NP-MRD: Showing NP-Card for (20r,21s)-4,5,6,10,11-pentamethoxy-16-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2(7),3,5,8(13),9,11-heptaen-21-ol (NP0146304)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 01:40:34 UTC

Updated at

2022-09-02 01:40:35 UTC

NP-MRD ID

NP0146304

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(20r,21s)-4,5,6,10,11-pentamethoxy-16-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2(7),3,5,8(13),9,11-heptaen-21-ol

Description

(20R,21S)-4,5,6,10,11-pentamethoxy-16-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]Henicosa-1(14),2,4,6,8,10,12-heptaen-21-ol belongs to the class of organic compounds known as phenanthroindolizidines. These are aromatic polycyclic compounds containing the phenanthroindolizidine skeleton, which is structurally characterized by an indolizidine and a phenanthrene, where the indolizidine is fused to the second benzene ring of a phenanthrene. (20r,21s)-4,5,6,10,11-pentamethoxy-16-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2(7),3,5,8(13),9,11-heptaen-21-ol is found in Ficus septica. Based on a literature review very few articles have been published on (20R,21S)-4,5,6,10,11-pentamethoxy-16-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]Henicosa-1(14),2,4,6,8,10,12-heptaen-21-ol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022203402D          

 32 36  0  0  1  0            999 V2000
    5.0884   -4.8700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2763   -4.7248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9960   -3.9489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1838   -3.8037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9035   -3.0277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0914   -2.8825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8111   -2.1066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3429   -1.4759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0626   -0.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5945   -0.0692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3142    0.7067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5021    0.8519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4066   -0.2145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9384    0.4162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7505    0.2710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6869   -0.9904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4990   -1.1356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7793   -1.9115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1551   -1.6211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4354   -2.3970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2475   -2.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5278   -3.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3399   -3.4634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6202   -4.2393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9990   -1.9614    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7187   -1.1854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4672   -2.5921    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3574   -2.6189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5867   -3.4114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0962   -3.8744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7475   -3.3680    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5596   -3.5132    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  2  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
 10 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  2  0  0  0  0
  8 19  1  0  0  0  0
 19 20  1  0  0  0  0
  5 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
  3 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  7 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 27 31  1  6  0  0  0
 31 32  1  0  0  0  0
  6 32  1  0  0  0  0
M  END

     RDKit          3D

 61 65  0  0  0  0  0  0  0  0999 V2000
   -0.2166    5.5684   -0.1883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4025    4.8275   -0.2315 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3615    3.4512   -0.1677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1166    2.8357   -0.0594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0620    1.4846    0.0030 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2071    0.9302    0.1454 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2433   -0.4316    0.2397 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1184   -1.2416    0.1977 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2373   -2.6138    0.2983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8782   -3.3965    0.2528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7278   -4.7688    0.3593 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5710   -5.2943    0.5097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1043   -2.7994    0.1038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2126   -3.6174    0.0614 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8538   -3.9227    1.3023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2627   -1.4246   -0.0037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5672   -1.0191   -0.1590 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0168   -1.1286   -1.5569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1282   -0.6523    0.0499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2258    0.7053   -0.0413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4392    1.3394   -0.1451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5156    2.7202   -0.2103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7344    3.3024   -0.3146 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9742    2.6853   -0.3676 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5324   -1.1545    0.4066 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5609   -1.7783    1.6889 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7139   -0.2779    0.3686 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3470   -0.0573   -0.9790 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3129    1.0711   -0.6950 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7426    1.7594    0.4979 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4889    1.0604    0.8475 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4014    1.7297    0.1799 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4469    5.1978   -1.0138 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3562    5.3887    0.7487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3810    6.6516   -0.3231 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7459    3.4365   -0.0356 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2337   -3.0368    0.4069 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5934   -6.3887    0.5437 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2132   -5.0032   -0.3726 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1100   -4.8305    1.3873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8543   -4.3764    1.1068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0131   -3.0311    1.9183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2892   -4.6554    1.8897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9853   -0.5985   -1.6614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2282   -0.7728   -2.2206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1995   -2.1996   -1.7837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3506    0.8467   -0.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8016    3.4126   -0.1961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0899    1.8145    0.3083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1270    2.2976   -1.4033 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6134   -1.8877   -0.4115 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4018   -2.3269    1.6679 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5430   -0.6917    1.0183 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9504   -0.9431   -1.2988 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6283    0.2504   -1.7605 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3216    0.6650   -0.4827 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4242    1.7320   -1.5782 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4729    2.7924    0.2103 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4446    1.7591    1.3623 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7491    1.8691   -0.8882 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3943    2.7361    0.6016 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 22  2  0
 22 23  1  0
 23 24  1  0
 22 21  1  0
 21 20  2  0
 20  5  1  0
  5  4  2  0
  5  6  1  0
  6  7  2  0
  7 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  2  0
 13 14  1  0
 14 15  1  0
 13 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  2  0
  4  3  1  0
 32  6  1  0
 19  8  1  0
 19 20  1  0
 31 27  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
 24 48  1  0
 24 49  1  0
 24 50  1  0
 21 47  1  0
  4 36  1  0
 25 51  1  6
 26 52  1  0
 27 53  1  1
 28 54  1  0
 28 55  1  0
 29 56  1  0
 29 57  1  0
 30 58  1  0
 30 59  1  0
 32 60  1  0
 32 61  1  0
  9 37  1  0
 12 38  1  0
 12 39  1  0
 12 40  1  0
 15 41  1  0
 15 42  1  0
 15 43  1  0
 18 44  1  0
 18 45  1  0
 18 46  1  0
M  END


