NP-MRD: Showing NP-Card for macarangioside A (NP0030033)

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Record Information

Version

2.0

Created at

2021-06-19 21:30:08 UTC

Updated at

2021-06-29 23:57:46 UTC

NP-MRD ID

NP0030033

Secondary Accession Numbers

None

Natural Product Identification

Common Name

macarangioside A

Provided By

JEOL Database JEOL Logo

Description

macarangioside A is found in Macaranga tanarius (L.) MULL.-ARG. macarangioside A was first documented in 2006 (Matsunami, K., et al.).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192123303D          

 74 76  0  0  0  0            999 V2000
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M  END

     RDKit          3D

 74 76  0  0  0  0  0  0  0  0999 V2000
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  6 43  1  0
  6 44  1  0
  3 42  1  0
  8 45  1  0
  8 46  1  0
  8 47  1  0
  9 48  1  0
  9 49  1  0
  9 50  1  0
 12 52  1  0
 12 53  1  0
 13 54  1  0
 13 55  1  0
 14 56  1  6
 15 57  1  0
 15 58  1  0
 15 59  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
 11 51  1  0
 34 70  1  0
 33 69  1  1
 17 60  1  6
 20 62  1  0
 20 63  1  0
 19 61  1  6
 37 73  1  1
 38 74  1  0
 35 71  1  6
 36 72  1  0
 32 68  1  0
 25 64  1  0
 27 65  1  0
 29 66  1  0
 31 67  1  0
M  END


