NP-MRD: Showing NP-Card for methyl 7-(acetyloxy)-9,12-dihydroxy-5a,5b,8,11a,13b-pentamethyl-3-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysene-8-carboxylate (NP0154084)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 10:50:54 UTC

Updated at

2022-09-02 10:50:54 UTC

NP-MRD ID

NP0154084

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 7-(acetyloxy)-9,12-dihydroxy-5a,5b,8,11a,13b-pentamethyl-3-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysene-8-carboxylate

Description

Methyl 20-(acetyloxy)-12,17-dihydroxy-1,2,9,14,18-pentamethyl-6-(prop-1-en-2-yl)pentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]Henicosane-18-carboxylate belongs to the class of organic compounds known as hopanoids. These are terpenoids containing hopane skeleton(A'-Neogammacerane), a pentacyclic structure with four cyclohexane rings and one cyclopentane ring (and often, a side chain emerging from C30). methyl 7-(acetyloxy)-9,12-dihydroxy-5a,5b,8,11a,13b-pentamethyl-3-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysene-8-carboxylate is found in Eurycorymbus cavaleriei. Methyl 20-(acetyloxy)-12,17-dihydroxy-1,2,9,14,18-pentamethyl-6-(prop-1-en-2-yl)pentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]Henicosane-18-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004261500362D          

 39 43  0  0  0  0            999 V2000
    1.4982   -4.1856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2690   -3.8916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3999   -3.0771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7599   -2.5565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1708   -2.7832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3264   -3.5934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7475   -2.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9225   -2.0876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1490   -1.3544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9739   -1.3418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3973   -2.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7988   -1.3293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2222   -2.0374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6238   -1.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2004   -0.6086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4487   -1.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8720   -2.0123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6969   -1.9998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3499   -1.2513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2395   -1.3783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9982   -1.7024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9245   -2.5241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1202   -2.7079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7186   -3.4285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8937   -3.4411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4704   -2.7330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0688   -3.4536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6455   -2.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5717   -3.5672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2439   -3.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4190   -3.4787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0174   -4.1994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4407   -4.9075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2656   -4.8950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0391   -5.6282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9957   -2.7706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5459   -3.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3265   -2.7999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3866   -3.8762    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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  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
 11 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
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  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
 18 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 17 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 13 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 31 36  1  0  0  0  0
  5 36  1  0  0  0  0
 11 36  1  0  0  0  0
 22 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
M  END

