NP-MRD: Showing NP-Card for Cyclocalopin A (NP0006638)

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Record Information

Version

2.0

Created at

2020-12-09 03:35:46 UTC

Updated at

2021-07-15 16:55:22 UTC

NP-MRD ID

NP0006638

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cyclocalopin A

Provided By

NPAtlas

Description

Cyclocalopin A is found in Caloboletus calopus, Caloboletus rubripes and Boletus. Cyclocalopin A was first documented in 2006 (PMID: 17091435). Based on a literature review very few articles have been published on Cyclocalopin A.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118293D          

 41 43  0  0  0  0            999 V2000
    3.1466   -2.6069    0.2829 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2825   -1.4123    0.2592 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6455   -1.0504    1.3495 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7586    0.1310    1.4213 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3199    0.6920    0.1148 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4264    0.6699   -0.8773 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0506    1.1256   -2.1388 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1172   -0.6282   -0.9367 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5581   -1.0465   -2.0234 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9993    0.2076   -0.3864 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2370   -1.2331   -0.4743 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3181   -1.4573   -1.5511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7692   -1.9061    0.7511 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8091   -1.1802    1.3494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6903    0.1799    1.4513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2166    0.8182    2.4277 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9649    0.9819    0.4660 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2281    1.9425    1.1564 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0460    2.1489    0.4477 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2523    3.0167   -0.7034 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9540    2.6530    1.2658 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6486   -3.4659    0.8021 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0624   -2.3989    0.9073 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4196   -2.9622   -0.7303 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7497   -1.6240    2.2689 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3495    0.9126    1.9856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1341   -0.0476    2.0487 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1996    1.4144   -0.5188 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6512    1.8123   -2.5043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1083    0.6344   -1.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3669   -1.7815   -0.8312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8929   -1.2802   -2.5440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7840   -2.4446   -1.4170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1174   -0.7066   -1.3009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0077   -2.2068    1.4836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2339   -2.8771    0.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7164    1.5482   -0.1382 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7182    3.5343   -0.9570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6708    2.6134   -1.6125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9301    3.8662   -0.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4355    3.4133    0.8241 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  1  0  0  0
  8  2  1  0  0  0  0
 17 10  1  0  0  0  0
 19  5  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  3 25  1  0  0  0  0
  4 26  1  0  0  0  0
  4 27  1  0  0  0  0
  6 28  1  1  0  0  0
  7 29  1  0  0  0  0
 10 30  1  6  0  0  0
 11 31  1  6  0  0  0
 12 32  1  0  0  0  0
 12 33  1  0  0  0  0
 12 34  1  0  0  0  0
 13 35  1  0  0  0  0
 13 36  1  0  0  0  0
 17 37  1  6  0  0  0
 20 38  1  0  0  0  0
 20 39  1  0  0  0  0
 20 40  1  0  0  0  0
 21 41  1  0  0  0  0
M  END

     RDKit          3D

 41 43  0  0  0  0  0  0  0  0999 V2000
    3.1466   -2.6069    0.2829 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2825   -1.4123    0.2592 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6455   -1.0504    1.3495 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7586    0.1310    1.4213 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3199    0.6920    0.1148 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4264    0.6699   -0.8773 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0506    1.1256   -2.1388 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1172   -0.6282   -0.9367 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5581   -1.0465   -2.0234 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9993    0.2076   -0.3864 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2370   -1.2331   -0.4743 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3181   -1.4573   -1.5511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7692   -1.9061    0.7511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8091   -1.1802    1.3494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6903    0.1799    1.4513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2166    0.8182    2.4277 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9649    0.9819    0.4660 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2281    1.9425    1.1564 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0460    2.1489    0.4477 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2523    3.0167   -0.7034 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9540    2.6530    1.2658 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6486   -3.4659    0.8021 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0624   -2.3989    0.9073 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4196   -2.9622   -0.7303 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7497   -1.6240    2.2689 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3495    0.9126    1.9856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1341   -0.0476    2.0487 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1996    1.4144   -0.5188 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6512    1.8123   -2.5043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1083    0.6344   -1.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3669   -1.7815   -0.8312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8929   -1.2802   -2.5440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7840   -2.4446   -1.4170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1174   -0.7066   -1.3009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0077   -2.2068    1.4836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2339   -2.8771    0.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7164    1.5482   -0.1382 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7182    3.5343   -0.9570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6708    2.6134   -1.6125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9301    3.8662   -0.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4355    3.4133    0.8241 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  5  4  1  1
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  5 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
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 19 20  1  0
 19 21  1  1
  8  2  1  0
 17 10  1  0
 19  5  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  6 28  1  1
  7 29  1  0
 10 30  1  6
 11 31  1  6
 12 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 17 37  1  6
 20 38  1  0
 20 39  1  0
 20 40  1  0
 21 41  1  0
M  END


