NP-MRD: Showing NP-Card for (12e,25e)-5,16,21,32,33,36-hexabromo-12,25-bis(hydroxyimino)-2,18-dioxa-10,27-diazapentacyclo[28.2.2.2¹⁴,¹⁷.1³,⁷.1¹⁹,²³]octatriaconta-1(32),3(38),4,6,10,14,16,19(35),20,22,26,30,33,36-tetradecaene-4,11,13,20,26-pentol (NP0154536)

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Record Information

Version

2.0

Created at

2022-09-02 11:27:59 UTC

Updated at

2022-09-02 11:28:00 UTC

NP-MRD ID

NP0154536

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(12e,25e)-5,16,21,32,33,36-hexabromo-12,25-bis(hydroxyimino)-2,18-dioxa-10,27-diazapentacyclo[28.2.2.2¹⁴,¹⁷.1³,⁷.1¹⁹,²³]octatriaconta-1(32),3(38),4,6,10,14,16,19(35),20,22,26,30,33,36-tetradecaene-4,11,13,20,26-pentol

Description

Bastadin 24 belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed. (12e,25e)-5,16,21,32,33,36-hexabromo-12,25-bis(hydroxyimino)-2,18-dioxa-10,27-diazapentacyclo[28.2.2.2¹⁴,¹⁷.1³,⁷.1¹⁹,²³]octatriaconta-1(32),3(38),4,6,10,14,16,19(35),20,22,26,30,33,36-tetradecaene-4,11,13,20,26-pentol is found in Ianthella quadrangulata. (12e,25e)-5,16,21,32,33,36-hexabromo-12,25-bis(hydroxyimino)-2,18-dioxa-10,27-diazapentacyclo[28.2.2.2¹⁴,¹⁷.1³,⁷.1¹⁹,²³]octatriaconta-1(32),3(38),4,6,10,14,16,19(35),20,22,26,30,33,36-tetradecaene-4,11,13,20,26-pentol was first documented in 2008 (PMID: 18298075). Based on a literature review very few articles have been published on bastadin 24.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309022213282D          

 53 57  0  0  0  0            999 V2000
   15.6833    1.7866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8892    2.0103    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2984    1.4344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7902    0.7247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9075   -0.1293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0726   -0.1366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6203   -0.8265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7959   -0.7940    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   14.0159   -1.5479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5583   -2.2343    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8449   -1.6368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2769   -0.9037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6913   -2.5090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1303   -3.1738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3811   -2.7985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3616   -1.9737    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   12.6602   -3.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6387   -4.0403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3784   -4.4395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1018   -4.0214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8093   -4.4457    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   11.7980   -4.2291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8848   -5.0495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9490   -4.2206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8668   -5.0415    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5367   -5.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1216   -4.0620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8666   -4.8466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3524   -3.7007    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7224   -3.1360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2654   -2.4053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8872   -1.6249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0422   -1.5777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6258   -0.8507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8009   -0.8413    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    7.0533   -0.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6352    0.5689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8897   -0.1130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2757   -0.8720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2937    0.6706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8340    1.3544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5811    0.9824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6107    0.1579    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   10.2943    1.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3144    2.2433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5666    2.6297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8481    2.2025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1344    2.6163    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   11.1564    2.4481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0104    2.4401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8410    2.2723    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6162    1.9334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0275    2.6485    0.0000 O   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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
  5 12  1  0  0  0  0
 11 13  1  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
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 18 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 29 30  1  4  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 38 39  2  0  0  0  0
 32 39  1  0  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 42 43  1  0  0  0  0
 42 44  1  0  0  0  0
 44 45  2  0  0  0  0
 45 46  1  0  0  0  0
 46 47  2  0  0  0  0
 41 47  1  0  0  0  0
 47 48  1  0  0  0  0
 45 49  1  0  0  0  0
 49 50  1  0  0  0  0
 51 50  1  4  0  0  0
 51 52  2  0  0  0  0
  3 52  1  0  0  0  0
 52 53  1  0  0  0  0
M  END


