NP-MRD: Showing NP-Card for (1s,4r,4as,13br)-4,4a-dimethyl-13b-(4-methylpent-3-en-1-yl)-1h,2h,3h,4h,5h,6h,8h-naphtho[2,1-b]carbazol-1-ol (NP0271897)

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Record Information

Version

2.0

Created at

2022-09-08 18:19:50 UTC

Updated at

2022-09-08 18:19:50 UTC

NP-MRD ID

NP0271897

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,4r,4as,13br)-4,4a-dimethyl-13b-(4-methylpent-3-en-1-yl)-1h,2h,3h,4h,5h,6h,8h-naphtho[2,1-b]carbazol-1-ol

Description

Tubingensin A belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene. (1s,4r,4as,13br)-4,4a-dimethyl-13b-(4-methylpent-3-en-1-yl)-1h,2h,3h,4h,5h,6h,8h-naphtho[2,1-b]carbazol-1-ol was first documented in 2008 (PMID: 18264578). Based on a literature review a small amount of articles have been published on Tubingensin A (PMID: 22537293) (PMID: 24524351).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082220192D          

 30 34  0  0  1  0            999 V2000
    2.6291    3.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2950    2.6940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0497    3.0271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2061    1.8738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8719    1.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7830    0.5665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4488    0.0794    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6941   -0.2537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0282    0.2334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2735   -0.0997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1845   -0.9199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8504   -1.4070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6052   -1.0739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2710   -1.5610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0258   -1.2279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1147   -0.4077    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7805   -0.8948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8695   -0.0746    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5353   -0.5617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9584    0.7456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2925    1.2327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5378    0.8996    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2854    1.6851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3770   -1.0888    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9668   -0.3730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1604   -0.1988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0919    0.5867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4621    1.1980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2685    1.0238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5209    0.2383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  7 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  7 22  1  0  0  0  0
 22 23  1  1  0  0  0
 11 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 25 30  2  0  0  0  0
 10 30  1  0  0  0  0
M  END

     RDKit          3D

 65 69  0  0  0  0  0  0  0  0999 V2000
    4.7768    2.8452    2.2783 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7512    2.4264    1.3068 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9187    2.7377   -0.1263 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6859    1.7761    1.7082 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6091    1.3280    0.7434 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5071   -0.1429    0.8247 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4989   -0.8554   -0.0128 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8884   -0.2823    0.2400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4541    0.6498   -0.6041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7124    1.1913   -0.3935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4434    0.7923    0.7015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8931   -0.1460    1.5653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6453   -0.6547    1.3176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0855   -1.6603    2.2470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4923   -2.7296    1.3945 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5233   -2.3142    0.3976 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8659   -2.7545    0.9434 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2404   -3.1384   -0.8610 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0817   -4.5744   -0.5093 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4415   -3.0795   -1.7404 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8033   -1.6655   -2.0079 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7631   -0.6689   -1.4721 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2863    0.5608   -1.8078 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6028    1.4652    0.6589 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6312    2.2708   -0.4177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5527    3.1511   -0.9226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3474    3.8834   -2.0755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1346    3.7128   -2.7574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1883    2.8358   -2.2758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4391    2.1288   -1.1231 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4289    2.7585    3.3336 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1738    3.8634    2.1028 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6650    2.1531    2.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0023    2.9821   -0.3280 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3539    3.6338   -0.4519 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7122    1.8402   -0.7423 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5608    1.5468    2.7581 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7459    1.8194   -0.1989 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6703    1.7826    1.1921 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5212   -0.5696    0.4915 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4782   -0.4644    1.8972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9367    0.9915   -1.4632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5015   -0.4308    2.4122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9180   -2.1695    2.8272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4345   -1.2501    3.0311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0846   -3.5022    2.1168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3558   -3.2692    0.9191 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0086   -2.4266    2.0063 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7171   -2.5718    0.3011 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7828   -3.8793    1.0284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6656   -2.7190   -1.3323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1245   -4.8515   -0.7854 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0300   -4.8060    0.5554 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6224   -5.2463   -1.0540 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1544   -3.6247   -2.6917 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2548   -3.6941   -1.3167 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7553   -1.5061   -3.1279 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8340   -1.3659   -1.7469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1519   -0.9051   -2.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8380    0.5614   -2.6090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3473    1.3545    1.3711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4890    3.2706   -0.3794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0975    4.5723   -2.4488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0119    4.3034   -3.6550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2702    2.7296   -2.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 18  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22  7  1  0
  7  6  1  1
  6  5  1  0
  5  4  1  0
  4  2  2  3
  2  1  1  0
  2  3  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 24  1  0
 24 25  1  0
 25 30  2  0
 30 29  1  0
 29 28  2  0
 28 27  1  0
 27 26  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  1
 16 18  1  0
 16  7  1  0
 13  8  1  0
 30 10  1  0
 26 25  1  0
 19 52  1  0
 19 53  1  0
 19 54  1  0
 18 51  1  6
 20 55  1  0
 20 56  1  0
 21 57  1  0
 21 58  1  0
 22 59  1  6
 23 60  1  0
  6 40  1  0
  6 41  1  0
  5 38  1  0
  5 39  1  0
  4 37  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  3 36  1  0
  9 42  1  0
 24 61  1  0
 29 65  1  0
 28 64  1  0
 27 63  1  0
 26 62  1  0
 12 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 17 48  1  0
 17 49  1  0
 17 50  1  0
M  END


