Structure

Physi-Chem Properties

Molecular Weight:  117.06
Volume:  136.182
LogP:  1.443
LogD:  1.461
LogS:  -2.405
# Rotatable Bonds:  1
TPSA:  23.79
# H-Bond Aceptor:  1
# H-Bond Donor:  0
# Rings:  1
# Heavy Atoms:  1

MedChem Properties

QED Drug-Likeness Score:  0.549
Synthetic Accessibility Score:  1.577
Fsp3:  0.125
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.257
MDCK Permeability:  0.0001346498029306531
Pgp-inhibitor:  0.0
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.005
30% Bioavailability (F30%):  0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.927
Plasma Protein Binding (PPB):  57.899051666259766%
Volume Distribution (VD):  2.883
Pgp-substrate:  40.979122161865234%

ADMET: Metabolism

CYP1A2-inhibitor:  0.93
CYP1A2-substrate:  0.498
CYP2C19-inhibitor:  0.398
CYP2C19-substrate:  0.06
CYP2C9-inhibitor:  0.118
CYP2C9-substrate:  0.287
CYP2D6-inhibitor:  0.013
CYP2D6-substrate:  0.128
CYP3A4-inhibitor:  0.021
CYP3A4-substrate:  0.36

ADMET: Excretion

Clearance (CL):  10.174
Half-life (T1/2):  0.85

ADMET: Toxicity

hERG Blockers:  0.013
Human Hepatotoxicity (H-HT):  0.092
Drug-inuced Liver Injury (DILI):  0.88
AMES Toxicity:  0.133
Rat Oral Acute Toxicity:  0.156
Maximum Recommended Daily Dose:  0.066
Skin Sensitization:  0.281
Carcinogencity:  0.746
Eye Corrosion:  0.923
Eye Irritation:  0.988
Respiratory Toxicity:  0.973

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  Natural Product: NPC50266

Natural Product ID:  NPC50266
Common Name*:   2-Phenylacetonitrile
IUPAC Name:   2-phenylacetonitrile
Synonyms:  
Standard InCHIKey:  SUSQOBVLVYHIEX-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C8H7N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6H2
SMILES:  N#CCc1ccccc1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3560735
PubChem CID:   8794
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002279] Benzene and substituted derivatives
        • [CHEMONTID:0001220] Benzyl cyanides

