NP-MRD: Showing NP-Card for Ergosterol (NP0002759)

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Record Information

Version

1.0

Created at

2020-11-23 19:39:42 UTC

Updated at

2024-04-19 10:07:05 UTC

NP-MRD ID

NP0002759

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ergosterol

Provided By

BMRB

Description

Ergosterol, also known as provitamin D2 or lumisterol, belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton. Thus, ergosterol is considered to be a sterol. Ergosterol is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Ergosterol is found in Collariella virescens, Agaricus blazei, Alisma plantago-aquatica, Allium obliquum , Alternaria mali, Amelaria mellea, Artemisia deserti, Aspergillus alliaceus, Aspergillus austroafricanus, Aspergillus flavipes, Aspergillus ochraceus, Aspergillus quadrilineatus, Emericella rugulosa, Emericella variecolor, Aspergillus unguis, Axinella cannabina, Beauveria felina, Bombyx mori, Botrytis cinerea, Bulgaria inquinans, Chaetomium elatum, Chlorella vulgaris, Clitocybula oculus, Conium maculatum, Cortinarius humidicola, Cortinarius rubellus, Cortinarius speciosissimus, Cryptoderma citrinum, Cryptoporus volvatus, Cuphea carthagenensis, Cyanidium caldarium, Cynodon dactylon, Dichotomophthora lutea, Debaryomyces hansenii, Dendrodoa grossularia, Diaporthe convolvuli, Dictyonella incisa, Dictyuchus monosporus, Dinemasporium strigosum, Dysidea avara, Aspergillus desertorum, Aspergillus purpureus, Aspergillus striatus, Eutreptia viridis, Eutypa lata, Festuca rubra, Fomitopsis officinalis, Gibberella fujikuroi, Phellinus gilvus , Gladiolus italicus, Gloephyllum sepiarium, Gymnopilus spectabilis, Hebeloma vinosophyllum, Heliopsis helianthoides, Hemispora stellata, Hericium erinaceus, Humulus lupulus, Hypholoma lateritium, Inonotus obliquus, Lactarius deliciosus, Lactarius hatsudake, Lactarius volemus, Lampteromyces japonicus, Leptosphaeria maculans, Lichtheimia corymbifera, Malva parviflora , Spicaria elegans, Microporous flabelliformis, Monascus pilosus, Monteverdia ilicifolia, Morchella esculenta, Mytilus edulis, Lentinus lepideus , Nervilia plicata, Ophiocordyceps sinensis, Ovatospora brasiliensis, Patrinia rupestris, Paxillus involutus, Penicillium notatum, Penicillium oxalicum, Penicillium solitum, Phaeolepiota aurea, Pisolithus arhizus, Pleurotus citrinopileatus, Polyporus tuberaster, Porodaedalea pini, Prototheca wickerhamii, Psilocybe argentipes, Pyrenophora graminea, Ramaria formosa, Rhizopus arrhizus, Rhodotorula glutinis, Rhodotorula mucilaginosa, Rodgersia sambucifolia, Russula subnigricans, Sarcodon scabrosus, Scleroderma aurantium, Smittium sp., Spongiporus leucomallellus (Murril), Chaetomium longicolleum, Stenocarpella macrospora, Sticta caulescens, Strachybotrys atra, Taiwanofungus camphoratus, Talaromyces flavus, Talaromyces verruculosus, Cortinarius vibratilis, Coriolus versicolor , Trichoderma koningii, Trichothecium roseum, Tuber melanosporum, Ustilago maydis , Ustilago nuda, Venturia inaequalis, Veronica officinalis , Veronica orchidea, Veronica teucrium, Vitis vinifera, Withania somnifera, Poria cocos , Xerocomus badius, Xylaria obovata and Zoophagus insidians. It was first documented in 1992 (PMID: 1287164). Based on a literature review a significant number of articles have been published on Ergosterol (PMID: 17984079) (PMID: 15917516) (PMID: 16110826) (PMID: 16110776).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652303062020122D          

 32 35  0  0  0  0            999 V2000
 9999.976210000.8067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8391 9999.5609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.6978 9997.4912    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5515 9998.3265    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9762 9998.3265    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1260 9999.1453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4115 9998.7328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4115 9997.9077    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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 9998.5519 9997.4953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2664 9997.9077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.264410000.3906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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10003.624210001.0580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.337810001.4685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.624210000.2330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.908510002.2935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.049910001.4685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.479210000.6435    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8  3  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
  9 11  1  0  0  0  0
  6 10  1  0  0  0  0
 10  2  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 10  1  0  0  0  0
 16  4  1  6  0  0  0
 13 17  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 22 23  1  0  0  0  0
 22 32  1  6  0  0  0
 23 24  1  0  0  0  0
 23 31  1  6  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 30  1  6  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 22 18  1  0  0  0  0
 22 21  1  0  0  0  0
 17 19  1  0  0  0  0
 19  5  1  6  0  0  0
 14 18  1  0  0  0  0
 18  1  1  1  0  0  0
M  END

