NP-MRD: Showing NP-Card for hostasine (NP0033217)

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Record Information

Version

2.0

Created at

2021-06-19 23:49:17 UTC

Updated at

2021-06-30 00:02:52 UTC

NP-MRD ID

NP0033217

Secondary Accession Numbers

None

Natural Product Identification

Common Name

hostasine

Provided By

JEOL Database JEOL Logo

Description

Hostasine belongs to the class of organic compounds known as homolycorine-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids compounds containing the homolycorine skeleton, made up of a [3,4-g]benzopyranone ring due to the oxidation of the hydroxyl group at the C6. They are biogenetically formed through a restructuring of lycorine-type alkaloids. hostasine is found in Hosta plantaginea. hostasine was first documented in 2007 (PMID: 17822295). Based on a literature review very few articles have been published on Hostasine.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202101493D          

 47 50  0  0  0  0            999 V2000
    3.2047   -0.6461    3.7807 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1800    0.3297    3.5950 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4695    0.1994    2.4264 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1560    1.4156    1.7902 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5561    2.6015    2.3451 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4512    1.4647    0.5913 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0431    0.2645    0.0290 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3225   -0.9361    0.6631 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0080   -1.0003    1.8721 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2529   -2.2013    2.4727 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1550   -2.5729    3.3097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2287   -2.0241   -0.1376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1868   -3.2150    0.0925 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7960   -1.4531   -1.2384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7237    0.0061   -1.2260 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0562    0.4593   -2.4954 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2148    1.8896   -2.5158 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6691   -0.0063   -3.7883 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3235   -1.3557   -4.0877 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1663    0.0584   -3.7155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8265    0.3475   -2.5837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3072    0.2438   -2.4004 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4744    0.4809   -0.9037 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1830    0.0935   -0.2994 N   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0783    0.6425    1.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1626    0.6194   -1.2482 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9752   -0.1968    4.4150 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8102   -1.5164    4.3122 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6822   -0.9387    2.8388 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0114    2.3586    3.1755 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2375    2.4192    0.1192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7778   -2.6599    2.7427 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3816   -3.5515    3.7429 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0318   -1.8580    4.1307 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7895    2.1041   -3.2733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3373    0.6088   -4.6322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7005   -1.9125   -3.3771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7139   -0.2014   -4.6180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8478    0.9961   -2.9822 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.6966    1.5422   -0.7259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9396    0.3324    1.6516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1990    0.2565    1.5677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0373    1.7375    1.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0974    1.7120   -1.1340 H   0  0  0  0  0  0  0  0  0  0  0  0
 15  7  1  0  0  0  0
 26 21  1  0  0  0  0
  4  3  2  0  0  0  0
 15 26  1  0  0  0  0
  3  9  1  0  0  0  0
  9  8  2  0  0  0  0
 16 18  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
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 12 13  2  0  0  0  0
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  4  5  1  0  0  0  0
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  3  2  1  0  0  0  0
 18 20  1  0  0  0  0
  9 10  1  0  0  0  0
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 10 11  1  0  0  0  0
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 15 16  1  0  0  0  0
 26 47  1  1  0  0  0
  8 12  1  0  0  0  0
 16 17  1  0  0  0  0
 12 14  1  0  0  0  0
 18 19  1  0  0  0  0
  2  1  1  0  0  0  0
 15 14  1  6  0  0  0
 16 35  1  1  0  0  0
 18 37  1  6  0  0  0
 20 39  1  0  0  0  0
  6 31  1  0  0  0  0
 22 40  1  0  0  0  0
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 23 43  1  0  0  0  0
  5 30  1  0  0  0  0
 11 32  1  0  0  0  0
 11 33  1  0  0  0  0
 11 34  1  0  0  0  0
 25 44  1  0  0  0  0
 25 45  1  0  0  0  0
 25 46  1  0  0  0  0
 17 36  1  0  0  0  0
 19 38  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
M  END

