NP-MRD: Showing NP-Card for Hypocrellin D (NP0006518)

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Record Information

Version

2.0

Created at

2020-12-09 03:30:45 UTC

Updated at

2021-07-15 16:55:02 UTC

NP-MRD ID

NP0006518

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Hypocrellin D

Provided By

NPAtlas

Description

(12S,13R)-12-acetyl-9,13,17-trihydroxy-5,10,16,21-tetramethoxy-13-methylpentacyclo[13.8.0.0²,¹¹.0³,⁸.0¹⁸,²³]Tricosa-1(15),2(11),3(8),5,9,16,18(23),20-octaene-4,7,19,22-tetrone belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone). Hypocrellin D is found in Shiraia bambusicola. Hypocrellin D was first documented in 2006 (PMID: 16915819). Based on a literature review very few articles have been published on (12S,13R)-12-acetyl-9,13,17-trihydroxy-5,10,16,21-tetramethoxy-13-methylpentacyclo[13.8.0.0²,¹¹.0³,⁸.0¹⁸,²³]Tricosa-1(15),2(11),3(8),5,9,16,18(23),20-octaene-4,7,19,22-tetrone.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118283D          

 68 72  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306242118283D          

 68 72  0  0  0  0            999 V2000
    4.1300    0.0516   -3.6863 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8759   -0.1496   -2.3130 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9896    0.6678   -1.6119 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2829    1.9513   -1.5194 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4349    2.9008   -0.8168 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7224    4.1297   -0.7413 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2218    2.4405   -0.1796 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3121    3.3036    0.3974 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6264    4.6427    0.4784 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9050    2.8779    0.8987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8419    3.7295    1.4767 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7373    3.9340    2.8796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2021    1.5886    0.8276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2608    0.7068    0.2467 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9444    1.0373   -0.2894 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7878    0.1084   -1.0056 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6431   -1.1013   -1.2169 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8087   -1.2399    0.8570 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9277   -2.6725    0.7576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0877   -3.4258    0.2066 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0188   -4.7756    0.1027 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2722   -2.8227   -0.2692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2995   -3.5788   -0.8161 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2982   -4.0561    0.0657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4375   -1.4901   -0.2047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7701   -0.9267   -0.5481 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8785   -1.0232   -2.0446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8519   -0.3479   -2.8829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7758   -1.6349   -2.6078 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1012    0.4298   -0.1398 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6367    0.5126    0.0053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8293    1.3536   -1.1821 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5842    1.0675    1.1399 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1033   -3.2600    1.3686 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2863   -4.5125    1.3056 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0692   -2.4043    2.0525 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9178   -1.1048    2.1505 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9207   -0.4055    2.8424 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9096    0.2239    2.0447 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7694   -0.4170    1.5632 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7694    0.8023    1.7839 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2399   -0.0342   -4.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8350   -0.7684   -3.9950 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5813    1.0540   -3.8802 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1923    2.3434   -1.9672 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0160    5.3379    0.8849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8683    4.5961    3.0400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5601    2.9368    3.3626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6915    4.3440    3.2236 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6365   -5.4617    0.3062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2014   -5.1732    0.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1883   -3.6337    1.0812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3189   -3.9045   -0.3345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5810   -1.6257   -0.1801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8777   -0.2343   -2.3922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6327   -0.9591   -3.8091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2569    0.6173   -3.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0754   -0.0350   -0.8382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9206    0.1080    1.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9409    1.5912   -0.0240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3993    2.1421   -1.0573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5163    0.3382    1.9583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2428    1.8892    1.4371 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9288   -2.9013    2.4699 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4399    0.9698    1.3669 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3526   -0.5613    1.4026 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7078    0.6780    2.6405 H   0  0  0  0  0  0  0  0  0  0  0  0
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  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
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 16  3  1  0  0  0  0
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 15  7  1  0  0  0  0
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 40 67  1  0  0  0  0
 40 68  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0006518

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2C(=O)C([H])=C(OC([H])([H])[H])C(=O)C2=C2C3=C4C(=O)C(OC([H])([H])[H])=C([H])C(=O)C4=C(O[H])C(OC([H])([H])[H])=C3[C@]([H])(C(=O)C([H])([H])[H])[C@@](O[H])(C([H])([H])[H])C([H])([H])C2=C1OC([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C30H26O12/c1-10(31)23-22-19(21-18(27(37)29(22)42-6)13(33)8-15(40-4)25(21)35)16-11(9-30(23,2)38)28(41-5)26(36)17-12(32)7-14(39-3)24(34)20(16)17/h7-8,23,36-38H,9H2,1-6H3/t23-,30+/m0/s1

