NP-MRD: Showing NP-Card for (3S,7R)-5,6-dehydro-1,7-bis(4-hydroxyphenyl)-4''-de-O-methylcentrolobine (NP0025598)

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Record Information

Version

2.0

Created at

2021-06-19 17:40:41 UTC

Updated at

2021-06-29 23:50:39 UTC

NP-MRD ID

NP0025598

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3S,7R)-5,6-dehydro-1,7-bis(4-hydroxyphenyl)-4''-de-O-methylcentrolobine

Provided By

JEOL Database JEOL Logo

Description

(3S,7R)-5,6-dehydro-1,7-bis(4-hydroxyphenyl)-4''-de-O-methylcentrolobine is found in Alpinia blepharocalyx and Alpinia roxburghii. (3S,7R)-5,6-dehydro-1,7-bis(4-hydroxyphenyl)-4''-de-O-methylcentrolobine was first documented in 2001 (Ali, M. S., et al.). Based on a literature review very few articles have been published on CHEMBL478712.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192119403D          

 42 44  0  0  0  0            999 V2000
   -4.7045    0.7226   -0.3990 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6535   -0.1120   -0.1573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6260   -0.2656   -1.0808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5666   -1.1268   -0.7896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5261   -1.8279    0.4235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3557   -2.7255    0.7447 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6064   -2.1245    1.7778 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3591   -0.8865    1.2692 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2539   -0.3081    2.3792 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1716    0.7443    1.8338 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4150    0.8147    0.5163 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8377   -0.1608   -0.4825 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9397    0.4464   -1.5498 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1528    1.5875   -1.3203 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3122    2.0879   -2.3175 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2462    1.4496   -3.5488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5975    1.9642   -4.4882 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0084    0.3158   -3.8032 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8475   -0.1850   -2.8041 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1664   -1.2680    0.1460 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5746   -1.6622    1.3387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6377   -0.8058    1.0466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5623    1.1461   -1.2617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6232    0.2748   -2.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7602   -1.2368   -1.5111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1852   -2.9864   -0.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7493   -3.6738    1.1331 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3364   -2.9029    2.0355 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0621   -1.8745    2.6967 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6330   -0.1269    0.9570 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8715   -1.0936    2.8309 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6274    0.1208    3.1693 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6376    1.4401    2.5245 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0799    1.5812    0.1281 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7008   -0.6001   -1.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1732    2.0917   -0.3568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2943    2.9687   -2.1273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4935    1.4530   -5.3076 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9572   -0.1967   -4.7585 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4261   -1.0861   -3.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5688   -2.1972    2.2852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4486   -0.6774    1.7575 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
 11 12  1  0  0  0  0
  3  2  2  0  0  0  0
 12 20  1  0  0  0  0
  2 22  1  0  0  0  0
 22 21  2  0  0  0  0
 21  5  1  0  0  0  0
  8  7  1  0  0  0  0
  8  9  1  0  0  0  0
 13 14  2  0  0  0  0
  7  6  1  0  0  0  0
 14 15  1  0  0  0  0
  8 20  1  0  0  0  0
 15 16  2  0  0  0  0
  6  5  1  0  0  0  0
 16 18  1  0  0  0  0
  9 10  1  0  0  0  0
 18 19  2  0  0  0  0
 19 13  1  0  0  0  0
 12 13  1  0  0  0  0
  5  4  2  0  0  0  0
  2  1  1  0  0  0  0
 10 11  2  0  0  0  0
 16 17  1  0  0  0  0
  8 30  1  6  0  0  0
  9 31  1  0  0  0  0
  9 32  1  0  0  0  0
 10 33  1  0  0  0  0
 11 34  1  0  0  0  0
 12 35  1  6  0  0  0
  7 28  1  0  0  0  0
  7 29  1  0  0  0  0
  6 26  1  0  0  0  0
  6 27  1  0  0  0  0
  4 25  1  0  0  0  0
  3 24  1  0  0  0  0
 22 42  1  0  0  0  0
 21 41  1  0  0  0  0
 14 36  1  0  0  0  0
 15 37  1  0  0  0  0
 18 39  1  0  0  0  0
 19 40  1  0  0  0  0
  1 23  1  0  0  0  0
 17 38  1  0  0  0  0
M  END

