NP-MRD: Showing NP-Card for lanceocrepidiaside D (NP0031064)

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Record Information

Version

2.0

Created at

2021-06-19 22:15:08 UTC

Updated at

2021-06-29 23:59:25 UTC

NP-MRD ID

NP0031064

Secondary Accession Numbers

None

Natural Product Identification

Common Name

lanceocrepidiaside D

Provided By

JEOL Database JEOL Logo

Description

Lanceocrepidiaside D belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. lanceocrepidiaside D is found in Crepidiastrum lanceolatum and Crepidiastrum lanceolatum NAKAI. lanceocrepidiaside D was first documented in 2005 (Takeda, Y., et al.). Based on a literature review very few articles have been published on Lanceocrepidiaside D.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202100153D          

 72 76  0  0  0  0            999 V2000
   -4.7293   -0.6367    4.4544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9260   -0.5765    3.3866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4221   -0.8023    2.0064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4859   -1.2899    1.6791 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4416   -0.3815    1.1573 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4810    0.3933    1.8975 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4711   -0.2671    3.2715 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8370    0.5746    4.3735 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3204    0.6967    4.2069 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1269    1.6538    3.1214 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9890    2.7775    3.6439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1986    1.4703    1.8244 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2615    2.3010    0.6671 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0979    3.1875    0.6685 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6599   -0.5765   -2.1447 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8748    2.6181    1.0480 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7907   -2.4928    1.5595 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1030   -4.2236   -6.4941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7781   -2.4430   -5.7974 H   0  0  0  0  0  0  0  0  0  0  0  0
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 31 63  1  0  0  0  0
  1 41  1  0  0  0  0
  1 42  1  0  0  0  0
M  END

     RDKit          3D

 72 76  0  0  0  0  0  0  0  0999 V2000
   -4.7293   -0.6367    4.4544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9260   -0.5765    3.3866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4221   -0.8023    2.0064 C   0  0  0  0  0  0  0  0  0  0  0  0
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 39 71  1  0
 22 57  1  0
 22 58  1  0
 21 56  1  6
 17 53  1  0
 17 54  1  0
 15 52  1  0
  9 47  1  0
  9 48  1  0
  8 45  1  0
  8 46  1  0
 11 49  1  0
 11 50  1  0
 11 51  1  0
  7 44  1  6
  6 43  1  1
 26 59  1  0
 26 60  1  0
 28 61  1  0
 29 62  1  0
 32 64  1  0
 33 65  1  0
 31 63  1  0
  1 41  1  0
  1 42  1  0
M  END