  Mrv1652306192123303D          

 74 76  0  0  0  0            999 V2000
   -1.0595    1.1788   -1.6644 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1478    1.9145   -1.1446 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2635    3.2332   -1.3884 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4641    4.0041   -0.9876 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4502    5.2283   -1.0950 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6639    3.2677   -0.4326 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6532    1.7546   -0.7482 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7952    1.0824    0.0501 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0153    1.5491   -2.2473 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2329    1.1427   -0.3943 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2175   -0.2203   -0.8096 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9628    1.1659    1.1432 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3437    0.5524    1.6746 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5171   -0.9677    1.5221 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5976   -1.7599    2.1976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7392   -1.3457    2.1848 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8558   -1.3940    1.2912 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7257   -2.5026    0.4049 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7972   -2.5506   -0.5539 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5156   -3.6857   -1.5516 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1476   -3.6633   -2.0116 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7951   -2.6310   -2.8102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5427   -1.7808   -3.2638 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3283   -2.6513   -3.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1854   -1.8396   -4.0719 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5560   -1.7976   -4.2845 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0578   -0.9911   -5.2628 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4147   -2.5526   -3.4974 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7616   -2.4780   -3.7244 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9119   -3.3564   -2.4813 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8081   -4.0625   -1.7289 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5422   -3.4128   -2.2456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1359   -2.7627    0.1681 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.2277   -2.7507   -0.7511 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3392   -1.6631    1.2165 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.5242   -1.9525    1.9750 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1266   -1.5595    2.1413 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3138   -0.4497    3.0332 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8400    1.8651   -2.0108 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.5092    0.5424   -0.9025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4963    3.8035   -1.9130 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6800    3.4452    0.6489 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5652    3.7325   -0.8511 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7462    1.3168    1.1180 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7739   -0.0070   -0.0622 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7749    1.4311   -0.2983 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9498    2.0654   -2.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1687    0.4900   -2.4802 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2469    1.9306   -2.9258 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2837   -0.2400   -1.7803 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9852    2.2041    1.4973 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7770    0.6541    1.6650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4047    0.7875    2.7472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2050    1.0758    1.2462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5602   -1.2594    0.4686 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5618   -1.6118    1.7039 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6941   -1.4817    3.2528 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3671   -2.8309    2.1758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9014   -0.4517    0.7316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8123   -1.6008   -1.1026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6390   -4.6550   -1.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2002   -3.6634   -2.4073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4760   -1.2395   -4.6926 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0236   -1.1527   -5.2534 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1528   -3.0875   -3.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3199   -4.5355   -1.0312 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1485   -4.0228   -1.4378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1462   -3.7388    0.6696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0328   -2.7038   -0.1955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5320   -0.7011    0.7251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5076   -1.3215    2.7235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0574   -2.4560    2.7698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4629   -0.3590    3.5082 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
 13 14  1  0  0  0  0
  2 10  1  0  0  0  0
 14 15  1  0  0  0  0
 10  7  1  0  0  0  0
 33 35  1  0  0  0  0
 35 37  1  0  0  0  0
 37 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 33  1  0  0  0  0
 17 16  1  0  0  0  0
 37 38  1  0  0  0  0
 35 36  1  0  0  0  0
  4  5  2  0  0  0  0
 20 21  1  0  0  0  0
  2  1  1  0  0  0  0
 28 30  1  0  0  0  0
  7  8  1  1  0  0  0
 30 32  2  0  0  0  0
 14 16  1  0  0  0  0
 32 24  1  0  0  0  0
  6  4  1  0  0  0  0
 24 25  2  0  0  0  0
 10 11  1  6  0  0  0
 25 26  1  0  0  0  0
 26 28  2  0  0  0  0
  7  9  1  0  0  0  0
 24 22  1  0  0  0  0
  6  7  1  0  0  0  0
 22 23  2  0  0  0  0
 22 21  1  0  0  0  0
 10 12  1  0  0  0  0
 26 27  1  0  0  0  0
  4  3  1  0  0  0  0
 28 29  1  0  0  0  0
 12 13  1  0  0  0  0
 30 31  1  0  0  0  0
 33 34  1  0  0  0  0
 19 20  1  0  0  0  0
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  9 50  1  0  0  0  0
 12 52  1  0  0  0  0
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 13 54  1  0  0  0  0
 13 55  1  0  0  0  0
 14 56  1  6  0  0  0
 15 57  1  0  0  0  0
 15 58  1  0  0  0  0
 15 59  1  0  0  0  0
  1 39  1  0  0  0  0
  1 40  1  0  0  0  0
  1 41  1  0  0  0  0
 11 51  1  0  0  0  0
 34 70  1  0  0  0  0
 33 69  1  1  0  0  0
 17 60  1  6  0  0  0
 20 62  1  0  0  0  0
 20 63  1  0  0  0  0
 19 61  1  6  0  0  0
 37 73  1  1  0  0  0
 38 74  1  0  0  0  0
 35 71  1  6  0  0  0
 36 72  1  0  0  0  0
 32 68  1  0  0  0  0
 25 64  1  0  0  0  0
 27 65  1  0  0  0  0
 29 66  1  0  0  0  0
 31 67  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0030033

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(=C([H])C(O[H])=C1O[H])C(=O)OC([H])([H])[C@]1([H])O[C@]([H])(O[C@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[C@@]2(O[H])C(=C([H])C(=O)C([H])([H])C2(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]1([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C26H36O12/c1-12-7-15(27)10-25(3,4)26(12,35)6-5-13(2)37-24-22(33)21(32)20(31)18(38-24)11-36-23(34)14-8-16(28)19(30)17(29)9-14/h7-9,13,18,20-22,24,28-33,35H,5-6,10-11H2,1-4H3/t13-,18+,20+,21-,22+,24+,26-/m1/s1

> <INCHI_KEY>
YTTZYTOMXNRFMJ-XYEREUESSA-N

> <FORMULA>
C26H36O12

> <MOLECULAR_WEIGHT>
540.562

> <EXACT_MASS>
540.220676599

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
53.21306126212521

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-{[(2R)-4-[(1S)-1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl]butan-2-yl]oxy}oxan-2-yl]methyl 3,4,5-trihydroxybenzoate

