NP-MRD: Showing NP-Card for 5-hydroxy-4-[(2e,4e,6r,7r,8s,9s,11r,12r)-1,7,9,11-tetrahydroxy-4,6,8,12-tetramethyl-13-oxotetradeca-2,4-dien-1-ylidene]-2h-pyrrol-3-one (NP0195477)

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Record Information

Version

2.0

Created at

2022-09-04 13:21:04 UTC

Updated at

2022-09-04 13:21:04 UTC

NP-MRD ID

NP0195477

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-hydroxy-4-[(2e,4e,6r,7r,8s,9s,11r,12r)-1,7,9,11-tetrahydroxy-4,6,8,12-tetramethyl-13-oxotetradeca-2,4-dien-1-ylidene]-2h-pyrrol-3-one

Description

Tirandamycin K belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. 5-hydroxy-4-[(2e,4e,6r,7r,8s,9s,11r,12r)-1,7,9,11-tetrahydroxy-4,6,8,12-tetramethyl-13-oxotetradeca-2,4-dien-1-ylidene]-2h-pyrrol-3-one was first documented in 2016 (PMID: 28989201). Based on a literature review very few articles have been published on Tirandamycin K.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042215212D          

 30 30  0  0  1  0            999 V2000
    5.7271   -5.9918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4416   -5.5793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4416   -4.7543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1561   -5.9918    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1561   -6.8168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8706   -5.5793    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8706   -4.7543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5850   -5.9918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2995   -5.5793    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2995   -4.7543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0140   -5.9918    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.0140   -6.8168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7284   -5.5793    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.7284   -4.7543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4429   -5.9918    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.4429   -6.8168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1574   -5.5793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8719   -5.9918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8719   -6.8168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5863   -5.5793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3008   -5.9918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0153   -5.5793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0153   -4.7543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7297   -5.9918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4834   -5.6563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6549   -4.8493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0354   -6.2694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6229   -6.9838    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8160   -6.8123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2029   -7.3643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  4  0  0  0
 22 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 24 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END

     RDKit          3D

 63 63  0  0  0  0  0  0  0  0999 V2000
    7.6822    0.9419   -0.2242 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9534    0.1814    0.8254 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3983    0.1077    1.9379 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6750   -0.4686    0.4439 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8248    0.6574   -0.1164 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0509   -1.1898    1.5685 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0638   -2.1273    1.9894 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8301   -1.9333    1.5181 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4896   -1.5010    1.1398 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4241   -1.3786   -0.2517 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7959   -0.4395    1.8563 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8377   -0.6861    3.4006 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3211   -0.2254    1.6193 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3378   -1.3829    2.0483 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1236    0.0936    0.2351 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5137    1.3203   -0.3345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5067   -0.1970   -0.1067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4910    0.6480   -0.4504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1440    2.0917   -0.4877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7539    0.2273   -0.8476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8555   -0.1348   -1.1940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1386   -0.5614   -1.5976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4694   -1.8981   -1.6350 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0999    0.2913   -1.9455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1310    1.7358   -2.0057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2726    2.5761   -1.7019 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4908    2.1401   -2.5492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1116    0.9034   -2.7536 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4465   -0.1084   -2.4617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8057   -1.4528   -2.5581 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2220    0.7958   -1.2259 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7170    2.0246   -0.0665 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7379    0.6177   -0.3387 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9355   -1.1379   -0.4281 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5020    1.4930   -0.5023 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2132    0.3979   -0.9859 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1645    1.0803    0.6610 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1146   -0.4536    2.4537 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6525   -2.7721    2.6179 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7291   -2.4713    2.5404 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0182   -2.8723    0.8637 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8522   -2.4490    1.3155 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1722   -1.8259   -0.7176 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2719    0.5373    1.7180 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9492   -1.2816    3.7089 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7068    0.2942    3.9322 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7200   -1.2367    3.7041 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0543    0.5905    2.3661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0831   -1.1653    2.6744 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4224   -0.7457   -0.3951 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1913    1.6208   -1.3300 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6169    2.1629    0.4132 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6428    1.1383   -0.5125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8784   -1.2479   -0.1052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9875    2.4185   -1.5255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5435    2.4719    0.2973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1774    2.5861   -0.2586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3568    1.4539   -0.4566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3518   -1.4407   -1.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8964   -2.5105   -2.2353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4058    2.7398   -3.4711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0143    2.7574   -1.7613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5934   -1.8015   -2.0178 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
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  4  2  1  0
  2  1  1  0
  2  3  2  0
 29 24  1  0
 16 51  1  0
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 16 53  1  0
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 19 56  1  0
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 30 63  1  0
 13 48  1  1
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  6 38  1  1
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  4 34  1  6
  5 35  1  0
  5 36  1  0
  5 37  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
M  END


