NP-MRD: Showing NP-Card for ent-(3R)-3-hydroxyatractylenolide III (NP0042080)

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Record Information

Version

2.0

Created at

2021-06-20 23:49:49 UTC

Updated at

2021-06-30 00:16:58 UTC

NP-MRD ID

NP0042080

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ent-(3R)-3-hydroxyatractylenolide III

Provided By

JEOL Database JEOL Logo

Description

(4AS,6S,8aS,9aR)-6,9a-dihydroxy-3,8a-dimethyl-5-methylidene-2H,4H,4aH,5H,6H,7H,8H,8aH,9H,9aH-naphtho[2,3-b]furan-2-one belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton. ent-(3R)-3-hydroxyatractylenolide III is found in Chloranthus multistachys. ent-(3R)-3-hydroxyatractylenolide III was first documented in 2013 (Liu, H.-Y., et al.). Based on a literature review very few articles have been published on (4aS,6S,8aS,9aR)-6,9a-dihydroxy-3,8a-dimethyl-5-methylidene-2H,4H,4aH,5H,6H,7H,8H,8aH,9H,9aH-naphtho[2,3-b]furan-2-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212101493D          

 39 41  0  0  0  0            999 V2000
    0.6615   -2.2395    3.2578 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4782   -1.4080    2.5878 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5759   -0.6474    3.3014 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8291   -1.1405    2.8377 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5036    0.8570    3.0303 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3612    1.1888    1.5379 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2065    0.4164    0.8370 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1436    0.9273    1.3978 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2876    0.7038   -0.6978 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3729   -0.1874   -1.5483 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9859    0.1743   -1.4198 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7315   -0.1391   -2.9180 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9480   -1.4088   -3.3582 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2291   -1.7149   -4.5032 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8438   -2.3491   -2.2332 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1298   -3.7907   -2.3940 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5250   -1.6088   -1.1719 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4143   -1.9821    0.2699 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4048   -1.1199    1.0914 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7659   -2.3935    4.3287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1400   -2.7891    2.7753 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5446   -0.8133    4.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8137   -2.1037    2.9721 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6657    1.2923    3.5867 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4147    1.3418    3.4025 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3122    0.9527    1.0418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2168    2.2705    1.4231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2836    1.9883    1.1613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2090    0.8283    2.4853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0010    0.3848    0.9938 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3243    0.5650   -1.0370 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0554    1.7601   -0.8881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0294    1.1182   -1.6444 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0358   -4.3355   -1.4503 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4325   -4.2406   -3.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1482   -3.9409   -2.7661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6184   -1.8365    0.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6464   -3.0436    0.4122 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4003   -1.3820    0.6963 H   0  0  0  0  0  0  0  0  0  0  0  0
  2 19  1  0  0  0  0
  7  6  1  0  0  0  0
  7 19  1  0  0  0  0
  5  3  1  0  0  0  0
 17 15  2  0  0  0  0
 15 13  1  0  0  0  0
 13 12  1  0  0  0  0
 12 10  1  0  0  0  0
  5  6  1  0  0  0  0
 15 16  1  0  0  0  0
  3  2  1  0  0  0  0
 13 14  2  0  0  0  0
  7  9  1  0  0  0  0
  2  1  2  3  0  0  0
 19 18  1  0  0  0  0
  3  4  1  0  0  0  0
 18 17  1  0  0  0  0
 19 39  1  6  0  0  0
 10  9  1  0  0  0  0
  7  8  1  1  0  0  0
 10 17  1  0  0  0  0
 10 11  1  6  0  0  0
  5 24  1  0  0  0  0
  5 25  1  0  0  0  0
  3 22  1  1  0  0  0
  6 26  1  0  0  0  0
  6 27  1  0  0  0  0
 18 37  1  0  0  0  0
 18 38  1  0  0  0  0
  9 31  1  0  0  0  0
  9 32  1  0  0  0  0
 16 34  1  0  0  0  0
 16 35  1  0  0  0  0
 16 36  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  4 23  1  0  0  0  0
  8 28  1  0  0  0  0
  8 29  1  0  0  0  0
  8 30  1  0  0  0  0
 11 33  1  0  0  0  0
M  END

