NP-MRD: Showing NP-Card for methyl 7,14,25-trihydroxy-4-methoxy-6,16,22-trimethyl-23-[(2-methylbut-2-enoyl)oxy]-3,9,11,17,20-pentaoxaoctacyclo[17.6.1.1⁸,¹⁵.0¹,⁵.0⁶,¹⁸.0⁷,¹⁶.0¹⁰,¹⁴.0²²,²⁶]heptacos-12-ene-4-carboxylate (NP0249077)

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Record Information

Version

2.0

Created at

2022-09-07 11:32:23 UTC

Updated at

2022-09-07 11:32:23 UTC

NP-MRD ID

NP0249077

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 7,14,25-trihydroxy-4-methoxy-6,16,22-trimethyl-23-[(2-methylbut-2-enoyl)oxy]-3,9,11,17,20-pentaoxaoctacyclo[17.6.1.1⁸,¹⁵.0¹,⁵.0⁶,¹⁸.0⁷,¹⁶.0¹⁰,¹⁴.0²²,²⁶]heptacos-12-ene-4-carboxylate

Description

Methyl 7,14,25-trihydroxy-4-methoxy-6,16,22-trimethyl-23-[(2-methylbut-2-enoyl)oxy]-3,9,11,17,20-pentaoxaoctacyclo[17.6.1.1⁸,¹⁵.0¹,⁵.0⁶,¹⁸.0⁷,¹⁶.0¹⁰,¹⁴.0²²,²⁶]Heptacos-12-ene-4-carboxylate 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. methyl 7,14,25-trihydroxy-4-methoxy-6,16,22-trimethyl-23-[(2-methylbut-2-enoyl)oxy]-3,9,11,17,20-pentaoxaoctacyclo[17.6.1.1⁸,¹⁵.0¹,⁵.0⁶,¹⁸.0⁷,¹⁶.0¹⁰,¹⁴.0²²,²⁶]heptacos-12-ene-4-carboxylate is found in Melia azedarach. Methyl 7,14,25-trihydroxy-4-methoxy-6,16,22-trimethyl-23-[(2-methylbut-2-enoyl)oxy]-3,9,11,17,20-pentaoxaoctacyclo[17.6.1.1⁸,¹⁵.0¹,⁵.0⁶,¹⁸.0⁷,¹⁶.0¹⁰,¹⁴.0²²,²⁶]Heptacos-12-ene-4-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004261505172D          

 46 53  0  0  0  0            999 V2000
    2.7106    2.6823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5431    1.8745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1589    1.3256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9423    1.5844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9915    0.5177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8124    0.4356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2939    1.1055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2056    0.7687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9570    0.1123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2123   -0.5661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5964   -0.0172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7639    0.7906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8131   -0.2760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6456   -1.0839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1377   -1.3427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7536   -0.7938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5369   -1.0527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5861    0.0140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1972    0.2729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3647    1.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2020    0.5630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2615   -1.6328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5567   -2.0617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5080   -2.5961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3289   -2.6782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6607   -1.9229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4440   -1.6640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1605   -2.0729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7708   -1.5178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9704   -2.3183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5703   -1.7214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4003   -0.7812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8079   -0.0317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6165    0.1318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2485   -0.3985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0392   -0.1632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5074   -0.8425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0060   -1.4976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2279   -1.2232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3550   -2.0384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4315   -0.7659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9633   -0.0866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6115   -0.8562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6073   -0.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9956   -0.3073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0448   -1.3740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  4  0  0  0
 18 21  1  0  0  0  0
 14 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 31 39  1  0  0  0  0
 35 39  1  0  0  0  0
 39 40  1  0  0  0  0
 33 41  1  0  0  0  0
 29 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  1  0  0  0  0
 27 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  1  0  0  0  0
  5 45  1  0  0  0  0
 10 45  1  0  0  0  0
 26 46  1  0  0  0  0
 10 46  1  0  0  0  0
 22 46  1  0  0  0  0
M  END


