NP-MRD: Showing NP-Card for methyl (2s)-2-[(1s,2r,5s,6s,10s,12s,13s,15s,16r,18s,19s)-6-(furan-3-yl)-15,18-dihydroxy-1,5,16-trimethyl-8,14-dioxo-7,11-dioxahexacyclo[14.2.1.0²,¹².0⁵,¹⁰.0¹⁰,¹².0¹³,¹⁸]nonadecan-19-yl]-2-hydroxyacetate (NP0270765)

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Record Information

Version

2.0

Created at

2022-09-08 16:49:10 UTC

Updated at

2022-09-08 16:49:10 UTC

NP-MRD ID

NP0270765

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (2s)-2-[(1s,2r,5s,6s,10s,12s,13s,15s,16r,18s,19s)-6-(furan-3-yl)-15,18-dihydroxy-1,5,16-trimethyl-8,14-dioxo-7,11-dioxahexacyclo[14.2.1.0²,¹².0⁵,¹⁰.0¹⁰,¹².0¹³,¹⁸]nonadecan-19-yl]-2-hydroxyacetate

Description

ZINC67903449 belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid. methyl (2s)-2-[(1s,2r,5s,6s,10s,12s,13s,15s,16r,18s,19s)-6-(furan-3-yl)-15,18-dihydroxy-1,5,16-trimethyl-8,14-dioxo-7,11-dioxahexacyclo[14.2.1.0²,¹².0⁵,¹⁰.0¹⁰,¹².0¹³,¹⁸]nonadecan-19-yl]-2-hydroxyacetate is found in Khaya ivorensis and Khaya senegalensis. Based on a literature review very few articles have been published on ZINC67903449.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082218492D          

 37 43  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309082218492D          

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  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 16 20  2  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 13 25  1  0  0  0  0
 25 26  1  6  0  0  0
 27 26  1  6  0  0  0
 10 27  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  1  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
  7 33  1  0  0  0  0
 33 34  1  1  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 28 36  1  0  0  0  0
  8 36  1  0  0  0  0
 36 37  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0270765

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@H](O)[C@H]1[C@@]2(C)C[C@]3(O)[C@H](C(=O)[C@H]2O)[C@]24O[C@]22CC(=O)O[C@@H](C5=COC=C5)[C@]2(C)CC[C@@H]4[C@]13C

> <INCHI_IDENTIFIER>
InChI=1S/C27H32O10/c1-22-11-25(33)18(15(29)19(22)31)27-13(24(25,3)17(22)16(30)21(32)34-4)5-7-23(2)20(12-6-8-35-10-12)36-14(28)9-26(23,27)37-27/h6,8,10,13,16-20,30-31,33H,5,7,9,11H2,1-4H3/t13-,16+,17+,18+,19-,20+,22-,23+,24-,25+,26+,27+/m1/s1

> <INCHI_KEY>
SZIDPCXTWHHMAY-LUUUZSLOSA-N

> <FORMULA>
C27H32O10

> <MOLECULAR_WEIGHT>
516.543

> <EXACT_MASS>
516.19954723

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
51.182715774609775

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (2S)-2-[(1S,2R,5S,6R,10S,12S,13S,15S,16R,18S,19S)-6-(furan-3-yl)-15,18-dihydroxy-1,5,16-trimethyl-8,14-dioxo-7,11-dioxahexacyclo[14.2.1.0^{2,12}.0^{5,10}.0^{10,12}.0^{13,18}]nonadecan-19-yl]-2-hydroxyacetate

> <JCHEM_LOGP>
0.30528502333333307

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.425252355296713

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.644685150199363

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8710296166814895

> <JCHEM_POLAR_SURFACE_AREA>
156.02999999999997

> <JCHEM_REFRACTIVITY>
121.94659999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(S)-(methyl [(1S,2R,5S,6R,10S,12S,13S,15S,16R,18S,19S)-6-(furan-3-yl)-15,18-dihydroxy-1,5,16-trimethyl-8,14-dioxo-7,11-dioxahexacyclo[14.2.1.0^{2,12}.0^{5,10}.0^{10,12}.0^{13,18}]nonadecan-19-yl](hydroxy)acetate)

