NP-MRD: Showing NP-Card for (E)-9-etheno-de-O-methyl-lasiodiplodin (NP0042880)

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Record Information

Version

1.0

Created at

2021-06-21 00:26:06 UTC

Updated at

2021-06-30 00:18:14 UTC

NP-MRD ID

NP0042880

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(E)-9-etheno-de-O-methyl-lasiodiplodin

Provided By

JEOL Database JEOL Logo

Description

(3R)-12,14-dihydroxy-3-methyl-3,4,5,6,7,8-hexahydro-1H-2-benzoxacyclododecin-1-one belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. (E)-9-etheno-de-O-methyl-lasiodiplodin is found in Lasiodiplodia theobromae. It was first documented in 2014 (Sultan, S., et al.). Based on a literature review a significant number of articles have been published on (3R)-12,14-dihydroxy-3-methyl-3,4,5,6,7,8-hexahydro-1H-2-benzoxacyclododecin-1-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102263D          

 40 41  0  0  0  0            999 V2000
   -2.7193   -0.6886    2.7532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3914   -1.4196    2.5692 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3530   -0.9971    3.6249 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1902    0.4320    3.4516 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6741    0.4301    3.0698 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1967    1.7899    2.5841 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5570    2.3198    1.2910 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5193    1.2822    0.2053 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3757    0.7965   -0.3007 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3723   -0.3552   -1.2069 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6364   -0.1142   -2.5647 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7183   -1.1726   -3.4639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9734   -0.8771   -4.7703 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5603   -2.4841   -3.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3069   -2.7352   -1.6894 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1965   -4.0598   -1.3457 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1809   -1.6821   -0.7633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1333   -2.0442    0.6439 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2189   -3.1130    1.1264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9320   -1.1278    1.2352 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6154    0.3890    2.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1308   -0.8564    3.7531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4480   -1.0423    2.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5931   -2.4937    2.6704 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4783   -1.7125    3.6019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8046   -1.0912    4.6204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4018    0.9850    2.7184 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0813    0.9718    4.4005 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8690   -0.3307    2.3053 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2594    0.1282    3.9478 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0655    2.5369    3.3764 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.6967    2.4245 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5493    2.6936    1.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1325    3.1826    0.9350 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4780    0.8742   -0.1108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5956    1.1694    0.0140 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7890    0.9008   -2.9259 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0048   -1.7054   -5.2781 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6394   -3.3184   -3.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2313   -4.1352   -0.3663 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 10  2  0  0  0  0
 20  2  1  0  0  0  0
  5  4  1  0  0  0  0
  4  3  1  0  0  0  0
  3  2  1  0  0  0  0
 12 11  2  0  0  0  0
 11 10  1  0  0  0  0
 17 18  1  0  0  0  0
 10  9  1  0  0  0  0
  9  8  2  0  0  0  0
  8  7  1  0  0  0  0
  7  6  1  0  0  0  0
  6  5  1  0  0  0  0
 20 18  1  0  0  0  0
 15 16  1  0  0  0  0
 14 12  1  0  0  0  0
 12 13  1  0  0  0  0
 17 15  1  0  0  0  0
 18 19  2  0  0  0  0
 15 14  2  0  0  0  0
  2  1  1  0  0  0  0
 14 39  1  0  0  0  0
 11 37  1  0  0  0  0
  4 27  1  0  0  0  0
  4 28  1  0  0  0  0
  3 25  1  0  0  0  0
  3 26  1  0  0  0  0
  2 24  1  6  0  0  0
  9 36  1  0  0  0  0
  8 35  1  0  0  0  0
  7 33  1  0  0  0  0
  7 34  1  0  0  0  0
  6 31  1  0  0  0  0
  6 32  1  0  0  0  0
  5 29  1  0  0  0  0
  5 30  1  0  0  0  0
 16 40  1  0  0  0  0
 13 38  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
M  END

