NP-MRD: Showing NP-Card for dihydroelymoclavine (NP0290906)

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Record Information

Version

1.0

Created at

2022-09-09 21:47:43 UTC

Updated at

2022-09-09 21:47:43 UTC

NP-MRD ID

NP0290906

Secondary Accession Numbers

None

Natural Product Identification

Common Name

dihydroelymoclavine

Description

9,10-Dihydrolysergol belongs to the class of organic compounds known as clavines and derivatives. These are hydroxy and dehydro derivatives of 6,8-dimethylergolenes and the corresponding ergolines. dihydroelymoclavine is found in Balansia henningsiana. It was first documented in 2002 (PMID: 12393061). Based on a literature review very few articles have been published on 9,10-Dihydrolysergol (PMID: 35389067).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 42  0  0  0  0  0  0  0  0999 V2000
    1.8519    2.6902    0.4090 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5582    1.2933    0.5137 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6208    0.5160   -0.0298 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3825   -0.9499    0.2371 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4369   -1.8281   -0.3557 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6968   -1.5249    0.1612 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0536   -1.2941   -0.4402 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0097   -0.5332    0.3335 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3709   -0.9044   -0.0639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7258   -2.1494   -0.4897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0445   -2.3713   -0.8382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9992   -1.3676   -0.7644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6309   -0.1139   -0.3332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2583    1.0683   -0.1378 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3547    1.9811    0.3147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1160    1.3615    0.4101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3178    0.0756    0.0052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7597    1.7581    0.8210 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2469    0.9408    0.0558 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7649    3.1282    1.4278 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9035    2.9021    0.0890 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1898    3.2402   -0.2830 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7947    0.7059   -1.1062 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5540    0.7904    0.5040 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3215   -1.1161    1.3134 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2145   -2.8722   -0.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4348   -1.8258   -1.4646 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6036   -1.4779    1.1418 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1234   -0.9029   -1.4852 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9603   -2.3768   -0.3932 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1590   -0.6946    1.4202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9961   -2.9182   -0.5464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3227   -3.3684   -1.1779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0332   -1.5248   -1.0330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2563    1.2228   -0.3114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5171    3.0182    0.5703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6484    1.4934    1.9048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6260    2.8363    0.7016 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0961    1.0921   -1.0288 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  1  0
  4  7  1  0
  7  8  1  0
  8 19  1  0
 19 18  1  0
 18 16  1  0
 16 15  2  0
 15 14  1  0
 14 13  1  0
 13 12  2  0
 12 11  1  0
 11 10  2  0
 10  9  1  0
  9 17  2  0
 19  2  1  0
 17 16  1  0
  9  8  1  0
 17 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  1
  5 26  1  0
  5 27  1  0
  6 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  1
 19 39  1  6
 18 37  1  0
 18 38  1  0
 15 36  1  0
 14 35  1  0
 12 34  1  0
 11 33  1  0
 10 32  1  0
M  END


  Mrv1652309092223472D          

 19 22  0  0  1  0            999 V2000
    3.2789    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8500   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5771   -1.3590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7925   -1.6139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1794   -1.0619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  1  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  1  0  0  0  0
  4  5  1  6  0  0  0
  5  6  1  0  0  0  0
  4  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
  9 17  2  0  0  0  0
 13 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
  8 19  1  0  0  0  0
 19  2  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0290906

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C[C@H](CO)C[C@H]2[C@H]1CC1=CNC3=CC=CC2=C13

> <INCHI_IDENTIFIER>
InChI=1S/C16H20N2O/c1-18-8-10(9-19)5-13-12-3-2-4-14-16(12)11(7-17-14)6-15(13)18/h2-4,7,10,13,15,17,19H,5-6,8-9H2,1H3/t10-,13-,15-/m1/s1

> <INCHI_KEY>
UFKTZIXVYHGAES-WDBKCZKBSA-N

> <FORMULA>
C16H20N2O

> <MOLECULAR_WEIGHT>
256.349

> <EXACT_MASS>
256.157563272

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
29.766897017692788

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(2R,4R,7R)-6-methyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),9,12,14-tetraen-4-yl]methanol

> <JCHEM_LOGP>
1.707580902333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
17.35606635270646

