NP-MRD: Showing NP-Card for (1s,19r,20r)-20-methoxy-5,7-dioxa-14-azapentacyclo[12.7.0.0¹,¹⁷.0²,¹⁰.0⁴,⁸]henicosa-2,4(8),9,17-tetraen-19-ol (NP0287107)

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Record Information

Version

2.0

Created at

2022-09-09 16:00:56 UTC

Updated at

2022-09-09 16:00:56 UTC

NP-MRD ID

NP0287107

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,19r,20r)-20-methoxy-5,7-dioxa-14-azapentacyclo[12.7.0.0¹,¹⁷.0²,¹⁰.0⁴,⁸]henicosa-2,4(8),9,17-tetraen-19-ol

Description

84471-41-0 Belongs to the class of organic compounds known as homoerythrinane alkaloids. These are erythrina alkaloids predominantly possessing a 6-5-7-6-membered indolobenzazepine skeleton or a derivative thereof. (1s,19r,20r)-20-methoxy-5,7-dioxa-14-azapentacyclo[12.7.0.0¹,¹⁷.0²,¹⁰.0⁴,⁸]henicosa-2,4(8),9,17-tetraen-19-ol is found in Athrotaxis cupressoides and Athrotaxis selaginoides. Based on a literature review very few articles have been published on 84471-41-0.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309092218002D          

 24 28  0  0  1  0            999 V2000
    4.1613   -0.6174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5736    0.2639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5506   -0.0620    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9357    0.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2570    0.5448    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9066   -0.2021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3783   -0.8789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2003   -0.8089    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1492   -1.6969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0880   -0.0997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0676    0.7105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6549    1.1089    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7166    1.9809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2167    2.6863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0586    2.7656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2435    1.9409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0626    1.8420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3865    1.0832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8913    0.4233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0722    0.5222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7484    1.2810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3658   -0.2515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1543   -0.0087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1670    0.8162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  6  0  0  0
  6 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  5 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  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
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
  5 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 18 24  1  0  0  0  0
M  END


  Mrv1652309092218002D          

 24 28  0  0  1  0            999 V2000
    4.1613   -0.6174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5736    0.2639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5506   -0.0620    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9357    0.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2570    0.5448    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9066   -0.2021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3783   -0.8789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2003   -0.8089    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1492   -1.6969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0880   -0.0997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0676    0.7105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6549    1.1089    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7166    1.9809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2167    2.6863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0586    2.7656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2435    1.9409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0626    1.8420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3865    1.0832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8913    0.4233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0722    0.5222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7484    1.2810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3658   -0.2515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1543   -0.0087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1670    0.8162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  6  0  0  0
  6 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  5 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  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
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
  5 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 18 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0287107

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H]1C[C@]23N(CCC2=C[C@H]1O)CCCC1=CC2=C(OCO2)C=C31

> <INCHI_IDENTIFIER>
InChI=1S/C19H23NO4/c1-22-18-10-19-13(8-15(18)21)4-6-20(19)5-2-3-12-7-16-17(9-14(12)19)24-11-23-16/h7-9,15,18,21H,2-6,10-11H2,1H3/t15-,18-,19+/m1/s1

> <INCHI_KEY>
FCLDQBDXFYQJPD-LZQZEXGQSA-N

> <FORMULA>
C19H23NO4

> <MOLECULAR_WEIGHT>
329.396

> <EXACT_MASS>
329.162708225

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
34.993734833189095

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,19R,20R)-20-methoxy-5,7-dioxa-14-azapentacyclo[12.7.0.0^{1,17}.0^{2,10}.0^{4,8}]henicosa-2,4(8),9,17-tetraen-19-ol

> <JCHEM_LOGP>
1.573804482999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.805423287902748

> <JCHEM_PKA_STRONGEST_BASIC>
9.117459137702715

> <JCHEM_POLAR_SURFACE_AREA>
51.16000000000001

> <JCHEM_REFRACTIVITY>
90.27960000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,19R,20R)-20-methoxy-5,7-dioxa-14-azapentacyclo[12.7.0.0^{1,17}.0^{2,10}.0^{4,8}]henicosa-2,4(8),9,17-tetraen-19-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       7.768  -1.153   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.671   0.493   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.761  -0.116   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.613   1.492   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.346   1.017   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.692  -0.377   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.573  -1.641   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.107  -1.510   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.012  -3.168   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.164  -0.186   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.126   1.326   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       1.222   2.070   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       1.338   3.698   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.271   5.014   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.843   5.162   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.188   3.623   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.717   3.438   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.321   2.022   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.397   0.790   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.868   0.975   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.264   2.391   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.283  -0.469   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.755  -0.016   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       7.778   1.524   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   12   21                                             
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8                                                            
CONECT   10    6   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    5   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   24                                                  
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20   16    5                                                  
CONECT   22   19   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   18                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₃NO₄

Average Mass

329.3960 Da

Monoisotopic Mass

329.16271 Da

IUPAC Name

(1S,19R,20R)-20-methoxy-5,7-dioxa-14-azapentacyclo[12.7.0.0^{1,17}.0^{2,10}.0^{4,8}]henicosa-2,4(8),9,17-tetraen-19-ol