  Mrv1652309042215212D          

 30 30  0  0  1  0            999 V2000
    5.7271   -5.9918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4416   -5.5793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4416   -4.7543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1561   -5.9918    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1561   -6.8168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8706   -5.5793    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8706   -4.7543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5850   -5.9918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2995   -5.5793    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2995   -4.7543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0140   -5.9918    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.0140   -6.8168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7284   -5.5793    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.7284   -4.7543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4429   -5.9918    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.4429   -6.8168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1574   -5.5793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.8719   -6.8168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5863   -5.5793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3008   -5.9918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0153   -5.5793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0153   -4.7543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7297   -5.9918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4834   -5.6563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6549   -4.8493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0354   -6.2694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6229   -6.9838    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8160   -6.8123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2029   -7.3643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  1  0  0  0
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 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  4  0  0  0
 22 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 24 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0195477

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](\C=C(/C)\C=C\C(O)=C1C(=O)CN=C1O)[C@@H](O)[C@@H](C)[C@@H](O)C[C@@H](O)[C@@H](C)C(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H33NO7/c1-11(6-7-16(25)20-19(28)10-23-22(20)30)8-12(2)21(29)14(4)18(27)9-17(26)13(3)15(5)24/h6-8,12-14,17-18,21,25-27,29H,9-10H2,1-5H3,(H,23,30)/b7-6+,11-8+,20-16?/t12-,13+,14+,17-,18+,21-/m1/s1

> <INCHI_KEY>
GNAYWSKUDSTFNI-LGOCCUDOSA-N

> <FORMULA>
C22H33NO7

> <MOLECULAR_WEIGHT>
423.506

> <EXACT_MASS>
423.225702407

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
45.13728567234086

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-hydroxy-4-[(2E,4E,6R,7R,8S,9S,11R,12R)-1,7,9,11-tetrahydroxy-4,6,8,12-tetramethyl-13-oxotetradeca-2,4-dien-1-ylidene]-3,4-dihydro-2H-pyrrol-3-one

> <JCHEM_LOGP>
0.7598741630000003

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.72888803693627

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.056118031845722

> <JCHEM_PKA_STRONGEST_BASIC>
1.3200802255993607

> <JCHEM_POLAR_SURFACE_AREA>
147.65

> <JCHEM_REFRACTIVITY>
115.73659999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-4-[(2E,4E,6R,7R,8S,9S,11R,12R)-1,7,9,11-tetrahydroxy-4,6,8,12-tetramethyl-13-oxotetradeca-2,4-dien-1-ylidene]-2H-pyrrol-3-one

> <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      10.691 -11.185   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.024 -10.415   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      12.024  -8.875   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      13.358 -11.185   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.358 -12.725   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.692 -10.415   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      14.692  -8.875   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      16.025 -11.185   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      17.359 -10.415   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      17.359  -8.875   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      18.693 -11.185   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      18.693 -12.725   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      20.026 -10.415   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      20.026  -8.875   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      21.360 -11.185   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      21.360 -12.725   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      22.694 -10.415   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      24.027 -11.185   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      24.027 -12.725   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      25.361 -10.415   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      26.695 -11.185   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      28.028 -10.415   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      28.028  -8.875   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      29.362 -11.185   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      30.769 -10.558   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      31.089  -9.052   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      31.799 -11.703   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0      31.029 -13.037   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0      29.523 -12.716   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      28.379 -13.747   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   29                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   24   30                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₃NO₇

Average Mass

423.5060 Da

Monoisotopic Mass

423.22570 Da

IUPAC Name

5-hydroxy-4-[(2E,4E,6R,7R,8S,9S,11R,12R)-1,7,9,11-tetrahydroxy-4,6,8,12-tetramethyl-13-oxotetradeca-2,4-dien-1-ylidene]-3,4-dihydro-2H-pyrrol-3-one

Traditional Name

5-hydroxy-4-[(2E,4E,6R,7R,8S,9S,11R,12R)-1,7,9,11-tetrahydroxy-4,6,8,12-tetramethyl-13-oxotetradeca-2,4-dien-1-ylidene]-2H-pyrrol-3-one

CAS Registry Number

Not Available

SMILES

C[C@H](\C=C(/C)\C=C\C(O)=C1C(=O)CN=C1O)[C@@H](O)[C@@H](C)[C@@H](O)C[C@@H](O)[C@@H](C)C(C)=O

InChI Identifier

InChI=1S/C22H33NO7/c1-11(6-7-16(25)20-19(28)10-23-22(20)30)8-12(2)21(29)14(4)18(27)9-17(26)13(3)15(5)24/h6-8,12-14,17-18,21,25-27,29H,9-10H2,1-5H3,(H,23,30)/b7-6+,11-8+,20-16?/t12-,13+,14+,17-,18+,21-/m1/s1