     RDKit          3D

 42 44  0  0  0  0  0  0  0  0999 V2000
   -4.7045    0.7226   -0.3990 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6535   -0.1120   -0.1573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6260   -0.2656   -1.0808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5666   -1.1268   -0.7896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5261   -1.8279    0.4235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3557   -2.7255    0.7447 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6064   -2.1245    1.7778 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3591   -0.8865    1.2692 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2539   -0.3081    2.3792 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1716    0.7443    1.8338 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4150    0.8147    0.5163 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8377   -0.1608   -0.4825 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9397    0.4464   -1.5498 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1528    1.5875   -1.3203 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3122    2.0879   -2.3175 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2462    1.4496   -3.5488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5975    1.9642   -4.4882 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0084    0.3158   -3.8032 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8475   -0.1850   -2.8041 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1664   -1.2680    0.1460 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5746   -1.6622    1.3387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6377   -0.8058    1.0466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5623    1.1461   -1.2617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6232    0.2748   -2.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7602   -1.2368   -1.5111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1852   -2.9864   -0.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7493   -3.6738    1.1331 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3364   -2.9029    2.0355 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0621   -1.8745    2.6967 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6330   -0.1269    0.9570 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8715   -1.0936    2.8309 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6274    0.1208    3.1693 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6376    1.4401    2.5245 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0799    1.5812    0.1281 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7008   -0.6001   -1.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1732    2.0917   -0.3568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2943    2.9687   -2.1273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4935    1.4530   -5.3076 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9572   -0.1967   -4.7585 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4261   -1.0861   -3.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5688   -2.1972    2.2852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4486   -0.6774    1.7575 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0
 11 12  1  0
  3  2  2  0
 12 20  1  0
  2 22  1  0
 22 21  2  0
 21  5  1  0
  8  7  1  0
  8  9  1  0
 13 14  2  0
  7  6  1  0
 14 15  1  0
  8 20  1  0
 15 16  2  0
  6  5  1  0
 16 18  1  0
  9 10  1  0
 18 19  2  0
 19 13  1  0
 12 13  1  0
  5  4  2  0
  2  1  1  0
 10 11  2  0
 16 17  1  0
  8 30  1  6
  9 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 12 35  1  6
  7 28  1  0
  7 29  1  0
  6 26  1  0
  6 27  1  0
  4 25  1  0
  3 24  1  0
 22 42  1  0
 21 41  1  0
 14 36  1  0
 15 37  1  0
 18 39  1  0
 19 40  1  0
  1 23  1  0
 17 38  1  0
M  END


