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Showing NP-Card for (1s,11r,15r,16s)-4,14-diazahexacyclo[12.4.3.0¹,¹⁵.0⁴,¹⁶.0⁵,¹⁰.0¹¹,¹⁶]henicosa-5,7,9-trien-3-one (NP0252643)

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Record Information
Version2.0
Created at2022-09-07 16:13:26 UTC
Updated at2022-09-07 16:13:26 UTC
NP-MRD IDNP0252643
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1s,11r,15r,16s)-4,14-diazahexacyclo[12.4.3.0¹,¹⁵.0⁴,¹⁶.0⁵,¹⁰.0¹¹,¹⁶]henicosa-5,7,9-trien-3-one
DescriptionStrempeliopine belongs to the class of organic compounds known as schizozygine alkaloids. These are alkaloids with a structure based o the hexacyclic schizozygine skeleton, consisting of quinolizidine, indole, and piperidine. (1s,11r,15r,16s)-4,14-diazahexacyclo[12.4.3.0¹,¹⁵.0⁴,¹⁶.0⁵,¹⁰.0¹¹,¹⁶]henicosa-5,7,9-trien-3-one is found in Strempeliopsis strempelioides. (1s,11r,15r,16s)-4,14-diazahexacyclo[12.4.3.0¹,¹⁵.0⁴,¹⁶.0⁵,¹⁰.0¹¹,¹⁶]henicosa-5,7,9-trien-3-one was first documented in 2009 (PMID: 19711927). Based on a literature review a small amount of articles have been published on Strempeliopine (PMID: 34994369) (PMID: 34797070) (PMID: 34324817) (PMID: 30091755).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0252643 ((1s,11r,15r,16s)-4,14-diazahexacyclo[12.4.3.0¹,¹⁵.0⁴,¹⁶.0⁵,¹⁰.0¹¹,¹⁶]henicosa-5,7,9-trien-3-one)


  Mrv1652309072218132D          

 22 27  0  0  1  0            999 V2000
    3.3656   -3.0828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9946   -2.3459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1709   -2.2988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7999   -1.5619    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9763   -1.5147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6053   -0.7779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0579   -0.0881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8816   -0.1353    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3343    0.5545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1579    0.5073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5289   -0.2296    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3248   -0.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0188   -0.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7521   -0.3790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7913   -1.2031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0972   -1.6491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3640   -1.2710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5343   -1.5785    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0762   -0.9193    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2859   -1.7172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5919   -2.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2526   -0.8721    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  2  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
  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  1  6  0  0  0
 12 13  2  0  0  0  0
 13 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
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
  2 18  1  0  0  0  0
 19 18  1  6  0  0  0
 11 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  4 21  1  6  0  0  0
 19 22  1  0  0  0  0
 22  8  1  1  0  0  0
  4 22  1  0  0  0  0
M  END
Download

3D MOL for NP0252643 ((1s,11r,15r,16s)-4,14-diazahexacyclo[12.4.3.0¹,¹⁵.0⁴,¹⁶.0⁵,¹⁰.0¹¹,¹⁶]henicosa-5,7,9-trien-3-one)

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3D SDF for NP0252643 ((1s,11r,15r,16s)-4,14-diazahexacyclo[12.4.3.0¹,¹⁵.0⁴,¹⁶.0⁵,¹⁰.0¹¹,¹⁶]henicosa-5,7,9-trien-3-one)

  Mrv1652309072218132D          

 22 27  0  0  1  0            999 V2000
    3.3656   -3.0828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9946   -2.3459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1709   -2.2988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7999   -1.5619    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9763   -1.5147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6053   -0.7779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0579   -0.0881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8816   -0.1353    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3343    0.5545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1579    0.5073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5289   -0.2296    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3248   -0.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0188   -0.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7521   -0.3790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7913   -1.2031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0972   -1.6491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3640   -1.2710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5343   -1.5785    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0762   -0.9193    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2859   -1.7172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5919   -2.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2526   -0.8721    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  2  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
  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  1  6  0  0  0
 12 13  2  0  0  0  0
 13 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
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
  2 18  1  0  0  0  0
 19 18  1  6  0  0  0
 11 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  4 21  1  6  0  0  0
 19 22  1  0  0  0  0
 22  8  1  1  0  0  0
  4 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0252643

