NP-MRD: Showing NP-Card for Euphylonane C (NP0332079)

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Record Information

Version

2.0

Created at

2023-11-02 00:01:23 UTC

Updated at

2024-09-03 04:17:53 UTC

NP-MRD ID

NP0332079

Natural Product DOI

https://doi.org/10.57994/1207

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Euphylonane C

Description

Euphylonane C belongs to the class of organic compounds known as tigliane and ingenane diterpenoids. These are diterpenoids containing the tigliane or ingenane carbon skeleton. The tigliane skeleton is a tetracyclic ring that consists of the 4/7/6/3 ring junction. It is derived from casbane by 6,10- and 5,14-cyclizations and is a framework of phorbol. The ingenane skeleton is derived by rearrangement of tigliane. Based on a literature review very few articles have been published on Euphylonane C.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 11022300012D          

 27 31  0  0  1  0            999 V2000
    6.1583    0.1334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8344    0.8921    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5254    1.3429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2613    0.9698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0310    0.7049    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2706    1.4944    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8728    2.0582    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7067    2.0966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9032    1.9094    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3394    2.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2181   -0.0985    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2275    0.5178    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4402    0.2710    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1082   -0.2986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3956   -0.7143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4609   -1.5367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6263   -0.4163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3795    0.3709    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8032   -0.2194    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8412    1.0546    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3336    1.7050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5582    1.4232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8745    1.8849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5866    0.5987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9363    0.0911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6636    1.1200    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1958    1.7995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  6  0  0  0
  3  4  1  0  0  0  0
  5  2  1  0  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  9  8  1  0  0  0  0
  9 10  1  6  0  0  0
  5 11  1  6  0  0  0
  5 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 18 17  1  0  0  0  0
 18 19  1  1  0  0  0
 20 18  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 18 24  1  0  0  0  0
 24 25  2  0  0  0  0
 26 20  1  0  0  0  0
 12 26  1  0  0  0  0
 26  9  1  0  0  0  0
 26 27  1  6  0  0  0
 20 27  1  6  0  0  0
M  END


  Mrv2104 11022300012D          

 27 31  0  0  1  0            999 V2000
    6.1583    0.1334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8344    0.8921    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5254    1.3429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2613    0.9698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0310    0.7049    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2706    1.4944    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8728    2.0582    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7067    2.0966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9032    1.9094    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3394    2.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2181   -0.0985    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2275    0.5178    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4402    0.2710    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1082   -0.2986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3956   -0.7143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4609   -1.5367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6263   -0.4163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3795    0.3709    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8032   -0.2194    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8412    1.0546    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3336    1.7050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5582    1.4232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8745    1.8849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5866    0.5987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9363    0.0911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6636    1.1200    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1958    1.7995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  6  0  0  0
  3  4  1  0  0  0  0
  5  2  1  0  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  9  8  1  0  0  0  0
  9 10  1  6  0  0  0
  5 11  1  6  0  0  0
  5 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 18 17  1  0  0  0  0
 18 19  1  1  0  0  0
 20 18  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 18 24  1  0  0  0  0
 24 25  2  0  0  0  0
 26 20  1  0  0  0  0
 12 26  1  0  0  0  0
 26  9  1  0  0  0  0
 26 27  1  6  0  0  0
 20 27  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0332079

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12C[C@@H](C)[C@]34O[C@]33C=C(C)C(=O)[C@@]3([H])CC(C)=C[C@@]4([H])[C@]1([H])[C@@]2(C)CO

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O3/c1-10-5-14-16-13(18(16,4)9-21)7-12(3)20(14)19(23-20)8-11(2)17(22)15(19)6-10/h5,8,12-16,21H,6-7,9H2,1-4H3/t12-,13-,14+,15-,16-,18+,19+,20-/m1/s1

> <INCHI_KEY>
ITVNNFOGQJMLIN-WWLBDMNDSA-N

> <FORMULA>
C20H26O3

> <MOLECULAR_WEIGHT>
314.425

> <EXACT_MASS>
314.188194697

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
36.28167116695171

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,3S,7S,11S,12R,13S,14R,16R)-13-(hydroxymethyl)-5,9,13,16-tetramethyl-2-oxapentacyclo[9.5.0.0^{1,3}.0^{3,7}.0^{12,14}]hexadeca-4,9-dien-6-one

> <JCHEM_LOGP>
2.587758484000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.58814863044568

