NP-MRD: Showing NP-Card for 4-epi-aubergenone-11-O-2',4'-di-O-acetyl-alpha-L-rhamnopyranoside (NP0042482)

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Record Information

Version

2.0

Created at

2021-06-21 00:08:03 UTC

Updated at

2021-06-30 00:17:35 UTC

NP-MRD ID

NP0042482

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-epi-aubergenone-11-O-2',4'-di-O-acetyl-alpha-L-rhamnopyranoside

Provided By

JEOL Database JEOL Logo

Description

4-epi-aubergenone-11-O-2',4'-di-O-acetyl-alpha-L-rhamnopyranoside is found in Cananga latifolia. 4-epi-aubergenone-11-O-2',4'-di-O-acetyl-alpha-L-rhamnopyranoside was first documented in 2013 (Yang, H., et al.).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102083D          

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M  END

     RDKit          3D

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 17 49  1  0
 17 50  1  0
 11 41  1  0
 11 42  1  0
 11 43  1  0
M  END


  Mrv1652306212102083D          

 71 73  0  0  0  0            999 V2000
    4.6904   -2.1779   -1.5898 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4586   -0.7258   -1.3094 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0486    0.1940   -1.8608 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4974   -0.5774   -0.3567 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1726    0.7867   -0.0107 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1244    1.3490   -0.9894 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6115    1.4104   -2.3398 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6664    2.7428   -0.5406 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8004    3.6403   -0.6510 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4969    4.9650   -0.6353 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7416    5.7811   -0.7982 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3747    5.4292   -0.4958 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1543    2.6696    0.9148 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0264    1.8704    0.9498 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0027    2.1554    1.9661 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3873    2.1388    3.3774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6385    3.5377    1.7159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0982    1.0298    1.8366 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5295   -0.3736    2.1417 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5446   -1.4960    1.9203 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1500   -1.4834    0.5015 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0572   -1.8180   -0.5387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2076   -2.5642    0.3873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3419   -2.4269   -0.3120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6342   -1.1829   -1.0692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6753   -1.1335   -1.7219 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6015   -0.0518   -1.0513 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3090    1.2856   -1.2862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8156   -0.0927    0.2828 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7990    1.0516    0.4524 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1676    2.1345    1.7782 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5955    0.8184    1.4141 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6335    0.3818    2.4444 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4704   -2.2801   -2.3497 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7720   -2.6328   -1.9691 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0230   -2.6826   -0.6794 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0807    1.4044   -0.0394 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2653    0.6679   -1.0237 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5860    1.5064   -2.3116 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8753    3.0788   -1.2238 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2300    5.5280   -1.7427 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4791    6.8427   -0.8170 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4147    5.6014    0.0437 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9539    3.6803    1.2751 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2681    3.0020    3.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1636    2.1702    4.1492 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2345    1.2526    3.5386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9655    4.3523    2.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8586    3.6918    0.6543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5597    3.6633    2.2950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8734    1.2308    2.5906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6373   -0.5641    1.5356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2066   -0.4253    3.1876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3432   -1.3997    2.6690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0555   -2.4585    2.1207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4690   -1.9249   -1.5484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2744   -1.0562   -0.5899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5654   -2.7682   -0.2955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0171   -3.5135    0.8849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0792   -3.2179   -0.3850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9251   -0.2227   -1.8971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9334    1.2515   -2.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9597    1.5427   -0.4434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5911    2.0980   -1.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5603    0.0447    1.0848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3289    2.0044    0.3595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0628    1.0251   -0.3584 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7493    0.1248    1.4950 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5005    1.0515    2.4335 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2107    0.4325    3.4539 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9774   -0.6411    2.2648 H   0  0  0  0  0  0  0  0  0  0  0  0
 25 27  1  0  0  0  0
 27 29  1  0  0  0  0
 21 23  1  0  0  0  0
 21 29  1  0  0  0  0
  6  8  1  0  0  0  0
  8 13  1  0  0  0  0
 13 31  1  0  0  0  0
 21 20  1  0  0  0  0
 29 30  1  0  0  0  0
 30 18  1  0  0  0  0
 31 32  1  0  0  0  0
 20 19  1  0  0  0  0
 32  5  1  0  0  0  0
 21 22  1  6  0  0  0
 19 18  1  0  0  0  0
 13 14  1  0  0  0  0
 27 28  1  0  0  0  0
 25 26  2  0  0  0  0
  6  7  1  0  0  0  0
 18 15  1  0  0  0  0
 24 25  1  0  0  0  0
 29 65  1  1  0  0  0
  2  3  2  0  0  0  0
 15 16  1  0  0  0  0
  2  1  1  0  0  0  0
 15 17  1  0  0  0  0
 15 14  1  6  0  0  0
  9 10  1  0  0  0  0
  5  6  1  0  0  0  0
 10 12  2  0  0  0  0
 24 23  2  0  0  0  0
 10 11  1  0  0  0  0
  4  2  1  0  0  0  0
  5  4  1  0  0  0  0
  8  9  1  0  0  0  0
 32 33  1  0  0  0  0
  1 34  1  0  0  0  0
  1 35  1  0  0  0  0
  1 36  1  0  0  0  0
  5 37  1  1  0  0  0
 13 44  1  1  0  0  0
 33 69  1  0  0  0  0
 33 70  1  0  0  0  0
 33 71  1  0  0  0  0
 32 68  1  6  0  0  0
  8 40  1  6  0  0  0
  6 38  1  6  0  0  0
  7 39  1  0  0  0  0
 24 60  1  0  0  0  0
 27 61  1  6  0  0  0
 23 59  1  0  0  0  0
 30 66  1  0  0  0  0
 30 67  1  0  0  0  0
 20 54  1  0  0  0  0
 20 55  1  0  0  0  0
 22 56  1  0  0  0  0
 22 57  1  0  0  0  0
 22 58  1  0  0  0  0
 19 52  1  0  0  0  0
 19 53  1  0  0  0  0
 18 51  1  1  0  0  0
 28 62  1  0  0  0  0
 28 63  1  0  0  0  0
 28 64  1  0  0  0  0
 16 45  1  0  0  0  0
 16 46  1  0  0  0  0
 16 47  1  0  0  0  0
 17 48  1  0  0  0  0
 17 49  1  0  0  0  0
 17 50  1  0  0  0  0
 11 41  1  0  0  0  0
 11 42  1  0  0  0  0
 11 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0042482

