NP-MRD: Showing NP-Card for celafolin a-1 (NP0210943)

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Record Information

Version

2.0

Created at

2022-09-05 08:59:37 UTC

Updated at

2022-09-05 08:59:38 UTC

NP-MRD ID

NP0210943

Secondary Accession Numbers

None

Natural Product Identification

Common Name

celafolin a-1

Description

Celafolin A-1 belongs to the class of organic compounds known as agarofurans. These are organic compounds containing an agarofuran moiety( a three-ring system, with core fragment oxatricyclo[7.2.1.0^{1,6}]Dodec-2-ene). celafolin a-1 is found in Celastrus orbiculatus. Based on a literature review very few articles have been published on Celafolin A-1.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052210592D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309052210592D          

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    0.1488   -2.1391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4203   -2.7503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2243   -2.5653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7865   -3.1691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5905   -2.9842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8323   -2.1954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2701   -1.5916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4661   -1.7766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 21 26  1  0  0  0  0
 17 27  1  0  0  0  0
  5 27  1  0  0  0  0
 10 27  1  0  0  0  0
 27 28  1  6  0  0  0
 15 29  1  0  0  0  0
 10 29  1  0  0  0  0
 29 30  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 35 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0210943

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CC[C@H](OC(C)=O)[C@@]2(C)[C@H](C[C@@H]3[C@@H](OC(=O)\C=C\C4=CC=CC=C4)[C@]12OC3(C)C)OC(=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C33H38O7/c1-21-16-18-26(37-22(2)34)32(5)27(38-30(36)24-14-10-7-11-15-24)20-25-29(33(21,32)40-31(25,3)4)39-28(35)19-17-23-12-8-6-9-13-23/h6-15,17,19,21,25-27,29H,16,18,20H2,1-5H3/b19-17+/t21-,25-,26+,27+,29-,32+,33-/m1/s1

> <INCHI_KEY>
HYPWFAUBYBMXNJ-DMRFDBRWSA-N

> <FORMULA>
C33H38O7

> <MOLECULAR_WEIGHT>
546.66

> <EXACT_MASS>
546.261753564

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
59.571208935512665

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5S,6S,7S,9R,12R)-5-(acetyloxy)-2,6,10,10-tetramethyl-12-{[(2E)-3-phenylprop-2-enoyl]oxy}-11-oxatricyclo[7.2.1.0^{1,6}]dodecan-7-yl benzoate

> <JCHEM_LOGP>
6.435078229333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.231340066729673

> <JCHEM_POLAR_SURFACE_AREA>
88.13

> <JCHEM_REFRACTIVITY>
149.35989999999993

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,6S,7S,9R,12R)-5-(acetyloxy)-2,6,10,10-tetramethyl-12-{[(2E)-3-phenylprop-2-enoyl]oxy}-11-oxatricyclo[7.2.1.0^{1,6}]dodecan-7-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

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      11.176  -0.803   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.095  -1.965   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      11.324  -3.027   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       8.416  -2.095   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.690  -1.749   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.528  -0.443   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.832   0.943   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.292   1.038   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.256   2.648   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.358  -0.230   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.086   0.855   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.668   0.065   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.730   1.395   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.092  -0.334   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.976  -1.516   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.664  -2.977   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.264  -3.104   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.520  -4.771   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.519  -6.290   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.159  -7.182   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.553  -7.487   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.093  -7.453   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.892  -8.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.151 -10.120   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.611 -10.154   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.812  -8.837   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.118  -1.701   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.394  -2.925   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.242  -0.958   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       3.441  -2.491   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.011  -3.548   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       3.142  -4.806   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       0.278  -3.993   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.785  -5.134   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -2.285  -4.789   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -3.335  -5.916   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -4.836  -5.570   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -5.287  -4.098   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -4.238  -2.971   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -2.737  -3.316   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   27                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   27   29                                             
CONECT   11   10   12                                                       
CONECT   12   11   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   12   16   29                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   27                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   21                                                       
CONECT   27   17    5   10   28                                             
CONECT   28   27                                                            
CONECT   29   15   10   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   40                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   35                                                       
MASTER        0    0    0    0    0    0    0    0   40    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₃₈O₇

Average Mass

546.6600 Da

Monoisotopic Mass

546.26175 Da

IUPAC Name

(1S,2R,5S,6S,7S,9R,12R)-5-(acetyloxy)-2,6,10,10-tetramethyl-12-{[(2E)-3-phenylprop-2-enoyl]oxy}-11-oxatricyclo[7.2.1.0^{1,6}]dodecan-7-yl benzoate

Traditional Name

(1S,2R,5S,6S,7S,9R,12R)-5-(acetyloxy)-2,6,10,10-tetramethyl-12-{[(2E)-3-phenylprop-2-enoyl]oxy}-11-oxatricyclo[7.2.1.0^{1,6}]dodecan-7-yl benzoate

CAS Registry Number

Not Available

SMILES

C[C@@H]1CC[C@H](OC(C)=O)[C@@]2(C)[C@H](C[C@@H]3[C@@H](OC(=O)\C=C\C4=CC=CC=C4)[C@]12OC3(C)C)OC(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C33H38O7/c1-21-16-18-26(37-22(2)34)32(5)27(38-30(36)24-14-10-7-11-15-24)20-25-29(33(21,32)40-31(25,3)4)39-28(35)19-17-23-12-8-6-9-13-23/h6-15,17,19,21,25-27,29H,16,18,20H2,1-5H3/b19-17+/t21-,25-,26+,27+,29-,32+,33-/m1/s1

InChI Key

HYPWFAUBYBMXNJ-DMRFDBRWSA-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
Celastrus orbiculatus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as agarofurans. These are organic compounds containing an agarofuran moiety( a three-ring system, with core fragment oxatricyclo[7.2.1.0^{1,6}]Dodec-2-ene).

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Agarofurans

Alternative Parents

Substituents

Agarofuran
Cinnamic acid or derivatives
Cinnamic acid ester
Benzoate ester
Benzoic acid or derivatives
Tricarboxylic acid or derivatives
Benzoyl
Styrene
Fatty acid ester
Oxepane
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Tetrahydrofuran
Enoate ester
Carboxylic acid ester
Organoheterocyclic compound
Ether
Dialkyl ether
Carboxylic acid derivative
Oxacycle
Organic oxygen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

sesquiterpenoid (CHEBI:66831 )

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	6.44	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	88.13 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	149.36 m³·mol⁻¹	ChemAxon
Polarizability	59.57 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

23339045

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44593483

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for celafolin a-1 (NP0210943)

MOL for NP0210943 (celafolin a-1)

3D MOL for NP0210943 (celafolin a-1)

3D SDF for NP0210943 (celafolin a-1)

3D-SDF for NP0210943 (celafolin a-1)

PDB for NP0210943 (celafolin a-1)

3D PDB for NP0210943 (celafolin a-1)

SMILES for NP0210943 (celafolin a-1)

INCHI for NP0210943 (celafolin a-1)

Structure for NP0210943 (celafolin a-1)

3D Structure for NP0210943 (celafolin a-1)