     RDKit          3D

 91 95  0  0  0  0  0  0  0  0999 V2000
    6.5672   -0.8444   -0.9902 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0555   -0.2818    0.0862 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5318   -0.7973    1.3986 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0709    0.7992    0.0779 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6955    1.2923   -1.3016 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4826    2.1206   -0.9672 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7800    1.4500    0.1719 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6025    2.5812    1.2103 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7487    0.4666    0.7636 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3609   -0.9445    0.6905 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4389   -1.4024   -0.3518 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3927   -0.4167   -0.8410 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6684   -0.2667   -2.3457 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4225    0.8667   -0.1012 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7815    0.7600    1.2512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2588   -0.2416    1.5114 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0561   -0.9075    2.7675 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6485   -1.2165    0.4610 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1254   -1.5350    0.3917 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2328   -2.9882   -0.0586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7505   -1.6038    1.7612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2048   -1.9497    1.7288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9895   -1.2529    0.6836 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6494   -2.1666   -0.1211 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2256   -0.1944   -0.1002 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1942    1.0295    0.7460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1017    0.0812   -1.2866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1662   -0.5973   -1.5181 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8622    1.0617   -2.2209 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6663    1.3314   -3.3277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9238   -0.7130   -0.5869 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0845    0.3189   -1.2957 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8074    1.4760   -0.5515 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0474    2.7450   -0.9565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7077    3.8797   -0.0571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5491    3.0071   -2.0690 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8122   -0.2946   -1.8606 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0035   -1.0639   -0.8621 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2916   -2.4286   -1.5249 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2882   -1.6360   -0.8859 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3114   -0.5644   -2.0134 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5370   -1.8921    1.4685 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5490   -0.3682    1.6404 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8858   -0.4256    2.2472 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5094    1.7118    0.5856 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5902    0.5291   -2.0456 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5524    1.9386   -1.6629 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8867    2.4818   -1.7882 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9773    3.0983   -0.6170 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6808    2.2094    2.2480 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7854    3.2512    0.9790 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5168    3.2611    1.1557 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9434    0.6970    1.8467 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9604   -1.3073    1.6863 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3227   -1.5411    0.6188 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0715   -1.8093   -1.1990 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8723   -2.3026   -0.0025 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9631   -0.8208   -2.9957 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6665    0.7443   -2.7138 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6654   -0.7089   -2.6264 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9229    1.6208   -0.7491 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5609    0.5771    2.0584 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4753    1.8241    1.5026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1386    0.4035    1.8398 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4889   -0.2851    3.3166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2154   -2.2046    0.8426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5631   -3.6431    0.5368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2486   -3.3430    0.2113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1919   -3.1218   -1.1349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6460   -0.7465    2.4032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2517   -2.4585    2.3149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6516   -1.6256    2.7272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4149   -3.0603    1.8000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8502   -0.6440    1.1351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1590   -2.5384   -0.8625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5511    1.9095    0.1683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9528    0.9601    1.5881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2662    1.2916    1.2286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2110    1.0790   -4.3011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5999    0.7190   -3.2595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9494    2.4191   -3.2678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2507   -1.3824   -1.4517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5955    0.7015   -2.1977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7948    4.4226   -0.3811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5880    3.4988    0.9672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6042    4.5610   -0.0403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1177   -0.9170   -2.7237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2980    0.5866   -2.2997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3186   -2.5624   -2.4572 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2806   -3.2592   -0.8301 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3341   -2.4886   -1.9556 H   0  0  0  0  0  0  0  0  0  0  0  0
 30 29  1  0
 29 27  1  0
 27 28  2  0
 25 27  1  6
 25 26  1  0
 25 23  1  0
 23 24  1  0
 23 22  1  0
 22 21  1  0
 21 19  1  0
 19 20  1  6
 19 18  1  0
 18 16  1  0
 16 17  1  0
 16 15  1  0
 15 14  1  0
 14  7  1  0
  7  8  1  1
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  6
 12 38  1  0
 38 39  1  6
 38 37  1  0
 37 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 34 36  2  0
 32 31  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  3
 31 25  1  0
 31 19  1  0
 38 18  1  0
 12 14  1  0
  9  7  1  0
 30 79  1  0
 30 80  1  0
 30 81  1  0
 26 76  1  0
 26 77  1  0
 26 78  1  0
 23 74  1  1
 24 75  1  0
 22 72  1  0
 22 73  1  0
 21 70  1  0
 21 71  1  0
 20 67  1  0
 20 68  1  0
 20 69  1  0
 18 66  1  1
 16 64  1  1
 17 65  1  0
 15 62  1  0
 15 63  1  0
 14 61  1  6
  8 50  1  0
  8 51  1  0
  8 52  1  0
  6 48  1  0
  6 49  1  0
  5 46  1  0
  5 47  1  0
  4 45  1  1
  9 53  1  1
 10 54  1  0
 10 55  1  0
 11 56  1  0
 11 57  1  0
 13 58  1  0
 13 59  1  0
 13 60  1  0
 39 89  1  0
 39 90  1  0
 39 91  1  0
 37 87  1  0
 37 88  1  0
 32 83  1  6
 35 84  1  0
 35 85  1  0
 35 86  1  0
 31 82  1  6
  3 42  1  0
  3 43  1  0
  3 44  1  0
  1 40  1  0
  1 41  1  0
M  END


