NP-MRD: Showing NP-Card for 2a,7-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 3-chloro-4,6-dihydroxy-2-methylbenzoate (NP0289917)

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Record Information

Version

2.0

Created at

2022-09-09 20:20:21 UTC

Updated at

2022-09-09 20:20:21 UTC

NP-MRD ID

NP0289917

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2a,7-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 3-chloro-4,6-dihydroxy-2-methylbenzoate

Description

Melleolide M belongs to the class of organic compounds known as melleolides and analogues. Melleolides and analogues are compounds with a structure characterized by the presence of a 2-hydroxy-4-methoxy-6-methylbenzoic acid derivative linked to a 3,6,6,7b-tetramethyl-cyclobuta[e]indene moiety. Melleolide M is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Melleolide M has been detected, but not quantified in, mushrooms. This could make melleolide m a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061308132D          

 31 34  0  0  0  0            999 V2000
   -0.8241   -1.2904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7863    1.5151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2702    2.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0897    2.3068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6180    0.0598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5079    0.5236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8695    0.8998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1480    1.9572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3548   -0.6082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3853   -0.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0567    0.7584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7935    0.0905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7036    0.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7509   -0.2648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7092    1.2586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1423    0.1027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6711    1.4877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1896   -0.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2455    2.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3380    0.2864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9862    1.7165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8467    1.5184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4079    0.8198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4326   -1.6579    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.7404   -1.3375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4606    1.4957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5551   -0.4486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1041    2.8927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2232   -0.3182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8032    0.2585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0950    1.0748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 10  1  1  0  0  0  0
 11  5  1  0  0  0  0
 11  7  1  0  0  0  0
 12  5  2  0  0  0  0
 12  9  1  0  0  0  0
 13  6  2  0  0  0  0
 14  6  1  0  0  0  0
 15  8  1  0  0  0  0
 16 10  2  0  0  0  0
 16 13  1  0  0  0  0
 17 11  1  0  0  0  0
 18 10  1  0  0  0  0
 18 14  2  0  0  0  0
 19 17  1  0  0  0  0
 20 16  1  0  0  0  0
 21  2  1  0  0  0  0
 21  3  1  0  0  0  0
 21  7  1  0  0  0  0
 21 19  1  0  0  0  0
 22  4  1  0  0  0  0
 22  8  1  0  0  0  0
 22 17  1  0  0  0  0
 23 12  1  0  0  0  0
 23 15  1  0  0  0  0
 23 22  1  0  0  0  0
 24 18  1  0  0  0  0
 25  9  1  0  0  0  0
 26 13  1  0  0  0  0
 27 14  1  0  0  0  0
 28 19  1  0  0  0  0
 29 20  2  0  0  0  0
 30 23  1  0  0  0  0
 31 15  1  0  0  0  0
 31 20  1  0  0  0  0
M  END

