NP-MRD: Showing NP-Card for hostasinine A epimer (NP0038891)

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Record Information

Version

2.0

Created at

2021-06-20 21:27:48 UTC

Updated at

2021-06-30 00:11:55 UTC

NP-MRD ID

NP0038891

Secondary Accession Numbers

None

Natural Product Identification

Common Name

hostasinine A epimer

Provided By

JEOL Database JEOL Logo

Description

(1S,11R,12R,16R,19R)-11,16-dihydroxy-19-methoxy-5,7-dioxa-14λ⁵-azapentacyclo[10.4.3.0¹,¹³.0²,¹⁰.0⁴,⁸]Nonadeca-2,4(8),9,13,17-pentaen-14-one belongs to the class of organic compounds known as tetralins. These are polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane. hostasinine A epimer is found in Hosta plantaginea. hostasinine A epimer was first documented in 2007 (Wang, Y.-H., et al.). Based on a literature review very few articles have been published on (1S,11R,12R,16R,19R)-11,16-dihydroxy-19-methoxy-5,7-dioxa-14λ⁵-azapentacyclo[10.4.3.0¹,¹³.0²,¹⁰.0⁴,⁸]Nonadeca-2,4(8),9,13,17-pentaen-14-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202123273D          

 41 45  0  0  0  0            999 V2000
    5.0048    1.9933    2.1270 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0435    1.7115    1.1113 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4180    0.4401    1.2934 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0930   -0.0769   -0.0898 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9129   -0.6315   -0.4229 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7561   -0.7687    0.5494 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3360   -0.6301    1.9113 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8469   -1.4923    2.7441 N   0  3  0  0  0  4  0  0  0  0  0  0
    1.1299   -1.5106    3.9802 O   0  5  0  0  0  1  0  0  0  0  0  0
   -0.1581   -2.3887    2.1630 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1171   -2.1843    0.6729 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0104   -3.2271    0.2612 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1983    0.5199    2.2467 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2404    1.7417    2.1136 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9291    2.9757    1.9529 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1151    1.6452    1.0686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7041    2.7721    0.8617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7427    2.6747   -0.0376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9959    1.5150   -0.7273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2307    0.3807   -0.5590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1689    0.4266    0.3616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0571    1.6325   -1.5703 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4417    3.0032   -1.3309 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6166    3.6675   -0.3531 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5393    1.9833    3.1167 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4120    2.9910    1.9428 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8245    1.2698    2.0858 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1454   -0.2722    1.7089 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8790    0.0048   -0.8370 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7553   -0.9587   -1.4478 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0145   -3.4067    2.5198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1387   -2.0099    2.4648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8018   -2.3112    0.0937 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1464   -3.1503   -0.6997 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5712    0.4861    3.2760 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7110    1.8174    3.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6393    2.8192    1.2976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5235    3.7014    1.3944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4524   -0.5016   -1.1487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4808    3.0192   -0.9824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3795    3.5546   -2.2762 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 18  1  0  0  0  0
 21 16  2  0  0  0  0
  7  8  2  0  0  0  0
 21  6  1  0  0  0  0
  8 10  1  0  0  0  0
 16 14  1  0  0  0  0
  6 11  1  0  0  0  0
 10 11  1  0  0  0  0
 14 13  1  0  0  0  0
 13  3  1  0  0  0  0
 13  7  1  0  0  0  0
  6  5  1  6  0  0  0
  7  6  1  0  0  0  0
  5  4  2  0  0  0  0
  4  3  1  0  0  0  0
 18 19  1  0  0  0  0
  8  9  1  0  0  0  0
 18 17  2  0  0  0  0
 11 12  1  0  0  0  0
 17 16  1  0  0  0  0
  3  2  1  0  0  0  0
 14 15  1  0  0  0  0
 21 20  1  0  0  0  0
  2  1  1  0  0  0  0
 20 19  2  0  0  0  0
 13 35  1  1  0  0  0
 17 38  1  0  0  0  0
 20 39  1  0  0  0  0
 14 36  1  1  0  0  0
 23 40  1  0  0  0  0
 23 41  1  0  0  0  0
 10 31  1  0  0  0  0
 10 32  1  0  0  0  0
 11 33  1  6  0  0  0
  3 28  1  1  0  0  0
  5 30  1  0  0  0  0
  4 29  1  0  0  0  0
 12 34  1  0  0  0  0
 15 37  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
M  CHG  2   8   1   9  -1
M  END

