NP-MRD: Showing NP-Card for 3,4-dihydro-1-(1-beta-D-glucopyranosyloxy-1,4a,5,7atetrahydro-4-methoxyca+ (NP0038247)

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Record Information

Version

2.0

Created at

2021-06-20 20:59:08 UTC

Updated at

2021-06-30 00:10:56 UTC

NP-MRD ID

NP0038247

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,4-dihydro-1-(1-beta-D-glucopyranosyloxy-1,4a,5,7atetrahydro-4-methoxyca+

Provided By

JEOL Database JEOL Logo

Description

3,4-dihydro-1-(1-beta-D-glucopyranosyloxy-1,4a,5,7atetrahydro-4-methoxyca+ is found in Palicourea crocea. 3,4-dihydro-1-(1-beta-D-glucopyranosyloxy-1,4a,5,7atetrahydro-4-methoxyca+ was first documented in 2009 (Narine, L. L., et al.).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202122593D          

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M  CHG  2  24   1  25  -1
M  END

     RDKit          3D

 69 74  0  0  0  0  0  0  0  0999 V2000
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M  CHG  2  24   1  25  -1
M  END


  Mrv1652306202122593D          

 69 74  0  0  0  0            999 V2000
   -2.6305   -5.8133    1.3004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3631   -4.5283    0.7369 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9481   -3.6050    1.6396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7898   -3.8040    2.8353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6819   -2.2892    0.9988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0469   -2.0451   -0.2679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9308   -0.8431   -0.9123 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7829    0.2940   -0.0460 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0534    0.6208    0.5412 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6268    1.7710   -0.0808 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8408    2.9163    0.2255 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3412    4.1098   -0.3993 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3523    5.2406   -0.0993 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0608    4.9039   -0.6143 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7474    4.4272    0.1258 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3057    5.5621   -0.5377 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6650    3.2186   -0.0916 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.9370    3.4783    0.5238 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0448    1.9471    0.4859 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8867    0.8296    0.1624 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7637    0.0885    1.0815 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6769   -0.0332    0.6506 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3535    0.8442   -0.3428 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1450    2.1628   -0.3935 N   0  3  0  0  0  4  0  0  0  0  0  0
    0.3480    2.7424    0.4247 O   0  5  0  0  0  1  0  0  0  0  0  0
    1.7678    3.0266   -1.4528 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1707    2.5247   -1.8037 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1573    1.0518   -2.0077 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2857    0.2655   -1.2858 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4811   -1.0340   -1.6628 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4788   -1.1010   -2.6128 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0146   -2.2104   -3.2776 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0350   -1.9794   -4.2050 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4993   -0.6902   -4.4566 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9531    0.4098   -3.7852 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9238    0.2036   -2.8469 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3151   -0.9895    1.3374 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4038   -1.6652    2.3112 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0069   -1.2358    1.8490 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9614   -6.4741    0.4945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7220   -6.2342    1.7426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4304   -5.7471    2.0446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4808   -2.7773   -0.9390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4437    1.1079   -0.6957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6684    1.5998   -1.1654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3540    3.9529   -1.4863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2447    5.4021    0.9785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6657    6.1784   -0.5670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7611    4.1181   -0.0992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7097    4.6626    1.1970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2453    5.5841   -0.2631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8769    3.0910   -1.1608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4113    2.6221    0.4995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0179    2.0090    1.5810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3825    0.0374    0.4371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8437    0.9172    1.7984 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0938    2.9775   -2.3159 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8029    4.0560   -1.0825 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5332    3.0418   -2.6985 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8616    2.7590   -0.9844 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9676   -1.8304   -1.3113 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6565   -3.2164   -3.0848 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4728   -2.8205   -4.7380 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2941   -0.5346   -5.1820 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3225    1.4102   -3.9894 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3698   -1.2214    1.2670 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6130   -1.3006    3.3232 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5614   -2.7474    2.2948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6474   -1.0454    2.7204 H   0  0  0  0  0  0  0  0  0  0  0  0
 31 36  2  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 19 20  1  0  0  0  0
 13 14  1  0  0  0  0
 31 32  1  0  0  0  0
 36 35  1  0  0  0  0
 35 34  2  0  0  0  0
 34 33  1  0  0  0  0
 33 32  2  0  0  0  0
 31 30  1  0  0  0  0
 24 25  1  0  0  0  0
 10 19  1  0  0  0  0
 23 22  1  0  0  0  0
 22 21  1  0  0  0  0
 30 29  1  0  0  0  0
 28 36  1  0  0  0  0
 39 38  1  0  0  0  0
 38 37  1  0  0  0  0
 37 22  2  0  0  0  0
 39 21  1  0  0  0  0
 28 29  2  0  0  0  0
 19 17  1  0  0  0  0
 17 15  1  0  0  0  0
 15 12  1  0  0  0  0
 12 11  1  0  0  0  0
 11 10  1  0  0  0  0
 39  5  1  0  0  0  0
 21  8  1  0  0  0  0
  8  7  1  0  0  0  0
  7  6  1  0  0  0  0
  6  5  2  0  0  0  0
  8  9  1  0  0  0  0
  5  3  1  0  0  0  0
 28 27  1  0  0  0  0
  3  4  2  0  0  0  0
 29 23  1  0  0  0  0
  3  2  1  0  0  0  0
 23 24  2  0  0  0  0
  2  1  1  0  0  0  0
 24 26  1  0  0  0  0
 39 69  1  1  0  0  0
 26 27  1  0  0  0  0
 21 56  1  1  0  0  0
 12 13  1  0  0  0  0
 10  9  1  0  0  0  0
 10 45  1  6  0  0  0
 15 50  1  1  0  0  0
 16 51  1  0  0  0  0
 17 52  1  6  0  0  0
 18 53  1  0  0  0  0
 19 54  1  1  0  0  0
 20 55  1  0  0  0  0
 13 47  1  0  0  0  0
 13 48  1  0  0  0  0
 12 46  1  6  0  0  0
 14 49  1  0  0  0  0
 30 61  1  0  0  0  0
 26 57  1  0  0  0  0
 26 58  1  0  0  0  0
 27 59  1  0  0  0  0
 27 60  1  0  0  0  0
 35 65  1  0  0  0  0
 34 64  1  0  0  0  0
 33 63  1  0  0  0  0
 32 62  1  0  0  0  0
 38 67  1  0  0  0  0
 38 68  1  0  0  0  0
 37 66  1  0  0  0  0
  8 44  1  6  0  0  0
  6 43  1  0  0  0  0
  1 40  1  0  0  0  0
  1 41  1  0  0  0  0
  1 42  1  0  0  0  0
M  CHG  2  24   1  25  -1
M  END
> <DATABASE_ID>
NP0038247

