NP-MRD: Showing NP-Card for lasiodonin acetonide (NP0218799)

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Record Information

Version

2.0

Created at

2022-09-05 19:34:59 UTC

Updated at

2022-09-05 19:34:59 UTC

NP-MRD ID

NP0218799

Secondary Accession Numbers

None

Natural Product Identification

Common Name

lasiodonin acetonide

Description

Lasiodonin acetonide 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. lasiodonin acetonide is found in Isodon rubescens. Based on a literature review a small amount of articles have been published on Lasiodonin acetonide.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052221352D          

 29 34  0  0  1  0            999 V2000
    8.3361    0.1688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5536    0.4301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8629   -0.0733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0110   -0.8849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0021    0.1639    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.6119    0.7684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3054    1.2427    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8018    1.9283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9584    1.7597    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6073    2.5344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7805    2.6374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9671    3.4411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0006    2.9064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4273    1.8796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4457    1.0235    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5975    1.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9154    0.6595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3646   -0.0494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5966   -0.3506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5145   -0.8606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2200   -0.0566    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4607   -0.8566    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1380   -1.6158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2091   -0.4720    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7602    0.2202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6289   -1.1863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7111   -0.3508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0179    0.3237    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6321    0.9426    0.0000 C   0  0  1  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
  3  5  1  0  0  0  0
  5  6  1  6  0  0  0
  7  6  1  1  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 21 18  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
  5 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 28 27  1  6  0  0  0
 15 28  1  0  0  0  0
 21 28  1  0  0  0  0
 28 29  1  0  0  0  0
  9 29  1  0  0  0  0
 29  5  1  6  0  0  0
M  END

     RDKit          2D

 61 66  0  0  0  0  0  0  0  0999 V2000
   -6.5654    0.3560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0737    0.5128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3237    1.8119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2472    2.9938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8564    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1555    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1555   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8564   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5574   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3846   -1.6852    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0777   -1.3515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5401   -1.6852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0777   -2.8515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7286    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0777    1.3515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0980    2.4510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6559    3.8844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1935    4.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0666    5.0320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7761    5.6004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8268    3.1186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2892    3.4524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7065    4.8346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3094    2.3528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7718    2.6866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8673    0.9194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4049    0.5857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3846    1.6852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5574    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4471    1.5696    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1755   -1.0143    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2703    1.7536    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6518    0.8547    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4545   -1.5000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8206   -2.6491    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0395   -2.7580    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4863   -2.2483    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0025   -2.0190    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3871   -3.1774    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8739   -0.2228    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0777   -4.3515    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5666   -3.0343    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4223   -2.8515    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5227    0.9488    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4328    3.1353    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1427    1.3747    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9127    5.3622    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1442    4.0709    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2180    5.9933    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4124    6.3818    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1611    4.0063    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3588    6.9826    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5247    6.3472    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2191    5.1906    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2689    4.5520    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5492    4.2662    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7512    5.9110    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2140    4.1199    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6358   -0.8965    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1449   -0.2282    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6695    2.2458    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 18  1  0
 18 20  1  0
 18 17  1  0
 17 16  1  0
 16 15  1  0
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 14 11  1  0
 11 12  1  0
 11 13  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5 29  1  0
 29 28  1  0
 28 27  1  6
 27 26  1  0
 26 24  1  0
 24 25  1  1
 24 22  1  0
 22 23  1  0
 22 21  1  0
  5  3  1  1
  3  4  2  0
  3  2  1  0
  2  1  2  3
 21 18  1  0
 28 15  1  0
 21 28  1  0
 29  9  1  0
  2  7  1  0
 24  5  1  0
 19 49  1  0
 19 50  1  0
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 20 53  1  0
 20 54  1  0
 17 47  1  0
 17 48  1  0
 16 45  1  0
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 12 38  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  0
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 13 43  1  0
  9 37  1  6
  8 35  1  0
  8 36  1  0
  7 34  1  1
  6 32  1  0
  6 33  1  0
 29 61  1  1
 27 59  1  0
 27 60  1  0
 25 58  1  0
 22 56  1  6
 23 57  1  0
 21 55  1  1
  1 30  1  0
  1 31  1  0
M  END


  Mrv1652309052221352D          

 29 34  0  0  1  0            999 V2000
    8.3361    0.1688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5536    0.4301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8629   -0.0733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0110   -0.8849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0021    0.1639    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.6119    0.7684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3054    1.2427    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8018    1.9283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9584    1.7597    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6073    2.5344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7805    2.6374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9671    3.4411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0006    2.9064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4273    1.8796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4457    1.0235    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5975    1.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9154    0.6595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3646   -0.0494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5966   -0.3506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5145   -0.8606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2200   -0.0566    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4607   -0.8566    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1380   -1.6158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2091   -0.4720    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7602    0.2202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6289   -1.1863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7111   -0.3508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0179    0.3237    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6321    0.9426    0.0000 C   0  0  1  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
  3  5  1  0  0  0  0
  5  6  1  6  0  0  0
  7  6  1  1  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 21 18  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
  5 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 28 27  1  6  0  0  0
 15 28  1  0  0  0  0
 21 28  1  0  0  0  0
 28 29  1  0  0  0  0
  9 29  1  0  0  0  0
 29  5  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0218799