     RDKit          3D

 41 45  0  0  0  0  0  0  0  0999 V2000
    5.0048    1.9933    2.1270 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0435    1.7115    1.1113 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4180    0.4401    1.2934 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0930   -0.0769   -0.0898 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9129   -0.6315   -0.4229 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7561   -0.7687    0.5494 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3360   -0.6301    1.9113 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8469   -1.4923    2.7441 N   0  0  0  0  0  4  0  0  0  0  0  0
    1.1299   -1.5106    3.9802 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.1581   -2.3887    2.1630 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1171   -2.1843    0.6729 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0104   -3.2271    0.2612 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1983    0.5199    2.2467 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2404    1.7417    2.1136 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9291    2.9757    1.9529 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1151    1.6452    1.0686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7041    2.7721    0.8617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7427    2.6747   -0.0376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9959    1.5150   -0.7273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2307    0.3807   -0.5590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1689    0.4266    0.3616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0571    1.6325   -1.5703 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4417    3.0032   -1.3309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6166    3.6675   -0.3531 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5393    1.9833    3.1167 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4120    2.9910    1.9428 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8245    1.2698    2.0858 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1454   -0.2722    1.7089 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8790    0.0048   -0.8370 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7553   -0.9587   -1.4478 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0145   -3.4067    2.5198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1387   -2.0099    2.4648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8018   -2.3112    0.0937 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1464   -3.1503   -0.6997 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5712    0.4861    3.2760 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7110    1.8174    3.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6393    2.8192    1.2976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5235    3.7014    1.3944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4524   -0.5016   -1.1487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4808    3.0192   -0.9824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3795    3.5546   -2.2762 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 22  1  0
 22 23  1  0
 23 24  1  0
 24 18  1  0
 21 16  2  0
  7  8  2  0
 21  6  1  0
  8 10  1  0
 16 14  1  0
  6 11  1  0
 10 11  1  0
 14 13  1  0
 13  3  1  0
 13  7  1  0
  6  5  1  6
  7  6  1  0
  5  4  2  0
  4  3  1  0
 18 19  1  0
  8  9  1  0
 18 17  2  0
 11 12  1  0
 17 16  1  0
  3  2  1  0
 14 15  1  0
 21 20  1  0
  2  1  1  0
 20 19  2  0
 13 35  1  1
 17 38  1  0
 20 39  1  0
 14 36  1  1
 23 40  1  0
 23 41  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  6
  3 28  1  1
  5 30  1  0
  4 29  1  0
 12 34  1  0
 15 37  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
M  CHG  2   8   1   9  -1
M  END


