NP-MRD: Showing NP-Card for [(3s,4s)-4-(3,4,5-trimethoxybenzoyl)oxolan-3-yl](3,4,5-trimethoxyphenyl)methanol (NP0148806)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 04:36:40 UTC

Updated at

2022-09-02 04:36:41 UTC

NP-MRD ID

NP0148806

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(3s,4s)-4-(3,4,5-trimethoxybenzoyl)oxolan-3-yl](3,4,5-trimethoxyphenyl)methanol

Description

Aglacin K belongs to the class of organic compounds known as 9,9'-epoxylignans. These are lignans with a structure based on the 9,9'-epoxylignan skeleton, which consists of a tetrahydrofuran that carries two benzyl groups at the 3- and 4-positions. Additionally they are oxygenated at the 2-position to form dibenzylbutyrolactones (oxo group) or a dibenzylbutyrolactols (hydroxyl group). [(3s,4s)-4-(3,4,5-trimethoxybenzoyl)oxolan-3-yl](3,4,5-trimethoxyphenyl)methanol is found in Aglaia tomentosa. [(3s,4s)-4-(3,4,5-trimethoxybenzoyl)oxolan-3-yl](3,4,5-trimethoxyphenyl)methanol was first documented in 2004 (PMID: 15104504). Based on a literature review very few articles have been published on Aglacin K.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022206362D          

 33 35  0  0  1  0            999 V2000
    2.9646   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2501   -0.4741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5356   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8212   -0.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1067   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6078   -0.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3222   -0.0616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6078   -1.2991    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0597   -1.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1953   -2.5687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0203   -2.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2752   -1.7840    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0598   -1.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2314   -0.7221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6729   -2.0811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5014   -2.8881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1145   -3.4401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9430   -4.2471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5561   -4.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8991   -3.1852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5122   -3.7372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2968   -3.4823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0706   -2.3782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8553   -2.1233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0268   -1.3163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4575   -1.8262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1067    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8212    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8212    2.0009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5356    2.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5356    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2501    1.1759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2501    2.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  8  6  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  8 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  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
 17 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 26  2  0  0  0  0
 15 26  1  0  0  0  0
  5 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 28 31  2  0  0  0  0
  3 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
M  END

     RDKit          3D

 63 65  0  0  0  0  0  0  0  0999 V2000
    4.1075   -1.0271   -2.8183 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3383    0.1647   -2.0963 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5391    0.4616   -0.9754 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5344   -0.4261   -0.5982 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7066   -0.2165    0.4825 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6451   -1.1164    0.9027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0052   -0.7595    1.9512 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2752   -2.3634    0.2340 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3621   -3.3853    0.1437 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4492   -3.8796   -1.1211 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4928   -3.3298   -1.9156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1884   -2.2118   -1.1747 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6960   -2.4021   -1.2105 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1350   -2.3819   -2.5510 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3636   -1.2974   -0.4792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9401   -1.4722    0.7742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5607   -0.4445    1.4527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1404   -0.6042    2.7041 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0709   -1.8971    3.2776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5957    0.7849    0.8448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2029    1.8378    1.4827 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5716    2.7354    2.3557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0427    1.0282   -0.3991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1063    2.2893   -0.9670 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5173    2.4565   -2.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4329   -0.0248   -1.0421 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9500    0.9688    1.1855 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9391    1.8588    0.8275 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1140    3.0258    1.5908 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2953    3.2859    2.7032 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7458    1.6139   -0.2592 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7385    2.5011   -0.6236 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5474    3.5738   -1.5232 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3996   -1.9329   -2.2326 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7623   -0.9908   -3.7170 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0412   -1.0442   -3.1256 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4123   -1.3285   -1.1957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5504   -2.8300    0.8385 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1548   -4.2339    0.8622 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3596   -2.9898    0.4907 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9512   -2.9528   -2.8422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2711   -4.0944   -2.2271 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0967   -1.2280   -1.5740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0021   -3.3618   -0.7786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0856   -2.6407   -2.6076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8900   -2.4569    1.2165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0513   -2.0989    3.6869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8090   -1.9513    4.1294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3950   -2.6921    2.5737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5256    2.4737    2.5813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2017    2.8430    3.2534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5471    3.7266    1.8527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8749    1.6695   -2.9687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4258    2.3865   -2.2313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8676    3.4231   -2.7089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9888    0.1051   -2.0048 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3092    1.1659    2.0507 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2433    3.4639    2.3751 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6729    4.1915    3.2119 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2406    2.4234    3.4082 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4915    3.6379   -2.1301 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4467    4.5480   -0.9806 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6936    3.4220   -2.2067 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 18  1  0
 18 17  1  0
 17 16  2  0
 16 15  1  0
 15 26  2  0
 26 23  1  0
 23 24  1  0
 24 25  1  0
 23 20  2  0
 20 21  1  0
 21 22  1  0
 15 13  1  0
 13 14  1  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  6  1  0
  6  7  2  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  3  2  1  0
  2  1  1  0
  3 31  2  0
 31 32  1  0
 32 33  1  0
 31 28  1  0
 28 29  1  0
 29 30  1  0
 28 27  2  0
 20 17  1  0
  8 12  1  0
 27  5  1  0
 19 47  1  0
 19 48  1  0
 19 49  1  0
 16 46  1  0
 26 56  1  0
 25 53  1  0
 25 54  1  0
 25 55  1  0
 22 50  1  0
 22 51  1  0
 22 52  1  0
 13 44  1  1
 14 45  1  0
 12 43  1  6
 11 41  1  0
 11 42  1  0
  9 39  1  0
  9 40  1  0
  8 38  1  1
  4 37  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
 33 61  1  0
 33 62  1  0
 33 63  1  0
 30 58  1  0
 30 59  1  0
 30 60  1  0
 27 57  1  0
M  END


