NP-MRD: Showing NP-Card for 3-{[(1s,2s,7s,9s,10s,12r,13s)-9-hydroxy-2,6,6,13-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0²,⁷]hexadecan-12-yl]oxy}-3-oxopropanoic acid (NP0188748)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-04 05:07:59 UTC

Updated at

2022-09-04 05:07:59 UTC

NP-MRD ID

NP0188748

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-{[(1s,2s,7s,9s,10s,12r,13s)-9-hydroxy-2,6,6,13-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0²,⁷]hexadecan-12-yl]oxy}-3-oxopropanoic acid

Description

Thyrsiflorin B belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. 3-{[(1s,2s,7s,9s,10s,12r,13s)-9-hydroxy-2,6,6,13-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0²,⁷]hexadecan-12-yl]oxy}-3-oxopropanoic acid is found in Calceolaria thyrsiflora. 3-{[(1s,2s,7s,9s,10s,12r,13s)-9-hydroxy-2,6,6,13-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0²,⁷]hexadecan-12-yl]oxy}-3-oxopropanoic acid was first documented in 2005 (PMID: 16106476). Based on a literature review very few articles have been published on Thyrsiflorin B (PMID: 35965943).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042207082D          

 28 31  0  0  1  0            999 V2000
    4.6111   -0.6744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8471   -0.3631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6732   -1.1696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2863    0.3352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9011    1.0648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0767    1.0960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6375    0.3976    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2801    1.1412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0227   -0.3319    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5824   -1.0401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7547   -1.0134    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3188   -1.7139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3624   -0.2774    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4958   -0.3451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0623    0.3922    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7626    0.3815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1844    1.0905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7812    1.8103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0093    1.0798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4311    1.7888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2560    1.7781    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0279    2.5086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4824    1.1512    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1809    1.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0837    1.7738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8688    1.3897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7900    0.4940    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1261    0.7837    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 15 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 13 27  1  0  0  0  0
  7 27  1  0  0  0  0
 27 28  1  6  0  0  0
 23 28  1  0  0  0  0
M  END

     RDKit          3D

 64 67  0  0  0  0  0  0  0  0999 V2000
   -4.5570    1.4458   -1.1800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9520    0.2336   -0.4352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2737   -0.9587   -1.2838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5878    0.2150    0.9223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7215    0.7674    1.9884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3072    0.3407    2.0443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7453   -0.2226    0.7188 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0377   -1.6989    0.7817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5005    0.5378   -0.3067 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8584    0.5799   -1.6836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5735    1.3868   -1.4161 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0681    1.7094   -2.5847 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2739    0.3824   -0.6716 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6913    0.8396   -0.5954 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5262   -0.3858   -0.2350 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8105    0.1275    0.1244 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9775   -0.2446   -0.5160 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8960   -1.0681   -1.4507 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2970    0.2997   -0.1277 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3378   -0.2949   -0.9959 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7317   -1.4668   -0.7671 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8530    0.4497   -2.0372 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9340   -0.9428    1.0319 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7984   -2.0517    1.5661 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7641    0.1918    1.9763 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3325    0.6320    1.8486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2591   -0.0878    0.6307 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4899   -1.4200    0.8278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9319    2.3334   -1.0740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5514    1.7020   -0.7385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7149    1.2331   -2.2351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8367   -0.6973   -2.2314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9756   -1.6493   -0.7553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3650   -1.4874   -1.6735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5305    0.8512    0.9287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0361   -0.7894    1.1899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8616    1.8927    1.9823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2042    0.4795    2.9727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7201    1.3011    2.1789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1356   -0.3783    2.8579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4538   -2.2971    0.0409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0684   -1.9948    0.6440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7976   -2.0127    1.8439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4786    1.6272    0.0237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5388    1.1076   -2.3512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6138   -0.4487   -1.9708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7812    2.2258   -0.7454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1197    2.6803   -2.7712 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2875   -0.5033   -1.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9697    1.1750   -1.6395 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8677    1.7005    0.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5616   -1.0927   -1.0574 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2483    1.3986   -0.2911 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5436    0.0925    0.9375 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4559    0.3640   -2.9661 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0147   -2.7530    0.7600 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7309   -1.5651    1.9641 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2913   -2.5033    2.4374 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4990    1.0222    1.8435 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0161   -0.2062    3.0046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1779    0.1438    2.7327 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2388    1.7068    1.8064 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5373   -2.0043   -0.1111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2225   -1.9509    1.7236 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 24  1  1
 23 25  1  0
 25 26  1  0
 27 26  1  1
 27 28  1  0
 27 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 22  1  0
 20 21  2  0
 13 11  1  0
 11 12  1  0
 11 10  1  0
 10  9  1  0
  9  2  1  0
  2  1  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  6
 28 23  1  0
  7  9  1  0
 15 23  1  0
  7 27  1  0
 24 56  1  0
 24 57  1  0
 24 58  1  0
 25 59  1  0
 25 60  1  0
 26 61  1  0
 26 62  1  0
 28 63  1  0
 28 64  1  0
 13 49  1  6
 14 50  1  0
 14 51  1  0
 15 52  1  6
 19 53  1  0
 19 54  1  0
 22 55  1  0
 11 47  1  1
 12 48  1  0
 10 45  1  0
 10 46  1  0
  9 44  1  1
  1 29  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  0
  5 38  1  0
  6 39  1  0
  6 40  1  0
  8 41  1  0
  8 42  1  0
  8 43  1  0
M  END


