NP-MRD: Showing NP-Card for (1s,19r)-5,7-dioxa-13-azapentacyclo[11.7.0.0¹,¹⁶.0²,¹⁰.0⁴,⁸]icosa-2,4(8),9,15,17-pentaen-19-ol (NP0157845)

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Record Information

Version

2.0

Created at

2022-09-02 15:19:58 UTC

Updated at

2022-09-02 15:19:58 UTC

NP-MRD ID

NP0157845

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,19r)-5,7-dioxa-13-azapentacyclo[11.7.0.0¹,¹⁶.0²,¹⁰.0⁴,⁸]icosa-2,4(8),9,15,17-pentaen-19-ol

Description

Erythrocarine belongs to the class of organic compounds known as erythrinanes. These are erythrina alkaloids possessing either a 6-5-6-6-membered indoloisoquinoline core or a derivative thereof. (1s,19r)-5,7-dioxa-13-azapentacyclo[11.7.0.0¹,¹⁶.0²,¹⁰.0⁴,⁸]icosa-2,4(8),9,15,17-pentaen-19-ol was first documented in 2003 (PMID: 12816439). Based on a literature review very few articles have been published on Erythrocarine.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 42  0  0  0  0  0  0  0  0999 V2000
   -2.9945    2.7312    0.0693 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6699    2.2670    0.3954 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8460    1.5134    1.6573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9939    0.1619    1.5471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9561   -0.3846    0.1984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7333   -1.2014   -0.4521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2629   -1.3522   -1.8472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0319   -0.5913   -1.8607 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0136   -1.5492   -2.2382 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3609   -2.3942   -0.9896 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0793   -1.3454   -0.1747 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3024   -1.5755    0.4080 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9740   -0.5647    1.1022 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3841    0.6895    1.1971 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1546    0.9236    0.6133 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4962   -0.1122   -0.0798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8390    0.1255   -0.6689 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0935    1.6104   -0.7728 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2855    1.4629    1.9355 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5824    0.8516    1.8482 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1913   -0.5252    1.7709 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3850    3.1517    0.8944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1656    3.2335    0.6836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8539    2.0235    2.5883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1529   -0.4330    2.4127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5946   -1.6987   -0.0097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9467   -0.8145   -2.5612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1429   -2.4143   -2.1375 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9136   -1.0376   -2.5387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3114   -2.2533   -3.0034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5090   -2.8070   -0.4938 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0403   -3.1740   -1.3638 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7259   -2.5667    0.3096 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7620    1.9142    0.7089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8015    1.7080   -1.6550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1724    2.1610   -1.0782 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0108    1.1991    0.8741 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2071    1.0670    2.7110 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2 18  1  0
 17 18  1  6
 17  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  2  0
  5  4  1  0
  4  3  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 19  1  0
 19 20  1  0
 20 21  1  0
 14 15  1  0
 15 16  2  0
  3  2  1  0
 16 11  1  0
  5 17  1  0
 21 13  1  0
 16 17  1  0
  1 22  1  0
  2 23  1  1
 18 35  1  0
 18 36  1  0
  7 27  1  0
  7 28  1  0
  6 26  1  0
  4 25  1  0
  3 24  1  0
  9 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 12 33  1  0
 20 37  1  0
 20 38  1  0
 15 34  1  0
M  END


  Mrv1652309022217192D          

 21 25  0  0  1  0            999 V2000
    3.3245   -0.2444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4995   -0.2397    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0829   -0.9518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2579   -0.9471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8495   -0.2302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0436   -0.0541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0380    0.7669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7176    1.0981    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9770    1.8813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7849    2.0482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3335    1.4319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1414    1.5988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6899    0.9826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4305    0.1995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6226    0.0325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8935    0.7967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2661    0.4819    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0911    0.4772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0952   -0.2893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7654    0.1918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5149    0.9779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  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  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
  5 17  1  0  0  0  0
 17  8  1  1  0  0  0
 17 18  1  0  0  0  0
  2 18  1  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 13 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0157845

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1C[C@]23N(CC=C2C=C1)CCC1=CC2=C(OCO2)C=C31

> <INCHI_IDENTIFIER>
InChI=1S/C17H17NO3/c19-13-2-1-12-4-6-18-5-3-11-7-15-16(21-10-20-15)8-14(11)17(12,18)9-13/h1-2,4,7-8,13,19H,3,5-6,9-10H2/t13-,17-/m0/s1

> <INCHI_KEY>
BQGXJXYASMDFSV-GUYCJALGSA-N

> <FORMULA>
C17H17NO3

> <MOLECULAR_WEIGHT>
283.327

> <EXACT_MASS>
283.120843411

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
29.939525362894603

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,19R)-5,7-dioxa-13-azapentacyclo[11.7.0.0^{1,16}.0^{2,10}.0^{4,8}]icosa-2,4(8),9,15,17-pentaen-19-ol

> <ALOGPS_LOGP>
1.00

> <JCHEM_LOGP>
1.3549987246666675

> <ALOGPS_LOGS>
-2.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.798482339256207

