Hmdb loader

Showing metabocard for Isorheagenine (HMDB0029360)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:29:57 UTC
Update Date2022-03-07 02:52:08 UTC
HMDB IDHMDB0029360
Secondary Accession Numbers
  • HMDB29360
Metabolite Identification
Common NameIsorheagenine
DescriptionIsorheagenine belongs to the class of organic compounds known as rhoeadine alkaloids. These are alkaloids with a structure based on rhoeadine. They usually contain a benzazepine system fused with a six-membered hemiacetal or acetal. Isorheagenine is a very strong basic compound (based on its pKa). Alkaloid from Papaver rhoeas (corn poppy).
Structure
Data?1582753408
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0029360 (Isorheagenine)


  Mrv0541 02241210212D          

 27 32  0  0  0  0            999 V2000
   -1.8877    0.6153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2310    1.0257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3952    1.8467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7385    2.4213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7385    3.2423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0004    3.4885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4922    2.8318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0004    2.1751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1638    1.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4101    0.7795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1638    0.0407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6563   -0.0415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0668   -0.6974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6563   -1.4362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0668   -2.1751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8877   -2.3392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9698   -3.1602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1489   -3.4885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6563   -2.8318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1638   -2.8318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5742   -2.1751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1638   -1.4362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5742   -0.6974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3952   -0.7795    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7235   -1.5183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9698   -0.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8877   -0.6974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 26  1  0  0  0  0
  2  3  1  0  0  0  0
  2 10  2  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4  8  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 23  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 27  1  0  0  0  0
 14 15  1  0  0  0  0
 14 22  2  0  0  0  0
 15 16  1  0  0  0  0
 15 19  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
M  END
Download

3D MOL for HMDB0029360 (Isorheagenine)

HMDB0029360
     RDKit          3D
Isorheagenine
 46 51  0  0  0  0  0  0  0  0999 V2000
   -1.2466   -1.5097   -2.2713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1638   -1.2993   -1.3279 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0752   -1.5271   -2.0169 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1985   -1.9023   -1.0721 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6493   -0.7423   -0.2690 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0188   -0.5723   -0.2669 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6283    0.4514    0.4230 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8240    1.3260    1.1297 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4501    1.1517    1.1248 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8412    0.1247    0.4325 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3874    0.1354    0.5692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0928   -0.8413    1.3977 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4370   -0.8401    1.5966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6699   -0.4066    2.9216 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2499   -0.0684    0.6475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7034    0.3659   -0.5288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4469    1.0826   -1.4226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7883    1.3954   -1.1650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3393    0.9577    0.0211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5911    0.2371    0.9192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3568   -0.0892    2.0295 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7029    0.3129    1.7339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6259    1.1004    0.5684 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2965    0.0456   -0.8050 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6647    2.2621    1.7354 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9061    2.1741    1.0612 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9665    0.8430    0.5890 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1892   -2.5089   -2.7486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2381   -1.3477   -1.7791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1431   -0.7075   -3.0493 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9202   -2.4344   -2.6718 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3568   -0.7077   -2.7013 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0427   -2.2457   -1.6821 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8058   -2.6832   -0.4014 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6433   -1.2537   -0.8173 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8671    1.8604    1.6914 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0173    1.1196    0.9843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7653   -1.9220    1.6135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4138   -0.9170    3.3382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0019    1.4258   -2.3609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3705    1.9598   -1.8711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0880    0.8531    2.6038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2468   -0.6222    1.4979 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1986    0.7340   -1.5058 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6936    2.3057    1.8406 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0121    2.9246    0.2641 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 16 24  1  0
  8 25  1  0
 25 26  1  0
 26 27  1  0
 24  2  1  0
 10  5  1  0
 24 11  1  0
 27  7  1  0
 20 15  1  0
 23 19  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  6 35  1  0
  9 36  1  0
 11 37  1  0
 13 38  1  0
 14 39  1  0
 17 40  1  0
 18 41  1  0
 22 42  1  0
 22 43  1  0
 24 44  1  0
 26 45  1  0
 26 46  1  0
M  END
Download

3D SDF for HMDB0029360 (Isorheagenine)


