NP-MRD: Showing NP-Card for 11R,12-Dihydroxystigolone (NP0331128)

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Record Information

Version

2.0

Created at

2022-11-16 21:39:12 UTC

Updated at

2024-09-03 04:15:31 UTC

NP-MRD ID

NP0331128

Natural Product DOI

https://doi.org/10.57994/0295

Secondary Accession Numbers

None

Natural Product Identification

Common Name

11R,12-Dihydroxystigolone

Description

11R,12-Dihydroxystigolone was first documented in 2022 (PMID: 35142496).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652311162222392D          

 22 23  0  0  1  0            999 V2000
   -1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   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
    0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  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
    2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2704   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 H   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
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
  9 13  1  1  0  0  0
  8 14  1  1  0  0  0
  8 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
  4 17  1  0  0  0  0
 17 18  1  1  0  0  0
  6 19  1  6  0  0  0
  6 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
  2 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331128

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(C[C@]2([H])C(C)=CC(=O)C[C@@]2(C)[C@H](O)[C@@H]1O)[C@@](C)(O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O5/c1-8-4-9(17)6-14(2)10(8)5-11(12(18)13(14)19)15(3,20)7-16/h4,10-13,16,18-20H,5-7H2,1-3H3/t10-,11+,12-,13-,14-,15+/m1/s1

> <INCHI_KEY>
SABNXPXZUNKNJG-FVUFVHQMSA-N

> <FORMULA>
C15H24O5

> <MOLECULAR_WEIGHT>
284.352

> <EXACT_MASS>
284.162373873

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
30.067511449255846

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4aR,6S,7R,8S,8aR)-6-[(2R)-1,2-dihydroxypropan-2-yl]-7,8-dihydroxy-4,8a-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-2-one

> <JCHEM_LOGP>
-0.6567462449999998

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.968129950755895

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.314992220360836

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0735950428748184

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
74.374

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4aR,6S,7R,8S,8aR)-6-[(2R)-1,2-dihydroxypropan-2-yl]-7,8-dihydroxy-4,8a-dimethyl-1,4a,5,6,7,8-hexahydronaphthalen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-NOV-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-NOV-22         0                                  
HETATM    1  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.105  -1.334   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.668   0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.565   1.334   0.000  0.00  0.00           C+0
HETATM   14  H   UNK     0       5.335  -1.540   0.000  0.00  0.00           H+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   19  H   UNK     0       1.334   0.770   0.000  0.00  0.00           H+0
HETATM   20  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   22                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6   17                                             
CONECT    5    4                                                            
CONECT    6    4    7   19   20                                             
CONECT    7    6    8                                                       
CONECT    8    7    9   14   15                                             
CONECT    9    8   10   11   13                                             
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11                                                            
CONECT   13    9                                                            
CONECT   14    8                                                            
CONECT   15    8   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    4   18                                                  
CONECT   18   17                                                            
CONECT   19    6                                                            
CONECT   20    6   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20    2                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₁NO₇

Average Mass

411.4100 Da

Monoisotopic Mass

411.13180 Da

IUPAC Name

(4aR,6S,7R,8S,8aR)-6-[(2R)-1,2-dihydroxypropan-2-yl]-7,8-dihydroxy-4,8a-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-2-one

Traditional Name

(4aR,6S,7R,8S,8aR)-6-[(2R)-1,2-dihydroxypropan-2-yl]-7,8-dihydroxy-4,8a-dimethyl-1,4a,5,6,7,8-hexahydronaphthalen-2-one

CAS Registry Number

Not Available

SMILES

[H][C@]1(CCC2=C3C=CC(=O)C4=C3C(N12)=C1C(=O)[C@H](CC(O)=O)O[C@@H](C)C1=C4O)[C@@H](C)O

InChI Identifier

InChI=1S/C22H21NO7/c1-8(24)11-4-5-12-10-3-6-13(25)18-17(10)20(23(11)12)19-16(22(18)29)9(2)30-14(21(19)28)7-15(26)27/h3,6,8-9,11,14,24,29H,4-5,7H2,1-2H3,(H,26,27)/t8-,9+,11+,14+/m1/s1

InChI Key

XQKQNMOKOZIAQO-DKZXUEBISA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D_TOCSY NMR	¹H NMR Spectrum (1D, 500 MHz, CD3OD, experimental)	philipwi@hawaii.edu	Not Available	Not Available	2024-05-12	View Spectrum
1D_TOCSY NMR	¹H NMR Spectrum (1D, 500 MHz, CD3OD, experimental)	philipwi@hawaii.edu	Not Available	Not Available	2024-05-12	View Spectrum
1D_TOCSY NMR	¹H NMR Spectrum (1D, 500 MHz, CD3OD, experimental)	philipwi@hawaii.edu	Not Available	Not Available	2024-05-12	View Spectrum
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	philipwi@hawaii.edu	Not Available	Not Available	2024-05-12	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	philipwi@hawaii.edu	Not Available	Not Available	2024-05-12	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	philipwi@hawaii.edu	Not Available	Not Available	2024-05-12	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	philipwi@hawaii.edu	Not Available	Not Available	2024-05-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, CD3OD, experimental)	philipwi@hawaii.edu	Not Available	Not Available	2024-05-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD3OD, experimental)	philipwi@hawaii.edu	Not Available	Not Available	2024-05-12	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
sp. U-3-3		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	-0.66	ChemAxon
pKa (Strongest Acidic)	13.31	ChemAxon
pKa (Strongest Basic)	-3.1	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	2	ChemAxon
Refractivity	74.37 m³·mol⁻¹	ChemAxon
Polarizability	30.07 Å³	ChemAxon
Number of Rings	2	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

Not Available

References

General References

Not Available

Showing NP-Card for 11R,12-Dihydroxystigolone (NP0331128)

MOL for NP0331128 (11R,12-Dihydroxystigolone)

3D MOL for NP0331128 (11R,12-Dihydroxystigolone)

3D SDF for NP0331128 (11R,12-Dihydroxystigolone)

3D-SDF for NP0331128 (11R,12-Dihydroxystigolone)

PDB for NP0331128 (11R,12-Dihydroxystigolone)

3D PDB for NP0331128 (11R,12-Dihydroxystigolone)

SMILES for NP0331128 (11R,12-Dihydroxystigolone)

INCHI for NP0331128 (11R,12-Dihydroxystigolone)

Structure for NP0331128 (11R,12-Dihydroxystigolone)

3D Structure for NP0331128 (11R,12-Dihydroxystigolone)