NP-MRD: Showing NP-Card for Sesamin (NP0005798)

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Record Information

Version

2.0

Created at

2020-12-09 02:57:00 UTC

Updated at

2021-08-19 23:59:38 UTC

NP-MRD ID

NP0005798

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Sesamin

Provided By

NPAtlas

Description

(+)-Sesamin, also known as epi-sesamin or fagarol, belongs to the class of organic compounds known as furanoid lignans. These are lignans with a structure that contains either a tetrahydrofuran ring, a furan ring, or a furofuan ring system, that arises from the joining of the two phenylpropanoid units (+)-Sesamin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Sesamin is found in Acanthopanax divaricatus var.albeofructus C.S.YOOK et T.H.KIM, Achillea biserrata, Achillea clavennae, Achillea millefolium, Aiouea trinervis, Anacyclus pyrethrum, Aristolochia tagala, Aristolochia tomentosa, Artemisia absinthium, Artemisia giraldii, Artemisia gorgonum, Artemisia sieversiana, Asarum heterotropoides, Asarum sieboldii, Boronia bowmanii, Boronia pancheri, Buddleja cordata, Callicarpa furfuracea, Camellia oleifera, Cinnamomum kotoense, Cinnamomum subavenium, Cinnamomum triplinerve, Cleistanthus collinus, Corymbia citriodora, Cratoxylum cochinchinense, Cucumis sativus, Cuscuta chinensis, Dinosperma stipitatum, Eremophila phyllopoda, Esenbeckia leiocarpa, Forsythia suspensa, Gonospermum fruticosum, Gonospermum gomerae, Horsfieldia irya, Hypenia salzmannii, Hypericum chinense, Juniperus communis, Leucanthemopsis pallida, Lindera praecox, Magnolia kobus, Markhamia platycalyx, Melicope elleryana, Nectandra amazonum, Oplopanax horridus, Pandanus boninensis, Peperomia blanda, Peperomia leptostachya, Peperomia pellucida, Peperomia vulcanica, Piper guineense, Piper sintenense, Podolepis rugata, Samadera bidwillii, Senecio magnificus, Sesamum capense, Sideritis candicans, Sideritis cretica, Streptomyces, Antrodia camphorata, Turraeanthus africanus, Virola flexuosa, Vitex negundo, Xanthoxylum tingoassuiba, Zanthoxylum ailanthoides, Zanthoxylum beecheyanum, Zanthoxylum gilletii, Zanthoxylum leprieurii, Zanthoxylum rhoifolium, Zanthoxylum setulosum and Zanthoxylum zanthoxyloides. Sesamin was first documented in 2005 (PMID: 15792856). Based on a literature review a small amount of articles have been published on (+)-Sesamin (PMID: 16785429) (PMID: 16309310).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118223D          

 44 49  0  0  0  0            999 V2000
    3.4381    1.4962   -1.4884 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8114    1.6204   -1.5385 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5439    0.8943   -0.6159 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9539    0.0762    0.3218 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5692   -0.0415    0.3632 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8304    0.6727   -0.5456 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3417    0.5991   -0.5644 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9640    0.4598   -1.8940 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2835   -0.1145   -1.9479 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4583   -0.8897   -0.6889 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4138   -0.1958    0.2223 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8302   -0.3733   -0.0686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2658   -0.8513   -1.2786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6275   -1.0193   -1.5539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5754   -0.7051   -0.6054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1486   -0.2237    0.6144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7898   -0.0628    0.8713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2964    0.0048    1.3613 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4384    0.0471    0.5006 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.9815   -0.7592   -0.5742 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0359   -0.6842    1.4700 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3364   -0.4556    1.4698 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8537   -0.6877    0.0850 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9636   -0.5104    1.0973 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1935    0.1096    0.7334 C   0  0  1  0  0  0  0  0  0  0  0  0
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    2.8128    2.0486   -2.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0908   -0.6844    1.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8799    1.4600   -0.0600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0183    0.7299   -2.0558 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6640   -1.9584   -0.8357 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5582   -1.1073   -2.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9667   -1.3960   -2.5079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4523    0.3138    1.8253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5724    1.0721    0.0719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3406   -0.3439    0.9824 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8195   -1.0858    2.2326 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5394   -1.5235   -0.0285 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5258    0.8512    1.4893 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9745   -0.6396    0.4905 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
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  1 27  1  0  0  0  0
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  9 31  1  0  0  0  0
  9 32  1  0  0  0  0
 10 33  1  6  0  0  0
 11 34  1  1  0  0  0
 13 35  1  0  0  0  0
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 17 37  1  0  0  0  0
 19 38  1  0  0  0  0
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 22 40  1  0  0  0  0
 22 41  1  0  0  0  0
 23 42  1  1  0  0  0
 25 43  1  0  0  0  0
 25 44  1  0  0  0  0
M  END

