NP-MRD: Showing NP-Card for Phorbol 13-acetate (NP0140977)

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Record Information

Version

2.0

Created at

2022-06-29 22:01:24 UTC

Updated at

2022-06-29 22:01:24 UTC

NP-MRD ID

NP0140977

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Phorbol 13-acetate

Description

13-Acetylphorbol, also known as phorbol-13-acetate, belongs to the class of organic compounds known as phorbol esters. These are tigliane diterpenoids which are esters of phorbol. Thus, 13-acetylphorbol is considered to be an isoprenoid lipid molecule. Phorbol 13-acetate is found in Croton tiglium. 13-Acetylphorbol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

PRB
  Mrv0541 02231217382D          

 34 37  0  0  0  0            999 V2000
    1.5670    0.5942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3423    0.3124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3139   -0.5121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9643   -1.0197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5210   -0.7399    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0974   -1.3302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2743   -1.5272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5050   -1.8251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2076   -1.4094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3269   -0.5931    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2369    0.0092    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7542    0.6519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0594   -0.0562    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0027    0.7986    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8062    0.9858    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0458    1.7752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3700    0.3836    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1304   -0.4059    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9339   -0.2187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7180    0.0378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4431   -0.8678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5612    1.4008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0261    0.7741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4396   -2.6475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3053   -3.0021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9723    0.9474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7851    1.7509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3873    2.3148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1083    2.2227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7567   -0.9883    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8242    0.4783    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5770    0.8686    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4071    1.4121    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2629   -0.9746    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1 13  1  0  0  0  0
  2  3  1  0  0  0  0
  2 23  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  5 13  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 24  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 18  1  0  0  0  0
 10 30  1  6  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 13 31  1  1  0  0  0
 14 15  1  0  0  0  0
 14 22  1  1  0  0  0
 14 32  1  6  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 15 33  1  1  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 17 26  1  1  0  0  0
 18 19  1  0  0  0  0
 18 34  1  1  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 24 25  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
M  END

     RDKit          3D

 59 62  0  0  0  0  0  0  0  0999 V2000
    5.2260    1.0820   -2.2053 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2718    0.9222   -1.0576 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4047    1.6544   -0.0518 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2771   -0.0098   -1.1178 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3279   -0.2100   -0.0499 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8993    1.0079    0.6418 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5918    1.2998    1.8183 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3924    1.1394    0.9131 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0993    2.5617    1.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3094    0.4285   -0.1469 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3222    0.7439   -1.3780 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0395   -1.0628    0.1460 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0142   -1.9479   -0.4885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3162   -2.0296   -0.3122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0814   -3.0435   -1.1068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6994   -3.9093   -0.2113 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1776   -1.2317    0.5963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6345    0.1725    0.7866 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0820    0.3588    2.0336 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7739    1.1119    0.6117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9113    1.0138    1.1342 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3825    2.2037   -0.2800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1190    3.4602   -0.5570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2201    1.8888   -0.8278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7472    0.5756   -0.3512 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3671   -1.2665   -0.3335 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4797   -1.5326    0.6065 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1853   -1.7535    2.0531 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5369   -2.5160    0.0767 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1031    1.7006   -1.9173 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7257    1.5442   -3.0713 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6223    0.1007   -2.5160 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1028    1.9060   -0.0178 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9585    1.5294    2.5329 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2369    0.5903    1.8894 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4419    2.8468    2.1915 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7320    3.2027    0.4781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9186    2.9003    1.0644 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3086    1.7380   -1.4125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0062   -1.2150    1.2669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6089   -2.6409   -1.2118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7720   -2.5847   -1.8163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3321   -3.6679   -1.6658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1296   -3.9477    0.5971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1907   -1.1899    0.1484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3049   -1.7113    1.5869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2475   -0.4033    2.6442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6940    3.8071    0.3397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8717    3.3455   -1.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4611    4.2931   -0.8366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6943    2.4999   -1.5203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0108   -0.1280   -1.2038 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3750   -1.8062   -1.3288 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9825   -0.8665    2.6420 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3143   -2.4544    2.1993 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0331   -2.2853    2.5793 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3419   -3.5199    0.4729 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5445   -2.5145   -1.0365 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5458   -2.1808    0.4130 H   0  0  0  0  0  0  0  0  0  0  0  0
 26 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 18 19  1  1
 18 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 25 10  1  0
 10 11  1  6
 10  8  1  0
  8  9  1  0
  8  6  1  0
  6  7  1  0
  6  5  1  0
  5  4  1  6
  4  2  1  0
  2  1  1  0
  2  3  2  0
  5 27  1  0
 27 28  1  0
 27 29  1  0
  5 26  1  0
 27 26  1  0
 10 12  1  0
 25 18  1  0
 26 53  1  6
 12 40  1  1
 13 41  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  0
 17 45  1  0
 17 46  1  0
 19 47  1  0
 23 48  1  0
 23 49  1  0
 23 50  1  0
 24 51  1  0
 25 52  1  6
 11 39  1  0
  8 35  1  1
  9 36  1  0
  9 37  1  0
  9 38  1  0
  6 33  1  6
  7 34  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
 28 54  1  0
 28 55  1  0
 28 56  1  0
 29 57  1  0
 29 58  1  0
 29 59  1  0
M  END

