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Showing NP-Card for Torreyanic acid (NP0050365)

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Record Information
Version2.0
Created at2022-04-27 20:55:51 UTC
Updated at2022-04-27 20:55:51 UTC
NP-MRD IDNP0050365
Secondary Accession NumbersNone
Natural Product Identification
Common NameTorreyanic acid
Description(2E)-4-[(1S,2S,4S,6R,11S,12S,13S,16S,18R,22R)-16-[(2E)-3-carboxy-3-methylprop-2-en-1-yl]-3,7,15,19-tetraoxo-11,22-dipentyl-5,10,17,21-tetraoxaheptacyclo[11.7.2.0²,⁸.0²,¹².0⁴,⁶.0¹⁴,²⁰.0¹⁶,¹⁸]Docosa-8,14(20)-dien-4-yl]-2-methylbut-2-enoic acid belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system. Torreyanic acid is found in Pestalotiopsis microspora. Based on a literature review very few articles have been published on (2E)-4-[(1S,2S,4S,6R,11S,12S,13S,16S,18R,22R)-16-[(2E)-3-carboxy-3-methylprop-2-en-1-yl]-3,7,15,19-tetraoxo-11,22-dipentyl-5,10,17,21-tetraoxaheptacyclo[11.7.2.0²,⁸.0²,¹².0⁴,⁶.0¹⁴,²⁰.0¹⁶,¹⁸]Docosa-8,14(20)-dien-4-yl]-2-methylbut-2-enoic acid.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0050365 (Torreyanic acid)


  Mrv1652304272222552D          

 50 56  0  0  1  0            999 V2000
    3.8884    3.2849    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4483    2.5332    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3975    2.6936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7365    3.4457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3262    4.3490    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6188    4.1315    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2256    4.9370    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4744    5.2815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9363    4.6397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2293    3.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2504    3.6710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6034    4.3616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1043    2.8475    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6732    2.2501    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4585    2.5406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7768    1.7151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8713    2.0561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7295    1.3415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3041    0.6090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4791    0.6110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0684    1.3265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0649   -0.1024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2399   -0.1004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4756   -0.8179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8411    5.5914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7618    6.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4987    6.9064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3713    7.7329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0146    8.2494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0473    3.7192    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8513    3.0714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0838    3.8033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2267    3.3065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5381    4.0141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5663    3.6176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4543    2.8002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5574    3.5282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8434    4.3341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0393    2.8585    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7003    2.1064    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8794    2.0239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8396    1.1648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5211    2.1889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8373    3.3057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6744    3.1501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9494    2.3723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4132    1.7452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7605    2.2215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2966    2.8485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0355    1.4437    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  2  0  0  0  0
  5  4  1  1  0  0  0
  6  5  1  1  0  0  0
  1  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  2  0  0  0  0
  1 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  1 15  1  0  0  0  0
 15 16  2  0  0  0  0
 14 17  1  0  0  0  0
 13 17  1  1  0  0  0
 14 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
  7 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
  5 30  1  0  0  0  0
 30 31  1  0  0  0  0
  2 31  1  6  0  0  0
 30 32  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
  4 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
  3 41  1  0  0  0  0
 41 42  2  0  0  0  0
 40 43  1  1  0  0  0
 39 43  1  0  0  0  0
 39 44  1  6  0  0  0
 44 45  1  0  0  0  0
 45 46  2  0  0  0  0
 46 47  1  0  0  0  0
 46 48  1  0  0  0  0
 48 49  2  0  0  0  0
 48 50  1  0  0  0  0
M  END
Download

3D MOL for NP0050365 (Torreyanic acid)

Download
3D SDF for NP0050365 (Torreyanic acid)

  Mrv1652304272222552D          

 50 56  0  0  1  0            999 V2000
    3.8884    3.2849    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4483    2.5332    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3975    2.6936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7365    3.4457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3262    4.3490    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6188    4.1315    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2256    4.9370    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4744    5.2815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9363    4.6397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2293    3.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2504    3.6710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6034    4.3616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1043    2.8475    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6732    2.2501    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4585    2.5406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7768    1.7151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8713    2.0561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7295    1.3415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3041    0.6090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4791    0.6110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0684    1.3265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0649   -0.1024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2399   -0.1004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4756   -0.8179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8411    5.5914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7618    6.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4987    6.9064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3713    7.7329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0146    8.2494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0473    3.7192    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8513    3.0714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0838    3.8033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2267    3.3065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5381    4.0141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5663    3.6176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4543    2.8002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5574    3.5282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8434    4.3341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0393    2.8585    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7003    2.1064    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8794    2.0239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8396    1.1648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5211    2.1889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8373    3.3057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6744    3.1501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9494    2.3723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4132    1.7452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7605    2.2215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2966    2.8485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0355    1.4437    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  2  0  0  0  0
  5  4  1  1  0  0  0
  6  5  1  1  0  0  0
  1  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  2  0  0  0  0
  1 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  1 15  1  0  0  0  0
 15 16  2  0  0  0  0
 14 17  1  0  0  0  0
 13 17  1  1  0  0  0
 14 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
  7 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
  5 30  1  0  0  0  0
 30 31  1  0  0  0  0
  2 31  1  6  0  0  0
 30 32  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
  4 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
  3 41  1  0  0  0  0
 41 42  2  0  0  0  0
 40 43  1  1  0  0  0
 39 43  1  0  0  0  0
 39 44  1  6  0  0  0
 44 45  1  0  0  0  0
 45 46  2  0  0  0  0
 46 47  1  0  0  0  0
 46 48  1  0  0  0  0
 48 49  2  0  0  0  0
 48 50  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050365

