NP-MRD: Showing NP-Card for Caesalmin C (NP0071997)

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Record Information

Version

2.0

Created at

2022-04-28 17:23:10 UTC

Updated at

2022-04-28 17:23:10 UTC

NP-MRD ID

NP0071997

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Caesalmin C

Description

Caesalmin C belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Caesalmin C is found in Caesalpinia minax and Caesalpinia crista . Caesalmin C was first documented in 2005 (PMID: 16204987). Based on a literature review a small amount of articles have been published on Caesalmin C (PMID: 26125942) (PMID: 35480829) (PMID: 29979518) (PMID: 25489969).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282219232D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304282219232D          

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M  END
> <DATABASE_ID>
NP0071997

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1CCC(C)(C)[C@]2(O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H]3[C@H](CC4=C(C=CO4)C3=C)[C@@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C26H34O8/c1-13-17-9-11-31-19(17)12-18-21(13)22(33-15(3)28)23(34-16(4)29)26(30)24(5,6)10-8-20(25(18,26)7)32-14(2)27/h9,11,18,20-23,30H,1,8,10,12H2,2-7H3/t18-,20-,21-,22+,23-,25-,26+/m0/s1

> <INCHI_KEY>
LNEQDVOGNPILGB-WOWNGYFCSA-N

> <FORMULA>
C26H34O8

> <MOLECULAR_WEIGHT>
474.55

> <EXACT_MASS>
474.225368055

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
50.10504227550942

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,3S,7R,8S,9R,10R)-3,9-bis(acetyloxy)-7-hydroxy-2,6,6-trimethyl-11-methylidene-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadeca-12(16),13-dien-8-yl acetate

> <ALOGPS_LOGP>
3.65

> <JCHEM_LOGP>
2.311277776

> <ALOGPS_LOGS>
-4.11

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.009794925604727

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7872168360975422

> <JCHEM_POLAR_SURFACE_AREA>
112.27000000000001

> <JCHEM_REFRACTIVITY>
119.8941

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.72e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,3S,7R,8S,9R,10R)-3,9-bis(acetyloxy)-7-hydroxy-2,6,6-trimethyl-11-methylidene-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadeca-12(16),13-dien-8-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       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       6.928  -2.940   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.889  -1.221   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.366   0.228   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.358   1.405   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.850   0.499   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.857  -0.678   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.380  -2.127   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.896  -2.398   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.419  -3.846   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.890  -5.397   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.537  -4.216   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.950  -6.472   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.387  -3.304   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.911  -4.752   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.427  -5.024   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.918  -5.930   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.341  -0.407   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.182   1.041   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.810   2.218   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.326   1.947   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.319   3.125   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.796   4.573   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.280   4.844   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.789   5.750   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.088  -0.981   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  O   UNK     0       0.864  -1.856   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       3.842   1.676   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.937  -0.264   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       9.365   1.215   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       8.090   2.079   0.000  0.00  0.00           O+0
CONECT    1    2    7   34                                                  
CONECT    2    1    3   32                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   11                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6    1                                                       
CONECT    8    6    9   23   31                                             
CONECT    9    8   10   20   30                                             
CONECT   10    9   11   16                                                  
CONECT   11   10    5   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   10   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20    9   21   28   29                                             
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22    8   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   20                                                            
CONECT   29   20                                                            
CONECT   30    9                                                            
CONECT   31    8                                                            
CONECT   32    2   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33    1                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₄O₈

Average Mass

474.5500 Da

Monoisotopic Mass

474.22537 Da

IUPAC Name

(1S,2S,3S,7R,8S,9R,10R)-3,9-bis(acetyloxy)-7-hydroxy-2,6,6-trimethyl-11-methylidene-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadeca-12(16),13-dien-8-yl acetate

Traditional Name

(1S,2S,3S,7R,8S,9R,10R)-3,9-bis(acetyloxy)-7-hydroxy-2,6,6-trimethyl-11-methylidene-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadeca-12(16),13-dien-8-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1CCC(C)(C)[C@]2(O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H]3[C@H](CC4=C(C=CO4)C3=C)[C@@]12C

InChI Identifier

InChI=1S/C26H34O8/c1-13-17-9-11-31-19(17)12-18-21(13)22(33-15(3)28)23(34-16(4)29)26(30)24(5,6)10-8-20(25(18,26)7)32-14(2)27/h9,11,18,20-23,30H,1,8,10,12H2,2-7H3/t18-,20-,21-,22+,23-,25-,26+/m0/s1

InChI Key

LNEQDVOGNPILGB-WOWNGYFCSA-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 minax	Plant	KNApSAcK
Guilandina crista	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
Tricarboxylic acid or derivatives
Cyclic alcohol
Heteroaromatic compound
Furan
Tertiary alcohol
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	3.65	ALOGPS
logP	2.31	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	13.01	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	112.27 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	119.89 m³·mol⁻¹	ChemAxon
Polarizability	50.11 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	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00029419

Chemspider ID

8633020

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10457606

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Dong R, Yuan J, Wu S, Huang J, Xu X, Wu Z, Gao H: Anti-inflammation furanoditerpenoids from Caesalpinia minax Hance. Phytochemistry. 2015 Sep;117:325-331. doi: 10.1016/j.phytochem.2015.06.025. Epub 2015 Jun 27. [PubMed:26125942 ]
Kalauni SK, Awale S, Tezuka Y, Banskota AH, Linn TZ, Kadota S: Methyl migrated cassane-type furanoditerpenes of Caesalpinia crista from Myanmar. Chem Pharm Bull (Tokyo). 2005 Oct;53(10):1300-4. doi: 10.1248/cpb.53.1300. [PubMed:16204987 ]
Liu T, Ning Z, Yin Y, Qi S, Gao H: Acid-catalyzed transformation of cassane diterpenoids from Caesalpinia bonduc to aromatic derivatives. RSC Adv. 2021 Jun 22;11(36):22070-22078. doi: 10.1039/d1ra03636j. eCollection 2021 Jun 21. [PubMed:35480829 ]
Tu WC, Ding LF, Yang H, Song LD, Wu XD: [A new cassane diterpene from Caesalpinia bonduc]. Yao Xue Xue Bao. 2017 Feb;52(2):279-82. [PubMed:29979518 ]
Li C, Lin D, Gao H, Hua H, Peng Y, Zheng J: N-acetyl lysine/glutathione-derived pyrroles as potential ex vivo biomarkers of bioactivated furan-containing compounds. Chem Res Toxicol. 2015 Mar 16;28(3):384-93. doi: 10.1021/tx500334m. Epub 2014 Dec 26. [PubMed:25489969 ]

Showing NP-Card for Caesalmin C (NP0071997)

MOL for NP0071997 (Caesalmin C)

3D MOL for NP0071997 (Caesalmin C)

3D SDF for NP0071997 (Caesalmin C)

3D-SDF for NP0071997 (Caesalmin C)

PDB for NP0071997 (Caesalmin C)

3D PDB for NP0071997 (Caesalmin C)

SMILES for NP0071997 (Caesalmin C)

INCHI for NP0071997 (Caesalmin C)

Structure for NP0071997 (Caesalmin C)

3D Structure for NP0071997 (Caesalmin C)