NP-MRD: Showing NP-Card for (-)-Deacetylhectochlorin (NP0078428)

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Record Information

Version

2.0

Created at

2022-04-28 23:30:47 UTC

Updated at

2022-04-28 23:30:47 UTC

NP-MRD ID

NP0078428

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Deacetylhectochlorin

Description

CHEMBL486608 belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating. (-)-Deacetylhectochlorin is found in Bursatella leachii and Lyngbya majuscula. Based on a literature review very few articles have been published on CHEMBL486608.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292201302D          

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M  END

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 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  1 21  1  0  0  0  0
 21 22  2  0  0  0  0
 19 23  1  0  0  0  0
 19 24  1  0  0  0  0
 18 25  1  1  0  0  0
 17 26  1  0  0  0  0
 26 27  1  0  0  0  0
 15 27  2  0  0  0  0
 11 28  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 31 34  1  0  0  0  0
 10 35  1  6  0  0  0
  6 36  1  1  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 36 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0078428

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1[C@H](CCCC(C)(Cl)Cl)OC(=O)C2=CSC(=N2)[C@@H](O)C(C)(C)OC(=O)C2=CSC(=N2)[C@@H](OC1=O)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C25H32Cl2N2O8S2/c1-12-15(8-7-9-25(6,26)27)35-21(32)13-10-38-18(28-13)16(30)24(4,5)37-22(33)14-11-39-19(29-14)17(23(2,3)34)36-20(12)31/h10-12,15-17,30,34H,7-9H2,1-6H3/t12-,15-,16+,17+/m0/s1

> <INCHI_KEY>
VZEAHVQDYHOSRG-KKBVYLPWSA-N

> <FORMULA>
C25H32Cl2N2O8S2

> <MOLECULAR_WEIGHT>
623.56

> <EXACT_MASS>
622.0977137

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
60.84416830323216

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5S,12S,13S,16S)-12-(4,4-dichloropentyl)-5-hydroxy-16-(2-hydroxypropan-2-yl)-4,4,13-trimethyl-3,11,15-trioxa-7,18-dithia-20,21-diazatricyclo[15.2.1.1^{6,9}]henicosa-1(19),6(21),8,17(20)-tetraene-2,10,14-trione

> <ALOGPS_LOGP>
3.68

> <JCHEM_LOGP>
4.567617106666667

> <ALOGPS_LOGS>
-5.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.928099466135489

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.939321770409007

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7404950627296069

> <JCHEM_POLAR_SURFACE_AREA>
145.14000000000001

> <JCHEM_REFRACTIVITY>
145.23020000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.79e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5S,12S,13S,16S)-12-(4,4-dichloropentyl)-5-hydroxy-16-(2-hydroxypropan-2-yl)-4,4,13-trimethyl-3,11,15-trioxa-7,18-dithia-20,21-diazatricyclo[15.2.1.1^{6,9}]henicosa-1(19),6(21),8,17(20)-tetraene-2,10,14-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0      11.583   4.053   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.977   3.400   0.000  0.00  0.00           C+0
HETATM    3  S   UNK     0      12.787   1.872   0.000  0.00  0.00           S+0
HETATM    4  C   UNK     0      10.978   1.455   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      10.530   2.929   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       9.925   0.331   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      10.373  -1.142   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       9.320  -2.267   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       9.799  -3.730   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       7.664  -1.956   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.315  -2.700   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.191  -1.648   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.845  -0.253   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       7.378  -0.397   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.426   1.379   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       6.478   2.503   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       6.031   3.977   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.083   5.101   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.583   4.752   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       9.635   5.876   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      11.135   5.527   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      12.188   6.651   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.792   6.074   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.505   6.290   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.636   6.575   0.000  0.00  0.00           O+0
HETATM   26  S   UNK     0       4.456   3.675   0.000  0.00  0.00           S+0
HETATM   27  C   UNK     0       4.107   2.175   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.125  -4.228   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.706  -4.827   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.478  -3.898   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.059  -4.497   0.000  0.00  0.00           C+0
HETATM   32 Cl   UNK     0       0.641  -5.096   0.000  0.00  0.00          Cl+0
HETATM   33 Cl   UNK     0       1.460  -3.078   0.000  0.00  0.00          Cl+0
HETATM   34  C   UNK     0       2.658  -5.916   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.901  -0.434   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      11.425  -0.018   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      11.076  -1.518   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      12.221   1.300   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      12.925  -0.367   0.000  0.00  0.00           C+0
CONECT    1    2    5   21                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4    1                                                       
CONECT    6    4    7   36                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   35                                                  
CONECT   11   10   12   28                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   27                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   26                                                  
CONECT   18   17   19   25                                                  
CONECT   19   18   20   23   24                                             
CONECT   20   19   21                                                       
CONECT   21   20    1   22                                                  
CONECT   22   21                                                            
CONECT   23   19                                                            
CONECT   24   19                                                            
CONECT   25   18                                                            
CONECT   26   17   27                                                       
CONECT   27   26   15                                                       
CONECT   28   11   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33   34                                             
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   31                                                            
CONECT   35   10                                                            
CONECT   36    6   37   38   39                                             
CONECT   37   36                                                            
CONECT   38   36                                                            
CONECT   39   36                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₂Cl₂N₂O₈S₂

