NP-MRD: Showing NP-Card for [(1r,4r,10s,11s,13s,16r)-2,11,16-trihydroxy-5,5-dimethyl-14-methylidene-15-oxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-9-yl]methyl acetate (NP0226512)

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Record Information

Version

2.0

Created at

2022-09-06 05:34:47 UTC

Updated at

2022-09-06 05:34:47 UTC

NP-MRD ID

NP0226512

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(1r,4r,10s,11s,13s,16r)-2,11,16-trihydroxy-5,5-dimethyl-14-methylidene-15-oxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-9-yl]methyl acetate

Description

Flexicaulin A belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. [(1r,4r,10s,11s,13s,16r)-2,11,16-trihydroxy-5,5-dimethyl-14-methylidene-15-oxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-9-yl]methyl acetate is found in Isodon flexicaulis. [(1r,4r,10s,11s,13s,16r)-2,11,16-trihydroxy-5,5-dimethyl-14-methylidene-15-oxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-9-yl]methyl acetate was first documented in 2017 (PMID: 28337333). Based on a literature review a small amount of articles have been published on Flexicaulin A (PMID: 32883640) (PMID: 31494472) (PMID: 31003485).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062207342D          

 28 31  0  0  1  0            999 V2000
    0.0435   -0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8566   -0.1407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4794    0.4660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3435    1.2798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2893    0.0832    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5946    0.8699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0619    1.4998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4039    1.0366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9582    0.4175    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7638    0.5954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4487    1.3579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4599    1.0381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3206   -0.0133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0719   -0.7999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2663   -0.9778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7095   -0.3691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4700   -1.1586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0340   -1.7607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7946   -2.5502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3586   -3.1523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9911   -2.7376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8883   -0.5708    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6431   -1.4156    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1975   -2.0266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7976   -1.5743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2377   -0.9152    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8140   -0.4494    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3829   -1.0469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 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
  9 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 16 22  1  0  0  0  0
 22  5  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26  2  1  1  0  0  0
 26 27  1  0  0  0  0
  5 27  1  0  0  0  0
 27 28  1  6  0  0  0
M  END

     RDKit          3D

 60 63  0  0  0  0  0  0  0  0999 V2000
    4.5162   -0.2023    1.4600 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5950    0.1229    0.5960 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7312   -0.7988   -0.1282 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8405   -2.0144   -0.2932 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6179    0.0731   -0.6643 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0602   -0.6191   -1.8253 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0056   -1.5547   -2.3460 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2389   -1.3150   -1.7329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7045   -1.4087   -0.3161 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9039   -2.2122   -0.0848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5927   -3.4122    0.8436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3459   -2.9259   -1.3917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1336   -1.5853    0.4526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8891   -0.4540    1.3878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4464   -0.1039    1.5588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7445    0.0579    0.1989 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5551    0.8764   -0.6877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9368    2.1525   -0.4339 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3565    3.3692   -0.4118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1274    4.5963   -0.0443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1396    3.4545   -0.7098 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6948    0.3340    0.4783 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0559    1.4057    1.4197 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2259    0.8979    2.7578 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3050    2.1575    1.1413 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2263    1.5148    0.1616 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4602    1.2344   -1.0816 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3987    0.7010   -2.0093 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1147    0.5433    1.9542 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7074   -1.2266    1.7065 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9760    0.1036   -2.7027 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5177   -2.1973   -2.9221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0092   -0.9179   -2.4268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1298   -2.3920   -2.0719 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1293   -1.8752    0.2540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1539   -4.3042    0.5641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8698   -3.1085    1.8959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5026   -3.5272    0.8233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5620   -2.2135   -2.1850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3095   -3.4471   -1.1336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6162   -3.7197   -1.6487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6728   -2.3759    1.0714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9025   -1.3650   -0.3313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2931   -0.6396    2.4059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4943    0.4288    1.0214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3639    0.7902    2.1715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9123   -0.9242    2.0705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9759    0.9601   -1.6974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4734    0.3286   -1.0775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4075    5.3820    0.2197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7770    4.8399   -0.9007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7193    4.3433    0.8581 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9027   -0.6252    1.1486 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2486    2.1577    1.5878 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8237    0.1065    2.7096 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0590    3.1694    0.7407 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8299    2.3796    2.1089 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1301    2.1318    0.0080 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9955    2.0532   -1.5887 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0920    0.7994   -2.9290 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  1  0
 19 21  2  0
 19 18  1  0
 18 17  1  0
 16 17  1  6
 16 15  1  0
 15 14  1  0
 14 13  1  0
 13 10  1  0
 10 11  1  0
 10 12  1  0
 10  9  1  0
  9  8  1  0
  8  6  1  0
  6  7  1  0
  6  5  1  0
  5 27  1  0
 27 28  1  0
 27 26  1  0
 26 25  1  0
 25 23  1  0
 23 24  1  0
 23 22  1  0
 26  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  2  0
  9 16  1  0
 22  5  1  0
 22 16  1  0
  5  3  1  1
 20 50  1  0
 20 51  1  0
 20 52  1  0
 17 48  1  0
 17 49  1  0
 15 46  1  0
 15 47  1  0
 14 44  1  0
 14 45  1  0
 13 42  1  0
 13 43  1  0
 11 36  1  0
 11 37  1  0
 11 38  1  0
 12 39  1  0
 12 40  1  0
 12 41  1  0
  9 35  1  1
  8 33  1  0
  8 34  1  0
  6 31  1  6
  7 32  1  0
 27 59  1  6
 28 60  1  0
 26 58  1  6
 25 56  1  0
 25 57  1  0
 23 54  1  1
 24 55  1  0
 22 53  1  1
  1 29  1  0
  1 30  1  0
M  END


