NP-MRD: Showing NP-Card for (3r,4r,5s,7r)-4-hydroxy-3-[(2-methylpropanoyl)oxy]-6-(prop-2-en-1-yl)-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-9(16),10,12,14-tetraen-7-yl (2e)-3-phenylprop-2-enoate (NP0147410)

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Record Information

Version

2.0

Created at

2022-09-02 03:00:30 UTC

Updated at

2022-09-02 03:00:30 UTC

NP-MRD ID

NP0147410

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r,4r,5s,7r)-4-hydroxy-3-[(2-methylpropanoyl)oxy]-6-(prop-2-en-1-yl)-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-9(16),10,12,14-tetraen-7-yl (2e)-3-phenylprop-2-enoate

Description

Henrycinol B belongs to the class of organic compounds known as indolonaphthyridine alkaloids. These are a numerous and relatively straightforward subgroup of the b-carbolines, e.G. Canthin-6-one, in which an additional C3 unit is attached between C-1 and the indole nitrogen to form an additional ring. The group includes a few dimeric examples, such as Haplophytine. (3r,4r,5s,7r)-4-hydroxy-3-[(2-methylpropanoyl)oxy]-6-(prop-2-en-1-yl)-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-9(16),10,12,14-tetraen-7-yl (2e)-3-phenylprop-2-enoate is found in Melodinus cochinchinensis. Based on a literature review very few articles have been published on Henrycinol B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022205002D          

 37 41  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309022205002D          

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  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
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
  6 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 16 23  1  0  0  0  0
  5 23  1  0  0  0  0
 23 24  1  6  0  0  0
  7 25  1  0  0  0  0
 25 26  1  0  0  0  0
  4 26  1  0  0  0  0
 26 27  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 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
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 32 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0147410

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(=O)O[C@@H]1CN2C3=CC=CC=C3C3=C2[C@@H]([C@H]1O)N(CC=C)[C@@H](C3)OC(=O)\C=C\C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H32N2O5/c1-4-16-31-25(37-26(33)15-14-20-10-6-5-7-11-20)17-22-21-12-8-9-13-23(21)32-18-24(36-30(35)19(2)3)29(34)28(31)27(22)32/h4-15,19,24-25,28-29,34H,1,16-18H2,2-3H3/b15-14+/t24-,25-,28+,29+/m1/s1

> <INCHI_KEY>
BSOONBGJBDPZMD-CQYVTVQGSA-N

> <FORMULA>
C30H32N2O5

> <MOLECULAR_WEIGHT>
500.595

> <EXACT_MASS>
500.231122138

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
54.65609148524241

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R,4R,5S,7R)-4-hydroxy-3-[(2-methylpropanoyl)oxy]-6-(prop-2-en-1-yl)-1,6-diazatetracyclo[7.6.1.0^{5,16}.0^{10,15}]hexadeca-9(16),10,12,14-tetraen-7-yl (2E)-3-phenylprop-2-enoate

> <ALOGPS_LOGP>
4.01

> <JCHEM_LOGP>
5.681405183666667

> <ALOGPS_LOGS>
-4.94

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.427462129611047

> <JCHEM_PKA_STRONGEST_BASIC>
0.6021353467963886

> <JCHEM_POLAR_SURFACE_AREA>
81.0

> <JCHEM_REFRACTIVITY>
141.62079999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.70e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,4R,5S,7R)-4-hydroxy-3-[(2-methylpropanoyl)oxy]-6-(prop-2-en-1-yl)-1,6-diazatetracyclo[7.6.1.0^{5,16}.0^{10,15}]hexadeca-9(16),10,12,14-tetraen-7-yl (2E)-3-phenylprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.675  -3.932   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.168  -3.611   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.693  -2.147   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      -1.186  -1.827   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      -0.156  -2.971   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.351  -2.651   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.827  -1.186   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.367  -1.186   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.397  -0.042   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.903  -0.362   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.379  -1.827   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.349  -2.971   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.842  -2.651   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       2.597  -3.556   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       2.436  -5.088   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.029  -5.714   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.868  -7.245   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.114  -8.151   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.520  -7.524   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.953  -9.682   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.199 -10.587   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.546 -10.309   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.217  -4.809   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.601  -5.485   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.796  -0.042   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.710  -0.362   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.741   0.783   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -3.247   0.462   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -3.723  -1.002   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -4.278   1.607   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -5.784   1.287   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -6.814   2.431   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -8.321   2.111   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -9.351   3.255   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -8.875   4.720   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -7.369   5.040   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -6.338   3.896   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   26                                                  
CONECT    5    4    6   23                                                  
CONECT    6    5    7   14                                                  
CONECT    7    6    8   25                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8   14                                                  
CONECT   14   13    6   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   23                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   16    5   24                                                  
CONECT   24   23                                                            
CONECT   25    7   26                                                       
CONECT   26   25    4   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   37                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   32                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₂N₂O₅

