NP-MRD: Showing NP-Card for (1r,2s,4r,5r,10r,11s,17s)-11-hydroxy-5-[(2r)-2-hydroxy-1-methanesulfinylpropan-2-yl]-10,14-dimethyl-3,6,16-trioxapentacyclo[8.6.1.0²,⁴.0⁴,⁹.0¹⁴,¹⁷]heptadec-8-ene-7,15-dione (NP0294747)

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Record Information

Version

2.0

Created at

2022-09-10 03:26:11 UTC

Updated at

2022-09-10 03:26:11 UTC

NP-MRD ID

NP0294747

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2s,4r,5r,10r,11s,17s)-11-hydroxy-5-[(2r)-2-hydroxy-1-methanesulfinylpropan-2-yl]-10,14-dimethyl-3,6,16-trioxapentacyclo[8.6.1.0²,⁴.0⁴,⁹.0¹⁴,¹⁷]heptadec-8-ene-7,15-dione

Description

Makilactone Q belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. (1r,2s,4r,5r,10r,11s,17s)-11-hydroxy-5-[(2r)-2-hydroxy-1-methanesulfinylpropan-2-yl]-10,14-dimethyl-3,6,16-trioxapentacyclo[8.6.1.0²,⁴.0⁴,⁹.0¹⁴,¹⁷]heptadec-8-ene-7,15-dione is found in Podocarpus macrophyllus. Based on a literature review very few articles have been published on Makilactone Q.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102205262D          

 29 33  0  0  1  0            999 V2000
    0.6711   -4.5289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6808   -3.7040    0.0000 S   0  3  0  0  0  0  0  0  0  0  0  0
   -0.0288   -3.2831    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.4000   -3.2998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4097   -2.4749    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2346   -2.4845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5847   -2.4652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4193   -1.6499    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7097   -1.2291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7193   -0.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0097    0.0166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4386   -0.0001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1482   -0.4209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8674   -0.0168    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1578    0.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8771    0.8082    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1675    1.2290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5963    1.2123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3059    0.7915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2963   -0.0334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0881    0.1981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8417   -0.8649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6663   -0.8894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3490   -1.5266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5674   -1.2625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5770   -0.4376    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8481   -1.6666    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1289   -2.0708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1385   -1.2458    0.0000 C   0  0  1  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  1  0  0  0
  5  7  1  1  0  0  0
  8  5  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 25 24  1  1  0  0  0
 26 25  1  1  0  0  0
 20 26  1  0  0  0  0
 14 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  6  0  0  0
 29 28  1  6  0  0  0
 13 29  1  0  0  0  0
 27 29  1  0  0  0  0
  8 29  1  0  0  0  0
M  CHG  2   2   1   3  -1
M  END

