Structure

Physi-Chem Properties

Molecular Weight:  254.09
Volume:  273.458
LogP:  3.693
LogD:  3.013
LogS:  -3.507
# Rotatable Bonds:  4
TPSA:  57.53
# H-Bond Aceptor:  3
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.65
Synthetic Accessibility Score:  2.382
Fsp3:  0.062
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.655
MDCK Permeability:  1.5211341633403208e-05
Pgp-inhibitor:  0.007
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.008
20% Bioavailability (F20%):  0.934
30% Bioavailability (F30%):  0.926

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.144
Plasma Protein Binding (PPB):  99.57957458496094%
Volume Distribution (VD):  0.528
Pgp-substrate:  0.7547723054885864%

ADMET: Metabolism

CYP1A2-inhibitor:  0.953
CYP1A2-substrate:  0.101
CYP2C19-inhibitor:  0.655
CYP2C19-substrate:  0.056
CYP2C9-inhibitor:  0.466
CYP2C9-substrate:  0.74
CYP2D6-inhibitor:  0.774
CYP2D6-substrate:  0.856
CYP3A4-inhibitor:  0.663
CYP3A4-substrate:  0.214

ADMET: Excretion

Clearance (CL):  6.697
Half-life (T1/2):  0.772

ADMET: Toxicity

hERG Blockers:  0.013
Human Hepatotoxicity (H-HT):  0.036
Drug-inuced Liver Injury (DILI):  0.169
AMES Toxicity:  0.246
Rat Oral Acute Toxicity:  0.04
Maximum Recommended Daily Dose:  0.308
Skin Sensitization:  0.868
Carcinogencity:  0.539
Eye Corrosion:  0.104
Eye Irritation:  0.957
Respiratory Toxicity:  0.676

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
Source Organisms  
Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC216216

