NP-MRD: Showing NP-Card for (9r,10r,11r,12r,13r,15r,16r)-13-chloro-12-ethenyl-11-isocyano-8,8,12,19,19-pentamethyl-6-azapentacyclo[13.3.1.0⁵,¹⁸.0⁷,¹⁷.0¹¹,¹⁶]nonadeca-1(18),2,4,7(17)-tetraene-9,10,16-triol (NP0210772)

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Record Information

Version

2.0

Created at

2022-09-05 08:44:09 UTC

Updated at

2022-09-05 08:44:09 UTC

NP-MRD ID

NP0210772

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(9r,10r,11r,12r,13r,15r,16r)-13-chloro-12-ethenyl-11-isocyano-8,8,12,19,19-pentamethyl-6-azapentacyclo[13.3.1.0⁵,¹⁸.0⁷,¹⁷.0¹¹,¹⁶]nonadeca-1(18),2,4,7(17)-tetraene-9,10,16-triol

Description

Ambiguine F isonitrile belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. (9r,10r,11r,12r,13r,15r,16r)-13-chloro-12-ethenyl-11-isocyano-8,8,12,19,19-pentamethyl-6-azapentacyclo[13.3.1.0⁵,¹⁸.0⁷,¹⁷.0¹¹,¹⁶]nonadeca-1(18),2,4,7(17)-tetraene-9,10,16-triol was first documented in 2007 (PMID: 17315959). Based on a literature review very few articles have been published on ambiguine F isonitrile.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052210442D          

 32 36  0  0  1  0            999 V2000
   -0.0914    0.2304    0.0000 C   0  5  0  0  0  0  0  0  0  0  0  0
    0.6591    0.5731    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.4096    0.9158    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1715    0.1259    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3565   -0.0024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6406   -0.5528    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2328   -1.2699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4637   -0.6091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2256   -1.3990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1808   -1.0170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0209   -0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8905   -0.0725    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3216    0.8235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0334    1.2406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0281    2.0656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3110    2.4734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5992    2.0563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6045    1.2314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8927    0.8143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1756    1.2221    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1193    0.3991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1703    2.0471    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4531    2.4550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7414    2.0379    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0242    2.4458    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.7467    1.2129    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1508    0.6424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0758    1.1486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5428    1.8287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8821    2.4642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4900    3.1901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2647    3.1951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 11 19  2  0  0  0  0
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  3 20  1  0  0  0  0
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  3 26  1  0  0  0  0
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 17 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
M  CHG  2   1  -1   2   1
M  END

     RDKit          3D

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    3.4696    0.8983   -1.5022 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6553    1.3142    0.0695 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7774    2.6086    0.5113 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5903    3.1839    0.6463 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0797    4.4267    1.0393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2821    4.6542    1.0477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1807    3.6687    0.6706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6831    2.4205    0.2749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3384    2.2363    0.2807 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3097    1.0764   -0.0768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4903   -0.1259   -0.5091 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5277   -0.1159   -1.8722 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8304    0.0180    0.1736 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6619   -1.2004   -0.0181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9630   -2.3539    0.6739 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8672   -3.8686    0.5254 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.5627   -2.5592    0.1453 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6768   -3.2636   -1.1853 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1165   -3.4746    1.1187 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7948   -4.5477    0.7819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5495    1.3017   -0.1620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8818    1.3261    0.5049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8074    1.4243   -1.6530 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.7897    0.2506    0.8296 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4960    1.0432    1.8880 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3048    0.2080   -1.7160 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7110    0.9634   -2.2790 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9309    1.9127   -1.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6730    3.1231    0.7289 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7807    5.1907    1.3317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6424    5.6285    1.3580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2131    3.8844    0.6909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2510   -0.5817   -2.3130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5972    0.0846    1.2774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9431   -1.4115   -1.0508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6307   -1.0913    0.5541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8835   -2.0844    1.7470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9112   -4.3560   -1.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5838   -2.8805   -1.7440 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1595   -3.1179   -1.8636 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0285   -3.2119    2.1790 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8913   -4.8198   -0.2498 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.9329    1.7151   -2.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
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 30 32  1  0
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 23 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
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  3  2  1  1
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  6  8  1  0
  8  9  1  0
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 17 16  1  0
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 13 12  1  0
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 20 21  1  6
 17 30  1  0
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 12 11  1  0
 13 18  1  0
 31 58  1  0
 31 59  1  0
 31 60  1  0
 32 61  1  0
 32 62  1  0
 32 63  1  0
 22 48  1  1
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 24 51  1  1
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 27 54  1  0
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 29 56  1  0
 29 57  1  0
  4 33  1  6
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  6 35  1  6
  7 36  1  0
  9 37  1  0
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 10 40  1  0
 10 41  1  0
 10 42  1  0
 16 46  1  0
 15 45  1  0
 14 44  1  0
 12 43  1  0
 21 47  1  0
M  CHG  2   1  -1   2   1
M  END


