NP-MRD: Showing NP-Card for methyl (3s)-3-[(1's,2s,3s,4'r,6's,7'r,11'r)-3,6'-dihydroxy-6'-methyl-2',5-dioxo-3'-oxaspiro[oxolane-2,8'-tricyclo[5.3.1.0⁴,¹¹]undecan]-9'-en-9'-yl]-4-methylpent-4-enoate (NP0300371)

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Record Information

Version

2.0

Created at

2022-09-10 12:44:17 UTC

Updated at

2022-09-10 12:44:17 UTC

NP-MRD ID

NP0300371

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (3s)-3-[(1's,2s,3s,4'r,6's,7'r,11'r)-3,6'-dihydroxy-6'-methyl-2',5-dioxo-3'-oxaspiro[oxolane-2,8'-tricyclo[5.3.1.0⁴,¹¹]undecan]-9'-en-9'-yl]-4-methylpent-4-enoate

Description

Not Available

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309102214442D          

 29 32  0  0  1  0            999 V2000
    1.9869    3.2299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8098    3.1718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2716    3.8554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1772    2.4172    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7412    3.0857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5987    2.9965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3472    2.2108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4060    3.1718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9607    2.5611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6219    1.6594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3614    1.2937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4145    0.4704    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9246   -0.5789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7804   -0.7499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3483   -1.1693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6087   -0.8036    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7955   -0.9424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4122   -0.2119    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7799   -0.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6072   -0.5740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9885    0.3785    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7280    0.0128    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9354    1.2018    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2049    0.8184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6146    1.3947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2418    1.4906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803    2.1343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7966    2.0150    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7555    2.8777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 16 15  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  6  0  0  0
 21 18  1  6  0  0  0
 22 21  1  6  0  0  0
 12 22  1  0  0  0  0
 16 22  1  0  0  0  0
 21 23  1  0  0  0  0
 10 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  6  0  0  0
M  END


  Mrv1652309102214442D          

 29 32  0  0  1  0            999 V2000
    1.9869    3.2299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8098    3.1718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2716    3.8554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1772    2.4172    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7412    3.0857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5987    2.9965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3472    2.2108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4060    3.1718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9607    2.5611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6219    1.6594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3614    1.2937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4145    0.4704    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9246   -0.5789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7804   -0.7499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3483   -1.1693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6087   -0.8036    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7955   -0.9424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4122   -0.2119    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7799   -0.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6072   -0.5740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9885    0.3785    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7280    0.0128    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9354    1.2018    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2049    0.8184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6146    1.3947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2418    1.4906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803    2.1343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7966    2.0150    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7555    2.8777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 16 15  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  6  0  0  0
 21 18  1  6  0  0  0
 22 21  1  6  0  0  0
 12 22  1  0  0  0  0
 16 22  1  0  0  0  0
 21 23  1  0  0  0  0
 10 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0300371

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C[C@@H](C(C)=C)C1=C[C@H]2[C@@H]3[C@@H](C[C@](C)(O)[C@@H]3[C@]11OC(=O)C[C@@H]1O)OC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H26O8/c1-9(2)10(6-15(23)27-4)12-5-11-17-13(28-19(11)25)8-20(3,26)18(17)21(12)14(22)7-16(24)29-21/h5,10-11,13-14,17-18,22,26H,1,6-8H2,2-4H3/t10?,11-,13+,14-,17+,18+,20-,21-/m0/s1

> <INCHI_KEY>
LGDPFSGSVUCBTJ-YPLQEJOMSA-N

> <FORMULA>
C21H26O8

> <MOLECULAR_WEIGHT>
406.431

> <EXACT_MASS>
406.162767797

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
40.0363916366294

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (3S)-3-[(1'S,2S,3S,4'R,6'S,7'R,11'R)-3,6'-dihydroxy-6'-methyl-2',5-dioxo-3'-oxaspiro[oxolane-2,8'-tricyclo[5.3.1.0^{4,11}]undecan]-9'-en-9'-yl]-4-methylpent-4-enoate

> <JCHEM_LOGP>
-0.5494014649999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.632798682128954

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.574579186924215

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9819020848048217

> <JCHEM_POLAR_SURFACE_AREA>
119.36000000000003

> <JCHEM_REFRACTIVITY>
99.1007

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (3S)-3-[(1'S,2S,3S,4'R,6'S,7'R,11'R)-3,6'-dihydroxy-6'-methyl-2',5-dioxo-3'-oxaspiro[oxolane-2,8'-tricyclo[5.3.1.0^{4,11}]undecan]-9'-en-9'-yl]-4-methylpent-4-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       3.709   6.029   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.245   5.921   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.107   7.197   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.931   4.512   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.984   5.760   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.584   5.594   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       8.115   4.127   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      10.091   5.921   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      11.127   4.781   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.894   3.097   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.275   2.415   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.374   0.878   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.326  -1.081   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.923  -1.400   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       6.250  -2.183   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.870  -1.500   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.352  -1.759   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.636  -0.395   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.456  -1.594   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.134  -1.071   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.712   0.706   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.092   0.024   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.613   2.243   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.249   1.528   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.147   2.604   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -0.451   2.782   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.830   3.984   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.354   3.761   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       3.277   5.372   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8                                                            
CONECT   10    4   11   23                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   22                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   22                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18   22   23                                                  
CONECT   22   21   12   16                                                  
CONECT   23   21   10   24   28                                             
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   23   29                                                  
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₆O₈

Average Mass

406.4310 Da

Monoisotopic Mass

406.16277 Da

IUPAC Name

methyl (3S)-3-[(1'S,2S,3S,4'R,6'S,7'R,11'R)-3,6'-dihydroxy-6'-methyl-2',5-dioxo-3'-oxaspiro[oxolane-2,8'-tricyclo[5.3.1.0^{4,11}]undecan]-9'-en-9'-yl]-4-methylpent-4-enoate

