NP-MRD: Showing NP-Card for (1r,12'r,16's)-9'-hydroxy-3,4-dimethoxy-5',5'-dimethyl-6',14',17'-trioxaspiro[cyclohexane-1,13'-tetracyclo[8.7.0.0²,⁷.0¹²,¹⁶]heptadecane]-1',2,3',4,7',9'-hexaene-6,11'-dione (NP0152514)

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Record Information

Version

2.0

Created at

2022-09-02 09:00:52 UTC

Updated at

2022-09-02 09:00:52 UTC

NP-MRD ID

NP0152514

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,12'r,16's)-9'-hydroxy-3,4-dimethoxy-5',5'-dimethyl-6',14',17'-trioxaspiro[cyclohexane-1,13'-tetracyclo[8.7.0.0²,⁷.0¹²,¹⁶]heptadecane]-1',2,3',4,7',9'-hexaene-6,11'-dione

Description

CHEMBL491618 belongs to the class of organic compounds known as pyranochromenes. These are organic heterocyclic compounds containing a pyran ring fused to a chromene (1-benzopyran) moiety. (1r,12'r,16's)-9'-hydroxy-3,4-dimethoxy-5',5'-dimethyl-6',14',17'-trioxaspiro[cyclohexane-1,13'-tetracyclo[8.7.0.0²,⁷.0¹²,¹⁶]heptadecane]-1',2,3',4,7',9'-hexaene-6,11'-dione is found in Amorpha fruticosa. Based on a literature review very few articles have been published on CHEMBL491618.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022211002D          

 31 35  0  0  1  0            999 V2000
   -0.8708   -2.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9770   -3.3056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3215   -3.8066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4401   -3.4894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0956   -3.9904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8572   -3.6732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9894   -4.8085    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2278   -5.1257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4276   -4.6247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1892   -4.9419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2954   -5.7600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9694   -5.6333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7476   -5.9072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2486   -5.2517    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0709   -5.1855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4247   -4.4402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2470   -4.3739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6008   -3.6286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1322   -2.9495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3099   -3.0158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8413   -2.3368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9561   -3.7611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1338   -3.8274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8980   -3.0368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7800   -4.5727    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4231   -3.5623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8917   -4.2413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4790   -3.6619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5642   -4.7191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5379   -4.9866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7156   -5.0529    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  7 12  1  1  0  0  0
 12 13  1  0  0  0  0
 14 13  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 16 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 25 23  1  6  0  0  0
 14 25  1  0  0  0  0
  7 25  1  0  0  0  0
 18 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 27 30  1  0  0  0  0
 30 31  2  0  0  0  0
 17 31  1  0  0  0  0
M  END

     RDKit          3D

 53 57  0  0  0  0  0  0  0  0999 V2000
   -6.9148    1.9609    0.3303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3777    0.6916   -0.0333 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9980    0.6232   -0.1743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3925    1.3207   -1.1414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9437    1.2508   -1.2919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4396    1.9318   -2.2206 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0785    0.4295   -0.4130 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8720   -0.2853    0.6070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1874   -0.1989    0.7155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8969   -0.9026    1.7076 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7318   -1.9497    1.2288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1623    1.2918    0.1827 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2540    1.6373   -0.8086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1620    0.4851   -1.7547 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1603   -0.0801   -1.8019 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7230   -0.5629   -0.6300 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0350   -0.3661   -0.2531 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5365   -0.8766    0.9326 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6621   -1.5879    1.7141 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3205   -1.8022    1.3522 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5109   -2.5187    2.1826 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8551   -1.2891    0.1804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5181   -1.4494   -0.3012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1377   -2.4772    0.1029 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1747   -0.4839   -1.2108 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8521   -0.6505    1.2585 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7528    0.0751    0.4661 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9619   -0.8081    0.1947 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2463    1.3258    1.2232 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1588    0.5878   -0.7749 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9169    0.3847   -1.1008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0157    1.8877    0.4111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5461    2.2800    1.3280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6805    2.7469   -0.3993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0205    1.9206   -1.7850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3748   -0.9199    1.3172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1193   -2.7219    0.6787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4781   -1.5842    0.4933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3003   -2.4308    2.0400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4212    2.6116   -1.2634 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7467    1.7065   -0.2883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3769    0.7662   -2.8084 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0361   -1.9984    2.6519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4181   -2.7850    2.1612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7372   -1.0018   -2.0240 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0917   -1.5808    0.9779 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8851   -1.2557   -0.8186 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8597   -0.1629    0.1935 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9058    1.8492    0.4725 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4155    1.9951    1.4496 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8556    1.0359    2.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7662    1.1649   -1.4654 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4758    0.7702   -2.0308 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
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7 12  1  1
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 31  1  0
 31 30  2  0
 30 27  1  0
 27 28  1  0
 27 29  1  0
 27 26  1  0
 26 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
  9  3  1  0
 25  7  1  0
 25 14  1  0
 22 16  1  0
 18 17  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  4 35  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  6
 31 53  1  0
 30 52  1  0
 28 46  1  0
 28 47  1  0
 28 48  1  0
 29 49  1  0
 29 50  1  0
 29 51  1  0
 19 43  1  0
 21 44  1  0
 25 45  1  6
  8 36  1  0
 11 37  1  0
 11 38  1  0
 11 39  1  0
M  END