  Mrv1652309022213282D          

 53 57  0  0  0  0            999 V2000
   15.6833    1.7866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8892    2.0103    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2984    1.4344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7902    0.7247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9075   -0.1293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0726   -0.1366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6203   -0.8265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7959   -0.7940    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   14.0159   -1.5479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5583   -2.2343    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8449   -1.6368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2769   -0.9037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6913   -2.5090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1303   -3.1738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3811   -2.7985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3616   -1.9737    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   12.6602   -3.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6387   -4.0403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3784   -4.4395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1018   -4.0214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8093   -4.4457    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   11.7980   -4.2291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8848   -5.0495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9490   -4.2206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8668   -5.0415    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5367   -5.5230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1216   -4.0620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8666   -4.8466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3524   -3.7007    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7224   -3.1360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2654   -2.4053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8872   -1.6249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0422   -1.5777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6258   -0.8507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8009   -0.8413    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    7.0533   -0.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6352    0.5689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8897   -0.1130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2757   -0.8720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2937    0.6706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8340    1.3544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5811    0.9824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6107    0.1579    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   10.2943    1.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3144    2.2433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5666    2.6297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8481    2.2025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1344    2.6163    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   11.1564    2.4481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0104    2.4401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8410    2.2723    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6162    1.9334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0275    2.6485    0.0000 O   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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
  5 12  1  0  0  0  0
 11 13  1  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
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 18 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 29 30  1  4  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 38 39  2  0  0  0  0
 32 39  1  0  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 42 43  1  0  0  0  0
 42 44  1  0  0  0  0
 44 45  2  0  0  0  0
 45 46  1  0  0  0  0
 46 47  2  0  0  0  0
 41 47  1  0  0  0  0
 47 48  1  0  0  0  0
 45 49  1  0  0  0  0
 49 50  1  0  0  0  0
 51 50  1  4  0  0  0
 51 52  2  0  0  0  0
  3 52  1  0  0  0  0
 52 53  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0154536

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O\N=C1/CC2=CC(Br)=C(O)C(OC3=C(Br)C=C(C=C3Br)C(O)\C(=N/O)C(O)=NCCC3=CC(Br)=C(O)C(OC4=C(Br)C=C(CCN=C1O)C=C4Br)=C3)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C34H26Br6N4O9/c35-18-5-15-2-4-42-34(49)27(44-51)28(45)17-12-22(39)32(23(40)13-17)53-26-11-16(8-19(36)30(26)47)9-24(43-50)33(48)41-3-1-14-6-20(37)31(21(38)7-14)52-25(10-15)29(18)46/h5-8,10-13,28,45-47,50-51H,1-4,9H2,(H,41,48)(H,42,49)/b43-24+,44-27+

> <INCHI_KEY>
MHAGECXZXFMEGD-OJYBBUQISA-N

> <FORMULA>
C34H26Br6N4O9

> <MOLECULAR_WEIGHT>
1114.025

> <EXACT_MASS>
1107.680006

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
82.02047202733095

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(12E,25E)-5,16,21,32,33,36-hexabromo-12,25-bis(hydroxyimino)-2,18-dioxa-10,27-diazapentacyclo[28.2.2.2^{14,17}.1^{3,7}.1^{19,23}]octatriaconta-1(32),3(38),4,6,10,14,16,19(35),20,22,26,30,33,36-tetradecaene-4,11,13,20,26-pentol

> <ALOGPS_LOGP>
6.30

> <JCHEM_LOGP>
9.902622098514465

> <ALOGPS_LOGS>
-5.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
2.127000475663408

