NP-MRD: Showing NP-Card for (2r,10s,12s)-13-hydroxy-10-(2-methylbut-3-en-2-yl)-21-oxo-1,3,14-triazapentacyclo[10.9.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-4,6,8,13,15,17,19-heptaene-3-carbaldehyde (NP0145014)

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Record Information

Version

2.0

Created at

2022-09-02 00:07:03 UTC

Updated at

2022-09-02 00:07:03 UTC

NP-MRD ID

NP0145014

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,10s,12s)-13-hydroxy-10-(2-methylbut-3-en-2-yl)-21-oxo-1,3,14-triazapentacyclo[10.9.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-4,6,8,13,15,17,19-heptaene-3-carbaldehyde

Description

Epi-aszonalenin B belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. (2r,10s,12s)-13-hydroxy-10-(2-methylbut-3-en-2-yl)-21-oxo-1,3,14-triazapentacyclo[10.9.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-4,6,8,13,15,17,19-heptaene-3-carbaldehyde was first documented in 2022 (PMID: 35131506). Based on a literature review very few articles have been published on Epi-aszonalenin B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022202072D          

 30 34  0  0  1  0            999 V2000
    3.1710   -0.2149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8376   -0.9695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3244   -1.6356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6583   -2.1224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9904   -1.1488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8112   -2.3016    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2942   -1.6328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0795   -1.8856    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7231   -1.3694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5372   -0.5656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5279   -1.5507    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8880   -2.2930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7105   -2.2290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1771   -2.9093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8213   -3.6536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9988   -3.7176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5321   -3.0373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7283   -3.2231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5470   -4.0279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0819   -2.7105    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2980   -2.9677    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8149   -3.6365    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0721   -4.4204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5218   -5.0351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0296   -3.3838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3163   -3.7983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6006   -3.3878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5983   -2.5628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3116   -2.1483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0273   -2.5588    0.0000 C   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  0  0  0  0
  3  5  1  0  0  0  0
  6  3  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
  8 20  1  1  0  0  0
 21 20  1  1  0  0  0
  6 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 22 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 25 30  1  0  0  0  0
  6 30  1  0  0  0  0
M  END

     RDKit          3D

 53 57  0  0  0  0  0  0  0  0999 V2000
   -0.5882   -2.9718    0.6358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2895   -2.3711   -0.2968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1972   -1.2564    0.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8036   -1.4793    1.4000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3110   -1.2885   -0.9924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4583    0.0438   -0.0017 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8283    0.3265   -1.3717 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5628   -0.2554   -1.3269 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5162    0.5599   -2.0992 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9350    1.4138   -3.0157 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8028    0.6137   -2.0666 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7203   -0.1106   -1.2594 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9984   -0.2050   -1.7171 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9599   -0.8921   -0.9895 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6667   -1.4997    0.2101 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3734   -1.4119    0.6862 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4353   -0.7265   -0.0497 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1186   -0.7535    0.6346 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0741   -1.1813    1.8139 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8965   -0.3381    0.0775 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2388    0.0950    0.8649 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0466    1.5525    0.9908 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1343    2.3063    1.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1565    3.5573    1.1355 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3730    2.0655    1.0776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8879    3.2363    1.6251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2271    3.5480    1.6129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1043    2.6616    1.0321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6019    1.4938    0.4844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2573    1.1822    0.4971 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0880   -3.8053    0.3740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5941   -2.7380    1.6921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2057   -2.7009   -1.3141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1213   -2.5493    1.4270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0179   -1.3726    2.1569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6170   -0.7904    1.6423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2149   -2.1716   -1.6956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2895   -1.4797   -0.4897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3254   -0.4171   -1.6691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7328    1.4385   -1.4228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4284   -0.0421   -2.2004 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6293   -1.2826   -1.7435 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4301    1.0604   -3.8425 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2836    0.2434   -2.6358 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9859   -0.9792   -1.3370 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3921   -2.0404    0.7979 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954   -1.8791    1.6343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3065   -0.3823    1.8351 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1220    1.8328    0.9502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1892    3.9337    2.0831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5945    4.4664    2.0472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1782    2.8960    1.0143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3486    0.8446    0.0479 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0
  3  5  1  0
  3  2  1  0
  2  1  2  3
  6  3  1  6
  6  7  1  0
  7  8  1  0
  8 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 22 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 20 18  1  0
 18 19  2  0
 18 17  1  0
 17 16  2  0
 16 15  1  0
 15 14  2  0
 14 13  1  0
 13 12  2  0
 12 11  1  0
 11  9  2  0
  9 10  1  0
 21  6  1  0
 30 25  1  0
 12 17  1  0
 30  6  1  0
  9  8  1  0
  4 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  0
  5 38  1  0
  5 39  1  0
  2 33  1  0
  1 31  1  0
  1 32  1  0
  7 40  1  0
  7 41  1  0
  8 42  1  6
 21 48  1  1
 23 49  1  0
 26 50  1  0
 27 51  1  0
 28 52  1  0
 29 53  1  0
 16 47  1  0
 15 46  1  0
 14 45  1  0
 13 44  1  0
 10 43  1  0
M  END