  Mrv0541 02241210212D          

 27 32  0  0  0  0            999 V2000
   -1.8877    0.6153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2310    1.0257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3952    1.8467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7385    2.4213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7385    3.2423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0004    3.4885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4922    2.8318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0004    2.1751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1638    1.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4101    0.7795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1638    0.0407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6563   -0.0415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0668   -0.6974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6563   -1.4362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0668   -2.1751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8877   -2.3392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9698   -3.1602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1489   -3.4885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6563   -2.8318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1638   -2.8318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5742   -2.1751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1638   -1.4362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5742   -0.6974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3952   -0.7795    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7235   -1.5183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9698   -0.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8877   -0.6974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 26  1  0  0  0  0
  2  3  1  0  0  0  0
  2 10  2  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4  8  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 23  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 27  1  0  0  0  0
 14 15  1  0  0  0  0
 14 22  2  0  0  0  0
 15 16  1  0  0  0  0
 15 19  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029360

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1CCC2=C(C=C3OCOC3=C2)C2OC(O)C3=C(C=CC4=C3OCO4)C12

> <INCHI_IDENTIFIER>
InChI=1S/C20H19NO6/c1-21-5-4-10-6-14-15(25-8-24-14)7-12(10)18-17(21)11-2-3-13-19(26-9-23-13)16(11)20(22)27-18/h2-3,6-7,17-18,20,22H,4-5,8-9H2,1H3

> <INCHI_KEY>
XUYAYNRYVXHNOQ-UHFFFAOYSA-N

> <FORMULA>
C20H19NO6

> <MOLECULAR_WEIGHT>
369.368

> <EXACT_MASS>
369.121237345

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
38.327772685483744

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
13-methyl-5,7,19,21,25-pentaoxa-13-azahexacyclo[12.11.0.0²,¹⁰.0⁴,⁸.0¹⁵,²³.0¹⁸,²²]pentacosa-2(10),3,8,15(23),16,18(22)-hexaen-24-ol

> <ALOGPS_LOGP>
1.45

> <JCHEM_LOGP>
2.385033133333334

> <ALOGPS_LOGS>
-2.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.258075544207356

> <JCHEM_PKA_STRONGEST_BASIC>
5.88080530188729

> <JCHEM_POLAR_SURFACE_AREA>
69.62

> <JCHEM_REFRACTIVITY>
94.0251

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.32e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
13-methyl-5,7,19,21,25-pentaoxa-13-azahexacyclo[12.11.0.0²,¹⁰.0⁴,⁸.0¹⁵,²³.0¹⁸,²²]pentacosa-2(10),3,8,15(23),16,18(22)-hexaen-24-ol

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0029360 (Isorheagenine)

HMDB0029360
     RDKit          3D
Isorheagenine
 46 51  0  0  0  0  0  0  0  0999 V2000
   -1.2466   -1.5097   -2.2713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1638   -1.2993   -1.3279 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0752   -1.5271   -2.0169 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1985   -1.9023   -1.0721 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6493   -0.7423   -0.2690 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0188   -0.5723   -0.2669 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6283    0.4514    0.4230 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8240    1.3260    1.1297 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4501    1.1517    1.1248 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8412    0.1247    0.4325 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3874    0.1354    0.5692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0928   -0.8413    1.3977 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4370   -0.8401    1.5966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6699   -0.4066    2.9216 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2499   -0.0684    0.6475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7034    0.3659   -0.5288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4469    1.0826   -1.4226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7883    1.3954   -1.1650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3393    0.9577    0.0211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5911    0.2371    0.9192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3568   -0.0892    2.0295 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7029    0.3129    1.7339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6259    1.1004    0.5684 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2965    0.0456   -0.8050 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6647    2.2621    1.7354 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9061    2.1741    1.0612 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9665    0.8430    0.5890 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1892   -2.5089   -2.7486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2381   -1.3477   -1.7791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1431   -0.7075   -3.0493 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9202   -2.4344   -2.6718 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3568   -0.7077   -2.7013 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0427   -2.2457   -1.6821 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8058   -2.6832   -0.4014 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6433   -1.2537   -0.8173 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8671    1.8604    1.6914 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0173    1.1196    0.9843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7653   -1.9220    1.6135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4138   -0.9170    3.3382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0019    1.4258   -2.3609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3705    1.9598   -1.8711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0880    0.8531    2.6038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2468   -0.6222    1.4979 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1986    0.7340   -1.5058 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6936    2.3057    1.8406 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0121    2.9246    0.2641 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 16 24  1  0
  8 25  1  0
 25 26  1  0
 26 27  1  0
 24  2  1  0
 10  5  1  0
 24 11  1  0
 27  7  1  0
 20 15  1  0
 23 19  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  3 31  1  0
  3 32  1  0
  4 33  1  0
  4 34  1  0
  6 35  1  0
  9 36  1  0
 11 37  1  0
 13 38  1  0
 14 39  1  0
 17 40  1  0
 18 41  1  0
 22 42  1  0
 22 43  1  0
 24 44  1  0
 26 45  1  0
 26 46  1  0
M  END
Download