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CC[C@@H]2OC(C)(C)O[C@H]3C[C@H]4C[C@]5([C@@H]3[C@]22CO[C@]5(O)[C@@H](O)[C@H]12)C(=O)C4=C

> <INCHI_IDENTIFIER>
InChI=1S/C23H32O6/c1-11-12-8-13-15-21-10-27-23(26,22(15,9-12)17(11)24)18(25)16(21)19(2,3)7-6-14(21)29-20(4,5)28-13/h12-16,18,25-26H,1,6-10H2,2-5H3/t12-,13-,14-,15-,16+,18-,21-,22-,23+/m0/s1

> <INCHI_KEY>
FTUVGFINORCONN-AWHSDHHNSA-N

> <FORMULA>
C23H32O6

> <MOLECULAR_WEIGHT>
404.503

> <EXACT_MASS>
404.21988875

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
29.05593451989781

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,3R,6S,7S,8R,12S,16S,18R)-6,7-dihydroxy-9,9,14,14-tetramethyl-19-methylidene-5,13,15-trioxahexacyclo[16.2.1.0^{1,6}.0^{2,16}.0^{3,8}.0^{3,12}]henicosan-20-one

> <JCHEM_LOGP>
2.087125349666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.79591733803392

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.588733263335245

> <JCHEM_PKA_STRONGEST_BASIC>
-3.683082448691806

> <JCHEM_POLAR_SURFACE_AREA>
85.22000000000001

> <JCHEM_REFRACTIVITY>
104.23830000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,3R,6S,7S,8R,12S,16S,18R)-6,7-dihydroxy-9,9,14,14-tetramethyl-19-methylidene-5,13,15-trioxahexacyclo[16.2.1.0^{1,6}.0^{2,16}.0^{3,8}.0^{3,12}]henicosan-20-one

> <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      15.561   0.315   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.100   0.803   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.811  -0.137   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      13.087  -1.652   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      11.204   0.306   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.342   1.434   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.637   2.320   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.697   3.599   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.122   3.285   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      10.467   4.731   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       8.924   4.923   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.272   6.423   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.468   5.425   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.264   3.509   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.299   1.911   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.715   2.123   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.442   1.231   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.281  -0.092   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.847  -0.654   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.560  -1.607   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.877  -0.106   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.327  -1.599   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       7.724  -3.016   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       9.724  -0.881   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       8.886   0.411   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      10.507  -2.214   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      10.661  -0.655   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.367   0.604   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.513   1.760   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   24   29                                             
CONECT    6    5    7                                                       
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   29                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11   15                                                       
CONECT   15   14   16   28                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18   22   28                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22    5   25   26                                             
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   15   21   29                                             
CONECT   29   28    9    5                                                  
MASTER        0    0    0    0    0    0    0    0   29    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₃₂O₆

Average Mass

404.5030 Da

Monoisotopic Mass

404.21989 Da

IUPAC Name

(1S,2S,3R,6S,7S,8R,12S,16S,18R)-6,7-dihydroxy-9,9,14,14-tetramethyl-19-methylidene-5,13,15-trioxahexacyclo[16.2.1.0^{1,6}.0^{2,16}.0^{3,8}.0^{3,12}]henicosan-20-one

Traditional Name

(1S,2S,3R,6S,7S,8R,12S,16S,18R)-6,7-dihydroxy-9,9,14,14-tetramethyl-19-methylidene-5,13,15-trioxahexacyclo[16.2.1.0^{1,6}.0^{2,16}.0^{3,8}.0^{3,12}]henicosan-20-one

CAS Registry Number

Not Available

SMILES

CC1(C)CC[C@@H]2OC(C)(C)O[C@H]3C[C@H]4C[C@]5([C@@H]3[C@]22CO[C@]5(O)[C@@H](O)[C@H]12)C(=O)C4=C

InChI Identifier

InChI=1S/C23H32O6/c1-11-12-8-13-15-21-10-27-23(26,22(15,9-12)17(11)24)18(25)16(21)19(2,3)7-6-14(21)29-20(4,5)28-13/h12-16,18,25-26H,1,6-10H2,2-5H3/t12-,13-,14-,15-,16+,18-,21-,22-,23+/m0/s1

InChI Key

FTUVGFINORCONN-AWHSDHHNSA-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 rubescens	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
1,3-dioxepane
Ketal
Dioxepane
Oxane
Cyclic alcohol
Secondary alcohol
Ketone
Hemiacetal
Acetal
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Alcohol
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

oxacycle (CHEBI:67678 )

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	2.09	ChemAxon
pKa (Strongest Acidic)	10.59	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.22 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	104.24 m³·mol⁻¹	ChemAxon
Polarizability	29.06 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

35518078

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

70697945

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for lasiodonin acetonide (NP0218799)

MOL for NP0218799 (lasiodonin acetonide)

3D MOL for NP0218799 (lasiodonin acetonide)

3D SDF for NP0218799 (lasiodonin acetonide)

3D-SDF for NP0218799 (lasiodonin acetonide)

PDB for NP0218799 (lasiodonin acetonide)

3D PDB for NP0218799 (lasiodonin acetonide)

SMILES for NP0218799 (lasiodonin acetonide)

INCHI for NP0218799 (lasiodonin acetonide)

Structure for NP0218799 (lasiodonin acetonide)

3D Structure for NP0218799 (lasiodonin acetonide)