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])[C@@]1([H])O[C@@]([H])(O[C@]2([H])OC([H])=C(C(=O)OC([H])([H])[H])[C@@]3([H])C([H])([H])C([H])=C(C4=[N+]([O-])C([H])([H])C([H])([H])C5=C4N([H])C4=C5C([H])=C([H])C([H])=C4[H])[C@@]23[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C27H30N2O10/c1-36-25(34)16-11-37-26(39-27-24(33)23(32)22(31)18(10-30)38-27)19-13(16)6-7-15(19)21-20-14(8-9-29(21)35)12-4-2-3-5-17(12)28-20/h2-5,7,11,13,18-19,22-24,26-28,30-33H,6,8-10H2,1H3/t13-,18-,19+,22-,23+,24-,26+,27+/m1/s1

> <INCHI_KEY>
UZURUCQWUPTZLR-RFRAKBMSSA-N

> <FORMULA>
C27H30N2O10

> <MOLECULAR_WEIGHT>
542.541

> <EXACT_MASS>
542.190045174

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
55.841623345617165

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-[(1S,4aS,7aS)-4-(methoxycarbonyl)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-7-yl]-3H,4H,9H-pyrido[3,4-b]indol-2-ium-2-olate

> <ALOGPS_LOGP>
0.09

> <JCHEM_LOGP>
-3.1116798251384106

> <ALOGPS_LOGS>
-3.03

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
12.207072732001714

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.353220011553088

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810847615684217

> <JCHEM_POLAR_SURFACE_AREA>
176.77

> <JCHEM_REFRACTIVITY>
136.9507

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.11e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-[(1S,4aS,7aS)-4-(methoxycarbonyl)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-7-yl]-3H,4H,9H-pyrido[3,4-b]indol-2-ium-2-olate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 69 74  0  0  0  0  0  0  0  0999 V2000
   -2.6305   -5.8133    1.3004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3631   -4.5283    0.7369 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9481   -3.6050    1.6396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7898   -3.8040    2.8353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6819   -2.2892    0.9988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0469   -2.0451   -0.2679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9308   -0.8431   -0.9123 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7829    0.2940   -0.0460 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0534    0.6208    0.5412 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6268    1.7710   -0.0808 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8408    2.9163    0.2255 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3412    4.1098   -0.3993 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3523    5.2406   -0.0993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0608    4.9039   -0.6143 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7474    4.4272    0.1258 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3057    5.5621   -0.5377 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6650    3.2186   -0.0916 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.9370    3.4783    0.5238 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0448    1.9471    0.4859 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8867    0.8296    0.1624 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7637    0.0885    1.0815 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6769   -0.0332    0.6506 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3535    0.8442   -0.3428 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1450    2.1628   -0.3935 N   0  0  0  0  0  4  0  0  0  0  0  0
    0.3480    2.7424    0.4247 O   0  0  0  0  0  1  0  0  0  0  0  0
    1.7678    3.0266   -1.4528 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1707    2.5247   -1.8037 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1573    1.0518   -2.0077 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2857    0.2655   -1.2858 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4811   -1.0340   -1.6628 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4788   -1.1010   -2.6128 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0146   -2.2104   -3.2776 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0350   -1.9794   -4.2050 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4993   -0.6902   -4.4566 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9531    0.4098   -3.7852 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9238    0.2036   -2.8469 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3151   -0.9895    1.3374 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4038   -1.6652    2.3112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0069   -1.2358    1.8490 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9614   -6.4741    0.4945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7220   -6.2342    1.7426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4304   -5.7471    2.0446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4808   -2.7773   -0.9390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4437    1.1079   -0.6957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6684    1.5998   -1.1654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3540    3.9529   -1.4863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2447    5.4021    0.9785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6657    6.1784   -0.5670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7611    4.1181   -0.0992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7097    4.6626    1.1970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2453    5.5841   -0.2631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8769    3.0910   -1.1608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4113    2.6221    0.4995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0179    2.0090    1.5810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3825    0.0374    0.4371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8437    0.9172    1.7984 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0938    2.9775   -2.3159 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8029    4.0560   -1.0825 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5332    3.0418   -2.6985 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8616    2.7590   -0.9844 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9676   -1.8304   -1.3113 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6565   -3.2164   -3.0848 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4728   -2.8205   -4.7380 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2941   -0.5346   -5.1820 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3225    1.4102   -3.9894 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3698   -1.2214    1.2670 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6130   -1.3006    3.3232 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5614   -2.7474    2.2948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6474   -1.0454    2.7204 H   0  0  0  0  0  0  0  0  0  0  0  0
