NP-MRD: Showing NP-Card for (1r,2r,5s,6s,7r,10s,12r,15r,16s,18r,20r)-9-hydroxy-7-isopropyl-4,5,16,18,20-pentamethyl-8-azapentacyclo[10.8.0.0²,¹⁰.0⁶,¹⁰.0¹⁵,²⁰]icosa-3,8,13-trien-11-one (NP0218712)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-05 19:28:05 UTC

Updated at

2022-09-05 19:28:05 UTC

NP-MRD ID

NP0218712

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,5s,6s,7r,10s,12r,15r,16s,18r,20r)-9-hydroxy-7-isopropyl-4,5,16,18,20-pentamethyl-8-azapentacyclo[10.8.0.0²,¹⁰.0⁶,¹⁰.0¹⁵,²⁰]icosa-3,8,13-trien-11-one

Description

Chaetochalasin 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. (1r,2r,5s,6s,7r,10s,12r,15r,16s,18r,20r)-9-hydroxy-7-isopropyl-4,5,16,18,20-pentamethyl-8-azapentacyclo[10.8.0.0²,¹⁰.0⁶,¹⁰.0¹⁵,²⁰]icosa-3,8,13-trien-11-one is found in Ovatospora brasiliensis. (1r,2r,5s,6s,7r,10s,12r,15r,16s,18r,20r)-9-hydroxy-7-isopropyl-4,5,16,18,20-pentamethyl-8-azapentacyclo[10.8.0.0²,¹⁰.0⁶,¹⁰.0¹⁵,²⁰]icosa-3,8,13-trien-11-one was first documented in 2014 (PMID: 25119649). Based on a literature review very few articles have been published on Chaetochalasin A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052221282D          

 30 34  0  0  1  0            999 V2000
    2.1528    4.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1643    3.3946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8397    2.9209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7673    2.0991    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3295    1.4953    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9290    0.7740    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3534    0.0666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1783    0.0804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5788    0.8017    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4036    0.8155    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9175    0.1278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8041    1.5368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3797    2.2442    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9108    2.9313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5548    2.2304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1544    1.5091    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8384    2.3021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1193    0.9320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4809    0.2247    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0193    1.7510    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7775    0.9622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1700    0.1191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9526    0.9484    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6846    1.7286    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1574    1.9293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8681    1.4380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5627    2.6901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3438    2.2246    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4163    3.0464    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8284    3.6695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  4  3  1  6  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
  9 16  1  0  0  0  0
  5 16  1  0  0  0  0
 16 17  1  1  0  0  0
  6 18  1  1  0  0  0
 18 19  2  0  0  0  0
 20 18  1  6  0  0  0
  4 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 28 24  1  1  0  0  0
 20 28  1  0  0  0  0
 28 29  1  0  0  0  0
  2 29  1  0  0  0  0
 29 30  1  6  0  0  0
M  END

