NP-MRD: Showing NP-Card for (+)-Pulcherrin C (NP0081887)

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Record Information

Version

2.0

Created at

2022-04-29 02:57:29 UTC

Updated at

2022-04-29 02:57:29 UTC

NP-MRD ID

NP0081887

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Pulcherrin C

Description

Methyl (1S,2R,5S,7S,8R,9R,10S,11S)-9-(acetyloxy)-5-(benzoyloxy)-7,8-dihydroxy-2,6,6-trimethyl-15-oxatetracyclo[8.7.0.0²,⁷.0¹²,¹⁶]Heptadeca-12(16),13-diene-11-carboxylate belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. (+)-Pulcherrin C is found in Caesalpinia pulcherrima . Based on a literature review very few articles have been published on methyl (1S,2R,5S,7S,8R,9R,10S,11S)-9-(acetyloxy)-5-(benzoyloxy)-7,8-dihydroxy-2,6,6-trimethyl-15-oxatetracyclo[8.7.0.0²,⁷.0¹²,¹⁶]Heptadeca-12(16),13-diene-11-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292204572D          

 39 43  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652304292204572D          

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    3.1796   -2.2057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5235   -1.7202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0554   -1.0895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -0.1416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340    1.1139    0.0000 O   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
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  1  6  1  0  0  0  0
  5  7  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
  4 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
  9 15  1  1  0  0  0
  8 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  7 19  1  0  0  0  0
 17 20  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 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
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 23 28  1  0  0  0  0
 16 29  1  0  0  0  0
 16 30  1  0  0  0  0
  8 31  1  6  0  0  0
  7 32  1  1  0  0  0
  3 33  1  1  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
  2 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
  1 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0081887

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@H]1[C@H]2[C@@H](OC(C)=O)[C@@H](O)[C@@]3(O)C(C)(C)[C@H](CC[C@]3(C)[C@H]2CC2=C1C=CO2)OC(=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H36O9/c1-16(31)38-24-23-19(15-20-18(12-14-37-20)22(23)27(34)36-5)29(4)13-11-21(28(2,3)30(29,35)25(24)32)39-26(33)17-9-7-6-8-10-17/h6-10,12,14,19,21-25,32,35H,11,13,15H2,1-5H3/t19-,21-,22+,23-,24+,25+,29+,30+/m0/s1

> <INCHI_KEY>
YDLIYKIYHNWUMX-KQYGWRDBSA-N

> <FORMULA>
C30H36O9

> <MOLECULAR_WEIGHT>
540.609

> <EXACT_MASS>
540.235932739

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
56.55892890366207

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1S,2R,5S,7S,8R,9R,10S,11S)-9-(acetyloxy)-5-(benzoyloxy)-7,8-dihydroxy-2,6,6-trimethyl-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadeca-12(16),13-diene-11-carboxylate

