NP-MRD: Showing NP-Card for ent-Kauran-16-beta-ol (NP0046731)

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Record Information

Version

2.0

Created at

2022-03-17 20:11:58 UTC

Updated at

2022-03-17 20:11:58 UTC

NP-MRD ID

NP0046731

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ent-Kauran-16-beta-ol

Description

Ent-Kauran-16-beta-ol 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-Kauran-16-beta-ol is found in Amentotaxus formosana, Annona cherimola, Araucaria columnaris, Araucaria scopulorum, Baccharis minutiflora, Cryptomeria japonica, Espeletiopsis guacharaca, Frullanoides densifolia, Helianthus occidentalis, Iostephane heterophylla, Iostephane madrensis, Niebla ceruchis, Oyedaea verbesinoides, Prangos pabularia , Saelania glaucescens, Steiractinia sodiroi, Taiwania cryptomerioides, Tripterygium doianum, Xylopia frutescens and Xylopia sericea . Ent-Kauran-16-beta-ol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241212502D          

 23 26  0  0  1  0            999 V2000
    0.9459   -0.8176    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6599   -1.2401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3801   -0.8377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4339    0.0030    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7262    0.6533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1346    1.2699    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4032    1.7289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6460    1.3231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6668    0.4452    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9459    0.0060    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9362    0.8297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2326    0.4178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4807    0.0060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4807   -0.8176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2326   -1.2294    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1542   -1.9569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6192   -1.9569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7307    0.6473    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2641    0.2578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3202   -0.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1518    1.3769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9459   -1.6600    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6668   -0.3972    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
  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 21  1  1  0  0  0
  1 22  1  1  0  0  0
  9 23  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0046731

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H34O/c1-17(2)9-5-10-18(3)15(17)8-11-20-12-14(6-7-16(18)20)19(4,21)13-20/h14-16,21H,5-13H2,1-4H3/t14-,15-,16+,18-,19-,20+/m1/s1

> <INCHI_KEY>
FZSRMADKTOBCNT-HFJXXIIPSA-N

> <FORMULA>
C20H34O

> <MOLECULAR_WEIGHT>
290.4834

> <EXACT_MASS>
290.26096571

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
35.874369840056865

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
4.96

> <JCHEM_LOGP>
4.648576751333334

> <ALOGPS_LOGS>
-6.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.845155663627263

> <JCHEM_PKA_STRONGEST_BASIC>
-0.6795289127294345

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
87.55099999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.96e-04 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$

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       1.766  -1.526   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.098  -2.315   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.443  -1.564   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.543   0.006   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.089   1.219   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.851   2.370   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.486   3.227   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.073   2.470   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.111   0.831   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.766   0.011   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.748   1.549   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.434   0.780   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.897   0.011   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.897  -1.526   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.434  -2.295   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.288  -3.653   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.156  -3.653   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.964   1.208   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       7.960   0.481   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.198  -0.220   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.750   2.570   0.000  0.00  0.00           C+0
HETATM   22  H   UNK     0       1.766  -3.099   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0       3.111  -0.741   0.000  0.00  0.00           H+0
CONECT    1    2   10   15   22                                             
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   23                                             
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                                                            
CONECT   18    6   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18    4                                                       
CONECT   21   18                                                            
CONECT   22    1                                                            
CONECT   23    9                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

View in JSmol

Synonyms

Value	Source
ent-Kauran-16-b-ol	Generator
ent-Kauran-16-β-ol	Generator

Chemical Formula

C₂₀H₃₄O

Average Mass

290.4834 Da

Monoisotopic Mass

290.26097 Da

IUPAC Name

(1S,4R,9R,10R,13R,14R)-5,5,9,14-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-ol

Traditional Name

(1S,4R,9R,10R,13R,14R)-5,5,9,14-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-ol

CAS Registry Number

58-55-9

SMILES

[H][C@@]12CC[C@@H]3C[C@]1(C[C@@]3(C)O)CC[C@]1([H])C(C)(C)CCC[C@@]21C

InChI Identifier

InChI=1S/C20H34O/c1-17(2)9-5-10-18(3)15(17)8-11-20-12-14(6-7-16(18)20)19(4,21)13-20/h14-16,21H,5-13H2,1-4H3/t14-,15-,16+,18-,19-,20+/m1/s1

InChI Key

FZSRMADKTOBCNT-HFJXXIIPSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Amentotaxus formosana	LOTUS Database	35616633
Annona cherimola	LOTUS Database	35616633
Araucaria columnaris	Plant	KNApSAcK
Araucaria scopulorum	Plant	KNApSAcK
Baccharis minutiflora	LOTUS Database	35616633
Cryptomeria japonica	LOTUS Database	35616633
Espeletiopsis guacharaca	LOTUS Database	35616633
Frullanoides densifolia	LOTUS Database	35616633
Helianthus annuus L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Helianthus occidentalis	LOTUS Database	35616633
Iostephane heterophylla	LOTUS Database	35616633
Iostephane madrensis	LOTUS Database	35616633
Niebla ceruchis	LOTUS Database	35616633
Oyedaea verbesinoides	LOTUS Database	35616633
Prangos pabularia	Plant	KNApSAcK
Saelania glaucescens	LOTUS Database	35616633
Steiractinia sodiroi	LOTUS Database	35616633
Taiwania cryptomerioides	Plant	KNApSAcK
Tripterygium doianum	LOTUS Database	35616633
Xylopia frutescens	LOTUS Database	35616633
Xylopia sericea	Plant	KNApSAcK

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Kaurane diterpenoids

Alternative Parents

Substituents

Kaurane diterpenoid
Tertiary alcohol
Cyclic alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
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	4.96	ALOGPS
logP	4.65	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Acidic)	19.85	ChemAxon
pKa (Strongest Basic)	-0.68	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	87.55 m³·mol⁻¹	ChemAxon
Polarizability	35.87 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB005671

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

21593607

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for ent-Kauran-16-beta-ol (NP0046731)

MOL for NP0046731 (ent-Kauran-16-beta-ol)

3D MOL for NP0046731 (ent-Kauran-16-beta-ol)

3D SDF for NP0046731 (ent-Kauran-16-beta-ol)

3D-SDF for NP0046731 (ent-Kauran-16-beta-ol)

PDB for NP0046731 (ent-Kauran-16-beta-ol)

3D PDB for NP0046731 (ent-Kauran-16-beta-ol)

SMILES for NP0046731 (ent-Kauran-16-beta-ol)

INCHI for NP0046731 (ent-Kauran-16-beta-ol)

Structure for NP0046731 (ent-Kauran-16-beta-ol)

3D Structure for NP0046731 (ent-Kauran-16-beta-ol)