NP-MRD: Showing NP-Card for Chiricanine B (NP0025734)

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Record Information

Version

2.0

Created at

2021-06-19 17:46:50 UTC

Updated at

2021-06-29 23:50:51 UTC

NP-MRD ID

NP0025734

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Chiricanine B

Provided By

JEOL Database JEOL Logo

Description

Chiricanine B belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. Chiricanine B is found in Lonchocarpus chiricanus. Chiricanine B was first documented in 2001 (Ioset, J.-R., et al.). Based on a literature review very few articles have been published on Chiricanine B.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192119463D          

 42 44  0  0  0  0            999 V2000
   -1.4959    0.9290    5.7892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7123   -0.1969    4.7642 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7935   -1.3717    5.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2866    0.3489    3.4981 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7009   -0.3102    2.3720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0317    0.0365    1.1947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3572   -0.5771   -0.0204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6891   -0.2204   -1.2798 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6304    0.0079   -1.3815 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3023    0.3473   -2.6436 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5722   -0.1853   -2.9004 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2539    0.1361   -4.0768 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6772    1.0027   -5.0028 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4217    1.5520   -4.7510 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7394    1.2300   -3.5748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3851   -1.5260   -0.0429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0563   -1.8580    1.1350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0496   -2.7977    1.1166 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7369   -1.2470    2.3519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4776   -1.6089    3.6110 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2027   -0.6029    4.7271 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0425    0.5472    4.5308 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8143    0.6266    6.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4387    1.2164    5.8343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0413    1.8366    5.5075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8335   -2.1815    4.4056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0574   -1.7851    6.1199 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2536   -1.0481    5.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2534    0.7948    1.2399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3291   -0.1811   -2.1579 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2814   -0.0836   -0.5152 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0390   -0.8631   -2.1892 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2356   -0.2893   -4.2681 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2082    1.2545   -5.9171 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9746    2.2370   -5.4667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2298    1.6865   -3.3895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6501   -2.0077   -0.9799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1612   -3.1228    0.2080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1566   -2.6098    3.9228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5551   -1.6390    3.4090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5067   -1.0368    5.6866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7197    0.9945    3.7257 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  1  0  0  0  0
 17 19  2  0  0  0  0
 10 11  2  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
 11 12  1  0  0  0  0
 17 18  1  0  0  0  0
  5 19  1  0  0  0  0
 12 13  2  0  0  0  0
 10  9  1  0  0  0  0
 14 15  2  0  0  0  0
  9  8  2  0  0  0  0
  8  7  1  0  0  0  0
  5  4  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21  2  1  0  0  0  0
  2  4  1  0  0  0  0
 15 10  1  0  0  0  0
  2  1  1  1  0  0  0
  7 16  2  0  0  0  0
  2  3  1  0  0  0  0
 13 14  1  0  0  0  0
 21 22  1  0  0  0  0
 12 33  1  0  0  0  0
 13 34  1  0  0  0  0
 14 35  1  0  0  0  0
 15 36  1  0  0  0  0
 11 32  1  0  0  0  0
  9 31  1  0  0  0  0
  8 30  1  0  0  0  0
 16 37  1  0  0  0  0
  6 29  1  0  0  0  0
 18 38  1  0  0  0  0
 20 39  1  0  0  0  0
 20 40  1  0  0  0  0
 21 41  1  1  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  3 26  1  0  0  0  0
  3 27  1  0  0  0  0
  3 28  1  0  0  0  0
 22 42  1  0  0  0  0
M  END

