NP-MRD: Showing NP-Card for (+)-Geyerline (NP0079060)

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Record Information

Version

1.0

Created at

2022-04-29 00:08:03 UTC

Updated at

2022-04-29 00:08:03 UTC

NP-MRD ID

NP0079060

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Geyerline

Description

[(1R,2S,3R,4S,5R,6S,8R,9R,10R,13S,16S,17R,18S)-6-(acetyloxy)-11-ethyl-8,9-dihydroxy-4,16,18-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]Nonadecan-13-yl]methyl 2-[(3S)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoate belongs to the class of organic compounds known as aconitane-type diterpenoid alkaloids. These are alkaloid diterpenoids with a structure based on the hexacyclic aconitane skeleton. These compounds have no oxygen functionality at the C7 atom. (+)-Geyerline is found in Delphinium glaucum and Delphinium scabriflorum. Based on a literature review very few articles have been published on [(1R,2S,3R,4S,5R,6S,8R,9R,10R,13S,16S,17R,18S)-6-(acetyloxy)-11-ethyl-8,9-dihydroxy-4,16,18-trimethoxy-11-azahexacyclo[7.7.2.1²,⁵.0¹,¹⁰.0³,⁸.0¹³,¹⁷]Nonadecan-13-yl]methyl 2-[(3S)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304292202082D          

 51 58  0  0  1  0            999 V2000
   -0.0658   -0.0809    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4480    0.8611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1238    1.4236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6604   -0.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3182   -1.5674    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4233   -1.2323    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0833   -1.1729    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7818   -0.1701    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3551   -0.0202    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3237   -0.3602    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5263    0.1673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3892    0.3975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2971   -0.2217    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3905   -1.0257    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9370   -1.5782    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7321   -2.1312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5447   -1.4331    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7789   -0.5704    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1226   -0.0132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6153   -0.3157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0562    0.4284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8952    0.5276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8374    1.2502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0960   -1.7277    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7128   -2.4213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5290   -2.6941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3697    0.6499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3414    0.8566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2713   -2.0278    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6909   -2.6434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1068   -2.3897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3445   -2.9330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7802   -3.6901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9852   -2.1251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5651   -2.7527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4005   -2.7443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9569   -2.1095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7979   -3.4821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6227   -3.4646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0502   -4.1702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6530   -4.8932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8282   -4.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4006   -4.2051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0199   -2.7415    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8384   -2.6379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5668   -3.0802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9928   -1.8275    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2697   -1.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6685   -1.9951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8986   -1.4733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7392   -1.4760    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
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  1  6  0  0  0
  8  1  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
  7 15  1  0  0  0  0
 15 16  1  6  0  0  0
 17 16  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 13 19  1  0  0  0  0
 18 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 17 24  1  0  0  0  0
 14 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 13 27  1  6  0  0  0
  9 28  1  1  0  0  0
  7 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
  5 31  1  0  0  0  0
 29 32  1  1  0  0  0
 32 33  1  0  0  0  0
  5 34  1  6  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 38 43  1  0  0  0  0
 39 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  2  0  0  0  0
 45 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 44 49  1  0  0  0  0
 49 50  2  0  0  0  0
 47 51  1  1  0  0  0
M  END


  Mrv1652304292202082D          

 51 58  0  0  1  0            999 V2000
   -0.0658   -0.0809    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4480    0.8611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1238    1.4236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6604   -0.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3182   -1.5674    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4233   -1.2323    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0833   -1.1729    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7818   -0.1701    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3551   -0.0202    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3237   -0.3602    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5263    0.1673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3892    0.3975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2971   -0.2217    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3905   -1.0257    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9370   -1.5782    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7321   -2.1312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5447   -1.4331    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7789   -0.5704    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1226   -0.0132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6153   -0.3157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0562    0.4284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8952    0.5276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8374    1.2502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0960   -1.7277    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7128   -2.4213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5290   -2.6941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3697    0.6499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3414    0.8566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2713   -2.0278    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6909   -2.6434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1068   -2.3897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3445   -2.9330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7802   -3.6901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9852   -2.1251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5651   -2.7527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4005   -2.7443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9569   -2.1095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7979   -3.4821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6227   -3.4646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0502   -4.1702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6530   -4.8932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8282   -4.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4006   -4.2051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0199   -2.7415    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8384   -2.6379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5668   -3.0802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9928   -1.8275    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2697   -1.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6685   -1.9951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8986   -1.4733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7392   -1.4760    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
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  1  6  0  0  0
  8  1  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
  7 15  1  0  0  0  0
 15 16  1  6  0  0  0
 17 16  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 13 19  1  0  0  0  0
 18 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 17 24  1  0  0  0  0
 14 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 13 27  1  6  0  0  0
  9 28  1  1  0  0  0
  7 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
  5 31  1  0  0  0  0
 29 32  1  1  0  0  0
 32 33  1  0  0  0  0
  5 34  1  6  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 38 43  1  0  0  0  0
 39 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  2  0  0  0  0
 45 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 44 49  1  0  0  0  0
 49 50  2  0  0  0  0
 47 51  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0079060

