NP-MRD: Showing NP-Card for 6-{[9a-formyl-3a,5a-dihydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthren-7-yl]oxy}-3-[(3,4-dihydroxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-2-methyloxan-4-yl acetate (NP0272953)

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Record Information

Version

2.0

Created at

2022-09-08 19:48:23 UTC

Updated at

2022-09-08 19:48:23 UTC

NP-MRD ID

NP0272953

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-{[9a-formyl-3a,5a-dihydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthren-7-yl]oxy}-3-[(3,4-dihydroxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-2-methyloxan-4-yl acetate

Description

3-[(3,4-Dihydroxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-6-{[2-formyl-7,11-dihydroxy-15-methyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-5-yl]oxy}-2-methyloxan-4-yl acetate belongs to the class of organic compounds known as cerveratrum-type alkaloids. These are steroidal alkaloids containing the cevane (23-methyl-4- azahexacyclo[12.11.0.0^{2,11}.0^{4,9}.0^{15,24}.0^{18,23}]Pentacosane) moiety, which is a six ring system. Cerveratrum alkaloids have 7-9 oxygen atoms and occur as free alkamines or esters of simple aliphatic or aromatic acids. 6-{[9a-formyl-3a,5a-dihydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthren-7-yl]oxy}-3-[(3,4-dihydroxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-2-methyloxan-4-yl acetate is found in Erysimum cheiranthoides. 3-[(3,4-Dihydroxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-6-{[2-formyl-7,11-dihydroxy-15-methyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-5-yl]oxy}-2-methyloxan-4-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161505462D          

 62 69  0  0  0  0            999 V2000
   -3.0946   -4.1952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2825   -4.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0022   -3.2741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1901   -3.1289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6582   -3.7596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9385   -4.5355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4067   -5.1662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4054   -5.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6857   -4.2451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9372   -5.6517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7507   -4.6807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0310   -5.4566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4991   -6.0873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6870   -5.9421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1552   -6.5728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6569   -6.4276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4355   -7.3487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0963   -7.9795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.5279   -8.2699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7794   -6.8633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.9098   -2.3529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1827   -1.4318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8069   -1.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2751   -0.5107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387   -1.7721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6190   -0.9961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311   -0.8509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629   -1.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3228   -0.7393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -1.5084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168   -2.3009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340   -2.7639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826   -2.2576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8705   -2.4028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5902   -3.1787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7781   -3.3239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463   -2.6932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9660   -3.4691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.2939   -0.8571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0646   -0.0646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7474    0.3984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7742    1.2229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3987   -0.1080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1184   -0.8839    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  6 11  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 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
 21 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 19 28  1  0  0  0  0
 28 29  1  0  0  0  0
 17 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
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 32 33  1  0  0  0  0
  4 34  1  0  0  0  0
 34 35  1  0  0  0  0
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 38 54  1  0  0  0  0
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 54 56  1  0  0  0  0
 35 56  1  0  0  0  0
 46 57  1  0  0  0  0
 57 58  2  0  0  0  0
 58 59  1  0  0  0  0
 59 60  2  0  0  0  0
 59 61  1  0  0  0  0
 61 62  1  0  0  0  0
 57 62  1  0  0  0  0
M  END