     RDKit          3D

 44 49  0  0  0  0  0  0  0  0999 V2000
    3.4381    1.4962   -1.4884 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8114    1.6204   -1.5385 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5439    0.8943   -0.6159 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9539    0.0762    0.3218 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5692   -0.0415    0.3632 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8304    0.6727   -0.5456 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3417    0.5991   -0.5644 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9640    0.4598   -1.8940 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2835   -0.1145   -1.9479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4583   -0.8897   -0.6889 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -2.8302   -0.3733   -0.0686 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.5754   -0.7051   -0.6054 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0359   -0.6842    1.4700 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3364   -0.4556    1.4698 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8537   -0.6877    0.0850 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9636   -0.5104    1.0973 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1935    0.1096    0.7334 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9269    0.8395   -0.4507 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8128    2.0486   -2.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2902    2.2639   -2.2750 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0908   -0.6844    1.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8799    1.4600   -0.0600 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6640   -1.9584   -0.8357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1057    0.8924    0.2331 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306242118223D          

 44 49  0  0  0  0            999 V2000
    3.4381    1.4962   -1.4884 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8114    1.6204   -1.5385 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5439    0.8943   -0.6159 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9539    0.0762    0.3218 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5692   -0.0415    0.3632 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8304    0.6727   -0.5456 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3417    0.5991   -0.5644 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9640    0.4598   -1.8940 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2835   -0.1145   -1.9479 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4583   -0.8897   -0.6889 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4138   -0.1958    0.2223 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8302   -0.3733   -0.0686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2658   -0.8513   -1.2786 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  0  0  0  0
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 11 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  4 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  6  1  1  0  0  0  0
 23  7  1  0  0  0  0
 26  3  1  0  0  0  0
 23 10  1  0  0  0  0
 17 12  1  0  0  0  0
 20 15  1  0  0  0  0
  1 27  1  0  0  0  0
  2 28  1  0  0  0  0
  5 29  1  0  0  0  0
  7 30  1  1  0  0  0
  9 31  1  0  0  0  0
  9 32  1  0  0  0  0
 10 33  1  6  0  0  0
 11 34  1  1  0  0  0
 13 35  1  0  0  0  0
 14 36  1  0  0  0  0
 17 37  1  0  0  0  0
 19 38  1  0  0  0  0
 19 39  1  0  0  0  0
 22 40  1  0  0  0  0
 22 41  1  0  0  0  0
 23 42  1  1  0  0  0
 25 43  1  0  0  0  0
 25 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0005798

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1=C([H])C(=C([H])C2=C1OC([H])([H])O2)[C@@]1([H])OC([H])([H])[C@]2([H])[C@]([H])(OC([H])([H])[C@]12[H])C1=C([H])C([H])=C2OC([H])([H])OC2=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H18O6/c1-3-15-17(25-9-23-15)5-11(1)19-13-7-22-20(14(13)8-21-19)12-2-4-16-18(6-12)26-10-24-16/h1-6,13-14,19-20H,7-10H2/t13-,14-,19+,20+/m0/s1

> <INCHI_KEY>
PEYUIKBAABKQKQ-AFHBHXEDSA-N

> <FORMULA>
C20H18O6

> <MOLECULAR_WEIGHT>
354.3533

> <EXACT_MASS>
354.110338308

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
36.740784967537024

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[(1S,3aR,4S,6aR)-4-(2H-1,3-benzodioxol-5-yl)-hexahydrofuro[3,4-c]furan-1-yl]-2H-1,3-benzodioxole

> <ALOGPS_LOGP>
2.25

> <JCHEM_LOGP>
2.446699657333334

> <ALOGPS_LOGS>
-4.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7750497381707224

> <JCHEM_POLAR_SURFACE_AREA>
55.38000000000001

> <JCHEM_REFRACTIVITY>
89.74580000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.24e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
asarinin

