NP-MRD: Showing NP-Card for Calanolide A (NP0051435)

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Record Information

Version

2.0

Created at

2022-04-27 22:48:08 UTC

Updated at

2022-04-27 22:48:08 UTC

NP-MRD ID

NP0051435

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Calanolide A

Description

Calanolide A 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 A is a drug which is used for use in combination treatment of hiv infection (aids). Calanolide A is an extremely weak basic (essentially neutral) compound (based on its pKa). Calanolide A is found in Calophyllum brasiliense , Calophyllum lanigerum, Calophyllum lanigerum var. austrocoriaceum and Calophyllum teysmannii. Calanolide A was first documented in 1998 (PMID: 9784162). An organic heterotetracyclic compound that is 11,12-dihydro-2H,6H,10H-dipyranochromen-2-one substituted by a hydroxy group at position 12, methyl groups at positions 6, 6, 10 and 11 and a propyl group at position 4 (the 10R,11S,12S stereoisomer) (PMID: 10901131) (PMID: 12501127) (PMID: 14980631).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02231218002D          

 27 30  0  0  1  0            999 V2000
    3.7637    1.8273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2785    0.3490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5060   -0.3702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7408   -1.0897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7495   -2.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4748    1.0898    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9102    0.3490    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9045    1.8339    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7694    0.3622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1819    1.0766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0068    1.0766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1819   -0.3523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0068   -0.3523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4193    0.3622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6499    1.0866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7138    1.0898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4947    2.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4479   -1.0897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4249    1.8273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2842    1.8339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2727   -1.0801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4299    1.4995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4267    0.6746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0240   -1.8372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1647   -1.8372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6935   -1.7897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5184   -1.7802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  1 10  1  0  0  0  0
  2 14  1  0  0  0  0
  2 16  1  0  0  0  0
  7  3  1  1  0  0  0
  4 12  1  0  0  0  0
  4 25  1  0  0  0  0
  5 25  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6 15  1  6  0  0  0
  7  9  1  0  0  0  0
  8 17  1  1  0  0  0
  9 10  2  0  0  0  0
  9 12  1  0  0  0  0
 10 11  1  0  0  0  0
 11 14  2  0  0  0  0
 11 19  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 18  1  0  0  0  0
 16 20  1  0  0  0  0
 16 22  1  0  0  0  0
 16 23  1  0  0  0  0
 18 21  1  0  0  0  0
 18 24  2  0  0  0  0
 19 20  2  0  0  0  0
 21 26  1  0  0  0  0
 24 25  1  0  0  0  0
 26 27  1  0  0  0  0
M  END

     RDKit          3D

 53 56  0  0  0  0  0  0  0  0999 V2000
   -4.2440   -2.9864   -0.7288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1215   -2.1329    0.4919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9947   -1.0953    0.3746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6709   -1.7044    0.2035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4027   -3.0526    0.2151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1317   -3.5681    0.0472 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0900   -4.8186    0.0615 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8699   -2.7470   -0.1314 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6816   -1.4459   -0.1523 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8119   -0.6789   -0.3467 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6739    0.6920   -0.3763 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4510    1.3145   -0.2190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6558    0.5031   -0.0265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5860   -0.8743    0.0129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8635    1.1140    0.1300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1223    2.4994    0.1186 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7268    2.9551    1.4506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1064    2.8615   -0.9749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9022    3.2995   -0.0901 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2845    2.7501   -0.2457 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8219    1.4452   -0.5728 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0674    1.0398   -0.0068 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1630    1.4818   -0.9399 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1184   -0.4179    0.3316 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7638   -0.6948    1.7786 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1739   -1.2222   -0.5278 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4901   -1.0767   -1.8869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1642   -2.7038   -1.3273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4105   -2.8226   -1.4574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3642   -4.0634   -0.5482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0600   -1.5501    0.5949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0190   -2.7146    1.4286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0163   -0.5333    1.3081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3187   -0.5151   -0.5262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1885   -3.7455    0.3643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6930    4.0605    1.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7790    2.6619    1.5031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1111    2.6008    2.2950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8904    3.5566   -0.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6491    1.9767   -1.3676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6216    3.3446   -1.8431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0032    4.3696   -0.1136 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1628    3.3580   -0.3972 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1757    1.6550    0.9213 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9634    1.1567   -1.9922 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1635    1.1865   -0.6003 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1507    2.5989   -0.9386 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1535   -0.8348    0.1932 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6529   -0.4834    2.4140 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9289   -0.0555    2.1188 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5330   -1.7795    1.8475 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2429   -2.2905   -0.2953 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2283   -1.8739   -2.4113 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 14  2  0
 14 13  1  0
 13 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
 12 11  1  0
 11 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
 14  4  1  0
 15 13  1  0
 21 11  1  0
 10  9  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
 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
 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  1
 23 45  1  0
 23 46  1  0
 23 47  1  0
M  END