  Mrv1652306242118293D          

 41 43  0  0  0  0            999 V2000
    3.1466   -2.6069    0.2829 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2825   -1.4123    0.2592 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6455   -1.0504    1.3495 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7586    0.1310    1.4213 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3199    0.6920    0.1148 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4264    0.6699   -0.8773 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0506    1.1256   -2.1388 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1172   -0.6282   -0.9367 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5581   -1.0465   -2.0234 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9993    0.2076   -0.3864 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2370   -1.2331   -0.4743 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3181   -1.4573   -1.5511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7692   -1.9061    0.7511 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8091   -1.1802    1.3494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6903    0.1799    1.4513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2166    0.8182    2.4277 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9649    0.9819    0.4660 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2281    1.9425    1.1564 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0460    2.1489    0.4477 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2523    3.0167   -0.7034 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9540    2.6530    1.2658 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6486   -3.4659    0.8021 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0624   -2.3989    0.9073 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4196   -2.9622   -0.7303 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7497   -1.6240    2.2689 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3495    0.9126    1.9856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1341   -0.0476    2.0487 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1996    1.4144   -0.5188 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6512    1.8123   -2.5043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1083    0.6344   -1.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3669   -1.7815   -0.8312 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.1174   -0.7066   -1.3009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0077   -2.2068    1.4836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2339   -2.8771    0.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7164    1.5482   -0.1382 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7182    3.5343   -0.9570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6708    2.6134   -1.6125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9301    3.8662   -0.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4355    3.4133    0.8241 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  1  0  0  0
  8  2  1  0  0  0  0
 17 10  1  0  0  0  0
 19  5  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  3 25  1  0  0  0  0
  4 26  1  0  0  0  0
  4 27  1  0  0  0  0
  6 28  1  1  0  0  0
  7 29  1  0  0  0  0
 10 30  1  6  0  0  0
 11 31  1  6  0  0  0
 12 32  1  0  0  0  0
 12 33  1  0  0  0  0
 12 34  1  0  0  0  0
 13 35  1  0  0  0  0
 13 36  1  0  0  0  0
 17 37  1  6  0  0  0
 20 38  1  0  0  0  0
 20 39  1  0  0  0  0
 20 40  1  0  0  0  0
 21 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0006638

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])C(=O)C(=C([H])C([H])([H])[C@]11[C@]2([H])[C@]([H])(O[C@]1(O[H])C([H])([H])[H])C(=O)OC([H])([H])[C@@]2([H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O6/c1-7-4-5-15(12(17)10(7)16)9-8(2)6-20-13(18)11(9)21-14(15,3)19/h4,8-9,11-12,17,19H,5-6H2,1-3H3/t8-,9+,11+,12-,14-,15+/m1/s1

> <INCHI_KEY>
OGOHSCJKRSLFLO-UOMAJYNRSA-N

> <FORMULA>
C15H20O6

> <MOLECULAR_WEIGHT>
296.319

> <EXACT_MASS>
296.125988364

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
29.167261048998427

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2'R,3'aR,4'S,6S,7'aS)-2',6-dihydroxy-2',4,4'-trimethyl-2',3'a,4',5',7',7'a-hexahydrospiro[cyclohexane-1,3'-furo[2,3-c]pyra]-3-ene-5,7'-dione

> <ALOGPS_LOGP>
-0.27

> <JCHEM_LOGP>
0.6183836689999999

> <ALOGPS_LOGS>
-1.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.9076301227886