> <INCHI_KEY>
UVHNWRDTZAYVST-YUDQIZAISA-N

> <FORMULA>
C30H26O12

> <MOLECULAR_WEIGHT>
578.526

> <EXACT_MASS>
578.142426277

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
56.01157920250319

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(12S,13R)-12-acetyl-9,13,17-trihydroxy-5,10,16,21-tetramethoxy-13-methylpentacyclo[13.8.0.0^{2,11}.0^{3,8}.0^{18,23}]tricosa-1(23),2,5,8,10,15,17,20-octaene-4,7,19,22-tetrone

> <ALOGPS_LOGP>
3.04

> <JCHEM_LOGP>
1.8383028670000001

> <ALOGPS_LOGS>
-4.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.553277139223598

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.873531467863682

> <JCHEM_PKA_STRONGEST_BASIC>
-3.144096726919484

> <JCHEM_POLAR_SURFACE_AREA>
182.95999999999995

> <JCHEM_REFRACTIVITY>
150.59589999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.20e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(12S,13R)-12-acetyl-9,13,17-trihydroxy-5,10,16,21-tetramethoxy-13-methylpentacyclo[13.8.0.0^{2,11}.0^{3,8}.0^{18,23}]tricosa-1(23),2,5,8,10,15,17,20-octaene-4,7,19,22-tetrone