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC[C@@H]1OC=C2C(=O)[C@@H]3O[C@]3(C\C=C(/C)C(O)=O)C(=O)[C@]22[C@H]3O[C@H](CCCCC)[C@@H]([C@H]12)C1=C3C(=O)[C@@H]2O[C@]2(C\C=C(/C)C(O)=O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C38H44O12/c1-5-7-9-11-21-23-24-25(28(40)32-36(49-32,29(24)41)15-13-18(3)33(42)43)30(48-21)38-20(17-47-22(26(23)38)12-10-8-6-2)27(39)31-37(50-31,35(38)46)16-14-19(4)34(44)45/h13-14,17,21-23,26,30-32H,5-12,15-16H2,1-4H3,(H,42,43)(H,44,45)/b18-13+,19-14+/t21-,22+,23-,26+,30+,31+,32+,36-,37+,38-/m1/s1

> <INCHI_KEY>
DQBVXDMPCDAQGS-OYKCDUBWSA-N

> <FORMULA>
C38H44O12

> <MOLECULAR_WEIGHT>
692.758

> <EXACT_MASS>
692.283276857

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
94

> <JCHEM_AVERAGE_POLARIZABILITY>
71.31659392065745

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-4-[(1S,2S,4S,6R,11S,12S,13S,16S,18R,22R)-16-[(2E)-3-carboxy-3-methylprop-2-en-1-yl]-3,7,15,19-tetraoxo-11,22-dipentyl-5,10,17,21-tetraoxaheptacyclo[11.7.2.0^{2,8}.0^{2,12}.0^{4,6}.0^{14,20}.0^{16,18}]docosa-8,14(20)-dien-4-yl]-2-methylbut-2-enoic acid

> <ALOGPS_LOGP>
3.58

> <JCHEM_LOGP>
5.772786605666665

> <ALOGPS_LOGS>
-5.31

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.186003377426353

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5839307369172464

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7749324894954044

> <JCHEM_POLAR_SURFACE_AREA>
186.39999999999998

> <JCHEM_REFRACTIVITY>
176.86380000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.37e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-4-[(1S,2S,4S,6R,11S,12S,13S,16S,18R,22R)-16-[(2E)-3-carboxy-3-methylprop-2-en-1-yl]-3,7,15,19-tetraoxo-11,22-dipentyl-5,10,17,21-tetraoxaheptacyclo[11.7.2.0^{2,8}.0^{2,12}.0^{4,6}.0^{14,20}.0^{16,18}]docosa-8,14(20)-dien-4-yl]-2-methylbut-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0050365 (Torreyanic acid)
Download
PDB for NP0050365 (Torreyanic acid)
HEADER    PROTEIN                                 27-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-22         0                                  
HETATM    1  C   UNK     0       7.258   6.132   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.304   4.729   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.075   5.028   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.708   6.432   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.942   8.118   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.622   7.712   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.888   9.216   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.486   9.859   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.481   8.661   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.028   7.109   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.201   6.852   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.993   8.142   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.928   5.315   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.990   4.200   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.456   4.742   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       7.050   3.202   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       3.493   3.838   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.095   2.504   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.301   1.137   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.761   1.141   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.994   2.476   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.988  -0.191   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.448  -0.187   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       2.755  -1.527   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       9.037  10.437   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.889  12.018   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.264  12.892   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.026  14.435   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.227  15.399   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.422   6.943   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       9.056   5.733   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       7.623   7.099   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.023   6.172   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.738   7.493   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.924   6.753   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.715   5.227   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      12.240   6.586   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      12.774   8.090   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      13.140   5.336   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      12.507   3.932   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      10.975   3.778   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      10.901   2.174   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      14.039   4.086   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      14.630   6.171   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      16.192   5.880   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      16.706   4.428   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      15.705   3.258   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      18.220   4.147   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      19.220   5.317   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0      18.733   2.695   0.000  0.00  0.00           O+0
CONECT    1    2    6   10   15                                             
CONECT    2    1    3   31                                                  
CONECT    3    2    4   41                                                  
CONECT    4    3    5   37                                                  
CONECT    5    4    6   30                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8   25                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    1   11                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   17                                                  
CONECT   14   13   15   17   18                                             
CONECT   15   14    1   16                                                  
CONECT   16   15                                                            
CONECT   17   14   13                                                       
CONECT   18   14   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25    7   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30    5   31   32                                                  
CONECT   31   30    2                                                       
CONECT   32   30   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35                                                            
CONECT   37    4   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40   43   44                                             
CONECT   40   39   41   43                                                  
CONECT   41   40    3   42                                                  
CONECT   42   41                                                            
CONECT   43   40   39                                                       
CONECT   44   39   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47   48                                                  
CONECT   47   46                                                            
CONECT   48   46   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48                                                            
MASTER        0    0    0    0    0    0    0    0   50    0  112    0
END

