NP-MRD: Showing NP-Card for methyl (1r,3s,6r,7r,10s,11r,12r)-11-hydroxy-10-isopropyl-3,7-dimethyl-15-oxatetracyclo[9.3.1.0¹,⁶.0⁷,¹²]pentadec-13-ene-13-carboxylate (NP0207457)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-05 04:04:44 UTC

Updated at

2022-09-05 04:04:45 UTC

NP-MRD ID

NP0207457

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1r,3s,6r,7r,10s,11r,12r)-11-hydroxy-10-isopropyl-3,7-dimethyl-15-oxatetracyclo[9.3.1.0¹,⁶.0⁷,¹²]pentadec-13-ene-13-carboxylate

Description

Chatancin belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. methyl (1r,3s,6r,7r,10s,11r,12r)-11-hydroxy-10-isopropyl-3,7-dimethyl-15-oxatetracyclo[9.3.1.0¹,⁶.0⁷,¹²]pentadec-13-ene-13-carboxylate was first documented in 2003 (PMID: 14682691). Based on a literature review a small amount of articles have been published on Chatancin (PMID: 30908860) (PMID: 32202757) (PMID: 28405231) (PMID: 25470723).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052206042D          

 25 28  0  0  1  0            999 V2000
    3.1425    2.3508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3375    2.1704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0912    1.3831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2861    1.2027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6499    0.7761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5192    0.8075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6814   -0.0370    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5114    0.1676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0332   -0.4910    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8377   -0.3084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8451   -1.3180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0568   -1.6153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5673   -0.9190    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7287   -1.0317    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1060   -1.7654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1497   -1.6478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4156   -1.2364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3603   -0.3799    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5800   -0.1122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4216    0.6975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0420   -0.6541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9363    0.2697    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6073    1.0263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8768    0.2461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5349   -0.1867    0.0000 C   0  0  1  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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  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  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  6  0  0  0
  7 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 18 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
  7 24  1  1  0  0  0
 22 25  1  0  0  0  0
 25  5  1  1  0  0  0
 14 25  1  0  0  0  0
M  END

     RDKit          3D

 57 60  0  0  0  0  0  0  0  0999 V2000
   -1.9093    5.1464   -1.2907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6891    3.7619   -1.1616 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6345    3.1980   -0.4722 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1873    3.9724    0.0792 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4204    1.7773   -0.3474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2302    0.8564   -0.8925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7817   -0.5518   -0.5811 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7398   -1.4698   -1.2743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0923   -1.2597   -0.6251 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1254   -2.0160   -1.4195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9941   -1.7517    0.7978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0368   -0.9080    1.5675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7013   -0.7496    0.9008 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1131    0.3431    1.5059 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6958    1.2833    2.3744 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2542   -0.1874    2.3310 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3485   -0.8128    1.5701 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5618   -0.3901    0.1771 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0366   -1.6043   -0.6286 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3276   -2.0657    0.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3237   -1.2448   -2.0520 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3944    0.1881   -0.5356 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8870    0.9611   -1.6134 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5309   -0.7321   -1.0691 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7211    1.1855    0.3991 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6278    5.4512   -0.5067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9796    5.7336   -1.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2458    5.4359   -2.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0884    1.0874   -1.4764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4458   -2.5196   -1.2026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8399   -1.1159   -2.3232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3897   -0.2121   -0.5967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1026   -2.0500   -0.9218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2811   -1.4401   -2.3701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7592   -3.0213   -1.7386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0011   -1.6368    1.2791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7754   -2.8317    0.8209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5230    0.0657    1.7881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8653   -1.3920    2.5515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1469   -1.7154    1.0676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4632    1.8252    1.7826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1340    0.7675    3.2545 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0232    2.0694    2.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7930   -0.9165    3.0617 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6015    0.6592    2.9781 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2205   -1.9343    1.6325 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3113   -0.6320    2.1364 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4100    0.3502    0.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2792   -2.4171   -0.5691 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2635   -2.1205    1.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6649   -3.0405   -0.3967 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0812   -1.2566   -0.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4181   -1.1529   -2.6831 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9272   -2.0679   -2.4890 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9590   -0.3381   -2.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6280    1.5297   -1.2931 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4529    1.9064    0.7428 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  6
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  1
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 18 22  1  0
 22 23  1  6
 22 24  1  0
 22 25  1  0
 25  5  1  0
 13  7  1  0
 25 14  1  0
 24  7  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  6 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  1
 10 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  6
 15 41  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  0
 16 45  1  0
 17 46  1  0
 17 47  1  0
 18 48  1  1
 19 49  1  0
 20 50  1  0
 20 51  1  0
 20 52  1  0
 21 53  1  0
 21 54  1  0
 21 55  1  0
 23 56  1  0
 25 57  1  1
M  END