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])[C@]([H])(OC(=O)C([H])([H])[H])[C@@]([H])(OC(C([H])([H])[H])(C([H])([H])[H])[C@]2([H])C([H])([H])C([H])([H])[C@]3(C([H])=C([H])C(=O)[C@@]([H])(C([H])([H])[H])[C@]3([H])C2([H])[H])C([H])([H])[H])O[C@]([H])(C([H])([H])[H])[C@@]1([H])OC(=O)C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C25H38O8/c1-13-18-12-17(8-10-25(18,7)11-9-19(13)28)24(5,6)33-23-22(32-16(4)27)20(29)21(14(2)30-23)31-15(3)26/h9,11,13-14,17-18,20-23,29H,8,10,12H2,1-7H3/t13-,14+,17+,18-,20-,21+,22-,23+,25-/m0/s1

> <INCHI_KEY>
MFXOXMMWHYLYQN-NXZQXLHISA-N

> <FORMULA>
C25H38O8

> <MOLECULAR_WEIGHT>
466.571

> <EXACT_MASS>
466.256668184

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
50.141409153953006

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S,4S,5S,6R)-2-({2-[(2R,4aS,8S,8aS)-4a,8-dimethyl-7-oxo-1,2,3,4,4a,7,8,8a-octahydronaphthalen-2-yl]propan-2-yl}oxy)-5-(acetyloxy)-4-hydroxy-6-methyloxan-3-yl acetate