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCN1C[C@]2(COC(=O)C3=C(C=CC=C3)N3C(=O)C[C@H](C)C3=O)CC[C@H](OC)[C@]34[C@H]5C[C@H]6[C@H](OC)[C@@H]5[C@](O)(C[C@@H]6OC(C)=O)[C@](O)([C@@H](OC)[C@H]23)[C@H]14

> <INCHI_IDENTIFIER>
InChI=1S/C38H50N2O11/c1-7-39-17-35(18-50-33(44)21-10-8-9-11-24(21)40-27(42)14-19(2)32(40)43)13-12-26(47-4)37-23-15-22-25(51-20(3)41)16-36(45,28(23)29(22)48-5)38(46,34(37)39)31(49-6)30(35)37/h8-11,19,22-23,25-26,28-31,34,45-46H,7,12-18H2,1-6H3/t19-,22+,23-,25-,26-,28+,29-,30+,31-,34+,35-,36+,37+,38-/m0/s1

> <INCHI_KEY>
JBEXWLNBXSCEPW-ORMPUAHWSA-N

> <FORMULA>
C38H50N2O11

> <MOLECULAR_WEIGHT>
710.821

> <EXACT_MASS>
710.341460438

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
101

> <JCHEM_AVERAGE_POLARIZABILITY>
57.61755761837376

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1R,2S,3R,4S,5R,6S,8R,9R,10R,13S,16S,17R,18S)-6-(acetyloxy)-11-ethyl-8,9-dihydroxy-4,16,18-trimethoxy-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecan-13-yl]methyl 2-[(3S)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoate

> <ALOGPS_LOGP>
1.93

> <JCHEM_LOGP>
0.3161920479999994

> <ALOGPS_LOGS>
-4.09

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.992994891980459

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.218982611191388

> <JCHEM_PKA_STRONGEST_BASIC>
9.658283273122105

> <JCHEM_POLAR_SURFACE_AREA>
161.37

> <JCHEM_REFRACTIVITY>
180.0095

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.84e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1R,2S,3R,4S,5R,6S,8R,9R,10R,13S,16S,17R,18S)-6-(acetyloxy)-11-ethyl-8,9-dihydroxy-4,16,18-trimethoxy-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecan-13-yl]methyl 2-[(3S)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  N   UNK     0      -0.123  -0.151   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      -0.836   1.607   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.098   2.657   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.233  -1.434   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.594  -2.926   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.790  -2.300   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.022  -2.189   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.459  -0.318   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.530  -0.038   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.604  -0.672   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.982   0.312   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.593   0.742   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.288  -0.414   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.462  -1.915   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.616  -2.946   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.100  -3.978   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.617  -2.675   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.054  -1.065   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.829  -0.025   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.615  -0.589   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       9.438   0.800   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      11.004   0.985   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       9.030   2.334   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.779  -3.225   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.931  -4.520   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       8.454  -5.029   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.423   1.213   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       2.504   1.599   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.373  -3.785   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.290  -4.934   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.199  -4.461   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.510  -5.475   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       3.323  -6.888   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.839  -3.967   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -2.921  -5.138   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -4.481  -5.123   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -5.520  -3.938   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -5.223  -6.500   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -6.762  -6.467   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -7.560  -7.784   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -6.819  -9.134   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -5.279  -9.167   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -4.481  -7.850   0.000  0.00  0.00           C+0
HETATM   44  N   UNK     0      -7.504  -5.118   0.000  0.00  0.00           N+0
HETATM   45  C   UNK     0      -9.032  -4.924   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0     -10.391  -5.750   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      -9.320  -3.411   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      -7.970  -2.670   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      -6.848  -3.724   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      -5.411  -2.750   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0     -10.713  -2.755   0.000  0.00  0.00           C+0
CONECT    1    2    4    8                                                  
CONECT    2    1    3                                                       
CONECT    3    2                                                            
CONECT    4    1    5                                                       
CONECT    5    4    6   31   34                                             
CONECT    6    5    7   10                                                  
CONECT    7    6    8   15   29                                             
CONECT    8    7    1    9                                                  
CONECT    9    8   10   13   28                                             
CONECT   10    9    6   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13    9   14   19   27                                             
CONECT   14   13   15   24                                                  
CONECT   15   14    7   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   24                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18   13                                                       
CONECT   20   18   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   17   14   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   13                                                            
CONECT   28    9                                                            
CONECT   29    7   30   32                                                  
CONECT   30   29   31                                                       
CONECT   31   30    5                                                       
CONECT   32   29   33                                                       
CONECT   33   32                                                            
CONECT   34    5   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39   43                                                  
CONECT   39   38   40   44                                                  
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   38                                                       
CONECT   44   39   45   49                                                  
CONECT   45   44   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45   48   51                                                  
CONECT   48   47   49                                                       
CONECT   49   48   44   50                                                  
CONECT   50   49                                                            
CONECT   51   47                                                            
MASTER        0    0    0    0    0    0    0    0   51    0  116    0
END