NP0002759
     RDKit          3D

 73 76  0  0  0  0  0  0  0  0999 V2000
   -7.1701   -0.5039   -1.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0900   -0.1054   -0.0628 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.3724    0.1817    1.2019 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.9396    1.9011   -1.3852 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5621    2.5205    0.1650 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0372    0.0354    1.6944 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0392    1.8605   -0.5417 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7711    2.2619    1.0997 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
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 10 11  1  0
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 13 14  1  0
 14 15  2  0
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 17 18  1  0
 18 19  1  0
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 21 22  1  0
 22 23  1  0
 23 24  1  6
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  1 30  1  0
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  5 39  1  0
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  8 43  1  6
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 27 70  1  0
 29 71  1  0
 29 72  1  0
 29 73  1  0
M  END


  Mrv1652303062020122D          

 32 35  0  0  0  0            999 V2000
 9999.976210000.8067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8391 9999.5609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 9997.1260 9999.1453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 9996.4115 9997.9077    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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 9999.264410000.3906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5499 9999.9781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5499 9999.1530    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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10004.337810001.4685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.624210000.2330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.908510002.2935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.049910001.4685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.479210000.6435    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8  3  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
  9 11  1  0  0  0  0
  6 10  1  0  0  0  0
 10  2  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 10  1  0  0  0  0
 16  4  1  6  0  0  0
 13 17  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 22 23  1  0  0  0  0
 22 32  1  6  0  0  0
 23 24  1  0  0  0  0
 23 31  1  6  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 30  1  6  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 22 18  1  0  0  0  0
 22 21  1  0  0  0  0
 17 19  1  0  0  0  0
 19  5  1  6  0  0  0
 14 18  1  0  0  0  0
 18  1  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0002759

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)\C=C\[C@H](C)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C28H44O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-10,18-20,22,24-26,29H,11-17H2,1-6H3/b8-7+/t19-,20+,22-,24+,25-,26-,27-,28+/m0/s1

> <INCHI_KEY>
DNVPQKQSNYMLRS-APGDWVJJSA-N

> <FORMULA>
C28H44O

> <MOLECULAR_WEIGHT>
396.659

> <EXACT_MASS>
396.339216037

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
51.061177321579876

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5S,11R,14R,15R)-14-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,9-dien-5-ol

> <ALOGPS_LOGP>
7.39

> <JCHEM_LOGP>
6.632406989000003

> <ALOGPS_LOGS>
-6.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.270805421445605

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3681497086596925

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
127.13169999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.56e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,11R,14R,15R)-14-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,9-dien-5-ol

> <JCHEM_VEBER_RULE>
1

$$$$

NP0002759
     RDKit          3D

 73 76  0  0  0  0  0  0  0  0999 V2000
   -7.1701   -0.5039   -1.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0900   -0.1054   -0.0628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9660    1.3954    0.1238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9003   -0.7648    0.5672 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.0778   -2.2631    0.4437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6389   -0.3055   -0.0814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7020    0.3078    0.6021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4154    0.7946    0.0189 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4233    2.2757    0.0458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3038    0.1115    0.7230 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4977   -1.3961    0.4860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1337   -1.9029   -0.0071 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7622   -0.9206    0.6273 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1303   -0.8650    0.0605 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5275   -1.7562   -0.8542 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -1.5934   -1.3259 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7283   -0.6674   -0.9302 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1251   -0.6402   -1.5233 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1510   -0.4802   -0.4495 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.3676   -0.0676   -1.0232 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7653    0.3684    0.7063 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3724    0.1817    1.2019 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3458    0.3369    0.0705 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6495    1.6950   -0.5580 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9844    0.2216    0.5736 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2040    1.5280    0.4808 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8600    1.3664    1.1446 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0709    0.3922    0.2958 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2561    0.6272   -1.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2668   -1.0104   -1.8866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3563    0.3671   -2.1902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0287   -1.2261   -1.6000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9885   -0.4338    0.5105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5545    1.8734   -0.7854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9739    1.8116    0.2982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3237    1.6481    1.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8734   -0.4613    1.6284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1254   -2.7721    0.1823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4607   -2.6289    1.4220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8897   -2.5116   -0.2933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4474   -0.4617   -1.1470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9040    0.4610    1.6765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4477    0.4824   -1.0595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1479    2.7335    1.0020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4875    2.6102   -0.1458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8562    2.6975   -0.8174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3859    0.2602    1.8201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7260   -1.9301    1.4056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1983   -1.5885   -0.3403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1027   -1.9192   -1.1121 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0487   -2.9127    0.4197 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7910   -1.0955    1.7142 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8442   -2.5230   -1.1857 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2772   -2.3069   -2.0878 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1438    0.2244   -2.2101 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2793   -1.5378   -2.1469 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3684   -1.5184   -0.0589 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6792   -0.8214   -1.6019 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0295    1.4227    0.4795 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4380    0.1048    1.5704 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1877    0.8929    2.0177 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2745   -0.8649    1.5565 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6686    1.7540   -0.9818 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9396    1.9011   -1.3852 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5621    2.5205    0.1650 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0372    0.0354    1.6944 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0392    1.8605   -0.5417 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7711    2.2619    1.0997 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9387    0.9397    2.1618 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3803    2.3491    1.2413 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2248    1.6928   -1.4657 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2460    0.2453   -1.5005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4980    0.0044   -1.7041 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  6
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  6
 28 10  1  0
 28 13  1  0
 25 14  1  0
 23 17  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  3 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  1
  5 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  0
  7 42  1  0
  8 43  1  6
  9 44  1  0
  9 45  1  0
  9 46  1  0
 10 47  1  1
 11 48  1  0
 11 49  1  0
 12 50  1  0
 12 51  1  0
 13 52  1  1
 15 53  1  0
 16 54  1  0
 18 55  1  0
 18 56  1  0
 19 57  1  1
 20 58  1  0
 21 59  1  0
 21 60  1  0
 22 61  1  0
 22 62  1  0
 24 63  1  0
 24 64  1  0
 24 65  1  0
 25 66  1  1
 26 67  1  0
 26 68  1  0
 27 69  1  0
 27 70  1  0
 29 71  1  0
 29 72  1  0
 29 73  1  0
M  END