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 44 49  0  0  0  0  0  0  0  0999 V2000
    3.4381    1.4962   -1.4884 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8114    1.6204   -1.5385 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5439    0.8943   -0.6159 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9539    0.0762    0.3218 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5692   -0.0415    0.3632 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8304    0.6727   -0.5456 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3417    0.5991   -0.5644 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9640    0.4598   -1.8940 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2835   -0.1145   -1.9479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4583   -0.8897   -0.6889 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4138   -0.1958    0.2223 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8302   -0.3733   -0.0686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2658   -0.8513   -1.2786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6275   -1.0193   -1.5539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5754   -0.7051   -0.6054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1486   -0.2237    0.6144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7898   -0.0628    0.8713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2964    0.0048    1.3613 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4384    0.0471    0.5006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9815   -0.7592   -0.5742 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0359   -0.6842    1.4700 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3364   -0.4556    1.4698 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8537   -0.6877    0.0850 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9636   -0.5104    1.0973 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1935    0.1096    0.7334 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9269    0.8395   -0.4507 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8128    2.0486   -2.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2902    2.2639   -2.2750 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0908   -0.6844    1.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8799    1.4600   -0.0600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0183    0.7299   -2.0558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3491   -0.7643   -2.8566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6640   -1.9584   -0.8357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1057    0.8924    0.2331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5582   -1.1073   -2.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9667   -1.3960   -2.5079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4523    0.3138    1.8253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5724    1.0721    0.0719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3406   -0.3439    0.9824 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8195   -1.0858    2.2326 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5130    0.6259    1.7431 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5394   -1.5235   -0.0285 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5258    0.8512    1.4893 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9745   -0.6396    0.4905 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 11 21  1  0
 21 22  1  0
 22 23  1  0
  4 24  1  0
 24 25  1  0
 25 26  1  0
  6  1  1  0
 23  7  1  0
 26  3  1  0
 23 10  1  0
 17 12  1  0
 20 15  1  0
  1 27  1  0
  2 28  1  0
  5 29  1  0
  7 30  1  1
  9 31  1  0
  9 32  1  0
 10 33  1  6
 11 34  1  1
 13 35  1  0
 14 36  1  0
 17 37  1  0
 19 38  1  0
 19 39  1  0
 22 40  1  0
 22 41  1  0
 23 42  1  1
 25 43  1  0
 25 44  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       3.438   1.496  -1.488  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.811   1.620  -1.539  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.544   0.894  -0.616  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.954   0.076   0.322  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.569  -0.042   0.363  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.830   0.673  -0.546  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.342   0.599  -0.564  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.964   0.460  -1.894  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.284  -0.115  -1.948  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.458  -0.890  -0.689  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.414  -0.196   0.222  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.830  -0.373  -0.069  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.266  -0.851  -1.279  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.628  -1.019  -1.554  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.575  -0.705  -0.605  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.149  -0.224   0.614  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.790  -0.063   0.871  0.00  0.00           C+0
HETATM   18  O   UNK     0      -6.296   0.005   1.361  0.00  0.00           O+0
HETATM   19  C   UNK     0      -7.438   0.047   0.501  0.00  0.00           C+0
HETATM   20  O   UNK     0      -6.981  -0.759  -0.574  0.00  0.00           O+0
HETATM   21  O   UNK     0      -1.036  -0.684   1.470  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.336  -0.456   1.470  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.854  -0.688   0.085  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.964  -0.510   1.097  0.00  0.00           O+0
HETATM   25  C   UNK     0       7.194   0.110   0.733  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.927   0.840  -0.451  0.00  0.00           O+0
HETATM   27  H   UNK     0       2.813   2.049  -2.195  0.00  0.00           H+0
HETATM   28  H   UNK     0       5.290   2.264  -2.275  0.00  0.00           H+0
HETATM   29  H   UNK     0       3.091  -0.684   1.099  0.00  0.00           H+0
HETATM   30  H   UNK     0       0.880   1.460  -0.060  0.00  0.00           H+0
HETATM   31  H   UNK     0      -1.018   0.730  -2.056  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.349  -0.764  -2.857  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.664  -1.958  -0.836  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.106   0.892   0.233  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.558  -1.107  -2.040  0.00  0.00           H+0
HETATM   36  H   UNK     0      -4.967  -1.396  -2.508  0.00  0.00           H+0
HETATM   37  H   UNK     0      -3.452   0.314   1.825  0.00  0.00           H+0
HETATM   38  H   UNK     0      -7.572   1.072   0.072  0.00  0.00           H+0
HETATM   39  H   UNK     0      -8.341  -0.344   0.982  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.820  -1.086   2.233  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.513   0.626   1.743  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.539  -1.524  -0.029  0.00  0.00           H+0
HETATM   43  H   UNK     0       7.526   0.851   1.489  0.00  0.00           H+0
HETATM   44  H   UNK     0       7.974  -0.640   0.491  0.00  0.00           H+0
CONECT    1    2    6   27                                                  
CONECT    2    1    3   28                                                  
CONECT    3    2    4   26                                                  
CONECT    4    3    5   24                                                  
CONECT    5    4    6   29                                                  
CONECT    6    5    7    1                                                  
CONECT    7    6    8   23   30                                             
CONECT    8    7    9                                                       
CONECT    9    8   10   31   32                                             
CONECT   10    9   11   23   33                                             
CONECT   11   10   12   21   34                                             
CONECT   12   11   13   17                                                  
CONECT   13   12   14   35                                                  
CONECT   14   13   15   36                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   12   37                                                  
CONECT   18   16   19                                                       
CONECT   19   18   20   38   39                                             
CONECT   20   19   15                                                       
CONECT   21   11   22                                                       
CONECT   22   21   23   40   41                                             
CONECT   23   22    7   10   42                                             
CONECT   24    4   25                                                       
CONECT   25   24   26   43   44                                             
CONECT   26   25    3                                                       
CONECT   27    1                                                            
CONECT   28    2                                                            
CONECT   29    5                                                            
CONECT   30    7                                                            
CONECT   31    9                                                            
CONECT   32    9                                                            
CONECT   33   10                                                            
CONECT   34   11                                                            
CONECT   35   13                                                            
CONECT   36   14                                                            
CONECT   37   17                                                            
CONECT   38   19                                                            
CONECT   39   19                                                            
CONECT   40   22                                                            
CONECT   41   22                                                            
CONECT   42   23                                                            
CONECT   43   25                                                            
CONECT   44   25                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   98    0
END