  Mrv1652306202123273D          

 41 45  0  0  0  0            999 V2000
    5.0048    1.9933    2.1270 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0435    1.7115    1.1113 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4180    0.4401    1.2934 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0930   -0.0769   -0.0898 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9129   -0.6315   -0.4229 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7561   -0.7687    0.5494 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3360   -0.6301    1.9113 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8469   -1.4923    2.7441 N   0  3  0  0  0  4  0  0  0  0  0  0
    1.1299   -1.5106    3.9802 O   0  5  0  0  0  1  0  0  0  0  0  0
   -0.1581   -2.3887    2.1630 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1171   -2.1843    0.6729 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0104   -3.2271    0.2612 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1983    0.5199    2.2467 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2404    1.7417    2.1136 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9291    2.9757    1.9529 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1151    1.6452    1.0686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7041    2.7721    0.8617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7427    2.6747   -0.0376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9959    1.5150   -0.7273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2307    0.3807   -0.5590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1689    0.4266    0.3616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0571    1.6325   -1.5703 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4417    3.0032   -1.3309 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6166    3.6675   -0.3531 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5393    1.9833    3.1167 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4120    2.9910    1.9428 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8245    1.2698    2.0858 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1454   -0.2722    1.7089 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8790    0.0048   -0.8370 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7553   -0.9587   -1.4478 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0145   -3.4067    2.5198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1387   -2.0099    2.4648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8018   -2.3112    0.0937 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1464   -3.1503   -0.6997 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5712    0.4861    3.2760 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7110    1.8174    3.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6393    2.8192    1.2976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5235    3.7014    1.3944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4524   -0.5016   -1.1487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4808    3.0192   -0.9824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3795    3.5546   -2.2762 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 18  1  0  0  0  0
 21 16  2  0  0  0  0
  7  8  2  0  0  0  0
 21  6  1  0  0  0  0
  8 10  1  0  0  0  0
 16 14  1  0  0  0  0
  6 11  1  0  0  0  0
 10 11  1  0  0  0  0
 14 13  1  0  0  0  0
 13  3  1  0  0  0  0
 13  7  1  0  0  0  0
  6  5  1  6  0  0  0
  7  6  1  0  0  0  0
  5  4  2  0  0  0  0
  4  3  1  0  0  0  0
 18 19  1  0  0  0  0
  8  9  1  0  0  0  0
 18 17  2  0  0  0  0
 11 12  1  0  0  0  0
 17 16  1  0  0  0  0
  3  2  1  0  0  0  0
 14 15  1  0  0  0  0
 21 20  1  0  0  0  0
  2  1  1  0  0  0  0
 20 19  2  0  0  0  0
 13 35  1  1  0  0  0
 17 38  1  0  0  0  0
 20 39  1  0  0  0  0
 14 36  1  1  0  0  0
 23 40  1  0  0  0  0
 23 41  1  0  0  0  0
 10 31  1  0  0  0  0
 10 32  1  0  0  0  0
 11 33  1  6  0  0  0
  3 28  1  1  0  0  0
  5 30  1  0  0  0  0
  4 29  1  0  0  0  0
 12 34  1  0  0  0  0
 15 37  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
M  CHG  2   8   1   9  -1
M  END
> <DATABASE_ID>
NP0038891

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])C([H])([H])[N+]([O-])=C2[C@@]3([H])[C@]([H])(OC([H])([H])[H])C([H])=C([H])[C@@]12C1=C(C([H])=C2OC([H])([H])OC2=C1[H])[C@]3([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C17H17NO6/c1-22-10-2-3-17-9-5-12-11(23-7-24-12)4-8(9)15(20)14(10)16(17)18(21)6-13(17)19/h2-5,10,13-15,19-20H,6-7H2,1H3/t10-,13+,14+,15+,17-/m1/s1

> <INCHI_KEY>
SOXMOSOZKDGVHZ-MEELUSRTSA-N

> <FORMULA>
C17H17NO6

> <MOLECULAR_WEIGHT>
331.324

> <EXACT_MASS>
331.105587271

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
32.79042504607225

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,11R,12R,16R,19R)-11,16-dihydroxy-19-methoxy-5,7-dioxa-14-azapentacyclo[10.4.3.0^{1,13}.0^{2,10}.0^{4,8}]nonadeca-2(10),3,8,13,17-pentaen-14-ium-14-olate

> <ALOGPS_LOGP>
-0.75

> <JCHEM_LOGP>
-2.951088959138412

> <ALOGPS_LOGS>
-2.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.33407991694519