     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
    0.6615   -2.2395    3.2578 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4782   -1.4080    2.5878 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5759   -0.6474    3.3014 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8291   -1.1405    2.8377 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5036    0.8570    3.0303 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3612    1.1888    1.5379 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2065    0.4164    0.8370 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1436    0.9273    1.3978 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2876    0.7038   -0.6978 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3729   -0.1874   -1.5483 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9859    0.1743   -1.4198 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7315   -0.1391   -2.9180 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9480   -1.4088   -3.3582 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2291   -1.7149   -4.5032 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8438   -2.3491   -2.2332 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1298   -3.7907   -2.3940 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5250   -1.6088   -1.1719 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4143   -1.9821    0.2699 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4048   -1.1199    1.0914 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7659   -2.3935    4.3287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1400   -2.7891    2.7753 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5446   -0.8133    4.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8137   -2.1037    2.9721 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6657    1.2923    3.5867 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4147    1.3418    3.4025 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3122    0.9527    1.0418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2168    2.2705    1.4231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2836    1.9883    1.1613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2090    0.8283    2.4853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0010    0.3848    0.9938 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3243    0.5650   -1.0370 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0554    1.7601   -0.8881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0294    1.1182   -1.6444 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0358   -4.3355   -1.4503 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4325   -4.2406   -3.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1482   -3.9409   -2.7661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6184   -1.8365    0.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6464   -3.0436    0.4122 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4003   -1.3820    0.6963 H   0  0  0  0  0  0  0  0  0  0  0  0
  2 19  1  0
  7  6  1  0
  7 19  1  0
  5  3  1  0
 17 15  2  0
 15 13  1  0
 13 12  1  0
 12 10  1  0
  5  6  1  0
 15 16  1  0
  3  2  1  0
 13 14  2  0
  7  9  1  0
  2  1  2  3
 19 18  1  0
  3  4  1  0
 18 17  1  0
 19 39  1  6
 10  9  1  0
  7  8  1  1
 10 17  1  0
 10 11  1  6
  5 24  1  0
  5 25  1  0
  3 22  1  1
  6 26  1  0
  6 27  1  0
 18 37  1  0
 18 38  1  0
  9 31  1  0
  9 32  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
  1 20  1  0
  1 21  1  0
  4 23  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
 11 33  1  0
M  END


  Mrv1652306212101493D          

 39 41  0  0  0  0            999 V2000
    0.6615   -2.2395    3.2578 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4782   -1.4080    2.5878 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5759   -0.6474    3.3014 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8291   -1.1405    2.8377 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5036    0.8570    3.0303 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3612    1.1888    1.5379 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2065    0.4164    0.8370 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1436    0.9273    1.3978 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2876    0.7038   -0.6978 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3729   -0.1874   -1.5483 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9859    0.1743   -1.4198 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7315   -0.1391   -2.9180 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9480   -1.4088   -3.3582 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2291   -1.7149   -4.5032 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8438   -2.3491   -2.2332 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1298   -3.7907   -2.3940 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5250   -1.6088   -1.1719 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4143   -1.9821    0.2699 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4048   -1.1199    1.0914 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7659   -2.3935    4.3287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1400   -2.7891    2.7753 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5446   -0.8133    4.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8137   -2.1037    2.9721 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6657    1.2923    3.5867 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4147    1.3418    3.4025 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3122    0.9527    1.0418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2168    2.2705    1.4231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2836    1.9883    1.1613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2090    0.8283    2.4853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0010    0.3848    0.9938 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3243    0.5650   -1.0370 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0554    1.7601   -0.8881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0294    1.1182   -1.6444 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0358   -4.3355   -1.4503 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4325   -4.2406   -3.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1482   -3.9409   -2.7661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6184   -1.8365    0.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6464   -3.0436    0.4122 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4003   -1.3820    0.6963 H   0  0  0  0  0  0  0  0  0  0  0  0
  2 19  1  0  0  0  0
  7  6  1  0  0  0  0
  7 19  1  0  0  0  0
  5  3  1  0  0  0  0
 17 15  2  0  0  0  0
 15 13  1  0  0  0  0
 13 12  1  0  0  0  0
 12 10  1  0  0  0  0
  5  6  1  0  0  0  0
 15 16  1  0  0  0  0
  3  2  1  0  0  0  0
 13 14  2  0  0  0  0
  7  9  1  0  0  0  0
  2  1  2  3  0  0  0
 19 18  1  0  0  0  0
  3  4  1  0  0  0  0
 18 17  1  0  0  0  0
 19 39  1  6  0  0  0
 10  9  1  0  0  0  0
  7  8  1  1  0  0  0
 10 17  1  0  0  0  0
 10 11  1  6  0  0  0
  5 24  1  0  0  0  0
  5 25  1  0  0  0  0
  3 22  1  1  0  0  0
  6 26  1  0  0  0  0
  6 27  1  0  0  0  0
 18 37  1  0  0  0  0
 18 38  1  0  0  0  0
  9 31  1  0  0  0  0
  9 32  1  0  0  0  0
 16 34  1  0  0  0  0
 16 35  1  0  0  0  0
 16 36  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  4 23  1  0  0  0  0
  8 28  1  0  0  0  0
  8 29  1  0  0  0  0
  8 30  1  0  0  0  0
 11 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0042080

