NP-MRD: Showing NP-Card for (1r,2r,4s,7s,9r,10r,14r)-7-(furan-3-yl)-2-hydroxy-9-methyl-6,16-dioxatetracyclo[8.7.0.0¹,¹⁴.0⁴,⁹]heptadec-12-ene-5,11,15-trione (NP0286337)

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Record Information

Version

2.0

Created at

2022-09-09 14:52:00 UTC

Updated at

2022-09-09 14:52:00 UTC

NP-MRD ID

NP0286337

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,4s,7s,9r,10r,14r)-7-(furan-3-yl)-2-hydroxy-9-methyl-6,16-dioxatetracyclo[8.7.0.0¹,¹⁴.0⁴,⁹]heptadec-12-ene-5,11,15-trione

Description

Rhynchosperin b belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. (1r,2r,4s,7s,9r,10r,14r)-7-(furan-3-yl)-2-hydroxy-9-methyl-6,16-dioxatetracyclo[8.7.0.0¹,¹⁴.0⁴,⁹]heptadec-12-ene-5,11,15-trione is found in Aster verticillatus. Based on a literature review very few articles have been published on rhynchosperin b.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309092216522D          

 27 31  0  0  1  0            999 V2000
    2.0906    0.5057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1283   -0.3184    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8232    0.1262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5557   -0.2533    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2506    0.1913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2994    1.0149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0977    1.2230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5423    0.5281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0188   -0.1095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5933   -1.0774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8984   -1.5221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9360   -2.3462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1659   -1.1426    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4709   -1.5872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9107   -1.3650    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0435   -1.6524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7008   -0.3836    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5662   -1.1975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2495   -1.3211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6190   -0.5835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4330   -0.4489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0317   -0.0041    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0693    0.8201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6256    1.2647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3581    0.8852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0530    1.3298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3957    0.0611    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  5  9  2  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 13 11  1  1  0  0  0
  2 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 22 20  1  6  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 27 25  1  6  0  0  0
  2 27  1  0  0  0  0
 17 27  1  0  0  0  0
M  END


  Mrv1652309092216522D          

 27 31  0  0  1  0            999 V2000
    2.0906    0.5057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1283   -0.3184    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8232    0.1262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5557   -0.2533    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2506    0.1913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2994    1.0149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0977    1.2230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5423    0.5281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0188   -0.1095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5933   -1.0774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8984   -1.5221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9360   -2.3462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1659   -1.1426    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4709   -1.5872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9107   -1.3650    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0435   -1.6524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7008   -0.3836    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5662   -1.1975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2495   -1.3211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6190   -0.5835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4330   -0.4489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0317   -0.0041    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0693    0.8201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6256    1.2647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3581    0.8852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0530    1.3298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3957    0.0611    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  5  9  2  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 13 11  1  1  0  0  0
  2 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 22 20  1  6  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 27 25  1  6  0  0  0
  2 27  1  0  0  0  0
 17 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0286337

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]12C[C@H](OC(=O)[C@H]1C[C@@H](O)[C@@]13COC(=O)[C@@H]1C=CC(=O)[C@H]23)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H20O7/c1-19-7-14(10-4-5-25-8-10)27-18(24)12(19)6-15(22)20-9-26-17(23)11(20)2-3-13(21)16(19)20/h2-5,8,11-12,14-16,22H,6-7,9H2,1H3/t11-,12+,14-,15+,16+,19-,20+/m0/s1

> <INCHI_KEY>
PZAUPCCHLQWMAF-IAXXMGCBSA-N

> <FORMULA>
C20H20O7

> <MOLECULAR_WEIGHT>
372.373

> <EXACT_MASS>
372.120902984

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
36.37764544492926

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,4S,7S,9R,10R,14R)-7-(furan-3-yl)-2-hydroxy-9-methyl-6,16-dioxatetracyclo[8.7.0.0^{1,14}.0^{4,9}]heptadec-12-ene-5,11,15-trione

> <JCHEM_LOGP>
0.8237727010000006

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.909797342253459

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.668300406981103

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8878400660227053

> <JCHEM_POLAR_SURFACE_AREA>
103.03999999999999

> <JCHEM_REFRACTIVITY>
91.4739

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,4S,7S,9R,10R,14R)-7-(furan-3-yl)-2-hydroxy-9-methyl-6,16-dioxatetracyclo[8.7.0.0^{1,14}.0^{4,9}]heptadec-12-ene-5,11,15-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       3.903   0.944   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.973  -0.594   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.270   0.236   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.637  -0.473   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.935   0.357   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.026   1.894   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.516   2.283   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      10.346   0.986   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       9.368  -0.204   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.708  -2.011   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.410  -2.841   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.481  -4.380   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.043  -2.133   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.746  -2.963   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.700  -2.548   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.081  -3.084   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.308  -0.716   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.057  -2.235   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.466  -2.466   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.156  -1.089   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.675  -0.838   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.059  -0.008   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.129   1.531   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.168   2.361   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.535   1.652   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       3.832   2.482   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.605   0.114   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   13   27                                             
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    5                                                       
CONECT   10    4   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    2   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   22   27                                             
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   17   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25    2   17                                                  
MASTER        0    0    0    0    0    0    0    0   27    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₀O₇