  Mrv1652306192119403D          

 42 44  0  0  0  0            999 V2000
   -4.7045    0.7226   -0.3990 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6535   -0.1120   -0.1573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6260   -0.2656   -1.0808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5666   -1.1268   -0.7896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5261   -1.8279    0.4235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3557   -2.7255    0.7447 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6064   -2.1245    1.7778 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3591   -0.8865    1.2692 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2539   -0.3081    2.3792 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1716    0.7443    1.8338 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4150    0.8147    0.5163 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8377   -0.1608   -0.4825 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9397    0.4464   -1.5498 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1528    1.5875   -1.3203 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3122    2.0879   -2.3175 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2462    1.4496   -3.5488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5975    1.9642   -4.4882 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0084    0.3158   -3.8032 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8475   -0.1850   -2.8041 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1664   -1.2680    0.1460 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5746   -1.6622    1.3387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6377   -0.8058    1.0466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5623    1.1461   -1.2617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6232    0.2748   -2.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7602   -1.2368   -1.5111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1852   -2.9864   -0.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7493   -3.6738    1.1331 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3364   -2.9029    2.0355 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0621   -1.8745    2.6967 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6330   -0.1269    0.9570 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8715   -1.0936    2.8309 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6274    0.1208    3.1693 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6376    1.4401    2.5245 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0799    1.5812    0.1281 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7008   -0.6001   -1.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1732    2.0917   -0.3568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2943    2.9687   -2.1273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4935    1.4530   -5.3076 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9572   -0.1967   -4.7585 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4261   -1.0861   -3.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5688   -2.1972    2.2852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4486   -0.6774    1.7575 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
 11 12  1  0  0  0  0
  3  2  2  0  0  0  0
 12 20  1  0  0  0  0
  2 22  1  0  0  0  0
 22 21  2  0  0  0  0
 21  5  1  0  0  0  0
  8  7  1  0  0  0  0
  8  9  1  0  0  0  0
 13 14  2  0  0  0  0
  7  6  1  0  0  0  0
 14 15  1  0  0  0  0
  8 20  1  0  0  0  0
 15 16  2  0  0  0  0
  6  5  1  0  0  0  0
 16 18  1  0  0  0  0
  9 10  1  0  0  0  0
 18 19  2  0  0  0  0
 19 13  1  0  0  0  0
 12 13  1  0  0  0  0
  5  4  2  0  0  0  0
  2  1  1  0  0  0  0
 10 11  2  0  0  0  0
 16 17  1  0  0  0  0
  8 30  1  6  0  0  0
  9 31  1  0  0  0  0
  9 32  1  0  0  0  0
 10 33  1  0  0  0  0
 11 34  1  0  0  0  0
 12 35  1  6  0  0  0
  7 28  1  0  0  0  0
  7 29  1  0  0  0  0
  6 26  1  0  0  0  0
  6 27  1  0  0  0  0
  4 25  1  0  0  0  0
  3 24  1  0  0  0  0
 22 42  1  0  0  0  0
 21 41  1  0  0  0  0
 14 36  1  0  0  0  0
 15 37  1  0  0  0  0
 18 39  1  0  0  0  0
 19 40  1  0  0  0  0
  1 23  1  0  0  0  0
 17 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0025598

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])[C@]1([H])O[C@]([H])(C([H])=C([H])C1([H])[H])C1=C([H])C([H])=C(O[H])C([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C19H20O3/c20-16-9-4-14(5-10-16)6-13-18-2-1-3-19(22-18)15-7-11-17(21)12-8-15/h1,3-5,7-12,18-21H,2,6,13H2/t18-,19-/m1/s1

> <INCHI_KEY>
WNMSDVNIAXMQRI-RTBURBONSA-N

> <FORMULA>
C19H20O3

> <MOLECULAR_WEIGHT>
296.366

> <EXACT_MASS>
296.141244504

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
31.96707802799103

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(2R,6S)-6-[2-(4-hydroxyphenyl)ethyl]-5,6-dihydro-2H-pyran-2-yl]phenol

> <ALOGPS_LOGP>
4.01

> <JCHEM_LOGP>
4.4634809713333325

> <ALOGPS_LOGS>
-4.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.356136946805085

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.40791448588664

> <JCHEM_PKA_STRONGEST_BASIC>
-4.227871695242909

> <JCHEM_POLAR_SURFACE_AREA>
49.69

> <JCHEM_REFRACTIVITY>
88.00050000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.10e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[(2R,6S)-6-[2-(4-hydroxyphenyl)ethyl]-5,6-dihydro-2H-pyran-2-yl]phenol