PDB for HMDB0029360 (Isorheagenine)

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -3.524   1.149   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.298   1.915   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.604   3.447   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.379   4.520   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.379   6.052   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.001   6.512   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.919   5.286   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.001   4.060   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.306   2.528   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.766   1.455   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.306   0.076   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.225  -0.077   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.991  -1.302   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.225  -2.681   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.991  -4.060   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.524  -4.367   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.677  -5.899   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.145  -6.512   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.225  -5.286   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.306  -5.286   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.072  -4.060   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.306  -2.681   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.072  -1.302   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0      -2.604  -1.455   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0      -3.217  -2.834   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.677  -0.384   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.524  -1.302   0.000  0.00  0.00           O+0
CONECT    1    2   26                                                       
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    4    7    9                                                  
CONECT    9    8   10                                                       
CONECT   10    2    9   11                                                  
CONECT   11   10   12   23                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   27                                                  
CONECT   14   13   15   22                                                  
CONECT   15   14   16   19                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   15   18   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   14   21   23                                                  
CONECT   23   11   22   24                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26    1   24                                                       
CONECT   27   13                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   64    0
END
Download

3D PDB for HMDB0029360 (Isorheagenine)

COMPND    HMDB0029360
HETATM    1  C1  UNL     1      -1.247  -1.510  -2.271  1.00  0.00           C  
HETATM    2  N1  UNL     1      -0.164  -1.299  -1.328  1.00  0.00           N  
HETATM    3  C2  UNL     1       1.075  -1.527  -2.017  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.198  -1.902  -1.072  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.649  -0.742  -0.269  1.00  0.00           C  
HETATM    6  C5  UNL     1       4.019  -0.572  -0.267  1.00  0.00           C  
HETATM    7  C6  UNL     1       4.628   0.451   0.423  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.824   1.326   1.130  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.450   1.152   1.125  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.841   0.125   0.433  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.387   0.135   0.569  1.00  0.00           C  
