NP-MRD: Showing NP-Card for 1-({15-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9-trien-18-yl}oxy)butan-2-ol (NP0284068)

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Record Information

Version

2.0

Created at

2022-09-09 11:36:58 UTC

Updated at

2022-09-09 11:36:59 UTC

NP-MRD ID

NP0284068

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-({15-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9-trien-18-yl}oxy)butan-2-ol

Description

1-({15-Methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]Nonadeca-2,4(8),9-trien-18-yl}oxy)butan-2-ol belongs to the class of organic compounds known as crinine- and haemanthamine-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids compounds with a structure based on the crinine or haemanthamine backbone. Both backbones have a common 5,10b-ethano bridge moiety in their frameworks, which is a very significant taxonomic feature, and the configurations of the 5,10b-ethano bridge are opposite to each other. 1-({15-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9-trien-18-yl}oxy)butan-2-ol is found in Narcissus poeticus. 1-({15-Methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]Nonadeca-2,4(8),9-trien-18-yl}oxy)butan-2-ol is a very strong basic compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004251509502D          

 27 31  0  0  0  0            999 V2000
   -2.9591    2.0918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4041    1.4814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5980    1.6569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3468    2.4427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0430    1.0464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2368    1.2219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3182    0.6115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0090   -0.1534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4142   -0.8720    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2287   -1.0032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9418   -0.5038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5788   -0.8137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2651   -0.3559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0646   -0.5596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5053    0.1378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9783    0.7725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2118    0.4674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5277    0.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7858    0.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1089    0.8466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8737    1.1561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5241    0.6485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4096   -0.1686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6449   -0.4780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9945    0.0296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0600   -0.6762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9456   -1.4932    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  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  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  1  0  0  0  0
 13 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 11 19  1  0  0  0  0
 19 20  1  0  0  0  0
  7 20  1  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
  9 25  1  0  0  0  0
 20 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END


  Mrv1533004251509502D          

 27 31  0  0  0  0            999 V2000
   -2.9591    2.0918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4041    1.4814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5980    1.6569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3468    2.4427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0430    1.0464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2368    1.2219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3182    0.6115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0090   -0.1534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4142   -0.8720    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2287   -1.0032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9418   -0.5038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5788   -0.8137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2651   -0.3559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0646   -0.5596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5053    0.1378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9783    0.7725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2118    0.4674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5277    0.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7858    0.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1089    0.8466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8737    1.1561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5241    0.6485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4096   -0.1686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6449   -0.4780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9945    0.0296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0600   -0.6762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9456   -1.4932    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  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  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  1  0  0  0  0
 13 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 11 19  1  0  0  0  0
 19 20  1  0  0  0  0
  7 20  1  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
  9 25  1  0  0  0  0
 20 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0284068

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(O)COC1CN2CC3=CC4=C(OCO4)C=C3C11CCC(CC21)OC

> <INCHI_IDENTIFIER>
InChI=1S/C21H29NO5/c1-3-14(23)11-25-20-10-22-9-13-6-17-18(27-12-26-17)8-16(13)21(20)5-4-15(24-2)7-19(21)22/h6,8,14-15,19-20,23H,3-5,7,9-12H2,1-2H3

> <INCHI_KEY>
CAWUOMCIUGNLPP-UHFFFAOYSA-N

> <FORMULA>
C21H29NO5

> <MOLECULAR_WEIGHT>
375.465

> <EXACT_MASS>
375.204573038

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
41.744771885546164

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-({15-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9-trien-18-yl}oxy)butan-2-ol

> <ALOGPS_LOGP>
1.75

> <JCHEM_LOGP>
1.923885267333333

> <ALOGPS_LOGS>
-2.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.47643538297994