Average Mass

500.5950 Da

Monoisotopic Mass

500.23112 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(C)C(=O)O[C@@H]1CN2C3=CC=CC=C3C3=C2[C@@H]([C@H]1O)N(CC=C)[C@@H](C3)OC(=O)\C=C\C1=CC=CC=C1

InChI Identifier

InChI=1S/C30H32N2O5/c1-4-16-31-25(37-26(33)15-14-20-10-6-5-7-11-20)17-22-21-12-8-9-13-23(21)32-18-24(36-30(35)19(2)3)29(34)28(31)27(22)32/h4-15,19,24-25,28-29,34H,1,16-18H2,2-3H3/b15-14+/t24-,25-,28+,29+/m1/s1

InChI Key

BSOONBGJBDPZMD-CQYVTVQGSA-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
Melodinus cochinchinensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolonaphthyridine alkaloids. These are a numerous and relatively straightforward subgroup of the b-carbolines, e.G. Canthin-6-one, in which an additional C3 unit is attached between C-1 and the indole nitrogen to form an additional ring. The group includes a few dimeric examples, such as Haplophytine.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Indolonaphthyridine alkaloids

Sub Class

Not Available

Direct Parent

Indolonaphthyridine alkaloids

Alternative Parents

Substituents

Indolo[3,2-1de][1,5]naphthyridine
Beta-carboline
Pyridoindole
Cinnamic acid or derivatives
Cinnamic acid ester
Naphthyridine
3-alkylindole
Indole
Indole or derivatives
Styrene
Fatty acid ester
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Fatty acyl
Benzenoid
Pyrrole
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Heteroaromatic compound
Secondary alcohol
Carboxylic acid ester
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organonitrogen compound
Organic nitrogen compound
Organooxygen 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	4.01	ALOGPS
logS	-4.9	ALOGPS

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

101244126

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3r,4r,5s,7r)-4-hydroxy-3-[(2-methylpropanoyl)oxy]-6-(prop-2-en-1-yl)-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-9(16),10,12,14-tetraen-7-yl (2e)-3-phenylprop-2-enoate (NP0147410)

MOL for NP0147410 ((3r,4r,5s,7r)-4-hydroxy-3-[(2-methylpropanoyl)oxy]-6-(prop-2-en-1-yl)-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-9(16),10,12,14-tetraen-7-yl (2e)-3-phenylprop-2-enoate)

3D MOL for NP0147410 ((3r,4r,5s,7r)-4-hydroxy-3-[(2-methylpropanoyl)oxy]-6-(prop-2-en-1-yl)-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-9(16),10,12,14-tetraen-7-yl (2e)-3-phenylprop-2-enoate)

3D SDF for NP0147410 ((3r,4r,5s,7r)-4-hydroxy-3-[(2-methylpropanoyl)oxy]-6-(prop-2-en-1-yl)-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-9(16),10,12,14-tetraen-7-yl (2e)-3-phenylprop-2-enoate)

3D-SDF for NP0147410 ((3r,4r,5s,7r)-4-hydroxy-3-[(2-methylpropanoyl)oxy]-6-(prop-2-en-1-yl)-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-9(16),10,12,14-tetraen-7-yl (2e)-3-phenylprop-2-enoate)

PDB for NP0147410 ((3r,4r,5s,7r)-4-hydroxy-3-[(2-methylpropanoyl)oxy]-6-(prop-2-en-1-yl)-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-9(16),10,12,14-tetraen-7-yl (2e)-3-phenylprop-2-enoate)

3D PDB for NP0147410 ((3r,4r,5s,7r)-4-hydroxy-3-[(2-methylpropanoyl)oxy]-6-(prop-2-en-1-yl)-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-9(16),10,12,14-tetraen-7-yl (2e)-3-phenylprop-2-enoate)

SMILES for NP0147410 ((3r,4r,5s,7r)-4-hydroxy-3-[(2-methylpropanoyl)oxy]-6-(prop-2-en-1-yl)-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-9(16),10,12,14-tetraen-7-yl (2e)-3-phenylprop-2-enoate)

INCHI for NP0147410 ((3r,4r,5s,7r)-4-hydroxy-3-[(2-methylpropanoyl)oxy]-6-(prop-2-en-1-yl)-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-9(16),10,12,14-tetraen-7-yl (2e)-3-phenylprop-2-enoate)

Structure for NP0147410 ((3r,4r,5s,7r)-4-hydroxy-3-[(2-methylpropanoyl)oxy]-6-(prop-2-en-1-yl)-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-9(16),10,12,14-tetraen-7-yl (2e)-3-phenylprop-2-enoate)

3D Structure for NP0147410 ((3r,4r,5s,7r)-4-hydroxy-3-[(2-methylpropanoyl)oxy]-6-(prop-2-en-1-yl)-1,6-diazatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁵]hexadeca-9(16),10,12,14-tetraen-7-yl (2e)-3-phenylprop-2-enoate)