NP-MRD: Showing NP-Card for 11S,12-Dihydroxystigolone (NP0331131)

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Record Information

Version

2.0

Created at

2022-11-16 21:39:47 UTC

Updated at

2024-09-03 04:15:31 UTC

NP-MRD ID

NP0331131

Natural Product DOI

https://doi.org/10.57994/0298

Secondary Accession Numbers

None

Natural Product Identification

Common Name

11S,12-Dihydroxystigolone

Description

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

Structure

MOL SDF PDB SMILES InChI


  Mrv1652311172218512D          

 28 33  0  0  1  0            999 V2000
    5.2705    4.7057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8644    3.9876    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3352    3.3101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0990    2.5196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7486    2.0110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5612    2.1534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9477    1.4245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3740    0.8317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6329    1.1941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8676    0.8859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2181    1.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3338    2.2114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6156    2.6175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4854    3.4321    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2118    4.2105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3871    4.1908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8863    4.8464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1509    3.4003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8297    2.9314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7631    2.1091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0177    1.7557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7815    0.9652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9568    0.9455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6832    1.7238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3388    2.2245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4055    3.0468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0412    4.0419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7329    4.8071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  4 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 21 25  1  0  0  0  0
 25 26  2  0  0  0  0
 18 26  1  0  0  0  0
 14 27  1  0  0  0  0
  2 27  1  0  0  0  0
 27 28  2  0  0  0  0
M  END


  Mrv1652311172218512D          

 28 33  0  0  1  0            999 V2000
    5.2705    4.7057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8644    3.9876    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3352    3.3101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0990    2.5196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7486    2.0110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5612    2.1534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9477    1.4245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3740    0.8317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6329    1.1941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8676    0.8859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2181    1.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3338    2.2114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6156    2.6175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4854    3.4321    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2118    4.2105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3871    4.1908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8863    4.8464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1509    3.4003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8297    2.9314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7631    2.1091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0177    1.7557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7815    0.9652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9568    0.9455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6832    1.7238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3388    2.2245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4055    3.0468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0412    4.0419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7329    4.8071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  4 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 21 25  1  0  0  0  0
 25 26  2  0  0  0  0
 18 26  1  0  0  0  0
 14 27  1  0  0  0  0
  2 27  1  0  0  0  0
 27 28  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0331131

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1CC2=C3OCOC3=CC=C2C[C@@]2(OC(=O)C3=C2C=C2OCOC2=C3)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H15NO7/c1-21-7-12-10(2-3-14-17(12)27-9-24-14)6-20(19(21)23)13-5-16-15(25-8-26-16)4-11(13)18(22)28-20/h2-5H,6-9H2,1H3/t20-/m0/s1

> <INCHI_KEY>
UFSZAONJOVCRPX-FQEVSTJZSA-N

> <FORMULA>
C20H15NO7

> <MOLECULAR_WEIGHT>
381.34

> <EXACT_MASS>
381.084851827

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
37.90844531765718

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4S)-13'-methyl-3',5,5',10,12-pentaoxa-13'-azaspiro[tricyclo[7.3.0.0^{3,7}]dodecane-4,11'-tricyclo[7.5.0.0^{2,6}]tetradecane]-1,1',3(7),6',8,8'-hexaene-6,12'-dione

> <JCHEM_LOGP>
1.9450856853333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.451800535623739

> <JCHEM_POLAR_SURFACE_AREA>
83.53

> <JCHEM_REFRACTIVITY>
93.50410000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4S)-13'-methyl-3',5,5',10,12-pentaoxa-13'-azaspiro[tricyclo[7.3.0.0^{3,7}]dodecane-4,11'-tricyclo[7.5.0.0^{2,6}]tetradecane]-1,1',3(7),6',8,8'-hexaene-6,12'-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-NOV-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-NOV-22         0                                  
HETATM    1  C   UNK     0       9.838   8.784   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       9.080   7.443   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       9.959   6.179   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.518   4.703   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.731   3.754   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      12.248   4.020   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      12.969   2.659   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      11.898   1.552   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      10.515   2.229   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.086   1.654   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.874   2.603   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.090   4.128   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.749   4.886   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.506   6.407   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.995   7.860   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.456   7.823   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.521   9.047   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.015   6.347   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.282   5.472   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.158   3.937   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.766   3.277   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.325   1.802   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.786   1.765   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.275   3.218   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.499   4.152   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.624   5.687   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.543   7.545   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.968   8.973   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   27                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   12                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    5   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    4   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   19   27                                             
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   26                                                  
CONECT   19   18   14   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   25                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   21   26                                                  
CONECT   26   25   18                                                       
CONECT   27   14    2   28                                                  
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₄O₅

Average Mass

284.3520 Da

Monoisotopic Mass

284.16237 Da

IUPAC Name

(4S)-13'-methyl-3',5,5',10,12-pentaoxa-13'-azaspiro[tricyclo[7.3.0.0^{3,7}]dodecane-4,11'-tricyclo[7.5.0.0^{2,6}]tetradecane]-1,1',3(7),6',8,8'-hexaene-6,12'-dione

Traditional Name

(4S)-13'-methyl-3',5,5',10,12-pentaoxa-13'-azaspiro[tricyclo[7.3.0.0^{3,7}]dodecane-4,11'-tricyclo[7.5.0.0^{2,6}]tetradecane]-1,1',3(7),6',8,8'-hexaene-6,12'-dione

CAS Registry Number

Not Available

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-RBTXIFOQSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
NOESY NMR	[¹H, ¹H] 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
HMBC 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	¹H NMR Spectrum (1D, 500 MHz, CD3OD, experimental)	philipwi@hawaii.edu	Not Available	Not Available	2024-05-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, C6D6, experimental)	philipwi@hawaii.edu	Not Available	Not Available	2024-05-12	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

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	1.95	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	83.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	93.5 m³·mol⁻¹	ChemAxon
Polarizability	37.91 Å³	ChemAxon
Number of Rings	6	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

Not Available

References

General References

Not Available

Showing NP-Card for 11S,12-Dihydroxystigolone (NP0331131)

MOL for NP0331131 (11S,12-Dihydroxystigolone)

3D MOL for NP0331131 (11S,12-Dihydroxystigolone)

3D SDF for NP0331131 (11S,12-Dihydroxystigolone)

3D-SDF for NP0331131 (11S,12-Dihydroxystigolone)

PDB for NP0331131 (11S,12-Dihydroxystigolone)

3D PDB for NP0331131 (11S,12-Dihydroxystigolone)

SMILES for NP0331131 (11S,12-Dihydroxystigolone)

INCHI for NP0331131 (11S,12-Dihydroxystigolone)

Structure for NP0331131 (11S,12-Dihydroxystigolone)

3D Structure for NP0331131 (11S,12-Dihydroxystigolone)