     RDKit          3D

126133  0  0  0  0  0  0  0  0999 V2000
    3.2226   -3.5468    2.9672 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5302   -2.3561    2.3866 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0524   -1.5238    3.2079 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3813   -2.1097    1.0534 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7486   -1.0146    0.4789 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5372   -1.3815   -0.3806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1543   -0.1047   -0.7502 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1374    0.2133    0.1782 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3704    0.5301   -0.3488 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8456    1.9061   -0.0488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3211    1.9469   -0.4278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0444    1.2498    0.7297 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8955    2.1916    1.9057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3042    1.8803    3.0106 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4791    1.1584    0.4418 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.3899    1.6572    1.5348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8018    1.7504    0.9359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2457    0.3661    0.6289 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.1499   -0.5442    1.8553 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5938    0.1347    0.0788 C   0  0  1  0  0  0  0  0  0  0  0  0
  -11.4496    1.2255   -0.3734 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3350    2.4911   -0.4715 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5762    3.1035   -1.0200 C   0  0  0  0  0  0  0  0  0  0  0  0
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  -10.4116   -0.8869   -1.0801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9748   -1.3648   -0.9208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3326   -0.1080   -0.4727 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -6.8794   -0.1282   -0.1877 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.3509   -1.3762    0.4148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2939   -1.1628    1.4551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3659   -0.0217    1.0945 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5638    0.2168    2.2015 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9733    0.5184   -1.4574 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8806   -0.2558   -2.7226 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7341   -0.2134   -0.3365 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7815   -0.9084   -0.8448 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.8354   -0.9314    0.2860 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8822   -0.0014    0.5112 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5926   -0.4200    1.7658 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8422   -0.0154   -0.6408 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.0921   -0.2899   -0.3111 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0716    0.5862   -0.7348 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.8000   -0.1234   -1.7102 O   0  0  0  0  0  0  0  0  0  0  0  0
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   11.2166   -1.9004   -0.1033 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.8468   -0.0726   -0.6219 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.3551    0.6370   -1.7121 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2967    0.8001    0.4538 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.4407    0.1317    1.6727 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8926    1.2836    0.2513 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.3206    1.4098    1.5159 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1669   -0.8639   -1.7149 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8948   -0.6809   -2.8731 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7769   -0.2800   -1.9738 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9753    1.0412   -2.4040 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6459   -4.4745    2.7633 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4034   -3.4036    4.0361 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2216   -3.6654    2.4606 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3725   -0.3576    1.2831 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7530   -1.9998   -1.2329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1700   -1.9977    0.2599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6998   -0.2199   -1.7109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2290    0.4600   -1.4726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3554    2.6679   -0.6951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8210    2.1605    1.0368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3965    1.3770   -1.3771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7290    2.9594   -0.4901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4336    3.1337    1.7799 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.4364    1.1369    2.4498 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.5989    2.2452   -0.0485 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


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M  END
> <DATABASE_ID>
NP0272953

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC(CC(OC(C)=O)C1OC1OC(C)C(OC2OC(CO)C(O)C(O)C2O)C(O)C1O)OC1CCC2(C=O)C3CCC4(C)C(CCC4(O)C3CCC2(O)C1)C1=CC(=O)OC1

> <INCHI_IDENTIFIER>
InChI=1S/C43H64O19/c1-19-36(61-38-35(52)33(50)37(20(2)57-38)62-39-34(51)32(49)31(48)28(16-44)60-39)27(58-21(3)46)14-30(56-19)59-23-5-10-41(18-45)25-6-9-40(4)24(22-13-29(47)55-17-22)8-12-43(40,54)26(25)7-11-42(41,53)15-23/h13,18-20,23-28,30-39,44,48-54H,5-12,14-17H2,1-4H3

> <INCHI_KEY>
BXXHNQDTEFIKSJ-UHFFFAOYSA-N

> <FORMULA>
C43H64O19

> <MOLECULAR_WEIGHT>
884.966

> <EXACT_MASS>
884.404179841

> <JCHEM_ACCEPTOR_COUNT>
17

> <JCHEM_ATOM_COUNT>
126

> <JCHEM_AVERAGE_POLARIZABILITY>
92.08458856836589

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(3,4-dihydroxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-6-{[2-formyl-7,11-dihydroxy-15-methyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxy}-2-methyloxan-4-yl acetate