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3D PDB for NP0050365 (Torreyanic acid)
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SMILES for NP0050365 (Torreyanic acid)
CCCCC[C@@H]1OC=C2C(=O)[C@@H]3O[C@]3(C\C=C(/C)C(O)=O)C(=O)[C@]22[C@H]3O[C@H](CCCCC)[C@@H]([C@H]12)C1=C3C(=O)[C@@H]2O[C@]2(C\C=C(/C)C(O)=O)C1=O
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INCHI for NP0050365 (Torreyanic acid)
InChI=1S/C38H44O12/c1-5-7-9-11-21-23-24-25(28(40)32-36(49-32,29(24)41)15-13-18(3)33(42)43)30(48-21)38-20(17-47-22(26(23)38)12-10-8-6-2)27(39)31-37(50-31,35(38)46)16-14-19(4)34(44)45/h13-14,17,21-23,26,30-32H,5-12,15-16H2,1-4H3,(H,42,43)(H,44,45)/b18-13+,19-14+/t21-,22+,23-,26+,30+,31+,32+,36-,37+,38-/m1/s1
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View in JSmol
Synonyms
ValueSource
(2E)-4-[(1S,2S,4S,6R,11S,12S,13S,16S,18R,22R)-16-[(2E)-3-Carboxy-3-methylprop-2-en-1-yl]-3,7,15,19-tetraoxo-11,22-dipentyl-5,10,17,21-tetraoxaheptacyclo[11.7.2.0,.0,.0,.0,.0,]docosa-8,14(20)-dien-4-yl]-2-methylbut-2-enoateGenerator
Chemical FormulaC38H44O12
Average Mass692.7580 Da
Monoisotopic Mass692.28328 Da
IUPAC Name(2E)-4-[(1S,2S,4S,6R,11S,12S,13S,16S,18R,22R)-16-[(2E)-3-carboxy-3-methylprop-2-en-1-yl]-3,7,15,19-tetraoxo-11,22-dipentyl-5,10,17,21-tetraoxaheptacyclo[11.7.2.0^{2,8}.0^{2,12}.0^{4,6}.0^{14,20}.0^{16,18}]docosa-8,14(20)-dien-4-yl]-2-methylbut-2-enoic acid
Traditional Name(2E)-4-[(1S,2S,4S,6R,11S,12S,13S,16S,18R,22R)-16-[(2E)-3-carboxy-3-methylprop-2-en-1-yl]-3,7,15,19-tetraoxo-11,22-dipentyl-5,10,17,21-tetraoxaheptacyclo[11.7.2.0^{2,8}.0^{2,12}.0^{4,6}.0^{14,20}.0^{16,18}]docosa-8,14(20)-dien-4-yl]-2-methylbut-2-enoic acid
CAS Registry NumberNot Available
SMILES
CCCCC[C@@H]1OC=C2C(=O)[C@@H]3O[C@]3(C\C=C(/C)C(O)=O)C(=O)[C@]22[C@H]3O[C@H](CCCCC)[C@@H]([C@H]12)C1=C3C(=O)[C@@H]2O[C@]2(C\C=C(/C)C(O)=O)C1=O
InChI Identifier
InChI=1S/C38H44O12/c1-5-7-9-11-21-23-24-25(28(40)32-36(49-32,29(24)41)15-13-18(3)33(42)43)30(48-21)38-20(17-47-22(26(23)38)12-10-8-6-2)27(39)31-37(50-31,35(38)46)16-14-19(4)34(44)45/h13-14,17,21-23,26,30-32H,5-12,15-16H2,1-4H3,(H,42,43)(H,44,45)/b18-13+,19-14+/t21-,22+,23-,26+,30+,31+,32+,36-,37+,38-/m1/s1
InChI KeyDQBVXDMPCDAQGS-OYKCDUBWSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Pestalotiopsis microsporaFungi
Chemical Taxonomy
Description Belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassNaphthopyrans  
Sub ClassNaphthopyranones  
Direct ParentNaphthopyranones  
Alternative Parents
Substituents
  • Naphthopyranone
    • 

  • Naphthalene
    • 

  • Cyclohexenone
    • 

  • Methyl-branched fatty acid
    • 

  • Pyranone
    • 

  • Oxepane
    • 

  • Heterocyclic fatty acid
    • 

  • Branched fatty acid
    • 

  • Fatty acyl
    • 

  • Fatty acid
    • 

  • Unsaturated fatty acid
    • 

  • Pyran
    • 

  • Oxane
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Vinylogous ester
    • 

  • Ketone
    • 

  • Oxacycle
    • 

  • Ether
    • 

  • Oxirane
    • 

  • Dialkyl ether
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.58ALOGPS
logP5.77ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)3.58ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area186.4 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity176.86 m³·mol⁻¹ChemAxon
Polarizability71.32 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound163055371  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available