  Mrv0541 02231218002D          

 27 30  0  0  1  0            999 V2000
    3.7637    1.8273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2785    0.3490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5060   -0.3702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7408   -1.0897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7495   -2.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4748    1.0898    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9102    0.3490    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9045    1.8339    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7694    0.3622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1819    1.0766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0068    1.0766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1819   -0.3523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0068   -0.3523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4193    0.3622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6499    1.0866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7138    1.0898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4947    2.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4479   -1.0897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4249    1.8273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2842    1.8339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2727   -1.0801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4299    1.4995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4267    0.6746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0240   -1.8372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1647   -1.8372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6935   -1.7897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5184   -1.7802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  1 10  1  0  0  0  0
  2 14  1  0  0  0  0
  2 16  1  0  0  0  0
  7  3  1  1  0  0  0
  4 12  1  0  0  0  0
  4 25  1  0  0  0  0
  5 25  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6 15  1  6  0  0  0
  7  9  1  0  0  0  0
  8 17  1  1  0  0  0
  9 10  2  0  0  0  0
  9 12  1  0  0  0  0
 10 11  1  0  0  0  0
 11 14  2  0  0  0  0
 11 19  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 18  1  0  0  0  0
 16 20  1  0  0  0  0
 16 22  1  0  0  0  0
 16 23  1  0  0  0  0
 18 21  1  0  0  0  0
 18 24  2  0  0  0  0
 19 20  2  0  0  0  0
 21 26  1  0  0  0  0
 24 25  1  0  0  0  0
 26 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051435

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC1=CC(=O)OC2=C1C1=C(C=CC(C)(C)O1)C1=C2[C@@H](O)[C@H](C)[C@@H](C)O1

> <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-FMTVUPSXSA-N

> <FORMULA>
C22H26O5

> <MOLECULAR_WEIGHT>
370.4388

> <EXACT_MASS>
370.178023942

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
40.99482070187777

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(10R,11S,12S)-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>
13.625542014318452

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3999879229371084

> <JCHEM_POLAR_SURFACE_AREA>
64.99000000000001

> <JCHEM_REFRACTIVITY>
104.10690000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.78e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
calanolide A

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       7.026   3.411   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      11.720   0.651   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       4.678  -0.691   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       6.983  -2.034   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       6.999  -4.760   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.620   2.034   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.432   0.651   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.422   3.423   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.036   0.676   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.806   2.010   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.346   2.010   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.806  -0.658   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.346  -0.658   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.116   0.676   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.080   2.028   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.532   2.034   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.657   4.760   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.169  -2.034   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.126   3.411   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.731   3.423   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.709  -2.016   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.869   2.799   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.863   1.259   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.378  -3.429   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.774  -3.429   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.495  -3.341   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      14.034  -3.323   0.000  0.00  0.00           C+0
CONECT    1    8   10                                                       
CONECT    2   14   16                                                       
CONECT    3    7                                                            
CONECT    4   12   25                                                       
CONECT    5   25                                                            
CONECT    6    7    8   15                                                  
CONECT    7    3    6    9                                                  
CONECT    8    1    6   17                                                  
CONECT    9    7   10   12                                                  
CONECT   10    1    9   11                                                  
CONECT   11   10   14   19                                                  
CONECT   12    4    9   13                                                  
CONECT   13   12   14   18                                                  
CONECT   14    2   11   13                                                  
CONECT   15    6                                                            
CONECT   16    2   20   22   23                                             
CONECT   17    8                                                            
CONECT   18   13   21   24                                                  
CONECT   19   11   20                                                       
CONECT   20   16   19                                                       
CONECT   21   18   26                                                       
CONECT   22   16                                                            
CONECT   23   16                                                            
CONECT   24   18   25                                                       
CONECT   25    4    5   24                                                  
CONECT   26   21   27                                                       
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

