NP-MRD: Showing NP-Card for 13-(acetyloxy)-1,7-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate (NP0296801)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-10 06:37:02 UTC

Updated at

2022-09-10 06:37:02 UTC

NP-MRD ID

NP0296801

Secondary Accession Numbers

None

Natural Product Identification

Common Name

13-(acetyloxy)-1,7-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate

Description

13-(Acetyloxy)-1,7-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]Pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate belongs to the class of organic compounds known as tigliane and ingenane diterpenoids. These are diterpenoids containing the tigliane or ingenane carbon skeleton. The tigliane skeleton is a tetracyclic ring that consists of the 4/7/6/3 ring junction. It is derived from casbane by 6,10- and 5,14-cyclizations and is a framework of phorbol. The ingenane skeleton is derived by rearrangement of tigliane. 13-(Acetyloxy)-1,7-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]Pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate is a moderately basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161518202D          

 39 43  0  0  0  0            999 V2000
    4.8042    2.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2403    2.2623    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4369    2.4495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1972    3.2390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3937    3.4262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8299    2.8239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0695    2.0345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8730    1.8473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1126    1.0579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9161    0.8707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5488    0.4556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7884   -0.3338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5919   -0.5210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1557    0.0812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8315   -1.3104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3488   -0.6677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6539   -1.3758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1615   -0.7254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9369   -1.0072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6206   -0.5456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9085   -1.8317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5589   -2.3393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1156   -2.0595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8689   -2.8468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4711   -3.4106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0995   -3.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3869   -2.7290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2676   -1.9127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4642   -1.7255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6607   -1.5383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9697   -1.0876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3368   -2.2971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2245   -0.9360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6223   -0.3722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8095    0.4313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2073    0.9951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4862    0.9031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0342   -3.9671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2893   -4.3217    0.0000 O   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  2  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  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 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
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 17 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 15 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
 30 32  1  0  0  0  0
 30 33  1  0  0  0  0
 12 33  1  0  0  0  0
 29 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 26 38  1  0  0  0  0
 38 39  1  0  0  0  0
M  END

     RDKit          3D

 76 80  0  0  0  0  0  0  0  0999 V2000
    7.0225    2.1154   -0.6267 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6786    1.5844   -0.5191 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1174    1.1722    0.7096 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9739    1.2993    1.8118 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5328    0.9232    3.0455 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2578    0.4229    3.2084 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4297    0.3058    2.1110 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8572    0.6836    0.8376 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9252    0.5402   -0.2387 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1824    0.8632   -1.4154 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6381    0.0229   -0.0659 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7141   -0.1196   -1.1003 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4513    0.8666   -0.9556 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2234    0.7597   -2.2559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3113    0.5499    0.2491 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7989    1.3443    1.3068 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1941   -0.8721    0.6201 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2580   -1.4661    1.4330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5601   -1.2673    1.5978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2985   -2.1354    2.5700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8463   -1.3017    3.5416 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3764   -0.2492    0.9000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.6742   -0.1873    1.3731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6477    1.0702    1.0575 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4996    2.2412    0.7104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7220    2.3963    0.8021 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5556    3.2374    0.2080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7620    4.7230    0.1993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4744    2.5932   -0.2399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6433    1.1111   -0.0609 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9592   -1.8184   -0.5344 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3298   -2.6688   -0.5353 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9736   -2.7976    0.7802 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1149   -4.0442   -1.1961 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2177   -1.4941   -1.3737 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0194   -1.7852   -2.7680 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0547   -1.7157   -3.6343 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8362   -2.0091   -5.1003 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2152   -1.4169   -3.2548 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7964    1.3705   -0.4400 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1565    2.5720   -1.6234 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1864    2.9534    0.0988 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1531    1.5209   -1.3940 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9791    1.6897    1.7066 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2140    1.0305    3.8829 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9448    0.1340    4.2111 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4453   -0.0844    2.2885 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2220    0.2588   -2.0270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0603    1.8789   -0.8883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7464   -0.2183   -2.3375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8510    1.6148   -2.4874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4339    0.7229   -3.0644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0045    1.8401    1.0569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2549   -0.9440    1.2550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9229   -2.2900    2.0806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6502   -2.9067    3.0061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1460   -2.5843    2.0153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3691   -1.7820    4.2167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4299   -0.5478   -0.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7726    0.4614    2.1171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1911    1.1592    2.0546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7863    5.2493    0.3688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1664    5.0380   -0.7736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4320    5.0512    0.9949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6393    3.1396   -0.6567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1241    0.7146   -0.9631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8697   -2.2501   -0.9567 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5121   -1.9484    1.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2115   -3.2072    1.5081 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7387   -3.6331    0.7366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5036   -4.6385   -0.4965 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1019   -4.5406   -1.2526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3722   -3.8887   -2.1630 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2795   -1.2044   -5.5928 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7925   -2.2724   -5.5514 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1964   -2.9360   -5.1252 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  1
 15 30  1  0
 30 29  1  0
 29 27  2  0
 27 28  1  0
 27 25  1  0
 25 26  2  0
 25 24  1  0
 24 22  1  0
 22 23  1  0
 22 19  1  0
 19 20  1  0
 20 21  1  0
 19 18  2  0
 18 17  1  0
 17 31  1  0
 31 32  1  0
 32 33  1  0
 32 34  1  0
 32 35  1  0
 35 36  1  6
 36 37  1  0
 37 38  1  0
 37 39  2  0
  8  3  1  0
 35 12  1  0
 17 15  1  0
 35 31  1  0
 24 30  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
  2 43  1  0
  4 44  1  0
  5 45  1  0
  6 46  1  0
  7 47  1  0
 12 48  1  6
 13 49  1  1
 14 50  1  0
 14 51  1  0
 14 52  1  0
 16 53  1  0
 30 66  1  6
 29 65  1  0
 28 62  1  0
 28 63  1  0
 28 64  1  0
 24 61  1  1
 22 59  1  6
 23 60  1  0
 20 56  1  0
 20 57  1  0
 21 58  1  0
 18 55  1  0
 17 54  1  1
 31 67  1  6
 33 68  1  0
 33 69  1  0
 33 70  1  0
 34 71  1  0
 34 72  1  0
 34 73  1  0
 38 74  1  0
 38 75  1  0
 38 76  1  0
M  END