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 68 72  0  0  0  0  0  0  0  0999 V2000
    4.1300    0.0516   -3.6863 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8759   -0.1496   -2.3130 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9896    0.6678   -1.6119 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2829    1.9513   -1.5194 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4349    2.9008   -0.8168 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7224    4.1297   -0.7413 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2218    2.4405   -0.1796 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3121    3.3036    0.3974 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6264    4.6427    0.4784 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9050    2.8779    0.8987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8419    3.7295    1.4767 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7373    3.9340    2.8796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2021    1.5886    0.8276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2608    0.7068    0.2467 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9444    1.0373   -0.2894 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7878    0.1084   -1.0056 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6431   -1.1013   -1.2169 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3599   -0.7645    0.3544 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8087   -1.2399    0.8570 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9277   -2.6725    0.7576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0877   -3.4258    0.2066 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0188   -4.7756    0.1027 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2722   -2.8227   -0.2692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2995   -3.5788   -0.8161 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2982   -4.0561    0.0657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4375   -1.4901   -0.2047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7701   -0.9267   -0.5481 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8785   -1.0232   -2.0446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8519   -0.3479   -2.8829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7758   -1.6349   -2.6078 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1012    0.4298   -0.1398 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6367    0.5126    0.0053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8293    1.3536   -1.1821 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1033   -3.2600    1.3686 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2863   -4.5125    1.3056 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0692   -2.4043    2.0525 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9178   -1.1048    2.1505 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9207   -0.4055    2.8424 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9096    0.2239    2.0447 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7694   -0.4170    1.5632 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7694    0.8023    1.7839 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2399   -0.0342   -4.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8350   -0.7684   -3.9950 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5813    1.0540   -3.8802 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1923    2.3434   -1.9672 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0160    5.3379    0.8849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8683    4.5961    3.0400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5601    2.9368    3.3626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6915    4.3440    3.2236 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6365   -5.4617    0.3062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2014   -5.1732    0.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1883   -3.6337    1.0812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3189   -3.9045   -0.3345 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.6327   -0.9591   -3.8091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2569    0.6173   -3.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0754   -0.0350   -0.8382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9206    0.1080    1.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9409    1.5912   -0.0240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3993    2.1421   -1.0573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5163    0.3382    1.9583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2428    1.8892    1.4371 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9288   -2.9013    2.4699 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4399    0.9698    1.3669 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3526   -0.5613    1.4026 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7078    0.6780    2.6405 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
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 13 14  1  0
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 15 16  1  0
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 14 18  1  0
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 27 31  1  0
 31 32  1  0
 31 33  1  6
 31 34  1  0
 20 35  1  0
 35 36  2  0
 35 37  1  0
 37 38  2  0
 38 39  1  0
 39 40  1  0
 38 41  1  0
 41 42  2  0
 16  3  1  0
 26 18  1  0
 15  7  1  0
 41 19  1  0
 34 13  1  0
  1 43  1  0
  1 44  1  0
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  9 47  1  0
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 37 65  1  0
 40 66  1  0
 40 67  1  0
 40 68  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       4.130   0.052  -3.686  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.876  -0.150  -2.313  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.990   0.668  -1.612  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.283   1.951  -1.519  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.435   2.901  -0.817  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.722   4.130  -0.741  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.222   2.441  -0.180  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.312   3.304   0.397  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.626   4.643   0.478  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.905   2.878   0.899  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.842   3.729   1.477  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.737   3.934   2.880  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.202   1.589   0.828  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.261   0.707   0.247  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.944   1.037  -0.289  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.788   0.108  -1.006  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.643  -1.101  -1.217  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.360  -0.765   0.354  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.809  -1.240   0.857  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.928  -2.672   0.758  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.088  -3.426   0.207  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.019  -4.776   0.103  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.272  -2.823  -0.269  0.00  0.00           C+0
HETATM   24  O   UNK     0      -2.300  -3.579  -0.816  0.00  0.00           O+0
HETATM   25  C   UNK     0      -3.298  -4.056   0.066  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.438  -1.490  -0.205  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.770  -0.927  -0.548  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.878  -1.023  -2.045  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.852  -0.348  -2.883  0.00  0.00           C+0
HETATM   30  O   UNK     0      -3.776  -1.635  -2.608  0.00  0.00           O+0
HETATM   31  C   UNK     0      -3.101   0.430  -0.140  0.00  0.00           C+0
HETATM   32  C   UNK     0      -4.637   0.513   0.005  0.00  0.00           C+0
HETATM   33  O   UNK     0      -2.829   1.354  -1.182  0.00  0.00           O+0
HETATM   34  C   UNK     0      -2.584   1.067   1.140  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.103  -3.260   1.369  0.00  0.00           C+0
HETATM   36  O   UNK     0       2.286  -4.513   1.306  0.00  0.00           O+0
HETATM   37  C   UNK     0       3.069  -2.404   2.053  0.00  0.00           C+0
HETATM   38  C   UNK     0       2.918  -1.105   2.151  0.00  0.00           C+0
HETATM   39  O   UNK     0       3.921  -0.406   2.842  0.00  0.00           O+0
HETATM   40  C   UNK     0       4.910   0.224   2.045  0.00  0.00           C+0
HETATM   41  C   UNK     0       1.769  -0.417   1.563  0.00  0.00           C+0
HETATM   42  O   UNK     0       1.769   0.802   1.784  0.00  0.00           O+0
HETATM   43  H   UNK     0       3.240  -0.034  -4.320  0.00  0.00           H+0
HETATM   44  H   UNK     0       4.835  -0.768  -3.995  0.00  0.00           H+0
HETATM   45  H   UNK     0       4.581   1.054  -3.880  0.00  0.00           H+0
HETATM   46  H   UNK     0       4.192   2.343  -1.967  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.016   5.338   0.885  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.868   4.596   3.040  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.560   2.937   3.363  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.692   4.344   3.224  0.00  0.00           H+0
HETATM   51  H   UNK     0       0.637  -5.462   0.306  0.00  0.00           H+0
HETATM   52  H   UNK     0      -3.201  -5.173   0.196  0.00  0.00           H+0
HETATM   53  H   UNK     0      -3.188  -3.634   1.081  0.00  0.00           H+0
HETATM   54  H   UNK     0      -4.319  -3.905  -0.335  0.00  0.00           H+0
HETATM   55  H   UNK     0      -3.581  -1.626  -0.180  0.00  0.00           H+0
HETATM   56  H   UNK     0      -0.878  -0.234  -2.392  0.00  0.00           H+0
HETATM   57  H   UNK     0      -1.633  -0.959  -3.809  0.00  0.00           H+0
HETATM   58  H   UNK     0      -2.257   0.617  -3.303  0.00  0.00           H+0
HETATM   59  H   UNK     0      -5.075  -0.035  -0.838  0.00  0.00           H+0
HETATM   60  H   UNK     0      -4.921   0.108   1.000  0.00  0.00           H+0
HETATM   61  H   UNK     0      -4.941   1.591  -0.024  0.00  0.00           H+0
HETATM   62  H   UNK     0      -3.399   2.142  -1.057  0.00  0.00           H+0
HETATM   63  H   UNK     0      -2.516   0.338   1.958  0.00  0.00           H+0
HETATM   64  H   UNK     0      -3.243   1.889   1.437  0.00  0.00           H+0
HETATM   65  H   UNK     0       3.929  -2.901   2.470  0.00  0.00           H+0
HETATM   66  H   UNK     0       4.440   0.970   1.367  0.00  0.00           H+0
HETATM   67  H   UNK     0       5.353  -0.561   1.403  0.00  0.00           H+0
HETATM   68  H   UNK     0       5.708   0.678   2.640  0.00  0.00           H+0
CONECT    1    2   43   44   45                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   16                                                  
CONECT    4    3    5   46                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   15                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8   47                                                       
CONECT   10    8   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11   48   49   50                                             
CONECT   13   10   14   34                                                  
CONECT   14   13   15   18                                                  
CONECT   15   14   16    7                                                  
CONECT   16   15   17    3                                                  
CONECT   17   16                                                            
CONECT   18   14   19   26                                                  
CONECT   19   18   20   41                                                  
CONECT   20   19   21   35                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21   51                                                       
CONECT   23   21   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24   52   53   54                                             
CONECT   26   23   27   18                                                  
CONECT   27   26   28   31   55                                             
CONECT   28   27   29   30                                                  
CONECT   29   28   56   57   58                                             
CONECT   30   28                                                            
CONECT   31   27   32   33   34                                             
CONECT   32   31   59   60   61                                             
CONECT   33   31   62                                                       
CONECT   34   31   13   63   64                                             
CONECT   35   20   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   65                                                  
CONECT   38   37   39   41                                                  
CONECT   39   38   40                                                       
CONECT   40   39   66   67   68                                             
CONECT   41   38   42   19                                                  
CONECT   42   41                                                            
CONECT   43    1                                                            
CONECT   44    1                                                            
CONECT   45    1                                                            
CONECT   46    4                                                            
CONECT   47    9                                                            
CONECT   48   12                                                            
CONECT   49   12                                                            
CONECT   50   12                                                            
CONECT   51   22                                                            
CONECT   52   25                                                            
CONECT   53   25                                                            
CONECT   54   25                                                            
CONECT   55   27                                                            
CONECT   56   29                                                            
CONECT   57   29                                                            
CONECT   58   29                                                            
CONECT   59   32                                                            
CONECT   60   32                                                            
CONECT   61   32                                                            
CONECT   62   33                                                            
CONECT   63   34                                                            
CONECT   64   34                                                            
CONECT   65   37                                                            
CONECT   66   40                                                            
CONECT   67   40                                                            
CONECT   68   40                                                            
MASTER        0    0    0    0    0    0    0    0   68    0  144    0
END

