NP-MRD: Showing NP-Card for 16,18,19-trimethoxy-13-methyl-5,7,22-trioxa-13-azapentacyclo[12.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]docosa-2,4(8),9,15,17,19-hexaen-21-ol (NP0255432)

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Record Information

Version

1.0

Created at

2022-09-07 19:56:08 UTC

Updated at

2022-09-07 19:56:08 UTC

NP-MRD ID

NP0255432

Secondary Accession Numbers

None

Natural Product Identification

Common Name

16,18,19-trimethoxy-13-methyl-5,7,22-trioxa-13-azapentacyclo[12.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]docosa-2,4(8),9,15,17,19-hexaen-21-ol

Description

16,18,19-Trimethoxy-13-methyl-5,7,22-trioxa-13-azapentacyclo[12.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]Docosa-2,4(8),9,15(20),16,18-hexaen-21-ol 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. 16,18,19-Trimethoxy-13-methyl-5,7,22-trioxa-13-azapentacyclo[12.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]Docosa-2,4(8),9,15(20),16,18-hexaen-21-ol is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241509452D          

 30 34  0  0  0  0            999 V2000
    5.6394    1.1517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5532    1.9722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7995    2.3077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7132    3.1282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9595    3.4637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8732    4.2842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5407    4.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2921    2.9788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5384    3.3143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8710    2.8294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9573    2.0089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7110    1.6734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7972    0.8529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3784    2.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1321    1.8228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2183    1.0023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9720    0.6668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0757    3.0488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5809    2.3887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2382    2.4871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8595    1.9443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5677    2.3674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3842    3.1717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5625    3.2457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0677    3.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7514    3.8074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1423    4.5339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9541    4.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5754    4.1385    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3340    4.4628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  2  0  0  0  0
  8  9  1  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
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  2  0  0  0  0
  3 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 10 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  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
 20 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 18 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
  9 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END

     RDKit          3D

 55 59  0  0  0  0  0  0  0  0999 V2000
   -6.1750   -0.1918    0.5813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1570    0.7531    0.4350 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8362    0.4447    0.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4717   -0.8748    0.0577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1456   -1.2386   -0.2004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7576   -2.5672   -0.3277 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7650   -3.5517   -0.1849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1929   -0.2309   -0.3322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6046    1.0625   -0.2020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9008    1.4400    0.0512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1910    2.7846    0.1612 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5646    3.6271   -0.8784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5830    2.1296   -0.3378 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9496    3.2944    0.3161 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5429    1.6123    0.3518 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1244    0.5887   -0.4267 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4502    0.3616    0.1555 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2668    1.4489   -0.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5770    1.5361    0.2461 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1227    0.5179    0.9956 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3645   -0.5747    1.3343 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0384   -0.6216    0.9006 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4365   -1.8648    1.3781 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9270   -1.7458    1.3529 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5246   -1.7733    0.0077 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1983   -2.7164   -0.8370 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2247   -0.5273   -0.6096 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4445    0.8449    1.2736 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8451    1.9231    0.4434 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5974    2.4748    0.0830 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0448    0.2414    1.1110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4912   -0.5660   -0.4173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8162   -1.0309    1.2349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1990   -1.6667    0.1573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5165   -3.3577   -0.9737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2772   -3.4238    0.7903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3601   -4.5788   -0.2382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1899    3.2633   -1.8506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6793    3.6787   -0.9251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1772    4.6546   -0.7358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2756    2.3223   -1.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1844    3.7817    0.7074 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3174    1.1224   -1.4110 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8799    2.2780   -0.7503 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7971   -1.3764    1.9255 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8060   -2.1782    2.3804 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7643   -2.6937    0.6866 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5319   -2.5559    1.9935 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6641   -0.7346    1.7818 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5677   -2.9263   -1.7497 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2751   -3.6713   -0.3064 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1449   -2.3135   -1.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2092   -0.7852   -1.7223 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3749    1.5192   -0.4268 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4888    2.6318    1.0039 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  5  8  2  0
  8 27  1  0
 27 16  1  0
 16 15  1  0
 15 13  1  0
 13 14  1  0
 13  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 28  1  0
 28 29  1  0
 29 30  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 10  3  1  0
 22 17  1  0
  9  8  1  0
 30 19  1  0
 25 27  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  4 34  1  0
  7 35  1  0
  7 36  1  0
  7 37  1  0
 27 53  1  6
 16 43  1  6
 13 41  1  6
 14 42  1  0
 12 38  1  0
 12 39  1  0
 12 40  1  0
 18 44  1  0
 29 54  1  0
 29 55  1  0
 21 45  1  0
 23 46  1  0
 23 47  1  0
 24 48  1  0
 24 49  1  0
 26 50  1  0
 26 51  1  0
 26 52  1  0
M  END