PRB
  Mrv0541 02231217382D          

 34 37  0  0  0  0            999 V2000
    1.5670    0.5942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3423    0.3124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3139   -0.5121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9643   -1.0197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5210   -0.7399    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0974   -1.3302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2743   -1.5272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5050   -1.8251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2076   -1.4094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3269   -0.5931    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2369    0.0092    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7542    0.6519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0594   -0.0562    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0027    0.7986    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8062    0.9858    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0458    1.7752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3700    0.3836    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1304   -0.4059    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9339   -0.2187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7180    0.0378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4431   -0.8678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5612    1.4008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0261    0.7741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4396   -2.6475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3053   -3.0021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9723    0.9474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7851    1.7509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3873    2.3148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1083    2.2227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7567   -0.9883    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8242    0.4783    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5770    0.8686    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4071    1.4121    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2629   -0.9746    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1 13  1  0  0  0  0
  2  3  1  0  0  0  0
  2 23  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  5 13  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 24  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 18  1  0  0  0  0
 10 30  1  6  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 13 31  1  1  0  0  0
 14 15  1  0  0  0  0
 14 22  1  1  0  0  0
 14 32  1  6  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 15 33  1  1  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 17 26  1  1  0  0  0
 18 19  1  0  0  0  0
 18 34  1  1  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 24 25  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0140977

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12[C@]3([H])C=C(CO)C[C@]4(O)C(=O)C(C)=C[C@@]4([H])[C@@]3(O)[C@]([H])(C)[C@@]([H])(O)[C@@]1(OC(C)=O)C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C22H30O7/c1-10-6-15-20(27,17(10)25)8-13(9-23)7-14-16-19(4,5)22(16,29-12(3)24)18(26)11(2)21(14,15)28/h6-7,11,14-16,18,23,26-28H,8-9H2,1-5H3/t11-,14+,15-,16-,18-,20-,21-,22-/m1/s1

> <INCHI_KEY>
SDSVJYOOAPRSDA-RPCQODIISA-N

> <FORMULA>
C22H30O7

> <MOLECULAR_WEIGHT>
406.4694

> <EXACT_MASS>
406.199153314

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
43.05399752218722

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,6R,10S,11R,13S,14R,15R)-1,6,14-trihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl acetate

> <ALOGPS_LOGP>
0.63

> <JCHEM_LOGP>
-0.3397573340000003

> <ALOGPS_LOGS>
-2.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.507530535424806

