NP-MRD: Showing NP-Card for alpha-Peltatin (NP0051513)

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Record Information

Version

2.0

Created at

2022-04-27 22:51:07 UTC

Updated at

2022-04-27 22:51:07 UTC

NP-MRD ID

NP0051513

Secondary Accession Numbers

None

Natural Product Identification

Common Name

alpha-Peltatin

Description

Alpha-peltatin, also known as α-peltatin a or nci 1074, belongs to the class of organic compounds known as lignan lactones. These are lignans that contain a lactone moiety. They include 1-aryltetralin lactones, dibenzylbutyrolactone lignans, and podophyllotoxins, among others. Alpha-peltatin 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. alpha-Peltatin is found in Amanoa oblongifolia, Diphylleia grayi, Eriope blanchetii, Eriope latifolia, Eriope macrostachya, Hugonia tomentosa, Linum album, Linum capitatum, Linum flavum var. compactum, Linum perenne, Podophyllum hexandrum and Podophyllum peltatum . alpha-Peltatin was first documented in 2011 (PMID: 21889175). Based on a literature review a small amount of articles have been published on alpha-peltatin (PMID: 23418155) (PMID: 33645032) (PMID: 29905994).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282200512D          

 29 33  0  0  1  0            999 V2000
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5658    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0508    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5658    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    4.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    5.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    5.6479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2089    4.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2089    5.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    2.9750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   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
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  3 10  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  1 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 18 23  1  0  0  0  0
 17 24  1  0  0  0  0
 24 25  1  0  0  0  0
 13 26  1  6  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 12 29  1  1  0  0  0
M  END

     RDKit          3D

 49 53  0  0  0  0  0  0  0  0999 V2000
    3.9939   -2.4425    1.8912 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3652   -1.1618    1.4324 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4584   -0.4028    0.7130 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1900   -0.8979    0.4435 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2682   -0.1880   -0.2572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0558   -0.7260   -0.5197 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1927    0.2304   -0.3587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1169    1.4510    0.2494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2635    2.2528    0.2672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4462    1.8390   -0.3073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4822    0.5653   -0.9258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6934    0.2041   -1.4841 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3781   -0.2105   -0.9436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3568   -1.5897   -1.4919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8989   -2.3529   -0.3368 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8181   -3.8040   -0.2516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9473   -3.9371    0.9161 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3615   -2.6451    1.1729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0251   -2.3453    2.3264 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3738   -2.0805   -0.1573 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3803    2.8330   -0.1311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6837    4.0259    0.1543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5040    3.5164    0.7939 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6188    1.0636   -0.7117 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8688    1.6039   -0.4713 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2631    2.8444   -0.9026 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3796    3.6901   -1.6541 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7752    0.8503    0.2457 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0479    1.3415    0.5190 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1953   -2.4281    2.6482 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6546   -3.1037    1.0717 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9014   -2.9165    2.3559 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0121   -1.9139    0.8211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0234   -0.7730   -1.7056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2243    1.8032    0.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9198   -0.6311   -1.9552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6599   -1.6734   -2.3404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3557   -1.8921   -1.8874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3506   -1.9521    0.6203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7526   -4.3493   -0.0799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2777   -4.2473   -1.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1239   -2.8418   -0.8335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2548    4.6928    0.8137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4351    4.4919   -0.8279 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9537    1.7056   -1.2952 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8989    3.0910   -2.4764 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9158    4.5036   -2.1431 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6369    4.1156   -0.9626 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7103    0.7912    1.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5 24  2  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 25 28  2  0
 28 29  1  0
  5  6  1  0
  6 20  1  0
 20 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 15 14  1  0
 14 13  1  0
 13  7  2  0
  7  8  1  0
  8  9  2  0
  9 23  1  0
 23 22  1  0
 22 21  1  0
 21 10  1  0
 10 11  2  0
 11 12  1  0
 28  3  1  0
  7  6  1  0
 10  9  1  0
 18 20  1  0
 11 13  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  4 33  1  0
 24 45  1  0
 27 46  1  0
 27 47  1  0
 27 48  1  0
 29 49  1  0
  6 34  1  6
 20 42  1  6
 15 39  1  1
 16 40  1  0
 16 41  1  0
 14 37  1  0
 14 38  1  0
  8 35  1  0
 22 43  1  0
 22 44  1  0
 12 36  1  0
M  END


  Mrv1652304282200512D          

 29 33  0  0  1  0            999 V2000
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5658    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0508    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5658    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    4.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    5.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    5.6479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2089    4.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2089    5.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    2.9750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   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
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  3 10  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  1 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 18 23  1  0  0  0  0
 17 24  1  0  0  0  0
 24 25  1  0  0  0  0
 13 26  1  6  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 12 29  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0051513