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])C(=C([H])[H])[C@@]2([H])C([H])([H])C3=C(C(=O)O[C@]3(O[H])C([H])([H])[C@]2(C([H])([H])[H])C([H])([H])C1([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O4/c1-8-10-6-11-9(2)13(17)19-15(11,18)7-14(10,3)5-4-12(8)16/h10,12,16,18H,1,4-7H2,2-3H3/t10-,12+,14+,15-/m1/s1

> <INCHI_KEY>
VITHJONQLOCSGP-UEEZHKSASA-N

> <FORMULA>
C15H20O4

> <MOLECULAR_WEIGHT>
264.321

> <EXACT_MASS>
264.136159124

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
28.045692006265092

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4aS,6S,8aS,9aR)-6,9a-dihydroxy-3,8a-dimethyl-5-methylidene-2H,4H,4aH,5H,6H,7H,8H,8aH,9H,9aH-naphtho[2,3-b]furan-2-one

> <ALOGPS_LOGP>
0.81

> <JCHEM_LOGP>
1.6851409823333332

> <ALOGPS_LOGS>
-1.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.161710991064655

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.2495947270821

> <JCHEM_PKA_STRONGEST_BASIC>
-1.415866381146118

> <JCHEM_POLAR_SURFACE_AREA>
66.75999999999999

> <JCHEM_REFRACTIVITY>
70.01950000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.91e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4aS,6S,8aS,9aR)-6,9a-dihydroxy-3,8a-dimethyl-5-methylidene-4H,4aH,6H,7H,8H,9H-naphtho[2,3-b]furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
    0.6615   -2.2395    3.2578 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4782   -1.4080    2.5878 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5759   -0.6474    3.3014 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8291   -1.1405    2.8377 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5036    0.8570    3.0303 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3612    1.1888    1.5379 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2065    0.4164    0.8370 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1436    0.9273    1.3978 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2876    0.7038   -0.6978 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3729   -0.1874   -1.5483 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9859    0.1743   -1.4198 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7315   -0.1391   -2.9180 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9480   -1.4088   -3.3582 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2291   -1.7149   -4.5032 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8438   -2.3491   -2.2332 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1298   -3.7907   -2.3940 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5250   -1.6088   -1.1719 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4143   -1.9821    0.2699 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4048   -1.1199    1.0914 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7659   -2.3935    4.3287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1400   -2.7891    2.7753 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5446   -0.8133    4.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8137   -2.1037    2.9721 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6657    1.2923    3.5867 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4147    1.3418    3.4025 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3122    0.9527    1.0418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2168    2.2705    1.4231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2836    1.9883    1.1613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2090    0.8283    2.4853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0010    0.3848    0.9938 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3243    0.5650   -1.0370 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0554    1.7601   -0.8881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0294    1.1182   -1.6444 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0358   -4.3355   -1.4503 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4325   -4.2406   -3.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1482   -3.9409   -2.7661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6184   -1.8365    0.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6464   -3.0436    0.4122 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4003   -1.3820    0.6963 H   0  0  0  0  0  0  0  0  0  0  0  0
  2 19  1  0
  7  6  1  0
  7 19  1  0
  5  3  1  0
 17 15  2  0
 15 13  1  0
 13 12  1  0
 12 10  1  0
  5  6  1  0
 15 16  1  0
  3  2  1  0
 13 14  2  0
  7  9  1  0
  2  1  2  3
 19 18  1  0
  3  4  1  0
 18 17  1  0
 19 39  1  6
 10  9  1  0
  7  8  1  1
 10 17  1  0
 10 11  1  6
  5 24  1  0
  5 25  1  0
  3 22  1  1
  6 26  1  0
  6 27  1  0
 18 37  1  0
 18 38  1  0
  9 31  1  0
  9 32  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
  1 20  1  0
  1 21  1  0
  4 23  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
