NP-MRD: Showing NP-Card for methyl (2e)-3-[(1r,2s,3r,6r,7r,10s,11s,14s)-11-(furan-3-yl)-3-hydroxy-2,6,10-trimethyl-4,13-dioxo-5-(propan-2-ylidene)-12,15-dioxatetracyclo[8.5.0.0¹,¹⁴.0²,⁷]pentadecan-6-yl]prop-2-enoate (NP0304113)

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Record Information

Version

2.0

Created at

2022-09-10 18:57:59 UTC

Updated at

2022-09-10 18:57:59 UTC

NP-MRD ID

NP0304113

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (2e)-3-[(1r,2s,3r,6r,7r,10s,11s,14s)-11-(furan-3-yl)-3-hydroxy-2,6,10-trimethyl-4,13-dioxo-5-(propan-2-ylidene)-12,15-dioxatetracyclo[8.5.0.0¹,¹⁴.0²,⁷]pentadecan-6-yl]prop-2-enoate

Description

Atalantolide belongs to the class of organic compounds known as steroid lactones. These are sterol lipids containing a lactone moiety linked to the steroid skeleton. methyl (2e)-3-[(1r,2s,3r,6r,7r,10s,11s,14s)-11-(furan-3-yl)-3-hydroxy-2,6,10-trimethyl-4,13-dioxo-5-(propan-2-ylidene)-12,15-dioxatetracyclo[8.5.0.0¹,¹⁴.0²,⁷]pentadecan-6-yl]prop-2-enoate is found in Atalantia buxifolia and Harrisonia abyssinica. Based on a literature review very few articles have been published on Atalantolide.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102220582D          

 35 39  0  0  1  0            999 V2000
    4.4362   -3.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5794   -2.9875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9474   -2.4572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1722   -2.7394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0907   -1.6447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4587   -1.1144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3772   -0.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    0.4125    0.0000 C   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


  Mrv1652309102220582D          

 35 39  0  0  1  0            999 V2000
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 31 33  1  0  0  0  0
 33 34  1  1  0  0  0
 35 34  1  1  0  0  0
 33 35  1  0  0  0  0
 22 35  1  0  0  0  0
 17 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0304113

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)\C=C\[C@]1(C)[C@H]2CC[C@@]3(C)[C@@H](OC(=O)[C@H]4O[C@@]34[C@]2(C)[C@@H](O)C(=O)C1=C(C)C)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C27H32O8/c1-14(2)18-19(29)20(30)26(5)16(24(18,3)10-8-17(28)32-6)7-11-25(4)21(15-9-12-33-13-15)34-23(31)22-27(25,26)35-22/h8-10,12-13,16,20-22,30H,7,11H2,1-6H3/b10-8+/t16-,20+,21+,22-,24-,25+,26+,27-/m1/s1

> <INCHI_KEY>
RIVWJURWTHLRFT-AOERXXKASA-N

> <FORMULA>
C27H32O8

> <MOLECULAR_WEIGHT>
484.545

> <EXACT_MASS>
484.20971799

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
50.44502219774819

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (2E)-3-[(1R,2S,3R,6R,7R,10S,11R,14S)-11-(furan-3-yl)-3-hydroxy-2,6,10-trimethyl-4,13-dioxo-5-(propan-2-ylidene)-12,15-dioxatetracyclo[8.5.0.0^{1,14}.0^{2,7}]pentadecan-6-yl]prop-2-enoate

