NP-MRD: Showing NP-Card for 5-[(1s,2r,3s,4e,11r)-11-[(1r)-1-hydroxypropyl]-3-methyl-5-oxa-10-azatricyclo[8.4.0.0²,⁶]tetradec-6-en-4-ylidene]-4-methoxy-3-methylfuran-2-one (NP0208451)

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Record Information

Version

2.0

Created at

2022-09-05 05:27:50 UTC

Updated at

2022-09-05 05:27:50 UTC

NP-MRD ID

NP0208451

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-[(1s,2r,3s,4e,11r)-11-[(1r)-1-hydroxypropyl]-3-methyl-5-oxa-10-azatricyclo[8.4.0.0²,⁶]tetradec-6-en-4-ylidene]-4-methoxy-3-methylfuran-2-one

Description

5-[(1S,2R,3S,4E,11R)-11-[(1R)-1-hydroxypropyl]-3-methyl-5-oxa-10-azatricyclo[8.4.0.0²,⁶]Tetradec-6-en-4-ylidene]-4-methoxy-3-methyl-2,5-dihydrofuran-2-one belongs to the class of organic compounds known as azepines. These are organic compounds containing an unsaturated seven-member heterocycle with one nitrogen atom replacing a carbon atom. 5-[(1s,2r,3s,4e,11r)-11-[(1r)-1-hydroxypropyl]-3-methyl-5-oxa-10-azatricyclo[8.4.0.0²,⁶]tetradec-6-en-4-ylidene]-4-methoxy-3-methylfuran-2-one is found in Stemona kerrii. Based on a literature review very few articles have been published on 5-[(1S,2R,3S,4E,11R)-11-[(1R)-1-hydroxypropyl]-3-methyl-5-oxa-10-azatricyclo[8.4.0.0²,⁶]Tetradec-6-en-4-ylidene]-4-methoxy-3-methyl-2,5-dihydrofuran-2-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052207272D          

 28 31  0  0  1  0            999 V2000
   -1.0802   -3.0219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5914   -2.3573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2285   -2.4483    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5597   -3.2040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7173   -1.7837    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3862   -1.0281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8750   -0.3635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6950   -0.4546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0261   -1.2102    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8505   -1.1780    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3897   -1.8024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2376   -2.6133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5088   -3.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7521   -2.6713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5373   -1.8748    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1501   -1.4826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0810   -0.6605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7054   -0.1213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6363    0.7008    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3968    1.0206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5850    1.8238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9359    0.3961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7580    0.4653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5087   -0.3096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8285   -1.0701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3298   -1.7273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2778   -0.4722    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9579    0.2883    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  6  0  0  0
  5  3  1  1  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  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  9 15  1  1  0  0  0
  5 15  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 18 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 17 27  1  0  0  0  0
 10 27  1  0  0  0  0
 27 28  1  6  0  0  0
M  END

     RDKit          3D

 59 62  0  0  0  0  0  0  0  0999 V2000
    3.4314   -1.9042   -1.7226 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4781   -0.8983   -1.4123 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5755   -0.5006    0.0450 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6378    0.4559    0.0432 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4003    0.2680    0.5401 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1737    1.3605   -0.4910 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3861    2.4374    0.1601 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5636    1.8848    1.2540 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1861    0.4331    1.1803 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2026    0.2699    0.7865 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7147   -1.1039    1.1145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0548   -2.0420    1.7476 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2916   -2.1399    2.3304 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4019   -1.5772    1.5941 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1738   -0.4704    0.6837 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9952   -1.0872    0.5881 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1290    0.0171   -0.2853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2615    0.5467   -0.6746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3631    1.6297   -1.5289 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7143    1.8905   -1.6997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1566    2.8231   -2.4260 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4952    0.9264   -0.9161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9755    0.9309   -0.8806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6334    0.1404   -0.3168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9623   -0.9023    0.5169 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6743   -2.0499    0.1073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7032    0.3542   -0.5904 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5503    1.6052   -1.3491 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6071   -2.8771   -1.2088 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4073   -1.5231   -1.4370 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3549   -2.1326   -2.8030 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3249   -0.0222   -2.0741 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4645   -1.3278   -1.7150 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9418   -1.3210    0.6394 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7055    0.8805    0.9476 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6512    0.7372    1.5032 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1634    1.8139   -0.7961 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6501    0.9377   -1.3563 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1103    3.1937    0.6006 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8169    3.0863   -0.5707 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6011    2.4681    1.2815 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329    2.1599    2.2468 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1514    0.1654    2.3082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8186    0.9359    1.4746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6420   -2.9397    1.8625 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4907   -3.2041    2.5700 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2274   -1.6349    3.3421 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9161   -2.3789    1.0349 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1840   -1.2044    2.3208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3488    0.3853   -1.7706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3941    0.5142    0.0507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3906    1.9739   -0.9620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1378   -2.5914   -0.6879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7462   -2.7195    0.9952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7187   -1.8195   -0.1972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3157   -0.5231   -1.1588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6520    2.5116   -0.7611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2226    1.5610   -2.2462 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4719    1.5967   -1.8318 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 27  1  0
 27 28  1  0
 27 17  1  0
 17 16  1  0
 16 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 25 26  1  0
 15  5  1  0
 24 18  1  0
 15  9  1  0
 11 10  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  3 34  1  1
  4 35  1  0
  5 36  1  1
  6 37  1  0
  6 38  1  0
  7 39  1  0
  7 40  1  0
  8 41  1  0
  8 42  1  0
  9 43  1  1
 10 44  1  1
 27 56  1  6
 28 57  1  0
 28 58  1  0
 28 59  1  0
 12 45  1  0
 13 46  1  0
 13 47  1  0
 14 48  1  0
 14 49  1  0
 23 50  1  0
 23 51  1  0
 23 52  1  0
 26 53  1  0
 26 54  1  0
 26 55  1  0
M  END