  Mrv1652309022206362D          

 33 35  0  0  1  0            999 V2000
    2.9646   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2501   -0.4741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5356   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8212   -0.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1067   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6078   -0.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3222   -0.0616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6078   -1.2991    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0597   -1.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1953   -2.5687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0203   -2.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2752   -1.7840    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0598   -1.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2314   -0.7221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6729   -2.0811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5014   -2.8881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1145   -3.4401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9430   -4.2471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5561   -4.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8991   -3.1852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5122   -3.7372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2968   -3.4823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0706   -2.3782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8553   -2.1233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0268   -1.3163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4575   -1.8262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1067    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8212    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8212    2.0009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5356    2.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5356    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2501    1.1759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2501    2.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  8  6  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  8 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  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
 17 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 26  2  0  0  0  0
 15 26  1  0  0  0  0
  5 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 28 31  2  0  0  0  0
  3 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0148806

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC(OC)=C1OC)C(O)[C@@H]1COC[C@H]1C(=O)C1=CC(OC)=C(OC)C(OC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C24H30O9/c1-27-17-7-13(8-18(28-2)23(17)31-5)21(25)15-11-33-12-16(15)22(26)14-9-19(29-3)24(32-6)20(10-14)30-4/h7-10,15-16,21,25H,11-12H2,1-6H3/t15-,16-,21?/m1/s1

> <INCHI_KEY>
RXZQMOJDZOQMMZ-BLRYKZMTSA-N

> <FORMULA>
C24H30O9

> <MOLECULAR_WEIGHT>
462.495

> <EXACT_MASS>
462.188982546

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
47.29000309019099

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(3S,4S)-4-(3,4,5-trimethoxybenzoyl)oxolan-3-yl](3,4,5-trimethoxyphenyl)methanol

> <ALOGPS_LOGP>
2.42

> <JCHEM_LOGP>
1.4713014539999998

> <ALOGPS_LOGS>
-4.30

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.378061746139643

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.58122868956994

> <JCHEM_PKA_STRONGEST_BASIC>
-3.222737029199304

> <JCHEM_POLAR_SURFACE_AREA>
101.91000000000003

> <JCHEM_REFRACTIVITY>
119.82

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.29e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(3S,4S)-4-(3,4,5-trimethoxybenzoyl)oxolan-3-yl](3,4,5-trimethoxyphenyl)methanol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       5.534  -0.115   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.200  -0.885   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.867  -0.115   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.533  -0.885   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.199  -0.115   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.134  -0.885   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.468  -0.115   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.134  -2.425   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.111  -3.330   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.364  -4.795   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.904  -4.795   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.380  -3.330   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.845  -2.854   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -4.165  -1.348   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -4.989  -3.885   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.669  -5.391   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.814  -6.422   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -5.494  -7.928   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -6.638  -8.958   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -7.278  -5.946   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -8.423  -6.976   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -9.887  -6.500   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -7.599  -4.439   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -9.063  -3.963   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -9.383  -2.457   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -6.454  -3.409   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.199   1.425   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.533   2.195   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.533   3.735   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.867   4.505   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.867   1.425   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       4.200   2.195   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       4.200   3.735   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   31                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   27                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    8   13                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   26                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23   15                                                       
CONECT   27    5   28                                                       
CONECT   28   27   29   31                                                  
CONECT   29   28   30                                                       
CONECT   30   29                                                            
CONECT   31   28    3   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Value	Source
7'-Hydroxy-3,3',4,4',5,5'-hexamethoxy-7'-keto-9,9'-epoxylignan	MeSH