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8564921751168368

> <JCHEM_PKA_STRONGEST_BASIC>
2.9748545927746233

> <JCHEM_POLAR_SURFACE_AREA>
209.51000000000002

> <JCHEM_REFRACTIVITY>
217.6854

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.68e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(12E,25E)-5,16,21,32,33,36-hexabromo-12,25-bis(hydroxyimino)-2,18-dioxa-10,27-diazapentacyclo[28.2.2.2^{14,17}.1^{3,7}.1^{19,23}]octatriaconta-1(32),3(38),4,6,10,14,16,19(35),20,22,26,30,33,36-tetradecaene-4,11,13,20,26-pentol

> <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  O   UNK     0      29.275   3.335   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0      27.793   3.752   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      26.690   2.678   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      27.608   1.353   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      27.827  -0.241   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      26.269  -0.255   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      25.424  -1.543   0.000  0.00  0.00           C+0
HETATM    8 Br   UNK     0      23.886  -1.482   0.000  0.00  0.00          Br+0
HETATM    9  C   UNK     0      26.163  -2.889   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      25.309  -4.171   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      27.710  -3.055   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      28.517  -1.687   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      27.424  -4.683   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      26.377  -5.924   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      24.978  -5.224   0.000  0.00  0.00           C+0
HETATM   16 Br   UNK     0      24.942  -3.684   0.000  0.00  0.00          Br+0
HETATM   17  C   UNK     0      23.632  -5.980   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      23.592  -7.542   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      24.973  -8.287   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      26.323  -7.507   0.000  0.00  0.00           C+0
HETATM   21 Br   UNK     0      27.644  -8.299   0.000  0.00  0.00          Br+0
HETATM   22  C   UNK     0      22.023  -7.894   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      22.185  -9.426   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      20.438  -7.878   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0      20.285  -9.411   0.000  0.00  0.00           N+0
HETATM   26  O   UNK     0      21.535 -10.310   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      18.894  -7.582   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      18.418  -9.047   0.000  0.00  0.00           O+0
HETATM   29  N   UNK     0      17.458  -6.908   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0      16.282  -5.854   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      15.429  -4.490   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      14.723  -3.033   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      13.145  -2.945   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      12.368  -1.588   0.000  0.00  0.00           C+0
HETATM   35 Br   UNK     0      10.828  -1.570   0.000  0.00  0.00          Br+0
HETATM   36  C   UNK     0      13.166  -0.266   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      12.386   1.062   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      14.727  -0.211   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      15.448  -1.628   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      15.481   1.252   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      16.490   2.528   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      17.885   1.834   0.000  0.00  0.00           C+0
HETATM   43 Br   UNK     0      17.940   0.295   0.000  0.00  0.00          Br+0
HETATM   44  C   UNK     0      19.216   2.621   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      19.254   4.187   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      17.858   4.909   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      16.516   4.111   0.000  0.00  0.00           C+0
HETATM   48 Br   UNK     0      15.184   4.884   0.000  0.00  0.00          Br+0
HETATM   49  C   UNK     0      20.825   4.570   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      22.419   4.555   0.000  0.00  0.00           C+0
HETATM   51  N   UNK     0      23.970   4.242   0.000  0.00  0.00           N+0
HETATM   52  C   UNK     0      25.417   3.609   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0      26.185   4.944   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   52                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11    5                                                       
CONECT   13   11   14                                                       
CONECT   14   13   15   20                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   22                                                  
CONECT   19   18   20                                                       
CONECT   20   19   14   21                                                  
CONECT   21   20                                                            
CONECT   22   18   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   39                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39   40                                                  
CONECT   39   38   32                                                       
CONECT   40   38   41                                                       
CONECT   41   40   42   47                                                  
CONECT   42   41   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   45                                                       
CONECT   45   44   46   49                                                  
CONECT   46   45   47                                                       
CONECT   47   46   41   48                                                  
CONECT   48   47                                                            
CONECT   49   45   50                                                       
CONECT   50   49   51                                                       
CONECT   51   50   52                                                       
CONECT   52   51    3   53                                                  
CONECT   53   52                                                            
MASTER        0    0    0    0    0    0    0    0   53    0  114    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₄H₂₆Br₆N₄O₉

