NP-MRD: Showing NP-Card for siamenol (NP0029111)

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Record Information

Version

2.0

Created at

2021-06-19 20:48:48 UTC

Updated at

2021-06-29 23:56:17 UTC

NP-MRD ID

NP0029111

Secondary Accession Numbers

None

Natural Product Identification

Common Name

siamenol

Provided By

JEOL Database JEOL Logo

Description

Siamenol is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. siamenol is found in Murraya siamensis. siamenol was first documented in 2000 (PMID: 10757740). Based on a literature review a small amount of articles have been published on siamenol (PMID: 31355567) (PMID: 17602532) (PMID: 17036106) (PMID: 16755064).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192122483D          

 39 41  0  0  0  0            999 V2000
    5.0164    1.8482   -2.1916 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2727    1.7983   -0.8807 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1376    2.0531    0.3232 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9473    1.5517   -0.8585 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0352    1.4513    0.3355 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2451    0.1605    0.3513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1245    0.2004    0.0153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9054   -0.9757    0.0485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2917   -2.1688    0.4206 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0636   -2.2485    0.7540 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8138   -1.0709    0.6995 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1406   -1.2053    1.0095 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2546   -3.1489    0.3793 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4684   -2.6312   -0.0073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7059   -3.2610   -0.1757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7861   -2.4700   -0.5822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6385   -1.1004   -0.8239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8228   -0.2709   -1.2265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3864   -0.4917   -0.6322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2804   -1.2675   -0.2237 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3628    1.6578   -3.0494 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8097    1.0935   -2.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4708    2.8344   -2.3325 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6346    3.0246    0.2297 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9076    1.2785    0.4021 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5847    2.0638    1.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4371    1.4020   -1.8117 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3473    2.3060    0.3061 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5648    1.5395    1.2885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5958    1.1382   -0.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5281   -3.1874    1.0358 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6184   -0.4453    0.6386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0915   -4.1190    0.6041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8328   -4.3235    0.0039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7587   -2.9416   -0.7108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3318    0.1109   -0.3362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5325   -0.8625   -1.8144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5135    0.5758   -1.8484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2619    0.5746   -0.7981 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  2  0  0  0  0
  9 10  2  0  0  0  0
  8 20  1  0  0  0  0
 10 11  1  0  0  0  0
 19 17  1  0  0  0  0
 11  6  2  0  0  0  0
 14 13  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
 17 16  2  0  0  0  0
 17 18  1  0  0  0  0
  6  5  1  0  0  0  0
 16 15  1  0  0  0  0
  5  4  1  0  0  0  0
 15 14  2  0  0  0  0
  4  2  2  3  0  0  0
 14 20  1  0  0  0  0
  2  1  1  0  0  0  0
 13  9  1  0  0  0  0
  2  3  1  0  0  0  0
  8  9  1  0  0  0  0
 11 12  1  0  0  0  0
 13 33  1  0  0  0  0
 19 39  1  0  0  0  0
 16 35  1  0  0  0  0
 15 34  1  0  0  0  0
 10 31  1  0  0  0  0
  7 30  1  0  0  0  0
 18 36  1  0  0  0  0
 18 37  1  0  0  0  0
 18 38  1  0  0  0  0
  5 28  1  0  0  0  0
  5 29  1  0  0  0  0
  4 27  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  3 24  1  0  0  0  0
  3 25  1  0  0  0  0
  3 26  1  0  0  0  0
 12 32  1  0  0  0  0
M  END