> <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      -2.574   1.276   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.178   1.925   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.082   1.040   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.054  -0.494   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.479   1.688   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.616   3.222   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.739   0.803   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.382   1.323   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.015   2.818   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.120   1.631   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.095   2.915   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.667   2.885   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.452   1.518   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.257   2.831   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.053   1.436   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.876   2.737   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.308   4.169   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.493   5.152   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      13.794   4.328   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      13.413   2.836   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      11.792   0.062   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      10.988  -1.263   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      11.703  -2.627   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       9.464  -1.172   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.598   0.182   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       7.737  -1.098   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.943   0.251   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.708  -0.823   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.276  -2.315   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       6.324  -3.444   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       3.728  -2.642   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       3.137  -4.064   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       2.820  -1.241   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.353  -1.707   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.581  -0.215   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.400  -0.033   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       4.061  -1.536   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   33                                                  
CONECT    8    7    9   10   36                                             
CONECT    9    8                                                            
CONECT   10    8   11   27                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   25                                             
CONECT   14   13                                                            
CONECT   15   13   16   21                                                  
CONECT   16   15   17   20                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   16                                                       
CONECT   21   15   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   13   26   27                                             
CONECT   26   25   27                                                       
CONECT   27   26   10   25   28                                             
CONECT   28   27   29   36                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31    7   34   35                                             
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35   28    8   37                                             
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₂O₁₀

Average Mass

516.5430 Da

Monoisotopic Mass

516.19955 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@H](O)[C@H]1[C@@]2(C)C[C@]3(O)[C@H](C(=O)[C@H]2O)[C@]24O[C@]22CC(=O)O[C@@H](C5=COC=C5)[C@]2(C)CC[C@@H]4[C@]13C

InChI Identifier

InChI=1S/C27H32O10/c1-22-11-25(33)18(15(29)19(22)31)27-13(24(25,3)17(22)16(30)21(32)34-4)5-7-23(2)20(12-6-8-35-10-12)36-14(28)9-26(23,27)37-27/h6,8,10,13,16-20,30-31,33H,5,7,9,11H2,1-4H3/t13-,16+,17+,18+,19-,20+,22-,23+,24-,25+,26+,27+/m1/s1

InChI Key

SZIDPCXTWHHMAY-LUUUZSLOSA-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
Khaya ivorensis	LOTUS Database	35616633
Khaya senegalensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Prostaglandins and related compounds

Alternative Parents

Substituents

Prostaglandin skeleton
Delta valerolactone
Delta_valerolactone
Oxepane
Dicarboxylic acid or derivatives
Oxane
Cyclic alcohol
Heteroaromatic compound
Furan
Methyl ester
Tertiary alcohol
Carboxylic acid ester
Ketone
Lactone
Secondary alcohol
Oxacycle
Ether
Oxirane
Dialkyl ether
Organoheterocyclic compound
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Organooxygen compound
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

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

8681426

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10506025

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (2s)-2-[(1s,2r,5s,6s,10s,12s,13s,15s,16r,18s,19s)-6-(furan-3-yl)-15,18-dihydroxy-1,5,16-trimethyl-8,14-dioxo-7,11-dioxahexacyclo[14.2.1.0²,¹².0⁵,¹⁰.0¹⁰,¹².0¹³,¹⁸]nonadecan-19-yl]-2-hydroxyacetate (NP0270765)

MOL for NP0270765 (methyl (2s)-2-[(1s,2r,5s,6s,10s,12s,13s,15s,16r,18s,19s)-6-(furan-3-yl)-15,18-dihydroxy-1,5,16-trimethyl-8,14-dioxo-7,11-dioxahexacyclo[14.2.1.0²,¹².0⁵,¹⁰.0¹⁰,¹².0¹³,¹⁸]nonadecan-19-yl]-2-hydroxyacetate)