*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
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flowers n.a. n.a. DOI[10.1002/elan.200403102]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flowers n.a. n.a. DOI[10.1016/j.foodchem.2012.02.124]
NPO681 Mesua ferrea Species Calophyllaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0040-4020(01)83306-8]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flowers n.a. n.a. PMID[11077184]
NPO20379 Schistocerca gregaria Species Acrididae Eukaryota n.a. n.a. n.a. PMID[12770022]
NPO4410 Laggera alata Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[12932128]
NPO1745 Myriapora truncata n.a. n.a. n.a. n.a. n.a. n.a. PMID[17284072]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flowers n.a. n.a. PMID[17328234]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flower buds n.a. n.a. PMID[18321056]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. flower n.a. PMID[21804227]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota flower buds Henan province, China 2005-MAY PMID[21942812]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. flower bud n.a. PMID[21942812]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. leaf n.a. PMID[23265495]
NPO7576 Brassica oleracea Species Brassicaceae Eukaryota n.a. n.a. n.a. PMID[24014097]
NPO11021 Moringa oleifera Species Moringaceae Eukaryota n.a. leaf n.a. PMID[24024688]
NPO7576 Brassica oleracea Species Brassicaceae Eukaryota n.a. n.a. n.a. PMID[24128451]
NPO5705 Rorippa sylvestris Species Brassicaceae Eukaryota n.a. n.a. n.a. PMID[24253962]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flower buds n.a. n.a. PMID[24279769]
NPO3302 Fusarium avenaceum Species Nectriaceae Eukaryota n.a. n.a. n.a. PMID[25475336]
NPO11021 Moringa oleifera Species Moringaceae Eukaryota n.a. n.a. n.a. PMID[7798960]
NPO17752 Mentha X piperita Strain Lamiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO7576 Brassica oleracea Species Brassicaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO17752 Mentha X piperita Strain Lamiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO11021 Moringa oleifera Species Moringaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO7576 Brassica oleracea Species Brassicaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO11021 Moringa oleifera Species Moringaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO17752 Mentha X piperita Strain Lamiaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO7576 Brassica oleracea Species Brassicaceae Eukaryota Sprout Seedling n.a. n.a. Database[FooDB]
NPO7576 Brassica oleracea Species Brassicaceae Eukaryota Stem n.a. n.a. Database[FooDB]
NPO17752 Mentha X piperita Strain Lamiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO11021 Moringa oleifera Species Moringaceae Eukaryota n.a. n.a. Database[FooDB]
NPO7576 Brassica oleracea Species Brassicaceae Eukaryota n.a. n.a. Database[FooDB]
NPO17752 Mentha X piperita Strain Lamiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO11021 Moringa oleifera Species Moringaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO11021 Moringa oleifera Species Moringaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO7255 Pterocarpus indicus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO681 Mesua ferrea Species Calophyllaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6187 Sequoia sempervirens Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5536 Papaver persicum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25645 Flos lonicerae Species Lycaenidae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO495 Daemonorops draco Species Arecaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7576 Brassica oleracea Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17752 Mentha X piperita Strain Lamiaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO7255 Pterocarpus indicus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17752 Mentha X piperita Strain Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7576 Brassica oleracea Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6187 Sequoia sempervirens Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO681 Mesua ferrea Species Calophyllaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO495 Daemonorops draco Species Arecaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3905 Medinilla magnifica Species Melastomataceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25645 Flos lonicerae Species Lycaenidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4410 Laggera alata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5536 Papaver persicum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7576 Brassica oleracea Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO495 Daemonorops draco Species Arecaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5536 Papaver persicum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO495 Daemonorops draco Species Arecaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO4858 Helipterum gnaphaloides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10178 Achillea chamaemelifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7266 Goupia glabra Species Goupiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5021 Podospora curvicolla Species Lasiosphaeriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20379 Schistocerca gregaria Species Acrididae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO823 Senecio cathcartensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3410 Ocotea glaziovii Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25818 Aframomum mala Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11714 Alnus maximowiczii Species Betulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3905 Medinilla magnifica Species Melastomataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5705 Rorippa sylvestris Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11561 Eucalyptus andrewsi Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8703 Monopteryx uaucu Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6187 Sequoia sempervirens Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO681 Mesua ferrea Species Calophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1962 Piper cuneifolium Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5536 Papaver persicum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8339 Lithothamnion corallioides Species Hapalidiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1745 Myriapora truncata n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO1585 Onobrychis bobrovii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17752 Mentha X piperita Strain Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO495 Daemonorops draco Species Arecaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11021 Moringa oleifera Species Moringaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4221 Fusarium sacchari Species Nectriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7576 Brassica oleracea Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7963 Excoecaria acerifolia Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2501 Trifolium strepens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17990 Lepidium didymum Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO193 Trichogonia grazielae Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5937 Garrya laurifolia Species Garryaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7255 Pterocarpus indicus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4410 Laggera alata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2703 Petteria ramentacea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3302 Fusarium avenaceum Species Nectriaceae 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
NPO17752 NPC50266 Other Leaf 0.0011 0.0002 0.002 mg/100g Database [DUKE]
NPO7576 NPC50266 Other Stem 0.019 0.019 0.019 mg/100g Database [DUKE]

☑ 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
NPT2 Others Unspecified Potency n.a. 56234.1 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 891.3 nM PubChem BioAssay data set