> <ALOGPS_LOGP>
-1.05

> <JCHEM_LOGP>
-1.0085863676666673

> <ALOGPS_LOGS>
-3.02

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.939165267003785

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.1826285803834065

> <JCHEM_PKA_STRONGEST_BASIC>
0.26896009723720404

> <JCHEM_POLAR_SURFACE_AREA>
286.89

> <JCHEM_REFRACTIVITY>
207.71020000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.50e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[(3,4-dihydroxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-6-{[2-formyl-7,11-dihydroxy-15-methyl-14-(5-oxo-2H-furan-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxy}-2-methyloxan-4-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      -5.777  -7.831   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.261  -7.560   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -3.737  -6.112   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -2.221  -5.841   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.229  -7.018   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.752  -8.466   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.759  -9.644   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.757  -9.372   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.280  -7.924   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.749 -10.550   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.268  -8.737   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -3.791 -10.186   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.798 -11.363   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.282 -11.092   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.290 -12.269   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.226 -11.998   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.813 -13.718   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.180 -14.895   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.343 -16.343   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.859 -16.614   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.383 -18.063   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.899 -18.334   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -4.422 -19.782   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -1.390 -19.240   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -1.913 -20.689   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.126 -18.969   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.119 -20.146   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.649 -17.521   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.165 -17.250   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -2.329 -13.989   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -2.852 -15.437   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -3.322 -12.811   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -4.838 -13.082   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -1.698  -4.392   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -0.182  -4.121   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       0.341  -2.673   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       1.857  -2.402   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       2.850  -3.579   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       3.373  -2.131   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       2.380  -0.953   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       4.366  -3.308   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       4.889  -1.859   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       6.405  -1.588   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       7.398  -2.766   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       8.069  -1.380   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       8.937  -2.816   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       9.365  -4.295   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       8.090  -5.159   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       6.874  -4.214   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0       6.505  -5.709   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0       5.358  -4.485   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       4.835  -5.934   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       3.319  -6.205   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       2.326  -5.027   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0       1.803  -6.476   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0       0.810  -5.298   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       9.882  -1.600   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0       9.454  -0.121   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      10.728   0.744   0.000  0.00  0.00           C+0
HETATM   60  O   UNK     0      10.779   2.283   0.000  0.00  0.00           O+0
HETATM   61  O   UNK     0      11.944  -0.202   0.000  0.00  0.00           O+0
HETATM   62  C   UNK     0      11.421  -1.650   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   34                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    6    2   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   32                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   30                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   28                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   19   29                                                  
CONECT   29   28                                                            
CONECT   30   17   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   13   33                                                  
CONECT   33   32                                                            
CONECT   34    4   35                                                       
CONECT   35   34   36   56                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39   41   54                                             
CONECT   39   38   40                                                       
CONECT   40   39                                                            
CONECT   41   38   42   51                                                  
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45   46   49                                             
CONECT   45   44                                                            
CONECT   46   44   47   57                                                  
CONECT   47   46   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   44   50   51                                             
CONECT   50   49                                                            
CONECT   51   49   41   52                                                  
CONECT   52   51   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   38   55   56                                             
CONECT   55   54                                                            
CONECT   56   54   35                                                       
CONECT   57   46   58   62                                                  
CONECT   58   57   59                                                       
CONECT   59   58   60   61                                                  
CONECT   60   59                                                            
CONECT   61   59   62                                                       
CONECT   62   61   57                                                       
MASTER        0    0    0    0    0    0    0    0   62    0  138    0
END

View in JSmol

Synonyms

Value	Source
3-[(3,4-Dihydroxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-6-{[2-formyl-7,11-dihydroxy-15-methyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0,.0,]heptadecan-5-yl]oxy}-2-methyloxan-4-yl acetic acid	Generator
3-[(3,4-Dihydroxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-6-{[2-formyl-7,11-dihydroxy-15-methyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxy}-2-methyloxan-4-yl acetic acid	Generator

Chemical Formula

C₄₃H₆₄O₁₉

Average Mass

884.9660 Da

Monoisotopic Mass

884.40418 Da

IUPAC Name

3-[(3,4-dihydroxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-6-{[2-formyl-7,11-dihydroxy-15-methyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxy}-2-methyloxan-4-yl acetate

Traditional Name

3-[(3,4-dihydroxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-6-{[2-formyl-7,11-dihydroxy-15-methyl-14-(5-oxo-2H-furan-3-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxy}-2-methyloxan-4-yl acetate

