NP-MRD: Showing NP-Card for (3r,5s,8s,11s,12s,13s,15r,16s)-5-[(acetyloxy)methyl]-13-hydroxy-2,11,12-trimethyl-6-oxo-7,17-dioxapentacyclo[10.3.1.1³,¹⁵.0⁵,¹⁵.0⁸,¹³]heptadec-1-en-16-yl 2-methylprop-2-enoate (NP0218688)

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Record Information

Version

2.0

Created at

2022-09-05 19:26:00 UTC

Updated at

2022-09-05 19:26:01 UTC

NP-MRD ID

NP0218688

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r,5s,8s,11s,12s,13s,15r,16s)-5-[(acetyloxy)methyl]-13-hydroxy-2,11,12-trimethyl-6-oxo-7,17-dioxapentacyclo[10.3.1.1³,¹⁵.0⁵,¹⁵.0⁸,¹³]heptadec-1-en-16-yl 2-methylprop-2-enoate

Description

Ligulaverin C 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. (3r,5s,8s,11s,12s,13s,15r,16s)-5-[(acetyloxy)methyl]-13-hydroxy-2,11,12-trimethyl-6-oxo-7,17-dioxapentacyclo[10.3.1.1³,¹⁵.0⁵,¹⁵.0⁸,¹³]heptadec-1-en-16-yl 2-methylprop-2-enoate is found in Ligularia veitchiana. Based on a literature review very few articles have been published on Ligulaverin C.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052221262D          

 33 37  0  0  1  0            999 V2000
    3.3941   -1.6560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6157   -1.3827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9898   -1.9202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4632   -0.5719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0891   -0.0344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6848   -0.2986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5322    0.5122    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -0.0616    0.4546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5821    1.6794    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309052221262D          

 33 37  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0218688

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CC[C@@H]2OC(=O)[C@]3(COC(C)=O)C[C@H]4O[C@@]33C[C@]2(O)[C@]1(C)[C@H](OC(=O)C(C)=C)C3=C4C

> <INCHI_IDENTIFIER>
InChI=1S/C25H32O8/c1-12(2)20(27)32-19-18-14(4)16-9-23(11-30-15(5)26)21(28)31-17-8-7-13(3)22(19,6)24(17,29)10-25(18,23)33-16/h13,16-17,19,29H,1,7-11H2,2-6H3/t13-,16+,17-,19+,22-,23+,24+,25+/m0/s1

> <INCHI_KEY>
XOMIIMFMCRPSTG-XEYIFKCBSA-N

> <FORMULA>
C25H32O8

> <MOLECULAR_WEIGHT>
460.523

> <EXACT_MASS>
460.20971799

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
47.49892176757017

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,5S,8S,11S,12S,13S,15R,16S)-5-[(acetyloxy)methyl]-13-hydroxy-2,11,12-trimethyl-6-oxo-7,17-dioxapentacyclo[10.3.1.1^{3,15}.0^{5,15}.0^{8,13}]heptadec-1-en-16-yl 2-methylprop-2-enoate

> <JCHEM_LOGP>
2.066644885666666

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.248483687260293

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5649132351923463

> <JCHEM_POLAR_SURFACE_AREA>
108.36000000000001

> <JCHEM_REFRACTIVITY>
114.67389999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3R,5S,8S,11S,12S,13S,15R,16S)-5-[(acetyloxy)methyl]-13-hydroxy-2,11,12-trimethyl-6-oxo-7,17-dioxapentacyclo[10.3.1.1^{3,15}.0^{5,15}.0^{8,13}]heptadec-1-en-16-yl 2-methylprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       6.336  -3.091   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.883  -2.581   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.714  -3.584   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.598  -1.068   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.766  -0.064   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       3.145  -0.557   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.860   0.956   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.267   1.513   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.115   0.849   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.438  -0.657   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.178   2.111   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.144   4.136   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.452   4.637   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.410   5.913   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.946   5.805   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.808   7.082   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.344   6.974   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -2.133   8.466   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.552   5.977   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.863   7.353   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       3.168   6.051   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.149   4.823   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.747   4.784   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.512   3.420   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.696   2.074   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.478   0.747   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.089   2.009   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.652   0.575   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.558   3.412   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       5.098   3.385   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.053   3.288   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.763   3.082   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -1.087   3.135   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   27                                                  
CONECT    8    7    9   32                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   33                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   19   32                                             
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   13   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   29                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25    7   28   29                                             
CONECT   28   27                                                            
CONECT   29   27   22   30   31                                             
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31    8   13   33                                             
CONECT   33   32   11                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₂O₈

Average Mass

460.5230 Da

Monoisotopic Mass

460.20972 Da

IUPAC Name

(3R,5S,8S,11S,12S,13S,15R,16S)-5-[(acetyloxy)methyl]-13-hydroxy-2,11,12-trimethyl-6-oxo-7,17-dioxapentacyclo[10.3.1.1^{3,15}.0^{5,15}.0^{8,13}]heptadec-1-en-16-yl 2-methylprop-2-enoate

Traditional Name

(3R,5S,8S,11S,12S,13S,15R,16S)-5-[(acetyloxy)methyl]-13-hydroxy-2,11,12-trimethyl-6-oxo-7,17-dioxapentacyclo[10.3.1.1^{3,15}.0^{5,15}.0^{8,13}]heptadec-1-en-16-yl 2-methylprop-2-enoate

