NP-MRD: Showing NP-Card for (1s,17r,19e,22s,24s,26s)-26-benzyl-8,9,22,28-tetrahydroxy-11-methoxy-17,24-dimethyl-23-methylidene-3,13-dioxo-2-oxa-27-azapentacyclo[19.7.0.0¹,²⁵.0⁶,¹².0⁷,¹⁰]octacosa-4,6(12),19,27-tetraene-7-carboximidic acid (NP0225933)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-06 04:48:36 UTC

Updated at

2022-09-06 04:48:36 UTC

NP-MRD ID

NP0225933

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,17r,19e,22s,24s,26s)-26-benzyl-8,9,22,28-tetrahydroxy-11-methoxy-17,24-dimethyl-23-methylidene-3,13-dioxo-2-oxa-27-azapentacyclo[19.7.0.0¹,²⁵.0⁶,¹².0⁷,¹⁰]octacosa-4,6(12),19,27-tetraene-7-carboximidic acid

Description

Phomachalasin A belongs to the class of organic compounds known as isoindoles and derivatives. These are polycyclic compounds containing an isoindole moiety, which is structurally characterized by a cyclohexadiene fused to a pyrrole ring. (1s,17r,19e,22s,24s,26s)-26-benzyl-8,9,22,28-tetrahydroxy-11-methoxy-17,24-dimethyl-23-methylidene-3,13-dioxo-2-oxa-27-azapentacyclo[19.7.0.0¹,²⁵.0⁶,¹².0⁷,¹⁰]octacosa-4,6(12),19,27-tetraene-7-carboximidic acid is found in Boeremia exigua. Based on a literature review very few articles have been published on Phomachalasin A.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062206482D          

 49 54  0  0  1  0            999 V2000
   -0.9611   -2.0104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1102   -2.0402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3214   -1.3371    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1636   -0.6392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1461   -1.3594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7145   -0.7615    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5457    0.0739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7874    0.3259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1707   -0.2221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6122    0.0381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7784    0.8462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1617    1.3941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6212    1.1340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4589   -1.1173    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1900   -1.7657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4873   -2.6535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5392   -2.0848    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3639   -2.1071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7955   -1.4040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3697   -0.5183    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6202   -1.4263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9330   -2.0670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5816   -2.8547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9747   -3.5801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5430   -4.2831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8848   -4.8441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9361   -5.0085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5044   -5.7116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6797   -5.6893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2867   -4.9639    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5602   -4.2338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4620   -4.9416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0689   -4.2163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5006   -3.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1075   -2.7879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2828   -2.7656    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3346   -3.3824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7860   -3.4304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5006   -3.9408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3294   -3.7439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8943   -2.6126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2501   -1.8682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0798   -1.5738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5058   -1.5124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9619   -0.7276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1500   -2.2568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3787   -1.7990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9146   -2.3616    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5083   -0.7816    0.0000 O   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  1  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
  6 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 17 15  1  1  0  0  0
  5 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 21 19  1  4  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 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  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 17 35  1  0  0  0  0
 35 36  1  0  0  0  0
  2 36  1  0  0  0  0
 36 37  1  6  0  0  0
 24 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 38 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 44  1  0  0  0  0
 44 45  1  0  0  0  0
 44 46  1  0  0  0  0
 23 46  1  0  0  0  0
 41 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  2  0  0  0  0
 47 49  1  0  0  0  0
M  END