  Mrv1652309052207272D          

 28 31  0  0  1  0            999 V2000
   -1.0802   -3.0219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5914   -2.3573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2285   -2.4483    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5597   -3.2040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7173   -1.7837    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3862   -1.0281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8750   -0.3635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6950   -0.4546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0261   -1.2102    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8505   -1.1780    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3897   -1.8024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2376   -2.6133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5088   -3.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7521   -2.6713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5373   -1.8748    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1501   -1.4826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0810   -0.6605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7054   -0.1213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6363    0.7008    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3968    1.0206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5850    1.8238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9359    0.3961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7580    0.4653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5087   -0.3096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8285   -1.0701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3298   -1.7273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2778   -0.4722    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9579    0.2883    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  6  0  0  0
  5  3  1  1  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  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  9 15  1  1  0  0  0
  5 15  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 18 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 17 27  1  0  0  0  0
 10 27  1  0  0  0  0
 27 28  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0208451

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@H](O)[C@H]1CCC[C@H]2[C@H]3[C@H](C)\C(OC3=CCCN12)=C1/OC(=O)C(C)=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C22H31NO5/c1-5-16(24)14-8-6-9-15-18-12(2)20(27-17(18)10-7-11-23(14)15)21-19(26-4)13(3)22(25)28-21/h10,12,14-16,18,24H,5-9,11H2,1-4H3/b21-20+/t12-,14+,15-,16+,18+/m0/s1

> <INCHI_KEY>
KLADGQYNEYECIT-HRNNGTMRSA-N

> <FORMULA>
C22H31NO5

> <MOLECULAR_WEIGHT>
389.492

> <EXACT_MASS>
389.220223102

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
44.16426548553147

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[(1S,2R,3S,4E,11R)-11-[(1R)-1-hydroxypropyl]-3-methyl-5-oxa-10-azatricyclo[8.4.0.0^{2,6}]tetradec-6-en-4-ylidene]-4-methoxy-3-methyl-2,5-dihydrofuran-2-one

> <JCHEM_LOGP>
1.6338701076666653

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.605756819932946

> <JCHEM_PKA_STRONGEST_BASIC>
10.48372290653449

> <JCHEM_POLAR_SURFACE_AREA>
68.23

> <JCHEM_REFRACTIVITY>
110.27309999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
5-[(1S,2R,3S,4E,11R)-11-[(1R)-1-hydroxypropyl]-3-methyl-5-oxa-10-azatricyclo[8.4.0.0^{2,6}]tetradec-6-en-4-ylidene]-4-methoxy-3-methylfuran-2-one

> <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      -2.016  -5.641   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.104  -4.400   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.427  -4.570   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.045  -5.981   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.339  -3.330   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.721  -1.919   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.633  -0.679   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.164  -0.848   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.782  -2.259   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.321  -2.199   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.327  -3.365   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.044  -4.878   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.683  -5.600   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.271  -4.986   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       2.870  -3.500   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0       7.747  -2.768   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       7.618  -1.233   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.783  -0.227   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.654   1.308   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      10.074   1.905   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      10.425   3.404   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      11.080   0.739   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.615   0.869   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.283  -0.578   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      10.880  -1.998   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       9.949  -3.224   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.118  -0.882   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.522   0.538   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   15                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   15                                                  
CONECT   10    9   11   27                                                  
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    9    5                                                  
CONECT   16   11   17                                                       
CONECT   17   16   18   27                                                  
CONECT   18   17   19   24                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   18   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   17   10   28                                                  
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₁NO₅

Average Mass

389.4920 Da

Monoisotopic Mass

389.22022 Da

IUPAC Name

5-[(1S,2R,3S,4E,11R)-11-[(1R)-1-hydroxypropyl]-3-methyl-5-oxa-10-azatricyclo[8.4.0.0^{2,6}]tetradec-6-en-4-ylidene]-4-methoxy-3-methyl-2,5-dihydrofuran-2-one

Traditional Name

5-[(1S,2R,3S,4E,11R)-11-[(1R)-1-hydroxypropyl]-3-methyl-5-oxa-10-azatricyclo[8.4.0.0^{2,6}]tetradec-6-en-4-ylidene]-4-methoxy-3-methylfuran-2-one