 31 36  2  0
 15 16  1  0
 17 18  1  0
 19 20  1  0
 13 14  1  0
 31 32  1  0
 36 35  1  0
 35 34  2  0
 34 33  1  0
 33 32  2  0
 31 30  1  0
 24 25  1  0
 10 19  1  0
 23 22  1  0
 22 21  1  0
 30 29  1  0
 28 36  1  0
 39 38  1  0
 38 37  1  0
 37 22  2  0
 39 21  1  0
 28 29  2  0
 19 17  1  0
 17 15  1  0
 15 12  1  0
 12 11  1  0
 11 10  1  0
 39  5  1  0
 21  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  2  0
  8  9  1  0
  5  3  1  0
 28 27  1  0
  3  4  2  0
 29 23  1  0
  3  2  1  0
 23 24  2  0
  2  1  1  0
 24 26  1  0
 39 69  1  1
 26 27  1  0
 21 56  1  1
 12 13  1  0
 10  9  1  0
 10 45  1  6
 15 50  1  1
 16 51  1  0
 17 52  1  6
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 19 54  1  1
 20 55  1  0
 13 47  1  0
 13 48  1  0
 12 46  1  6
 14 49  1  0
 30 61  1  0
 26 57  1  0
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 27 60  1  0
 35 65  1  0
 34 64  1  0
 33 63  1  0
 32 62  1  0
 38 67  1  0
 38 68  1  0
 37 66  1  0
  8 44  1  6
  6 43  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
M  CHG  2  24   1  25  -1
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -2.631  -5.813   1.300  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.363  -4.528   0.737  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.948  -3.605   1.640  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.790  -3.804   2.835  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.682  -2.289   0.999  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.047  -2.045  -0.268  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.931  -0.843  -0.912  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.783   0.294  -0.046  0.00  0.00           C+0
HETATM    9  O   UNK     0      -3.053   0.621   0.541  0.00  0.00           O+0
HETATM   10  C   UNK     0      -3.627   1.771  -0.081  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.841   2.916   0.226  0.00  0.00           O+0
HETATM   12  C   UNK     0      -3.341   4.110  -0.399  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.352   5.241  -0.099  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.061   4.904  -0.614  0.00  0.00           O+0
HETATM   15  C   UNK     0      -4.747   4.427   0.126  0.00  0.00           C+0
HETATM   16  O   UNK     0      -5.306   5.562  -0.538  0.00  0.00           O+0
HETATM   17  C   UNK     0      -5.665   3.219  -0.092  0.00  0.00           C+0
HETATM   18  O   UNK     0      -6.937   3.478   0.524  0.00  0.00           O+0
HETATM   19  C   UNK     0      -5.045   1.947   0.486  0.00  0.00           C+0
HETATM   20  O   UNK     0      -5.887   0.830   0.162  0.00  0.00           O+0
HETATM   21  C   UNK     0      -0.764   0.089   1.081  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.677  -0.033   0.651  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.353   0.844  -0.343  0.00  0.00           C+0
HETATM   24  N   UNK     0       1.145   2.163  -0.394  0.00  0.00           N+1
HETATM   25  O   UNK     0       0.348   2.742   0.425  0.00  0.00           O-1
HETATM   26  C   UNK     0       1.768   3.027  -1.453  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.171   2.525  -1.804  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.157   1.052  -2.008  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.286   0.266  -1.286  0.00  0.00           C+0
HETATM   30  N   UNK     0       2.481  -1.034  -1.663  0.00  0.00           N+0
HETATM   31  C   UNK     0       3.479  -1.101  -2.613  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.015  -2.210  -3.278  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.035  -1.979  -4.205  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.499  -0.690  -4.457  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.953   0.410  -3.785  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.924   0.204  -2.847  0.00  0.00           C+0
HETATM   37  C   UNK     0       1.315  -0.990   1.337  0.00  0.00           C+0
HETATM   38  C   UNK     0       0.404  -1.665   2.311  0.00  0.00           C+0
HETATM   39  C   UNK     0      -1.007  -1.236   1.849  0.00  0.00           C+0
HETATM   40  H   UNK     0      -2.961  -6.474   0.495  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.722  -6.234   1.743  0.00  0.00           H+0
HETATM   42  H   UNK     0      -3.430  -5.747   2.045  0.00  0.00           H+0
HETATM   43  H   UNK     0      -2.481  -2.777  -0.939  0.00  0.00           H+0
HETATM   44  H   UNK     0      -1.444   1.108  -0.696  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.668   1.600  -1.165  0.00  0.00           H+0
HETATM   46  H   UNK     0      -3.354   3.953  -1.486  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.245   5.402   0.979  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.666   6.178  -0.567  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.761   4.118  -0.099  0.00  0.00           H+0
HETATM   50  H   UNK     0      -4.710   4.663   1.197  0.00  0.00           H+0
HETATM   51  H   UNK     0      -6.245   5.584  -0.263  0.00  0.00           H+0
HETATM   52  H   UNK     0      -5.877   3.091  -1.161  0.00  0.00           H+0
HETATM   53  H   UNK     0      -7.411   2.622   0.500  0.00  0.00           H+0
HETATM   54  H   UNK     0      -5.018   2.009   1.581  0.00  0.00           H+0
HETATM   55  H   UNK     0      -5.383   0.037   0.437  0.00  0.00           H+0
HETATM   56  H   UNK     0      -0.844   0.917   1.798  0.00  0.00           H+0
HETATM   57  H   UNK     0       1.094   2.978  -2.316  0.00  0.00           H+0