  Mrv1652309042207082D          

 28 31  0  0  1  0            999 V2000
    4.6111   -0.6744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8471   -0.3631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6732   -1.1696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2863    0.3352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9011    1.0648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0767    1.0960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6375    0.3976    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2801    1.1412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0227   -0.3319    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5824   -1.0401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7547   -1.0134    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3188   -1.7139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3624   -0.2774    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4958   -0.3451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0623    0.3922    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7626    0.3815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1844    1.0905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7812    1.8103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0093    1.0798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4311    1.7888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2560    1.7781    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0279    2.5086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4824    1.1512    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1809    1.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0837    1.7738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8688    1.3897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7900    0.4940    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1261    0.7837    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 15 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 13 27  1  0  0  0  0
  7 27  1  0  0  0  0
 27 28  1  6  0  0  0
 23 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0188748

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]12CC[C@]3(C1)[C@H](C[C@H]2OC(=O)CC(O)=O)[C@@H](O)C[C@H]1C(C)(C)CCC[C@]31C

> <INCHI_IDENTIFIER>
InChI=1S/C23H36O5/c1-20(2)6-5-7-22(4)16(20)11-15(24)14-10-17(28-19(27)12-18(25)26)21(3)8-9-23(14,22)13-21/h14-17,24H,5-13H2,1-4H3,(H,25,26)/t14-,15+,16+,17-,21+,22+,23+/m1/s1

> <INCHI_KEY>
DJKCFSCOAVLGIR-MEJZBLFSSA-N

> <FORMULA>
C23H36O5

> <MOLECULAR_WEIGHT>
392.536

> <EXACT_MASS>
392.256274259

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
44.338306756068505

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-{[(1S,2S,7S,9S,10S,12R,13S)-9-hydroxy-2,6,6,13-tetramethyltetracyclo[11.2.1.0^{1,10}.0^{2,7}]hexadecan-12-yl]oxy}-3-oxopropanoic acid

> <JCHEM_LOGP>
3.770589992333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.917055684784376

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.988201018388222

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8350798454121566

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
104.399

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3-{[(1S,2S,7S,9S,10S,12R,13S)-9-hydroxy-2,6,6,13-tetramethyltetracyclo[11.2.1.0^{1,10}.0^{2,7}]hexadecan-12-yl]oxy}-3-oxopropanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       8.607  -1.259   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.181  -0.678   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.857  -2.183   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.001   0.626   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.282   1.988   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.743   2.046   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.923   0.742   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.256   2.130   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.642  -0.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.820  -1.942   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.275  -1.892   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.462  -3.199   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.543  -0.518   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.926  -0.644   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.116   0.732   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.424   0.712   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.211   2.036   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.458   3.379   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -3.751   2.016   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.538   3.339   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -6.078   3.319   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -3.785   4.683   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.901   2.149   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.338   3.065   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.023   3.311   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.488   2.594   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.341   0.922   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.102   1.463   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4    9                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   27                                             
CONECT    8    7                                                            
CONECT    9    7    2   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   27                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   23                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   15   24   25   28                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   13    7   28                                             
CONECT   28   27   23                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₃₆O₅

Average Mass

392.5360 Da

Monoisotopic Mass

392.25627 Da

IUPAC Name

3-{[(1S,2S,7S,9S,10S,12R,13S)-9-hydroxy-2,6,6,13-tetramethyltetracyclo[11.2.1.0^{1,10}.0^{2,7}]hexadecan-12-yl]oxy}-3-oxopropanoic acid

