NP-MRD: Showing NP-Card for methyl 14-hydroxy-2,6,6,10,13-pentamethyl-16-methylidene-7,15-dioxotetracyclo[11.2.1.0²,¹¹.0⁵,¹⁰]hexadecane-1-carboxylate (NP0278040)

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Record Information

Version

2.0

Created at

2022-09-09 02:55:36 UTC

Updated at

2022-09-09 02:55:36 UTC

NP-MRD ID

NP0278040

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 14-hydroxy-2,6,6,10,13-pentamethyl-16-methylidene-7,15-dioxotetracyclo[11.2.1.0²,¹¹.0⁵,¹⁰]hexadecane-1-carboxylate

Description

Methyl 14-hydroxy-2,6,6,10,13-pentamethyl-16-methylidene-7,15-dioxotetracyclo[11.2.1.0²,¹¹.0⁵,¹⁰]Hexadecane-1-carboxylate belongs to the class of organic compounds known as steroids and steroid derivatives. Steroids and steroid derivatives are compounds based on the cyclopenta[a]phenanthrene carbon skeleton, partially or completely hydrogenated; there are usually methyl groups at C-10 and C-13, and often an alkyl group at C-17. By extension, one or more bond scissions, ring expansions and/or ring contractions of the skeleton may have occurred. methyl 14-hydroxy-2,6,6,10,13-pentamethyl-16-methylidene-7,15-dioxotetracyclo[11.2.1.0²,¹¹.0⁵,¹⁰]hexadecane-1-carboxylate is found in Melia azedarach. Methyl 14-hydroxy-2,6,6,10,13-pentamethyl-16-methylidene-7,15-dioxotetracyclo[11.2.1.0²,¹¹.0⁵,¹⁰]Hexadecane-1-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241506482D          

 29 32  0  0  0  0            999 V2000
    0.0109    2.6523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2261    1.8559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0235    1.6442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6056    2.2288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2388    0.8477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6146    0.3082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1423    0.6365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6473   -0.5161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0812   -0.9032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3122   -1.0046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1606   -1.8155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1086   -0.7893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4368   -0.0324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2613   -0.0614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8239   -0.7609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6484   -0.7900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4729   -0.8190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9103   -0.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7348   -0.1485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5232    0.6090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3079    0.8638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4086    1.4260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6987    0.6381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3116    1.3666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4871    1.3957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0497    0.6961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7182    1.4516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0439   -0.0876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2196   -0.1203    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  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  5 26  1  0  0  0  0
 13 26  1  0  0  0  0
 26 27  1  0  0  0  0
 10 28  1  0  0  0  0
  5 28  1  0  0  0  0
 28 29  2  0  0  0  0
M  END

     RDKit          3D

 63 66  0  0  0  0  0  0  0  0999 V2000
    4.0468    0.2707   -0.6252 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7678    0.1204   -0.9400 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9351    1.1166   -1.6678 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7302    2.1676   -2.3651 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9566    1.6889   -0.6494 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0437    0.5575   -0.1876 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1297    1.0463    0.6077 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7522    1.9460    1.7784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9346    1.9608   -0.3294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2638    2.3638    0.2552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7496    1.4207    1.2778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3994    1.7809    2.2416 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3963   -0.0081    1.0606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9614   -0.8048    2.2453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0646   -0.5719   -0.1682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9219   -0.1361    1.0582 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5779   -1.3951    0.2778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1427   -1.7914    0.4730 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7872   -0.6060    0.3558 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4995   -0.4171    1.6355 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8258   -1.0029   -0.6890 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5944   -2.1914   -0.3264 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6393   -3.2084   -1.0782 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3104   -2.2641    0.8552 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0493   -3.4169    1.1954 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1523   -1.1173   -1.9996 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6393   -2.1166   -2.4477 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2261    0.2137   -2.6521 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0884    0.1038   -3.7651 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5564   -0.5375   -0.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6144    1.1577   -0.8766 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6960    1.7137   -2.6851 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9792    3.0194   -1.7114 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1471    2.5028   -3.2534 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3536    2.4018   -1.2499 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266    2.1500    0.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4133    0.1869   -1.1599 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2532    2.3560    1.7182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9869    1.4344    2.7591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4252    2.8564    1.8377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3461    2.9256   -0.3434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9665    1.6007   -1.3520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2855    3.3907    0.6733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9973    2.3877   -0.6006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2909   -1.8156    1.9109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8680   -0.3108    2.6581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2397   -0.9198    3.0522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0379   -1.6775   -0.1091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5590   -0.2857   -1.1085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1015   -0.2113   -0.2135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5923   -0.3554    2.1167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8097   -1.3269   -0.7829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2043   -2.2064    0.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0350   -2.2850    1.4850 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0757   -2.6072   -0.2441 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0200    0.2020    2.3967 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5614   -1.4357    2.1273 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5835   -0.1423    1.4856 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8164   -3.6523    2.2575 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1585   -3.2382    1.1577 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7475   -4.2841    0.5883 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2828    0.6004   -3.0282 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7883    0.6958   -4.5079 H   0  0  0  0  0  0  0  0  0  0  0  0
 25 24  1  0
 24 22  1  0
 22 23  2  0
 21 22  1  1
 21 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  1  0
 28  3  1  0
  3  4  1  6
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  1
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  1
  3  2  1  0
  2  1  2  3
 19 21  1  0
  2 21  1  0
 19  6  1  0
 16  7  1  0
 25 59  1  0
 25 60  1  0
 25 61  1  0
 28 62  1  6
 29 63  1  0
  4 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  6
  8 38  1  0
  8 39  1  0
  8 40  1  0
  9 41  1  0
  9 42  1  0
 10 43  1  0
 10 44  1  0
 14 45  1  0
 14 46  1  0
 14 47  1  0
 15 48  1  0
 15 49  1  0
 15 50  1  0
 16 51  1  1
 17 52  1  0
 17 53  1  0
 18 54  1  0
 18 55  1  0
 20 56  1  0
 20 57  1  0
 20 58  1  0
  1 30  1  0
  1 31  1  0
M  END


