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

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Record Information

Version

1.0

Created at

2022-09-02 02:26:35 UTC

Updated at

2022-09-02 02:26:35 UTC

NP-MRD ID

NP0146941

Secondary Accession Numbers

None

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. It was first documented in 2022 (PMID: 36006164). Based on a literature review a significant number of articles have been published on (+)-geosmin (PMID: 35736037) (PMID: 35954649) (PMID: 35931264) (PMID: 35810865).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     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

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

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₂H₂₂O

Average Mass

182.3070 Da

Monoisotopic Mass

182.16707 Da

IUPAC Name

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

Traditional Name

(+)-geosmin

CAS Registry Number

Not 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 Key

JLPUXFOGCDVKGO-GRYCIOLGSA-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
Streptomyces avermitilis	LOTUS Database	35616633

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 ).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Tertiary alcohols

Alternative Parents

Substituents

Tertiary alcohol
Cyclic alcohol
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

geosmin (CHEBI:46705 )
Germacrane sesquiterpenoids (LMPR0103090008 )

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	3.66	ALOGPS
logP	3.17	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Basic)	-0.0047	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	54.58 m³·mol⁻¹	ChemAxon
Polarizability	22.19 Å³	ChemAxon
Number of Rings	2	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

21169652

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15559490

PDB ID

Not Available

ChEBI ID

46705

Good Scents ID

Not Available

References

General References

Ezediokpu MN, Krause K, Kunert M, Hoffmeister D, Boland W, Kothe E: Ectomycorrhizal Influence on the Dynamics of Sesquiterpene Release by Tricholoma vaccinum. J Fungi (Basel). 2022 May 24;8(6):555. doi: 10.3390/jof8060555. [PubMed:35736037 ]
Luo F, Chen H, Wu X, Liu L, Chen Y, Wang Z: Insights into the Seasonal Olfactory Mechanism of Geosmin in Raw Water of Huangpu River. Toxics. 2022 Aug 19;10(8):485. doi: 10.3390/toxics10080485. [PubMed:36006164 ]
Shin JK, Park Y, Kim NY, Hwang SJ: Downstream Transport of Geosmin Based on Harmful Cyanobacterial Outbreak Upstream in a Reservoir Cascade. Int J Environ Res Public Health. 2022 Jul 29;19(15):9294. doi: 10.3390/ijerph19159294. [PubMed:35954649 ]
Whangchai N, Klahan R, Balakrishnan D, Unpaprom Y, Ramaraj R, Pimpimol T: Development of aeration devices and feeding frequencies for oxygen concentration improvement in 60-tones freshwater recirculating aquaculture and biofloc ponds of Asian seabass (Lates calcarifer) rearing. Chemosphere. 2022 Nov;307(Pt 3):135761. doi: 10.1016/j.chemosphere.2022.135761. Epub 2022 Aug 2. [PubMed:35931264 ]
Meng T, Su X, Sun P: Degradation of geosmin and 2-methylisoborneol in UV-based AOPs for photoreactors with reflective inner surfaces: Kinetics and transformation products. Chemosphere. 2022 Nov;306:135611. doi: 10.1016/j.chemosphere.2022.135611. Epub 2022 Jul 7. [PubMed:35810865 ]
LOTUS database [Link]

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

MOL for NP0146941 ((+)-geosmin)

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

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

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

PDB for NP0146941 ((+)-geosmin)

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

SMILES for NP0146941 ((+)-geosmin)

INCHI for NP0146941 ((+)-geosmin)

Structure for NP0146941 ((+)-geosmin)

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