NP-MRD: Showing NP-Card for (3beta,5alpha,9alpha,14alpha,22E,24R)-3,5,9,14-Tetrahydroxyergosta-7,22-dien-6-one (NP0335189)

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Record Information

Version

2.0

Created at

2024-09-11 00:26:35 UTC

Updated at

2024-09-11 00:26:36 UTC

NP-MRD ID

NP0335189

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3beta,5alpha,9alpha,14alpha,22E,24R)-3,5,9,14-Tetrahydroxyergosta-7,22-dien-6-one

Description

Based on a literature review very few articles have been published on (3beta,5alpha,9alpha,14alpha,22E,24R)-3,5,9,14-Tetrahydroxyergosta-7,22-dien-6-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05262302582D          

 33 36  0  0  0  0            999 V2000
   -3.7066   -0.4094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7066   -1.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9924   -1.6480    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    0.0020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5654   -1.6480    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
   -1.5654    0.0020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1411    0.0020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1411    0.8236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8525    1.2337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5654    0.8236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6391   -0.2511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1194    0.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6391    1.0755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4222   -1.6480    0.0000 O   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
   -2.2795    0.4162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5654   -0.8236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5654   -2.4736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0543    1.6451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0720   -0.7960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8951    1.8599    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    2.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2547    1.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0626    1.5874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6145    0.9736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3186    2.3717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3586    0.1891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4222    1.1442    0.0000 C   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 19  1  0  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  5 20  1  0  0  0  0
  7  8  1  0  0  0  0
  7 22  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
 11 24  1  0  0  0  0
 12 13  1  0  0  0  0
 12 17  1  0  0  0  0
 12 23  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 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 30 32  1  0  0  0  0
 30 33  1  0  0  0  0
M  END


  Mrv2104 05262302582D          

 33 36  0  0  0  0            999 V2000
   -3.7066   -0.4094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7066   -1.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9924   -1.6480    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    0.0020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5654   -1.6480    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
   -1.5654    0.0020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1411    0.0020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1411    0.8236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8525    1.2337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5654    0.8236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6391   -0.2511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1194    0.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6391    1.0755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4222   -1.6480    0.0000 O   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
   -2.2795    0.4162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5654   -0.8236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5654   -2.4736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0543    1.6451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0720   -0.7960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8951    1.8599    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    2.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2547    1.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0626    1.5874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6145    0.9736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3186    2.3717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3586    0.1891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4222    1.1442    0.0000 C   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 19  1  0  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  5 20  1  0  0  0  0
  7  8  1  0  0  0  0
  7 22  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
 11 24  1  0  0  0  0
 12 13  1  0  0  0  0
 12 17  1  0  0  0  0
 12 23  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 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 30 32  1  0  0  0  0
 30 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0335189

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(C)\C=C\C(C)C1CCC2(O)C3=CC(=O)C4(O)CC(O)CCC4(C)C3(O)CCC12C

> <INCHI_IDENTIFIER>
InChI=1/C28H44O5/c1-17(2)18(3)7-8-19(4)21-10-12-26(31)22-15-23(30)28(33)16-20(29)9-11-25(28,6)27(22,32)14-13-24(21,26)5/h7-8,15,17-21,29,31-33H,9-14,16H2,1-6H3/b8-7+

> <INCHI_KEY>
RLODFSODJNFIMP-BQYQJAHWNA-N

> <FORMULA>
C28H44O5

> <MOLECULAR_WEIGHT>
460.655

> <EXACT_MASS>
460.318874517

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
53.086216082993765

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-[(3E)-5,6-dimethylhept-3-en-2-yl]-3a,5a,7,9b-tetrahydroxy-9a,11a-dimethyl-1H,2H,3H,3aH,5H,5aH,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-5-one

