NP-MRD: Showing NP-Card for croceaine A (NP0027570)

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Record Information

Version

2.0

Created at

2021-06-19 19:41:41 UTC

Updated at

2021-06-29 23:53:45 UTC

NP-MRD ID

NP0027570

Secondary Accession Numbers

None

Natural Product Identification

Common Name

croceaine A

Provided By

JEOL Database JEOL Logo

Description

croceaine A is found in Palicourea crocea and Psychotria umbellata. croceaine A was first documented in 2004 (Dusman, L. T., et al.).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


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M  END


  Mrv1652306192121413D          

 70 75  0  0  0  0            999 V2000
    6.2217    1.9903   -0.1558 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8035    2.1503   -0.0989 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1097    1.1369   -0.6742 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6013    0.1470   -1.1962 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6433    1.3549   -0.5779 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1250    2.5092   -0.1317 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7871    2.7905   -0.0119 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0729    1.6326    0.0148 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0535    0.9866    1.2913 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7142    1.6441    2.2970 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0836    1.2503    2.1954 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8996    1.8747    3.1960 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3674    1.5002    2.9495 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2561    2.2305    3.7875 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4437    1.4368    4.5984 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2220    2.0697    5.6202 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9663    1.7851    4.7870 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5244    1.2725    6.0533 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1319    1.1985    3.6514 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2302    1.6264    3.8082 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2666    0.6521   -1.1300 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4042   -0.7034   -1.0270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8450   -0.9135   -1.3923 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6824    0.0821   -0.6971 N   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0831    0.0621   -1.1634 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2291    0.4607   -2.6528 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1987   -0.2394   -3.4682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1122   -0.8395   -2.8646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3389   -1.3962   -3.8462 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9015   -1.1520   -5.0813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4616   -1.5182   -6.3590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2438   -1.1282   -7.4505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4182   -0.4008   -7.2697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8455   -0.0418   -5.9860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0759   -0.4232   -4.8701 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4550   -1.6348   -0.5802 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8179   -1.0668   -0.3374 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7611    0.2620   -1.1085 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6799    2.8586    0.3258 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5278    1.0910    0.3878 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5621    1.9509   -1.1953 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7075    3.3742    0.1641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0938    2.0056   -0.1184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6161    2.7326    2.1865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8172    2.9667    3.1071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5304    0.4289    3.1108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6388    1.7057    1.9087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8576    2.2465    4.6846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5766    0.3542    4.7196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7324    1.8973    6.4528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8332    2.8726    4.8453 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4506    1.3638    6.0388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1217    0.1036    3.7232 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6818    1.3576    2.9828 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0530    1.1327   -2.0936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1561   -1.9121   -1.0545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6513   -0.1130    0.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6696    0.7598   -0.5554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5080   -0.9364   -0.9976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0904    1.5435   -2.7582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2367    0.2134   -3.0039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4766   -1.9013   -3.6956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5470   -2.0834   -6.5043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9288   -1.3967   -8.4562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0102   -0.1073   -8.1328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7611    0.5264   -5.8543 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2077   -2.6722   -0.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9957   -0.9368    0.7355 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5926   -1.7237   -0.7454 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0606    0.0610   -2.1496 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0  0  0  0
 19 20  1  0  0  0  0
 17 18  1  0  0  0  0
 35 27  1  0  0  0  0
 27 26  1  0  0  0  0
 28 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 23 22  1  0  0  0  0
 22 21  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 38 37  1  0  0  0  0
 37 36  1  0  0  0  0
 36 22  2  0  0  0  0
 38 21  1  0  0  0  0
 15 17  1  0  0  0  0
 17 19  1  0  0  0  0
 30 35  2  0  0  0  0
 19 10  1  0  0  0  0
 35 34  1  0  0  0  0
 10 11  1  0  0  0  0
 38  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
 34 33  2  0  0  0  0
 23 56  1  1  0  0  0
 11 12  1  0  0  0  0
 21 55  1  6  0  0  0
 33 32  1  0  0  0  0
 38 70  1  6  0  0  0
  8  9  1  0  0  0  0
 12 15  1  0  0  0  0
 13 14  1  0  0  0  0
 32 31  2  0  0  0  0
  5  3  1  0  0  0  0
 31 30  1  0  0  0  0
  3  4  2  0  0  0  0
 27 28  2  0  0  0  0
  3  2  1  0  0  0  0
  2  1  1  0  0  0  0
 15 16  1  0  0  0  0
 12 13  1  0  0  0  0
 16 50  1  0  0  0  0
 15 49  1  6  0  0  0
 10 44  1  6  0  0  0
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 12 45  1  1  0  0  0
 19 53  1  6  0  0  0
 20 54  1  0  0  0  0
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 18 52  1  0  0  0  0
 29 62  1  0  0  0  0
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 33 65  1  0  0  0  0
 32 64  1  0  0  0  0
 31 63  1  0  0  0  0
 24 57  1  0  0  0  0
 25 58  1  0  0  0  0
 25 59  1  0  0  0  0
 26 60  1  0  0  0  0
 26 61  1  0  0  0  0
 37 68  1  0  0  0  0
 37 69  1  0  0  0  0
 36 67  1  0  0  0  0
  8 43  1  6  0  0  0
  6 42  1  0  0  0  0
 14 48  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
M  ISO  1   1  23
M  END
> <DATABASE_ID>
NP0027570

