NP-MRD: Showing NP-Card for verrucosan-2b-ol (NP0286888)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-09 15:41:31 UTC

Updated at

2022-09-09 15:41:31 UTC

NP-MRD ID

NP0286888

Secondary Accession Numbers

None

Natural Product Identification

Common Name

verrucosan-2b-ol

Description

Verrucosan-2b-ol belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Thus, verrucosan-2b-ol is considered to be an isoprenoid lipid molecule. verrucosan-2b-ol is found in Chloroflexus aurantiacus and Scapania bolanderi. Verrucosan-2b-ol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 55 58  0  0  0  0  0  0  0  0999 V2000
   -3.1933   -0.1812   -1.5987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9329    0.1418   -0.1575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7999    1.6222    0.0511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9110   -0.6706    0.5310 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4321   -2.1277    0.4631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2394   -2.8466    1.0432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0647   -2.1268    0.3579 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2833   -3.0143   -0.8408 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0489   -2.1558    1.3295 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9861   -1.0178    1.2962 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3094    0.3330    1.1935 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4553    0.5186    2.4571 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3549    1.3662    1.1810 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4553    2.2728    0.0184 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3169    3.0934   -0.4716 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7838    1.9508   -1.2175 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5710    2.2436   -2.5062 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2030    0.5857   -1.2092 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4449    0.4225   -2.3670 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3608    0.3414    0.0388 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5616   -0.7924   -0.0862 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9316    0.6046   -1.9462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6261   -1.1635   -1.7714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2778    0.0450   -2.1727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9250   -0.1118    0.3590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3680    1.8349    1.0282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2538    2.0756   -0.8154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8116    2.1272    0.0704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9135   -0.4228    1.5948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5948   -2.4270   -0.5711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3009   -2.2072    1.1270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2304   -2.6704    2.1336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2276   -3.9212    0.8507 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9422   -3.8311   -0.4811 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7944   -2.4110   -1.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6798   -3.4087   -1.2461 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6925   -2.3156    2.3912 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6573   -3.0911    1.1385 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5712   -1.0039    2.2370 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6515   -1.1214    0.4033 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1030    0.9926    3.2535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3474    1.2619    2.2745 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1128   -0.4257    2.8769 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2779    2.0424    2.0911 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3883    0.9204    1.3321 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4465    2.8168   -0.0335 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5350    4.1187   -0.8983 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4582    3.1484    0.2127 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2853    1.5754   -3.3206 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4029    3.3198   -2.7912 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6608    2.1667   -2.2958 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0349   -0.1479   -1.2783 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0559    1.3084   -2.5792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2560    1.2542    0.1439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7649   -0.8913   -1.2010 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  6
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  1
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  6
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21  4  1  0
 21  7  1  0
 20 11  1  0
 16 14  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  1
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  8 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 10 40  1  0
 12 41  1  0
 12 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  6
 15 47  1  0
 15 48  1  0
 17 49  1  0
 17 50  1  0
 17 51  1  0
 18 52  1  6
 19 53  1  0
 20 54  1  1
 21 55  1  6
M  END


  Mrv1533004241517482D          

 21 24  0  0  0  0            999 V2000
    2.7690   -2.8909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -2.2423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0955   -2.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9721   -1.4765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1722   -1.2745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1171   -0.4513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8830   -0.1446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2913    0.4303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1675    0.6298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9804    0.7706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5088    0.1371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7933    0.9115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3217    0.2779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8501   -0.3557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3785   -0.9893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5656   -1.1301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7064   -1.9430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7527   -1.2709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4682   -2.0453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2243   -0.6373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4114   -0.7781    0.0000 C   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
  2  4  1  0  0  0  0
  4  5  1  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
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  0  0  0  0
  4 21  1  0  0  0  0
  7 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0286888

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1CCC2(C)CCC3(C)CC4CC4(C)C(O)C3C12

> <INCHI_IDENTIFIER>
InChI=1S/C20H34O/c1-12(2)14-6-7-18(3)8-9-19(4)10-13-11-20(13,5)17(21)16(19)15(14)18/h12-17,21H,6-11H2,1-5H3

> <INCHI_KEY>
QQHDEGUZXBOWLH-UHFFFAOYSA-N

> <FORMULA>
C20H34O

> <MOLECULAR_WEIGHT>
290.491

> <EXACT_MASS>
290.260965715

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
35.81457089000769

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,9,13-trimethyl-3-(propan-2-yl)tetracyclo[7.5.0.0²,⁶.0¹¹,¹³]tetradecan-14-ol

> <ALOGPS_LOGP>
3.99

> <JCHEM_LOGP>
4.653377070666665

> <ALOGPS_LOGS>
-5.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-0.2301552931653622

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
87.255

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.40e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
verrucosan-2b-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       5.169  -5.396   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.121  -4.186   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.645  -4.405   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.548  -2.756   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.055  -2.379   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.952  -0.842   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.382  -0.270   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.277   0.803   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.913   1.176   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.430   1.439   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.416   0.256   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.947   1.701   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.934   0.519   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.920  -0.664   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.906  -1.847   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.389  -2.109   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.652  -3.627   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.872  -2.372   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.341  -3.818   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       7.885  -1.190   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.368  -1.453   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   21                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   21                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   20                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14   16                                                       
CONECT   16   15   14   17   18                                             
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   11   21                                                  
CONECT   21   20    4    7                                                  
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

View in JSmol

Synonyms

Value	Source
Verrucosan-2beta-ol	MeSH
Verrucosan-2-ol	MeSH

Chemical Formula

C₂₀H₃₄O

Average Mass

290.4910 Da

Monoisotopic Mass

290.26097 Da

IUPAC Name

6,9,13-trimethyl-3-(propan-2-yl)tetracyclo[7.5.0.0²,⁶.0¹¹,¹³]tetradecan-14-ol

Traditional Name

verrucosan-2b-ol

CAS Registry Number

Not Available

SMILES

CC(C)C1CCC2(C)CCC3(C)CC4CC4(C)C(O)C3C12

InChI Identifier

InChI=1S/C20H34O/c1-12(2)14-6-7-18(3)8-9-19(4)10-13-11-20(13,5)17(21)16(19)15(14)18/h12-17,21H,6-11H2,1-5H3

InChI Key

QQHDEGUZXBOWLH-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Chloroflexus aurantiacus	LOTUS Database	35616633
Scapania bolanderi	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Verrucosane, neoverrucosane, homoverrucosane, or homoneoverrucosane diterpenoid
Diterpenoid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Verrucosane and modified verrucosane diterpenoids (LMPR0104280002 )

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	3.99	ALOGPS
logP	4.65	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Basic)	-0.23	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	1	ChemAxon
Refractivity	87.26 m³·mol⁻¹	ChemAxon
Polarizability	35.81 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

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

194329

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for verrucosan-2b-ol (NP0286888)

MOL for NP0286888 (verrucosan-2b-ol)

3D MOL for NP0286888 (verrucosan-2b-ol)

3D SDF for NP0286888 (verrucosan-2b-ol)

3D-SDF for NP0286888 (verrucosan-2b-ol)

PDB for NP0286888 (verrucosan-2b-ol)

3D PDB for NP0286888 (verrucosan-2b-ol)

SMILES for NP0286888 (verrucosan-2b-ol)

INCHI for NP0286888 (verrucosan-2b-ol)

Structure for NP0286888 (verrucosan-2b-ol)

3D Structure for NP0286888 (verrucosan-2b-ol)