> <JCHEM_LOGP>
3.5925072749999996

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.854996067771008

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8718545923811827

> <JCHEM_POLAR_SURFACE_AREA>
115.57000000000002

> <JCHEM_REFRACTIVITY>
124.61019999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2E)-3-[(1R,2S,3R,6R,7R,10S,11R,14S)-11-(furan-3-yl)-3-hydroxy-2,6,10-trimethyl-4,13-dioxo-5-(propan-2-ylidene)-12,15-dioxatetracyclo[8.5.0.0^{1,14}.0^{2,7}]pentadecan-6-yl]prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       8.281  -7.093   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       8.548  -5.577   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.369  -4.587   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       5.921  -5.113   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       7.636  -3.070   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.456  -2.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.171  -1.090   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.034   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.804  -0.564   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.804   2.104   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       7.494   3.437   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.414   3.437   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.575   2.302   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.414  -1.897   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.334  -1.897   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.206  -1.897   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.420  -3.304   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.724  -4.335   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -2.058  -3.565   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -1.738  -2.058   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -0.206   0.770   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -0.206   3.437   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       3.644   2.104   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   19                                             
CONECT    8    7                                                            
CONECT    9    7   10   13                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    9   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19   35                                             
CONECT   18   17                                                            
CONECT   19   17    7   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24   35                                             
CONECT   23   22                                                            
CONECT   24   22   25   30                                                  
CONECT   25   24   26   29                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   25                                                       
CONECT   30   24   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33   35                                                       
CONECT   35   34   33   22   17                                             
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₂O₈

Average Mass

484.5450 Da

Monoisotopic Mass

484.20972 Da

IUPAC Name

methyl (2E)-3-[(1R,2S,3R,6R,7R,10S,11R,14S)-11-(furan-3-yl)-3-hydroxy-2,6,10-trimethyl-4,13-dioxo-5-(propan-2-ylidene)-12,15-dioxatetracyclo[8.5.0.0^{1,14}.0^{2,7}]pentadecan-6-yl]prop-2-enoate

Traditional Name

methyl (2E)-3-[(1R,2S,3R,6R,7R,10S,11R,14S)-11-(furan-3-yl)-3-hydroxy-2,6,10-trimethyl-4,13-dioxo-5-(propan-2-ylidene)-12,15-dioxatetracyclo[8.5.0.0^{1,14}.0^{2,7}]pentadecan-6-yl]prop-2-enoate

CAS Registry Number

Not Available

SMILES

COC(=O)\C=C\[C@]1(C)[C@H]2CC[C@@]3(C)[C@@H](OC(=O)[C@H]4O[C@@]34[C@]2(C)[C@@H](O)C(=O)C1=C(C)C)C1=COC=C1

InChI Identifier

InChI=1S/C27H32O8/c1-14(2)18-19(29)20(30)26(5)16(24(18,3)10-8-17(28)32-6)7-11-25(4)21(15-9-12-33-13-15)34-23(31)22-27(25,26)35-22/h8-10,12-13,16,20-22,30H,7,11H2,1-6H3/b10-8+/t16-,20+,21+,22-,24-,25+,26+,27-/m1/s1

InChI Key

RIVWJURWTHLRFT-AOERXXKASA-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
Atalantia buxifolia	LOTUS Database	35616633
Harrisonia abyssinica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroid lactones. These are sterol lipids containing a lactone moiety linked to the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Steroid lactones

Alternative Parents

Substituents

Steroid lactone
11-hydroxysteroid
11-beta-hydroxysteroid
2-oxosteroid
Oxosteroid
12-oxosteroid
Hydroxysteroid
Naphthopyran
Naphthalene
Delta_valerolactone
Fatty acid ester
Dioxepane
Delta valerolactone
1,4-dioxepane
Fatty acyl
Pyran
Oxane
Dicarboxylic acid or derivatives
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Furan
Cyclic alcohol
Cyclic ketone
Secondary alcohol
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	3.59	ChemAxon
pKa (Strongest Acidic)	12.85	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	115.57 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	124.61 m³·mol⁻¹	ChemAxon
Polarizability	50.45 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

C00042251

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

101281328

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (2e)-3-[(1r,2s,3r,6r,7r,10s,11s,14s)-11-(furan-3-yl)-3-hydroxy-2,6,10-trimethyl-4,13-dioxo-5-(propan-2-ylidene)-12,15-dioxatetracyclo[8.5.0.0¹,¹⁴.0²,⁷]pentadecan-6-yl]prop-2-enoate (NP0304113)