Natural Product ID:  NPC216216
Common Name*:   Magnaledehyde E
IUPAC Name:   4-hydroxy-3-(4-hydroxy-3-prop-2-enylphenyl)benzaldehyde
Synonyms:   Magnaledehyde E
Standard InCHIKey:  GTEXHGPQCNGASJ-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C16H14O3/c1-2-3-13-9-12(5-7-15(13)18)14-8-11(10-17)4-6-16(14)19/h2,4-10,18-19H,1,3H2
SMILES:  C=CCc1cc(ccc1O)c1cc(ccc1O)C=O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL251060
PubChem CID:   5319190
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002279] Benzene and substituted derivatives
        • [CHEMONTID:0000041] Biphenyls and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO15299 Sandoricum koetjape Species Meliaceae Eukaryota n.a. n.a. n.a. PMID[10479314]
NPO12483 Holarrhena floribunda Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[10650079]
NPO15299 Sandoricum koetjape Species Meliaceae Eukaryota stems n.a. n.a. PMID[1517737]
NPO13353 Sedum sarmentosum Species Crassulaceae Eukaryota n.a. aerial part n.a. PMID[15577228]
NPO13465 Salvia broussonetii Species Lamiaceae Eukaryota roots n.a. n.a. PMID[15969497]
NPO12483 Holarrhena floribunda Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[16441070]
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota n.a. n.a. n.a. PMID[1659613]
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota stem bark n.a. n.a. PMID[17918910]
NPO11791 Magnolia obovata Species Magnoliaceae Eukaryota n.a. stem n.a. PMID[18175990]
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota Stems; Barks n.a. n.a. PMID[19086868]
NPO12483 Holarrhena floribunda Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[19299148]
NPO11791 Magnolia obovata Species Magnoliaceae Eukaryota n.a. n.a. n.a. PMID[21625478]
NPO13353 Sedum sarmentosum Species Crassulaceae Eukaryota n.a. n.a. n.a. PMID[22085682]
NPO15299 Sandoricum koetjape Species Meliaceae Eukaryota n.a. n.a. n.a. PMID[22672802]
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota n.a. bark n.a. PMID[23823874]
NPO13745 Gynoxys verrucosa Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[27057812]
NPO15190 Chloranthus fortunei Species Chloranthaceae Eukaryota n.a. n.a. n.a. PMID[27997206]
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota n.a. n.a. n.a. PMID[28485933]
NPO6698 Euphorbia pithyusa Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[28671832]
NPO8583 Angelica japonica Species Apiaceae Eukaryota n.a. root n.a. PMID[9987830]
NPO17336 Benincasa hispida Species Cucurbitaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO10532 Pinus edulis Species Pinaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO17336 Benincasa hispida Species Cucurbitaceae Eukaryota n.a. n.a. Database[FooDB]
NPO10532 Pinus edulis Species Pinaceae Eukaryota n.a. n.a. Database[FooDB]
NPO8583 Angelica japonica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13228 Farfugium japonicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11791 Magnolia obovata Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17336 Benincasa hispida Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7844 Fritillaria hupehensis Species Liliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13018 Thelephora aurantiotincta Species Thelephoraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13353 Sedum sarmentosum Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12483 Holarrhena floribunda Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17336 Benincasa hispida Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9133 Lathyrus latifolius Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15299 Sandoricum koetjape Species Meliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11791 Magnolia obovata Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13353 Sedum sarmentosum Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3482 Alpinia flabellata Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13018 Thelephora aurantiotincta Species Thelephoraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7844 Fritillaria hupehensis Species Liliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13228 Farfugium japonicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8583 Angelica japonica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12483 Holarrhena floribunda Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13228 Farfugium japonicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO13353 Sedum sarmentosum Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17166 Euphorbia palustris Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9133 Lathyrus latifolius Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17336 Benincasa hispida Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11791 Magnolia obovata Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11791 Magnolia obovata Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7844 Fritillaria hupehensis Species Liliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO13353 Sedum sarmentosum Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO17336 Benincasa hispida Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15299 Sandoricum koetjape Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10532 Pinus edulis Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15514 Pedicularis rex Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27148 Chuquiraga erinacea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13745 Gynoxys verrucosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25118 Centaurea benedicta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO273 Phyllobates bicolor Species Dendrobatidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5998 Echinoclathria subhispida Species Microcionidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14329 Sigillina signifera Species Polycitoridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11246 Ononis viscosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13228 Farfugium japonicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4368 Magnolia officinalis Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14455 Triunia erythrocarpa Species Proteaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15405 Suaeda maritima Species Chenopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18026 Bipolaris sacchari Species Pleosporaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2568 Posidonia oceanica Species Posidoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8583 Angelica japonica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17336 Benincasa hispida Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9133 Lathyrus latifolius Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12018 Alternaria bataticola Species Pleosporaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17166 Euphorbia palustris Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13617 Eria rigida Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3482 Alpinia flabellata Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11592 Cuphea hyssopifolia Species Lythraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12483 Holarrhena floribunda Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4282 Fouquieria diguetii Species Fouquieriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2043 Pseudocyphellaria coronata Species Lobariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2680 Holothuria squamifera Species Holothuriidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9538 Pterocarpus erinaceus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10905 Baccharis truncata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13018 Thelephora aurantiotincta Species Thelephoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7009 Callyspongia spinosissima Species Callyspongiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14194 Mamestra brassicae Species 0ctuidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7844 Fritillaria hupehensis Species Liliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11791 Magnolia obovata Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2070 Thioalkalivibrio versutus Species Ectothiorhodospiraceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO8721 Parectatosoma mocquerysi Species Anisacanthidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15992 Hypogymnia vittata Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17358 Sorbus torminalis Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13353 Sedum sarmentosum Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10048 Pyrus bourgaeana Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15190 Chloranthus fortunei Species Chloranthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13465 Salvia broussonetii Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6698 Euphorbia pithyusa Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT165 Cell Line HeLa Homo sapiens IC50 > 5.0 ug.mL-1 PMID[548480]
NPT81 Cell Line A549 Homo sapiens IC50 > 5.0 ug.mL-1 PMID[548480]
NPT111 Cell Line K562 Homo sapiens IC50 > 5.0 ug.mL-1 PMID[548480]
NPT2341 Cell Line NCI-H1975 Homo sapiens IC50 > 40000.0 nM PMID[548481]
NPT397 Cell Line NCI-H460 Homo sapiens IC50 > 40000.0 nM PMID[548481]
NPT22158 CELL-LINE HCC827 Homo sapiens IC50 > 40000.0 nM PMID[548481]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

  Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

●  The left chart: Distribution of similarity level between NPC216216 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
0.9912 High Similarity NPC295034
0.9224 High Similarity NPC184527
0.9187 High Similarity NPC245395
0.9035 High Similarity NPC228988
0.8974 High Similarity NPC174087
0.8966 High Similarity NPC322197
0.8871 High Similarity NPC3009
0.8824 High Similarity NPC473767
0.8793 High Similarity NPC242136
0.8739 High Similarity NPC249435
0.872 High Similarity NPC96024
0.8707 High Similarity NPC286222
0.8696 High Similarity NPC116842
0.8684 High Similarity NPC17525
0.8661 High Similarity NPC41847
0.8651 High Similarity NPC476119
0.8596 High Similarity NPC141523
0.8584 High Similarity NPC219913
0.8583 High Similarity NPC474890
0.8583 High Similarity NPC161943
0.8583 High Similarity NPC273282
0.8527 High Similarity NPC477139
0.8516 High Similarity NPC85342
0.8516 High Similarity NPC93015
0.8512 High Similarity NPC182240
0.8504 High Similarity NPC276238
0.8462 Intermediate Similarity NPC212718
0.8462 Intermediate Similarity NPC114682
0.8462 Intermediate Similarity NPC268388
0.8455 Intermediate Similarity NPC120545
0.8448 Intermediate Similarity NPC95172
0.8443 Intermediate Similarity NPC159525
0.8443 Intermediate Similarity NPC473136
0.8435 Intermediate Similarity NPC226699
0.8425 Intermediate Similarity NPC229894
0.8417 Intermediate Similarity NPC83718
0.8413 Intermediate Similarity NPC254492
0.8413 Intermediate Similarity NPC62952
0.84 Intermediate Similarity NPC164014
0.84 Intermediate Similarity NPC199273
0.8387 Intermediate Similarity NPC475192
0.8387 Intermediate Similarity NPC91478
0.8387 Intermediate Similarity NPC282577
0.8385 Intermediate Similarity NPC213485
0.8385 Intermediate Similarity NPC40524
0.8385 Intermediate Similarity NPC139074
0.8385 Intermediate Similarity NPC52407
0.8374 Intermediate Similarity NPC190971
0.8374 Intermediate Similarity NPC131868
0.8372 Intermediate Similarity NPC475042
0.8372 Intermediate Similarity NPC275504
0.8372 Intermediate Similarity NPC471851
0.8361 Intermediate Similarity NPC158222
0.8359 Intermediate Similarity NPC117899
0.8359 Intermediate Similarity NPC474998
0.8348 Intermediate Similarity NPC69332
0.8348 Intermediate Similarity NPC95178
0.8348 Intermediate Similarity NPC6984
0.8348 Intermediate Similarity NPC29989
0.8346 Intermediate Similarity NPC30501
0.8346 Intermediate Similarity NPC266689
0.8346 Intermediate Similarity NPC78364
0.8346 Intermediate Similarity NPC162612
0.8346 Intermediate Similarity NPC100067
0.8346 Intermediate Similarity NPC84672
0.8346 Intermediate Similarity NPC105157
0.8346 Intermediate Similarity NPC190043
0.8346 Intermediate Similarity NPC23126
0.8346 Intermediate Similarity NPC169250
0.8346 Intermediate Similarity NPC477593
0.8346 Intermediate Similarity NPC72158
0.8346 Intermediate Similarity NPC72667
0.8346 Intermediate Similarity NPC69424
0.8346 Intermediate Similarity NPC176130
0.8346 Intermediate Similarity NPC98254
0.8346 Intermediate Similarity NPC103356
0.8333 Intermediate Similarity NPC137750
0.8321 Intermediate Similarity NPC50924
0.832 Intermediate Similarity NPC174991
0.8319 Intermediate Similarity NPC11824
0.8306 Intermediate Similarity NPC156139
0.8306 Intermediate Similarity NPC251259
0.8306 Intermediate Similarity NPC31936
0.8291 Intermediate Similarity NPC88141
0.8281 Intermediate Similarity NPC193203
0.8281 Intermediate Similarity NPC473017
0.8281 Intermediate Similarity NPC21305
0.8281 Intermediate Similarity NPC221777
0.8276 Intermediate Similarity NPC303264
0.8268 Intermediate Similarity NPC267846
0.8268 Intermediate Similarity NPC160499
0.8258 Intermediate Similarity NPC283590
0.8258 Intermediate Similarity NPC130899
0.8258 Intermediate Similarity NPC61153
0.8258 Intermediate Similarity NPC70859
0.8254 Intermediate Similarity NPC184219
0.825 Intermediate Similarity NPC285350
0.8246 Intermediate Similarity NPC168829
0.8244 Intermediate Similarity NPC78307
0.824 Intermediate Similarity NPC133909