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 42 44  0  0  0  0  0  0  0  0999 V2000
   -4.7045    0.7226   -0.3990 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6535   -0.1120   -0.1573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6260   -0.2656   -1.0808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5666   -1.1268   -0.7896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5261   -1.8279    0.4235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3557   -2.7255    0.7447 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6064   -2.1245    1.7778 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3591   -0.8865    1.2692 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2539   -0.3081    2.3792 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1716    0.7443    1.8338 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4150    0.8147    0.5163 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8377   -0.1608   -0.4825 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9397    0.4464   -1.5498 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1528    1.5875   -1.3203 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3122    2.0879   -2.3175 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2462    1.4496   -3.5488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5975    1.9642   -4.4882 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0084    0.3158   -3.8032 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8475   -0.1850   -2.8041 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1664   -1.2680    0.1460 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5746   -1.6622    1.3387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6377   -0.8058    1.0466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5623    1.1461   -1.2617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6232    0.2748   -2.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7602   -1.2368   -1.5111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1852   -2.9864   -0.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7493   -3.6738    1.1331 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3364   -2.9029    2.0355 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0621   -1.8745    2.6967 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6330   -0.1269    0.9570 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8715   -1.0936    2.8309 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6274    0.1208    3.1693 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6376    1.4401    2.5245 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0799    1.5812    0.1281 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7008   -0.6001   -1.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1732    2.0917   -0.3568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2943    2.9687   -2.1273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4935    1.4530   -5.3076 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9572   -0.1967   -4.7585 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4261   -1.0861   -3.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5688   -2.1972    2.2852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4486   -0.6774    1.7575 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0
 11 12  1  0
  3  2  2  0
 12 20  1  0
  2 22  1  0
 22 21  2  0
 21  5  1  0
  8  7  1  0
  8  9  1  0
 13 14  2  0
  7  6  1  0
 14 15  1  0
  8 20  1  0
 15 16  2  0
  6  5  1  0
 16 18  1  0
  9 10  1  0
 18 19  2  0
 19 13  1  0
 12 13  1  0
  5  4  2  0
  2  1  1  0
 10 11  2  0
 16 17  1  0
  8 30  1  6
  9 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 12 35  1  6
  7 28  1  0
  7 29  1  0
  6 26  1  0
  6 27  1  0
  4 25  1  0
  3 24  1  0
 22 42  1  0
 21 41  1  0
 14 36  1  0
 15 37  1  0
 18 39  1  0
 19 40  1  0
  1 23  1  0
 17 38  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  O   UNK     0      -4.705   0.723  -0.399  0.00  0.00           O+0
HETATM    2  C   UNK     0      -3.654  -0.112  -0.157  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.626  -0.266  -1.081  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.567  -1.127  -0.790  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.526  -1.828   0.424  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.356  -2.725   0.745  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.606  -2.124   1.778  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.359  -0.887   1.269  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.254  -0.308   2.379  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.172   0.744   1.834  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.415   0.815   0.516  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.838  -0.161  -0.483  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.940   0.446  -1.550  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.153   1.587  -1.320  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.312   2.088  -2.317  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.246   1.450  -3.549  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.598   1.964  -4.488  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.008   0.316  -3.803  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.847  -0.185  -2.804  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.166  -1.268   0.146  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.575  -1.662   1.339  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.638  -0.806   1.047  0.00  0.00           C+0
HETATM   23  H   UNK     0      -4.562   1.146  -1.262  0.00  0.00           H+0
HETATM   24  H   UNK     0      -2.623   0.275  -2.022  0.00  0.00           H+0
HETATM   25  H   UNK     0      -0.760  -1.237  -1.511  0.00  0.00           H+0
HETATM   26  H   UNK     0       0.185  -2.986  -0.173  0.00  0.00           H+0
HETATM   27  H   UNK     0      -0.749  -3.674   1.133  0.00  0.00           H+0
HETATM   28  H   UNK     0       1.336  -2.903   2.035  0.00  0.00           H+0
HETATM   29  H   UNK     0       0.062  -1.875   2.697  0.00  0.00           H+0
HETATM   30  H   UNK     0       0.633  -0.127   0.957  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.872  -1.094   2.831  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.627   0.121   3.169  0.00  0.00           H+0
HETATM   33  H   UNK     0       3.638   1.440   2.525  0.00  0.00           H+0
HETATM   34  H   UNK     0       4.080   1.581   0.128  0.00  0.00           H+0
HETATM   35  H   UNK     0       3.701  -0.600  -1.000  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.173   2.092  -0.357  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.294   2.969  -2.127  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.494   1.453  -5.308  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.957  -0.197  -4.758  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.426  -1.086  -3.001  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.569  -2.197   2.285  0.00  0.00           H+0
HETATM   42  H   UNK     0      -4.449  -0.677   1.758  0.00  0.00           H+0
CONECT    1    2   23                                                       
CONECT    2    3   22    1                                                  
CONECT    3    4    2   24                                                  
CONECT    4    3    5   25                                                  
CONECT    5   21    6    4                                                  
CONECT    6    7    5   26   27                                             
CONECT    7    8    6   28   29                                             
CONECT    8    7    9   20   30                                             
CONECT    9    8   10   31   32                                             
CONECT   10    9   11   33                                                  
CONECT   11   12   10   34                                                  
CONECT   12   11   20   13   35                                             
CONECT   13   14   19   12                                                  
CONECT   14   13   15   36                                                  
CONECT   15   14   16   37                                                  
CONECT   16   15   18   17                                                  
CONECT   17   16   38                                                       
CONECT   18   16   19   39                                                  
CONECT   19   18   13   40                                                  
CONECT   20   12    8                                                       
CONECT   21   22    5   41                                                  
CONECT   22    2   21   42                                                  
CONECT   23    1                                                            
CONECT   24    3                                                            
CONECT   25    4                                                            
CONECT   26    6                                                            
CONECT   27    6                                                            
CONECT   28    7                                                            
CONECT   29    7                                                            
CONECT   30    8                                                            
CONECT   31    9                                                            
CONECT   32    9                                                            
CONECT   33   10                                                            
CONECT   34   11                                                            
CONECT   35   12                                                            
CONECT   36   14                                                            
CONECT   37   15                                                            
CONECT   38   17                                                            
CONECT   39   18                                                            
CONECT   40   19                                                            
CONECT   41   21                                                            
CONECT   42   22                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   88    0
END

