NP-MRD: Showing NP-Card for (+)-dihydrodiscorhabdin A (NP0038053)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2021-06-20 20:50:25 UTC

Updated at

2021-06-30 00:10:37 UTC

NP-MRD ID

NP0038053

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-dihydrodiscorhabdin A

Provided By

JEOL Database JEOL Logo

Description

(+)-dihydrodiscorhabdin A is found in Higginsia and Spongosorites. (+)-dihydrodiscorhabdin A was first documented in 2009 (El-Naggar, M., et al.).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202122503D          

 42 47  0  0  0  0            999 V2000
    3.4348    2.9701   -0.7851 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3234    2.4961   -0.9808 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0759    0.9824   -0.9469 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8481    0.4077   -1.1313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3721    1.2849   -1.3040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6197    0.9484   -1.3301 N   0  3  0  0  0  4  0  0  0  0  0  0
   -2.7776    1.9297   -1.3593 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4271    3.2927   -2.0074 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0187    3.6774   -1.7272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3350    4.8732   -1.7258 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9942    4.6095   -1.4353 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1492    3.2573   -1.2674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0763    2.6830   -1.4249 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7817   -1.1525   -1.0906 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2825   -1.7031   -2.0162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2094   -2.5981   -1.6310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5764   -3.1058   -2.8055 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -1.2501   -3.2263   -0.2541 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4997   -4.6225   -0.3294 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0726   -3.0572    0.4998 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6168   -1.6318    0.3867 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3069   -1.5796    1.0963 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.1274   -1.2332   -0.4902 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1446   -1.7613   -1.5267 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1823    0.1947   -0.6685 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8894   -0.0293   -1.2339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0781    2.0596   -0.3141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5941    1.4435   -1.9020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5506    3.2115   -3.0949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1261    4.0600   -1.6576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6538    5.8920   -1.9143 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7395    5.2970   -1.3731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2659   -1.3588   -3.0520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0632   -2.7685    0.3219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2198   -4.7811   -0.9656 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7960   -3.7932    0.1209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0820   -3.3258    1.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0278   -0.9520    0.9570 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1171   -1.6921   -0.5556 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4231   -1.4427   -2.5409 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1284   -2.8592   -1.5354 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0420    0.6909   -0.4217 H   0  0  0  0  0  0  0  0  0  0  0  0
  3 25  1  0  0  0  0
  4 14  1  0  0  0  0
 14 24  1  0  0  0  0
 24 23  1  0  0  0  0
 23 25  1  0  0  0  0
  5 13  1  0  0  0  0
 12 13  2  0  0  0  0
 14 15  1  6  0  0  0
 12  2  1  0  0  0  0
  5  4  1  0  0  0  0
  3  2  1  0  0  0  0
  5  6  2  0  0  0  0
 13  9  1  0  0  0  0
  9  8  1  0  0  0  0
  8  7  1  0  0  0  0
  7  6  1  0  0  0  0
  3  4  2  0  0  0  0
 12 11  1  0  0  0  0
 14 21  1  0  0  0  0
  9 10  2  0  0  0  0
 11 10  1  0  0  0  0
 15 16  2  0  0  0  0
  2  1  2  0  0  0  0
 16 18  1  0  0  0  0
 16 17  1  0  0  0  0
 18 20  1  0  0  0  0
 18 19  1  0  0  0  0
 20 21  1  0  0  0  0
 23 22  1  0  0  0  0
 22 21  1  0  0  0  0
 15 33  1  0  0  0  0
 18 34  1  1  0  0  0
 20 36  1  0  0  0  0
 20 37  1  0  0  0  0
 21 38  1  1  0  0  0
 24 40  1  0  0  0  0
 24 41  1  0  0  0  0
 23 39  1  1  0  0  0
 25 42  1  0  0  0  0
  8 29  1  0  0  0  0
  8 30  1  0  0  0  0
  7 27  1  0  0  0  0
  7 28  1  0  0  0  0
  6 26  1  0  0  0  0
 11 32  1  0  0  0  0
 10 31  1  0  0  0  0
 19 35  1  0  0  0  0
M  CHG  1   6   1
M  END

