NP-MRD: Showing NP-Card for Cycloclavin (NP0057943)

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Record Information

Version

2.0

Created at

2022-04-28 03:17:57 UTC

Updated at

2022-04-28 03:17:57 UTC

NP-MRD ID

NP0057943

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cycloclavin

Description

Cycloclavine 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. Cycloclavin is found in Aspergillus japonicus, Ipomoea hildebrandii and Ipomoea hildebrandtii. Cycloclavin was first documented in 2018 (PMID: 29976068). Based on a literature review a small amount of articles have been published on Cycloclavine (PMID: 35389067) (PMID: 31560525) (PMID: 31411477).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 40  0  0  0  0  0  0  0  0999 V2000
   -2.4151    2.5349    0.1559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9315    1.4395   -0.6641 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7739    0.2904   -0.3988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8128   -0.9054   -0.2877 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2239   -2.0637    0.5477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0676   -1.1209   -1.5898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4757   -0.4006   -0.4538 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7758   -0.8851    0.0971 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0248   -2.1435    0.6211 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3004   -2.4435    1.1146 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3354   -1.5290    1.1022 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0860   -0.2553    0.5724 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8357    0.8494    0.4037 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0407    1.7989   -0.1770 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7764    1.2899   -0.3775 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8343    0.0021    0.1013 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4830    1.8121   -0.9578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6035    1.0745   -0.2540 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5189    2.6370    0.0191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2598    2.2898    1.2274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9184    3.4955   -0.0995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4298    0.1144   -1.2922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3821    0.3964    0.5002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3439   -1.9671    0.6876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0861   -3.0577    0.0780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7873   -1.9778    1.5636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3677   -0.6067   -2.5036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6808   -2.1490   -1.7619 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2232   -2.8513    0.6278 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4543   -3.4430    1.5176 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3167   -1.7759    1.4876 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8341    0.9209    0.6804 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3820    2.7755   -0.4235 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4287    2.8867   -0.6502 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4632    1.6764   -2.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5157    1.2911    0.8377 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  1
  4  6  1  0
  7  6  1  6
  7 18  1  0
 18 17  1  0
 17 15  1  0
 15 14  2  0
 14 13  1  0
 13 12  1  0
 12 11  2  0
 11 10  1  0
 10  9  2  0
  9  8  1  0
  8 16  2  0
 18  2  1  0
 16 15  1  0
  7  4  1  0
  8  7  1  0
 16 12  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  5 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
 18 36  1  1
 17 34  1  0
 17 35  1  0
 14 33  1  0
 13 32  1  0
 11 31  1  0
 10 30  1  0
  9 29  1  0
M  END


  Mrv1652304282205172D          

 18 22  0  0  1  0            999 V2000
    2.8047   -0.0934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7945    0.7315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0750    1.1351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3657    0.7138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3759   -0.1111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0954   -0.5147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6462    1.1175    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6360    1.9424    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3453    2.3637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0648    1.9601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8462    2.2247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3394    1.5633    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1517    2.1877    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1352    0.8529    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7415    0.2933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4846    0.3085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4164    2.9691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  2  0  0  0  0
  1  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  3 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
  2 12  1  0  0  0  0
  8 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  7 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
  7 17  1  6  0  0  0
 13 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0057943

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C[C@@]2(C)C[C@@]22[C@H]1CC1=CNC3=CC=CC2=C13

> <INCHI_IDENTIFIER>
InChI=1S/C16H18N2/c1-15-8-16(15)11-4-3-5-12-14(11)10(7-17-12)6-13(16)18(2)9-15/h3-5,7,13,17H,6,8-9H2,1-2H3/t13-,15-,16-/m1/s1

> <INCHI_KEY>
ZWJHDICNUKHUGE-FVQBIDKESA-N

> <FORMULA>
C16H18N2

> <MOLECULAR_WEIGHT>
238.334

> <EXACT_MASS>
238.146998588

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
27.588472012714085

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,4S,7R)-4,6-dimethyl-6,11-diazapentacyclo[7.6.1.0^{2,4}.0^{2,7}.0^{12,16}]hexadeca-1(16),9,12,14-tetraene

> <ALOGPS_LOGP>
3.23

> <JCHEM_LOGP>
2.5058412593333332

> <ALOGPS_LOGS>
-3.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.263503488635333