HETATM   12  O1  UNL     1      -0.093  -0.841   1.398  1.00  0.00           O  
HETATM   13  C11 UNL     1      -1.437  -0.840   1.597  1.00  0.00           C  
HETATM   14  O2  UNL     1      -1.670  -0.407   2.922  1.00  0.00           O  
HETATM   15  C12 UNL     1      -2.250  -0.068   0.648  1.00  0.00           C  
HETATM   16  C13 UNL     1      -1.703   0.366  -0.529  1.00  0.00           C  
HETATM   17  C14 UNL     1      -2.447   1.083  -1.423  1.00  0.00           C  
HETATM   18  C15 UNL     1      -3.788   1.395  -1.165  1.00  0.00           C  
HETATM   19  C16 UNL     1      -4.339   0.958   0.021  1.00  0.00           C  
HETATM   20  C17 UNL     1      -3.591   0.237   0.919  1.00  0.00           C  
HETATM   21  O3  UNL     1      -4.357  -0.089   2.029  1.00  0.00           O  
HETATM   22  C18 UNL     1      -5.703   0.313   1.734  1.00  0.00           C  
HETATM   23  O4  UNL     1      -5.626   1.100   0.568  1.00  0.00           O  
HETATM   24  C19 UNL     1      -0.296   0.046  -0.805  1.00  0.00           C  
HETATM   25  O5  UNL     1       4.665   2.262   1.735  1.00  0.00           O  
HETATM   26  C20 UNL     1       5.906   2.174   1.061  1.00  0.00           C  
HETATM   27  O6  UNL     1       5.967   0.843   0.589  1.00  0.00           O  
HETATM   28  H1  UNL     1      -1.189  -2.509  -2.749  1.00  0.00           H  
HETATM   29  H2  UNL     1      -2.238  -1.348  -1.779  1.00  0.00           H  
HETATM   30  H3  UNL     1      -1.143  -0.708  -3.049  1.00  0.00           H  
HETATM   31  H4  UNL     1       0.920  -2.434  -2.672  1.00  0.00           H  
HETATM   32  H5  UNL     1       1.357  -0.708  -2.701  1.00  0.00           H  
HETATM   33  H6  UNL     1       3.043  -2.246  -1.682  1.00  0.00           H  
HETATM   34  H7  UNL     1       1.806  -2.683  -0.401  1.00  0.00           H  
HETATM   35  H8  UNL     1       4.643  -1.254  -0.817  1.00  0.00           H  
HETATM   36  H9  UNL     1       1.867   1.860   1.691  1.00  0.00           H  
HETATM   37  H10 UNL     1       0.017   1.120   0.984  1.00  0.00           H  
HETATM   38  H11 UNL     1      -1.765  -1.922   1.614  1.00  0.00           H  
HETATM   39  H12 UNL     1      -2.414  -0.917   3.338  1.00  0.00           H  
HETATM   40  H13 UNL     1      -2.002   1.426  -2.361  1.00  0.00           H  
HETATM   41  H14 UNL     1      -4.370   1.960  -1.871  1.00  0.00           H  
HETATM   42  H15 UNL     1      -6.088   0.853   2.604  1.00  0.00           H  
HETATM   43  H16 UNL     1      -6.247  -0.622   1.498  1.00  0.00           H  
HETATM   44  H17 UNL     1       0.199   0.734  -1.506  1.00  0.00           H  
HETATM   45  H18 UNL     1       6.694   2.306   1.841  1.00  0.00           H  
HETATM   46  H19 UNL     1       6.012   2.925   0.264  1.00  0.00           H  
CONECT    1    2   28   29   30
CONECT    2    3   24
CONECT    3    4   31   32
CONECT    4    5   33   34
CONECT    5    6    6   10
CONECT    6    7   35
CONECT    7    8    8   27
CONECT    8    9   25
CONECT    9   10   10   36
CONECT   10   11
CONECT   11   12   24   37
CONECT   12   13
CONECT   13   14   15   38
CONECT   14   39
CONECT   15   16   16   20
CONECT   16   17   24
CONECT   17   18   18   40
CONECT   18   19   41
CONECT   19   20   20   23
CONECT   20   21
CONECT   21   22
CONECT   22   23   42   43
CONECT   24   44
CONECT   25   26
CONECT   26   27   45   46
END
Download

SMILES for HMDB0029360 (Isorheagenine)

CN1CCC2=C(C=C3OCOC3=C2)C2OC(O)C3=C(C=CC4=C3OCO4)C12
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INCHI for HMDB0029360 (Isorheagenine)

