NP-MRD: Showing NP-Card for nimbocinol (NP0220053)

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Record Information

Version

2.0

Created at

2022-09-05 21:15:15 UTC

Updated at

2022-09-05 21:15:16 UTC

NP-MRD ID

NP0220053

Secondary Accession Numbers

None

Natural Product Identification

Common Name

nimbocinol

Description

Nimbocinol belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. nimbocinol is found in Azadirachta indica. nimbocinol was first documented in 2009 (PMID: 19551731). Based on a literature review a small amount of articles have been published on nimbocinol (PMID: 31872594) (PMID: 33815808) (PMID: 33176643).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052223152D          

 30 34  0  0  1  0            999 V2000
    1.8641    0.3651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5776   -0.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8616    0.7255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0458   -0.6798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2336   -0.5346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3261   -1.4557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1382   -1.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6700   -0.9702    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9503   -1.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3897   -0.1943    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9215    0.4364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7336    0.2912    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2655    0.9219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0139   -0.4847    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5458    0.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8261   -0.6299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4774   -0.1236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1602   -0.5866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9362   -0.3063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9309   -1.3791    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4373   -2.0304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2618   -2.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5421   -2.7795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8908   -3.2859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2080   -2.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1064   -1.4059    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4662   -2.1482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5745   -2.0366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7624   -1.8914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4821   -1.1154    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 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
 14 16  1  0  0  0  0
 16 17  2  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  1  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 21 25  2  0  0  0  0
 20 26  1  0  0  0  0
 16 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 30 29  1  6  0  0  0
  8 30  1  0  0  0  0
 14 30  1  0  0  0  0
M  END

     RDKit          3D

 62 66  0  0  0  0  0  0  0  0999 V2000
    4.6753    0.4445    0.6715 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9352    0.2152   -0.5912 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3377    1.2988   -1.6100 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2554   -1.0717   -1.2586 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4450   -1.3137   -1.5552 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2079   -2.0497   -1.5704 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0294   -2.0254   -0.9744 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7850   -0.9746    0.0291 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3831   -1.4673    1.2956 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4389    0.2841   -0.5118 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9072    1.5497    0.0362 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9781    1.4448    1.1893 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4158    2.7353    1.3459 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0406    0.3618    1.1157 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1182   -0.2560    2.5263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4126    0.8472    0.8139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1280    1.9074    1.1943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4783    1.8169    0.5897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2224    2.7552    0.2867 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6666    0.3328    0.4603 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7914   -0.0344   -0.3658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4726    0.6886   -1.3200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5072   -0.0778   -1.8212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4593   -1.2287   -1.1943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4797   -1.2520   -0.3388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2843   -0.0075   -0.0864 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2169    0.3776   -1.5107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0363   -1.4631    0.2125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5895   -1.8483    0.0144 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3081   -0.6687    0.0713 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2005    1.1082    1.3888 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6449    0.9600    0.3939 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0180   -0.5299    1.0893 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8115    2.2379   -1.4129 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1087    0.9192   -2.6263 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4360    1.3773   -1.5243 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3893   -2.8224   -2.3096 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2941   -2.7478   -1.2105 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8013   -0.7359    1.9775 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2545   -2.1452    1.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6835   -2.1209    1.8125 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1212    0.2818   -1.6084 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7898    2.1709    0.3718 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4110    2.2184   -0.7293 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6273    1.3361    2.1094 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4875    3.0733    2.2668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4210   -1.2968    2.5240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9277    0.3031    3.0892 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8117   -0.1141    3.0926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8455    2.7331    1.8312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7271   -0.0836    1.5034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2766    1.6967   -1.6569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2465    0.1508   -2.5743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2404   -2.0871    0.2923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6077    1.3304   -1.5824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1816    0.6566   -1.9742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8169   -0.4194   -2.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3972   -1.6700    1.2399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7008   -2.0450   -0.4566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2790   -2.6948    0.6485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5604   -2.2459   -1.0510 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1392   -0.1162   -0.9068 H   0  0  0  0  0  0  0  0  0  0  0  0
 26 27  1  6
 26 28  1  0
 28 29  1  0
 29 30  1  0
 30  8  1  0
  8  9  1  1
  8  7  1  0
  7  6  2  0
  6  4  1  0
  4  5  2  0
  4  2  1  0
  2  1  1  0
  2  3  1  0
  2 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  1
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 25  2  0
 25 24  1  0
 24 23  1  0
 23 22  2  0
 16 26  1  0
 22 21  1  0
 20 26  1  0
 14 30  1  0
 10  8  1  0
 27 55  1  0
 27 56  1  0
 27 57  1  0
 28 58  1  0
 28 59  1  0
 29 60  1  0
 29 61  1  0
 30 62  1  6
  9 39  1  0
  9 40  1  0
  9 41  1  0
  7 38  1  0
  6 37  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  3 36  1  0
 10 42  1  6
 11 43  1  0
 11 44  1  0
 12 45  1  1
 13 46  1  0
 15 47  1  0
 15 48  1  0
 15 49  1  0
 17 50  1  0
 20 51  1  1
 25 54  1  0
 23 53  1  0
 22 52  1  0
M  END