> <ALOGPS_LOGP>
3.05

> <JCHEM_LOGP>
3.112271816999998

> <ALOGPS_LOGS>
-4.34

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.925642118926607

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7061241371815017

> <JCHEM_POLAR_SURFACE_AREA>
108.36000000000003

> <JCHEM_REFRACTIVITY>
119.5172

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.12e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,4S,5S,6R)-2-({2-[(2R,4aS,8S,8aS)-4a,8-dimethyl-7-oxo-1,2,3,4,8,8a-hexahydronaphthalen-2-yl]propan-2-yl}oxy)-5-(acetyloxy)-4-hydroxy-6-methyloxan-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 71 73  0  0  0  0  0  0  0  0999 V2000
    4.6904   -2.1779   -1.5898 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4586   -0.7258   -1.3094 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0486    0.1940   -1.8608 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4974   -0.5774   -0.3567 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1726    0.7867   -0.0107 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1244    1.3490   -0.9894 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6115    1.4104   -2.3398 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6664    2.7428   -0.5406 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8004    3.6403   -0.6510 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4969    4.9650   -0.6353 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7416    5.7811   -0.7982 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3747    5.4292   -0.4958 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1543    2.6696    0.9148 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0264    1.8704    0.9498 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0027    2.1554    1.9661 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3873    2.1388    3.3774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6385    3.5377    1.7159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0982    1.0298    1.8366 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5295   -0.3736    2.1417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5446   -1.4960    1.9203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1500   -1.4834    0.5015 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0572   -1.8180   -0.5387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2076   -2.5642    0.3873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3419   -2.4269   -0.3120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6342   -1.1829   -1.0692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6753   -1.1335   -1.7219 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6015   -0.0518   -1.0513 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3090    1.2856   -1.2862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8156   -0.0927    0.2828 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7990    1.0516    0.4524 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1676    2.1345    1.7782 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5955    0.8184    1.4141 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6335    0.3818    2.4444 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4704   -2.2801   -2.3497 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7720   -2.6328   -1.9691 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0230   -2.6826   -0.6794 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0807    1.4044   -0.0394 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2653    0.6679   -1.0237 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5860    1.5064   -2.3116 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8753    3.0788   -1.2238 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2300    5.5280   -1.7427 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4791    6.8427   -0.8170 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4147    5.6014    0.0437 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9539    3.6803    1.2751 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2681    3.0020    3.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1636    2.1702    4.1492 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2345    1.2526    3.5386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9655    4.3523    2.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8586    3.6918    0.6543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5597    3.6633    2.2950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8734    1.2308    2.5906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6373   -0.5641    1.5356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2066   -0.4253    3.1876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3432   -1.3997    2.6690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0555   -2.4585    2.1207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4690   -1.9249   -1.5484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2744   -1.0562   -0.5899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5654   -2.7682   -0.2955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0171   -3.5135    0.8849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0792   -3.2179   -0.3850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9251   -0.2227   -1.8971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9334    1.2515   -2.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9597    1.5427   -0.4434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5911    2.0980   -1.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5603    0.0447    1.0848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3289    2.0044    0.3595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0628    1.0251   -0.3584 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7493    0.1248    1.4950 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5005    1.0515    2.4335 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2107    0.4325    3.4539 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9774   -0.6411    2.2648 H   0  0  0  0  0  0  0  0  0  0  0  0
 25 27  1  0
 27 29  1  0
 21 23  1  0
 21 29  1  0
  6  8  1  0
  8 13  1  0
 13 31  1  0
 21 20  1  0
 29 30  1  0
 30 18  1  0
 31 32  1  0
 20 19  1  0
 32  5  1  0
 21 22  1  6
 19 18  1  0
 13 14  1  0
 27 28  1  0
 25 26  2  0
  6  7  1  0
 18 15  1  0
 24 25  1  0
 29 65  1  1
  2  3  2  0
 15 16  1  0
  2  1  1  0
 15 17  1  0
 15 14  1  6
  9 10  1  0
  5  6  1  0
 10 12  2  0
 24 23  2  0
 10 11  1  0
  4  2  1  0
  5  4  1  0
  8  9  1  0
 32 33  1  0
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 11 41  1  0
 11 42  1  0
 11 43  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0       4.690  -2.178  -1.590  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.459  -0.726  -1.309  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.049   0.194  -1.861  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.497  -0.577  -0.357  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.173   0.787  -0.011  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.124   1.349  -0.989  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.611   1.410  -2.340  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.666   2.743  -0.541  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.800   3.640  -0.651  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.497   4.965  -0.635  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.742   5.781  -0.798  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.375   5.429  -0.496  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.154   2.670   0.915  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.026   1.870   0.950  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.003   2.155   1.966  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.387   2.139   3.377  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.639   3.538   1.716  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.098   1.030   1.837  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.530  -0.374   2.142  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.545  -1.496   1.920  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.150  -1.483   0.501  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.057  -1.818  -0.539  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.208  -2.564   0.387  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.342  -2.427  -0.312  0.00  0.00           C+0
HETATM   25  C   UNK     0      -5.634  -1.183  -1.069  0.00  0.00           C+0
HETATM   26  O   UNK     0      -6.675  -1.133  -1.722  0.00  0.00           O+0