     RDKit          3D

 55 59  0  0  0  0  0  0  0  0999 V2000
    5.2464   -0.3033    1.4851 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4405    0.0133   -0.2234 S   0  0  0  0  0  3  0  0  0  0  0  0
    5.7108    1.6095   -0.5721 O   0  0  0  0  0  1  0  0  0  0  0  0
    4.2395   -0.7344   -1.2611 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8672   -0.2217   -0.8790 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9338    1.2800   -1.0729 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6939   -0.4636    0.4775 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7877   -0.8549   -1.7011 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8494   -2.2704   -1.4459 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2623   -2.8167   -0.3336 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6731   -3.9128    0.1223 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1636   -2.1018    0.2976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2257   -0.9631   -0.2227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3412   -0.1543    0.4030 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6281    1.0160    1.0435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1092   -0.9198    1.4160 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3313   -1.0036    2.5986 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4167   -0.3581    1.7702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9073    0.8413    1.0559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4559    1.0158   -0.3363 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5537    0.6581   -1.3164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9613    2.4210   -0.5758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6405    3.4487   -0.3236 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6612    2.3702   -1.1081 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5583    1.1364   -1.7270 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2371    0.2227   -0.7179 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2034    0.6555   -2.0858 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4256   -0.7310   -2.6425 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3965   -0.3787   -1.4194 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3753    0.1819    1.9217 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1319   -1.4155    1.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1911   -0.0768    2.0525 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2839   -1.8435   -1.2494 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3829   -0.4429   -2.3348 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6023    1.5321   -1.9212 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9354    1.7403   -1.1410 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4117    1.6972   -0.1610 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9276   -1.3799    0.7411 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0762   -0.7490   -2.7656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3312   -2.4933    1.1824 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0993    1.4906    0.3851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3168    1.7318    1.5368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0288    0.5716    1.8941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2474   -1.9600    0.9966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7821   -1.7250    3.1366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4511   -0.0965    2.8724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1927   -1.1816    1.7096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7095    1.8027    1.6169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0387    0.7944    1.0469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4222    0.1940   -0.7767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2292   -0.1043   -2.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8813    1.5372   -1.9095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1863    1.1649   -2.6540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5078   -0.6975   -1.2751 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2992    1.2266   -2.8817 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  1
  2  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  1
  5  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 29  1  0
 29 28  1  6
 28 27  1  0
 27 25  1  0
 25 24  1  0
 24 22  1  0
 22 23  2  0
 22 20  1  0
 20 21  1  6
 20 19  1  0
 19 18  1  0
 18 16  1  0
 16 17  1  0
 16 14  1  0
 14 15  1  1
 14 26  1  0
 29  8  1  0
 27 29  1  0
 26 25  1  0
 14 13  1  0
 26 20  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  4 33  1  0
  4 34  1  0
  6 35  1  0
  6 36  1  0
  6 37  1  0
  7 38  1  0
  8 39  1  6
 12 40  1  0
 27 55  1  6
 25 53  1  6
 21 50  1  0
 21 51  1  0
 21 52  1  0
 19 48  1  0
 19 49  1  0
 18 46  1  0
 18 47  1  0
 16 44  1  6
 17 45  1  0
 15 41  1  0
 15 42  1  0
 15 43  1  0
 26 54  1  6
M  CHG  2   2   1   3  -1
M  END


  Mrv1652309102205262D          

 29 33  0  0  1  0            999 V2000
    0.6711   -4.5289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6808   -3.7040    0.0000 S   0  3  0  0  0  0  0  0  0  0  0  0
   -0.0288   -3.2831    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.4000   -3.2998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4097   -2.4749    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2346   -2.4845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5847   -2.4652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4193   -1.6499    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7097   -1.2291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7193   -0.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0097    0.0166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4386   -0.0001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1482   -0.4209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8674   -0.0168    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1578    0.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8771    0.8082    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1675    1.2290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5963    1.2123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3059    0.7915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2963   -0.0334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0881    0.1981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8417   -0.8649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6663   -0.8894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3490   -1.5266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5674   -1.2625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5770   -0.4376    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8481   -1.6666    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1289   -2.0708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1385   -1.2458    0.0000 C   0  0  1  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  1  0  0  0
  5  7  1  1  0  0  0
  8  5  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 25 24  1  1  0  0  0
 26 25  1  1  0  0  0
 20 26  1  0  0  0  0
 14 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  6  0  0  0
 29 28  1  6  0  0  0
 13 29  1  0  0  0  0
 27 29  1  0  0  0  0
  8 29  1  0  0  0  0
M  CHG  2   2   1   3  -1
M  END
> <DATABASE_ID>
NP0294747

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[S+]([O-])C[C@](C)(O)[C@H]1OC(=O)C=C2[C@]11O[C@H]1[C@@H]1OC(=O)C3(C)CC[C@H](O)[C@]2(C)[C@H]13

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O8S/c1-17-6-5-10(21)19(3)9-7-11(22)26-15(18(2,24)8-29(4)25)20(9)14(28-20)12(13(17)19)27-16(17)23/h7,10,12-15,21,24H,5-6,8H2,1-4H3/t10-,12+,13+,14-,15+,17?,18-,19+,20+,29?/m0/s1

> <INCHI_KEY>
SHHRLBQDNFCBIA-ZUDGZSMOSA-N

> <FORMULA>
C20H26O8S

> <MOLECULAR_WEIGHT>
426.48

> <EXACT_MASS>
426.134838971

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
42.01739473379769

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,4R,5R,10R,11S,17S)-11-hydroxy-5-[(2R)-2-hydroxy-1-methanesulfinylpropan-2-yl]-10,14-dimethyl-3,6,16-trioxapentacyclo[8.6.1.0^{2,4}.0^{4,9}.0^{14,17}]heptadec-8-ene-7,15-dione

