NP-MRD: Showing NP-Card for (3S,5R,6R,7E)-3,5,6-trihydroxy-7-megastigmen-9-one (NP0331982)

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Record Information

Version

2.0

Created at

2023-10-17 16:02:49 UTC

Updated at

2024-09-03 04:17:36 UTC

NP-MRD ID

NP0331982

Natural Product DOI

https://doi.org/10.57994/1102

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3S,5R,6R,7E)-3,5,6-trihydroxy-7-megastigmen-9-one

Description

SCHEMBL17512155 belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (3S,5R,6R,7E)-3,5,6-trihydroxy-7-megastigmen-9-one was first documented in 2023 (PMID: 37714249). Based on a literature review very few articles have been published on SCHEMBL17512155.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 10172316022D          

 17 17  0  0  1  0            999 V2000
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  1  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
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2822   -0.7752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8125    0.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8125    0.6817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3428    1.3137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1552    1.1705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4374    0.3952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6855    1.8025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2822    1.6002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1842    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  7  4  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  7 13  1  1  0  0  0
  7 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  6  0  0  0
 14 17  1  0  0  0  0
  2 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331982

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)\C=C\[C@@]1(O)C(C)(C)C[C@H](O)C[C@@]1(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C13H22O4/c1-9(14)5-6-13(17)11(2,3)7-10(15)8-12(13,4)16/h5-6,10,15-17H,7-8H2,1-4H3/b6-5+/t10-,12+,13+/m0/s1

> <INCHI_KEY>
QASOACWKTAXFSE-FSEPPJMSSA-N

> <FORMULA>
C13H22O4

> <MOLECULAR_WEIGHT>
242.315

> <EXACT_MASS>
242.151809188

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
26.30611868360292

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3E)-4-[(1R,2R,4S)-1,2,4-trihydroxy-2,6,6-trimethylcyclohexyl]but-3-en-2-one

> <JCHEM_LOGP>
0.1806101033333336

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.457415168984893

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.880723159873964

> <JCHEM_PKA_STRONGEST_BASIC>
-2.737440634594247

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
65.68979999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3E)-4-[(1R,2R,4S)-1,2,4-trihydroxy-2,6,6-trimethylcyclohexyl]but-3-en-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-OCT-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-OCT-23         0                                  
HETATM    1  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.527  -1.447   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.517   0.267   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.517   1.273   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.506   2.452   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.023   2.185   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.550   0.738   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -5.013   3.365   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -0.527   2.987   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.344   3.490   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.324   3.490   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6    7                                             
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    4    8   13   14                                             
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    7                                                            
CONECT   14    7   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14    2                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₂₂O₄

Average Mass

242.3150 Da

Monoisotopic Mass

242.15181 Da

IUPAC Name

(3E)-4-[(1R,2R,4S)-1,2,4-trihydroxy-2,6,6-trimethylcyclohexyl]but-3-en-2-one

Traditional Name

(3E)-4-[(1R,2R,4S)-1,2,4-trihydroxy-2,6,6-trimethylcyclohexyl]but-3-en-2-one

CAS Registry Number

Not Available

SMILES

CC(=O)\C=C\[C@@]1(O)C(C)(C)C[C@H](O)C[C@@]1(C)O

InChI Identifier

InChI=1S/C13H22O4/c1-9(14)5-6-13(17)11(2,3)7-10(15)8-12(13,4)16/h5-6,10,15-17H,7-8H2,1-4H3/b6-5+/t10-,12+,13+/m0/s1

InChI Key

QASOACWKTAXFSE-FSEPPJMSSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	wuhonghua2011@tjutcm.edu.cn	Tianjin University of Traditional Chinese Medicine	Hong-Hua Wu	2023-10-17	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600, CD₃OD, simulated)	wuhonghua2011@tjutcm.edu.cn	Tianjin University of Traditional Chinese Medicine	Hong-Hua Wu	2024-05-14	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
erecta		Not Available

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

Sesquiterpenoid
Megastigmane sesquiterpenoid
Cyclofarsesane sesquiterpenoid
Ionone derivative
Cyclohexanol
Cyclitol or derivatives
Acryloyl-group
Cyclic alcohol
Enone
Alpha,beta-unsaturated ketone
Tertiary alcohol
Ketone
Secondary alcohol
Polyol
Organooxygen compound
Organic oxide
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
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	0.18	ChemAxon
pKa (Strongest Acidic)	12.88	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	65.69 m³·mol⁻¹	ChemAxon
Polarizability	26.31 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

51537162

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (3S,5R,6R,7E)-3,5,6-trihydroxy-7-megastigmen-9-one (NP0331982)

MOL for NP0331982 ((3S,5R,6R,7E)-3,5,6-trihydroxy-7-megastigmen-9-one)

3D MOL for NP0331982 ((3S,5R,6R,7E)-3,5,6-trihydroxy-7-megastigmen-9-one)

3D SDF for NP0331982 ((3S,5R,6R,7E)-3,5,6-trihydroxy-7-megastigmen-9-one)

3D-SDF for NP0331982 ((3S,5R,6R,7E)-3,5,6-trihydroxy-7-megastigmen-9-one)

PDB for NP0331982 ((3S,5R,6R,7E)-3,5,6-trihydroxy-7-megastigmen-9-one)

3D PDB for NP0331982 ((3S,5R,6R,7E)-3,5,6-trihydroxy-7-megastigmen-9-one)

SMILES for NP0331982 ((3S,5R,6R,7E)-3,5,6-trihydroxy-7-megastigmen-9-one)

INCHI for NP0331982 ((3S,5R,6R,7E)-3,5,6-trihydroxy-7-megastigmen-9-one)

Structure for NP0331982 ((3S,5R,6R,7E)-3,5,6-trihydroxy-7-megastigmen-9-one)

3D Structure for NP0331982 ((3S,5R,6R,7E)-3,5,6-trihydroxy-7-megastigmen-9-one)