NP-MRD: Showing NP-Card for (1s,2r,3s,5r,8r,9s,10r,11r,12r)-11,12-dihydroxy-3,10-dimethyl-3-[(2s)-3-methyl-5-oxo-2h-furan-2-yl]-7-oxo-6,13-dioxatetracyclo[7.5.0.0¹,⁵.0²,¹²]tetradecan-8-yl acetate (NP0314758)

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Record Information

Version

2.0

Created at

2022-09-11 13:01:44 UTC

Updated at

2022-09-11 13:01:44 UTC

NP-MRD ID

NP0314758

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,3s,5r,8r,9s,10r,11r,12r)-11,12-dihydroxy-3,10-dimethyl-3-[(2s)-3-methyl-5-oxo-2h-furan-2-yl]-7-oxo-6,13-dioxatetracyclo[7.5.0.0¹,⁵.0²,¹²]tetradecan-8-yl acetate

Description

15-O-Acetyl-5(S)-polyandrol belongs to the class of organic compounds known as quassinoids. These are a group of compounds chemically degraded from triterpenes. According to their basic skeleton, quassinoids are categorized into five distinct groups, C-18, C-19, C-20, C-22 and C-25 types. The C-20 quassinoids can be further classified into two types, tetracyclic and the pentacyclic. The tetracyclic variety does not have oxygenation at C-20, while the pentacyclic quassinoids possess additional oxygenation at C-20 that allows for the formation of an additional ring. Based on a literature review very few articles have been published on 15-O-Acetyl-5(S)-polyandrol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112215012D          

 30 34  0  0  1  0            999 V2000
    0.5927   -3.1382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6790   -2.3177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0115   -1.8328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4326   -1.9821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5189   -1.1617    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8514   -0.6767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0978   -1.0123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9377    0.1437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6913    0.4793    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9463    1.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7713    1.2639    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5782    1.4355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6850    2.0844    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2981    2.6364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9626    3.3901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3751    4.1046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1421    3.3039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9706    2.4969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2169    2.1614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0262    0.4793    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3588   -0.0056    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6137   -0.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4387   -0.7902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7799    0.1437    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8809    0.9625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8661   -0.6767    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6198   -1.0123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1987   -1.1617    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3141   -1.9785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2725   -0.8261    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  6  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 11  1  1  0  0  0
 20 21  1  0  0  0  0
  9 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 20 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
  5 30  1  0  0  0  0
 30 21  1  6  0  0  0
M  END