Traditional Name

(1S,19R,20R)-20-methoxy-5,7-dioxa-14-azapentacyclo[12.7.0.0^{1,17}.0^{2,10}.0^{4,8}]henicosa-2,4(8),9,17-tetraen-19-ol

CAS Registry Number

Not Available

SMILES

CO[C@@H]1C[C@]23N(CCC2=C[C@H]1O)CCCC1=CC2=C(OCO2)C=C31

InChI Identifier

InChI=1S/C19H23NO4/c1-22-18-10-19-13(8-15(18)21)4-6-20(19)5-2-3-12-7-16-17(9-14(12)19)24-11-23-16/h7-9,15,18,21H,2-6,10-11H2,1H3/t15-,18-,19+/m1/s1

InChI Key

FCLDQBDXFYQJPD-LZQZEXGQSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Athrotaxis cupressoides	LOTUS Database	35616633
Athrotaxis selaginoides	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as homoerythrinane alkaloids. These are erythrina alkaloids predominantly possessing a 6-5-7-6-membered indolobenzazepine skeleton or a derivative thereof.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Erythrina alkaloids

Sub Class

Homoerythrinane alkaloids

Direct Parent

Homoerythrinane alkaloids

Alternative Parents

Substituents

Homoerythrinane skeleton
Benzazepine
Benzodioxole
Indole or derivatives
Azepine
Aralkylamine
N-alkylpyrrolidine
Benzenoid
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Azacycle
Acetal
Organoheterocyclic compound
Dialkyl ether
Oxacycle
Ether
Organooxygen compound
Hydrocarbon derivative
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
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
logP	1.57	ChemAxon
pKa (Strongest Acidic)	13.81	ChemAxon
pKa (Strongest Basic)	9.12	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	51.16 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	90.28 m³·mol⁻¹	ChemAxon
Polarizability	34.99 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	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

Not Available

Chemspider ID

139562

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

158648

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,19r,20r)-20-methoxy-5,7-dioxa-14-azapentacyclo[12.7.0.0¹,¹⁷.0²,¹⁰.0⁴,⁸]henicosa-2,4(8),9,17-tetraen-19-ol (NP0287107)

MOL for NP0287107 ((1s,19r,20r)-20-methoxy-5,7-dioxa-14-azapentacyclo[12.7.0.0¹,¹⁷.0²,¹⁰.0⁴,⁸]henicosa-2,4(8),9,17-tetraen-19-ol)

3D MOL for NP0287107 ((1s,19r,20r)-20-methoxy-5,7-dioxa-14-azapentacyclo[12.7.0.0¹,¹⁷.0²,¹⁰.0⁴,⁸]henicosa-2,4(8),9,17-tetraen-19-ol)

3D SDF for NP0287107 ((1s,19r,20r)-20-methoxy-5,7-dioxa-14-azapentacyclo[12.7.0.0¹,¹⁷.0²,¹⁰.0⁴,⁸]henicosa-2,4(8),9,17-tetraen-19-ol)

3D-SDF for NP0287107 ((1s,19r,20r)-20-methoxy-5,7-dioxa-14-azapentacyclo[12.7.0.0¹,¹⁷.0²,¹⁰.0⁴,⁸]henicosa-2,4(8),9,17-tetraen-19-ol)

PDB for NP0287107 ((1s,19r,20r)-20-methoxy-5,7-dioxa-14-azapentacyclo[12.7.0.0¹,¹⁷.0²,¹⁰.0⁴,⁸]henicosa-2,4(8),9,17-tetraen-19-ol)

3D PDB for NP0287107 ((1s,19r,20r)-20-methoxy-5,7-dioxa-14-azapentacyclo[12.7.0.0¹,¹⁷.0²,¹⁰.0⁴,⁸]henicosa-2,4(8),9,17-tetraen-19-ol)

SMILES for NP0287107 ((1s,19r,20r)-20-methoxy-5,7-dioxa-14-azapentacyclo[12.7.0.0¹,¹⁷.0²,¹⁰.0⁴,⁸]henicosa-2,4(8),9,17-tetraen-19-ol)

INCHI for NP0287107 ((1s,19r,20r)-20-methoxy-5,7-dioxa-14-azapentacyclo[12.7.0.0¹,¹⁷.0²,¹⁰.0⁴,⁸]henicosa-2,4(8),9,17-tetraen-19-ol)

Structure for NP0287107 ((1s,19r,20r)-20-methoxy-5,7-dioxa-14-azapentacyclo[12.7.0.0¹,¹⁷.0²,¹⁰.0⁴,⁸]henicosa-2,4(8),9,17-tetraen-19-ol)

3D Structure for NP0287107 ((1s,19r,20r)-20-methoxy-5,7-dioxa-14-azapentacyclo[12.7.0.0¹,¹⁷.0²,¹⁰.0⁴,⁸]henicosa-2,4(8),9,17-tetraen-19-ol)