentamethyl-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione (NP0226514)

MOL for NP0226514 (7,11-dihydroxy-3-{1-[2-(hydroxymethyl)-1,3-thiazol-4-yl]prop-1-en-2-yl}-8,8,10,12,16-pentamethyl-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione)

3D MOL for NP0226514 (7,11-dihydroxy-3-{1-[2-(hydroxymethyl)-1,3-thiazol-4-yl]prop-1-en-2-yl}-8,8,10,12,16-pentamethyl-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione)

3D SDF for NP0226514 (7,11-dihydroxy-3-{1-[2-(hydroxymethyl)-1,3-thiazol-4-yl]prop-1-en-2-yl}-8,8,10,12,16-pentamethyl-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione)

3D-SDF for NP0226514 (7,11-dihydroxy-3-{1-[2-(hydroxymethyl)-1,3-thiazol-4-yl]prop-1-en-2-yl}-8,8,10,12,16-pentamethyl-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione)

PDB for NP0226514 (7,11-dihydroxy-3-{1-[2-(hydroxymethyl)-1,3-thiazol-4-yl]prop-1-en-2-yl}-8,8,10,12,16-pentamethyl-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione)

3D PDB for NP0226514 (7,11-dihydroxy-3-{1-[2-(hydroxymethyl)-1,3-thiazol-4-yl]prop-1-en-2-yl}-8,8,10,12,16-pentamethyl-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione)

SMILES for NP0226514 (7,11-dihydroxy-3-{1-[2-(hydroxymethyl)-1,3-thiazol-4-yl]prop-1-en-2-yl}-8,8,10,12,16-pentamethyl-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione)

INCHI for NP0226514 (7,11-dihydroxy-3-{1-[2-(hydroxymethyl)-1,3-thiazol-4-yl]prop-1-en-2-yl}-8,8,10,12,16-pentamethyl-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione)

Structure for NP0226514 (7,11-dihydroxy-3-{1-[2-(hydroxymethyl)-1,3-thiazol-4-yl]prop-1-en-2-yl}-8,8,10,12,16-pentamethyl-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione)

3D Structure for NP0226514 (7,11-dihydroxy-3-{1-[2-(hydroxymethyl)-1,3-thiazol-4-yl]prop-1-en-2-yl}-8,8,10,12,16-pentamethyl-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione)