NP-MRD: Showing NP-Card for 21,26-Dihydroxyepothilone D (NP0060998)

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Record Information

Version

2.0

Created at

2022-04-28 05:56:23 UTC

Updated at

2022-04-28 05:56:23 UTC

NP-MRD ID

NP0060998

Secondary Accession Numbers

None

Natural Product Identification

Common Name

21,26-Dihydroxyepothilone D

Description

(4S,7R,8S,9S,13E,16S)-4,8-Dihydroxy-5,5,7,9-tetramethyl-13-(hydroxymethyl)-16-[(E)-1-methyl-2-[2-(hydroxymethyl)-4-thiazolyl]ethenyl]-1-oxacyclohexadeca-13-ene-2,6-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. 21,26-Dihydroxyepothilone D is found in Amycolata autotrophica. Based on a literature review very few articles have been published on (4S,7R,8S,9S,13E,16S)-4,8-Dihydroxy-5,5,7,9-tetramethyl-13-(hydroxymethyl)-16-[(E)-1-methyl-2-[2-(hydroxymethyl)-4-thiazolyl]ethenyl]-1-oxacyclohexadeca-13-ene-2,6-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282207562D          

 36 37  0  0  1  0            999 V2000
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M  END

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M  END


  Mrv1652304282207562D          

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  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  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  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  1 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 17 21  1  6  0  0  0
 12 22  1  6  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 24 28  2  0  0  0  0
 26 29  1  0  0  0  0
 29 30  1  0  0  0  0
 22 31  1  0  0  0  0
  9 32  1  0  0  0  0
 32 33  1  0  0  0  0
  5 34  1  1  0  0  0
  4 35  1  1  0  0  0
  3 36  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0060998

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CCC\C(CO)=C/C[C@H](OC(=O)C[C@H](O)C(C)(C)C(=O)[C@H](C)[C@H]1O)C(\C)=C\C1=CSC(CO)=N1

> <INCHI_IDENTIFIER>
InChI=1S/C27H41NO7S/c1-16-7-6-8-19(13-29)9-10-21(17(2)11-20-15-36-23(14-30)28-20)35-24(32)12-22(31)27(4,5)26(34)18(3)25(16)33/h9,11,15-16,18,21-22,25,29-31,33H,6-8,10,12-14H2,1-5H3/b17-11+,19-9+/t16-,18+,21-,22-,25-/m0/s1

> <INCHI_KEY>
WFGBIZQKLKDZTA-XQRCBBSISA-N

> <FORMULA>
C27H41NO7S

> <MOLECULAR_WEIGHT>
523.69

> <EXACT_MASS>
523.260373838

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
57.198079819563844

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4S,7R,8S,9S,13E,16S)-4,8-dihydroxy-13-(hydroxymethyl)-16-[(1E)-1-[2-(hydroxymethyl)-1,3-thiazol-4-yl]prop-1-en-2-yl]-5,5,7,9-tetramethyl-1-oxacyclohexadec-13-ene-2,6-dione

> <ALOGPS_LOGP>
2.68

> <JCHEM_LOGP>
2.998290069999998

> <ALOGPS_LOGS>
-4.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.185891425945442