  Mrv1533004261500362D          

 39 43  0  0  0  0            999 V2000
    1.4982   -4.1856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2690   -3.8916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3999   -3.0771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7599   -2.5565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1708   -2.7832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3264   -3.5934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7475   -2.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9225   -2.0876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1490   -1.3544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9739   -1.3418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3973   -2.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7988   -1.3293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2222   -2.0374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6238   -1.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2004   -0.6086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4487   -1.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8720   -2.0123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6969   -1.9998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3499   -1.2513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2395   -1.3783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9982   -1.7024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9245   -2.5241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1202   -2.7079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7186   -3.4285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8937   -3.4411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4704   -2.7330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0688   -3.4536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6455   -2.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5717   -3.5672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2439   -3.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4190   -3.4787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0174   -4.1994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4407   -4.9075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2656   -4.8950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0391   -5.6282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9957   -2.7706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5459   -3.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3265   -2.7999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3866   -3.8762    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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  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
 11 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
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  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
 18 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 17 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 13 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 31 36  1  0  0  0  0
  5 36  1  0  0  0  0
 11 36  1  0  0  0  0
 22 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0154084

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1(C)C(O)CCC2(C)C3C(O)CC4C5(C)CCC(C5CCC4(C)C3(C)CC(OC(C)=O)C12)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C33H52O6/c1-18(2)20-10-13-29(4)21(20)11-15-31(6)24(29)16-22(35)26-30(5)14-12-25(36)33(8,28(37)38-9)27(30)23(39-19(3)34)17-32(26,31)7/h20-27,35-36H,1,10-17H2,2-9H3

> <INCHI_KEY>
DICJXAYCQPWCBL-UHFFFAOYSA-N

> <FORMULA>
C33H52O6

> <MOLECULAR_WEIGHT>
544.773

> <EXACT_MASS>
544.376389394

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
91

> <JCHEM_AVERAGE_POLARIZABILITY>
62.83384457724731

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 20-(acetyloxy)-12,17-dihydroxy-1,2,9,14,18-pentamethyl-6-(prop-1-en-2-yl)pentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosane-18-carboxylate

> <ALOGPS_LOGP>
4.73

> <JCHEM_LOGP>
4.609228952333332

> <ALOGPS_LOGS>
-5.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.44925026216237

> <JCHEM_PKA_STRONGEST_BASIC>
-0.25695518845607246

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
149.7311

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.89e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 20-(acetyloxy)-12,17-dihydroxy-1,2,9,14,18-pentamethyl-6-(prop-1-en-2-yl)pentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosane-18-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0       2.797  -7.813   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.235  -7.264   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.480  -5.744   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.285  -4.772   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.919  -5.195   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.209  -6.708   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.129  -3.873   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.589  -3.897   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.878  -2.528   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.418  -2.505   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.208  -3.827   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.958  -2.481   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.748  -3.803   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.498  -2.458   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       9.707  -1.136   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      12.037  -2.435   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.828  -3.756   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.368  -3.733   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.720  -2.336   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      15.380  -2.573   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      16.797  -3.178   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      16.659  -4.712   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.158  -5.055   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.408  -6.400   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.868  -6.423   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.078  -5.102   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.328  -6.447   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.538  -5.125   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.401  -6.659   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.789  -6.470   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.249  -6.494   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       7.499  -7.839   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       8.289  -9.161   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       9.829  -9.137   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       7.540 -10.506   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       7.459  -5.172   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      17.819  -5.725   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      19.276  -5.226   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      17.522  -7.236   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7   36                                             
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   36                                             
CONECT   12   11                                                            
CONECT   13   11   14   28                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   26                                                  
CONECT   18   17   19   20   23                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   37                                                  
CONECT   23   22   18   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   17   27   28                                             
CONECT   27   26                                                            
CONECT   28   26   13   29   30                                             
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32   36                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   31    5   11                                                  
CONECT   37   22   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   86    0
END

View in JSmol

Synonyms

Value	Source
Methyl 20-(acetyloxy)-12,17-dihydroxy-1,2,9,14,18-pentamethyl-6-(prop-1-en-2-yl)pentacyclo[11.8.0.0,.0,.0,]henicosane-18-carboxylic acid	Generator
Methyl 20-(acetyloxy)-12,17-dihydroxy-1,2,9,14,18-pentamethyl-6-(prop-1-en-2-yl)pentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosane-18-carboxylic acid	Generator