HETATM   27  C   UNK     0      -4.601  -0.052  -1.051  0.00  0.00           C+0
HETATM   28  C   UNK     0      -5.309   1.286  -1.286  0.00  0.00           C+0
HETATM   29  C   UNK     0      -3.816  -0.093   0.283  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.799   1.052   0.452  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.168   2.135   1.778  0.00  0.00           O+0
HETATM   32  C   UNK     0       2.595   0.818   1.414  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.634   0.382   2.444  0.00  0.00           C+0
HETATM   34  H   UNK     0       5.470  -2.280  -2.350  0.00  0.00           H+0
HETATM   35  H   UNK     0       3.772  -2.633  -1.969  0.00  0.00           H+0
HETATM   36  H   UNK     0       5.023  -2.683  -0.679  0.00  0.00           H+0
HETATM   37  H   UNK     0       4.081   1.404  -0.039  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.265   0.668  -1.024  0.00  0.00           H+0
HETATM   39  H   UNK     0       3.586   1.506  -2.312  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.875   3.079  -1.224  0.00  0.00           H+0
HETATM   41  H   UNK     0       4.230   5.528  -1.743  0.00  0.00           H+0
HETATM   42  H   UNK     0       3.479   6.843  -0.817  0.00  0.00           H+0
HETATM   43  H   UNK     0       4.415   5.601   0.044  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.954   3.680   1.275  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.268   3.002   3.538  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.164   2.170   4.149  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.235   1.253   3.539  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.966   4.352   2.005  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.859   3.692   0.654  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.560   3.663   2.295  0.00  0.00           H+0
HETATM   51  H   UNK     0      -2.873   1.231   2.591  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.637  -0.564   1.536  0.00  0.00           H+0
HETATM   53  H   UNK     0      -1.207  -0.425   3.188  0.00  0.00           H+0
HETATM   54  H   UNK     0      -3.343  -1.400   2.669  0.00  0.00           H+0
HETATM   55  H   UNK     0      -2.055  -2.458   2.121  0.00  0.00           H+0
HETATM   56  H   UNK     0      -2.469  -1.925  -1.548  0.00  0.00           H+0
HETATM   57  H   UNK     0      -1.274  -1.056  -0.590  0.00  0.00           H+0
HETATM   58  H   UNK     0      -1.565  -2.768  -0.296  0.00  0.00           H+0
HETATM   59  H   UNK     0      -4.017  -3.514   0.885  0.00  0.00           H+0
HETATM   60  H   UNK     0      -6.079  -3.218  -0.385  0.00  0.00           H+0
HETATM   61  H   UNK     0      -3.925  -0.223  -1.897  0.00  0.00           H+0
HETATM   62  H   UNK     0      -5.933   1.252  -2.186  0.00  0.00           H+0
HETATM   63  H   UNK     0      -5.960   1.543  -0.443  0.00  0.00           H+0
HETATM   64  H   UNK     0      -4.591   2.098  -1.433  0.00  0.00           H+0
HETATM   65  H   UNK     0      -4.560   0.045   1.085  0.00  0.00           H+0
HETATM   66  H   UNK     0      -3.329   2.004   0.360  0.00  0.00           H+0
HETATM   67  H   UNK     0      -2.063   1.025  -0.358  0.00  0.00           H+0
HETATM   68  H   UNK     0       1.749   0.125   1.495  0.00  0.00           H+0
HETATM   69  H   UNK     0       4.500   1.052   2.434  0.00  0.00           H+0
HETATM   70  H   UNK     0       3.211   0.433   3.454  0.00  0.00           H+0
HETATM   71  H   UNK     0       3.977  -0.641   2.265  0.00  0.00           H+0
CONECT    1    2   34   35   36                                             
CONECT    2    3    1    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5   32    6    4   37                                             
CONECT    6    8    7    5   38                                             
CONECT    7    6   39                                                       
CONECT    8    6   13    9   40                                             
CONECT    9   10    8                                                       
CONECT   10    9   12   11                                                  
CONECT   11   10   41   42   43                                             
CONECT   12   10                                                            
CONECT   13    8   31   14   44                                             
CONECT   14   13   15                                                       
CONECT   15   18   16   17   14                                             
CONECT   16   15   45   46   47                                             
CONECT   17   15   48   49   50                                             
CONECT   18   30   19   15   51                                             
CONECT   19   20   18   52   53                                             
CONECT   20   21   19   54   55                                             
CONECT   21   23   29   20   22                                             
CONECT   22   21   56   57   58                                             
CONECT   23   21   24   59                                                  
CONECT   24   25   23   60                                                  
CONECT   25   27   26   24                                                  
CONECT   26   25                                                            
CONECT   27   25   29   28   61                                             
CONECT   28   27   62   63   64                                             
CONECT   29   27   21   30   65                                             
CONECT   30   29   18   66   67                                             
CONECT   31   13   32                                                       
CONECT   32   31    5   33   68                                             
CONECT   33   32   69   70   71                                             
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    5                                                            
CONECT   38    6                                                            
CONECT   39    7                                                            
CONECT   40    8                                                            
CONECT   41   11                                                            
CONECT   42   11                                                            
CONECT   43   11                                                            
CONECT   44   13                                                            
CONECT   45   16                                                            
CONECT   46   16                                                            
CONECT   47   16                                                            
CONECT   48   17                                                            
CONECT   49   17                                                            
CONECT   50   17                                                            
CONECT   51   18                                                            
CONECT   52   19                                                            
CONECT   53   19                                                            
CONECT   54   20                                                            
CONECT   55   20                                                            
CONECT   56   22                                                            
CONECT   57   22                                                            
CONECT   58   22                                                            
CONECT   59   23                                                            
CONECT   60   24                                                            
CONECT   61   27                                                            
CONECT   62   28                                                            
CONECT   63   28                                                            
CONECT   64   28                                                            
CONECT   65   29                                                            
CONECT   66   30                                                            
CONECT   67   30                                                            
CONECT   68   32                                                            
CONECT   69   33                                                            
CONECT   70   33                                                            
CONECT   71   33                                                            
MASTER        0    0    0    0    0    0    0    0   71    0  146    0
END