     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
    5.0164    1.8482   -2.1916 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2727    1.7983   -0.8807 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1376    2.0531    0.3232 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9473    1.5517   -0.8585 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0352    1.4513    0.3355 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2451    0.1605    0.3513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1245    0.2004    0.0153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9054   -0.9757    0.0485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2917   -2.1688    0.4206 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0636   -2.2485    0.7540 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8138   -1.0709    0.6995 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1406   -1.2053    1.0095 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2546   -3.1489    0.3793 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4684   -2.6312   -0.0073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7059   -3.2610   -0.1757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7861   -2.4700   -0.5822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6385   -1.1004   -0.8239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8228   -0.2709   -1.2265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3864   -0.4917   -0.6322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2804   -1.2675   -0.2237 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3628    1.6578   -3.0494 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8097    1.0935   -2.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4708    2.8344   -2.3325 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6346    3.0246    0.2297 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9076    1.2785    0.4021 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5847    2.0638    1.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4371    1.4020   -1.8117 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3473    2.3060    0.3061 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5648    1.5395    1.2885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5958    1.1382   -0.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5281   -3.1874    1.0358 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6184   -0.4453    0.6386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0915   -4.1190    0.6041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8328   -4.3235    0.0039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7587   -2.9416   -0.7108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3318    0.1109   -0.3362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5325   -0.8625   -1.8144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5135    0.5758   -1.8484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2619    0.5746   -0.7981 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  2  0
  9 10  2  0
  8 20  1  0
 10 11  1  0
 19 17  1  0
 11  6  2  0
 14 13  1  0
  6  7  1  0
  7  8  2  0
 17 16  2  0
 17 18  1  0
  6  5  1  0
 16 15  1  0
  5  4  1  0
 15 14  2  0
  4  2  2  3
 14 20  1  0
  2  1  1  0
 13  9  1  0
  2  3  1  0
  8  9  1  0
 11 12  1  0
 13 33  1  0
 19 39  1  0
 16 35  1  0
 15 34  1  0
 10 31  1  0
  7 30  1  0
 18 36  1  0
 18 37  1  0
 18 38  1  0
  5 28  1  0
  5 29  1  0
  4 27  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
 12 32  1  0
M  END


  Mrv1652306192122483D          

 39 41  0  0  0  0            999 V2000
    5.0164    1.8482   -2.1916 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2727    1.7983   -0.8807 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1376    2.0531    0.3232 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9473    1.5517   -0.8585 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0352    1.4513    0.3355 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2451    0.1605    0.3513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1245    0.2004    0.0153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9054   -0.9757    0.0485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2917   -2.1688    0.4206 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0636   -2.2485    0.7540 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8138   -1.0709    0.6995 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1406   -1.2053    1.0095 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2546   -3.1489    0.3793 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4684   -2.6312   -0.0073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7059   -3.2610   -0.1757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7861   -2.4700   -0.5822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6385   -1.1004   -0.8239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8228   -0.2709   -1.2265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3864   -0.4917   -0.6322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2804   -1.2675   -0.2237 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3628    1.6578   -3.0494 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8097    1.0935   -2.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4708    2.8344   -2.3325 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6346    3.0246    0.2297 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9076    1.2785    0.4021 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5847    2.0638    1.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4371    1.4020   -1.8117 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3473    2.3060    0.3061 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5648    1.5395    1.2885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5958    1.1382   -0.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5281   -3.1874    1.0358 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6184   -0.4453    0.6386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0915   -4.1190    0.6041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8328   -4.3235    0.0039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7587   -2.9416   -0.7108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3318    0.1109   -0.3362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5325   -0.8625   -1.8144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5135    0.5758   -1.8484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2619    0.5746   -0.7981 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  2  0  0  0  0
  9 10  2  0  0  0  0
  8 20  1  0  0  0  0
 10 11  1  0  0  0  0
 19 17  1  0  0  0  0
 11  6  2  0  0  0  0
 14 13  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
 17 16  2  0  0  0  0
 17 18  1  0  0  0  0
  6  5  1  0  0  0  0
 16 15  1  0  0  0  0
  5  4  1  0  0  0  0
 15 14  2  0  0  0  0
  4  2  2  3  0  0  0
 14 20  1  0  0  0  0
  2  1  1  0  0  0  0
 13  9  1  0  0  0  0
  2  3  1  0  0  0  0
  8  9  1  0  0  0  0
 11 12  1  0  0  0  0
 13 33  1  0  0  0  0
 19 39  1  0  0  0  0
 16 35  1  0  0  0  0
 15 34  1  0  0  0  0
 10 31  1  0  0  0  0
  7 30  1  0  0  0  0
 18 36  1  0  0  0  0
 18 37  1  0  0  0  0
 18 38  1  0  0  0  0
  5 28  1  0  0  0  0
  5 29  1  0  0  0  0
  4 27  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  3 24  1  0  0  0  0
  3 25  1  0  0  0  0
  3 26  1  0  0  0  0
 12 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0029111

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(C([H])=C2C(N([H])C3=C([H])C([H])=C(C([H])=C23)C([H])([H])[H])=C1[H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C18H19NO/c1-11(2)4-6-13-9-15-14-8-12(3)5-7-16(14)19-17(15)10-18(13)20/h4-5,7-10,19-20H,6H2,1-3H3