     RDKit          3D

 42 44  0  0  0  0  0  0  0  0999 V2000
   -1.4959    0.9290    5.7892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7123   -0.1969    4.7642 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7935   -1.3717    5.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2866    0.3489    3.4981 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7009   -0.3102    2.3720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0317    0.0365    1.1947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3572   -0.5771   -0.0204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6891   -0.2204   -1.2798 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6304    0.0079   -1.3815 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3023    0.3473   -2.6436 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5722   -0.1853   -2.9004 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2539    0.1361   -4.0768 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6772    1.0027   -5.0028 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4217    1.5520   -4.7510 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7394    1.2300   -3.5748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3851   -1.5260   -0.0429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0563   -1.8580    1.1350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0496   -2.7977    1.1166 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7369   -1.2470    2.3519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4776   -1.6089    3.6110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2027   -0.6029    4.7271 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0425    0.5472    4.5308 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8143    0.6266    6.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4387    1.2164    5.8343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0413    1.8366    5.5075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8335   -2.1815    4.4056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0574   -1.7851    6.1199 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2536   -1.0481    5.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2534    0.7948    1.2399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3291   -0.1811   -2.1579 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2814   -0.0836   -0.5152 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0390   -0.8631   -2.1892 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2356   -0.2893   -4.2681 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2082    1.2545   -5.9171 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9746    2.2370   -5.4667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2298    1.6865   -3.3895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6501   -2.0077   -0.9799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1612   -3.1228    0.2080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1566   -2.6098    3.9228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5551   -1.6390    3.4090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5067   -1.0368    5.6866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7197    0.9945    3.7257 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  1  0
 17 19  2  0
 10 11  2  0
  5  6  2  0
  6  7  1  0
 11 12  1  0
 17 18  1  0
  5 19  1  0
 12 13  2  0
 10  9  1  0
 14 15  2  0
  9  8  2  0
  8  7  1  0
  5  4  1  0
 19 20  1  0
 20 21  1  0
 21  2  1  0
  2  4  1  0
 15 10  1  0
  2  1  1  1
  7 16  2  0
  2  3  1  0
 13 14  1  0
 21 22  1  0
 12 33  1  0
 13 34  1  0
 14 35  1  0
 15 36  1  0
 11 32  1  0
  9 31  1  0
  8 30  1  0
 16 37  1  0
  6 29  1  0
 18 38  1  0
 20 39  1  0
 20 40  1  0
 21 41  1  1
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
 22 42  1  0
M  END


  Mrv1652306192119463D          

 42 44  0  0  0  0            999 V2000
   -1.4959    0.9290    5.7892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7123   -0.1969    4.7642 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7935   -1.3717    5.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2866    0.3489    3.4981 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7009   -0.3102    2.3720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0317    0.0365    1.1947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3572   -0.5771   -0.0204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6891   -0.2204   -1.2798 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6304    0.0079   -1.3815 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3023    0.3473   -2.6436 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5722   -0.1853   -2.9004 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2539    0.1361   -4.0768 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6772    1.0027   -5.0028 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4217    1.5520   -4.7510 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7394    1.2300   -3.5748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3851   -1.5260   -0.0429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0563   -1.8580    1.1350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0496   -2.7977    1.1166 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7369   -1.2470    2.3519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4776   -1.6089    3.6110 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2027   -0.6029    4.7271 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0425    0.5472    4.5308 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8143    0.6266    6.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4387    1.2164    5.8343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0413    1.8366    5.5075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8335   -2.1815    4.4056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0574   -1.7851    6.1199 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2536   -1.0481    5.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2534    0.7948    1.2399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3291   -0.1811   -2.1579 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2814   -0.0836   -0.5152 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0390   -0.8631   -2.1892 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2356   -0.2893   -4.2681 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2082    1.2545   -5.9171 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9746    2.2370   -5.4667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2298    1.6865   -3.3895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6501   -2.0077   -0.9799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1612   -3.1228    0.2080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1566   -2.6098    3.9228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5551   -1.6390    3.4090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5067   -1.0368    5.6866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7197    0.9945    3.7257 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  1  0  0  0  0
 17 19  2  0  0  0  0
 10 11  2  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
 11 12  1  0  0  0  0
 17 18  1  0  0  0  0
  5 19  1  0  0  0  0
 12 13  2  0  0  0  0
 10  9  1  0  0  0  0
 14 15  2  0  0  0  0
  9  8  2  0  0  0  0
  8  7  1  0  0  0  0
  5  4  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21  2  1  0  0  0  0
  2  4  1  0  0  0  0
 15 10  1  0  0  0  0
  2  1  1  1  0  0  0
  7 16  2  0  0  0  0
  2  3  1  0  0  0  0
 13 14  1  0  0  0  0
 21 22  1  0  0  0  0
 12 33  1  0  0  0  0
 13 34  1  0  0  0  0
 14 35  1  0  0  0  0
 15 36  1  0  0  0  0
 11 32  1  0  0  0  0
  9 31  1  0  0  0  0
  8 30  1  0  0  0  0
 16 37  1  0  0  0  0
  6 29  1  0  0  0  0
 18 38  1  0  0  0  0
 20 39  1  0  0  0  0
 20 40  1  0  0  0  0
 21 41  1  1  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  3 26  1  0  0  0  0
  3 27  1  0  0  0  0
  3 28  1  0  0  0  0
 22 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0025734

