NP-MRD: Showing NP-Card for (12s,13s)-15-[5-(3-chloro-1h-pyrrol-2-yl)-3-methoxyfuran-2-yl]-13-isopropyl-2-azatricyclo[10.2.1.1³,¹⁴]hexadeca-1(15),2,14(16)-triene (NP0187729)

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Record Information

Version

2.0

Created at

2022-09-04 03:57:01 UTC

Updated at

2022-09-04 03:57:01 UTC

NP-MRD ID

NP0187729

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(12s,13s)-15-[5-(3-chloro-1h-pyrrol-2-yl)-3-methoxyfuran-2-yl]-13-isopropyl-2-azatricyclo[10.2.1.1³,¹⁴]hexadeca-1(15),2,14(16)-triene

Description

Roseophilin belongs to the class of organic compounds known as alkyl aryl ethers. These are organic compounds containing the alkyl aryl ether functional group with the generic formula R-O-R' , where R is an alkyl group and R' is an aryl group. (12s,13s)-15-[5-(3-chloro-1h-pyrrol-2-yl)-3-methoxyfuran-2-yl]-13-isopropyl-2-azatricyclo[10.2.1.1³,¹⁴]hexadeca-1(15),2,14(16)-triene is found in Streptomyces griseoviridis. (12s,13s)-15-[5-(3-chloro-1h-pyrrol-2-yl)-3-methoxyfuran-2-yl]-13-isopropyl-2-azatricyclo[10.2.1.1³,¹⁴]hexadeca-1(15),2,14(16)-triene was first documented in 2015 (PMID: 26019371). Based on a literature review a small amount of articles have been published on Roseophilin (PMID: 27460763) (PMID: 29348526) (PMID: 33507727) (PMID: 31008613).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042205572D          

 32 36  0  0  1  0            999 V2000
    1.4907    2.8977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9954    3.5504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8129    3.4396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3831    4.0359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1264    3.6780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8528    4.0689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9636    4.8865    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7753    5.0338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1663    4.3073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5961    3.7110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7435    2.8992    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.0156    2.8604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2039    2.7131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8459    1.9698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4909    1.4555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7799    0.2997    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4909   -0.8561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8489   -0.1128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8489    0.7122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7651    1.2069    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2507    0.5619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4349    0.6848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5521   -0.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0416    2.1534    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2373    1.9698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5923    1.4555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2343    0.7122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2343   -0.1128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5923   -0.8561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2373   -1.3705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0416   -1.5541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8459   -1.3705    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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  6 10  2  0  0  0  0
 10 11  1  0  0  0  0
  5 12  1  0  0  0  0
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  3 13  2  0  0  0  0
 13 14  1  0  0  0  0
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 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
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 19 20  1  0  0  0  0
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 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 17 32  1  0  0  0  0
M  END

     RDKit          3D

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    2.6461   -4.1472   -0.1329 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.4484   -1.1654   -0.0943 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8735    0.0102   -0.2398 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4849    0.2803   -0.5952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4588    0.0318   -1.4200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0902   -0.9463   -2.0910 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1942   -0.4096   -2.6325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3046    0.9986   -2.3531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3117    1.2824   -1.6263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6411    2.2258   -0.7217 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3123    3.4257   -0.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5056    4.3959   -1.4149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6241    3.2519    0.4288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3921    1.1777    0.3391 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1823    1.1759    1.6969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2975    0.2209    2.3346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3033   -1.1230    1.6568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5818   -1.7856    1.3505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3672   -1.5341    0.1247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5530   -2.6144   -0.8678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8894   -2.6837   -2.1561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0419   -1.4892   -3.1431 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.1855    3.0698    1.3090 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.9986    0.6081    0.5807 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4643   -1.4357    1.0336 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3083   -3.8750    1.2458 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3247   -5.5111    0.6361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0808    1.7392   -2.7055 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3290    2.4795   -1.1825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6337    3.9688    0.4501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6928    5.1635   -1.4490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4774    4.9573   -1.2821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5685    3.8173   -2.3543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4550    3.2756    1.5255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0994    2.2629    0.2232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3423    4.0945    0.2278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3964    0.5543    0.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7448    0.5949    2.0067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1627    2.0663    2.3180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0930    0.2251    3.3951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2723    0.7063    2.1404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5129   -1.2782    0.9178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8764   -1.8014    2.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2573   -1.6139    2.2476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3795   -2.9182    1.4688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0966   -0.5973   -0.3453 H   0  0  0  0  0  0  0  0  0  0  0  0
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 18 17  1  0
  1 33  1  0
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  9 39  1  0
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 24 49  1  1
 20 41  1  6
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 22 43  1  0
 22 44  1  0
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 18 40  1  0
M  END


  Mrv1652309042205572D          

 32 36  0  0  1  0            999 V2000
    1.4907    2.8977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9954    3.5504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8129    3.4396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3831    4.0359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1264    3.6780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8528    4.0689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9636    4.8865    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7753    5.0338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1663    4.3073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5961    3.7110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7435    2.8992    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.0156    2.8604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7799    0.2997    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4909   -0.8561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8489   -0.1128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8489    0.7122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7651    1.2069    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2507    0.5619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4349    0.6848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5521   -0.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0416    2.1534    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2373    1.9698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5923    1.4555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2343   -0.1128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5923   -0.8561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8459   -1.3705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0187729

