NP-MRD: Showing NP-Card for (2r,3s,4r,5r,7r)-5-chloro-4-ethenyl-3-isocyano-4,8,8-trimethyl-15-(2-methylbut-3-en-2-yl)-14-azatetracyclo[7.6.1.0²,⁷.0¹³,¹⁶]hexadeca-1(15),9(16),10,12-tetraen-2-ol (NP0208080)

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Record Information

Version

2.0

Created at

2022-09-05 04:56:50 UTC

Updated at

2022-09-05 04:56:50 UTC

NP-MRD ID

NP0208080

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3s,4r,5r,7r)-5-chloro-4-ethenyl-3-isocyano-4,8,8-trimethyl-15-(2-methylbut-3-en-2-yl)-14-azatetracyclo[7.6.1.0²,⁷.0¹³,¹⁶]hexadeca-1(15),9(16),10,12-tetraen-2-ol

Description

Ambiguine B 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. (2r,3s,4r,5r,7r)-5-chloro-4-ethenyl-3-isocyano-4,8,8-trimethyl-15-(2-methylbut-3-en-2-yl)-14-azatetracyclo[7.6.1.0²,⁷.0¹³,¹⁶]hexadeca-1(15),9(16),10,12-tetraen-2-ol is found in Hapalosiphon delicatulus. (2r,3s,4r,5r,7r)-5-chloro-4-ethenyl-3-isocyano-4,8,8-trimethyl-15-(2-methylbut-3-en-2-yl)-14-azatetracyclo[7.6.1.0²,⁷.0¹³,¹⁶]hexadeca-1(15),9(16),10,12-tetraen-2-ol was first documented in 2007 (PMID: 17315959). Based on a literature review a small amount of articles have been published on ambiguine B isonitrile.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052206562D          

 30 33  0  0  1  0            999 V2000
    4.3769    2.1591    0.0000 C   0  5  0  0  0  0  0  0  0  0  0  0
    4.4208    1.3352    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    4.4648    0.5114    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2002    0.1375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4407    0.9267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0191    0.0377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5150    0.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2441   -0.6863    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9795   -1.0602    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.5526   -1.1363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8172   -0.7624    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1257   -1.2123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6889   -1.8152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6298   -1.8716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3902   -0.8384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4481   -1.1259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8065   -0.6073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9348    0.2077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7047    0.5040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9997    1.2745    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8236    1.2320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3422    1.8736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7006    2.3923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9838    1.3550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8608    2.5153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5645    3.2852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0378    0.4353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3463   -0.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7732    0.0615    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7293    0.8853    0.0000 O   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  1  0  0  0
  6  7  2  0  0  0  0
  4  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  2  0  0  0  0
 21 27  2  0  0  0  0
 27 28  1  0  0  0  0
 15 28  2  0  0  0  0
 19 28  1  0  0  0  0
 27 29  1  0  0  0  0
  3 29  1  0  0  0  0
 11 29  1  0  0  0  0
 29 30  1  6  0  0  0
M  CHG  2   1  -1   2   1
M  END