RDKit          3D

42 44  0  0  0  0  0  0  0  0999 V2000
   -4.7045    0.7226   -0.3990 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6535   -0.1120   -0.1573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6260   -0.2656   -1.0808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5666   -1.1268   -0.7896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5261   -1.8279    0.4235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3557   -2.7255    0.7447 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6064   -2.1245    1.7778 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3591   -0.8865    1.2692 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2539   -0.3081    2.3792 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1716    0.7443    1.8338 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4150    0.8147    0.5163 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8377   -0.1608   -0.4825 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9397    0.4464   -1.5498 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1528    1.5875   -1.3203 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3122    2.0879   -2.3175 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2462    1.4496   -3.5488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5975    1.9642   -4.4882 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0084    0.3158   -3.8032 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8475   -0.1850   -2.8041 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1664   -1.2680    0.1460 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5746   -1.6622    1.3387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6377   -0.8058    1.0466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5623    1.1461   -1.2617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6232    0.2748   -2.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7602   -1.2368   -1.5111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1852   -2.9864   -0.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7493   -3.6738    1.1331 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3364   -2.9029    2.0355 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0621   -1.8745    2.6967 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6330   -0.1269    0.9570 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8715   -1.0936    2.8309 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6274    0.1208    3.1693 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6376    1.4401    2.5245 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0799    1.5812    0.1281 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7008   -0.6001   -1.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1732    2.0917   -0.3568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2943    2.9687   -2.1273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4935    1.4530   -5.3076 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9572   -0.1967   -4.7585 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4261   -1.0861   -3.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5688   -2.1972    2.2852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4486   -0.6774    1.7575 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0
 11 12  1  0
  3  2  2  0
 12 20  1  0
  2 22  1  0
 22 21  2  0
 21  5  1  0
  8  7  1  0
  8  9  1  0
 13 14  2  0
  7  6  1  0
 14 15  1  0
  8 20  1  0
 15 16  2  0
  6  5  1  0
 16 18  1  0
  9 10  1  0
 18 19  2  0
 19 13  1  0
 12 13  1  0
  5  4  2  0
  2  1  1  0
 10 11  2  0
 16 17  1  0
  8 30  1  6
  9 31  1  0
  9 32  1  0
 10 33  1  0
 11 34  1  0
 12 35  1  6
  7 28  1  0
  7 29  1  0
  6 26  1  0
  6 27  1  0
  4 25  1  0
  3 24  1  0
 22 42  1  0
 21 41  1  0
 14 36  1  0
 15 37  1  0
 18 39  1  0
 19 40  1  0
  1 23  1  0
 17 38  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₀O₃

