NP-MRD: Showing NP-Card for Crotokilwaepoxide B (NP0331520)

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Record Information

Version

2.0

Created at

2023-02-18 00:09:14 UTC

Updated at

2024-09-03 04:16:00 UTC

NP-MRD ID

NP0331520

Natural Product DOI

https://doi.org/10.57994/0490

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Crotokilwaepoxide B

Description

Crotokilwaepoxide B belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. Based on a literature review very few articles have been published on Crotokilwaepoxide B.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652302182301092D          

 28 34  0  0  1  0            999 V2000
    5.4111   -0.4075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7152    0.0356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6647    0.8590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8659    1.0654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5981    1.8457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8210    2.1228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1198    1.6881    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2956    1.7239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7387    2.4198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0226    0.8688    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8029    1.1367    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6024    0.2820    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3842   -0.5136    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1798   -0.7319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5860   -0.7224    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1659   -1.3092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0061   -0.1355    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1820   -0.1738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1090    0.5982    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9046    0.8165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8043    0.0732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2244    0.6601    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5352    1.1135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4970    1.9376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1368   -0.3465    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4228    0.3695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9477   -0.2670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7414   -1.0658    0.0000 C   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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7  9  1  6  0  0  0
  7 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  6  0  0  0
 13 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 17 21  1  6  0  0  0
 17 22  1  0  0  0  0
 10 22  1  0  0  0  0
 22 21  1  6  0  0  0
 22 23  1  0  0  0  0
 19 23  1  0  0  0  0
 23 24  2  0  0  0  0
 12 25  1  6  0  0  0
 12 26  1  0  0  0  0
  4 26  1  0  0  0  0
 26 27  2  0  0  0  0
  2 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  END


  Mrv1652302182301092D          

 28 34  0  0  1  0            999 V2000
    5.4111   -0.4075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7152    0.0356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6647    0.8590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8659    1.0654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5981    1.8457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8210    2.1228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1198    1.6881    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2956    1.7239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7387    2.4198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0226    0.8688    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8029    1.1367    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6024    0.2820    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3842   -0.5136    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1798   -0.7319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5860   -0.7224    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1659   -1.3092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0061   -0.1355    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1820   -0.1738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1090    0.5982    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9046    0.8165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8043    0.0732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2244    0.6601    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5352    1.1135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4970    1.9376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1368   -0.3465    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4228    0.3695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9477   -0.2670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7414   -1.0658    0.0000 C   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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7  9  1  6  0  0  0
  7 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  6  0  0  0
 13 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 17 21  1  6  0  0  0
 17 22  1  0  0  0  0
 10 22  1  0  0  0  0
 22 21  1  6  0  0  0
 22 23  1  0  0  0  0
 19 23  1  0  0  0  0
 23 24  2  0  0  0  0
 12 25  1  6  0  0  0
 12 26  1  0  0  0  0
  4 26  1  0  0  0  0
 26 27  2  0  0  0  0
  2 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331520

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12C3=C(C)C(=O)OC3=CC[C@]3(CO3)[C@@]1([H])[C@@]13O[C@@]1(C[C@@H](C)C3=O)[C@H]1O[C@@]21C

> <INCHI_IDENTIFIER>
InChI=1S/C20H20O6/c1-8-6-19-16-17(3,25-16)12-11-9(2)15(22)24-10(11)4-5-18(7-23-18)13(12)20(19,26-19)14(8)21/h4,8,12-13,16H,5-7H2,1-3H3/t8-,12-,13+,16+,17+,18+,19+,20+/m1/s1

> <INCHI_KEY>
STCVPWDGXBXQQN-ZQJKXGJFSA-N

> <FORMULA>
C20H20O6

> <MOLECULAR_WEIGHT>
356.374

> <EXACT_MASS>
356.125988364

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
35.38044217937372

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,4S,5S,13R,14S,15R,17R)-4,7,17-trimethyl-3,9,19-trioxaspiro[hexacyclo[13.3.1.0^{1,15}.0^{2,4}.0^{5,14}.0^{6,10}]nonadecane-13,2'-oxirane]-6,10-diene-8,16-dione

> <JCHEM_LOGP>
1.1354135486666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.490243729253045