  Mrv1652309082220192D          

 30 34  0  0  1  0            999 V2000
    2.6291    3.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2950    2.6940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0497    3.0271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2061    1.8738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8719    1.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7830    0.5665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4488    0.0794    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6941   -0.2537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0282    0.2334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2735   -0.0997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1845   -0.9199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8504   -1.4070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6052   -1.0739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2710   -1.5610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0258   -1.2279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1147   -0.4077    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7805   -0.8948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8695   -0.0746    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5353   -0.5617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9584    0.7456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2925    1.2327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5378    0.8996    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2854    1.6851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3770   -1.0888    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9668   -0.3730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1604   -0.1988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0919    0.5867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4621    1.1980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2685    1.0238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5209    0.2383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  7 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
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 21 22  1  0  0  0  0
  7 22  1  0  0  0  0
 22 23  1  1  0  0  0
 11 24  1  0  0  0  0
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 29 30  1  0  0  0  0
 25 30  2  0  0  0  0
 10 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0271897

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CC[C@H](O)[C@@]2(CCC=C(C)C)C3=CC4=C(NC5=C4C=CC=C5)C=C3CC[C@@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C28H35NO/c1-18(2)8-7-14-28-23-17-22-21-9-5-6-10-24(21)29-25(22)16-20(23)13-15-27(28,4)19(3)11-12-26(28)30/h5-6,8-10,16-17,19,26,29-30H,7,11-15H2,1-4H3/t19-,26+,27+,28-/m1/s1

> <INCHI_KEY>
BWCQRIGHZTXFEA-AIERRPMVSA-N

> <FORMULA>
C28H35NO

> <MOLECULAR_WEIGHT>
401.594

> <EXACT_MASS>
401.271864751

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
48.68401192763186

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(16S,17R,20S,21R)-16,17-dimethyl-21-(4-methylpent-3-en-1-yl)-10-azapentacyclo[11.8.0.0^{3,11}.0^{4,9}.0^{16,21}]henicosa-1,3(11),4,6,8,12-hexaen-20-ol

> <JCHEM_LOGP>
6.858606059666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.305958581743369

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.469407370598166

> <JCHEM_PKA_STRONGEST_BASIC>
-2.985870392946337

> <JCHEM_POLAR_SURFACE_AREA>
36.019999999999996

> <JCHEM_REFRACTIVITY>
126.26829999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(16S,17R,20S,21R)-16,17-dimethyl-21-(4-methylpent-3-en-1-yl)-10-azapentacyclo[11.8.0.0^{3,11}.0^{4,9}.0^{16,21}]henicosa-1,3(11),4,6,8,12-hexaen-20-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       4.908   5.938   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.151   5.029   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.560   5.651   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.985   3.498   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.228   2.589   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.062   1.057   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.304   0.148   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.896  -0.474   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.653   0.436   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.244  -0.186   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.078  -1.717   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.321  -2.626   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.730  -2.005   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.973  -2.914   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.381  -2.292   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.547  -0.761   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.790  -1.670   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.956  -0.139   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.199  -1.049   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.122   1.392   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.879   2.301   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.470   1.679   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       7.999   3.145   0.000  0.00  0.00           O+0
HETATM   24  N   UNK     0       2.570  -2.032   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       1.805  -0.696   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.299  -0.371   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.172   1.095   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.863   2.236   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.368   1.911   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.839   0.445   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   16   22                                             
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   30                                                  
CONECT   11   10   12   24                                                  
CONECT   12   11   13                                                       
CONECT   13   12    8   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    7   17   18                                             
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21    7   23                                                  
CONECT   23   22                                                            
CONECT   24   11   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   25   10                                                  
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₅NO

Average Mass

401.5940 Da

Monoisotopic Mass

401.27186 Da

IUPAC Name

(16S,17R,20S,21R)-16,17-dimethyl-21-(4-methylpent-3-en-1-yl)-10-azapentacyclo[11.8.0.0^{3,11}.0^{4,9}.0^{16,21}]henicosa-1,3(11),4,6,8,12-hexaen-20-ol

Traditional Name

(16S,17R,20S,21R)-16,17-dimethyl-21-(4-methylpent-3-en-1-yl)-10-azapentacyclo[11.8.0.0^{3,11}.0^{4,9}.0^{16,21}]henicosa-1,3(11),4,6,8,12-hexaen-20-ol

CAS Registry Number

Not Available

SMILES

C[C@@H]1CC[C@H](O)[C@@]2(CCC=C(C)C)C3=CC4=C(NC5=C4C=CC=C5)C=C3CC[C@@]12C

InChI Identifier

InChI=1S/C28H35NO/c1-18(2)8-7-14-28-23-17-22-21-9-5-6-10-24(21)29-25(22)16-20(23)13-15-27(28,4)19(3)11-12-26(28)30/h5-6,8-10,16-17,19,26,29-30H,7,11-15H2,1-4H3/t19-,26+,27+,28-/m1/s1

InChI Key

BWCQRIGHZTXFEA-AIERRPMVSA-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 phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Not Available

Direct Parent

Phenanthrenes and derivatives

Alternative Parents

Substituents

Phenanthrene
Carbazole
Tetralin
Indole
Indole or derivatives
Cyclic alcohol
Pyrrole
Heteroaromatic compound
Secondary alcohol
Organoheterocyclic compound
Azacycle
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Alcohol
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	6.86	ChemAxon
pKa (Strongest Acidic)	14.47	ChemAxon
pKa (Strongest Basic)	-3	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	3	ChemAxon
Refractivity	126.27 m³·mol⁻¹	ChemAxon
Polarizability	48.68 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

C00023603

Chemspider ID

10267469

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14413056

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Bian M, Wang Z, Xiong X, Sun Y, Matera C, Nicolaou KC, Li A: Total syntheses of anominine and tubingensin A. J Am Chem Soc. 2012 May 16;134(19):8078-81. doi: 10.1021/ja302765m. Epub 2012 May 2. [PubMed:22537293 ]
Bradshaw B, Etxebarria-Jardi G, Bonjoch J: Polycyclic framework synthesis of anominine and tubingensin A indole diterpenoids. Org Biomol Chem. 2008 Feb 21;6(4):772-8. doi: 10.1039/b718280e. Epub 2008 Jan 17. [PubMed:18264578 ]
Goetz AE, Silberstein AL, Corsello MA, Garg NK: Concise enantiospecific total synthesis of tubingensin A. J Am Chem Soc. 2014 Feb 26;136(8):3036-9. doi: 10.1021/ja501142e. Epub 2014 Feb 18. [PubMed:24524351 ]
LOTUS database [Link]

Showing NP-Card for (1s,4r,4as,13br)-4,4a-dimethyl-13b-(4-methylpent-3-en-1-yl)-1h,2h,3h,4h,5h,6h,8h-naphtho[2,1-b]carbazol-1-ol (NP0271897)

MOL for NP0271897 ((1s,4r,4as,13br)-4,4a-dimethyl-13b-(4-methylpent-3-en-1-yl)-1h,2h,3h,4h,5h,6h,8h-naphtho[2,1-b]carbazol-1-ol)

3D MOL for NP0271897 ((1s,4r,4as,13br)-4,4a-dimethyl-13b-(4-methylpent-3-en-1-yl)-1h,2h,3h,4h,5h,6h,8h-naphtho[2,1-b]carbazol-1-ol)

3D SDF for NP0271897 ((1s,4r,4as,13br)-4,4a-dimethyl-13b-(4-methylpent-3-en-1-yl)-1h,2h,3h,4h,5h,6h,8h-naphtho[2,1-b]carbazol-1-ol)

3D-SDF for NP0271897 ((1s,4r,4as,13br)-4,4a-dimethyl-13b-(4-methylpent-3-en-1-yl)-1h,2h,3h,4h,5h,6h,8h-naphtho[2,1-b]carbazol-1-ol)

PDB for NP0271897 ((1s,4r,4as,13br)-4,4a-dimethyl-13b-(4-methylpent-3-en-1-yl)-1h,2h,3h,4h,5h,6h,8h-naphtho[2,1-b]carbazol-1-ol)

3D PDB for NP0271897 ((1s,4r,4as,13br)-4,4a-dimethyl-13b-(4-methylpent-3-en-1-yl)-1h,2h,3h,4h,5h,6h,8h-naphtho[2,1-b]carbazol-1-ol)

SMILES for NP0271897 ((1s,4r,4as,13br)-4,4a-dimethyl-13b-(4-methylpent-3-en-1-yl)-1h,2h,3h,4h,5h,6h,8h-naphtho[2,1-b]carbazol-1-ol)

INCHI for NP0271897 ((1s,4r,4as,13br)-4,4a-dimethyl-13b-(4-methylpent-3-en-1-yl)-1h,2h,3h,4h,5h,6h,8h-naphtho[2,1-b]carbazol-1-ol)

Structure for NP0271897 ((1s,4r,4as,13br)-4,4a-dimethyl-13b-(4-methylpent-3-en-1-yl)-1h,2h,3h,4h,5h,6h,8h-naphtho[2,1-b]carbazol-1-ol)

3D Structure for NP0271897 ((1s,4r,4as,13br)-4,4a-dimethyl-13b-(4-methylpent-3-en-1-yl)-1h,2h,3h,4h,5h,6h,8h-naphtho[2,1-b]carbazol-1-ol)