     RDKit          3D

 60 63  0  0  0  0  0  0  0  0999 V2000
    5.0616   -1.0486    0.8349 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2511    0.3248    0.3983 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4294    0.7378    0.0463 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8620   -0.3521    0.3538 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.7638    1.9163   -0.5441 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0237    2.2785   -0.8866 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6296    2.7118   -0.7558 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4963    2.1763   -0.3483 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2856    3.1373   -0.6165 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8173    1.2220    0.1903 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0939    0.2049    0.7643 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1590   -0.7053    1.5472 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6700    0.1764    0.2310 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7750   -0.7568    0.6779 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0826   -1.4718   -0.3382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1618   -1.4965    0.6703 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9252   -2.6393    1.6548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5736   -1.3357    0.3413 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9585   -1.1164   -1.0846 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3031   -0.0695   -1.6765 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4193   -0.7602   -0.9692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3066   -1.9802   -1.1002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8851    0.2403   -1.9999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5804   -0.1482    0.4127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2002   -0.0965    1.0056 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4135    1.0417    0.4593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0632    0.9890    0.5669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3161    2.1237    0.0174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1717    3.0929   -0.5344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5296   -0.2029    1.2266 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6622   -0.1821    2.5893 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0548   -1.1254    1.9271 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2765   -1.5654    0.2817 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0310   -1.6473    0.5125 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8312    1.6673   -0.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7745    3.6606   -1.2096 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5789    3.9400   -1.0110 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1398   -1.5042    1.4398 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3460   -2.4515   -0.6431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1829   -0.8268   -1.2321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3559   -3.4525    1.1433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9186   -3.0879    1.9379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3813   -2.2984    2.5286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1832   -2.2113    0.7121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8985   -2.0369   -1.7024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8271    0.6277   -2.1016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3404   -2.5005   -0.1189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3156   -1.6665   -1.4083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9176   -2.6534   -1.8994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0150    0.1360   -2.0347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5329    0.0015   -3.0181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6917    1.2746   -1.6688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2781   -0.7651    1.0534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0005    0.8838    0.3241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1411   -0.1568    2.0892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9267    1.8527    0.0012 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2563    2.6350    0.8164 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3696    1.7544   -0.8126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6787    2.7887   -1.3054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8384    0.7160    2.9641 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  1
 16 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 27 30  1  0
 30 31  1  1
 10  8  1  0
  8  9  1  0
  8  7  2  0
  7  5  1  0
  5  6  1  0
  5  3  2  0
  3  4  1  0
  3  2  1  0
 30 14  1  0
 30 16  1  0
 25 18  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
 14 38  1  1
 15 39  1  0
 15 40  1  0
 17 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  1
 19 45  1  6
 20 46  1  0
 22 47  1  0
 22 48  1  0
 22 49  1  0
 23 50  1  0
 23 51  1  0
 23 52  1  0
 24 53  1  0
 24 54  1  0
 25 55  1  1
 26 56  1  0
 28 57  1  0
 28 58  1  0
 29 59  1  0
 31 60  1  0
  9 37  1  0
  7 36  1  0
  6 35  1  0
M  END


  Mrv0541 05061308132D          

 31 34  0  0  0  0            999 V2000
   -0.8241   -1.2904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7863    1.5151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2702    2.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0897    2.3068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6180    0.0598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5079    0.5236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8695    0.8998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1480    1.9572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3548   -0.6082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3853   -0.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0567    0.7584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7935    0.0905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7036    0.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7509   -0.2648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7092    1.2586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1423    0.1027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6711    1.4877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1896   -0.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2455    2.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3380    0.2864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9862    1.7165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8467    1.5184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4079    0.8198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4326   -1.6579    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.7404   -1.3375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4606    1.4957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5551   -0.4486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1041    2.8927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2232   -0.3182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8032    0.2585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0950    1.0748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 10  1  1  0  0  0  0
 11  5  1  0  0  0  0
 11  7  1  0  0  0  0
 12  5  2  0  0  0  0
 12  9  1  0  0  0  0
 13  6  2  0  0  0  0
 14  6  1  0  0  0  0
 15  8  1  0  0  0  0
 16 10  2  0  0  0  0
 16 13  1  0  0  0  0
 17 11  1  0  0  0  0
 18 10  1  0  0  0  0
 18 14  2  0  0  0  0
 19 17  1  0  0  0  0
 20 16  1  0  0  0  0
 21  2  1  0  0  0  0
 21  3  1  0  0  0  0
 21  7  1  0  0  0  0
 21 19  1  0  0  0  0
 22  4  1  0  0  0  0
 22  8  1  0  0  0  0
 22 17  1  0  0  0  0
 23 12  1  0  0  0  0
 23 15  1  0  0  0  0
 23 22  1  0  0  0  0
 24 18  1  0  0  0  0
 25  9  1  0  0  0  0
 26 13  1  0  0  0  0
 27 14  1  0  0  0  0
 28 19  1  0  0  0  0
 29 20  2  0  0  0  0
 30 23  1  0  0  0  0
 31 15  1  0  0  0  0
 31 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0289917

