NP-MRD: Showing NP-Card for Rhodomollein III (NP0078693)

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Record Information

Version

2.0

Created at

2022-04-28 23:44:05 UTC

Updated at

2022-04-28 23:44:05 UTC

NP-MRD ID

NP0078693

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Rhodomollein III

Description

(1S,3R,4R,6R,7S,8S,9R,10R,13R,14R,16S)-4,6,7,9,14,16-hexahydroxy-5,5,9,14-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]Hexadecan-3-yl acetate belongs to the class of organic compounds known as leucothol and grayanotoxane diterpenoids. These are diterpenoids with a structure based either on the leucothol or the grayanotoxane skeleton. Rhodomollein III is found in Rhododendron molle and Rhododendron molle G.Don . Based on a literature review very few articles have been published on (1S,3R,4R,6R,7S,8S,9R,10R,13R,14R,16S)-4,6,7,9,14,16-hexahydroxy-5,5,9,14-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁸]Hexadecan-3-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292201442D          

 30 33  0  0  1  0            999 V2000
    0.9359   -0.2018    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1362    0.6499    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5350    1.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3896    1.4568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8050    0.6987    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3985   -0.0856    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6901   -0.6356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8493   -0.8074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6677   -0.9700    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2905   -0.4216    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2660    0.4030    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6087    0.9021    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1222    1.5477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3882    1.6971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0427    0.6812    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5472    0.0284    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0824   -0.6531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7060   -1.1933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9434   -1.4664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3719    0.0530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2742    1.4730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4695   -1.2270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8820   -1.7666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2993   -2.3506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5137   -3.1473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5022   -2.1380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7927    0.3109    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2084    1.0236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4392   -0.8605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1156   -0.1137    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  6  0  0  0
  3  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  1  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  1  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 16 20  1  6  0  0  0
 15 21  1  6  0  0  0
 10 22  1  6  0  0  0
  9 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
  6 27  1  0  0  0  0
  2 27  1  0  0  0  0
 27 28  1  6  0  0  0
  1 29  1  6  0  0  0
  1 30  1  1  0  0  0
M  END

     RDKit          3D

 66 69  0  0  0  0  0  0  0  0999 V2000
   -0.9255    4.7605    1.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1570    3.3461    1.4118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7890    3.0845    2.4409 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7047    2.3223    0.6734 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8309    0.9424    0.8769 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4391    0.2672    1.2965 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4341   -0.1265    0.3302 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4617    1.0189    0.1949 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7505    0.5517    0.7537 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9623    1.1591    0.1404 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7141    0.6763    2.1349 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6708   -0.9444    0.4040 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5909   -0.9983   -1.0936 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2569   -1.3835   -1.6280 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1022   -0.5573   -1.0305 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1302   -1.2886   -1.3397 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6081   -0.9068   -2.7394 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1389   -2.6788   -1.4567 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2142   -1.1887   -0.3085 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3989   -2.0552   -0.5707 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3445   -2.7635   -1.7697 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6223   -1.1844   -0.4550 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1484   -0.7805   -1.6502 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1119   -0.0424    0.4032 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0978   -0.5565    1.8363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0097    1.1395    0.2637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6847    0.2210   -0.0915 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8657    0.9060   -1.2981 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3098   -1.2144    0.9685 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8343   -2.4678    0.8164 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1765    4.9623    1.0496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2800    4.9707   -0.0129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4872    5.4306    1.6895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4226    0.9469    1.8292 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2504   -0.5601    2.0402 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8972    1.0427    2.0015 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5968    1.3316   -0.8374 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1315    1.9106    0.7702 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5818    1.6318    0.9554 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6140    0.3672   -0.3010 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7613    1.9103   -0.6340 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5488    0.3740    2.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4695   -1.5228    0.8532 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3149   -1.7622   -1.4328 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8976   -0.0486   -1.5857 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3003   -1.2497   -2.7427 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0459   -2.4870   -1.5081 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1373    0.3620   -1.6942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1860    0.1199   -2.9518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6776   -0.8198   -2.8532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1695   -1.5666   -3.5176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2817   -3.2134   -0.7697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7585   -1.5727    0.6360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5414   -2.8627    0.2129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9019   -3.5627   -1.7367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4461   -1.6650    0.1303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0419   -1.4964   -2.3145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2048    0.2677    2.5755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0012   -1.2138    1.9948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2233   -1.2033    2.0363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7435    1.0947    1.1211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6685    1.0404   -0.6481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5341    2.1163    0.3238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7337    1.3367   -1.3810 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3616   -0.9878    2.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1964   -2.6794    1.5428 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  7  6  1  1
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  1
  9 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  6
 16 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  1
 24 26  1  0
 24 27  1  0
 27 28  1  6
 12 29  1  0
 29 30  1  0
 27  5  1  0
 15  7  1  0
 27 19  1  0
 29  7  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  5 34  1  1
  6 35  1  0
  6 36  1  0
  8 37  1  0
  8 38  1  0
 10 39  1  0
 10 40  1  0
 10 41  1  0
 11 42  1  0
 12 43  1  1
 13 44  1  0
 13 45  1  0
 14 46  1  0
 14 47  1  0
 15 48  1  6
 17 49  1  0
 17 50  1  0
 17 51  1  0
 18 52  1  0
 19 53  1  1
 20 54  1  1
 21 55  1  0
 22 56  1  1
 23 57  1  0
 25 58  1  0
 25 59  1  0
 25 60  1  0
 26 61  1  0
 26 62  1  0
 26 63  1  0
 28 64  1  0
 29 65  1  1
 30 66  1  0
M  END