  Mrv1533004241509452D          

 30 34  0  0  0  0            999 V2000
    5.6394    1.1517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5532    1.9722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7995    2.3077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7132    3.1282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9595    3.4637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8732    4.2842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5407    4.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2921    2.9788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5384    3.3143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8710    2.8294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9573    2.0089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7110    1.6734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7972    0.8529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3784    2.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1321    1.8228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2183    1.0023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9720    0.6668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0757    3.0488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5809    2.3887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2382    2.4871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8595    1.9443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5677    2.3674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3842    3.1717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5625    3.2457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0677    3.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7514    3.8074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1423    4.5339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9541    4.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5754    4.1385    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3340    4.4628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  2  0  0  0  0
  8  9  1  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
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  2  0  0  0  0
  3 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 10 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  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
 20 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 18 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
  9 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0255432

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(OC)=C2C3C(OC(O)C2=C1OC)C1=CC2=C(OCO2)C=C1CCN3C

> <INCHI_IDENTIFIER>
InChI=1S/C22H25NO7/c1-23-6-5-11-7-13-14(29-10-28-13)8-12(11)20-19(23)17-15(25-2)9-16(26-3)21(27-4)18(17)22(24)30-20/h7-9,19-20,22,24H,5-6,10H2,1-4H3

> <INCHI_KEY>
OYKXUBNSGAJQOO-UHFFFAOYSA-N

> <FORMULA>
C22H25NO7

> <MOLECULAR_WEIGHT>
415.442

> <EXACT_MASS>
415.163102149

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
43.673652476107236

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
16,18,19-trimethoxy-13-methyl-5,7,22-trioxa-13-azapentacyclo[12.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]docosa-2,4(8),9,15,17,19-hexaen-21-ol

> <ALOGPS_LOGP>
1.68

> <JCHEM_LOGP>
2.2887858686666664

> <ALOGPS_LOGS>
-2.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.218857422312553

> <JCHEM_PKA_STRONGEST_BASIC>
5.263064933970194

> <JCHEM_POLAR_SURFACE_AREA>
78.85000000000001

> <JCHEM_REFRACTIVITY>
107.64779999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.35e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
16,18,19-trimethoxy-13-methyl-5,7,22-trioxa-13-azapentacyclo[12.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]docosa-2,4(8),9,15,17,19-hexaen-21-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      10.527   2.150   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      10.366   3.681   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.959   4.308   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.798   5.839   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.391   6.466   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       7.230   7.997   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       8.476   8.902   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.145   5.560   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.738   6.187   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.493   5.281   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.654   3.750   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.060   3.124   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.221   1.592   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       6.306   4.029   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.713   3.403   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       7.874   1.871   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       9.281   1.245   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.008   5.691   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.084   4.459   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.445   4.643   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.604   3.629   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -2.926   4.419   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.584   5.921   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -1.050   6.059   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.126   7.291   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.403   7.107   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.132   8.463   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.648   8.738   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0       4.807   7.725   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0       6.223   8.331   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   15                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5    9   14                                                  
CONECT    9    8   10   29                                                  
CONECT   10    9   11   18                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    8   15                                                  
CONECT   15   14    3   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   10   19   26                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   24                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   20   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   18   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28    9   30                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₅NO₇

Average Mass

415.4420 Da

Monoisotopic Mass

415.16310 Da

IUPAC Name

16,18,19-trimethoxy-13-methyl-5,7,22-trioxa-13-azapentacyclo[12.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]docosa-2,4(8),9,15,17,19-hexaen-21-ol