> <INCHI_KEY>
BBPNJGRZPSCZBB-UHFFFAOYSA-N

> <FORMULA>
C18H19NO

> <MOLECULAR_WEIGHT>
265.356

> <EXACT_MASS>
265.146664236

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
32.02700213764652

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-methyl-3-(3-methylbut-2-en-1-yl)-9H-carbazol-2-ol

> <ALOGPS_LOGP>
4.78

> <JCHEM_LOGP>
5.029308756333334

> <ALOGPS_LOGS>
-5.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.844618405435856

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.806211009349429

> <JCHEM_PKA_STRONGEST_BASIC>
-6.062796653887415

> <JCHEM_POLAR_SURFACE_AREA>
36.019999999999996

> <JCHEM_REFRACTIVITY>
84.73709999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.81e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-methyl-3-(3-methylbut-2-en-1-yl)-9H-carbazol-2-ol

> <JCHEM_VEBER_RULE>
1

$$$$

     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
    5.0164    1.8482   -2.1916 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2727    1.7983   -0.8807 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1376    2.0531    0.3232 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9473    1.5517   -0.8585 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0352    1.4513    0.3355 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2451    0.1605    0.3513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1245    0.2004    0.0153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9054   -0.9757    0.0485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2917   -2.1688    0.4206 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0636   -2.2485    0.7540 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8138   -1.0709    0.6995 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1406   -1.2053    1.0095 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2546   -3.1489    0.3793 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4684   -2.6312   -0.0073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7059   -3.2610   -0.1757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7861   -2.4700   -0.5822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6385   -1.1004   -0.8239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8228   -0.2709   -1.2265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3864   -0.4917   -0.6322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2804   -1.2675   -0.2237 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3628    1.6578   -3.0494 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8097    1.0935   -2.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4708    2.8344   -2.3325 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6346    3.0246    0.2297 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9076    1.2785    0.4021 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5847    2.0638    1.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4371    1.4020   -1.8117 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3473    2.3060    0.3061 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5648    1.5395    1.2885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5958    1.1382   -0.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5281   -3.1874    1.0358 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6184   -0.4453    0.6386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0915   -4.1190    0.6041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8328   -4.3235    0.0039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7587   -2.9416   -0.7108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3318    0.1109   -0.3362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5325   -0.8625   -1.8144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5135    0.5758   -1.8484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2619    0.5746   -0.7981 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  2  0
  9 10  2  0
  8 20  1  0
 10 11  1  0
 19 17  1  0
 11  6  2  0
 14 13  1  0
  6  7  1  0
  7  8  2  0
 17 16  2  0
 17 18  1  0
  6  5  1  0
 16 15  1  0
  5  4  1  0
 15 14  2  0
  4  2  2  3
 14 20  1  0
  2  1  1  0
 13  9  1  0
  2  3  1  0
  8  9  1  0
 11 12  1  0
 13 33  1  0
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 18 36  1  0
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  5 28  1  0
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  1 21  1  0
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  3 24  1  0
  3 25  1  0
  3 26  1  0
 12 32  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       5.016   1.848  -2.192  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.273   1.798  -0.881  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.138   2.053   0.323  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.947   1.552  -0.859  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.035   1.451   0.336  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.245   0.161   0.351  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.125   0.200   0.015  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.905  -0.976   0.049  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.292  -2.169   0.421  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.064  -2.248   0.754  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.814  -1.071   0.700  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.141  -1.205   1.010  0.00  0.00           O+0
HETATM   13  N   UNK     0      -1.255  -3.149   0.379  0.00  0.00           N+0
HETATM   14  C   UNK     0      -2.468  -2.631  -0.007  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.706  -3.261  -0.176  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.786  -2.470  -0.582  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.638  -1.100  -0.824  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.823  -0.271  -1.226  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.386  -0.492  -0.632  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.280  -1.268  -0.224  0.00  0.00           C+0
HETATM   21  H   UNK     0       4.363   1.658  -3.049  0.00  0.00           H+0
HETATM   22  H   UNK     0       5.810   1.093  -2.205  0.00  0.00           H+0
HETATM   23  H   UNK     0       5.471   2.834  -2.333  0.00  0.00           H+0
HETATM   24  H   UNK     0       5.635   3.025   0.230  0.00  0.00           H+0
HETATM   25  H   UNK     0       5.908   1.278   0.402  0.00  0.00           H+0
HETATM   26  H   UNK     0       4.585   2.064   1.264  0.00  0.00           H+0
HETATM   27  H   UNK     0       2.437   1.402  -1.812  0.00  0.00           H+0
HETATM   28  H   UNK     0       1.347   2.306   0.306  0.00  0.00           H+0
HETATM   29  H   UNK     0       2.565   1.540   1.289  0.00  0.00           H+0
HETATM   30  H   UNK     0      -0.596   1.138  -0.266  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.528  -3.187   1.036  0.00  0.00           H+0
HETATM   32  H   UNK     0       3.618  -0.445   0.639  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.091  -4.119   0.604  0.00  0.00           H+0
HETATM   34  H   UNK     0      -3.833  -4.324   0.004  0.00  0.00           H+0
HETATM   35  H   UNK     0      -5.759  -2.942  -0.711  0.00  0.00           H+0
HETATM   36  H   UNK     0      -6.332   0.111  -0.336  0.00  0.00           H+0
HETATM   37  H   UNK     0      -6.532  -0.863  -1.814  0.00  0.00           H+0
HETATM   38  H   UNK     0      -5.513   0.576  -1.848  0.00  0.00           H+0
HETATM   39  H   UNK     0      -3.262   0.575  -0.798  0.00  0.00           H+0
CONECT    1    2   21   22   23                                             
CONECT    2    4    1    3                                                  
CONECT    3    2   24   25   26                                             
CONECT    4    5    2   27                                                  
CONECT    5    6    4   28   29                                             
CONECT    6   11    7    5                                                  
CONECT    7    6    8   30                                                  
CONECT    8   20    7    9                                                  
CONECT    9   10   13    8                                                  
CONECT   10    9   11   31                                                  
CONECT   11   10    6   12                                                  
CONECT   12   11   32                                                       
CONECT   13   14    9   33                                                  
CONECT   14   13   15   20                                                  
CONECT   15   16   14   34                                                  
CONECT   16   17   15   35                                                  
CONECT   17   19   16   18                                                  
CONECT   18   17   36   37   38                                             
CONECT   19   20   17   39                                                  
CONECT   20   19    8   14                                                  
CONECT   21    1                                                            
CONECT   22    1                                                            
CONECT   23    1                                                            
CONECT   24    3                                                            
CONECT   25    3                                                            
CONECT   26    3                                                            
CONECT   27    4                                                            
CONECT   28    5                                                            
CONECT   29    5                                                            
CONECT   30    7                                                            
CONECT   31   10                                                            
CONECT   32   12                                                            
CONECT   33   13                                                            
CONECT   34   15                                                            
CONECT   35   16                                                            
CONECT   36   18                                                            
CONECT   37   18                                                            
CONECT   38   18                                                            
CONECT   39   19                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   82    0
END

