NP-MRD: Showing NP-Card for Physovenine (NP0050895)

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Record Information

Version

2.0

Created at

2022-04-27 22:22:04 UTC

Updated at

2022-04-27 22:22:04 UTC

NP-MRD ID

NP0050895

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Physovenine

Description

Physovenine belongs to the class of organic compounds known as indoles and derivatives. These are organic compounds containing an indole, which is a bicyclic ring system made up of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. Physovenine is found in Physostigma venenosum . Physovenine was first documented in 2020 (PMID: 32239787). Based on a literature review a small amount of articles have been published on Physovenine (PMID: 35357198) (PMID: 34493725) (PMID: 34058527) (PMID: 33793030).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 39  0  0  0  0  0  0  0  0999 V2000
    6.2698   -0.1747    0.5681 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2395   -0.7684   -0.2498 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9342   -0.2445   -0.2100 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6667    0.7259    0.5259 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8839   -0.7549   -0.9639 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5959   -0.2344   -0.9216 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2687    0.7710   -1.8042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0060    1.2805   -1.7566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9690    0.8176   -0.8533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6476   -0.1883    0.0324 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6544   -0.6962   -0.0290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7919   -0.5163    0.8802 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6512   -0.0103    2.2953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2700   -1.9238    0.7936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7690   -1.7111    0.5359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7118   -0.6836   -0.4047 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9308    0.2565    0.2324 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3195    1.2007   -0.6443 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9547    2.3552   -1.2277 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0905    0.1805   -0.0976 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8664    0.6401    1.1989 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7293   -0.9070    1.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4703   -1.5648   -0.8503 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0130    1.1312   -2.5048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2500    2.0727   -2.4581 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8951   -1.4800    0.6654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6932    0.2157    2.6524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1040   -0.6857    2.9524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1431    0.9822    2.2268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8554   -2.4202   -0.1071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1137   -2.5072    1.7216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2396   -2.6266    0.1337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2076   -1.3693    1.4842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5828    0.7373    1.0190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1748    2.1982   -2.2971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8919    2.6384   -0.7072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3003    3.2635   -1.1802 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6 11  2  0
 11 10  1  0
 10  9  2  0
  9  8  1  0
  8  7  2  0
  9 18  1  0
 18 19  1  0
 18 17  1  0
 17 16  1  0
 16 15  1  0
 15 14  1  0
 14 12  1  0
 12 13  1  1
  7  6  1  0
 12 17  1  0
 12 10  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
 11 26  1  0
  8 25  1  0
  7 24  1  0
 19 35  1  0
 19 36  1  0
 19 37  1  0
 17 34  1  1
 15 32  1  0
 15 33  1  0
 14 30  1  0
 14 31  1  0
 13 27  1  0
 13 28  1  0
 13 29  1  0
M  END


  Mrv1652304282200222D          

 19 21  0  0  1  0            999 V2000
    0.8636   -2.0309    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6885   -2.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9279   -1.2251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2510   -0.7535    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5933   -1.2515    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2316   -1.2677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4710   -2.0572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2059   -2.5289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2348    0.0714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7313   -1.0377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2953   -1.6398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0559   -2.4293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2525   -2.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6199   -3.0314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4234   -2.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6628   -2.0545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9874   -3.4461    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7908   -3.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1340   -2.8103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  6  0  0  0
  1  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
  1  8  1  0  0  0  0
  4  9  1  0  0  0  0
  3 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  2 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
  1 19  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0050895

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CNC(=O)OC1=CC2=C(C=C1)N(C)[C@H]1OCC[C@@]21C

> <INCHI_IDENTIFIER>
InChI=1S/C14H18N2O3/c1-14-6-7-18-12(14)16(3)11-5-4-9(8-10(11)14)19-13(17)15-2/h4-5,8,12H,6-7H2,1-3H3,(H,15,17)/t12-,14-/m0/s1

> <INCHI_KEY>
LXTKNVLLWOLCOV-JSGCOSHPSA-N

> <FORMULA>
C14H18N2O3

> <MOLECULAR_WEIGHT>
262.309

> <EXACT_MASS>
262.131742448

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
28.074495899744697

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aS,8aS)-3a,8-dimethyl-2H,3H,3aH,8H,8aH-furo[2,3-b]indol-5-yl N-methylcarbamate

> <ALOGPS_LOGP>
1.48

> <JCHEM_LOGP>
2.1669130426666667

> <ALOGPS_LOGS>
-2.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.772475811298666

> <JCHEM_PKA_STRONGEST_BASIC>
-4.226781280880897

> <JCHEM_POLAR_SURFACE_AREA>
50.800000000000004

> <JCHEM_REFRACTIVITY>
71.42119999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.82e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3aS,8aS)-3a,8-dimethyl-2H,3H,8aH-furo[2,3-b]indol-5-yl N-methylcarbamate

