NP-MRD: Showing NP-Card for pereniporin b (NP0213778)

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Record Information

Version

2.0

Created at

2022-09-05 12:52:07 UTC

Updated at

2022-09-05 12:52:07 UTC

NP-MRD ID

NP0213778

Secondary Accession Numbers

None

Natural Product Identification

Common Name

pereniporin b

Description

Pereniporin B belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. pereniporin b is found in Cinnamosma madagascariensis, Perenniporia medulla-panis and Warburgia ugandensis. pereniporin b was first documented in 2008 (PMID: 18179176). Pereniporin B is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 24971618).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 43  0  0  0  0  0  0  0  0999 V2000
   -2.8207   -0.7810    0.9076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8086   -0.4088   -0.1696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0978   -1.3367   -1.3554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1638    0.9780   -0.6337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1582    1.6055   -1.5293 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0912    0.7669   -1.7211 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5741    0.3876   -0.3442 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7216    1.6529    0.4348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4170   -0.5956    0.2953 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2077   -0.5788    1.7712 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8376    0.4417    2.4395 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2484   -0.6450    2.0472 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1867   -0.5463    1.1403 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6471   -0.5745    1.1280 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3796   -0.9519    2.0726 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1241   -0.1183   -0.0937 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0510    0.3281   -0.9038 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8632   -0.3488   -0.3260 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6878   -1.6408   -0.8426 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4813   -1.7410    1.3432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9884    0.0171    1.6327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7724   -1.0279    0.3629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9102   -2.0345   -1.1572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1837   -1.9719   -1.5466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3037   -0.7932   -2.2750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1102    0.8582   -1.2434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4921    1.6327    0.2187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8787    2.5947   -1.1098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5432    1.8171   -2.5631 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8566    1.4663   -2.1427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0241   -0.0573   -2.4107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2219    2.0463    0.8592 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5423    1.6360    1.1830 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0506    2.4540   -0.2959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1323   -1.6527   -0.0094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6345   -1.5400    2.1836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1733    0.1936    3.3379 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5456   -0.7855    3.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2283   -0.0913   -1.9185 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9880    1.4105   -0.9978 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5753   -2.0657   -0.8446 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  6
 18  7  1  0
  7  8  1  1
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  1  0
  7  9  1  0
  2  9  1  0
 18 13  1  0
  9 35  1  6
 10 36  1  1
 11 37  1  0
 12 38  1  0
 17 39  1  0
 17 40  1  0
 19 41  1  0
  8 32  1  0
  8 33  1  0
  8 34  1  0
  6 30  1  0
  6 31  1  0
  5 28  1  0
  5 29  1  0
  4 26  1  0
  4 27  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
M  END


  Mrv1652309272006262D          

 20 22  0  0  0  0            999 V2000
 9999.9508 9999.8038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.195510000.7588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.6487 9999.8490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.664410001.0415    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.949910000.6285    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.9499 9998.9785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.6644 9999.3909    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.664410000.2160    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.665210001.8665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.950710001.4540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.379710000.6289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.379710001.4540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.450710000.4709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.9658 9999.8034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.4508 9999.1360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2354 9999.3909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.3788 9998.9783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.235310000.2158    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.235310001.0409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1958 9998.3513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  8  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9 10  1  0  0  0  0
  9 12  1  0  0  0  0
 11 12  1  0  0  0  0
 11  2  1  0  0  0  0
 11  3  1  0  0  0  0
 10  5  1  0  0  0  0
  5  1  1  6  0  0  0
  8 11  1  0  0  0  0
  8  4  1  1  0  0  0
 15 16  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16  6  2  0  0  0  0
  7 17  1  6  0  0  0
 18 19  1  1  0  0  0
 13 18  1  0  0  0  0
 16 18  1  0  0  0  0
  5 18  1  0  0  0  0
 15 20  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0213778

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12[C@H](O)C=C3C(=O)OC[C@]3(O)[C@@]1(C)CCCC2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O4/c1-13(2)5-4-6-14(3)11(13)10(16)7-9-12(17)19-8-15(9,14)18/h7,10-11,16,18H,4-6,8H2,1-3H3/t10-,11+,14+,15-/m1/s1

> <INCHI_KEY>
HLEGAPKZEJEXHT-FDRIWYBQSA-N

> <FORMULA>
C15H22O4

> <MOLECULAR_WEIGHT>
266.337

> <EXACT_MASS>
266.151809188

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
27.933902845691833

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5R,5aS,9aS,9bS)-5,9b-dihydroxy-6,6,9a-trimethyl-1H,3H,5H,5aH,6H,7H,8H,9H,9aH,9bH-naphtho[1,2-c]furan-3-one

