NP-MRD: Showing NP-Card for (2s,10s,12s)-3-acetyl-13-hydroxy-10-(2-methylbut-3-en-2-yl)-1,3,14-triazapentacyclo[10.9.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-4,6,8,13,15,17,19-heptaen-21-one (NP0322262)

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Record Information

Version

2.0

Created at

2022-09-12 00:56:27 UTC

Updated at

2022-09-12 00:56:27 UTC

NP-MRD ID

NP0322262

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Epi-Aszonalenin A 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. (2s,10s,12s)-3-acetyl-13-hydroxy-10-(2-methylbut-3-en-2-yl)-1,3,14-triazapentacyclo[10.9.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-4,6,8,13,15,17,19-heptaen-21-one was first documented in 2022 (PMID: 35704971). Based on a literature review very few articles have been published on epi-Aszonalenin A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122202562D          

 31 35  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 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8795   -4.5897    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
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 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  1  0  0  0  0
 23 25  2  0  0  0  0
 22 26  1  0  0  0  0
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 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 26 31  1  0  0  0  0
  6 31  1  0  0  0  0
M  END

     RDKit          3D

 56 60  0  0  0  0  0  0  0  0999 V2000
   -3.4434   -3.3307   -0.6279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5977   -2.3645   -0.9708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7681   -1.7627    0.1098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7171   -2.7970    0.4472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6567   -1.5744    1.3153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2362   -0.4489   -0.3228 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3132   -0.4613   -1.4930 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0639   -0.7190   -0.9540 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0629   -0.0467   -1.7681 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6362    0.3371   -3.0194 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3132    0.2596   -1.5117 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0331   -0.0084   -0.3049 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3881   -0.0821   -0.4706 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2305   -0.3306    0.5871 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6905   -0.5084    1.8405 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3310   -0.4405    2.0412 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5041   -0.1895    0.9621 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0709   -0.1420    1.3243 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8394   -0.0315    2.5469 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9855   -0.2115    0.4036 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3449    0.2166    0.7405 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4496    1.6440    0.3681 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5385    2.6356    0.3042 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2284    3.9731   -0.2531 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7246    2.4562    0.7038 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8452    1.8054    0.0298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6401    2.9183    0.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9842    2.8318   -0.3133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4581    1.6156   -0.7431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6312    0.4918   -0.7878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3228    0.5601   -0.4067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0890   -3.8276   -1.3512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5503   -3.6937    0.3998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5624   -2.0767   -2.0017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4381   -3.3684   -0.4606 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1216   -2.4197    1.0256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2537   -3.5590    1.0914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7366   -1.7760    1.0647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3965   -2.2845    2.1300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6281   -0.5261    1.6842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3757    0.5349   -2.0186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5596   -1.2291   -2.2507 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2906   -1.8060   -0.9562 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2363   -0.3809   -3.6153 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7689    0.0662   -1.4852 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3146   -0.3841    0.4235 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3258   -0.7031    2.6800 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9008   -0.5761    3.0070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6713    0.0361    1.7561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5279    3.9487   -1.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1933    4.3951   -0.6735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1031    4.6521    0.5510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3058    3.8839    0.4267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6244    3.7176   -0.2744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4887    1.5103   -1.0561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0728   -0.4292   -1.1364 H   0  0  0  0  0  0  0  0  0  0  0  0
 24 23  1  0
 23 25  2  0
 23 22  1  0
 22 21  1  0
 21 20  1  0
 20  8  1  0
  8  7  1  0
  7  6  1  0
  6 31  1  0
 31 30  2  0
 30 29  1  0
 29 28  2  0
 28 27  1  0
 27 26  2  0
  6  3  1  1
  3  4  1  0
  3  5  1  0
  3  2  1  0
  2  1  2  3
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 26 22  1  0
 17 12  1  0
  6 21  1  0
 26 31  1  0
 18 20  1  0
 24 50  1  0
 24 51  1  0
 24 52  1  0
 21 49  1  1
  8 43  1  1
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 30 56  1  0
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 27 53  1  0
  4 35  1  0
  4 36  1  0
  4 37  1  0
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  5 39  1  0
  5 40  1  0
  2 34  1  0
  1 32  1  0
  1 33  1  0
 10 44  1  0
 13 45  1  0
 14 46  1  0
 15 47  1  0
 16 48  1  0
M  END


  Mrv1652309122202562D          

 31 35  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 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8795   -4.5897    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  1  0  0  0  0
 23 25  2  0  0  0  0
 22 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 26 31  1  0  0  0  0
  6 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0322262

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)N1[C@@H]2N3[C@@H](C[C@@]2(C2=CC=CC=C12)C(C)(C)C=C)C(O)=NC1=CC=CC=C1C3=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H25N3O3/c1-5-24(3,4)25-14-20-21(30)26-18-12-8-6-10-16(18)22(31)28(20)23(25)27(15(2)29)19-13-9-7-11-17(19)25/h5-13,20,23H,1,14H2,2-4H3,(H,26,30)/t20-,23+,25-/m0/s1