Traditional Name

methyl (3S)-3-[(1'S,2S,3S,4'R,6'S,7'R,11'R)-3,6'-dihydroxy-6'-methyl-2',5-dioxo-3'-oxaspiro[oxolane-2,8'-tricyclo[5.3.1.0^{4,11}]undecan]-9'-en-9'-yl]-4-methylpent-4-enoate

CAS Registry Number

Not Available

SMILES

COC(=O)C[C@@H](C(C)=C)C1=C[C@H]2[C@@H]3[C@@H](C[C@](C)(O)[C@@H]3[C@]11OC(=O)C[C@@H]1O)OC2=O

InChI Identifier

InChI=1S/C21H26O8/c1-9(2)10(6-15(23)27-4)12-5-11-17-13(28-19(11)25)8-20(3,26)18(17)21(12)14(22)7-16(24)29-21/h5,10-11,13-14,17-18,22,26H,1,6-8H2,2-4H3/t10?,11-,13+,14-,17+,18+,20-,21-/m0/s1

InChI Key

LGDPFSGSVUCBTJ-YPLQEJOMSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

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	-0.55	ChemAxon
pKa (Strongest Acidic)	13.57	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	119.36 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	99.1 m³·mol⁻¹	ChemAxon
Polarizability	40.04 Å³	ChemAxon
Number of Rings	4	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

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (3s)-3-[(1's,2s,3s,4'r,6's,7'r,11'r)-3,6'-dihydroxy-6'-methyl-2',5-dioxo-3'-oxaspiro[oxolane-2,8'-tricyclo[5.3.1.0⁴,¹¹]undecan]-9'-en-9'-yl]-4-methylpent-4-enoate (NP0300371)

MOL for NP0300371 (methyl (3s)-3-[(1's,2s,3s,4'r,6's,7'r,11'r)-3,6'-dihydroxy-6'-methyl-2',5-dioxo-3'-oxaspiro[oxolane-2,8'-tricyclo[5.3.1.0⁴,¹¹]undecan]-9'-en-9'-yl]-4-methylpent-4-enoate)

3D MOL for NP0300371 (methyl (3s)-3-[(1's,2s,3s,4'r,6's,7'r,11'r)-3,6'-dihydroxy-6'-methyl-2',5-dioxo-3'-oxaspiro[oxolane-2,8'-tricyclo[5.3.1.0⁴,¹¹]undecan]-9'-en-9'-yl]-4-methylpent-4-enoate)

3D SDF for NP0300371 (methyl (3s)-3-[(1's,2s,3s,4'r,6's,7'r,11'r)-3,6'-dihydroxy-6'-methyl-2',5-dioxo-3'-oxaspiro[oxolane-2,8'-tricyclo[5.3.1.0⁴,¹¹]undecan]-9'-en-9'-yl]-4-methylpent-4-enoate)

3D-SDF for NP0300371 (methyl (3s)-3-[(1's,2s,3s,4'r,6's,7'r,11'r)-3,6'-dihydroxy-6'-methyl-2',5-dioxo-3'-oxaspiro[oxolane-2,8'-tricyclo[5.3.1.0⁴,¹¹]undecan]-9'-en-9'-yl]-4-methylpent-4-enoate)

PDB for NP0300371 (methyl (3s)-3-[(1's,2s,3s,4'r,6's,7'r,11'r)-3,6'-dihydroxy-6'-methyl-2',5-dioxo-3'-oxaspiro[oxolane-2,8'-tricyclo[5.3.1.0⁴,¹¹]undecan]-9'-en-9'-yl]-4-methylpent-4-enoate)

3D PDB for NP0300371 (methyl (3s)-3-[(1's,2s,3s,4'r,6's,7'r,11'r)-3,6'-dihydroxy-6'-methyl-2',5-dioxo-3'-oxaspiro[oxolane-2,8'-tricyclo[5.3.1.0⁴,¹¹]undecan]-9'-en-9'-yl]-4-methylpent-4-enoate)

SMILES for NP0300371 (methyl (3s)-3-[(1's,2s,3s,4'r,6's,7'r,11'r)-3,6'-dihydroxy-6'-methyl-2',5-dioxo-3'-oxaspiro[oxolane-2,8'-tricyclo[5.3.1.0⁴,¹¹]undecan]-9'-en-9'-yl]-4-methylpent-4-enoate)

INCHI for NP0300371 (methyl (3s)-3-[(1's,2s,3s,4'r,6's,7'r,11'r)-3,6'-dihydroxy-6'-methyl-2',5-dioxo-3'-oxaspiro[oxolane-2,8'-tricyclo[5.3.1.0⁴,¹¹]undecan]-9'-en-9'-yl]-4-methylpent-4-enoate)

Structure for NP0300371 (methyl (3s)-3-[(1's,2s,3s,4'r,6's,7'r,11'r)-3,6'-dihydroxy-6'-methyl-2',5-dioxo-3'-oxaspiro[oxolane-2,8'-tricyclo[5.3.1.0⁴,¹¹]undecan]-9'-en-9'-yl]-4-methylpent-4-enoate)

3D Structure for NP0300371 (methyl (3s)-3-[(1's,2s,3s,4'r,6's,7'r,11'r)-3,6'-dihydroxy-6'-methyl-2',5-dioxo-3'-oxaspiro[oxolane-2,8'-tricyclo[5.3.1.0⁴,¹¹]undecan]-9'-en-9'-yl]-4-methylpent-4-enoate)