> <ALOGPS_LOGP>
1.49

> <JCHEM_LOGP>
1.5308173759999992

> <ALOGPS_LOGS>
-2.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.478429524212718

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.742102697698815

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0398390889263256

> <JCHEM_POLAR_SURFACE_AREA>
66.75999999999999

> <JCHEM_REFRACTIVITY>
70.2073

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.43e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pereniporin B

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8666.5758666.300   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8670.7658668.083   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8669.7448666.385   0.000  0.00  0.00           C+0
HETATM    4  H   UNK     0    8667.9078668.611   0.000  0.00  0.00           H+0
HETATM    5  C   UNK     0    8666.5738667.840   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8666.5738664.760   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8667.9078665.530   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8667.9078667.070   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8667.9088670.151   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8666.5758669.381   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8669.2428667.841   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8669.2428669.381   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8663.7758667.546   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0    8662.8698666.300   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0    8663.7758665.054   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8665.2398665.530   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0    8669.2408664.759   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0    8665.2398667.069   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0    8665.2398668.610   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0    8663.2998663.589   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2   11                                                            
CONECT    3   11                                                            
CONECT    4    8                                                            
CONECT    5    8   10    1   18                                             
CONECT    6    7   16                                                       
CONECT    7    6    8   17                                                  
CONECT    8    5    7   11    4                                             
CONECT    9   10   12                                                       
CONECT   10    9    5                                                       
CONECT   11   12    2    3    8                                             
CONECT   12    9   11                                                       
CONECT   13   14   18                                                       
CONECT   14   13   15                                                       
CONECT   15   16   14   20                                                  
CONECT   16   15    6   18                                                  
CONECT   17    7                                                            
CONECT   18   19   13   16    5                                             
CONECT   19   18                                                            
CONECT   20   15                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Value	Source
(-)-Pereniporin B	PhytoBank

Chemical Formula

C₁₅H₂₂O₄

Average Mass

266.3370 Da

Monoisotopic Mass

266.15181 Da

IUPAC Name

(5R,5aS,9aS,9bS)-5,9b-dihydroxy-6,6,9a-trimethyl-1H,3H,5H,5aH,6H,7H,8H,9H,9aH,9bH-naphtho[1,2-c]furan-3-one

Traditional Name

pereniporin B

CAS Registry Number

Not Available

SMILES

[H][C@@]12[C@H](O)C=C3C(=O)OC[C@]3(O)[C@@]1(C)CCCC2(C)C

InChI Identifier

InChI=1S/C15H22O4/c1-13(2)5-4-6-14(3)11(13)10(16)7-9-12(17)19-8-15(9,14)18/h7,10-11,16,18H,4-6,8H2,1-3H3/t10-,11+,14+,15-/m1/s1

InChI Key

HLEGAPKZEJEXHT-FDRIWYBQSA-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

Species Name	Source	Reference
Cinnamosma madagascariensis	LOTUS Database	35616633
Perenniporia medulla-panis	LOTUS Database	35616633
Warburgia ugandensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthofurans

Sub Class

Not Available

Direct Parent

Naphthofurans

Alternative Parents

Substituents

Naphthofuran
Gamma butyrolactone
Tertiary alcohol
Tetrahydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Lactone
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Organooxygen compound
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	1.49	ALOGPS
logP	1.53	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	12.74	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	70.21 m³·mol⁻¹	ChemAxon
Polarizability	27.93 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

Not Available

Chemspider ID

141600

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

161192

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ciocarlan A, Aricu A, Ungur N, Biriiac A, Coltsa M, Nicolescu A, Deleanu C, Vornicu N: Formal synthesis of ( - )-pereniporin B and ( - )-cinnamosmolide. Nat Prod Res. 2014;28(19):1619-25. doi: 10.1080/14786419.2014.930860. Epub 2014 Jun 27. [PubMed:24971618 ]
Harinantenaina L, Matsunami K, Otsuka H, Kawahata M, Yamaguchi K, Asakawa Y: Secondary metabolites of Cinnamosma madagascariensis and their alpha-glucosidase inhibitory properties. J Nat Prod. 2008 Jan;71(1):123-6. doi: 10.1021/np070474c. Epub 2008 Jan 8. [PubMed:18179176 ]
LOTUS database [Link]

Showing NP-Card for pereniporin b (NP0213778)

MOL for NP0213778 (pereniporin b)

3D MOL for NP0213778 (pereniporin b)

3D SDF for NP0213778 (pereniporin b)

3D-SDF for NP0213778 (pereniporin b)

PDB for NP0213778 (pereniporin b)

3D PDB for NP0213778 (pereniporin b)

SMILES for NP0213778 (pereniporin b)

INCHI for NP0213778 (pereniporin b)

Structure for NP0213778 (pereniporin b)

3D Structure for NP0213778 (pereniporin b)