> <ALOGPS_LOGP>
1.15

> <JCHEM_LOGP>
1.2828740096666664

> <ALOGPS_LOGS>
-2.91

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.235918100222584

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.107865629705906

> <JCHEM_PKA_STRONGEST_BASIC>
-3.325702908087968

> <JCHEM_POLAR_SURFACE_AREA>
203.43999999999997

> <JCHEM_REFRACTIVITY>
132.2966

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.67e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-{[(2R)-4-[(1S)-1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl]butan-2-yl]oxy}oxan-2-yl]methyl 3,4,5-trihydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 74 76  0  0  0  0  0  0  0  0999 V2000
   -1.0595    1.1788   -1.6644 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1478    1.9145   -1.1446 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2635    3.2332   -1.3884 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4641    4.0041   -0.9876 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4502    5.2283   -1.0950 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6639    3.2677   -0.4326 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6532    1.7546   -0.7482 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7952    1.0824    0.0501 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0153    1.5491   -2.2473 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2329    1.1427   -0.3943 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2175   -0.2203   -0.8096 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9628    1.1659    1.1432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3437    0.5524    1.6746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5171   -0.9677    1.5221 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5976   -1.7599    2.1976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7392   -1.3457    2.1848 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8558   -1.3940    1.2912 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7257   -2.5026    0.4049 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7972   -2.5506   -0.5539 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5156   -3.6857   -1.5516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1476   -3.6633   -2.0116 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7951   -2.6310   -2.8102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5427   -1.7808   -3.2638 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3283   -2.6513   -3.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1854   -1.8396   -4.0719 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5560   -1.7976   -4.2845 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0578   -0.9911   -5.2628 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4147   -2.5526   -3.4974 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7616   -2.4780   -3.7244 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9119   -3.3564   -2.4813 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8081   -4.0625   -1.7289 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5422   -3.4128   -2.2456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1359   -2.7627    0.1681 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.2277   -2.7507   -0.7511 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3392   -1.6631    1.2165 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.5242   -1.9525    1.9750 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1266   -1.5595    2.1413 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3138   -0.4497    3.0332 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8400    1.8651   -2.0108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7775    0.5509   -2.5138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5092    0.5424   -0.9025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4963    3.8035   -1.9130 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6800    3.4452    0.6489 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5652    3.7325   -0.8511 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7462    1.3168    1.1180 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7739   -0.0070   -0.0622 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7749    1.4311   -0.2983 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9498    2.0654   -2.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1687    0.4900   -2.4802 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2469    1.9306   -2.9258 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2837   -0.2400   -1.7803 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9852    2.2041    1.4973 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7770    0.6541    1.6650 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2050    1.0758    1.2462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5602   -1.2594    0.4686 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5618   -1.6118    1.7039 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6941   -1.4817    3.2528 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3671   -2.8309    2.1758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9014   -0.4517    0.7316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8123   -1.6008   -1.1026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6390   -4.6550   -1.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2002   -3.6634   -2.4073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4760   -1.2395   -4.6926 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0236   -1.1527   -5.2534 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1528   -3.0875   -3.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3199   -4.5355   -1.0312 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1485   -4.0228   -1.4378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1462   -3.7388    0.6696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0328   -2.7038   -0.1955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5320   -0.7011    0.7251 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.0574   -2.4560    2.7698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4629   -0.3590    3.5082 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0