  Mrv1652309052210442D          

 32 36  0  0  1  0            999 V2000
   -0.0914    0.2304    0.0000 C   0  5  0  0  0  0  0  0  0  0  0  0
    0.6591    0.5731    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.4096    0.9158    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1715    0.1259    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3565   -0.0024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6406   -0.5528    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2328   -1.2699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4637   -0.6091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2256   -1.3990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1808   -1.0170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.8905   -0.0725    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3216    0.8235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0334    1.2406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0281    2.0656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3110    2.4734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5992    2.0563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6045    1.2314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8927    0.8143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1756    1.2221    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1193    0.3991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1703    2.0471    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4531    2.4550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7414    2.0379    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0242    2.4458    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.7467    1.2129    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1508    0.6424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0758    1.1486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5428    1.8287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8821    2.4642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4900    3.1901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2647    3.1951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0  0  0  0
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 22 30  1  0  0  0  0
 17 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
M  CHG  2   1  -1   2   1
M  END
> <DATABASE_ID>
NP0210772

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)[C@H]2C[C@@H](Cl)[C@](C)(C=C)[C@@]3([N+]#[C-])[C@@H](O)[C@H](O)C(C)(C)C4=C(C5=C1C=CC=C5N4)[C@]23O

> <INCHI_IDENTIFIER>
InChI=1S/C26H31ClN2O3/c1-8-24(6)16(27)12-15-22(2,3)13-10-9-11-14-17(13)18-19(29-14)23(4,5)20(30)21(31)26(24,28-7)25(15,18)32/h8-11,15-16,20-21,29-32H,1,12H2,2-6H3/t15-,16-,20+,21+,24+,25-,26+/m1/s1

> <INCHI_KEY>
UZVWRTZJFCDKBF-OODLVNIASA-N

> <FORMULA>
C26H31ClN2O3

> <MOLECULAR_WEIGHT>
455.0

> <EXACT_MASS>
454.2023206

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
48.86683295788465

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(9R,10R,11R,12R,13R,15R,16R)-13-chloro-12-ethenyl-11-isocyano-8,8,12,19,19-pentamethyl-6-azapentacyclo[13.3.1.0^{5,18}.0^{7,17}.0^{11,16}]nonadeca-1(18),2,4,7(17)-tetraene-9,10,16-triol

> <JCHEM_LOGP>
1.4434248897907214

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
12.543426026637796

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.840350545424009

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4666106569697117

> <JCHEM_POLAR_SURFACE_AREA>
80.84

> <JCHEM_REFRACTIVITY>
133.562

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(9R,10R,11R,12R,13R,15R,16R)-13-chloro-12-ethenyl-11-isocyano-8,8,12,19,19-pentamethyl-6-azapentacyclo[13.3.1.0^{5,18}.0^{7,17}.0^{11,16}]nonadeca-1(18),2,4,7(17)-tetraene-9,10,16-triol