☑ 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 NPC50266 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
0.9219 High Similarity NPC200936
0.8667 High Similarity NPC198841
0.8525 High Similarity NPC120441
0.8525 High Similarity NPC300345
0.8525 High Similarity NPC212114
0.8525 High Similarity NPC65873
0.85 High Similarity NPC149436
0.8429 Intermediate Similarity NPC110264
0.8361 Intermediate Similarity NPC269586
0.8197 Intermediate Similarity NPC277704
0.8125 Intermediate Similarity NPC210849
0.8125 Intermediate Similarity NPC246588
0.8125 Intermediate Similarity NPC238023
0.8125 Intermediate Similarity NPC248705
0.8125 Intermediate Similarity NPC135924
0.8125 Intermediate Similarity NPC150196
0.8125 Intermediate Similarity NPC54368
0.8125 Intermediate Similarity NPC310758
0.8095 Intermediate Similarity NPC8235
0.8095 Intermediate Similarity NPC36357
0.8095 Intermediate Similarity NPC114327
0.806 Intermediate Similarity NPC52330
0.8 Intermediate Similarity NPC22786
0.8 Intermediate Similarity NPC29680
0.8 Intermediate Similarity NPC71009
0.8 Intermediate Similarity NPC66517
0.7971 Intermediate Similarity NPC229235
0.7969 Intermediate Similarity NPC169110
0.7969 Intermediate Similarity NPC147062
0.7879 Intermediate Similarity NPC21211
0.7879 Intermediate Similarity NPC113670
0.7879 Intermediate Similarity NPC88566
0.7812 Intermediate Similarity NPC64270
0.7761 Intermediate Similarity NPC198023
0.7761 Intermediate Similarity NPC32312
0.7761 Intermediate Similarity NPC155172
0.7761 Intermediate Similarity NPC291066
0.7746 Intermediate Similarity NPC244738
0.7727 Intermediate Similarity NPC200745
0.7692 Intermediate Similarity NPC147578
0.7647 Intermediate Similarity NPC178527
0.7639 Intermediate Similarity NPC122327
0.7639 Intermediate Similarity NPC112609
0.7639 Intermediate Similarity NPC113000
0.7612 Intermediate Similarity NPC45756
0.7576 Intermediate Similarity NPC45255
0.7576 Intermediate Similarity NPC200624
0.7536 Intermediate Similarity NPC6107
0.7536 Intermediate Similarity NPC267443
0.7534 Intermediate Similarity NPC276699
0.7465 Intermediate Similarity NPC219246
0.7432 Intermediate Similarity NPC139658
0.7397 Intermediate Similarity NPC299134
0.7391 Intermediate Similarity NPC36440
0.7391 Intermediate Similarity NPC289915
0.7391 Intermediate Similarity NPC113837
0.7361 Intermediate Similarity NPC121708
0.7361 Intermediate Similarity NPC125144
0.7333 Intermediate Similarity NPC290638
0.7333 Intermediate Similarity NPC325662
0.7333 Intermediate Similarity NPC98269
0.7324 Intermediate Similarity NPC246822
0.7324 Intermediate Similarity NPC213570
0.7324 Intermediate Similarity NPC139416
0.7324 Intermediate Similarity NPC473206
0.7297 Intermediate Similarity NPC98976
0.7288 Intermediate Similarity NPC11150
0.7284 Intermediate Similarity NPC211237
0.7246 Intermediate Similarity NPC264470
0.7222 Intermediate Similarity NPC72670
0.7222 Intermediate Similarity NPC251490
0.7222 Intermediate Similarity NPC263385
0.72 Intermediate Similarity NPC271642
0.7183 Intermediate Similarity NPC82770
0.7183 Intermediate Similarity NPC78954
0.7183 Intermediate Similarity NPC239931
0.7183 Intermediate Similarity NPC311343
0.7123 Intermediate Similarity NPC193578
0.7123 Intermediate Similarity NPC226999
0.7123 Intermediate Similarity NPC280135
0.7123 Intermediate Similarity NPC1008
0.7123 Intermediate Similarity NPC87099
0.7123 Intermediate Similarity NPC135433
0.7123 Intermediate Similarity NPC158028
0.7123 Intermediate Similarity NPC208302
0.7123 Intermediate Similarity NPC74458
0.7123 Intermediate Similarity NPC39799
0.7083 Intermediate Similarity NPC16190
0.7083 Intermediate Similarity NPC98880
0.7083 Intermediate Similarity NPC235059
0.7083 Intermediate Similarity NPC5324
0.7083 Intermediate Similarity NPC169222