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.006097063407233

> <JCHEM_PKA_STRONGEST_BASIC>
-3.338678013316044

> <JCHEM_POLAR_SURFACE_AREA>
94.22000000000001

> <JCHEM_REFRACTIVITY>
84.8749

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.34e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,11R,12R,16R,19R)-11,16-dihydroxy-19-methoxy-5,7-dioxa-14-azapentacyclo[10.4.3.0^{1,13}.0^{2,10}.0^{4,8}]nonadeca-2(10),3,8,13,17-pentaen-14-ium-14-olate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 41 45  0  0  0  0  0  0  0  0999 V2000
    5.0048    1.9933    2.1270 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0435    1.7115    1.1113 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4180    0.4401    1.2934 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0930   -0.0769   -0.0898 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9129   -0.6315   -0.4229 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7561   -0.7687    0.5494 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3360   -0.6301    1.9113 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8469   -1.4923    2.7441 N   0  0  0  0  0  4  0  0  0  0  0  0
    1.1299   -1.5106    3.9802 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.1581   -2.3887    2.1630 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1171   -2.1843    0.6729 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0104   -3.2271    0.2612 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1983    0.5199    2.2467 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2404    1.7417    2.1136 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9291    2.9757    1.9529 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1151    1.6452    1.0686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7041    2.7721    0.8617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7427    2.6747   -0.0376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9959    1.5150   -0.7273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2307    0.3807   -0.5590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1689    0.4266    0.3616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0571    1.6325   -1.5703 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4417    3.0032   -1.3309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6166    3.6675   -0.3531 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5393    1.9833    3.1167 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4120    2.9910    1.9428 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8245    1.2698    2.0858 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1454   -0.2722    1.7089 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8790    0.0048   -0.8370 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7553   -0.9587   -1.4478 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0145   -3.4067    2.5198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1387   -2.0099    2.4648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8018   -2.3112    0.0937 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1464   -3.1503   -0.6997 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5712    0.4861    3.2760 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7110    1.8174    3.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6393    2.8192    1.2976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5235    3.7014    1.3944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4524   -0.5016   -1.1487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4808    3.0192   -0.9824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3795    3.5546   -2.2762 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 22  1  0
 22 23  1  0
 23 24  1  0
 24 18  1  0
 21 16  2  0
  7  8  2  0
 21  6  1  0
  8 10  1  0
 16 14  1  0
  6 11  1  0
 10 11  1  0
 14 13  1  0
 13  3  1  0
 13  7  1  0
  6  5  1  6
  7  6  1  0
  5  4  2  0
  4  3  1  0
 18 19  1  0
  8  9  1  0
 18 17  2  0
 11 12  1  0
 17 16  1  0
  3  2  1  0
 14 15  1  0
 21 20  1  0
  2  1  1  0
 20 19  2  0
 13 35  1  1
 17 38  1  0
 20 39  1  0
 14 36  1  1
 23 40  1  0
 23 41  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  6
  3 28  1  1
  5 30  1  0
  4 29  1  0
 12 34  1  0
 15 37  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
M  CHG  2   8   1   9  -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       5.005   1.993   2.127  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.043   1.712   1.111  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.418   0.440   1.293  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.093  -0.077  -0.090  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.913  -0.632  -0.423  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.756  -0.769   0.549  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.336  -0.630   1.911  0.00  0.00           C+0
HETATM    8  N   UNK     0       0.847  -1.492   2.744  0.00  0.00           N+1
HETATM    9  O   UNK     0       1.130  -1.511   3.980  0.00  0.00           O-1
HETATM   10  C   UNK     0      -0.158  -2.389   2.163  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.117  -2.184   0.673  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.010  -3.227   0.261  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.198   0.520   2.247  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.240   1.742   2.114  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.929   2.976   1.953  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.115   1.645   1.069  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.704   2.772   0.862  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.743   2.675  -0.038  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.996   1.515  -0.727  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.231   0.381  -0.559  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.169   0.427   0.362  0.00  0.00           C+0
HETATM   22  O   UNK     0      -3.057   1.633  -1.570  0.00  0.00           O+0
HETATM   23  C   UNK     0      -3.442   3.003  -1.331  0.00  0.00           C+0
HETATM   24  O   UNK     0      -2.617   3.668  -0.353  0.00  0.00           O+0
HETATM   25  H   UNK     0       4.539   1.983   3.117  0.00  0.00           H+0
HETATM   26  H   UNK     0       5.412   2.991   1.943  0.00  0.00           H+0
HETATM   27  H   UNK     0       5.824   1.270   2.086  0.00  0.00           H+0
HETATM   28  H   UNK     0       4.145  -0.272   1.709  0.00  0.00           H+0
HETATM   29  H   UNK     0       3.879   0.005  -0.837  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.755  -0.959  -1.448  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.015  -3.407   2.520  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.139  -2.010   2.465  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.802  -2.311   0.094  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.146  -3.150  -0.700  0.00  0.00           H+0
HETATM   35  H   UNK     0       2.571   0.486   3.276  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.711   1.817   3.074  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.639   2.819   1.298  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.524   3.701   1.394  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.452  -0.502  -1.149  0.00  0.00           H+0
HETATM   40  H   UNK     0      -4.481   3.019  -0.982  0.00  0.00           H+0
HETATM   41  H   UNK     0      -3.380   3.555  -2.276  0.00  0.00           H+0
CONECT    1    2   25   26   27                                             
CONECT    2    3    1                                                       
CONECT    3   13    4    2   28                                             
CONECT    4    5    3   29                                                  
CONECT    5    6    4   30                                                  
CONECT    6   21   11    5    7                                             
CONECT    7    8   13    6                                                  
CONECT    8    7   10    9                                                  
CONECT    9    8                                                            
CONECT   10    8   11   31   32                                             
CONECT   11    6   10   12   33                                             
CONECT   12   11   34                                                       
CONECT   13   14    3    7   35                                             
CONECT   14   16   13   15   36                                             
CONECT   15   14   37                                                       
CONECT   16   21   14   17                                                  
CONECT   17   18   16   38                                                  
CONECT   18   24   19   17                                                  
CONECT   19   22   18   20                                                  
CONECT   20   21   19   39                                                  
CONECT   21   16    6   20                                                  
CONECT   22   19   23                                                       
CONECT   23   22   24   40   41                                             
CONECT   24   23   18                                                       
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    3                                                            
CONECT   29    4                                                            
CONECT   30    5                                                            
CONECT   31   10                                                            
CONECT   32   10                                                            
CONECT   33   11                                                            
CONECT   34   12                                                            
CONECT   35   13                                                            
CONECT   36   14                                                            
CONECT   37   15                                                            
CONECT   38   17                                                            
CONECT   39   20                                                            
CONECT   40   23                                                            
CONECT   41   23                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   90    0
END