     RDKit          3D

 56 60  0  0  0  0  0  0  0  0999 V2000
    4.9271    0.0862    2.4221 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5621    0.3871    1.9017 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5838    0.6251    2.6468 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3205    0.4151    0.5401 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0582    0.6908   -0.0259 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1058    2.0984   -0.6119 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1502    2.7747   -0.6325 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9161    2.5714   -1.1164 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0956    1.7190   -1.8702 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3977    1.9323   -1.6111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7754    0.8694   -0.5932 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1641    0.4043   -0.9578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7756    1.5500    0.7752 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6914    2.6163    0.6930 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6524    2.4616    1.6546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6515    3.2376    1.8723 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3397    1.2538    2.3920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2401    0.7282    1.8741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6518   -0.5245    2.4489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7278   -0.1210   -0.6745 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3255    0.2901   -1.6817 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0143   -0.5591   -2.8957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1958   -1.1789   -2.6021 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0301   -1.4793   -1.2239 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2011   -2.0492   -0.8139 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1865   -2.3149   -1.1111 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0620   -3.2277   -0.0525 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4941   -1.6575   -0.8255 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0374   -2.0646    0.5410 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6199   -0.1981   -1.1272 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9969    0.3460    3.4998 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1885   -0.9847    2.3024 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6399    0.7531    1.8967 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3537    0.8177    0.8209 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2456    1.9864   -2.9451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9716    1.7697   -2.5539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5864    2.9265   -1.1858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1202   -0.0036   -1.9823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6012   -0.2732   -0.2234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7870    1.3441   -1.0365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7429    1.9581    0.9799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9199    0.8747    3.2141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5745   -0.3390    2.6669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8253   -1.3640    1.7781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1228   -0.7730    3.4470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2881   -0.2823    0.3324 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7614   -1.3574   -3.0696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0292    0.0399   -3.8252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1411   -2.7544   -0.1525 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2041   -2.9949   -2.0156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5590   -4.0243   -0.3618 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2289   -2.1710   -1.5284 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7495   -3.1604    0.6469 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5476   -1.5707    1.3678 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1436   -2.0994    0.5564 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3690   -0.0005   -1.9638 H   0  0  0  0  0  0  0  0  0  0  0  0
 29 28  1  0
 28 26  1  0
 26 27  1  0
 26 24  1  0
 24 25  1  1
 24 23  1  0
 23 22  1  0
 21 22  1  6
 21  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  6
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 11 20  1  0
  9  8  1  0
  8  6  1  0
  6  7  2  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
  5 30  1  0
 30 28  1  0
 20 24  1  0
 20 21  1  0
 30 21  1  0
 18 13  1  0
 29 53  1  0
 29 54  1  0
 29 55  1  0
 28 52  1  6
 26 50  1  6
 27 51  1  0
 25 49  1  0
 22 47  1  0
 22 48  1  0
  9 35  1  6
 10 36  1  0
 10 37  1  0
 12 38  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  1
 17 42  1  0
 19 43  1  0
 19 44  1  0
 19 45  1  0
 20 46  1  1
  5 34  1  1
  1 31  1  0
  1 32  1  0
  1 33  1  0
 30 56  1  6
M  END


  Mrv1652309112215012D          

 30 34  0  0  1  0            999 V2000
    0.5927   -3.1382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6790   -2.3177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0115   -1.8328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4326   -1.9821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5189   -1.1617    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8514   -0.6767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0978   -1.0123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9377    0.1437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6913    0.4793    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9463    1.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7713    1.2639    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5782    1.4355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6850    2.0844    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2981    2.6364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9626    3.3901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3751    4.1046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1421    3.3039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9706    2.4969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2169    2.1614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0262    0.4793    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3588   -0.0056    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6137   -0.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4387   -0.7902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7799    0.1437    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8809    0.9625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8661   -0.6767    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6198   -1.0123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1987   -1.1617    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3141   -1.9785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2725   -0.8261    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  6  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 11  1  1  0  0  0
 20 21  1  0  0  0  0
  9 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 20 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
  5 30  1  0  0  0  0
 30 21  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0314758

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1[C@@H](O)[C@]2(O)OC[C@@]34[C@@H](C[C@](C)([C@H]5OC(=O)C=C5C)[C@@H]23)OC(=O)[C@H](OC(C)=O)[C@@H]14

> <INCHI_IDENTIFIER>
InChI=1S/C21H26O9/c1-8-5-12(23)30-16(8)19(4)6-11-20-7-27-21(26,18(19)20)15(24)9(2)13(20)14(17(25)29-11)28-10(3)22/h5,9,11,13-16,18,24,26H,6-7H2,1-4H3/t9-,11-,13-,14-,15-,16+,18-,19-,20+,21+/m1/s1

> <INCHI_KEY>
DYGAUOPJXMDDON-GBXCSXSHSA-N

> <FORMULA>
C21H26O9

> <MOLECULAR_WEIGHT>
422.43

> <EXACT_MASS>
422.157682417

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
40.824572901194536

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,3S,5R,8R,9S,10R,11R,12R)-11,12-dihydroxy-3,10-dimethyl-3-[(2S)-3-methyl-5-oxo-2,5-dihydrofuran-2-yl]-7-oxo-6,13-dioxatetracyclo[7.5.0.0^{1,5}.0^{2,12}]tetradecan-8-yl acetate