InChI=1S/C20H19NO6/c1-21-5-4-10-6-14-15(25-8-24-14)7-12(10)18-17(21)11-2-3-13-19(26-9-23-13)16(11)20(22)27-18/h2-3,6-7,17-18,20,22H,4-5,8-9H2,1H3
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View in JSmolView Stereo Labels
Synonyms
ValueSource
IsorhoeagenineHMDB
Chemical FormulaC20H19NO6
Average Molecular Weight369.368
Monoisotopic Molecular Weight369.121237345
IUPAC Name13-methyl-5,7,19,21,25-pentaoxa-13-azahexacyclo[12.11.0.0²,¹⁰.0⁴,⁸.0¹⁵,²³.0¹⁸,²²]pentacosa-2(10),3,8,15(23),16,18(22)-hexaen-24-ol
Traditional Name13-methyl-5,7,19,21,25-pentaoxa-13-azahexacyclo[12.11.0.0²,¹⁰.0⁴,⁸.0¹⁵,²³.0¹⁸,²²]pentacosa-2(10),3,8,15(23),16,18(22)-hexaen-24-ol
CAS Registry Number17948-35-5
SMILES
CN1CCC2=C(C=C3OCOC3=C2)C2OC(O)C3=C(C=CC4=C3OCO4)C12
InChI Identifier
InChI=1S/C20H19NO6/c1-21-5-4-10-6-14-15(25-8-24-14)7-12(10)18-17(21)11-2-3-13-19(26-9-23-13)16(11)20(22)27-18/h2-3,6-7,17-18,20,22H,4-5,8-9H2,1H3
InChI KeyXUYAYNRYVXHNOQ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as rhoeadine alkaloids. These are alkaloids with a structure based on rhoeadine. They usually contain a benzazepine system fused with a six-membered hemiacetal or acetal.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassRhoeadine alkaloids
Sub ClassNot Available
Direct ParentRhoeadine alkaloids
Alternative Parents
Substituents
  • Rhoeadine-skeleton
  • Benzazepine
  • Benzopyran
  • Isochromane
  • 2-benzopyran
  • Benzodioxole
  • Azepine
  • Aralkylamine
  • Benzenoid
  • Hemiacetal
  • Tertiary amine
  • Tertiary aliphatic amine
  • Azacycle
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point210 - 215 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.32 g/LALOGPS
logP1.45ALOGPS
logP2.39ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)11.26ChemAxon
pKa (Strongest Basic)5.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area69.62 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity94.03 m³·mol⁻¹ChemAxon
Polarizability38.33 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+182.55231661259
DarkChem[M-H]-179.27431661259
DeepCCS[M-2H]-218.85130932474
DeepCCS[M+Na]+194.55630932474
AllCCS[M+H]+187.732859911
AllCCS[M+H-H2O]+184.732859911
AllCCS[M+NH4]+190.532859911
AllCCS[M+Na]+191.332859911
AllCCS[M-H]-191.432859911
AllCCS[M+Na-2H]-190.732859911
AllCCS[M+HCOO]-190.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
IsorheagenineCN1CCC2=C(C=C3OCOC3=C2)C2OC(O)C3=C(C=CC4=C3OCO4)C124447.3Standard polar33892256
IsorheagenineCN1CCC2=C(C=C3OCOC3=C2)C2OC(O)C3=C(C=CC4=C3OCO4)C122917.8Standard non polar33892256
IsorheagenineCN1CCC2=C(C=C3OCOC3=C2)C2OC(O)C3=C(C=CC4=C3OCO4)C123124.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Isorheagenine,1TMS,isomer #1CN1CCC2=CC3=C(C=C2C2OC(O[Si](C)(C)C)C4=C(C=CC5=C4OCO5)C21)OCO33161.4Semi standard non polar33892256
Isorheagenine,1TBDMS,isomer #1CN1CCC2=CC3=C(C=C2C2OC(O[Si](C)(C)C(C)(C)C)C4=C(C=CC5=C4OCO5)C21)OCO33395.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Isorheagenine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-0449000000-5ceba6819f90d7fa391d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isorheagenine GC-MS (1 TMS) - 70eV, Positivesplash10-0uk9-6395500000-79f6f5bc32d938174a1c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isorheagenine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Isorheagenine , positive-QTOFsplash10-0udi-0798000000-b81abc4df0462fac88422017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isorheagenine 10V, Positive-QTOFsplash10-00di-0009000000-330cb64395c1a180db372015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isorheagenine 20V, Positive-QTOFsplash10-0fk9-0009000000-2ab60a0f104f145938062015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isorheagenine 40V, Positive-QTOFsplash10-0f6t-3921000000-7597371b1f5941fb92ed2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isorheagenine 10V, Negative-QTOFsplash10-014i-0019000000-be1ce02fe67d98da62af2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isorheagenine 20V, Negative-QTOFsplash10-00xr-0019000000-fdda811e9f8c73342f172015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isorheagenine 40V, Negative-QTOFsplash10-00dl-8696000000-a1a80a0e9b70faa04eea2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isorheagenine 10V, Positive-QTOFsplash10-00di-0009000000-4c8e187b071c1383f5162021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isorheagenine 20V, Positive-QTOFsplash10-00di-0009000000-56f615d88bf31c7613992021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isorheagenine 40V, Positive-QTOFsplash10-0fk9-0259000000-9e5d327ee5a9bd2d7da72021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isorheagenine 10V, Negative-QTOFsplash10-014i-0009000000-321b928b876644c5d7542021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isorheagenine 20V, Negative-QTOFsplash10-014i-0009000000-412695ab5f3c7624cec92021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isorheagenine 40V, Negative-QTOFsplash10-014i-0119000000-d84766f3011f8fbca6cb2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB000425
KNApSAcK IDC00025464
Chemspider ID530117
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound609840
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .