NP-MRD: Showing NP-Card for 15-[4-(2-aminoethyl)phenoxy]-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9,16-tetraen-18-ol (NP0187575)

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Record Information

Version

2.0

Created at

2022-09-04 03:46:15 UTC

Updated at

2022-09-04 03:46:15 UTC

NP-MRD ID

NP0187575

Secondary Accession Numbers

None

Natural Product Identification

Common Name

15-[4-(2-aminoethyl)phenoxy]-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9,16-tetraen-18-ol

Description

15-[4-(2-Aminoethyl)phenoxy]-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]Nonadeca-2,4(8),9,16-tetraen-18-ol belongs to the class of organic compounds known as crinine- and haemanthamine-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids compounds with a structure based on the crinine or haemanthamine backbone. Both backbones have a common 5,10b-ethano bridge moiety in their frameworks, which is a very significant taxonomic feature, and the configurations of the 5,10b-ethano bridge are opposite to each other. 15-[4-(2-aminoethyl)phenoxy]-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9,16-tetraen-18-ol is found in Crinum moorei. 15-[4-(2-Aminoethyl)phenoxy]-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]Nonadeca-2,4(8),9,16-tetraen-18-ol is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241510502D          

 30 35  0  0  0  0            999 V2000
    1.9844    5.2586    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1118    4.4435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8814    4.1463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0088    3.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7784    3.0340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9058    2.2189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2636    1.7010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3911    0.8859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7489    0.3680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8836    0.7321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3371    0.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7627    0.9108    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3689    0.1858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6902   -0.5740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1938   -1.2330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4645   -0.6678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2341   -0.9650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8763   -0.4471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1539   -0.3143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8475   -0.7611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5812   -0.3839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3524   -0.6768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8693   -0.0338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4175    0.6565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6214    0.4401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9279    0.8869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1941    0.5098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5750    1.0550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4940    1.9982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3666    2.8133    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  2  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  0  0  0  0
 11 12  1  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
 14 16  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
  9 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 21 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 19 27  1  0  0  0  0
 27 28  1  0  0  0  0
 12 28  1  0  0  0  0
  7 29  1  0  0  0  0
 29 30  2  0  0  0  0
  4 30  1  0  0  0  0
M  END

     RDKit          3D

 56 61  0  0  0  0  0  0  0  0999 V2000
    8.8406   -0.0343   -0.8776 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4889    0.2670   -0.4736 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6340   -0.9549   -0.7698 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2423   -0.6967   -0.3748 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8122   -0.9956    0.8945 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4877   -0.7479    1.2635 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5867   -0.2027    0.3728 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3172    0.0190    0.7741 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2310    0.5534    0.0688 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3357    1.7257    0.7825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4603    1.7395    1.4821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2796    0.5425    1.6176 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3418    0.3952    0.6063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9403    1.4824   -0.0066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9308    1.3477   -0.9480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3434    0.0697   -1.2939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7538   -1.0304   -0.6891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7636   -0.8677    0.2509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1722   -2.0820    0.8600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1477   -1.7276    1.8182 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7348   -1.2560    3.0807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7948    0.2543    2.9979 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1405    0.6207    3.0402 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3200   -0.6484    1.4482 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8288   -0.5681    0.0516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3378    0.1873   -2.2483 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5009    1.5389   -2.6277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6853    2.2297   -1.7021 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0103    0.0977   -0.8957 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3381   -0.1507   -1.2653 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4817    0.2838   -0.1246 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0528    0.6002   -1.7031 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0637    1.1314   -1.0140 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4579    0.4914    0.6114 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6949   -1.2073   -1.8369 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0660   -1.8157   -0.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5069   -1.4255    1.6097 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2335   -1.0128    2.2814 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5468    0.7995   -0.9514 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2354    2.6557    0.7176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8107    2.6556    1.9827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5985    2.4651    0.2827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1016   -2.0232   -0.9842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9315   -2.6865    1.4065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7122   -2.7621    0.1155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6995   -1.7206    3.2913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9569   -1.4815    3.8666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2320    0.7574    3.7884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3685    1.3294    2.4162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4892   -0.5622    2.1772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5871   -0.2118   -0.6742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3912   -1.5030   -0.3363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5605    1.8377   -2.5265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1613    1.6919   -3.6802 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3942    0.5246   -1.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6900    0.0807   -2.2633 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
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 25  1  0
 25 24  1  0
 24 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 12  1  0
 12 11  1  1
 11 10  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 26  1  0
 26 27  1  0
 27 28  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
  7 29  1  0
 29 30  2  0
 30  4  1  0
 10  9  1  0
 18 13  1  0
 12 24  1  0
 28 15  1  0
 19 20  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  3 35  1  0
  3 36  1  0
  5 37  1  0
  6 38  1  0
  9 39  1  6
 25 51  1  0
 25 52  1  0
 24 50  1  1
 21 46  1  0
 21 47  1  0
 22 48  1  1
 23 49  1  0
 11 41  1  0
 10 40  1  0
 14 42  1  0
 27 53  1  0
 27 54  1  0
 17 43  1  0
 19 44  1  0
 19 45  1  0
 29 55  1  0
 30 56  1  0
M  END


  Mrv1533004241510502D          

 30 35  0  0  0  0            999 V2000
    1.9844    5.2586    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1118    4.4435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8814    4.1463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0088    3.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7784    3.0340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9058    2.2189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2636    1.7010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3911    0.8859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7489    0.3680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8836    0.7321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3371    0.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7627    0.9108    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3689    0.1858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6902   -0.5740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1938   -1.2330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4645   -0.6678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2341   -0.9650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8763   -0.4471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1539   -0.3143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8475   -0.7611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5812   -0.3839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3524   -0.6768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8693   -0.0338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4175    0.6565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6214    0.4401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9279    0.8869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1941    0.5098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5750    1.0550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4940    1.9982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3666    2.8133    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  2  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  0  0  0  0
 11 12  1  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
 14 16  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
  9 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 21 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 19 27  1  0  0  0  0
 27 28  1  0  0  0  0
 12 28  1  0  0  0  0
  7 29  1  0  0  0  0
 29 30  2  0  0  0  0
  4 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0187575

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NCCC1=CC=C(OC2CC3N4CC(O)C3(C=C2)C2=CC3=C(OCO3)C=C2C4)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C24H26N2O4/c25-8-6-15-1-3-17(4-2-15)30-18-5-7-24-19-11-21-20(28-14-29-21)9-16(19)12-26(13-23(24)27)22(24)10-18/h1-5,7,9,11,18,22-23,27H,6,8,10,12-14,25H2

> <INCHI_KEY>
WMQYROIEIDIUPE-UHFFFAOYSA-N

> <FORMULA>
C24H26N2O4

> <MOLECULAR_WEIGHT>
406.482

> <EXACT_MASS>
406.189257325

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
43.95364563717224

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
15-[4-(2-aminoethyl)phenoxy]-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9,16-tetraen-18-ol

> <ALOGPS_LOGP>
1.72

> <JCHEM_LOGP>
1.931203915666667

> <ALOGPS_LOGS>
-3.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.1254063306104

> <JCHEM_PKA_STRONGEST_BASIC>
9.822948343876066

> <JCHEM_POLAR_SURFACE_AREA>
77.18

> <JCHEM_REFRACTIVITY>
113.8412

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.41e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
15-[4-(2-aminoethyl)phenoxy]-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9,16-tetraen-18-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  N   UNK     0       3.704   9.816   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       3.942   8.295   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.379   7.740   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.616   6.218   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.053   5.664   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.291   4.142   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.092   3.175   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.330   1.654   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.131   0.687   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.516   1.367   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.496   0.275   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       1.424   1.700   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       0.689   0.347   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.288  -1.072   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.362  -2.302   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.734  -1.246   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.170  -1.801   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.369  -0.835   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.021  -0.587   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.315  -1.421   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.685  -0.717   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       8.125  -1.263   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       9.089  -0.063   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.246   1.225   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.760   0.822   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.465   1.656   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.096   0.952   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.940   1.969   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.656   3.730   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.418   5.252   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   30                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   29                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   18                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13   28                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   11   17   19                                             
CONECT   17   16   18                                                       
CONECT   18   17    9                                                       
CONECT   19   16   20   27                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   25                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   21   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   19   28                                                  
CONECT   28   27   12                                                       
CONECT   29    7   30                                                       
CONECT   30   29    4                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₂₆N₂O₄

Average Mass

406.4820 Da

Monoisotopic Mass

406.18926 Da

IUPAC Name

15-[4-(2-aminoethyl)phenoxy]-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9,16-tetraen-18-ol

Traditional Name

15-[4-(2-aminoethyl)phenoxy]-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9,16-tetraen-18-ol

CAS Registry Number

Not Available

SMILES

NCCC1=CC=C(OC2CC3N4CC(O)C3(C=C2)C2=CC3=C(OCO3)C=C2C4)C=C1

InChI Identifier

InChI=1S/C24H26N2O4/c25-8-6-15-1-3-17(4-2-15)30-18-5-7-24-19-11-21-20(28-14-29-21)9-16(19)12-26(13-23(24)27)22(24)10-18/h1-5,7,9,11,18,22-23,27H,6,8,10,12-14,25H2

InChI Key

WMQYROIEIDIUPE-UHFFFAOYSA-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
Crinum moorei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as crinine- and haemanthamine-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids compounds with a structure based on the crinine or haemanthamine backbone. Both backbones have a common 5,10b-ethano bridge moiety in their frameworks, which is a very significant taxonomic feature, and the configurations of the 5,10b-ethano bridge are opposite to each other.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Amaryllidaceae alkaloids

Sub Class

Crinine- and Haemanthamine-type amaryllidaceae alkaloids

Direct Parent

Crinine- and Haemanthamine-type amaryllidaceae alkaloids

Alternative Parents

Substituents

Hemanthamine/crinine alkaloid skeleton
Phenanthridine
Benzoquinoline
Benzazepine
Quinoline
Tetrahydroisoquinoline
Phenethylamine
Benzodioxole
Indole or derivatives
Phenoxy compound
2-arylethylamine
Phenol ether
Alkyl aryl ether
Azepine
Aralkylamine
Monocyclic benzene moiety
Benzenoid
N-alkylpyrrolidine
Pyrrolidine
1,2-aminoalcohol
Tertiary aliphatic amine
Secondary alcohol
Tertiary amine
Acetal
Oxacycle
Azacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Alcohol
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Amine
Primary amine
Primary aliphatic amine
Organonitrogen compound
Organooxygen 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	1.72	ALOGPS
logP	1.93	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	14.13	ChemAxon
pKa (Strongest Basic)	9.82	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	77.18 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	113.84 m³·mol⁻¹	ChemAxon
Polarizability	43.95 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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 15-[4-(2-aminoethyl)phenoxy]-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9,16-tetraen-18-ol (NP0187575)

MOL for NP0187575 (15-[4-(2-aminoethyl)phenoxy]-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9,16-tetraen-18-ol)

3D MOL for NP0187575 (15-[4-(2-aminoethyl)phenoxy]-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9,16-tetraen-18-ol)

3D SDF for NP0187575 (15-[4-(2-aminoethyl)phenoxy]-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9,16-tetraen-18-ol)

3D-SDF for NP0187575 (15-[4-(2-aminoethyl)phenoxy]-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9,16-tetraen-18-ol)

PDB for NP0187575 (15-[4-(2-aminoethyl)phenoxy]-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9,16-tetraen-18-ol)

3D PDB for NP0187575 (15-[4-(2-aminoethyl)phenoxy]-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9,16-tetraen-18-ol)

SMILES for NP0187575 (15-[4-(2-aminoethyl)phenoxy]-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9,16-tetraen-18-ol)

INCHI for NP0187575 (15-[4-(2-aminoethyl)phenoxy]-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9,16-tetraen-18-ol)

Structure for NP0187575 (15-[4-(2-aminoethyl)phenoxy]-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9,16-tetraen-18-ol)

3D Structure for NP0187575 (15-[4-(2-aminoethyl)phenoxy]-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9,16-tetraen-18-ol)