NP-MRD: Showing NP-Card for (3beta,5alpha,9alpha,22E,24R)-5,9-Epidioxy-3-hydroxyergosta-7,22-dien-6-one (NP0047427)

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Record Information

Version

2.0

Created at

2022-03-17 20:40:01 UTC

Updated at

2022-03-17 20:40:01 UTC

NP-MRD ID

NP0047427

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3beta,5alpha,9alpha,22E,24R)-5,9-Epidioxy-3-hydroxyergosta-7,22-dien-6-one

Description

Humulenol I belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Humulenol I is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Humulenol I has been detected, but not quantified in, herbs and spices. This could make humulenol I a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241219522D          

 32 36  0  0  0  0            999 V2000
   -3.7067   -0.4094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7067   -1.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9924   -1.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2795   -1.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2795   -0.4094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9924    0.0019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5653   -1.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8525   -1.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8525   -0.4094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5653    0.0019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1410    0.0019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1410    0.8236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8525    1.2336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5653    0.8236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6390   -0.2511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1195    0.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6390    1.0753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4222   -1.6479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2795    0.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2795   -2.0607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5653   -0.8236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1410    1.6492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8951    1.8598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3432    2.4736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7029    2.0304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2548    1.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0625    1.5874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6144    0.9735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3185    2.3718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3584    0.1891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4222    1.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5653   -2.4736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  2 18  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  4 20  1  0  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  5 19  1  0  0  0  0
  7  8  1  0  0  0  0
  7 32  2  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 14  1  0  0  0  0
 10 21  1  0  0  0  0
 11 12  1  0  0  0  0
 11 15  1  0  0  0  0
 12 13  1  0  0  0  0
 12 17  1  0  0  0  0
 12 22  1  0  0  0  0
 13 14  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 23  1  0  0  0  0
 20 21  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 28 30  1  0  0  0  0
 28 31  1  0  0  0  0
M  END


  Mrv0541 02241219522D          

 32 36  0  0  0  0            999 V2000
   -3.7067   -0.4094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7067   -1.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9924   -1.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2795   -1.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2795   -0.4094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9924    0.0019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5653   -1.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8525   -1.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8525   -0.4094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5653    0.0019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1410    0.0019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1410    0.8236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8525    1.2336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5653    0.8236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6390   -0.2511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1195    0.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6390    1.0753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4222   -1.6479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2795    0.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2795   -2.0607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5653   -0.8236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1410    1.6492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8951    1.8598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3432    2.4736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7029    2.0304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2548    1.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0625    1.5874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6144    0.9735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3185    2.3718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3584    0.1891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4222    1.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5653   -2.4736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  2 18  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  4 20  1  0  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  5 19  1  0  0  0  0
  7  8  1  0  0  0  0
  7 32  2  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 14  1  0  0  0  0
 10 21  1  0  0  0  0
 11 12  1  0  0  0  0
 11 15  1  0  0  0  0
 12 13  1  0  0  0  0
 12 17  1  0  0  0  0
 12 22  1  0  0  0  0
 13 14  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 23  1  0  0  0  0
 20 21  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 28 30  1  0  0  0  0
 28 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047427

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(C)\C=C\C(C)C1CCC2C3=CC(=O)C45CC(O)CCC4(C)C3(CCC12C)OO5

> <INCHI_IDENTIFIER>
InChI=1S/C28H42O4/c1-17(2)18(3)7-8-19(4)21-9-10-22-23-15-24(30)28-16-20(29)11-12-26(28,6)27(23,31-32-28)14-13-25(21,22)5/h7-8,15,17-22,29H,9-14,16H2,1-6H3/b8-7+

> <INCHI_KEY>
VXKGRYVCJKAYFC-BQYQJAHWSA-N

> <FORMULA>
C28H42O4

> <MOLECULAR_WEIGHT>
442.6307

> <EXACT_MASS>
442.308309832

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
51.827019411780796

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
8-[(3E)-5,6-dimethylhept-3-en-2-yl]-16-hydroxy-9,13-dimethyl-18,19-dioxapentacyclo[10.5.2.0¹,¹³.0⁴,¹².0⁵,⁹]nonadec-3-en-2-one

> <ALOGPS_LOGP>
5.19

> <JCHEM_LOGP>
5.996742807999999

> <ALOGPS_LOGS>
-6.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.641943853391147

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.141266549421221

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7369499112751123

> <JCHEM_POLAR_SURFACE_AREA>
55.76

> <JCHEM_REFRACTIVITY>
127.22739999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.98e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-[(3E)-5,6-dimethylhept-3-en-2-yl]-16-hydroxy-9,13-dimethyl-18,19-dioxapentacyclo[10.5.2.0¹,¹³.0⁴,¹².0⁵,⁹]nonadec-3-en-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