HEADER    PROTEIN                                 06-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAR-20         0                                  
HETATM    1  C   UNK     0    8666.6228668.173   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8662.6338665.847   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8658.6368661.984   0.000  0.00  0.00           O+0
HETATM    4  H   UNK     0    8663.9638663.543   0.000  0.00  0.00           H+0
HETATM    5  H   UNK     0    8666.6228663.543   0.000  0.00  0.00           H+0
HETATM    6  C   UNK     0    8661.3028665.071   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8659.9688664.301   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8659.9688662.761   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8661.3028661.991   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8662.6308664.301   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8662.6308662.761   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8663.9648661.991   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8665.2978662.761   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8665.2948667.396   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8663.9608666.626   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8663.9608665.086   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8665.2948664.316   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8666.6278666.626   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8666.6278665.086   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8668.0928664.610   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8668.9978665.856   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8668.0928667.102   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8668.0928668.642   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8669.4288669.408   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8670.7608668.642   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8672.0968669.408   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8673.4328668.642   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8674.7648669.408   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8673.4328667.102   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0    8672.0968670.948   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0    8666.7608669.408   0.000  0.00  0.00           C+0
HETATM   32  H   UNK     0    8669.4288667.868   0.000  0.00  0.00           H+0
CONECT    1   18                                                            
CONECT    2   10                                                            
CONECT    3    8                                                            
CONECT    4   16                                                            
CONECT    5   19                                                            
CONECT    6    7   10                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9    3                                                  
CONECT    9    8   11                                                       
CONECT   10   11    6    2   16                                             
CONECT   11   10   12    9                                                  
CONECT   12   11   13                                                       
CONECT   13   12   17                                                       
CONECT   14   15   18                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   10    4                                             
CONECT   17   16   13   19                                                  
CONECT   18   19   22   14    1                                             
CONECT   19   18   20   17    5                                             
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   23   32   18   21                                             
CONECT   23   22   24   31                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   30                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   26                                                            
CONECT   31   23                                                            
CONECT   32   22                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