RDKit          3D

44 49  0  0  0  0  0  0  0  0999 V2000
    3.4381    1.4962   -1.4884 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8114    1.6204   -1.5385 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5439    0.8943   -0.6159 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9539    0.0762    0.3218 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5692   -0.0415    0.3632 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8304    0.6727   -0.5456 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3417    0.5991   -0.5644 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9640    0.4598   -1.8940 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2835   -0.1145   -1.9479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4583   -0.8897   -0.6889 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4138   -0.1958    0.2223 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8302   -0.3733   -0.0686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2658   -0.8513   -1.2786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6275   -1.0193   -1.5539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5754   -0.7051   -0.6054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1486   -0.2237    0.6144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7898   -0.0628    0.8713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2964    0.0048    1.3613 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4384    0.0471    0.5006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9815   -0.7592   -0.5742 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0359   -0.6842    1.4700 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3364   -0.4556    1.4698 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8537   -0.6877    0.0850 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9636   -0.5104    1.0973 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1935    0.1096    0.7334 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9269    0.8395   -0.4507 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8128    2.0486   -2.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2902    2.2639   -2.2750 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0908   -0.6844    1.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8799    1.4600   -0.0600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0183    0.7299   -2.0558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3491   -0.7643   -2.8566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6640   -1.9584   -0.8357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1057    0.8924    0.2331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5582   -1.1073   -2.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9667   -1.3960   -2.5079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4523    0.3138    1.8253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5724    1.0721    0.0719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3406   -0.3439    0.9824 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8195   -1.0858    2.2326 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5130    0.6259    1.7431 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5394   -1.5235   -0.0285 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5258    0.8512    1.4893 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9745   -0.6396    0.4905 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 11 21  1  0
 21 22  1  0
 22 23  1  0
  4 24  1  0
 24 25  1  0
 25 26  1  0
  6  1  1  0
 23  7  1  0
 26  3  1  0
 23 10  1  0
 17 12  1  0
 20 15  1  0
  1 27  1  0
  2 28  1  0
  5 29  1  0
  7 30  1  1
  9 31  1  0
  9 32  1  0
 10 33  1  6
 11 34  1  1
 13 35  1  0
 14 36  1  0
 17 37  1  0
 19 38  1  0
 19 39  1  0
 22 40  1  0
 22 41  1  0
 23 42  1  1
 25 43  1  0
 25 44  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Fagarol	ChEBI
Sezamin	ChEBI
Asarinin	HMDB
Sesamin, (1R-(1alpha,3aalpha,4alpha,6aalpha))-isomer	HMDB
Sesamin, (1R-(1alpha,3aalpha,4beta,6aalpha))-isomer	HMDB
Epi-sesamin	HMDB
Episesamin	HMDB
Sesamin	HMDB
Tetrahydro-1,4-bis[3,4-(methylenedioxy)phenyl]-1H,3H-furo[3,4-c]furan	HMDB
delta-Sesamin	HMDB
Δ-sesamin	HMDB
(+)-Sesamin	KEGG

