NP-MRD: Showing NP-Card for Apohaemanthamine (NP0069586)

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Record Information

Version

2.0

Created at

2022-04-28 14:57:33 UTC

Updated at

2022-04-28 14:57:34 UTC

NP-MRD ID

NP0069586

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Apohaemanthamine

Description

Apohemanthamine 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. Apohaemanthamine is found in Brunsvigia radulosa and Eucharis amazonica. Based on a literature review very few articles have been published on Apohemanthamine.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 40  0  0  0  0  0  0  0  0999 V2000
   -2.4635   -2.2505   -0.0447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1681   -1.9573    0.0316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8501   -0.5071   -0.0772 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5598   -0.1753   -0.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5156   -1.0907   -0.4446 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8719   -0.7288   -0.4344 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2506    0.5359   -0.0624 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3053    1.4510    0.3006 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9739    1.0780    0.2850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0563    2.0718    0.6713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3985    1.5943    0.6079 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8233    1.5553   -0.7781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6020    0.1304   -1.2554 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8364   -0.4536   -1.4185 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3201   -1.0144   -0.2280 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0198   -0.1234    0.9596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5681    0.2513    1.0616 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6501    0.6169   -0.1445 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1536   -0.7120   -0.2267 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0364   -1.4126   -0.7411 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8701   -3.2331    0.0141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3707   -2.6612    0.1644 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3052   -2.0915   -0.7503 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5938    2.4574    0.5975 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1961    2.5197    1.6748 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0817    2.9379   -0.0414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8963    1.8348   -0.7895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2955    2.2940   -1.3995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9809    0.1015   -2.1724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3799   -1.2377   -0.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2670   -0.7323    1.8676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6944    0.7541    1.0023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1133    0.0237    2.0285 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4777   -1.0973    0.7577 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0025   -0.7292   -0.9377 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 18  1  0
 18  7  1  0
  7  8  2  0
  8  9  1  0
  9  4  2  0
  4  5  1  0
  5  6  2  0
  6 20  1  0
  3  4  1  6
  3  2  1  0
  2  1  2  0
  1 15  1  0
 15 16  1  0
 16 17  1  0
 17 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 11 10  1  0
 20 19  1  0
 17  3  1  0
  6  7  1  0
 13  3  1  0
 10  9  1  0
 14 15  1  0
 19 34  1  0
 19 35  1  0
  8 24  1  0
  5 23  1  0
  2 22  1  0
  1 21  1  0
 15 30  1  6
 16 31  1  0
 16 32  1  0
 17 33  1  1
 12 27  1  0
 12 28  1  0
 13 29  1  6
 10 25  1  0
 10 26  1  0
M  END


  Mrv1652304282216572D          

 20 25  0  0  1  0            999 V2000
    1.4535    0.6949    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5199    1.4881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2691    1.3188    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9956    0.3778    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4333    0.1309    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5308   -0.7711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7090   -1.1832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9012   -0.5927    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4999   -0.6032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7293    0.2505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3352    0.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5945    1.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0250    1.6612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4025    1.2293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9510    0.6131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6917   -0.1701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8837   -0.3370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3564   -0.6587    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0265   -0.1776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7760    0.6084    0.0000 O   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
  4  5  1  0  0  0  0
  1  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  6  0  0  0
  8 10  1  6  0  0  0
  1 10  1  1  0  0  0
  5 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
  3 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 11 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 15 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0069586

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C1OC2=CC3=C(C=C2O1)[C@@]12C=C[C@H]4C[C@@H]1N(C[C@@H]2O4)C3

> <INCHI_IDENTIFIER>
InChI=1S/C16H15NO3/c1-2-16-11-5-13-12(18-8-19-13)3-9(11)6-17-7-15(16)20-10(1)4-14(16)17/h1-3,5,10,14-15H,4,6-8H2/t10-,14-,15-,16-/m0/s1

> <INCHI_KEY>
QMGIUGSXVRJVRE-MVWHLILJSA-N

> <FORMULA>
C16H15NO3

> <MOLECULAR_WEIGHT>
269.3

> <EXACT_MASS>
269.105193347

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
27.93888791324014

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(12S,15R,17R,19S)-6,8,16-trioxa-1-azahexacyclo[13.3.2.0^{3,11}.0^{5,9}.0^{12,17}.0^{12,19}]icosa-3(11),4,9,13-tetraene

