NP-MRD: Showing NP-Card for Sinulalide A (NP0333135)

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Record Information

Version

1.0

Created at

2024-05-11 06:40:57 UTC

Updated at

2024-05-13 01:12:25 UTC

NP-MRD ID

NP0333135

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Sinulalide A

Description

Not Available

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01232309172D          

 20 20  0  0  1  0            999 V2000
   -2.9672    2.5196    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2136    2.1840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4991    2.5965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8860    2.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4011    2.7119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7366    3.4656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1715    1.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5429    2.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5429    2.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2574    1.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9719    2.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6864    1.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4008    2.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1153    1.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8298    2.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4008    2.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2216    1.2908    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8091    0.5763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0420    1.3770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5941    0.7639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  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  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  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
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 13 16  2  0  0  0  0
 17  4  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19  2  1  0  0  0  0
 19 20  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0333135

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1(CC(C)CCCC(=C)C=C)OC(=O)[C@@H](C)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C16H26O4/c1-6-11(2)8-7-9-12(3)10-16(19-5)14(17)13(4)15(18)20-16/h6,12-14,17H,1-2,7-10H2,3-5H3/t12?,13-,14+,16?/m0/s1

> <INCHI_KEY>
BIIXYXUGLPBCSV-IOSBVQAASA-N

> <FORMULA>
C16H26O4

> <MOLECULAR_WEIGHT>
282.38

> <EXACT_MASS>
282.183109317

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
31.78838846616768

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,4R)-4-hydroxy-5-methoxy-3-methyl-5-(2-methyl-6-methylideneoct-7-en-1-yl)oxolan-2-one

> <JCHEM_LOGP>
3.5271962379999993

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.779116648756677

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7702143778338297

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
77.88659999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3S,4R)-4-hydroxy-5-methoxy-3-methyl-5-(2-methyl-6-methylideneoct-7-en-1-yl)oxolan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-JAN-23         0                                  
HETATM    1  O   UNK     0      -5.539   4.703   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -4.132   4.077   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.798   4.847   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -1.654   3.816   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.749   5.062   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.375   6.469   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.320   3.046   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.013   3.816   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.013   5.356   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.347   3.046   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.681   3.816   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.015   3.046   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.348   3.816   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.682   3.046   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.016   3.816   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.348   5.356   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.280   2.409   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.510   1.076   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -3.812   2.570   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.842   1.426   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   19                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7   17                                             
CONECT    5    4    6                                                       
CONECT    6    5                                                            
CONECT    7    4    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13                                                            
CONECT   17    4   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17    2   20                                                  
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₂₆O₄

Average Mass

282.3800 Da

Monoisotopic Mass

282.18311 Da

IUPAC Name

(3S,4R)-4-hydroxy-5-methoxy-3-methyl-5-(2-methyl-6-methylideneoct-7-en-1-yl)oxolan-2-one

Traditional Name

(3S,4R)-4-hydroxy-5-methoxy-3-methyl-5-(2-methyl-6-methylideneoct-7-en-1-yl)oxolan-2-one

CAS Registry Number

Not Available

SMILES

COC1(CC(C)CCCC(=C)C=C)OC(=O)[C@@H](C)[C@H]1O

InChI Identifier

InChI=1S/C16H26O4/c1-6-11(2)8-7-9-12(3)10-16(19-5)14(17)13(4)15(18)20-16/h6,12-14,17H,1-2,7-10H2,3-5H3/t12?,13-,14+,16?/m0/s1

InChI Key

BIIXYXUGLPBCSV-IOSBVQAASA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)	yanxia@nbu.edu.cn	Not Available	Not Available	2024-05-11	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)	yanxia@nbu.edu.cn	Not Available	Not Available	2024-05-11	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)	yanxia@nbu.edu.cn	Not Available	Not Available	2024-05-11	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)	yanxia@nbu.edu.cn	Not Available	Not Available	2024-05-11	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)	yanxia@nbu.edu.cn	Not Available	Not Available	2024-05-11	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	yanxia@nbu.edu.cn	Not Available	Not Available	2024-05-11	View Spectrum
1D_DEPT NMR	¹³C NMR Spectrum (1D, 151 MHz, CDCl3, experimental)	yanxia@nbu.edu.cn	Not Available	Not Available	2024-05-11	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	yanxia@nbu.edu.cn	Not Available	Not Available	2024-05-11	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	yanxia@nbu.edu.cn	Not Available	Not Available	2024-05-11	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)	yanxia@nbu.edu.cn	Not Available	Not Available	2024-05-11	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, CDCl3, experimental)	yanxia@nbu.edu.cn	Not Available	Not Available	2024-05-11	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
scabra		Not Available

Chemical Taxonomy

Classification

Not classified

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	3.53	ChemAxon
pKa (Strongest Acidic)	12.78	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	77.89 m³·mol⁻¹	ChemAxon
Polarizability	31.79 Å³	ChemAxon
Number of Rings	1	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

Not Available

References

General References

Wang K, Liu J, Huang J, Leng X, Li T, Ouyang H, Lin W, Yan X, He S: Discovery of uncommon terpenoids from the South China Sea soft coral Sinularia scabra. Phytochemistry. 2023 May;209:113616. doi: 10.1016/j.phytochem.2023.113616. Epub 2023 Feb 23. [PubMed:36828101 ]

Showing NP-Card for Sinulalide A (NP0333135)

MOL for NP0333135 (Sinulalide A)

3D MOL for NP0333135 (Sinulalide A)

3D SDF for NP0333135 (Sinulalide A)

3D-SDF for NP0333135 (Sinulalide A)

PDB for NP0333135 (Sinulalide A)

3D PDB for NP0333135 (Sinulalide A)

SMILES for NP0333135 (Sinulalide A)

INCHI for NP0333135 (Sinulalide A)

Structure for NP0333135 (Sinulalide A)

3D Structure for NP0333135 (Sinulalide A)