  Mrv1652304292201442D          

 30 33  0  0  1  0            999 V2000
    0.9359   -0.2018    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1362    0.6499    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5350    1.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3896    1.4568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8050    0.6987    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3985   -0.0856    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6901   -0.6356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8493   -0.8074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6677   -0.9700    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2905   -0.4216    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2660    0.4030    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6087    0.9021    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1222    1.5477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3882    1.6971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0427    0.6812    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5472    0.0284    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0824   -0.6531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7060   -1.1933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9434   -1.4664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3719    0.0530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2742    1.4730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4695   -1.2270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8820   -1.7666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2993   -2.3506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5137   -3.1473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5022   -2.1380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7927    0.3109    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2084    1.0236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4392   -0.8605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1156   -0.1137    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  6  0  0  0
  3  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  1  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  1  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 16 20  1  6  0  0  0
 15 21  1  6  0  0  0
 10 22  1  6  0  0  0
  9 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
  6 27  1  0  0  0  0
  2 27  1  0  0  0  0
 27 28  1  6  0  0  0
  1 29  1  6  0  0  0
  1 30  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0078693

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H]1C[C@]23C[C@@](C)(O)[C@H](CC[C@H]2[C@@](C)(O)[C@@H]2[C@H](O)[C@H](O)C(C)(C)[C@@]12O)[C@@H]3O

> <INCHI_IDENTIFIER>
InChI=1S/C22H36O8/c1-10(23)30-13-8-21-9-19(4,27)11(16(21)25)6-7-12(21)20(5,28)15-14(24)17(26)18(2,3)22(13,15)29/h11-17,24-29H,6-9H2,1-5H3/t11-,12+,13-,14+,15+,16+,17+,19-,20-,21+,22-/m1/s1

> <INCHI_KEY>
VNEMCNXMJWNLDK-KEROZRELSA-N

> <FORMULA>
C22H36O8

> <MOLECULAR_WEIGHT>
428.522

> <EXACT_MASS>
428.241018119

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
44.89752996635083

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3R,4R,6R,7S,8S,9R,10R,13R,14R,16S)-4,6,7,9,14,16-hexahydroxy-5,5,9,14-tetramethyltetracyclo[11.2.1.0^{1,10}.0^{4,8}]hexadecan-3-yl acetate

> <ALOGPS_LOGP>
0.26

> <JCHEM_LOGP>
-1.5871158649999995

> <ALOGPS_LOGS>
-1.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.528986146611995

