NP-MRD: Showing NP-Card for (1s,18s,20r)-19-ethenyl-18-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaen-14-one (NP0183587)

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Record Information

Version

2.0

Created at

2022-09-03 22:31:23 UTC

Updated at

2022-09-03 22:31:23 UTC

NP-MRD ID

NP0183587

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,18s,20r)-19-ethenyl-18-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaen-14-one

Description

Strictosidine lactam belongs to the class of organic compounds known as beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety. (1s,18s,20r)-19-ethenyl-18-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaen-14-one is found in Catharanthus roseus and Rauvolfia serpentina. Based on a literature review very few articles have been published on Strictosidine lactam.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042200312D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309042200312D          

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 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 25 33  1  0  0  0  0
 28 33  1  0  0  0  0
 34 26  1  1  0  0  0
 22 34  1  0  0  0  0
 34 35  1  0  0  0  0
 36 35  1  1  0  0  0
 19 36  1  0  0  0  0
  3 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0183587

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](O[C@@H]2OC=C3[C@H](C[C@@H]4N(CCC5=C4NC4=CC=CC=C54)C3=O)C2C=C)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H30N2O8/c1-2-12-15-9-18-20-14(13-5-3-4-6-17(13)27-20)7-8-28(18)24(33)16(15)11-34-25(12)36-26-23(32)22(31)21(30)19(10-29)35-26/h2-6,11-12,15,18-19,21-23,25-27,29-32H,1,7-10H2/t12?,15-,18+,19-,21-,22+,23-,25+,26+/m1/s1

> <INCHI_KEY>
LBRPLJCNRZUXLS-QJWUKCNESA-N

> <FORMULA>
C26H30N2O8

> <MOLECULAR_WEIGHT>
498.532

> <EXACT_MASS>
498.200215934

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
51.50230070070089

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,18S,20R)-19-ethenyl-18-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8,15-pentaen-14-one

> <JCHEM_LOGP>
-0.025120791666666198

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.195573720660832

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.20665776487562

> <JCHEM_PKA_STRONGEST_BASIC>
0.04894351832158861

> <JCHEM_POLAR_SURFACE_AREA>
144.71

> <JCHEM_REFRACTIVITY>
126.85089999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,18S,20R)-19-ethenyl-18-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8,15-pentaen-14-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       7.804  -4.387   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.291  -4.674   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.783  -6.128   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.270  -6.415   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.265  -5.248   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.752  -5.535   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.244  -6.989   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.269  -7.276   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.777  -8.730   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.291  -9.017   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.275  -6.109   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.788  -6.396   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.767  -4.655   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.772  -3.488   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.747  -4.368   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.255  -2.914   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       3.762  -7.869   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.767  -9.036   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.280  -8.749   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.285  -9.916   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.777 -11.369   0.000  0.00  0.00           O+0
HETATM   22  N   UNK     0       8.798  -9.629   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       9.803 -10.795   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.316 -10.508   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.824  -9.055   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.819  -7.888   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0      11.618  -6.571   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0      13.117  -6.925   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      14.382  -6.047   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      15.775  -6.704   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      15.902  -8.239   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      14.637  -9.117   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      13.244  -8.459   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.306  -8.175   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.301  -7.008   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.788  -7.295   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   36                                                  
CONECT    4    3    5   17                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    6   16                                                  
CONECT   16   15                                                            
CONECT   17    4   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   36                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   34                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   33                                                  
CONECT   26   25   27   34                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   25   28                                                  
CONECT   34   26   22   35                                                  
CONECT   35   34   36                                                       
CONECT   36   35   19    3                                                  
MASTER        0    0    0    0    0    0    0    0   36    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₀N₂O₈

Average Mass

498.5320 Da

Monoisotopic Mass

498.20022 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](O[C@@H]2OC=C3[C@H](C[C@@H]4N(CCC5=C4NC4=CC=CC=C54)C3=O)C2C=C)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C26H30N2O8/c1-2-12-15-9-18-20-14(13-5-3-4-6-17(13)27-20)7-8-28(18)24(33)16(15)11-34-25(12)36-26-23(32)22(31)21(30)19(10-29)35-26/h2-6,11-12,15,18-19,21-23,25-27,29-32H,1,7-10H2/t12?,15-,18+,19-,21-,22+,23-,25+,26+/m1/s1

InChI Key

LBRPLJCNRZUXLS-QJWUKCNESA-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
Catharanthus roseus	LOTUS Database	35616633
Rauvolfia serpentina	LOTUS Database	35616633

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
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
3-alkylindole
Indole
Delta-lactam
Piperidinone
Monosaccharide
Oxane
Piperidine
Benzenoid
Vinylogous ester
Pyrrole
Tertiary carboxylic acid amide
Heteroaromatic compound
Secondary alcohol
Carboxamide group
Lactam
Polyol
Acetal
Azacycle
Carboxylic acid derivative
Oxacycle
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Primary alcohol
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

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

102271368

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,18s,20r)-19-ethenyl-18-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaen-14-one (NP0183587)

MOL for NP0183587 ((1s,18s,20r)-19-ethenyl-18-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaen-14-one)

3D MOL for NP0183587 ((1s,18s,20r)-19-ethenyl-18-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaen-14-one)

3D SDF for NP0183587 ((1s,18s,20r)-19-ethenyl-18-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaen-14-one)

3D-SDF for NP0183587 ((1s,18s,20r)-19-ethenyl-18-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaen-14-one)

PDB for NP0183587 ((1s,18s,20r)-19-ethenyl-18-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaen-14-one)

3D PDB for NP0183587 ((1s,18s,20r)-19-ethenyl-18-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaen-14-one)

SMILES for NP0183587 ((1s,18s,20r)-19-ethenyl-18-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaen-14-one)

INCHI for NP0183587 ((1s,18s,20r)-19-ethenyl-18-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaen-14-one)

Structure for NP0183587 ((1s,18s,20r)-19-ethenyl-18-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaen-14-one)

3D Structure for NP0183587 ((1s,18s,20r)-19-ethenyl-18-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-17-oxa-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8,15-pentaen-14-one)