Average Mass

1114.0250 Da

Monoisotopic Mass

1107.68001 Da

IUPAC Name

(12E,25E)-5,16,21,32,33,36-hexabromo-12,25-bis(hydroxyimino)-2,18-dioxa-10,27-diazapentacyclo[28.2.2.2^{14,17}.1^{3,7}.1^{19,23}]octatriaconta-1(32),3(38),4,6,10,14,16,19(35),20,22,26,30,33,36-tetradecaene-4,11,13,20,26-pentol

Traditional Name

CAS Registry Number

Not Available

SMILES

O\N=C1/CC2=CC(Br)=C(O)C(OC3=C(Br)C=C(C=C3Br)C(O)\C(=N/O)C(O)=NCCC3=CC(Br)=C(O)C(OC4=C(Br)C=C(CCN=C1O)C=C4Br)=C3)=C2

InChI Identifier

InChI=1S/C34H26Br6N4O9/c35-18-5-15-2-4-42-34(49)27(44-51)28(45)17-12-22(39)32(23(40)13-17)53-26-11-16(8-19(36)30(26)47)9-24(43-50)33(48)41-3-1-14-6-20(37)31(21(38)7-14)52-25(10-15)29(18)46/h5-8,10-13,28,45-47,50-51H,1-4,9H2,(H,41,48)(H,42,49)/b43-24+,44-27+

InChI Key

MHAGECXZXFMEGD-OJYBBUQISA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ianthella quadrangulata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Not Available

Sub Class

Not Available

Direct Parent

Lignans, neolignans and related compounds

Alternative Parents

Substituents

Oxyneolignan skeleton
Macrolactam
Diaryl ether
2-halophenol
2-bromophenol
Phenol
Aryl bromide
Aryl halide
Benzenoid
Carboxamide group
Lactam
Secondary carboxylic acid amide
Secondary alcohol
Polyol
Oxime
Carboxylic acid derivative
Ether
Organoheterocyclic compound
Azacycle
Oxacycle
Organic oxygen compound
Hydrocarbon derivative
Organohalogen compound
Organic oxide
Organobromide
Alcohol
Carbonyl group
Organonitrogen compound
Organic nitrogen 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	6.3	ALOGPS
logP	9.9	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	0.86	ChemAxon
pKa (Strongest Basic)	2.97	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	209.51 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	217.69 m³·mol⁻¹	ChemAxon
Polarizability	82.02 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00038584

Chemspider ID

23314557

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44448206

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Greve H, Kehraus S, Krick A, Kelter G, Maier A, Fiebig HH, Wright AD, Konig GM: Cytotoxic bastadin 24 from the Australian sponge Ianthella quadrangulata. J Nat Prod. 2008 Mar;71(3):309-12. doi: 10.1021/np070373e. Epub 2008 Feb 26. [PubMed:18298075 ]
LOTUS database [Link]

Showing NP-Card for (12e,25e)-5,16,21,32,33,36-hexabromo-12,25-bis(hydroxyimino)-2,18-dioxa-10,27-diazapentacyclo[28.2.2.2¹⁴,¹⁷.1³,⁷.1¹⁹,²³]octatriaconta-1(32),3(38),4,6,10,14,16,19(35),20,22,26,30,33,36-tetradecaene-4,11,13,20,26-pentol (NP0154536)

MOL for NP0154536 ((12e,25e)-5,16,21,32,33,36-hexabromo-12,25-bis(hydroxyimino)-2,18-dioxa-10,27-diazapentacyclo[28.2.2.2¹⁴,¹⁷.1³,⁷.1¹⁹,²³]octatriaconta-1(32),3(38),4,6,10,14,16,19(35),20,22,26,30,33,36-tetradecaene-4,11,13,20,26-pentol)