HETATM   58  H   UNK     0       1.803   4.056  -1.083  0.00  0.00           H+0
HETATM   59  H   UNK     0       3.533   3.042  -2.699  0.00  0.00           H+0
HETATM   60  H   UNK     0       3.862   2.759  -0.984  0.00  0.00           H+0
HETATM   61  H   UNK     0       1.968  -1.830  -1.311  0.00  0.00           H+0
HETATM   62  H   UNK     0       3.656  -3.216  -3.085  0.00  0.00           H+0
HETATM   63  H   UNK     0       5.473  -2.821  -4.738  0.00  0.00           H+0
HETATM   64  H   UNK     0       6.294  -0.535  -5.182  0.00  0.00           H+0
HETATM   65  H   UNK     0       5.322   1.410  -3.989  0.00  0.00           H+0
HETATM   66  H   UNK     0       2.370  -1.221   1.267  0.00  0.00           H+0
HETATM   67  H   UNK     0       0.613  -1.301   3.323  0.00  0.00           H+0
HETATM   68  H   UNK     0       0.561  -2.747   2.295  0.00  0.00           H+0
HETATM   69  H   UNK     0      -1.647  -1.045   2.720  0.00  0.00           H+0
CONECT    1    2   40   41   42                                             
CONECT    2    3    1                                                       
CONECT    3    5    4    2                                                  
CONECT    4    3                                                            
CONECT    5   39    6    3                                                  
CONECT    6    7    5   43                                                  
CONECT    7    8    6                                                       
CONECT    8   21    7    9   44                                             
CONECT    9    8   10                                                       
CONECT   10   19   11    9   45                                             
CONECT   11   12   10                                                       
CONECT   12   15   11   13   46                                             
CONECT   13   14   12   47   48                                             
CONECT   14   13   49                                                       
CONECT   15   16   17   12   50                                             
CONECT   16   15   51                                                       
CONECT   17   18   19   15   52                                             
CONECT   18   17   53                                                       
CONECT   19   20   10   17   54                                             
CONECT   20   19   55                                                       
CONECT   21   22   39    8   56                                             
CONECT   22   23   21   37                                                  
CONECT   23   22   29   24                                                  
CONECT   24   25   23   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   57   58                                             
CONECT   27   28   26   59   60                                             
CONECT   28   36   29   27                                                  
CONECT   29   30   28   23                                                  
CONECT   30   31   29   61                                                  
CONECT   31   36   32   30                                                  
CONECT   32   31   33   62                                                  
CONECT   33   34   32   63                                                  
CONECT   34   35   33   64                                                  
CONECT   35   36   34   65                                                  
CONECT   36   31   35   28                                                  
CONECT   37   38   22   66                                                  
CONECT   38   39   37   67   68                                             
CONECT   39   38   21    5   69                                             
CONECT   40    1                                                            
CONECT   41    1                                                            
CONECT   42    1                                                            
CONECT   43    6                                                            
CONECT   44    8                                                            
CONECT   45   10                                                            
CONECT   46   12                                                            
CONECT   47   13                                                            
CONECT   48   13                                                            
CONECT   49   14                                                            
CONECT   50   15                                                            
CONECT   51   16                                                            
CONECT   52   17                                                            
CONECT   53   18                                                            
CONECT   54   19                                                            
CONECT   55   20                                                            
CONECT   56   21                                                            
CONECT   57   26                                                            
CONECT   58   26                                                            
CONECT   59   27                                                            
CONECT   60   27                                                            
CONECT   61   30                                                            
CONECT   62   32                                                            
CONECT   63   33                                                            
CONECT   64   34                                                            
CONECT   65   35                                                            
CONECT   66   37                                                            
CONECT   67   38                                                            
CONECT   68   38                                                            
CONECT   69   39                                                            
MASTER        0    0    0    0    0    0    0    0   69    0  148    0
END