COMPND    NP0002759
HETATM    1  C1  UNL     1      -7.170  -0.504  -1.508  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.090  -0.105  -0.063  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.966   1.395   0.124  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.900  -0.765   0.567  1.00  0.00           C  
HETATM    5  C5  UNL     1      -6.078  -2.263   0.444  1.00  0.00           C  
HETATM    6  C6  UNL     1      -4.639  -0.306  -0.081  1.00  0.00           C  
HETATM    7  C7  UNL     1      -3.702   0.308   0.602  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.415   0.795   0.019  1.00  0.00           C  
HETATM    9  C9  UNL     1      -2.423   2.276   0.046  1.00  0.00           C  
HETATM   10  C10 UNL     1      -1.304   0.112   0.723  1.00  0.00           C  
HETATM   11  C11 UNL     1      -1.498  -1.396   0.486  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.134  -1.903  -0.007  1.00  0.00           C  
HETATM   13  C13 UNL     1       0.762  -0.921   0.627  1.00  0.00           C  
HETATM   14  C14 UNL     1       2.130  -0.865   0.060  1.00  0.00           C  
HETATM   15  C15 UNL     1       2.528  -1.756  -0.854  1.00  0.00           C  
HETATM   16  C16 UNL     1       3.893  -1.593  -1.326  1.00  0.00           C  
HETATM   17  C17 UNL     1       4.728  -0.667  -0.930  1.00  0.00           C  
HETATM   18  C18 UNL     1       6.125  -0.640  -1.523  1.00  0.00           C  
HETATM   19  C19 UNL     1       7.151  -0.480  -0.449  1.00  0.00           C  
HETATM   20  O1  UNL     1       8.368  -0.068  -1.023  1.00  0.00           O  
HETATM   21  C20 UNL     1       6.765   0.368   0.706  1.00  0.00           C  
HETATM   22  C21 UNL     1       5.372   0.182   1.202  1.00  0.00           C  
HETATM   23  C22 UNL     1       4.346   0.337   0.071  1.00  0.00           C  
HETATM   24  C23 UNL     1       4.649   1.695  -0.558  1.00  0.00           C  
HETATM   25  C24 UNL     1       2.984   0.222   0.574  1.00  0.00           C  
HETATM   26  C25 UNL     1       2.204   1.528   0.481  1.00  0.00           C  
HETATM   27  C26 UNL     1       0.860   1.366   1.145  1.00  0.00           C  
HETATM   28  C27 UNL     1       0.071   0.392   0.296  1.00  0.00           C  
HETATM   29  C28 UNL     1       0.256   0.627  -1.174  1.00  0.00           C  
HETATM   30  H1  UNL     1      -6.267  -1.010  -1.887  1.00  0.00           H  
HETATM   31  H2  UNL     1      -7.356   0.367  -2.190  1.00  0.00           H  
HETATM   32  H3  UNL     1      -8.029  -1.226  -1.600  1.00  0.00           H  
HETATM   33  H4  UNL     1      -7.988  -0.434   0.511  1.00  0.00           H  
HETATM   34  H5  UNL     1      -6.554   1.873  -0.785  1.00  0.00           H  
HETATM   35  H6  UNL     1      -7.974   1.812   0.298  1.00  0.00           H  
HETATM   36  H7  UNL     1      -6.324   1.648   1.012  1.00  0.00           H  
HETATM   37  H8  UNL     1      -5.873  -0.461   1.628  1.00  0.00           H  
HETATM   38  H9  UNL     1      -5.125  -2.772   0.182  1.00  0.00           H  
HETATM   39  H10 UNL     1      -6.461  -2.629   1.422  1.00  0.00           H  
HETATM   40  H11 UNL     1      -6.890  -2.512  -0.293  1.00  0.00           H  
HETATM   41  H12 UNL     1      -4.447  -0.462  -1.147  1.00  0.00           H  
HETATM   42  H13 UNL     1      -3.904   0.461   1.677  1.00  0.00           H  
HETATM   43  H14 UNL     1      -2.448   0.482  -1.060  1.00  0.00           H  
HETATM   44  H15 UNL     1      -2.148   2.733   1.002  1.00  0.00           H  
HETATM   45  H16 UNL     1      -3.487   2.610  -0.146  1.00  0.00           H  
HETATM   46  H17 UNL     1      -1.856   2.698  -0.817  1.00  0.00           H  
HETATM   47  H18 UNL     1      -1.386   0.260   1.820  1.00  0.00           H  
HETATM   48  H19 UNL     1      -1.726  -1.930   1.406  1.00  0.00           H  
HETATM   49  H20 UNL     1      -2.198  -1.589  -0.340  1.00  0.00           H  
HETATM   50  H21 UNL     1      -0.103  -1.919  -1.112  1.00  0.00           H  
HETATM   51  H22 UNL     1       0.049  -2.913   0.420  1.00  0.00           H  
HETATM   52  H23 UNL     1       0.791  -1.095   1.714  1.00  0.00           H  
HETATM   53  H24 UNL     1       1.844  -2.523  -1.186  1.00  0.00           H  
HETATM   54  H25 UNL     1       4.277  -2.307  -2.088  1.00  0.00           H  
HETATM   55  H26 UNL     1       6.144   0.224  -2.210  1.00  0.00           H  
HETATM   56  H27 UNL     1       6.279  -1.538  -2.147  1.00  0.00           H  
HETATM   57  H28 UNL     1       7.368  -1.518  -0.059  1.00  0.00           H  
HETATM   58  H29 UNL     1       8.679  -0.821  -1.602  1.00  0.00           H  
HETATM   59  H30 UNL     1       7.029   1.423   0.480  1.00  0.00           H  
HETATM   60  H31 UNL     1       7.438   0.105   1.570  1.00  0.00           H  
HETATM   61  H32 UNL     1       5.188   0.893   2.018  1.00  0.00           H  
HETATM   62  H33 UNL     1       5.274  -0.865   1.557  1.00  0.00           H  
HETATM   63  H34 UNL     1       5.669   1.754  -0.982  1.00  0.00           H  
HETATM   64  H35 UNL     1       3.940   1.901  -1.385  1.00  0.00           H  
HETATM   65  H36 UNL     1       4.562   2.521   0.165  1.00  0.00           H  
HETATM   66  H37 UNL     1       3.037   0.035   1.694  1.00  0.00           H  
HETATM   67  H38 UNL     1       2.039   1.861  -0.542  1.00  0.00           H  
HETATM   68  H39 UNL     1       2.771   2.262   1.100  1.00  0.00           H  
HETATM   69  H40 UNL     1       0.939   0.940   2.162  1.00  0.00           H  
HETATM   70  H41 UNL     1       0.380   2.349   1.241  1.00  0.00           H  
HETATM   71  H42 UNL     1       0.225   1.693  -1.466  1.00  0.00           H  
HETATM   72  H43 UNL     1       1.246   0.245  -1.501  1.00  0.00           H  
HETATM   73  H44 UNL     1      -0.498   0.004  -1.704  1.00  0.00           H  
CONECT    1    2   30   31   32
CONECT    2    3    4   33
CONECT    3   34   35   36
CONECT    4    5    6   37
CONECT    5   38   39   40
CONECT    6    7    7   41
CONECT    7    8   42
CONECT    8    9   10   43
CONECT    9   44   45   46
CONECT   10   11   28   47
CONECT   11   12   48   49
CONECT   12   13   50   51
CONECT   13   14   28   52
CONECT   14   15   15   25
CONECT   15   16   53
CONECT   16   17   17   54
CONECT   17   18   23
CONECT   18   19   55   56
CONECT   19   20   21   57
CONECT   20   58
CONECT   21   22   59   60
CONECT   22   23   61   62
CONECT   23   24   25
CONECT   24   63   64   65
CONECT   25   26   66
CONECT   26   27   67   68
CONECT   27   28   69   70
CONECT   28   29
CONECT   29   71   72   73
END