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])[C@]1([H])O[C@]([H])(O[C@@]2([H])OC([H])=C(C(=O)O[23C]([H])([H])[H])[C@@]3([H])C([H])([H])C([H])=C([C@@]23[H])[C@@]2([H])N([H])C([H])([H])C([H])([H])C3=C2N([H])C2=C3C([H])=C([H])C([H])=C2[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]1([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C27H32N2O9/c1-35-25(34)16-11-36-26(38-27-24(33)23(32)22(31)18(10-30)37-27)19-13(16)6-7-15(19)20-21-14(8-9-28-20)12-4-2-3-5-17(12)29-21/h2-5,7,11,13,18-20,22-24,26-33H,6,8-10H2,1H3/t13-,18+,19+,20-,22+,23-,24+,26-,27-/m1/s1/i1+11

> <INCHI_KEY>
CNDZNSRMCKQXEC-PHECFNKCSA-N

> <FORMULA>
C27H32N2O9

> <MOLECULAR_WEIGHT>
517.0

> <EXACT_MASS>
516.0

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
55.1563435074879

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(23C)methyl (1R,4aS,7aS)-7-[(1R)-1H,2H,3H,4H,9H-pyrido[3,4-b]indol-1-yl]-1-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-4-carboxylate

> <ALOGPS_LOGP>
0.53

> <JCHEM_LOGP>
-0.04614089799999872

> <ALOGPS_LOGS>
-2.78

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.198411615190278

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.207084664513967

> <JCHEM_PKA_STRONGEST_BASIC>
8.63644160361802

> <JCHEM_POLAR_SURFACE_AREA>
162.73000000000002

> <JCHEM_REFRACTIVITY>
133.4951

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.87e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(23C)methyl (1R,4aS,7aS)-7-[(1R)-1H,2H,3H,4H,9H-pyrido[3,4-b]indol-1-yl]-1-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-4-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 70 75  0  0  0  0  0  0  0  0999 V2000
    6.2217    1.9903   -0.1558 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8035    2.1503   -0.0989 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1097    1.1369   -0.6742 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6013    0.1470   -1.1962 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6433    1.3549   -0.5779 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1250    2.5092   -0.1317 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7871    2.7905   -0.0119 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0729    1.6326    0.0148 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0535    0.9866    1.2913 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7142    1.6441    2.2970 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0836    1.2503    2.1954 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8996    1.8747    3.1960 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3674    1.5002    2.9495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2561    2.2305    3.7875 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4437    1.4368    4.5984 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2220    2.0697    5.6202 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9663    1.7851    4.7870 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5244    1.2725    6.0533 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1319    1.1985    3.6514 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2302    1.6264    3.8082 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2666    0.6521   -1.1300 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4042   -0.7034   -1.0270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8450   -0.9135   -1.3923 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6824    0.0821   -0.6971 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0831    0.0621   -1.1634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2291    0.4607   -2.6528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1987   -0.2394   -3.4682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1122   -0.8395   -2.8646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3389   -1.3962   -3.8462 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9015   -1.1520   -5.0813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4616   -1.5182   -6.3590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2438   -1.1282   -7.4505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4182   -0.4008   -7.2697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8455   -0.0418   -5.9860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0759   -0.4232   -4.8701 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4550   -1.6348   -0.5802 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8179   -1.0668   -0.3374 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7611    0.2620   -1.1085 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6799    2.8586    0.3258 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5278    1.0910    0.3878 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5621    1.9509   -1.1953 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7075    3.3742    0.1641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0938    2.0056   -0.1184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6161    2.7326    2.1865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8172    2.9667    3.1071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5304    0.4289    3.1108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6388    1.7057    1.9087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8576    2.2465    4.6846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5766    0.3542    4.7196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7324    1.8973    6.4528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8332    2.8726    4.8453 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4506    1.3638    6.0388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1217    0.1036    3.7232 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6818    1.3576    2.9828 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0530    1.1327   -2.0936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1561   -1.9121   -1.0545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6513   -0.1130    0.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6696    0.7598   -0.5554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5080   -0.9364   -0.9976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0904    1.5435   -2.7582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2367    0.2134   -3.0039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4766   -1.9013   -3.6956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5470   -2.0834   -6.5043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9288   -1.3967   -8.4562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0102   -0.1073   -8.1328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7611    0.5264   -5.8543 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2077   -2.6722   -0.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9957   -0.9368    0.7355 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5926   -1.7237   -0.7454 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0606    0.0610   -2.1496 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