InChI Key

GNAYWSKUDSTFNI-LGOCCUDOSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Farsesane sesquiterpenoid
Sesquiterpenoid
Beta-hydroxy ketone
Vinylogous acid
Cyclic carboximidic acid
Pyrroline
Cyclic ketone
Lactim
Secondary alcohol
Ketone
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Polyol
Enol
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
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
logP	0.76	ChemAxon
pKa (Strongest Acidic)	4.06	ChemAxon
pKa (Strongest Basic)	1.32	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	147.65 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	115.74 m³·mol⁻¹	ChemAxon
Polarizability	45.14 Å³	ChemAxon
Number of Rings	1	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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78436600

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139583977

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhang X, Li Z, Du L, Chlipala GE, Lopez PC, Zhang W, Sherman DH, Li S: Identification of an unexpected shunt pathway product provides new insights into tirandamycin biosynthesis. Tetrahedron Lett. 2016 Dec 28;57(52):5919-5923. doi: 10.1016/j.tetlet.2016.11.080. Epub 2016 Nov 19. [PubMed:28989201 ]
LOTUS database [Link]

Showing NP-Card for 5-hydroxy-4-[(2e,4e,6r,7r,8s,9s,11r,12r)-1,7,9,11-tetrahydroxy-4,6,8,12-tetramethyl-13-oxotetradeca-2,4-dien-1-ylidene]-2h-pyrrol-3-one (NP0195477)

MOL for NP0195477 (5-hydroxy-4-[(2e,4e,6r,7r,8s,9s,11r,12r)-1,7,9,11-tetrahydroxy-4,6,8,12-tetramethyl-13-oxotetradeca-2,4-dien-1-ylidene]-2h-pyrrol-3-one)

3D MOL for NP0195477 (5-hydroxy-4-[(2e,4e,6r,7r,8s,9s,11r,12r)-1,7,9,11-tetrahydroxy-4,6,8,12-tetramethyl-13-oxotetradeca-2,4-dien-1-ylidene]-2h-pyrrol-3-one)

3D SDF for NP0195477 (5-hydroxy-4-[(2e,4e,6r,7r,8s,9s,11r,12r)-1,7,9,11-tetrahydroxy-4,6,8,12-tetramethyl-13-oxotetradeca-2,4-dien-1-ylidene]-2h-pyrrol-3-one)

3D-SDF for NP0195477 (5-hydroxy-4-[(2e,4e,6r,7r,8s,9s,11r,12r)-1,7,9,11-tetrahydroxy-4,6,8,12-tetramethyl-13-oxotetradeca-2,4-dien-1-ylidene]-2h-pyrrol-3-one)

PDB for NP0195477 (5-hydroxy-4-[(2e,4e,6r,7r,8s,9s,11r,12r)-1,7,9,11-tetrahydroxy-4,6,8,12-tetramethyl-13-oxotetradeca-2,4-dien-1-ylidene]-2h-pyrrol-3-one)

3D PDB for NP0195477 (5-hydroxy-4-[(2e,4e,6r,7r,8s,9s,11r,12r)-1,7,9,11-tetrahydroxy-4,6,8,12-tetramethyl-13-oxotetradeca-2,4-dien-1-ylidene]-2h-pyrrol-3-one)

SMILES for NP0195477 (5-hydroxy-4-[(2e,4e,6r,7r,8s,9s,11r,12r)-1,7,9,11-tetrahydroxy-4,6,8,12-tetramethyl-13-oxotetradeca-2,4-dien-1-ylidene]-2h-pyrrol-3-one)

INCHI for NP0195477 (5-hydroxy-4-[(2e,4e,6r,7r,8s,9s,11r,12r)-1,7,9,11-tetrahydroxy-4,6,8,12-tetramethyl-13-oxotetradeca-2,4-dien-1-ylidene]-2h-pyrrol-3-one)

Structure for NP0195477 (5-hydroxy-4-[(2e,4e,6r,7r,8s,9s,11r,12r)-1,7,9,11-tetrahydroxy-4,6,8,12-tetramethyl-13-oxotetradeca-2,4-dien-1-ylidene]-2h-pyrrol-3-one)

3D Structure for NP0195477 (5-hydroxy-4-[(2e,4e,6r,7r,8s,9s,11r,12r)-1,7,9,11-tetrahydroxy-4,6,8,12-tetramethyl-13-oxotetradeca-2,4-dien-1-ylidene]-2h-pyrrol-3-one)