> <ALOGPS_LOGP>
1.12

> <JCHEM_LOGP>
1.344326228

> <ALOGPS_LOGS>
-1.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
7.863908418887298

> <JCHEM_POLAR_SURFACE_AREA>
30.930000000000003

> <JCHEM_REFRACTIVITY>
72.84280000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.81e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(12S,15R,17R,19S)-6,8,16-trioxa-1-azahexacyclo[13.3.2.0^{3,11}.0^{5,9}.0^{12,17}.0^{12,19}]icosa-3(11),4,9,13-tetraene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       2.713   1.297   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.837   2.778   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       4.236   2.462   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       3.725   0.705   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.542   0.244   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.724  -1.439   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.190  -2.209   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.682  -1.106   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.800  -1.126   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.361   0.468   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.226   0.521   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.710   1.983   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.647   3.101   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.218   2.295   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.242   1.144   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.758  -0.317   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.250  -0.629   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.999  -1.230   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      11.249  -0.332   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      10.782   1.136   0.000  0.00  0.00           O+0
CONECT    1    2    5   10                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    1    6   11                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8    4                                                       
CONECT   10    8    1                                                       
CONECT   11    5   12   17                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12    3                                                       
CONECT   14   12   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   11                                                       
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   15                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   50    0
END

View in JSmol

Synonyms

Value	Source
Apohaemanthamine	MeSH

Chemical Formula

C₁₆H₁₅NO₃

Average Mass

269.3000 Da

Monoisotopic Mass

269.10519 Da

IUPAC Name

(12S,15R,17R,19S)-6,8,16-trioxa-1-azahexacyclo[13.3.2.0^{3,11}.0^{5,9}.0^{12,17}.0^{12,19}]icosa-3(11),4,9,13-tetraene

Traditional Name

(12S,15R,17R,19S)-6,8,16-trioxa-1-azahexacyclo[13.3.2.0^{3,11}.0^{5,9}.0^{12,17}.0^{12,19}]icosa-3(11),4,9,13-tetraene

CAS Registry Number

Not Available

SMILES

C1OC2=CC3=C(C=C2O1)[C@@]12C=C[C@H]4C[C@@H]1N(C[C@@H]2O4)C3

InChI Identifier

InChI=1S/C16H15NO3/c1-2-16-11-5-13-12(18-8-19-13)3-9(11)6-17-7-15(16)20-10(1)4-14(16)17/h1-3,5,10,14-15H,4,6-8H2/t10-,14-,15-,16-/m0/s1

InChI Key

QMGIUGSXVRJVRE-MVWHLILJSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Brunsvigia radulosa	Plant	KNApSAcK
Eucharis amazonica	Plant	KNApSAcK

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
Tetrahydroisoquinoline
Quinoline
Benzodioxole
Indole or derivatives
Para-oxazepine
Azepine
Aralkylamine
Oxane
Benzenoid
N-alkylpyrrolidine
Pyran
Pyrrolidine
Tertiary amine
Tertiary aliphatic amine
Organoheterocyclic compound
Azacycle
Ether
Dialkyl ether
Oxacycle
Acetal
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Amine
Organic nitrogen 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	1.12	ALOGPS
logP	1.34	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Basic)	7.86	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	30.93 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	72.84 m³·mol⁻¹	ChemAxon
Polarizability	27.94 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

10492187

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Apohaemanthamine (NP0069586)

MOL for NP0069586 (Apohaemanthamine)

3D MOL for NP0069586 (Apohaemanthamine)

3D SDF for NP0069586 (Apohaemanthamine)

3D-SDF for NP0069586 (Apohaemanthamine)

PDB for NP0069586 (Apohaemanthamine)

3D PDB for NP0069586 (Apohaemanthamine)

SMILES for NP0069586 (Apohaemanthamine)

INCHI for NP0069586 (Apohaemanthamine)

Structure for NP0069586 (Apohaemanthamine)

3D Structure for NP0069586 (Apohaemanthamine)