  Mrv1652309062206482D          

 49 54  0  0  1  0            999 V2000
   -0.9611   -2.0104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1102   -2.0402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3214   -1.3371    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1636   -0.6392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1461   -1.3594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7145   -0.7615    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5457    0.0739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7874    0.3259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1707   -0.2221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6122    0.0381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7784    0.8462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1617    1.3941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6212    1.1340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4589   -1.1173    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1900   -1.7657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4873   -2.6535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5392   -2.0848    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3639   -2.1071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7955   -1.4040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3697   -0.5183    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6202   -1.4263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9330   -2.0670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5816   -2.8547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9747   -3.5801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5430   -4.2831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8848   -4.8441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9361   -5.0085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5044   -5.7116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6797   -5.6893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2867   -4.9639    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5602   -4.2338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4620   -4.9416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0689   -4.2163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5006   -3.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1075   -2.7879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2828   -2.7656    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3346   -3.3824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7860   -3.4304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5006   -3.9408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3294   -3.7439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8943   -2.6126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2501   -1.8682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0798   -1.5738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5058   -1.5124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9619   -0.7276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1500   -2.2568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3787   -1.7990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9146   -2.3616    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5083   -0.7816    0.0000 O   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  1  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
  6 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 17 15  1  1  0  0  0
  5 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 21 19  1  4  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 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  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 17 35  1  0  0  0  0
 35 36  1  0  0  0  0
  2 36  1  0  0  0  0
 36 37  1  6  0  0  0
 24 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 38 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 44  1  0  0  0  0
 44 45  1  0  0  0  0
 44 46  1  0  0  0  0
 23 46  1  0  0  0  0
 41 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  2  0  0  0  0
 47 49  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0225933

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1C2C(O)C(O)C2(C(O)=N)C2=C1C(=O)CCC[C@@H](C)C\C=C\C1[C@H](O)C(=C)[C@@H](C)C3[C@H](CC4=CC=CC=C4)N=C(O)[C@@]13OC(=O)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C38H46N2O9/c1-19-10-8-14-24-31(43)21(3)20(2)29-25(18-22-12-6-5-7-13-22)40-36(47)38(24,29)49-27(42)17-16-23-28(26(41)15-9-11-19)33(48-4)30-32(44)34(45)37(23,30)35(39)46/h5-8,12-14,16-17,19-20,24-25,29-34,43-45H,3,9-11,15,18H2,1-2,4H3,(H2,39,46)(H,40,47)/b14-8+,17-16?/t19-,20+,24?,25-,29?,30?,31+,32?,33?,34?,37?,38+/m0/s1

> <INCHI_KEY>
ZYWWYGXERSNBPU-LLUMNTQPSA-N

> <FORMULA>
C38H46N2O9

> <MOLECULAR_WEIGHT>
674.791

> <EXACT_MASS>
674.320331069

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
95

> <JCHEM_AVERAGE_POLARIZABILITY>
69.95799912288967

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,17R,19E,22S,24S,26S)-26-benzyl-8,9,22,28-tetrahydroxy-11-methoxy-17,24-dimethyl-23-methylidene-3,13-dioxo-2-oxa-27-azapentacyclo[19.7.0.0^{1,25}.0^{6,12}.0^{7,10}]octacosa-4,6(12),19,27-tetraene-7-carboximidic acid

> <JCHEM_LOGP>
-0.6916480459573402

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
1.5822553221796336

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.329214406563052

> <JCHEM_PKA_STRONGEST_BASIC>
12.264826502287054

> <JCHEM_POLAR_SURFACE_AREA>
189.96

> <JCHEM_REFRACTIVITY>
193.01179999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,17R,19E,22S,24S,26S)-26-benzyl-8,9,22,28-tetrahydroxy-11-methoxy-17,24-dimethyl-23-methylidene-3,13-dioxo-2-oxa-27-azapentacyclo[19.7.0.0^{1,25}.0^{6,12}.0^{7,10}]octacosa-4,6(12),19,27-tetraene-7-carboximidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.794  -3.753   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.206  -3.808   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.600  -2.496   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.305  -1.193   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.139  -2.538   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.200  -1.421   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.885   0.138   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.470   0.608   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.319  -0.415   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.143   0.071   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.453   1.580   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.302   2.602   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.160   2.117   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       4.590  -2.086   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       4.088  -3.296   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.643  -4.953   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.873  -3.892   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.413  -3.933   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.218  -2.621   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.423  -0.967   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.758  -2.662   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.342  -3.858   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.686  -5.329   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.419  -6.683   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.614  -7.995   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.385  -9.042   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       7.347  -9.349   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.542 -10.662   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.002 -10.620   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.268  -9.266   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.779  -7.903   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.729  -9.224   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.995  -7.870   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.801  -6.558   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.067  -5.204   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       0.528  -5.162   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -0.625  -6.314   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       8.934  -6.403   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      10.268  -7.356   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      11.815  -6.989   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       9.136  -4.877   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       9.800  -3.487   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      11.349  -2.938   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       8.411  -2.823   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0       9.262  -1.358   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0       7.747  -4.213   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       6.307  -3.358   0.000  0.00  0.00           C+0
HETATM   48  N   UNK     0       5.441  -4.408   0.000  0.00  0.00           N+0
HETATM   49  O   UNK     0       6.549  -1.459   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   36                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   17                                                  
CONECT    6    5    7   14                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
CONECT   14    6   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    5   18   35                                             
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   46                                                  
CONECT   24   23   25   38                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   17   36                                                  
CONECT   36   35    2   37                                                  
CONECT   37   36                                                            
CONECT   38   24   39   41                                                  
CONECT   39   38   40                                                       
CONECT   40   39                                                            
CONECT   41   38   42   46                                                  
CONECT   42   41   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44   23   41   47                                             
CONECT   47   46   48   49                                                  
CONECT   48   47                                                            
CONECT   49   47                                                            
MASTER        0    0    0    0    0    0    0    0   49    0  108    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₈H₄₆N₂O₉