CAS Registry Number

Not Available

SMILES

CC[C@@H](O)[C@H]1CCC[C@H]2[C@H]3[C@H](C)\C(OC3=CCCN12)=C1/OC(=O)C(C)=C1OC

InChI Identifier

InChI=1S/C22H31NO5/c1-5-16(24)14-8-6-9-15-18-12(2)20(27-17(18)10-7-11-23(14)15)21-19(26-4)13(3)22(25)28-21/h10,12,14-16,18,24H,5-9,11H2,1-4H3/b21-20+/t12-,14+,15-,16+,18+/m0/s1

InChI Key

KLADGQYNEYECIT-HRNNGTMRSA-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
Stemona kerrii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as azepines. These are organic compounds containing an unsaturated seven-member heterocycle with one nitrogen atom replacing a carbon atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azepines

Sub Class

Not Available

Direct Parent

Azepines

Alternative Parents

Substituents

Azepine
Piperidine
2-furanone
Enol ester
Dihydrofuran
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Vinylogous ester
Lactone
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Carboxylic acid ester
1,2-aminoalcohol
Amino acid or derivatives
Monocarboxylic acid or derivatives
Azacycle
Oxacycle
Carboxylic acid derivative
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
Amine
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	1.63	ChemAxon
pKa (Strongest Acidic)	14.61	ChemAxon
pKa (Strongest Basic)	10.48	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	68.23 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	110.27 m³·mol⁻¹	ChemAxon
Polarizability	44.16 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162974134

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-[(1s,2r,3s,4e,11r)-11-[(1r)-1-hydroxypropyl]-3-methyl-5-oxa-10-azatricyclo[8.4.0.0²,⁶]tetradec-6-en-4-ylidene]-4-methoxy-3-methylfuran-2-one (NP0208451)

MOL for NP0208451 (5-[(1s,2r,3s,4e,11r)-11-[(1r)-1-hydroxypropyl]-3-methyl-5-oxa-10-azatricyclo[8.4.0.0²,⁶]tetradec-6-en-4-ylidene]-4-methoxy-3-methylfuran-2-one)

3D MOL for NP0208451 (5-[(1s,2r,3s,4e,11r)-11-[(1r)-1-hydroxypropyl]-3-methyl-5-oxa-10-azatricyclo[8.4.0.0²,⁶]tetradec-6-en-4-ylidene]-4-methoxy-3-methylfuran-2-one)

3D SDF for NP0208451 (5-[(1s,2r,3s,4e,11r)-11-[(1r)-1-hydroxypropyl]-3-methyl-5-oxa-10-azatricyclo[8.4.0.0²,⁶]tetradec-6-en-4-ylidene]-4-methoxy-3-methylfuran-2-one)

3D-SDF for NP0208451 (5-[(1s,2r,3s,4e,11r)-11-[(1r)-1-hydroxypropyl]-3-methyl-5-oxa-10-azatricyclo[8.4.0.0²,⁶]tetradec-6-en-4-ylidene]-4-methoxy-3-methylfuran-2-one)

PDB for NP0208451 (5-[(1s,2r,3s,4e,11r)-11-[(1r)-1-hydroxypropyl]-3-methyl-5-oxa-10-azatricyclo[8.4.0.0²,⁶]tetradec-6-en-4-ylidene]-4-methoxy-3-methylfuran-2-one)

3D PDB for NP0208451 (5-[(1s,2r,3s,4e,11r)-11-[(1r)-1-hydroxypropyl]-3-methyl-5-oxa-10-azatricyclo[8.4.0.0²,⁶]tetradec-6-en-4-ylidene]-4-methoxy-3-methylfuran-2-one)

SMILES for NP0208451 (5-[(1s,2r,3s,4e,11r)-11-[(1r)-1-hydroxypropyl]-3-methyl-5-oxa-10-azatricyclo[8.4.0.0²,⁶]tetradec-6-en-4-ylidene]-4-methoxy-3-methylfuran-2-one)

INCHI for NP0208451 (5-[(1s,2r,3s,4e,11r)-11-[(1r)-1-hydroxypropyl]-3-methyl-5-oxa-10-azatricyclo[8.4.0.0²,⁶]tetradec-6-en-4-ylidene]-4-methoxy-3-methylfuran-2-one)

Structure for NP0208451 (5-[(1s,2r,3s,4e,11r)-11-[(1r)-1-hydroxypropyl]-3-methyl-5-oxa-10-azatricyclo[8.4.0.0²,⁶]tetradec-6-en-4-ylidene]-4-methoxy-3-methylfuran-2-one)

3D Structure for NP0208451 (5-[(1s,2r,3s,4e,11r)-11-[(1r)-1-hydroxypropyl]-3-methyl-5-oxa-10-azatricyclo[8.4.0.0²,⁶]tetradec-6-en-4-ylidene]-4-methoxy-3-methylfuran-2-one)