NP-MRD: Showing NP-Card for 4-methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.0²,⁶.0⁶,¹⁰.0¹⁵,¹⁹]icosa-1(20),4,13,15(19)-tetraen-3-yl 1-methyl 2,3-dihydroxy-3-(3-methylbutyl)butanedioate (NP0249874)

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Record Information

Version

2.0

Created at

2022-09-07 12:33:32 UTC

Updated at

2022-09-07 12:33:32 UTC

NP-MRD ID

NP0249874

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.0²,⁶.0⁶,¹⁰.0¹⁵,¹⁹]icosa-1(20),4,13,15(19)-tetraen-3-yl 1-methyl 2,3-dihydroxy-3-(3-methylbutyl)butanedioate

Description

OHARRINGTONINE belongs to the class of organic compounds known as cephalotaxus alkaloids. These are alkaloids with a structure based on the cephalotaxine skeleton, a tetracyclic 1,3-benzodioxole-containing compound which arises from the skeletal rearrangement of the hydroaromatic component of the Erythrina group. 4-methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.0²,⁶.0⁶,¹⁰.0¹⁵,¹⁹]icosa-1(20),4,13,15(19)-tetraen-3-yl 1-methyl 2,3-dihydroxy-3-(3-methylbutyl)butanedioate is found in Cephalotaxus mannii. OHARRINGTONINE is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004151516412D          

 38 42  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004151516412D          

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    2.8357    0.0527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3154    0.6929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7636    1.3856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4666    2.1553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6515    2.2830    0.0000 C   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
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
  7 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 21 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 19 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 18 34  1  0  0  0  0
 30 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 17 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0249874

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C(O)C(O)(CCC(C)C)C(=O)OC1C2C3=CC4=C(OCO4)C=C3CCN3CCCC23C=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C28H37NO9/c1-16(2)6-9-28(33,24(30)25(31)35-4)26(32)38-23-21(34-3)14-27-8-5-10-29(27)11-7-17-12-19-20(37-15-36-19)13-18(17)22(23)27/h12-14,16,22-24,30,33H,5-11,15H2,1-4H3

> <INCHI_KEY>
CAOHZEUEVKYHPF-UHFFFAOYSA-N

> <FORMULA>
C28H37NO9

> <MOLECULAR_WEIGHT>
531.602

> <EXACT_MASS>
531.246831775

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
56.116746166705475

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.0²,⁶.0⁶,¹⁰.0¹⁵,¹⁹]icosa-1(20),4,13,15(19)-tetraen-3-yl 1-methyl 2,3-dihydroxy-3-(3-methylbutyl)butanedioate

> <ALOGPS_LOGP>
2.48

> <JCHEM_LOGP>
2.0503539205898704

> <ALOGPS_LOGS>
-3.38

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
12.354646843127053

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.978298102795938

> <JCHEM_PKA_STRONGEST_BASIC>
9.40659254634028

> <JCHEM_POLAR_SURFACE_AREA>
123.99000000000002

> <JCHEM_REFRACTIVITY>
136.97599999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.23e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.0²,⁶.0⁶,¹⁰.0¹⁵,¹⁹]icosa-1(20),4,13,15(19)-tetraen-3-yl 1-methyl 2,3-dihydroxy-3-(3-methylbutyl)butanedioate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-APR-15         0                                  
HETATM    1  C   UNK     0      10.697  10.637   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      10.940   9.117   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       9.745   8.145   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.307   8.695   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       9.989   6.625   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      11.427   6.075   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       8.794   5.653   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       7.822   6.849   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       9.765   4.458   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.285   4.702   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.257   3.507   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.707   2.068   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.777   3.750   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.599   4.682   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.160   5.232   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       7.842   3.162   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.647   2.190   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.730   0.653   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.059  -0.125   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.269   0.828   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.699   0.257   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      12.080   0.938   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      13.155  -0.165   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      12.438  -1.528   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      10.920  -1.267   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.710  -2.220   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.280  -1.649   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.226  -2.772   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.691  -2.648   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0       4.831  -1.371   0.000  0.00  0.00           N+0
HETATM   31  C   UNK     0       3.291  -1.385   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.802   0.075   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.909   0.818   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.293   0.098   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.322   1.294   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       5.159   2.586   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       4.604   4.023   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       3.083   4.262   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9   14                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    7   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   36                                                  
CONECT   18   17   19   34                                                  
CONECT   19   18   20   27                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   25                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   21   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   19   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   34                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   18   30   35                                             
CONECT   35   34   36                                                       
CONECT   36   35   17   37                                                  
CONECT   37   36   38                                                       
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₇NO₉

Average Mass

531.6020 Da

Monoisotopic Mass

531.24683 Da

IUPAC Name

4-methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.0²,⁶.0⁶,¹⁰.0¹⁵,¹⁹]icosa-1(20),4,13,15(19)-tetraen-3-yl 1-methyl 2,3-dihydroxy-3-(3-methylbutyl)butanedioate

Traditional Name

4-methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.0²,⁶.0⁶,¹⁰.0¹⁵,¹⁹]icosa-1(20),4,13,15(19)-tetraen-3-yl 1-methyl 2,3-dihydroxy-3-(3-methylbutyl)butanedioate