Chemical Formula

C₃₃H₅₂O₆

Average Mass

544.7730 Da

Monoisotopic Mass

544.37639 Da

IUPAC Name

methyl 20-(acetyloxy)-12,17-dihydroxy-1,2,9,14,18-pentamethyl-6-(prop-1-en-2-yl)pentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosane-18-carboxylate

Traditional Name

methyl 20-(acetyloxy)-12,17-dihydroxy-1,2,9,14,18-pentamethyl-6-(prop-1-en-2-yl)pentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosane-18-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1(C)C(O)CCC2(C)C3C(O)CC4C5(C)CCC(C5CCC4(C)C3(C)CC(OC(C)=O)C12)C(C)=C

InChI Identifier

InChI=1S/C33H52O6/c1-18(2)20-10-13-29(4)21(20)11-15-31(6)24(29)16-22(35)26-30(5)14-12-25(36)33(8,28(37)38-9)27(30)23(39-19(3)34)17-32(26,31)7/h20-27,35-36H,1,10-17H2,2-9H3

InChI Key

DICJXAYCQPWCBL-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
Eurycorymbus cavaleriei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hopanoids. These are terpenoids containing hopane skeleton(A'-Neogammacerane), a pentacyclic structure with four cyclohexane rings and one cyclopentane ring (and often, a side chain emerging from C30).

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Hopanoids

Direct Parent

Hopanoids

Alternative Parents

Substituents

Hopane-skeleton
Triterpenoid
Steroid ester
6-hydroxysteroid
Hydroxysteroid
1-hydroxysteroid
Steroid
Beta-hydroxy acid
Hydroxy acid
Dicarboxylic acid or derivatives
Cyclic alcohol
Methyl ester
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Organic oxide
Organooxygen compound
Alcohol
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic 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	4.73	ALOGPS
logP	4.61	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	14.45	ChemAxon
pKa (Strongest Basic)	-0.26	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	149.73 m³·mol⁻¹	ChemAxon
Polarizability	62.83 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	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 methyl 7-(acetyloxy)-9,12-dihydroxy-5a,5b,8,11a,13b-pentamethyl-3-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysene-8-carboxylate (NP0154084)

MOL for NP0154084 (methyl 7-(acetyloxy)-9,12-dihydroxy-5a,5b,8,11a,13b-pentamethyl-3-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysene-8-carboxylate)

3D MOL for NP0154084 (methyl 7-(acetyloxy)-9,12-dihydroxy-5a,5b,8,11a,13b-pentamethyl-3-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysene-8-carboxylate)

3D SDF for NP0154084 (methyl 7-(acetyloxy)-9,12-dihydroxy-5a,5b,8,11a,13b-pentamethyl-3-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysene-8-carboxylate)

3D-SDF for NP0154084 (methyl 7-(acetyloxy)-9,12-dihydroxy-5a,5b,8,11a,13b-pentamethyl-3-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysene-8-carboxylate)

PDB for NP0154084 (methyl 7-(acetyloxy)-9,12-dihydroxy-5a,5b,8,11a,13b-pentamethyl-3-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysene-8-carboxylate)

3D PDB for NP0154084 (methyl 7-(acetyloxy)-9,12-dihydroxy-5a,5b,8,11a,13b-pentamethyl-3-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysene-8-carboxylate)

SMILES for NP0154084 (methyl 7-(acetyloxy)-9,12-dihydroxy-5a,5b,8,11a,13b-pentamethyl-3-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysene-8-carboxylate)

INCHI for NP0154084 (methyl 7-(acetyloxy)-9,12-dihydroxy-5a,5b,8,11a,13b-pentamethyl-3-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysene-8-carboxylate)

Structure for NP0154084 (methyl 7-(acetyloxy)-9,12-dihydroxy-5a,5b,8,11a,13b-pentamethyl-3-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysene-8-carboxylate)

3D Structure for NP0154084 (methyl 7-(acetyloxy)-9,12-dihydroxy-5a,5b,8,11a,13b-pentamethyl-3-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysene-8-carboxylate)