Average Mass

623.5600 Da

Monoisotopic Mass

622.09771 Da

IUPAC Name

(5S,12S,13S,16S)-12-(4,4-dichloropentyl)-5-hydroxy-16-(2-hydroxypropan-2-yl)-4,4,13-trimethyl-3,11,15-trioxa-7,18-dithia-20,21-diazatricyclo[15.2.1.1^{6,9}]henicosa-1(19),6(21),8,17(20)-tetraene-2,10,14-trione

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@H]1[C@H](CCCC(C)(Cl)Cl)OC(=O)C2=CSC(=N2)[C@@H](O)C(C)(C)OC(=O)C2=CSC(=N2)[C@@H](OC1=O)C(C)(C)O

InChI Identifier

InChI=1S/C25H32Cl2N2O8S2/c1-12-15(8-7-9-25(6,26)27)35-21(32)13-10-38-18(28-13)16(30)24(4,5)37-22(33)14-11-39-19(29-14)17(23(2,3)34)36-20(12)31/h10-12,15-17,30,34H,7-9H2,1-6H3/t12-,15-,16+,17+/m0/s1

InChI Key

VZEAHVQDYHOSRG-KKBVYLPWSA-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
Bursatella leachii	Animalia	KNApSAcK
Lyngbya majuscula	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Peptidomimetics

Sub Class

Depsipeptides

Direct Parent

Cyclic depsipeptides

Alternative Parents

Substituents

Cyclic depsipeptide
Macrolactam
Macrolide
Tricarboxylic acid or derivatives
Thiazolecarboxylic acid or derivatives
Azole
Heteroaromatic compound
Tertiary alcohol
Thiazole
Carboxylic acid ester
Lactone
Secondary alcohol
Carboxylic acid derivative
Oxacycle
Azacycle
Organoheterocyclic compound
Organochloride
Organohalogen compound
Alkyl chloride
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Alcohol
Carbonyl group
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Alkyl halide
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	3.68	ALOGPS
logP	4.57	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	11.94	ChemAxon
pKa (Strongest Basic)	-0.74	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	145.14 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	145.23 m³·mol⁻¹	ChemAxon
Polarizability	60.84 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

9367975

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11192900

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Deacetylhectochlorin (NP0078428)

MOL for NP0078428 ((-)-Deacetylhectochlorin)

3D MOL for NP0078428 ((-)-Deacetylhectochlorin)

3D SDF for NP0078428 ((-)-Deacetylhectochlorin)

3D-SDF for NP0078428 ((-)-Deacetylhectochlorin)

PDB for NP0078428 ((-)-Deacetylhectochlorin)

3D PDB for NP0078428 ((-)-Deacetylhectochlorin)

SMILES for NP0078428 ((-)-Deacetylhectochlorin)

INCHI for NP0078428 ((-)-Deacetylhectochlorin)

Structure for NP0078428 ((-)-Deacetylhectochlorin)

3D Structure for NP0078428 ((-)-Deacetylhectochlorin)