  Mrv1533004241506482D          

 29 32  0  0  0  0            999 V2000
    0.0109    2.6523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2261    1.8559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0235    1.6442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6056    2.2288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2388    0.8477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6146    0.3082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1423    0.6365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6473   -0.5161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0812   -0.9032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3122   -1.0046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1606   -1.8155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1086   -0.7893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4368   -0.0324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2613   -0.0614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8239   -0.7609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6484   -0.7900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4729   -0.8190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9103   -0.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7348   -0.1485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5232    0.6090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3079    0.8638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4086    1.4260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6987    0.6381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3116    1.3666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4871    1.3957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0497    0.6961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7182    1.4516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0439   -0.0876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2196   -0.1203    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  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  5 26  1  0  0  0  0
 13 26  1  0  0  0  0
 26 27  1  0  0  0  0
 10 28  1  0  0  0  0
  5 28  1  0  0  0  0
 28 29  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0278040

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C12C(=O)C(O)C(C)(CC3C4(C)CCC(=O)C(C)(C)C4CCC13C)C2=C

> <INCHI_IDENTIFIER>
InChI=1S/C24H34O5/c1-13-22(5)12-15-21(4)10-9-16(25)20(2,3)14(21)8-11-23(15,6)24(13,19(28)29-7)18(27)17(22)26/h14-15,17,26H,1,8-12H2,2-7H3

> <INCHI_KEY>
UXIVDLDIDDQRTQ-UHFFFAOYSA-N

> <FORMULA>
C24H34O5

> <MOLECULAR_WEIGHT>
402.531

> <EXACT_MASS>
402.240624195

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
44.197668932456544

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 14-hydroxy-2,6,6,10,13-pentamethyl-16-methylidene-7,15-dioxotetracyclo[11.2.1.0²,¹¹.0⁵,¹⁰]hexadecane-1-carboxylate

> <ALOGPS_LOGP>
2.92

> <JCHEM_LOGP>
3.791112973333335

> <ALOGPS_LOGS>
-4.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.960214000813203

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.862307750197363

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7338223500394294

> <JCHEM_POLAR_SURFACE_AREA>
80.67000000000002

> <JCHEM_REFRACTIVITY>
108.35609999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.07e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 14-hydroxy-2,6,6,10,13-pentamethyl-16-methylidene-7,15-dioxotetracyclo[11.2.1.0²,¹¹.0⁵,¹⁰]hexadecane-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       0.020   4.951   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.422   3.464   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.911   3.069   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.997   4.160   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.312   1.582   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.147   0.575   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.266   1.188   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.208  -0.963   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.152  -1.686   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.449  -1.875   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.166  -3.389   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.936  -1.473   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.549  -0.060   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.088  -0.115   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.271  -1.420   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.810  -1.475   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.349  -1.529   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.166  -0.223   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      10.705  -0.277   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.443   1.137   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.908   1.612   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.229   2.662   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.904   1.191   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.182   2.551   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.643   2.605   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.826   1.299   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.207   2.710   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.949  -0.164   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.410  -0.224   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   26   28                                             
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12   28                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   26                                                  
CONECT   14   13   15   16   23                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   20   14   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25    5   13   27                                             
CONECT   27   26                                                            
CONECT   28   10    5   29                                                  
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Value	Source
Methyl 14-hydroxy-2,6,6,10,13-pentamethyl-16-methylidene-7,15-dioxotetracyclo[11.2.1.0,.0,]hexadecane-1-carboxylic acid	Generator
Methyl 14-hydroxy-2,6,6,10,13-pentamethyl-16-methylidene-7,15-dioxotetracyclo[11.2.1.0²,¹¹.0⁵,¹⁰]hexadecane-1-carboxylic acid	Generator