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.689887532801913

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7738944100816285

> <JCHEM_POLAR_SURFACE_AREA>
93.06000000000002

> <JCHEM_REFRACTIVITY>
72.71630000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.81e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2'R,3'aR,4'S,6S,7'aS)-2',6-dihydroxy-2',4,4'-trimethyl-3'a,4',5',7'a-tetrahydrospiro[cyclohexane-1,3'-furo[2,3-c]pyra]-3-ene-5,7'-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 41 43  0  0  0  0  0  0  0  0999 V2000
    3.1466   -2.6069    0.2829 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2825   -1.4123    0.2592 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6455   -1.0504    1.3495 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7586    0.1310    1.4213 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3199    0.6920    0.1148 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4264    0.6699   -0.8773 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0506    1.1256   -2.1388 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1172   -0.6282   -0.9367 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5581   -1.0465   -2.0234 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9993    0.2076   -0.3864 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2370   -1.2331   -0.4743 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3181   -1.4573   -1.5511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7692   -1.9061    0.7511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8091   -1.1802    1.3494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6903    0.1799    1.4513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2166    0.8182    2.4277 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9649    0.9819    0.4660 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2281    1.9425    1.1564 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0460    2.1489    0.4477 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2523    3.0167   -0.7034 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9540    2.6530    1.2658 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6486   -3.4659    0.8021 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0624   -2.3989    0.9073 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4196   -2.9622   -0.7303 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7497   -1.6240    2.2689 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3495    0.9126    1.9856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1341   -0.0476    2.0487 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1996    1.4144   -0.5188 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6512    1.8123   -2.5043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1083    0.6344   -1.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3669   -1.7815   -0.8312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8929   -1.2802   -2.5440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7840   -2.4446   -1.4170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1174   -0.7066   -1.3009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0077   -2.2068    1.4836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2339   -2.8771    0.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7164    1.5482   -0.1382 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7182    3.5343   -0.9570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6708    2.6134   -1.6125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9301    3.8662   -0.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4355    3.4133    0.8241 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  5  4  1  1
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  5 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  1
  8  2  1  0
 17 10  1  0
 19  5  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  6 28  1  1
  7 29  1  0
 10 30  1  6
 11 31  1  6
 12 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 17 37  1  6
 20 38  1  0
 20 39  1  0
 20 40  1  0
 21 41  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       3.147  -2.607   0.283  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.283  -1.412   0.259  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.646  -1.050   1.349  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.759   0.131   1.421  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.320   0.692   0.115  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.426   0.670  -0.877  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.051   1.126  -2.139  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.117  -0.628  -0.937  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.558  -1.046  -2.023  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.999   0.208  -0.386  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.237  -1.233  -0.474  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.318  -1.457  -1.551  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.769  -1.906   0.751  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.809  -1.180   1.349  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.690   0.180   1.451  0.00  0.00           C+0
HETATM   16  O   UNK     0      -3.217   0.818   2.428  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.965   0.982   0.466  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.228   1.942   1.156  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.046   2.149   0.448  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.252   3.017  -0.703  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.954   2.653   1.266  0.00  0.00           O+0
HETATM   22  H   UNK     0       2.649  -3.466   0.802  0.00  0.00           H+0
HETATM   23  H   UNK     0       4.062  -2.399   0.907  0.00  0.00           H+0
HETATM   24  H   UNK     0       3.420  -2.962  -0.730  0.00  0.00           H+0
HETATM   25  H   UNK     0       1.750  -1.624   2.269  0.00  0.00           H+0
HETATM   26  H   UNK     0       1.349   0.913   1.986  0.00  0.00           H+0
HETATM   27  H   UNK     0      -0.134  -0.048   2.049  0.00  0.00           H+0
HETATM   28  H   UNK     0       2.200   1.414  -0.519  0.00  0.00           H+0
HETATM   29  H   UNK     0       1.651   1.812  -2.504  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.108   0.634  -1.430  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.367  -1.782  -0.831  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.893  -1.280  -2.544  0.00  0.00           H+0
HETATM   33  H   UNK     0      -2.784  -2.445  -1.417  0.00  0.00           H+0
HETATM   34  H   UNK     0      -3.117  -0.707  -1.301  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.008  -2.207   1.484  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.234  -2.877   0.404  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.716   1.548  -0.138  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.718   3.534  -0.957  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.671   2.613  -1.613  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.930   3.866  -0.392  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.436   3.413   0.824  0.00  0.00           H+0
CONECT    1    2   22   23   24                                             
CONECT    2    1    3    8                                                  
CONECT    3    2    4   25                                                  
CONECT    4    3    5   26   27                                             
CONECT    5    4    6   10   19                                             
CONECT    6    5    7    8   28                                             
CONECT    7    6   29                                                       
CONECT    8    6    9    2                                                  
CONECT    9    8                                                            
CONECT   10    5   11   17   30                                             
CONECT   11   10   12   13   31                                             
CONECT   12   11   32   33   34                                             
CONECT   13   11   14   35   36                                             
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   10   37                                             
CONECT   18   17   19                                                       
CONECT   19   18   20   21    5                                             
CONECT   20   19   38   39   40                                             
CONECT   21   19   41                                                       
CONECT   22    1                                                            
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    3                                                            
CONECT   26    4                                                            
CONECT   27    4                                                            
CONECT   28    6                                                            
CONECT   29    7                                                            
CONECT   30   10                                                            
CONECT   31   11                                                            
CONECT   32   12                                                            
CONECT   33   12                                                            
CONECT   34   12                                                            
CONECT   35   13                                                            
CONECT   36   13                                                            
CONECT   37   17                                                            
CONECT   38   20                                                            
CONECT   39   20                                                            
CONECT   40   20                                                            
CONECT   41   21                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   86    0
END

