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Showing NP-Card for Arnamiol (NP0048140)

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Record Information
Version2.0
Created at2022-03-17 20:51:44 UTC
Updated at2022-03-17 20:51:44 UTC
NP-MRD IDNP0048140
Secondary Accession NumbersNone
Natural Product Identification
Common NameArnamiol
DescriptionArnamiol belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Arnamiol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Arnamiol has been detected, but not quantified in, mushrooms. Arnamiol is found in Armillaria mellea and Armillaria ostoyae. This could make arnamiol a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0048140 (Arnamiol)


  Mrv0541 05061308132D          

 31 34  0  0  0  0            999 V2000
   -0.8971    0.5197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3497    0.5391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8336    1.5152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6532    1.3308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2347   -2.2130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6261   -1.8455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4330   -0.0762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8090    1.1039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7115    0.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9182   -1.5842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1401   -0.2687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6202   -0.2176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3570   -0.8855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2346    0.5118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8218   -1.6617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1874   -1.2408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2727    0.2826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5788   -0.8733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9714   -0.1562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9444   -0.4524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1815   -0.9162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2254   -0.6896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5497    0.7406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4102    0.5424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5056    0.1522    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.3039   -2.3135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2606   -2.2664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5671   -1.6455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7867   -1.2942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9917   -1.4246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4685    0.0988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 11  1  1  0  0  0  0
 12  7  1  0  0  0  0
 13 10  1  0  0  0  0
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 24 14  1  0  0  0  0
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 27 15  1  0  0  0  0
 28 21  1  0  0  0  0
 29 22  2  0  0  0  0
 30  5  1  0  0  0  0
 30 16  1  0  0  0  0
 31 17  1  0  0  0  0
 31 22  1  0  0  0  0
M  END
Download

3D MOL for NP0048140 (Arnamiol)

Download
3D SDF for NP0048140 (Arnamiol)

  Mrv0541 05061308132D          

 31 34  0  0  0  0            999 V2000
   -0.8971    0.5197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3497    0.5391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8336    1.5152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6532    1.3308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2347   -2.2130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6261   -1.8455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4330   -0.0762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8090    1.1039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7115    0.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9182   -1.5842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1401   -0.2687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6202   -0.2176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3570   -0.8855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2346    0.5118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8218   -1.6617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1874   -1.2408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2727    0.2826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5788   -0.8733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9714   -0.1562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9444   -0.4524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1815   -0.9162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2254   -0.6896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5497    0.7406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4102    0.5424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5056    0.1522    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.3039   -2.3135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2606   -2.2664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5671   -1.6455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7867   -1.2942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9917   -1.4246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4685    0.0988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 11  1  1  0  0  0  0
 12  7  1  0  0  0  0
 13 10  1  0  0  0  0
 14  8  1  0  0  0  0
 14 12  1  0  0  0  0
 15  6  2  0  0  0  0
 16  6  1  0  0  0  0
 17  9  1  0  0  0  0
 18 11  2  0  0  0  0
 18 15  1  0  0  0  0
 19 13  2  0  0  0  0
 19 17  1  0  0  0  0
 20 11  1  0  0  0  0
 20 16  2  0  0  0  0
 21 12  1  0  0  0  0
 21 13  1  0  0  0  0
 22 18  1  0  0  0  0
 23  2  1  0  0  0  0
 23  3  1  0  0  0  0
 23  7  1  0  0  0  0
 23  8  1  0  0  0  0
 24  4  1  0  0  0  0
 24  9  1  0  0  0  0
 24 14  1  0  0  0  0
 24 19  1  0  0  0  0
 25 20  1  0  0  0  0
 26 10  1  0  0  0  0
 27 15  1  0  0  0  0
 28 21  1  0  0  0  0
 29 22  2  0  0  0  0
 30  5  1  0  0  0  0
 30 16  1  0  0  0  0
 31 17  1  0  0  0  0
 31 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048140

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(Cl)C(C)=C(C(=O)OC2CC3(C)C4CC(C)(C)CC4C(O)C(CO)=C23)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C24H31ClO6/c1-11-18(15(27)6-16(30-5)20(11)25)22(29)31-17-9-24(4)14-8-23(2,3)7-12(14)21(28)13(10-26)19(17)24/h6,12,14,17,21,26-28H,7-10H2,1-5H3

> <INCHI_KEY>
OMAGQTXDHXASNM-UHFFFAOYSA-N

> <FORMULA>
C24H31ClO6

> <MOLECULAR_WEIGHT>
450.952

> <EXACT_MASS>
450.180916431

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
48.80536670635909

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-hydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1H,2H,4H,4aH,5H,6H,7H,7aH,7bH-cyclobuta[e]inden-2-yl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate

> <ALOGPS_LOGP>
3.41

> <JCHEM_LOGP>
4.194590127999999

> <ALOGPS_LOGS>
-4.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.19222938893536