     RDKit          3D

 40 41  0  0  0  0  0  0  0  0999 V2000
   -2.7193   -0.6886    2.7532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3914   -1.4196    2.5692 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3530   -0.9971    3.6249 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1902    0.4320    3.4516 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6741    0.4301    3.0698 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1967    1.7899    2.5841 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5570    2.3198    1.2910 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5193    1.2822    0.2053 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3757    0.7965   -0.3007 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3723   -0.3552   -1.2069 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6364   -0.1142   -2.5647 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7183   -1.1726   -3.4639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9734   -0.8771   -4.7703 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5603   -2.4841   -3.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3069   -2.7352   -1.6894 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1965   -4.0598   -1.3457 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1809   -1.6821   -0.7633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1333   -2.0442    0.6439 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2189   -3.1130    1.1264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9320   -1.1278    1.2352 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6154    0.3890    2.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1308   -0.8564    3.7531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4480   -1.0423    2.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5931   -2.4937    2.6704 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4783   -1.7125    3.6019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8046   -1.0912    4.6204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4018    0.9850    2.7184 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0813    0.9718    4.4005 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8690   -0.3307    2.3053 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2594    0.1282    3.9478 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0655    2.5369    3.3764 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.6967    2.4245 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5493    2.6936    1.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1325    3.1826    0.9350 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4780    0.8742   -0.1108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5956    1.1694    0.0140 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7890    0.9008   -2.9259 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0048   -1.7054   -5.2781 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6394   -3.3184   -3.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2313   -4.1352   -0.3663 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 10  2  0
 20  2  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
 12 11  2  0
 11 10  1  0
 17 18  1  0
 10  9  1  0
  9  8  2  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
 20 18  1  0
 15 16  1  0
 14 12  1  0
 12 13  1  0
 17 15  1  0
 18 19  2  0
 15 14  2  0
  2  1  1  0
 14 39  1  0
 11 37  1  0
  4 27  1  0
  4 28  1  0
  3 25  1  0
  3 26  1  0
  2 24  1  6
  9 36  1  0
  8 35  1  0
  7 33  1  0
  7 34  1  0
  6 31  1  0
  6 32  1  0
  5 29  1  0
  5 30  1  0
 16 40  1  0
 13 38  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
M  END


  Mrv1652306212102263D          

 40 41  0  0  0  0            999 V2000
   -2.7193   -0.6886    2.7532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3914   -1.4196    2.5692 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3530   -0.9971    3.6249 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1902    0.4320    3.4516 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6741    0.4301    3.0698 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1967    1.7899    2.5841 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5570    2.3198    1.2910 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5193    1.2822    0.2053 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3757    0.7965   -0.3007 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3723   -0.3552   -1.2069 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6364   -0.1142   -2.5647 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7183   -1.1726   -3.4639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9734   -0.8771   -4.7703 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5603   -2.4841   -3.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3069   -2.7352   -1.6894 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1965   -4.0598   -1.3457 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1809   -1.6821   -0.7633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1333   -2.0442    0.6439 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2189   -3.1130    1.1264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9320   -1.1278    1.2352 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6154    0.3890    2.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1308   -0.8564    3.7531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4480   -1.0423    2.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5931   -2.4937    2.6704 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4783   -1.7125    3.6019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8046   -1.0912    4.6204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4018    0.9850    2.7184 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0813    0.9718    4.4005 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8690   -0.3307    2.3053 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2594    0.1282    3.9478 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0655    2.5369    3.3764 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.6967    2.4245 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5493    2.6936    1.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1325    3.1826    0.9350 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4780    0.8742   -0.1108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5956    1.1694    0.0140 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7890    0.9008   -2.9259 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0048   -1.7054   -5.2781 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6394   -3.3184   -3.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2313   -4.1352   -0.3663 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 10  2  0  0  0  0
 20  2  1  0  0  0  0
  5  4  1  0  0  0  0
  4  3  1  0  0  0  0
  3  2  1  0  0  0  0
 12 11  2  0  0  0  0
 11 10  1  0  0  0  0
 17 18  1  0  0  0  0
 10  9  1  0  0  0  0
  9  8  2  0  0  0  0
  8  7  1  0  0  0  0
  7  6  1  0  0  0  0
  6  5  1  0  0  0  0
 20 18  1  0  0  0  0
 15 16  1  0  0  0  0
 14 12  1  0  0  0  0
 12 13  1  0  0  0  0
 17 15  1  0  0  0  0
 18 19  2  0  0  0  0
 15 14  2  0  0  0  0
  2  1  1  0  0  0  0
 14 39  1  0  0  0  0
 11 37  1  0  0  0  0
  4 27  1  0  0  0  0
  4 28  1  0  0  0  0
  3 25  1  0  0  0  0
  3 26  1  0  0  0  0
  2 24  1  6  0  0  0
  9 36  1  0  0  0  0
  8 35  1  0  0  0  0
  7 33  1  0  0  0  0
  7 34  1  0  0  0  0
  6 31  1  0  0  0  0
  6 32  1  0  0  0  0
  5 29  1  0  0  0  0
  5 30  1  0  0  0  0
 16 40  1  0  0  0  0
 13 38  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0042880