3D MOL for NP0270765 (methyl (2s)-2-[(1s,2r,5s,6s,10s,12s,13s,15s,16r,18s,19s)-6-(furan-3-yl)-15,18-dihydroxy-1,5,16-trimethyl-8,14-dioxo-7,11-dioxahexacyclo[14.2.1.0²,¹².0⁵,¹⁰.0¹⁰,¹².0¹³,¹⁸]nonadecan-19-yl]-2-hydroxyacetate)

3D SDF for NP0270765 (methyl (2s)-2-[(1s,2r,5s,6s,10s,12s,13s,15s,16r,18s,19s)-6-(furan-3-yl)-15,18-dihydroxy-1,5,16-trimethyl-8,14-dioxo-7,11-dioxahexacyclo[14.2.1.0²,¹².0⁵,¹⁰.0¹⁰,¹².0¹³,¹⁸]nonadecan-19-yl]-2-hydroxyacetate)

3D-SDF for NP0270765 (methyl (2s)-2-[(1s,2r,5s,6s,10s,12s,13s,15s,16r,18s,19s)-6-(furan-3-yl)-15,18-dihydroxy-1,5,16-trimethyl-8,14-dioxo-7,11-dioxahexacyclo[14.2.1.0²,¹².0⁵,¹⁰.0¹⁰,¹².0¹³,¹⁸]nonadecan-19-yl]-2-hydroxyacetate)

PDB for NP0270765 (methyl (2s)-2-[(1s,2r,5s,6s,10s,12s,13s,15s,16r,18s,19s)-6-(furan-3-yl)-15,18-dihydroxy-1,5,16-trimethyl-8,14-dioxo-7,11-dioxahexacyclo[14.2.1.0²,¹².0⁵,¹⁰.0¹⁰,¹².0¹³,¹⁸]nonadecan-19-yl]-2-hydroxyacetate)

3D PDB for NP0270765 (methyl (2s)-2-[(1s,2r,5s,6s,10s,12s,13s,15s,16r,18s,19s)-6-(furan-3-yl)-15,18-dihydroxy-1,5,16-trimethyl-8,14-dioxo-7,11-dioxahexacyclo[14.2.1.0²,¹².0⁵,¹⁰.0¹⁰,¹².0¹³,¹⁸]nonadecan-19-yl]-2-hydroxyacetate)

SMILES for NP0270765 (methyl (2s)-2-[(1s,2r,5s,6s,10s,12s,13s,15s,16r,18s,19s)-6-(furan-3-yl)-15,18-dihydroxy-1,5,16-trimethyl-8,14-dioxo-7,11-dioxahexacyclo[14.2.1.0²,¹².0⁵,¹⁰.0¹⁰,¹².0¹³,¹⁸]nonadecan-19-yl]-2-hydroxyacetate)

INCHI for NP0270765 (methyl (2s)-2-[(1s,2r,5s,6s,10s,12s,13s,15s,16r,18s,19s)-6-(furan-3-yl)-15,18-dihydroxy-1,5,16-trimethyl-8,14-dioxo-7,11-dioxahexacyclo[14.2.1.0²,¹².0⁵,¹⁰.0¹⁰,¹².0¹³,¹⁸]nonadecan-19-yl]-2-hydroxyacetate)

Structure for NP0270765 (methyl (2s)-2-[(1s,2r,5s,6s,10s,12s,13s,15s,16r,18s,19s)-6-(furan-3-yl)-15,18-dihydroxy-1,5,16-trimethyl-8,14-dioxo-7,11-dioxahexacyclo[14.2.1.0²,¹².0⁵,¹⁰.0¹⁰,¹².0¹³,¹⁸]nonadecan-19-yl]-2-hydroxyacetate)

3D Structure for NP0270765 (methyl (2s)-2-[(1s,2r,5s,6s,10s,12s,13s,15s,16r,18s,19s)-6-(furan-3-yl)-15,18-dihydroxy-1,5,16-trimethyl-8,14-dioxo-7,11-dioxahexacyclo[14.2.1.0²,¹².0⁵,¹⁰.0¹⁰,¹².0¹³,¹⁸]nonadecan-19-yl]-2-hydroxyacetate)