NP-MRD: Showing NP-Card for (-)-Stephalonine H (NP0078768)

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Record Information

Version

2.0

Created at

2022-04-28 23:50:08 UTC

Updated at

2022-04-28 23:50:08 UTC

NP-MRD ID

NP0078768

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Stephalonine H

Description

(1S,8S,10S,11R,12S,13S)-3-hydroxy-4,11,12-trimethoxy-17-methyl-18-oxa-17-azapentacyclo[8.4.3.1⁸,¹¹.0¹,¹⁰.0²,⁷]Octadeca-2(7),3,5-trien-13-yl 4-hydroxy-3-methoxybenzoate belongs to the class of organic compounds known as hasubanan alkaloids. These are alkaloids with a structure based on the hasubanan skeleton, a tetracyclic propellane. (-)-Stephalonine H is found in Stephania longa . Based on a literature review very few articles have been published on (1S,8S,10S,11R,12S,13S)-3-hydroxy-4,11,12-trimethoxy-17-methyl-18-oxa-17-azapentacyclo[8.4.3.1⁸,¹¹.0¹,¹⁰.0²,⁷]Octadeca-2(7),3,5-trien-13-yl 4-hydroxy-3-methoxybenzoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292201502D          

 38 43  0  0  1  0            999 V2000
    0.7837    0.6984    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652304292201502D          

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  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
  8 11  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
  1 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
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 15 24  1  0  0  0  0
 20 24  1  0  0  0  0
 24 25  1  1  0  0  0
 17 25  1  1  0  0  0
 23 26  1  0  0  0  0
 20 27  1  0  0  0  0
  1 27  1  0  0  0  0
 19 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 18 31  1  0  0  0  0
 29 32  1  0  0  0  0
 32 33  1  0  0  0  0
 28 34  1  0  0  0  0
 15 35  1  1  0  0  0
 35 36  1  0  0  0  0
 14 37  1  6  0  0  0
 37 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0078768

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H]1[C@H](C[C@]23CCN(C)[C@@]22C[C@H](O[C@@]12OC)C1=C3C(O)=C(OC)C=C1)OC(=O)C1=CC(OC)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H33NO9/c1-29-11-10-26-13-21(37-25(32)15-6-8-17(30)19(12-15)34-3)24(35-4)28(36-5)27(26,29)14-20(38-28)16-7-9-18(33-2)23(31)22(16)26/h6-9,12,20-21,24,30-31H,10-11,13-14H2,1-5H3/t20-,21-,24-,26-,27-,28-/m0/s1

> <INCHI_KEY>
DTWWCAVKBUKGQG-WYDMWVAWSA-N

> <FORMULA>
C28H33NO9

> <MOLECULAR_WEIGHT>
527.57

> <EXACT_MASS>
527.215531647

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
53.55094260739186

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,8S,10S,11R,12S,13S)-3-hydroxy-4,11,12-trimethoxy-17-methyl-18-oxa-17-azapentacyclo[8.4.3.1^{8,11}.0^{1,10}.0^{2,7}]octadeca-2(7),3,5-trien-13-yl 4-hydroxy-3-methoxybenzoate

> <ALOGPS_LOGP>
2.40

> <JCHEM_LOGP>
2.8853622472797325

> <ALOGPS_LOGS>
-3.31

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
9.670912005889138

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.907350857497784

> <JCHEM_PKA_STRONGEST_BASIC>
7.640272112325635

> <JCHEM_POLAR_SURFACE_AREA>
116.15000000000002

> <JCHEM_REFRACTIVITY>
135.76179999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.58e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,8S,10S,11R,12S,13S)-3-hydroxy-4,11,12-trimethoxy-17-methyl-18-oxa-17-azapentacyclo[8.4.3.1^{8,11}.0^{1,10}.0^{2,7}]octadeca-2(7),3,5-trien-13-yl 4-hydroxy-3-methoxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       1.463   1.304   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.376   0.213   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.776  -1.274   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.311  -2.364   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.265  -1.670   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.665  -3.157   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.154  -3.553   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.241  -2.463   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.840  -0.976   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.352  -0.580   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.729  -2.859   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       4.554  -5.040   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.042  -5.437   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.980   3.119   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.177   4.562   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.518   6.087   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.771   5.093   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.897   3.836   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.365   2.391   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.841   2.230   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.459   1.542   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.050   2.181   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0       1.739   3.619   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0       3.238   3.690   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.109   5.289   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.888   4.903   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.108   0.872   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.350   1.208   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.867   1.469   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.400   2.914   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.415   4.097   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       8.852   0.285   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      10.370   0.546   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       5.817  -0.237   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       1.005   5.562   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       1.286   7.076   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -0.524   3.450   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -1.562   2.312   0.000  0.00  0.00           C+0
CONECT    1    2   14   27                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9    5                                                       
CONECT   11    8                                                            
CONECT   12    7   13                                                       
CONECT   13   12                                                            
CONECT   14    1   15   37                                                  
CONECT   15   14   16   24   35                                             
CONECT   16   15   17                                                       
CONECT   17   16   18   25                                                  
CONECT   18   17   19   31                                                  
CONECT   19   18   20   28                                                  
CONECT   20   19   21   24   27                                             
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   26                                                  
CONECT   24   23   15   20   25                                             
CONECT   25   24   17                                                       
CONECT   26   23                                                            
CONECT   27   20    1                                                       
CONECT   28   19   29   34                                                  
CONECT   29   28   30   32                                                  
CONECT   30   29   31                                                       
CONECT   31   30   18                                                       
CONECT   32   29   33                                                       
CONECT   33   32                                                            
CONECT   34   28                                                            
CONECT   35   15   36                                                       
CONECT   36   35                                                            
CONECT   37   14   38                                                       
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   86    0
END