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2C(OC(C([H])([H])[H])(C([H])([H])[H])[C@@]([H])(O[H])C2([H])[H])=C([H])C(\C([H])=C(/[H])C2=C([H])C([H])=C([H])C([H])=C2[H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C19H20O3/c1-19(2)18(21)12-15-16(20)10-14(11-17(15)22-19)9-8-13-6-4-3-5-7-13/h3-11,18,20-21H,12H2,1-2H3/b9-8+/t18-/m0/s1

> <INCHI_KEY>
HSGNBZVGNHDAMS-BLGFXRMMSA-N

> <FORMULA>
C19H20O3

> <MOLECULAR_WEIGHT>
296.366

> <EXACT_MASS>
296.141244504

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
33.8266283094627

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S)-2,2-dimethyl-7-[(E)-2-phenylethenyl]-3,4-dihydro-2H-1-benzopyran-3,5-diol

> <ALOGPS_LOGP>
3.71

> <JCHEM_LOGP>
3.9585555213333334

> <ALOGPS_LOGS>
-4.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.860201131031943

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.058262085180449

> <JCHEM_PKA_STRONGEST_BASIC>
-3.332678526301052

> <JCHEM_POLAR_SURFACE_AREA>
49.69

> <JCHEM_REFRACTIVITY>
88.28600000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.50e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-2,2-dimethyl-7-[(E)-2-phenylethenyl]-3,4-dihydro-1-benzopyran-3,5-diol