     RDKit          3D

 61 64  0  0  0  0  0  0  0  0999 V2000
    0.7593   -1.3477   -2.8840 C   0  0  0  0  0  3  0  0  0  0  0  0
    0.7323   -1.3480   -1.7184 N   0  0  0  0  0  4  0  0  0  0  0  0
    0.6855   -1.3733   -0.2903 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0897   -1.8098    0.1403 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0876   -2.4511    1.5107 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4893   -2.8931   -0.8276 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6806   -3.4655   -0.7462 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0863   -0.7275    0.1146 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6265   -0.1977    1.7487 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.6841    0.4102   -0.7513 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2823    0.8710   -0.6816 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2766    2.3090   -0.3156 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9584    2.7048    0.9328 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9248    3.0565   -1.4850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1172    2.7676   -0.2813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3892    4.1100   -0.4812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7132    4.5064   -0.4478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7394    3.5823   -0.2200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3882    2.2659   -0.0302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1118    1.1614    0.2053 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2848    0.0932    0.3191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7447   -1.2873    0.5269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2242   -1.9564    1.7692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5697   -2.1248   -0.7409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2222   -1.3394    0.7071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8712   -2.4799    0.5544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9639    0.5028    0.1548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0982    1.8768   -0.0621 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3668   -0.0165    0.1900 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8179    0.0673    1.5295 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1098   -2.2134    0.0712 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0163   -2.1809    2.0435 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0503   -3.5753    1.4086 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1755   -2.1659    2.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8219   -3.2313   -1.6085 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9723   -4.2391   -1.4335 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3538   -3.1323    0.0328 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0390   -1.1502   -0.3311 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9787    0.1600   -1.8152 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4179    1.2361   -0.4996 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8202    0.7961   -1.6955 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5908    2.2399    1.8451 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7574    3.8112    1.0654 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0616    2.6322    0.9332 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7850    2.5460   -1.9100 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1418    3.0558   -2.2994 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1566    4.0915   -1.2339 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3525    4.8504   -0.6577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0042    5.5359   -0.5949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7557    3.8886   -0.1948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1614    1.2044    0.2724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1840   -1.7399    2.0170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8956   -1.7505    2.6384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2634   -3.0663    1.5609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0365   -3.0404   -0.4638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9620   -1.5401   -1.4423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4989   -2.3991   -1.2435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7603   -0.4636    0.9716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3297   -3.3654    0.3014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9404   -2.5558    0.6758 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0804    0.2944    2.1476 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 22  1  0
 22 24  1  0
 22 25  1  0
 25 26  2  3
 22 21  1  0
 21 27  2  0
 27 28  1  0
 28 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 15 12  1  0
 12 13  1  0
 12 14  1  0
 12 11  1  0
 11 10  1  0
 10  8  1  0
  8  9  1  0
  8  4  1  0
  4  5  1  0
  4  6  1  6
  6  7  2  3
  4  3  1  0
  3  2  1  0
  2  1  3  0
  3 29  1  0
 29 30  1  1
 20 21  1  0
 29 11  1  0
 29 27  1  0
 19 28  1  0
 23 52  1  0
 23 53  1  0
 23 54  1  0
 24 55  1  0
 24 56  1  0
 24 57  1  0
 25 58  1  0
 26 59  1  0
 26 60  1  0
 16 48  1  0
 17 49  1  0
 18 50  1  0
 20 51  1  0
 13 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  0
 14 46  1  0
 14 47  1  0
 11 41  1  6
 10 39  1  0
 10 40  1  0
  8 38  1  6
  5 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  7 36  1  0
  7 37  1  0
  3 31  1  6
 30 61  1  0
M  CHG  2   1  -1   2   1
M  END


  Mrv1652309052206562D          

 30 33  0  0  1  0            999 V2000
    4.3769    2.1591    0.0000 C   0  5  0  0  0  0  0  0  0  0  0  0
    4.4208    1.3352    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    4.4648    0.5114    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2002    0.1375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4407    0.9267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0191    0.0377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5150    0.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2441   -0.6863    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9795   -1.0602    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.5526   -1.1363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8172   -0.7624    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1257   -1.2123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6889   -1.8152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6298   -1.8716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3902   -0.8384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4481   -1.1259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8065   -0.6073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9348    0.2077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7047    0.5040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9997    1.2745    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8236    1.2320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3422    1.8736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7006    2.3923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9838    1.3550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8608    2.5153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5645    3.2852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0378    0.4353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3463   -0.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7732    0.0615    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7293    0.8853    0.0000 O   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  1  0  0  0
  6  7  2  0  0  0  0
  4  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  2  0  0  0  0
 21 27  2  0  0  0  0
 27 28  1  0  0  0  0
 15 28  2  0  0  0  0
 19 28  1  0  0  0  0
 27 29  1  0  0  0  0
  3 29  1  0  0  0  0
 11 29  1  0  0  0  0
 29 30  1  6  0  0  0
M  CHG  2   1  -1   2   1
M  END
> <DATABASE_ID>
NP0208080

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(C=C)C1=C2C3=C(C=CC=C3N1)C(C)(C)[C@H]1C[C@@H](Cl)[C@](C)(C=C)[C@H]([N+]#[C-])[C@]21O

> <INCHI_IDENTIFIER>
InChI=1S/C26H31ClN2O/c1-9-23(3,4)21-20-19-15(12-11-13-16(19)29-21)24(5,6)17-14-18(27)25(7,10-2)22(28-8)26(17,20)30/h9-13,17-18,22,29-30H,1-2,14H2,3-7H3/t17-,18-,22+,25+,26-/m1/s1

