NP-MRD: Showing NP-Card for (2s,3s,5r,7r,11s)-3,5-dihydroxy-2,7-dimethyl-6-oxo-15-oxa-9-azahexacyclo[12.6.1.0²,¹¹.0³,⁹.0⁵,²⁰.0¹⁸,²¹]henicosa-1(20),14(21),18-trien-19-yl acetate (NP0211610)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-05 09:58:16 UTC

Updated at

2022-09-05 09:58:16 UTC

NP-MRD ID

NP0211610

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3s,5r,7r,11s)-3,5-dihydroxy-2,7-dimethyl-6-oxo-15-oxa-9-azahexacyclo[12.6.1.0²,¹¹.0³,⁹.0⁵,²⁰.0¹⁸,²¹]henicosa-1(20),14(21),18-trien-19-yl acetate

Description

(2S,3S,5R,7R,11S)-3,5-dihydroxy-2,7-dimethyl-6-oxo-15-oxa-9-azahexacyclo[12.6.1.0²,¹¹.0³,⁹.0⁵,²⁰.0¹⁸,²¹]Henicosa-1(20),14(21),18-trien-19-yl acetate belongs to the class of organic compounds known as indoles and derivatives. These are organic compounds containing an indole, which is a bicyclic ring system made up of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. (2s,3s,5r,7r,11s)-3,5-dihydroxy-2,7-dimethyl-6-oxo-15-oxa-9-azahexacyclo[12.6.1.0²,¹¹.0³,⁹.0⁵,²⁰.0¹⁸,²¹]henicosa-1(20),14(21),18-trien-19-yl acetate is found in Daphniphyllum macropodum. Based on a literature review very few articles have been published on (2S,3S,5R,7R,11S)-3,5-dihydroxy-2,7-dimethyl-6-oxo-15-oxa-9-azahexacyclo[12.6.1.0²,¹¹.0³,⁹.0⁵,²⁰.0¹⁸,²¹]Henicosa-1(20),14(21),18-trien-19-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052211582D          

 30 35  0  0  1  0            999 V2000
    3.1277   -1.7075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0845   -0.8837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7763   -0.4343    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3494   -0.5092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3061    0.3147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9882    0.8212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8171    0.7024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3496    1.3438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0548    2.1225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2290    2.2925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7242    1.6142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9141    1.5594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5814    0.7431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6664    0.5930    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7243   -0.2300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6228    1.2305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6762    2.0338    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8618    2.8376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0718    2.5363    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5919    3.2531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4415    3.0490    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1996    3.4239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9760    3.1055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4193    2.2154    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2051    2.4669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6870    2.1138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8495    1.2589    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6414    1.0273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2394    0.6130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743   -0.1410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  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  2  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 20  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 10 23  1  0  0  0  0
 21 24  1  0  0  0  0
 12 24  1  0  0  0  0
 17 24  1  0  0  0  0
 24 25  1  6  0  0  0
 19 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 14 29  1  0  0  0  0
 29 30  2  0  0  0  0
M  END

