NP-MRD: Showing NP-Card for (+)-Caesalpin H (NP0070979)

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Record Information

Version

2.0

Created at

2022-04-28 16:22:57 UTC

Updated at

2022-04-28 16:22:57 UTC

NP-MRD ID

NP0070979

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Caesalpin H

Description

CAESALMIN E belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. (+)-Caesalpin H is found in Caesalpinia minax, Caesalpinia bonduc and Caesalpinia crista . (+)-Caesalpin H was first documented in 2019 (PMID: 31145477). Based on a literature review very few articles have been published on CAESALMIN E.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282218222D          

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M  END

     RDKit          3D

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  Mrv1652304282218222D          

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M  END
> <DATABASE_ID>
NP0070979

> <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)[C@@]3(C)O)[C@@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C26H36O9/c1-13(27)33-19-8-10-23(4,5)26(31)22(35-15(3)29)21(34-14(2)28)20-17(24(19,26)6)12-18-16(9-11-32-18)25(20,7)30/h9,11,17,19-22,30-31H,8,10,12H2,1-7H3/t17-,19-,20-,21+,22-,24-,25+,26+/m0/s1

> <INCHI_KEY>
ZMDJQZBKCANBDV-GZEDFXFRSA-N

> <FORMULA>
C26H36O9

> <MOLECULAR_WEIGHT>
492.565

> <EXACT_MASS>
492.235932739

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
51.31780562806205

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,3S,7R,8S,9R,10S,11S)-3,9-bis(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-8-yl acetate

> <ALOGPS_LOGP>
2.68

> <JCHEM_LOGP>
1.324493485666665

> <ALOGPS_LOGS>
-3.77

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.725206929545127

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.917431988644456

> <JCHEM_PKA_STRONGEST_BASIC>
-2.831142652840075

> <JCHEM_POLAR_SURFACE_AREA>
132.5

> <JCHEM_REFRACTIVITY>
121.6229

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.37e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,3S,7R,8S,9R,10S,11S)-3,9-bis(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-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       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       2.890  -5.397   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.537  -4.216   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.950  -6.472   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       1.911  -4.752   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.427  -5.024   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.918  -5.930   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.341  -0.407   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.182   1.041   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.810   2.218   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.326   1.947   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.319   3.125   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.796   4.573   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.280   4.844   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       3.789   5.750   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.088  -0.981   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.017  -1.913   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       0.864  -1.856   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       3.842   1.676   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.547  -2.525   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       6.187  -3.016   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       8.937  -0.264   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.365   1.215   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       8.090   2.079   0.000  0.00  0.00           O+0
CONECT    1    2    6   35                                                  
CONECT    2    1    3   33                                                  
CONECT    3    2    4   31   32                                             
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   22   30                                             
CONECT    8    7    9   19   29                                             
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   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19    8   20   27   28                                             
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21    7   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   19                                                            
CONECT   28   19                                                            
CONECT   29    8                                                            
CONECT   30    7                                                            
CONECT   31    3                                                            
CONECT   32    3                                                            
CONECT   33    2   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34    1                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₆O₉

Average Mass

492.5650 Da

Monoisotopic Mass

492.23593 Da

IUPAC Name

(1S,2S,3S,7R,8S,9R,10S,11S)-3,9-bis(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-8-yl acetate

Traditional Name

(1S,2S,3S,7R,8S,9R,10S,11S)-3,9-bis(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-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)[C@@]3(C)O)[C@@]12C

InChI Identifier

InChI=1S/C26H36O9/c1-13(27)33-19-8-10-23(4,5)26(31)22(35-15(3)29)21(34-14(2)28)20-17(24(19,26)6)12-18-16(9-11-32-18)25(20,7)30/h9,11,17,19-22,30-31H,8,10,12H2,1-7H3/t17-,19-,20-,21+,22-,24-,25+,26+/m0/s1

InChI Key

ZMDJQZBKCANBDV-GZEDFXFRSA-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 bonduc	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	2.68	ALOGPS
logP	1.32	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	12.92	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	6	ChemAxon
Refractivity	121.62 m³·mol⁻¹	ChemAxon
Polarizability	51.32 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

C00029869

Chemspider ID

8656223

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10480816

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wang M, Wang D, Gao C, Li X, Sha L, Zhao Q, Gao H, Wu Z: Pharmacokinetic and tissue distribution studies of cassane diterpenoids, in rats through an ultra-high-performance liquid chromatography-Q exactive hybrid quadrupole-Orbitrap high-resolution accurate mass spectrometry. Biomed Chromatogr. 2019 Oct;33(10):e4610. doi: 10.1002/bmc.4610. Epub 2019 Jul 11. [PubMed:31145477 ]

Showing NP-Card for (+)-Caesalpin H (NP0070979)

MOL for NP0070979 ((+)-Caesalpin H)

3D MOL for NP0070979 ((+)-Caesalpin H)

3D SDF for NP0070979 ((+)-Caesalpin H)

3D-SDF for NP0070979 ((+)-Caesalpin H)

PDB for NP0070979 ((+)-Caesalpin H)

3D PDB for NP0070979 ((+)-Caesalpin H)

SMILES for NP0070979 ((+)-Caesalpin H)

INCHI for NP0070979 ((+)-Caesalpin H)

Structure for NP0070979 ((+)-Caesalpin H)

3D Structure for NP0070979 ((+)-Caesalpin H)