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C1C[C@@]23CC[C@]45[C@H](CCN(CCC2)[C@H]34)C2=CC=CC=C2N15

> <INCHI_IDENTIFIER>
InChI=1S/C19H22N2O/c22-16-12-18-7-3-10-20-11-6-14-13-4-1-2-5-15(13)21(16)19(14,9-8-18)17(18)20/h1-2,4-5,14,17H,3,6-12H2/t14-,17-,18+,19+/m1/s1

> <INCHI_KEY>
BBBSLAHJKPIMRU-OAOYMFHYSA-N

> <FORMULA>
C19H22N2O

> <MOLECULAR_WEIGHT>
294.398

> <EXACT_MASS>
294.173213336

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
67.20206041467391

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,11R,15R,16S)-4,14-diazahexacyclo[12.4.3.0^{1,15}.0^{4,16}.0^{5,10}.0^{11,16}]henicosa-5,7,9-trien-3-one

> <JCHEM_LOGP>
1.9803462819999988

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.737188827952634

> <JCHEM_POLAR_SURFACE_AREA>
23.550000000000004

> <JCHEM_REFRACTIVITY>
84.83940000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,11R,15R,16S)-4,14-diazahexacyclo[12.4.3.0^{1,15}.0^{4,16}.0^{5,10}.0^{11,16}]henicosa-5,7,9-trien-3-one

> <JCHEM_VEBER_RULE>
1

$$$$

Download
3D-SDF for NP0252643 ((1s,11r,15r,16s)-4,14-diazahexacyclo[12.4.3.0¹,¹⁵.0⁴,¹⁶.0⁵,¹⁰.0¹¹,¹⁶]henicosa-5,7,9-trien-3-one)
Download
PDB for NP0252643 ((1s,11r,15r,16s)-4,14-diazahexacyclo[12.4.3.0¹,¹⁵.0⁴,¹⁶.0⁵,¹⁰.0¹¹,¹⁶]henicosa-5,7,9-trien-3-one)
HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  O   UNK     0       6.282  -5.755   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.590  -4.379   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.052  -4.291   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.360  -2.916   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.822  -2.827   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.130  -1.452   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.975  -0.164   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       3.512  -0.253   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       4.357   1.035   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.895   0.947   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.587  -0.429   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.073  -0.834   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.368  -0.002   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.737  -0.707   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.810  -2.246   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.515  -3.078   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.146  -2.373   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       6.597  -2.947   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       5.742  -1.716   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.134  -3.205   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.838  -4.038   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.205  -1.628   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   21   22                                             
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   22                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   19                                                  
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   18                                                  
CONECT   18   17    2   19                                                  
CONECT   19   18   11   20   22                                             
CONECT   20   19   21                                                       
CONECT   21   20    4                                                       
CONECT   22   19    8    4                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   54    0
END