> <INCHI_KEY>
XNSXDDHLEKKURV-PJYKFWTKSA-N

> <FORMULA>
C26H31ClN2O

> <MOLECULAR_WEIGHT>
423.0

> <EXACT_MASS>
422.2124913

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
47.120502261625745

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S,4R,5R,7R)-5-chloro-4-ethenyl-3-isocyano-4,8,8-trimethyl-15-(2-methylbut-3-en-2-yl)-14-azatetracyclo[7.6.1.0^{2,7}.0^{13,16}]hexadeca-1(15),9(16),10,12-tetraen-2-ol

> <JCHEM_LOGP>
3.6831008267907204

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
15.548788761758644

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.23771346873237

> <JCHEM_PKA_STRONGEST_BASIC>
-4.006801346864063

> <JCHEM_POLAR_SURFACE_AREA>
40.379999999999995

> <JCHEM_REFRACTIVITY>
132.87910000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,4R,5R,7R)-5-chloro-4-ethenyl-3-isocyano-4,8,8-trimethyl-15-(2-methylbut-3-en-2-yl)-14-azatetracyclo[7.6.1.0^{2,7}.0^{13,16}]hexadeca-1(15),9(16),10,12-tetraen-2-ol

> <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       8.170   4.030   0.000  0.00  0.00           C-1
HETATM    2  N   UNK     0       8.252   2.492   0.000  0.00  0.00           N+1
HETATM    3  C   UNK     0       8.334   0.955   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.707   0.257   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.156   1.730   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.236   0.070   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.161   1.301   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.789  -1.281   0.000  0.00  0.00           C+0
HETATM    9 Cl   UNK     0      11.162  -1.979   0.000  0.00  0.00          Cl+0
HETATM   10  C   UNK     0       8.498  -2.121   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.125  -1.423   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.835  -2.263   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.886  -3.388   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.909  -3.494   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.462  -1.565   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.703  -2.102   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.505  -1.134   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.745   0.388   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.182   0.941   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       3.733   2.379   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       5.271   2.300   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.239   3.497   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.041   4.466   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.436   2.529   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.207   4.695   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.654   6.132   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.671   0.813   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.380  -0.027   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.043   0.115   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       6.961   1.653   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   29                                                  
CONECT    4    3    5    6    8                                             
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6                                                            
CONECT    8    4    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   29                                                  
CONECT   12   11   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   12   16   28                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   28                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   27                                                  
CONECT   22   21   23   24   25                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   22   26                                                       
CONECT   26   25                                                            
CONECT   27   21   28   29                                                  
CONECT   28   27   15   19                                                  
CONECT   29   27    3   11   30                                             
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₁ClN₂O

Average Mass

423.0000 Da

Monoisotopic Mass

422.21249 Da

IUPAC Name

(2R,3S,4R,5R,7R)-5-chloro-4-ethenyl-3-isocyano-4,8,8-trimethyl-15-(2-methylbut-3-en-2-yl)-14-azatetracyclo[7.6.1.0^{2,7}.0^{13,16}]hexadeca-1(15),9(16),10,12-tetraen-2-ol

Traditional Name

(2R,3S,4R,5R,7R)-5-chloro-4-ethenyl-3-isocyano-4,8,8-trimethyl-15-(2-methylbut-3-en-2-yl)-14-azatetracyclo[7.6.1.0^{2,7}.0^{13,16}]hexadeca-1(15),9(16),10,12-tetraen-2-ol

CAS Registry Number

Not Available

SMILES

CC(C)(C=C)C1=C2C3=C(C=CC=C3N1)C(C)(C)[C@H]1C[C@@H](Cl)[C@](C)(C=C)[C@H]([N+]#[C-])[C@]21O

InChI Identifier

InChI=1S/C26H31ClN2O/c1-9-23(3,4)21-20-19-15(12-11-13-16(19)29-21)24(5,6)17-14-18(27)25(7,10-2)22(28-8)26(17,20)30/h9-13,17-18,22,29-30H,1-2,14H2,3-7H3/t17-,18-,22+,25+,26-/m1/s1

InChI Key

XNSXDDHLEKKURV-PJYKFWTKSA-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
Hapalosiphon delicatulus	LOTUS Database	35616633