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      -6.919  -0.764   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.919  -2.305   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.586  -3.076   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.255  -2.305   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.255  -0.764   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.586   0.004   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.922  -3.076   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.591  -2.305   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.591  -0.764   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.922   0.004   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.263   0.004   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.263   1.537   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.591   2.303   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.922   1.537   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.193  -0.469   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.090   0.772   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.193   2.007   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -8.255  -3.076   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -4.255   0.772   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -4.255  -3.847   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -2.922  -1.537   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.263   3.079   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.671   3.472   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.641   4.617   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.179   3.790   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.209   2.645   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.717   2.963   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.747   1.817   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.195   4.427   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.269   0.353   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.255   2.136   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -2.922  -4.617   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7   20                                             
CONECT    5    4    6   10   19                                             
CONECT    6    1    5                                                       
CONECT    7    4    8   32                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    5    9   14   21                                             
CONECT   11    9   12   15                                                  
CONECT   12   11   13   17   22                                             
CONECT   13   12   14                                                       
CONECT   14   10   13                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   12   16   23                                                  
CONECT   18    2                                                            
CONECT   19    5                                                            
CONECT   20    4   21                                                       
CONECT   21   10   20                                                       
CONECT   22   12                                                            
CONECT   23   17   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27   30   31                                                  
CONECT   29   27                                                            
CONECT   30   28                                                            
CONECT   31   28                                                            
CONECT   32    7                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

View in JSmol

Synonyms

Value	Source
(+)-Humulenol I	HMDB
4-[(2,5-dioxo-4-Imidazolidinylidene)methyl)-benzaldehyde	HMDB
(3b,5a,9a,22E,24R)-5,9-Epidioxy-3-hydroxyergosta-7,22-dien-6-one	Generator
(3Β,5α,9α,22E,24R)-5,9-epidioxy-3-hydroxyergosta-7,22-dien-6-one	Generator

Chemical Formula

C₂₈H₄₂O₄

Average Mass

442.6307 Da

Monoisotopic Mass

442.30831 Da

IUPAC Name

8-[(3E)-5,6-dimethylhept-3-en-2-yl]-16-hydroxy-9,13-dimethyl-18,19-dioxapentacyclo[10.5.2.0¹,¹³.0⁴,¹².0⁵,⁹]nonadec-3-en-2-one

Traditional Name

8-[(3E)-5,6-dimethylhept-3-en-2-yl]-16-hydroxy-9,13-dimethyl-18,19-dioxapentacyclo[10.5.2.0¹,¹³.0⁴,¹².0⁵,⁹]nonadec-3-en-2-one

CAS Registry Number

211486-16-7

SMILES

CC(C)C(C)\C=C\C(C)C1CCC2C3=CC(=O)C45CC(O)CCC4(C)C3(CCC12C)OO5

InChI Identifier

InChI=1S/C28H42O4/c1-17(2)18(3)7-8-19(4)21-9-10-22-23-15-24(30)28-16-20(29)11-12-26(28,6)27(23,31-32-28)14-13-25(21,22)5/h7-8,15,17-22,29H,9-14,16H2,1-6H3/b8-7+

InChI Key

VXKGRYVCJKAYFC-BQYQJAHWSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Agaricus bisporus	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Pleurotus ostreatus	FooDB	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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Humulane sesquiterpenoid
Sesquiterpenoid
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic 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	5.19	ALOGPS
logP	6	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	15.14	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	127.23 m³·mol⁻¹	ChemAxon
Polarizability	51.83 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0038211

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB017453

KNApSAcK ID

C00012464

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

101417891

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (3beta,5alpha,9alpha,22E,24R)-5,9-Epidioxy-3-hydroxyergosta-7,22-dien-6-one (NP0047427)

MOL for NP0047427 ((3beta,5alpha,9alpha,22E,24R)-5,9-Epidioxy-3-hydroxyergosta-7,22-dien-6-one)

3D MOL for NP0047427 ((3beta,5alpha,9alpha,22E,24R)-5,9-Epidioxy-3-hydroxyergosta-7,22-dien-6-one)

3D SDF for NP0047427 ((3beta,5alpha,9alpha,22E,24R)-5,9-Epidioxy-3-hydroxyergosta-7,22-dien-6-one)

3D-SDF for NP0047427 ((3beta,5alpha,9alpha,22E,24R)-5,9-Epidioxy-3-hydroxyergosta-7,22-dien-6-one)

PDB for NP0047427 ((3beta,5alpha,9alpha,22E,24R)-5,9-Epidioxy-3-hydroxyergosta-7,22-dien-6-one)

3D PDB for NP0047427 ((3beta,5alpha,9alpha,22E,24R)-5,9-Epidioxy-3-hydroxyergosta-7,22-dien-6-one)

SMILES for NP0047427 ((3beta,5alpha,9alpha,22E,24R)-5,9-Epidioxy-3-hydroxyergosta-7,22-dien-6-one)

INCHI for NP0047427 ((3beta,5alpha,9alpha,22E,24R)-5,9-Epidioxy-3-hydroxyergosta-7,22-dien-6-one)

Structure for NP0047427 ((3beta,5alpha,9alpha,22E,24R)-5,9-Epidioxy-3-hydroxyergosta-7,22-dien-6-one)

3D Structure for NP0047427 ((3beta,5alpha,9alpha,22E,24R)-5,9-Epidioxy-3-hydroxyergosta-7,22-dien-6-one)