     RDKit          3D

 42 47  0  0  0  0  0  0  0  0999 V2000
    3.4348    2.9701   -0.7851 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3234    2.4961   -0.9808 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0759    0.9824   -0.9469 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8481    0.4077   -1.1313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3721    1.2849   -1.3040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6197    0.9484   -1.3301 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.7776    1.9297   -1.3593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4271    3.2927   -2.0074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0187    3.6774   -1.7272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3350    4.8732   -1.7258 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9942    4.6095   -1.4353 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1492    3.2573   -1.2674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0763    2.6830   -1.4249 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7817   -1.1525   -1.0906 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2825   -1.7031   -2.0162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2094   -2.5981   -1.6310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5764   -3.1058   -2.8055 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -1.2501   -3.2263   -0.2541 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4997   -4.6225   -0.3294 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0726   -3.0572    0.4998 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6168   -1.6318    0.3867 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3069   -1.5796    1.0963 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.1274   -1.2332   -0.4902 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1446   -1.7613   -1.5267 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1823    0.1947   -0.6685 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8894   -0.0293   -1.2339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0781    2.0596   -0.3141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5941    1.4435   -1.9020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5506    3.2115   -3.0949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1261    4.0600   -1.6576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6538    5.8920   -1.9143 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7395    5.2970   -1.3731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2659   -1.3588   -3.0520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0632   -2.7685    0.3219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2198   -4.7811   -0.9656 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7960   -3.7932    0.1209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0820   -3.3258    1.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0278   -0.9520    0.9570 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1171   -1.6921   -0.5556 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4231   -1.4427   -2.5409 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1284   -2.8592   -1.5354 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0420    0.6909   -0.4217 H   0  0  0  0  0  0  0  0  0  0  0  0
  3 25  1  0
  4 14  1  0
 14 24  1  0
 24 23  1  0
 23 25  1  0
  5 13  1  0
 12 13  2  0
 14 15  1  6
 12  2  1  0
  5  4  1  0
  3  2  1  0
  5  6  2  0
 13  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  3  4  2  0
 12 11  1  0
 14 21  1  0
  9 10  2  0
 11 10  1  0
 15 16  2  0
  2  1  2  0
 16 18  1  0
 16 17  1  0
 18 20  1  0
 18 19  1  0
 20 21  1  0
 23 22  1  0
 22 21  1  0
 15 33  1  0
 18 34  1  1
 20 36  1  0
 20 37  1  0
 21 38  1  1
 24 40  1  0
 24 41  1  0
 23 39  1  1
 25 42  1  0
  8 29  1  0
  8 30  1  0
  7 27  1  0
  7 28  1  0
  6 26  1  0
 11 32  1  0
 10 31  1  0
 19 35  1  0
M  CHG  1   6   1
M  END


  Mrv1652306202122503D          

 42 47  0  0  0  0            999 V2000
    3.4348    2.9701   -0.7851 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3234    2.4961   -0.9808 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0759    0.9824   -0.9469 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8481    0.4077   -1.1313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3721    1.2849   -1.3040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6197    0.9484   -1.3301 N   0  3  0  0  0  4  0  0  0  0  0  0
   -2.7776    1.9297   -1.3593 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4271    3.2927   -2.0074 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0187    3.6774   -1.7272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3350    4.8732   -1.7258 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9942    4.6095   -1.4353 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1492    3.2573   -1.2674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0763    2.6830   -1.4249 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7817   -1.1525   -1.0906 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2825   -1.7031   -2.0162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2094   -2.5981   -1.6310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5764   -3.1058   -2.8055 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -1.2501   -3.2263   -0.2541 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4997   -4.6225   -0.3294 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0726   -3.0572    0.4998 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6168   -1.6318    0.3867 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3069   -1.5796    1.0963 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.1274   -1.2332   -0.4902 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1446   -1.7613   -1.5267 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1823    0.1947   -0.6685 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8894   -0.0293   -1.2339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0781    2.0596   -0.3141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5941    1.4435   -1.9020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5506    3.2115   -3.0949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1261    4.0600   -1.6576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6538    5.8920   -1.9143 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7395    5.2970   -1.3731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2659   -1.3588   -3.0520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0632   -2.7685    0.3219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2198   -4.7811   -0.9656 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7960   -3.7932    0.1209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0820   -3.3258    1.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0278   -0.9520    0.9570 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1171   -1.6921   -0.5556 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4231   -1.4427   -2.5409 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1284   -2.8592   -1.5354 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0420    0.6909   -0.4217 H   0  0  0  0  0  0  0  0  0  0  0  0
  3 25  1  0  0  0  0
  4 14  1  0  0  0  0
 14 24  1  0  0  0  0
 24 23  1  0  0  0  0
 23 25  1  0  0  0  0
  5 13  1  0  0  0  0
 12 13  2  0  0  0  0
 14 15  1  6  0  0  0
 12  2  1  0  0  0  0
  5  4  1  0  0  0  0
  3  2  1  0  0  0  0
  5  6  2  0  0  0  0
 13  9  1  0  0  0  0
  9  8  1  0  0  0  0
  8  7  1  0  0  0  0
  7  6  1  0  0  0  0
  3  4  2  0  0  0  0
 12 11  1  0  0  0  0
 14 21  1  0  0  0  0
  9 10  2  0  0  0  0
 11 10  1  0  0  0  0
 15 16  2  0  0  0  0
  2  1  2  0  0  0  0
 16 18  1  0  0  0  0
 16 17  1  0  0  0  0
 18 20  1  0  0  0  0
 18 19  1  0  0  0  0
 20 21  1  0  0  0  0
 23 22  1  0  0  0  0
 22 21  1  0  0  0  0
 15 33  1  0  0  0  0
 18 34  1  1  0  0  0
 20 36  1  0  0  0  0
 20 37  1  0  0  0  0
 21 38  1  1  0  0  0
 24 40  1  0  0  0  0
 24 41  1  0  0  0  0
 23 39  1  1  0  0  0
 25 42  1  0  0  0  0
  8 29  1  0  0  0  0
  8 30  1  0  0  0  0
  7 27  1  0  0  0  0
  7 28  1  0  0  0  0
  6 26  1  0  0  0  0
 11 32  1  0  0  0  0
 10 31  1  0  0  0  0
 19 35  1  0  0  0  0
M  CHG  1   6   1
M  END
> <DATABASE_ID>
NP0038053