CAS Registry Number

Not Available

SMILES

COC(=O)C(O)C(O)(CCC(C)C)C(=O)OC1C2C3=CC4=C(OCO4)C=C3CCN3CCCC23C=C1OC

InChI Identifier

InChI=1S/C28H37NO9/c1-16(2)6-9-28(33,24(30)25(31)35-4)26(32)38-23-21(34-3)14-27-8-5-10-29(27)11-7-17-12-19-20(37-15-36-19)13-18(17)22(23)27/h12-14,16,22-24,30,33H,5-11,15H2,1-4H3

InChI Key

CAOHZEUEVKYHPF-UHFFFAOYSA-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
Cephalotaxus mannii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cephalotaxus alkaloids. These are alkaloids with a structure based on the cephalotaxine skeleton, a tetracyclic 1,3-benzodioxole-containing compound which arises from the skeletal rearrangement of the hydroaromatic component of the Erythrina group.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Cephalotaxus alkaloids

Sub Class

Not Available

Direct Parent

Cephalotaxus alkaloids

Alternative Parents

Substituents

Cephalotaxine
Cephalotaxus alkaloid skeleton
Benzazepine
Benzodioxole
Azepine
Beta-hydroxy acid
Fatty acid ester
Aralkylamine
Dicarboxylic acid or derivatives
Hydroxy acid
Monosaccharide
Fatty acyl
N-alkylpyrrolidine
Benzenoid
Tertiary alcohol
Pyrrolidine
Methyl ester
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Amino acid or derivatives
1,2-diol
Carboxylic acid ester
Acetal
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Alcohol
Organonitrogen compound
Organooxygen compound
Organic oxide
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	2.48	ALOGPS
logP	2.05	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	10.98	ChemAxon
pKa (Strongest Basic)	9.41	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	123.99 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	136.98 m³·mol⁻¹	ChemAxon
Polarizability	56.12 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

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

626936

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.0²,⁶.0⁶,¹⁰.0¹⁵,¹⁹]icosa-1(20),4,13,15(19)-tetraen-3-yl 1-methyl 2,3-dihydroxy-3-(3-methylbutyl)butanedioate (NP0249874)

MOL for NP0249874 (4-methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.0²,⁶.0⁶,¹⁰.0¹⁵,¹⁹]icosa-1(20),4,13,15(19)-tetraen-3-yl 1-methyl 2,3-dihydroxy-3-(3-methylbutyl)butanedioate)

3D MOL for NP0249874 (4-methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.0²,⁶.0⁶,¹⁰.0¹⁵,¹⁹]icosa-1(20),4,13,15(19)-tetraen-3-yl 1-methyl 2,3-dihydroxy-3-(3-methylbutyl)butanedioate)

3D SDF for NP0249874 (4-methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.0²,⁶.0⁶,¹⁰.0¹⁵,¹⁹]icosa-1(20),4,13,15(19)-tetraen-3-yl 1-methyl 2,3-dihydroxy-3-(3-methylbutyl)butanedioate)

3D-SDF for NP0249874 (4-methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.0²,⁶.0⁶,¹⁰.0¹⁵,¹⁹]icosa-1(20),4,13,15(19)-tetraen-3-yl 1-methyl 2,3-dihydroxy-3-(3-methylbutyl)butanedioate)

PDB for NP0249874 (4-methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.0²,⁶.0⁶,¹⁰.0¹⁵,¹⁹]icosa-1(20),4,13,15(19)-tetraen-3-yl 1-methyl 2,3-dihydroxy-3-(3-methylbutyl)butanedioate)

3D PDB for NP0249874 (4-methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.0²,⁶.0⁶,¹⁰.0¹⁵,¹⁹]icosa-1(20),4,13,15(19)-tetraen-3-yl 1-methyl 2,3-dihydroxy-3-(3-methylbutyl)butanedioate)

SMILES for NP0249874 (4-methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.0²,⁶.0⁶,¹⁰.0¹⁵,¹⁹]icosa-1(20),4,13,15(19)-tetraen-3-yl 1-methyl 2,3-dihydroxy-3-(3-methylbutyl)butanedioate)

INCHI for NP0249874 (4-methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.0²,⁶.0⁶,¹⁰.0¹⁵,¹⁹]icosa-1(20),4,13,15(19)-tetraen-3-yl 1-methyl 2,3-dihydroxy-3-(3-methylbutyl)butanedioate)

Structure for NP0249874 (4-methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.0²,⁶.0⁶,¹⁰.0¹⁵,¹⁹]icosa-1(20),4,13,15(19)-tetraen-3-yl 1-methyl 2,3-dihydroxy-3-(3-methylbutyl)butanedioate)

3D Structure for NP0249874 (4-methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.0²,⁶.0⁶,¹⁰.0¹⁵,¹⁹]icosa-1(20),4,13,15(19)-tetraen-3-yl 1-methyl 2,3-dihydroxy-3-(3-methylbutyl)butanedioate)