     RDKit          3D

 69 73  0  0  0  0  0  0  0  0999 V2000
    2.9008   -3.1766   -1.4843 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3105   -1.8922   -1.0318 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2491   -1.9005   -0.2857 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5330   -0.6852    0.2525 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7946   -0.5945   -0.4156 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5535    0.4686   -1.4362 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7761    1.0284   -2.0290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7951    1.2723   -1.2197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6069    0.9546    0.2242 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8645    1.1536    1.0090 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5149    2.4234    0.4809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8207    0.0120    1.0035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3393   -1.3289    0.6598 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3341   -2.0533   -0.2689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9930   -1.5103    0.0792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9876   -0.4266    0.4338 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8063   -0.5488    1.9192 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3410    1.4114   -0.8007 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4364    2.6282   -0.8432 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2794    0.5825    0.0455 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5153    1.2610    1.3505 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6210    2.0461    2.0790 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7118    1.0076    1.7264 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4260    0.1710    0.7835 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8699    0.5741    0.6579 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9149    2.0070    0.1759 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4363    0.5438    2.0837 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6332    0.4896   -0.5083 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9586   -0.6293   -1.4440 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7805   -0.2937   -2.9048 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8659   -3.2160   -2.5916 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4284   -4.0553   -1.0142 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9641   -3.1770   -1.1454 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8056   -2.8480   -0.0011 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4787   -0.8845    1.3421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9463   -1.5450   -1.0247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0154   -0.0152   -2.3036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9017    1.2552   -3.0800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7433    1.6922   -1.5947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8565    1.6679    0.6062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6383    1.3904    2.0731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7645    3.1680    0.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2547    2.1889   -0.3197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1009    2.9104    1.2889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4110    0.0038    1.9722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6379    0.2841    0.2641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3828   -1.9655    1.5981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2792   -3.1478   -0.1123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0120   -1.8742   -1.3177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3562   -1.7001   -0.1066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5163   -2.4657    0.3904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0291   -1.5476   -1.0311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8450   -0.7282    2.3439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2492   -1.4427    2.2388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5088    0.3895    2.3828 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6939    3.0455    2.1513 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3467   -0.9110    0.9961 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4361   -0.1060    0.0026 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8053    2.4783    0.6496 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0094    2.5302    0.5149 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0426    2.0263   -0.9108 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8442   -0.1469    2.7253 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4302    1.5626    2.4987 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4593    0.1335    2.0465 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9775    1.4537   -0.8771 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0747   -0.7998   -1.3267 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7374   -0.1665   -3.4007 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1452   -1.0857   -3.3579 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1727    0.6527   -3.0140 H   0  0  0  0  0  0  0  0  0  0  0  0
 26 25  1  0
 25 27  1  0
 25 24  1  0
 24 23  1  0
 23 21  2  0
 21 22  1  0
 20 21  1  1
 20  4  1  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  2 29  1  0
 29 30  1  0
 29 28  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  1
  6 18  1  0
 18 19  2  0
 28 24  1  0
 16  5  1  0
 28 20  1  0
 16  9  1  0
 18 20  1  0
 26 59  1  0
 26 60  1  0
 26 61  1  0
 25 58  1  0
 27 62  1  0
 27 63  1  0
 27 64  1  0
 24 57  1  1
 22 56  1  0
  4 35  1  1
  3 34  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
 29 66  1  6
 30 67  1  0
 30 68  1  0
 30 69  1  0
 28 65  1  6
  5 36  1  6
  6 37  1  6
  7 38  1  0
  8 39  1  0
  9 40  1  1
 10 41  1  1
 11 42  1  0
 11 43  1  0
 11 44  1  0
 12 45  1  0
 12 46  1  0
 13 47  1  1
 14 48  1  0
 14 49  1  0
 14 50  1  0
 15 51  1  0
 15 52  1  0
 17 53  1  0
 17 54  1  0
 17 55  1  0
M  END


  Mrv1652309052221282D          

 30 34  0  0  1  0            999 V2000
    2.1528    4.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1643    3.3946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8397    2.9209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7673    2.0991    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3295    1.4953    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9290    0.7740    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3534    0.0666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1783    0.0804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5788    0.8017    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4036    0.8155    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9175    0.1278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8041    1.5368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3797    2.2442    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9108    2.9313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5548    2.2304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1544    1.5091    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8384    2.3021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1193    0.9320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4809    0.2247    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0193    1.7510    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7775    0.9622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1700    0.1191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9526    0.9484    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6846    1.7286    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1574    1.9293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8681    1.4380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5627    2.6901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3438    2.2246    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4163    3.0464    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8284    3.6695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  4  3  1  6  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
  9 16  1  0  0  0  0
  5 16  1  0  0  0  0
 16 17  1  1  0  0  0
  6 18  1  1  0  0  0
 18 19  2  0  0  0  0
 20 18  1  6  0  0  0
  4 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 28 24  1  1  0  0  0
 20 28  1  0  0  0  0
 28 29  1  0  0  0  0
  2 29  1  0  0  0  0
 29 30  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0218712

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@H]1N=C(O)[C@]23[C@H](C=C(C)[C@@H](C)[C@H]12)[C@@H]1[C@@H](C=C[C@H]2[C@@H](C)C[C@@H](C)C[C@@]12C)C3=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H39NO2/c1-13(2)23-21-17(6)15(4)11-20-22-18(24(29)27(20,21)25(30)28-23)8-9-19-16(5)10-14(3)12-26(19,22)7/h8-9,11,13-14,16-23H,10,12H2,1-7H3,(H,28,30)/t14-,16+,17-,18-,19+,20-,21-,22+,23-,26-,27-/m1/s1