Average Mass

372.3730 Da

Monoisotopic Mass

372.12090 Da

IUPAC Name

(1R,2R,4S,7S,9R,10R,14R)-7-(furan-3-yl)-2-hydroxy-9-methyl-6,16-dioxatetracyclo[8.7.0.0^{1,14}.0^{4,9}]heptadec-12-ene-5,11,15-trione

Traditional Name

(1R,2R,4S,7S,9R,10R,14R)-7-(furan-3-yl)-2-hydroxy-9-methyl-6,16-dioxatetracyclo[8.7.0.0^{1,14}.0^{4,9}]heptadec-12-ene-5,11,15-trione

CAS Registry Number

Not Available

SMILES

C[C@]12C[C@H](OC(=O)[C@H]1C[C@@H](O)[C@@]13COC(=O)[C@@H]1C=CC(=O)[C@H]23)C1=COC=C1

InChI Identifier

InChI=1S/C20H20O7/c1-19-7-14(10-4-5-25-8-10)27-18(24)12(19)6-15(22)20-9-26-17(23)11(20)2-3-13(21)16(19)20/h2-5,8,11-12,14-16,22H,6-7,9H2,1H3/t11-,12+,14-,15+,16+,19-,20+/m0/s1

InChI Key

PZAUPCCHLQWMAF-IAXXMGCBSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aster verticillatus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five 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

Naphthopyrans

Sub Class

Not Available

Direct Parent

Naphthopyrans

Alternative Parents

Substituents

Naphthopyran
Naphthalene
Delta valerolactone
Delta_valerolactone
Cyclohexenone
Pyran
Oxane
Dicarboxylic acid or derivatives
Gamma butyrolactone
Heteroaromatic compound
Tetrahydrofuran
Cyclic alcohol
Furan
Carboxylic acid ester
Secondary alcohol
Ketone
Lactone
Oxacycle
Carboxylic acid derivative
Organic oxide
Organooxygen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxygen 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	0.82	ChemAxon
pKa (Strongest Acidic)	13.67	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	103.04 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	91.47 m³·mol⁻¹	ChemAxon
Polarizability	36.38 Å³	ChemAxon
Number of Rings	5	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13967150

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2r,4s,7s,9r,10r,14r)-7-(furan-3-yl)-2-hydroxy-9-methyl-6,16-dioxatetracyclo[8.7.0.0¹,¹⁴.0⁴,⁹]heptadec-12-ene-5,11,15-trione (NP0286337)

MOL for NP0286337 ((1r,2r,4s,7s,9r,10r,14r)-7-(furan-3-yl)-2-hydroxy-9-methyl-6,16-dioxatetracyclo[8.7.0.0¹,¹⁴.0⁴,⁹]heptadec-12-ene-5,11,15-trione)

3D MOL for NP0286337 ((1r,2r,4s,7s,9r,10r,14r)-7-(furan-3-yl)-2-hydroxy-9-methyl-6,16-dioxatetracyclo[8.7.0.0¹,¹⁴.0⁴,⁹]heptadec-12-ene-5,11,15-trione)

3D SDF for NP0286337 ((1r,2r,4s,7s,9r,10r,14r)-7-(furan-3-yl)-2-hydroxy-9-methyl-6,16-dioxatetracyclo[8.7.0.0¹,¹⁴.0⁴,⁹]heptadec-12-ene-5,11,15-trione)

3D-SDF for NP0286337 ((1r,2r,4s,7s,9r,10r,14r)-7-(furan-3-yl)-2-hydroxy-9-methyl-6,16-dioxatetracyclo[8.7.0.0¹,¹⁴.0⁴,⁹]heptadec-12-ene-5,11,15-trione)

PDB for NP0286337 ((1r,2r,4s,7s,9r,10r,14r)-7-(furan-3-yl)-2-hydroxy-9-methyl-6,16-dioxatetracyclo[8.7.0.0¹,¹⁴.0⁴,⁹]heptadec-12-ene-5,11,15-trione)

3D PDB for NP0286337 ((1r,2r,4s,7s,9r,10r,14r)-7-(furan-3-yl)-2-hydroxy-9-methyl-6,16-dioxatetracyclo[8.7.0.0¹,¹⁴.0⁴,⁹]heptadec-12-ene-5,11,15-trione)

SMILES for NP0286337 ((1r,2r,4s,7s,9r,10r,14r)-7-(furan-3-yl)-2-hydroxy-9-methyl-6,16-dioxatetracyclo[8.7.0.0¹,¹⁴.0⁴,⁹]heptadec-12-ene-5,11,15-trione)

INCHI for NP0286337 ((1r,2r,4s,7s,9r,10r,14r)-7-(furan-3-yl)-2-hydroxy-9-methyl-6,16-dioxatetracyclo[8.7.0.0¹,¹⁴.0⁴,⁹]heptadec-12-ene-5,11,15-trione)

Structure for NP0286337 ((1r,2r,4s,7s,9r,10r,14r)-7-(furan-3-yl)-2-hydroxy-9-methyl-6,16-dioxatetracyclo[8.7.0.0¹,¹⁴.0⁴,⁹]heptadec-12-ene-5,11,15-trione)

3D Structure for NP0286337 ((1r,2r,4s,7s,9r,10r,14r)-7-(furan-3-yl)-2-hydroxy-9-methyl-6,16-dioxatetracyclo[8.7.0.0¹,¹⁴.0⁴,⁹]heptadec-12-ene-5,11,15-trione)