Average Mass

674.7910 Da

Monoisotopic Mass

674.32033 Da

IUPAC Name

(1S,17R,19E,22S,24S,26S)-26-benzyl-8,9,22,28-tetrahydroxy-11-methoxy-17,24-dimethyl-23-methylidene-3,13-dioxo-2-oxa-27-azapentacyclo[19.7.0.0^{1,25}.0^{6,12}.0^{7,10}]octacosa-4,6(12),19,27-tetraene-7-carboximidic acid

Traditional Name

CAS Registry Number

Not Available

SMILES

COC1C2C(O)C(O)C2(C(O)=N)C2=C1C(=O)CCC[C@@H](C)C\C=C\C1[C@H](O)C(=C)[C@@H](C)C3[C@H](CC4=CC=CC=C4)N=C(O)[C@@]13OC(=O)C=C2

InChI Identifier

InChI=1S/C38H46N2O9/c1-19-10-8-14-24-31(43)21(3)20(2)29-25(18-22-12-6-5-7-13-22)40-36(47)38(24,29)49-27(42)17-16-23-28(26(41)15-9-11-19)33(48-4)30-32(44)34(45)37(23,30)35(39)46/h5-8,12-14,16-17,19-20,24-25,29-34,43-45H,3,9-11,15,18H2,1-2,4H3,(H2,39,46)(H,40,47)/b14-8+,17-16?/t19-,20+,24?,25-,29?,30?,31+,32?,33?,34?,37?,38+/m0/s1

InChI Key

ZYWWYGXERSNBPU-LLUMNTQPSA-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
Phoma exigua	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoindoles and derivatives. These are polycyclic compounds containing an isoindole moiety, which is structurally characterized by a cyclohexadiene fused to a pyrrole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoindoles and derivatives

Sub Class

Not Available

Direct Parent

Isoindoles and derivatives

Alternative Parents

Substituents

Isoindole or derivatives
Benzenoid
Monocyclic benzene moiety
Cyclic carboximidic acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Pyrroline
Cyclic alcohol
Secondary alcohol
Lactone
Ketone
Cyclobutanol
Carboxylic acid ester
Oxacycle
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Polyol
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Carboximidic acid derivative
Carboximidic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	-0.69	ChemAxon
pKa (Strongest Acidic)	-2.3	ChemAxon
pKa (Strongest Basic)	12.26	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	189.96 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	193.01 m³·mol⁻¹	ChemAxon
Polarizability	69.96 Å³	ChemAxon
Number of Rings	6	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139587245

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,17r,19e,22s,24s,26s)-26-benzyl-8,9,22,28-tetrahydroxy-11-methoxy-17,24-dimethyl-23-methylidene-3,13-dioxo-2-oxa-27-azapentacyclo[19.7.0.0¹,²⁵.0⁶,¹².0⁷,¹⁰]octacosa-4,6(12),19,27-tetraene-7-carboximidic acid (NP0225933)