 11 33  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0       0.662  -2.240   3.258  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.478  -1.408   2.588  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.576  -0.647   3.301  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.829  -1.141   2.838  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.504   0.857   3.030  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.361   1.189   1.538  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.206   0.416   0.837  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.144   0.927   1.398  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.288   0.704  -0.698  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.373  -0.187  -1.548  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.986   0.174  -1.420  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.732  -0.139  -2.918  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.948  -1.409  -3.358  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.229  -1.715  -4.503  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.844  -2.349  -2.233  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.130  -3.791  -2.394  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.525  -1.609  -1.172  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.414  -1.982   0.270  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.405  -1.120   1.091  0.00  0.00           C+0
HETATM   20  H   UNK     0       0.766  -2.393   4.329  0.00  0.00           H+0
HETATM   21  H   UNK     0      -0.140  -2.789   2.775  0.00  0.00           H+0
HETATM   22  H   UNK     0       2.545  -0.813   4.384  0.00  0.00           H+0
HETATM   23  H   UNK     0       3.814  -2.104   2.972  0.00  0.00           H+0
HETATM   24  H   UNK     0       1.666   1.292   3.587  0.00  0.00           H+0
HETATM   25  H   UNK     0       3.415   1.342   3.402  0.00  0.00           H+0
HETATM   26  H   UNK     0       3.312   0.953   1.042  0.00  0.00           H+0
HETATM   27  H   UNK     0       2.217   2.271   1.423  0.00  0.00           H+0
HETATM   28  H   UNK     0      -0.284   1.988   1.161  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.209   0.828   2.485  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.001   0.385   0.994  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.324   0.565  -1.037  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.055   1.760  -0.888  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.029   1.118  -1.644  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.036  -4.335  -1.450  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.433  -4.241  -3.108  0.00  0.00           H+0
HETATM   36  H   UNK     0       2.148  -3.941  -2.766  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.618  -1.837   0.606  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.646  -3.044   0.412  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.400  -1.382   0.696  0.00  0.00           H+0
CONECT    1    2   20   21                                                  
CONECT    2   19    3    1                                                  
CONECT    3    5    2    4   22                                             
CONECT    4    3   23                                                       
CONECT    5    3    6   24   25                                             
CONECT    6    7    5   26   27                                             
CONECT    7    6   19    9    8                                             
CONECT    8    7   28   29   30                                             
CONECT    9    7   10   31   32                                             
CONECT   10   12    9   17   11                                             
CONECT   11   10   33                                                       
CONECT   12   13   10                                                       
CONECT   13   15   12   14                                                  
CONECT   14   13                                                            
CONECT   15   17   13   16                                                  
CONECT   16   15   34   35   36                                             
CONECT   17   15   18   10                                                  
CONECT   18   19   17   37   38                                             
CONECT   19    2    7   18   39                                             
CONECT   20    1                                                            
CONECT   21    1                                                            
CONECT   22    3                                                            
CONECT   23    4                                                            
CONECT   24    5                                                            
CONECT   25    5                                                            
CONECT   26    6                                                            
CONECT   27    6                                                            
CONECT   28    8                                                            
CONECT   29    8                                                            
CONECT   30    8                                                            
CONECT   31    9                                                            
CONECT   32    9                                                            
CONECT   33   11                                                            
CONECT   34   16                                                            
CONECT   35   16                                                            
CONECT   36   16                                                            
CONECT   37   18                                                            
CONECT   38   18                                                            
CONECT   39   19                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   82    0
END