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.53587869153182

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7316135453168844

> <JCHEM_POLAR_SURFACE_AREA>
124.29000000000002

> <JCHEM_REFRACTIVITY>
104.92889999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.44e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phorbol-13-acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: PRB                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       2.925   1.109   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.372   0.583   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.319  -0.956   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       5.533  -1.903   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.839  -1.381   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.915  -2.483   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.379  -2.851   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.943  -3.407   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.388  -2.631   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.610  -1.107   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.442   0.017   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.408   1.217   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.978  -0.105   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.005   1.491   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.505   1.840   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.952   3.314   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.557   0.716   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.110  -0.758   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.610  -0.408   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.074   0.071   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.560  -1.620   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.048   2.615   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.649   1.445   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.821  -4.942   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -0.570  -5.604   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -3.682   1.768   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -3.332   3.268   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -4.456   4.321   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -2.069   4.149   0.000  0.00  0.00           C+0
HETATM   30  H   UNK     0      -1.413  -1.845   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.539   0.893   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.077   1.621   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.760   2.636   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0      -2.357  -1.819   0.000  0.00  0.00           H+0
CONECT    1    2   13                                                       
CONECT    2    1    3   23                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7   13                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   24                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   18   30                                             
CONECT   11   10   12   13   14                                             
CONECT   12   11                                                            
CONECT   13    1    5   11   31                                             
CONECT   14   11   15   22   32                                             
CONECT   15   14   16   17   33                                             
CONECT   16   15                                                            
CONECT   17   15   18   19   26                                             
CONECT   18   10   17   19   34                                             
CONECT   19   17   18   20   21                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   14                                                            
CONECT   23    2                                                            
CONECT   24    8   25                                                       
CONECT   25   24                                                            
CONECT   26   17   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   10                                                            
CONECT   31   13                                                            
CONECT   32   14                                                            
CONECT   33   15                                                            
CONECT   34   18                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
Phorbol 13-monoacetate	ChEBI
Phorbol-13-acetate	ChEBI
Phorbol 13-monoacetic acid	Generator
Phorbol-13-acetic acid	Generator
Phorbol 13-monoacetate, (1ar-(1aalpha,1bbeta,4abeta,7aalpha,7balpa,8alpha,9beta,9aalpha))-isomer	MeSH
13-ACETYLPHORBOL	ChEBI
Phorbol 13-acetic acid	Generator

Chemical Formula

C₂₂H₃₀O₇

Average Mass

406.4694 Da

Monoisotopic Mass

406.19915 Da

IUPAC Name

(1S,2S,6R,10S,11R,13S,14R,15R)-1,6,14-trihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0²,⁶.0¹¹,¹³]pentadeca-3,8-dien-13-yl acetate

Traditional Name

phorbol-13-acetate

CAS Registry Number

Not Available

SMILES

[H][C@]12[C@]3([H])C=C(CO)C[C@]4(O)C(=O)C(C)=C[C@@]4([H])[C@@]3(O)[C@]([H])(C)[C@@]([H])(O)[C@@]1(OC(C)=O)C2(C)C

InChI Identifier

InChI=1S/C22H30O7/c1-10-6-15-20(27,17(10)25)8-13(9-23)7-14-16-19(4,5)22(16,29-12(3)24)18(26)11(2)21(14,15)28/h6-7,11,14-16,18,23,26-28H,8-9H2,1-5H3/t11-,14+,15-,16-,18-,20-,21-,22-/m1/s1

InChI Key

SDSVJYOOAPRSDA-RPCQODIISA-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
Croton tiglium	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phorbol esters. These are tigliane diterpenoids which are esters of phorbol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Phorbol esters

Alternative Parents

Substituents

Phorbol ester
Cyclic alcohol
Tertiary alcohol
Carboxylic acid ester
Ketone
Secondary alcohol
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Alcohol
Primary alcohol
Carbonyl group
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

phorbol ester (CHEBI:45127 )
Tigliane and ingenane diterpenoids (LMPR0104330003 )

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	0.63	ALOGPS
logP	-0.34	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	12.54	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	124.29 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	104.93 m³·mol⁻¹	ChemAxon
Polarizability	43.05 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

DB04376

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

499953

PDB ID

Not Available

ChEBI ID

45127

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Phorbol 13-acetate (NP0140977)

MOL for NP0140977 (Phorbol 13-acetate)

3D MOL for NP0140977 (Phorbol 13-acetate)

3D SDF for NP0140977 (Phorbol 13-acetate)

3D-SDF for NP0140977 (Phorbol 13-acetate)

PDB for NP0140977 (Phorbol 13-acetate)

3D PDB for NP0140977 (Phorbol 13-acetate)

SMILES for NP0140977 (Phorbol 13-acetate)

INCHI for NP0140977 (Phorbol 13-acetate)

Structure for NP0140977 (Phorbol 13-acetate)

3D Structure for NP0140977 (Phorbol 13-acetate)