> <INCHI_KEY>
MYAIFNPIHQINJU-SCDLYVQXSA-N

> <FORMULA>
C27H39NO2

> <MOLECULAR_WEIGHT>
409.614

> <EXACT_MASS>
409.2980795

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
48.600758521123545

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,5S,6S,7R,10S,12R,15R,16S,18R,20R)-9-hydroxy-4,5,16,18,20-pentamethyl-7-(propan-2-yl)-8-azapentacyclo[10.8.0.0^{2,10}.0^{6,10}.0^{15,20}]icosa-3,8,13-trien-11-one

> <JCHEM_LOGP>
5.969517195333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.666946364374638

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.6411273583580614

> <JCHEM_PKA_STRONGEST_BASIC>
2.001941215674394

> <JCHEM_POLAR_SURFACE_AREA>
49.66

> <JCHEM_REFRACTIVITY>
122.83749999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5S,6S,7R,10S,12R,15R,16S,18R,20R)-9-hydroxy-7-isopropyl-4,5,16,18,20-pentamethyl-8-azapentacyclo[10.8.0.0^{2,10}.0^{6,10}.0^{15,20}]icosa-3,8,13-trien-11-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       4.018   7.954   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.040   6.337   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.301   5.452   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.166   3.918   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.215   2.791   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.467   1.445   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.260   0.124   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.799   0.150   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.547   1.496   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.087   1.522   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.046   0.239   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.834   2.869   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.042   4.189   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.033   5.472   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.502   4.163   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.755   2.817   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.165   4.297   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.956   1.740   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.764   0.419   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.769   3.268   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.318   1.796   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.051   0.222   0.000  0.00  0.00           O+0
HETATM   23  N   UNK     0       1.778   1.770   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0       1.278   3.227   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.294   3.601   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.621   2.684   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.050   5.021   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.508   4.153   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.644   5.687   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.546   6.850   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   29                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   20                                                  
CONECT    5    4    6   16                                                  
CONECT    6    5    7   18                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   16                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15    9    5   17                                             
CONECT   17   16                                                            
CONECT   18    6   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18    4   21   28                                             
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   28                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   24   20   29                                                  
CONECT   29   28    2   30                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₉NO₂

Average Mass

409.6140 Da

Monoisotopic Mass

409.29808 Da

IUPAC Name

(1R,2R,5S,6S,7R,10S,12R,15R,16S,18R,20R)-9-hydroxy-4,5,16,18,20-pentamethyl-7-(propan-2-yl)-8-azapentacyclo[10.8.0.0^{2,10}.0^{6,10}.0^{15,20}]icosa-3,8,13-trien-11-one

Traditional Name

(1R,2R,5S,6S,7R,10S,12R,15R,16S,18R,20R)-9-hydroxy-7-isopropyl-4,5,16,18,20-pentamethyl-8-azapentacyclo[10.8.0.0^{2,10}.0^{6,10}.0^{15,20}]icosa-3,8,13-trien-11-one

CAS Registry Number

Not Available

SMILES

CC(C)[C@H]1N=C(O)[C@]23[C@H](C=C(C)[C@@H](C)[C@H]12)[C@@H]1[C@@H](C=C[C@H]2[C@@H](C)C[C@@H](C)C[C@@]12C)C3=O

InChI Identifier

InChI=1S/C27H39NO2/c1-13(2)23-21-17(6)15(4)11-20-22-18(24(29)27(20,21)25(30)28-23)8-9-19-16(5)10-14(3)12-26(19,22)7/h8-9,11,13-14,16-23H,10,12H2,1-7H3,(H,28,30)/t14-,16+,17-,18-,19+,20-,21-,22+,23-,26-,27-/m1/s1

InChI Key

MYAIFNPIHQINJU-SCDLYVQXSA-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
Ovatospora brasiliensis	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
Pyrroline
Cyclic carboximidic acid
Ketone
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Azacycle
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	5.97	ChemAxon
pKa (Strongest Acidic)	4.64	ChemAxon
pKa (Strongest Basic)	2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.66 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	122.84 m³·mol⁻¹	ChemAxon
Polarizability	48.6 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	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