3D MOL for NP0154536 ((12e,25e)-5,16,21,32,33,36-hexabromo-12,25-bis(hydroxyimino)-2,18-dioxa-10,27-diazapentacyclo[28.2.2.2¹⁴,¹⁷.1³,⁷.1¹⁹,²³]octatriaconta-1(32),3(38),4,6,10,14,16,19(35),20,22,26,30,33,36-tetradecaene-4,11,13,20,26-pentol)

3D SDF for NP0154536 ((12e,25e)-5,16,21,32,33,36-hexabromo-12,25-bis(hydroxyimino)-2,18-dioxa-10,27-diazapentacyclo[28.2.2.2¹⁴,¹⁷.1³,⁷.1¹⁹,²³]octatriaconta-1(32),3(38),4,6,10,14,16,19(35),20,22,26,30,33,36-tetradecaene-4,11,13,20,26-pentol)

3D-SDF for NP0154536 ((12e,25e)-5,16,21,32,33,36-hexabromo-12,25-bis(hydroxyimino)-2,18-dioxa-10,27-diazapentacyclo[28.2.2.2¹⁴,¹⁷.1³,⁷.1¹⁹,²³]octatriaconta-1(32),3(38),4,6,10,14,16,19(35),20,22,26,30,33,36-tetradecaene-4,11,13,20,26-pentol)

PDB for NP0154536 ((12e,25e)-5,16,21,32,33,36-hexabromo-12,25-bis(hydroxyimino)-2,18-dioxa-10,27-diazapentacyclo[28.2.2.2¹⁴,¹⁷.1³,⁷.1¹⁹,²³]octatriaconta-1(32),3(38),4,6,10,14,16,19(35),20,22,26,30,33,36-tetradecaene-4,11,13,20,26-pentol)

3D PDB for NP0154536 ((12e,25e)-5,16,21,32,33,36-hexabromo-12,25-bis(hydroxyimino)-2,18-dioxa-10,27-diazapentacyclo[28.2.2.2¹⁴,¹⁷.1³,⁷.1¹⁹,²³]octatriaconta-1(32),3(38),4,6,10,14,16,19(35),20,22,26,30,33,36-tetradecaene-4,11,13,20,26-pentol)

SMILES for NP0154536 ((12e,25e)-5,16,21,32,33,36-hexabromo-12,25-bis(hydroxyimino)-2,18-dioxa-10,27-diazapentacyclo[28.2.2.2¹⁴,¹⁷.1³,⁷.1¹⁹,²³]octatriaconta-1(32),3(38),4,6,10,14,16,19(35),20,22,26,30,33,36-tetradecaene-4,11,13,20,26-pentol)

INCHI for NP0154536 ((12e,25e)-5,16,21,32,33,36-hexabromo-12,25-bis(hydroxyimino)-2,18-dioxa-10,27-diazapentacyclo[28.2.2.2¹⁴,¹⁷.1³,⁷.1¹⁹,²³]octatriaconta-1(32),3(38),4,6,10,14,16,19(35),20,22,26,30,33,36-tetradecaene-4,11,13,20,26-pentol)

Structure for NP0154536 ((12e,25e)-5,16,21,32,33,36-hexabromo-12,25-bis(hydroxyimino)-2,18-dioxa-10,27-diazapentacyclo[28.2.2.2¹⁴,¹⁷.1³,⁷.1¹⁹,²³]octatriaconta-1(32),3(38),4,6,10,14,16,19(35),20,22,26,30,33,36-tetradecaene-4,11,13,20,26-pentol)

3D Structure for NP0154536 ((12e,25e)-5,16,21,32,33,36-hexabromo-12,25-bis(hydroxyimino)-2,18-dioxa-10,27-diazapentacyclo[28.2.2.2¹⁴,¹⁷.1³,⁷.1¹⁹,²³]octatriaconta-1(32),3(38),4,6,10,14,16,19(35),20,22,26,30,33,36-tetradecaene-4,11,13,20,26-pentol)