> <ALOGPS_LOGP>
3.41

> <JCHEM_LOGP>
3.2148587546666647

> <ALOGPS_LOGS>
-4.13

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.090987896225496

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.718005141487762

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8237265139856382

> <JCHEM_POLAR_SURFACE_AREA>
132.50000000000003

> <JCHEM_REFRACTIVITY>
138.09599999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.04e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1S,2R,5S,7S,8R,9R,10S,11S)-9-(acetyloxy)-5-(benzoyloxy)-7,8-dihydroxy-2,6,6-trimethyl-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadeca-12(16),13-diene-11-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       6.874   1.134   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.398  -0.314   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.405  -1.492   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.889  -1.221   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.366   0.228   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.358   1.405   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.850   0.499   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.857  -0.678   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.380  -2.127   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.896  -2.398   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.419  -3.846   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.427  -5.024   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.950  -6.472   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.911  -4.752   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.387  -3.304   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.341  -0.407   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.182   1.041   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.810   2.218   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.326   1.947   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.698   1.312   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.221   2.761   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.229   3.938   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -3.737   3.032   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.730   1.854   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -6.246   2.125   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -6.769   3.574   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -5.777   4.751   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -4.261   4.480   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.017  -1.913   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.088  -0.981   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       0.864  -1.856   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       3.842   1.676   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.928  -2.940   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       5.935  -4.117   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       8.444  -3.211   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       9.437  -2.034   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       8.937  -0.264   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       9.365   1.215   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       8.090   2.079   0.000  0.00  0.00           O+0
CONECT    1    2    6   39                                                  
CONECT    2    1    3   37                                                  
CONECT    3    2    4   33                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   19   32                                             
CONECT    8    7    9   16   31                                             
CONECT    9    8   10   15                                                  
CONECT   10    9    4   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    9                                                            
CONECT   16    8   17   29   30                                             
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18    7                                                       
CONECT   20   17   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   23                                                       
CONECT   29   16                                                            
CONECT   30   16                                                            
CONECT   31    8                                                            
CONECT   32    7                                                            
CONECT   33    3   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35                                                            
CONECT   37    2   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38    1                                                       
MASTER        0    0    0    0    0    0    0    0   39    0   86    0
END

View in JSmol

Synonyms

Value	Source
Methyl (1S,2R,5S,7S,8R,9R,10S,11S)-9-(acetyloxy)-5-(benzoyloxy)-7,8-dihydroxy-2,6,6-trimethyl-15-oxatetracyclo[8.7.0.0,.0,]heptadeca-12(16),13-diene-11-carboxylic acid	Generator

Chemical Formula

C₃₀H₃₆O₉

Average Mass

540.6090 Da

Monoisotopic Mass

540.23593 Da

IUPAC Name

methyl (1S,2R,5S,7S,8R,9R,10S,11S)-9-(acetyloxy)-5-(benzoyloxy)-7,8-dihydroxy-2,6,6-trimethyl-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadeca-12(16),13-diene-11-carboxylate

Traditional Name

methyl (1S,2R,5S,7S,8R,9R,10S,11S)-9-(acetyloxy)-5-(benzoyloxy)-7,8-dihydroxy-2,6,6-trimethyl-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadeca-12(16),13-diene-11-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@H]1[C@H]2[C@@H](OC(C)=O)[C@@H](O)[C@@]3(O)C(C)(C)[C@H](CC[C@]3(C)[C@H]2CC2=C1C=CO2)OC(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C30H36O9/c1-16(31)38-24-23-19(15-20-18(12-14-37-20)22(23)27(34)36-5)29(4)13-11-21(28(2,3)30(29,35)25(24)32)39-26(33)17-9-7-6-8-10-17/h6-10,12,14,19,21-25,32,35H,11,13,15H2,1-5H3/t19-,21-,22+,23-,24+,25+,29+,30+/m0/s1

InChI Key

YDLIYKIYHNWUMX-KQYGWRDBSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Caesalpinia pulcherrima	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Naphthofuran
Benzoate ester
Tricarboxylic acid or derivatives
Benzoic acid or derivatives
Benzofuran
Benzoyl
Benzenoid
Monocyclic benzene moiety
Heteroaromatic compound
Methyl ester
Tertiary alcohol
Furan
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
1,2-diol
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	3.41	ALOGPS
logP	3.21	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	12.72	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	132.5 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	138.1 m³·mol⁻¹	ChemAxon
Polarizability	56.56 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	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

75569392

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

134844448

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Pulcherrin C (NP0081887)

MOL for NP0081887 ((+)-Pulcherrin C)

3D MOL for NP0081887 ((+)-Pulcherrin C)

3D SDF for NP0081887 ((+)-Pulcherrin C)

3D-SDF for NP0081887 ((+)-Pulcherrin C)

PDB for NP0081887 ((+)-Pulcherrin C)

3D PDB for NP0081887 ((+)-Pulcherrin C)

SMILES for NP0081887 ((+)-Pulcherrin C)

INCHI for NP0081887 ((+)-Pulcherrin C)

Structure for NP0081887 ((+)-Pulcherrin C)

3D Structure for NP0081887 ((+)-Pulcherrin C)