Chemical Formula

C₂₄H₃₀O₉

Average Mass

462.4950 Da

Monoisotopic Mass

462.18898 Da

IUPAC Name

[(3S,4S)-4-(3,4,5-trimethoxybenzoyl)oxolan-3-yl](3,4,5-trimethoxyphenyl)methanol

Traditional Name

[(3S,4S)-4-(3,4,5-trimethoxybenzoyl)oxolan-3-yl](3,4,5-trimethoxyphenyl)methanol

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC(OC)=C1OC)C(O)[C@@H]1COC[C@H]1C(=O)C1=CC(OC)=C(OC)C(OC)=C1

InChI Identifier

InChI=1S/C24H30O9/c1-27-17-7-13(8-18(28-2)23(17)31-5)21(25)15-11-33-12-16(15)22(26)14-9-19(29-3)24(32-6)20(10-14)30-4/h7-10,15-16,21,25H,11-12H2,1-6H3/t15-,16-,21?/m1/s1

InChI Key

RXZQMOJDZOQMMZ-BLRYKZMTSA-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
Aglaia tomentosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 9,9'-epoxylignans. These are lignans with a structure based on the 9,9'-epoxylignan skeleton, which consists of a tetrahydrofuran that carries two benzyl groups at the 3- and 4-positions. Additionally they are oxygenated at the 2-position to form dibenzylbutyrolactones (oxo group) or a dibenzylbutyrolactols (hydroxyl group).

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Furanoid lignans

Sub Class

Tetrahydrofuran lignans

Direct Parent

9,9'-epoxylignans

Alternative Parents

Substituents

9,9p-epoxylignan
Alkyl-phenylketone
Phenylketone
Phenoxy compound
Anisole
Benzoyl
Methoxybenzene
Aryl alkyl ketone
Aryl ketone
Phenol ether
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Oxolane
Ketone
Secondary alcohol
Oxacycle
Dialkyl ether
Ether
Organoheterocyclic compound
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	2.42	ALOGPS
logP	1.47	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	12.58	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	101.91 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	119.82 m³·mol⁻¹	ChemAxon
Polarizability	47.29 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00043253

Chemspider ID

10189036

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21578050

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wang BG, Ebel R, Wang CY, Edrada RA, Wray V, Proksch P: Aglacins I-K, three highly methoxylated lignans from Aglaia cordata. J Nat Prod. 2004 Apr;67(4):682-4. doi: 10.1021/np034057l. [PubMed:15104504 ]
LOTUS database [Link]

Showing NP-Card for [(3s,4s)-4-(3,4,5-trimethoxybenzoyl)oxolan-3-yl](3,4,5-trimethoxyphenyl)methanol (NP0148806)

MOL for NP0148806 ([(3s,4s)-4-(3,4,5-trimethoxybenzoyl)oxolan-3-yl](3,4,5-trimethoxyphenyl)methanol)

3D MOL for NP0148806 ([(3s,4s)-4-(3,4,5-trimethoxybenzoyl)oxolan-3-yl](3,4,5-trimethoxyphenyl)methanol)

3D SDF for NP0148806 ([(3s,4s)-4-(3,4,5-trimethoxybenzoyl)oxolan-3-yl](3,4,5-trimethoxyphenyl)methanol)

3D-SDF for NP0148806 ([(3s,4s)-4-(3,4,5-trimethoxybenzoyl)oxolan-3-yl](3,4,5-trimethoxyphenyl)methanol)

PDB for NP0148806 ([(3s,4s)-4-(3,4,5-trimethoxybenzoyl)oxolan-3-yl](3,4,5-trimethoxyphenyl)methanol)

3D PDB for NP0148806 ([(3s,4s)-4-(3,4,5-trimethoxybenzoyl)oxolan-3-yl](3,4,5-trimethoxyphenyl)methanol)

SMILES for NP0148806 ([(3s,4s)-4-(3,4,5-trimethoxybenzoyl)oxolan-3-yl](3,4,5-trimethoxyphenyl)methanol)

INCHI for NP0148806 ([(3s,4s)-4-(3,4,5-trimethoxybenzoyl)oxolan-3-yl](3,4,5-trimethoxyphenyl)methanol)

Structure for NP0148806 ([(3s,4s)-4-(3,4,5-trimethoxybenzoyl)oxolan-3-yl](3,4,5-trimethoxyphenyl)methanol)

3D Structure for NP0148806 ([(3s,4s)-4-(3,4,5-trimethoxybenzoyl)oxolan-3-yl](3,4,5-trimethoxyphenyl)methanol)