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Showing NP-Card for (+)-geosmin (NP0146941)

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Record Information
Version2.0
Created at2022-09-02 02:26:35 UTC
Updated at2022-09-02 02:26:35 UTC
NP-MRD IDNP0146941
Secondary Accession NumbersNone
Natural Product Identification
Common Name(+)-geosmin
Description(+)-Geosmin belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ). Thus, (+)-geosmin is considered to be an isoprenoid. (+)-geosmin is found in Streptomyces avermitilis. Based on a literature review very few articles have been published on (+)-geosmin.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0146941 ((+)-geosmin)


  Mrv1652309022204262D          

 13 14  0  0  1  0            999 V2000
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  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
  2 12  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  6  0  0  0
M  END
Download

3D MOL for NP0146941 ((+)-geosmin)

     RDKit          3D

 35 36  0  0  0  0  0  0  0  0999 V2000
   -1.6998   -2.2573    0.2309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3402   -0.7709    0.3601 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3830    0.0150   -0.3248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0090    1.2758   -0.9736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5503    1.5262   -1.1878 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3269    0.9486   -0.1128 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0647    1.6261    1.1848 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7509    1.2587   -0.4465 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5775    0.0353   -0.7408 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4313   -1.0536    0.2639 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0453   -1.1671    0.8464 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0597   -0.5384   -0.0809 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1950   -1.0028   -1.3892 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3998   -2.5396    1.0341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2791   -2.3782   -0.7293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8278   -2.8979    0.1808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3598   -0.5888    1.4763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2004    0.2216    0.4311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9157   -0.6312   -1.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4850    1.3962   -1.9938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4089    2.1610   -0.4029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3266    2.6127   -1.2428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2023    1.1046   -2.1650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1269    1.4459    1.3924 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0281    2.7301    0.9877 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6167    1.4060    2.0127 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8676    1.9467   -1.3096 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2354    1.7900    0.4204 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6547    0.3740   -0.7049 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4429   -0.3345   -1.7881 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6446   -2.0254   -0.2688 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1660   -1.0104    1.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0538   -0.5950    1.8020 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8600   -2.2093    1.0967 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6228   -1.8743   -1.4546 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  1
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  6
 12  2  1  0
 12  6  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  1
  3 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  0
  5 23  1  0
  7 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 13 35  1  0
M  END
Download

3D SDF for NP0146941 ((+)-geosmin)


  Mrv1652309022204262D          

 13 14  0  0  1  0            999 V2000
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  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
  2 12  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0146941

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CCC[C@]2(C)CCCC[C@@]12O

> <INCHI_IDENTIFIER>
InChI=1S/C12H22O/c1-10-6-5-8-11(2)7-3-4-9-12(10,11)13/h10,13H,3-9H2,1-2H3/t10-,11+,12-/m1/s1

> <INCHI_KEY>
JLPUXFOGCDVKGO-GRYCIOLGSA-N

> <FORMULA>
C12H22O

> <MOLECULAR_WEIGHT>
182.307

> <EXACT_MASS>
182.167065328

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
22.187314303854

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4R,4aR,8aS)-4,8a-dimethyl-decahydronaphthalen-4a-ol

> <ALOGPS_LOGP>
3.66

> <JCHEM_LOGP>
3.172581791333333

> <ALOGPS_LOGS>
-3.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-0.004709431003981135

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
54.577799999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.12e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(+)-geosmin

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0146941 ((+)-geosmin)

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PDB for NP0146941 ((+)-geosmin)
HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.001  -3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8   12                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    2    6   13                                             
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

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3D PDB for NP0146941 ((+)-geosmin)
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SMILES for NP0146941 ((+)-geosmin)
C[C@@H]1CCC[C@]2(C)CCCC[C@@]12O
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INCHI for NP0146941 ((+)-geosmin)
InChI=1S/C12H22O/c1-10-6-5-8-11(2)7-3-4-9-12(10,11)13/h10,13H,3-9H2,1-2H3/t10-,11+,12-/m1/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC12H22O
Average Mass182.3070 Da
Monoisotopic Mass182.16707 Da
IUPAC Name(4R,4aR,8aS)-4,8a-dimethyl-decahydronaphthalen-4a-ol
Traditional Name(+)-geosmin
CAS Registry NumberNot Available
SMILES
C[C@@H]1CCC[C@]2(C)CCCC[C@@]12O
InChI Identifier
InChI=1S/C12H22O/c1-10-6-5-8-11(2)7-3-4-9-12(10,11)13/h10,13H,3-9H2,1-2H3/t10-,11+,12-/m1/s1
InChI KeyJLPUXFOGCDVKGO-GRYCIOLGSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Streptomyces avermitilisLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassAlcohols and polyols  
Direct ParentTertiary alcohols  
Alternative Parents
Substituents
  • Tertiary alcohol
    • 

  • Cyclic alcohol
    • 

  • Hydrocarbon derivative
    • 

  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
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
logP3.66ALOGPS
logP3.17ChemAxon
logS-3.6ALOGPS
pKa (Strongest Basic)-0.0047ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity54.58 m³·mol⁻¹ChemAxon
Polarizability22.19 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID21169652  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound15559490  
PDB IDNot Available
ChEBI ID46705  
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]