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.110241642541236

> <JCHEM_PKA_STRONGEST_BASIC>
-1.4377655837382974

> <JCHEM_POLAR_SURFACE_AREA>
49.83

> <JCHEM_REFRACTIVITY>
89.24139999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3S,7S,11S,12R,13S,14R,16R)-13-(hydroxymethyl)-5,9,13,16-tetramethyl-2-oxapentacyclo[9.5.0.0^{1,3}.0^{3,7}.0^{12,14}]hexadeca-4,9-dien-6-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-NOV-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-NOV-23         0                                  
HETATM    1  C   UNK     0      11.496   0.249   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.891   1.665   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.181   2.507   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      13.554   1.810   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       9.391   1.316   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.838   2.790   0.000  0.00  0.00           C+0
HETATM    7  H   UNK     0      10.963   3.842   0.000  0.00  0.00           H+0
HETATM    8  C   UNK     0       8.786   3.914   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.286   3.564   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.234   4.688   0.000  0.00  0.00           C+0
HETATM   11  H   UNK     0       9.741  -0.184   0.000  0.00  0.00           H+0
HETATM   12  C   UNK     0       7.891   0.966   0.000  0.00  0.00           C+0
HETATM   13  H   UNK     0       6.422   0.506   0.000  0.00  0.00           H+0
HETATM   14  C   UNK     0       7.669  -0.557   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.338  -1.333   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.460  -2.868   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.902  -0.777   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.442   0.692   0.000  0.00  0.00           C+0
HETATM   19  H   UNK     0       3.366  -0.410   0.000  0.00  0.00           H+0
HETATM   20  C   UNK     0       5.304   1.969   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.356   3.183   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.909   2.657   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.632   3.518   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.962   1.118   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.748   0.170   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.839   2.091   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.966   3.359   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    5    6                                             
CONECT    3    2    4                                                       
CONECT    4    3                                                            
CONECT    5    2    6   11   12                                             
CONECT    6    5    2    7    8                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   26                                                  
CONECT   10    9                                                            
CONECT   11    5                                                            
CONECT   12    5   13   14   26                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20   24                                             
CONECT   19   18                                                            
CONECT   20   18   21   26   27                                             
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   18   25                                                  
CONECT   25   24                                                            
CONECT   26   20   12    9   27                                             
CONECT   27   26   20                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₆O₃

Average Mass

314.4250 Da

Monoisotopic Mass

314.18819 Da

IUPAC Name

(1R,3S,7S,11S,12R,13S,14R,16R)-13-(hydroxymethyl)-5,9,13,16-tetramethyl-2-oxapentacyclo[9.5.0.0^{1,3}.0^{3,7}.0^{12,14}]hexadeca-4,9-dien-6-one

Traditional Name

(1R,3S,7S,11S,12R,13S,14R,16R)-13-(hydroxymethyl)-5,9,13,16-tetramethyl-2-oxapentacyclo[9.5.0.0^{1,3}.0^{3,7}.0^{12,14}]hexadeca-4,9-dien-6-one

CAS Registry Number

Not Available

SMILES

[H][C@@]12C[C@@H](C)[C@]34O[C@]33C=C(C)C(=O)[C@@]3([H])CC(C)=C[C@@]4([H])[C@]1([H])[C@@]2(C)CO

InChI Identifier

InChI=1S/C20H26O3/c1-10-5-14-16-13(18(16,4)9-21)7-12(3)20(14)19(23-20)8-11(2)17(22)15(19)6-10/h5,8,12-16,21H,6-7,9H2,1-4H3/t12-,13-,14+,15-,16-,18+,19+,20-/m1/s1

InChI Key

ITVNNFOGQJMLIN-WWLBDMNDSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View

Predicted Spectra

Not Available

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 tigliane and ingenane diterpenoids. These are diterpenoids containing the tigliane or ingenane carbon skeleton. The tigliane skeleton is a tetracyclic ring that consists of the 4/7/6/3 ring junction. It is derived from casbane by 6,10- and 5,14-cyclizations and is a framework of phorbol. The ingenane skeleton is derived by rearrangement of tigliane.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Tigliane and ingenane diterpenoids

Alternative Parents

Substituents

Tigliane diterpenoid
Daphnane diterpenoid
Rhamnofolane diterpenoid
Long chain fatty alcohol
Fatty alcohol
Fatty acyl
Alpha-branched alpha,beta-unsaturated-ketone
Alpha,beta-unsaturated ketone
Enone
Acryloyl-group
Ketone
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Alcohol
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	2.59	ChemAxon
pKa (Strongest Acidic)	18.11	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.83 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	89.24 m³·mol⁻¹	ChemAxon
Polarizability	36.28 Å³	ChemAxon
Number of Rings	5	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Euphylonane C (NP0332079)

MOL for NP0332079 (Euphylonane C)

3D MOL for NP0332079 (Euphylonane C)

3D SDF for NP0332079 (Euphylonane C)

3D-SDF for NP0332079 (Euphylonane C)

PDB for NP0332079 (Euphylonane C)

3D PDB for NP0332079 (Euphylonane C)

SMILES for NP0332079 (Euphylonane C)

INCHI for NP0332079 (Euphylonane C)

Structure for NP0332079 (Euphylonane C)

3D Structure for NP0332079 (Euphylonane C)