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Showing NP-Card for (4s,8s)-8,11,13-trihydroxy-4-methyl-1,4,5,6,8,9-hexahydro-3-benzoxacyclododecine-2,7,10-trione (NP0217403)

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Record Information
Version2.0
Created at2022-09-05 17:44:31 UTC
Updated at2022-09-05 17:44:31 UTC
NP-MRD IDNP0217403
Secondary Accession NumbersNone
Natural Product Identification
Common Name(4s,8s)-8,11,13-trihydroxy-4-methyl-1,4,5,6,8,9-hexahydro-3-benzoxacyclododecine-2,7,10-trione
Description8-Beta-Hydroxy-oxocurvularin 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. Based on a literature review very few articles have been published on 8-beta-Hydroxy-oxocurvularin.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0217403 ((4s,8s)-8,11,13-trihydroxy-4-methyl-1,4,5,6,8,9-hexahydro-3-benzoxacyclododecine-2,7,10-trione)


  Mrv1652309052219442D          

 23 24  0  0  1  0            999 V2000
    7.4701    1.7627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6906    1.4927    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5347    0.6825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1583    0.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0024   -0.6677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6260   -1.2078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2228   -0.9377    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0669   -1.7479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5992   -0.3976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8196   -0.6677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6637   -1.4778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1960   -0.1276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4164   -0.3976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2605   -1.2078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7928    0.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9487    0.9526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3251    1.4927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7283    1.2226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3519    0.6825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1315    0.9526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2874    1.7627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6637    2.3028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0669    2.0328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 12 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
  2 23  1  0  0  0  0
M  END
Download

3D MOL for NP0217403 ((4s,8s)-8,11,13-trihydroxy-4-methyl-1,4,5,6,8,9-hexahydro-3-benzoxacyclododecine-2,7,10-trione)

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3D SDF for NP0217403 ((4s,8s)-8,11,13-trihydroxy-4-methyl-1,4,5,6,8,9-hexahydro-3-benzoxacyclododecine-2,7,10-trione)

  Mrv1652309052219442D          

 23 24  0  0  1  0            999 V2000
    7.4701    1.7627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6906    1.4927    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5347    0.6825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1583    0.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0024   -0.6677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6260   -1.2078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2228   -0.9377    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0669   -1.7479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5992   -0.3976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8196   -0.6677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6637   -1.4778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1960   -0.1276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4164   -0.3976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2605   -1.2078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7928    0.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9487    0.9526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3251    1.4927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7283    1.2226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3519    0.6825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1315    0.9526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2874    1.7627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6637    2.3028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0669    2.0328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 12 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
  2 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0217403

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CCC(=O)[C@@H](O)CC(=O)C2=C(O)C=C(O)C=C2CC(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C16H18O7/c1-8-2-3-11(18)12(19)7-14(21)16-9(5-15(22)23-8)4-10(17)6-13(16)20/h4,6,8,12,17,19-20H,2-3,5,7H2,1H3/t8-,12-/m0/s1

> <INCHI_KEY>
PCSBVPMYIHSHPB-UFBFGSQYSA-N

> <FORMULA>
C16H18O7

> <MOLECULAR_WEIGHT>
322.313

> <EXACT_MASS>
322.10525292

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
31.290236392891945

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4S,8S)-8,11,13-trihydroxy-4-methyl-2,4,5,6,7,8,9,10-octahydro-1H-3-benzoxacyclododecine-2,7,10-trione

> <JCHEM_LOGP>
1.4403128343333336

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.652034370815894

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.769864370062767

> <JCHEM_PKA_STRONGEST_BASIC>
-3.578526167103986

> <JCHEM_POLAR_SURFACE_AREA>
121.13000000000001

> <JCHEM_REFRACTIVITY>
79.59599999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4S,8S)-8,11,13-trihydroxy-4-methyl-1,4,5,6,8,9-hexahydro-3-benzoxacyclododecine-2,7,10-trione