> <INCHI_KEY>
TXNJQKDZOVFCAQ-ZWSUVBHBSA-N

> <FORMULA>
C25H25N3O3

> <MOLECULAR_WEIGHT>
415.493

> <EXACT_MASS>
415.189591677

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
44.20588054044783

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
3.860610828333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.137885282747327

> <JCHEM_PKA_STRONGEST_BASIC>
0.06606064514629895

> <JCHEM_POLAR_SURFACE_AREA>
73.21000000000001

> <JCHEM_REFRACTIVITY>
119.25709999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-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  C   UNK     0       6.574  -9.399   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       9.108  -8.567   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.655  -6.316   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.324  -7.090   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.988  -6.324   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.984  -4.784   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.315  -4.010   0.000  0.00  0.00           C+0
HETATM   31  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   31                                             
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   26                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   22   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   26    6                                                  
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₅N₃O₃

Average Mass

415.4930 Da

Monoisotopic Mass

415.18959 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC(=O)N1[C@@H]2N3[C@@H](C[C@@]2(C2=CC=CC=C12)C(C)(C)C=C)C(O)=NC1=CC=CC=C1C3=O

InChI Identifier

InChI=1S/C25H25N3O3/c1-5-24(3,4)25-14-20-21(30)26-18-12-8-6-10-16(18)22(31)28(20)23(25)27(15(2)29)19-13-9-7-11-17(19)25/h5-13,20,23H,1,14H2,2-4H3,(H,26,30)/t20-,23+,25-/m0/s1

InChI Key

TXNJQKDZOVFCAQ-ZWSUVBHBSA-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
Acetamide
Lactam
Secondary carboxylic acid amide
Carboxamide group
Azacycle
Carboxylic acid derivative
Organic nitrogen compound
Organic oxide
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
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	3.86	ChemAxon
pKa (Strongest Acidic)	4.14	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	119.26 m³·mol⁻¹	ChemAxon
Polarizability	44.21 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

28283630

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102254364

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Liu Y, Li Y, Chen M, Liu Y, Liang J, Zhang Y, Qian ZJ: Mechanism of two alkaloids isolated from coral endophytic fungus for suppressing angiogenesis in atherosclerotic plaque in HUVEC. Int Immunopharmacol. 2022 Aug;109:108931. doi: 10.1016/j.intimp.2022.108931. Epub 2022 Jun 12. [PubMed:35704971 ]
LOTUS database [Link]

Showing NP-Card for (2s,10s,12s)-3-acetyl-13-hydroxy-10-(2-methylbut-3-en-2-yl)-1,3,14-triazapentacyclo[10.9.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-4,6,8,13,15,17,19-heptaen-21-one (NP0322262)

MOL for NP0322262 ((2s,10s,12s)-3-acetyl-13-hydroxy-10-(2-methylbut-3-en-2-yl)-1,3,14-triazapentacyclo[10.9.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-4,6,8,13,15,17,19-heptaen-21-one)

3D MOL for NP0322262 ((2s,10s,12s)-3-acetyl-13-hydroxy-10-(2-methylbut-3-en-2-yl)-1,3,14-triazapentacyclo[10.9.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-4,6,8,13,15,17,19-heptaen-21-one)

3D SDF for NP0322262 ((2s,10s,12s)-3-acetyl-13-hydroxy-10-(2-methylbut-3-en-2-yl)-1,3,14-triazapentacyclo[10.9.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-4,6,8,13,15,17,19-heptaen-21-one)

3D-SDF for NP0322262 ((2s,10s,12s)-3-acetyl-13-hydroxy-10-(2-methylbut-3-en-2-yl)-1,3,14-triazapentacyclo[10.9.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-4,6,8,13,15,17,19-heptaen-21-one)

PDB for NP0322262 ((2s,10s,12s)-3-acetyl-13-hydroxy-10-(2-methylbut-3-en-2-yl)-1,3,14-triazapentacyclo[10.9.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-4,6,8,13,15,17,19-heptaen-21-one)

3D PDB for NP0322262 ((2s,10s,12s)-3-acetyl-13-hydroxy-10-(2-methylbut-3-en-2-yl)-1,3,14-triazapentacyclo[10.9.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-4,6,8,13,15,17,19-heptaen-21-one)

SMILES for NP0322262 ((2s,10s,12s)-3-acetyl-13-hydroxy-10-(2-methylbut-3-en-2-yl)-1,3,14-triazapentacyclo[10.9.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-4,6,8,13,15,17,19-heptaen-21-one)

INCHI for NP0322262 ((2s,10s,12s)-3-acetyl-13-hydroxy-10-(2-methylbut-3-en-2-yl)-1,3,14-triazapentacyclo[10.9.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-4,6,8,13,15,17,19-heptaen-21-one)

Structure for NP0322262 ((2s,10s,12s)-3-acetyl-13-hydroxy-10-(2-methylbut-3-en-2-yl)-1,3,14-triazapentacyclo[10.9.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-4,6,8,13,15,17,19-heptaen-21-one)

3D Structure for NP0322262 ((2s,10s,12s)-3-acetyl-13-hydroxy-10-(2-methylbut-3-en-2-yl)-1,3,14-triazapentacyclo[10.9.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-4,6,8,13,15,17,19-heptaen-21-one)