NP-MRD: Showing NP-Card for Isodomoic acid G (NP0140764)

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Record Information

Version

2.0

Created at

2022-06-29 21:50:46 UTC

Updated at

2022-06-29 21:50:46 UTC

NP-MRD ID

NP0140764

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isodomoic acid G

Description

Isodomoic acid G, also known as isodomoate g, belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Isodomoic acid G is found in Chondria armata. Isodomoic acid G was first documented in 2003 (PMID: 14507227). Based on a literature review a small amount of articles have been published on Isodomoic acid G (PMID: 21121685) (PMID: 19899794) (PMID: 19807173).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 43 43  0  0  0  0  0  0  0  0999 V2000
    0.2282    2.7686   -0.7472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2288    1.3816   -0.5090 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7116    0.2800   -0.6171 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9987    0.4699   -0.9287 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9787   -0.6403   -1.0450 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0711   -0.3648   -0.0151 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4632   -0.3235    1.3827 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1078   -1.3930   -0.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2827   -1.1093   -0.2771 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7739   -2.6949    0.2789 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4755    1.1044   -0.1979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6055    2.0532   -0.0321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7556    1.2333    0.2909 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1890    0.0860    0.9736 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6971    0.5345    2.2840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7656    1.7118    2.7208 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0952   -0.3976    3.1477 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0038   -0.2433    0.0529 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5400   -0.9010   -1.1981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0584   -2.2568   -0.9108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0174   -2.7461    0.2410 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6070   -3.0224   -1.9248 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1914    2.9046   -0.1904 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4739    2.9104   -1.8116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4710    3.5179   -0.3493 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4440   -0.7549   -0.4571 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3474    1.4711   -1.1047 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4722   -0.5697   -2.0350 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5312   -1.6244   -0.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5436    0.6202   -0.1857 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3936    0.0124    1.2723 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4537   -1.3749    1.7428 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0538    0.3581    1.9984 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9930   -3.4228   -0.3691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7737    2.5165   -1.0398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4389    2.8347    0.7011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4079    1.7755    0.8796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9063   -0.7542    1.0423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6707   -0.9646    3.7801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3144   -0.9404    0.5354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7452   -1.0047   -1.9553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3094   -0.2364   -1.6391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4374   -2.8048   -2.9168 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  1  0
  2 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 18  1  0
 18 19  1  0
 19 20  1  0
 20 22  1  0
 20 21  2  0
 14 15  1  0
 15 17  1  0
 15 16  2  0
  6  8  1  0
  8 10  1  0
  8  9  2  0
 18 11  1  0
  7 31  1  0
  7 32  1  0
  7 33  1  0
  6 30  1  6
  5 28  1  0
  5 29  1  0
  4 27  1  0
  3 26  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 14 38  1  1
 18 40  1  1
 19 41  1  0
 19 42  1  0
 22 43  1  0
 17 39  1  0
 10 34  1  0
M  END


  Mrv1652306292223502D          

 22 22  0  0  1  0            999 V2000
   -1.5757    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5757    3.1768    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8612    3.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4974    0.3323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2820    0.5872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3259   -0.4747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0059   -1.5764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1501   -0.7365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2901    3.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2901    4.4143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0046    3.1768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  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  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 10 16  1  6  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
  6 19  1  0  0  0  0
  2 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0140764

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](C\C=C\C(\C)=C1\CN[C@@H]([C@H]1CC(O)=O)C(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H21NO6/c1-8(4-3-5-9(2)14(19)20)11-7-16-13(15(21)22)10(11)6-12(17)18/h3-4,9-10,13,16H,5-7H2,1-2H3,(H,17,18)(H,19,20)(H,21,22)/b4-3+,11-8-/t9-,10+,13+/m1/s1

> <INCHI_KEY>
MKCCCBSBSRCARB-NMWGDLGCSA-N

> <FORMULA>
C15H21NO6

> <MOLECULAR_WEIGHT>
311.334

> <EXACT_MASS>
311.1368874

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0      -2.941   4.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.941   5.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.608   6.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.274   5.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.274   4.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       1.830  -0.290   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.651   1.651   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.795   0.620   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -4.260   1.096   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -2.475  -0.886   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.615  -1.536   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.011  -2.943   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -2.147  -1.375   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.393   4.390   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.275   6.700   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -4.275   8.240   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -5.609   5.930   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   19                                                  
CONECT    7    6    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10    7   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   10   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19    6                                                            
CONECT   20    2   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

View in JSmol

Synonyms

Value	Source
Isodomoate g	Generator

Chemical Formula

C₁₅H₂₁NO₆

Average Mass

311.3340 Da

Monoisotopic Mass

311.13689 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@H](C\C=C\C(\C)=C1\CN[C@@H]([C@H]1CC(O)=O)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C15H21NO6/c1-8(4-3-5-9(2)14(19)20)11-7-16-13(15(21)22)10(11)6-12(17)18/h3-4,9-10,13,16H,5-7H2,1-2H3,(H,17,18)(H,19,20)(H,21,22)/b4-3+,11-8-/t9-,10+,13+/m1/s1

InChI Key

MKCCCBSBSRCARB-NMWGDLGCSA-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
Chondria armata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Proline and derivatives

Alternative Parents

Substituents

Proline or derivatives
Alpha-amino acid
L-alpha-amino acid
Tricarboxylic acid or derivatives
Pyrrolidine carboxylic acid
Pyrrolidine carboxylic acid or derivatives
Pyrrolidine
Amino acid
Carboxylic acid
Secondary aliphatic amine
Secondary amine
Azacycle
Organoheterocyclic compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Amine
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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

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

9337806

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11162706

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Denmark SE, Liu JH, Muhuhi JM: Stereocontrolled total syntheses of isodomoic acids G and H via a unified strategy. J Org Chem. 2011 Jan 7;76(1):201-15. doi: 10.1021/jo101790z. Epub 2010 Dec 1. [PubMed:21121685 ]
Ni Y, Kassab RM, Chevliakov MV, Montgomery J: Total syntheses of isodomoic acids G and H: an exercise in tetrasubstituted alkene synthesis. J Am Chem Soc. 2009 Dec 9;131(48):17714-8. doi: 10.1021/ja907931u. [PubMed:19899794 ]
Denmark SE, Liu JH, Muhuhi JM: Total syntheses of isodomoic acids G and H. J Am Chem Soc. 2009 Oct 14;131(40):14188-9. doi: 10.1021/ja9063475. [PubMed:19807173 ]
Ni Y, Amarasinghe KK, Ksebati B, Montgomery J: First total synthesis and stereochemical definition of isodomoic acid G. Org Lett. 2003 Oct 2;5(20):3771-3. doi: 10.1021/ol0355783. [PubMed:14507227 ]

Showing NP-Card for Isodomoic acid G (NP0140764)

MOL for NP0140764 (Isodomoic acid G)

3D MOL for NP0140764 (Isodomoic acid G)

3D SDF for NP0140764 (Isodomoic acid G)

3D-SDF for NP0140764 (Isodomoic acid G)

PDB for NP0140764 (Isodomoic acid G)

3D PDB for NP0140764 (Isodomoic acid G)

SMILES for NP0140764 (Isodomoic acid G)

INCHI for NP0140764 (Isodomoic acid G)

Structure for NP0140764 (Isodomoic acid G)

3D Structure for NP0140764 (Isodomoic acid G)