Chemical Formula

C₂₀H₁₈O₆

Average Mass

354.3533 Da

Monoisotopic Mass

354.11034 Da

IUPAC Name

5-[(1S,3aR,4S,6aR)-4-(2H-1,3-benzodioxol-5-yl)-hexahydrofuro[3,4-c]furan-1-yl]-2H-1,3-benzodioxole

Traditional Name

asarinin

CAS Registry Number

Not Available

SMILES

C1OC2=C(O1)C=C(C=C2)[C@H]1OC[C@H]2[C@@H]1CO[C@@H]2C1=CC2=C(OCO2)C=C1

InChI Identifier

InChI=1S/C20H18O6/c1-3-15-17(25-9-23-15)5-11(1)19-13-7-22-20(14(13)8-21-19)12-2-4-16-18(6-12)26-10-24-16/h1-6,13-14,19-20H,7-10H2/t13-,14-,19+,20+/m0/s1

InChI Key

PEYUIKBAABKQKQ-AFHBHXEDSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Acanthopanax divaricatus var.albeofructus C.S.YOOK et T.H.KIM	Plant	KNApSAcK
Achillea biserrata	LOTUS Database	35616633
Achillea clavennae	LOTUS Database	35616633
Achillea millefolium	LOTUS Database	35616633
Achillea spirokensis	KNApSAcK Database	22123792
Actinodaphne longifolia	KNApSAcK Database	22123792
Ageratina virburnoides	KNApSAcK Database	22123792
Ageratum conyzoides	KNApSAcK Database	22123792
Aiouea trinervis	LOTUS Database	35616633
Amanoa oblongifolia	KNApSAcK Database	22123792
Anacyclus pyrethrum	LOTUS Database	35616633
Apollonias barbujana	KNApSAcK Database	22123792
Aptosimum spinescens	KNApSAcK Database	22123792
Aristolochia flos-avis	KNApSAcK Database	22123792
Aristolochia pubescens	KNApSAcK Database	22123792
Aristolochia tagala	LOTUS Database	35616633
Aristolochia tomentosa	LOTUS Database	35616633
Artemisia absinthium	LOTUS Database	35616633
Artemisia arborescens	KNApSAcK Database	22123792
Artemisia argentea	KNApSAcK Database	22123792
Artemisia capillaris	KNApSAcK Database	22123792
Artemisia caruifolia	KNApSAcK Database	22123792
Artemisia giraldii	LOTUS Database	35616633
Artemisia gorgonum	LOTUS Database	35616633
Artemisia sieversiana	LOTUS Database	35616633
Asarum heterotropoides	LOTUS Database	35616633
Asarum heterotropoides var. mandshuricum	KNApSAcK Database	22123792
Asarum maximum	KNApSAcK Database	22123792
Asarum sieboldii	LOTUS Database	35616633
Asiasarum sieboldii	KNApSAcK Database	22123792
Asiasarum sp.	KNApSAcK Database	22123792
Boronella pancheri	KNApSAcK Database	22123792
Boronia bowmanii	Plant	KNApSAcK
Boronia pancheri	LOTUS Database	35616633
Bridelia retusa	KNApSAcK Database	22123792
Buddleja cordata	LOTUS Database	35616633
Callicarpa furfuracea	LOTUS Database	35616633
Calocedrus formosana	KNApSAcK Database	22123792
Camellia oleifera	LOTUS Database	35616633
Caryodaphnopsis baviensis	KNApSAcK Database	22123792
Catalpa ovata	KNApSAcK Database	22123792
Chamaecyparis obtusa	KNApSAcK Database	22123792
Chrysanthemum cinerariifolium	KNApSAcK Database	22123792
Cinnamomum camphora	KNApSAcK Database	22123792
Cinnamomum kotoense	LOTUS Database	35616633
Cinnamomum subavenium	Plant	KNApSAcK
Cinnamomum tenuifolium	KNApSAcK Database	22123792
Cinnamomum triplinerve	LOTUS Database	35616633
Cleistanthus collinus	LOTUS Database	35616633
Cleistanthus patulus	KNApSAcK Database	22123792
Coleonema pulchellum	KNApSAcK Database	22123792
Corymbia citriodora	LOTUS Database	35616633
Cratoxylum cochinchinense	LOTUS Database	35616633
Cucumis sativus	LOTUS Database	35616633
Cuscuta australis	KNApSAcK Database	22123792
Cuscuta chinensis	LOTUS Database	35616633
Cuscuta japonica	KNApSAcK Database	22123792
Dinosperma stipitatum	LOTUS Database	35616633
Drimys winteri	KNApSAcK Database	22123792
Eleutherococcus divaricatus var. albeofructus	KNApSAcK Database	22123792
Eleutherococcus divaricatus var. chiisanensis	KNApSAcK Database	22123792
Eleutherococcus gracilistylus	KNApSAcK Database	22123792