RDKit          3D

39 41  0  0  0  0  0  0  0  0999 V2000
    5.0164    1.8482   -2.1916 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2727    1.7983   -0.8807 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1376    2.0531    0.3232 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9473    1.5517   -0.8585 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0352    1.4513    0.3355 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2451    0.1605    0.3513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1245    0.2004    0.0153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9054   -0.9757    0.0485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2917   -2.1688    0.4206 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0636   -2.2485    0.7540 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8138   -1.0709    0.6995 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1406   -1.2053    1.0095 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2546   -3.1489    0.3793 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4684   -2.6312   -0.0073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7059   -3.2610   -0.1757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7861   -2.4700   -0.5822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6385   -1.1004   -0.8239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8228   -0.2709   -1.2265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3864   -0.4917   -0.6322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2804   -1.2675   -0.2237 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3628    1.6578   -3.0494 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8097    1.0935   -2.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4708    2.8344   -2.3325 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6346    3.0246    0.2297 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9076    1.2785    0.4021 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5847    2.0638    1.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4371    1.4020   -1.8117 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3473    2.3060    0.3061 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5648    1.5395    1.2885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5958    1.1382   -0.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5281   -3.1874    1.0358 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6184   -0.4453    0.6386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0915   -4.1190    0.6041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8328   -4.3235    0.0039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7587   -2.9416   -0.7108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3318    0.1109   -0.3362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5325   -0.8625   -1.8144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5135    0.5758   -1.8484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2619    0.5746   -0.7981 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  2  0
  9 10  2  0
  8 20  1  0
 10 11  1  0
 19 17  1  0
 11  6  2  0
 14 13  1  0
  6  7  1  0
  7  8  2  0
 17 16  2  0
 17 18  1  0
  6  5  1  0
 16 15  1  0
  5  4  1  0
 15 14  2  0
  4  2  2  3
 14 20  1  0
  2  1  1  0
 13  9  1  0
  2  3  1  0
  8  9  1  0
 11 12  1  0
 13 33  1  0
 19 39  1  0
 16 35  1  0
 15 34  1  0
 10 31  1  0
  7 30  1  0
 18 36  1  0
 18 37  1  0
 18 38  1  0
  5 28  1  0
  5 29  1  0
  4 27  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
 12 32  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₁₉NO