0.7051 Intermediate Similarity NPC192623
0.7027 Intermediate Similarity NPC271437
0.7027 Intermediate Similarity NPC285679
0.7027 Intermediate Similarity NPC1901
0.7027 Intermediate Similarity NPC54269
0.7027 Intermediate Similarity NPC212463
0.7013 Intermediate Similarity NPC12857
0.6986 Remote Similarity NPC95289
0.6962 Remote Similarity NPC231986
0.6944 Remote Similarity NPC181786
0.6944 Remote Similarity NPC22760
0.6933 Remote Similarity NPC258492
0.6933 Remote Similarity NPC96835
0.6933 Remote Similarity NPC108218
0.6933 Remote Similarity NPC208075
0.6892 Remote Similarity NPC155429
0.6892 Remote Similarity NPC326200
0.6875 Remote Similarity NPC14326
0.6849 Remote Similarity NPC297358
0.6842 Remote Similarity NPC189371
0.6842 Remote Similarity NPC307195
0.6835 Remote Similarity NPC475573
0.6835 Remote Similarity NPC475289
0.6835 Remote Similarity NPC309279
0.679 Remote Similarity NPC474088
0.679 Remote Similarity NPC119677
0.679 Remote Similarity NPC104070
0.6707 Remote Similarity NPC133162
0.6707 Remote Similarity NPC169016
0.6667 Remote Similarity NPC245966
0.6667 Remote Similarity NPC249018
0.6667 Remote Similarity NPC298023
0.6667 Remote Similarity NPC3190
0.6667 Remote Similarity NPC9796
0.6627 Remote Similarity NPC3210
0.6623 Remote Similarity NPC206800
0.6623 Remote Similarity NPC32203
0.6582 Remote Similarity NPC137847
0.6582 Remote Similarity NPC224544
0.6582 Remote Similarity NPC36342
0.6582 Remote Similarity NPC103488
0.6582 Remote Similarity NPC76455
0.6582 Remote Similarity NPC255345
0.6582 Remote Similarity NPC66270
0.6582 Remote Similarity NPC2785
0.6582 Remote Similarity NPC245896
0.6582 Remote Similarity NPC285470
0.6552 Remote Similarity NPC151764
0.6548 Remote Similarity NPC258046
0.6548 Remote Similarity NPC203076
0.6538 Remote Similarity NPC175393
0.6538 Remote Similarity NPC302129
0.65 Remote Similarity NPC170484
0.65 Remote Similarity NPC151405
0.65 Remote Similarity NPC139901
0.65 Remote Similarity NPC272260
0.65 Remote Similarity NPC300205
0.65 Remote Similarity NPC159661
0.6471 Remote Similarity NPC471638
0.6471 Remote Similarity NPC60408
0.6471 Remote Similarity NPC473031
0.6456 Remote Similarity NPC329318
0.6456 Remote Similarity NPC3672
0.6456 Remote Similarity NPC287790
0.6456 Remote Similarity NPC179726
0.642 Remote Similarity NPC95868
0.642 Remote Similarity NPC315216
0.642 Remote Similarity NPC164086
0.642 Remote Similarity NPC50063
0.642 Remote Similarity NPC190567
0.642 Remote Similarity NPC71664
0.642 Remote Similarity NPC164449
0.642 Remote Similarity NPC127343
0.642 Remote Similarity NPC157055
0.642 Remote Similarity NPC328178
0.642 Remote Similarity NPC477703
0.642 Remote Similarity NPC121800
0.642 Remote Similarity NPC184030
0.642 Remote Similarity NPC17408
0.642 Remote Similarity NPC285716
0.6395 Remote Similarity NPC325441
0.6395 Remote Similarity NPC30445
0.6395 Remote Similarity NPC12429
0.6386 Remote Similarity NPC146703
0.6375 Remote Similarity NPC176228
0.6375 Remote Similarity NPC50192
0.6341 Remote Similarity NPC117180
0.6341 Remote Similarity NPC73978
0.6341 Remote Similarity NPC133050
0.6341 Remote Similarity NPC145053
0.6341 Remote Similarity NPC12936
0.6341 Remote Similarity NPC273033
0.6341 Remote Similarity NPC242628
0.6329 Remote Similarity NPC78500
0.6324 Remote Similarity NPC56072
0.6322 Remote Similarity NPC470877
0.6322 Remote Similarity NPC176858
0.6296 Remote Similarity NPC167577
0.6296 Remote Similarity NPC78517
0.6296 Remote Similarity NPC469894
0.6279 Remote Similarity NPC53492
0.6279 Remote Similarity NPC198747
0.6279 Remote Similarity NPC305602
0.6279 Remote Similarity NPC17497
0.6265 Remote Similarity NPC103387
0.6265 Remote Similarity NPC87299
0.6265 Remote Similarity NPC73637
0.6265 Remote Similarity NPC323103