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C2=C(C(O[H])=C1[H])C(=O)O[C@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])\C([H])=C2/[H]

> <INCHI_IDENTIFIER>
InChI=1S/C16H20O4/c1-11-7-5-3-2-4-6-8-12-9-13(17)10-14(18)15(12)16(19)20-11/h6,8-11,17-18H,2-5,7H2,1H3/b8-6+/t11-/m1/s1

> <INCHI_KEY>
XHBTYLCYPRAQGX-LXSSAFMLSA-N

> <FORMULA>
C16H20O4

> <MOLECULAR_WEIGHT>
276.332

> <EXACT_MASS>
276.136159124

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
29.8253119605062

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R)-12,14-dihydroxy-3-methyl-3,4,5,6,7,8-hexahydro-1H-2-benzoxacyclododecin-1-one

> <ALOGPS_LOGP>
3.77

> <JCHEM_LOGP>
4.664246001

> <ALOGPS_LOGS>
-3.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.383903328843813

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.537726153093184

> <JCHEM_PKA_STRONGEST_BASIC>
-4.015715865817321

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
78.49609999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.66e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R)-12,14-dihydroxy-3-methyl-3,4,5,6,7,8-hexahydro-2-benzoxacyclododecin-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 40 41  0  0  0  0  0  0  0  0999 V2000
   -2.7193   -0.6886    2.7532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3914   -1.4196    2.5692 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3530   -0.9971    3.6249 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1902    0.4320    3.4516 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6741    0.4301    3.0698 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1967    1.7899    2.5841 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5570    2.3198    1.2910 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5193    1.2822    0.2053 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3757    0.7965   -0.3007 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3723   -0.3552   -1.2069 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6364   -0.1142   -2.5647 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7183   -1.1726   -3.4639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9734   -0.8771   -4.7703 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5603   -2.4841   -3.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3069   -2.7352   -1.6894 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1965   -4.0598   -1.3457 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1809   -1.6821   -0.7633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1333   -2.0442    0.6439 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2189   -3.1130    1.1264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9320   -1.1278    1.2352 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6154    0.3890    2.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1308   -0.8564    3.7531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4480   -1.0423    2.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5931   -2.4937    2.6704 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4783   -1.7125    3.6019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8046   -1.0912    4.6204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4018    0.9850    2.7184 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0813    0.9718    4.4005 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8690   -0.3307    2.3053 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2594    0.1282    3.9478 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0655    2.5369    3.3764 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.6967    2.4245 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5493    2.6936    1.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1325    3.1826    0.9350 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4780    0.8742   -0.1108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5956    1.1694    0.0140 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7890    0.9008   -2.9259 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0048   -1.7054   -5.2781 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6394   -3.3184   -3.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2313   -4.1352   -0.3663 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 10  2  0
 20  2  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
 12 11  2  0
 11 10  1  0
 17 18  1  0
 10  9  1  0
  9  8  2  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
 20 18  1  0
 15 16  1  0
 14 12  1  0
 12 13  1  0
 17 15  1  0
 18 19  2  0
 15 14  2  0
  2  1  1  0
 14 39  1  0
 11 37  1  0
  4 27  1  0
  4 28  1  0
  3 25  1  0
  3 26  1  0
  2 24  1  6
  9 36  1  0
  8 35  1  0
  7 33  1  0
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  6 31  1  0
  6 32  1  0
  5 29  1  0
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 16 40  1  0