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])C(Br)=C([H])[C@@]23C4=C(N([H])[C@@]([H])(S[C@]2([H])C1([H])[H])C3([H])[H])C(=O)C1=C2C(=C([H])N1[H])C([H])([H])C([H])([H])[N+]([H])=C42

> <INCHI_IDENTIFIER>
InChI=1S/C18H16BrN3O2S/c19-8-4-18-5-11(25-10(18)3-9(8)23)22-16-13(18)14-12-7(1-2-20-14)6-21-15(12)17(16)24/h4,6,9-11,21-23H,1-3,5H2/p+1/t9-,10+,11-,18-/m0/s1

> <INCHI_KEY>
YVUJBORJTOZQQY-DPNGTGFASA-O

> <FORMULA>
C18H17BrN3O2S

> <MOLECULAR_WEIGHT>
419.32

> <EXACT_MASS>
418.021937

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
38.959603400147756

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,6S,8R,10S)-5-bromo-6-hydroxy-13-oxo-9-thia-11,15,20-triazahexacyclo[12.6.1.1^{3,10}.0^{2,12}.0^{3,8}.0^{17,21}]docosa-1(20),2(12),4,14(21),16-pentaen-20-ium

> <ALOGPS_LOGP>
1.22

> <JCHEM_LOGP>
0.4481503516666666

> <ALOGPS_LOGS>
-3.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.835589996893347

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.149110091780216

> <JCHEM_PKA_STRONGEST_BASIC>
7.774383404838405

> <JCHEM_POLAR_SURFACE_AREA>
79.09

> <JCHEM_REFRACTIVITY>
114.43529999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.95e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,6S,8R,10S)-5-bromo-6-hydroxy-13-oxo-9-thia-11,15,20-triazahexacyclo[12.6.1.1^{3,10}.0^{2,12}.0^{3,8}.0^{17,21}]docosa-1(20),2(12),4,14(21),16-pentaen-20-ium