RDKit          3D

71 73  0  0  0  0  0  0  0  0999 V2000
    4.6904   -2.1779   -1.5898 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4586   -0.7258   -1.3094 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0486    0.1940   -1.8608 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4974   -0.5774   -0.3567 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1726    0.7867   -0.0107 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1244    1.3490   -0.9894 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6115    1.4104   -2.3398 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6664    2.7428   -0.5406 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8004    3.6403   -0.6510 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4969    4.9650   -0.6353 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7416    5.7811   -0.7982 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3747    5.4292   -0.4958 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1543    2.6696    0.9148 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0264    1.8704    0.9498 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0027    2.1554    1.9661 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3873    2.1388    3.3774 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.1500   -1.4834    0.5015 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0572   -1.8180   -0.5387 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.3419   -2.4269   -0.3120 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.8156   -0.0927    0.2828 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7990    1.0516    0.4524 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1676    2.1345    1.7782 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5955    0.8184    1.4141 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6335    0.3818    2.4444 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4704   -2.2801   -2.3497 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7720   -2.6328   -1.9691 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0230   -2.6826   -0.6794 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0807    1.4044   -0.0394 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2653    0.6679   -1.0237 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5860    1.5064   -2.3116 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8753    3.0788   -1.2238 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2300    5.5280   -1.7427 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4791    6.8427   -0.8170 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4147    5.6014    0.0437 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9539    3.6803    1.2751 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2681    3.0020    3.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1636    2.1702    4.1492 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2345    1.2526    3.5386 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.0792   -3.2179   -0.3850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9251   -0.2227   -1.8971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9334    1.2515   -2.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.5603    0.0447    1.0848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3289    2.0044    0.3595 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7493    0.1248    1.4950 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5005    1.0515    2.4335 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2107    0.4325    3.4539 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9774   -0.6411    2.2648 H   0  0  0  0  0  0  0  0  0  0  0  0
 25 27  1  0
 27 29  1  0
 21 23  1  0
 21 29  1  0
  6  8  1  0
  8 13  1  0
 13 31  1  0
 21 20  1  0
 29 30  1  0
 30 18  1  0
 31 32  1  0
 20 19  1  0
 32  5  1  0
 21 22  1  6
 19 18  1  0
 13 14  1  0
 27 28  1  0
 25 26  2  0
  6  7  1  0
 18 15  1  0
 24 25  1  0
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  2  3  2  0
 15 16  1  0
  2  1  1  0
 15 17  1  0
 15 14  1  6
  9 10  1  0
  5  6  1  0
 10 12  2  0
 24 23  2  0
 10 11  1  0
  4  2  1  0
  5  4  1  0
  8  9  1  0
 32 33  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  5 37  1  1
 13 44  1  1
 33 69  1  0
 33 70  1  0
 33 71  1  0
 32 68  1  6
  8 40  1  6
  6 38  1  6
  7 39  1  0
 24 60  1  0
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 17 49  1  0
 17 50  1  0
 11 41  1  0
 11 42  1  0
 11 43  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₈O₈