 13 38  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0      -2.719  -0.689   2.753  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.391  -1.420   2.569  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.353  -0.997   3.625  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.190   0.432   3.452  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.674   0.430   3.070  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.197   1.790   2.584  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.557   2.320   1.291  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.519   1.282   0.205  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.376   0.797  -0.301  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.372  -0.355  -1.207  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.636  -0.114  -2.565  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.718  -1.173  -3.464  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.973  -0.877  -4.770  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.560  -2.484  -3.037  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.307  -2.735  -1.689  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.197  -4.060  -1.346  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.181  -1.682  -0.763  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.133  -2.044   0.644  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.219  -3.113   1.126  0.00  0.00           O+0
HETATM   20  O   UNK     0      -0.932  -1.128   1.235  0.00  0.00           O+0
HETATM   21  H   UNK     0      -2.615   0.389   2.591  0.00  0.00           H+0
HETATM   22  H   UNK     0      -3.131  -0.856   3.753  0.00  0.00           H+0
HETATM   23  H   UNK     0      -3.448  -1.042   2.015  0.00  0.00           H+0
HETATM   24  H   UNK     0      -1.593  -2.494   2.670  0.00  0.00           H+0
HETATM   25  H   UNK     0       0.478  -1.712   3.602  0.00  0.00           H+0
HETATM   26  H   UNK     0      -0.805  -1.091   4.620  0.00  0.00           H+0
HETATM   27  H   UNK     0      -0.402   0.985   2.718  0.00  0.00           H+0
HETATM   28  H   UNK     0       0.081   0.972   4.401  0.00  0.00           H+0
HETATM   29  H   UNK     0       1.869  -0.331   2.305  0.00  0.00           H+0
HETATM   30  H   UNK     0       2.259   0.128   3.948  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.066   2.537   3.376  0.00  0.00           H+0
HETATM   32  H   UNK     0       3.279   1.697   2.425  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.549   2.694   1.508  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.132   3.183   0.935  0.00  0.00           H+0
HETATM   35  H   UNK     0       2.478   0.874  -0.111  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.596   1.169   0.014  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.789   0.901  -2.926  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.005  -1.705  -5.278  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.639  -3.318  -3.727  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.231  -4.135  -0.366  0.00  0.00           H+0
CONECT    1    2   21   22   23                                             
CONECT    2   20    3    1   24                                             
CONECT    3    4    2   25   26                                             
CONECT    4    5    3   27   28                                             
CONECT    5    4    6   29   30                                             
CONECT    6    7    5   31   32                                             
CONECT    7    8    6   33   34                                             
CONECT    8    9    7   35                                                  
CONECT    9   10    8   36                                                  
CONECT   10   17   11    9                                                  
CONECT   11   12   10   37                                                  
CONECT   12   11   14   13                                                  
CONECT   13   12   38                                                       
CONECT   14   12   15   39                                                  
CONECT   15   16   17   14                                                  
CONECT   16   15   40                                                       
CONECT   17   10   18   15                                                  
CONECT   18   17   20   19                                                  
CONECT   19   18                                                            
CONECT   20    2   18                                                       
CONECT   21    1                                                            
CONECT   22    1                                                            
CONECT   23    1                                                            
CONECT   24    2                                                            
CONECT   25    3                                                            
CONECT   26    3                                                            
CONECT   27    4                                                            
CONECT   28    4                                                            
CONECT   29    5                                                            
CONECT   30    5                                                            
CONECT   31    6                                                            
CONECT   32    6                                                            
CONECT   33    7                                                            
CONECT   34    7                                                            
CONECT   35    8                                                            
CONECT   36    9                                                            
CONECT   37   11                                                            
CONECT   38   13                                                            
CONECT   39   14                                                            
CONECT   40   16                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   82    0
END