Chemical Formula

C₂₄H₃₄O₅

Average Mass

402.5310 Da

Monoisotopic Mass

402.24062 Da

IUPAC Name

methyl 14-hydroxy-2,6,6,10,13-pentamethyl-16-methylidene-7,15-dioxotetracyclo[11.2.1.0²,¹¹.0⁵,¹⁰]hexadecane-1-carboxylate

Traditional Name

methyl 14-hydroxy-2,6,6,10,13-pentamethyl-16-methylidene-7,15-dioxotetracyclo[11.2.1.0²,¹¹.0⁵,¹⁰]hexadecane-1-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C12C(=O)C(O)C(C)(CC3C4(C)CCC(=O)C(C)(C)C4CCC13C)C2=C

InChI Identifier

InChI=1S/C24H34O5/c1-13-22(5)12-15-21(4)10-9-16(25)20(2,3)14(21)8-11-23(15,6)24(13,19(28)29-7)18(27)17(22)26/h14-15,17,26H,1,8-12H2,2-7H3

InChI Key

UXIVDLDIDDQRTQ-UHFFFAOYSA-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
Melia azedarach	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroids and steroid derivatives. Steroids and steroid derivatives are compounds based on the cyclopenta[a]phenanthrene carbon skeleton, partially or completely hydrogenated; there are usually methyl groups at C-10 and C-13, and often an alkyl group at C-17. By extension, one or more bond scissions, ring expansions and/or ring contractions of the skeleton may have occurred.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Not Available

Direct Parent

Steroids and steroid derivatives

Alternative Parents

Substituents

Steroid
Cyclic alcohol
Methyl ester
Carboxylic acid ester
Ketone
Secondary alcohol
Cyclic ketone
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organooxygen compound
Organic oxygen compound
Alcohol
Carbonyl group
Organic oxide
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	2.92	ALOGPS
logP	3.79	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	12.86	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	80.67 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	108.36 m³·mol⁻¹	ChemAxon
Polarizability	44.2 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

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 methyl 14-hydroxy-2,6,6,10,13-pentamethyl-16-methylidene-7,15-dioxotetracyclo[11.2.1.0²,¹¹.0⁵,¹⁰]hexadecane-1-carboxylate (NP0278040)

MOL for NP0278040 (methyl 14-hydroxy-2,6,6,10,13-pentamethyl-16-methylidene-7,15-dioxotetracyclo[11.2.1.0²,¹¹.0⁵,¹⁰]hexadecane-1-carboxylate)

3D MOL for NP0278040 (methyl 14-hydroxy-2,6,6,10,13-pentamethyl-16-methylidene-7,15-dioxotetracyclo[11.2.1.0²,¹¹.0⁵,¹⁰]hexadecane-1-carboxylate)

3D SDF for NP0278040 (methyl 14-hydroxy-2,6,6,10,13-pentamethyl-16-methylidene-7,15-dioxotetracyclo[11.2.1.0²,¹¹.0⁵,¹⁰]hexadecane-1-carboxylate)

3D-SDF for NP0278040 (methyl 14-hydroxy-2,6,6,10,13-pentamethyl-16-methylidene-7,15-dioxotetracyclo[11.2.1.0²,¹¹.0⁵,¹⁰]hexadecane-1-carboxylate)

PDB for NP0278040 (methyl 14-hydroxy-2,6,6,10,13-pentamethyl-16-methylidene-7,15-dioxotetracyclo[11.2.1.0²,¹¹.0⁵,¹⁰]hexadecane-1-carboxylate)

3D PDB for NP0278040 (methyl 14-hydroxy-2,6,6,10,13-pentamethyl-16-methylidene-7,15-dioxotetracyclo[11.2.1.0²,¹¹.0⁵,¹⁰]hexadecane-1-carboxylate)

SMILES for NP0278040 (methyl 14-hydroxy-2,6,6,10,13-pentamethyl-16-methylidene-7,15-dioxotetracyclo[11.2.1.0²,¹¹.0⁵,¹⁰]hexadecane-1-carboxylate)

INCHI for NP0278040 (methyl 14-hydroxy-2,6,6,10,13-pentamethyl-16-methylidene-7,15-dioxotetracyclo[11.2.1.0²,¹¹.0⁵,¹⁰]hexadecane-1-carboxylate)

Structure for NP0278040 (methyl 14-hydroxy-2,6,6,10,13-pentamethyl-16-methylidene-7,15-dioxotetracyclo[11.2.1.0²,¹¹.0⁵,¹⁰]hexadecane-1-carboxylate)

3D Structure for NP0278040 (methyl 14-hydroxy-2,6,6,10,13-pentamethyl-16-methylidene-7,15-dioxotetracyclo[11.2.1.0²,¹¹.0⁵,¹⁰]hexadecane-1-carboxylate)