NP-MRD: Showing NP-Card for Celastranhydride (NP0066518)

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Record Information

Version

2.0

Created at

2022-04-28 10:46:22 UTC

Updated at

2022-04-28 10:46:22 UTC

NP-MRD ID

NP0066518

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Celastranhydride

Description

118075-30-2 Belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. Celastranhydride is found in Kokoona zeylanica THW.(Celastraceae), Pleurostylia opposita and Pristimera indica. Based on a literature review very few articles have been published on 118075-30-2.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282212462D          

 33 37  0  0  1  0            999 V2000
    6.0770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    5.2520   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3645    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    2.3645    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 10 33  1  1  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304282212462D          

 33 37  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0066518

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@]1(C)CC[C@]2(C)CC[C@]3(C)C4=CC=C5C(=O)OC(=O)C=C5[C@]4(C)CC[C@@]3(C)[C@@H]2C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H36O5/c1-24-9-10-25(2,23(31)32-6)16-20(24)28(5)14-12-26(3)18-15-21(29)33-22(30)17(18)7-8-19(26)27(28,4)13-11-24/h7-8,15,20H,9-14,16H2,1-6H3/t20-,24-,25-,26+,27-,28+/m1/s1

> <INCHI_KEY>
AFYNUVCDKLFCAU-PTDFUWQFSA-N

> <FORMULA>
C28H36O5

> <MOLECULAR_WEIGHT>
452.591

> <EXACT_MASS>
452.256274259

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
49.9306246222788

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1S,11R,14S,15R,17R,20S)-1,11,14,17,20-pentamethyl-6,8-dioxo-7-oxapentacyclo[12.8.0.0^{2,11}.0^{5,10}.0^{15,20}]docosa-2,4,9-triene-17-carboxylate

> <ALOGPS_LOGP>
6.23

> <JCHEM_LOGP>
5.424505272333333

> <ALOGPS_LOGS>
-5.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.633804753339345

> <JCHEM_POLAR_SURFACE_AREA>
69.67

> <JCHEM_REFRACTIVITY>
126.90949999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.66e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1S,11R,14S,15R,17R,20S)-1,11,14,17,20-pentamethyl-6,8-dioxo-7-oxapentacyclo[12.8.0.0^{2,11}.0^{5,10}.0^{15,20}]docosa-2,4,9-triene-17-carboxylate

> <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      11.344  -0.564   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      12.114  -1.897   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      12.114   0.770   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      11.344   2.104   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      12.114   3.437   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       9.804   2.104   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.034   3.437   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.494   3.437   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.034   0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.804  -0.564   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.414   3.437   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.510  -2.103   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.742  -1.380   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -0.689  -2.919   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -2.102  -0.657   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -3.408  -1.473   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.334   3.437   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.644  -0.564   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.264  -0.564   0.000  0.00  0.00           C+0
CONECT    1    2    3   12                                                  
CONECT    2    1                                                            
CONECT    3    1    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   16                                                  
CONECT   10    9   11   13   33                                             
CONECT   11   10    6   12                                                  
CONECT   12   11    1                                                       
CONECT   13   10   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   20   32                                             
CONECT   16   15    9   17   31                                             
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   24   30                                             
CONECT   20   19   15   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   25   26                                             
CONECT   23   22   24                                                       
CONECT   24   23   19                                                       
CONECT   25   22                                                            
CONECT   26   22   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28                                                            
CONECT   30   19                                                            
CONECT   31   16                                                            
CONECT   32   15                                                            
CONECT   33   10                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₆O₅

Average Mass

452.5910 Da

Monoisotopic Mass

452.25627 Da

IUPAC Name

methyl (1S,11R,14S,15R,17R,20S)-1,11,14,17,20-pentamethyl-6,8-dioxo-7-oxapentacyclo[12.8.0.0^{2,11}.0^{5,10}.0^{15,20}]docosa-2,4,9-triene-17-carboxylate

Traditional Name

methyl (1S,11R,14S,15R,17R,20S)-1,11,14,17,20-pentamethyl-6,8-dioxo-7-oxapentacyclo[12.8.0.0^{2,11}.0^{5,10}.0^{15,20}]docosa-2,4,9-triene-17-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@]1(C)CC[C@]2(C)CC[C@]3(C)C4=CC=C5C(=O)OC(=O)C=C5[C@]4(C)CC[C@@]3(C)[C@@H]2C1

InChI Identifier

InChI=1S/C28H36O5/c1-24-9-10-25(2,23(31)32-6)16-20(24)28(5)14-12-26(3)18-15-21(29)33-22(30)17(18)7-8-19(26)27(28,4)13-11-24/h7-8,15,20H,9-14,16H2,1-6H3/t20-,24-,25-,26+,27-,28+/m1/s1

InChI Key

AFYNUVCDKLFCAU-PTDFUWQFSA-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
Kokoona zeylanica THW.(Celastraceae)	Plant	KNApSAcK
Pleurostylia opposita	LOTUS Database	35616633
Pristimera indica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Not Available

Direct Parent

Naphthopyrans

Alternative Parents

Substituents

Naphthopyran
Naphthalene
Tricarboxylic acid or derivatives
Dihydropyranone
Pyran
Carboxylic acid anhydride
Methyl ester
Carboxylic acid ester
Carboxylic acid derivative
Oxacycle
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	6.23	ALOGPS
logP	5.42	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Basic)	-6.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	69.67 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	126.91 m³·mol⁻¹	ChemAxon
Polarizability	49.93 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

C00024085

Chemspider ID

10270941

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14707061

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Celastranhydride (NP0066518)

MOL for NP0066518 (Celastranhydride)

3D MOL for NP0066518 (Celastranhydride)

3D SDF for NP0066518 (Celastranhydride)

3D-SDF for NP0066518 (Celastranhydride)

PDB for NP0066518 (Celastranhydride)

3D PDB for NP0066518 (Celastranhydride)

SMILES for NP0066518 (Celastranhydride)

INCHI for NP0066518 (Celastranhydride)

Structure for NP0066518 (Celastranhydride)

3D Structure for NP0066518 (Celastranhydride)