MOL for NP0304113 (methyl (2e)-3-[(1r,2s,3r,6r,7r,10s,11s,14s)-11-(furan-3-yl)-3-hydroxy-2,6,10-trimethyl-4,13-dioxo-5-(propan-2-ylidene)-12,15-dioxatetracyclo[8.5.0.0¹,¹⁴.0²,⁷]pentadecan-6-yl]prop-2-enoate)

3D MOL for NP0304113 (methyl (2e)-3-[(1r,2s,3r,6r,7r,10s,11s,14s)-11-(furan-3-yl)-3-hydroxy-2,6,10-trimethyl-4,13-dioxo-5-(propan-2-ylidene)-12,15-dioxatetracyclo[8.5.0.0¹,¹⁴.0²,⁷]pentadecan-6-yl]prop-2-enoate)

3D SDF for NP0304113 (methyl (2e)-3-[(1r,2s,3r,6r,7r,10s,11s,14s)-11-(furan-3-yl)-3-hydroxy-2,6,10-trimethyl-4,13-dioxo-5-(propan-2-ylidene)-12,15-dioxatetracyclo[8.5.0.0¹,¹⁴.0²,⁷]pentadecan-6-yl]prop-2-enoate)

3D-SDF for NP0304113 (methyl (2e)-3-[(1r,2s,3r,6r,7r,10s,11s,14s)-11-(furan-3-yl)-3-hydroxy-2,6,10-trimethyl-4,13-dioxo-5-(propan-2-ylidene)-12,15-dioxatetracyclo[8.5.0.0¹,¹⁴.0²,⁷]pentadecan-6-yl]prop-2-enoate)

PDB for NP0304113 (methyl (2e)-3-[(1r,2s,3r,6r,7r,10s,11s,14s)-11-(furan-3-yl)-3-hydroxy-2,6,10-trimethyl-4,13-dioxo-5-(propan-2-ylidene)-12,15-dioxatetracyclo[8.5.0.0¹,¹⁴.0²,⁷]pentadecan-6-yl]prop-2-enoate)

3D PDB for NP0304113 (methyl (2e)-3-[(1r,2s,3r,6r,7r,10s,11s,14s)-11-(furan-3-yl)-3-hydroxy-2,6,10-trimethyl-4,13-dioxo-5-(propan-2-ylidene)-12,15-dioxatetracyclo[8.5.0.0¹,¹⁴.0²,⁷]pentadecan-6-yl]prop-2-enoate)

SMILES for NP0304113 (methyl (2e)-3-[(1r,2s,3r,6r,7r,10s,11s,14s)-11-(furan-3-yl)-3-hydroxy-2,6,10-trimethyl-4,13-dioxo-5-(propan-2-ylidene)-12,15-dioxatetracyclo[8.5.0.0¹,¹⁴.0²,⁷]pentadecan-6-yl]prop-2-enoate)

INCHI for NP0304113 (methyl (2e)-3-[(1r,2s,3r,6r,7r,10s,11s,14s)-11-(furan-3-yl)-3-hydroxy-2,6,10-trimethyl-4,13-dioxo-5-(propan-2-ylidene)-12,15-dioxatetracyclo[8.5.0.0¹,¹⁴.0²,⁷]pentadecan-6-yl]prop-2-enoate)

Structure for NP0304113 (methyl (2e)-3-[(1r,2s,3r,6r,7r,10s,11s,14s)-11-(furan-3-yl)-3-hydroxy-2,6,10-trimethyl-4,13-dioxo-5-(propan-2-ylidene)-12,15-dioxatetracyclo[8.5.0.0¹,¹⁴.0²,⁷]pentadecan-6-yl]prop-2-enoate)

3D Structure for NP0304113 (methyl (2e)-3-[(1r,2s,3r,6r,7r,10s,11s,14s)-11-(furan-3-yl)-3-hydroxy-2,6,10-trimethyl-4,13-dioxo-5-(propan-2-ylidene)-12,15-dioxatetracyclo[8.5.0.0¹,¹⁴.0²,⁷]pentadecan-6-yl]prop-2-enoate)