NP-MRD: Showing NP-Card for (4s,7r,8r,9e,13z,16s)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(1e)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadeca-9,13-diene-2,6-dione (NP0271891)

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Record Information

Version

1.0

Created at

2022-09-08 18:19:24 UTC

Updated at

2022-09-08 18:19:24 UTC

NP-MRD ID

NP0271891

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4s,7r,8r,9e,13z,16s)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(1e)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadeca-9,13-diene-2,6-dione

Description

Epothilone D5 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. (4s,7r,8r,9e,13z,16s)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(1e)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadeca-9,13-diene-2,6-dione is found in Sorangium cellulosum. Based on a literature review very few articles have been published on epothilone D5.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082220192D          

 34 35  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309082220192D          

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 26 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
  2 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0271891

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C27H39NO5S/c1-16-9-8-10-17(2)25(31)19(4)26(32)27(6,7)23(29)14-24(30)33-22(12-11-16)18(3)13-21-15-34-20(5)28-21/h10-11,13,15,19,22-23,25,29,31H,8-9,12,14H2,1-7H3/b16-11-,17-10+,18-13+/t19-,22+,23+,25+/m1/s1

> <INCHI_KEY>
OQUHUZWYEYDRMH-JGMJILQLSA-N

> <FORMULA>
C27H39NO5S

> <MOLECULAR_WEIGHT>
489.67

> <EXACT_MASS>
489.254894534

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
54.2768157395396

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4S,7R,8R,9E,13Z,16S)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadeca-9,13-diene-2,6-dione

> <JCHEM_LOGP>
4.768683521333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.544073702063852

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.936957390872937

> <JCHEM_PKA_STRONGEST_BASIC>
2.7263000319206507

> <JCHEM_POLAR_SURFACE_AREA>
96.72000000000001

> <JCHEM_REFRACTIVITY>
136.8161

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4S,7R,8R,9E,13Z,16S)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadeca-9,13-diene-2,6-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       1.533   3.735   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.199   4.505   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.134   3.735   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.468   4.505   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.802   3.735   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.802   2.195   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.468   1.425   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.136   1.425   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.136  -0.115   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.890  -1.020   0.000  0.00  0.00           C+0
HETATM   11  S   UNK     0      -4.366  -2.485   0.000  0.00  0.00           S+0
HETATM   12  C   UNK     0      -5.906  -2.485   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.811  -3.731   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      -6.381  -1.020   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0      -5.136   4.505   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -5.136   6.045   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -6.469   6.815   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -3.802   6.815   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.802   8.355   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -5.136   9.125   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.468   9.125   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.985   9.392   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.458  10.305   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.468  10.665   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -3.802  11.435   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -1.134  11.435   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.134  12.975   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.199  10.665   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.533  11.435   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.199   9.125   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.134   8.355   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.533   8.355   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.533   6.815   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.199   6.045   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   34                                                  
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                                                       
CONECT   33   32   34                                                       
CONECT   34   33    2                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₉NO₅S

Average Mass

489.6700 Da

Monoisotopic Mass

489.25489 Da

IUPAC Name

(4S,7R,8R,9E,13Z,16S)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadeca-9,13-diene-2,6-dione

Traditional Name

(4S,7R,8R,9E,13Z,16S)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadeca-9,13-diene-2,6-dione

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C27H39NO5S/c1-16-9-8-10-17(2)25(31)19(4)26(32)27(6,7)23(29)14-24(30)33-22(12-11-16)18(3)13-21-15-34-20(5)28-21/h10-11,13,15,19,22-23,25,29,31H,8-9,12,14H2,1-7H3/b16-11-,17-10+,18-13+/t19-,22+,23+,25+/m1/s1

InChI Key

OQUHUZWYEYDRMH-JGMJILQLSA-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-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
Carbonyl group
Aldehyde
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
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	4.77	ChemAxon
pKa (Strongest Acidic)	13.94	ChemAxon
pKa (Strongest Basic)	2.73	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	96.72 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	136.82 m³·mol⁻¹	ChemAxon
Polarizability	54.28 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

C00045913

Chemspider ID

8089094

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11134719

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (4s,7r,8r,9e,13z,16s)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(1e)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadeca-9,13-diene-2,6-dione (NP0271891)

MOL for NP0271891 ((4s,7r,8r,9e,13z,16s)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(1e)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadeca-9,13-diene-2,6-dione)

3D MOL for NP0271891 ((4s,7r,8r,9e,13z,16s)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(1e)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadeca-9,13-diene-2,6-dione)

3D SDF for NP0271891 ((4s,7r,8r,9e,13z,16s)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(1e)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadeca-9,13-diene-2,6-dione)

3D-SDF for NP0271891 ((4s,7r,8r,9e,13z,16s)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(1e)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadeca-9,13-diene-2,6-dione)

PDB for NP0271891 ((4s,7r,8r,9e,13z,16s)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(1e)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadeca-9,13-diene-2,6-dione)

3D PDB for NP0271891 ((4s,7r,8r,9e,13z,16s)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(1e)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadeca-9,13-diene-2,6-dione)

SMILES for NP0271891 ((4s,7r,8r,9e,13z,16s)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(1e)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadeca-9,13-diene-2,6-dione)

INCHI for NP0271891 ((4s,7r,8r,9e,13z,16s)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(1e)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadeca-9,13-diene-2,6-dione)

Structure for NP0271891 ((4s,7r,8r,9e,13z,16s)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(1e)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadeca-9,13-diene-2,6-dione)

3D Structure for NP0271891 ((4s,7r,8r,9e,13z,16s)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(1e)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadeca-9,13-diene-2,6-dione)