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
Substituted pyrrole
Benzenoid
Cyclic alcohol
Pyrrole
Tertiary alcohol
Heteroaromatic compound
Organic isocyanide
Azacycle
Organopnictogen compound
Alkyl halide
Organic oxygen compound
Alkyl chloride
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Organic nitrogen compound
Alcohol
Organic zwitterion
Hydrocarbon derivative
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	3.68	ChemAxon
pKa (Strongest Acidic)	12.24	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.38 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	132.88 m³·mol⁻¹	ChemAxon
Polarizability	47.12 Å³	ChemAxon
Number of Rings	4	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

C00027103

Chemspider ID

10249744

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21610113

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 (2r,3s,4r,5r,7r)-5-chloro-4-ethenyl-3-isocyano-4,8,8-trimethyl-15-(2-methylbut-3-en-2-yl)-14-azatetracyclo[7.6.1.0²,⁷.0¹³,¹⁶]hexadeca-1(15),9(16),10,12-tetraen-2-ol (NP0208080)

MOL for NP0208080 ((2r,3s,4r,5r,7r)-5-chloro-4-ethenyl-3-isocyano-4,8,8-trimethyl-15-(2-methylbut-3-en-2-yl)-14-azatetracyclo[7.6.1.0²,⁷.0¹³,¹⁶]hexadeca-1(15),9(16),10,12-tetraen-2-ol)

3D MOL for NP0208080 ((2r,3s,4r,5r,7r)-5-chloro-4-ethenyl-3-isocyano-4,8,8-trimethyl-15-(2-methylbut-3-en-2-yl)-14-azatetracyclo[7.6.1.0²,⁷.0¹³,¹⁶]hexadeca-1(15),9(16),10,12-tetraen-2-ol)

3D SDF for NP0208080 ((2r,3s,4r,5r,7r)-5-chloro-4-ethenyl-3-isocyano-4,8,8-trimethyl-15-(2-methylbut-3-en-2-yl)-14-azatetracyclo[7.6.1.0²,⁷.0¹³,¹⁶]hexadeca-1(15),9(16),10,12-tetraen-2-ol)

3D-SDF for NP0208080 ((2r,3s,4r,5r,7r)-5-chloro-4-ethenyl-3-isocyano-4,8,8-trimethyl-15-(2-methylbut-3-en-2-yl)-14-azatetracyclo[7.6.1.0²,⁷.0¹³,¹⁶]hexadeca-1(15),9(16),10,12-tetraen-2-ol)

PDB for NP0208080 ((2r,3s,4r,5r,7r)-5-chloro-4-ethenyl-3-isocyano-4,8,8-trimethyl-15-(2-methylbut-3-en-2-yl)-14-azatetracyclo[7.6.1.0²,⁷.0¹³,¹⁶]hexadeca-1(15),9(16),10,12-tetraen-2-ol)

3D PDB for NP0208080 ((2r,3s,4r,5r,7r)-5-chloro-4-ethenyl-3-isocyano-4,8,8-trimethyl-15-(2-methylbut-3-en-2-yl)-14-azatetracyclo[7.6.1.0²,⁷.0¹³,¹⁶]hexadeca-1(15),9(16),10,12-tetraen-2-ol)

SMILES for NP0208080 ((2r,3s,4r,5r,7r)-5-chloro-4-ethenyl-3-isocyano-4,8,8-trimethyl-15-(2-methylbut-3-en-2-yl)-14-azatetracyclo[7.6.1.0²,⁷.0¹³,¹⁶]hexadeca-1(15),9(16),10,12-tetraen-2-ol)

INCHI for NP0208080 ((2r,3s,4r,5r,7r)-5-chloro-4-ethenyl-3-isocyano-4,8,8-trimethyl-15-(2-methylbut-3-en-2-yl)-14-azatetracyclo[7.6.1.0²,⁷.0¹³,¹⁶]hexadeca-1(15),9(16),10,12-tetraen-2-ol)

Structure for NP0208080 ((2r,3s,4r,5r,7r)-5-chloro-4-ethenyl-3-isocyano-4,8,8-trimethyl-15-(2-methylbut-3-en-2-yl)-14-azatetracyclo[7.6.1.0²,⁷.0¹³,¹⁶]hexadeca-1(15),9(16),10,12-tetraen-2-ol)

3D Structure for NP0208080 ((2r,3s,4r,5r,7r)-5-chloro-4-ethenyl-3-isocyano-4,8,8-trimethyl-15-(2-methylbut-3-en-2-yl)-14-azatetracyclo[7.6.1.0²,⁷.0¹³,¹⁶]hexadeca-1(15),9(16),10,12-tetraen-2-ol)