  Mrv1652309062207342D          

 28 31  0  0  1  0            999 V2000
    0.0435   -0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8566   -0.1407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4794    0.4660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3435    1.2798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2893    0.0832    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5946    0.8699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0619    1.4998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4039    1.0366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9582    0.4175    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7638    0.5954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4487    1.3579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4599    1.0381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3206   -0.0133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0719   -0.7999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2663   -0.9778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7095   -0.3691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4700   -1.1586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0340   -1.7607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7946   -2.5502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3586   -3.1523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9911   -2.7376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8883   -0.5708    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6431   -1.4156    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1975   -2.0266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7976   -1.5743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2377   -0.9152    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8140   -0.4494    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3829   -1.0469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 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
  9 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 16 22  1  0  0  0  0
 22  5  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26  2  1  1  0  0  0
 26 27  1  0  0  0  0
  5 27  1  0  0  0  0
 27 28  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0226512

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OCC12CCCC(C)(C)[C@H]1CC(O)[C@@]13[C@H](O)[C@@H](C[C@H](O)[C@@H]21)C(=C)C3=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H32O6/c1-11-13-8-14(24)17-21(10-28-12(2)23)7-5-6-20(3,4)15(21)9-16(25)22(17,18(11)26)19(13)27/h13-17,19,24-25,27H,1,5-10H2,2-4H3/t13-,14-,15+,16?,17-,19+,21?,22+/m0/s1

> <INCHI_KEY>
OHNVJXDBOKZLFC-VLNMMGBWSA-N

> <FORMULA>
C22H32O6

> <MOLECULAR_WEIGHT>
392.492

> <EXACT_MASS>
392.21988875

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
41.657789935079116

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(1R,4R,10S,11S,13S,16R)-2,11,16-trihydroxy-5,5-dimethyl-14-methylidene-15-oxotetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-9-yl]methyl acetate

> <JCHEM_LOGP>
0.9287102206666668

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.519257640441886

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.893055313944782

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8602277389829203

> <JCHEM_POLAR_SURFACE_AREA>
104.06

> <JCHEM_REFRACTIVITY>
101.8641

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
[(1R,4R,10S,11S,13S,16R)-2,11,16-trihydroxy-5,5-dimethyl-14-methylidene-15-oxotetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-9-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       0.081  -0.001   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.599  -0.263   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.761   0.870   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.508   2.389   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.273   0.155   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.843   1.624   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.849   2.800   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.354   1.935   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.389   0.779   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.892   1.111   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.304   2.535   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.192   1.938   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.932  -0.025   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.468  -1.493   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.964  -1.825   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.924  -0.689   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.477  -2.163   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       7.530  -3.287   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       7.083  -4.760   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.136  -5.884   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.583  -5.110   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.392  -1.066   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.934  -2.642   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.969  -3.783   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.356  -2.939   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.310  -1.708   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.386  -0.839   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.448  -1.954   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   26                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   22   27                                             
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   16                                                  
CONECT   10    9   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    9   17   22                                             
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   16    5   23                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25    2   27                                                  
CONECT   27   26    5   28                                                  
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₂O₆

Average Mass

392.4920 Da

Monoisotopic Mass

392.21989 Da

IUPAC Name

[(1R,4R,10S,11S,13S,16R)-2,11,16-trihydroxy-5,5-dimethyl-14-methylidene-15-oxotetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-9-yl]methyl acetate

Traditional Name

[(1R,4R,10S,11S,13S,16R)-2,11,16-trihydroxy-5,5-dimethyl-14-methylidene-15-oxotetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-9-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OCC12CCCC(C)(C)[C@H]1CC(O)[C@@]13[C@H](O)[C@@H](C[C@H](O)[C@@H]21)C(=C)C3=O

InChI Identifier

InChI=1S/C22H32O6/c1-11-13-8-14(24)17-21(10-28-12(2)23)7-5-6-20(3,4)15(21)9-16(25)22(17,18(11)26)19(13)27/h13-17,19,24-25,27H,1,5-10H2,2-4H3/t13-,14-,15+,16?,17-,19+,21?,22+/m0/s1