> <JCHEM_PKA_STRONGEST_BASIC>
8.59472569572747

> <JCHEM_POLAR_SURFACE_AREA>
41.93000000000001

> <JCHEM_REFRACTIVITY>
80.52850000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.59e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,19R)-5,7-dioxa-13-azapentacyclo[11.7.0.0^{1,16}.0^{2,10}.0^{4,8}]icosa-2,4(8),9,15,17-pentaen-19-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  O   UNK     0       6.206  -0.456   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.666  -0.447   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.888  -1.777   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.348  -1.768   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.586  -0.430   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.081  -0.101   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.071   1.431   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       1.339   2.050   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       1.824   3.512   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.332   3.823   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.356   2.673   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.864   2.985   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.888   1.834   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.404   0.372   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.895   0.061   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.535   1.487   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.363   0.899   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.903   0.891   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       7.644  -0.540   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.895   0.358   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.428   1.825   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   17                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   17                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   21                                                  
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   11   17                                                  
CONECT   17   16    5    8   18                                             
CONECT   18   17    2                                                       
CONECT   19   14   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   13                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₁₇NO₃

Average Mass

283.3270 Da

Monoisotopic Mass

283.12084 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

O[C@@H]1C[C@]23N(CC=C2C=C1)CCC1=CC2=C(OCO2)C=C31

InChI Identifier

InChI=1S/C17H17NO3/c19-13-2-1-12-4-6-18-5-3-11-7-15-16(21-10-20-15)8-14(11)17(12,18)9-13/h1-2,4,7-8,13,19H,3,5-6,9-10H2/t13-,17-/m0/s1

InChI Key

BQGXJXYASMDFSV-GUYCJALGSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as erythrinanes. These are erythrina alkaloids possessing either a 6-5-6-6-membered indoloisoquinoline core or a derivative thereof.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Erythrina alkaloids

Sub Class

Erythrinanes

Direct Parent

Erythrinanes

Alternative Parents

Substituents

Erythrinane skeleton
Tetrahydroisoquinoline
Benzodioxole
Indole or derivatives
Aralkylamine
Benzenoid
Pyrroline
Secondary alcohol
Tertiary amine
Tertiary aliphatic amine
Oxacycle
Azacycle
Acetal
Organoheterocyclic compound
Hydrocarbon derivative
Alcohol
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
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

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

9360273

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11185188

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Shimizu K, Takimoto M, Mori M: Novel synthesis of heterocycles having a functionalized carbon center via nickel-mediated carboxylation: total synthesis of erythrocarine. Org Lett. 2003 Jun 26;5(13):2323-5. doi: 10.1021/ol034670w. [PubMed:12816439 ]
LOTUS database [Link]

Showing NP-Card for (1s,19r)-5,7-dioxa-13-azapentacyclo[11.7.0.0¹,¹⁶.0²,¹⁰.0⁴,⁸]icosa-2,4(8),9,15,17-pentaen-19-ol (NP0157845)

MOL for NP0157845 ((1s,19r)-5,7-dioxa-13-azapentacyclo[11.7.0.0¹,¹⁶.0²,¹⁰.0⁴,⁸]icosa-2,4(8),9,15,17-pentaen-19-ol)

3D MOL for NP0157845 ((1s,19r)-5,7-dioxa-13-azapentacyclo[11.7.0.0¹,¹⁶.0²,¹⁰.0⁴,⁸]icosa-2,4(8),9,15,17-pentaen-19-ol)

3D SDF for NP0157845 ((1s,19r)-5,7-dioxa-13-azapentacyclo[11.7.0.0¹,¹⁶.0²,¹⁰.0⁴,⁸]icosa-2,4(8),9,15,17-pentaen-19-ol)

3D-SDF for NP0157845 ((1s,19r)-5,7-dioxa-13-azapentacyclo[11.7.0.0¹,¹⁶.0²,¹⁰.0⁴,⁸]icosa-2,4(8),9,15,17-pentaen-19-ol)

PDB for NP0157845 ((1s,19r)-5,7-dioxa-13-azapentacyclo[11.7.0.0¹,¹⁶.0²,¹⁰.0⁴,⁸]icosa-2,4(8),9,15,17-pentaen-19-ol)

3D PDB for NP0157845 ((1s,19r)-5,7-dioxa-13-azapentacyclo[11.7.0.0¹,¹⁶.0²,¹⁰.0⁴,⁸]icosa-2,4(8),9,15,17-pentaen-19-ol)

SMILES for NP0157845 ((1s,19r)-5,7-dioxa-13-azapentacyclo[11.7.0.0¹,¹⁶.0²,¹⁰.0⁴,⁸]icosa-2,4(8),9,15,17-pentaen-19-ol)

INCHI for NP0157845 ((1s,19r)-5,7-dioxa-13-azapentacyclo[11.7.0.0¹,¹⁶.0²,¹⁰.0⁴,⁸]icosa-2,4(8),9,15,17-pentaen-19-ol)

Structure for NP0157845 ((1s,19r)-5,7-dioxa-13-azapentacyclo[11.7.0.0¹,¹⁶.0²,¹⁰.0⁴,⁸]icosa-2,4(8),9,15,17-pentaen-19-ol)

3D Structure for NP0157845 ((1s,19r)-5,7-dioxa-13-azapentacyclo[11.7.0.0¹,¹⁶.0²,¹⁰.0⁴,⁸]icosa-2,4(8),9,15,17-pentaen-19-ol)