NP0002759
     RDKit          3D

73 76  0  0  0  0  0  0  0  0999 V2000
   -7.1701   -0.5039   -1.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0900   -0.1054   -0.0628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9660    1.3954    0.1238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9003   -0.7648    0.5672 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.0778   -2.2631    0.4437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6389   -0.3055   -0.0814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7020    0.3078    0.6021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4154    0.7946    0.0189 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4233    2.2757    0.0458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3038    0.1115    0.7230 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4977   -1.3961    0.4860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1337   -1.9029   -0.0071 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7622   -0.9206    0.6273 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1303   -0.8650    0.0605 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5275   -1.7562   -0.8542 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -1.5934   -1.3259 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7283   -0.6674   -0.9302 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1251   -0.6402   -1.5233 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1510   -0.4802   -0.4495 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.3676   -0.0676   -1.0232 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7653    0.3684    0.7063 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3724    0.1817    1.2019 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3458    0.3369    0.0705 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6495    1.6950   -0.5580 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9844    0.2216    0.5736 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2040    1.5280    0.4808 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8600    1.3664    1.1446 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0709    0.3922    0.2958 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2561    0.6272   -1.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2668   -1.0104   -1.8866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3563    0.3671   -2.1902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0287   -1.2261   -1.6000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9885   -0.4338    0.5105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5545    1.8734   -0.7854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9739    1.8116    0.2982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3237    1.6481    1.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8734   -0.4613    1.6284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1254   -2.7721    0.1823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4607   -2.6289    1.4220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8897   -2.5116   -0.2933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4474   -0.4617   -1.1470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9040    0.4610    1.6765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4477    0.4824   -1.0595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1479    2.7335    1.0020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4875    2.6102   -0.1458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8562    2.6975   -0.8174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3859    0.2602    1.8201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7260   -1.9301    1.4056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1983   -1.5885   -0.3403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1027   -1.9192   -1.1121 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0487   -2.9127    0.4197 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7910   -1.0955    1.7142 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8442   -2.5230   -1.1857 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2772   -2.3069   -2.0878 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1438    0.2244   -2.2101 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2793   -1.5378   -2.1469 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3684   -1.5184   -0.0589 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6792   -0.8214   -1.6019 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0295    1.4227    0.4795 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4380    0.1048    1.5704 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1877    0.8929    2.0177 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2745   -0.8649    1.5565 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6686    1.7540   -0.9818 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9396    1.9011   -1.3852 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5621    2.5205    0.1650 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0372    0.0354    1.6944 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0392    1.8605   -0.5417 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7711    2.2619    1.0997 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9387    0.9397    2.1618 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3803    2.3491    1.2413 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2248    1.6928   -1.4657 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2460    0.2453   -1.5005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4980    0.0044   -1.7041 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  6
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  6
 28 10  1  0
 28 13  1  0
 25 14  1  0
 23 17  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  3 34  1  0
  3 35  1  0
  3 36  1  0
  4 37  1  1
  5 38  1  0
  5 39  1  0
  5 40  1  0
  6 41  1  0
  7 42  1  0
  8 43  1  6
  9 44  1  0
  9 45  1  0
  9 46  1  0
 10 47  1  1
 11 48  1  0
 11 49  1  0
 12 50  1  0
 12 51  1  0
 13 52  1  1
 15 53  1  0
 16 54  1  0
 18 55  1  0
 18 56  1  0
 19 57  1  1
 20 58  1  0
 21 59  1  0
 21 60  1  0
 22 61  1  0
 22 62  1  0
 24 63  1  0
 24 64  1  0
 24 65  1  0
 25 66  1  1
 26 67  1  0
 26 68  1  0
 27 69  1  0
 27 70  1  0
 29 71  1  0
 29 72  1  0
 29 73  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(22E,24S)-24-Methylcholesta-5,7,22-trien-3beta-ol	ChEBI
Provitamin D2	ChEBI
(22E,24S)-24-Methylcholesta-5,7,22-trien-3b-ol	Generator
(22E,24S)-24-Methylcholesta-5,7,22-trien-3β-ol	Generator
Lumisterol	HMDB
Provitamin D 2	HMDB
D2, Pro-vitamin	HMDB
Pro vitamin D2	HMDB
Pro-vitamin D2	HMDB
(22E,24R)-Ergosta-5,7,22-trien-3beta-ol	HMDB
(22E,24R)-Ergosta-5,7,22-trien-3β-ol	HMDB
(24R)-Ergosta-5,7,22-trien-3beta-ol	HMDB
(24R)-Ergosta-5,7,22-trien-3β-ol	HMDB
(3beta,22E)-Ergosta-5,7,22-trien-3-ol	HMDB
(3Β,22E)-ergosta-5,7,22-trien-3-ol	HMDB
24-Methylcholesta-5,7,22-trien-3beta-ol	HMDB
24-Methylcholesta-5,7,22-trien-3β-ol	HMDB
24R-Methylcholesta-5,7,22E-trien-3beta-ol	HMDB
24R-Methylcholesta-5,7,22E-trien-3β-ol	HMDB
24alpha-Methyl-22E-dehydrocholesterol	HMDB
24Α-methyl-22E-dehydrocholesterol	HMDB
3beta-Hydroxyergosta-5,7,22-triene	HMDB
3Β-hydroxyergosta-5,7,22-triene	HMDB
Ergosterin	HMDB
Provitamin D	HMDB
Ergosterol	HMDB

Chemical Formula

C₂₈H₄₄O

Average Mass

396.6590 Da

Monoisotopic Mass

396.33922 Da

IUPAC Name

(1S,2R,5S,11R,14R,15R)-14-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,9-dien-5-ol