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0217403 ((4s,8s)-8,11,13-trihydroxy-4-methyl-1,4,5,6,8,9-hexahydro-3-benzoxacyclododecine-2,7,10-trione)
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PDB for NP0217403 ((4s,8s)-8,11,13-trihydroxy-4-methyl-1,4,5,6,8,9-hexahydro-3-benzoxacyclododecine-2,7,10-trione)
HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      13.944   3.290   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.489   2.786   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.198   1.274   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.362   0.266   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.071  -1.246   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      14.235  -2.254   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      11.616  -1.750   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      11.325  -3.263   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      10.452  -0.742   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.997  -1.246   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.706  -2.759   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.833  -0.238   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.377  -0.742   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.086  -2.254   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.213   0.266   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.504   1.778   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.340   2.786   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.959   2.282   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.124   1.274   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.579   1.778   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.870   3.290   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       8.706   4.299   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      11.325   3.794   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   23                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   19                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   12   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21    2                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

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3D PDB for NP0217403 ((4s,8s)-8,11,13-trihydroxy-4-methyl-1,4,5,6,8,9-hexahydro-3-benzoxacyclododecine-2,7,10-trione)
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SMILES for NP0217403 ((4s,8s)-8,11,13-trihydroxy-4-methyl-1,4,5,6,8,9-hexahydro-3-benzoxacyclododecine-2,7,10-trione)
C[C@H]1CCC(=O)[C@@H](O)CC(=O)C2=C(O)C=C(O)C=C2CC(=O)O1
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INCHI for NP0217403 ((4s,8s)-8,11,13-trihydroxy-4-methyl-1,4,5,6,8,9-hexahydro-3-benzoxacyclododecine-2,7,10-trione)
InChI=1S/C16H18O7/c1-8-2-3-11(18)12(19)7-14(21)16-9(5-15(22)23-8)4-10(17)6-13(16)20/h4,6,8,12,17,19-20H,2-3,5,7H2,1H3/t8-,12-/m0/s1
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Synonyms
ValueSource
8-b-Hydroxy-oxocurvularinGenerator
8-Β-hydroxy-oxocurvularinGenerator
Chemical FormulaC16H18O7
Average Mass322.3130 Da
Monoisotopic Mass322.10525 Da
IUPAC Name(4S,8S)-8,11,13-trihydroxy-4-methyl-2,4,5,6,7,8,9,10-octahydro-1H-3-benzoxacyclododecine-2,7,10-trione
Traditional Name(4S,8S)-8,11,13-trihydroxy-4-methyl-1,4,5,6,8,9-hexahydro-3-benzoxacyclododecine-2,7,10-trione
CAS Registry NumberNot Available
SMILES
C[C@H]1CCC(=O)[C@@H](O)CC(=O)C2=C(O)C=C(O)C=C2CC(=O)O1
InChI Identifier
InChI=1S/C16H18O7/c1-8-2-3-11(18)12(19)7-14(21)16-9(5-15(22)23-8)4-10(17)6-13(16)20/h4,6,8,12,17,19-20H,2-3,5,7H2,1H3/t8-,12-/m0/s1
InChI KeyPCSBVPMYIHSHPB-UFBFGSQYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
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.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassMacrolides and analogues  
Sub ClassNot Available
Direct ParentMacrolides and analogues  
Alternative Parents
Substituents
  • Macrolide
    • 

  • Aryl ketone
    • 

  • Aryl alkyl ketone
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Benzenoid
    • 

  • Vinylogous acid
    • 

  • Carboxylic acid ester
    • 

  • Ketone
    • 

  • Lactone
    • 

  • Secondary alcohol
    • 

  • Cyclic ketone
    • 

  • Carboxylic acid derivative
    • 

  • Polyol
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Organooxygen compound
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Alcohol
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.44ChemAxon
pKa (Strongest Acidic)7.77ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area121.13 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity79.6 m³·mol⁻¹ChemAxon
Polarizability31.29 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID24608523  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14582210  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]