NP-MRD: Showing NP-Card for n-{7-benzyl-2-hydroxy-4-isopropyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0²,⁶]dodecan-4-yl}-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboximidic acid (NP0221997)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-05 23:43:04 UTC

Updated at

2022-09-05 23:43:04 UTC

NP-MRD ID

NP0221997

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-{7-benzyl-2-hydroxy-4-isopropyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0²,⁶]dodecan-4-yl}-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboximidic acid

Description

Ergocristine belongs to the class of organic compounds known as ergotamines, dihydroergotamines, and derivatives. These are organic compounds containing an ergotamine moiety, which is structurally characterized by a benzyl substituent attached to the piperazine ring of the ergopeptine backbone. Ingestion of ergoline alkaloids is known to cause the disease ergotism. Ergoline alkaloids tend to act as a group, producing complex and variable effects of partial agonism or antagonism at adrenergic, dopaminergic, and serotonergic receptors. Ergocristine is a very strong basic compound (based on its pKa). Ergocristine is a potentially toxic compound. Ergocristine is an alkaloid of the ergoline family. Ergometrine is also known to have a non-receptor specific oxytocic activity. In particular, ergoline alkaloids have been shown to have the significant affinity towards the 5-HT1 and 5-HT2 serotonin receptors, D1 and D2 dopamine receptors, and alpha-adrenergic receptors. n-{7-benzyl-2-hydroxy-4-isopropyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0²,⁶]dodecan-4-yl}-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboximidic acid is found in Calamagrostis arundinacea and Scolochloa festucacea. If necessary, a sympathetic nerve blockade may be carried out, such as brachial plexus blockade.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241212302D          

 45 52  0  0  0  0            999 V2000
   -0.4029   -3.8535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7394   -4.6067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2553   -5.2748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5600   -4.6920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3804   -4.6048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7920   -3.8898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7168   -5.3581    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5017   -5.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6742   -6.4188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4592   -6.6728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0618   -6.9716    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0628   -7.7966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2785   -8.0525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7928   -7.3856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2769   -6.7176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1044   -5.9108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3894   -5.4992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4375   -6.3965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1142   -5.0593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8991   -5.3133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0716   -6.1201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8565   -6.3741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4690   -5.8213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2965   -5.0145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5115   -4.7605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5590   -3.8670    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8440   -3.4554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0373   -3.6278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8430   -2.6304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5570   -2.2170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5560   -1.3920    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8411   -0.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8411   -0.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1286    0.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1714    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9964    1.1143    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3018    0.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0143   -0.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0143   -0.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3018   -1.3929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5839   -0.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5839   -0.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1271   -1.3937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1281   -2.2187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2700   -0.9786    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
  7 16  1  0  0  0  0
 16 17  1  0  0  0  0
  4 17  1  0  0  0  0
 16 18  1  0  0  0  0
  8 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  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 20 25  1  0  0  0  0
  4 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 34 42  1  0  0  0  0
 37 42  1  0  0  0  0
 41 43  1  0  0  0  0
 32 43  1  0  0  0  0
 43 44  2  0  0  0  0
 29 44  1  0  0  0  0
 31 45  1  0  0  0  0
M  END


  Mrv0541 02241212302D          

 45 52  0  0  0  0            999 V2000
   -0.4029   -3.8535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7394   -4.6067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2553   -5.2748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5600   -4.6920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3804   -4.6048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7920   -3.8898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7168   -5.3581    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5017   -5.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6742   -6.4188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4592   -6.6728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0618   -6.9716    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0628   -7.7966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2785   -8.0525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7928   -7.3856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2769   -6.7176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1044   -5.9108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3894   -5.4992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4375   -6.3965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1142   -5.0593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8991   -5.3133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0716   -6.1201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8565   -6.3741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4690   -5.8213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2965   -5.0145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5115   -4.7605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5590   -3.8670    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8440   -3.4554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0373   -3.6278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8430   -2.6304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5570   -2.2170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5560   -1.3920    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8411   -0.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8411   -0.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1286    0.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1714    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9964    1.1143    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3018    0.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0143   -0.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0143   -0.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3018   -1.3929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5839   -0.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5839   -0.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1271   -1.3937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1281   -2.2187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2700   -0.9786    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
  7 16  1  0  0  0  0
 16 17  1  0  0  0  0
  4 17  1  0  0  0  0
 16 18  1  0  0  0  0
  8 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  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 20 25  1  0  0  0  0
  4 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 34 42  1  0  0  0  0
 37 42  1  0  0  0  0
 41 43  1  0  0  0  0
 32 43  1  0  0  0  0
 43 44  2  0  0  0  0
 29 44  1  0  0  0  0
 31 45  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0221997