  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 NPC50266 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
0.9833 High Similarity NPD173 Clinical (unspecified phase)
0.7879 Intermediate Similarity NPD675 Discontinued
0.7857 Intermediate Similarity NPD294 Approved
0.7857 Intermediate Similarity NPD292 Approved
0.7746 Intermediate Similarity NPD9728 Phase 1
0.7639 Intermediate Similarity NPD9590 Approved
0.7639 Intermediate Similarity NPD505 Clinical (unspecified phase)
0.7639 Intermediate Similarity NPD80 Approved
0.7639 Intermediate Similarity NPD9594 Approved
0.7639 Intermediate Similarity NPD9588 Approved
0.7639 Intermediate Similarity NPD9593 Approved
0.7639 Intermediate Similarity NPD9591 Approved
0.7639 Intermediate Similarity NPD9592 Approved
0.7639 Intermediate Similarity NPD9589 Approved
0.7468 Intermediate Similarity NPD2205 Approved
0.7468 Intermediate Similarity NPD2208 Approved
0.7342 Intermediate Similarity NPD785 Approved
0.7333 Intermediate Similarity NPD4144 Approved
0.7333 Intermediate Similarity NPD4147 Approved
0.7324 Intermediate Similarity NPD9497 Clinical (unspecified phase)
0.7237 Intermediate Similarity NPD9563 Approved
0.7237 Intermediate Similarity NPD9564 Approved
0.7237 Intermediate Similarity NPD295 Approved
0.7237 Intermediate Similarity NPD9397 Approved
0.7237 Intermediate Similarity NPD293 Approved
0.7237 Intermediate Similarity NPD296 Approved
0.7237 Intermediate Similarity NPD79 Approved
0.7237 Intermediate Similarity NPD9393 Approved
0.7195 Intermediate Similarity NPD5675 Discontinued
0.7143 Intermediate Similarity NPD1053 Approved
0.7143 Intermediate Similarity NPD589 Approved
0.7143 Intermediate Similarity NPD1051 Approved
0.7143 Intermediate Similarity NPD1052 Approved
0.7143 Intermediate Similarity NPD590 Approved
0.7105 Intermediate Similarity NPD603 Approved
0.7051 Intermediate Similarity NPD5372 Approved
0.7051 Intermediate Similarity NPD3979 Approved
0.7051 Intermediate Similarity NPD3981 Approved
0.7051 Intermediate Similarity NPD5371 Approved
0.7051 Intermediate Similarity NPD1617 Discontinued
0.7051 Intermediate Similarity NPD3903 Approved
0.7051 Intermediate Similarity NPD3904 Approved
0.7051 Intermediate Similarity NPD260 Discontinued
0.6962 Remote Similarity NPD472 Approved
0.6962 Remote Similarity NPD4027 Approved
0.6962 Remote Similarity NPD4026 Approved
0.6962 Remote Similarity NPD3035 Approved
0.6923 Remote Similarity NPD507 Approved
0.6923 Remote Similarity NPD508 Approved
0.6875 Remote Similarity NPD4170 Approved
0.6875 Remote Similarity NPD4701 Clinical (unspecified phase)
0.6875 Remote Similarity NPD4169 Approved
0.6849 Remote Similarity NPD1673 Approved
0.679 Remote Similarity NPD262 Approved
0.679 Remote Similarity NPD4635 Approved
0.679 Remote Similarity NPD831 Approved
0.679 Remote Similarity NPD263 Approved
0.679 Remote Similarity NPD2001 Discontinued
0.679 Remote Similarity NPD830 Approved
0.6707 Remote Similarity NPD3427 Approved
0.6707 Remote Similarity NPD5178 Approved
0.6707 Remote Similarity NPD9395 Approved