> <JCHEM_LOGP>
0.23817746066666626

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.950273415478714

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.661843172571282

> <JCHEM_PKA_STRONGEST_BASIC>
-3.655973325932342

> <JCHEM_POLAR_SURFACE_AREA>
128.59

> <JCHEM_REFRACTIVITY>
98.33150000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,3S,5R,8R,9S,10R,11R,12R)-11,12-dihydroxy-3,10-dimethyl-3-[(2S)-3-methyl-5-oxo-2H-furan-2-yl]-7-oxo-6,13-dioxatetracyclo[7.5.0.0^{1,5}.0^{2,12}]tetradecan-8-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       1.106  -5.858   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.267  -4.326   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.021  -3.421   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       2.674  -3.700   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.835  -2.168   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.589  -1.263   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.182  -1.890   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       1.750   0.268   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       3.157   0.895   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.633   2.359   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.173   2.359   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.679   2.680   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.012   3.891   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.157   4.921   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.530   6.328   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.300   7.662   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.999   6.167   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.678   4.661   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.272   4.035   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.649   0.895   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.403  -0.010   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.879  -1.475   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.419  -1.475   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       7.056   0.268   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       7.244   1.797   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       7.217  -1.263   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       8.624  -1.890   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       5.971  -2.168   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.186  -3.693   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.242  -1.542   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   30                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   21                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13   20                                             
CONECT   12   11                                                            
CONECT   13   11   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   13   19                                                  
CONECT   19   18                                                            
CONECT   20   11   21   24                                                  
CONECT   21   20    9   22   30                                             
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   20   25   26                                             
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28    5   21                                                  
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₆O₉

Average Mass

422.4300 Da

Monoisotopic Mass

422.15768 Da

IUPAC Name

(1S,2R,3S,5R,8R,9S,10R,11R,12R)-11,12-dihydroxy-3,10-dimethyl-3-[(2S)-3-methyl-5-oxo-2,5-dihydrofuran-2-yl]-7-oxo-6,13-dioxatetracyclo[7.5.0.0^{1,5}.0^{2,12}]tetradecan-8-yl acetate

Traditional Name

(1S,2R,3S,5R,8R,9S,10R,11R,12R)-11,12-dihydroxy-3,10-dimethyl-3-[(2S)-3-methyl-5-oxo-2H-furan-2-yl]-7-oxo-6,13-dioxatetracyclo[7.5.0.0^{1,5}.0^{2,12}]tetradecan-8-yl acetate

CAS Registry Number

Not Available

SMILES

C[C@H]1[C@@H](O)[C@]2(O)OC[C@@]34[C@@H](C[C@](C)([C@H]5OC(=O)C=C5C)[C@@H]23)OC(=O)[C@H](OC(C)=O)[C@@H]14

InChI Identifier

InChI=1S/C21H26O9/c1-8-5-12(23)30-16(8)19(4)6-11-20-7-27-21(26,18(19)20)15(24)9(2)13(20)14(17(25)29-11)28-10(3)22/h5,9,11,13-16,18,24,26H,6-7H2,1-4H3/t9-,11-,13-,14-,15-,16+,18-,19-,20+,21+/m1/s1

InChI Key

DYGAUOPJXMDDON-GBXCSXSHSA-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 quassinoids. These are a group of compounds chemically degraded from triterpenes. According to their basic skeleton, quassinoids are categorized into five distinct groups, C-18, C-19, C-20, C-22 and C-25 types. The C-20 quassinoids can be further classified into two types, tetracyclic and the pentacyclic. The tetracyclic variety does not have oxygenation at C-20, while the pentacyclic quassinoids possess additional oxygenation at C-20 that allows for the formation of an additional ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Quassinoids

Alternative Parents

Substituents

Quassinoid
Tricarboxylic acid or derivatives
Delta valerolactone
Delta_valerolactone
Oxepane
2-furanone
Oxane
Cyclic alcohol
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Tetrahydrofuran
Enoate ester
Lactone
Hemiacetal
Carboxylic acid ester
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.24	ChemAxon
pKa (Strongest Acidic)	7.66	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	128.59 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	98.33 m³·mol⁻¹	ChemAxon
Polarizability	40.82 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