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 31 67  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.060   1.179  -1.664  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.148   1.915  -1.145  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.264   3.233  -1.388  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.464   4.004  -0.988  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.450   5.228  -1.095  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.664   3.268  -0.433  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.653   1.755  -0.748  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.795   1.082   0.050  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.015   1.549  -2.247  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.233   1.143  -0.394  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.218  -0.220  -0.810  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.963   1.166   1.143  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.344   0.552   1.675  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.517  -0.968   1.522  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.598  -1.760   2.198  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.739  -1.346   2.185  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.856  -1.394   1.291  0.00  0.00           C+0
HETATM   18  O   UNK     0      -2.726  -2.503   0.405  0.00  0.00           O+0
HETATM   19  C   UNK     0      -3.797  -2.551  -0.554  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.516  -3.686  -1.552  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.148  -3.663  -2.012  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.795  -2.631  -2.810  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.543  -1.781  -3.264  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.328  -2.651  -3.048  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.185  -1.840  -4.072  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.556  -1.798  -4.285  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.058  -0.991  -5.263  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.415  -2.553  -3.497  0.00  0.00           C+0
HETATM   29  O   UNK     0       3.762  -2.478  -3.724  0.00  0.00           O+0
HETATM   30  C   UNK     0       1.912  -3.356  -2.481  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.808  -4.063  -1.729  0.00  0.00           O+0
HETATM   32  C   UNK     0       0.542  -3.413  -2.246  0.00  0.00           C+0
HETATM   33  C   UNK     0      -5.136  -2.763   0.168  0.00  0.00           C+0
HETATM   34  O   UNK     0      -6.228  -2.751  -0.751  0.00  0.00           O+0
HETATM   35  C   UNK     0      -5.339  -1.663   1.216  0.00  0.00           C+0
HETATM   36  O   UNK     0      -6.524  -1.952   1.975  0.00  0.00           O+0
HETATM   37  C   UNK     0      -4.127  -1.560   2.141  0.00  0.00           C+0
HETATM   38  O   UNK     0      -4.314  -0.450   3.033  0.00  0.00           O+0
HETATM   39  H   UNK     0      -1.840   1.865  -2.011  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.778   0.551  -2.514  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.509   0.542  -0.903  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.496   3.804  -1.913  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.680   3.445   0.649  0.00  0.00           H+0
HETATM   44  H   UNK     0       3.565   3.732  -0.851  0.00  0.00           H+0
HETATM   45  H   UNK     0       3.746   1.317   1.118  0.00  0.00           H+0
HETATM   46  H   UNK     0       3.774  -0.007  -0.062  0.00  0.00           H+0
HETATM   47  H   UNK     0       4.775   1.431  -0.298  0.00  0.00           H+0
HETATM   48  H   UNK     0       3.950   2.065  -2.498  0.00  0.00           H+0
HETATM   49  H   UNK     0       3.169   0.490  -2.480  0.00  0.00           H+0
HETATM   50  H   UNK     0       2.247   1.931  -2.926  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.284  -0.240  -1.780  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.985   2.204   1.497  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.777   0.654   1.665  0.00  0.00           H+0
HETATM   54  H   UNK     0      -0.405   0.788   2.747  0.00  0.00           H+0
HETATM   55  H   UNK     0      -1.205   1.076   1.246  0.00  0.00           H+0
HETATM   56  H   UNK     0      -0.560  -1.259   0.469  0.00  0.00           H+0
HETATM   57  H   UNK     0       1.562  -1.612   1.704  0.00  0.00           H+0
HETATM   58  H   UNK     0       0.694  -1.482   3.253  0.00  0.00           H+0
HETATM   59  H   UNK     0       0.367  -2.831   2.176  0.00  0.00           H+0
HETATM   60  H   UNK     0      -2.901  -0.452   0.732  0.00  0.00           H+0
HETATM   61  H   UNK     0      -3.812  -1.601  -1.103  0.00  0.00           H+0
HETATM   62  H   UNK     0      -3.639  -4.655  -1.056  0.00  0.00           H+0
HETATM   63  H   UNK     0      -4.200  -3.663  -2.407  0.00  0.00           H+0
HETATM   64  H   UNK     0      -0.476  -1.240  -4.693  0.00  0.00           H+0
HETATM   65  H   UNK     0       3.024  -1.153  -5.253  0.00  0.00           H+0
HETATM   66  H   UNK     0       4.153  -3.087  -3.064  0.00  0.00           H+0
HETATM   67  H   UNK     0       2.320  -4.535  -1.031  0.00  0.00           H+0
HETATM   68  H   UNK     0       0.149  -4.023  -1.438  0.00  0.00           H+0
HETATM   69  H   UNK     0      -5.146  -3.739   0.670  0.00  0.00           H+0
HETATM   70  H   UNK     0      -7.033  -2.704  -0.196  0.00  0.00           H+0
HETATM   71  H   UNK     0      -5.532  -0.701   0.725  0.00  0.00           H+0
HETATM   72  H   UNK     0      -6.508  -1.321   2.724  0.00  0.00           H+0