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC(OC)=C1O)[C@H]1[C@@H]2[C@H](COC2=O)CC2=C1C=C1OCOC1=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C21H20O8/c1-25-13-4-9(5-14(26-2)19(13)23)16-11-6-15-20(29-8-28-15)18(22)12(11)3-10-7-27-21(24)17(10)16/h4-6,10,16-17,22-23H,3,7-8H2,1-2H3/t10-,16+,17-/m0/s1

> <INCHI_KEY>
JGGWNGRBXJWAOC-HKJPBSJPSA-N

> <FORMULA>
C21H20O8

> <MOLECULAR_WEIGHT>
400.383

> <EXACT_MASS>
400.115817604

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
39.825527112062616

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(10R,11R,15R)-2-hydroxy-10-(4-hydroxy-3,5-dimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1(9),2,7-trien-12-one

> <ALOGPS_LOGP>
2.36

> <JCHEM_LOGP>
2.3625932316666667

> <ALOGPS_LOGS>
-3.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.771738639390003

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.13526515299749

> <JCHEM_PKA_STRONGEST_BASIC>
-4.380947854764271

> <JCHEM_POLAR_SURFACE_AREA>
103.68000000000002

> <JCHEM_REFRACTIVITY>
99.98689999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.24e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(10R,11R,15R)-2-hydroxy-10-(4-hydroxy-3,5-dimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1(9),2,7-trien-12-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.591   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.925   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.925   3.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      10.390   4.089   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      11.295   2.843   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      10.390   1.597   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       7.591  -0.237   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.924   5.923   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.590   6.693   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.590   8.233   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.924   9.003   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.258   8.233   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.258   6.693   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.591   9.003   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       7.591  10.543   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.924  10.543   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       2.257   9.003   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.257  10.543   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.650   5.553   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       1.220   2.843   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
CONECT    1    2    6   14                                                  
CONECT    2    1    3   11                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    4                                                       
CONECT   10    3                                                            
CONECT   11    2   12                                                       
CONECT   12   11   13   29                                                  
CONECT   13   12   14   26                                                  
CONECT   14   13    1   15                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   24                                                  
CONECT   18   17   19   23                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19   15                                                       
CONECT   21   19   22                                                       
CONECT   22   21                                                            
CONECT   23   18                                                            
CONECT   24   17   25                                                       
CONECT   25   24                                                            
CONECT   26   13   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   12                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

View in JSmol

Synonyms

Value	Source
8-Hydroxy-2-hydroxymethyl-6,7-methylenedioxy-4-(4'-hydroxy-3',5'-dimethoxyphenyl)-1,2,3,4-tetrahydronaphthalene-3-carboxylic acid lactone	ChEBI
[5R-(5alpha,5Aalpha,5abeta,8aalpha)]-5,8,8a,9-tetrahydro-10-hydroxy-5-(4-hydroxy-3,5-dimethoxyphenyl)furo[3',3':6,7]naphtho[2,3-D]-1,3-dioxo-6(5ah)-one	ChEBI
alpha-Peltatin a	ChEBI
NCI 1074	ChEBI
NSC 24817	ChEBI
8-Hydroxy-2-hydroxymethyl-6,7-methylenedioxy-4-(4'-hydroxy-3',5'-dimethoxyphenyl)-1,2,3,4-tetrahydronaphthalene-3-carboxylate lactone	Generator
[5R-(5a,5Aalpha,5abeta,8aalpha)]-5,8,8a,9-tetrahydro-10-hydroxy-5-(4-hydroxy-3,5-dimethoxyphenyl)furo[3',3':6,7]naphtho[2,3-D]-1,3-dioxo-6(5ah)-one	Generator
[5R-(5Α,5aalpha,5abeta,8aalpha)]-5,8,8a,9-tetrahydro-10-hydroxy-5-(4-hydroxy-3,5-dimethoxyphenyl)furo[3',3':6,7]naphtho[2,3-D]-1,3-dioxo-6(5ah)-one	Generator
a-Peltatin a	Generator
Α-peltatin a	Generator
a-Peltatin	Generator
Α-peltatin	Generator

Chemical Formula

C₂₁H₂₀O₈

Average Mass

400.3830 Da

Monoisotopic Mass

400.11582 Da

IUPAC Name

(10R,11R,15R)-2-hydroxy-10-(4-hydroxy-3,5-dimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1(9),2,7-trien-12-one

Traditional Name

(10R,11R,15R)-2-hydroxy-10-(4-hydroxy-3,5-dimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1(9),2,7-trien-12-one