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.425200468604288

> <JCHEM_PKA_STRONGEST_BASIC>
8.582753742826085

> <JCHEM_POLAR_SURFACE_AREA>
39.26

> <JCHEM_REFRACTIVITY>
77.06449999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,4R,7R)-6-methyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),9,12,14-tetraen-4-yl]methanol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       6.121   3.850   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       6.121   2.310   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.788  -0.770   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      10.122   0.000   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.453  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.944  -2.537   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.479  -3.013   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.335  -1.982   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.655  -0.476   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      -0.250   0.770   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       0.655   2.016   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.120   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.120  -0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.453   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   19                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5                                                            
CONECT    7    4    8                                                       
CONECT    8    7    9   19                                                  
CONECT    9    8   10   17                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16    9   13                                                  
CONECT   18   16   19                                                       
CONECT   19   18    8    2                                                  
MASTER        0    0    0    0    0    0    0    0   19    0   44    0
END

View in JSmol

Synonyms

Value	Source
9,10-Dihydrolysergol, (8alpha)-isomer	MeSH
9,10-Dihydrolysergol, (8beta)-isomer	MeSH
9,10-Dihydrolysergol, (8alpha,10beta)-isomer	MeSH
Dihydrolysergol-I	MeSH

Chemical Formula

C₁₆H₂₀N₂O

Average Mass

256.3490 Da

Monoisotopic Mass

256.15756 Da

IUPAC Name

[(2R,4R,7R)-6-methyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),9,12,14-tetraen-4-yl]methanol

Traditional Name

[(2R,4R,7R)-6-methyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),9,12,14-tetraen-4-yl]methanol

CAS Registry Number

Not Available

SMILES

CN1C[C@H](CO)C[C@H]2[C@H]1CC1=CNC3=CC=CC2=C13

InChI Identifier

InChI=1S/C16H20N2O/c1-18-8-10(9-19)5-13-12-3-2-4-14-16(12)11(7-17-14)6-15(13)18/h2-4,7,10,13,15,17,19H,5-6,8-9H2,1H3/t10-,13-,15-/m1/s1

InChI Key

UFKTZIXVYHGAES-WDBKCZKBSA-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
Balansia henningsiana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as clavines and derivatives. These are hydroxy and dehydro derivatives of 6,8-dimethylergolenes and the corresponding ergolines.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Ergoline and derivatives

Sub Class

Clavines and derivatives

Direct Parent

Clavines and derivatives

Alternative Parents

Substituents

Clavine skeleton
Indoloquinoline
Benzoquinoline
Pyrroloquinoline
3-alkylindole
Quinoline
Indole
Indole or derivatives
Isoindole or derivatives
Aralkylamine
Benzenoid
Piperidine
1,3-aminoalcohol
Heteroaromatic compound
Pyrrole
Tertiary aliphatic amine
Tertiary amine
Organoheterocyclic compound
Azacycle
Organooxygen compound
Organonitrogen compound
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Primary alcohol
Amine
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	1.71	ChemAxon
pKa (Strongest Acidic)	15.43	ChemAxon
pKa (Strongest Basic)	8.58	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	39.26 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	77.06 m³·mol⁻¹	ChemAxon
Polarizability	29.77 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

4438476

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5274124

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

An C, Zhu F, Yao Y, Zhang K, Wang W, Zhang J, Wei G, Xia Y, Gao Q, Gao SS: Beyond the cyclopropyl ring formation: fungal Aj_EasH catalyzes asymmetric hydroxylation of ergot alkaloids. Appl Microbiol Biotechnol. 2022 Apr;106(8):2981-2991. doi: 10.1007/s00253-022-11892-4. Epub 2022 Apr 7. [PubMed:35389067 ]
Vairetti M, Battaglia A, Carfagna N, Luigi Canonico P, Berte F, Richelmi P: Antioxidant properties of MDL and MMDL, two nicergoline metabolites, during chronic administration of haloperidol. Eur J Pharmacol. 2002 Oct 18;453(1):69-73. doi: 10.1016/s0014-2999(02)02386-5. [PubMed:12393061 ]
LOTUS database [Link]

Showing NP-Card for dihydroelymoclavine (NP0290906)

MOL for NP0290906 (dihydroelymoclavine)

3D MOL for NP0290906 (dihydroelymoclavine)

3D SDF for NP0290906 (dihydroelymoclavine)

3D-SDF for NP0290906 (dihydroelymoclavine)

PDB for NP0290906 (dihydroelymoclavine)

3D PDB for NP0290906 (dihydroelymoclavine)

SMILES for NP0290906 (dihydroelymoclavine)

INCHI for NP0290906 (dihydroelymoclavine)

Structure for NP0290906 (dihydroelymoclavine)

3D Structure for NP0290906 (dihydroelymoclavine)