0.824 Intermediate Similarity NPC67300
0.824 Intermediate Similarity NPC68167
0.824 Intermediate Similarity NPC32032
0.8235 Intermediate Similarity NPC231717
0.8231 Intermediate Similarity NPC244699
0.8231 Intermediate Similarity NPC18798
0.8226 Intermediate Similarity NPC248363
0.8226 Intermediate Similarity NPC297186
0.8217 Intermediate Similarity NPC474546
0.8217 Intermediate Similarity NPC171460
0.8205 Intermediate Similarity NPC262365
0.8203 Intermediate Similarity NPC116513
0.819 Intermediate Similarity NPC70843
0.8189 Intermediate Similarity NPC123506
0.8182 Intermediate Similarity NPC166480
0.8182 Intermediate Similarity NPC23402
0.8182 Intermediate Similarity NPC274876
0.8182 Intermediate Similarity NPC202225
0.8182 Intermediate Similarity NPC282780
0.8174 Intermediate Similarity NPC288411
0.8174 Intermediate Similarity NPC120693
0.8174 Intermediate Similarity NPC8931
0.8174 Intermediate Similarity NPC261573
0.816 Intermediate Similarity NPC115159
0.816 Intermediate Similarity NPC267552
0.816 Intermediate Similarity NPC45438
0.816 Intermediate Similarity NPC224273
0.816 Intermediate Similarity NPC143427
0.816 Intermediate Similarity NPC253627
0.816 Intermediate Similarity NPC73532
0.816 Intermediate Similarity NPC242895
0.816 Intermediate Similarity NPC19174
0.8154 Intermediate Similarity NPC62219
0.8154 Intermediate Similarity NPC27659
0.8154 Intermediate Similarity NPC199253
0.8154 Intermediate Similarity NPC136588
0.8154 Intermediate Similarity NPC108129
0.814 Intermediate Similarity NPC95537
0.814 Intermediate Similarity NPC48248
0.814 Intermediate Similarity NPC473744
0.8134 Intermediate Similarity NPC24394
0.8134 Intermediate Similarity NPC44960
0.8134 Intermediate Similarity NPC477592
0.8134 Intermediate Similarity NPC474110
0.813 Intermediate Similarity NPC283844
0.8125 Intermediate Similarity NPC473751
0.8125 Intermediate Similarity NPC49647
0.8125 Intermediate Similarity NPC136342
0.8125 Intermediate Similarity NPC295202
0.8125 Intermediate Similarity NPC8745
0.8125 Intermediate Similarity NPC227741
0.812 Intermediate Similarity NPC228737
0.812 Intermediate Similarity NPC470210
0.8116 Intermediate Similarity NPC275278
0.811 Intermediate Similarity NPC13238
0.811 Intermediate Similarity NPC231767
0.811 Intermediate Similarity NPC236189
0.8106 Intermediate Similarity NPC225051
0.8103 Intermediate Similarity NPC163734
0.8103 Intermediate Similarity NPC138942
0.8102 Intermediate Similarity NPC477209
0.8102 Intermediate Similarity NPC73061
0.8095 Intermediate Similarity NPC300274
0.8095 Intermediate Similarity NPC309765
0.8095 Intermediate Similarity NPC139171
0.8095 Intermediate Similarity NPC283514
0.8095 Intermediate Similarity NPC11250
0.8095 Intermediate Similarity NPC176208
0.8092 Intermediate Similarity NPC474517
0.8092 Intermediate Similarity NPC72669
0.8088 Intermediate Similarity NPC476534
0.8077 Intermediate Similarity NPC120488
0.8077 Intermediate Similarity NPC99731
0.8077 Intermediate Similarity NPC102829
0.8077 Intermediate Similarity NPC303910
0.8077 Intermediate Similarity NPC92624
0.8074 Intermediate Similarity NPC23870
0.8074 Intermediate Similarity NPC62735
0.8074 Intermediate Similarity NPC206207
0.8067 Intermediate Similarity NPC321252
0.8067 Intermediate Similarity NPC44732
0.8067 Intermediate Similarity NPC252544
0.8067 Intermediate Similarity NPC21162
0.8062 Intermediate Similarity NPC473787
0.806 Intermediate Similarity NPC163029
0.8051 Intermediate Similarity NPC224584
0.8047 Intermediate Similarity NPC131799
0.8047 Intermediate Similarity NPC10926
0.8047 Intermediate Similarity NPC127975
0.8045 Intermediate Similarity NPC27643
0.8045 Intermediate Similarity NPC477594
0.8034 Intermediate Similarity NPC188677
0.8033 Intermediate Similarity NPC278102
0.8031 Intermediate Similarity NPC275145
0.8031 Intermediate Similarity NPC375356
0.803 Intermediate Similarity NPC175738
0.803 Intermediate Similarity NPC70622
0.8016 Intermediate Similarity NPC196976
0.8016 Intermediate Similarity NPC198336
0.8016 Intermediate Similarity NPC303737

  Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

●  The left chart: Distribution of similarity level between NPC216216 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
0.848 Intermediate Similarity NPD1164 Approved
0.8361 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.8016 Intermediate Similarity NPD1201 Approved
0.7966 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7907 Intermediate Similarity NPD1470 Approved
0.784 Intermediate Similarity NPD9545 Approved
0.7823 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.781 Intermediate Similarity NPD2344 Approved
0.7794 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7794 Intermediate Similarity NPD1510 Phase 2
0.7761 Intermediate Similarity NPD1240 Approved
0.7761 Intermediate Similarity NPD943 Approved
0.7737 Intermediate Similarity NPD5405 Approved
0.7737 Intermediate Similarity NPD5406 Approved
0.7737 Intermediate Similarity NPD5408 Approved
0.7737 Intermediate Similarity NPD5404 Approved
0.7737 Intermediate Similarity NPD2935 Discontinued
0.7712 Intermediate Similarity NPD1237 Approved
0.7698 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7681 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7674 Intermediate Similarity NPD3972 Approved
0.7672 Intermediate Similarity NPD3020 Approved
0.7647 Intermediate Similarity NPD1607 Approved
0.7643 Intermediate Similarity NPD7003 Approved
0.7612 Intermediate Similarity NPD3764 Approved
0.7603 Intermediate Similarity NPD9266 Approved
0.7603 Intermediate Similarity NPD74 Approved
0.7589 Intermediate Similarity NPD2309 Approved
0.7565 Intermediate Similarity NPD2859 Approved
0.7565 Intermediate Similarity NPD2860 Approved
0.7552 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.754 Intermediate Similarity NPD9493 Approved
0.7536 Intermediate Similarity NPD2799 Discontinued
0.7521 Intermediate Similarity NPD9263 Approved
0.7521 Intermediate Similarity NPD9267 Approved
0.7521 Intermediate Similarity NPD9264 Approved
0.7519 Intermediate Similarity NPD9494 Approved
0.75 Intermediate Similarity NPD1549 Phase 2
0.7483 Intermediate Similarity NPD7390 Discontinued
0.7479 Intermediate Similarity NPD1929 Approved
0.7479 Intermediate Similarity NPD1931 Clinical (unspecified phase)
0.7479 Intermediate Similarity NPD1930 Approved
0.7478 Intermediate Similarity NPD2933 Approved
0.7478 Intermediate Similarity NPD2934 Approved
0.7466 Intermediate Similarity NPD7458 Discontinued
0.7444 Intermediate Similarity NPD2798 Approved
0.7442 Intermediate Similarity NPD2932 Approved
0.7442 Intermediate Similarity NPD3019 Approved
0.7431 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7429 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7429 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7424 Intermediate Similarity NPD1876 Approved
0.7424 Intermediate Similarity NPD1283 Approved
0.7415 Intermediate Similarity NPD4380 Phase 2
0.7394 Intermediate Similarity NPD4628 Phase 3
0.7381 Intermediate Similarity NPD5951 Approved
0.7377 Intermediate Similarity NPD2342 Discontinued
0.7353 Intermediate Similarity NPD2313 Discontinued
0.7328 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD3750 Approved
0.7265 Intermediate Similarity NPD1809 Phase 2
0.7241 Intermediate Similarity NPD845 Approved
0.7239 Intermediate Similarity NPD1203 Approved