  Mrv1652306202100153D          

 72 76  0  0  0  0            999 V2000
   -4.7293   -0.6367    4.4544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9260   -0.5765    3.3866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4221   -0.8023    2.0064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4859   -1.2899    1.6791 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4416   -0.3815    1.1573 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4810    0.3933    1.8975 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4711   -0.2671    3.2715 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8370    0.5746    4.3735 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3204    0.6967    4.2069 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1269    1.6538    3.1214 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9890    2.7775    3.6439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1986    1.4703    1.8244 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2615    2.3010    0.6671 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0979    3.1875    0.6685 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3885    1.8188   -0.5553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1268    0.7453   -0.2484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8209   -0.1572   -1.2205 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2333   -0.0021   -2.5139 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3505   -1.1975   -3.2945 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6136   -2.2489   -2.6845 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6559   -3.4813   -3.4150 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0806   -4.5547   -2.5965 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4340   -4.1435   -2.3192 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6414   -3.5220   -1.1189 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8080   -3.3997   -0.2301 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0763   -3.0462   -1.0393 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2186   -1.6982   -0.3750 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9568   -0.5252   -1.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0704    0.7234   -0.4874 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4285    0.7998    0.8535 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4979    2.0029    1.4923 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7016   -0.3484    1.5846 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5913   -1.5987    0.9734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0395   -3.2905   -4.8082 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1646   -4.4823   -5.5881 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7548   -2.1467   -5.5346 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0920   -1.8998   -6.7852 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7657   -0.8814   -4.6813 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5268    0.1306   -5.3585 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0934    0.3999    1.2268 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3639   -0.4643    5.4606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7853   -0.8738    4.3449 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0896    1.0261    5.1708 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9558    2.3856    3.9758 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4994    3.2534    4.5014 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1722    3.5758    2.9255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1964    2.2401   -1.5272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8827    0.0972   -1.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7298   -1.1908   -0.8683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4140   -1.4603   -3.3697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7006   -3.8055   -3.5120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4605   -4.7595   -1.6654 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1316   -5.4992   -3.1480 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6565   -3.8082   -0.5064 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4997   -2.9791   -2.0494 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6599   -0.5765   -2.1447 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8733    1.6246   -1.0602 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8748    2.6181    1.0480 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9831   -0.2709    2.6304 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7907   -2.4928    1.5595 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0299   -3.0579   -4.7334 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1030   -4.2236   -6.4941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7781   -2.4430   -5.7974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4808   -1.0657   -7.1196 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2549   -0.4892   -4.5869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5918    0.8727   -4.7245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6128   -0.5829    1.3236 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0  0  0  0
 36 37  1  0  0  0  0
  9  8  1  0  0  0  0
  7  8  1  0  0  0  0
 38 39  1  0  0  0  0
 10 11  1  0  0  0  0
  7  6  1  0  0  0  0
 22 23  1  0  0  0  0
 19 38  1  0  0  0  0
 18 17  1  0  0  0  0
  6  5  1  0  0  0  0
  5  3  1  0  0  0  0
  3  2  1  0  0  0  0
 16 40  1  0  0  0  0
  3  4  2  0  0  0  0
 16 17  1  0  0  0  0
 38 36  1  0  0  0  0
 23 24  1  0  0  0  0
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 36 34  1  0  0  0  0
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 34 21  1  0  0  0  0
 27 26  1  0  0  0  0
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 27 28  2  0  0  0  0
 15 16  2  0  0  0  0
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 29 30  2  0  0  0  0
 20 19  1  0  0  0  0
 30 32  1  0  0  0  0
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 12 10  2  0  0  0  0
 13 14  2  0  0  0  0
 40  6  1  0  0  0  0
  2  1  2  3  0  0  0
 34 35  1  0  0  0  0
 40 72  1  6  0  0  0
  7  2  1  0  0  0  0
 21 22  1  0  0  0  0
 19 18  1  0  0  0  0
 19 55  1  6  0  0  0
 34 66  1  1  0  0  0
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 15 52  1  0  0  0  0
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 11 50  1  0  0  0  0
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  7 44  1  6  0  0  0
  6 43  1  1  0  0  0
 26 59  1  0  0  0  0
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 31 63  1  0  0  0  0
  1 41  1  0  0  0  0
  1 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0031064

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C(=O)OC([H])([H])[C@@]1([H])O[C@@]([H])(OC([H])([H])C2=C([H])C(=O)C3=C(C([H])([H])[H])C([H])([H])C([H])([H])[C@@]4([H])C(=C([H])[H])C(=O)O[C@]4([H])[C@@]23[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C29H32O11/c1-13-3-8-18-14(2)28(36)40-27(18)23-16(10-19(31)22(13)23)11-38-29-26(35)25(34)24(33)20(39-29)12-37-21(32)9-15-4-6-17(30)7-5-15/h4-7,10,18,20,23-27,29-30,33-35H,2-3,8-9,11-12H2,1H3/t18-,20+,23-,24+,25-,26+,27-,29+/m0/s1

> <INCHI_KEY>
UCMHARQJSJFNCT-PUWZVNQMSA-N

> <FORMULA>
C29H32O11

> <MOLECULAR_WEIGHT>
556.564

> <EXACT_MASS>
556.19446185

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
55.275289300548096

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3S,4S,5R,6R)-6-{[(3aS,9aS,9bS)-6-methyl-3-methylidene-2,7-dioxo-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-9-yl]methoxy}-3,4,5-trihydroxyoxan-2-yl]methyl 2-(4-hydroxyphenyl)acetate

