NP-MRD: Showing NP-Card for (3S,5R,6R,7E,9S)-3,5,6,9-tetrahydroxymegastigman-7-ene (NP0342022)

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Record Information

Version

2.0

Created at

2024-12-04 23:47:03 UTC

Updated at

2026-01-07 06:35:16 UTC

NP-MRD ID

NP0342022

Natural Product DOI

https://doi.org/10.57994/3517

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3S,5R,6R,7E,9S)-3,5,6,9-tetrahydroxymegastigman-7-ene

Description

Based on a literature review very few articles have been published on (3S,5R,6R,7E,9S)-3,5,6,9-tetrahydroxymegastigman-7-ene.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 03032323572D          

 17 17  0  0  1  0            999 V2000
    2.3054    3.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4929    3.2767    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2107    4.0520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9626    2.6447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1842    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  1  0  0  0  0  0  0  0  0  0
    1.7111    1.6002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2414    0.6817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8245    0.8538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4372    1.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  2  3  1  6  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  1  0  0  0
  8 11  1  0  0  0  0
 12 11  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0342022

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C13H24O4/c1-9(14)5-6-13(17)11(2,3)7-10(15)8-12(13,4)16/h5-6,9-10,14-17H,7-8H2,1-4H3/b6-5+/t9-,10+,12-,13+/m1/s1

> <INCHI_KEY>
CTCKPFXFWVNGLG-CLTYBQGASA-N

> <FORMULA>
C13H24O4

> <MOLECULAR_WEIGHT>
244.331

> <EXACT_MASS>
244.167459253

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
26.853691828014263

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,4S)-1-[(1E,3R)-3-hydroxybut-1-en-1-yl]-2,6,6-trimethylcyclohexane-1,2,4-triol

> <JCHEM_LOGP>
-0.05271493266666652

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.406782078540154

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.909331308641269

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6683503747245894

> <JCHEM_POLAR_SURFACE_AREA>
80.92

> <JCHEM_REFRACTIVITY>
66.6901

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,4S)-1-[(1E,3R)-3-hydroxybut-1-en-1-yl]-2,6,6-trimethylcyclohexane-1,2,4-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-MAR-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-MAR-23         0                                  
HETATM    1  C   UNK     0       4.303   5.849   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.787   6.117   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.260   7.564   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.797   4.937   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.324   3.490   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.344   3.490   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.194   2.987   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.184   1.273   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.539   1.594   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.816   2.846   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8   15                                             
CONECT    7    6                                                            
CONECT    8    6    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14    6   16   17                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₂₄O₄

Average Mass

244.3310 Da

Monoisotopic Mass

244.16746 Da

IUPAC Name

(1S,2R,4S)-1-[(1E,3R)-3-hydroxybut-1-en-1-yl]-2,6,6-trimethylcyclohexane-1,2,4-triol

Traditional Name

(1S,2R,4S)-1-[(1E,3R)-3-hydroxybut-1-en-1-yl]-2,6,6-trimethylcyclohexane-1,2,4-triol

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C13H24O4/c1-9(14)5-6-13(17)11(2,3)7-10(15)8-12(13,4)16/h5-6,9-10,14-17H,7-8H2,1-4H3/b6-5+/t9-,10+,12-,13+/m1/s1

InChI Key

CTCKPFXFWVNGLG-CLTYBQGASA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	[email protected]	University of Mississippi	Sophie Fadime Aydogan	2024-12-04	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	[email protected]	University of Mississippi	Sophie Fadime Aydogan	2024-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD3OD, experimental)	[email protected]	University of Mississippi	Sophie Fadime Aydogan	2024-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD3OD, experimental)	[email protected]	University of Mississippi	Sophie Fadime Aydogan	2024-12-04	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	[email protected]	University of Mississippi	Sophie Fadime Aydogan	2024-12-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, CD3OD, experimental)	[email protected]	University of Mississippi	Sophie Fadime Aydogan	2024-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD3OD, experimental)	[email protected]	University of Mississippi	Sophie Fadime Aydogan	2024-12-04	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Dalbergiella welwitschii		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	-0.053	ChemAxon
pKa (Strongest Acidic)	12.91	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	80.92 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	66.69 m³·mol⁻¹	ChemAxon
Polarizability	26.85 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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (3S,5R,6R,7E,9S)-3,5,6,9-tetrahydroxymegastigman-7-ene (NP0342022)

MOL for NP0342022 ((3S,5R,6R,7E,9S)-3,5,6,9-tetrahydroxymegastigman-7-ene)

3D MOL for NP0342022 ((3S,5R,6R,7E,9S)-3,5,6,9-tetrahydroxymegastigman-7-ene)

3D SDF for NP0342022 ((3S,5R,6R,7E,9S)-3,5,6,9-tetrahydroxymegastigman-7-ene)

3D-SDF for NP0342022 ((3S,5R,6R,7E,9S)-3,5,6,9-tetrahydroxymegastigman-7-ene)

PDB for NP0342022 ((3S,5R,6R,7E,9S)-3,5,6,9-tetrahydroxymegastigman-7-ene)

3D PDB for NP0342022 ((3S,5R,6R,7E,9S)-3,5,6,9-tetrahydroxymegastigman-7-ene)

SMILES for NP0342022 ((3S,5R,6R,7E,9S)-3,5,6,9-tetrahydroxymegastigman-7-ene)

INCHI for NP0342022 ((3S,5R,6R,7E,9S)-3,5,6,9-tetrahydroxymegastigman-7-ene)

Structure for NP0342022 ((3S,5R,6R,7E,9S)-3,5,6,9-tetrahydroxymegastigman-7-ene)

3D Structure for NP0342022 ((3S,5R,6R,7E,9S)-3,5,6,9-tetrahydroxymegastigman-7-ene)