> <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      -0.171   0.430   0.000  0.00  0.00           C-1
HETATM    2  N   UNK     0       1.230   1.070   0.000  0.00  0.00           N+1
HETATM    3  C   UNK     0       2.631   1.709   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.187   0.235   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.666  -0.004   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.063  -1.032   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.301  -2.370   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.599  -1.137   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.155  -2.611   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.938  -1.898   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.639  -0.001   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       7.262  -0.135   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       8.067   1.537   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.396   2.316   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.386   3.856   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.047   4.617   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.718   3.839   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.728   2.299   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.400   1.520   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.061   2.281   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.956   0.745   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.051   3.821   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.713   4.583   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.384   3.804   0.000  0.00  0.00           C+0
HETATM   25 Cl   UNK     0       0.045   4.565   0.000  0.00  0.00          Cl+0
HETATM   26  C   UNK     0       1.394   2.264   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.281   1.199   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.142   2.144   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.013   3.414   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.380   4.600   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.648   5.955   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.094   5.964   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   20   26                                             
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8   12   19                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   30                                                  
CONECT   18   17   13   19                                                  
CONECT   19   18   11   20                                                  
CONECT   20   19    3   21   22                                             
CONECT   21   20                                                            
CONECT   22   20   23   30                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24    3   27   28                                             
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28                                                            
CONECT   30   22   17   31   32                                             
CONECT   31   30                                                            
CONECT   32   30                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₁ClN₂O₃

Average Mass

455.0000 Da

Monoisotopic Mass

454.20232 Da

IUPAC Name

(9R,10R,11R,12R,13R,15R,16R)-13-chloro-12-ethenyl-11-isocyano-8,8,12,19,19-pentamethyl-6-azapentacyclo[13.3.1.0^{5,18}.0^{7,17}.0^{11,16}]nonadeca-1(18),2,4,7(17)-tetraene-9,10,16-triol

Traditional Name

(9R,10R,11R,12R,13R,15R,16R)-13-chloro-12-ethenyl-11-isocyano-8,8,12,19,19-pentamethyl-6-azapentacyclo[13.3.1.0^{5,18}.0^{7,17}.0^{11,16}]nonadeca-1(18),2,4,7(17)-tetraene-9,10,16-triol

CAS Registry Number

Not Available

SMILES

CC1(C)[C@H]2C[C@@H](Cl)[C@](C)(C=C)[C@@]3([N+]#[C-])[C@@H](O)[C@H](O)C(C)(C)C4=C(C5=C1C=CC=C5N4)[C@]23O

InChI Identifier

InChI=1S/C26H31ClN2O3/c1-8-24(6)16(27)12-15-22(2,3)13-10-9-11-14-17(13)18-19(29-14)23(4,5)20(30)21(31)26(24,28-7)25(15,18)32/h8-11,15-16,20-21,29-32H,1,12H2,2-6H3/t15-,16-,20+,21+,24+,25-,26+/m1/s1

InChI Key

UZVWRTZJFCDKBF-OODLVNIASA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

3-alkylindoles

Alternative Parents

Substituents

3-alkylindole
Isoindole or derivatives
Benzenoid
Cyclic alcohol
Pyrrole
Tertiary alcohol
Heteroaromatic compound
Secondary alcohol
Azacycle
Organic isocyanide
Polyol
Hydrocarbon derivative
Alkyl chloride
Alkyl halide
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Organic nitrogen compound
Organic oxygen compound
Alcohol
Organopnictogen compound
Organic zwitterion
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	1.44	ChemAxon
pKa (Strongest Acidic)	11.84	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	80.84 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	133.56 m³·mol⁻¹	ChemAxon
Polarizability	48.87 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

C00038431

Chemspider ID

10249748

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21610117

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Raveh A, Carmeli S: Antimicrobial ambiguines from the cyanobacterium Fischerella sp. collected in Israel. J Nat Prod. 2007 Feb;70(2):196-201. doi: 10.1021/np060495r. [PubMed:17315959 ]
LOTUS database [Link]

Showing NP-Card for (9r,10r,11r,12r,13r,15r,16r)-13-chloro-12-ethenyl-11-isocyano-8,8,12,19,19-pentamethyl-6-azapentacyclo[13.3.1.0⁵,¹⁸.0⁷,¹⁷.0¹¹,¹⁶]nonadeca-1(18),2,4,7(17)-tetraene-9,10,16-triol (NP0210772)