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 42 47  0  0  0  0  0  0  0  0999 V2000
    3.4348    2.9701   -0.7851 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3234    2.4961   -0.9808 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0759    0.9824   -0.9469 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8481    0.4077   -1.1313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3721    1.2849   -1.3040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6197    0.9484   -1.3301 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.7776    1.9297   -1.3593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4271    3.2927   -2.0074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0187    3.6774   -1.7272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3350    4.8732   -1.7258 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9942    4.6095   -1.4353 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1492    3.2573   -1.2674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0763    2.6830   -1.4249 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7817   -1.1525   -1.0906 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2825   -1.7031   -2.0162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2094   -2.5981   -1.6310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5764   -3.1058   -2.8055 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -1.2501   -3.2263   -0.2541 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4997   -4.6225   -0.3294 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0726   -3.0572    0.4998 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6168   -1.6318    0.3867 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3069   -1.5796    1.0963 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.1274   -1.2332   -0.4902 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1446   -1.7613   -1.5267 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1823    0.1947   -0.6685 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8894   -0.0293   -1.2339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0781    2.0596   -0.3141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5941    1.4435   -1.9020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5506    3.2115   -3.0949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1261    4.0600   -1.6576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6538    5.8920   -1.9143 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7395    5.2970   -1.3731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2659   -1.3588   -3.0520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0632   -2.7685    0.3219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2198   -4.7811   -0.9656 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7960   -3.7932    0.1209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0820   -3.3258    1.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0278   -0.9520    0.9570 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1171   -1.6921   -0.5556 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4231   -1.4427   -2.5409 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1284   -2.8592   -1.5354 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0420    0.6909   -0.4217 H   0  0  0  0  0  0  0  0  0  0  0  0
  3 25  1  0
  4 14  1  0
 14 24  1  0
 24 23  1  0
 23 25  1  0
  5 13  1  0
 12 13  2  0
 14 15  1  6
 12  2  1  0
  5  4  1  0
  3  2  1  0
  5  6  2  0
 13  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  3  4  2  0
 12 11  1  0
 14 21  1  0
  9 10  2  0
 11 10  1  0
 15 16  2  0
  2  1  2  0
 16 18  1  0
 16 17  1  0
 18 20  1  0
 18 19  1  0
 20 21  1  0
 23 22  1  0
 22 21  1  0
 15 33  1  0
 18 34  1  1
 20 36  1  0
 20 37  1  0
 21 38  1  1
 24 40  1  0
 24 41  1  0
 23 39  1  1
 25 42  1  0
  8 29  1  0
  8 30  1  0
  7 27  1  0
  7 28  1  0
  6 26  1  0
 11 32  1  0
 10 31  1  0
 19 35  1  0
M  CHG  1   6   1
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  O   UNK     0       3.435   2.970  -0.785  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.323   2.496  -0.981  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.076   0.982  -0.947  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.848   0.408  -1.131  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.372   1.285  -1.304  0.00  0.00           C+0
HETATM    6  N   UNK     0      -1.620   0.948  -1.330  0.00  0.00           N+1
HETATM    7  C   UNK     0      -2.778   1.930  -1.359  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.427   3.293  -2.007  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.019   3.677  -1.727  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.335   4.873  -1.726  0.00  0.00           C+0
HETATM   11  N   UNK     0       0.994   4.609  -1.435  0.00  0.00           N+0
HETATM   12  C   UNK     0       1.149   3.257  -1.267  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.076   2.683  -1.425  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.782  -1.153  -1.091  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.283  -1.703  -2.016  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.209  -2.598  -1.631  0.00  0.00           C+0
HETATM   17 Br   UNK     0      -2.576  -3.106  -2.805  0.00  0.00          Br+0
HETATM   18  C   UNK     0      -1.250  -3.226  -0.254  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.500  -4.622  -0.329  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.073  -3.057   0.500  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.617  -1.632   0.387  0.00  0.00           C+0
HETATM   22  S   UNK     0       2.307  -1.580   1.096  0.00  0.00           S+0
HETATM   23  C   UNK     0       3.127  -1.233  -0.490  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.145  -1.761  -1.527  0.00  0.00           C+0
HETATM   25  N   UNK     0       3.182   0.195  -0.669  0.00  0.00           N+0
HETATM   26  H   UNK     0      -1.889  -0.029  -1.234  0.00  0.00           H+0
HETATM   27  H   UNK     0      -3.078   2.060  -0.314  0.00  0.00           H+0
HETATM   28  H   UNK     0      -3.594   1.444  -1.902  0.00  0.00           H+0
HETATM   29  H   UNK     0      -2.551   3.212  -3.095  0.00  0.00           H+0
HETATM   30  H   UNK     0      -3.126   4.060  -1.658  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.654   5.892  -1.914  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.740   5.297  -1.373  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.266  -1.359  -3.052  0.00  0.00           H+0
HETATM   34  H   UNK     0      -2.063  -2.769   0.322  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.220  -4.781  -0.966  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.796  -3.793   0.121  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.082  -3.326   1.554  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.028  -0.952   0.957  0.00  0.00           H+0
HETATM   39  H   UNK     0       4.117  -1.692  -0.556  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.423  -1.443  -2.541  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.128  -2.859  -1.535  0.00  0.00           H+0
HETATM   42  H   UNK     0       4.042   0.691  -0.422  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2   12    3    1                                                  
CONECT    3   25    2    4                                                  
CONECT    4   14    5    3                                                  
CONECT    5   13    4    6                                                  
CONECT    6    5    7   26                                                  
CONECT    7    8    6   27   28                                             
CONECT    8    9    7   29   30                                             
CONECT    9   13    8   10                                                  
CONECT   10    9   11   31                                                  
CONECT   11   12   10   32                                                  
CONECT   12   13    2   11                                                  
CONECT   13    5   12    9                                                  
CONECT   14    4   24   15   21                                             
CONECT   15   14   16   33                                                  
CONECT   16   15   18   17                                                  
CONECT   17   16                                                            
CONECT   18   16   20   19   34                                             
CONECT   19   18   35                                                       
CONECT   20   18   21   36   37                                             
CONECT   21   14   20   22   38                                             
CONECT   22   23   21                                                       
CONECT   23   24   25   22   39                                             
CONECT   24   14   23   40   41                                             
CONECT   25    3   23   42                                                  
CONECT   26    6                                                            
CONECT   27    7                                                            
CONECT   28    7                                                            
CONECT   29    8                                                            
CONECT   30    8                                                            
CONECT   31   10                                                            
CONECT   32   11                                                            
CONECT   33   15                                                            
CONECT   34   18                                                            
CONECT   35   19                                                            
CONECT   36   20                                                            
CONECT   37   20                                                            
CONECT   38   21                                                            
CONECT   39   23                                                            
CONECT   40   24                                                            
CONECT   41   24                                                            
CONECT   42   25                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   94    0
END

