NP-MRD: Showing NP-Card for (1s,3r,6r,8e,11r,14s,15r,16s,17s,19r,20r)-3-ethyl-15,17,21-trihydroxy-4,6,16,20-tetramethyl-24-oxapentacyclo[20.2.1.0¹,⁶.0¹¹,²⁰.0¹⁴,¹⁹]pentacosa-4,8,12,21-tetraene-23,25-dione (NP0327447)

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Record Information

Version

1.0

Created at

2022-09-12 10:02:03 UTC

Updated at

2022-09-12 10:02:04 UTC

NP-MRD ID

NP0327447

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3r,6r,8e,11r,14s,15r,16s,17s,19r,20r)-3-ethyl-15,17,21-trihydroxy-4,6,16,20-tetramethyl-24-oxapentacyclo[20.2.1.0¹,⁶.0¹¹,²⁰.0¹⁴,¹⁹]pentacosa-4,8,12,21-tetraene-23,25-dione

Description

Based on a literature review very few articles have been published on (1S,3R,6R,8Z,11R,14S,15R,16S,17S,19R,20R)-3-ethyl-15,17,21-trihydroxy-4,6,16,20-tetramethyl-24-oxapentacyclo[20.2.1.0¹,⁶.0¹¹,²⁰.0¹⁴,¹⁹]Pentacosa-4,8,12,21-tetraene-23,25-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122212022D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309122212022D          

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   -0.3348   -1.5876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8819   -2.1474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0200   -1.3341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  4  0  0  0
 10 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  2  0  0  0  0
 17 16  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 25 24  1  1  0  0  0
 17 25  1  0  0  0  0
 12 25  1  0  0  0  0
 14 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
  5 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
  3 33  1  0  0  0  0
 33 34  1  0  0  0  0
  9 35  1  0  0  0  0
  5 35  1  0  0  0  0
 35 36  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0327447

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@H]1C[C@@]23OC(=O)C(C2=O)=C(O)[C@]2(C)[C@H](C\C=C/C[C@]3(C)C=C1C)C=C[C@@H]1[C@@H](O)[C@@H](C)[C@@H](O)C[C@@H]21

> <INCHI_IDENTIFIER>
InChI=1S/C30H40O6/c1-6-18-15-30-26(34)23(27(35)36-30)25(33)29(5)19(9-7-8-12-28(30,4)14-16(18)2)10-11-20-21(29)13-22(31)17(3)24(20)32/h7-8,10-11,14,17-22,24,31-33H,6,9,12-13,15H2,1-5H3/b8-7-,25-23?/t17-,18+,19+,20-,21+,22-,24-,28+,29+,30+/m0/s1

> <INCHI_KEY>
AUPHDHHHJBUJQK-QYGFYMAWSA-N

> <FORMULA>
C30H40O6

> <MOLECULAR_WEIGHT>
496.644

> <EXACT_MASS>
496.282489008

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
55.33720687861678

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3R,6R,8E,11R,14S,15R,16S,17S,19R,20R)-3-ethyl-15,17,21-trihydroxy-4,6,16,20-tetramethyl-24-oxapentacyclo[20.2.1.0^{1,6}.0^{11,20}.0^{14,19}]pentacosa-4,8,12,21-tetraene-23,25-dione

> <JCHEM_LOGP>
4.230277177999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.382514215267694

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7983754352417107

> <JCHEM_PKA_STRONGEST_BASIC>
-2.857534687955334

> <JCHEM_POLAR_SURFACE_AREA>
104.05999999999999

> <JCHEM_REFRACTIVITY>
141.10340000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3R,6R,8E,11R,14S,15R,16S,17S,19R,20R)-3-ethyl-15,17,21-trihydroxy-4,6,16,20-tetramethyl-24-oxapentacyclo[20.2.1.0^{1,6}.0^{11,20}.0^{14,19}]pentacosa-4,8,12,21-tetraene-23,25-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.549  -5.520   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.099  -6.038   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.075  -5.041   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.539  -5.539   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.883  -4.612   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.296  -6.174   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       5.827  -6.426   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.518  -7.802   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.546  -5.032   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.987  -4.251   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.124  -5.290   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.631  -2.754   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.184  -4.191   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.485  -1.221   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.740  -0.329   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.141  -0.970   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.286  -2.503   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.686  -3.144   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      13.941  -2.251   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      12.832  -4.677   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.232  -5.318   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.576  -5.569   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      11.722  -7.102   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      10.176  -4.928   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.031  -3.395   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.655   0.203   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.220   0.833   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.061  -0.221   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.140  -1.546   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.499  -3.014   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.878  -1.604   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.019  -2.509   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.818  -3.502   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.625  -2.963   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.380  -4.009   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       5.637  -2.490   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   33                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   30   35                                             
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   35                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14   25                                             
CONECT   13   12                                                            
CONECT   14   12   15   26                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   25                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   17   12                                                  
CONECT   26   14   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29    5   31   32                                             
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32    3   34                                                  
CONECT   34   33                                                            
CONECT   35    9    5   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₀O₆

Average Mass

496.6440 Da

Monoisotopic Mass

496.28249 Da

IUPAC Name

(1S,3R,6R,8E,11R,14S,15R,16S,17S,19R,20R)-3-ethyl-15,17,21-trihydroxy-4,6,16,20-tetramethyl-24-oxapentacyclo[20.2.1.0^{1,6}.0^{11,20}.0^{14,19}]pentacosa-4,8,12,21-tetraene-23,25-dione

