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Showing NP-Card for ent-16b-Kauran-16,19-diol (NP0046730)

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Record Information
Version2.0
Created at2022-03-17 20:11:57 UTC
Updated at2022-03-17 20:11:57 UTC
NP-MRD IDNP0046730
Secondary Accession NumbersNone
Natural Product Identification
Common Nameent-16b-Kauran-16,19-diol
DescriptionEnt-16b-Kauran-16,19-diol belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. ent-16b-Kauran-16,19-diol is found in Sideritis canariensis, Sideritis discolor and Tripterygium wilfordii . Ent-16b-Kauran-16,19-diol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0046730 (ent-16b-Kauran-16,19-diol)


  Mrv0541 02241212502D          

 24 27  0  0  1  0            999 V2000
    0.9471   -0.8187    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6621   -1.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3831   -0.8389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4370    0.0030    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7297    0.6541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1386    1.2715    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4062    1.7311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6482    1.3248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6688    0.4457    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9471    0.0060    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9373    0.8307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2327    0.4183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4814    0.0060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4814   -0.8187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2327   -1.2311    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1544   -1.9595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6201   -1.9595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7354    0.6481    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2442    0.2588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3244   -0.1178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1831   -2.6588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2174    1.2949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9471   -1.6546    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6688   -0.3902    0.0000 H   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  1  6  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
  1 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  1 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  6  0  0  0
 17 21  1  0  0  0  0
  6 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
  4 20  1  0  0  0  0
 18 22  1  1  0  0  0
  1 23  1  1  0  0  0
  9 24  1  1  0  0  0
M  END
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3D MOL for NP0046730 (ent-16b-Kauran-16,19-diol)

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3D SDF for NP0046730 (ent-16b-Kauran-16,19-diol)

  Mrv0541 02241212502D          

 24 27  0  0  1  0            999 V2000
    0.9471   -0.8187    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6621   -1.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3831   -0.8389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4370    0.0030    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7297    0.6541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1386    1.2715    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4062    1.7311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6482    1.3248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6688    0.4457    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9471    0.0060    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9373    0.8307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2327    0.4183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4814    0.0060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4814   -0.8187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2327   -1.2311    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1544   -1.9595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6201   -1.9595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7354    0.6481    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2442    0.2588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3244   -0.1178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1831   -2.6588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2174    1.2949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9471   -1.6546    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6688   -0.3902    0.0000 H   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  1  6  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
  1 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  1 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  6  0  0  0
 17 21  1  0  0  0  0
  6 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
  4 20  1  0  0  0  0
 18 22  1  1  0  0  0
  1 23  1  1  0  0  0
  9 24  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0046730

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC[C@@H]3C[C@]1(C[C@@]3(C)O)CC[C@]1([H])[C@](C)(CO)CCC[C@@]21C

> <INCHI_IDENTIFIER>
InChI=1S/C20H34O2/c1-17(13-21)8-4-9-18(2)15(17)7-10-20-11-14(5-6-16(18)20)19(3,22)12-20/h14-16,21-22H,4-13H2,1-3H3/t14-,15-,16+,17+,18-,19-,20+/m1/s1

> <INCHI_KEY>
XZESVXVYTBMYCR-WVMNWVHYSA-N

> <FORMULA>
C20H34O2

> <MOLECULAR_WEIGHT>
306.4828

> <EXACT_MASS>
306.255880332

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
36.87565703755948

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4S,5R,9S,10R,13R,14R)-5-(hydroxymethyl)-5,9,14-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-ol

> <ALOGPS_LOGP>
3.72

> <JCHEM_LOGP>
3.3678055946666676

> <ALOGPS_LOGS>
-4.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.84515566362301

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.592349955083975

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5712501125163608

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
89.32569999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.44e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4S,5R,9S,10R,13R,14R)-5-(hydroxymethyl)-5,9,14-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-ol

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0046730 (ent-16b-Kauran-16,19-diol)
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PDB for NP0046730 (ent-16b-Kauran-16,19-diol)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       1.768  -1.528   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.103  -2.318   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.448  -1.566   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.549   0.006   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.095   1.221   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.859   2.373   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.492   3.231   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.077   2.473   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.115   0.832   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.768   0.011   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.750   1.551   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.434   0.781   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.899   0.011   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.899  -1.528   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.434  -2.298   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.288  -3.658   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.158  -3.658   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.973   1.210   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       7.923   0.483   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.206  -0.220   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.342  -4.963   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       7.872   2.417   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0       1.768  -3.089   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0       3.115  -0.728   0.000  0.00  0.00           H+0
CONECT    1    2   10   15   23                                             
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9   20                                             
CONECT    5    4    6                                                       
CONECT    6    5    7   18                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    4   10   24                                             
CONECT   10    9    1   11   12                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    1   16   17                                             
CONECT   16   15                                                            
CONECT   17   15   21                                                       
CONECT   18    6   19   20   22                                             
CONECT   19   18                                                            
CONECT   20   18    4                                                       
CONECT   21   17                                                            
CONECT   22   18                                                            
CONECT   23    1                                                            
CONECT   24    9                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

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3D PDB for NP0046730 (ent-16b-Kauran-16,19-diol)
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SMILES for NP0046730 (ent-16b-Kauran-16,19-diol)
[H][C@@]12CC[C@@H]3C[C@]1(C[C@@]3(C)O)CC[C@]1([H])[C@](C)(CO)CCC[C@@]21C
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INCHI for NP0046730 (ent-16b-Kauran-16,19-diol)
InChI=1S/C20H34O2/c1-17(13-21)8-4-9-18(2)15(17)7-10-20-11-14(5-6-16(18)20)19(3,22)12-20/h14-16,21-22H,4-13H2,1-3H3/t14-,15-,16+,17+,18-,19-,20+/m1/s1
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SynonymsNot Available
Chemical FormulaC20H34O2
Average Mass306.4828 Da
Monoisotopic Mass306.25588 Da
IUPAC Name(1S,4S,5R,9S,10R,13R,14R)-5-(hydroxymethyl)-5,9,14-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-ol
Traditional Name(1S,4S,5R,9S,10R,13R,14R)-5-(hydroxymethyl)-5,9,14-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-ol
CAS Registry Number68-22-4
SMILES
[H][C@@]12CC[C@@H]3C[C@]1(C[C@@]3(C)O)CC[C@]1([H])[C@](C)(CO)CCC[C@@]21C
InChI Identifier
InChI=1S/C20H34O2/c1-17(13-21)8-4-9-18(2)15(17)7-10-20-11-14(5-6-16(18)20)19(3,22)12-20/h14-16,21-22H,4-13H2,1-3H3/t14-,15-,16+,17+,18-,19-,20+/m1/s1
InChI KeyXZESVXVYTBMYCR-WVMNWVHYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Helianthus annuus L.FooDB
Sideritis canariensisPlant
Sideritis discolorPlant
Tripterygium wilfordiiPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassDiterpenoids  
Direct ParentKaurane diterpenoids  
Alternative Parents
Substituents
  • Kaurane diterpenoid
    • 

  • Tertiary alcohol
    • 

  • Cyclic alcohol
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Primary alcohol
    • 

  • Organooxygen compound
    • 

  • Alcohol
    • 

  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.72ALOGPS
logP3.37ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)18.59ChemAxon
pKa (Strongest Basic)-0.57ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity89.33 m³·mol⁻¹ChemAxon
Polarizability36.88 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB005670  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52916190  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available