  Mrv1652309022211002D          

 31 35  0  0  1  0            999 V2000
   -0.8708   -2.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9770   -3.3056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3215   -3.8066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4401   -3.4894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0956   -3.9904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8572   -3.6732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9894   -4.8085    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2278   -5.1257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4276   -4.6247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1892   -4.9419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2954   -5.7600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9694   -5.6333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7476   -5.9072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2486   -5.2517    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0709   -5.1855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4247   -4.4402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2470   -4.3739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6008   -3.6286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1322   -2.9495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3099   -3.0158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8413   -2.3368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9561   -3.7611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1338   -3.8274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8980   -3.0368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7800   -4.5727    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4231   -3.5623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8917   -4.2413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4790   -3.6619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5642   -4.7191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5379   -4.9866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7156   -5.0529    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  7 12  1  1  0  0  0
 12 13  1  0  0  0  0
 14 13  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 16 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 25 23  1  6  0  0  0
 14 25  1  0  0  0  0
  7 25  1  0  0  0  0
 18 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 27 30  1  0  0  0  0
 30 31  2  0  0  0  0
 17 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0152514

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=O)[C@@]2(OC[C@H]3OC4=C5C=CC(C)(C)OC5=CC(O)=C4C(=O)[C@@H]23)C=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C23H22O8/c1-22(2)6-5-11-13(31-22)7-12(24)18-20(26)19-16(30-21(11)18)10-29-23(19)9-15(28-4)14(27-3)8-17(23)25/h5-9,16,19,24H,10H2,1-4H3/t16-,19+,23+/m1/s1

> <INCHI_KEY>
ZBTGBOZTIJWBIP-ICPLQIHGSA-N

> <FORMULA>
C23H22O8

> <MOLECULAR_WEIGHT>
426.421

> <EXACT_MASS>
426.131467668

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
43.12575572532006

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,12'R,16'S)-9'-hydroxy-3,4-dimethoxy-5',5'-dimethyl-6',14',17'-trioxaspiro[cyclohexane-1,13'-tetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadecane]-1',2,3',4,7',9'-hexaene-6,11'-dione

> <ALOGPS_LOGP>
2.70

> <JCHEM_LOGP>
2.2396392780000003

> <ALOGPS_LOGS>
-3.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.724673987904147

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.079674808754573

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9891099717746124

> <JCHEM_POLAR_SURFACE_AREA>
100.52000000000002

> <JCHEM_REFRACTIVITY>
113.02610000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.99e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,12'R,16'S)-9'-hydroxy-3,4-dimethoxy-5',5'-dimethyl-6',14',17'-trioxaspiro[cyclohexane-1,13'-tetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadecane]-1',2,3',4,7',9'-hexaene-6,11'-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.626  -4.643   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.824  -6.170   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.600  -7.106   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.822  -6.514   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.045  -7.449   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.467  -6.857   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.847  -8.976   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.425  -9.568   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.798  -8.633   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.220  -9.225   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -2.418 -10.752   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.810 -10.516   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.262 -11.027   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.197  -9.803   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.732  -9.680   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.393  -8.288   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.928  -8.165   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.588  -6.773   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.713  -5.506   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.178  -5.630   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.304  -4.362   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.518  -7.021   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.983  -7.145   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.543  -5.669   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.323  -8.536   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      10.123  -6.650   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      10.998  -7.917   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.094  -6.836   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.253  -8.809   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.337  -9.308   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.802  -9.432   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   12   25                                             
CONECT    8    7    9                                                       
CONECT    9    8    3   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    7   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   25                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   22                                                  
CONECT   17   16   18   31                                                  
CONECT   18   17   19   26                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   16   23                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   14    7                                                  
CONECT   26   18   27                                                       
CONECT   27   26   28   29   30                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   27   31                                                       
CONECT   31   30   17                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₂O₈

Average Mass

426.4210 Da

Monoisotopic Mass

426.13147 Da

IUPAC Name

(1R,12'R,16'S)-9'-hydroxy-3,4-dimethoxy-5',5'-dimethyl-6',14',17'-trioxaspiro[cyclohexane-1,13'-tetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadecane]-1',2,3',4,7',9'-hexaene-6,11'-dione

Traditional Name

(1R,12'R,16'S)-9'-hydroxy-3,4-dimethoxy-5',5'-dimethyl-6',14',17'-trioxaspiro[cyclohexane-1,13'-tetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadecane]-1',2,3',4,7',9'-hexaene-6,11'-dione

CAS Registry Number

Not Available

SMILES

COC1=CC(=O)[C@@]2(OC[C@H]3OC4=C5C=CC(C)(C)OC5=CC(O)=C4C(=O)[C@@H]23)C=C1OC

InChI Identifier

InChI=1S/C23H22O8/c1-22(2)6-5-11-13(31-22)7-12(24)18-20(26)19-16(30-21(11)18)10-29-23(19)9-15(28-4)14(27-3)8-17(23)25/h5-9,16,19,24H,10H2,1-4H3/t16-,19+,23+/m1/s1