RDKit          3D

41 43  0  0  0  0  0  0  0  0999 V2000
    3.1466   -2.6069    0.2829 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2825   -1.4123    0.2592 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6455   -1.0504    1.3495 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7586    0.1310    1.4213 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3199    0.6920    0.1148 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4264    0.6699   -0.8773 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0506    1.1256   -2.1388 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1172   -0.6282   -0.9367 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5581   -1.0465   -2.0234 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9993    0.2076   -0.3864 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2370   -1.2331   -0.4743 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3181   -1.4573   -1.5511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7692   -1.9061    0.7511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8091   -1.1802    1.3494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6903    0.1799    1.4513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2166    0.8182    2.4277 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9649    0.9819    0.4660 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2281    1.9425    1.1564 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0460    2.1489    0.4477 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2523    3.0167   -0.7034 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9540    2.6530    1.2658 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6486   -3.4659    0.8021 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0624   -2.3989    0.9073 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4196   -2.9622   -0.7303 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7497   -1.6240    2.2689 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3495    0.9126    1.9856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1341   -0.0476    2.0487 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1996    1.4144   -0.5188 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6512    1.8123   -2.5043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1083    0.6344   -1.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3669   -1.7815   -0.8312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8929   -1.2802   -2.5440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7840   -2.4446   -1.4170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1174   -0.7066   -1.3009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0077   -2.2068    1.4836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2339   -2.8771    0.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7164    1.5482   -0.1382 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7182    3.5343   -0.9570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6708    2.6134   -1.6125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9301    3.8662   -0.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4355    3.4133    0.8241 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  5  4  1  1
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  5 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  1
  8  2  1  0
 17 10  1  0
 19  5  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  6 28  1  1
  7 29  1  0
 10 30  1  6
 11 31  1  6
 12 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 17 37  1  6
 20 38  1  0
 20 39  1  0
 20 40  1  0
 21 41  1  0
M  END

View in JSmol View NMR Assignments View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₁₅H₂₀O₆

Average Mass

296.3190 Da

Monoisotopic Mass

296.12599 Da

IUPAC Name

(1S,2'R,3'aR,4'S,6S,7'aS)-2',6-dihydroxy-2',4,4'-trimethyl-2',3'a,4',5',7',7'a-hexahydrospiro[cyclohexane-1,3'-furo[2,3-c]pyra]-3-ene-5,7'-dione

Traditional Name

(1S,2'R,3'aR,4'S,6S,7'aS)-2',6-dihydroxy-2',4,4'-trimethyl-3'a,4',5',7'a-tetrahydrospiro[cyclohexane-1,3'-furo[2,3-c]pyra]-3-ene-5,7'-dione

CAS Registry Number

Not Available

SMILES

C[C@@H]1COC(=O)[C@H]2O[C@@](C)(O)[C@@]3(CC=C(C)C(=O)[C@H]3O)[C@@H]12

InChI Identifier

InChI=1S/C15H20O6/c1-7-4-5-15(12(17)10(7)16)9-8(2)6-20-13(18)11(9)21-14(15,3)19/h4,8-9,11-12,17,19H,5-6H2,1-3H3/t8-,9+,11+,12-,14-,15+/m1/s1

InChI Key

OGOHSCJKRSLFLO-UOMAJYNRSA-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
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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
Agaricus bisporus	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Caloboletus calopus	LOTUS Database	35616633
Caloboletus rubripes	LOTUS Database	35616633
Melittangium boletus	NPAtlas	17091435
Pleurotus ostreatus	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...

Chemical Taxonomy

Classification

Not classified

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	-0.27	ALOGPS
logP	0.62	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	11.69	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	72.72 m³·mol⁻¹	ChemAxon
Polarizability	29.17 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

NPAtlas ID

NPA006087

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9088718

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10913461

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kim JW, Yoo ID, Kim WG: Free radical-scavenging delta-lactones from Boletus calopus. Planta Med. 2006 Dec;72(15):1431-2. doi: 10.1055/s-2006-951722. Epub 2006 Nov 7. [PubMed:17091435 ]

Showing NP-Card for Cyclocalopin A (NP0006638)

MOL for NP0006638 (Cyclocalopin A)

3D MOL for NP0006638 (Cyclocalopin A)

3D SDF for NP0006638 (Cyclocalopin A)

3D-SDF for NP0006638 (Cyclocalopin A)

PDB for NP0006638 (Cyclocalopin A)

3D PDB for NP0006638 (Cyclocalopin A)

SMILES for NP0006638 (Cyclocalopin A)

INCHI for NP0006638 (Cyclocalopin A)

Structure for NP0006638 (Cyclocalopin A)

3D Structure for NP0006638 (Cyclocalopin A)