  Mrv1652309052223152D          

 30 34  0  0  1  0            999 V2000
    1.8641    0.3651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5776   -0.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8616    0.7255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0458   -0.6798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2336   -0.5346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3261   -1.4557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1382   -1.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6700   -0.9702    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9503   -1.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3897   -0.1943    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9215    0.4364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7336    0.2912    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2655    0.9219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0139   -0.4847    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5458    0.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8261   -0.6299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4774   -0.1236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1602   -0.5866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9362   -0.3063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9309   -1.3791    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4373   -2.0304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2618   -2.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5421   -2.7795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8908   -3.2859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2080   -2.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1064   -1.4059    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4662   -2.1482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5745   -2.0366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7624   -1.8914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4821   -1.1154    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 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
 14 16  1  0  0  0  0
 16 17  2  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  1  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 21 25  2  0  0  0  0
 20 26  1  0  0  0  0
 16 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 30 29  1  6  0  0  0
  8 30  1  0  0  0  0
 14 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0220053

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@]12CC[C@@H]3[C@@]4(C)C=CC(=O)C(C)(C)[C@@H]4C[C@@H](O)[C@@]3(C)C1=CC(=O)[C@H]2C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H32O4/c1-23(2)18-13-21(29)26(5)17(24(18,3)10-7-20(23)28)6-9-25(4)19(26)12-16(27)22(25)15-8-11-30-14-15/h7-8,10-12,14,17-18,21-22,29H,6,9,13H2,1-5H3/t17-,18+,21-,22-,24-,25-,26-/m1/s1

> <INCHI_KEY>
BAMHPKTZTBFUOH-WWBRISJOSA-N

> <FORMULA>
C26H32O4

> <MOLECULAR_WEIGHT>
408.538

> <EXACT_MASS>
408.23005951

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
45.563449670816205

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,7R,9R,10R,14R,15S)-14-(furan-3-yl)-9-hydroxy-2,6,6,10,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,11-diene-5,13-dione

> <JCHEM_LOGP>
4.400112533666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.395657580794243

> <JCHEM_PKA_STRONGEST_BASIC>
-0.2784742287051908

> <JCHEM_POLAR_SURFACE_AREA>
67.50999999999999

> <JCHEM_REFRACTIVITY>
116.89799999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,7R,9R,10R,14R,15S)-14-(furan-3-yl)-9-hydroxy-2,6,6,10,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,11-diene-5,13-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       3.480   0.682   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.811  -0.092   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.342   1.354   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.819  -1.269   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.303  -0.998   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.342  -2.717   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.858  -2.988   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.851  -1.811   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.374  -3.259   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.327  -0.363   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.320   0.815   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.836   0.544   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.829   1.721   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       9.359  -0.905   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.352   0.273   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.875  -1.176   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.091  -0.231   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.366  -1.095   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      14.814  -0.572   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      12.938  -2.574   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.883  -3.790   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      15.422  -3.740   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.945  -5.188   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      14.730  -6.134   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      13.455  -5.269   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.399  -2.624   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.070  -4.010   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.406  -3.802   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.890  -3.531   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.367  -2.082   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   10                                             
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   30                                             
CONECT    9    8                                                            
CONECT   10    8    2   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16   30                                             
CONECT   15   14                                                            
CONECT   16   14   17   26                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   26                                                  
CONECT   21   20   22   25                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   21                                                       
CONECT   26   20   16   27   28                                             
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29    8   14                                                  
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₂O₄