InChI Key

ZBTGBOZTIJWBIP-ICPLQIHGSA-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

Species Name	Source	Reference
Amorpha fruticosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranochromenes. These are organic heterocyclic compounds containing a pyran ring fused to a chromene (1-benzopyran) moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Pyranochromenes

Alternative Parents

Substituents

Pyranochromene
2,2-dimethyl-1-benzopyran
Chromone
Aryl ketone
Aryl alkyl ketone
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Tetrahydrofuran
Vinylogous ester
Vinylogous acid
Ketone
Ether
Dialkyl ether
Oxacycle
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Organic oxide
Carbonyl group
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	2.7	ALOGPS
logP	2.24	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	8.08	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	100.52 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	113.03 m³·mol⁻¹	ChemAxon
Polarizability	43.13 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

Not Available

Chemspider ID

24705785

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25135580

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,12'r,16's)-9'-hydroxy-3,4-dimethoxy-5',5'-dimethyl-6',14',17'-trioxaspiro[cyclohexane-1,13'-tetracyclo[8.7.0.0²,⁷.0¹²,¹⁶]heptadecane]-1',2,3',4,7',9'-hexaene-6,11'-dione (NP0152514)

MOL for NP0152514 ((1r,12'r,16's)-9'-hydroxy-3,4-dimethoxy-5',5'-dimethyl-6',14',17'-trioxaspiro[cyclohexane-1,13'-tetracyclo[8.7.0.0²,⁷.0¹²,¹⁶]heptadecane]-1',2,3',4,7',9'-hexaene-6,11'-dione)

3D MOL for NP0152514 ((1r,12'r,16's)-9'-hydroxy-3,4-dimethoxy-5',5'-dimethyl-6',14',17'-trioxaspiro[cyclohexane-1,13'-tetracyclo[8.7.0.0²,⁷.0¹²,¹⁶]heptadecane]-1',2,3',4,7',9'-hexaene-6,11'-dione)

3D SDF for NP0152514 ((1r,12'r,16's)-9'-hydroxy-3,4-dimethoxy-5',5'-dimethyl-6',14',17'-trioxaspiro[cyclohexane-1,13'-tetracyclo[8.7.0.0²,⁷.0¹²,¹⁶]heptadecane]-1',2,3',4,7',9'-hexaene-6,11'-dione)

3D-SDF for NP0152514 ((1r,12'r,16's)-9'-hydroxy-3,4-dimethoxy-5',5'-dimethyl-6',14',17'-trioxaspiro[cyclohexane-1,13'-tetracyclo[8.7.0.0²,⁷.0¹²,¹⁶]heptadecane]-1',2,3',4,7',9'-hexaene-6,11'-dione)

PDB for NP0152514 ((1r,12'r,16's)-9'-hydroxy-3,4-dimethoxy-5',5'-dimethyl-6',14',17'-trioxaspiro[cyclohexane-1,13'-tetracyclo[8.7.0.0²,⁷.0¹²,¹⁶]heptadecane]-1',2,3',4,7',9'-hexaene-6,11'-dione)

3D PDB for NP0152514 ((1r,12'r,16's)-9'-hydroxy-3,4-dimethoxy-5',5'-dimethyl-6',14',17'-trioxaspiro[cyclohexane-1,13'-tetracyclo[8.7.0.0²,⁷.0¹²,¹⁶]heptadecane]-1',2,3',4,7',9'-hexaene-6,11'-dione)

SMILES for NP0152514 ((1r,12'r,16's)-9'-hydroxy-3,4-dimethoxy-5',5'-dimethyl-6',14',17'-trioxaspiro[cyclohexane-1,13'-tetracyclo[8.7.0.0²,⁷.0¹²,¹⁶]heptadecane]-1',2,3',4,7',9'-hexaene-6,11'-dione)

INCHI for NP0152514 ((1r,12'r,16's)-9'-hydroxy-3,4-dimethoxy-5',5'-dimethyl-6',14',17'-trioxaspiro[cyclohexane-1,13'-tetracyclo[8.7.0.0²,⁷.0¹²,¹⁶]heptadecane]-1',2,3',4,7',9'-hexaene-6,11'-dione)

Structure for NP0152514 ((1r,12'r,16's)-9'-hydroxy-3,4-dimethoxy-5',5'-dimethyl-6',14',17'-trioxaspiro[cyclohexane-1,13'-tetracyclo[8.7.0.0²,⁷.0¹²,¹⁶]heptadecane]-1',2,3',4,7',9'-hexaene-6,11'-dione)

3D Structure for NP0152514 ((1r,12'r,16's)-9'-hydroxy-3,4-dimethoxy-5',5'-dimethyl-6',14',17'-trioxaspiro[cyclohexane-1,13'-tetracyclo[8.7.0.0²,⁷.0¹²,¹⁶]heptadecane]-1',2,3',4,7',9'-hexaene-6,11'-dione)