  Mrv1652309052206042D          

 25 28  0  0  1  0            999 V2000
    3.1425    2.3508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3375    2.1704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0912    1.3831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2861    1.2027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6499    0.7761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5192    0.8075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6814   -0.0370    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5114    0.1676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0332   -0.4910    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8377   -0.3084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8451   -1.3180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0568   -1.6153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5673   -0.9190    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7287   -1.0317    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1060   -1.7654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1497   -1.6478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4156   -1.2364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3603   -0.3799    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5800   -0.1122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4216    0.6975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0420   -0.6541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9363    0.2697    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6073    1.0263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8768    0.2461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5349   -0.1867    0.0000 C   0  0  1  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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  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  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  6  0  0  0
  7 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 18 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
  7 24  1  1  0  0  0
 22 25  1  0  0  0  0
 25  5  1  1  0  0  0
 14 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0207457

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=C[C@]23C[C@@H](C)CC[C@@H]2[C@@]2(C)CC[C@@H](C(C)C)[C@@](O)(O3)[C@@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C21H32O4/c1-12(2)15-8-9-19(4)16-7-6-13(3)10-20(16)11-14(18(22)24-5)17(19)21(15,23)25-20/h11-13,15-17,23H,6-10H2,1-5H3/t13-,15-,16+,17-,19+,20+,21+/m0/s1

> <INCHI_KEY>
CWSSNRJGRZWATA-DIGXBJOVSA-N

> <FORMULA>
C21H32O4

> <MOLECULAR_WEIGHT>
348.483

> <EXACT_MASS>
348.23005951

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
39.768022158717095

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1R,3S,6R,7R,10S,11R,12R)-11-hydroxy-3,7-dimethyl-10-(propan-2-yl)-15-oxatetracyclo[9.3.1.0^{1,6}.0^{7,12}]pentadec-13-ene-13-carboxylate

> <JCHEM_LOGP>
4.15550487

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.525849128404735

> <JCHEM_PKA_STRONGEST_BASIC>
-4.318393591235769

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
96.241

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,3S,6R,7R,10S,11R,12R)-11-hydroxy-10-isopropyl-3,7-dimethyl-15-oxatetracyclo[9.3.1.0^{1,6}.0^{7,12}]pentadec-13-ene-13-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       5.866   4.388   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.363   4.052   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.904   2.582   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.401   2.245   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.946   1.449   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.569   1.507   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.872  -0.069   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.421   0.313   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.395  -0.917   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.897  -0.576   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.044  -2.460   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.573  -3.015   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.659  -1.716   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.094  -1.926   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.798  -3.295   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.013  -3.076   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.642  -2.308   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.539  -0.709   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.083  -0.209   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.787   1.302   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.078  -1.221   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.614   0.504   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.000   1.916   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       5.370   0.459   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.732  -0.349   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   25                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   13   24                                             
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    7   14                                                  
CONECT   14   13   15   16   25                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   22                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   18   23   24   25                                             
CONECT   23   22                                                            
CONECT   24   22    7                                                       
CONECT   25   22    5   14                                                  
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₃₂O₄

Average Mass

348.4830 Da

Monoisotopic Mass

348.23006 Da

IUPAC Name

methyl (1R,3S,6R,7R,10S,11R,12R)-11-hydroxy-3,7-dimethyl-10-(propan-2-yl)-15-oxatetracyclo[9.3.1.0^{1,6}.0^{7,12}]pentadec-13-ene-13-carboxylate

Traditional Name

methyl (1R,3S,6R,7R,10S,11R,12R)-11-hydroxy-10-isopropyl-3,7-dimethyl-15-oxatetracyclo[9.3.1.0^{1,6}.0^{7,12}]pentadec-13-ene-13-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=C[C@]23C[C@@H](C)CC[C@@H]2[C@@]2(C)CC[C@@H](C(C)C)[C@@](O)(O3)[C@@H]12

InChI Identifier

InChI=1S/C21H32O4/c1-12(2)15-8-9-19(4)16-7-6-13(3)10-20(16)11-14(18(22)24-5)17(19)21(15,23)25-20/h11-13,15-17,23H,6-10H2,1-5H3/t13-,15-,16+,17-,19+,20+,21+/m0/s1

InChI Key

CWSSNRJGRZWATA-DIGXBJOVSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Oxane
Pyran
Cyclic alcohol
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Hemiacetal
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	4.16	ChemAxon
pKa (Strongest Acidic)	11.53	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	96.24 m³·mol⁻¹	ChemAxon
Polarizability	39.77 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