0.7234 Intermediate Similarity NPD2796 Approved
0.7234 Intermediate Similarity NPD1551 Phase 2
0.7231 Intermediate Similarity NPD1651 Approved
0.7222 Intermediate Similarity NPD7635 Approved
0.7219 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7197 Intermediate Similarity NPD1281 Approved
0.7192 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.719 Intermediate Similarity NPD9261 Approved
0.7179 Intermediate Similarity NPD1432 Clinical (unspecified phase)
0.7177 Intermediate Similarity NPD6831 Clinical (unspecified phase)
0.7172 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7171 Intermediate Similarity NPD7768 Phase 2
0.7165 Intermediate Similarity NPD1241 Discontinued
0.7163 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7153 Intermediate Similarity NPD3400 Discontinued
0.7152 Intermediate Similarity NPD7819 Suspended
0.7152 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7133 Intermediate Similarity NPD7411 Suspended
0.7132 Intermediate Similarity NPD4208 Discontinued
0.7124 Intermediate Similarity NPD7075 Discontinued
0.712 Intermediate Similarity NPD3021 Approved
0.712 Intermediate Similarity NPD3022 Approved
0.7114 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7113 Intermediate Similarity NPD4476 Approved
0.7113 Intermediate Similarity NPD4477 Approved
0.7111 Intermediate Similarity NPD2797 Approved
0.7109 Intermediate Similarity NPD9281 Approved
0.7107 Intermediate Similarity NPD1932 Approved
0.7075 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.707 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD2346 Discontinued
0.7059 Intermediate Similarity NPD288 Approved
0.705 Intermediate Similarity NPD6663 Approved
0.7045 Intermediate Similarity NPD4626 Approved
0.7045 Intermediate Similarity NPD7163 Clinical (unspecified phase)
0.7042 Intermediate Similarity NPD4308 Phase 3
0.7039 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7034 Intermediate Similarity NPD688 Clinical (unspecified phase)
0.7029 Intermediate Similarity NPD7008 Discontinued
0.7025 Intermediate Similarity NPD289 Clinical (unspecified phase)
0.7023 Intermediate Similarity NPD1894 Discontinued
0.7015 Intermediate Similarity NPD1608 Approved
0.7015 Intermediate Similarity NPD9269 Phase 2
0.7014 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7008 Intermediate Similarity NPD6124 Clinical (unspecified phase)
0.7007 Intermediate Similarity NPD5736 Approved
0.6993 Remote Similarity NPD2296 Approved
0.6983 Remote Similarity NPD9258 Approved
0.6983 Remote Similarity NPD9256 Approved
0.698 Remote Similarity NPD920 Approved
0.6978 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6978 Remote Similarity NPD3268 Approved
0.6975 Remote Similarity NPD844 Approved
0.6974 Remote Similarity NPD1934 Approved
0.697 Remote Similarity NPD9268 Approved
0.6967 Remote Similarity NPD940 Approved
0.6967 Remote Similarity NPD846 Approved
0.6963 Remote Similarity NPD1755 Approved
0.6963 Remote Similarity NPD3600 Clinical (unspecified phase)
0.6957 Remote Similarity NPD6832 Phase 2
0.695 Remote Similarity NPD6355 Discontinued
0.695 Remote Similarity NPD230 Phase 1
0.6949 Remote Similarity NPD1202 Approved
0.6943 Remote Similarity NPD6232 Discontinued
0.6942 Remote Similarity NPD1238 Approved
0.6939 Remote Similarity NPD3300 Phase 2