RDKit          3D

42 47  0  0  0  0  0  0  0  0999 V2000
    3.4348    2.9701   -0.7851 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3234    2.4961   -0.9808 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0759    0.9824   -0.9469 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8481    0.4077   -1.1313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3721    1.2849   -1.3040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6197    0.9484   -1.3301 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.7776    1.9297   -1.3593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4271    3.2927   -2.0074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0187    3.6774   -1.7272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3350    4.8732   -1.7258 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9942    4.6095   -1.4353 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1492    3.2573   -1.2674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0763    2.6830   -1.4249 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7817   -1.1525   -1.0906 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2825   -1.7031   -2.0162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2094   -2.5981   -1.6310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5764   -3.1058   -2.8055 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -1.2501   -3.2263   -0.2541 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4997   -4.6225   -0.3294 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0726   -3.0572    0.4998 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6168   -1.6318    0.3867 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3069   -1.5796    1.0963 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.1274   -1.2332   -0.4902 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1446   -1.7613   -1.5267 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1823    0.1947   -0.6685 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8894   -0.0293   -1.2339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0781    2.0596   -0.3141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5941    1.4435   -1.9020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5506    3.2115   -3.0949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1261    4.0600   -1.6576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6538    5.8920   -1.9143 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7395    5.2970   -1.3731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2659   -1.3588   -3.0520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0632   -2.7685    0.3219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2198   -4.7811   -0.9656 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7960   -3.7932    0.1209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0820   -3.3258    1.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0278   -0.9520    0.9570 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1171   -1.6921   -0.5556 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4231   -1.4427   -2.5409 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1284   -2.8592   -1.5354 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0420    0.6909   -0.4217 H   0  0  0  0  0  0  0  0  0  0  0  0
  3 25  1  0
  4 14  1  0
 14 24  1  0
 24 23  1  0
 23 25  1  0
  5 13  1  0
 12 13  2  0
 14 15  1  6
 12  2  1  0
  5  4  1  0
  3  2  1  0
  5  6  2  0
 13  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  3  4  2  0
 12 11  1  0
 14 21  1  0
  9 10  2  0
 11 10  1  0
 15 16  2  0
  2  1  2  0
 16 18  1  0
 16 17  1  0
 18 20  1  0
 18 19  1  0
 20 21  1  0
 23 22  1  0
 22 21  1  0
 15 33  1  0
 18 34  1  1
 20 36  1  0
 20 37  1  0
 21 38  1  1
 24 40  1  0
 24 41  1  0
 23 39  1  1
 25 42  1  0
  8 29  1  0
  8 30  1  0
  7 27  1  0
  7 28  1  0
  6 26  1  0
 11 32  1  0
 10 31  1  0
 19 35  1  0
M  CHG  1   6   1
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₁₇BrN₃O₂S