     RDKit          3D

 57 62  0  0  0  0  0  0  0  0999 V2000
    4.5998   -2.9030    1.0095 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7009   -1.8220    0.5623 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9767   -1.2527   -0.5266 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5739   -1.4209    1.3003 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8128   -0.3758    0.7449 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9747    0.9153    0.9503 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9135    1.6952    1.7530 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6885    3.1581    1.7500 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8622    3.6630    0.7253 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8532    2.9272    0.1742 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9585    1.5964    0.1674 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1762    0.5800   -0.5259 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6748   -0.5601   -0.1863 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0987   -1.8135   -0.7055 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1251   -2.6520   -1.1621 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8655   -1.6229   -1.8209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7512   -0.4300   -1.6930 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3989   -0.2519   -2.9204 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7062   -0.4326   -0.6686 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8415    0.8548   -0.0788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9550    1.7957   -0.9183 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5483    2.9140   -0.0736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3065    3.6630   -0.3865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9549    0.8496   -1.4413 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4368    1.2651   -2.8285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8934   -1.5621    0.1349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8129   -1.9217    1.1032 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3264   -2.9773    2.0712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6384   -2.4526    0.4014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2262   -3.5181    0.7578 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5233   -3.0909    2.0916 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6465   -2.5724    0.7916 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3713   -3.8148    0.4051 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9727    1.4223    1.4728 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8210    1.3294    2.8171 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6852    3.6657    1.6289 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2833    3.5564    2.7087 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4013   -3.3066   -0.4848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3229   -1.5750   -2.7769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5184   -2.5207   -1.8692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0870    0.4501   -2.7920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8920    1.2342   -0.2206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6075    0.9204    0.9851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5633    2.1674   -1.7957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3911    3.6633   -0.0552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4696    2.5703    0.9967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1862    3.9552   -1.4332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3467    4.6346    0.1890 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3709    2.0261   -2.7389 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0558    0.3639   -3.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2933    1.5849   -3.4210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1068   -2.4555   -0.4808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8312   -1.4035    0.7445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4772   -1.0618    1.7251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8632   -2.4610    2.9154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0270   -3.6800    1.6052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4752   -3.5098    2.5667 H   0  0  0  0  0  0  0  0  0  0  0  0
 28 27  1  0
 27 26  1  0
 26 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 10  1  0
 10 11  2  0
 11  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  6  5  2  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
  5 13  1  0
 13 12  2  0
 12 24  1  0
 24 25  1  6
 24 17  1  0
 17 18  1  6
 17 16  1  0
 16 14  1  0
 14 15  1  6
 14 29  1  0
 29 30  2  0
 29 27  1  0
 17 19  1  0
 24 21  1  0
  9 10  1  0
 14 13  1  0
 12 11  1  0
 28 55  1  0
 28 56  1  0
 28 57  1  0
 27 54  1  1
 26 52  1  0
 26 53  1  0
 20 42  1  0
 20 43  1  0
 21 44  1  6
 22 45  1  0
 22 46  1  0
 23 47  1  0
 23 48  1  0
  7 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
 25 49  1  0
 25 50  1  0
 25 51  1  0
 18 41  1  0
 16 39  1  0
 16 40  1  0
 15 38  1  0
M  END


  Mrv1652309052211582D          

 30 35  0  0  1  0            999 V2000
    3.1277   -1.7075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0845   -0.8837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7763   -0.4343    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3494   -0.5092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3061    0.3147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9882    0.8212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8171    0.7024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3496    1.3438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0548    2.1225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2290    2.2925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7242    1.6142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9141    1.5594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5814    0.7431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6664    0.5930    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7243   -0.2300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6228    1.2305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6762    2.0338    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8618    2.8376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0718    2.5363    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5919    3.2531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4415    3.0490    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1996    3.4239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9760    3.1055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4193    2.2154    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2051    2.4669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6870    2.1138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8495    1.2589    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6414    1.0273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2394    0.6130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743   -0.1410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  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  2  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 20  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 10 23  1  0  0  0  0
 21 24  1  0  0  0  0
 12 24  1  0  0  0  0
 17 24  1  0  0  0  0
 24 25  1  6  0  0  0
 19 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 14 29  1  0  0  0  0
 29 30  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0211610

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CN2C[C@H]3CCC4=C5C(CCO4)=C(OC(C)=O)C4=C5[C@@]3(C)[C@@]2(O)C[C@]4(O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H27NO6/c1-11-8-24-9-13-4-5-15-16-14(6-7-29-15)19(30-12(2)25)18-17(16)21(13,3)23(24,28)10-22(18,27)20(11)26/h11,13,27-28H,4-10H2,1-3H3/t11-,13-,21+,22-,23+/m1/s1

> <INCHI_KEY>
KWYZCNYHPWIREB-MTQPCCQXSA-N

> <FORMULA>
C23H27NO6

> <MOLECULAR_WEIGHT>
413.47

> <EXACT_MASS>
413.183837593

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
43.006586863195686

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3S,5R,7R,11S)-3,5-dihydroxy-2,7-dimethyl-6-oxo-15-oxa-9-azahexacyclo[12.6.1.0^{2,11}.0^{3,9}.0^{5,20}.0^{18,21}]henicosa-1(20),14(21),18-trien-19-yl acetate