 19 20  1  0
 17 18  1  0
 35 27  1  0
 27 26  1  0
 28 23  1  0
 23 24  1  0
 24 25  1  0
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 23 22  1  0
 22 21  1  0
 28 29  1  0
 29 30  1  0
 38 37  1  0
 37 36  1  0
 36 22  2  0
 38 21  1  0
 15 17  1  0
 17 19  1  0
 30 35  2  0
 19 10  1  0
 35 34  1  0
 10 11  1  0
 38  5  1  0
 21  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  2  0
 34 33  2  0
 23 56  1  1
 11 12  1  0
 21 55  1  6
 33 32  1  0
 38 70  1  6
  8  9  1  0
 12 15  1  0
 13 14  1  0
 32 31  2  0
  5  3  1  0
 31 30  1  0
  3  4  2  0
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  3  2  1  0
  2  1  1  0
 15 16  1  0
 12 13  1  0
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  8 43  1  6
  6 42  1  0
 14 48  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
M  ISO  1   1  23
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       6.222   1.990  -0.156  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.803   2.150  -0.099  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.110   1.137  -0.674  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.601   0.147  -1.196  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.643   1.355  -0.578  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.125   2.509  -0.132  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.787   2.791  -0.012  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.073   1.633   0.015  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.054   0.987   1.291  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.714   1.644   2.297  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.084   1.250   2.195  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.900   1.875   3.196  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.367   1.500   2.950  0.00  0.00           C+0
HETATM   14  O   UNK     0      -5.256   2.231   3.788  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.444   1.437   4.598  0.00  0.00           C+0
HETATM   16  O   UNK     0      -3.222   2.070   5.620  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.966   1.785   4.787  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.524   1.272   6.053  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.132   1.198   3.651  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.230   1.626   3.808  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.267   0.652  -1.130  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.404  -0.703  -1.027  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.845  -0.914  -1.392  0.00  0.00           C+0
HETATM   24  N   UNK     0      -2.682   0.082  -0.697  0.00  0.00           N+0
HETATM   25  C   UNK     0      -4.083   0.062  -1.163  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.229   0.461  -2.653  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.199  -0.239  -3.468  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.112  -0.840  -2.865  0.00  0.00           C+0
HETATM   29  N   UNK     0      -1.339  -1.396  -3.846  0.00  0.00           N+0
HETATM   30  C   UNK     0      -1.902  -1.152  -5.081  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.462  -1.518  -6.359  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.244  -1.128  -7.450  0.00  0.00           C+0
HETATM   33  C   UNK     0      -3.418  -0.401  -7.270  0.00  0.00           C+0
HETATM   34  C   UNK     0      -3.845  -0.042  -5.986  0.00  0.00           C+0
HETATM   35  C   UNK     0      -3.076  -0.423  -4.870  0.00  0.00           C+0
HETATM   36  C   UNK     0       0.455  -1.635  -0.580  0.00  0.00           C+0
HETATM   37  C   UNK     0       1.818  -1.067  -0.337  0.00  0.00           C+0
HETATM   38  C   UNK     0       1.761   0.262  -1.109  0.00  0.00           C+0
HETATM   39  H   UNK     0       6.680   2.859   0.326  0.00  0.00           H+0
HETATM   40  H   UNK     0       6.528   1.091   0.388  0.00  0.00           H+0
HETATM   41  H   UNK     0       6.562   1.951  -1.195  0.00  0.00           H+0
HETATM   42  H   UNK     0       2.708   3.374   0.164  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.094   2.006  -0.118  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.616   2.733   2.187  0.00  0.00           H+0
HETATM   45  H   UNK     0      -2.817   2.967   3.107  0.00  0.00           H+0
HETATM   46  H   UNK     0      -4.530   0.429   3.111  0.00  0.00           H+0
HETATM   47  H   UNK     0      -4.639   1.706   1.909  0.00  0.00           H+0
HETATM   48  H   UNK     0      -4.858   2.247   4.685  0.00  0.00           H+0
HETATM   49  H   UNK     0      -2.577   0.354   4.720  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.732   1.897   6.453  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.833   2.873   4.845  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.451   1.364   6.039  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.122   0.104   3.723  0.00  0.00           H+0
HETATM   54  H   UNK     0       1.682   1.358   2.983  0.00  0.00           H+0
HETATM   55  H   UNK     0       0.053   1.133  -2.094  0.00  0.00           H+0
HETATM   56  H   UNK     0      -2.156  -1.912  -1.054  0.00  0.00           H+0
HETATM   57  H   UNK     0      -2.651  -0.113   0.305  0.00  0.00           H+0
HETATM   58  H   UNK     0      -4.670   0.760  -0.555  0.00  0.00           H+0
HETATM   59  H   UNK     0      -4.508  -0.936  -0.998  0.00  0.00           H+0
HETATM   60  H   UNK     0      -4.090   1.544  -2.758  0.00  0.00           H+0