Average Mass

419.3200 Da

Monoisotopic Mass

418.02194 Da

IUPAC Name

(3S,6S,8R,10S)-5-bromo-6-hydroxy-13-oxo-9-thia-11,15,20-triazahexacyclo[12.6.1.1^{3,10}.0^{2,12}.0^{3,8}.0^{17,21}]docosa-1(20),2(12),4,14(21),16-pentaen-20-ium

Traditional Name

(3S,6S,8R,10S)-5-bromo-6-hydroxy-13-oxo-9-thia-11,15,20-triazahexacyclo[12.6.1.1^{3,10}.0^{2,12}.0^{3,8}.0^{17,21}]docosa-1(20),2(12),4,14(21),16-pentaen-20-ium

CAS Registry Number

Not Available

SMILES

[H]O[C@]1([H])C(Br)=C([H])[C@@]23C4=C(N([H])[C@@]([H])(S[C@]2([H])C1([H])[H])C3([H])[H])C(=O)C1=C2C(=C([H])N1[H])C([H])([H])C([H])([H])[N+]([H])=C42

InChI Identifier

InChI=1S/C18H16BrN3O2S/c19-8-4-18-5-11(25-10(18)3-9(8)23)22-16-13(18)14-12-7(1-2-20-14)6-21-15(12)17(16)24/h4,6,9-11,21-23H,1-3,5H2/p+1/t9-,10+,11-,18-/m0/s1

InChI Key

YVUJBORJTOZQQY-DPNGTGFASA-O

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Higginsia	JEOL database	El-Naggar, M., et al, J. Nat. Prod. 71, 460 (2009)
Spongosorites	JEOL database	El-Naggar, M., et al, J. Nat. Prod. 71, 460 (2009)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthrolines. These are aromatic polycyclic compounds containing the phenanthroline skeleton, which is a derivative of phenanthrene, and consists of two pyridine rings non-linearly joined by a benzene ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Phenanthrolines

Sub Class

Not Available

Direct Parent

Phenanthrolines

Alternative Parents

Substituents

1,7-phenanthroline
Pyrrolo[4,3,2-de]quinoline
Pyrroloquinoline
Indole or derivatives
Aryl ketone
Tetrahydropyridine
Heteroaromatic compound
Pyrrole
Thiolane
Bromohydrin
Halohydrin
Ketone
Secondary alcohol
Secondary aliphatic amine
Enamine
Azacycle
Bromoalkene
Haloalkene
Dialkylthioether
Secondary amine
Thioether
Hemithioaminal
Vinyl halide
Vinyl bromide
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic nitrogen compound
Alcohol
Amine
Organic oxygen compound
Organopnictogen compound
Organic oxide
Organohalogen compound
Organobromide
Organic cation
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	1.22	ALOGPS
logP	0.45	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	13.15	ChemAxon
pKa (Strongest Basic)	7.77	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	79.09 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	114.44 m³·mol⁻¹	ChemAxon
Polarizability	38.96 Å³	ChemAxon
Number of Rings	6	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

29394137

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

El-Naggar, M., et al. (2009). El-Naggar, M., et al, J. Nat. Prod. 71, 460 (2009). J. Nat. Prod..

Showing NP-Card for (+)-dihydrodiscorhabdin A (NP0038053)

MOL for NP0038053 ((+)-dihydrodiscorhabdin A)

3D MOL for NP0038053 ((+)-dihydrodiscorhabdin A)

3D SDF for NP0038053 ((+)-dihydrodiscorhabdin A)

3D-SDF for NP0038053 ((+)-dihydrodiscorhabdin A)

PDB for NP0038053 ((+)-dihydrodiscorhabdin A)

3D PDB for NP0038053 ((+)-dihydrodiscorhabdin A)

SMILES for NP0038053 ((+)-dihydrodiscorhabdin A)

INCHI for NP0038053 ((+)-dihydrodiscorhabdin A)

Structure for NP0038053 ((+)-dihydrodiscorhabdin A)

3D Structure for NP0038053 ((+)-dihydrodiscorhabdin A)