  Mrv1652309022203402D          

 32 36  0  0  1  0            999 V2000
    5.0884   -4.8700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2763   -4.7248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9960   -3.9489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1838   -3.8037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9035   -3.0277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0914   -2.8825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8111   -2.1066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3429   -1.4759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0626   -0.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5945   -0.0692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3142    0.7067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5021    0.8519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4066   -0.2145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9384    0.4162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7505    0.2710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6869   -0.9904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4990   -1.1356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7793   -1.9115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1551   -1.6211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4354   -2.3970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2475   -2.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5278   -3.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3399   -3.4634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6202   -4.2393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9990   -1.9614    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7187   -1.1854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4672   -2.5921    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3574   -2.6189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5867   -3.4114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0962   -3.8744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7475   -3.3680    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5596   -3.5132    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  2  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
 10 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  2  0  0  0  0
  8 19  1  0  0  0  0
 19 20  1  0  0  0  0
  5 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
  3 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  7 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 27 31  1  6  0  0  0
 31 32  1  0  0  0  0
  6 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0146304

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC)C=C2C(=C1)C1=C([C@H](O)[C@H]3CCCN3C1)C1=CC(OC)=C(OC)C(OC)=C21

> <INCHI_IDENTIFIER>
InChI=1S/C25H29NO6/c1-28-18-9-13-14(10-19(18)29-2)22-15(11-20(30-3)24(31-4)25(22)32-5)21-16(13)12-26-8-6-7-17(26)23(21)27/h9-11,17,23,27H,6-8,12H2,1-5H3/t17-,23-/m1/s1

> <INCHI_KEY>
NYKPXBAWFYIQBH-UZUQRXQVSA-N

> <FORMULA>
C25H29NO6

> <MOLECULAR_WEIGHT>
439.508

> <EXACT_MASS>
439.199487658

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
48.36780023896228

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(20R,21S)-4,5,6,10,11-pentamethoxy-16-azapentacyclo[12.7.0.0^{2,7}.0^{8,13}.0^{16,20}]henicosa-1(14),2,4,6,8,10,12-heptaen-21-ol

> <ALOGPS_LOGP>
2.84

> <JCHEM_LOGP>
2.691696663999999

> <ALOGPS_LOGS>
-4.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.858609215909627

> <JCHEM_PKA_STRONGEST_BASIC>
8.124488519539597

> <JCHEM_POLAR_SURFACE_AREA>
69.62

> <JCHEM_REFRACTIVITY>
121.54539999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.57e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(20R,21S)-4,5,6,10,11-pentamethoxy-16-azapentacyclo[12.7.0.0^{2,7}.0^{8,13}.0^{16,20}]henicosa-1(14),2,4,6,8,10,12-heptaen-21-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       9.498  -9.091   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.982  -8.820   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.459  -7.371   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.943  -7.100   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.420  -5.652   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.904  -5.381   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.381  -3.932   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.374  -2.755   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.850  -1.307   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.843  -0.129   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.320   1.319   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.804   1.590   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.359  -0.400   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       7.352   0.777   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.868   0.506   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.882  -1.849   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.398  -2.120   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.921  -3.568   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.889  -3.026   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.413  -4.474   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.929  -4.746   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.452  -6.194   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       9.968  -6.465   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      10.491  -7.913   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.865  -3.661   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.342  -2.213   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.872  -4.839   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.667  -4.889   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.095  -6.368   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.179  -7.232   0.000  0.00  0.00           C+0
HETATM   31  N   UNK     0       1.395  -6.287   0.000  0.00  0.00           N+0
HETATM   32  C   UNK     0       2.911  -6.558   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   22                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   20                                                  
CONECT    6    5    7   32                                                  
CONECT    7    6    8   25                                                  
CONECT    8    7    9   19                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16    8   20                                                  
CONECT   20   19    5   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21    3   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25    7   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   31                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   27   32                                                  
CONECT   32   31    6                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₉NO₆