     RDKit          3D

 47 50  0  0  0  0  0  0  0  0999 V2000
    3.2047   -0.6461    3.7807 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1800    0.3297    3.5950 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4695    0.1994    2.4264 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1560    1.4156    1.7902 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5561    2.6015    2.3451 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4512    1.4647    0.5913 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0431    0.2645    0.0290 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3225   -0.9361    0.6631 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0080   -1.0003    1.8721 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2529   -2.2013    2.4727 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1550   -2.5729    3.3097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2287   -2.0241   -0.1376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1868   -3.2150    0.0925 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7960   -1.4531   -1.2384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7237    0.0061   -1.2260 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0562    0.4593   -2.4954 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2148    1.8896   -2.5158 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6691   -0.0063   -3.7883 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3235   -1.3557   -4.0877 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1663    0.0584   -3.7155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8265    0.3475   -2.5837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3072    0.2438   -2.4004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4744    0.4809   -0.9037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1830    0.0935   -0.2994 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0783    0.6425    1.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1626    0.6194   -1.2482 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9752   -0.1968    4.4150 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8102   -1.5164    4.3122 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6822   -0.9387    2.8388 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0114    2.3586    3.1755 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2375    2.4192    0.1192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7778   -2.6599    2.7427 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3816   -3.5515    3.7429 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0318   -1.8580    4.1307 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0625    0.0196   -2.4796 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7895    2.1041   -3.2733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3373    0.6088   -4.6322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7005   -1.9125   -3.3771 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306202101493D          

 47 50  0  0  0  0            999 V2000
    3.2047   -0.6461    3.7807 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1800    0.3297    3.5950 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4695    0.1994    2.4264 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1560    1.4156    1.7902 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5561    2.6015    2.3451 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4512    1.4647    0.5913 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3225   -0.9361    0.6631 C   0  0  0  0  0  0  0  0  0  0  0  0
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 15  7  1  0  0  0  0
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  4  3  2  0  0  0  0
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  6 31  1  0  0  0  0
 22 40  1  0  0  0  0
 22 41  1  0  0  0  0
 23 42  1  0  0  0  0
 23 43  1  0  0  0  0
  5 30  1  0  0  0  0
 11 32  1  0  0  0  0
 11 33  1  0  0  0  0
 11 34  1  0  0  0  0
 25 44  1  0  0  0  0
 25 45  1  0  0  0  0
 25 46  1  0  0  0  0
 17 36  1  0  0  0  0
 19 38  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0033217

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C2C(=O)O[C@]3(C2=C1[H])[C@]1([H])N(C([H])([H])[H])C([H])([H])C([H])([H])C1=C([H])[C@]([H])(O[H])[C@@]3([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C18H21NO7/c1-19-5-4-8-6-11(21)16(22)18(15(8)19)9-7-10(20)13(24-2)14(25-3)12(9)17(23)26-18/h6-7,11,15-16,20-22H,4-5H2,1-3H3/t11-,15+,16+,18+/m0/s1

> <INCHI_KEY>
LDKRJBWKYCDFHG-TWIYPKMFSA-N

> <FORMULA>
C18H21NO7

> <MOLECULAR_WEIGHT>
363.366

> <EXACT_MASS>
363.13180202

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
36.1134560279548

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,5'S,6'R,7'aR)-5',6,6'-trihydroxy-4,5-dimethoxy-1'-methyl-1',2',3',5',6',7'a-hexahydro-3H-spiro[2-benzofuran-1,7'-indole]-3-one

> <ALOGPS_LOGP>
0.27

> <JCHEM_LOGP>
-0.1641611610000001

> <ALOGPS_LOGS>
-1.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.712386122608642