  Mrv1533004261505172D          

 46 53  0  0  0  0            999 V2000
    2.7106    2.6823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5431    1.8745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1589    1.3256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9423    1.5844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9915    0.5177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8124    0.4356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2939    1.1055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2056    0.7687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9570    0.1123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2123   -0.5661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5964   -0.0172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7639    0.7906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8131   -0.2760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6456   -1.0839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1377   -1.3427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7536   -0.7938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5369   -1.0527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5861    0.0140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1972    0.2729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3647    1.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2020    0.5630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2615   -1.6328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5567   -2.0617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5080   -2.5961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3289   -2.6782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6607   -1.9229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4440   -1.6640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1605   -2.0729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7708   -1.5178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9704   -2.3183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5703   -1.7214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4003   -0.7812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8079   -0.0317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6165    0.1318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2485   -0.3985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0392   -0.1632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5074   -0.8425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0060   -1.4976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2279   -1.2232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3550   -2.0384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4315   -0.7659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9633   -0.0866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6115   -0.8562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6073   -0.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9956   -0.3073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0448   -1.3740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  4  0  0  0
 18 21  1  0  0  0  0
 14 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 31 39  1  0  0  0  0
 35 39  1  0  0  0  0
 39 40  1  0  0  0  0
 33 41  1  0  0  0  0
 29 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  1  0  0  0  0
 27 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  1  0  0  0  0
  5 45  1  0  0  0  0
 10 45  1  0  0  0  0
 26 46  1  0  0  0  0
 10 46  1  0  0  0  0
 22 46  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0249077

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1(OC)OCC23C4C(OCC4(C)C(CC2O)OC(=O)C(C)=CC)C2OC4(C)C5CC(OC6OC=CC56O)C4(O)C2(C)C13

> <INCHI_IDENTIFIER>
InChI=1S/C33H44O13/c1-8-15(2)23(35)44-18-12-17(34)30-14-43-32(40-7,25(36)39-6)24(30)28(4)22(20-21(30)27(18,3)13-42-20)46-29(5)16-11-19(33(28,29)38)45-26-31(16,37)9-10-41-26/h8-10,16-22,24,26,34,37-38H,11-14H2,1-7H3

> <INCHI_KEY>
FZBWVXCNRRALKQ-UHFFFAOYSA-N

> <FORMULA>
C33H44O13

> <MOLECULAR_WEIGHT>
648.702

> <EXACT_MASS>
648.278191477

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
90

> <JCHEM_AVERAGE_POLARIZABILITY>
65.74658980747844

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 7,14,25-trihydroxy-4-methoxy-6,16,22-trimethyl-23-[(2-methylbut-2-enoyl)oxy]-3,9,11,17,20-pentaoxaoctacyclo[17.6.1.1⁸,¹⁵.0¹,⁵.0⁶,¹⁸.0⁷,¹⁶.0¹⁰,¹⁴.0²²,²⁶]heptacos-12-ene-4-carboxylate

> <ALOGPS_LOGP>
1.49

> <JCHEM_LOGP>
0.7322535526666653

> <ALOGPS_LOGS>
-3.05

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.651667657404293

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.038218226602906

> <JCHEM_PKA_STRONGEST_BASIC>
-3.012235101769556

> <JCHEM_POLAR_SURFACE_AREA>
168.67000000000002

> <JCHEM_REFRACTIVITY>
155.35230000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.78e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 7,14,25-trihydroxy-4-methoxy-6,16,22-trimethyl-23-[(2-methylbut-2-enoyl)oxy]-3,9,11,17,20-pentaoxaoctacyclo[17.6.1.1⁸,¹⁵.0¹,⁵.0⁶,¹⁸.0⁷,¹⁶.0¹⁰,¹⁴.0²²,²⁶]heptacos-12-ene-4-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0       5.060   5.007   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.747   3.499   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.897   2.474   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       7.359   2.958   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.584   0.966   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       7.116   0.813   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       8.015   2.064   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.117   1.435   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       3.653   0.210   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.130  -1.057   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.980  -0.032   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.293   1.476   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.518  -0.515   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.205  -2.023   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.257  -2.506   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.407  -1.482   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.869  -1.965   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.094   0.026   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.368   0.509   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.681   2.017   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.244   1.051   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.355  -3.048   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.039  -3.848   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.815  -4.846   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.347  -4.999   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.967  -3.589   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.429  -3.106   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       7.766  -3.869   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       8.906  -2.833   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.278  -4.328   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.398  -3.213   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.081  -1.458   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.975  -0.059   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      10.484   0.246   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      11.664  -0.744   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      13.140  -0.305   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      14.014  -1.573   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      13.078  -2.796   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      11.626  -2.283   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      11.863  -3.805   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       8.272  -1.430   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       7.398  -0.162   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       6.741  -1.598   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       6.734  -0.058   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       5.592  -0.574   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       3.817  -2.565   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    8   45                                             
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   45   46                                             
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   22                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18                                                            
CONECT   22   14   23   24   46                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   46                                                  
CONECT   27   26   28   43                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31   41                                             
CONECT   30   29                                                            
CONECT   31   29   32   39                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   41                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   39                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   31   35   40                                             
CONECT   40   39                                                            
CONECT   41   33   29   42   43                                             
CONECT   42   41                                                            
CONECT   43   41   27   44   45                                             
CONECT   44   43                                                            
CONECT   45   43    5   10                                                  
CONECT   46   26   10   22                                                  
MASTER        0    0    0    0    0    0    0    0   46    0  106    0
END