RDKit          3D

41 45  0  0  0  0  0  0  0  0999 V2000
    5.0048    1.9933    2.1270 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0435    1.7115    1.1113 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4180    0.4401    1.2934 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0930   -0.0769   -0.0898 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9129   -0.6315   -0.4229 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7561   -0.7687    0.5494 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3360   -0.6301    1.9113 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8469   -1.4923    2.7441 N   0  0  0  0  0  4  0  0  0  0  0  0
    1.1299   -1.5106    3.9802 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.1581   -2.3887    2.1630 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1171   -2.1843    0.6729 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0104   -3.2271    0.2612 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1983    0.5199    2.2467 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2404    1.7417    2.1136 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9291    2.9757    1.9529 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1151    1.6452    1.0686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7041    2.7721    0.8617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7427    2.6747   -0.0376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9959    1.5150   -0.7273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2307    0.3807   -0.5590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1689    0.4266    0.3616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0571    1.6325   -1.5703 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4417    3.0032   -1.3309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6166    3.6675   -0.3531 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5393    1.9833    3.1167 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4120    2.9910    1.9428 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8245    1.2698    2.0858 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1454   -0.2722    1.7089 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8790    0.0048   -0.8370 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7553   -0.9587   -1.4478 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0145   -3.4067    2.5198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1387   -2.0099    2.4648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8018   -2.3112    0.0937 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1464   -3.1503   -0.6997 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5712    0.4861    3.2760 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7110    1.8174    3.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6393    2.8192    1.2976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5235    3.7014    1.3944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4524   -0.5016   -1.1487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4808    3.0192   -0.9824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3795    3.5546   -2.2762 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 22  1  0
 22 23  1  0
 23 24  1  0
 24 18  1  0
 21 16  2  0
  7  8  2  0
 21  6  1  0
  8 10  1  0
 16 14  1  0
  6 11  1  0
 10 11  1  0
 14 13  1  0
 13  3  1  0
 13  7  1  0
  6  5  1  6
  7  6  1  0
  5  4  2  0
  4  3  1  0
 18 19  1  0
  8  9  1  0
 18 17  2  0
 11 12  1  0
 17 16  1  0
  3  2  1  0
 14 15  1  0
 21 20  1  0
  2  1  1  0
 20 19  2  0
 13 35  1  1
 17 38  1  0
 20 39  1  0
 14 36  1  1
 23 40  1  0
 23 41  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  6
  3 28  1  1
  5 30  1  0
  4 29  1  0
 12 34  1  0
 15 37  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
M  CHG  2   8   1   9  -1
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₁₇NO₆