0.6934 Remote Similarity NPD6007 Clinical (unspecified phase)
0.6929 Remote Similarity NPD520 Approved
0.6923 Remote Similarity NPD3299 Clinical (unspecified phase)
0.6923 Remote Similarity NPD256 Approved
0.6923 Remote Similarity NPD255 Approved
0.6923 Remote Similarity NPD3748 Approved
0.6918 Remote Similarity NPD8166 Discontinued
0.6917 Remote Similarity NPD4589 Approved
0.6917 Remote Similarity NPD2286 Discontinued
0.6913 Remote Similarity NPD6273 Approved
0.6906 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6903 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6903 Remote Similarity NPD3749 Approved
0.6899 Remote Similarity NPD7159 Clinical (unspecified phase)
0.6894 Remote Similarity NPD5304 Approved
0.6894 Remote Similarity NPD3091 Approved
0.6894 Remote Similarity NPD5303 Approved
0.6892 Remote Similarity NPD6799 Approved
0.6892 Remote Similarity NPD1511 Approved
0.6889 Remote Similarity NPD9717 Approved
0.6889 Remote Similarity NPD4878 Approved
0.6889 Remote Similarity NPD1481 Phase 2
0.6887 Remote Similarity NPD3226 Approved
0.6885 Remote Similarity NPD1242 Phase 1
0.6879 Remote Similarity NPD2979 Phase 3
0.6879 Remote Similarity NPD6959 Discontinued
0.6879 Remote Similarity NPD4060 Phase 1
0.6866 Remote Similarity NPD3026 Approved
0.6866 Remote Similarity NPD3023 Approved
0.6863 Remote Similarity NPD6801 Discontinued
0.6857 Remote Similarity NPD6798 Discontinued
0.6849 Remote Similarity NPD1243 Approved
0.6849 Remote Similarity NPD2800 Approved
0.6846 Remote Similarity NPD2534 Approved
0.6846 Remote Similarity NPD2532 Approved
0.6846 Remote Similarity NPD2533 Approved
0.6842 Remote Similarity NPD3025 Approved
0.6842 Remote Similarity NPD5691 Approved
0.6842 Remote Similarity NPD111 Approved
0.6842 Remote Similarity NPD3024 Approved
0.6842 Remote Similarity NPD6599 Discontinued
0.6839 Remote Similarity NPD3882 Suspended
0.6839 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6838 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6835 Remote Similarity NPD4207 Discontinued
0.6832 Remote Similarity NPD5844 Phase 1
0.6815 Remote Similarity NPD1610 Phase 2
0.6815 Remote Similarity NPD1535 Discovery
0.6813 Remote Similarity NPD7473 Discontinued
0.6803 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6803 Remote Similarity NPD2066 Phase 3
0.68 Remote Similarity NPD1512 Approved
0.6797 Remote Similarity NPD4141 Clinical (unspecified phase)
0.6791 Remote Similarity NPD17 Approved
0.6791 Remote Similarity NPD3412 Clinical (unspecified phase)
0.6783 Remote Similarity NPD6651 Approved
0.678 Remote Similarity NPD1239 Approved
0.6772 Remote Similarity NPD2329 Discontinued
0.6769 Remote Similarity NPD2229 Approved
0.6769 Remote Similarity NPD2234 Approved
0.6769 Remote Similarity NPD2228 Approved
0.6761 Remote Similarity NPD4307 Phase 2
0.6761 Remote Similarity NPD3142 Approved
0.6761 Remote Similarity NPD3140 Approved
0.6757 Remote Similarity NPD2354 Approved
0.6757 Remote Similarity NPD6190 Approved
0.6757 Remote Similarity NPD3295 Clinical (unspecified phase)
0.6753 Remote Similarity NPD7577 Discontinued
0.6753 Remote Similarity NPD6280 Approved
0.6753 Remote Similarity NPD6279 Approved
0.6744 Remote Similarity NPD1609 Clinical (unspecified phase)

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data