NP-MRD: Showing NP-Card for Cuscutamine (NP0140040)

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Record Information

Version

2.0

Created at

2022-06-29 20:43:16 UTC

Updated at

2022-06-29 20:43:16 UTC

NP-MRD ID

NP0140040

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cuscutamine

Description

Cuscutamine belongs to the class of organic compounds known as beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety. Cuscutamine was first documented in 2004 (PMID: 15095143). Based on a literature review very few articles have been published on Cuscutamine (PMID: 29450982).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 37  0  0  0  0  0  0  0  0999 V2000
   -1.5542    3.9641    0.2116 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0856    2.8056    0.1178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4127    2.7889   -0.2231 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2774    1.6168    0.3707 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0422    1.6077   -0.4123 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7597    0.3627   -0.0383 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1339   -0.7042    0.5458 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1140   -1.6414    0.7321 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2950   -1.1809    0.2856 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5765   -1.7159    0.2379 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6160   -0.9849   -0.2927 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4438    0.2868   -0.7928 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1728    0.8123   -0.7433 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1256    0.0875   -0.2137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3161   -0.7762    0.8873 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9873   -2.0088    0.3985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3325   -1.5386   -0.1200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0553   -0.1170   -0.5146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7584    0.4897   -1.3508 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9327    0.3561    0.1907 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8655    3.4066   -0.8712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9372    1.6606    1.4452 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6206    2.4989   -0.1159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1828    1.6295   -1.4796 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9587   -2.5750    1.1594 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6923   -2.7151    0.6349 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6281   -1.4209   -0.3247 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3097    0.7884   -1.1894 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9955    1.8011   -1.1228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4944   -0.6308    1.9719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4392   -2.5178   -0.4137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1477   -2.6996    1.2634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0498   -1.5809    0.7233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6554   -2.1552   -0.9572 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  7 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20  4  1  0
 14  6  1  0
 20 15  1  0
 14  9  1  0
  3 21  1  0
  4 22  1  1
  5 23  1  0
  5 24  1  0
  8 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 15 30  1  1
 16 31  1  0
 16 32  1  0
 17 33  1  0
 17 34  1  0
M  END


  Mrv1652306292222432D          

 20 23  0  0  1  0            999 V2000
    4.0936    1.1040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8339    0.7399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7163   -0.0767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3078   -0.6518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9033   -0.2172    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5185    0.5125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6941    0.5441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2545   -0.1540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6394   -0.8837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4638   -0.9154    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8486   -1.6451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6730   -1.6767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4090   -2.3432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4547    0.0483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7692   -0.4107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0289   -0.0465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0258    0.7767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6597    1.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4000    0.8715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1660    1.1779    0.0000 N   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
  3  5  1  0  0  0  0
  6  5  1  6  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
  7 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0140040

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)[C@@H]1CC2=C(NC3=CC=CC=C23)[C@@H]2CCC(=O)N12

> <INCHI_IDENTIFIER>
InChI=1S/C15H14N2O3/c18-13-6-5-11-14-9(7-12(15(19)20)17(11)13)8-3-1-2-4-10(8)16-14/h1-4,11-12,16H,5-7H2,(H,19,20)/t11-,12-/m0/s1

> <INCHI_KEY>
NVWTUEWEKRBVPS-RYUDHWBXSA-N

> <FORMULA>
C15H14N2O3

> <MOLECULAR_WEIGHT>
270.288

> <EXACT_MASS>
270.100442319

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
27.96654061795028

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5S,11bS)-3-oxo-1H,2H,3H,5H,6H,11H,11bH-indolo[3,2-g]indolizine-5-carboxylic acid

> <ALOGPS_LOGP>
1.25

> <JCHEM_LOGP>
1.176898173666667

> <ALOGPS_LOGS>
-2.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.291663055071826

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.943825751509129

> <JCHEM_PKA_STRONGEST_BASIC>
-1.8580305591091753

> <JCHEM_POLAR_SURFACE_AREA>
73.4

> <JCHEM_REFRACTIVITY>
71.54090000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.78e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5S,11bS)-3-oxo-1H,2H,5H,6H,11H,11bH-indolo[3,2-g]indolizine-5-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0       7.641   2.061   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.023   1.381   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.804  -0.143   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       9.908  -1.217   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       7.286  -0.405   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       6.568   0.957   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.029   1.016   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.208  -0.287   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.927  -1.650   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.466  -1.709   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.184  -3.071   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       8.723  -3.130   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       6.364  -4.374   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.716   0.090   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.436  -0.767   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.054  -0.087   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.048   1.450   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.231   2.307   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.613   1.627   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       4.043   2.199   0.000  0.00  0.00           N+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   10                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8   20                                                  
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9    5   11                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    8   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   14   20                                                  
CONECT   20   19    7                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₄N₂O₃

Average Mass

270.2880 Da

Monoisotopic Mass

270.10044 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

OC(=O)[C@@H]1CC2=C(NC3=CC=CC=C23)[C@@H]2CCC(=O)N12

InChI Identifier

InChI=1S/C15H14N2O3/c18-13-6-5-11-14-9(7-12(15(19)20)17(11)13)8-3-1-2-4-10(8)16-14/h1-4,11-12,16H,5-7H2,(H,19,20)/t11-,12-/m0/s1

InChI Key

NVWTUEWEKRBVPS-RYUDHWBXSA-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 beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Pyridoindoles

Direct Parent

Beta carbolines

Alternative Parents

Substituents

Beta-carboline
Alpha-amino acid or derivatives
3-alkylindole
Indole
Pyrrolidone
2-pyrrolidone
N-alkylpyrrolidine
Benzenoid
Pyrrole
Pyrrolidine
Heteroaromatic compound
Tertiary carboxylic acid amide
Lactam
Carboxamide group
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Azacycle
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
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

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

5363570

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6995636

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Rho T, Yoon KD: Application of off-line two-dimensional high-performance countercurrent chromatography on the chloroform-soluble extract of Cuscuta auralis seeds. J Sep Sci. 2018 May;41(10):2169-2177. doi: 10.1002/jssc.201701498. Epub 2018 Mar 23. [PubMed:29450982 ]
Umehara K, Nemoto K, Ohkubo T, Miyase T, Degawa M, Noguchi H: Isolation of a new 15-membered macrocyclic glycolipid lactone, Cuscutic Resinoside a from the seeds of Cuscuta chinensis: a stimulator of breast cancer cell proliferation. Planta Med. 2004 Apr;70(4):299-304. doi: 10.1055/s-2004-818939. [PubMed:15095143 ]

Showing NP-Card for Cuscutamine (NP0140040)

MOL for NP0140040 (Cuscutamine)

3D MOL for NP0140040 (Cuscutamine)

3D SDF for NP0140040 (Cuscutamine)

3D-SDF for NP0140040 (Cuscutamine)

PDB for NP0140040 (Cuscutamine)

3D PDB for NP0140040 (Cuscutamine)

SMILES for NP0140040 (Cuscutamine)

INCHI for NP0140040 (Cuscutamine)

Structure for NP0140040 (Cuscutamine)

3D Structure for NP0140040 (Cuscutamine)