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 42 44  0  0  0  0  0  0  0  0999 V2000
   -1.4959    0.9290    5.7892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7123   -0.1969    4.7642 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7935   -1.3717    5.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2866    0.3489    3.4981 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7009   -0.3102    2.3720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0317    0.0365    1.1947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3572   -0.5771   -0.0204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6891   -0.2204   -1.2798 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6304    0.0079   -1.3815 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3023    0.3473   -2.6436 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5722   -0.1853   -2.9004 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2539    0.1361   -4.0768 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6772    1.0027   -5.0028 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4217    1.5520   -4.7510 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7394    1.2300   -3.5748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3851   -1.5260   -0.0429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0563   -1.8580    1.1350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0496   -2.7977    1.1166 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7369   -1.2470    2.3519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4776   -1.6089    3.6110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2027   -0.6029    4.7271 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0425    0.5472    4.5308 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8143    0.6266    6.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4387    1.2164    5.8343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0413    1.8366    5.5075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8335   -2.1815    4.4056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0574   -1.7851    6.1199 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2536   -1.0481    5.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2534    0.7948    1.2399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3291   -0.1811   -2.1579 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2814   -0.0836   -0.5152 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0390   -0.8631   -2.1892 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2356   -0.2893   -4.2681 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2082    1.2545   -5.9171 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9746    2.2370   -5.4667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2298    1.6865   -3.3895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6501   -2.0077   -0.9799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1612   -3.1228    0.2080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1566   -2.6098    3.9228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5551   -1.6390    3.4090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5067   -1.0368    5.6866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7197    0.9945    3.7257 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  1  0
 17 19  2  0
 10 11  2  0
  5  6  2  0
  6  7  1  0
 11 12  1  0
 17 18  1  0
  5 19  1  0
 12 13  2  0
 10  9  1  0
 14 15  2  0
  9  8  2  0
  8  7  1  0
  5  4  1  0
 19 20  1  0
 20 21  1  0
 21  2  1  0
  2  4  1  0
 15 10  1  0
  2  1  1  1
  7 16  2  0
  2  3  1  0
 13 14  1  0
 21 22  1  0
 12 33  1  0
 13 34  1  0
 14 35  1  0
 15 36  1  0
 11 32  1  0
  9 31  1  0
  8 30  1  0
 16 37  1  0
  6 29  1  0
 18 38  1  0
 20 39  1  0
 20 40  1  0
 21 41  1  1
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
 22 42  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  C   UNK     0      -1.496   0.929   5.789  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.712  -0.197   4.764  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.794  -1.372   5.141  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.287   0.349   3.498  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.701  -0.310   2.372  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.032   0.037   1.195  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.357  -0.577  -0.020  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.689  -0.220  -1.280  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.630   0.008  -1.381  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.302   0.347  -2.644  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.572  -0.185  -2.900  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.254   0.136  -4.077  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.677   1.003  -5.003  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.422   1.552  -4.751  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.739   1.230  -3.575  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.385  -1.526  -0.043  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.056  -1.858   1.135  0.00  0.00           C+0
HETATM   18  O   UNK     0      -4.050  -2.798   1.117  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.737  -1.247   2.352  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.478  -1.609   3.611  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.203  -0.603   4.727  0.00  0.00           C+0
HETATM   22  O   UNK     0      -4.043   0.547   4.531  0.00  0.00           O+0
HETATM   23  H   UNK     0      -1.814   0.627   6.792  0.00  0.00           H+0
HETATM   24  H   UNK     0      -0.439   1.216   5.834  0.00  0.00           H+0
HETATM   25  H   UNK     0      -2.041   1.837   5.508  0.00  0.00           H+0
HETATM   26  H   UNK     0      -0.834  -2.182   4.406  0.00  0.00           H+0
HETATM   27  H   UNK     0      -1.057  -1.785   6.120  0.00  0.00           H+0
HETATM   28  H   UNK     0       0.254  -1.048   5.173  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.253   0.795   1.240  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.329  -0.181  -2.158  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.281  -0.084  -0.515  0.00  0.00           H+0
HETATM   32  H   UNK     0       3.039  -0.863  -2.189  0.00  0.00           H+0
HETATM   33  H   UNK     0       4.236  -0.289  -4.268  0.00  0.00           H+0
HETATM   34  H   UNK     0       3.208   1.254  -5.917  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.975   2.237  -5.467  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.230   1.687  -3.389  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.650  -2.008  -0.980  0.00  0.00           H+0
HETATM   38  H   UNK     0      -4.161  -3.123   0.208  0.00  0.00           H+0
HETATM   39  H   UNK     0      -3.157  -2.610   3.923  0.00  0.00           H+0
HETATM   40  H   UNK     0      -4.555  -1.639   3.409  0.00  0.00           H+0
HETATM   41  H   UNK     0      -3.507  -1.037   5.687  0.00  0.00           H+0
HETATM   42  H   UNK     0      -3.720   0.995   3.726  0.00  0.00           H+0
CONECT    1    2   23   24   25                                             
CONECT    2   21    4    1    3                                             
CONECT    3    2   26   27   28                                             
CONECT    4    5    2                                                       
CONECT    5    6   19    4                                                  
CONECT    6    5    7   29                                                  
CONECT    7    6    8   16                                                  
CONECT    8    9    7   30                                                  
CONECT    9   10    8   31                                                  
CONECT   10   11    9   15                                                  
CONECT   11   10   12   32                                                  
CONECT   12   11   13   33                                                  
CONECT   13   12   14   34                                                  
CONECT   14   15   13   35                                                  
CONECT   15   14   10   36                                                  
CONECT   16   17    7   37                                                  
CONECT   17   16   19   18                                                  
CONECT   18   17   38                                                       
CONECT   19   17    5   20                                                  
CONECT   20   19   21   39   40                                             
CONECT   21   20    2   22   41                                             
CONECT   22   21   42                                                       
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    3                                                            
CONECT   27    3                                                            
CONECT   28    3                                                            
CONECT   29    6                                                            
CONECT   30    8                                                            
CONECT   31    9                                                            
CONECT   32   11                                                            
CONECT   33   12                                                            
CONECT   34   13                                                            
CONECT   35   14                                                            
CONECT   36   15                                                            
CONECT   37   16                                                            
CONECT   38   18                                                            
CONECT   39   20                                                            
CONECT   40   20                                                            
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
   -1.4959    0.9290    5.7892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7123   -0.1969    4.7642 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7935   -1.3717    5.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2866    0.3489    3.4981 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7009   -0.3102    2.3720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0317    0.0365    1.1947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3572   -0.5771   -0.0204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6891   -0.2204   -1.2798 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6304    0.0079   -1.3815 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3023    0.3473   -2.6436 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5722   -0.1853   -2.9004 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2539    0.1361   -4.0768 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6772    1.0027   -5.0028 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4217    1.5520   -4.7510 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7394    1.2300   -3.5748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3851   -1.5260   -0.0429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0563   -1.8580    1.1350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0496   -2.7977    1.1166 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7369   -1.2470    2.3519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4776   -1.6089    3.6110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2027   -0.6029    4.7271 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0425    0.5472    4.5308 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8143    0.6266    6.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4387    1.2164    5.8343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0413    1.8366    5.5075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8335   -2.1815    4.4056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0574   -1.7851    6.1199 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2536   -1.0481    5.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2534    0.7948    1.2399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3291   -0.1811   -2.1579 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2814   -0.0836   -0.5152 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0390   -0.8631   -2.1892 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2356   -0.2893   -4.2681 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2082    1.2545   -5.9171 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9746    2.2370   -5.4667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2298    1.6865   -3.3895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6501   -2.0077   -0.9799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1612   -3.1228    0.2080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1566   -2.6098    3.9228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5551   -1.6390    3.4090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5067   -1.0368    5.6866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7197    0.9945    3.7257 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  1  0
 17 19  2  0
 10 11  2  0
  5  6  2  0
  6  7  1  0
 11 12  1  0
 17 18  1  0
  5 19  1  0
 12 13  2  0
 10  9  1  0
 14 15  2  0
  9  8  2  0
  8  7  1  0
  5  4  1  0
 19 20  1  0
 20 21  1  0
 21  2  1  0
  2  4  1  0
 15 10  1  0
  2  1  1  1
  7 16  2  0
  2  3  1  0
 13 14  1  0
 21 22  1  0
 12 33  1  0
 13 34  1  0
 14 35  1  0
 15 36  1  0
 11 32  1  0
  9 31  1  0
  8 30  1  0
 16 37  1  0
  6 29  1  0
 18 38  1  0
 20 39  1  0
 20 40  1  0
 21 41  1  1
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
 22 42  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