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.926753570467362

> <JCHEM_PKA_STRONGEST_BASIC>
6.233831200322626

> <JCHEM_POLAR_SURFACE_AREA>
108.69

> <JCHEM_REFRACTIVITY>
91.61929999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.12e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,5'S,6'R,7'aR)-5',6,6'-trihydroxy-4,5-dimethoxy-1'-methyl-3',5',6',7'a-tetrahydro-2'H-spiro[2-benzofuran-1,7'-indole]-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 47 50  0  0  0  0  0  0  0  0999 V2000
    3.2047   -0.6461    3.7807 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1800    0.3297    3.5950 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4695    0.1994    2.4264 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1560    1.4156    1.7902 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5561    2.6015    2.3451 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4512    1.4647    0.5913 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0431    0.2645    0.0290 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3225   -0.9361    0.6631 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0080   -1.0003    1.8721 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2529   -2.2013    2.4727 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1550   -2.5729    3.3097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2287   -2.0241   -0.1376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1868   -3.2150    0.0925 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7960   -1.4531   -1.2384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7237    0.0061   -1.2260 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0562    0.4593   -2.4954 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2148    1.8896   -2.5158 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6691   -0.0063   -3.7883 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3235   -1.3557   -4.0877 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1663    0.0584   -3.7155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8265    0.3475   -2.5837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3072    0.2438   -2.4004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4744    0.4809   -0.9037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1830    0.0935   -0.2994 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0783    0.6425    1.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1626    0.6194   -1.2482 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9752   -0.1968    4.4150 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8102   -1.5164    4.3122 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6822   -0.9387    2.8388 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0114    2.3586    3.1755 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2375    2.4192    0.1192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7778   -2.6599    2.7427 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3816   -3.5515    3.7429 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0318   -1.8580    4.1307 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0625    0.0196   -2.4796 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7895    2.1041   -3.2733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3373    0.6088   -4.6322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7005   -1.9125   -3.3771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7139   -0.2014   -4.6180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8478    0.9961   -2.9822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6557   -0.7580   -2.6743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3009   -0.1122   -0.4980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6966    1.5422   -0.7259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9396    0.3324    1.6516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1990    0.2565    1.5677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0373    1.7375    1.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0974    1.7120   -1.1340 H   0  0  0  0  0  0  0  0  0  0  0  0
 15  7  1  0
 26 21  1  0
  4  3  2  0
 15 26  1  0
  3  9  1  0
  9  8  2  0
 16 18  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 26  1  0
  7  6  2  0
 12 13  2  0
  6  4  1  0
  4  5  1  0
  7  8  1  0
  3  2  1  0
 18 20  1  0
  9 10  1  0
 20 21  2  0
 10 11  1  0
 24 25  1  0
 15 16  1  0
 26 47  1  1
  8 12  1  0
 16 17  1  0
 12 14  1  0
 18 19  1  0
  2  1  1  0
 15 14  1  6
 16 35  1  1
 18 37  1  6
 20 39  1  0
  6 31  1  0
 22 40  1  0
 22 41  1  0
 23 42  1  0
 23 43  1  0
  5 30  1  0
 11 32  1  0
 11 33  1  0
 11 34  1  0
 25 44  1  0
 25 45  1  0
 25 46  1  0
 17 36  1  0
 19 38  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
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       3.205  -0.646   3.781  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.180   0.330   3.595  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.470   0.199   2.426  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.156   1.416   1.790  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.556   2.602   2.345  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.451   1.465   0.591  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.043   0.265   0.029  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.323  -0.936   0.663  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.008  -1.000   1.872  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.253  -2.201   2.473  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.155  -2.573   3.310  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.229  -2.024  -0.138  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.187  -3.215   0.093  0.00  0.00           O+0
HETATM   14  O   UNK     0      -0.796  -1.453  -1.238  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.724   0.006  -1.226  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.056   0.459  -2.495  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.215   1.890  -2.516  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.669  -0.006  -3.788  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.324  -1.356  -4.088  0.00  0.00           O+0
HETATM   20  C   UNK     0      -2.166   0.058  -3.716  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.826   0.348  -2.584  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.307   0.244  -2.400  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.474   0.481  -0.904  0.00  0.00           C+0
HETATM   24  N   UNK     0      -3.183   0.094  -0.299  0.00  0.00           N+0
HETATM   25  C   UNK     0      -3.078   0.643   1.048  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.163   0.619  -1.248  0.00  0.00           C+0
HETATM   27  H   UNK     0       3.975  -0.197   4.415  0.00  0.00           H+0
HETATM   28  H   UNK     0       2.810  -1.516   4.312  0.00  0.00           H+0
HETATM   29  H   UNK     0       3.682  -0.939   2.839  0.00  0.00           H+0
HETATM   30  H   UNK     0       2.011   2.359   3.176  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.238   2.419   0.119  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.778  -2.660   2.743  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.382  -3.551   3.743  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.032  -1.858   4.131  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.063   0.020  -2.480  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.790   2.104  -3.273  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.337   0.609  -4.632  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.701  -1.913  -3.377  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.714  -0.201  -4.618  0.00  0.00           H+0
HETATM   40  H   UNK     0      -4.848   0.996  -2.982  0.00  0.00           H+0
HETATM   41  H   UNK     0      -4.656  -0.758  -2.674  0.00  0.00           H+0
HETATM   42  H   UNK     0      -5.301  -0.112  -0.498  0.00  0.00           H+0
HETATM   43  H   UNK     0      -4.697   1.542  -0.726  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.940   0.332   1.652  0.00  0.00           H+0
HETATM   45  H   UNK     0      -2.199   0.257   1.568  0.00  0.00           H+0
HETATM   46  H   UNK     0      -3.037   1.738   1.055  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.097   1.712  -1.134  0.00  0.00           H+0
CONECT    1    2   27   28   29                                             
CONECT    2    3    1                                                       
CONECT    3    4    9    2                                                  
CONECT    4    3    6    5                                                  
CONECT    5    4   30                                                       
CONECT    6    7    4   31                                                  
CONECT    7   15    6    8                                                  
CONECT    8    9    7   12                                                  
CONECT    9    3    8   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   32   33   34                                             
CONECT   12   13    8   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15    7   26   16   14                                             
CONECT   16   18   15   17   35                                             
CONECT   17   16   36                                                       
CONECT   18   16   20   19   37                                             
CONECT   19   18   38                                                       
CONECT   20   18   21   39                                                  
CONECT   21   26   22   20                                                  
CONECT   22   21   23   40   41                                             
CONECT   23   22   24   42   43                                             
CONECT   24   23   26   25                                                  
CONECT   25   24   44   45   46                                             
CONECT   26   21   15   24   47                                             
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    5                                                            
CONECT   31    6                                                            
CONECT   32   11                                                            
CONECT   33   11                                                            
CONECT   34   11                                                            
CONECT   35   16                                                            
CONECT   36   17                                                            
CONECT   37   18                                                            
CONECT   38   19                                                            
CONECT   39   20                                                            
CONECT   40   22                                                            
CONECT   41   22                                                            
CONECT   42   23                                                            
CONECT   43   23                                                            
CONECT   44   25                                                            
CONECT   45   25                                                            
CONECT   46   25                                                            
CONECT   47   26                                                            
MASTER        0    0    0    0    0    0    0    0   47    0  100    0
END