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3D PDB for NP0252643 ((1s,11r,15r,16s)-4,14-diazahexacyclo[12.4.3.0¹,¹⁵.0⁴,¹⁶.0⁵,¹⁰.0¹¹,¹⁶]henicosa-5,7,9-trien-3-one)
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SMILES for NP0252643 ((1s,11r,15r,16s)-4,14-diazahexacyclo[12.4.3.0¹,¹⁵.0⁴,¹⁶.0⁵,¹⁰.0¹¹,¹⁶]henicosa-5,7,9-trien-3-one)
O=C1C[C@@]23CC[C@]45[C@H](CCN(CCC2)[C@H]34)C2=CC=CC=C2N15
Download
INCHI for NP0252643 ((1s,11r,15r,16s)-4,14-diazahexacyclo[12.4.3.0¹,¹⁵.0⁴,¹⁶.0⁵,¹⁰.0¹¹,¹⁶]henicosa-5,7,9-trien-3-one)
InChI=1S/C19H22N2O/c22-16-12-18-7-3-10-20-11-6-14-13-4-1-2-5-15(13)21(16)19(14,9-8-18)17(18)20/h1-2,4-5,14,17H,3,6-12H2/t14-,17-,18+,19+/m1/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC19H22N2O
Average Mass294.3980 Da
Monoisotopic Mass294.17321 Da
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILES
O=C1C[C@@]23CC[C@]45[C@H](CCN(CCC2)[C@H]34)C2=CC=CC=C2N15
InChI Identifier
InChI=1S/C19H22N2O/c22-16-12-18-7-3-10-20-11-6-14-13-4-1-2-5-15(13)21(16)19(14,9-8-18)17(18)20/h1-2,4-5,14,17H,3,6-12H2/t14-,17-,18+,19+/m1/s1
InChI KeyBBBSLAHJKPIMRU-OAOYMFHYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Strempeliopsis strempelioidesLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as schizozygine alkaloids. These are alkaloids with a structure based o the hexacyclic schizozygine skeleton, consisting of quinolizidine, indole, and piperidine.
KingdomOrganic compounds  
Super ClassAlkaloids and derivatives  
ClassSchizozygine alkaloids  
Sub ClassNot Available
Direct ParentSchizozygine alkaloids  
Alternative Parents
Substituents
  • Schizozygine skeleton
    • 

  • Indolo[3,2-1de][1,5]naphthyridine
    • 

  • Beta-carboline
    • 

  • Pyridoindole
    • 

  • Azaspirodecane
    • 

  • Naphthyridine
    • 

  • Quinolizidine
    • 

  • Indole or derivatives
    • 

  • Caprolactam
    • 

  • Azepane
    • 

  • Delta-lactam
    • 

  • Aralkylamine
    • 

  • Piperidinone
    • 

  • Benzenoid
    • 

  • Piperidine
    • 

  • Tertiary carboxylic acid amide
    • 

  • Tertiary aliphatic amine
    • 

  • Amino acid or derivatives
    • 

  • Tertiary amine
    • 

  • Carboxamide group
    • 

  • Lactam
    • 

  • Organoheterocyclic compound
    • 

  • Azacycle
    • 

  • Carboxylic acid derivative
    • 

  • Organooxygen compound
    • 

  • Amine
    • 

  • Carbonyl group
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Organic nitrogen compound
    • 

  • Organonitrogen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00025054  
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound13422342  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. An Y, Wu M, Li W, Li Y, Wang Z, Xue Y, Tang P, Chen F: The total synthesis of (-)-strempeliopine via palladium-catalyzed decarboxylative asymmetric allylic alkylation. Chem Commun (Camb). 2022 Jan 27;58(9):1402-1405. doi: 10.1039/d1cc06278f. [PubMed:34994369  ] 
  2. Zhou W, Zhou T, Tian M, Jiang Y, Yang J, Lei S, Wang Q, Zhang C, Qiu H, He L, Wang Z, Deng J, Zhang M: Asymmetric Total Syntheses of Schizozygane Alkaloids. J Am Chem Soc. 2021 Dec 1;143(47):19975-19982. doi: 10.1021/jacs.1c10279. Epub  2021 Nov 19. [PubMed:34797070  ] 
  3. Zeng X, Boger DL: Total Synthesis of (-)-Strempeliopine. J Am Chem Soc. 2021 Aug 11;143(31):12412-12417. doi: 10.1021/jacs.1c06913. Epub  2021 Jul 29. [PubMed:34324817  ] 
  4. Zhou Q, Dai X, Song H, He H, Wang X, Liu XY, Qin Y: Concise syntheses of eburnane indole alkaloids. Chem Commun (Camb). 2018 Aug 21;54(68):9510-9512. doi: 10.1039/c8cc05374j. [PubMed:30091755  ] 
  5. Bobeck DR, Lee HI, Flick AC, Padwa A: Application of cross-conjugated heteroaromatic betaines to the synthesis of the schizozygane alkaloid (+/-)-strempeliopine. J Org Chem. 2009 Oct 2;74(19):7389-402. doi: 10.1021/jo901336z. [PubMed:19711927  ] 
  6. LOTUS database [Link]