NP-MRD: Showing NP-Card for 13-chloro-7,8,9,16-tetrahydroxy-14-methoxy-3-methyl-3,4,7,8,9,10-hexahydro-2-benzoxacyclotetradecin-1-one (NP0296647)

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Record Information

Version

2.0

Created at

2022-09-10 06:21:19 UTC

Updated at

2022-09-10 06:21:19 UTC

NP-MRD ID

NP0296647

Secondary Accession Numbers

None

Natural Product Identification

Common Name

13-chloro-7,8,9,16-tetrahydroxy-14-methoxy-3-methyl-3,4,7,8,9,10-hexahydro-2-benzoxacyclotetradecin-1-one

Description

13-Chloro-7,8,9,16-tetrahydroxy-14-methoxy-3-methyl-3,4,7,8,9,10-hexahydro-1H-2-benzoxacyclotetradecin-1-one 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. 13-chloro-7,8,9,16-tetrahydroxy-14-methoxy-3-methyl-3,4,7,8,9,10-hexahydro-2-benzoxacyclotetradecin-1-one is found in Curvularia lunata. Based on a literature review very few articles have been published on 13-chloro-7,8,9,16-tetrahydroxy-14-methoxy-3-methyl-3,4,7,8,9,10-hexahydro-1H-2-benzoxacyclotetradecin-1-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102208212D          

 27 28  0  0  0  0            999 V2000
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   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  7 26  1  0  0  0  0
 26 27  2  0  0  0  0
M  END

     RDKit          3D

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 24 50  1  0
M  END


  Mrv1652309102208212D          

 27 28  0  0  0  0            999 V2000
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0296647

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C2C(C=CCC(O)C(O)C(O)C=CCC(C)OC2=O)=C1Cl

> <INCHI_IDENTIFIER>
InChI=1S/C19H23ClO7/c1-10-5-3-7-12(21)18(24)13(22)8-4-6-11-16(19(25)27-10)14(23)9-15(26-2)17(11)20/h3-4,6-7,9-10,12-13,18,21-24H,5,8H2,1-2H3

> <INCHI_KEY>
ASZQCWYVQBKBBJ-UHFFFAOYSA-N

> <FORMULA>
C19H23ClO7

> <MOLECULAR_WEIGHT>
398.84

> <EXACT_MASS>
398.1132308

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
39.38805492279369

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
13-chloro-7,8,9,16-tetrahydroxy-14-methoxy-3-methyl-3,4,7,8,9,10-hexahydro-1H-2-benzoxacyclotetradecin-1-one

> <JCHEM_LOGP>
2.560782125666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.02611514040829

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.209095148286082

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2111784104842096

> <JCHEM_POLAR_SURFACE_AREA>
116.45000000000002

> <JCHEM_REFRACTIVITY>
102.3403

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
13-chloro-7,8,9,16-tetrahydroxy-14-methoxy-3-methyl-3,4,7,8,9,10-hexahydro-2-benzoxacyclotetradecin-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
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HETATM    3  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10 Cl   UNK     0       1.334  -0.770   0.000  0.00  0.00          Cl+0
HETATM   11  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   26                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8    3   10                                                  
CONECT   10    9                                                            
CONECT   11    8   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25    7   27                                                  
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₃ClO₇

Average Mass

398.8400 Da

Monoisotopic Mass

398.11323 Da

IUPAC Name

13-chloro-7,8,9,16-tetrahydroxy-14-methoxy-3-methyl-3,4,7,8,9,10-hexahydro-1H-2-benzoxacyclotetradecin-1-one

Traditional Name

13-chloro-7,8,9,16-tetrahydroxy-14-methoxy-3-methyl-3,4,7,8,9,10-hexahydro-2-benzoxacyclotetradecin-1-one

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C2C(C=CCC(O)C(O)C(O)C=CCC(C)OC2=O)=C1Cl

InChI Identifier

InChI=1S/C19H23ClO7/c1-10-5-3-7-12(21)18(24)13(22)8-4-6-11-16(19(25)27-10)14(23)9-15(26-2)17(11)20/h3-4,6-7,9-10,12-13,18,21-24H,5,8H2,1-2H3

InChI Key

ASZQCWYVQBKBBJ-UHFFFAOYSA-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
Curvularia lunata	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
Anisole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Aryl chloride
Aryl halide
Benzenoid
Vinylogous acid
Carboxylic acid ester
Secondary alcohol
Lactone
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Ether
Polyol
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Organohalogen compound
Organochloride
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	2.56	ChemAxon
pKa (Strongest Acidic)	9.21	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.45 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	102.34 m³·mol⁻¹	ChemAxon
Polarizability	39.39 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

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

72304475

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 13-chloro-7,8,9,16-tetrahydroxy-14-methoxy-3-methyl-3,4,7,8,9,10-hexahydro-2-benzoxacyclotetradecin-1-one (NP0296647)

MOL for NP0296647 (13-chloro-7,8,9,16-tetrahydroxy-14-methoxy-3-methyl-3,4,7,8,9,10-hexahydro-2-benzoxacyclotetradecin-1-one)

3D MOL for NP0296647 (13-chloro-7,8,9,16-tetrahydroxy-14-methoxy-3-methyl-3,4,7,8,9,10-hexahydro-2-benzoxacyclotetradecin-1-one)

3D SDF for NP0296647 (13-chloro-7,8,9,16-tetrahydroxy-14-methoxy-3-methyl-3,4,7,8,9,10-hexahydro-2-benzoxacyclotetradecin-1-one)

3D-SDF for NP0296647 (13-chloro-7,8,9,16-tetrahydroxy-14-methoxy-3-methyl-3,4,7,8,9,10-hexahydro-2-benzoxacyclotetradecin-1-one)

PDB for NP0296647 (13-chloro-7,8,9,16-tetrahydroxy-14-methoxy-3-methyl-3,4,7,8,9,10-hexahydro-2-benzoxacyclotetradecin-1-one)

3D PDB for NP0296647 (13-chloro-7,8,9,16-tetrahydroxy-14-methoxy-3-methyl-3,4,7,8,9,10-hexahydro-2-benzoxacyclotetradecin-1-one)

SMILES for NP0296647 (13-chloro-7,8,9,16-tetrahydroxy-14-methoxy-3-methyl-3,4,7,8,9,10-hexahydro-2-benzoxacyclotetradecin-1-one)

INCHI for NP0296647 (13-chloro-7,8,9,16-tetrahydroxy-14-methoxy-3-methyl-3,4,7,8,9,10-hexahydro-2-benzoxacyclotetradecin-1-one)

Structure for NP0296647 (13-chloro-7,8,9,16-tetrahydroxy-14-methoxy-3-methyl-3,4,7,8,9,10-hexahydro-2-benzoxacyclotetradecin-1-one)

3D Structure for NP0296647 (13-chloro-7,8,9,16-tetrahydroxy-14-methoxy-3-methyl-3,4,7,8,9,10-hexahydro-2-benzoxacyclotetradecin-1-one)