Not Available

Chemspider ID

9998900

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11824249

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

He C, Xuan J, Rao P, Xie PP, Hong X, Lin X, Ding H: Total Syntheses of (+)-Sarcophytin, (+)-Chatancin, (-)-3-Oxochatancin, and (-)-Pavidolide B: A Divergent Approach. Angew Chem Int Ed Engl. 2019 Apr 1;58(15):5100-5104. doi: 10.1002/anie.201900782. Epub 2019 Mar 12. [PubMed:30908860 ]
Harmange Magnani CS, Thach DQ, Haelsig KT, Maimone TJ: Syntheses of Complex Terpenes from Simple Polyprenyl Precursors. Acc Chem Res. 2020 Apr 21;53(4):949-961. doi: 10.1021/acs.accounts.0c00055. Epub 2020 Mar 23. [PubMed:32202757 ]
Bogdanov A, Hertzer C, Kehraus S, Nietzer S, Rohde S, Schupp PJ, Wagele H, Konig GM: Secondary metabolome and its defensive role in the aeolidoidean Phyllodesmium longicirrum, (Gastropoda, Heterobranchia, Nudibranchia). Beilstein J Org Chem. 2017 Mar 13;13:502-519. doi: 10.3762/bjoc.13.50. eCollection 2017. [PubMed:28405231 ]
Zhao YM, Maimone TJ: Short, enantioselective total synthesis of chatancin. Angew Chem Int Ed Engl. 2015 Jan 19;54(4):1223-6. doi: 10.1002/anie.201410443. Epub 2014 Dec 2. [PubMed:25470723 ]
Soucy P, L'Heureux A, Toro A, Deslongchamps P: Pyranophane transannular diels-alder approach to (+)-chatancin: a biomimetic asymmetric total synthesis. J Org Chem. 2003 Dec 26;68(26):9983-7. doi: 10.1021/jo035193y. [PubMed:14682691 ]
LOTUS database [Link]

Showing NP-Card for methyl (1r,3s,6r,7r,10s,11r,12r)-11-hydroxy-10-isopropyl-3,7-dimethyl-15-oxatetracyclo[9.3.1.0¹,⁶.0⁷,¹²]pentadec-13-ene-13-carboxylate (NP0207457)

MOL for NP0207457 (methyl (1r,3s,6r,7r,10s,11r,12r)-11-hydroxy-10-isopropyl-3,7-dimethyl-15-oxatetracyclo[9.3.1.0¹,⁶.0⁷,¹²]pentadec-13-ene-13-carboxylate)

3D MOL for NP0207457 (methyl (1r,3s,6r,7r,10s,11r,12r)-11-hydroxy-10-isopropyl-3,7-dimethyl-15-oxatetracyclo[9.3.1.0¹,⁶.0⁷,¹²]pentadec-13-ene-13-carboxylate)

3D SDF for NP0207457 (methyl (1r,3s,6r,7r,10s,11r,12r)-11-hydroxy-10-isopropyl-3,7-dimethyl-15-oxatetracyclo[9.3.1.0¹,⁶.0⁷,¹²]pentadec-13-ene-13-carboxylate)

3D-SDF for NP0207457 (methyl (1r,3s,6r,7r,10s,11r,12r)-11-hydroxy-10-isopropyl-3,7-dimethyl-15-oxatetracyclo[9.3.1.0¹,⁶.0⁷,¹²]pentadec-13-ene-13-carboxylate)

PDB for NP0207457 (methyl (1r,3s,6r,7r,10s,11r,12r)-11-hydroxy-10-isopropyl-3,7-dimethyl-15-oxatetracyclo[9.3.1.0¹,⁶.0⁷,¹²]pentadec-13-ene-13-carboxylate)

3D PDB for NP0207457 (methyl (1r,3s,6r,7r,10s,11r,12r)-11-hydroxy-10-isopropyl-3,7-dimethyl-15-oxatetracyclo[9.3.1.0¹,⁶.0⁷,¹²]pentadec-13-ene-13-carboxylate)

SMILES for NP0207457 (methyl (1r,3s,6r,7r,10s,11r,12r)-11-hydroxy-10-isopropyl-3,7-dimethyl-15-oxatetracyclo[9.3.1.0¹,⁶.0⁷,¹²]pentadec-13-ene-13-carboxylate)

INCHI for NP0207457 (methyl (1r,3s,6r,7r,10s,11r,12r)-11-hydroxy-10-isopropyl-3,7-dimethyl-15-oxatetracyclo[9.3.1.0¹,⁶.0⁷,¹²]pentadec-13-ene-13-carboxylate)

Structure for NP0207457 (methyl (1r,3s,6r,7r,10s,11r,12r)-11-hydroxy-10-isopropyl-3,7-dimethyl-15-oxatetracyclo[9.3.1.0¹,⁶.0⁷,¹²]pentadec-13-ene-13-carboxylate)

3D Structure for NP0207457 (methyl (1r,3s,6r,7r,10s,11r,12r)-11-hydroxy-10-isopropyl-3,7-dimethyl-15-oxatetracyclo[9.3.1.0¹,⁶.0⁷,¹²]pentadec-13-ene-13-carboxylate)