NP-MRD: Showing NP-Card for 16-acetyl-6-hydroxy-9-(2-methylbut-3-en-2-yl)-4-(2-methylpropyl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one (NP0318754)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-11 19:25:58 UTC

Updated at

2022-09-11 19:25:58 UTC

NP-MRD ID

NP0318754

Secondary Accession Numbers

None

Natural Product Identification

Common Name

16-acetyl-6-hydroxy-9-(2-methylbut-3-en-2-yl)-4-(2-methylpropyl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one

Description

Verrucofortine 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. 16-acetyl-6-hydroxy-9-(2-methylbut-3-en-2-yl)-4-(2-methylpropyl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one is found in Penicillium verrucosum. Verrucofortine is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 04121512112D          

 30 33  0  0  0  0            999 V2000
    6.9125   -0.9356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2884   -0.3960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4437    0.4142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5091   -0.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8850   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0403    0.6832    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4162    1.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5715    2.0330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6369    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9143    1.3501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3124    0.7859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6630    0.0391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4816    0.1418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1057   -0.3978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9504   -1.2080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0612   -0.5251    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1639   -1.3437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5063   -1.8420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9242   -1.6641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3385   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5592   -0.3978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0649    0.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0904    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8697    1.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4938    0.6832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9617    1.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2150    1.1820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7085    1.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6111    2.2794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0825    2.9565    0.0000 C   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  2  0  0  0  0
 12 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 16 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 11 25  1  0  0  0  0
 20 25  1  0  0  0  0
 11 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 26 29  1  0  0  0  0
 29 30  2  0  0  0  0
M  END

     RDKit          3D

 61 64  0  0  0  0  0  0  0  0999 V2000
   -4.1777    2.2173    1.5626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3165    1.2691    1.2401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4637    1.4699    0.0327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3826    1.9732   -1.0559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4231    2.5150    0.2937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8154    0.1886   -0.4086 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0422    0.4664   -1.6836 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4239    0.2208   -1.3570 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3175    1.1708   -1.9909 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3261    1.2010   -3.2679 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1584    2.0427   -1.2495 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6384    1.5365    0.0373 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8431    0.6993   -0.2267 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4628    0.1056    0.9933 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6745   -0.7141    0.5316 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0122    1.1505    1.9416 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5532    0.8721    0.7500 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5903    0.8048    2.0046 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4673    0.3060    0.0710 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7722   -0.2781    0.5990 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6621   -1.7211    0.3188 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4936   -2.5023    0.3797 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5284   -3.9295    0.0243 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6100   -2.0023    0.7563 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9859   -2.0779   -0.0354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6272   -3.3061   -0.0028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9503   -3.4241   -0.4065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6724   -2.3409   -0.8501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0338   -1.1207   -0.8813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7048   -0.9699   -0.4821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2809    3.1394    0.9712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8350    2.1529    2.4229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2446    0.3965    1.8313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4544    2.0258   -0.7365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2364    1.4597   -2.0279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1490    3.0579   -1.3012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8714    2.3595    1.2375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9562    3.5041    0.3730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6804    2.6209   -0.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2041    1.4629   -2.0997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3757   -0.2683   -2.4519 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6251   -0.8410   -1.6247 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3982    2.9768   -1.6287 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0023    2.4580    0.5771 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6084    1.3585   -0.7030 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6655   -0.1204   -0.9514 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7971   -0.5583    1.5578 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4907   -0.0113    0.2621 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9873   -1.4128    1.3454 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3526   -1.2674   -0.3670 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5139    1.9755    1.4137 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1930    1.4681    2.5959 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7551    0.6314    2.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0013   -0.0343    1.6140 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1843   -4.5767    0.8463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0866   -4.1773   -0.8843 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5798   -4.2426   -0.2713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0918   -4.2000    0.3516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4370   -4.3928   -0.3749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7000   -2.4787   -1.1550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6184   -0.2887   -1.2311 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 14 16  1  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11  9  1  0
  9 10  2  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6 20  1  0
 20 19  1  0
 19 17  1  0
 17 18  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 21 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
  6  3  1  1
  3  4  1  0
  3  5  1  0
  3  2  1  0
  2  1  2  3
 17 12  1  0
 30 25  1  0
 19  8  1  0
 30  6  1  0
 15 48  1  0
 15 49  1  0
 15 50  1  0
 14 47  1  0
 16 51  1  0
 16 52  1  0
 16 53  1  0
 13 45  1  0
 13 46  1  0
 12 44  1  1
 11 43  1  0
  8 42  1  1
  7 40  1  0
  7 41  1  0
 20 54  1  1
 23 55  1  0
 23 56  1  0
 23 57  1  0
 26 58  1  0
 27 59  1  0
 28 60  1  0
 29 61  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
M  END