> <ALOGPS_LOGP>
1.12

> <JCHEM_LOGP>
1.5284849430000014

> <ALOGPS_LOGS>
-3.28

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.179556262719965

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.495522374890056

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6490852181186213

> <JCHEM_POLAR_SURFACE_AREA>
169.05

> <JCHEM_REFRACTIVITY>
138.562

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.91e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4S,5R,6R)-6-{[(3aS,9aS,9bS)-6-methyl-3-methylidene-2,7-dioxo-3aH,4H,5H,9aH,9bH-azuleno[4,5-b]furan-9-yl]methoxy}-3,4,5-trihydroxyoxan-2-yl]methyl (4-hydroxyphenyl)acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 72 76  0  0  0  0  0  0  0  0999 V2000
   -4.7293   -0.6367    4.4544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9260   -0.5765    3.3866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4221   -0.8023    2.0064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4859   -1.2899    1.6791 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4416   -0.3815    1.1573 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4810    0.3933    1.8975 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4711   -0.2671    3.2715 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8370    0.5746    4.3735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3204    0.6967    4.2069 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1269    1.6538    3.1214 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9890    2.7775    3.6439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1986    1.4703    1.8244 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2615    2.3010    0.6671 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0979    3.1875    0.6685 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3885    1.8188   -0.5553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1268    0.7453   -0.2484 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2333   -0.0021   -2.5139 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3505   -1.1975   -3.2945 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6136   -2.2489   -2.6845 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0806   -4.5547   -2.5965 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4340   -4.1435   -2.3192 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6414   -3.5220   -1.1189 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8080   -3.3997   -0.2301 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0763   -3.0462   -1.0393 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4979    2.0029    1.4923 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7016   -0.3484    1.5846 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5913   -1.5987    0.9734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0395   -3.2905   -4.8082 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -1.5268    0.1306   -5.3585 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0934    0.3999    1.2268 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3639   -0.4643    5.4606 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8725    1.4214    1.9450 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1287   -0.2887    4.0267 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7006   -3.8055   -3.5120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4605   -4.7595   -1.6654 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1316   -5.4992   -3.1480 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6565   -3.8082   -0.5064 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4997   -2.9791   -2.0494 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6599   -0.5765   -2.1447 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8733    1.6246   -1.0602 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7781   -2.4430   -5.7974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4808   -1.0657   -7.1196 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2549   -0.4892   -4.5869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5918    0.8727   -4.7245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6128   -0.5829    1.3236 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
 36 37  1  0
  9  8  1  0
  7  8  1  0
 38 39  1  0
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 23 24  1  0
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 40  6  1  0
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M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -4.729  -0.637   4.454  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.926  -0.577   3.387  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.422  -0.802   2.006  0.00  0.00           C+0
HETATM    4  O   UNK     0      -5.486  -1.290   1.679  0.00  0.00           O+0
HETATM    5  O   UNK     0      -3.442  -0.382   1.157  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.481   0.393   1.898  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.471  -0.267   3.272  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.837   0.575   4.373  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.320   0.697   4.207  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.127   1.654   3.121  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.989   2.777   3.644  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.199   1.470   1.824  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.262   2.301   0.667  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.098   3.188   0.669  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.389   1.819  -0.555  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.127   0.745  -0.248  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.821  -0.157  -1.220  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.233  -0.002  -2.514  0.00  0.00           O+0
HETATM   19  C   UNK     0      -1.351  -1.198  -3.295  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.614  -2.249  -2.684  0.00  0.00           O+0
HETATM   21  C   UNK     0      -0.656  -3.481  -3.415  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.081  -4.555  -2.596  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.434  -4.144  -2.319  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.641  -3.522  -1.119  0.00  0.00           C+0
HETATM   25  O   UNK     0       0.808  -3.400  -0.230  0.00  0.00           O+0
HETATM   26  C   UNK     0       3.076  -3.046  -1.039  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.219  -1.698  -0.375  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.957  -0.525  -1.099  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.070   0.723  -0.487  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.429   0.800   0.854  0.00  0.00           C+0
HETATM   31  O   UNK     0       3.498   2.003   1.492  0.00  0.00           O+0
HETATM   32  C   UNK     0       3.702  -0.348   1.585  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.591  -1.599   0.973  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.040  -3.291  -4.808  0.00  0.00           C+0
HETATM   35  O   UNK     0      -0.165  -4.482  -5.588  0.00  0.00           O+0
HETATM   36  C   UNK     0      -0.755  -2.147  -5.535  0.00  0.00           C+0
HETATM   37  O   UNK     0      -0.092  -1.900  -6.785  0.00  0.00           O+0
HETATM   38  C   UNK     0      -0.766  -0.881  -4.681  0.00  0.00           C+0
HETATM   39  O   UNK     0      -1.527   0.131  -5.359  0.00  0.00           O+0
HETATM   40  C   UNK     0      -1.093   0.400   1.227  0.00  0.00           C+0
HETATM   41  H   UNK     0      -4.364  -0.464   5.461  0.00  0.00           H+0
HETATM   42  H   UNK     0      -5.785  -0.874   4.345  0.00  0.00           H+0
HETATM   43  H   UNK     0      -2.873   1.421   1.945  0.00  0.00           H+0
HETATM   44  H   UNK     0      -1.951  -1.235   3.216  0.00  0.00           H+0