0.6707 Remote Similarity NPD4544 Approved
0.6707 Remote Similarity NPD2538 Approved
0.6707 Remote Similarity NPD3429 Approved
0.6707 Remote Similarity NPD2539 Approved
0.6629 Remote Similarity NPD5963 Phase 2
0.6629 Remote Similarity NPD5964 Phase 2
0.6627 Remote Similarity NPD5916 Discontinued
0.6627 Remote Similarity NPD9505 Clinical (unspecified phase)
0.6623 Remote Similarity NPD9716 Approved
0.6585 Remote Similarity NPD1800 Clinical (unspecified phase)
0.6582 Remote Similarity NPD227 Approved
0.6582 Remote Similarity NPD225 Approved
0.6548 Remote Similarity NPD4406 Approved
0.6548 Remote Similarity NPD5252 Clinical (unspecified phase)
0.6548 Remote Similarity NPD4636 Approved
0.6548 Remote Similarity NPD305 Approved
0.6548 Remote Similarity NPD4409 Approved
0.6548 Remote Similarity NPD304 Approved
0.65 Remote Similarity NPD9490 Approved
0.65 Remote Similarity NPD1475 Approved
0.6471 Remote Similarity NPD9538 Approved
0.6471 Remote Similarity NPD780 Approved
0.6471 Remote Similarity NPD783 Approved
0.6471 Remote Similarity NPD2002 Discontinued
0.6471 Remote Similarity NPD3426 Approved
0.6471 Remote Similarity NPD4145 Approved
0.6471 Remote Similarity NPD782 Approved
0.6471 Remote Similarity NPD4146 Approved
0.6471 Remote Similarity NPD3428 Approved
0.6471 Remote Similarity NPD781 Approved
0.642 Remote Similarity NPD914 Suspended
0.642 Remote Similarity NPD1507 Clinical (unspecified phase)
0.6395 Remote Similarity NPD1101 Approved
0.6395 Remote Similarity NPD3345 Approved
0.6386 Remote Similarity NPD4000 Phase 3
0.6353 Remote Similarity NPD3099 Discontinued
0.6341 Remote Similarity NPD942 Approved
0.6341 Remote Similarity NPD226 Approved
0.6322 Remote Similarity NPD5656 Clinical (unspecified phase)
0.6322 Remote Similarity NPD1629 Approved
0.6322 Remote Similarity NPD1628 Approved
0.6322 Remote Similarity NPD771 Phase 3
0.6308 Remote Similarity NPD9072 Clinical (unspecified phase)
0.6304 Remote Similarity NPD5926 Approved
0.6279 Remote Similarity NPD187 Approved
0.625 Remote Similarity NPD4728 Approved
0.625 Remote Similarity NPD3346 Approved
0.625 Remote Similarity NPD3344 Approved
0.625 Remote Similarity NPD5915 Approved
0.625 Remote Similarity NPD9294 Approved
0.6207 Remote Similarity NPD588 Approved
0.6207 Remote Similarity NPD531 Approved
0.6207 Remote Similarity NPD587 Approved
0.619 Remote Similarity NPD5288 Clinical (unspecified phase)
0.619 Remote Similarity NPD3971 Phase 1
0.619 Remote Similarity NPD9491 Approved
0.619 Remote Similarity NPD1185 Approved
0.619 Remote Similarity NPD423 Phase 3
0.618 Remote Similarity NPD4543 Discontinued
0.618 Remote Similarity NPD2998 Approved
0.618 Remote Similarity NPD2997 Approved
0.618 Remote Similarity NPD3000 Approved
0.618 Remote Similarity NPD517 Discontinued
0.618 Remote Similarity NPD530 Approved
0.6136 Remote Similarity NPD9 Approved
0.6136 Remote Similarity NPD297 Approved
0.6136 Remote Similarity NPD9351 Phase 3
0.6136 Remote Similarity NPD9348 Approved
0.6136 Remote Similarity NPD9350 Approved
0.6136 Remote Similarity NPD9349 Approved
