NP-MRD: Showing NP-Card for Tricyclodehydroisohumulone (NP0051555)

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Record Information

Version

2.0

Created at

2022-04-27 22:52:35 UTC

Updated at

2022-04-27 22:52:35 UTC

NP-MRD ID

NP0051555

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Tricyclodehydroisohumulone

Description

(1R,5R,8R,10R)-4,5-dihydroxy-9,9-dimethyl-3-(3-methylbutanoyl)-10-(prop-1-en-2-yl)tricyclo[6.3.0.0¹,⁵]Undec-3-ene-2,6-dione belongs to the class of organic compounds known as angular triquinanes. Tricyclodehydroisohumulone is found in Humulus lupulus . These are triquinane with a structure based on a [6.3.0.0^1,5] Undecane carbon skeleton (1R,5R,8R,10R)-4,5-dihydroxy-9,9-dimethyl-3-(3-methylbutanoyl)-10-(prop-1-en-2-yl)tricyclo[6.3.0.0¹,⁵]Undec-3-ene-2,6-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

Tricyclodehydroisohumulone
  Mrv1652309271700072D          

 28 30  0  0  1  0            999 V2000
    4.7977   -2.0894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4018    0.7255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8043   -2.4639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9612    0.2297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5395   -0.4596    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7246   -0.3306    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5983    0.4799    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9099    0.2721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6686   -1.2746    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3296    0.8516    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3501   -1.0657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2712   -0.0892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9335   -1.6491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2251    1.2157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7833    0.3521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4790   -1.4008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8507   -0.6696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2596    1.6001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6656   -0.5406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6185    1.9426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6763    2.1168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1848   -1.1816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9997   -1.0527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5190   -1.6938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2954   -0.2824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9099   -0.2005    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8110    1.3353    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8548   -2.1352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  1  1  6  0  0  0
  2 12  2  0  0  0  0
  3 13  2  0  0  0  0
  4 19  2  0  0  0  0
  6  5  1  0  0  0  0
  5  8  1  6  0  0  0
  5  9  1  0  0  0  0
  5 12  1  0  0  0  0
  6  7  1  0  0  0  0
  6 11  1  0  0  0  0
  7 10  1  0  0  0  0
  7 14  1  1  0  0  0
  7 15  1  0  0  0  0
  8 10  1  0  0  0  0
  9 13  1  0  0  0  0
  9 16  1  0  0  0  0
 10 18  1  1  0  0  0
 11 13  1  0  0  0  0
 16 17  2  0  0  0  0
 17 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  2  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
  6 26  1  1  0  0  0
 10 27  1  6  0  0  0
 17 12  1  0  0  0  0
 16 28  1  0  0  0  0
M  END

     RDKit          3D

 54 56  0  0  0  0  0  0  0  0999 V2000
   -3.3170   -2.4023   -0.9987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0271   -1.9376    0.1781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7025   -3.0099    1.2155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9584   -0.5883    0.6934 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5294   -0.2150    1.1318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8680    0.3534   -0.0796 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1599   -0.4950   -0.6622 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0162   -1.4467   -1.4446 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4324   -0.0045   -0.1396 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7142   -0.6822   -0.0977 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -1.8422   -0.5538 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8916    0.0016    0.4809 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1046   -0.9238    0.4030 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4022   -1.2840   -1.0191 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2932   -0.2220    1.0264 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2540    1.2377    0.3287 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2107    2.0685    0.9130 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1515    1.6407    0.1407 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6086    2.3735    1.2268 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3619    2.3613   -1.1451 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4507    3.1081   -1.6641 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7167    1.9919   -1.6406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9936    0.6980   -0.9956 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2648    0.5619   -0.2190 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5142    1.7216    0.7275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4620    0.4031   -1.0910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3107   -3.4752   -1.1797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5775   -1.8127   -1.8626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6595   -3.5483    1.3906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0129   -3.7365    0.7205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2619   -2.5962    2.1161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6240   -0.5440    1.6110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0211   -1.1847    1.3497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5031    0.3942    2.0301 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6552    0.2111    1.5411 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1317    0.9264   -0.0796 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8649   -1.8476    0.9602 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5147   -1.2443   -1.1581 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9402   -0.5623   -1.7327 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0605   -2.3023   -1.2725 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2547   -0.6105    0.6534 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2768   -0.4035    2.1256 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2096    0.8769    0.7901 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2738    3.0601    0.6558 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1024    2.9672    1.5771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6572    1.8979   -2.7693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4180    2.8124   -1.4820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0003   -0.0828   -1.7839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6375    1.7804    0.8522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2045    2.6944    0.3705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1618    1.5345    1.7624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2542    0.4164   -2.1816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1333   -0.4163   -0.7634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1087    1.3275   -0.9558 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0
  6  5  1  1
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
  9 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  1
 18 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  1
 24 26  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  3
 24  4  1  0
 18  6  1  0
 23  6  1  0
  4 32  1  1
  5 33  1  0
  5 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  1
 14 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 15 43  1  0
 17 44  1  0
 19 45  1  0
 22 46  1  0
 22 47  1  0
 23 48  1  6
 25 49  1  0
 25 50  1  0
 25 51  1  0
 26 52  1  0
 26 53  1  0
 26 54  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  1 27  1  0
  1 28  1  0
M  END