Average Mass

408.5380 Da

Monoisotopic Mass

408.23006 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@@]12CC[C@@H]3[C@@]4(C)C=CC(=O)C(C)(C)[C@@H]4C[C@@H](O)[C@@]3(C)C1=CC(=O)[C@H]2C1=COC=C1

InChI Identifier

InChI=1S/C26H32O4/c1-23(2)18-13-21(29)26(5)17(24(18,3)10-7-20(23)28)6-9-25(4)19(26)12-16(27)22(25)15-8-11-30-14-15/h7-8,10-12,14,17-18,21-22,29H,6,9,13H2,1-5H3/t17-,18+,21-,22-,24-,25-,26-/m1/s1

InChI Key

BAMHPKTZTBFUOH-WWBRISJOSA-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
Azadirachta indica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Limonoids

Alternative Parents

Substituents

Limonoid skeleton
17-furanylsteroid skeleton
3-oxo-delta-1-steroid
3-oxosteroid
Hydroxysteroid
16-oxosteroid
3-oxo-5-alpha-steroid
7-hydroxysteroid
Oxosteroid
Delta-1-steroid
Steroid
Cyclohexenone
Cyclic alcohol
Heteroaromatic compound
Furan
Ketone
Cyclic ketone
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

furans (CHEBI:67281 )
tetracyclic triterpenoid (CHEBI:67281 )
cyclic terpene ketone (CHEBI:67281 )
limonoid (CHEBI:67281 )

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

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

26346056

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13875741

PDB ID

Not Available

ChEBI ID

67281

Good Scents ID

Not Available

References

General References

Lu XF, Lin PC, Zi JC, Fan XN: [Limonoids from seeds of Azadirachta indica and their antibacterial activity]. Zhongguo Zhong Yao Za Zhi. 2019 Nov;44(22):4864-4873. doi: 10.19540/j.cnki.cjcmm.20190813.202. [PubMed:31872594 ]
Balkrishna A, Mittal R, Sharma G, Arya V: Computational insights of phytochemical-driven disruption of RNA-dependent RNA polymerase-mediated replication of coronavirus: a strategic treatment plan against coronavirus disease 2019. New Microbes New Infect. 2021 May;41:100878. doi: 10.1016/j.nmni.2021.100878. Epub 2021 Mar 31. [PubMed:33815808 ]
Gurulingappa H, Tare V, Pawar P, Tungikar V, Jorapur YR, Madhavi S, Bhat SV: Susceptibility of Aedes aegypti and Culex quinquefasciatus Larvae to gedunin-related limonoids. Chem Biodivers. 2009 Jun;6(6):897-902. doi: 10.1002/cbdv.200800105. [PubMed:19551731 ]
Balkrishna A, Mittal R, Arya V: Computational Evidences of Phytochemical Mediated Disruption of PLpro Driven Replication of SARS-CoV-2: A Therapeutic Approach against COVID-19. Curr Pharm Biotechnol. 2021;22(10):1350-1359. doi: 10.2174/1389201021999201110204116. [PubMed:33176643 ]
LOTUS database [Link]

Showing NP-Card for nimbocinol (NP0220053)

MOL for NP0220053 (nimbocinol)

3D MOL for NP0220053 (nimbocinol)

3D SDF for NP0220053 (nimbocinol)

3D-SDF for NP0220053 (nimbocinol)

PDB for NP0220053 (nimbocinol)

3D PDB for NP0220053 (nimbocinol)

SMILES for NP0220053 (nimbocinol)

INCHI for NP0220053 (nimbocinol)

Structure for NP0220053 (nimbocinol)

3D Structure for NP0220053 (nimbocinol)