RDKit          3D

68 72  0  0  0  0  0  0  0  0999 V2000
    4.1300    0.0516   -3.6863 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8759   -0.1496   -2.3130 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9896    0.6678   -1.6119 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2829    1.9513   -1.5194 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4349    2.9008   -0.8168 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7224    4.1297   -0.7413 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2218    2.4405   -0.1796 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3121    3.3036    0.3974 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6264    4.6427    0.4784 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9050    2.8779    0.8987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8419    3.7295    1.4767 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7373    3.9340    2.8796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2021    1.5886    0.8276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2608    0.7068    0.2467 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9444    1.0373   -0.2894 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7878    0.1084   -1.0056 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6431   -1.1013   -1.2169 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3599   -0.7645    0.3544 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8087   -1.2399    0.8570 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9277   -2.6725    0.7576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0877   -3.4258    0.2066 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0188   -4.7756    0.1027 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2722   -2.8227   -0.2692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2995   -3.5788   -0.8161 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2982   -4.0561    0.0657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4375   -1.4901   -0.2047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7701   -0.9267   -0.5481 C   0  0  2  0  0  0  0  0  0  0  0  0
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    2.1033   -3.2600    1.3686 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2863   -4.5125    1.3056 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0692   -2.4043    2.0525 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9178   -1.1048    2.1505 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9207   -0.4055    2.8424 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9096    0.2239    2.0447 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7694   -0.4170    1.5632 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7694    0.8023    1.7839 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2399   -0.0342   -4.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8350   -0.7684   -3.9950 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5813    1.0540   -3.8802 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1923    2.3434   -1.9672 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6365   -5.4617    0.3062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2014   -5.1732    0.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1883   -3.6337    1.0812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3189   -3.9045   -0.3345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5810   -1.6257   -0.1801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8777   -0.2343   -2.3922 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.0754   -0.0350   -0.8382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9206    0.1080    1.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9409    1.5912   -0.0240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3993    2.1421   -1.0573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5163    0.3382    1.9583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2428    1.8892    1.4371 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9288   -2.9013    2.4699 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4399    0.9698    1.3669 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3526   -0.5613    1.4026 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7078    0.6780    2.6405 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 14 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 23 26  2  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  2  0
 27 31  1  0
 31 32  1  0
 31 33  1  6
 31 34  1  0
 20 35  1  0
 35 36  2  0
 35 37  1  0
 37 38  2  0
 38 39  1  0
 39 40  1  0
 38 41  1  0
 41 42  2  0
 16  3  1  0
 26 18  1  0
 15  7  1  0
 41 19  1  0
 34 13  1  0
  1 43  1  0
  1 44  1  0
  1 45  1  0
  4 46  1  0
  9 47  1  0
 12 48  1  0
 12 49  1  0
 12 50  1  0
 22 51  1  0
 25 52  1  0
 25 53  1  0
 25 54  1  0
 27 55  1  1
 29 56  1  0
 29 57  1  0
 29 58  1  0
 32 59  1  0
 32 60  1  0
 32 61  1  0
 33 62  1  0
 34 63  1  0
 34 64  1  0
 37 65  1  0
 40 66  1  0
 40 67  1  0
 40 68  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₃₀H₂₆O₁₂