Tricyclodehydroisohumulone
  Mrv1652309271700072D          

 28 30  0  0  1  0            999 V2000
    4.7977   -2.0894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4018    0.7255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8043   -2.4639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9612    0.2297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5395   -0.4596    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7246   -0.3306    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5983    0.4799    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9099    0.2721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6686   -1.2746    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3296    0.8516    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3501   -1.0657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2712   -0.0892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9335   -1.6491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2251    1.2157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7833    0.3521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4790   -1.4008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8507   -0.6696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2596    1.6001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6656   -0.5406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6185    1.9426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6763    2.1168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1848   -1.1816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9997   -1.0527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5190   -1.6938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2954   -0.2824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9099   -0.2005    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8110    1.3353    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8548   -2.1352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  1  1  6  0  0  0
  2 12  2  0  0  0  0
  3 13  2  0  0  0  0
  4 19  2  0  0  0  0
  6  5  1  0  0  0  0
  5  8  1  6  0  0  0
  5  9  1  0  0  0  0
  5 12  1  0  0  0  0
  6  7  1  0  0  0  0
  6 11  1  0  0  0  0
  7 10  1  0  0  0  0
  7 14  1  1  0  0  0
  7 15  1  0  0  0  0
  8 10  1  0  0  0  0
  9 13  1  0  0  0  0
  9 16  1  0  0  0  0
 10 18  1  1  0  0  0
 11 13  1  0  0  0  0
 16 17  2  0  0  0  0
 17 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  2  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
  6 26  1  1  0  0  0
 10 27  1  6  0  0  0
 17 12  1  0  0  0  0
 16 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051555

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(C[C@]23C(=O)C(C(=O)CC(C)C)=C(O)[C@@]2(O)C(=O)C[C@]3([H])C1(C)C)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C21H28O5/c1-10(2)7-13(22)16-17(24)20-9-12(11(3)4)19(5,6)14(20)8-15(23)21(20,26)18(16)25/h10,12,14,25-26H,3,7-9H2,1-2,4-6H3/t12-,14-,20+,21+/m1/s1

> <INCHI_KEY>
FZQFCXBBPNGZEI-QZHPCCELSA-N

> <FORMULA>
C21H28O5

> <MOLECULAR_WEIGHT>
360.45

> <EXACT_MASS>
360.193674002

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
38.54877508105544

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,5R,8R,10R)-4,5-dihydroxy-9,9-dimethyl-3-(3-methylbutanoyl)-10-(prop-1-en-2-yl)tricyclo[6.3.0.0^{1,5}]undec-3-ene-2,6-dione

> <ALOGPS_LOGP>
2.00

> <JCHEM_LOGP>
3.0975777639999986

> <ALOGPS_LOGS>
-3.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.762063113290667