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(C(=O)OC2CC3(C)C4C(O)C(C)(C)CC4C=C(CO)C23O)C(O)=CC(O)=C1Cl

> <INCHI_IDENTIFIER>
InChI=1S/C23H29ClO7/c1-10-16(13(26)6-14(27)18(10)24)20(29)31-15-8-22(4)17-11(7-21(2,3)19(17)28)5-12(9-25)23(15,22)30/h5-6,11,15,17,19,25-28,30H,7-9H2,1-4H3

> <INCHI_KEY>
PBSFHHQIJGTBQH-UHFFFAOYSA-N

> <FORMULA>
C23H29ClO7

> <MOLECULAR_WEIGHT>
452.925

> <EXACT_MASS>
452.160180989

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
46.510747986835504

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2a,7-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1H,2H,2aH,4aH,5H,6H,7H,7aH,7bH-cyclobuta[e]inden-2-yl 3-chloro-4,6-dihydroxy-2-methylbenzoate

> <ALOGPS_LOGP>
2.01

> <JCHEM_LOGP>
3.244869051666666

> <ALOGPS_LOGS>
-3.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.025044968014907

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.208694711946623

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7659471047328115

> <JCHEM_POLAR_SURFACE_AREA>
127.45000000000002

> <JCHEM_REFRACTIVITY>
115.27299999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.29e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2a,7-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1H,2H,4aH,5H,7H,7aH-cyclobuta[e]inden-2-yl 3-chloro-4,6-dihydroxy-2-methylbenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -1.538  -2.409   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.934   2.828   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.971   4.650   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.901   4.306   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.887   0.112   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.681   0.977   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.223   1.680   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.143   3.653   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.529  -1.135   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.586  -1.280   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.706   1.416   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.348   0.169   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.180   1.320   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.135  -0.494   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.324   2.349   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.132   0.192   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.986   2.777   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.087  -1.623   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.058   3.882   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.631   0.535   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.441   3.204   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.447   2.834   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.628   1.530   0.000  0.00  0.00           C+0
HETATM   24 Cl   UNK     0      -4.541  -3.095   0.000  0.00  0.00          Cl+0
HETATM   25  O   UNK     0       3.249  -2.497   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -2.726   2.792   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -6.636  -0.837   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       5.794   5.400   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       0.417  -0.594   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       1.499   0.483   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -0.177   2.006   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   21                                                            
CONECT    3   21                                                            
CONECT    4   22                                                            
CONECT    5   11   12                                                       
CONECT    6   13   14                                                       
CONECT    7   11   21                                                       
CONECT    8   15   22                                                       
CONECT    9   12   25                                                       
CONECT   10    1   16   18                                                  
CONECT   11    5    7   17                                                  
CONECT   12    5    9   23                                                  
CONECT   13    6   16   26                                                  
CONECT   14    6   18   27                                                  
CONECT   15    8   23   31                                                  
CONECT   16   10   13   20                                                  
CONECT   17   11   19   22                                                  
CONECT   18   10   14   24                                                  
CONECT   19   17   21   28                                                  
CONECT   20   16   29   31                                                  
CONECT   21    2    3    7   19                                             
CONECT   22    4    8   17   23                                             
CONECT   23   12   15   22   30                                             
CONECT   24   18                                                            
CONECT   25    9                                                            
CONECT   26   13                                                            
CONECT   27   14                                                            
CONECT   28   19                                                            
CONECT   29   20                                                            
CONECT   30   23                                                            
CONECT   31   15   20                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Value	Source
2a,7-Dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1H,2H,2ah,4ah,5H,6H,7H,7ah,7BH-cyclobuta[e]inden-2-yl 3-chloro-4,6-dihydroxy-2-methylbenzoic acid	Generator
Melleolide-m	MeSH
Melleolide m	MeSH