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1(NC(=O)C2CN(C)C3CC4=CNC5=CC=CC(=C45)C3=C2)OC2(O)C3CCCN3C(=O)C(CC3=CC=CC=C3)N2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C35H39N5O5/c1-20(2)34(37-31(41)23-16-25-24-11-7-12-26-30(24)22(18-36-26)17-27(25)38(3)19-23)33(43)40-28(15-21-9-5-4-6-10-21)32(42)39-14-8-13-29(39)35(40,44)45-34/h4-7,9-12,16,18,20,23,27-29,36,44H,8,13-15,17,19H2,1-3H3,(H,37,41)

> <INCHI_KEY>
HEFIYUQVAZFDEE-UHFFFAOYSA-N

> <FORMULA>
C35H39N5O5

> <MOLECULAR_WEIGHT>
609.7147

> <EXACT_MASS>
609.295119383

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
64.19979864318816

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-[7-benzyl-2-hydroxy-5,8-dioxo-4-(propan-2-yl)-3-oxa-6,9-diazatricyclo[7.3.0.0²,⁶]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide

> <ALOGPS_LOGP>
3.60

> <JCHEM_LOGP>
3.7138986181809197

> <ALOGPS_LOGS>
-3.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
11.665306843643839

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.695264815276216

> <JCHEM_PKA_STRONGEST_BASIC>
7.7804876673810845

> <JCHEM_POLAR_SURFACE_AREA>
118.21000000000001

> <JCHEM_REFRACTIVITY>
169.05299999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.75e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-{7-benzyl-2-hydroxy-4-isopropyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0²,⁶]dodecan-4-yl}-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide

> <JCHEM_VEBER_RULE>
0

$$$$

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      -0.752  -7.193   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.380  -8.599   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.477  -9.846   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.912  -8.758   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.443  -8.596   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -5.212  -7.261   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0      -5.071 -10.002   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -6.537 -10.476   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.859 -11.982   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -8.324 -12.456   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0      -5.715 -13.014   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      -5.717 -14.554   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.253 -15.031   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.347 -13.786   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.250 -12.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.928 -11.033   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.594 -10.265   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -2.683 -11.940   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -7.680  -9.444   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -9.145  -9.918   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -9.467 -11.424   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -10.932 -11.898   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -12.075 -10.866   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -11.753  -9.360   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -10.288  -8.886   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0      -2.910  -7.218   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0      -1.575  -6.450   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -0.070  -6.772   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -1.574  -4.910   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.906  -4.138   0.000  0.00  0.00           C+0
HETATM   31  N   UNK     0      -2.905  -2.598   0.000  0.00  0.00           N+0
HETATM   32  C   UNK     0      -1.570  -1.830   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.570  -0.290   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.240   0.480   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       0.320   2.080   0.000  0.00  0.00           C+0
HETATM   36  N   UNK     0       1.860   2.080   0.000  0.00  0.00           N+0
HETATM   37  C   UNK     0       2.430   0.480   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       3.760  -0.290   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       3.760  -1.830   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       2.430  -2.600   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       1.090  -1.830   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       1.090  -0.290   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -0.237  -2.602   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -0.239  -4.142   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      -4.237  -1.827   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   17   26                                             
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   16                                                  
CONECT    8    7    9   19                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   15                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   11   16                                                  
CONECT   16   15    7   17   18                                             
CONECT   17   16    4                                                       
CONECT   18   16                                                            
CONECT   19    8   20                                                       
CONECT   20   19   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   20                                                       
CONECT   26    4   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   44                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   45                                                  
CONECT   32   31   33   43                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   42                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38   42                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42   43                                                  
CONECT   42   41   34   37                                                  
CONECT   43   41   32   44                                                  
CONECT   44   43   29                                                       
CONECT   45   31                                                            
MASTER        0    0    0    0    0    0    0    0   45    0  104    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₅H₃₉N₅O₅

Average Mass

609.7147 Da

Monoisotopic Mass

609.29512 Da

IUPAC Name

N-[7-benzyl-2-hydroxy-5,8-dioxo-4-(propan-2-yl)-3-oxa-6,9-diazatricyclo[7.3.0.0²,⁶]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide

Traditional Name

N-{7-benzyl-2-hydroxy-4-isopropyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0²,⁶]dodecan-4-yl}-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide

CAS Registry Number

Not Available

SMILES

CC(C)C1(NC(=O)C2CN(C)C3CC4=CNC5=CC=CC(=C45)C3=C2)OC2(O)C3CCCN3C(=O)C(CC3=CC=CC=C3)N2C1=O

InChI Identifier

InChI=1S/C35H39N5O5/c1-20(2)34(37-31(41)23-16-25-24-11-7-12-26-30(24)22(18-36-26)17-27(25)38(3)19-23)33(43)40-28(15-21-9-5-4-6-10-21)32(42)39-14-8-13-29(39)35(40,44)45-34/h4-7,9-12,16,18,20,23,27-29,36,44H,8,13-15,17,19H2,1-3H3,(H,37,41)

InChI Key

HEFIYUQVAZFDEE-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

Species Name	Source	Reference
Calamagrostis arundinacea	LOTUS Database	35616633
Scolochloa festucacea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ergotamines, dihydroergotamines, and derivatives. These are organic compounds containing an ergotamine moiety, which is structurally characterized by a benzyl substituent attached to the piperazine ring of the ergopeptine backbone.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Ergoline and derivatives

Sub Class

Lysergic acids and derivatives

Direct Parent

Ergotamines, dihydroergotamines, and derivatives

Alternative Parents

Substituents

Ergotamine
Hybrid peptide
Alpha-dipeptide
Lysergic acid amide
Indoloquinoline
Benzoquinoline
Quinoline-3-carboxamide
N-acyl-alpha amino acid or derivatives
Pyrroloquinoline
Quinoline
Alpha-amino acid or derivatives
3-alkylindole
Indole
Indole or derivatives
Isoindole or derivatives
Aralkylamine
N-alkylpiperazine
Monocyclic benzene moiety
1,4-diazinane
Benzenoid
Oxazolidinone
Piperazine
Pyrrole
Pyrrolidine
Heteroaromatic compound
Oxazolidine
Tertiary carboxylic acid amide
Carboxamide group
Tertiary amine
Amino acid or derivatives
Lactam
Tertiary aliphatic amine
Secondary carboxylic acid amide
Orthocarboxylic acid derivative
Carboxylic acid derivative
Organoheterocyclic compound
Alkanolamine
Oxacycle
Azacycle
Organooxygen compound
Organic nitrogen compound
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Amine
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	3.6	ALOGPS
logP	3.71	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	9.7	ChemAxon
pKa (Strongest Basic)	7.78	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	118.21 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	169.05 m³·mol⁻¹	ChemAxon
Polarizability	64.2 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ergocristine

METLIN ID

Not Available

PubChem Compound

98255

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for n-{7-benzyl-2-hydroxy-4-isopropyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0²,⁶]dodecan-4-yl}-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboximidic acid (NP0221997)

MOL for NP0221997 (n-{7-benzyl-2-hydroxy-4-isopropyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0²,⁶]dodecan-4-yl}-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboximidic acid)

3D MOL for NP0221997 (n-{7-benzyl-2-hydroxy-4-isopropyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0²,⁶]dodecan-4-yl}-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboximidic acid)

3D SDF for NP0221997 (n-{7-benzyl-2-hydroxy-4-isopropyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0²,⁶]dodecan-4-yl}-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboximidic acid)

3D-SDF for NP0221997 (n-{7-benzyl-2-hydroxy-4-isopropyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0²,⁶]dodecan-4-yl}-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboximidic acid)

PDB for NP0221997 (n-{7-benzyl-2-hydroxy-4-isopropyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0²,⁶]dodecan-4-yl}-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboximidic acid)

3D PDB for NP0221997 (n-{7-benzyl-2-hydroxy-4-isopropyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0²,⁶]dodecan-4-yl}-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboximidic acid)

SMILES for NP0221997 (n-{7-benzyl-2-hydroxy-4-isopropyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0²,⁶]dodecan-4-yl}-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboximidic acid)

INCHI for NP0221997 (n-{7-benzyl-2-hydroxy-4-isopropyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0²,⁶]dodecan-4-yl}-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboximidic acid)

Structure for NP0221997 (n-{7-benzyl-2-hydroxy-4-isopropyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0²,⁶]dodecan-4-yl}-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboximidic acid)

3D Structure for NP0221997 (n-{7-benzyl-2-hydroxy-4-isopropyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0²,⁶]dodecan-4-yl}-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboximidic acid)