100990343

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2r,3s,5r,8r,9s,10r,11r,12r)-11,12-dihydroxy-3,10-dimethyl-3-[(2s)-3-methyl-5-oxo-2h-furan-2-yl]-7-oxo-6,13-dioxatetracyclo[7.5.0.0¹,⁵.0²,¹²]tetradecan-8-yl acetate (NP0314758)

MOL for NP0314758 ((1s,2r,3s,5r,8r,9s,10r,11r,12r)-11,12-dihydroxy-3,10-dimethyl-3-[(2s)-3-methyl-5-oxo-2h-furan-2-yl]-7-oxo-6,13-dioxatetracyclo[7.5.0.0¹,⁵.0²,¹²]tetradecan-8-yl acetate)

3D MOL for NP0314758 ((1s,2r,3s,5r,8r,9s,10r,11r,12r)-11,12-dihydroxy-3,10-dimethyl-3-[(2s)-3-methyl-5-oxo-2h-furan-2-yl]-7-oxo-6,13-dioxatetracyclo[7.5.0.0¹,⁵.0²,¹²]tetradecan-8-yl acetate)

3D SDF for NP0314758 ((1s,2r,3s,5r,8r,9s,10r,11r,12r)-11,12-dihydroxy-3,10-dimethyl-3-[(2s)-3-methyl-5-oxo-2h-furan-2-yl]-7-oxo-6,13-dioxatetracyclo[7.5.0.0¹,⁵.0²,¹²]tetradecan-8-yl acetate)

3D-SDF for NP0314758 ((1s,2r,3s,5r,8r,9s,10r,11r,12r)-11,12-dihydroxy-3,10-dimethyl-3-[(2s)-3-methyl-5-oxo-2h-furan-2-yl]-7-oxo-6,13-dioxatetracyclo[7.5.0.0¹,⁵.0²,¹²]tetradecan-8-yl acetate)

PDB for NP0314758 ((1s,2r,3s,5r,8r,9s,10r,11r,12r)-11,12-dihydroxy-3,10-dimethyl-3-[(2s)-3-methyl-5-oxo-2h-furan-2-yl]-7-oxo-6,13-dioxatetracyclo[7.5.0.0¹,⁵.0²,¹²]tetradecan-8-yl acetate)

3D PDB for NP0314758 ((1s,2r,3s,5r,8r,9s,10r,11r,12r)-11,12-dihydroxy-3,10-dimethyl-3-[(2s)-3-methyl-5-oxo-2h-furan-2-yl]-7-oxo-6,13-dioxatetracyclo[7.5.0.0¹,⁵.0²,¹²]tetradecan-8-yl acetate)

SMILES for NP0314758 ((1s,2r,3s,5r,8r,9s,10r,11r,12r)-11,12-dihydroxy-3,10-dimethyl-3-[(2s)-3-methyl-5-oxo-2h-furan-2-yl]-7-oxo-6,13-dioxatetracyclo[7.5.0.0¹,⁵.0²,¹²]tetradecan-8-yl acetate)

INCHI for NP0314758 ((1s,2r,3s,5r,8r,9s,10r,11r,12r)-11,12-dihydroxy-3,10-dimethyl-3-[(2s)-3-methyl-5-oxo-2h-furan-2-yl]-7-oxo-6,13-dioxatetracyclo[7.5.0.0¹,⁵.0²,¹²]tetradecan-8-yl acetate)

Structure for NP0314758 ((1s,2r,3s,5r,8r,9s,10r,11r,12r)-11,12-dihydroxy-3,10-dimethyl-3-[(2s)-3-methyl-5-oxo-2h-furan-2-yl]-7-oxo-6,13-dioxatetracyclo[7.5.0.0¹,⁵.0²,¹²]tetradecan-8-yl acetate)

3D Structure for NP0314758 ((1s,2r,3s,5r,8r,9s,10r,11r,12r)-11,12-dihydroxy-3,10-dimethyl-3-[(2s)-3-methyl-5-oxo-2h-furan-2-yl]-7-oxo-6,13-dioxatetracyclo[7.5.0.0¹,⁵.0²,¹²]tetradecan-8-yl acetate)