NP-MRD: Showing NP-Card for Sinulobatin C (NP0332357)

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Record Information

Version

1.0

Created at

2024-01-11 16:03:28 UTC

Updated at

2024-09-03 04:18:56 UTC

NP-MRD ID

NP0332357

DOI

https://doi.org/10.57994/1572

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Sinulobatin C

Description

Not Available

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01112416032D          

 29 32  0  0  1  0            999 V2000
    0.7145   -2.8875    0.0000 C   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
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -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  1  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4125   -2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2195   -2.8948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0445   -2.8948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5834   -1.0666    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 H   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
    3.5724   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   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
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  2  1  0  0  0  0
  5  6  1  6  0  0  0
  7  5  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 12  1  0  0  0  0
  8 12  1  1  0  0  0
  8 13  1  6  0  0  0
  7 14  1  1  0  0  0
  7 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 26 25  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
  4 28  1  0  0  0  0
 28 29  2  0  0  0  0
 22 29  1  0  0  0  0
  5 29  1  0  0  0  0
M  END


  Mrv2104 01112416032D          

 29 32  0  0  1  0            999 V2000
    0.7145   -2.8875    0.0000 C   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
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -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  1  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4125   -2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2195   -2.8948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0445   -2.8948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5834   -1.0666    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 H   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
    3.5724   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   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
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  2  1  0  0  0  0
  5  6  1  6  0  0  0
  7  5  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 12  1  0  0  0  0
  8 12  1  1  0  0  0
  8 13  1  6  0  0  0
  7 14  1  1  0  0  0
  7 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 26 25  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
  4 28  1  0  0  0  0
 28 29  2  0  0  0  0
 22 29  1  0  0  0  0
  5 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0332357

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]1(OC1(C)C)[C@]1([H])[C@@H](OC(C)=O)[C@H](C)[C@@]2([H])CC[C@H](C)C3=C2[C@@]1([H])C(=C)CC3

> <INCHI_IDENTIFIER>
InChI=1S/C22H32O3/c1-11-7-10-16-13(3)20(24-14(4)23)19(21-22(5,6)25-21)17-12(2)8-9-15(11)18(16)17/h11,13,16-17,19-21H,2,7-10H2,1,3-6H3/t11-,13+,16+,17+,19-,20-,21-/m0/s1

> <INCHI_KEY>
SEMOPQVZELKPIB-CBLWJWSESA-N

> <FORMULA>
C22H32O3

> <MOLECULAR_WEIGHT>
344.495

> <EXACT_MASS>
344.23514489

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
39.879908459981124

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,3S,3aR,7S,9aR)-3-[(2S)-3,3-dimethyloxiran-2-yl]-1,7-dimethyl-4-methylidene-2,3,3a,4,5,6,7,8,9,9a-decahydro-1H-phenalen-2-yl acetate

> <JCHEM_LOGP>
3.616648610333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.224599378815756

> <JCHEM_POLAR_SURFACE_AREA>
38.83

> <JCHEM_REFRACTIVITY>
98.5606

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,3S,3aR,7S,9aR)-3-[(2S)-3,3-dimethyloxiran-2-yl]-1,7-dimethyl-4-methylidene-1,2,3,3a,5,6,7,8,9,9a-decahydrophenalen-2-yl acetate

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 11-JAN-24   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-JAN-24         0                                  
HETATM    1  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    6  H   UNK     0       1.334  -3.850   0.000  0.00  0.00           H+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.770  -4.414   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.410  -5.404   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.950  -5.404   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.540  -3.080   0.000  0.00  0.00           O+0
HETATM   13  H   UNK     0      -1.089  -1.991   0.000  0.00  0.00           H+0
HETATM   14  H   UNK     0       0.000  -1.540   0.000  0.00  0.00           H+0
HETATM   15  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0       5.335  -1.540   0.000  0.00  0.00           H+0
HETATM   24  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    5                                                  
CONECT    3    2    4                                                       
CONECT    4    3   28                                                       
CONECT    5    2    6    7   29                                             
CONECT    6    5                                                            
CONECT    7    5    8   14   15                                             
CONECT    8    7    9   12   13                                             
CONECT    9    8   10   11   12                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    9    8                                                       
CONECT   13    8                                                            
CONECT   14    7                                                            
CONECT   15    7   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   15   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24   29                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26    4   29                                                  
CONECT   29   28   22    5                                                  
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₂O₃

Average Mass

344.4950 Da

Monoisotopic Mass

344.23514 Da

IUPAC Name

(1R,2S,3S,3aR,7S,9aR)-3-[(2S)-3,3-dimethyloxiran-2-yl]-1,7-dimethyl-4-methylidene-2,3,3a,4,5,6,7,8,9,9a-decahydro-1H-phenalen-2-yl acetate

Traditional Name

(1R,2S,3S,3aR,7S,9aR)-3-[(2S)-3,3-dimethyloxiran-2-yl]-1,7-dimethyl-4-methylidene-1,2,3,3a,5,6,7,8,9,9a-decahydrophenalen-2-yl acetate

CAS Registry Number

Not Available

SMILES

[H][C@]1(OC1(C)C)[C@]1([H])[C@@H](OC(C)=O)[C@H](C)[C@@]2([H])CC[C@H](C)C3=C2[C@@]1([H])C(=C)CC3

InChI Identifier

InChI=1S/C22H32O3/c1-11-7-10-16-13(3)20(24-14(4)23)19(21-22(5,6)25-21)17-12(2)8-9-15(11)18(16)17/h11,13,16-17,19-21H,2,7-10H2,1,3-6H3/t11-,13+,16+,17+,19-,20-,21-/m0/s1

InChI Key

SEMOPQVZELKPIB-CBLWJWSESA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D_DEPT NMR	¹³C NMR Spectrum (1D, 126 MHz, CDCl3, experimental)	simmswli@163.com	School of Medicine Shanghai University	Song-Wei Li	2024-05-02	View Spectrum
1D NMR	[¹³C, ] NMR Spectrum (2D, 126 MHz, CDCl3, experimental)	simmswli@163.com	School of Medicine Shanghai University	Song-Wei Li	2024-01-11	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)	simmswli@163.com	School of Medicine Shanghai University	Song-Wei Li	2024-01-11	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 400.13280091, CDCl₃, simulated)	simmswli@163.com	School of Medicine Shanghai University	Song-Wei Li	2024-05-02	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
brassica		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	3.62	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	38.83 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	98.56 m³·mol⁻¹	ChemAxon
Polarizability	39.88 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

Not Available

References

General References

Xia ZY, Sun MM, Jin Y, Su MZ, Li SW, Wang H, Guo YW: Four uncommon cycloamphilectane-type diterpenoids with antibacterial activity from the South China Sea soft coral Sinularia brassica. Phytochemistry. 2024 Mar;219:113960. doi: 10.1016/j.phytochem.2023.113960. Epub 2023 Dec 29. [PubMed:38159620 ]

Showing NP-Card for Sinulobatin C (NP0332357)

MOL for NP0332357 (Sinulobatin C)

3D MOL for NP0332357 (Sinulobatin C)

3D SDF for NP0332357 (Sinulobatin C)

3D-SDF for NP0332357 (Sinulobatin C)

PDB for NP0332357 (Sinulobatin C)

3D PDB for NP0332357 (Sinulobatin C)

SMILES for NP0332357 (Sinulobatin C)

INCHI for NP0332357 (Sinulobatin C)

Structure for NP0332357 (Sinulobatin C)

3D Structure for NP0332357 (Sinulobatin C)