0.6111 Remote Similarity NPD4405 Approved
0.6111 Remote Similarity NPD752 Approved
0.6111 Remote Similarity NPD1812 Approved
0.6111 Remote Similarity NPD4408 Approved
0.6111 Remote Similarity NPD6690 Approved
0.6111 Remote Similarity NPD4407 Approved
0.6111 Remote Similarity NPD9361 Approved
0.6111 Remote Similarity NPD1814 Approved
0.6047 Remote Similarity NPD5734 Clinical (unspecified phase)
0.6044 Remote Similarity NPD719 Approved
0.6044 Remote Similarity NPD243 Approved
0.6044 Remote Similarity NPD3982 Approved
0.6044 Remote Similarity NPD720 Approved
0.6044 Remote Similarity NPD8 Approved
0.6044 Remote Similarity NPD1066 Discontinued
0.6044 Remote Similarity NPD4545 Approved
0.6044 Remote Similarity NPD736 Approved
0.6044 Remote Similarity NPD6548 Approved
0.6044 Remote Similarity NPD3719 Approved
0.6044 Remote Similarity NPD199 Approved
0.6044 Remote Similarity NPD3718 Approved
0.6044 Remote Similarity NPD1409 Phase 3
0.6044 Remote Similarity NPD735 Approved
0.6044 Remote Similarity NPD6549 Approved
0.6044 Remote Similarity NPD4542 Approved
0.6044 Remote Similarity NPD3980 Approved
0.6044 Remote Similarity NPD2878 Approved
0.6044 Remote Similarity NPD197 Approved
0.6042 Remote Similarity NPD744 Clinical (unspecified phase)
0.6023 Remote Similarity NPD9186 Approved
0.6023 Remote Similarity NPD9184 Approved
0.6 Remote Similarity NPD7160 Approved
0.5978 Remote Similarity NPD2656 Approved
0.5978 Remote Similarity NPD3772 Phase 3
0.5978 Remote Similarity NPD4814 Discontinued
0.5978 Remote Similarity NPD7344 Phase 1
0.5978 Remote Similarity NPD4094 Approved
0.5978 Remote Similarity NPD7343 Discovery
0.5978 Remote Similarity NPD5554 Approved
0.5978 Remote Similarity NPD1081 Clinical (unspecified phase)
0.5978 Remote Similarity NPD2655 Approved
0.5952 Remote Similarity NPD9250 Approved
0.5934 Remote Similarity NPD159 Clinical (unspecified phase)
0.5914 Remote Similarity NPD2507 Clinical (unspecified phase)
0.5914 Remote Similarity NPD1738 Approved
0.5914 Remote Similarity NPD2005 Discontinued
0.5914 Remote Similarity NPD3457 Approved
0.5914 Remote Similarity NPD2895 Discontinued
0.5914 Remote Similarity NPD3458 Approved
0.5914 Remote Similarity NPD6472 Discontinued
0.5914 Remote Similarity NPD3456 Approved
0.5909 Remote Similarity NPD1087 Approved
0.5909 Remote Similarity NPD4793 Discontinued
0.5909 Remote Similarity NPD506 Clinical (unspecified phase)
0.5909 Remote Similarity NPD650 Approved
0.587 Remote Similarity NPD837 Approved
0.587 Remote Similarity NPD1080 Approved
0.5851 Remote Similarity NPD713 Clinical (unspecified phase)
0.5851 Remote Similarity NPD1076 Approved
0.5851 Remote Similarity NPD1099 Approved
0.5851 Remote Similarity NPD5597 Approved
0.5851 Remote Similarity NPD5598 Approved
0.5851 Remote Similarity NPD528 Clinical (unspecified phase)
0.5851 Remote Similarity NPD9489 Approved
0.5851 Remote Similarity NPD1875 Phase 1
0.5851 Remote Similarity NPD4657 Approved
0.5851 Remote Similarity NPD1100 Approved
0.5851 Remote Similarity NPD2487 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