Average Mass

466.5710 Da

Monoisotopic Mass

466.25667 Da

IUPAC Name

(2R,3S,4S,5S,6R)-2-({2-[(2R,4aS,8S,8aS)-4a,8-dimethyl-7-oxo-1,2,3,4,4a,7,8,8a-octahydronaphthalen-2-yl]propan-2-yl}oxy)-5-(acetyloxy)-4-hydroxy-6-methyloxan-3-yl acetate

Traditional Name

(2R,3S,4S,5S,6R)-2-({2-[(2R,4aS,8S,8aS)-4a,8-dimethyl-7-oxo-1,2,3,4,8,8a-hexahydronaphthalen-2-yl]propan-2-yl}oxy)-5-(acetyloxy)-4-hydroxy-6-methyloxan-3-yl acetate

CAS Registry Number

Not Available

SMILES

[H]O[C@]1([H])[C@]([H])(OC(=O)C([H])([H])[H])[C@@]([H])(OC(C([H])([H])[H])(C([H])([H])[H])[C@]2([H])C([H])([H])C([H])([H])[C@]3(C([H])=C([H])C(=O)[C@@]([H])(C([H])([H])[H])[C@]3([H])C2([H])[H])C([H])([H])[H])O[C@]([H])(C([H])([H])[H])[C@@]1([H])OC(=O)C([H])([H])[H]

InChI Identifier

InChI=1S/C25H38O8/c1-13-18-12-17(8-10-25(18,7)11-9-19(13)28)24(5,6)33-23-22(32-16(4)27)20(29)21(14(2)30-23)31-15(3)26/h9,11,13-14,17-18,20-23,29H,8,10,12H2,1-7H3/t13-,14+,17+,18-,20-,21+,22-,23+,25-/m0/s1

InChI Key

MFXOXMMWHYLYQN-NXZQXLHISA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cananga latifolia	JEOL database	Yang, H., et al, Phytochem. 94, 277 (2013)

Chemical Taxonomy

Classification

Not classified

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	3.05	ALOGPS
logP	3.11	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	12.93	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	108.36 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	119.52 m³·mol⁻¹	ChemAxon
Polarizability	50.14 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

Not Available

References

General References

Yang, H., et al. (2013). Yang, H., et al, Phytochem. 94, 277 (2013). Phytochem..

Showing NP-Card for 4-epi-aubergenone-11-O-2',4'-di-O-acetyl-alpha-L-rhamnopyranoside (NP0042482)

MOL for NP0042482 (4-epi-aubergenone-11-O-2',4'-di-O-acetyl-alpha-L-rhamnopyranoside)

3D MOL for NP0042482 (4-epi-aubergenone-11-O-2',4'-di-O-acetyl-alpha-L-rhamnopyranoside)

3D SDF for NP0042482 (4-epi-aubergenone-11-O-2',4'-di-O-acetyl-alpha-L-rhamnopyranoside)

3D-SDF for NP0042482 (4-epi-aubergenone-11-O-2',4'-di-O-acetyl-alpha-L-rhamnopyranoside)

PDB for NP0042482 (4-epi-aubergenone-11-O-2',4'-di-O-acetyl-alpha-L-rhamnopyranoside)

3D PDB for NP0042482 (4-epi-aubergenone-11-O-2',4'-di-O-acetyl-alpha-L-rhamnopyranoside)

SMILES for NP0042482 (4-epi-aubergenone-11-O-2',4'-di-O-acetyl-alpha-L-rhamnopyranoside)

INCHI for NP0042482 (4-epi-aubergenone-11-O-2',4'-di-O-acetyl-alpha-L-rhamnopyranoside)

Structure for NP0042482 (4-epi-aubergenone-11-O-2',4'-di-O-acetyl-alpha-L-rhamnopyranoside)

3D Structure for NP0042482 (4-epi-aubergenone-11-O-2',4'-di-O-acetyl-alpha-L-rhamnopyranoside)