Average Mass

578.5260 Da

Monoisotopic Mass

578.14243 Da

IUPAC Name

(12S,13R)-12-acetyl-9,13,17-trihydroxy-5,10,16,21-tetramethoxy-13-methylpentacyclo[13.8.0.0^{2,11}.0^{3,8}.0^{18,23}]tricosa-1(23),2,5,8,10,15,17,20-octaene-4,7,19,22-tetrone

Traditional Name

(12S,13R)-12-acetyl-9,13,17-trihydroxy-5,10,16,21-tetramethoxy-13-methylpentacyclo[13.8.0.0^{2,11}.0^{3,8}.0^{18,23}]tricosa-1(23),2,5,8,10,15,17,20-octaene-4,7,19,22-tetrone

CAS Registry Number

Not Available

SMILES

COC1=CC(=O)C2=C(O)C(OC)=C3C[C@@](C)(O)[C@@H](C(C)=O)C4=C(OC)C(O)=C5C(=O)C=C(OC)C(=O)C5=C4C3=C2C1=O

InChI Identifier

InChI=1S/C30H26O12/c1-10(31)23-22-19(21-18(27(37)29(22)42-6)13(33)8-15(40-4)25(21)35)16-11(9-30(23,2)38)28(41-5)26(36)17-12(32)7-14(39-3)24(34)20(16)17/h7-8,23,36-38H,9H2,1-6H3/t23-,30+/m0/s1

InChI Key

UVHNWRDTZAYVST-YUDQIZAISA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Shiraia bambusicola	NPAtlas	16915819

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone).

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Naphthoquinone
Anisole
Aryl ketone
Quinone
Alkyl aryl ether
Vinylogous ester
Vinylogous acid
Tertiary alcohol
Ketone
Ether
Polyol
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	3.04	ALOGPS
logP	1.84	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	7.87	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	182.96 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	150.6 m³·mol⁻¹	ChemAxon
Polarizability	56.01 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA012362

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78441216

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139586535

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Fang LZ, Qing C, Shao HJ, Yang YD, Dong ZJ, Wang F, Zhao W, Yang WQ, Liu JK: Hypocrellin D, a cytotoxic fungal pigment from fruiting bodies of the ascomycete Shiraia bambusicola. J Antibiot (Tokyo). 2006 Jun;59(6):351-4. doi: 10.1038/ja.2006.49. [PubMed:16915819 ]

Showing NP-Card for Hypocrellin D (NP0006518)

MOL for NP0006518 (Hypocrellin D)

3D MOL for NP0006518 (Hypocrellin D)

3D SDF for NP0006518 (Hypocrellin D)

3D-SDF for NP0006518 (Hypocrellin D)

PDB for NP0006518 (Hypocrellin D)

3D PDB for NP0006518 (Hypocrellin D)

SMILES for NP0006518 (Hypocrellin D)

INCHI for NP0006518 (Hypocrellin D)

Structure for NP0006518 (Hypocrellin D)

3D Structure for NP0006518 (Hypocrellin D)