Traditional Name

(1S,3R,6R,8E,11R,14S,15R,16S,17S,19R,20R)-3-ethyl-15,17,21-trihydroxy-4,6,16,20-tetramethyl-24-oxapentacyclo[20.2.1.0^{1,6}.0^{11,20}.0^{14,19}]pentacosa-4,8,12,21-tetraene-23,25-dione

CAS Registry Number

Not Available

SMILES

CC[C@@H]1C[C@@]23OC(=O)C(C2=O)=C(O)[C@]2(C)[C@H](C\C=C/C[C@]3(C)C=C1C)C=C[C@@H]1[C@@H](O)[C@@H](C)[C@@H](O)C[C@@H]21

InChI Identifier

InChI=1S/C30H40O6/c1-6-18-15-30-26(34)23(27(35)36-30)25(33)29(5)19(9-7-8-12-28(30,4)14-16(18)2)10-11-20-21(29)13-22(31)17(3)24(20)32/h7-8,10-11,14,17-22,24,31-33H,6,9,12-13,15H2,1-5H3/b8-7-,25-23?/t17-,18+,19+,20-,21+,22-,24-,28+,29+,30+/m0/s1

InChI Key

AUPHDHHHJBUJQK-QYGFYMAWSA-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

Not Available

Chemical Taxonomy

Classification

Not classified

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	4.23	ChemAxon
pKa (Strongest Acidic)	3.8	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	141.1 m³·mol⁻¹	ChemAxon
Polarizability	55.34 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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,3r,6r,8e,11r,14s,15r,16s,17s,19r,20r)-3-ethyl-15,17,21-trihydroxy-4,6,16,20-tetramethyl-24-oxapentacyclo[20.2.1.0¹,⁶.0¹¹,²⁰.0¹⁴,¹⁹]pentacosa-4,8,12,21-tetraene-23,25-dione (NP0327447)

MOL for NP0327447 ((1s,3r,6r,8e,11r,14s,15r,16s,17s,19r,20r)-3-ethyl-15,17,21-trihydroxy-4,6,16,20-tetramethyl-24-oxapentacyclo[20.2.1.0¹,⁶.0¹¹,²⁰.0¹⁴,¹⁹]pentacosa-4,8,12,21-tetraene-23,25-dione)

3D MOL for NP0327447 ((1s,3r,6r,8e,11r,14s,15r,16s,17s,19r,20r)-3-ethyl-15,17,21-trihydroxy-4,6,16,20-tetramethyl-24-oxapentacyclo[20.2.1.0¹,⁶.0¹¹,²⁰.0¹⁴,¹⁹]pentacosa-4,8,12,21-tetraene-23,25-dione)

3D SDF for NP0327447 ((1s,3r,6r,8e,11r,14s,15r,16s,17s,19r,20r)-3-ethyl-15,17,21-trihydroxy-4,6,16,20-tetramethyl-24-oxapentacyclo[20.2.1.0¹,⁶.0¹¹,²⁰.0¹⁴,¹⁹]pentacosa-4,8,12,21-tetraene-23,25-dione)

3D-SDF for NP0327447 ((1s,3r,6r,8e,11r,14s,15r,16s,17s,19r,20r)-3-ethyl-15,17,21-trihydroxy-4,6,16,20-tetramethyl-24-oxapentacyclo[20.2.1.0¹,⁶.0¹¹,²⁰.0¹⁴,¹⁹]pentacosa-4,8,12,21-tetraene-23,25-dione)

PDB for NP0327447 ((1s,3r,6r,8e,11r,14s,15r,16s,17s,19r,20r)-3-ethyl-15,17,21-trihydroxy-4,6,16,20-tetramethyl-24-oxapentacyclo[20.2.1.0¹,⁶.0¹¹,²⁰.0¹⁴,¹⁹]pentacosa-4,8,12,21-tetraene-23,25-dione)

3D PDB for NP0327447 ((1s,3r,6r,8e,11r,14s,15r,16s,17s,19r,20r)-3-ethyl-15,17,21-trihydroxy-4,6,16,20-tetramethyl-24-oxapentacyclo[20.2.1.0¹,⁶.0¹¹,²⁰.0¹⁴,¹⁹]pentacosa-4,8,12,21-tetraene-23,25-dione)

SMILES for NP0327447 ((1s,3r,6r,8e,11r,14s,15r,16s,17s,19r,20r)-3-ethyl-15,17,21-trihydroxy-4,6,16,20-tetramethyl-24-oxapentacyclo[20.2.1.0¹,⁶.0¹¹,²⁰.0¹⁴,¹⁹]pentacosa-4,8,12,21-tetraene-23,25-dione)

INCHI for NP0327447 ((1s,3r,6r,8e,11r,14s,15r,16s,17s,19r,20r)-3-ethyl-15,17,21-trihydroxy-4,6,16,20-tetramethyl-24-oxapentacyclo[20.2.1.0¹,⁶.0¹¹,²⁰.0¹⁴,¹⁹]pentacosa-4,8,12,21-tetraene-23,25-dione)

Structure for NP0327447 ((1s,3r,6r,8e,11r,14s,15r,16s,17s,19r,20r)-3-ethyl-15,17,21-trihydroxy-4,6,16,20-tetramethyl-24-oxapentacyclo[20.2.1.0¹,⁶.0¹¹,²⁰.0¹⁴,¹⁹]pentacosa-4,8,12,21-tetraene-23,25-dione)

3D Structure for NP0327447 ((1s,3r,6r,8e,11r,14s,15r,16s,17s,19r,20r)-3-ethyl-15,17,21-trihydroxy-4,6,16,20-tetramethyl-24-oxapentacyclo[20.2.1.0¹,⁶.0¹¹,²⁰.0¹⁴,¹⁹]pentacosa-4,8,12,21-tetraene-23,25-dione)