> <JCHEM_LOGP>
3.6474773343333338

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.445792113120374

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.446226557959154

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7340582031053904

> <JCHEM_POLAR_SURFACE_AREA>
97.99

> <JCHEM_REFRACTIVITY>
131.03029999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
1-[(3E)-5,6-dimethylhept-3-en-2-yl]-3a,5a,7,9b-tetrahydroxy-9a,11a-dimethyl-1H,2H,3H,6H,7H,8H,9H,10H,11H-cyclopenta[a]phenanthren-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         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   2.008   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  O   UNK     0      -4.255  -3.847   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -4.255   0.777   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.922  -1.537   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -2.922  -4.617   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.101   3.071   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.134  -1.486   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.671   3.472   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.641   4.617   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.179   3.790   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.209   2.645   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.717   2.963   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.747   1.817   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.195   4.427   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.269   0.353   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.255   2.136   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7   19                                             
CONECT    5    4    6   10   20                                             
CONECT    6    1    5                                                       
CONECT    7    4    8   22                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    5    9   14   21                                             
CONECT   11    9   12   15   24                                             
CONECT   12   11   13   17   23                                             
CONECT   13   12   14                                                       
CONECT   14   10   13                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   12   16   25                                                  
CONECT   18    2                                                            
CONECT   19    4                                                            
CONECT   20    5                                                            
CONECT   21   10                                                            
CONECT   22    7                                                            
CONECT   23   12                                                            
CONECT   24   11                                                            
CONECT   25   17   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29   32   33                                                  
CONECT   31   29                                                            
CONECT   32   30                                                            
CONECT   33   30                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
(3b,5a,9a,14a,22E,24R)-3,5,9,14-Tetrahydroxyergosta-7,22-dien-6-one	Generator
(3Β,5α,9α,14α,22E,24R)-3,5,9,14-tetrahydroxyergosta-7,22-dien-6-one	Generator

Chemical Formula

C₂₈H₄₄O₅

Average Mass

460.6550 Da

Monoisotopic Mass

460.31887 Da

IUPAC Name

1-[(3E)-5,6-dimethylhept-3-en-2-yl]-3a,5a,7,9b-tetrahydroxy-9a,11a-dimethyl-1H,2H,3H,3aH,5H,5aH,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-5-one

Traditional Name

1-[(3E)-5,6-dimethylhept-3-en-2-yl]-3a,5a,7,9b-tetrahydroxy-9a,11a-dimethyl-1H,2H,3H,6H,7H,8H,9H,10H,11H-cyclopenta[a]phenanthren-5-one

CAS Registry Number

Not Available

SMILES

CC(C)C(C)\C=C\C(C)C1CCC2(O)C3=CC(=O)C4(O)CC(O)CCC4(C)C3(O)CCC12C

InChI Identifier

InChI=1/C28H44O5/c1-17(2)18(3)7-8-19(4)21-10-12-26(31)22-15-23(30)28(33)16-20(29)9-11-25(28,6)27(22,32)14-13-24(21,26)5/h7-8,15,17-21,29,31-33H,9-14,16H2,1-6H3/b8-7+

InChI Key

RLODFSODJNFIMP-BQYQJAHWNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Classification

Not classified

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	3.65	ChemAxon
pKa (Strongest Acidic)	12.45	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	131.03 m³·mol⁻¹	ChemAxon
Polarizability	53.09 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (3beta,5alpha,9alpha,14alpha,22E,24R)-3,5,9,14-Tetrahydroxyergosta-7,22-dien-6-one (NP0335189)

MOL for NP0335189 ((3beta,5alpha,9alpha,14alpha,22E,24R)-3,5,9,14-Tetrahydroxyergosta-7,22-dien-6-one)

3D MOL for NP0335189 ((3beta,5alpha,9alpha,14alpha,22E,24R)-3,5,9,14-Tetrahydroxyergosta-7,22-dien-6-one)

3D SDF for NP0335189 ((3beta,5alpha,9alpha,14alpha,22E,24R)-3,5,9,14-Tetrahydroxyergosta-7,22-dien-6-one)

3D-SDF for NP0335189 ((3beta,5alpha,9alpha,14alpha,22E,24R)-3,5,9,14-Tetrahydroxyergosta-7,22-dien-6-one)

PDB for NP0335189 ((3beta,5alpha,9alpha,14alpha,22E,24R)-3,5,9,14-Tetrahydroxyergosta-7,22-dien-6-one)

3D PDB for NP0335189 ((3beta,5alpha,9alpha,14alpha,22E,24R)-3,5,9,14-Tetrahydroxyergosta-7,22-dien-6-one)

SMILES for NP0335189 ((3beta,5alpha,9alpha,14alpha,22E,24R)-3,5,9,14-Tetrahydroxyergosta-7,22-dien-6-one)

INCHI for NP0335189 ((3beta,5alpha,9alpha,14alpha,22E,24R)-3,5,9,14-Tetrahydroxyergosta-7,22-dien-6-one)

Structure for NP0335189 ((3beta,5alpha,9alpha,14alpha,22E,24R)-3,5,9,14-Tetrahydroxyergosta-7,22-dien-6-one)

3D Structure for NP0335189 ((3beta,5alpha,9alpha,14alpha,22E,24R)-3,5,9,14-Tetrahydroxyergosta-7,22-dien-6-one)