NP-MRD: Showing NP-Card for (+)-epsilon-Caesalpin (NP0076515)

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Record Information

Version

2.0

Created at

2022-04-28 21:41:29 UTC

Updated at

2022-04-28 21:41:30 UTC

NP-MRD ID

NP0076515

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-epsilon-Caesalpin

Description

Epsilon-Caesalpin belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. (+)-epsilon-Caesalpin is found in Caesalpinia major and Caesalpinia bonduc . (+)-epsilon-Caesalpin was first documented in 2006 (PMID: 17193240). Based on a literature review very few articles have been published on epsilon-Caesalpin (PMID: 34656025).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282223412D          

 31 34  0  0  1  0            999 V2000
    4.4661    0.8922    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1858    1.6682    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7176    2.2989    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5297    2.1537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8100    1.3777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2782    0.7470    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5585   -0.0289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3706   -0.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6509   -0.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9024    0.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7032    2.9602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2954    2.4609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4373    3.0748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6252    3.2200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0934    2.5893    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3737    1.8134    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8418    1.1827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0297    1.3279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7494    2.1038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2812    2.7345    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6695    3.2880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3980    3.5512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9249    2.0770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6955    1.2845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3784    0.8215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2494    2.9296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6540    1.0374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9343    0.2615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2146   -0.5144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0267   -0.6596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6827   -1.1451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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  2 27  1  1  0  0  0
  1 28  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
M  END

     RDKit          3D

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    5.2277    1.3354    0.8315 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5915   -0.4533   -1.6380 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4115   -1.5177    0.2757 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1253   -0.1290    0.4953 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0897   -0.3535    1.9655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1582    0.9124    0.2121 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2307    1.0423   -1.2176 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652304282223412D          

 31 34  0  0  1  0            999 V2000
    4.4661    0.8922    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1858    1.6682    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7176    2.2989    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5297    2.1537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6955    1.2845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3784    0.8215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2494    2.9296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0267   -0.6596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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  3  4  1  0  0  0  0
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  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
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 24 25  1  0  0  0  0
 18 25  1  0  0  0  0
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 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0076515

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1CC(C)(C)[C@]2(O)CC[C@@H]3[C@H](CC4=C(C=CO4)[C@@]3(C)O)[C@@]2(C)[C@H]1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H34O7/c1-13(25)30-19-12-21(3,4)24(28)9-7-15-17(22(24,5)20(19)31-14(2)26)11-18-16(8-10-29-18)23(15,6)27/h8,10,15,17,19-20,27-28H,7,9,11-12H2,1-6H3/t15-,17+,19+,20+,22+,23+,24-/m1/s1

> <INCHI_KEY>
SUJKNDTZWVVCQL-HMZQDCCASA-N

> <FORMULA>
C24H34O7

> <MOLECULAR_WEIGHT>
434.529

> <EXACT_MASS>
434.230453435

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
46.572048934900806

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,3R,4S,7R,10R,11S)-3-(acetyloxy)-7,11-dihydroxy-2,6,6,11-tetramethyl-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadeca-12(16),13-dien-4-yl acetate

> <ALOGPS_LOGP>
3.05

> <JCHEM_LOGP>
1.9167149553333311

> <ALOGPS_LOGS>
-3.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.157605216495973