HETATM   45  H   UNK     0      -2.024   0.094   5.342  0.00  0.00           H+0
HETATM   46  H   UNK     0      -2.299   1.569   4.424  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.129  -0.289   4.027  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.090   1.026   5.171  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.956   2.386   3.976  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.499   3.253   4.501  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.172   3.576   2.926  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.196   2.240  -1.527  0.00  0.00           H+0
HETATM   53  H   UNK     0      -2.883   0.097  -1.295  0.00  0.00           H+0
HETATM   54  H   UNK     0      -1.730  -1.191  -0.868  0.00  0.00           H+0
HETATM   55  H   UNK     0      -2.414  -1.460  -3.370  0.00  0.00           H+0
HETATM   56  H   UNK     0      -1.701  -3.805  -3.512  0.00  0.00           H+0
HETATM   57  H   UNK     0      -0.461  -4.760  -1.665  0.00  0.00           H+0
HETATM   58  H   UNK     0       0.132  -5.499  -3.148  0.00  0.00           H+0
HETATM   59  H   UNK     0       3.656  -3.808  -0.506  0.00  0.00           H+0
HETATM   60  H   UNK     0       3.500  -2.979  -2.049  0.00  0.00           H+0
HETATM   61  H   UNK     0       2.660  -0.577  -2.145  0.00  0.00           H+0
HETATM   62  H   UNK     0       2.873   1.625  -1.060  0.00  0.00           H+0
HETATM   63  H   UNK     0       2.875   2.618   1.048  0.00  0.00           H+0
HETATM   64  H   UNK     0       3.983  -0.271   2.630  0.00  0.00           H+0
HETATM   65  H   UNK     0       3.791  -2.493   1.560  0.00  0.00           H+0
HETATM   66  H   UNK     0       1.030  -3.058  -4.733  0.00  0.00           H+0
HETATM   67  H   UNK     0       0.103  -4.224  -6.494  0.00  0.00           H+0
HETATM   68  H   UNK     0      -1.778  -2.443  -5.797  0.00  0.00           H+0
HETATM   69  H   UNK     0      -0.481  -1.066  -7.120  0.00  0.00           H+0
HETATM   70  H   UNK     0       0.255  -0.489  -4.587  0.00  0.00           H+0
HETATM   71  H   UNK     0      -1.592   0.873  -4.724  0.00  0.00           H+0
HETATM   72  H   UNK     0      -0.613  -0.583   1.324  0.00  0.00           H+0
CONECT    1    2   41   42                                                  
CONECT    2    3    1    7                                                  
CONECT    3    5    2    4                                                  
CONECT    4    3                                                            
CONECT    5    6    3                                                       
CONECT    6    7    5   40   43                                             
CONECT    7    8    6    2   44                                             
CONECT    8    9    7   45   46                                             
CONECT    9   10    8   47   48                                             
CONECT   10    9   11   12                                                  
CONECT   11   10   49   50   51                                             
CONECT   12   13   40   10                                                  
CONECT   13   12   15   14                                                  
CONECT   14   13                                                            
CONECT   15   13   16   52                                                  
CONECT   16   40   17   15                                                  
CONECT   17   18   16   53   54                                             
CONECT   18   17   19                                                       
CONECT   19   38   20   18   55                                             
CONECT   20   21   19                                                       
CONECT   21   34   20   22   56                                             
CONECT   22   23   21   57   58                                             
CONECT   23   22   24                                                       
CONECT   24   23   26   25                                                  
CONECT   25   24                                                            
CONECT   26   24   27   59   60                                             
CONECT   27   26   28   33                                                  
CONECT   28   27   29   61                                                  
CONECT   29   28   30   62                                                  
CONECT   30   29   32   31                                                  
CONECT   31   30   63                                                       
CONECT   32   30   33   64                                                  
CONECT   33   32   27   65                                                  
CONECT   34   36   21   35   66                                             
CONECT   35   34   67                                                       
CONECT   36   37   38   34   68                                             
CONECT   37   36   69                                                       
CONECT   38   39   19   36   70                                             
CONECT   39   38   71                                                       
CONECT   40   16   12    6   72                                             
CONECT   41    1                                                            
CONECT   42    1                                                            
CONECT   43    6                                                            
CONECT   44    7                                                            
CONECT   45    8                                                            
CONECT   46    8                                                            
CONECT   47    9                                                            
CONECT   48    9                                                            
CONECT   49   11                                                            
CONECT   50   11                                                            
CONECT   51   11                                                            
CONECT   52   15                                                            
CONECT   53   17                                                            
CONECT   54   17                                                            
CONECT   55   19                                                            
CONECT   56   21                                                            
CONECT   57   22                                                            
CONECT   58   22                                                            
CONECT   59   26                                                            
CONECT   60   26                                                            
CONECT   61   28                                                            
CONECT   62   29                                                            
CONECT   63   31                                                            
CONECT   64   32                                                            
CONECT   65   33                                                            
CONECT   66   34                                                            
CONECT   67   35                                                            
CONECT   68   36                                                            
CONECT   69   37                                                            
CONECT   70   38                                                            
CONECT   71   39                                                            
CONECT   72   40                                                            
MASTER        0    0    0    0    0    0    0    0   72    0  152    0
END