> <JCHEM_LOGP>
-0.24012291266666688

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
12.871282755580395

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.045581742261843

> <JCHEM_PKA_STRONGEST_BASIC>
9.042062113353738

> <JCHEM_POLAR_SURFACE_AREA>
96.30000000000001

> <JCHEM_REFRACTIVITY>
109.71299999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,5R,7R,11S)-3,5-dihydroxy-2,7-dimethyl-6-oxo-15-oxa-9-azahexacyclo[12.6.1.0^{2,11}.0^{3,9}.0^{5,20}.0^{18,21}]henicosa-1(20),14(21),18-trien-19-yl acetate

> <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       5.838  -3.187   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.758  -1.649   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       7.049  -0.811   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       4.385  -0.950   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.305   0.587   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.578   1.533   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.125   1.311   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.119   2.508   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       7.569   3.962   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.027   4.279   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.085   3.013   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.573   2.911   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.952   1.387   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.244   1.107   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.352  -0.429   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.163   2.297   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.262   3.796   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.609   5.297   0.000  0.00  0.00           O+0
HETATM   19  N   UNK     0       0.134   4.735   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       1.105   6.072   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.691   5.692   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.106   6.391   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.555   5.797   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.649   4.135   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.116   4.605   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.282   3.946   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.586   2.350   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.064   1.918   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.447   1.144   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.072  -0.263   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   23                                                  
CONECT   11   10    6   12                                                  
CONECT   12   11   13   24                                                  
CONECT   13   12    5   14                                                  
CONECT   14   13   15   16   29                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   19   24                                             
CONECT   18   17                                                            
CONECT   19   17   20   26                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22   10                                                       
CONECT   24   21   12   17   25                                             
CONECT   25   24                                                            
CONECT   26   19   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   14   30                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   70    0
END

View in JSmol

Synonyms

Value	Source
(2S,3S,5R,7R,11S)-3,5-Dihydroxy-2,7-dimethyl-6-oxo-15-oxa-9-azahexacyclo[12.6.1.0,.0,.0,.0,]henicosa-1(20),14(21),18-trien-19-yl acetic acid	Generator

Chemical Formula

C₂₃H₂₇NO₆

Average Mass

413.4700 Da

Monoisotopic Mass

413.18384 Da

IUPAC Name

(2S,3S,5R,7R,11S)-3,5-dihydroxy-2,7-dimethyl-6-oxo-15-oxa-9-azahexacyclo[12.6.1.0^{2,11}.0^{3,9}.0^{5,20}.0^{18,21}]henicosa-1(20),14(21),18-trien-19-yl acetate

Traditional Name

(2S,3S,5R,7R,11S)-3,5-dihydroxy-2,7-dimethyl-6-oxo-15-oxa-9-azahexacyclo[12.6.1.0^{2,11}.0^{3,9}.0^{5,20}.0^{18,21}]henicosa-1(20),14(21),18-trien-19-yl acetate

CAS Registry Number

Not Available

SMILES

C[C@@H]1CN2C[C@H]3CCC4=C5C(CCO4)=C(OC(C)=O)C4=C5[C@@]3(C)[C@@]2(O)C[C@]4(O)C1=O

InChI Identifier

InChI=1S/C23H27NO6/c1-11-8-24-9-13-4-5-15-16-14(6-7-29-15)19(30-12(2)25)18-17(16)21(13,3)23(24,28)10-22(18,27)20(11)26/h11,13,27-28H,4-10H2,1-3H3/t11-,13-,21+,22-,23+/m1/s1

InChI Key

KWYZCNYHPWIREB-MTQPCCQXSA-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
Daphniphyllum macropodum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indoles and derivatives. These are organic compounds containing an indole, which is a bicyclic ring system made up of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Not Available

Direct Parent

Indoles and derivatives

Alternative Parents

Substituents

Indene
Indole or derivatives
Azepane
N-alkylpyrrolidine
Enol ester
Tertiary alcohol
Pyrrolidine
Carboxylic acid ester
Hemiaminal
Ketone
Alkanolamine
Carboxylic acid derivative
Oxacycle
Azacycle
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Alcohol
Organic nitrogen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
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	-0.24	ChemAxon
pKa (Strongest Acidic)	12.05	ChemAxon
pKa (Strongest Basic)	9.04	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	96.3 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	109.71 m³·mol⁻¹	ChemAxon
Polarizability	43.01 Å³	ChemAxon
Number of Rings	6	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