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.522238122445703

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8310829589423405

> <JCHEM_POLAR_SURFACE_AREA>
106.20000000000002

> <JCHEM_REFRACTIVITY>
111.20870000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.65e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,3R,4S,7R,10R,11S)-3-(acetyloxy)-7,11-dihydroxy-2,6,6,11-tetramethyl-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadeca-12(16),13-dien-4-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       8.337   1.666   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.813   3.114   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.806   4.291   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.322   4.020   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.845   2.572   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.853   1.394   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      10.376  -0.054   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      11.892  -0.325   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      12.415  -1.773   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      12.885   0.852   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.646   5.526   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.751   4.594   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.283   5.740   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.767   6.011   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.774   4.833   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.297   3.385   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.305   2.208   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.789   2.479   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.266   3.927   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.258   5.104   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.116   6.138   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.476   6.629   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.726   3.877   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.298   2.398   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.573   1.534   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       9.799   5.469   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.821   1.937   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       7.344   0.488   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       7.867  -0.960   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       9.383  -1.231   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       6.874  -2.138   0.000  0.00  0.00           C+0
CONECT    1    2    6   28                                                  
CONECT    2    1    3   16   27                                             
CONECT    3    2    4   13   26                                             
CONECT    4    3    5   11   12                                             
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    4                                                            
CONECT   12    4                                                            
CONECT   13    3   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15    2   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   25                                                  
CONECT   19   18   20   23                                                  
CONECT   20   19   15   21   22                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   19   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   18                                                       
CONECT   26    3                                                            
CONECT   27    2                                                            
CONECT   28    1   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₃₄O₇

Average Mass

434.5290 Da

Monoisotopic Mass

434.23045 Da

IUPAC Name

(1S,2S,3R,4S,7R,10R,11S)-3-(acetyloxy)-7,11-dihydroxy-2,6,6,11-tetramethyl-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadeca-12(16),13-dien-4-yl acetate

Traditional Name

(1S,2S,3R,4S,7R,10R,11S)-3-(acetyloxy)-7,11-dihydroxy-2,6,6,11-tetramethyl-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadeca-12(16),13-dien-4-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1CC(C)(C)[C@]2(O)CC[C@@H]3[C@H](CC4=C(C=CO4)[C@@]3(C)O)[C@@]2(C)[C@H]1OC(C)=O

InChI Identifier

InChI=1S/C24H34O7/c1-13(25)30-19-12-21(3,4)24(28)9-7-15-17(22(24,5)20(19)31-14(2)26)11-18-16(8-10-29-18)23(15,6)27/h8,10,15,17,19-20,27-28H,7,9,11-12H2,1-6H3/t15-,17+,19+,20+,22+,23+,24-/m1/s1

InChI Key

SUJKNDTZWVVCQL-HMZQDCCASA-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 major	LOTUS Database	35616633
Guilandina bonduc	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
Benzofuran
Dicarboxylic acid or derivatives
Cyclic alcohol
Heteroaromatic compound
Tertiary alcohol
Furan
Carboxylic acid ester
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Organooxygen compound
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	3.05	ALOGPS
logP	1.92	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	13.52	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	106.2 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	111.21 m³·mol⁻¹	ChemAxon
Polarizability	46.57 Å³	ChemAxon
Number of Rings	4	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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00036415

Chemspider ID

10295164

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21679153

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Li DM, Ma L, Liu GM, Hu LH: Cassane diterpene-lactones from the seed of Caesalpinia minax HANCE. Chem Biodivers. 2006 Nov;3(11):1260-5. doi: 10.1002/cbdv.200690128. [PubMed:17193240 ]
Tu WC, Ding LF, Peng LY, Song LD, Wu XD, Zhao QS: Cassane diterpenoids from the seeds of Caesalpinia bonduc and their nitric oxide production and alpha-glucosidase inhibitory activities. Phytochemistry. 2022 Jan;193:112973. doi: 10.1016/j.phytochem.2021.112973. Epub 2021 Oct 13. [PubMed:34656025 ]

Showing NP-Card for (+)-epsilon-Caesalpin (NP0076515)

MOL for NP0076515 ((+)-epsilon-Caesalpin)

3D MOL for NP0076515 ((+)-epsilon-Caesalpin)

3D SDF for NP0076515 ((+)-epsilon-Caesalpin)

3D-SDF for NP0076515 ((+)-epsilon-Caesalpin)

PDB for NP0076515 ((+)-epsilon-Caesalpin)

3D PDB for NP0076515 ((+)-epsilon-Caesalpin)

SMILES for NP0076515 ((+)-epsilon-Caesalpin)

INCHI for NP0076515 ((+)-epsilon-Caesalpin)

Structure for NP0076515 ((+)-epsilon-Caesalpin)

3D Structure for NP0076515 ((+)-epsilon-Caesalpin)