  Mrv1652309022202072D          

 30 34  0  0  1  0            999 V2000
    3.1710   -0.2149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8376   -0.9695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3244   -1.6356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6583   -2.1224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9904   -1.1488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8112   -2.3016    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2942   -1.6328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0795   -1.8856    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7231   -1.3694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5372   -0.5656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5279   -1.5507    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8880   -2.2930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7105   -2.2290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1771   -2.9093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8213   -3.6536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9988   -3.7176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5321   -3.0373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7283   -3.2231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5470   -4.0279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0819   -2.7105    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2980   -2.9677    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8149   -3.6365    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0721   -4.4204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5218   -5.0351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0296   -3.3838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3163   -3.7983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6006   -3.3878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5983   -2.5628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3116   -2.1483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0273   -2.5588    0.0000 C   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  0  0  0  0
  3  5  1  0  0  0  0
  6  3  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
  8 20  1  1  0  0  0
 21 20  1  1  0  0  0
  6 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 22 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 25 30  1  0  0  0  0
  6 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0145014

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(C=C)[C@]12C[C@@H]3N([C@H]1N(C=O)C1=CC=CC=C21)C(=O)C1=CC=CC=C1N=C3O

> <INCHI_IDENTIFIER>
InChI=1S/C24H23N3O3/c1-4-23(2,3)24-13-19-20(29)25-17-11-7-5-9-15(17)21(30)27(19)22(24)26(14-28)18-12-8-6-10-16(18)24/h4-12,14,19,22H,1,13H2,2-3H3,(H,25,29)/t19-,22+,24-/m0/s1

> <INCHI_KEY>
IWRNQJRIMSPELQ-KWOQKUFVSA-N

> <FORMULA>
C24H23N3O3

> <MOLECULAR_WEIGHT>
401.466

> <EXACT_MASS>
401.173941613

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
42.42207428079074

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,10S,12S)-13-hydroxy-10-(2-methylbut-3-en-2-yl)-21-oxo-1,3,14-triazapentacyclo[10.9.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-4,6,8,13,15,17,19-heptaene-3-carbaldehyde

> <ALOGPS_LOGP>
2.37

> <JCHEM_LOGP>
3.8119121203333326

> <ALOGPS_LOGS>
-4.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.099716051113254

> <JCHEM_PKA_STRONGEST_BASIC>
0.06595197893156712

> <JCHEM_POLAR_SURFACE_AREA>
73.21000000000001

> <JCHEM_REFRACTIVITY>
114.76659999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.39e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,10S,12S)-13-hydroxy-10-(2-methylbut-3-en-2-yl)-21-oxo-1,3,14-triazapentacyclo[10.9.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-4,6,8,13,15,17,19-heptaene-3-carbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       5.919  -0.401   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.297  -1.810   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.205  -3.053   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.962  -3.962   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.449  -2.144   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.114  -4.296   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.016  -3.048   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.482  -3.520   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.683  -2.556   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      10.336  -1.056   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0      12.185  -2.895   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      12.858  -4.280   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.393  -4.161   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.264  -5.431   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.600  -6.820   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.064  -6.940   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.193  -5.670   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.693  -6.016   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      10.354  -7.519   0.000  0.00  0.00           O+0
HETATM   20  N   UNK     0       9.486  -5.060   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       8.023  -5.540   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       7.121  -6.788   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       7.601  -8.251   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.574  -9.399   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.655  -6.316   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.324  -7.090   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.988  -6.324   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.984  -4.784   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.315  -4.010   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.651  -4.776   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5    6                                             
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    3    7   21   30                                             
CONECT    7    6    8                                                       
CONECT    8    7    9   20                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   18                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18    8   21                                                  
CONECT   21   20    6   22                                                  
CONECT   22   21   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   22   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   25    6                                                  
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₂₃N₃O₃

Average Mass

401.4660 Da

Monoisotopic Mass

401.17394 Da

IUPAC Name

(2R,10S,12S)-13-hydroxy-10-(2-methylbut-3-en-2-yl)-21-oxo-1,3,14-triazapentacyclo[10.9.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-4,6,8,13,15,17,19-heptaene-3-carbaldehyde

Traditional Name

(2R,10S,12S)-13-hydroxy-10-(2-methylbut-3-en-2-yl)-21-oxo-1,3,14-triazapentacyclo[10.9.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-4,6,8,13,15,17,19-heptaene-3-carbaldehyde