CAS Registry Number

Not Available

SMILES

C[C@H]1CC[C@@H]2OC(=O)[C@]3(COC(C)=O)C[C@H]4O[C@@]33C[C@]2(O)[C@]1(C)[C@H](OC(=O)C(C)=C)C3=C4C

InChI Identifier

InChI=1S/C25H32O8/c1-12(2)20(27)32-19-18-14(4)16-9-23(11-30-15(5)26)21(28)31-17-8-7-13(3)22(19,6)24(17,29)10-25(18,23)33-16/h13,16-17,19,29H,1,7-11H2,2-6H3/t13-,16+,17-,19+,22-,23+,24+,25+/m0/s1

InChI Key

XOMIIMFMCRPSTG-XEYIFKCBSA-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
Ligularia veitchiana	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
Tricarboxylic acid or derivatives
Caprolactone
Oxepane
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Dihydrofuran
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Lactone
Ether
Dialkyl ether
Oxacycle
Carboxylic acid derivative
Alcohol
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
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	2.07	ChemAxon
pKa (Strongest Acidic)	13.25	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	108.36 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	114.67 m³·mol⁻¹	ChemAxon
Polarizability	47.5 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	Yes	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

101702825

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3r,5s,8s,11s,12s,13s,15r,16s)-5-[(acetyloxy)methyl]-13-hydroxy-2,11,12-trimethyl-6-oxo-7,17-dioxapentacyclo[10.3.1.1³,¹⁵.0⁵,¹⁵.0⁸,¹³]heptadec-1-en-16-yl 2-methylprop-2-enoate (NP0218688)

MOL for NP0218688 ((3r,5s,8s,11s,12s,13s,15r,16s)-5-[(acetyloxy)methyl]-13-hydroxy-2,11,12-trimethyl-6-oxo-7,17-dioxapentacyclo[10.3.1.1³,¹⁵.0⁵,¹⁵.0⁸,¹³]heptadec-1-en-16-yl 2-methylprop-2-enoate)

3D MOL for NP0218688 ((3r,5s,8s,11s,12s,13s,15r,16s)-5-[(acetyloxy)methyl]-13-hydroxy-2,11,12-trimethyl-6-oxo-7,17-dioxapentacyclo[10.3.1.1³,¹⁵.0⁵,¹⁵.0⁸,¹³]heptadec-1-en-16-yl 2-methylprop-2-enoate)

3D SDF for NP0218688 ((3r,5s,8s,11s,12s,13s,15r,16s)-5-[(acetyloxy)methyl]-13-hydroxy-2,11,12-trimethyl-6-oxo-7,17-dioxapentacyclo[10.3.1.1³,¹⁵.0⁵,¹⁵.0⁸,¹³]heptadec-1-en-16-yl 2-methylprop-2-enoate)

3D-SDF for NP0218688 ((3r,5s,8s,11s,12s,13s,15r,16s)-5-[(acetyloxy)methyl]-13-hydroxy-2,11,12-trimethyl-6-oxo-7,17-dioxapentacyclo[10.3.1.1³,¹⁵.0⁵,¹⁵.0⁸,¹³]heptadec-1-en-16-yl 2-methylprop-2-enoate)

PDB for NP0218688 ((3r,5s,8s,11s,12s,13s,15r,16s)-5-[(acetyloxy)methyl]-13-hydroxy-2,11,12-trimethyl-6-oxo-7,17-dioxapentacyclo[10.3.1.1³,¹⁵.0⁵,¹⁵.0⁸,¹³]heptadec-1-en-16-yl 2-methylprop-2-enoate)

3D PDB for NP0218688 ((3r,5s,8s,11s,12s,13s,15r,16s)-5-[(acetyloxy)methyl]-13-hydroxy-2,11,12-trimethyl-6-oxo-7,17-dioxapentacyclo[10.3.1.1³,¹⁵.0⁵,¹⁵.0⁸,¹³]heptadec-1-en-16-yl 2-methylprop-2-enoate)

SMILES for NP0218688 ((3r,5s,8s,11s,12s,13s,15r,16s)-5-[(acetyloxy)methyl]-13-hydroxy-2,11,12-trimethyl-6-oxo-7,17-dioxapentacyclo[10.3.1.1³,¹⁵.0⁵,¹⁵.0⁸,¹³]heptadec-1-en-16-yl 2-methylprop-2-enoate)

INCHI for NP0218688 ((3r,5s,8s,11s,12s,13s,15r,16s)-5-[(acetyloxy)methyl]-13-hydroxy-2,11,12-trimethyl-6-oxo-7,17-dioxapentacyclo[10.3.1.1³,¹⁵.0⁵,¹⁵.0⁸,¹³]heptadec-1-en-16-yl 2-methylprop-2-enoate)

Structure for NP0218688 ((3r,5s,8s,11s,12s,13s,15r,16s)-5-[(acetyloxy)methyl]-13-hydroxy-2,11,12-trimethyl-6-oxo-7,17-dioxapentacyclo[10.3.1.1³,¹⁵.0⁵,¹⁵.0⁸,¹³]heptadec-1-en-16-yl 2-methylprop-2-enoate)

3D Structure for NP0218688 ((3r,5s,8s,11s,12s,13s,15r,16s)-5-[(acetyloxy)methyl]-13-hydroxy-2,11,12-trimethyl-6-oxo-7,17-dioxapentacyclo[10.3.1.1³,¹⁵.0⁵,¹⁵.0⁸,¹³]heptadec-1-en-16-yl 2-methylprop-2-enoate)