HETATM   61  H   UNK     0      -5.237   0.213  -3.004  0.00  0.00           H+0
HETATM   62  H   UNK     0      -0.477  -1.901  -3.696  0.00  0.00           H+0
HETATM   63  H   UNK     0      -0.547  -2.083  -6.504  0.00  0.00           H+0
HETATM   64  H   UNK     0      -1.929  -1.397  -8.456  0.00  0.00           H+0
HETATM   65  H   UNK     0      -4.010  -0.107  -8.133  0.00  0.00           H+0
HETATM   66  H   UNK     0      -4.761   0.526  -5.854  0.00  0.00           H+0
HETATM   67  H   UNK     0       0.208  -2.672  -0.398  0.00  0.00           H+0
HETATM   68  H   UNK     0       1.996  -0.937   0.736  0.00  0.00           H+0
HETATM   69  H   UNK     0       2.593  -1.724  -0.745  0.00  0.00           H+0
HETATM   70  H   UNK     0       2.061   0.061  -2.150  0.00  0.00           H+0
CONECT    1    2   39   40   41                                             
CONECT    2    3    1                                                       
CONECT    3    5    4    2                                                  
CONECT    4    3                                                            
CONECT    5   38    6    3                                                  
CONECT    6    7    5   42                                                  
CONECT    7    8    6                                                       
CONECT    8   21    7    9   43                                             
CONECT    9   10    8                                                       
CONECT   10    9   19   11   44                                             
CONECT   11   10   12                                                       
CONECT   12   11   15   13   45                                             
CONECT   13   14   12   46   47                                             
CONECT   14   13   48                                                       
CONECT   15   17   12   16   49                                             
CONECT   16   15   50                                                       
CONECT   17   18   15   19   51                                             
CONECT   18   17   52                                                       
CONECT   19   20   17   10   53                                             
CONECT   20   19   54                                                       
CONECT   21   22   38    8   55                                             
CONECT   22   23   21   36                                                  
CONECT   23   28   24   22   56                                             
CONECT   24   23   25   57                                                  
CONECT   25   24   26   58   59                                             
CONECT   26   27   25   60   61                                             
CONECT   27   35   26   28                                                  
CONECT   28   23   29   27                                                  
CONECT   29   28   30   62                                                  
CONECT   30   29   35   31                                                  
CONECT   31   32   30   63                                                  
CONECT   32   33   31   64                                                  
CONECT   33   34   32   65                                                  
CONECT   34   35   33   66                                                  
CONECT   35   27   30   34                                                  
CONECT   36   37   22   67                                                  
CONECT   37   38   36   68   69                                             
CONECT   38   37   21    5   70                                             
CONECT   39    1                                                            
CONECT   40    1                                                            
CONECT   41    1                                                            
CONECT   42    6                                                            
CONECT   43    8                                                            
CONECT   44   10                                                            
CONECT   45   12                                                            
CONECT   46   13                                                            
CONECT   47   13                                                            
CONECT   48   14                                                            
CONECT   49   15                                                            
CONECT   50   16                                                            
CONECT   51   17                                                            
CONECT   52   18                                                            
CONECT   53   19                                                            
CONECT   54   20                                                            
CONECT   55   21                                                            
CONECT   56   23                                                            
CONECT   57   24                                                            
CONECT   58   25                                                            
CONECT   59   25                                                            
CONECT   60   26                                                            
CONECT   61   26                                                            
CONECT   62   29                                                            
CONECT   63   31                                                            
CONECT   64   32                                                            
CONECT   65   33                                                            
CONECT   66   34                                                            
CONECT   67   36                                                            
CONECT   68   37                                                            
CONECT   69   37                                                            
CONECT   70   38                                                            
MASTER        0    0    0    0    0    0    0    0   70    0  150    0
END