  Mrv0541 04121512112D          

 30 33  0  0  0  0            999 V2000
    6.9125   -0.9356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2884   -0.3960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4437    0.4142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5091   -0.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8850   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0403    0.6832    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4162    1.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5715    2.0330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6369    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9143    1.3501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3124    0.7859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6630    0.0391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4816    0.1418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1057   -0.3978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9504   -1.2080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0612   -0.5251    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1639   -1.3437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5063   -1.8420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9242   -1.6641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3385   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5592   -0.3978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0649    0.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0904    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8697    1.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4938    0.6832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9617    1.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2150    1.1820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7085    1.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6111    2.2794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0825    2.9565    0.0000 C   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  2  0  0  0  0
 12 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 16 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 11 25  1  0  0  0  0
 20 25  1  0  0  0  0
 11 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 26 29  1  0  0  0  0
 29 30  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0318754

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CC1NC(=O)C2CC3(C(N2C1=O)N(C(C)=O)C1=CC=CC=C31)C(C)(C)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C24H31N3O3/c1-7-23(5,6)24-13-19-20(29)25-17(12-14(2)3)21(30)27(19)22(24)26(15(4)28)18-11-9-8-10-16(18)24/h7-11,14,17,19,22H,1,12-13H2,2-6H3,(H,25,29)

> <INCHI_KEY>
BMRZKNPRSPWNNW-UHFFFAOYSA-N

> <FORMULA>
C24H31N3O3

> <MOLECULAR_WEIGHT>
409.53

> <EXACT_MASS>
409.23654187

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
44.68619398362024

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
16-acetyl-9-(2-methylbut-3-en-2-yl)-4-(2-methylpropyl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-10,12,14-triene-3,6-dione

> <ALOGPS_LOGP>
2.75

> <JCHEM_LOGP>
2.758860511333333

> <ALOGPS_LOGS>
-3.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.009539772929323

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.346588596611218

> <JCHEM_PKA_STRONGEST_BASIC>
-2.835053097349445

> <JCHEM_POLAR_SURFACE_AREA>
69.72

> <JCHEM_REFRACTIVITY>
113.93950000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.33e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
16-acetyl-9-(2-methylbut-3-en-2-yl)-4-(2-methylpropyl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-10,12,14-triene-3,6-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-APR-15         0                                  
HETATM    1  C   UNK     0      12.903  -1.746   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.738  -0.739   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.028   0.773   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.284  -1.244   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.119  -0.237   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       9.409   1.275   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       8.244   2.282   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       8.533   3.795   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.789   1.777   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.440   2.520   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.316   1.467   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.971   0.073   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       6.499   0.265   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       7.664  -0.742   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       7.374  -2.255   0.000  0.00  0.00           O+0
HETATM   16  N   UNK     0       3.848  -0.980   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       4.039  -2.508   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.812  -3.438   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.458  -3.106   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.499  -0.237   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.044  -0.742   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.121   0.265   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.169   1.777   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.624   2.282   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.788   1.275   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.662   2.861   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.268   2.206   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.056   3.516   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.007   4.255   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.887   5.519   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   14                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   25   26                                             
CONECT   12   11   13   16                                                  
CONECT   13   12    9   14                                                  
CONECT   14   13    5   15                                                  
CONECT   15   14                                                            
CONECT   16   12   17   20                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   16   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   11   20                                                  
CONECT   26   11   27   28   29                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   26   30                                                       
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Value	Source
Verrucofortine	MeSH