RDKit          3D

69 74  0  0  0  0  0  0  0  0999 V2000
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 10 45  1  6
 15 50  1  1
 16 51  1  0
 17 52  1  6
 18 53  1  0
 19 54  1  1
 20 55  1  0
 13 47  1  0
 13 48  1  0
 12 46  1  6
 14 49  1  0
 30 61  1  0
 26 57  1  0
 26 58  1  0
 27 59  1  0
 27 60  1  0
 35 65  1  0
 34 64  1  0
 33 63  1  0
 32 62  1  0
 38 67  1  0
 38 68  1  0
 37 66  1  0
  8 44  1  6
  6 43  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
M  CHG  2  24   1  25  -1
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₀N₂O₁₀

Average Mass

542.5410 Da

Monoisotopic Mass

542.19005 Da

IUPAC Name

1-[(1S,4aS,7aS)-4-(methoxycarbonyl)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-7-yl]-3H,4H,9H-pyrido[3,4-b]indol-2-ium-2-olate

Traditional Name

1-[(1S,4aS,7aS)-4-(methoxycarbonyl)-1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-7-yl]-3H,4H,9H-pyrido[3,4-b]indol-2-ium-2-olate

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])[C@@]1([H])O[C@@]([H])(O[C@]2([H])OC([H])=C(C(=O)OC([H])([H])[H])[C@@]3([H])C([H])([H])C([H])=C(C4=[N+]([O-])C([H])([H])C([H])([H])C5=C4N([H])C4=C5C([H])=C([H])C([H])=C4[H])[C@@]23[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]

InChI Identifier

InChI=1S/C27H30N2O10/c1-36-25(34)16-11-37-26(39-27-24(33)23(32)22(31)18(10-30)38-27)19-13(16)6-7-15(19)21-20-14(8-9-29(21)35)12-4-2-3-5-17(12)28-20/h2-5,7,11,13,18-19,22-24,26-28,30-33H,6,8-10H2,1H3/t13-,18-,19+,22-,23+,24-,26+,27+/m1/s1

InChI Key

UZURUCQWUPTZLR-RFRAKBMSSA-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
Palicourea crocea	JEOL database	Narine, L. L., et al, Phytochem. Lett. 2, 25 (2009)

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	0.09	ALOGPS
logP	-3.1	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	9.35	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	176.77 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	136.95 m³·mol⁻¹	ChemAxon
Polarizability	55.84 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	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

Narine, L. L., et al. (2009). Narine, L. L., et al, Phytochem. Lett. 2, 25 (2009) . Phytochem..

Showing NP-Card for 3,4-dihydro-1-(1-beta-D-glucopyranosyloxy-1,4a,5,7atetrahydro-4-methoxyca+ (NP0038247)

MOL for NP0038247 (3,4-dihydro-1-(1-beta-D-glucopyranosyloxy-1,4a,5,7atetrahydro-4-methoxyca+)

3D MOL for NP0038247 (3,4-dihydro-1-(1-beta-D-glucopyranosyloxy-1,4a,5,7atetrahydro-4-methoxyca+)

3D SDF for NP0038247 (3,4-dihydro-1-(1-beta-D-glucopyranosyloxy-1,4a,5,7atetrahydro-4-methoxyca+)

3D-SDF for NP0038247 (3,4-dihydro-1-(1-beta-D-glucopyranosyloxy-1,4a,5,7atetrahydro-4-methoxyca+)

PDB for NP0038247 (3,4-dihydro-1-(1-beta-D-glucopyranosyloxy-1,4a,5,7atetrahydro-4-methoxyca+)

3D PDB for NP0038247 (3,4-dihydro-1-(1-beta-D-glucopyranosyloxy-1,4a,5,7atetrahydro-4-methoxyca+)

SMILES for NP0038247 (3,4-dihydro-1-(1-beta-D-glucopyranosyloxy-1,4a,5,7atetrahydro-4-methoxyca+)

INCHI for NP0038247 (3,4-dihydro-1-(1-beta-D-glucopyranosyloxy-1,4a,5,7atetrahydro-4-methoxyca+)

Structure for NP0038247 (3,4-dihydro-1-(1-beta-D-glucopyranosyloxy-1,4a,5,7atetrahydro-4-methoxyca+)

3D Structure for NP0038247 (3,4-dihydro-1-(1-beta-D-glucopyranosyloxy-1,4a,5,7atetrahydro-4-methoxyca+)