View in JSmol

Synonyms

Value	Source
Methyl 7,14,25-trihydroxy-4-methoxy-6,16,22-trimethyl-23-[(2-methylbut-2-enoyl)oxy]-3,9,11,17,20-pentaoxaoctacyclo[17.6.1.1,.0,.0,.0,.0,.0,]heptacos-12-ene-4-carboxylic acid	Generator
Methyl 7,14,25-trihydroxy-4-methoxy-6,16,22-trimethyl-23-[(2-methylbut-2-enoyl)oxy]-3,9,11,17,20-pentaoxaoctacyclo[17.6.1.1⁸,¹⁵.0¹,⁵.0⁶,¹⁸.0⁷,¹⁶.0¹⁰,¹⁴.0²²,²⁶]heptacos-12-ene-4-carboxylic acid	Generator

Chemical Formula

C₃₃H₄₄O₁₃

Average Mass

648.7020 Da

Monoisotopic Mass

648.27819 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

COC(=O)C1(OC)OCC23C4C(OCC4(C)C(CC2O)OC(=O)C(C)=CC)C2OC4(C)C5CC(OC6OC=CC56O)C4(O)C2(C)C13

InChI Identifier

InChI=1S/C33H44O13/c1-8-15(2)23(35)44-18-12-17(34)30-14-43-32(40-7,25(36)39-6)24(30)28(4)22(20-21(30)27(18,3)13-42-20)46-29(5)16-11-19(33(28,29)38)45-26-31(16,37)9-10-41-26/h8-10,16-22,24,26,34,37-38H,11-14H2,1-7H3

InChI Key

FZBWVXCNRRALKQ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Melia azedarach	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
Furopyran
Fatty acid ester
Ketal
Oxepane
Dicarboxylic acid or derivatives
Oxane
Pyran
Fatty acyl
Tetrahydrofuran
Tertiary alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Furan
Cyclic alcohol
Dihydrofuran
Secondary alcohol
Carboxylic acid ester
Polyol
Oxacycle
Carboxylic acid derivative
Ether
Acetal
Dialkyl ether
Carbonyl group
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Alcohol
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	1.49	ALOGPS
logP	0.73	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	12.04	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	168.67 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	155.35 m³·mol⁻¹	ChemAxon
Polarizability	65.75 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

73108491

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 7,14,25-trihydroxy-4-methoxy-6,16,22-trimethyl-23-[(2-methylbut-2-enoyl)oxy]-3,9,11,17,20-pentaoxaoctacyclo[17.6.1.1⁸,¹⁵.0¹,⁵.0⁶,¹⁸.0⁷,¹⁶.0¹⁰,¹⁴.0²²,²⁶]heptacos-12-ene-4-carboxylate (NP0249077)

MOL for NP0249077 (methyl 7,14,25-trihydroxy-4-methoxy-6,16,22-trimethyl-23-[(2-methylbut-2-enoyl)oxy]-3,9,11,17,20-pentaoxaoctacyclo[17.6.1.1⁸,¹⁵.0¹,⁵.0⁶,¹⁸.0⁷,¹⁶.0¹⁰,¹⁴.0²²,²⁶]heptacos-12-ene-4-carboxylate)