Average Mass

331.3240 Da

Monoisotopic Mass

331.10559 Da

IUPAC Name

(1S,11R,12R,16R,19R)-11,16-dihydroxy-19-methoxy-5,7-dioxa-14-azapentacyclo[10.4.3.0^{1,13}.0^{2,10}.0^{4,8}]nonadeca-2(10),3,8,13,17-pentaen-14-ium-14-olate

Traditional Name

(1S,11R,12R,16R,19R)-11,16-dihydroxy-19-methoxy-5,7-dioxa-14-azapentacyclo[10.4.3.0^{1,13}.0^{2,10}.0^{4,8}]nonadeca-2(10),3,8,13,17-pentaen-14-ium-14-olate

CAS Registry Number

Not Available

SMILES

[H]O[C@@]1([H])C([H])([H])[N+]([O-])=C2[C@@]3([H])[C@]([H])(OC([H])([H])[H])C([H])=C([H])[C@@]12C1=C(C([H])=C2OC([H])([H])OC2=C1[H])[C@]3([H])O[H]

InChI Identifier

InChI=1S/C17H17NO6/c1-22-10-2-3-17-9-5-12-11(23-7-24-12)4-8(9)15(20)14(10)16(17)18(21)6-13(17)19/h2-5,10,13-15,19-20H,6-7H2,1H3/t10-,13+,14+,15+,17-/m1/s1

InChI Key

SOXMOSOZKDGVHZ-MEELUSRTSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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
Hosta plantaginea	JEOL database	Wang, Y.-H., et al, Org. Lett. 9, 5279 (2007)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetralins. These are polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Tetralins

Sub Class

Not Available

Direct Parent

Tetralins

Alternative Parents

Substituents

Tetralin
Benzodioxole
Indole or derivatives
Pyrroline
Nitrone
Secondary alcohol
Acetal
Dialkyl ether
Ether
Oxacycle
Allyl-type 1,3-dipolar organic compound
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organoheterocyclic compound
Azacycle
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Organic zwitterion
Alcohol
Organic oxygen compound
Organic salt
Organopnictogen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.75	ALOGPS
logP	-3	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	3.01	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	94.22 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	84.87 m³·mol⁻¹	ChemAxon
Polarizability	32.79 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23729953

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wang, Y.-H., et al. (2007). Wang, Y.-H., et al, Org. Lett. 9, 5279 (2007). Org. Lett..

Showing NP-Card for hostasinine A epimer (NP0038891)

MOL for NP0038891 (hostasinine A epimer)

3D MOL for NP0038891 (hostasinine A epimer)

3D SDF for NP0038891 (hostasinine A epimer)

3D-SDF for NP0038891 (hostasinine A epimer)

PDB for NP0038891 (hostasinine A epimer)

3D PDB for NP0038891 (hostasinine A epimer)

SMILES for NP0038891 (hostasinine A epimer)

INCHI for NP0038891 (hostasinine A epimer)

Structure for NP0038891 (hostasinine A epimer)

3D Structure for NP0038891 (hostasinine A epimer)