Eleutherococcus obovatus	KNApSAcK Database	22123792
Eleutherococcus senticosus	KNApSAcK Database	22123792
Eleutherococcus sessiliflorus	KNApSAcK Database	22123792
Endiandra xanthocarpa	KNApSAcK Database	22123792
Eremophila phyllopoda	LOTUS Database	35616633
Esenbeckia leiocarpa	LOTUS Database	35616633
Eucalyptus citriodora	KNApSAcK Database	22123792
Fagara chalybea	KNApSAcK Database	22123792
Fagara heitzii	KNApSAcK Database	22123792
Fagara macrophylla	KNApSAcK Database	22123792
Fagara rhetze	KNApSAcK Database	22123792
Fagara xanthoxyloides	KNApSAcK Database	22123792
Fleischmannia microstemon	KNApSAcK Database	22123792
Forsythia suspensa	LOTUS Database	35616633
Ginkgo biloba	KNApSAcK Database	22123792
Gonospermum fruticosum	LOTUS Database	35616633
Gonospermum gomerae	LOTUS Database	35616633
Horsfieldia irya	LOTUS Database	35616633
Houttuynia cordata	KNApSAcK Database	22123792
Hydrocotyle sibthorpioides	KNApSAcK Database	22123792
Hypenia salzmannii	LOTUS Database	35616633
Hypericum chinense	LOTUS Database	35616633
Hyptis salzmanii	KNApSAcK Database	22123792
Hyptis tomentosa	KNApSAcK Database	22123792
Juniperus communis	LOTUS Database	35616633
Juniperus thurifera	KNApSAcK Database	22123792
Justicia hyssopifolia	KNApSAcK Database	22123792
Justicia simplex	KNApSAcK Database	22123792
Lancea tibetica	KNApSAcK Database	22123792
Leucanthemopsis pallida	LOTUS Database	35616633
Leucanthemopsis pulverulenta	KNApSAcK Database	22123792
Lindera praecox	LOTUS Database	35616633
Machilus glaucescens	KNApSAcK Database	22123792
Machilus thunbergii	KNApSAcK Database	22123792
Magnolia coco	KNApSAcK Database	22123792
Magnolia denudata	KNApSAcK Database	22123792
Magnolia grandiflora var. rubra	KNApSAcK Database	22123792
Magnolia kobus	LOTUS Database	35616633
Magnolia kobus var. borealis	KNApSAcK Database	22123792
Magnolia mutabilis	KNApSAcK Database	22123792
Magnolia praecocissima	KNApSAcK Database	22123792
Magnolia pterocarpa	KNApSAcK Database	22123792
Magnolia stellata	KNApSAcK Database	22123792
Markhamia platycalyx	LOTUS Database	35616633
Melicope elleryana	LOTUS Database	35616633
Melicope stipitata	KNApSAcK Database	22123792
Nectandra amazonum	LOTUS Database	35616633
Nectandra amazonumm	KNApSAcK Database	22123792
Nectandra turbacensis	KNApSAcK Database	22123792
Oplopanax horridus	LOTUS Database	35616633
Otanthus maritimus	KNApSAcK Database	22123792
Pandanus boninensis	LOTUS Database	35616633
Paulownia taiwaniana	KNApSAcK Database	22123792
Paulownia tomentosa	KNApSAcK Database	22123792
Peperomia blanda	LOTUS Database	35616633
Peperomia leptostachya	LOTUS Database	35616633
Peperomia pellucida	LOTUS Database	35616633
Peperomia sui	KNApSAcK Database	22123792
Peperomia vulcanica	LOTUS Database	35616633
Persea kurzii	KNApSAcK Database	22123792
Phaylopsis falcisepala	KNApSAcK Database	22123792
Philotheca citrina	KNApSAcK Database	22123792
Phoebe mexicana	KNApSAcK Database	22123792
Phyllarthron comorense	KNApSAcK Database	22123792
Piper austrosinense	KNApSAcK Database	22123792
Piper brachystachyum	KNApSAcK Database	22123792
Piper guineense	LOTUS Database	35616633
Piper longum	KNApSAcK Database	22123792
Piper mullesua	KNApSAcK Database	22123792
Piper retrofractum	KNApSAcK Database	22123792
Piper sarmentosum	KNApSAcK Database	22123792
Piper sintenense	LOTUS Database	35616633
Piper sylvaticum	KNApSAcK Database	22123792
Podolepis rugata	LOTUS Database	35616633
Raulinoa echinata	KNApSAcK Database	22123792
Ruta montana	KNApSAcK Database	22123792