HETATM   73  H   UNK     0      -4.057  -2.456   2.770  0.00  0.00           H+0
HETATM   74  H   UNK     0      -3.463  -0.359   3.508  0.00  0.00           H+0
CONECT    1    2   39   40   41                                             
CONECT    2    3   10    1                                                  
CONECT    3    2    4   42                                                  
CONECT    4    5    6    3                                                  
CONECT    5    4                                                            
CONECT    6    4    7   43   44                                             
CONECT    7   10    8    9    6                                             
CONECT    8    7   45   46   47                                             
CONECT    9    7   48   49   50                                             
CONECT   10    2    7   11   12                                             
CONECT   11   10   51                                                       
CONECT   12   10   13   52   53                                             
CONECT   13   14   12   54   55                                             
CONECT   14   13   15   16   56                                             
CONECT   15   14   57   58   59                                             
CONECT   16   17   14                                                       
CONECT   17   37   18   16   60                                             
CONECT   18   17   19                                                       
CONECT   19   18   33   20   61                                             
CONECT   20   21   19   62   63                                             
CONECT   21   20   22                                                       
CONECT   22   24   23   21                                                  
CONECT   23   22                                                            
CONECT   24   32   25   22                                                  
CONECT   25   24   26   64                                                  
CONECT   26   25   28   27                                                  
CONECT   27   26   65                                                       
CONECT   28   30   26   29                                                  
CONECT   29   28   66                                                       
CONECT   30   28   32   31                                                  
CONECT   31   30   67                                                       
CONECT   32   30   24   68                                                  
CONECT   33   35   19   34   69                                             
CONECT   34   33   70                                                       
CONECT   35   33   37   36   71                                             
CONECT   36   35   72                                                       
CONECT   37   35   17   38   73                                             
CONECT   38   37   74                                                       
CONECT   39    1                                                            
CONECT   40    1                                                            
CONECT   41    1                                                            
CONECT   42    3                                                            
CONECT   43    6                                                            
CONECT   44    6                                                            
CONECT   45    8                                                            
CONECT   46    8                                                            
CONECT   47    8                                                            
CONECT   48    9                                                            
CONECT   49    9                                                            
CONECT   50    9                                                            
CONECT   51   11                                                            
CONECT   52   12                                                            
CONECT   53   12                                                            
CONECT   54   13                                                            
CONECT   55   13                                                            
CONECT   56   14                                                            
CONECT   57   15                                                            
CONECT   58   15                                                            
CONECT   59   15                                                            
CONECT   60   17                                                            
CONECT   61   19                                                            
CONECT   62   20                                                            
CONECT   63   20                                                            
CONECT   64   25                                                            
CONECT   65   27                                                            
CONECT   66   29                                                            
CONECT   67   31                                                            
CONECT   68   32                                                            
CONECT   69   33                                                            
CONECT   70   34                                                            
CONECT   71   35                                                            
CONECT   72   36                                                            
CONECT   73   37                                                            
CONECT   74   38                                                            
MASTER        0    0    0    0    0    0    0    0   74    0  152    0
END