> <JCHEM_PKA_STRONGEST_BASIC>
8.460671299871311

> <JCHEM_POLAR_SURFACE_AREA>
60.390000000000015

> <JCHEM_REFRACTIVITY>
100.12779999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.60e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-({15-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9-trien-18-yl}oxy)butan-2-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0      -5.524   3.905   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.488   2.765   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.983   3.093   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.514   4.560   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.947   1.953   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.442   2.281   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.594   1.141   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.017  -0.286   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       0.773  -1.628   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       2.294  -1.873   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.625  -0.940   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.814  -1.519   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.095  -0.664   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       7.587  -1.045   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.410   0.257   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       7.426   1.442   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.995   0.872   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.718   1.746   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.334   0.700   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.070   1.580   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.498   2.158   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.712   1.210   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.498  -0.315   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.070  -0.892   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.856   0.055   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.712  -1.262   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       5.498  -2.787   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                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   20                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   25                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   19                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   13   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   11   20                                                  
CONECT   20   19    7   21   25                                             
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24    9   20                                                  
CONECT   26   23   27                                                       
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₉NO₅

Average Mass

375.4650 Da

Monoisotopic Mass

375.20457 Da

IUPAC Name

1-({15-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9-trien-18-yl}oxy)butan-2-ol

Traditional Name

1-({15-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9-trien-18-yl}oxy)butan-2-ol

CAS Registry Number

Not Available

SMILES

CCC(O)COC1CN2CC3=CC4=C(OCO4)C=C3C11CCC(CC21)OC

InChI Identifier

InChI=1S/C21H29NO5/c1-3-14(23)11-25-20-10-22-9-13-6-17-18(27-12-26-17)8-16(13)21(20)5-4-15(24-2)7-19(21)22/h6,8,14-15,19-20,23H,3-5,7,9-12H2,1-2H3

InChI Key

CAWUOMCIUGNLPP-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Narcissus poeticus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as crinine- and haemanthamine-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids compounds with a structure based on the crinine or haemanthamine backbone. Both backbones have a common 5,10b-ethano bridge moiety in their frameworks, which is a very significant taxonomic feature, and the configurations of the 5,10b-ethano bridge are opposite to each other.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Amaryllidaceae alkaloids

Sub Class

Crinine- and Haemanthamine-type amaryllidaceae alkaloids

Direct Parent

Crinine- and Haemanthamine-type amaryllidaceae alkaloids

Alternative Parents

Substituents

Hemanthamine/crinine alkaloid skeleton
Benzoquinoline
Phenanthridine
Benzazepine
Quinoline
Tetrahydroisoquinoline
Benzodioxole
Indole or derivatives
Aralkylamine
Azepine
Benzenoid
N-alkylpyrrolidine
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Azacycle
Acetal
Dialkyl ether
Ether
Hydrocarbon derivative
Organonitrogen compound
Organic oxygen compound
Organooxygen compound
Organic nitrogen compound
Organopnictogen 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	1.75	ALOGPS
logP	1.92	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	14.48	ChemAxon
pKa (Strongest Basic)	8.46	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	60.39 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	100.13 m³·mol⁻¹	ChemAxon
Polarizability	41.74 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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-({15-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9-trien-18-yl}oxy)butan-2-ol (NP0284068)

MOL for NP0284068 (1-({15-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9-trien-18-yl}oxy)butan-2-ol)

3D MOL for NP0284068 (1-({15-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9-trien-18-yl}oxy)butan-2-ol)

3D SDF for NP0284068 (1-({15-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9-trien-18-yl}oxy)butan-2-ol)

3D-SDF for NP0284068 (1-({15-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9-trien-18-yl}oxy)butan-2-ol)

PDB for NP0284068 (1-({15-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9-trien-18-yl}oxy)butan-2-ol)

3D PDB for NP0284068 (1-({15-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9-trien-18-yl}oxy)butan-2-ol)

SMILES for NP0284068 (1-({15-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9-trien-18-yl}oxy)butan-2-ol)

INCHI for NP0284068 (1-({15-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9-trien-18-yl}oxy)butan-2-ol)

Structure for NP0284068 (1-({15-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9-trien-18-yl}oxy)butan-2-ol)

3D Structure for NP0284068 (1-({15-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9-trien-18-yl}oxy)butan-2-ol)