Samadera bidwillii	LOTUS Database	35616633
Senecio magnificus	LOTUS Database	35616633
Sesamum alatum	KNApSAcK Database	22123792
Sesamum angolense	KNApSAcK Database	22123792
Sesamum angustifolium	KNApSAcK Database	22123792
Sesamum capense	LOTUS Database	35616633
Sesamum indicum	KNApSAcK Database	22123792
Sesamum latifolium	KNApSAcK Database	22123792
Sesamum radiatum	KNApSAcK Database	22123792
Sideritis argosphacelus var. spicata	KNApSAcK Database	22123792
Sideritis canariensis	KNApSAcK Database	22123792
Sideritis candicans	LOTUS Database	35616633
Sideritis cretica	LOTUS Database	35616633
Sideritis discolor	KNApSAcK Database	22123792
Sideritis kuegleriana	KNApSAcK Database	22123792
Sideritis massoniana	KNApSAcK Database	22123792
Sideritis tenoi	KNApSAcK Database	22123792
Stemona collinsae	KNApSAcK Database	22123792
Streptomyces	NPAtlas	15792856
Strychnos cathayensis	KNApSAcK Database	22123792
Taiwanofungus camphoratus	Fungi	KNApSAcK
Talauma hodgsoni	KNApSAcK Database	22123792
Talauma hodgsonii	KNApSAcK Database	22123792
Taxus mairei	KNApSAcK Database	22123792
Turraeanthus africanus	LOTUS Database	35616633
Virola flexuosa	LOTUS Database	35616633
Virola michelii	KNApSAcK Database	22123792
Virola sebifera	KNApSAcK Database	22123792
Virola surinamensis	KNApSAcK Database	22123792
Vismia guaramirangae	KNApSAcK Database	22123792
Vitex negundo	LOTUS Database	35616633
Xanthium spinosum	KNApSAcK Database	22123792
Xanthoxylum tingoassuiba	Plant	KNApSAcK
Zanthoxylum acanthopodium	KNApSAcK Database	22123792
Zanthoxylum ailanthoides	Plant	KNApSAcK
Zanthoxylum alatum	KNApSAcK Database	22123792
Zanthoxylum americanum	KNApSAcK Database	22123792
Zanthoxylum armatum	KNApSAcK Database	22123792
Zanthoxylum arnottianum	KNApSAcK Database	22123792
Zanthoxylum beecheyanum	LOTUS Database	35616633
Zanthoxylum bungeanum	KNApSAcK Database	22123792
Zanthoxylum capense	KNApSAcK Database	22123792
Zanthoxylum caudatum	KNApSAcK Database	22123792
Zanthoxylum chalybeum	KNApSAcK Database	22123792
Zanthoxylum clava-herculis	KNApSAcK Database	22123792
Zanthoxylum conspersipunctatum	KNApSAcK Database	22123792
Zanthoxylum culantrillo	KNApSAcK Database	22123792
Zanthoxylum gilletii	LOTUS Database	35616633
Zanthoxylum integrifoliolum	KNApSAcK Database	22123792
Zanthoxylum leprieurii	LOTUS Database	35616633
Zanthoxylum martinicense	KNApSAcK Database	22123792
Zanthoxylum naranjillo	KNApSAcK Database	22123792
Zanthoxylum nitidum	KNApSAcK Database	22123792
Zanthoxylum oxyphyllum	KNApSAcK Database	22123792
Zanthoxylum petiolare	KNApSAcK Database	22123792
Zanthoxylum piperitum	KNApSAcK Database	22123792
Zanthoxylum pluviatile	KNApSAcK Database	22123792
Zanthoxylum podocarpum	KNApSAcK Database	22123792
Zanthoxylum rhetsa	KNApSAcK Database	22123792
Zanthoxylum rhoifolium	LOTUS Database	35616633
Zanthoxylum rubescens	KNApSAcK Database	22123792
Zanthoxylum setulosum	LOTUS Database	35616633
Zanthoxylum sp.	KNApSAcK Database	22123792
Zanthoxylum sprucei	KNApSAcK Database	22123792
Zanthoxylum tetraspermum	KNApSAcK Database	22123792
Zanthoxylum tingoassuiba	KNApSAcK Database	22123792
Zanthoxylum usambarense	KNApSAcK Database	22123792
Zanthoxylum valens	KNApSAcK Database	22123792
Zanthoxylum zanthoxyloides	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furanoid lignans. These are lignans with a structure that contains either a tetrahydrofuran ring, a furan ring, or a furofuan ring system, that arises from the joining of the two phenylpropanoid units.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Furanoid lignans

