NP-MRD: Showing NP-Card for (2e)-4-[(1r,5s,7r)-1-[(2s,3e,5r,6z)-7-chloro-5,9-dihydroxynona-3,6-dien-2-yl]-6-azaspiro[4.5]decan-7-yl]-2-methyl-n-(2-sulfoethyl)but-2-enimidic acid (NP0188228)

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Record Information

Version

2.0

Created at

2022-09-04 04:31:19 UTC

Updated at

2022-09-04 04:31:19 UTC

NP-MRD ID

NP0188228

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e)-4-[(1r,5s,7r)-1-[(2s,3e,5r,6z)-7-chloro-5,9-dihydroxynona-3,6-dien-2-yl]-6-azaspiro[4.5]decan-7-yl]-2-methyl-n-(2-sulfoethyl)but-2-enimidic acid

Description

Tauropinnaic acid, also known as tauropinnaate, belongs to the class of organic compounds known as azaspirodecane derivatives. These are organic compounds containing a spirodecane moiety with at least one nitrogen atom. (2e)-4-[(1r,5s,7r)-1-[(2s,3e,5r,6z)-7-chloro-5,9-dihydroxynona-3,6-dien-2-yl]-6-azaspiro[4.5]decan-7-yl]-2-methyl-n-(2-sulfoethyl)but-2-enimidic acid is found in Pinna muricata. (2e)-4-[(1r,5s,7r)-1-[(2s,3e,5r,6z)-7-chloro-5,9-dihydroxynona-3,6-dien-2-yl]-6-azaspiro[4.5]decan-7-yl]-2-methyl-n-(2-sulfoethyl)but-2-enimidic acid was first documented in 2004 (PMID: 15299146). Based on a literature review very few articles have been published on Tauropinnaic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042206312D          

 35 36  0  0  1  0            999 V2000
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M  END

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M  END


  Mrv1652309042206312D          

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  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
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
  9 26  1  0  0  0  0
  5 26  1  0  0  0  0
  2 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 29 30  1  4  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  2  0  0  0  0
 32 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0188228

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H](\C=C\[C@@H](O)\C=C(/Cl)CCO)[C@H]1CCC[C@]11CCC[C@H](C\C=C(/C)C(O)=NCCS(O)(=O)=O)N1

> <INCHI_IDENTIFIER>
InChI=1S/C25H41ClN2O6S/c1-18(8-10-22(30)17-20(26)11-15-29)23-6-4-13-25(23)12-3-5-21(28-25)9-7-19(2)24(31)27-14-16-35(32,33)34/h7-8,10,17-18,21-23,28-30H,3-6,9,11-16H2,1-2H3,(H,27,31)(H,32,33,34)/b10-8+,19-7+,20-17-/t18-,21+,22+,23+,25+/m0/s1

> <INCHI_KEY>
DPTYZUYLNUDZOR-VOXYKYCVSA-N

> <FORMULA>
C25H41ClN2O6S

> <MOLECULAR_WEIGHT>
533.12

> <EXACT_MASS>
532.2373859

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
57.4949836958825

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-4-[(1R,5S,7R)-1-[(2S,3E,5R,6Z)-7-chloro-5,9-dihydroxynona-3,6-dien-2-yl]-6-azaspiro[4.5]decan-7-yl]-2-methyl-N-(2-sulfoethyl)but-2-enimidic acid