RDKit          3D

39 41  0  0  0  0  0  0  0  0999 V2000
    0.6615   -2.2395    3.2578 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4782   -1.4080    2.5878 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5759   -0.6474    3.3014 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8291   -1.1405    2.8377 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5036    0.8570    3.0303 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3612    1.1888    1.5379 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2065    0.4164    0.8370 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1436    0.9273    1.3978 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2876    0.7038   -0.6978 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3729   -0.1874   -1.5483 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9859    0.1743   -1.4198 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7315   -0.1391   -2.9180 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9480   -1.4088   -3.3582 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2291   -1.7149   -4.5032 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8438   -2.3491   -2.2332 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1298   -3.7907   -2.3940 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5250   -1.6088   -1.1719 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4143   -1.9821    0.2699 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4048   -1.1199    1.0914 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7659   -2.3935    4.3287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1400   -2.7891    2.7753 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5446   -0.8133    4.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8137   -2.1037    2.9721 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6657    1.2923    3.5867 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4147    1.3418    3.4025 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3122    0.9527    1.0418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2168    2.2705    1.4231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2836    1.9883    1.1613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2090    0.8283    2.4853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0010    0.3848    0.9938 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3243    0.5650   -1.0370 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0554    1.7601   -0.8881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0294    1.1182   -1.6444 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0358   -4.3355   -1.4503 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4325   -4.2406   -3.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1482   -3.9409   -2.7661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6184   -1.8365    0.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6464   -3.0436    0.4122 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4003   -1.3820    0.6963 H   0  0  0  0  0  0  0  0  0  0  0  0
  2 19  1  0
  7  6  1  0
  7 19  1  0
  5  3  1  0
 17 15  2  0
 15 13  1  0
 13 12  1  0
 12 10  1  0
  5  6  1  0
 15 16  1  0
  3  2  1  0
 13 14  2  0
  7  9  1  0
  2  1  2  3
 19 18  1  0
  3  4  1  0
 18 17  1  0
 19 39  1  6
 10  9  1  0
  7  8  1  1
 10 17  1  0
 10 11  1  6
  5 24  1  0
  5 25  1  0
  3 22  1  1
  6 26  1  0
  6 27  1  0
 18 37  1  0
 18 38  1  0
  9 31  1  0
  9 32  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
  1 20  1  0
  1 21  1  0
  4 23  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
 11 33  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₀O₄

Average Mass

264.3210 Da

Monoisotopic Mass

264.13616 Da

IUPAC Name

(4aS,6S,8aS,9aR)-6,9a-dihydroxy-3,8a-dimethyl-5-methylidene-2H,4H,4aH,5H,6H,7H,8H,8aH,9H,9aH-naphtho[2,3-b]furan-2-one

Traditional Name

(4aS,6S,8aS,9aR)-6,9a-dihydroxy-3,8a-dimethyl-5-methylidene-4H,4aH,6H,7H,8H,9H-naphtho[2,3-b]furan-2-one

CAS Registry Number

Not Available

SMILES

[H]O[C@]1([H])C(=C([H])[H])[C@@]2([H])C([H])([H])C3=C(C(=O)O[C@]3(O[H])C([H])([H])[C@]2(C([H])([H])[H])C([H])([H])C1([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C15H20O4/c1-8-10-6-11-9(2)13(17)19-15(11,18)7-14(10,3)5-4-12(8)16/h10,12,16,18H,1,4-7H2,2-3H3/t10-,12+,14+,15-/m1/s1

InChI Key

VITHJONQLOCSGP-UEEZHKSASA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Chloranthus multistachys	JEOL database	Liu, H.-Y., et al, Phytochemistry 88, 112 (2013)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Eudesmanolides, secoeudesmanolides, and derivatives

Alternative Parents

Substituents

Eudesmanolide
Sesquiterpenoid
Naphthofuran
2-furanone
Cyclic alcohol
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Hemiacetal
Lactone
Secondary alcohol
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.81	ALOGPS
logP	1.69	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	11.25	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	70.02 m³·mol⁻¹	ChemAxon
Polarizability	28.05 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

Not Available

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

71623932

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Liu, H.-Y., et al. (2013). Liu, H.-Y., et al, Phytochemistry 88, 112 (2013) . Phytochem..

Showing NP-Card for ent-(3R)-3-hydroxyatractylenolide III (NP0042080)

MOL for NP0042080 (ent-(3R)-3-hydroxyatractylenolide III)

3D MOL for NP0042080 (ent-(3R)-3-hydroxyatractylenolide III)

3D SDF for NP0042080 (ent-(3R)-3-hydroxyatractylenolide III)

3D-SDF for NP0042080 (ent-(3R)-3-hydroxyatractylenolide III)

PDB for NP0042080 (ent-(3R)-3-hydroxyatractylenolide III)

3D PDB for NP0042080 (ent-(3R)-3-hydroxyatractylenolide III)

SMILES for NP0042080 (ent-(3R)-3-hydroxyatractylenolide III)

INCHI for NP0042080 (ent-(3R)-3-hydroxyatractylenolide III)

Structure for NP0042080 (ent-(3R)-3-hydroxyatractylenolide III)

3D Structure for NP0042080 (ent-(3R)-3-hydroxyatractylenolide III)