Traditional Name

(1S,2R,5S,11R,14R,15R)-14-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,9-dien-5-ol

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)\C=C\[C@H](C)C(C)C

InChI Identifier

InChI=1S/C28H44O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-10,18-20,22,24-26,29H,11-17H2,1-6H3/b8-7+/t19-,20+,22-,24+,25-,26-,27-,28+/m0/s1

InChI Key

DNVPQKQSNYMLRS-APGDWVJJSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-26	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-26	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-26	View Spectrum
1D NMR	[¹³C, ] NMR Spectrum (2D, 201 MHz, CDCl3, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-26	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-26	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600.133705802 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201.216488466 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

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	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, 252 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, 50 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	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, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 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
Achaetomiella virescens	LOTUS Database	35616633
Agaricus bisporus	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Agaricus blazei	LOTUS Database	35616633
Alisma plantago-aquatica	LOTUS Database	35616633
Allium obliquum	Plant	KNApSAcK
Allium sativum	KNApSAcK Database	22123792
Alternaria mali	LOTUS Database	35616633
Amelaria mellea	-	KNApSAcK
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anethum graveolens	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Anser anser	FooDB	FooDB
Artemisia deserti	LOTUS Database	35616633
Aspergillus alliaceus	LOTUS Database	35616633
Aspergillus austroafricanus	LOTUS Database	35616633
Aspergillus flavipes	LOTUS Database	35616633
Aspergillus ochraceus	LOTUS Database	35616633
Aspergillus quadrilineatus	LOTUS Database	35616633
Aspergillus rugulosus	-	KNApSAcK
Aspergillus stellatus	-	KNApSAcK
Aspergillus unguis	LOTUS Database	35616633
Axinella cannabina	LOTUS Database	35616633
Beauveria felina	LOTUS Database	35616633
Bison bison	FooDB	FooDB
Bombyx mori	LOTUS Database	35616633
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Botrytis cinerea	LOTUS Database	35616633
Bubalus bubalis	FooDB	FooDB
Bulgaria inquinans	LOTUS Database	35616633
Cannabis sativa	CannabisDB	Not Available
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Chaetomium elatum	LOTUS Database	35616633
Chlorella vulgaris	LOTUS Database	35616633
Clitocybula oculus	LOTUS Database	35616633
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Conium maculatum	LOTUS Database	35616633
Cortinarius humidicola	LOTUS Database	35616633
Cortinarius rubellus	LOTUS Database	35616633
Cortinarius speciosissimus	LOTUS Database	35616633
Cryptoderma citrinum	-	KNApSAcK
Cryptoporus volvatus	LOTUS Database	35616633
Cuphea carthagenensis	LOTUS Database	35616633
Cyanidium caldarium	LOTUS Database	35616633
Cynodon dactylon	LOTUS Database	35616633
Dactylaria lutea	LOTUS Database	35616633
Debaryomyces hansenii	LOTUS Database	35616633
Dendrodoa grossularia	LOTUS Database	35616633
Diaporthe convolvuli	LOTUS Database	35616633
Dictyonella incisa	LOTUS Database	35616633
Dictyuchus monosporus	-	KNApSAcK
Dinemasporium strigosum	LOTUS Database	35616633
Dromaius novaehollandiae	FooDB	FooDB
Dysidea avara	LOTUS Database	35616633
Elettaria cardamomum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Emericella desertorum	LOTUS Database	35616633
Emericella purpurea	LOTUS Database	35616633
Emericella striata	LOTUS Database	35616633
Equus caballus	FooDB	FooDB
Eutreptia viridis	LOTUS Database	35616633
Eutypa lata	LOTUS Database	35616633
Festuca rubra	LOTUS Database	35616633
Fomitopsis officinalis	LOTUS Database	35616633
Fusarium fujikuroi	Fungi	KNApSAcK
Fuscoporia gilva	Fungi	KNApSAcK
Gallus gallus	FooDB	FooDB
Ginkgo biloba	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Gladiolus italicus	LOTUS Database	35616633
Gloephyllum sepiarium	-	KNApSAcK
Glycine max	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Gossypium	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Gymnopilus spectabilis	LOTUS Database	35616633
Hebeloma vinosophyllum	LOTUS Database	35616633
Heliopsis helianthoides	LOTUS Database	35616633
Hemispora stellata	-	KNApSAcK
Hericium erinaceus	LOTUS Database	35616633
Hibiscus sabbariffa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Hibiscus sabdariffa L.	KNApSAcK Database	22123792
Humulus lupulus	LOTUS Database	35616633
Hypholoma lateritium	LOTUS Database	35616633
Inonotus obliquus	LOTUS Database	35616633
Lactarius deliciosus	LOTUS Database	35616633
Lactarius hatsudake	LOTUS Database	35616633
Lactarius volemus	LOTUS Database	35616633
Lactuca sativa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Lagopus muta	FooDB	FooDB
Lampteromyces japonicus	-	KNApSAcK
Leporidae	FooDB	FooDB
Leptosphaeria maculans	LOTUS Database	35616633
Lepus timidus	FooDB	FooDB
Lichtheimia corymbifera	LOTUS Database	35616633
Malva parviflora	Plant	KNApSAcK
Mariannaea elegans	-	KNApSAcK
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Microporous flabelliformis	-	KNApSAcK
Monascus pilosus	LOTUS Database	35616633
Monteverdia ilicifolia	LOTUS Database	35616633
Morchella esculenta	LOTUS Database	35616633
Mytilus edulis	LOTUS Database	35616633
Neolentinus lepideus	Fungi	KNApSAcK
Nervilia plicata	LOTUS Database	35616633
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Ophiocordyceps sinensis	LOTUS Database	35616633
Oryctolagus	FooDB	FooDB
Oryza sativa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Ovatospora brasiliensis	LOTUS Database	35616633
Ovis aries	FooDB	FooDB
Patrinia rupestris	LOTUS Database	35616633
Paxillus involutus	LOTUS Database	35616633
Penicillium chrysogenum	Fungi	KNApSAcK
Penicillium oxalicum	LOTUS Database	35616633
Penicillium solitum	LOTUS Database	35616633
Phaeolepiota aurea	LOTUS Database	35616633