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.37972427744339443

> <JCHEM_PKA_STRONGEST_BASIC>
-4.426063314672024

> <JCHEM_POLAR_SURFACE_AREA>
91.67

> <JCHEM_REFRACTIVITY>
98.21689999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.18e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,5R,8R,10R)-4,5-dihydroxy-9,9-dimethyl-3-(3-methylbutanoyl)-10-(prop-1-en-2-yl)tricyclo[6.3.0.0^{1,5}]undec-3-ene-2,6-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-SEP-17   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Tricyclodehydroisohumulone                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-17         0                                  
HETATM    1  O   UNK     0       8.956  -3.900   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      10.083   1.354   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       7.101  -4.599   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      12.994   0.429   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       8.474  -0.858   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.953  -0.617   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.717   0.896   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.165   0.508   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.715  -2.379   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.082   1.590   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.254  -1.989   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.840  -0.167   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.343  -3.078   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.020   2.269   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.195   0.657   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.227  -2.615   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.921  -1.250   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.951   2.987   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.442  -1.009   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.755   3.626   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.729   3.951   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.412  -2.206   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.933  -1.965   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      15.902  -3.162   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      15.485  -0.527   0.000  0.00  0.00           C+0
HETATM   26  H   UNK     0       5.432  -0.374   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0       8.981   2.493   0.000  0.00  0.00           H+0
HETATM   28  O   UNK     0      10.929  -3.986   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   12                                                            
CONECT    3   13                                                            
CONECT    4   19                                                            
CONECT    5    6    8    9   12                                             
CONECT    6    5    7   11   26                                             
CONECT    7    6   10   14   15                                             
CONECT    8    5   10                                                       
CONECT    9    1    5   13   16                                             
CONECT   10    7    8   18   27                                             
CONECT   11    6   13                                                       
CONECT   12    2    5   17                                                  
CONECT   13    3    9   11                                                  
CONECT   14    7                                                            
CONECT   15    7                                                            
CONECT   16    9   17   28                                                  
CONECT   17   16   19   12                                                  
CONECT   18   10   20   21                                                  
CONECT   19    4   17   22                                                  
CONECT   20   18                                                            
CONECT   21   18                                                            
CONECT   22   19   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26    6                                                            
CONECT   27   10                                                            
CONECT   28   16                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₈O₅

Average Mass

360.4500 Da

Monoisotopic Mass

360.19367 Da

IUPAC Name

(1R,5R,8R,10R)-4,5-dihydroxy-9,9-dimethyl-3-(3-methylbutanoyl)-10-(prop-1-en-2-yl)tricyclo[6.3.0.0^{1,5}]undec-3-ene-2,6-dione

Traditional Name

(1R,5R,8R,10R)-4,5-dihydroxy-9,9-dimethyl-3-(3-methylbutanoyl)-10-(prop-1-en-2-yl)tricyclo[6.3.0.0^{1,5}]undec-3-ene-2,6-dione

CAS Registry Number

Not Available

SMILES

[H][C@@]1(C[C@]23C(=O)C(C(=O)CC(C)C)=C(O)[C@@]2(O)C(=O)C[C@]3([H])C1(C)C)C(C)=C

InChI Identifier

InChI=1S/C21H28O5/c1-10(2)7-13(22)16-17(24)20-9-12(11(3)4)19(5,6)14(20)8-15(23)21(20,26)18(16)25/h10,12,14,25-26H,3,7-9H2,1-2,4-6H3/t12-,14-,20+,21+/m1/s1

InChI Key

FZQFCXBBPNGZEI-QZHPCCELSA-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
Humulus lupulus	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as angular triquinanes. These are triquinane with a structure based on a [6.3.0.0^1,5] Undecane carbon skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Angular triquinanes

Alternative Parents

Substituents

Angular triquinane sesquiterpenoid
Vinylogous acid
Tertiary alcohol
Cyclic alcohol
Ketone
Enol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

sesquiterpenoid (CHEBI:9698 )

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	ALOGPS
logP	3.1	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	0.38	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	91.67 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	98.22 m³·mol⁻¹	ChemAxon
Polarizability	38.55 Å³	ChemAxon
Number of Rings	3	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

C00002709

Chemspider ID

Not Available

KEGG Compound ID

C10723

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

9698

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Tricyclodehydroisohumulone (NP0051555)

MOL for NP0051555 (Tricyclodehydroisohumulone)

3D MOL for NP0051555 (Tricyclodehydroisohumulone)

3D SDF for NP0051555 (Tricyclodehydroisohumulone)

3D-SDF for NP0051555 (Tricyclodehydroisohumulone)

PDB for NP0051555 (Tricyclodehydroisohumulone)

3D PDB for NP0051555 (Tricyclodehydroisohumulone)

SMILES for NP0051555 (Tricyclodehydroisohumulone)

INCHI for NP0051555 (Tricyclodehydroisohumulone)

Structure for NP0051555 (Tricyclodehydroisohumulone)

3D Structure for NP0051555 (Tricyclodehydroisohumulone)