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC(=C1)C1=C(Cl)C=CN1)C1=C2N=C3CCCCCCCC[C@H]1[C@H](C(C)C)C2=C3

> <INCHI_IDENTIFIER>
InChI=1S/C27H33ClN2O2/c1-16(2)23-18-11-9-7-5-4-6-8-10-17-14-19(23)25(30-17)24(18)27-22(31-3)15-21(32-27)26-20(28)12-13-29-26/h12-16,18,23,29H,4-11H2,1-3H3/t18-,23-/m0/s1

> <INCHI_KEY>
AKRWVQHAEBBOTI-MBSDFSHPSA-N

> <FORMULA>
C27H33ClN2O2

> <MOLECULAR_WEIGHT>
453.02

> <EXACT_MASS>
452.223056

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
51.49968723892975

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(12S,13S)-15-[5-(3-chloro-1H-pyrrol-2-yl)-3-methoxyfuran-2-yl]-13-(propan-2-yl)-2-azatricyclo[10.2.1.1^{3,14}]hexadeca-1(15),2,14(16)-triene

> <JCHEM_LOGP>
6.464737064333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.670856019183702

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.736732084993918

> <JCHEM_PKA_STRONGEST_BASIC>
5.419039948138041

> <JCHEM_POLAR_SURFACE_AREA>
50.519999999999996

> <JCHEM_REFRACTIVITY>
131.6616

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(12S,13S)-15-[5-(3-chloro-1H-pyrrol-2-yl)-3-methoxyfuran-2-yl]-13-isopropyl-2-azatricyclo[10.2.1.1^{3,14}]hexadeca-1(15),2,14(16)-triene

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       2.783   5.409   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.725   6.627   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.251   6.421   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.315   7.534   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.703   6.866   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.059   7.595   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       9.265   9.121   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      10.781   9.396   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.510   8.040   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.446   6.927   0.000  0.00  0.00           C+0
HETATM   11 Cl   UNK     0      10.721   5.412   0.000  0.00  0.00          Cl+0
HETATM   12  O   UNK     0       7.496   5.339   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.981   5.065   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.312   3.677   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.516   2.717   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       7.056   0.559   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       6.516  -1.598   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.185  -0.211   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.185   1.329   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.161   2.253   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.201   1.049   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.679   1.278   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.764  -0.385   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.811   4.020   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.310   3.677   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.106   2.717   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.437   1.329   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.437  -0.211   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.106  -1.598   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.310  -2.558   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.811  -2.901   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.312  -2.558   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    6   11                                                  
CONECT   11   10                                                            
CONECT   12    5   13                                                       
CONECT   13   12    3   14                                                  
CONECT   14   13   15   24                                                  
CONECT   15   14   16   19                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   32                                                  
CONECT   18   17   19                                                       
CONECT   19   18   15   20                                                  
CONECT   20   19   21   24                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   20   14   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   17                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₃ClN₂O₂

Average Mass

453.0200 Da

Monoisotopic Mass

452.22306 Da

IUPAC Name

(12S,13S)-15-[5-(3-chloro-1H-pyrrol-2-yl)-3-methoxyfuran-2-yl]-13-(propan-2-yl)-2-azatricyclo[10.2.1.1^{3,14}]hexadeca-1(15),2,14(16)-triene

Traditional Name

(12S,13S)-15-[5-(3-chloro-1H-pyrrol-2-yl)-3-methoxyfuran-2-yl]-13-isopropyl-2-azatricyclo[10.2.1.1^{3,14}]hexadeca-1(15),2,14(16)-triene

CAS Registry Number

Not Available

SMILES

COC1=C(OC(=C1)C1=C(Cl)C=CN1)C1=C2N=C3CCCCCCCC[C@H]1[C@H](C(C)C)C2=C3

InChI Identifier

InChI=1S/C27H33ClN2O2/c1-16(2)23-18-11-9-7-5-4-6-8-10-17-14-19(23)25(30-17)24(18)27-22(31-3)15-21(32-27)26-20(28)12-13-29-26/h12-16,18,23,29H,4-11H2,1-3H3/t18-,23-/m0/s1

InChI Key

AKRWVQHAEBBOTI-MBSDFSHPSA-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
Streptomyces griseoviridis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl aryl ethers. These are organic compounds containing the alkyl aryl ether functional group with the generic formula R-O-R' , where R is an alkyl group and R' is an aryl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Ethers

Direct Parent

Alkyl aryl ethers

Alternative Parents

Substituents

Alkyl aryl ether
Substituted pyrrole
Aryl halide
Aryl chloride
Heteroaromatic compound
Pyrrole
Furan
Ketimine
Oxacycle
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Organochloride
Organohalogen compound
Imine
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	6.46	ChemAxon
pKa (Strongest Acidic)	13.74	ChemAxon
pKa (Strongest Basic)	5.42	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	50.52 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	131.66 m³·mol⁻¹	ChemAxon
Polarizability	51.5 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