> <JCHEM_LOGP>
-1.1818431313333324

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.653136338507867

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.396691784443615

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9620455981522875

> <JCHEM_POLAR_SURFACE_AREA>
122.66000000000001

> <JCHEM_REFRACTIVITY>
101.435

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,4R,5R,10R,11S,17S)-11-hydroxy-5-[(2R)-2-hydroxy-1-methanesulfinylpropan-2-yl]-10,14-dimethyl-3,6,16-trioxapentacyclo[8.6.1.0^{2,4}.0^{4,9}.0^{14,17}]heptadec-8-ene-7,15-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       1.253  -8.454   0.000  0.00  0.00           C+0
HETATM    2  S   UNK     0       1.271  -6.914   0.000  0.00  0.00           S+1
HETATM    3  O   UNK     0      -0.054  -6.129   0.000  0.00  0.00           O-1
HETATM    4  C   UNK     0       2.613  -6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.631  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.171  -4.638   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.091  -4.602   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.649  -3.080   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.325  -2.294   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.343  -0.754   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.018   0.031   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.685  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.010  -0.786   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.353  -0.031   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.028   0.754   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.371   1.509   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.046   2.294   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.713   2.263   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.038   1.477   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.020  -0.062   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.498   0.370   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.038  -1.614   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      10.577  -1.660   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       8.118  -2.850   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.659  -2.357   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.677  -0.817   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.317  -3.111   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       3.974  -3.865   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       3.992  -2.326   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7    8                                             
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    5    9   29                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   29                                                  
CONECT   14   13   15   16   26                                             
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22   26                                             
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25   20   14                                                  
CONECT   27   25   28   29                                                  
CONECT   28   27   29                                                       
CONECT   29   28   13   27    8                                             
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₆O₈S

Average Mass

426.4800 Da

Monoisotopic Mass

426.13484 Da

IUPAC Name

(1R,2S,4R,5R,10R,11S,17S)-11-hydroxy-5-[(2R)-2-hydroxy-1-methanesulfinylpropan-2-yl]-10,14-dimethyl-3,6,16-trioxapentacyclo[8.6.1.0^{2,4}.0^{4,9}.0^{14,17}]heptadec-8-ene-7,15-dione

Traditional Name

(1R,2S,4R,5R,10R,11S,17S)-11-hydroxy-5-[(2R)-2-hydroxy-1-methanesulfinylpropan-2-yl]-10,14-dimethyl-3,6,16-trioxapentacyclo[8.6.1.0^{2,4}.0^{4,9}.0^{14,17}]heptadec-8-ene-7,15-dione

CAS Registry Number

Not Available

SMILES

C[S+]([O-])C[C@](C)(O)[C@H]1OC(=O)C=C2[C@]11O[C@H]1[C@@H]1OC(=O)C3(C)CC[C@H](O)[C@]2(C)[C@H]13

InChI Identifier

InChI=1S/C20H26O8S/c1-17-6-5-10(21)19(3)9-7-11(22)26-15(18(2,24)8-29(4)25)20(9)14(28-20)12(13(17)19)27-16(17)23/h7,10,12-15,21,24H,5-6,8H2,1-4H3/t10-,12+,13+,14-,15+,17?,18-,19+,20+,29?/m0/s1

InChI Key

SHHRLBQDNFCBIA-ZUDGZSMOSA-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
Podocarpus macrophyllus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Not Available

Direct Parent

Naphthopyrans

Alternative Parents

Substituents

Naphthopyran
Naphthalene
Oxepane
Dihydropyranone
Pyran
Gamma butyrolactone
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Tertiary alcohol
Cyclic alcohol
Sulfoxide
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Sulfinyl compound
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	-1.2	ChemAxon
pKa (Strongest Acidic)	13.4	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	122.66 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	101.44 m³·mol⁻¹	ChemAxon
Polarizability	42.02 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

