NP-MRD: Showing NP-Card for (+)-Caesalpinin O (NP0070982)

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Record Information

Version

2.0

Created at

2022-04-28 16:23:04 UTC

Updated at

2022-04-28 16:23:04 UTC

NP-MRD ID

NP0070982

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Caesalpinin O

Description

Caesalpinin O belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton. (+)-Caesalpinin O is found in Caesalpinia crista . (+)-Caesalpinin O was first documented in 2005 (PMID: 15684521). Based on a literature review very few articles have been published on Caesalpinin O (PMID: 31962203).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282218232D          

 29 33  0  0  1  0            999 V2000
   -0.6265   -2.9100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0926   -2.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7361   -1.4852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0865   -1.4220    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5525   -2.1027    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1960   -2.8467    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6621   -3.5275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3056   -4.2714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7717   -4.9522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5170   -4.3347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3751   -2.0395    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7316   -1.2955    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2655   -0.6147    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4430   -0.6780    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0231    0.0028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7689    0.0389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5461   -0.2379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2269    0.2282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5230   -1.0626    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1205   -1.6315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9264   -2.4334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1350   -2.6663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6291   -2.8657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2574   -2.3310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9430   -1.5683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0186   -2.7835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3796   -0.7412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4672   -1.1030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8280   -0.6654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
  4 14  1  0  0  0  0
 14 15  1  1  0  0  0
 13 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 19 17  1  6  0  0  0
 12 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 11 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 20 25  1  0  0  0  0
  5 26  1  6  0  0  0
  4 27  1  1  0  0  0
  3 28  1  0  0  0  0
  3 29  1  0  0  0  0
M  END

     RDKit          3D

 57 61  0  0  0  0  0  0  0  0999 V2000
   -2.9607    3.3010   -1.3222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3456    2.6446   -0.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0066    3.3432    0.8727 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1186    1.2809   -0.0794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5398    0.7225    1.0551 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5295   -0.2299    1.6841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9029   -1.3615    0.8157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8191   -1.9924    0.0273 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4800   -2.5865   -1.2081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3052   -3.2168    0.8016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6998   -1.0739   -0.3680 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1789   -0.3388   -1.4763 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4701   -1.8803   -0.9004 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0342   -2.7336   -1.8913 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4560   -0.9413   -1.5273 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7797   -1.4560   -1.6519 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6564   -0.3444   -1.5673 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8720   -0.4462   -1.8138 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8793    0.8567   -1.1584 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4348    1.6306   -0.0523 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6946    1.9886    0.3701 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5505    2.7415    1.5144 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2734    2.8150    1.7413 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5574    2.1821    0.8562 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0728    2.0416    0.7806 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6022    0.9342   -0.0667 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7270    0.1173   -0.5023 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3232   -0.0618    0.6621 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4144   -0.5761    1.8337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5794    2.8470   -2.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0597    3.1859   -1.2154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6475    4.3658   -1.3001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3328    1.5023    1.7915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4547    0.3903    1.8832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2200   -0.6011    2.6720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3750   -2.1557    1.4677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7611   -1.0273    0.1584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0894   -3.5950   -1.4534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4472   -1.8985   -2.0762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5853   -2.7579   -1.0313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0061   -2.9700    1.8174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2178   -3.8762    0.8990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5859   -3.7842    0.2072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8458   -0.6664   -2.3255 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9574   -2.4938   -0.1220 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7068   -3.4638   -2.0127 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1784   -0.5603   -2.5067 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5470    1.4557   -2.0237 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6557    1.7459   -0.0823 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3390    3.1833    2.1061 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6695    2.0628    1.8048 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7194    3.0081    0.3114 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0008    1.2545   -0.9520 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1892   -0.4124    0.3825 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2453    0.1340    2.1228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1864   -0.6855    2.7638 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9207   -1.5479    1.6840 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  6
  8 10  1  0
  8 11  1  0
 11 12  1  6
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 27  1  0
 27 26  1  0
 26 25  1  0
 25 24  1  0
 24 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 26 28  1  0
 28 29  1  1
 28  5  1  0
 28 11  1  0
 27 15  1  0
 23 24  1  0
 20 19  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  5 33  1  1
  6 34  1  0
  6 35  1  0
  7 36  1  0
  7 37  1  0
  9 38  1  0
  9 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 10 43  1  0
 12 44  1  0
 13 45  1  1
 14 46  1  0
 15 47  1  6
 19 48  1  6
 27 54  1  1
 26 53  1  6
 25 51  1  0
 25 52  1  0
 21 49  1  0
 22 50  1  0
 29 55  1  0
 29 56  1  0
 29 57  1  0
M  END