(3S)-2,2-dimethyl-7-[(E)-2-phenylethenyl]-3,4-dihydro-2H-1-benzopyran-3,5-diol

Traditional Name

(3S)-2,2-dimethyl-7-[(E)-2-phenylethenyl]-3,4-dihydro-1-benzopyran-3,5-diol

CAS Registry Number

Not Available

SMILES

[H]OC1=C2C(OC(C([H])([H])[H])(C([H])([H])[H])[C@@]([H])(O[H])C2([H])[H])=C([H])C(\C([H])=C(/[H])C2=C([H])C([H])=C([H])C([H])=C2[H])=C1[H]

InChI Identifier

InChI=1S/C19H20O3/c1-19(2)18(21)12-15-16(20)10-14(11-17(15)22-19)9-8-13-6-4-3-5-7-13/h3-11,18,20-21H,12H2,1-2H3/b9-8+/t18-/m0/s1

InChI Key

HSGNBZVGNHDAMS-BLGFXRMMSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, 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
Lonchocarpus chiricanus	JEOL database	Ioset, J.-R., et al, J. Nat. Prod. 64, 710 (2001)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Not Available

Direct Parent

Stilbenes

Alternative Parents

Substituents

Stilbene
2,2-dimethyl-1-benzopyran
Chromane
Benzopyran
1-benzopyran
Styrene
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Secondary alcohol
Oxacycle
Ether
Organoheterocyclic compound
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.71	ALOGPS
logP	3.96	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	9.06	ChemAxon
pKa (Strongest Basic)	-3.3	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	2	ChemAxon
Refractivity	88.29 m³·mol⁻¹	ChemAxon
Polarizability	33.83 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

C00045761

Chemspider ID

9521936

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11346998

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ioset, J.-R., et al. (2001). Ioset, J.-R., et al, J. Nat. Prod. 64, 710 (2001). J. Nat. Prod..

Showing NP-Card for Chiricanine B (NP0025734)

MOL for NP0025734 (Chiricanine B)

3D MOL for NP0025734 (Chiricanine B)

3D SDF for NP0025734 (Chiricanine B)

3D-SDF for NP0025734 (Chiricanine B)

PDB for NP0025734 (Chiricanine B)

3D PDB for NP0025734 (Chiricanine B)

SMILES for NP0025734 (Chiricanine B)

INCHI for NP0025734 (Chiricanine B)

Structure for NP0025734 (Chiricanine B)

3D Structure for NP0025734 (Chiricanine B)