RDKit          3D

70 75  0  0  0  0  0  0  0  0999 V2000
    6.2217    1.9903   -0.1558 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8035    2.1503   -0.0989 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6013    0.1470   -1.1962 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6433    1.3549   -0.5779 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1250    2.5092   -0.1317 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7871    2.7905   -0.0119 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0729    1.6326    0.0148 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0535    0.9866    1.2913 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7142    1.6441    2.2970 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0836    1.2503    2.1954 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8996    1.8747    3.1960 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3674    1.5002    2.9495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2561    2.2305    3.7875 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4437    1.4368    4.5984 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2220    2.0697    5.6202 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1319    1.1985    3.6514 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2302    1.6264    3.8082 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2666    0.6521   -1.1300 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4042   -0.7034   -1.0270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8450   -0.9135   -1.3923 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6824    0.0821   -0.6971 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0831    0.0621   -1.1634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2291    0.4607   -2.6528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1987   -0.2394   -3.4682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1122   -0.8395   -2.8646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3389   -1.3962   -3.8462 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9015   -1.1520   -5.0813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4616   -1.5182   -6.3590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2438   -1.1282   -7.4505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4182   -0.4008   -7.2697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8455   -0.0418   -5.9860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0759   -0.4232   -4.8701 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4550   -1.6348   -0.5802 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8179   -1.0668   -0.3374 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7611    0.2620   -1.1085 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6799    2.8586    0.3258 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7075    3.3742    0.1641 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1561   -1.9121   -1.0545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6513   -0.1130    0.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6696    0.7598   -0.5554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5080   -0.9364   -0.9976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0904    1.5435   -2.7582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2367    0.2134   -3.0039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4766   -1.9013   -3.6956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5470   -2.0834   -6.5043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9288   -1.3967   -8.4562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0102   -0.1073   -8.1328 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2077   -2.6722   -0.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9957   -0.9368    0.7355 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5926   -1.7237   -0.7454 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0606    0.0610   -2.1496 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
 19 20  1  0
 17 18  1  0
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 38 37  1  0
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 10 11  1  0
 38  5  1  0
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  8  7  1  0
  7  6  1  0
  6  5  2  0
 34 33  2  0
 23 56  1  1
 11 12  1  0
 21 55  1  6
 33 32  1  0
 38 70  1  6
  8  9  1  0
 12 15  1  0
 13 14  1  0
 32 31  2  0
  5  3  1  0
 31 30  1  0
  3  4  2  0
 27 28  2  0
  3  2  1  0
  2  1  1  0
 15 16  1  0
 12 13  1  0
 16 50  1  0
 15 49  1  6
 10 44  1  6
 13 46  1  0
 13 47  1  0
 12 45  1  1
 19 53  1  6
 20 54  1  0
 17 51  1  1
 18 52  1  0
 29 62  1  0
 34 66  1  0
 33 65  1  0
 32 64  1  0
 31 63  1  0
 24 57  1  0
 25 58  1  0
 25 59  1  0
 26 60  1  0
 26 61  1  0
 37 68  1  0
 37 69  1  0
 36 67  1  0
  8 43  1  6
  6 42  1  0
 14 48  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
M  ISO  1   1  23
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₂N₂O₉