Traditional Name

3-{[(1S,2S,7S,9S,10S,12R,13S)-9-hydroxy-2,6,6,13-tetramethyltetracyclo[11.2.1.0^{1,10}.0^{2,7}]hexadecan-12-yl]oxy}-3-oxopropanoic acid

CAS Registry Number

Not Available

SMILES

C[C@]12CC[C@]3(C1)[C@H](C[C@H]2OC(=O)CC(O)=O)[C@@H](O)C[C@H]1C(C)(C)CCC[C@]31C

InChI Identifier

InChI=1S/C23H36O5/c1-20(2)6-5-7-22(4)16(20)11-15(24)14-10-17(28-19(27)12-18(25)26)21(3)8-9-23(14,22)13-21/h14-17,24H,5-13H2,1-4H3,(H,25,26)/t14-,15+,16+,17-,21+,22+,23+/m1/s1

InChI Key

DJKCFSCOAVLGIR-MEJZBLFSSA-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
Calceolaria thyrsiflora	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
1,3-dicarbonyl compound
Dicarboxylic acid or derivatives
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	3.77	ChemAxon
pKa (Strongest Acidic)	3.99	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	104.4 m³·mol⁻¹	ChemAxon
Polarizability	44.34 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

101600698

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Sang YL, Dai L, Wang P, Chen LJ, Jiao ML, Liu JY, Zhang NZ, Fan GW, Hao YJ, Wang XL: Investigation of insecticidal activity of two Rhododendron species on stored-product insects. J Plant Dis Prot (2006). 2022 Aug 9:1-12. doi: 10.1007/s41348-022-00654-z. [PubMed:35965943 ]
Gonzalez MA, Zaragoza RJ: 1H and 13C NMR signal assignment of synthetic (-)-methyl thyrsiflorin B acetate, (-)-thyrsiflorin C and several scopadulane derivatives. Magn Reson Chem. 2005 Oct;43(10):877-80. doi: 10.1002/mrc.1629. [PubMed:16106476 ]
LOTUS database [Link]

Showing NP-Card for 3-{[(1s,2s,7s,9s,10s,12r,13s)-9-hydroxy-2,6,6,13-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0²,⁷]hexadecan-12-yl]oxy}-3-oxopropanoic acid (NP0188748)

MOL for NP0188748 (3-{[(1s,2s,7s,9s,10s,12r,13s)-9-hydroxy-2,6,6,13-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0²,⁷]hexadecan-12-yl]oxy}-3-oxopropanoic acid)

3D MOL for NP0188748 (3-{[(1s,2s,7s,9s,10s,12r,13s)-9-hydroxy-2,6,6,13-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0²,⁷]hexadecan-12-yl]oxy}-3-oxopropanoic acid)

3D SDF for NP0188748 (3-{[(1s,2s,7s,9s,10s,12r,13s)-9-hydroxy-2,6,6,13-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0²,⁷]hexadecan-12-yl]oxy}-3-oxopropanoic acid)

3D-SDF for NP0188748 (3-{[(1s,2s,7s,9s,10s,12r,13s)-9-hydroxy-2,6,6,13-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0²,⁷]hexadecan-12-yl]oxy}-3-oxopropanoic acid)

PDB for NP0188748 (3-{[(1s,2s,7s,9s,10s,12r,13s)-9-hydroxy-2,6,6,13-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0²,⁷]hexadecan-12-yl]oxy}-3-oxopropanoic acid)

3D PDB for NP0188748 (3-{[(1s,2s,7s,9s,10s,12r,13s)-9-hydroxy-2,6,6,13-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0²,⁷]hexadecan-12-yl]oxy}-3-oxopropanoic acid)

SMILES for NP0188748 (3-{[(1s,2s,7s,9s,10s,12r,13s)-9-hydroxy-2,6,6,13-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0²,⁷]hexadecan-12-yl]oxy}-3-oxopropanoic acid)

INCHI for NP0188748 (3-{[(1s,2s,7s,9s,10s,12r,13s)-9-hydroxy-2,6,6,13-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0²,⁷]hexadecan-12-yl]oxy}-3-oxopropanoic acid)

Structure for NP0188748 (3-{[(1s,2s,7s,9s,10s,12r,13s)-9-hydroxy-2,6,6,13-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0²,⁷]hexadecan-12-yl]oxy}-3-oxopropanoic acid)

3D Structure for NP0188748 (3-{[(1s,2s,7s,9s,10s,12r,13s)-9-hydroxy-2,6,6,13-tetramethyltetracyclo[11.2.1.0¹,¹⁰.0²,⁷]hexadecan-12-yl]oxy}-3-oxopropanoic acid)