Average Mass

265.3560 Da

Monoisotopic Mass

265.14666 Da

IUPAC Name

6-methyl-3-(3-methylbut-2-en-1-yl)-9H-carbazol-2-ol

Traditional Name

6-methyl-3-(3-methylbut-2-en-1-yl)-9H-carbazol-2-ol

CAS Registry Number

Not Available

SMILES

[H]OC1=C(C([H])=C2C(N([H])C3=C([H])C([H])=C(C([H])=C23)C([H])([H])[H])=C1[H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C18H19NO/c1-11(2)4-6-13-9-15-14-8-12(3)5-7-16(14)19-17(15)10-18(13)20/h4-5,7-10,19-20H,6H2,1-3H3

InChI Key

BBPNJGRZPSCZBB-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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
Mammea siamensis	KNApSAcK Database	22123792
Murraya siamensis	JEOL database	Meragelman, K. M., et al, J. Nat. Prod. 63, 427 (2000)

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as carbazoles. These are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Carbazoles

Direct Parent

Carbazoles

Alternative Parents

Substituents

Carbazole
Hydroxyindole
Indole
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Heteroaromatic compound
Pyrrole
Azacycle
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

phenols (CHEBI:66479 )
carbazole alkaloid (CHEBI:66479 )

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	4.78	ALOGPS
logP	5.03	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	8.81	ChemAxon
pKa (Strongest Basic)	-6.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	36.02 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	84.74 m³·mol⁻¹	ChemAxon
Polarizability	32.03 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

C00031375

Chemspider ID

419088

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

66479

Good Scents ID

Not Available

References

General References

Hu S, Guo JM, Zhang WH, Zhang MM, Liu YP, Fu YH: [Chemical constituents from stems and leaves of Clausena emarginata]. Zhongguo Zhong Yao Za Zhi. 2019 May;44(10):2096-2101. doi: 10.19540/j.cnki.cjcmm.20190321.204. [PubMed:31355567 ]
Naffziger MR, Ashburn BO, Perkins JR, Carter RG: Diels-Alder approach for the construction of halogenated, o-nitro biaryl templates and application to the total synthesis of the anti-HIV agent siamenol. J Org Chem. 2007 Dec 21;72(26):9857-65. doi: 10.1021/jo070740r. Epub 2007 Jun 29. [PubMed:17602532 ]
Krahl MP, Jager A, Krause T, Knolker HJ: First total synthesis of the 7-oxygenated carbazole alkaloids clauszoline-K, 3-formyl-7-hydroxycarbazole, clausine M, clausine N and the anti-HIV active siamenol using a highly efficient palladium-catalyzed approach. Org Biomol Chem. 2006 Sep 7;4(17):3215-9. doi: 10.1039/b607792g. Epub 2006 Jul 26. [PubMed:17036106 ]
Prachyawarakorn V, Mahidol C, Ruchirawat S: Siamenols A-D, four new coumarins from Mammea siamensis. Chem Pharm Bull (Tokyo). 2006 Jun;54(6):884-6. doi: 10.1248/cpb.54.884. [PubMed:16755064 ]
Meragelman KM, McKee TC, Boyd MR: Siamenol, a new carbazole alkaloid from Murraya siamensis. J Nat Prod. 2000 Mar;63(3):427-8. doi: 10.1021/np990570g. [PubMed:10757740 ]
Meragelman, K. M., et al. (2000). Meragelman, K. M., et al, J. Nat. Prod. 63, 427 (2000). J. Nat. Prod..

Showing NP-Card for siamenol (NP0029111)

MOL for NP0029111 (siamenol)

3D MOL for NP0029111 (siamenol)

3D SDF for NP0029111 (siamenol)

3D-SDF for NP0029111 (siamenol)

PDB for NP0029111 (siamenol)

3D PDB for NP0029111 (siamenol)

SMILES for NP0029111 (siamenol)

INCHI for NP0029111 (siamenol)

Structure for NP0029111 (siamenol)

3D Structure for NP0029111 (siamenol)