  Mrv1533004161518202D          

 39 43  0  0  0  0            999 V2000
    4.8042    2.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2403    2.2623    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4369    2.4495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1972    3.2390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3937    3.4262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8299    2.8239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0695    2.0345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8730    1.8473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1126    1.0579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9161    0.8707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5488    0.4556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7884   -0.3338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5919   -0.5210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1557    0.0812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8315   -1.3104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3488   -0.6677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6539   -1.3758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1615   -0.7254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9369   -1.0072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6206   -0.5456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9085   -1.8317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5589   -2.3393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1156   -2.0595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8689   -2.8468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4711   -3.4106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0995   -3.1447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3869   -2.7290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2676   -1.9127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4642   -1.7255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6607   -1.5383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9697   -1.0876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3368   -2.2971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2245   -0.9360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6223   -0.3722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8095    0.4313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2073    0.9951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4862    0.9031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0342   -3.9671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2893   -4.3217    0.0000 O   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  2  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  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 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
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 17 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 15 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
 30 32  1  0  0  0  0
 30 33  1  0  0  0  0
 12 33  1  0  0  0  0
 29 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 26 38  1  0  0  0  0
 38 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0296801

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CNC1=CC=CC=C1C(=O)OC1C(C)C2(O)C3C=C(C)C(=O)C3C(O)C(CO)=CC2C2C(C)(C)C12OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H37NO8/c1-14-11-19-22(23(14)34)24(35)17(13-32)12-20-25-28(4,5)30(25,39-16(3)33)26(15(2)29(19,20)37)38-27(36)18-9-7-8-10-21(18)31-6/h7-12,15,19-20,22,24-26,31-32,35,37H,13H2,1-6H3

> <INCHI_KEY>
CUWDQBAYWDKQOB-UHFFFAOYSA-N

> <FORMULA>
C30H37NO8

> <MOLECULAR_WEIGHT>
539.625

> <EXACT_MASS>
539.251917155

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
57.37159066940298

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
13-(acetyloxy)-1,7-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate

> <ALOGPS_LOGP>
2.51

> <JCHEM_LOGP>
2.0651928910000006

> <ALOGPS_LOGS>
-3.53

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.292495295505503

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.59180213398525

> <JCHEM_PKA_STRONGEST_BASIC>
2.129541575778355

> <JCHEM_POLAR_SURFACE_AREA>
142.39

> <JCHEM_REFRACTIVITY>
144.85100000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.60e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
13-(acetyloxy)-1,7-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       8.968   5.347   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       7.915   4.223   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       6.415   4.572   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.968   6.046   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.468   6.395   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.416   5.271   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.863   3.798   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.363   3.448   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.810   1.975   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       7.310   1.625   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       4.758   0.850   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.205  -0.623   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.705  -0.973   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.757   0.152   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.152  -2.446   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.118  -1.246   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.687  -2.568   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.635  -1.354   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.082  -1.880   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.358  -1.018   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.029  -3.419   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      12.243  -4.367   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       9.549  -3.844   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.089  -5.314   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      10.213  -6.366   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       7.652  -5.870   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.322  -5.094   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.100  -3.570   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.600  -3.221   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.100  -2.871   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.810  -2.030   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.495  -4.288   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.152  -1.747   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       3.028  -0.695   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       3.378   0.805   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       2.254   1.858   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       4.641   1.686   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       7.530  -7.405   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       6.140  -8.067   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   33                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17   28                                             
CONECT   16   15                                                            
CONECT   17   15   18   23                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   17   24                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   38                                                  
CONECT   27   26   28                                                       
CONECT   28   27   15   29                                                  
CONECT   29   28   30   33                                                  
CONECT   30   29   31   32   33                                             
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   30   12   29   34                                             
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38   26   39                                                       
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   86    0
END

View in JSmol

Synonyms

Value	Source
13-(Acetyloxy)-1,7-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0,.0,]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoic acid	Generator
13-(Acetyloxy)-1,7-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoic acid	Generator

Chemical Formula

C₃₀H₃₇NO₈

Average Mass

539.6250 Da

Monoisotopic Mass

539.25192 Da

IUPAC Name

13-(acetyloxy)-1,7-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate

Traditional Name

13-(acetyloxy)-1,7-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate

CAS Registry Number

Not Available

SMILES

CNC1=CC=CC=C1C(=O)OC1C(C)C2(O)C3C=C(C)C(=O)C3C(O)C(CO)=CC2C2C(C)(C)C12OC(C)=O

InChI Identifier

InChI=1S/C30H37NO8/c1-14-11-19-22(23(14)34)24(35)17(13-32)12-20-25-28(4,5)30(25,39-16(3)33)26(15(2)29(19,20)37)38-27(36)18-9-7-8-10-21(18)31-6/h7-12,15,19-20,22,24-26,31-32,35,37H,13H2,1-6H3

InChI Key

CUWDQBAYWDKQOB-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tigliane and ingenane diterpenoids. These are diterpenoids containing the tigliane or ingenane carbon skeleton. The tigliane skeleton is a tetracyclic ring that consists of the 4/7/6/3 ring junction. It is derived from casbane by 6,10- and 5,14-cyclizations and is a framework of phorbol. The ingenane skeleton is derived by rearrangement of tigliane.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Tigliane and ingenane diterpenoids

Alternative Parents

Substituents

Tigliane diterpenoid
Aminobenzoic acid or derivatives
Benzoate ester
Benzoic acid or derivatives
Benzoyl
Phenylalkylamine
Aniline or substituted anilines
Secondary aliphatic/aromatic amine
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Benzenoid
Cyclic alcohol
Vinylogous amide
Tertiary alcohol
Amino acid or derivatives
Secondary alcohol
Ketone
Carboxylic acid ester
Secondary amine
Carboxylic acid derivative
Primary alcohol
Alcohol
Amine
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	2.51	ALOGPS
logP	2.07	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	13.59	ChemAxon
pKa (Strongest Basic)	2.13	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	142.39 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	144.85 m³·mol⁻¹	ChemAxon
Polarizability	57.37 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

73814462

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 13-(acetyloxy)-1,7-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate (NP0296801)

MOL for NP0296801 (13-(acetyloxy)-1,7-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate)

3D MOL for NP0296801 (13-(acetyloxy)-1,7-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate)

3D SDF for NP0296801 (13-(acetyloxy)-1,7-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate)

3D-SDF for NP0296801 (13-(acetyloxy)-1,7-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate)

PDB for NP0296801 (13-(acetyloxy)-1,7-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate)

3D PDB for NP0296801 (13-(acetyloxy)-1,7-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate)

SMILES for NP0296801 (13-(acetyloxy)-1,7-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate)

INCHI for NP0296801 (13-(acetyloxy)-1,7-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate)

Structure for NP0296801 (13-(acetyloxy)-1,7-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate)

3D Structure for NP0296801 (13-(acetyloxy)-1,7-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-14-yl 2-(methylamino)benzoate)