NP-MRD: Showing NP-Card for 11,12-Didehydrospironostoic Acid (NP0331129)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-11-16 21:39:23 UTC

Updated at

2024-09-03 04:15:31 UTC

NP-MRD ID

NP0331129

Natural Product DOI

https://doi.org/10.57994/0296

Secondary Accession Numbers

None

Natural Product Identification

Common Name

11,12-Didehydrospironostoic Acid

Description

11,12-Didehydrospironostoic Acid was first documented in 2022 (PMID: 35142496).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652311162222392D          

 19 20  0  0  1  0            999 V2000
    3.7445    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9195    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5070   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6820   -0.3020    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2695   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6674   -0.4849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4211   -0.1494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0886   -0.6343    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5074    0.6711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5812   -1.3054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7351    0.3745    0.0000 H   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
    0.7846    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6820    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5070    1.1270    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  6  0  0  0
  4  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  9 13  2  0  0  0  0
  8 14  1  1  0  0  0
  8 15  1  0  0  0  0
 15 16  1  0  0  0  0
  6 16  1  0  0  0  0
  6 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
  2 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331129

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]1(CC[C@]2(C1)[C@@H](C)CC(=O)C=C2C)C(=C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O3/c1-9-6-13(16)7-10(2)15(9)5-4-12(8-15)11(3)14(17)18/h6,10,12H,3-5,7-8H2,1-2H3,(H,17,18)/t10-,12+,15+/m0/s1

> <INCHI_KEY>
LAWCKNORDBHEQP-JVLSTEMRSA-N

> <FORMULA>
C15H20O3

> <MOLECULAR_WEIGHT>
248.322

> <EXACT_MASS>
248.141244504

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
27.055200974605967

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(2R,5S,10S)-6,10-dimethyl-8-oxospiro[4.5]dec-6-en-2-yl]prop-2-enoic acid

> <JCHEM_LOGP>
2.891529411666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.761396930498114

> <JCHEM_PKA_STRONGEST_BASIC>
-4.729680557635453

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
69.7877

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2-[(2R,5S,10S)-6,10-dimethyl-8-oxospiro[4.5]dec-6-en-2-yl]prop-2-enoic acid

> <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       6.990   0.770   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.450   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.680  -0.564   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.140  -0.564   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.370  -1.897   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.370   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.465  -0.476   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.246  -0.905   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.653  -0.279   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -3.899  -1.184   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -2.814   1.253   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.085  -2.437   0.000  0.00  0.00           C+0
HETATM   14  H   UNK     0      -1.372   0.699   0.000  0.00  0.00           H+0
HETATM   15  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.465   2.016   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.140   2.104   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.370   3.437   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.680   2.104   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   19                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   16   17                                             
CONECT    7    6    8                                                       
CONECT    8    7    9   14   15                                             
CONECT    9    8   10   13                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    9                                                            
CONECT   14    8                                                            
CONECT   15    8   16                                                       
CONECT   16   15    6                                                       
CONECT   17    6   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17    2                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₁NO₆

Average Mass

395.4110 Da

Monoisotopic Mass

395.13689 Da

IUPAC Name

2-[(2R,5S,10S)-6,10-dimethyl-8-oxospiro[4.5]dec-6-en-2-yl]prop-2-enoic acid

Traditional Name

2-[(2R,5S,10S)-6,10-dimethyl-8-oxospiro[4.5]dec-6-en-2-yl]prop-2-enoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C22H21NO6/c1-9(24)14-4-5-15-12-3-6-16(25)20-19(12)21(23(14)15)13-7-11(8-17(26)27)29-10(2)18(13)22(20)28/h3,6-7,9-10,14,24,28H,4-5,8H2,1-2H3,(H,26,27)/t9-,10-,14+/m1/s1

InChI Key

OCIPLYCMVXSIDW-RULNRJAQSA-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
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	philipwi@hawaii.edu	Not Available	Not Available	2024-05-12	View Spectrum
1D_TOCSY NMR	¹H NMR Spectrum (1D, 600 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
1D NMR	¹H NMR Spectrum (1D, 600 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, 126 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. R-3-1		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	2.89	ChemAxon
pKa (Strongest Acidic)	4.76	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	69.79 m³·mol⁻¹	ChemAxon
Polarizability	27.06 Å³	ChemAxon
Number of Rings	2	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 11,12-Didehydrospironostoic Acid (NP0331129)

MOL for NP0331129 (11,12-Didehydrospironostoic Acid)

3D MOL for NP0331129 (11,12-Didehydrospironostoic Acid)

3D SDF for NP0331129 (11,12-Didehydrospironostoic Acid)

3D-SDF for NP0331129 (11,12-Didehydrospironostoic Acid)

PDB for NP0331129 (11,12-Didehydrospironostoic Acid)

3D PDB for NP0331129 (11,12-Didehydrospironostoic Acid)

SMILES for NP0331129 (11,12-Didehydrospironostoic Acid)

INCHI for NP0331129 (11,12-Didehydrospironostoic Acid)

Structure for NP0331129 (11,12-Didehydrospironostoic Acid)

3D Structure for NP0331129 (11,12-Didehydrospironostoic Acid)