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Phoenix dactylifera	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Pisolithus arhizus	LOTUS Database	35616633
Pleurotus citrinopileatus	LOTUS Database	35616633
Pleurotus ostreatus	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Polyporus tuberaster	LOTUS Database	35616633
Polytrichum commune	KNApSAcK Database	22123792
Porodaedalea pini	LOTUS Database	35616633
Prototheca wickerhamii	LOTUS Database	35616633
Psilocybe argentipes	LOTUS Database	35616633
Pyrenophora graminea	LOTUS Database	35616633
Ramaria formosa	LOTUS Database	35616633
Rhizopus oryzae	Fungi	KNApSAcK
Rhodotorula glutinis	LOTUS Database	35616633
Rhodotorula mucilaginosa	LOTUS Database	35616633
Rodgersia sambucifolia	LOTUS Database	35616633
Russula subnigricans	LOTUS Database	35616633
Sarcodon scabrosus	LOTUS Database	35616633
Scleroderma aurantium	-	KNApSAcK
Smittium sp.	-	KNApSAcK
Spongiporus leucomallellus (Murril)	-	KNApSAcK
Staphylotrichum longicolle	LOTUS Database	35616633
Stenocarpella macrospora	LOTUS Database	35616633
Sticta caulescens	LOTUS Database	35616633
Strachybotrys atra	-	KNApSAcK
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB
Taiwanofungus camphoratus	LOTUS Database	35616633
Talaromyces flavus	LOTUS Database	35616633
Talaromyces verruculosus	LOTUS Database	35616633
Thaxterogaster vibratilis	LOTUS Database	35616633
Theobroma cacao	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Trametes Versicolor	Fungi	KNApSAcK
Trichoderma koningii	Fungi	KNApSAcK
Trichothecium roseum	LOTUS Database	35616633
Triticum aestivum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Tuber melanosporum	LOTUS Database	35616633
Ustilago maydis	-	KNApSAcK
Ustilago nuda	-	KNApSAcK
Venturia inaequalis	LOTUS Database	35616633
Veronica officinalis	Plant	KNApSAcK
Veronica orchidea	Plant	KNApSAcK
Veronica teucrium	Plant	KNApSAcK
Vitis vinifera	LOTUS Database	35616633
Vitis vinifera L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Withania somnifera	LOTUS Database	35616633
Wolfiporia cocos	-	KNApSAcK
Xerocomus badius	LOTUS Database	35616633
Xylaria obovata	LOTUS Database	35616633
Zea mays L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Zoophagus insidians	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Agaricus campestris	KNApSAcK Database	22123792
Alternaria alternata	KNApSAcK Database	22123792
Alternaria brassicicola	KNApSAcK Database	22123792
Alternaria kikuchiana	KNApSAcK Database	22123792
Alternaria tenuis	KNApSAcK Database	22123792
Amanita caesarea	KNApSAcK Database	22123792
Amoebidium parasiticum	KNApSAcK Database	22123792
Aspergillus niger	KNApSAcK Database	22123792
Aspergillus oryzae IFO 4290	KNApSAcK Database	22123792
Boletus luridus	KNApSAcK Database	22123792
Boletus spp.	KNApSAcK Database	22123792
Candida albicans	KNApSAcK Database	22123792
Candida gulliermondii	KNApSAcK Database	22123792
Candida sp.	KNApSAcK Database	22123792
Candida tropicalis	KNApSAcK Database	22123792
Candida utilis	KNApSAcK Database	22123792
Cantharellus cibarius	KNApSAcK Database	22123792
Cladosporium sp.	KNApSAcK Database	22123792
Coprinus atramentarius	KNApSAcK Database	22123792
Coriolus pargamenus	KNApSAcK Database	22123792
Coriolus sangamenus	KNApSAcK Database	22123792
Coriolus versicolor	KNApSAcK Database	22123792
Cyathus helenae	KNApSAcK Database	22123792
Flammulina velutipes	KNApSAcK Database	22123792
Fomes allardii	KNApSAcK Database	22123792
Fomes annosus	KNApSAcK Database	22123792
Fomitopsis cytisina	KNApSAcK Database	22123792
Fomitopsis pinicola	KNApSAcK Database	22123792
Fomitopsis pubertatis	KNApSAcK Database	22123792
Fusarium sporotrichioides	KNApSAcK Database	22123792
Ganoderma applanatum	KNApSAcK Database	22123792
Ganoderma australe	KNApSAcK Database	22123792
Ganoderma colossum (FR.) C.F.BAKER	KNApSAcK Database	22123792
Ganoderma liplanatum	KNApSAcK Database	22123792
Ganoderma lipsiense	KNApSAcK Database	22123792
Ganoderma lucidum	KNApSAcK Database	22123792
Geotrichum flavo-brunneum	KNApSAcK Database	22123792
Gibberella fujikuroi	KNApSAcK Database	22123792
Glomus mosseae	KNApSAcK Database	22123792
Gnomonia leptostyla	KNApSAcK Database	22123792
Grifola frondosa	KNApSAcK Database	22123792
Grifola umbellata	KNApSAcK Database	22123792
Hygrocybe punicea	KNApSAcK Database	22123792
Inocybe macrosperma	KNApSAcK Database	22123792
Leccinum aurantiacum	KNApSAcK Database	22123792
Leccinum spp.	KNApSAcK Database	22123792
Lentinus edodes	KNApSAcK Database	22123792
Lentinus lepideus	KNApSAcK Database	22123792
Lenzites trabea	KNApSAcK Database	22123792
Leptosphaeria typhae	KNApSAcK Database	22123792
Leucopaxillus giganteus	KNApSAcK Database	22123792
Lobaria pulmonaria	KNApSAcK Database	22123792
Lobaria scobiculata	KNApSAcK Database	22123792
Monascus pilosus BCRC38072	KNApSAcK Database	22123792
Monilinia fructigena	KNApSAcK Database	22123792
Mucor pusillus	KNApSAcK Database	22123792
Nectria galligena	KNApSAcK Database	22123792
Neurospora crassa	KNApSAcK Database	22123792
Panellus serotinus (PERS.:FR.) KUHN.	KNApSAcK Database	22123792
Parmelia caperata	KNApSAcK Database	22123792
Phellinus gilvus	KNApSAcK Database	22123792
Phellinus igniarius	KNApSAcK Database	22123792
Phellinus robustus	KNApSAcK Database	22123792
Pholiota aegerita	KNApSAcK Database	22123792
Phycomyces blakesleeanus	KNApSAcK Database	22123792
Pichia sp.	KNApSAcK Database	22123792
Pleurocybella porrigens	KNApSAcK Database	22123792
Polyporus cretaceous	KNApSAcK Database	22123792
Polyporus dryadeus	KNApSAcK Database	22123792
Polyporus versicolor	KNApSAcK Database	22123792
Rhizopus arrhizus	KNApSAcK Database	22123792
Russula foetens	KNApSAcK Database	22123792
Russula nigricans	KNApSAcK Database	22123792
Russula senecis	KNApSAcK Database	22123792
Saccharomyces cerevisiae	KNApSAcK Database	22123792
Sclerotinia fructicola	KNApSAcK Database	22123792
Suillus bovinus	KNApSAcK Database	22123792
Suillus variegatus	KNApSAcK Database	22123792
Torulopsis glabrata	KNApSAcK Database	22123792
Trametes feei	KNApSAcK Database	22123792
Trametes lilacino-gilva	KNApSAcK Database	22123792
Usnea longissima	KNApSAcK Database	22123792
Xanthoria parietina	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Ergostane steroids