  Mrv1652304282218232D          

 29 33  0  0  1  0            999 V2000
   -0.6265   -2.9100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0926   -2.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7361   -1.4852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0865   -1.4220    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5525   -2.1027    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1960   -2.8467    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6621   -3.5275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3056   -4.2714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7717   -4.9522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5170   -4.3347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3751   -2.0395    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7316   -1.2955    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2655   -0.6147    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4430   -0.6780    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0231    0.0028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7689    0.0389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5461   -0.2379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2269    0.2282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5230   -1.0626    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1205   -1.6315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9264   -2.4334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1350   -2.6663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6291   -2.8657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2574   -2.3310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9430   -1.5683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0186   -2.7835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3796   -0.7412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4672   -1.1030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8280   -0.6654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
  4 14  1  0  0  0  0
 14 15  1  1  0  0  0
 13 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 19 17  1  6  0  0  0
 12 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 11 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 20 25  1  0  0  0  0
  5 26  1  6  0  0  0
  4 27  1  1  0  0  0
  3 28  1  0  0  0  0
  3 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0070982

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1CCC(C)(C)[C@]2(O)[C@@H](O)[C@@H]3OC(=O)[C@H]4[C@H]3[C@H](CC3=C4C=CO3)[C@@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C22H28O7/c1-10(23)28-14-5-7-20(2,3)22(26)18(24)17-16-12(21(14,22)4)9-13-11(6-8-27-13)15(16)19(25)29-17/h6,8,12,14-18,24,26H,5,7,9H2,1-4H3/t12-,14-,15+,16+,17+,18-,21-,22+/m0/s1

> <INCHI_KEY>
XGRZBPMXGMKFOF-ZCQRYNMDSA-N

> <FORMULA>
C22H28O7

> <MOLECULAR_WEIGHT>
404.459

> <EXACT_MASS>
404.183503242

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
42.02173650593444

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,8S,11R,12S,13R,17S,18S,19R)-12,13-dihydroxy-14,14,18-trimethyl-9-oxo-4,10-dioxapentacyclo[9.7.1.0^{3,7}.0^{8,19}.0^{13,18}]nonadeca-3(7),5-dien-17-yl acetate

> <ALOGPS_LOGP>
2.22

> <JCHEM_LOGP>
1.2381359746666663

> <ALOGPS_LOGS>
-3.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.090926577057218

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.717944695902503

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8238245322528073

> <JCHEM_POLAR_SURFACE_AREA>
106.20000000000002

> <JCHEM_REFRACTIVITY>
100.01270000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.33e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,8S,11R,12S,13R,17S,18S,19R)-12,13-dihydroxy-14,14,18-trimethyl-9-oxo-4,10-dioxapentacyclo[9.7.1.0^{3,7}.0^{8,19}.0^{13,18}]nonadeca-3(7),5-dien-17-yl acetate

> <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      -1.170  -5.432   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.040  -4.161   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.374  -2.772   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.161  -2.654   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.031  -3.925   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.366  -5.314   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.236  -6.585   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.570  -7.973   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.440  -9.244   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.965  -8.091   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.567  -3.807   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.232  -2.418   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.362  -1.147   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.827  -1.266   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.043   0.005   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       3.302   0.073   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.753  -0.444   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.023   0.426   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.710  -1.983   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.825  -3.046   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.463  -4.542   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.985  -4.977   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.774  -5.349   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       7.947  -4.351   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.360  -2.927   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.901  -5.196   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -0.709  -1.384   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -2.739  -2.059   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.546  -1.242   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   28   29                                             
CONECT    4    3    5   14   27                                             
CONECT    5    4    6   11   26                                             
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    5   12   22                                                  
CONECT   12   11   13   19                                                  
CONECT   13   12   14   16                                                  
CONECT   14   13    4   15                                                  
CONECT   15   14                                                            
CONECT   16   13   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   12   20                                                  
CONECT   20   19   21   25                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21   11                                                       
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   20                                                       
CONECT   26    5                                                            
CONECT   27    4                                                            
CONECT   28    3                                                            
CONECT   29    3                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₈O₇