3D MOL for NP0249077 (methyl 7,14,25-trihydroxy-4-methoxy-6,16,22-trimethyl-23-[(2-methylbut-2-enoyl)oxy]-3,9,11,17,20-pentaoxaoctacyclo[17.6.1.1⁸,¹⁵.0¹,⁵.0⁶,¹⁸.0⁷,¹⁶.0¹⁰,¹⁴.0²²,²⁶]heptacos-12-ene-4-carboxylate)

3D SDF for NP0249077 (methyl 7,14,25-trihydroxy-4-methoxy-6,16,22-trimethyl-23-[(2-methylbut-2-enoyl)oxy]-3,9,11,17,20-pentaoxaoctacyclo[17.6.1.1⁸,¹⁵.0¹,⁵.0⁶,¹⁸.0⁷,¹⁶.0¹⁰,¹⁴.0²²,²⁶]heptacos-12-ene-4-carboxylate)

3D-SDF for NP0249077 (methyl 7,14,25-trihydroxy-4-methoxy-6,16,22-trimethyl-23-[(2-methylbut-2-enoyl)oxy]-3,9,11,17,20-pentaoxaoctacyclo[17.6.1.1⁸,¹⁵.0¹,⁵.0⁶,¹⁸.0⁷,¹⁶.0¹⁰,¹⁴.0²²,²⁶]heptacos-12-ene-4-carboxylate)

PDB for NP0249077 (methyl 7,14,25-trihydroxy-4-methoxy-6,16,22-trimethyl-23-[(2-methylbut-2-enoyl)oxy]-3,9,11,17,20-pentaoxaoctacyclo[17.6.1.1⁸,¹⁵.0¹,⁵.0⁶,¹⁸.0⁷,¹⁶.0¹⁰,¹⁴.0²²,²⁶]heptacos-12-ene-4-carboxylate)

3D PDB for NP0249077 (methyl 7,14,25-trihydroxy-4-methoxy-6,16,22-trimethyl-23-[(2-methylbut-2-enoyl)oxy]-3,9,11,17,20-pentaoxaoctacyclo[17.6.1.1⁸,¹⁵.0¹,⁵.0⁶,¹⁸.0⁷,¹⁶.0¹⁰,¹⁴.0²²,²⁶]heptacos-12-ene-4-carboxylate)

SMILES for NP0249077 (methyl 7,14,25-trihydroxy-4-methoxy-6,16,22-trimethyl-23-[(2-methylbut-2-enoyl)oxy]-3,9,11,17,20-pentaoxaoctacyclo[17.6.1.1⁸,¹⁵.0¹,⁵.0⁶,¹⁸.0⁷,¹⁶.0¹⁰,¹⁴.0²²,²⁶]heptacos-12-ene-4-carboxylate)

INCHI for NP0249077 (methyl 7,14,25-trihydroxy-4-methoxy-6,16,22-trimethyl-23-[(2-methylbut-2-enoyl)oxy]-3,9,11,17,20-pentaoxaoctacyclo[17.6.1.1⁸,¹⁵.0¹,⁵.0⁶,¹⁸.0⁷,¹⁶.0¹⁰,¹⁴.0²²,²⁶]heptacos-12-ene-4-carboxylate)

Structure for NP0249077 (methyl 7,14,25-trihydroxy-4-methoxy-6,16,22-trimethyl-23-[(2-methylbut-2-enoyl)oxy]-3,9,11,17,20-pentaoxaoctacyclo[17.6.1.1⁸,¹⁵.0¹,⁵.0⁶,¹⁸.0⁷,¹⁶.0¹⁰,¹⁴.0²²,²⁶]heptacos-12-ene-4-carboxylate)

3D Structure for NP0249077 (methyl 7,14,25-trihydroxy-4-methoxy-6,16,22-trimethyl-23-[(2-methylbut-2-enoyl)oxy]-3,9,11,17,20-pentaoxaoctacyclo[17.6.1.1⁸,¹⁵.0¹,⁵.0⁶,¹⁸.0⁷,¹⁶.0¹⁰,¹⁴.0²²,²⁶]heptacos-12-ene-4-carboxylate)