MOL for NP0210772 ((9r,10r,11r,12r,13r,15r,16r)-13-chloro-12-ethenyl-11-isocyano-8,8,12,19,19-pentamethyl-6-azapentacyclo[13.3.1.0⁵,¹⁸.0⁷,¹⁷.0¹¹,¹⁶]nonadeca-1(18),2,4,7(17)-tetraene-9,10,16-triol)

3D MOL for NP0210772 ((9r,10r,11r,12r,13r,15r,16r)-13-chloro-12-ethenyl-11-isocyano-8,8,12,19,19-pentamethyl-6-azapentacyclo[13.3.1.0⁵,¹⁸.0⁷,¹⁷.0¹¹,¹⁶]nonadeca-1(18),2,4,7(17)-tetraene-9,10,16-triol)

3D SDF for NP0210772 ((9r,10r,11r,12r,13r,15r,16r)-13-chloro-12-ethenyl-11-isocyano-8,8,12,19,19-pentamethyl-6-azapentacyclo[13.3.1.0⁵,¹⁸.0⁷,¹⁷.0¹¹,¹⁶]nonadeca-1(18),2,4,7(17)-tetraene-9,10,16-triol)

3D-SDF for NP0210772 ((9r,10r,11r,12r,13r,15r,16r)-13-chloro-12-ethenyl-11-isocyano-8,8,12,19,19-pentamethyl-6-azapentacyclo[13.3.1.0⁵,¹⁸.0⁷,¹⁷.0¹¹,¹⁶]nonadeca-1(18),2,4,7(17)-tetraene-9,10,16-triol)

PDB for NP0210772 ((9r,10r,11r,12r,13r,15r,16r)-13-chloro-12-ethenyl-11-isocyano-8,8,12,19,19-pentamethyl-6-azapentacyclo[13.3.1.0⁵,¹⁸.0⁷,¹⁷.0¹¹,¹⁶]nonadeca-1(18),2,4,7(17)-tetraene-9,10,16-triol)

3D PDB for NP0210772 ((9r,10r,11r,12r,13r,15r,16r)-13-chloro-12-ethenyl-11-isocyano-8,8,12,19,19-pentamethyl-6-azapentacyclo[13.3.1.0⁵,¹⁸.0⁷,¹⁷.0¹¹,¹⁶]nonadeca-1(18),2,4,7(17)-tetraene-9,10,16-triol)

SMILES for NP0210772 ((9r,10r,11r,12r,13r,15r,16r)-13-chloro-12-ethenyl-11-isocyano-8,8,12,19,19-pentamethyl-6-azapentacyclo[13.3.1.0⁵,¹⁸.0⁷,¹⁷.0¹¹,¹⁶]nonadeca-1(18),2,4,7(17)-tetraene-9,10,16-triol)

INCHI for NP0210772 ((9r,10r,11r,12r,13r,15r,16r)-13-chloro-12-ethenyl-11-isocyano-8,8,12,19,19-pentamethyl-6-azapentacyclo[13.3.1.0⁵,¹⁸.0⁷,¹⁷.0¹¹,¹⁶]nonadeca-1(18),2,4,7(17)-tetraene-9,10,16-triol)

Structure for NP0210772 ((9r,10r,11r,12r,13r,15r,16r)-13-chloro-12-ethenyl-11-isocyano-8,8,12,19,19-pentamethyl-6-azapentacyclo[13.3.1.0⁵,¹⁸.0⁷,¹⁷.0¹¹,¹⁶]nonadeca-1(18),2,4,7(17)-tetraene-9,10,16-triol)

3D Structure for NP0210772 ((9r,10r,11r,12r,13r,15r,16r)-13-chloro-12-ethenyl-11-isocyano-8,8,12,19,19-pentamethyl-6-azapentacyclo[13.3.1.0⁵,¹⁸.0⁷,¹⁷.0¹¹,¹⁶]nonadeca-1(18),2,4,7(17)-tetraene-9,10,16-triol)