> <JCHEM_LOGP>
0.9705008194430602

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
4.590885205039409

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.356344602642146

> <JCHEM_PKA_STRONGEST_BASIC>
11.067282875281895

> <JCHEM_POLAR_SURFACE_AREA>
139.45

> <JCHEM_REFRACTIVITY>
141.9029

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-4-[(1R,5S,7R)-1-[(2S,3E,5R,6Z)-7-chloro-5,9-dihydroxynona-3,6-dien-2-yl]-6-azaspiro[4.5]decan-7-yl]-2-methyl-N-(2-sulfoethyl)but-2-enimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       6.990   6.105   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.450   6.105   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.680   4.771   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.450   3.437   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.680   2.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.450   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.680  -0.564   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.140  -0.564   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.370   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.465  -0.476   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.465   2.016   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.941   3.481   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.447   3.801   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.910   4.625   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.386   6.090   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.355   7.234   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.151   6.914   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.831   8.699   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.199   9.843   0.000  0.00  0.00           C+0
HETATM   22 Cl   UNK     0      -1.705   9.523   0.000  0.00  0.00          Cl+0
HETATM   23  C   UNK     0       0.277  11.308   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.754  12.452   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -2.260  12.132   0.000  0.00  0.00           O+0
HETATM   26  N   UNK     0       3.140   2.104   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0       4.680   7.438   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       3.140   7.438   0.000  0.00  0.00           O+0
HETATM   29  N   UNK     0       5.450   8.772   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0       4.680  10.106   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.140  10.106   0.000  0.00  0.00           C+0
HETATM   32  S   UNK     0       2.370  11.439   0.000  0.00  0.00           S+0
HETATM   33  O   UNK     0       1.600  12.773   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       3.703  12.209   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       1.036  10.669   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   27                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   26                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   13   26                                             
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    9   14                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26    9    5                                                       
CONECT   27    2   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34   35                                             
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   32                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   72    0
END

View in JSmol

Synonyms

Value	Source
Tauropinnaate	Generator

Chemical Formula

C₂₅H₄₁ClN₂O₆S

Average Mass

533.1200 Da

Monoisotopic Mass

532.23739 Da

IUPAC Name

(2E)-4-[(1R,5S,7R)-1-[(2S,3E,5R,6Z)-7-chloro-5,9-dihydroxynona-3,6-dien-2-yl]-6-azaspiro[4.5]decan-7-yl]-2-methyl-N-(2-sulfoethyl)but-2-enimidic acid

Traditional Name

(2E)-4-[(1R,5S,7R)-1-[(2S,3E,5R,6Z)-7-chloro-5,9-dihydroxynona-3,6-dien-2-yl]-6-azaspiro[4.5]decan-7-yl]-2-methyl-N-(2-sulfoethyl)but-2-enimidic acid

CAS Registry Number

Not Available

SMILES

C[C@@H](\C=C\[C@@H](O)\C=C(/Cl)CCO)[C@H]1CCC[C@]11CCC[C@H](C\C=C(/C)C(O)=NCCS(O)(=O)=O)N1

InChI Identifier

InChI=1S/C25H41ClN2O6S/c1-18(8-10-22(30)17-20(26)11-15-29)23-6-4-13-25(23)12-3-5-21(28-25)9-7-19(2)24(31)27-14-16-35(32,33)34/h7-8,10,17-18,21-23,28-30H,3-6,9,11-16H2,1-2H3,(H,27,31)(H,32,33,34)/b10-8+,19-7+,20-17-/t18-,21+,22+,23+,25+/m0/s1

InChI Key

DPTYZUYLNUDZOR-VOXYKYCVSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Pinna muricata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as azaspirodecane derivatives. These are organic compounds containing a spirodecane moiety with at least one nitrogen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azaspirodecane derivatives

Sub Class

Not Available

Direct Parent

Azaspirodecane derivatives

Alternative Parents

Substituents

Azaspirodecane
N-acyl-amine
Piperidine
Alkanesulfonic acid
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Sulfonyl
Organosulfonic acid
Amino acid or derivatives
Carboxamide group
Secondary alcohol
Secondary carboxylic acid amide
Carboxylic acid derivative
Secondary aliphatic amine
Azacycle
Chloroalkene
Secondary amine
Haloalkene
Vinyl halide
Vinyl chloride
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Hydrocarbon derivative
Organosulfur compound
Amine
Primary alcohol
Organic nitrogen compound
Organic oxygen compound
Carbonyl group
Organic oxide
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	0.97	ChemAxon
pKa (Strongest Acidic)	-1.4	ChemAxon
pKa (Strongest Basic)	11.07	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	139.45 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	141.9 m³·mol⁻¹	ChemAxon
Polarizability	57.49 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