CAS Registry Number

Not Available

SMILES

CC1OC(CC(OC(C)=O)C1OC1OC(C)C(OC2OC(CO)C(O)C(O)C2O)C(O)C1O)OC1CCC2(C=O)C3CCC4(C)C(CCC4(O)C3CCC2(O)C1)C1=CC(=O)OC1

InChI Identifier

InChI=1S/C43H64O19/c1-19-36(61-38-35(52)33(50)37(20(2)57-38)62-39-34(51)32(49)31(48)28(16-44)60-39)27(58-21(3)46)14-30(56-19)59-23-5-10-41(18-45)25-6-9-40(4)24(22-13-29(47)55-17-22)8-12-43(40,54)26(25)7-11-42(41,53)15-23/h13,18-20,23-28,30-39,44,48-54H,5-12,14-17H2,1-4H3

InChI Key

BXXHNQDTEFIKSJ-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
Erysimum cheiranthoides	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cerveratrum-type alkaloids. These are steroidal alkaloids containing the cevane (23-methyl-4- azahexacyclo[12.11.0.0^{2,11}.0^{4,9}.0^{15,24}.0^{18,23}]Pentacosane) moiety, which is a six ring system. Cerveratrum alkaloids have 7-9 oxygen atoms and occur as free alkamines or esters of simple aliphatic or aromatic acids.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal alkaloids

Direct Parent

Cerveratrum-type alkaloids

Alternative Parents

Substituents

Cerveratrum-type alkaloid
Azasteroid
Quinolizidine
Alkaloid or derivatives
Piperidine
Cyclic alcohol
Tertiary alcohol
1,2-aminoalcohol
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Azacycle
Polyol
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Amine
Organopnictogen compound
Alcohol
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	-1	ALOGPS
logP	-1	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	7.18	ChemAxon
pKa (Strongest Basic)	0.27	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	286.89 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	207.71 m³·mol⁻¹	ChemAxon
Polarizability	92.08 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

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 6-{[9a-formyl-3a,5a-dihydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthren-7-yl]oxy}-3-[(3,4-dihydroxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-2-methyloxan-4-yl acetate (NP0272953)

MOL for NP0272953 (6-{[9a-formyl-3a,5a-dihydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthren-7-yl]oxy}-3-[(3,4-dihydroxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-2-methyloxan-4-yl acetate)

3D MOL for NP0272953 (6-{[9a-formyl-3a,5a-dihydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthren-7-yl]oxy}-3-[(3,4-dihydroxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-2-methyloxan-4-yl acetate)

3D SDF for NP0272953 (6-{[9a-formyl-3a,5a-dihydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthren-7-yl]oxy}-3-[(3,4-dihydroxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-2-methyloxan-4-yl acetate)

3D-SDF for NP0272953 (6-{[9a-formyl-3a,5a-dihydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthren-7-yl]oxy}-3-[(3,4-dihydroxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-2-methyloxan-4-yl acetate)

PDB for NP0272953 (6-{[9a-formyl-3a,5a-dihydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthren-7-yl]oxy}-3-[(3,4-dihydroxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-2-methyloxan-4-yl acetate)

3D PDB for NP0272953 (6-{[9a-formyl-3a,5a-dihydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthren-7-yl]oxy}-3-[(3,4-dihydroxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-2-methyloxan-4-yl acetate)

SMILES for NP0272953 (6-{[9a-formyl-3a,5a-dihydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthren-7-yl]oxy}-3-[(3,4-dihydroxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-2-methyloxan-4-yl acetate)

INCHI for NP0272953 (6-{[9a-formyl-3a,5a-dihydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthren-7-yl]oxy}-3-[(3,4-dihydroxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-2-methyloxan-4-yl acetate)

Structure for NP0272953 (6-{[9a-formyl-3a,5a-dihydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthren-7-yl]oxy}-3-[(3,4-dihydroxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-2-methyloxan-4-yl acetate)

3D Structure for NP0272953 (6-{[9a-formyl-3a,5a-dihydroxy-11a-methyl-1-(5-oxo-2h-furan-3-yl)-dodecahydro-1h-cyclopenta[a]phenanthren-7-yl]oxy}-3-[(3,4-dihydroxy-6-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl)oxy]-2-methyloxan-4-yl acetate)