Chemical Formula

C₂₃H₂₉ClO₇

Average Mass

452.9250 Da

Monoisotopic Mass

452.16018 Da

IUPAC Name

2a,7-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1H,2H,2aH,4aH,5H,6H,7H,7aH,7bH-cyclobuta[e]inden-2-yl 3-chloro-4,6-dihydroxy-2-methylbenzoate

Traditional Name

2a,7-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1H,2H,4aH,5H,7H,7aH-cyclobuta[e]inden-2-yl 3-chloro-4,6-dihydroxy-2-methylbenzoate

CAS Registry Number

Not Available

SMILES

CC1=C(C(=O)OC2CC3(C)C4C(O)C(C)(C)CC4C=C(CO)C23O)C(O)=CC(O)=C1Cl

InChI Identifier

InChI=1S/C23H29ClO7/c1-10-16(13(26)6-14(27)18(10)24)20(29)31-15-8-22(4)17-11(7-21(2,3)19(17)28)5-12(9-25)23(15,22)30/h5-6,11,15,17,19,25-28,30H,7-9H2,1-4H3

InChI Key

PBSFHHQIJGTBQH-UHFFFAOYSA-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 melleolides and analogues. Melleolides and analogues are compounds with a structure characterized by the presence of a 2-hydroxy-4-methoxy-6-methylbenzoic acid derivative linked to a 3,6,6,7b-tetramethyl-cyclobuta[e]indene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Melleolides and analogues

Alternative Parents

Substituents

Melleolide-skeleton
P-hydroxybenzoic acid alkyl ester
P-hydroxybenzoic acid ester
O-hydroxybenzoic acid ester
Dihydroxybenzoic acid
Salicylic acid or derivatives
3-halobenzoic acid or derivatives
Halobenzoic acid or derivatives
Benzoate ester
Benzoic acid or derivatives
4-chlorophenol
Resorcinol
M-cresol
2-chlorophenol
2-halophenol
4-halophenol
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Chlorobenzene
Halobenzene
Toluene
Phenol
Aryl halide
Benzenoid
Monocyclic benzene moiety
Aryl chloride
Tertiary alcohol
Vinylogous acid
Cyclic alcohol
Secondary alcohol
Cyclobutanol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Organohalogen compound
Organochloride
Organooxygen compound
Primary alcohol
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	2.01	ALOGPS
logP	3.24	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	7.21	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	127.45 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	115.27 m³·mol⁻¹	ChemAxon
Polarizability	46.51 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

HMDB0035068

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013692

KNApSAcK ID

C00015497

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

85260457

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2a,7-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 3-chloro-4,6-dihydroxy-2-methylbenzoate (NP0289917)

MOL for NP0289917 (2a,7-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 3-chloro-4,6-dihydroxy-2-methylbenzoate)

3D MOL for NP0289917 (2a,7-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 3-chloro-4,6-dihydroxy-2-methylbenzoate)

3D SDF for NP0289917 (2a,7-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 3-chloro-4,6-dihydroxy-2-methylbenzoate)

3D-SDF for NP0289917 (2a,7-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 3-chloro-4,6-dihydroxy-2-methylbenzoate)

PDB for NP0289917 (2a,7-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 3-chloro-4,6-dihydroxy-2-methylbenzoate)

3D PDB for NP0289917 (2a,7-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 3-chloro-4,6-dihydroxy-2-methylbenzoate)

SMILES for NP0289917 (2a,7-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 3-chloro-4,6-dihydroxy-2-methylbenzoate)

INCHI for NP0289917 (2a,7-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 3-chloro-4,6-dihydroxy-2-methylbenzoate)

Structure for NP0289917 (2a,7-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 3-chloro-4,6-dihydroxy-2-methylbenzoate)

3D Structure for NP0289917 (2a,7-dihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1h,2h,4ah,5h,7h,7ah-cyclobuta[e]inden-2-yl 3-chloro-4,6-dihydroxy-2-methylbenzoate)