Average Mass

517.0000 Da

Monoisotopic Mass

516.00000 Da

IUPAC Name

(23C)methyl (1R,4aS,7aS)-7-[(1R)-1H,2H,3H,4H,9H-pyrido[3,4-b]indol-1-yl]-1-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-4-carboxylate

Traditional Name

(23C)methyl (1R,4aS,7aS)-7-[(1R)-1H,2H,3H,4H,9H-pyrido[3,4-b]indol-1-yl]-1-{[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,7aH-cyclopenta[c]pyran-4-carboxylate

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)O[23C]([H])([H])[H])[C@@]3([H])C([H])([H])C([H])=C([C@@]23[H])[C@@]2([H])N([H])C([H])([H])C([H])([H])C3=C2N([H])C2=C3C([H])=C([H])C([H])=C2[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]1([H])O[H]

InChI Identifier

InChI=1S/C27H32N2O9/c1-35-25(34)16-11-36-26(38-27-24(33)23(32)22(31)18(10-30)37-27)19-13(16)6-7-15(19)20-21-14(8-9-28-20)12-4-2-3-5-17(12)29-21/h2-5,7,11,13,18-20,22-24,26-33H,6,8-10H2,1H3/t13-,18+,19+,20-,22+,23-,24+,26-,27-/m1/s1/i1+11

InChI Key

CNDZNSRMCKQXEC-PHECFNKCSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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	Dusman, L. T., et al, J. Nat. Prod. 67, 1886 (2004)
Psychotria umbellata	Plant	KNApSAcK

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	0.53	ALOGPS
logP	-0.046	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	8.64	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	162.73 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	133.5 m³·mol⁻¹	ChemAxon
Polarizability	55.16 Å³	ChemAxon
Number of Rings	6	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

Dusman, L. T., et al. (2004). Dusman, L. T., et al, J. Nat. Prod. 67, 1886 (2004). J. Nat. Prod..

Showing NP-Card for croceaine A (NP0027570)

MOL for NP0027570 (croceaine A)

3D MOL for NP0027570 (croceaine A)

3D SDF for NP0027570 (croceaine A)

3D-SDF for NP0027570 (croceaine A)

PDB for NP0027570 (croceaine A)

3D PDB for NP0027570 (croceaine A)

SMILES for NP0027570 (croceaine A)

INCHI for NP0027570 (croceaine A)

Structure for NP0027570 (croceaine A)

3D Structure for NP0027570 (croceaine A)