View in JSmol

Synonyms

Value	Source
[(1R,2S,3R,4S,5R,6S,8R,9R,10R,13S,16S,17R,18S)-6-(Acetyloxy)-11-ethyl-8,9-dihydroxy-4,16,18-trimethoxy-11-azahexacyclo[7.7.2.1,.0,.0,.0,]nonadecan-13-yl]methyl 2-[(3S)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoic acid	Generator

Chemical Formula

C₃₈H₅₀N₂O₁₁

Average Mass

710.8210 Da

Monoisotopic Mass

710.34146 Da

IUPAC Name

[(1R,2S,3R,4S,5R,6S,8R,9R,10R,13S,16S,17R,18S)-6-(acetyloxy)-11-ethyl-8,9-dihydroxy-4,16,18-trimethoxy-11-azahexacyclo[7.7.2.1^{2,5}.0^{1,10}.0^{3,8}.0^{13,17}]nonadecan-13-yl]methyl 2-[(3S)-3-methyl-2,5-dioxopyrrolidin-1-yl]benzoate

Traditional Name

CAS Registry Number

Not Available

SMILES

CCN1C[C@]2(COC(=O)C3=C(C=CC=C3)N3C(=O)C[C@H](C)C3=O)CC[C@H](OC)[C@]34[C@H]5C[C@H]6[C@H](OC)[C@@H]5[C@](O)(C[C@@H]6OC(C)=O)[C@](O)([C@@H](OC)[C@H]23)[C@H]14

InChI Identifier

InChI=1S/C38H50N2O11/c1-7-39-17-35(18-50-33(44)21-10-8-9-11-24(21)40-27(42)14-19(2)32(40)43)13-12-26(47-4)37-23-15-22-25(51-20(3)41)16-36(45,28(23)29(22)48-5)38(46,34(37)39)31(49-6)30(35)37/h8-11,19,22-23,25-26,28-31,34,45-46H,7,12-18H2,1-6H3/t19-,22+,23-,25-,26-,28+,29-,30+,31-,34+,35-,36+,37+,38-/m0/s1

InChI Key

JBEXWLNBXSCEPW-ORMPUAHWSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Delphinium glaucum	Plant	KNApSAcK
Delphinium scabriflorum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aconitane-type diterpenoid alkaloids. These are alkaloid diterpenoids with a structure based on the hexacyclic aconitane skeleton. These compounds have no oxygen functionality at the C7 atom.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Aconitane-type diterpenoid alkaloids

Alternative Parents

Substituents

Aconitane-type diterpenoid alkaloid
Acylaminobenzoic acid or derivatives
1-phenylpyrrolidine
Quinolidine
Benzoate ester
Alkaloid or derivatives
Benzoic acid or derivatives
Benzoyl
Azepane
Benzenoid
2-pyrrolidone
Pyrrolidone
Piperidine
Carboxylic acid imide, n-substituted
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Tertiary alcohol
Pyrrolidine
Pyrrole
Dicarboximide
Cyclic alcohol
Carboxylic acid imide
Tertiary aliphatic amine
Tertiary amine
Lactam
Carboxylic acid ester
Amino acid or derivatives
1,2-diol
1,2-aminoalcohol
Azacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Alcohol
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	1.93	ALOGPS
logP	0.32	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	12.22	ChemAxon
pKa (Strongest Basic)	9.66	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	161.37 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	180.01 m³·mol⁻¹	ChemAxon
Polarizability	57.62 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

162875501

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Geyerline (NP0079060)

MOL for NP0079060 ((+)-Geyerline)

3D MOL for NP0079060 ((+)-Geyerline)

3D SDF for NP0079060 ((+)-Geyerline)

3D-SDF for NP0079060 ((+)-Geyerline)

PDB for NP0079060 ((+)-Geyerline)

3D PDB for NP0079060 ((+)-Geyerline)

SMILES for NP0079060 ((+)-Geyerline)

INCHI for NP0079060 ((+)-Geyerline)

Structure for NP0079060 ((+)-Geyerline)

3D Structure for NP0079060 ((+)-Geyerline)