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.508892866876213

> <JCHEM_PKA_STRONGEST_BASIC>
1.0718587280219547

> <JCHEM_POLAR_SURFACE_AREA>
137.18

> <JCHEM_REFRACTIVITY>
139.52

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.64e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4S,7R,8S,9S,13E,16S)-4,8-dihydroxy-13-(hydroxymethyl)-16-[(1E)-1-[2-(hydroxymethyl)-1,3-thiazol-4-yl]prop-1-en-2-yl]-5,5,7,9-tetramethyl-1-oxacyclohexadec-13-ene-2,6-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       7.803   7.585   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       9.137   6.815   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.803   9.125   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.137   9.895   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.470   9.125   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.470   7.585   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.804   6.815   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.804   5.275   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.138   4.505   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.138   2.965   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.804   2.195   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.470   2.965   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.137   2.195   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       7.803   2.965   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.469   2.195   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       7.803   4.505   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.469   5.275   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.469   6.815   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.930   6.869   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.653   8.121   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.136   4.505   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      10.470   1.425   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.804   0.655   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.804  -0.885   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0      13.050  -1.790   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0      12.574  -3.255   0.000  0.00  0.00           C+0
HETATM   27  S   UNK     0      11.034  -3.255   0.000  0.00  0.00           S+0
HETATM   28  C   UNK     0      10.558  -1.790   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.479  -4.501   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      12.853  -5.908   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       9.137   0.655   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      14.471   5.275   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      15.805   4.505   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      11.804   9.895   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       9.137  11.435   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       6.469   9.895   0.000  0.00  0.00           C+0
CONECT    1    2    3   18                                                  
CONECT    2    1                                                            
CONECT    3    1    4   36                                                  
CONECT    4    3    5   35                                                  
CONECT    5    4    6   34                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   32                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   22                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   21                                                  
CONECT   18   17    1   19   20                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   17                                                            
CONECT   22   12   23   31                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   28                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27   24                                                       
CONECT   29   26   30                                                       
CONECT   30   29                                                            
CONECT   31   22                                                            
CONECT   32    9   33                                                       
CONECT   33   32                                                            
CONECT   34    5                                                            
CONECT   35    4                                                            
CONECT   36    3                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₁NO₇S

Average Mass

523.6900 Da

Monoisotopic Mass

523.26037 Da

IUPAC Name

(4S,7R,8S,9S,13E,16S)-4,8-dihydroxy-13-(hydroxymethyl)-16-[(1E)-1-[2-(hydroxymethyl)-1,3-thiazol-4-yl]prop-1-en-2-yl]-5,5,7,9-tetramethyl-1-oxacyclohexadec-13-ene-2,6-dione

Traditional Name

(4S,7R,8S,9S,13E,16S)-4,8-dihydroxy-13-(hydroxymethyl)-16-[(1E)-1-[2-(hydroxymethyl)-1,3-thiazol-4-yl]prop-1-en-2-yl]-5,5,7,9-tetramethyl-1-oxacyclohexadec-13-ene-2,6-dione

CAS Registry Number

Not Available

SMILES

C[C@H]1CCC\C(CO)=C/C[C@H](OC(=O)C[C@H](O)C(C)(C)C(=O)[C@H](C)[C@H]1O)C(\C)=C\C1=CSC(CO)=N1

InChI Identifier

InChI=1S/C27H41NO7S/c1-16-7-6-8-19(13-29)9-10-21(17(2)11-20-15-36-23(14-30)28-20)35-24(32)12-22(31)27(4,5)26(34)18(3)25(16)33/h9,11,15-16,18,21-22,25,29-31,33H,6-8,10,12-14H2,1-5H3/b17-11+,19-9+/t16-,18+,21-,22-,25-/m0/s1

InChI Key

WFGBIZQKLKDZTA-XQRCBBSISA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Pseudonocardia autotrophica	-	KNApSAcK

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
Oxacycle
Azacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Primary alcohol
Carbonyl group
Aromatic alcohol
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	2.68	ALOGPS
logP	3	ChemAxon
logS	-4.8	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	4	ChemAxon
Polar Surface Area	137.18 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	139.52 m³·mol⁻¹	ChemAxon
Polarizability	57.2 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

8304114

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10128595

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 21,26-Dihydroxyepothilone D (NP0060998)

MOL for NP0060998 (21,26-Dihydroxyepothilone D)

3D MOL for NP0060998 (21,26-Dihydroxyepothilone D)

3D SDF for NP0060998 (21,26-Dihydroxyepothilone D)

3D-SDF for NP0060998 (21,26-Dihydroxyepothilone D)

PDB for NP0060998 (21,26-Dihydroxyepothilone D)

3D PDB for NP0060998 (21,26-Dihydroxyepothilone D)

SMILES for NP0060998 (21,26-Dihydroxyepothilone D)

INCHI for NP0060998 (21,26-Dihydroxyepothilone D)

Structure for NP0060998 (21,26-Dihydroxyepothilone D)

3D Structure for NP0060998 (21,26-Dihydroxyepothilone D)