NP-MRD: Showing NP-Card for 3alpha-Angeloyloxy-2alpha,4beta-dihydroxy-15,16-epoxy-cis-clerodane-1(10),13(16),14-trien-20,12-olide (NP0065432)

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Record Information

Version

2.0

Created at

2022-04-28 09:39:02 UTC

Updated at

2022-04-28 09:39:02 UTC

NP-MRD ID

NP0065432

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3alpha-Angeloyloxy-2alpha,4beta-dihydroxy-15,16-epoxy-cis-clerodane-1(10),13(16),14-trien-20,12-olide

Description

(1R,2R,4aS,5R,5'R,6R,7R)-5'-(furan-3-yl)-5,7-dihydroxy-2,4a,5-trimethyl-2'-oxo-3,4,4a,5,6,7-hexahydro-2H-spiro[naphthalene-1,3'-oxolane]-6-yl (2Z)-2-methylbut-2-enoate belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. 3alpha-Angeloyloxy-2alpha,4beta-dihydroxy-15,16-epoxy-cis-clerodane-1(10),13(16),14-trien-20,12-olide is found in Pteronia eenii. Based on a literature review very few articles have been published on (1R,2R,4aS,5R,5'R,6R,7R)-5'-(furan-3-yl)-5,7-dihydroxy-2,4a,5-trimethyl-2'-oxo-3,4,4a,5,6,7-hexahydro-2H-spiro[naphthalene-1,3'-oxolane]-6-yl (2Z)-2-methylbut-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282211392D          

 32 35  0  0  1  0            999 V2000
    1.6704    0.3724    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2728    0.9361    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0857    1.7396    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2964    1.9794    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6940    1.4157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8811    0.6122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0954    1.6554    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2824    2.4590    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3199    3.0227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1093    2.7829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0718    2.6987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5704    0.2344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7404    0.4868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.9055    1.8114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.4336    1.2394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6866    1.5894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8987    2.5432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8822    1.9546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3529    2.5202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0622    0.6963    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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    3.2058    3.5984    1.1045 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0694    4.1122    2.0751 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652304282211392D          

 32 35  0  0  1  0            999 V2000
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    2.0857    1.7396    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2964    1.9794    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0065432

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(\C)C(=O)O[C@@H]1[C@H](O)C=C2[C@@]3(C[C@@H](OC3=O)C3=COC=C3)[C@H](C)CC[C@]2(C)[C@@]1(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C25H32O7/c1-6-14(2)21(27)32-20-17(26)11-19-23(4,24(20,5)29)9-7-15(3)25(19)12-18(31-22(25)28)16-8-10-30-13-16/h6,8,10-11,13,15,17-18,20,26,29H,7,9,12H2,1-5H3/b14-6-/t15-,17-,18-,20-,23+,24+,25-/m1/s1

> <INCHI_KEY>
NQANRPPWFHFUBN-MPINMLMHSA-N

> <FORMULA>
C25H32O7

> <MOLECULAR_WEIGHT>
444.524

> <EXACT_MASS>
444.21480337

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
46.57804496467893

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,4aS,5R,5'R,6R,7R)-5'-(furan-3-yl)-5,7-dihydroxy-2,4a,5-trimethyl-2'-oxo-3,4,4a,5,6,7-hexahydro-2H-spiro[naphthalene-1,3'-oxolane]-6-yl (2Z)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
3.64

> <JCHEM_LOGP>
3.4927571229999987

> <ALOGPS_LOGS>
-3.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.99637921548981

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.264094050584383

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8885752409321475

> <JCHEM_POLAR_SURFACE_AREA>
106.2

> <JCHEM_REFRACTIVITY>
117.10379999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.81e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,4aS,5R,5'R,6R,7R)-5'-(furan-3-yl)-5,7-dihydroxy-2,4a,5-trimethyl-2'-oxo-3,4,6,7-tetrahydro-2H-spiro[naphthalene-1,3'-oxolane]-6-yl (2Z)-2-methylbut-2-enoate

> <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       3.118   0.695   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.243   1.747   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.893   3.247   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.420   3.695   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.295   2.643   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.645   1.143   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.178   3.090   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.527   4.590   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.597   5.642   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.071   5.195   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.001   5.038   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.012   1.562   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.065   0.438   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -1.382   0.909   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.434   2.033   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.690   3.381   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.963   1.843   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.707   0.494   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -6.219   0.785   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -6.409   2.314   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -5.015   2.967   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.544   4.747   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.380   3.649   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.392   4.704   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.716   1.300   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.065  -0.200   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.941  -1.252   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       7.539  -0.648   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.888  -2.148   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.763  -3.200   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.663   0.405   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       3.467  -0.805   0.000  0.00  0.00           O+0
CONECT    1    2    6   32                                                  
CONECT    2    1    3   25                                                  
CONECT    3    2    4   23   24                                             
CONECT    4    3    5   10   22                                             
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   12   16                                             
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4                                                       
CONECT   11    8                                                            
CONECT   12    7   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15    7                                                       
CONECT   17   15   18   21                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   17                                                       
CONECT   22    4                                                            
CONECT   23    3                                                            
CONECT   24    3                                                            
CONECT   25    2   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   31                                                  
CONECT   29   28   30                                                       
CONECT   30   29                                                            
CONECT   31   28                                                            
CONECT   32    1                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Value	Source
(1R,2R,4AS,5R,5'r,6R,7R)-5'-(furan-3-yl)-5,7-dihydroxy-2,4a,5-trimethyl-2'-oxo-3,4,4a,5,6,7-hexahydro-2H-spiro[naphthalene-1,3'-oxolane]-6-yl (2Z)-2-methylbut-2-enoic acid	Generator