> <JCHEM_PKA_STRONGEST_BASIC>
-3.782572061874847

> <JCHEM_POLAR_SURFACE_AREA>
80.96000000000001

> <JCHEM_REFRACTIVITY>
88.71489999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,4S,5S,13R,14S,15R,17R)-4,7,17-trimethyl-3,9,19-trioxaspiro[hexacyclo[13.3.1.0^{1,15}.0^{2,4}.0^{5,14}.0^{6,10}]nonadecane-13,2'-oxirane]-6,10-diene-8,16-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-FEB-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-FEB-23         0                                  
HETATM    1  O   UNK     0      10.101  -0.761   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       8.802   0.066   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       8.707   1.604   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       7.216   1.989   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.716   3.445   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.266   3.963   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.957   3.151   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.418   3.218   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.246   4.517   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.775   1.622   0.000  0.00  0.00           C+0
HETATM   11  H   UNK     0       5.232   2.122   0.000  0.00  0.00           H+0
HETATM   12  C   UNK     0       4.858   0.526   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.450  -0.959   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.936  -1.366   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.961  -1.348   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.043  -2.444   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.878  -0.253   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.340  -0.324   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.204   1.117   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.689   1.524   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.368   0.137   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.286   1.232   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.999   2.079   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.928   3.617   0.000  0.00  0.00           O+0
HETATM   25  H   UNK     0       5.855  -0.647   0.000  0.00  0.00           H+0
HETATM   26  C   UNK     0       6.389   0.690   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.369  -0.498   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.984  -1.989   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   27                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   26                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   10                                             
CONECT    8    7    9                                                       
CONECT    9    8    7                                                       
CONECT   10    7   11   12   22                                             
CONECT   11   10                                                            
CONECT   12   10   13   25   26                                             
CONECT   13   12   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15   13                                                       
CONECT   17   15   18   21   22                                             
CONECT   18   17   19                                                       
CONECT   19   18   20   23                                                  
CONECT   20   19                                                            
CONECT   21   17   22                                                       
CONECT   22   17   10   21   23                                             
CONECT   23   22   19   24                                                  
CONECT   24   23                                                            
CONECT   25   12                                                            
CONECT   26   12    4   27                                                  
CONECT   27   26    2   28                                                  
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₀O₆

Average Mass

356.3740 Da

Monoisotopic Mass

356.12599 Da

IUPAC Name

(1S,2S,4S,5S,13R,14S,15R,17R)-4,7,17-trimethyl-3,9,19-trioxaspiro[hexacyclo[13.3.1.0^{1,15}.0^{2,4}.0^{5,14}.0^{6,10}]nonadecane-13,2'-oxirane]-6,10-diene-8,16-dione

Traditional Name

(1S,2S,4S,5S,13R,14S,15R,17R)-4,7,17-trimethyl-3,9,19-trioxaspiro[hexacyclo[13.3.1.0^{1,15}.0^{2,4}.0^{5,14}.0^{6,10}]nonadecane-13,2'-oxirane]-6,10-diene-8,16-dione

CAS Registry Number

Not Available

SMILES

[H][C@@]12C3=C(C)C(=O)OC3=CC[C@]3(CO3)[C@@]1([H])[C@@]13O[C@@]1(C[C@@H](C)C3=O)[C@H]1O[C@@]21C

InChI Identifier

InChI=1S/C20H20O6/c1-8-6-19-16-17(3,25-16)12-11-9(2)15(22)24-10(11)4-5-18(7-23-18)13(12)20(19,26-19)14(8)21/h4,8,12-13,16H,5-7H2,1-3H3/t8-,12-,13+,16+,17+,18+,19+,20+/m1/s1

InChI Key

STCVPWDGXBXQQN-ZQJKXGJFSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	mate.erdelyi@kemi.uu.se	Not Available	Not Available	2023-02-18	View Spectrum
TOCSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	mate.erdelyi@kemi.uu.se	Not Available	Not Available	2023-02-18	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	mate.erdelyi@kemi.uu.se	Not Available	Not Available	2023-02-18	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	mate.erdelyi@kemi.uu.se	Not Available	Not Available	2023-02-18	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	mate.erdelyi@kemi.uu.se	Not Available	Not Available	2023-02-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, CDCl3, experimental)	mate.erdelyi@kemi.uu.se	Not Available	Not Available	2023-02-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)	mate.erdelyi@kemi.uu.se	Not Available	Not Available	2023-02-18	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpenoid
Diterpene lactone
Oxepane
Fatty acid ester
Fatty acyl
Oxane
2-furanone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Enol ester
Dihydrofuran
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
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	1.14	ChemAxon
pKa (Strongest Acidic)	16.49	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	80.96 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	88.71 m³·mol⁻¹	ChemAxon
Polarizability	35.38 Å³	ChemAxon
Number of Rings	7	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

171347265

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Crotokilwaepoxide B (NP0331520)

MOL for NP0331520 (Crotokilwaepoxide B)

3D MOL for NP0331520 (Crotokilwaepoxide B)

3D SDF for NP0331520 (Crotokilwaepoxide B)

3D-SDF for NP0331520 (Crotokilwaepoxide B)

PDB for NP0331520 (Crotokilwaepoxide B)

3D PDB for NP0331520 (Crotokilwaepoxide B)

SMILES for NP0331520 (Crotokilwaepoxide B)

INCHI for NP0331520 (Crotokilwaepoxide B)

Structure for NP0331520 (Crotokilwaepoxide B)

3D Structure for NP0331520 (Crotokilwaepoxide B)