Average Mass

296.3660 Da

Monoisotopic Mass

296.14124 Da

IUPAC Name

4-[(2R,6S)-6-[2-(4-hydroxyphenyl)ethyl]-5,6-dihydro-2H-pyran-2-yl]phenol

Traditional Name

4-[(2R,6S)-6-[2-(4-hydroxyphenyl)ethyl]-5,6-dihydro-2H-pyran-2-yl]phenol

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])[C@]1([H])O[C@]([H])(C([H])=C([H])C1([H])[H])C1=C([H])C([H])=C(O[H])C([H])=C1[H]

InChI Identifier

InChI=1S/C19H20O3/c20-16-9-4-14(5-10-16)6-13-18-2-1-3-19(22-18)15-7-11-17(21)12-8-15/h1,3-5,7-12,18-21H,2,6,13H2/t18-,19-/m1/s1

InChI Key

WNMSDVNIAXMQRI-RTBURBONSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Alpinia blepharocalyx	JEOL database	Ali, M. S., et al, J. Nat. Prod. 64, 491 (2001)
Alpinia roxburghii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as linear diarylheptanoids. These are diarylheptanoids with an open heptane chain. The two aromatic rings are linked only by the heptane chain.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Diarylheptanoids

Sub Class

Linear diarylheptanoids

Direct Parent

Linear diarylheptanoids

Alternative Parents

Substituents

Linear 1,7-diphenylheptane skeleton
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Pyran
Monocyclic benzene moiety
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
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	4.01	ALOGPS
logP	4.46	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	9.41	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.69 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	88 m³·mol⁻¹	ChemAxon
Polarizability	31.97 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	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8955580

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10780267

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ali, M. S., et al. (2001). Ali, M. S., et al, J. Nat. Prod. 64, 491 (2001). J. Nat. Prod..

Showing NP-Card for (3S,7R)-5,6-dehydro-1,7-bis(4-hydroxyphenyl)-4''-de-O-methylcentrolobine (NP0025598)

MOL for NP0025598 ((3S,7R)-5,6-dehydro-1,7-bis(4-hydroxyphenyl)-4''-de-O-methylcentrolobine)

3D MOL for NP0025598 ((3S,7R)-5,6-dehydro-1,7-bis(4-hydroxyphenyl)-4''-de-O-methylcentrolobine)

3D SDF for NP0025598 ((3S,7R)-5,6-dehydro-1,7-bis(4-hydroxyphenyl)-4''-de-O-methylcentrolobine)

3D-SDF for NP0025598 ((3S,7R)-5,6-dehydro-1,7-bis(4-hydroxyphenyl)-4''-de-O-methylcentrolobine)

PDB for NP0025598 ((3S,7R)-5,6-dehydro-1,7-bis(4-hydroxyphenyl)-4''-de-O-methylcentrolobine)

3D PDB for NP0025598 ((3S,7R)-5,6-dehydro-1,7-bis(4-hydroxyphenyl)-4''-de-O-methylcentrolobine)

SMILES for NP0025598 ((3S,7R)-5,6-dehydro-1,7-bis(4-hydroxyphenyl)-4''-de-O-methylcentrolobine)

INCHI for NP0025598 ((3S,7R)-5,6-dehydro-1,7-bis(4-hydroxyphenyl)-4''-de-O-methylcentrolobine)

Structure for NP0025598 ((3S,7R)-5,6-dehydro-1,7-bis(4-hydroxyphenyl)-4''-de-O-methylcentrolobine)

3D Structure for NP0025598 ((3S,7R)-5,6-dehydro-1,7-bis(4-hydroxyphenyl)-4''-de-O-methylcentrolobine)