Direct Parent

Ergosterols and derivatives

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	170.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	501.50 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	0.00028 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	9.300 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
logP	7.39	ALOGPS
logP	6.63	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Acidic)	18.27	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	127.13 m³·mol⁻¹	ChemAxon
Polarizability	51.06 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000878

DrugBank ID

DB04038

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00023755

Chemspider ID

392539

KEGG Compound ID

C01694

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ergosterol

METLIN ID

Not Available

PubChem Compound

444679

PDB ID

Not Available

ChEBI ID

16933

Good Scents ID

rw1242781

References

General References

Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
Liu TT, Lee RE, Barker KS, Lee RE, Wei L, Homayouni R, Rogers PD: Genome-wide expression profiling of the response to azole, polyene, echinocandin, and pyrimidine antifungal agents in Candida albicans. Antimicrob Agents Chemother. 2005 Jun;49(6):2226-36. doi: 10.1128/AAC.49.6.2226-2236.2005. [PubMed:15917516 ]
Ferreira ME, Colombo AL, Paulsen I, Ren Q, Wortman J, Huang J, Goldman MH, Goldman GH: The ergosterol biosynthesis pathway, transporter genes, and azole resistance in Aspergillus fumigatus. Med Mycol. 2005 May;43 Suppl 1:S313-9. doi: 10.1080/13693780400029114. [PubMed:16110826 ]
Ryder NS, Frank I: Interaction of terbinafine with human serum and serum proteins. J Med Vet Mycol. 1992;30(6):451-60. doi: 10.1080/02681219280000611. [PubMed:1287164 ]
Akins RA: An update on antifungal targets and mechanisms of resistance in Candida albicans. Med Mycol. 2005 Jun;43(4):285-318. doi: 10.1080/13693780500138971. [PubMed:16110776 ]

Showing NP-Card for Ergosterol (NP0002759)

MOL for NP0002759 (Ergosterol)

3D MOL for NP0002759 (Ergosterol)

3D SDF for NP0002759 (Ergosterol)

3D-SDF for NP0002759 (Ergosterol)

PDB for NP0002759 (Ergosterol)

3D PDB for NP0002759 (Ergosterol)

SMILES for NP0002759 (Ergosterol)

INCHI for NP0002759 (Ergosterol)

Structure for NP0002759 (Ergosterol)

3D Structure for NP0002759 (Ergosterol)