View in JSmol

Synonyms

Value	Source
(1S,8S,10S,11R,12S,13S)-3-Hydroxy-4,11,12-trimethoxy-17-methyl-18-oxa-17-azapentacyclo[8.4.3.1,.0,.0,]octadeca-2(7),3,5-trien-13-yl 4-hydroxy-3-methoxybenzoic acid	Generator

Chemical Formula

C₂₈H₃₃NO₉

Average Mass

527.5700 Da

Monoisotopic Mass

527.21553 Da

IUPAC Name

(1S,8S,10S,11R,12S,13S)-3-hydroxy-4,11,12-trimethoxy-17-methyl-18-oxa-17-azapentacyclo[8.4.3.1^{8,11}.0^{1,10}.0^{2,7}]octadeca-2(7),3,5-trien-13-yl 4-hydroxy-3-methoxybenzoate

Traditional Name

(1S,8S,10S,11R,12S,13S)-3-hydroxy-4,11,12-trimethoxy-17-methyl-18-oxa-17-azapentacyclo[8.4.3.1^{8,11}.0^{1,10}.0^{2,7}]octadeca-2(7),3,5-trien-13-yl 4-hydroxy-3-methoxybenzoate

CAS Registry Number

Not Available

SMILES

CO[C@H]1[C@H](C[C@]23CCN(C)[C@@]22C[C@H](O[C@@]12OC)C1=C3C(O)=C(OC)C=C1)OC(=O)C1=CC(OC)=C(O)C=C1

InChI Identifier

InChI=1S/C28H33NO9/c1-29-11-10-26-13-21(37-25(32)15-6-8-17(30)19(12-15)34-3)24(35-4)28(36-5)27(26,29)14-20(38-28)16-7-9-18(33-2)23(31)22(16)26/h6-9,12,20-21,24,30-31H,10-11,13-14H2,1-5H3/t20-,21-,24-,26-,27-,28-/m0/s1

InChI Key

DTWWCAVKBUKGQG-WYDMWVAWSA-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
Stephania longa	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hasubanan alkaloids. These are alkaloids with a structure based on the hasubanan skeleton, a tetracyclic propellane.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Hasubanan alkaloids

Sub Class

Not Available

Direct Parent

Hasubanan alkaloids

Alternative Parents

Substituents

Hasubanan skeleton
Phenanthrene
M-methoxybenzoic acid or derivatives
P-hydroxybenzoic acid alkyl ester
P-hydroxybenzoic acid ester
Methoxyphenol
Tetralin
Benzoate ester
Benzoic acid or derivatives
Indole or derivatives
Phenol ether
Benzoyl
Methoxybenzene
Anisole
Phenoxy compound
Ketal
1-hydroxy-4-unsubstituted benzenoid
Aralkylamine
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Benzenoid
N-alkylpyrrolidine
Monocyclic benzene moiety
Oxolane
Pyrrolidine
Amino acid or derivatives
Carboxylic acid ester
Tertiary aliphatic amine
Tertiary amine
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Azacycle
Ether
Dialkyl ether
Acetal
Carboxylic acid derivative
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Organonitrogen 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	2.4	ALOGPS
logP	2.89	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	8.91	ChemAxon
pKa (Strongest Basic)	7.64	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	116.15 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	135.76 m³·mol⁻¹	ChemAxon
Polarizability	53.55 Å³	ChemAxon
Number of Rings	6	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

9888156

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11713435

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Stephalonine H (NP0078768)

MOL for NP0078768 ((-)-Stephalonine H)

3D MOL for NP0078768 ((-)-Stephalonine H)

3D SDF for NP0078768 ((-)-Stephalonine H)

3D-SDF for NP0078768 ((-)-Stephalonine H)

PDB for NP0078768 ((-)-Stephalonine H)

3D PDB for NP0078768 ((-)-Stephalonine H)

SMILES for NP0078768 ((-)-Stephalonine H)

INCHI for NP0078768 ((-)-Stephalonine H)

Structure for NP0078768 ((-)-Stephalonine H)

3D Structure for NP0078768 ((-)-Stephalonine H)