Average Mass

404.4590 Da

Monoisotopic Mass

404.18350 Da

IUPAC Name

(1S,8S,11R,12S,13R,17S,18S,19R)-12,13-dihydroxy-14,14,18-trimethyl-9-oxo-4,10-dioxapentacyclo[9.7.1.0^{3,7}.0^{8,19}.0^{13,18}]nonadeca-3(7),5-dien-17-yl acetate

Traditional Name

(1S,8S,11R,12S,13R,17S,18S,19R)-12,13-dihydroxy-14,14,18-trimethyl-9-oxo-4,10-dioxapentacyclo[9.7.1.0^{3,7}.0^{8,19}.0^{13,18}]nonadeca-3(7),5-dien-17-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1CCC(C)(C)[C@]2(O)[C@@H](O)[C@@H]3OC(=O)[C@H]4[C@H]3[C@H](CC3=C4C=CO3)[C@@]12C

InChI Identifier

InChI=1S/C22H28O7/c1-10(23)28-14-5-7-20(2,3)22(26)18(24)17-16-12(21(14,22)4)9-13-11(6-8-27-13)15(16)19(25)29-17/h6,8,12,14-18,24,26H,5,7,9H2,1-4H3/t12-,14-,15+,16+,17+,18-,21-,22+/m0/s1

InChI Key

XGRZBPMXGMKFOF-ZCQRYNMDSA-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
Guilandina crista	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Eudesmanolides, secoeudesmanolides, and derivatives

Alternative Parents

Substituents

Eudesmanolide
Sesquiterpenoid
Naphthofuran
Benzofuran
Dicarboxylic acid or derivatives
Gamma butyrolactone
Cyclic alcohol
Heteroaromatic compound
Furan
Tetrahydrofuran
Tertiary alcohol
1,2-diol
Carboxylic acid ester
Secondary alcohol
Lactone
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
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	2.22	ALOGPS
logP	1.24	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	12.72	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	106.2 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	100.01 m³·mol⁻¹	ChemAxon
Polarizability	42.02 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00029879

Chemspider ID

9807532

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11632787

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kalauni SK, Awale S, Tezuka Y, Banskota AH, Linn TZ, Kadota S: New cassane-type diterpenes of Caesalpinia crista from Myanmar. Chem Pharm Bull (Tokyo). 2005 Feb;53(2):214-8. doi: 10.1248/cpb.53.214. [PubMed:15684521 ]
Liu T, Wang M, Qi S, Shen X, Wang Y, Jing W, Yang Y, Li X, Gao H: New cassane-type diterpenoids from kernels of Caesalpinia bonduc (Linn.) Roxb. and their inhibitory activities on phosphodiesterase (PDE) and nuclear factor-kappa B (NF-kappaB) expression. Bioorg Chem. 2020 Mar;96:103573. doi: 10.1016/j.bioorg.2020.103573. Epub 2020 Jan 9. [PubMed:31962203 ]

Showing NP-Card for (+)-Caesalpinin O (NP0070982)

MOL for NP0070982 ((+)-Caesalpinin O)

3D MOL for NP0070982 ((+)-Caesalpinin O)

3D SDF for NP0070982 ((+)-Caesalpinin O)

3D-SDF for NP0070982 ((+)-Caesalpinin O)

PDB for NP0070982 ((+)-Caesalpinin O)

3D PDB for NP0070982 ((+)-Caesalpinin O)

SMILES for NP0070982 ((+)-Caesalpinin O)

INCHI for NP0070982 ((+)-Caesalpinin O)

Structure for NP0070982 ((+)-Caesalpinin O)

3D Structure for NP0070982 ((+)-Caesalpinin O)