RDKit          3D

47 50  0  0  0  0  0  0  0  0999 V2000
    3.2047   -0.6461    3.7807 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1800    0.3297    3.5950 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4695    0.1994    2.4264 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1560    1.4156    1.7902 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5561    2.6015    2.3451 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4512    1.4647    0.5913 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0431    0.2645    0.0290 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3225   -0.9361    0.6631 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0080   -1.0003    1.8721 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2529   -2.2013    2.4727 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1550   -2.5729    3.3097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2287   -2.0241   -0.1376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1868   -3.2150    0.0925 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7960   -1.4531   -1.2384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7237    0.0061   -1.2260 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0562    0.4593   -2.4954 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2148    1.8896   -2.5158 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6691   -0.0063   -3.7883 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3235   -1.3557   -4.0877 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1663    0.0584   -3.7155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8265    0.3475   -2.5837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3072    0.2438   -2.4004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4744    0.4809   -0.9037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1830    0.0935   -0.2994 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0783    0.6425    1.0483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1626    0.6194   -1.2482 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9752   -0.1968    4.4150 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8102   -1.5164    4.3122 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6822   -0.9387    2.8388 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0114    2.3586    3.1755 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2375    2.4192    0.1192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7778   -2.6599    2.7427 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3816   -3.5515    3.7429 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0318   -1.8580    4.1307 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0625    0.0196   -2.4796 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7895    2.1041   -3.2733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3373    0.6088   -4.6322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7005   -1.9125   -3.3771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7139   -0.2014   -4.6180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8478    0.9961   -2.9822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6557   -0.7580   -2.6743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3009   -0.1122   -0.4980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6966    1.5422   -0.7259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9396    0.3324    1.6516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1990    0.2565    1.5677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0373    1.7375    1.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0974    1.7120   -1.1340 H   0  0  0  0  0  0  0  0  0  0  0  0
 15  7  1  0
 26 21  1  0
  4  3  2  0
 15 26  1  0
  3  9  1  0
  9  8  2  0
 16 18  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 26  1  0
  7  6  2  0
 12 13  2  0
  6  4  1  0
  4  5  1  0
  7  8  1  0
  3  2  1  0
 18 20  1  0
  9 10  1  0
 20 21  2  0
 10 11  1  0
 24 25  1  0
 15 16  1  0
 26 47  1  1
  8 12  1  0
 16 17  1  0
 12 14  1  0
 18 19  1  0
  2  1  1  0
 15 14  1  6
 16 35  1  1
 18 37  1  6
 20 39  1  0
  6 31  1  0
 22 40  1  0
 22 41  1  0
 23 42  1  0
 23 43  1  0
  5 30  1  0
 11 32  1  0
 11 33  1  0
 11 34  1  0
 25 44  1  0
 25 45  1  0
 25 46  1  0
 17 36  1  0
 19 38  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₂₁NO₇