InChI Key

OHNVJXDBOKZLFC-VLNMMGBWSA-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
Isodon flexicaulis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Kaurane diterpenoids

Alternative Parents

Substituents

Kaurane diterpenoid
Cyclic alcohol
Secondary alcohol
Ketone
Carboxylic acid ester
Polyol
Monocarboxylic acid or derivatives
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	0.93	ChemAxon
pKa (Strongest Acidic)	13.89	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	101.86 m³·mol⁻¹	ChemAxon
Polarizability	41.66 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

325715

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

366919

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Huo JF, Hu TX, Dong YL, Zhao JZ, Liu XJ, Li LL, Zhang XY, Li YF, Liu HM, Ke Y, Wang C: Synthesis and in vitro and in vivo biological evaluation of novel derivatives of flexicaulin A as antiproliferative agents. Eur J Med Chem. 2020 Dec 15;208:112789. doi: 10.1016/j.ejmech.2020.112789. Epub 2020 Aug 31. [PubMed:32883640 ]
Ke Y, Hu TX, Huo JF, Yan JK, Wang JY, Yang RH, Xie H, Liu Y, Wang N, Zheng ZJ, Sun YX, Wang C, Du J, Liu HM: Synthesis and in vitro biological evaluation of novel derivatives of Flexicaulin A condensation with amino acid trifluoroacetate. Eur J Med Chem. 2019 Nov 15;182:111645. doi: 10.1016/j.ejmech.2019.111645. Epub 2019 Sep 3. [PubMed:31494472 ]
Xia Y, Lam CS, Li W, Sarwar MS, Liu K, Lee KM, Zhang HJ, Tsang SW: Flexicaulin A, An ent-Kaurane Diterpenoid, Activates p21 and Inhibits the Proliferation of Colorectal Carcinoma Cells through a Non-Apoptotic Mechanism. Int J Mol Sci. 2019 Apr 18;20(8):1917. doi: 10.3390/ijms20081917. [PubMed:31003485 ]
Guo L, Tsang SW, Zhang TX, Liu KL, Guan YF, Wang B, Sun HD, Zhang HJ, Wong MS: Efficient Semisynthesis of (-)-Pseudoirroratin A from (-)-Flexicaulin A and Assessment of Their Antitumor Activities. ACS Med Chem Lett. 2017 Feb 28;8(3):372-376. doi: 10.1021/acsmedchemlett.7b00033. eCollection 2017 Mar 9. [PubMed:28337333 ]
LOTUS database [Link]

Showing NP-Card for [(1r,4r,10s,11s,13s,16r)-2,11,16-trihydroxy-5,5-dimethyl-14-methylidene-15-oxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-9-yl]methyl acetate (NP0226512)

MOL for NP0226512 ([(1r,4r,10s,11s,13s,16r)-2,11,16-trihydroxy-5,5-dimethyl-14-methylidene-15-oxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-9-yl]methyl acetate)

3D MOL for NP0226512 ([(1r,4r,10s,11s,13s,16r)-2,11,16-trihydroxy-5,5-dimethyl-14-methylidene-15-oxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-9-yl]methyl acetate)

3D SDF for NP0226512 ([(1r,4r,10s,11s,13s,16r)-2,11,16-trihydroxy-5,5-dimethyl-14-methylidene-15-oxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-9-yl]methyl acetate)

3D-SDF for NP0226512 ([(1r,4r,10s,11s,13s,16r)-2,11,16-trihydroxy-5,5-dimethyl-14-methylidene-15-oxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-9-yl]methyl acetate)

PDB for NP0226512 ([(1r,4r,10s,11s,13s,16r)-2,11,16-trihydroxy-5,5-dimethyl-14-methylidene-15-oxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-9-yl]methyl acetate)

3D PDB for NP0226512 ([(1r,4r,10s,11s,13s,16r)-2,11,16-trihydroxy-5,5-dimethyl-14-methylidene-15-oxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-9-yl]methyl acetate)

SMILES for NP0226512 ([(1r,4r,10s,11s,13s,16r)-2,11,16-trihydroxy-5,5-dimethyl-14-methylidene-15-oxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-9-yl]methyl acetate)

INCHI for NP0226512 ([(1r,4r,10s,11s,13s,16r)-2,11,16-trihydroxy-5,5-dimethyl-14-methylidene-15-oxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-9-yl]methyl acetate)

Structure for NP0226512 ([(1r,4r,10s,11s,13s,16r)-2,11,16-trihydroxy-5,5-dimethyl-14-methylidene-15-oxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-9-yl]methyl acetate)

3D Structure for NP0226512 ([(1r,4r,10s,11s,13s,16r)-2,11,16-trihydroxy-5,5-dimethyl-14-methylidene-15-oxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-9-yl]methyl acetate)