RDKit          3D

40 41  0  0  0  0  0  0  0  0999 V2000
   -2.7193   -0.6886    2.7532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3914   -1.4196    2.5692 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3530   -0.9971    3.6249 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1902    0.4320    3.4516 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6741    0.4301    3.0698 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1967    1.7899    2.5841 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5570    2.3198    1.2910 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5193    1.2822    0.2053 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3757    0.7965   -0.3007 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3723   -0.3552   -1.2069 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6364   -0.1142   -2.5647 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7183   -1.1726   -3.4639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9734   -0.8771   -4.7703 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5603   -2.4841   -3.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3069   -2.7352   -1.6894 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1965   -4.0598   -1.3457 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1809   -1.6821   -0.7633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1333   -2.0442    0.6439 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2189   -3.1130    1.1264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9320   -1.1278    1.2352 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6154    0.3890    2.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1308   -0.8564    3.7531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4480   -1.0423    2.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5931   -2.4937    2.6704 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4783   -1.7125    3.6019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8046   -1.0912    4.6204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4018    0.9850    2.7184 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0813    0.9718    4.4005 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8690   -0.3307    2.3053 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2594    0.1282    3.9478 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0655    2.5369    3.3764 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.6967    2.4245 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5493    2.6936    1.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1325    3.1826    0.9350 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4780    0.8742   -0.1108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5956    1.1694    0.0140 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7890    0.9008   -2.9259 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0048   -1.7054   -5.2781 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6394   -3.3184   -3.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2313   -4.1352   -0.3663 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 10  2  0
 20  2  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
 12 11  2  0
 11 10  1  0
 17 18  1  0
 10  9  1  0
  9  8  2  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
 20 18  1  0
 15 16  1  0
 14 12  1  0
 12 13  1  0
 17 15  1  0
 18 19  2  0
 15 14  2  0
  2  1  1  0
 14 39  1  0
 11 37  1  0
  4 27  1  0
  4 28  1  0
  3 25  1  0
  3 26  1  0
  2 24  1  6
  9 36  1  0
  8 35  1  0
  7 33  1  0
  7 34  1  0
  6 31  1  0
  6 32  1  0
  5 29  1  0
  5 30  1  0
 16 40  1  0
 13 38  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₂₀O₄

Average Mass

276.3320 Da

Monoisotopic Mass

276.13616 Da

IUPAC Name

(3R)-12,14-dihydroxy-3-methyl-3,4,5,6,7,8-hexahydro-1H-2-benzoxacyclododecin-1-one

Traditional Name

(3R)-12,14-dihydroxy-3-methyl-3,4,5,6,7,8-hexahydro-2-benzoxacyclododecin-1-one

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C2=C(C(O[H])=C1[H])C(=O)O[C@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])\C([H])=C2/[H]

InChI Identifier

InChI=1S/C16H20O4/c1-11-7-5-3-2-4-6-8-12-9-13(17)10-14(18)15(12)16(19)20-11/h6,8-11,17-18H,2-5,7H2,1H3/b8-6+/t11-/m1/s1

InChI Key

XHBTYLCYPRAQGX-LXSSAFMLSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol-d4, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Lasiodiplodia theobromae	JEOL database	Sultan, S., et al. J. Tetrahedron Lett. 55, 453 (2014)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Not Available

Direct Parent

Macrolides and analogues

Alternative Parents

Substituents

Macrolide
Dihydroxybenzoic acid
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Vinylogous acid
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	3.77	ALOGPS
logP	4.66	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	8.54	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	78.5 m³·mol⁻¹	ChemAxon
Polarizability	29.83 Å³	ChemAxon
Number of Rings	2	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

102233600

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Sultan, S., et al. (2014). Sultan, S., et al. J. Tetrahedron Lett. 55, 453 (2014). J. Tetrahedron Lett..

Showing NP-Card for (E)-9-etheno-de-O-methyl-lasiodiplodin (NP0042880)

MOL for NP0042880 ((E)-9-etheno-de-O-methyl-lasiodiplodin)

3D MOL for NP0042880 ((E)-9-etheno-de-O-methyl-lasiodiplodin)

3D SDF for NP0042880 ((E)-9-etheno-de-O-methyl-lasiodiplodin)

3D-SDF for NP0042880 ((E)-9-etheno-de-O-methyl-lasiodiplodin)

PDB for NP0042880 ((E)-9-etheno-de-O-methyl-lasiodiplodin)

3D PDB for NP0042880 ((E)-9-etheno-de-O-methyl-lasiodiplodin)

SMILES for NP0042880 ((E)-9-etheno-de-O-methyl-lasiodiplodin)

INCHI for NP0042880 ((E)-9-etheno-de-O-methyl-lasiodiplodin)

Structure for NP0042880 ((E)-9-etheno-de-O-methyl-lasiodiplodin)

3D Structure for NP0042880 ((E)-9-etheno-de-O-methyl-lasiodiplodin)