RDKit          3D

74 76  0  0  0  0  0  0  0  0999 V2000
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    0.2635    3.2332   -1.3884 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4502    5.2283   -1.0950 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6639    3.2677   -0.4326 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6532    1.7546   -0.7482 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7952    1.0824    0.0501 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0153    1.5491   -2.2473 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2175   -0.2203   -0.8096 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5171   -0.9677    1.5221 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5976   -1.7599    2.1976 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8081   -4.0625   -1.7289 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5422   -3.4128   -2.2456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1359   -2.7627    0.1681 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.2277   -2.7507   -0.7511 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3392   -1.6631    1.2165 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.5242   -1.9525    1.9750 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.3138   -0.4497    3.0332 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8400    1.8651   -2.0108 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4047    0.7875    2.7472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2050    1.0758    1.2462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5602   -1.2594    0.4686 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5618   -1.6118    1.7039 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6941   -1.4817    3.2528 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3671   -2.8309    2.1758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9014   -0.4517    0.7316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8123   -1.6008   -1.1026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6390   -4.6550   -1.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2002   -3.6634   -2.4073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4760   -1.2395   -4.6926 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0236   -1.1527   -5.2534 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1528   -3.0875   -3.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3199   -4.5355   -1.0312 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1485   -4.0228   -1.4378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1462   -3.7388    0.6696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0328   -2.7038   -0.1955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5320   -0.7011    0.7251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5076   -1.3215    2.7235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0574   -2.4560    2.7698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4629   -0.3590    3.5082 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0
 13 14  1  0
  2 10  1  0
 14 15  1  0
 10  7  1  0
 33 35  1  0
 35 37  1  0
 37 17  1  0
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 37 38  1  0
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  4  5  2  0
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  2  1  1  0
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  7  8  1  1
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  7  9  1  0
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  6  7  1  0
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  4  3  1  0
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 29 66  1  0
 31 67  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₆O₁₂

Average Mass

540.5620 Da

Monoisotopic Mass

540.22068 Da

IUPAC Name

[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-{[(2R)-4-[(1S)-1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl]butan-2-yl]oxy}oxan-2-yl]methyl 3,4,5-trihydroxybenzoate

Traditional Name

[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-{[(2R)-4-[(1S)-1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl]butan-2-yl]oxy}oxan-2-yl]methyl 3,4,5-trihydroxybenzoate

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C(=C([H])C(O[H])=C1O[H])C(=O)OC([H])([H])[C@]1([H])O[C@]([H])(O[C@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[C@@]2(O[H])C(=C([H])C(=O)C([H])([H])C2(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]1([H])O[H]

InChI Identifier

InChI=1S/C26H36O12/c1-12-7-15(27)10-25(3,4)26(12,35)6-5-13(2)37-24-22(33)21(32)20(31)18(38-24)11-36-23(34)14-8-16(28)19(30)17(29)9-14/h7-9,13,18,20-22,24,28-33,35H,5-6,10-11H2,1-4H3/t13-,18+,20+,21-,22+,24+,26-/m1/s1

InChI Key

YTTZYTOMXNRFMJ-XYEREUESSA-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
Macaranga tanarius	JEOL database	Matsunami, K., et al, Chem. Pharm. Bull. 54, 1403 (2006)

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	1.15	ALOGPS
logP	1.28	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	8.11	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	203.44 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	132.3 m³·mol⁻¹	ChemAxon
Polarizability	53.21 Å³	ChemAxon
Number of Rings	3	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

Not Available

References

General References

Matsunami, K., et al. (2006). Matsunami, K., et al, Chem. Pharm. Bull. 54, 1403 (2006). Chem. Pharm. Bull..

Showing NP-Card for macarangioside A (NP0030033)

MOL for NP0030033 (macarangioside A)

3D MOL for NP0030033 (macarangioside A)

3D SDF for NP0030033 (macarangioside A)

3D-SDF for NP0030033 (macarangioside A)

PDB for NP0030033 (macarangioside A)

3D PDB for NP0030033 (macarangioside A)

SMILES for NP0030033 (macarangioside A)

INCHI for NP0030033 (macarangioside A)

Structure for NP0030033 (macarangioside A)

3D Structure for NP0030033 (macarangioside A)