MOL for NP0225933 ((1s,17r,19e,22s,24s,26s)-26-benzyl-8,9,22,28-tetrahydroxy-11-methoxy-17,24-dimethyl-23-methylidene-3,13-dioxo-2-oxa-27-azapentacyclo[19.7.0.0¹,²⁵.0⁶,¹².0⁷,¹⁰]octacosa-4,6(12),19,27-tetraene-7-carboximidic acid)

3D MOL for NP0225933 ((1s,17r,19e,22s,24s,26s)-26-benzyl-8,9,22,28-tetrahydroxy-11-methoxy-17,24-dimethyl-23-methylidene-3,13-dioxo-2-oxa-27-azapentacyclo[19.7.0.0¹,²⁵.0⁶,¹².0⁷,¹⁰]octacosa-4,6(12),19,27-tetraene-7-carboximidic acid)

3D SDF for NP0225933 ((1s,17r,19e,22s,24s,26s)-26-benzyl-8,9,22,28-tetrahydroxy-11-methoxy-17,24-dimethyl-23-methylidene-3,13-dioxo-2-oxa-27-azapentacyclo[19.7.0.0¹,²⁵.0⁶,¹².0⁷,¹⁰]octacosa-4,6(12),19,27-tetraene-7-carboximidic acid)

3D-SDF for NP0225933 ((1s,17r,19e,22s,24s,26s)-26-benzyl-8,9,22,28-tetrahydroxy-11-methoxy-17,24-dimethyl-23-methylidene-3,13-dioxo-2-oxa-27-azapentacyclo[19.7.0.0¹,²⁵.0⁶,¹².0⁷,¹⁰]octacosa-4,6(12),19,27-tetraene-7-carboximidic acid)

PDB for NP0225933 ((1s,17r,19e,22s,24s,26s)-26-benzyl-8,9,22,28-tetrahydroxy-11-methoxy-17,24-dimethyl-23-methylidene-3,13-dioxo-2-oxa-27-azapentacyclo[19.7.0.0¹,²⁵.0⁶,¹².0⁷,¹⁰]octacosa-4,6(12),19,27-tetraene-7-carboximidic acid)

3D PDB for NP0225933 ((1s,17r,19e,22s,24s,26s)-26-benzyl-8,9,22,28-tetrahydroxy-11-methoxy-17,24-dimethyl-23-methylidene-3,13-dioxo-2-oxa-27-azapentacyclo[19.7.0.0¹,²⁵.0⁶,¹².0⁷,¹⁰]octacosa-4,6(12),19,27-tetraene-7-carboximidic acid)

SMILES for NP0225933 ((1s,17r,19e,22s,24s,26s)-26-benzyl-8,9,22,28-tetrahydroxy-11-methoxy-17,24-dimethyl-23-methylidene-3,13-dioxo-2-oxa-27-azapentacyclo[19.7.0.0¹,²⁵.0⁶,¹².0⁷,¹⁰]octacosa-4,6(12),19,27-tetraene-7-carboximidic acid)

INCHI for NP0225933 ((1s,17r,19e,22s,24s,26s)-26-benzyl-8,9,22,28-tetrahydroxy-11-methoxy-17,24-dimethyl-23-methylidene-3,13-dioxo-2-oxa-27-azapentacyclo[19.7.0.0¹,²⁵.0⁶,¹².0⁷,¹⁰]octacosa-4,6(12),19,27-tetraene-7-carboximidic acid)

Structure for NP0225933 ((1s,17r,19e,22s,24s,26s)-26-benzyl-8,9,22,28-tetrahydroxy-11-methoxy-17,24-dimethyl-23-methylidene-3,13-dioxo-2-oxa-27-azapentacyclo[19.7.0.0¹,²⁵.0⁶,¹².0⁷,¹⁰]octacosa-4,6(12),19,27-tetraene-7-carboximidic acid)

3D Structure for NP0225933 ((1s,17r,19e,22s,24s,26s)-26-benzyl-8,9,22,28-tetrahydroxy-11-methoxy-17,24-dimethyl-23-methylidene-3,13-dioxo-2-oxa-27-azapentacyclo[19.7.0.0¹,²⁵.0⁶,¹².0⁷,¹⁰]octacosa-4,6(12),19,27-tetraene-7-carboximidic acid)