NP-MRD: Showing NP-Card for Ingenol (NP0052017)

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Record Information

Version

2.0

Created at

2022-04-27 23:12:27 UTC

Updated at

2022-04-27 23:12:27 UTC

NP-MRD ID

NP0052017

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ingenol

Description

(1R,4S,5R,6R,9R,10S,12R,14R)-4,5,6-trihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyltetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]Pentadeca-2,7-dien-15-one 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. Ingenol is found in Euphorbia desmondi, Euphorbia esula, Euphorbia peplus, Euphorbia lathyris, Euphorbia seguieriana and Euphorbia spp.. Based on a literature review very few articles have been published on (1R,4S,5R,6R,9R,10S,12R,14R)-4,5,6-trihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyltetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]Pentadeca-2,7-dien-15-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304282201122D          

 25 28  0  0  1  0            999 V2000
    0.3141   -0.6393    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2778    0.0105    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2352    0.8720    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4675    1.3420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2598    1.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5715    0.2735    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9332   -0.1912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4178   -0.8588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2230   -0.2682    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2363   -1.0931    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5836   -1.6423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7673   -1.4018    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2612   -2.0532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9440   -0.6691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6273   -1.1314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6121   -0.1851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3662    2.1607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0246    2.6579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9530    1.2785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0553   -0.3029    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0093   -1.1284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2054   -1.3239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6436   -1.6560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7516    0.1396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9499    0.4889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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  6  0  0  0
  1  7  1  6  0  0  0
  7  8  2  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
  1 12  1  0  0  0  0
 12 13  1  1  0  0  0
 10 14  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
  4 17  1  0  0  0  0
 17 18  1  0  0  0  0
  3 19  1  6  0  0  0
  2 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
  1 22  1  0  0  0  0
 21 23  1  0  0  0  0
 20 24  1  6  0  0  0
  2 25  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0052017

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C[C@@H]2[C@@H]([C@H]3C=C(CO)[C@@H](O)[C@]4(O)[C@@H](O)C(C)=C[C@]14C3=O)C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O5/c1-9-7-19-10(2)5-13-14(18(13,3)4)12(17(19)24)6-11(8-21)16(23)20(19,25)15(9)22/h6-7,10,12-16,21-23,25H,5,8H2,1-4H3/t10-,12-,13-,14-,15+,16-,19-,20-/m1/s1

> <INCHI_KEY>
VEBVPUXQAPLADL-RGIVKYQRSA-N

> <FORMULA>
C20H28O5

> <MOLECULAR_WEIGHT>
348.439

> <EXACT_MASS>
348.193674002

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
38.043938556632895

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,4S,5R,6R,9R,10S,12R,14R)-4,5,6-trihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyltetracyclo[7.5.1.0^{1,5}.0^{10,12}]pentadeca-2,7-dien-15-one

> <ALOGPS_LOGP>
0.97

> <JCHEM_LOGP>
0.2926680263333336

> <ALOGPS_LOGS>
-2.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.016893548529097

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.004417870063111

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7637285942320906

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
94.0269

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.42e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4S,5R,6R,9R,10S,12R,14R)-4,5,6-trihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyltetracyclo[7.5.1.0^{1,5}.0^{10,12}]pentadeca-2,7-dien-15-one

> <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       0.586  -1.193   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.519   0.020   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.439   1.628   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.873   2.505   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.352   1.977   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.934   0.511   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.742  -0.357   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.647  -1.603   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.150  -0.501   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.174  -2.040   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.956  -3.066   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.432  -2.617   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.488  -3.833   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.496  -1.249   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.771  -2.112   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.743  -0.346   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.684   4.033   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.913   4.961   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -1.779   2.387   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.970  -0.565   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.884  -2.106   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.383  -2.471   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.068  -3.091   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -3.270   0.261   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -1.773   0.913   0.000  0.00  0.00           O+0
CONECT    1    2    7   12   22                                             
CONECT    2    1    3   20   25                                             
CONECT    3    2    4   19                                                  
CONECT    4    3    5   17                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6    1    8                                                  
CONECT    8    7                                                            
CONECT    9    6   10   14                                                  
CONECT   10    9   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11    1   13                                                  
CONECT   13   12                                                            
CONECT   14   10    9   15   16                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17    4   18                                                       
CONECT   18   17                                                            
CONECT   19    3                                                            
CONECT   20    2   21   24                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21    1                                                       
CONECT   23   21                                                            
CONECT   24   20                                                            
CONECT   25    2                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₈O₅

Average Mass

348.4390 Da

Monoisotopic Mass

348.19367 Da

IUPAC Name

(1R,4S,5R,6R,9R,10S,12R,14R)-4,5,6-trihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyltetracyclo[7.5.1.0^{1,5}.0^{10,12}]pentadeca-2,7-dien-15-one

Traditional Name

(1R,4S,5R,6R,9R,10S,12R,14R)-4,5,6-trihydroxy-7-(hydroxymethyl)-3,11,11,14-tetramethyltetracyclo[7.5.1.0^{1,5}.0^{10,12}]pentadeca-2,7-dien-15-one

CAS Registry Number

Not Available

SMILES

C[C@@H]1C[C@@H]2[C@@H]([C@H]3C=C(CO)[C@@H](O)[C@]4(O)[C@@H](O)C(C)=C[C@]14C3=O)C2(C)C

InChI Identifier

InChI=1S/C20H28O5/c1-9-7-19-10(2)5-13-14(18(13,3)4)12(17(19)24)6-11(8-21)16(23)20(19,25)15(9)22/h6-7,10,12-16,21-23,25H,5,8H2,1-4H3/t10-,12-,13-,14-,15+,16-,19-,20-/m1/s1

InChI Key

VEBVPUXQAPLADL-RGIVKYQRSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Euphorbia desmondi	LOTUS Database	35616633
Euphorbia esula	Plant	KNApSAcK
Euphorbia Euphorbia peplus	LOTUS Database	35616633
Euphorbia lathyris	LOTUS Database	35616633
Euphorbia seguieriana	Plant	KNApSAcK
Euphorbia spp.	Plant	KNApSAcK

Chemical Taxonomy

Description

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

Ingenane diterpenoid
Tertiary alcohol
Secondary alcohol
Ketone
Polyol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	0.97	ALOGPS
logP	0.29	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	12	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	94.03 m³·mol⁻¹	ChemAxon
Polarizability	38.04 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	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

162913159

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Ingenol (NP0052017)

MOL for NP0052017 (Ingenol)

3D MOL for NP0052017 (Ingenol)

3D SDF for NP0052017 (Ingenol)

3D-SDF for NP0052017 (Ingenol)

PDB for NP0052017 (Ingenol)

3D PDB for NP0052017 (Ingenol)

SMILES for NP0052017 (Ingenol)

INCHI for NP0052017 (Ingenol)

Structure for NP0052017 (Ingenol)

3D Structure for NP0052017 (Ingenol)