Traditional Name

16,18,19-trimethoxy-13-methyl-5,7,22-trioxa-13-azapentacyclo[12.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]docosa-2,4(8),9,15,17,19-hexaen-21-ol

CAS Registry Number

Not Available

SMILES

COC1=CC(OC)=C2C3C(OC(O)C2=C1OC)C1=CC2=C(OCO2)C=C1CCN3C

InChI Identifier

InChI=1S/C22H25NO7/c1-23-6-5-11-7-13-14(29-10-28-13)8-12(11)20-19(23)17-15(25-2)9-16(26-3)21(27-4)18(17)22(24)30-20/h7-9,19-20,22,24H,5-6,10H2,1-4H3

InChI Key

OYKXUBNSGAJQOO-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Rhoeadine alkaloids

Sub Class

Not Available

Direct Parent

Rhoeadine alkaloids

Alternative Parents

Substituents

Rhoeadine-skeleton
Benzazepine
Benzopyran
Isochromane
2-benzopyran
Benzodioxole
Anisole
Alkyl aryl ether
Azepine
Aralkylamine
Benzenoid
Tertiary aliphatic amine
Tertiary amine
Hemiacetal
Acetal
Oxacycle
Azacycle
Organoheterocyclic compound
Ether
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Amine
Organic oxygen compound
Organooxygen 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	1.68	ALOGPS
logP	2.29	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	11.22	ChemAxon
pKa (Strongest Basic)	5.26	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	78.85 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	107.65 m³·mol⁻¹	ChemAxon
Polarizability	43.67 Å³	ChemAxon
Number of Rings	5	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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 16,18,19-trimethoxy-13-methyl-5,7,22-trioxa-13-azapentacyclo[12.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]docosa-2,4(8),9,15,17,19-hexaen-21-ol (NP0255432)

MOL for NP0255432 (16,18,19-trimethoxy-13-methyl-5,7,22-trioxa-13-azapentacyclo[12.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]docosa-2,4(8),9,15,17,19-hexaen-21-ol)

3D MOL for NP0255432 (16,18,19-trimethoxy-13-methyl-5,7,22-trioxa-13-azapentacyclo[12.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]docosa-2,4(8),9,15,17,19-hexaen-21-ol)

3D SDF for NP0255432 (16,18,19-trimethoxy-13-methyl-5,7,22-trioxa-13-azapentacyclo[12.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]docosa-2,4(8),9,15,17,19-hexaen-21-ol)

3D-SDF for NP0255432 (16,18,19-trimethoxy-13-methyl-5,7,22-trioxa-13-azapentacyclo[12.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]docosa-2,4(8),9,15,17,19-hexaen-21-ol)

PDB for NP0255432 (16,18,19-trimethoxy-13-methyl-5,7,22-trioxa-13-azapentacyclo[12.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]docosa-2,4(8),9,15,17,19-hexaen-21-ol)

3D PDB for NP0255432 (16,18,19-trimethoxy-13-methyl-5,7,22-trioxa-13-azapentacyclo[12.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]docosa-2,4(8),9,15,17,19-hexaen-21-ol)

SMILES for NP0255432 (16,18,19-trimethoxy-13-methyl-5,7,22-trioxa-13-azapentacyclo[12.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]docosa-2,4(8),9,15,17,19-hexaen-21-ol)

INCHI for NP0255432 (16,18,19-trimethoxy-13-methyl-5,7,22-trioxa-13-azapentacyclo[12.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]docosa-2,4(8),9,15,17,19-hexaen-21-ol)

Structure for NP0255432 (16,18,19-trimethoxy-13-methyl-5,7,22-trioxa-13-azapentacyclo[12.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]docosa-2,4(8),9,15,17,19-hexaen-21-ol)

3D Structure for NP0255432 (16,18,19-trimethoxy-13-methyl-5,7,22-trioxa-13-azapentacyclo[12.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]docosa-2,4(8),9,15,17,19-hexaen-21-ol)