Not Available

Chemspider ID

25991557

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Roseophilin

METLIN ID

Not Available

PubChem Compound

135542556

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kimata S, Izawa M, Kawasaki T, Hayakawa Y: Identification of a prodigiosin cyclization gene in the roseophilin producer and production of a new cyclized prodigiosin in a heterologous host. J Antibiot (Tokyo). 2017 Feb;70(2):196-199. doi: 10.1038/ja.2016.94. Epub 2016 Jul 27. [PubMed:27460763 ]
Kimata S, Matsuda T, Suizu Y, Hayakawa Y: Prodigiosin R2, a new prodigiosin from the roseophilin producer Streptomyces griseoviridis 2464-S5. J Antibiot (Tokyo). 2018 Mar;71(3):393-396. doi: 10.1038/s41429-017-0011-1. Epub 2018 Jan 18. [PubMed:29348526 ]
Furstner A: Lessons from Natural Product Total Synthesis: Macrocyclization and Postcyclization Strategies. Acc Chem Res. 2021 Feb 16;54(4):861-874. doi: 10.1021/acs.accounts.0c00759. Epub 2021 Jan 28. [PubMed:33507727 ]
Zhang X, Zhang C, Wang X, Liang G: Mild Friedel-Crafts Reactions Enable a Robust Synthesis of Roseophilin. Org Lett. 2019 May 3;21(9):3357-3360. doi: 10.1021/acs.orglett.9b01100. Epub 2019 Apr 22. [PubMed:31008613 ]
Bracken JD, Carlson AD, Frederich JH, Nguyen M, Shore GC, Harran PG: Tailored fragments of roseophilin selectively antagonize Mcl-1 in vitro. Tetrahedron Lett. 2015 Jun 3;56(23):3612-3616. doi: 10.1016/j.tetlet.2015.01.191. [PubMed:26019371 ]
LOTUS database [Link]

Showing NP-Card for (12s,13s)-15-[5-(3-chloro-1h-pyrrol-2-yl)-3-methoxyfuran-2-yl]-13-isopropyl-2-azatricyclo[10.2.1.1³,¹⁴]hexadeca-1(15),2,14(16)-triene (NP0187729)

MOL for NP0187729 ((12s,13s)-15-[5-(3-chloro-1h-pyrrol-2-yl)-3-methoxyfuran-2-yl]-13-isopropyl-2-azatricyclo[10.2.1.1³,¹⁴]hexadeca-1(15),2,14(16)-triene)

3D MOL for NP0187729 ((12s,13s)-15-[5-(3-chloro-1h-pyrrol-2-yl)-3-methoxyfuran-2-yl]-13-isopropyl-2-azatricyclo[10.2.1.1³,¹⁴]hexadeca-1(15),2,14(16)-triene)

3D SDF for NP0187729 ((12s,13s)-15-[5-(3-chloro-1h-pyrrol-2-yl)-3-methoxyfuran-2-yl]-13-isopropyl-2-azatricyclo[10.2.1.1³,¹⁴]hexadeca-1(15),2,14(16)-triene)

3D-SDF for NP0187729 ((12s,13s)-15-[5-(3-chloro-1h-pyrrol-2-yl)-3-methoxyfuran-2-yl]-13-isopropyl-2-azatricyclo[10.2.1.1³,¹⁴]hexadeca-1(15),2,14(16)-triene)

PDB for NP0187729 ((12s,13s)-15-[5-(3-chloro-1h-pyrrol-2-yl)-3-methoxyfuran-2-yl]-13-isopropyl-2-azatricyclo[10.2.1.1³,¹⁴]hexadeca-1(15),2,14(16)-triene)

3D PDB for NP0187729 ((12s,13s)-15-[5-(3-chloro-1h-pyrrol-2-yl)-3-methoxyfuran-2-yl]-13-isopropyl-2-azatricyclo[10.2.1.1³,¹⁴]hexadeca-1(15),2,14(16)-triene)

SMILES for NP0187729 ((12s,13s)-15-[5-(3-chloro-1h-pyrrol-2-yl)-3-methoxyfuran-2-yl]-13-isopropyl-2-azatricyclo[10.2.1.1³,¹⁴]hexadeca-1(15),2,14(16)-triene)

INCHI for NP0187729 ((12s,13s)-15-[5-(3-chloro-1h-pyrrol-2-yl)-3-methoxyfuran-2-yl]-13-isopropyl-2-azatricyclo[10.2.1.1³,¹⁴]hexadeca-1(15),2,14(16)-triene)

Structure for NP0187729 ((12s,13s)-15-[5-(3-chloro-1h-pyrrol-2-yl)-3-methoxyfuran-2-yl]-13-isopropyl-2-azatricyclo[10.2.1.1³,¹⁴]hexadeca-1(15),2,14(16)-triene)

3D Structure for NP0187729 ((12s,13s)-15-[5-(3-chloro-1h-pyrrol-2-yl)-3-methoxyfuran-2-yl]-13-isopropyl-2-azatricyclo[10.2.1.1³,¹⁴]hexadeca-1(15),2,14(16)-triene)