Average Mass

439.5080 Da

Monoisotopic Mass

439.19949 Da

IUPAC Name

(20R,21S)-4,5,6,10,11-pentamethoxy-16-azapentacyclo[12.7.0.0^{2,7}.0^{8,13}.0^{16,20}]henicosa-1(14),2,4,6,8,10,12-heptaen-21-ol

Traditional Name

(20R,21S)-4,5,6,10,11-pentamethoxy-16-azapentacyclo[12.7.0.0^{2,7}.0^{8,13}.0^{16,20}]henicosa-1(14),2,4,6,8,10,12-heptaen-21-ol

CAS Registry Number

Not Available

SMILES

COC1=C(OC)C=C2C(=C1)C1=C([C@H](O)[C@H]3CCCN3C1)C1=CC(OC)=C(OC)C(OC)=C21

InChI Identifier

InChI=1S/C25H29NO6/c1-28-18-9-13-14(10-19(18)29-2)22-15(11-20(30-3)24(31-4)25(22)32-5)21-16(13)12-26-8-6-7-17(26)23(21)27/h9-11,17,23,27H,6-8,12H2,1-5H3/t17-,23-/m1/s1

InChI Key

NYKPXBAWFYIQBH-UZUQRXQVSA-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
Ficus septica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthroindolizidines. These are aromatic polycyclic compounds containing the phenanthroindolizidine skeleton, which is structurally characterized by an indolizidine and a phenanthrene, where the indolizidine is fused to the second benzene ring of a phenanthrene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Phenanthroindolizidines

Direct Parent

Phenanthroindolizidines

Alternative Parents

Substituents

Phenanthroindolizidine
Naphthalene
Tetrahydroisoquinoline
Indolizidine
Anisole
Alkyl aryl ether
Aralkylamine
N-alkylpyrrolidine
Pyrrolidine
1,2-aminoalcohol
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Ether
Azacycle
Organoheterocyclic compound
Alcohol
Hydrocarbon derivative
Organic nitrogen compound
Organopnictogen compound
Amine
Organonitrogen compound
Organooxygen compound
Organic oxygen 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	2.84	ALOGPS
logP	2.69	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	13.86	ChemAxon
pKa (Strongest Basic)	8.12	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	69.62 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	121.55 m³·mol⁻¹	ChemAxon
Polarizability	48.37 Å³	ChemAxon
Number of Rings	5	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

162955398

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (20r,21s)-4,5,6,10,11-pentamethoxy-16-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2(7),3,5,8(13),9,11-heptaen-21-ol (NP0146304)

MOL for NP0146304 ((20r,21s)-4,5,6,10,11-pentamethoxy-16-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2(7),3,5,8(13),9,11-heptaen-21-ol)

3D MOL for NP0146304 ((20r,21s)-4,5,6,10,11-pentamethoxy-16-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2(7),3,5,8(13),9,11-heptaen-21-ol)

3D SDF for NP0146304 ((20r,21s)-4,5,6,10,11-pentamethoxy-16-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2(7),3,5,8(13),9,11-heptaen-21-ol)

3D-SDF for NP0146304 ((20r,21s)-4,5,6,10,11-pentamethoxy-16-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2(7),3,5,8(13),9,11-heptaen-21-ol)

PDB for NP0146304 ((20r,21s)-4,5,6,10,11-pentamethoxy-16-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2(7),3,5,8(13),9,11-heptaen-21-ol)

3D PDB for NP0146304 ((20r,21s)-4,5,6,10,11-pentamethoxy-16-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2(7),3,5,8(13),9,11-heptaen-21-ol)

SMILES for NP0146304 ((20r,21s)-4,5,6,10,11-pentamethoxy-16-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2(7),3,5,8(13),9,11-heptaen-21-ol)

INCHI for NP0146304 ((20r,21s)-4,5,6,10,11-pentamethoxy-16-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2(7),3,5,8(13),9,11-heptaen-21-ol)

Structure for NP0146304 ((20r,21s)-4,5,6,10,11-pentamethoxy-16-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2(7),3,5,8(13),9,11-heptaen-21-ol)

3D Structure for NP0146304 ((20r,21s)-4,5,6,10,11-pentamethoxy-16-azapentacyclo[12.7.0.0²,⁷.0⁸,¹³.0¹⁶,²⁰]henicosa-1(14),2(7),3,5,8(13),9,11-heptaen-21-ol)