Sub Class

Not Available

Direct Parent

Furanoid lignans

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	123.00 to 124.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	504.00 to 505.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	6.56 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	4.064 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
logP	2.25	ALOGPS
logP	2.45	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	55.38 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	89.75 m³·mol⁻¹	ChemAxon
Polarizability	36.74 Å³	ChemAxon
Number of Rings	6	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

NPAtlas ID

NPA017796

HMDB ID

HMDB0034256

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Sesamin

METLIN ID

Not Available

PubChem Compound

72307

PDB ID

Not Available

ChEBI ID

66470

Good Scents ID

rw1538831

References

General References

Hsieh TJ, Lu LH, Su CC: NMR spectroscopic, mass spectroscopic, X-ray crystallographic, and theoretical studies of molecular mechanics of natural products: farformolide B and sesamin. Biophys Chem. 2005 Apr 1;114(1):13-20. doi: 10.1016/j.bpc.2004.10.001. Epub 2004 Nov 5. [PubMed:15792856 ]
Ono E, Nakai M, Fukui Y, Tomimori N, Fukuchi-Mizutani M, Saito M, Satake H, Tanaka T, Katsuta M, Umezawa T, Tanaka Y: Formation of two methylenedioxy bridges by a Sesamum CYP81Q protein yielding a furofuran lignan, (+)-sesamin. Proc Natl Acad Sci U S A. 2006 Jun 27;103(26):10116-21. doi: 10.1073/pnas.0603865103. Epub 2006 Jun 19. [PubMed:16785429 ]
Li CY, Chow TJ, Wu TS: The epimerization of sesamin and asarinin. J Nat Prod. 2005 Nov;68(11):1622-4. doi: 10.1021/np050106d. [PubMed:16309310 ]

Showing NP-Card for Sesamin (NP0005798)

MOL for NP0005798 (Sesamin)

3D MOL for NP0005798 (Sesamin)

3D SDF for NP0005798 (Sesamin)

3D-SDF for NP0005798 (Sesamin)

PDB for NP0005798 (Sesamin)

3D PDB for NP0005798 (Sesamin)

SMILES for NP0005798 (Sesamin)

INCHI for NP0005798 (Sesamin)

Structure for NP0005798 (Sesamin)

3D Structure for NP0005798 (Sesamin)