> <JCHEM_PKA_STRONGEST_BASIC>
8.152067387031913

> <JCHEM_POLAR_SURFACE_AREA>
19.03

> <JCHEM_REFRACTIVITY>
73.0266

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.12e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,4S,7R)-4,6-dimethyl-6,11-diazapentacyclo[7.6.1.0^{2,4}.0^{2,7}.0^{12,16}]hexadeca-1(16),9,12,14-tetraene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       5.235  -0.174   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.216   1.365   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.873   2.119   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.549   1.333   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.568  -0.207   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.911  -0.961   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.206   2.086   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.187   3.626   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.511   4.412   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.854   3.659   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.313   4.153   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       6.233   2.918   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0      -0.283   4.084   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      -1.173   2.827   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.252   1.592   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.384   0.548   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.905   0.576   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.777   5.542   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   12                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4    8   15   17                                             
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9    3   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11    2                                                       
CONECT   13    8   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14    7   16   17                                             
CONECT   16   15                                                            
CONECT   17   15    7                                                       
CONECT   18   13                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₈N₂

Average Mass

238.3340 Da

Monoisotopic Mass

238.14700 Da

IUPAC Name

(2S,4S,7R)-4,6-dimethyl-6,11-diazapentacyclo[7.6.1.0^{2,4}.0^{2,7}.0^{12,16}]hexadeca-1(16),9,12,14-tetraene

Traditional Name

(2S,4S,7R)-4,6-dimethyl-6,11-diazapentacyclo[7.6.1.0^{2,4}.0^{2,7}.0^{12,16}]hexadeca-1(16),9,12,14-tetraene

CAS Registry Number

Not Available

SMILES

CN1C[C@@]2(C)C[C@@]22[C@H]1CC1=CNC3=CC=CC2=C13

InChI Identifier

InChI=1S/C16H18N2/c1-15-8-16(15)11-4-3-5-12-14(11)10(7-17-12)6-13(16)18(2)9-15/h3-5,7,13,17H,6,8-9H2,1-2H3/t13-,15-,16-/m1/s1

InChI Key

ZWJHDICNUKHUGE-FVQBIDKESA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Aspergillus japonicus	Fungi	KNApSAcK
Ipomoea hildebrandii	Plant	KNApSAcK
Ipomoea hildebrandtii	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
N-alkylpyrrolidine
Piperidine
Heteroaromatic compound
Pyrrole
Pyrrolidine
Tertiary amine
Tertiary aliphatic amine
Azacycle
Organoheterocyclic compound
Organonitrogen compound
Hydrocarbon derivative
Amine
Organic nitrogen 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	3.23	ALOGPS
logP	2.51	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	17.26	ChemAxon
pKa (Strongest Basic)	8.15	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	19.03 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	73.03 m³·mol⁻¹	ChemAxon
Polarizability	27.59 Å³	ChemAxon
Number of Rings	5	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

C00011221

Chemspider ID

25991549

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cycloclavine

METLIN ID

Not Available

PubChem Compound

24823847

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 ]
Yan L, Liu Y: Insights into the Mechanism and Enantioselectivity in the Biosynthesis of Ergot Alkaloid Cycloclavine Catalyzed by Aj_EasH from Aspergillus japonicus. Inorg Chem. 2019 Oct 21;58(20):13771-13781. doi: 10.1021/acs.inorgchem.9b01168. Epub 2019 Sep 27. [PubMed:31560525 ]
Wang W, Mi Y, Cao XP, Shi ZF: Enantioselective Formal Synthesis of (+)-Cycloclavine and Total Synthesis of (+)-5-epi-Cycloclavine. Org Lett. 2019 Sep 6;21(17):6603-6607. doi: 10.1021/acs.orglett.9b02015. Epub 2019 Aug 14. [PubMed:31411477 ]
Deng L, Chen M, Dong G: Concise Synthesis of (-)-Cycloclavine and (-)-5- epi-Cycloclavine via Asymmetric C-C Activation. J Am Chem Soc. 2018 Aug 1;140(30):9652-9658. doi: 10.1021/jacs.8b05549. Epub 2018 Jul 17. [PubMed:29976068 ]

Showing NP-Card for Cycloclavin (NP0057943)

MOL for NP0057943 (Cycloclavin)

3D MOL for NP0057943 (Cycloclavin)

3D SDF for NP0057943 (Cycloclavin)

3D-SDF for NP0057943 (Cycloclavin)

PDB for NP0057943 (Cycloclavin)

3D PDB for NP0057943 (Cycloclavin)

SMILES for NP0057943 (Cycloclavin)

INCHI for NP0057943 (Cycloclavin)

Structure for NP0057943 (Cycloclavin)

3D Structure for NP0057943 (Cycloclavin)