RDKit          3D

72 76  0  0  0  0  0  0  0  0999 V2000
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   -1.8370    0.5746    4.3735 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1269    1.6538    3.1214 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1986    1.4703    1.8244 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2615    2.3010    0.6671 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4979    2.0029    1.4923 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0934    0.3999    1.2268 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3639   -0.4643    5.4606 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6599   -0.5765   -2.1447 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8733    1.6246   -1.0602 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8748    2.6181    1.0480 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9831   -0.2709    2.6304 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7907   -2.4928    1.5595 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0299   -3.0579   -4.7334 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1030   -4.2236   -6.4941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7781   -2.4430   -5.7974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4808   -1.0657   -7.1196 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2549   -0.4892   -4.5869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5918    0.8727   -4.7245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6128   -0.5829    1.3236 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
 36 37  1  0
  9  8  1  0
  7  8  1  0
 38 39  1  0
 10 11  1  0
  7  6  1  0
 22 23  1  0
 19 38  1  0
 18 17  1  0
  6  5  1  0
  5  3  1  0
  3  2  1  0
 16 40  1  0
  3  4  2  0
 16 17  1  0
 38 36  1  0
 23 24  1  0
 24 26  1  0
 36 34  1  0
 24 25  2  0
 34 21  1  0
 27 26  1  0
 12 13  1  0
 13 15  1  0
 27 28  2  0
 15 16  2  0
 28 29  1  0
 21 20  1  0
 29 30  2  0
 20 19  1  0
 30 32  1  0
 40 12  1  0
 32 33  2  0
 33 27  1  0
 30 31  1  0
 12 10  2  0
 13 14  2  0
 40  6  1  0
  2  1  2  3
 34 35  1  0
 40 72  1  6
  7  2  1  0
 21 22  1  0
 19 18  1  0
 19 55  1  6
 34 66  1  1
 35 67  1  0
 36 68  1  6
 37 69  1  0
 38 70  1  1
 39 71  1  0
 22 57  1  0
 22 58  1  0
 21 56  1  6
 17 53  1  0
 17 54  1  0
 15 52  1  0
  9 47  1  0
  9 48  1  0
  8 45  1  0
  8 46  1  0
 11 49  1  0
 11 50  1  0
 11 51  1  0
  7 44  1  6
  6 43  1  1
 26 59  1  0
 26 60  1  0
 28 61  1  0
 29 62  1  0
 32 64  1  0
 33 65  1  0
 31 63  1  0
  1 41  1  0
  1 42  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₂O₁₁