CAS Registry Number

Not Available

SMILES

CC(C)(C=C)[C@]12C[C@@H]3N([C@H]1N(C=O)C1=CC=CC=C21)C(=O)C1=CC=CC=C1N=C3O

InChI Identifier

InChI=1S/C24H23N3O3/c1-4-23(2,3)24-13-19-20(29)25-17-11-7-5-9-15(17)21(30)27(19)22(24)26(14-28)18-12-8-6-10-16(18)24/h4-12,14,19,22H,1,13H2,2-3H3,(H,25,29)/t19-,22+,24-/m0/s1

InChI Key

IWRNQJRIMSPELQ-KWOQKUFVSA-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 pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Pyrroloindoles

Direct Parent

Pyrroloindoles

Alternative Parents

Substituents

Pyrroloindole
Benzodiazepine
1,4-benzodiazepine
Alpha-amino acid or derivatives
Indole
Benzenoid
Pyrrole
Pyrrolidine
Tertiary carboxylic acid amide
Vinylogous amide
Lactam
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Azacycle
Hydrocarbon derivative
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organic oxide
Organic oxygen compound
Carbonyl group
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	2.37	ALOGPS
logP	3.81	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	4.1	ChemAxon
pKa (Strongest Basic)	0.066	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	73.21 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	114.77 m³·mol⁻¹	ChemAxon
Polarizability	42.42 Å³	ChemAxon
Number of Rings	5	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

78439634

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102254365

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ishikawa K, Ishii M, Yaguchi T, Katada T, Ichinose K, Ohata S: epi-Aszonalenin B from Aspergillus novofumigatus inhibits NF-kappaB activity induced by ZFTA-RELA fusion protein that drives ependymoma. Biochem Biophys Res Commun. 2022 Mar 12;596:104-110. doi: 10.1016/j.bbrc.2022.01.076. Epub 2022 Jan 22. [PubMed:35131506 ]
LOTUS database [Link]

Showing NP-Card for (2r,10s,12s)-13-hydroxy-10-(2-methylbut-3-en-2-yl)-21-oxo-1,3,14-triazapentacyclo[10.9.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-4,6,8,13,15,17,19-heptaene-3-carbaldehyde (NP0145014)

MOL for NP0145014 ((2r,10s,12s)-13-hydroxy-10-(2-methylbut-3-en-2-yl)-21-oxo-1,3,14-triazapentacyclo[10.9.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-4,6,8,13,15,17,19-heptaene-3-carbaldehyde)

3D MOL for NP0145014 ((2r,10s,12s)-13-hydroxy-10-(2-methylbut-3-en-2-yl)-21-oxo-1,3,14-triazapentacyclo[10.9.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-4,6,8,13,15,17,19-heptaene-3-carbaldehyde)

3D SDF for NP0145014 ((2r,10s,12s)-13-hydroxy-10-(2-methylbut-3-en-2-yl)-21-oxo-1,3,14-triazapentacyclo[10.9.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-4,6,8,13,15,17,19-heptaene-3-carbaldehyde)

3D-SDF for NP0145014 ((2r,10s,12s)-13-hydroxy-10-(2-methylbut-3-en-2-yl)-21-oxo-1,3,14-triazapentacyclo[10.9.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-4,6,8,13,15,17,19-heptaene-3-carbaldehyde)

PDB for NP0145014 ((2r,10s,12s)-13-hydroxy-10-(2-methylbut-3-en-2-yl)-21-oxo-1,3,14-triazapentacyclo[10.9.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-4,6,8,13,15,17,19-heptaene-3-carbaldehyde)

3D PDB for NP0145014 ((2r,10s,12s)-13-hydroxy-10-(2-methylbut-3-en-2-yl)-21-oxo-1,3,14-triazapentacyclo[10.9.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-4,6,8,13,15,17,19-heptaene-3-carbaldehyde)

SMILES for NP0145014 ((2r,10s,12s)-13-hydroxy-10-(2-methylbut-3-en-2-yl)-21-oxo-1,3,14-triazapentacyclo[10.9.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-4,6,8,13,15,17,19-heptaene-3-carbaldehyde)

INCHI for NP0145014 ((2r,10s,12s)-13-hydroxy-10-(2-methylbut-3-en-2-yl)-21-oxo-1,3,14-triazapentacyclo[10.9.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-4,6,8,13,15,17,19-heptaene-3-carbaldehyde)

Structure for NP0145014 ((2r,10s,12s)-13-hydroxy-10-(2-methylbut-3-en-2-yl)-21-oxo-1,3,14-triazapentacyclo[10.9.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-4,6,8,13,15,17,19-heptaene-3-carbaldehyde)

3D Structure for NP0145014 ((2r,10s,12s)-13-hydroxy-10-(2-methylbut-3-en-2-yl)-21-oxo-1,3,14-triazapentacyclo[10.9.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-4,6,8,13,15,17,19-heptaene-3-carbaldehyde)