> <JCHEM_VEBER_RULE>
0

$$$$

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       1.612  -3.791   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.152  -3.761   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.599  -2.287   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       2.335  -1.406   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       1.107  -2.336   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.432  -2.366   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.879  -3.840   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.384  -4.721   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.305   0.133   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.098  -1.937   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.151  -3.061   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.704  -4.535   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.205  -4.885   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.757  -5.659   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.257  -5.309   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.704  -3.835   0.000  0.00  0.00           O+0
HETATM   17  N   UNK     0       9.310  -6.433   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0      10.810  -6.083   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.117  -5.246   0.000  0.00  0.00           C+0
CONECT    1    2    5    8   19                                             
CONECT    2    1    3   13                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    1    6                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    1                                                       
CONECT    9    4                                                            
CONECT   10    3   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12    2                                                       
CONECT   14   12   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17                                                            
CONECT   19    1                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₄H₁₈N₂O₃

Average Mass

262.3090 Da

Monoisotopic Mass

262.13174 Da

IUPAC Name

(3aS,8aS)-3a,8-dimethyl-2H,3H,3aH,8H,8aH-furo[2,3-b]indol-5-yl N-methylcarbamate

Traditional Name

(3aS,8aS)-3a,8-dimethyl-2H,3H,8aH-furo[2,3-b]indol-5-yl N-methylcarbamate

CAS Registry Number

Not Available

SMILES

CNC(=O)OC1=CC2=C(C=C1)N(C)[C@H]1OCC[C@@]21C

InChI Identifier

InChI=1S/C14H18N2O3/c1-14-6-7-18-12(14)16(3)11-5-4-9(8-10(11)14)19-13(17)15-2/h4-5,8,12H,6-7H2,1-3H3,(H,15,17)/t12-,14-/m0/s1

InChI Key

LXTKNVLLWOLCOV-JSGCOSHPSA-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
Physostigma venenosum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indoles and derivatives. These are organic compounds containing an indole, which is a bicyclic ring system made up of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Not Available

Direct Parent

Indoles and derivatives

Alternative Parents

Substituents

Indole or derivatives
Dialkylarylamine
Benzenoid
Tetrahydrofuran
Carbamic acid ester
Carbonic acid derivative
Oxacycle
Azacycle
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

indoles (CHEBI:8188 )
Pyrroloindole alkaloids (C09232 )

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	1.48	ALOGPS
logP	2.17	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	14.77	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	50.8 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	71.42 m³·mol⁻¹	ChemAxon
Polarizability	28.07 Å³	ChemAxon
Number of Rings	3	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

C00001758

Chemspider ID

390640

KEGG Compound ID

C09232

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442113

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ren Y, Lu S, He L, Zhao Z, Li SW: Catalytic Asymmetric Decarboxylative Michael Addition To Construct an All-Carbon Quaternary Center with 3-Alkenyl-oxindoles. Org Lett. 2022 Apr 15;24(14):2585-2589. doi: 10.1021/acs.orglett.2c00411. Epub 2022 Mar 31. [PubMed:35357198 ]
Chen JQ, Tu X, Tang Q, Li K, Xu L, Wang S, Ji M, Li Z, Wu J: Efficient access to aliphatic esters by photocatalyzed alkoxycarbonylation of alkenes with alkyloxalyl chlorides. Nat Commun. 2021 Sep 7;12(1):5328. doi: 10.1038/s41467-021-25628-x. [PubMed:34493725 ]
Wang M, Xu J, Zhang Y, Yang N, Ge W, Song R: Integrated multiplatform-based metabonomics and network analysis to explore the mechanism of Polygonum cuspidatum on hyperlipidemia. J Chromatogr B Analyt Technol Biomed Life Sci. 2021 Jun 30;1176:122769. doi: 10.1016/j.jchromb.2021.122769. Epub 2021 May 18. [PubMed:34058527 ]
Chen XW, Yue JP, Wang K, Gui YY, Niu YN, Liu J, Ran CK, Kong W, Zhou WJ, Yu DG: Nickel-Catalyzed Asymmetric Reductive Carbo-Carboxylation of Alkenes with CO2. Angew Chem Int Ed Engl. 2021 Jun 14;60(25):14068-14075. doi: 10.1002/anie.202102769. Epub 2021 May 11. [PubMed:33793030 ]
Chen M, Wang X, Yang P, Kou X, Ren ZH, Guan ZH: Palladium-Catalyzed Enantioselective Heck Carbonylation with a Monodentate Phosphoramidite Ligand: Asymmetric Synthesis of (+)-Physostigmine, (+)-Physovenine, and (+)-Folicanthine. Angew Chem Int Ed Engl. 2020 Jul 13;59(29):12199-12205. doi: 10.1002/anie.202003288. Epub 2020 May 18. [PubMed:32239787 ]

Showing NP-Card for Physovenine (NP0050895)

MOL for NP0050895 (Physovenine)

3D MOL for NP0050895 (Physovenine)

3D SDF for NP0050895 (Physovenine)

3D-SDF for NP0050895 (Physovenine)

PDB for NP0050895 (Physovenine)

3D PDB for NP0050895 (Physovenine)

SMILES for NP0050895 (Physovenine)

INCHI for NP0050895 (Physovenine)

Structure for NP0050895 (Physovenine)

3D Structure for NP0050895 (Physovenine)