Average Mass

556.5640 Da

Monoisotopic Mass

556.19446 Da

IUPAC Name

[(2R,3S,4S,5R,6R)-6-{[(3aS,9aS,9bS)-6-methyl-3-methylidene-2,7-dioxo-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-9-yl]methoxy}-3,4,5-trihydroxyoxan-2-yl]methyl 2-(4-hydroxyphenyl)acetate

Traditional Name

[(2R,3S,4S,5R,6R)-6-{[(3aS,9aS,9bS)-6-methyl-3-methylidene-2,7-dioxo-3aH,4H,5H,9aH,9bH-azuleno[4,5-b]furan-9-yl]methoxy}-3,4,5-trihydroxyoxan-2-yl]methyl (4-hydroxyphenyl)acetate

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C(=O)OC([H])([H])[C@@]1([H])O[C@@]([H])(OC([H])([H])C2=C([H])C(=O)C3=C(C([H])([H])[H])C([H])([H])C([H])([H])[C@@]4([H])C(=C([H])[H])C(=O)O[C@]4([H])[C@@]23[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]

InChI Identifier

InChI=1S/C29H32O11/c1-13-3-8-18-14(2)28(36)40-27(18)23-16(10-19(31)22(13)23)11-38-29-26(35)25(34)24(33)20(39-29)12-37-21(32)9-15-4-6-17(30)7-5-15/h4-7,10,18,20,23-27,29-30,33-35H,2-3,8-9,11-12H2,1H3/t18-,20+,23-,24+,25-,26+,27-,29+/m0/s1

InChI Key

UCMHARQJSJFNCT-PUWZVNQMSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, C₅D₅N, 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
Crepidiastrum lanceolatum	JEOL database	Takeda, Y., et al, Phytochemistry 66, 727 (2005)
Crepidiastrum lanceolatum NAKAI	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glycosyl compounds

Alternative Parents

Substituents

O-glycosyl compound
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Gamma butyrolactone
Monosaccharide
Benzenoid
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Oxolane
Lactone
Ketone
Carboxylic acid ester
Secondary alcohol
Acetal
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Polyol
Alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxide
Aldehyde
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	1.12	ALOGPS
logP	1.53	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	9.5	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	169.05 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	138.56 m³·mol⁻¹	ChemAxon
Polarizability	55.28 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

10193287

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21580545

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Takeda, Y., et al. (2005). Takeda, Y., et al, Phytochemistry 66, 727 (2005) . Phytochem..

Showing NP-Card for lanceocrepidiaside D (NP0031064)

MOL for NP0031064 (lanceocrepidiaside D)

3D MOL for NP0031064 (lanceocrepidiaside D)

3D SDF for NP0031064 (lanceocrepidiaside D)

3D-SDF for NP0031064 (lanceocrepidiaside D)

PDB for NP0031064 (lanceocrepidiaside D)

3D PDB for NP0031064 (lanceocrepidiaside D)

SMILES for NP0031064 (lanceocrepidiaside D)

INCHI for NP0031064 (lanceocrepidiaside D)

Structure for NP0031064 (lanceocrepidiaside D)

3D Structure for NP0031064 (lanceocrepidiaside D)