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.324084973317882

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7730707526470066

> <JCHEM_POLAR_SURFACE_AREA>
96.22

> <JCHEM_REFRACTIVITY>
118.26859999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.66e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1H,2H,4H,4aH,5H,7H,7aH-cyclobuta[e]inden-2-yl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0048140 (Arnamiol)
Download
PDB for NP0048140 (Arnamiol)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -1.675   0.970   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.986   1.006   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.023   2.828   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.953   2.484   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.038  -4.131   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.035  -3.445   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.275  -0.142   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.110   2.061   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.195   1.832   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.581  -2.957   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.128  -0.502   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.758  -0.406   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.400  -1.653   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.038   0.955   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.534  -3.102   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.083  -2.316   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.376   0.528   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.080  -1.630   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.680  -0.292   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.630  -0.844   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.939  -1.710   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.421  -1.287   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.493   1.382   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.499   1.012   0.000  0.00  0.00           C+0
HETATM   25 Cl   UNK     0      -4.677   0.284   0.000  0.00  0.00          Cl+0
HETATM   26  O   UNK     0       4.301  -4.319   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -0.486  -4.231   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       6.659  -3.072   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       1.469  -2.416   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -5.585  -2.659   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       0.875   0.184   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   23                                                            
CONECT    3   23                                                            
CONECT    4   24                                                            
CONECT    5   30                                                            
CONECT    6   15   16                                                       
CONECT    7   12   23                                                       
CONECT    8   14   23                                                       
CONECT    9   17   24                                                       
CONECT   10   13   26                                                       
CONECT   11    1   18   20                                                  
CONECT   12    7   14   21                                                  
CONECT   13   10   19   21                                                  
CONECT   14    8   12   24                                                  
CONECT   15    6   18   27                                                  
CONECT   16    6   20   30                                                  
CONECT   17    9   19   31                                                  
CONECT   18   11   15   22                                                  
CONECT   19   13   17   24                                                  
CONECT   20   11   16   25                                                  
CONECT   21   12   13   28                                                  
CONECT   22   18   29   31                                                  
CONECT   23    2    3    7    8                                             
CONECT   24    4    9   14   19                                             
CONECT   25   20                                                            
CONECT   26   10                                                            
CONECT   27   15                                                            
CONECT   28   21                                                            
CONECT   29   22                                                            
CONECT   30    5   16                                                       
CONECT   31   17   22                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

Download
3D PDB for NP0048140 (Arnamiol)
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SMILES for NP0048140 (Arnamiol)
COC1=C(Cl)C(C)=C(C(=O)OC2CC3(C)C4CC(C)(C)CC4C(O)C(CO)=C23)C(O)=C1
Download
INCHI for NP0048140 (Arnamiol)
InChI=1S/C24H31ClO6/c1-11-18(15(27)6-16(30-5)20(11)25)22(29)31-17-9-24(4)14-8-23(2,3)7-12(14)21(28)13(10-26)19(17)24/h6,12,14,17,21,26-28H,7-10H2,1-5H3
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View in JSmol
Synonyms
ValueSource
4-Hydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1H,2H,4H,4ah,5H,6H,7H,7ah,7BH-cyclobuta[e]inden-2-yl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoic acidGenerator
Chemical FormulaC24H31ClO6
Average Mass450.9520 Da
Monoisotopic Mass450.18092 Da
IUPAC Name4-hydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1H,2H,4H,4aH,5H,6H,7H,7aH,7bH-cyclobuta[e]inden-2-yl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate
Traditional Name4-hydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1H,2H,4H,4aH,5H,7H,7aH-cyclobuta[e]inden-2-yl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate
CAS Registry Number102092-23-9
SMILES
COC1=C(Cl)C(C)=C(C(=O)OC2CC3(C)C4CC(C)(C)CC4C(O)C(CO)=C23)C(O)=C1
InChI Identifier
InChI=1S/C24H31ClO6/c1-11-18(15(27)6-16(30-5)20(11)25)22(29)31-17-9-24(4)14-8-23(2,3)7-12(14)21(28)13(10-26)19(17)24/h6,12,14,17,21,26-28H,7-10H2,1-5H3
InChI KeyOMAGQTXDHXASNM-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Agaricus bisporusFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Armillaria melleaFungi
Armillaria ostoyaeLOTUS Database
Pleurotus ostreatusFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassSesquiterpenoids  
Direct ParentSesquiterpenoids  
Alternative Parents
Substituents
  • Sesquiterpenoid
    • 

  • Oxepane
    • 

  • Monosaccharide
    • 

  • Cyclic alcohol
    • 

  • Tetrahydrofuran
    • 

  • Tertiary alcohol
    • 

  • Hemiacetal
    • 

  • Secondary alcohol
    • 

  • Polyol
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Alcohol
    • 

  • Organic oxygen compound
    • 

  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic 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
logP3.41ALOGPS
logP4.19ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)9.32ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area96.22 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity118.27 m³·mol⁻¹ChemAxon
Polarizability48.81 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0035062  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB013685  
KNApSAcK IDC00021472  
Chemspider ID28576292  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound71317588  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References