Average Mass

363.3660 Da

Monoisotopic Mass

363.13180 Da

IUPAC Name

(1R,5'S,6'R,7'aR)-5',6,6'-trihydroxy-4,5-dimethoxy-1'-methyl-1',2',3',5',6',7'a-hexahydro-3H-spiro[2-benzofuran-1,7'-indole]-3-one

Traditional Name

(1R,5'S,6'R,7'aR)-5',6,6'-trihydroxy-4,5-dimethoxy-1'-methyl-3',5',6',7'a-tetrahydro-2'H-spiro[2-benzofuran-1,7'-indole]-3-one

CAS Registry Number

Not Available

SMILES

[H]OC1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C2C(=O)O[C@]3(C2=C1[H])[C@]1([H])N(C([H])([H])[H])C([H])([H])C([H])([H])C1=C([H])[C@]([H])(O[H])[C@@]3([H])O[H]

InChI Identifier

InChI=1S/C18H21NO7/c1-19-5-4-8-6-11(21)16(22)18(15(8)19)9-7-10(20)13(24-2)14(25-3)12(9)17(23)26-18/h6-7,11,15-16,20-22H,4-5H2,1-3H3/t11-,15+,16+,18+/m0/s1

InChI Key

LDKRJBWKYCDFHG-TWIYPKMFSA-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, J. Nat. Prod. 70, 1458 (2007)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as homolycorine-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids compounds containing the homolycorine skeleton, made up of a [3,4-g]benzopyranone ring due to the oxidation of the hydroxyl group at the C6. They are biogenetically formed through a restructuring of lycorine-type alkaloids.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Amaryllidaceae alkaloids

Sub Class

Homolycorine-type amaryllidaceae alkaloids

Direct Parent

Homolycorine-type amaryllidaceae alkaloids

Alternative Parents

Substituents

Homolycorine skeleton
Benzofuranone
Isobenzofuranone
Phthalide
Isocoumaran
Isobenzofuran
Indole or derivatives
Anisole
Phenol ether
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aralkylamine
Benzenoid
N-alkylpyrrolidine
Pyrrolidine
1,2-diol
Amino acid or derivatives
Carboxylic acid ester
Lactone
Tertiary aliphatic amine
Secondary alcohol
Tertiary amine
Ether
Carboxylic acid derivative
Oxacycle
Azacycle
Organoheterocyclic compound
Polyol
Organooxygen compound
Organonitrogen compound
Amine
Hydrocarbon derivative
Organic nitrogen compound
Organic oxide
Alcohol
Organic oxygen 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	0.27	ALOGPS
logP	-0.16	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	8.93	ChemAxon
pKa (Strongest Basic)	6.23	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	108.69 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	91.62 m³·mol⁻¹	ChemAxon
Polarizability	36.11 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

28284469

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23642825

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wang YH, Zhang ZK, Yang FM, Sun QY, He HP, Di YT, Mu SZ, Lu Y, Chang Y, Zheng QT, Ding M, Dong JH, Hao XJ: Benzylphenethylamine alkaloids from Hosta plantaginea with inhibitory activity against tobacco mosaic virus and acetylcholinesterase. J Nat Prod. 2007 Sep;70(9):1458-61. doi: 10.1021/np0702077. Epub 2007 Sep 7. [PubMed:17822295 ]
Wang, Y. -H., et al. (2007). Wang, Y. -H., et al, J. Nat. Prod. 70, 1458 (2007). J. Nat. Prod..

Showing NP-Card for hostasine (NP0033217)

MOL for NP0033217 (hostasine)

3D MOL for NP0033217 (hostasine)

3D SDF for NP0033217 (hostasine)

3D-SDF for NP0033217 (hostasine)

PDB for NP0033217 (hostasine)

3D PDB for NP0033217 (hostasine)

SMILES for NP0033217 (hostasine)

INCHI for NP0033217 (hostasine)

Structure for NP0033217 (hostasine)

3D Structure for NP0033217 (hostasine)