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC(OC)=C1O)[C@H]1[C@@H]2[C@H](COC2=O)CC2=C1C=C1OCOC1=C2O

InChI Identifier

InChI=1S/C21H20O8/c1-25-13-4-9(5-14(26-2)19(13)23)16-11-6-15-20(29-8-28-15)18(22)12(11)3-10-7-27-21(24)17(10)16/h4-6,10,16-17,22-23H,3,7-8H2,1-2H3/t10-,16+,17-/m0/s1

InChI Key

JGGWNGRBXJWAOC-HKJPBSJPSA-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
Amanoa oblongifolia	Plant	KNApSAcK
Diphylleia grayi	LOTUS Database	35616633
Eriope blanchetii	Plant	KNApSAcK
Eriope latifolia	LOTUS Database	35616633
Eriope macrostachya	Plant	KNApSAcK
Hugonia tomentosa	Plant	KNApSAcK
Linum album	Plant	KNApSAcK
Linum capitatum	LOTUS Database	35616633
Linum flavum var. compactum	Plant	KNApSAcK
Linum perenne	LOTUS Database	35616633
Podophyllum hexandrum	Plant	KNApSAcK
Podophyllum peltatum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lignan lactones. These are lignans that contain a lactone moiety. They include 1-aryltetralin lactones, dibenzylbutyrolactone lignans, and podophyllotoxins, among others.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Lignan lactones

Sub Class

Not Available

Direct Parent

Lignan lactones

Alternative Parents

Substituents

Lignan lactone
1-aryltetralin lignan
Linear furanonaphthodioxole
Naphthofuran
Methoxyphenol
Tetralin
Dimethoxybenzene
M-dimethoxybenzene
Benzodioxole
Anisole
Phenoxy compound
Phenol ether
Methoxybenzene
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Gamma butyrolactone
Tetrahydrofuran
Lactone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Acetal
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic heterotetracyclic compound (CHEBI:10324 )
phenols (CHEBI:10324 )
gamma-lactone (CHEBI:10324 )
lignan (CHEBI:10324 )
furonaphthodioxole (CHEBI:10324 )
Lignans (C10729 )

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	2.36	ALOGPS
logP	2.36	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	9.14	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	103.68 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	99.99 m³·mol⁻¹	ChemAxon
Polarizability	39.83 Å³	ChemAxon
Number of Rings	5	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

C00002615

Chemspider ID

83175

KEGG Compound ID

C10729

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

92129

PDB ID

Not Available

ChEBI ID

10324

Good Scents ID

Not Available

References

General References

Yang Z, Liu X, Wang K, Cao X, Wu S: Novel linear and step-gradient counter-current chromatography for bio-guided isolation and purification of cytotoxic podophyllotoxins from Dysosma versipellis (Hance). J Sep Sci. 2013 Mar;36(6):1022-8. doi: 10.1002/jssc.201201038. Epub 2013 Feb 18. [PubMed:23418155 ]
Fan SS, Shang MY, Xu F, Liu GX, Li YL, Cai SQ: [Identification of chemical constituents in ethyl acetate soluble extract of Sinopodophylli Fructus based on HPLC-MS~n]. Zhongguo Zhong Yao Za Zhi. 2021 Feb;46(3):645-660. doi: 10.19540/j.cnki.cjcmm.20200629.203. [PubMed:33645032 ]
Peng LF, Lu LH, Yang LG, Lu XP, Cui T, Zhu ZY: [A new biflavone from Dysosma versipellis]. Yao Xue Xue Bao. 2016 Aug;51(8):1281-4. [PubMed:29905994 ]
Hendrawati O, Woerdenbag HJ, Michiels PJ, Aantjes HG, van Dam A, Kayser O: Identification of lignans and related compounds in Anthriscus sylvestris by LC-ESI-MS/MS and LC-SPE-NMR. Phytochemistry. 2011 Dec;72(17):2172-9. doi: 10.1016/j.phytochem.2011.08.009. Epub 2011 Aug 31. [PubMed:21889175 ]

Showing NP-Card for alpha-Peltatin (NP0051513)

MOL for NP0051513 (alpha-Peltatin)

3D MOL for NP0051513 (alpha-Peltatin)

3D SDF for NP0051513 (alpha-Peltatin)

3D-SDF for NP0051513 (alpha-Peltatin)

PDB for NP0051513 (alpha-Peltatin)

3D PDB for NP0051513 (alpha-Peltatin)

SMILES for NP0051513 (alpha-Peltatin)

INCHI for NP0051513 (alpha-Peltatin)

Structure for NP0051513 (alpha-Peltatin)

3D Structure for NP0051513 (alpha-Peltatin)