View in JSmol

Synonyms

Value	Source
(+)-(10R,11S,12S)-10,11-trans-Dihydro-12-hydroxy-6,6,10,11-tetramethyl-4-propyl-2H,6H-benzo[1,2-b:3,4-b':5,6-b'']tripyran-2-one	ChEBI
(10R,11S,12S)-11,12-Dihydro-12-hydroxy-6,6,10,11-tetramethyl-4-propyl-2H,6H,10H-benzo(1,2-b:3,4-b':5,6-b'')tripyran-2-one	ChEBI
Calanolide F	MeSH
Costatolide	MeSH
Calanolide a	ChEBI

Chemical Formula

C₂₂H₂₆O₅

Average Mass

370.4388 Da

Monoisotopic Mass

370.17802 Da

IUPAC Name

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

Traditional Name

calanolide A

CAS Registry Number

Not Available

SMILES

CCCC1=CC(=O)OC2=C1C1=C(C=CC(C)(C)O1)C1=C2[C@@H](O)[C@H](C)[C@@H](C)O1

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-FMTVUPSXSA-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 brasiliense	Plant	KNApSAcK
Calophyllum lanigerum	LOTUS Database	35616633
Calophyllum lanigerum var. austrocoriaceum	Plant	KNApSAcK
Calophyllum teysmannii	LOTUS Database	35616633

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

organic heterotetracyclic compound (CHEBI:65552 )
secondary alcohol (CHEBI:65552 )
delta-lactone (CHEBI:65552 )
cyclic ether (CHEBI:65552 )
coumarins (C09147 )

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	40.99 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

DB04886

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00002454

Chemspider ID

Not Available

KEGG Compound ID

C09147

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Calanolide A

METLIN ID

Not Available

PubChem Compound

64972

PDB ID

Not Available

ChEBI ID

65552

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 ]
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 ]
Eiznhamer DA, Creagh T, Ruckle JL, Tolbert DT, Giltner J, Dutta B, Flavin MT, Jenta T, Xu ZQ: Safety and pharmacokinetic profile of multiple escalating doses of (+)-calanolide A, a naturally occurring nonnucleoside reverse transcriptase inhibitor, in healthy HIV-negative volunteers. HIV Clin Trials. 2002 Nov-Dec;3(6):435-50. doi: 10.1310/9gde-f2r1-w2rl-e9fj. [PubMed:12501127 ]
Xu ZQ, Barrow WW, Suling WJ, Westbrook L, Barrow E, Lin YM, Flavin MT: Anti-HIV natural product (+)-calanolide A is active against both drug-susceptible and drug-resistant strains of Mycobacterium tuberculosis. Bioorg Med Chem. 2004 Mar 1;12(5):1199-207. doi: 10.1016/j.bmc.2003.11.012. [PubMed:14980631 ]

Showing NP-Card for Calanolide A (NP0051435)

MOL for NP0051435 (Calanolide A)

3D MOL for NP0051435 (Calanolide A)

3D SDF for NP0051435 (Calanolide A)

3D-SDF for NP0051435 (Calanolide A)

PDB for NP0051435 (Calanolide A)

3D PDB for NP0051435 (Calanolide A)

SMILES for NP0051435 (Calanolide A)

INCHI for NP0051435 (Calanolide A)

Structure for NP0051435 (Calanolide A)

3D Structure for NP0051435 (Calanolide A)