102354698

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2s,4r,5r,10r,11s,17s)-11-hydroxy-5-[(2r)-2-hydroxy-1-methanesulfinylpropan-2-yl]-10,14-dimethyl-3,6,16-trioxapentacyclo[8.6.1.0²,⁴.0⁴,⁹.0¹⁴,¹⁷]heptadec-8-ene-7,15-dione (NP0294747)

MOL for NP0294747 ((1r,2s,4r,5r,10r,11s,17s)-11-hydroxy-5-[(2r)-2-hydroxy-1-methanesulfinylpropan-2-yl]-10,14-dimethyl-3,6,16-trioxapentacyclo[8.6.1.0²,⁴.0⁴,⁹.0¹⁴,¹⁷]heptadec-8-ene-7,15-dione)

3D MOL for NP0294747 ((1r,2s,4r,5r,10r,11s,17s)-11-hydroxy-5-[(2r)-2-hydroxy-1-methanesulfinylpropan-2-yl]-10,14-dimethyl-3,6,16-trioxapentacyclo[8.6.1.0²,⁴.0⁴,⁹.0¹⁴,¹⁷]heptadec-8-ene-7,15-dione)

3D SDF for NP0294747 ((1r,2s,4r,5r,10r,11s,17s)-11-hydroxy-5-[(2r)-2-hydroxy-1-methanesulfinylpropan-2-yl]-10,14-dimethyl-3,6,16-trioxapentacyclo[8.6.1.0²,⁴.0⁴,⁹.0¹⁴,¹⁷]heptadec-8-ene-7,15-dione)

3D-SDF for NP0294747 ((1r,2s,4r,5r,10r,11s,17s)-11-hydroxy-5-[(2r)-2-hydroxy-1-methanesulfinylpropan-2-yl]-10,14-dimethyl-3,6,16-trioxapentacyclo[8.6.1.0²,⁴.0⁴,⁹.0¹⁴,¹⁷]heptadec-8-ene-7,15-dione)

PDB for NP0294747 ((1r,2s,4r,5r,10r,11s,17s)-11-hydroxy-5-[(2r)-2-hydroxy-1-methanesulfinylpropan-2-yl]-10,14-dimethyl-3,6,16-trioxapentacyclo[8.6.1.0²,⁴.0⁴,⁹.0¹⁴,¹⁷]heptadec-8-ene-7,15-dione)

3D PDB for NP0294747 ((1r,2s,4r,5r,10r,11s,17s)-11-hydroxy-5-[(2r)-2-hydroxy-1-methanesulfinylpropan-2-yl]-10,14-dimethyl-3,6,16-trioxapentacyclo[8.6.1.0²,⁴.0⁴,⁹.0¹⁴,¹⁷]heptadec-8-ene-7,15-dione)

SMILES for NP0294747 ((1r,2s,4r,5r,10r,11s,17s)-11-hydroxy-5-[(2r)-2-hydroxy-1-methanesulfinylpropan-2-yl]-10,14-dimethyl-3,6,16-trioxapentacyclo[8.6.1.0²,⁴.0⁴,⁹.0¹⁴,¹⁷]heptadec-8-ene-7,15-dione)

INCHI for NP0294747 ((1r,2s,4r,5r,10r,11s,17s)-11-hydroxy-5-[(2r)-2-hydroxy-1-methanesulfinylpropan-2-yl]-10,14-dimethyl-3,6,16-trioxapentacyclo[8.6.1.0²,⁴.0⁴,⁹.0¹⁴,¹⁷]heptadec-8-ene-7,15-dione)

Structure for NP0294747 ((1r,2s,4r,5r,10r,11s,17s)-11-hydroxy-5-[(2r)-2-hydroxy-1-methanesulfinylpropan-2-yl]-10,14-dimethyl-3,6,16-trioxapentacyclo[8.6.1.0²,⁴.0⁴,⁹.0¹⁴,¹⁷]heptadec-8-ene-7,15-dione)

3D Structure for NP0294747 ((1r,2s,4r,5r,10r,11s,17s)-11-hydroxy-5-[(2r)-2-hydroxy-1-methanesulfinylpropan-2-yl]-10,14-dimethyl-3,6,16-trioxapentacyclo[8.6.1.0²,⁴.0⁴,⁹.0¹⁴,¹⁷]heptadec-8-ene-7,15-dione)