Chemical Formula

C₂₄H₃₁N₃O₃

Average Mass

409.5300 Da

Monoisotopic Mass

409.23654 Da

IUPAC Name

16-acetyl-9-(2-methylbut-3-en-2-yl)-4-(2-methylpropyl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-10,12,14-triene-3,6-dione

Traditional Name

16-acetyl-9-(2-methylbut-3-en-2-yl)-4-(2-methylpropyl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-10,12,14-triene-3,6-dione

CAS Registry Number

Not Available

SMILES

CC(C)CC1NC(=O)C2CC3(C(N2C1=O)N(C(C)=O)C1=CC=CC=C31)C(C)(C)C=C

InChI Identifier

InChI=1S/C24H31N3O3/c1-7-23(5,6)24-13-19-20(29)25-17(12-14(2)3)21(30)27(19)22(24)26(15(4)28)18-11-9-8-10-16(18)24/h7-11,14,17,19,22H,1,12-13H2,2-6H3,(H,25,29)

InChI Key

BMRZKNPRSPWNNW-UHFFFAOYSA-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
Penicillium verrucosum	LOTUS Database	35616633

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
Alpha-amino acid or derivatives
Indole
Dioxopiperazine
2,5-dioxopiperazine
N-alkylpiperazine
1,4-diazinane
Piperazine
Benzenoid
Acetamide
Tertiary carboxylic acid amide
Pyrrolidine
Pyrrole
Secondary carboxylic acid amide
Carboxamide group
Lactam
Azacycle
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Organopnictogen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
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	2.75	ALOGPS
logP	2.76	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	11.35	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	69.72 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	113.94 m³·mol⁻¹	ChemAxon
Polarizability	44.69 Å³	ChemAxon
Number of Rings	4	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

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

494936

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 16-acetyl-6-hydroxy-9-(2-methylbut-3-en-2-yl)-4-(2-methylpropyl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one (NP0318754)

MOL for NP0318754 (16-acetyl-6-hydroxy-9-(2-methylbut-3-en-2-yl)-4-(2-methylpropyl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

3D MOL for NP0318754 (16-acetyl-6-hydroxy-9-(2-methylbut-3-en-2-yl)-4-(2-methylpropyl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

3D SDF for NP0318754 (16-acetyl-6-hydroxy-9-(2-methylbut-3-en-2-yl)-4-(2-methylpropyl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

3D-SDF for NP0318754 (16-acetyl-6-hydroxy-9-(2-methylbut-3-en-2-yl)-4-(2-methylpropyl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

PDB for NP0318754 (16-acetyl-6-hydroxy-9-(2-methylbut-3-en-2-yl)-4-(2-methylpropyl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

3D PDB for NP0318754 (16-acetyl-6-hydroxy-9-(2-methylbut-3-en-2-yl)-4-(2-methylpropyl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

SMILES for NP0318754 (16-acetyl-6-hydroxy-9-(2-methylbut-3-en-2-yl)-4-(2-methylpropyl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

INCHI for NP0318754 (16-acetyl-6-hydroxy-9-(2-methylbut-3-en-2-yl)-4-(2-methylpropyl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

Structure for NP0318754 (16-acetyl-6-hydroxy-9-(2-methylbut-3-en-2-yl)-4-(2-methylpropyl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)

3D Structure for NP0318754 (16-acetyl-6-hydroxy-9-(2-methylbut-3-en-2-yl)-4-(2-methylpropyl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-5,10,12,14-tetraen-3-one)