NP-MRD: Showing NP-Card for Calanolide B (NP0063046)

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Record Information

Version

2.0

Created at

2022-04-28 07:33:05 UTC

Updated at

2022-04-28 07:33:05 UTC

NP-MRD ID

NP0063046

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Calanolide B

Description

Calanolide B belongs to the class of organic compounds known as angular pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) angularly fused to a coumarin moiety. Calanolide B is found in Calophyllum lanigerum. Calanolide B was first documented in 1998 (PMID: 9934455). Based on a literature review a small amount of articles have been published on Calanolide B (PMID: 10901131) (PMID: 10428899) (PMID: 9784162) (PMID: 9724557).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282209332D          

 27 30  0  0  1  0            999 V2000
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -3.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7429    0.0252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7429    0.7998    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
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  1 10  1  0  0  0  0
  9 11  1  1  0  0  0
  8 12  1  6  0  0  0
  7 13  1  6  0  0  0
  5 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
  4 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  3 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
  2 25  1  0  0  0  0
 23 26  1  0  0  0  0
 23 27  1  0  0  0  0
M  END

     RDKit          3D

 53 56  0  0  0  0  0  0  0  0999 V2000
   -4.4212    2.0129    1.6105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4737    1.6191    0.1751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2683    0.7248   -0.1530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0152    1.4729    0.0517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9884    2.8281    0.3057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7752    3.4746    0.4961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8329    4.7092    0.7236 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3294    2.7809    0.4296 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3427    1.4790    0.1866 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5540    0.7881    0.1253 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6284   -0.5619   -0.1253 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4531   -1.2527   -0.3229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7605   -0.6007   -0.2689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8134    0.7517   -0.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8958   -1.3229   -0.4724 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9724   -2.7054   -0.7383 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8207   -3.4318    0.2811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5979   -2.8586   -2.1194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6328   -3.3399   -0.7823 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4969   -2.6800   -0.5921 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8693   -1.2337   -0.1812 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9944   -0.3892   -0.3567 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2863   -1.1591   -0.3468 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9144    0.6573    0.7147 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2191    1.3785    0.9329 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7963    1.6086    0.3496 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1571    2.3283   -0.7609 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7588    3.0422    1.8158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4374    1.8650    2.1044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1099    1.3199    2.1797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5262    2.4752   -0.5244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3726    1.0119   -0.0089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3640   -0.0710    0.6587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4384    0.3430   -1.1566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9197    3.3776    0.3402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2122   -4.1777    0.8301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6256   -3.9683   -0.2295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2116   -2.7295    1.0626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6151   -2.4259   -2.1012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5883   -3.9039   -2.4347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0056   -2.2416   -2.8413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6065   -4.4006   -0.9827 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4706   -3.1501   -0.6266 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9065    0.1176   -1.3478 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1169   -0.4333   -0.2358 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2959   -1.9588    0.3949 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3984   -1.6209   -1.3504 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6285    0.1493    1.6715 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6537    1.7037   -0.0341 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9943    2.2784    1.5447 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8865    0.7377    1.5188 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6316    2.2716    1.2487 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0364    3.3102   -0.6430 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 26  1  0
 26 27  1  0
 26 24  1  0
 24 25  1  0
 24 22  1  0
 22 23  1  0
 22 21  1  0
 21 11  1  0
 11 12  2  0
 12 20  1  0
 20 19  2  0
 19 16  1  0
 16 17  1  1
 16 18  1  0
 16 15  1  0
 15 13  1  0
 13 14  2  0
 14  4  1  0
 14  9  1  0
 11 10  1  0
 13 12  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  3 33  1  0
  3 34  1  0
  5 35  1  0
 26 52  1  1
 27 53  1  0
 24 48  1  1
 25 49  1  0
 25 50  1  0
 25 51  1  0
 22 44  1  6
 23 45  1  0
 23 46  1  0
 23 47  1  0
 20 43  1  0
 19 42  1  0
 17 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 18 41  1  0
M  END


  Mrv1652304282209332D          

 27 30  0  0  1  0            999 V2000
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -3.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7429    0.0252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7429    0.7998    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
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  1 10  1  0  0  0  0
  9 11  1  1  0  0  0
  8 12  1  6  0  0  0
  7 13  1  6  0  0  0
  5 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
  4 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  3 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
  2 25  1  0  0  0  0
 23 26  1  0  0  0  0
 23 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0063046

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC1=CC(=O)OC2=C3[C@H](O)[C@H](C)[C@@H](C)OC3=C3C=CC(C)(C)OC3=C12

> <INCHI_IDENTIFIER>
InChI=1S/C22H26O5/c1-6-7-13-10-15(23)26-21-16(13)20-14(8-9-22(4,5)27-20)19-17(21)18(24)11(2)12(3)25-19/h8-12,18,24H,6-7H2,1-5H3/t11-,12-,18-/m1/s1

> <INCHI_KEY>
NIDRYBLTWYFCFV-SEDUGSJDSA-N

> <FORMULA>
C22H26O5

> <MOLECULAR_WEIGHT>
370.445

> <EXACT_MASS>
370.178023937

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
41.03778783787327

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(10R,11S,12R)-12-hydroxy-6,6,10,11-tetramethyl-4-propyl-6,10,11,12-tetrahydro-2H-1,5,9-trioxatriphenylen-2-one

> <ALOGPS_LOGP>
4.18

> <JCHEM_LOGP>
3.7915943689999994

> <ALOGPS_LOGS>
-4.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.625542014318455