78440020

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139583452

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Thomas EJ, Willis M: Approaches to the total synthesis of chaetochalasin A. Org Biomol Chem. 2014 Oct 14;12(38):7537-50. doi: 10.1039/c4ob01308e. [PubMed:25119649 ]
LOTUS database [Link]

Showing NP-Card for (1r,2r,5s,6s,7r,10s,12r,15r,16s,18r,20r)-9-hydroxy-7-isopropyl-4,5,16,18,20-pentamethyl-8-azapentacyclo[10.8.0.0²,¹⁰.0⁶,¹⁰.0¹⁵,²⁰]icosa-3,8,13-trien-11-one (NP0218712)

MOL for NP0218712 ((1r,2r,5s,6s,7r,10s,12r,15r,16s,18r,20r)-9-hydroxy-7-isopropyl-4,5,16,18,20-pentamethyl-8-azapentacyclo[10.8.0.0²,¹⁰.0⁶,¹⁰.0¹⁵,²⁰]icosa-3,8,13-trien-11-one)

3D MOL for NP0218712 ((1r,2r,5s,6s,7r,10s,12r,15r,16s,18r,20r)-9-hydroxy-7-isopropyl-4,5,16,18,20-pentamethyl-8-azapentacyclo[10.8.0.0²,¹⁰.0⁶,¹⁰.0¹⁵,²⁰]icosa-3,8,13-trien-11-one)

3D SDF for NP0218712 ((1r,2r,5s,6s,7r,10s,12r,15r,16s,18r,20r)-9-hydroxy-7-isopropyl-4,5,16,18,20-pentamethyl-8-azapentacyclo[10.8.0.0²,¹⁰.0⁶,¹⁰.0¹⁵,²⁰]icosa-3,8,13-trien-11-one)

3D-SDF for NP0218712 ((1r,2r,5s,6s,7r,10s,12r,15r,16s,18r,20r)-9-hydroxy-7-isopropyl-4,5,16,18,20-pentamethyl-8-azapentacyclo[10.8.0.0²,¹⁰.0⁶,¹⁰.0¹⁵,²⁰]icosa-3,8,13-trien-11-one)

PDB for NP0218712 ((1r,2r,5s,6s,7r,10s,12r,15r,16s,18r,20r)-9-hydroxy-7-isopropyl-4,5,16,18,20-pentamethyl-8-azapentacyclo[10.8.0.0²,¹⁰.0⁶,¹⁰.0¹⁵,²⁰]icosa-3,8,13-trien-11-one)

3D PDB for NP0218712 ((1r,2r,5s,6s,7r,10s,12r,15r,16s,18r,20r)-9-hydroxy-7-isopropyl-4,5,16,18,20-pentamethyl-8-azapentacyclo[10.8.0.0²,¹⁰.0⁶,¹⁰.0¹⁵,²⁰]icosa-3,8,13-trien-11-one)

SMILES for NP0218712 ((1r,2r,5s,6s,7r,10s,12r,15r,16s,18r,20r)-9-hydroxy-7-isopropyl-4,5,16,18,20-pentamethyl-8-azapentacyclo[10.8.0.0²,¹⁰.0⁶,¹⁰.0¹⁵,²⁰]icosa-3,8,13-trien-11-one)

INCHI for NP0218712 ((1r,2r,5s,6s,7r,10s,12r,15r,16s,18r,20r)-9-hydroxy-7-isopropyl-4,5,16,18,20-pentamethyl-8-azapentacyclo[10.8.0.0²,¹⁰.0⁶,¹⁰.0¹⁵,²⁰]icosa-3,8,13-trien-11-one)

Structure for NP0218712 ((1r,2r,5s,6s,7r,10s,12r,15r,16s,18r,20r)-9-hydroxy-7-isopropyl-4,5,16,18,20-pentamethyl-8-azapentacyclo[10.8.0.0²,¹⁰.0⁶,¹⁰.0¹⁵,²⁰]icosa-3,8,13-trien-11-one)

3D Structure for NP0218712 ((1r,2r,5s,6s,7r,10s,12r,15r,16s,18r,20r)-9-hydroxy-7-isopropyl-4,5,16,18,20-pentamethyl-8-azapentacyclo[10.8.0.0²,¹⁰.0⁶,¹⁰.0¹⁵,²⁰]icosa-3,8,13-trien-11-one)