8182845

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10007265

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Christie HS, Heathcock CH: Total synthesis of (+/-)-halichlorine, (+/-)-pinnaic acid, and (+/-)-tauropinnaic acid. Proc Natl Acad Sci U S A. 2004 Aug 17;101(33):12079-84. doi: 10.1073/pnas.0403887101. Epub 2004 Aug 6. [PubMed:15299146 ]
LOTUS database [Link]

Showing NP-Card for (2e)-4-[(1r,5s,7r)-1-[(2s,3e,5r,6z)-7-chloro-5,9-dihydroxynona-3,6-dien-2-yl]-6-azaspiro[4.5]decan-7-yl]-2-methyl-n-(2-sulfoethyl)but-2-enimidic acid (NP0188228)

MOL for NP0188228 ((2e)-4-[(1r,5s,7r)-1-[(2s,3e,5r,6z)-7-chloro-5,9-dihydroxynona-3,6-dien-2-yl]-6-azaspiro[4.5]decan-7-yl]-2-methyl-n-(2-sulfoethyl)but-2-enimidic acid)

3D MOL for NP0188228 ((2e)-4-[(1r,5s,7r)-1-[(2s,3e,5r,6z)-7-chloro-5,9-dihydroxynona-3,6-dien-2-yl]-6-azaspiro[4.5]decan-7-yl]-2-methyl-n-(2-sulfoethyl)but-2-enimidic acid)

3D SDF for NP0188228 ((2e)-4-[(1r,5s,7r)-1-[(2s,3e,5r,6z)-7-chloro-5,9-dihydroxynona-3,6-dien-2-yl]-6-azaspiro[4.5]decan-7-yl]-2-methyl-n-(2-sulfoethyl)but-2-enimidic acid)

3D-SDF for NP0188228 ((2e)-4-[(1r,5s,7r)-1-[(2s,3e,5r,6z)-7-chloro-5,9-dihydroxynona-3,6-dien-2-yl]-6-azaspiro[4.5]decan-7-yl]-2-methyl-n-(2-sulfoethyl)but-2-enimidic acid)

PDB for NP0188228 ((2e)-4-[(1r,5s,7r)-1-[(2s,3e,5r,6z)-7-chloro-5,9-dihydroxynona-3,6-dien-2-yl]-6-azaspiro[4.5]decan-7-yl]-2-methyl-n-(2-sulfoethyl)but-2-enimidic acid)

3D PDB for NP0188228 ((2e)-4-[(1r,5s,7r)-1-[(2s,3e,5r,6z)-7-chloro-5,9-dihydroxynona-3,6-dien-2-yl]-6-azaspiro[4.5]decan-7-yl]-2-methyl-n-(2-sulfoethyl)but-2-enimidic acid)

SMILES for NP0188228 ((2e)-4-[(1r,5s,7r)-1-[(2s,3e,5r,6z)-7-chloro-5,9-dihydroxynona-3,6-dien-2-yl]-6-azaspiro[4.5]decan-7-yl]-2-methyl-n-(2-sulfoethyl)but-2-enimidic acid)

INCHI for NP0188228 ((2e)-4-[(1r,5s,7r)-1-[(2s,3e,5r,6z)-7-chloro-5,9-dihydroxynona-3,6-dien-2-yl]-6-azaspiro[4.5]decan-7-yl]-2-methyl-n-(2-sulfoethyl)but-2-enimidic acid)

Structure for NP0188228 ((2e)-4-[(1r,5s,7r)-1-[(2s,3e,5r,6z)-7-chloro-5,9-dihydroxynona-3,6-dien-2-yl]-6-azaspiro[4.5]decan-7-yl]-2-methyl-n-(2-sulfoethyl)but-2-enimidic acid)

3D Structure for NP0188228 ((2e)-4-[(1r,5s,7r)-1-[(2s,3e,5r,6z)-7-chloro-5,9-dihydroxynona-3,6-dien-2-yl]-6-azaspiro[4.5]decan-7-yl]-2-methyl-n-(2-sulfoethyl)but-2-enimidic acid)