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3999879229371075

> <JCHEM_POLAR_SURFACE_AREA>
64.99

> <JCHEM_REFRACTIVITY>
104.10690000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.78e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(10R,11S,12R)-12-hydroxy-6,6,10,11-tetramethyl-4-propyl-11,12-dihydro-10H-1,5,9-trioxatriphenylen-2-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       2.874   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.414  -1.897   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.104   2.104   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.206   3.437   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.746   0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.206  -1.897   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       2.104  -3.231   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.874  -4.565   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.104  -5.898   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.414  -4.565   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.184  -3.231   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.724  -3.231   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.494  -4.565   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.034  -4.565   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.724  -0.564   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.853   0.047   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.853   1.493   0.000  0.00  0.00           C+0
CONECT    1    2    6   10                                                  
CONECT    2    1    3   25                                                  
CONECT    3    2    4   22                                                  
CONECT    4    3    5   18                                                  
CONECT    5    4    6   14                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8   13                                                  
CONECT    8    7    9   12                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9    1                                                       
CONECT   11    9                                                            
CONECT   12    8                                                            
CONECT   13    7                                                            
CONECT   14    5   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17    4   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22    3   23                                                       
CONECT   23   22   24   26   27                                             
CONECT   24   23   25                                                       
CONECT   25   24    2                                                       
CONECT   26   23                                                            
CONECT   27   23                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₆O₅

Average Mass

370.4450 Da

Monoisotopic Mass

370.17802 Da

IUPAC Name

(10R,11S,12R)-12-hydroxy-6,6,10,11-tetramethyl-4-propyl-6,10,11,12-tetrahydro-2H-1,5,9-trioxatriphenylen-2-one

Traditional Name

(10R,11S,12R)-12-hydroxy-6,6,10,11-tetramethyl-4-propyl-11,12-dihydro-10H-1,5,9-trioxatriphenylen-2-one

CAS Registry Number

Not Available

SMILES

CCCC1=CC(=O)OC2=C3[C@H](O)[C@H](C)[C@@H](C)OC3=C3C=CC(C)(C)OC3=C12

InChI Identifier

InChI=1S/C22H26O5/c1-6-7-13-10-15(23)26-21-16(13)20-14(8-9-22(4,5)27-20)19-17(21)18(24)11(2)12(3)25-19/h8-12,18,24H,6-7H2,1-5H3/t11-,12-,18-/m1/s1

InChI Key

NIDRYBLTWYFCFV-SEDUGSJDSA-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
Calophyllum lanigerum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as angular pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) angularly fused to a coumarin moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Pyranocoumarins

Direct Parent

Angular pyranocoumarins

Alternative Parents

Substituents

Angular pyranocoumarin
Pyranochromene
2,2-dimethyl-1-benzopyran
Chromane
Benzopyran
1-benzopyran
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Lactone
Secondary alcohol
Ether
Oxacycle
Organoheterocyclic compound
Alcohol
Hydrocarbon derivative
Organic oxide
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	4.18	ALOGPS
logP	3.79	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	13.63	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	104.11 m³·mol⁻¹	ChemAxon
Polarizability	41.04 Å³	ChemAxon
Number of Rings	4	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

C00019765

Chemspider ID

58527

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

65008

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Xu ZQ, Norris KJ, Weinberg DS, Kardatzke J, Wertz P, Frank P, Flavin MT: Quantification of (+)-calanolide A, a novel and naturally occurring anti-HIV agent, by high-performance liquid chromatography in plasma from rat, dog and human. J Chromatogr B Biomed Sci Appl. 2000 Jun 9;742(2):267-75. doi: 10.1016/s0378-4347(00)00170-5. [PubMed:10901131 ]
Buckheit RW Jr, White EL, Fliakas-Boltz V, Russell J, Stup TL, Kinjerski TL, Osterling MC, Weigand A, Bader JP: Unique anti-human immunodeficiency virus activities of the nonnucleoside reverse transcriptase inhibitors calanolide A, costatolide, and dihydrocostatolide. Antimicrob Agents Chemother. 1999 Aug;43(8):1827-34. doi: 10.1128/AAC.43.8.1827. [PubMed:10428899 ]
Spino C, Dodier M, Sotheeswaran S: Anti-HIV coumarins from Calophyllum seed oil. Bioorg Med Chem Lett. 1998 Dec 15;8(24):3475-8. doi: 10.1016/s0960-894x(98)00628-3. [PubMed:9934455 ]
McKee TC, Covington CD, Fuller RW, Bokesch HR, Young S, Cardellina II JH, Kadushin MR, Soejarto DD, Stevens PF, Cragg GM, Boyd MR: Pyranocoumarins from tropical species of the genus Calophyllum: a chemotaxonomic study of extracts in the National Cancer Institute collection. J Nat Prod. 1998 Oct;61(10):1252-6. doi: 10.1021/np980140a. [PubMed:9784162 ]
Newman RA, Chen W, Madden TL: Pharmaceutical properties of related calanolide compounds with activity against human immunodeficiency virus. J Pharm Sci. 1998 Sep;87(9):1077-80. doi: 10.1021/js980122d. [PubMed:9724557 ]

Showing NP-Card for Calanolide B (NP0063046)

MOL for NP0063046 (Calanolide B)

3D MOL for NP0063046 (Calanolide B)

3D SDF for NP0063046 (Calanolide B)

3D-SDF for NP0063046 (Calanolide B)

PDB for NP0063046 (Calanolide B)

3D PDB for NP0063046 (Calanolide B)

SMILES for NP0063046 (Calanolide B)

INCHI for NP0063046 (Calanolide B)

Structure for NP0063046 (Calanolide B)

3D Structure for NP0063046 (Calanolide B)