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.857271119654285

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9365822713321243

> <JCHEM_POLAR_SURFACE_AREA>
147.68

> <JCHEM_REFRACTIVITY>
105.10479999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.15e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3R,4R,6R,7S,8S,9R,10R,13R,14R,16S)-4,6,7,9,14,16-hexahydroxy-5,5,9,14-tetramethyltetracyclo[11.2.1.0^{1,10}.0^{4,8}]hexadecan-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       1.747  -0.377   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.121   1.213   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.865   2.662   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.461   2.719   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.236   1.304   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.477  -0.160   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.155  -1.187   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.319  -1.507   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.846  -1.811   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.009  -0.787   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.963   0.752   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.736   1.684   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.695   2.889   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.325   3.168   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       9.413   1.271   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.355   0.053   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.487  -1.219   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.651  -2.227   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.228  -2.737   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      11.894   0.099   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       9.845   2.750   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       8.343  -2.290   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       7.246  -3.298   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       6.159  -4.388   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.559  -5.875   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.671  -3.991   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.346   0.580   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.122   1.911   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.820  -1.606   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       0.216  -0.212   0.000  0.00  0.00           O+0
CONECT    1    2    7   29   30                                             
CONECT    2    1    3   27                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7    8   27                                             
CONECT    7    6    1                                                       
CONECT    8    6    9                                                       
CONECT    9    8   10   23                                                  
CONECT   10    9   11   17   22                                             
CONECT   11   10   12   15                                                  
CONECT   12   11    5   13   14                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   11   16   21                                                  
CONECT   16   15   17   20                                                  
CONECT   17   16   10   18   19                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   16                                                            
CONECT   21   15                                                            
CONECT   22   10                                                            
CONECT   23    9   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27    6    2   28                                                  
CONECT   28   27                                                            
CONECT   29    1                                                            
CONECT   30    1                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Value	Source
(1S,3R,4R,6R,7S,8S,9R,10R,13R,14R,16S)-4,6,7,9,14,16-Hexahydroxy-5,5,9,14-tetramethyltetracyclo[11.2.1.0,.0,]hexadecan-3-yl acetic acid	Generator

Chemical Formula

C₂₂H₃₆O₈

Average Mass

428.5220 Da

Monoisotopic Mass

428.24102 Da

IUPAC Name

(1S,3R,4R,6R,7S,8S,9R,10R,13R,14R,16S)-4,6,7,9,14,16-hexahydroxy-5,5,9,14-tetramethyltetracyclo[11.2.1.0^{1,10}.0^{4,8}]hexadecan-3-yl acetate

Traditional Name

(1S,3R,4R,6R,7S,8S,9R,10R,13R,14R,16S)-4,6,7,9,14,16-hexahydroxy-5,5,9,14-tetramethyltetracyclo[11.2.1.0^{1,10}.0^{4,8}]hexadecan-3-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H]1C[C@]23C[C@@](C)(O)[C@H](CC[C@H]2[C@@](C)(O)[C@@H]2[C@H](O)[C@H](O)C(C)(C)[C@@]12O)[C@@H]3O

InChI Identifier

InChI=1S/C22H36O8/c1-10(23)30-13-8-21-9-19(4,27)11(16(21)25)6-7-12(21)20(5,28)15-14(24)17(26)18(2,3)22(13,15)29/h11-17,24-29H,6-9H2,1-5H3/t11-,12+,13-,14+,15+,16+,17+,19-,20-,21+,22-/m1/s1

InChI Key

VNEMCNXMJWNLDK-KEROZRELSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Rhododendron molle	LOTUS Database	35616633
Rhododendron molle G.Don	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as leucothol and grayanotoxane diterpenoids. These are diterpenoids with a structure based either on the leucothol or the grayanotoxane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Leucothol and grayanotoxane diterpenoids

Alternative Parents

Substituents

Grayanotoxane diterpenoid
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	0.26	ALOGPS
logP	-1.6	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	12.86	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	147.68 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	105.1 m³·mol⁻¹	ChemAxon
Polarizability	44.9 Å³	ChemAxon
Number of Rings	4	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

154497360

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Rhodomollein III (NP0078693)

MOL for NP0078693 (Rhodomollein III)

3D MOL for NP0078693 (Rhodomollein III)

3D SDF for NP0078693 (Rhodomollein III)

3D-SDF for NP0078693 (Rhodomollein III)

PDB for NP0078693 (Rhodomollein III)

3D PDB for NP0078693 (Rhodomollein III)

SMILES for NP0078693 (Rhodomollein III)

INCHI for NP0078693 (Rhodomollein III)

Structure for NP0078693 (Rhodomollein III)

3D Structure for NP0078693 (Rhodomollein III)