163030866

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3s,5r,7r,11s)-3,5-dihydroxy-2,7-dimethyl-6-oxo-15-oxa-9-azahexacyclo[12.6.1.0²,¹¹.0³,⁹.0⁵,²⁰.0¹⁸,²¹]henicosa-1(20),14(21),18-trien-19-yl acetate (NP0211610)

MOL for NP0211610 ((2s,3s,5r,7r,11s)-3,5-dihydroxy-2,7-dimethyl-6-oxo-15-oxa-9-azahexacyclo[12.6.1.0²,¹¹.0³,⁹.0⁵,²⁰.0¹⁸,²¹]henicosa-1(20),14(21),18-trien-19-yl acetate)

3D MOL for NP0211610 ((2s,3s,5r,7r,11s)-3,5-dihydroxy-2,7-dimethyl-6-oxo-15-oxa-9-azahexacyclo[12.6.1.0²,¹¹.0³,⁹.0⁵,²⁰.0¹⁸,²¹]henicosa-1(20),14(21),18-trien-19-yl acetate)

3D SDF for NP0211610 ((2s,3s,5r,7r,11s)-3,5-dihydroxy-2,7-dimethyl-6-oxo-15-oxa-9-azahexacyclo[12.6.1.0²,¹¹.0³,⁹.0⁵,²⁰.0¹⁸,²¹]henicosa-1(20),14(21),18-trien-19-yl acetate)

3D-SDF for NP0211610 ((2s,3s,5r,7r,11s)-3,5-dihydroxy-2,7-dimethyl-6-oxo-15-oxa-9-azahexacyclo[12.6.1.0²,¹¹.0³,⁹.0⁵,²⁰.0¹⁸,²¹]henicosa-1(20),14(21),18-trien-19-yl acetate)

PDB for NP0211610 ((2s,3s,5r,7r,11s)-3,5-dihydroxy-2,7-dimethyl-6-oxo-15-oxa-9-azahexacyclo[12.6.1.0²,¹¹.0³,⁹.0⁵,²⁰.0¹⁸,²¹]henicosa-1(20),14(21),18-trien-19-yl acetate)

3D PDB for NP0211610 ((2s,3s,5r,7r,11s)-3,5-dihydroxy-2,7-dimethyl-6-oxo-15-oxa-9-azahexacyclo[12.6.1.0²,¹¹.0³,⁹.0⁵,²⁰.0¹⁸,²¹]henicosa-1(20),14(21),18-trien-19-yl acetate)

SMILES for NP0211610 ((2s,3s,5r,7r,11s)-3,5-dihydroxy-2,7-dimethyl-6-oxo-15-oxa-9-azahexacyclo[12.6.1.0²,¹¹.0³,⁹.0⁵,²⁰.0¹⁸,²¹]henicosa-1(20),14(21),18-trien-19-yl acetate)

INCHI for NP0211610 ((2s,3s,5r,7r,11s)-3,5-dihydroxy-2,7-dimethyl-6-oxo-15-oxa-9-azahexacyclo[12.6.1.0²,¹¹.0³,⁹.0⁵,²⁰.0¹⁸,²¹]henicosa-1(20),14(21),18-trien-19-yl acetate)

Structure for NP0211610 ((2s,3s,5r,7r,11s)-3,5-dihydroxy-2,7-dimethyl-6-oxo-15-oxa-9-azahexacyclo[12.6.1.0²,¹¹.0³,⁹.0⁵,²⁰.0¹⁸,²¹]henicosa-1(20),14(21),18-trien-19-yl acetate)

3D Structure for NP0211610 ((2s,3s,5r,7r,11s)-3,5-dihydroxy-2,7-dimethyl-6-oxo-15-oxa-9-azahexacyclo[12.6.1.0²,¹¹.0³,⁹.0⁵,²⁰.0¹⁸,²¹]henicosa-1(20),14(21),18-trien-19-yl acetate)