NP-MRD: Showing NP-Card for (4s,5r,7r,8s,9s,11r,15z,18s)-4,8-dihydroxy-5,7,9,11,15-pentamethyl-18-[(1e)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclooctadec-15-ene-2,6-dione (NP0241128)

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Record Information

Version

2.0

Created at

2022-09-07 01:07:09 UTC

Updated at

2022-09-07 01:07:09 UTC

NP-MRD ID

NP0241128

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4s,5r,7r,8s,9s,11r,15z,18s)-4,8-dihydroxy-5,7,9,11,15-pentamethyl-18-[(1e)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclooctadec-15-ene-2,6-dione

Description

(4S,5R,7R,8S,9S,11R,15Z,18S)-4,8-dihydroxy-5,7,9,11,15-pentamethyl-18-[1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclooctadec-15-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. (4s,5r,7r,8s,9s,11r,15z,18s)-4,8-dihydroxy-5,7,9,11,15-pentamethyl-18-[(1e)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclooctadec-15-ene-2,6-dione is found in Sorangium cellulosum. Based on a literature review very few articles have been published on (4S,5R,7R,8S,9S,11R,15Z,18S)-4,8-dihydroxy-5,7,9,11,15-pentamethyl-18-[1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclooctadec-15-ene-2,6-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072203072D          

 36 37  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309072203072D          

 36 37  0  0  1  0            999 V2000
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   -0.6078    6.9509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1067    5.7134    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1067    4.8884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8212    6.1259    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8212    6.9509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5356    5.7134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5356    4.8884    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2501    4.4759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8212    4.4759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8212    3.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1067    3.2384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  1  0  0  0  0
  6  8  2  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
 12 14  2  0  0  0  0
  9 14  1  0  0  0  0
  5 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  6  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
  2 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0241128

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C29H45NO5S/c1-17-9-8-10-18(2)13-20(4)28(33)22(6)29(34)21(5)25(31)15-27(32)35-26(12-11-17)19(3)14-24-16-36-23(7)30-24/h11,14,16,18,20-22,25-26,28,31,33H,8-10,12-13,15H2,1-7H3/b17-11-,19-14+/t18-,20+,21-,22-,25+,26+,28+/m1/s1

> <INCHI_KEY>
LUSOGNSOTZPASB-BTOPGAJLSA-N

> <FORMULA>
C29H45NO5S

> <MOLECULAR_WEIGHT>
519.74

> <EXACT_MASS>
519.301844727

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
58.86049430252945

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4S,5R,7R,8S,9S,11R,15Z,18S)-4,8-dihydroxy-5,7,9,11,15-pentamethyl-18-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclooctadec-15-ene-2,6-dione

> <JCHEM_LOGP>
5.716451396999998

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.827986596501663

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.203239462136683

> <JCHEM_PKA_STRONGEST_BASIC>
2.7263000319259025

> <JCHEM_POLAR_SURFACE_AREA>
96.72000000000001

> <JCHEM_REFRACTIVITY>
145.29269999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(4S,5R,7R,8S,9S,11R,15Z,18S)-4,8-dihydroxy-5,7,9,11,15-pentamethyl-18-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclooctadec-15-ene-2,6-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-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      -1.134   8.355   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.468  10.665   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -3.802  11.435   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -1.134  11.435   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.134  12.975   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.199  10.665   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       0.199   9.125   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       1.533  11.435   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.533  12.975   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.867  10.665   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.867   9.125   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.200   8.355   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.533   8.355   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.533   6.815   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       0.199   6.045   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   36                                                  
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                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35    2                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₄₅NO₅S

Average Mass

519.7400 Da

Monoisotopic Mass

519.30184 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C29H45NO5S/c1-17-9-8-10-18(2)13-20(4)28(33)22(6)29(34)21(5)25(31)15-27(32)35-26(12-11-17)19(3)14-24-16-36-23(7)30-24/h11,14,16,18,20-22,25-26,28,31,33H,8-10,12-13,15H2,1-7H3/b17-11-,19-14+/t18-,20+,21-,22-,25+,26+,28+/m1/s1

InChI Key

LUSOGNSOTZPASB-BTOPGAJLSA-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
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

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

163190266

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (4s,5r,7r,8s,9s,11r,15z,18s)-4,8-dihydroxy-5,7,9,11,15-pentamethyl-18-[(1e)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclooctadec-15-ene-2,6-dione (NP0241128)

MOL for NP0241128 ((4s,5r,7r,8s,9s,11r,15z,18s)-4,8-dihydroxy-5,7,9,11,15-pentamethyl-18-[(1e)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclooctadec-15-ene-2,6-dione)

3D MOL for NP0241128 ((4s,5r,7r,8s,9s,11r,15z,18s)-4,8-dihydroxy-5,7,9,11,15-pentamethyl-18-[(1e)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclooctadec-15-ene-2,6-dione)

3D SDF for NP0241128 ((4s,5r,7r,8s,9s,11r,15z,18s)-4,8-dihydroxy-5,7,9,11,15-pentamethyl-18-[(1e)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclooctadec-15-ene-2,6-dione)

3D-SDF for NP0241128 ((4s,5r,7r,8s,9s,11r,15z,18s)-4,8-dihydroxy-5,7,9,11,15-pentamethyl-18-[(1e)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclooctadec-15-ene-2,6-dione)

PDB for NP0241128 ((4s,5r,7r,8s,9s,11r,15z,18s)-4,8-dihydroxy-5,7,9,11,15-pentamethyl-18-[(1e)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclooctadec-15-ene-2,6-dione)

3D PDB for NP0241128 ((4s,5r,7r,8s,9s,11r,15z,18s)-4,8-dihydroxy-5,7,9,11,15-pentamethyl-18-[(1e)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclooctadec-15-ene-2,6-dione)

SMILES for NP0241128 ((4s,5r,7r,8s,9s,11r,15z,18s)-4,8-dihydroxy-5,7,9,11,15-pentamethyl-18-[(1e)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclooctadec-15-ene-2,6-dione)

INCHI for NP0241128 ((4s,5r,7r,8s,9s,11r,15z,18s)-4,8-dihydroxy-5,7,9,11,15-pentamethyl-18-[(1e)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclooctadec-15-ene-2,6-dione)

Structure for NP0241128 ((4s,5r,7r,8s,9s,11r,15z,18s)-4,8-dihydroxy-5,7,9,11,15-pentamethyl-18-[(1e)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclooctadec-15-ene-2,6-dione)

3D Structure for NP0241128 ((4s,5r,7r,8s,9s,11r,15z,18s)-4,8-dihydroxy-5,7,9,11,15-pentamethyl-18-[(1e)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclooctadec-15-ene-2,6-dione)