Chemical Formula

C₂₅H₃₂O₇

Average Mass

444.5240 Da

Monoisotopic Mass

444.21480 Da

IUPAC Name

(1R,2R,4aS,5R,5'R,6R,7R)-5'-(furan-3-yl)-5,7-dihydroxy-2,4a,5-trimethyl-2'-oxo-3,4,4a,5,6,7-hexahydro-2H-spiro[naphthalene-1,3'-oxolane]-6-yl (2Z)-2-methylbut-2-enoate

Traditional Name

(1R,2R,4aS,5R,5'R,6R,7R)-5'-(furan-3-yl)-5,7-dihydroxy-2,4a,5-trimethyl-2'-oxo-3,4,6,7-tetrahydro-2H-spiro[naphthalene-1,3'-oxolane]-6-yl (2Z)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

C\C=C(\C)C(=O)O[C@@H]1[C@H](O)C=C2[C@@]3(C[C@@H](OC3=O)C3=COC=C3)[C@H](C)CC[C@]2(C)[C@@]1(C)O

InChI Identifier

InChI=1S/C25H32O7/c1-6-14(2)21(27)32-20-17(26)11-19-23(4,24(20,5)29)9-7-15(3)25(19)12-18(31-22(25)28)16-8-10-30-13-16/h6,8,10-11,13,15,17-18,20,26,29H,7,9,12H2,1-5H3/b14-6-/t15-,17-,18-,20-,23+,24+,25-/m1/s1

InChI Key

NQANRPPWFHFUBN-MPINMLMHSA-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
Pteronia eenii	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Diterpenoid
Clerodane diterpenoid
Fatty acid ester
Cyclitol or derivatives
Dicarboxylic acid or derivatives
Fatty acyl
Gamma butyrolactone
Heteroaromatic compound
Furan
Tertiary alcohol
Tetrahydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Lactone
Secondary alcohol
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Carbonyl group
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	3.64	ALOGPS
logP	3.49	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	13.26	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	106.2 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	117.1 m³·mol⁻¹	ChemAxon
Polarizability	46.58 Å³	ChemAxon
Number of Rings	4	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

162854968

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 3alpha-Angeloyloxy-2alpha,4beta-dihydroxy-15,16-epoxy-cis-clerodane-1(10),13(16),14-trien-20,12-olide (NP0065432)

MOL for NP0065432 (3alpha-Angeloyloxy-2alpha,4beta-dihydroxy-15,16-epoxy-cis-clerodane-1(10),13(16),14-trien-20,12-olide)

3D MOL for NP0065432 (3alpha-Angeloyloxy-2alpha,4beta-dihydroxy-15,16-epoxy-cis-clerodane-1(10),13(16),14-trien-20,12-olide)

3D SDF for NP0065432 (3alpha-Angeloyloxy-2alpha,4beta-dihydroxy-15,16-epoxy-cis-clerodane-1(10),13(16),14-trien-20,12-olide)

3D-SDF for NP0065432 (3alpha-Angeloyloxy-2alpha,4beta-dihydroxy-15,16-epoxy-cis-clerodane-1(10),13(16),14-trien-20,12-olide)

PDB for NP0065432 (3alpha-Angeloyloxy-2alpha,4beta-dihydroxy-15,16-epoxy-cis-clerodane-1(10),13(16),14-trien-20,12-olide)

3D PDB for NP0065432 (3alpha-Angeloyloxy-2alpha,4beta-dihydroxy-15,16-epoxy-cis-clerodane-1(10),13(16),14-trien-20,12-olide)

SMILES for NP0065432 (3alpha-Angeloyloxy-2alpha,4beta-dihydroxy-15,16-epoxy-cis-clerodane-1(10),13(16),14-trien-20,12-olide)

INCHI for NP0065432 (3alpha-Angeloyloxy-2alpha,4beta-dihydroxy-15,16-epoxy-cis-clerodane-1(10),13(16),14-trien-20,12-olide)

Structure for NP0065432 (3alpha-Angeloyloxy-2alpha,4beta-dihydroxy-15,16-epoxy-cis-clerodane-1(10),13(16),14-trien-20,12-olide)

3D Structure for NP0065432 (3alpha-Angeloyloxy-2alpha,4beta-dihydroxy-15,16-epoxy-cis-clerodane-1(10),13(16),14-trien-20,12-olide)