Structure

Physi-Chem Properties

Molecular Weight:  120.09
Volume:  147.754
LogP:  3.593
LogD:  3.497
LogS:  -3.683
# Rotatable Bonds:  1
TPSA:  0.0
# H-Bond Aceptor:  0
# H-Bond Donor:  0
# Rings:  1
# Heavy Atoms:  0

MedChem Properties

QED Drug-Likeness Score:  0.534
Synthetic Accessibility Score:  1.13
Fsp3:  0.333
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -4.242
MDCK Permeability:  2.122902515111491e-05
Pgp-inhibitor:  0.009
Pgp-substrate:  0.005
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.257
30% Bioavailability (F30%):  0.41

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.896
Plasma Protein Binding (PPB):  92.10958099365234%
Volume Distribution (VD):  2.134
Pgp-substrate:  6.407780170440674%

ADMET: Metabolism

CYP1A2-inhibitor:  0.966
CYP1A2-substrate:  0.938
CYP2C19-inhibitor:  0.899
CYP2C19-substrate:  0.798
CYP2C9-inhibitor:  0.578
CYP2C9-substrate:  0.464
CYP2D6-inhibitor:  0.671
CYP2D6-substrate:  0.774
CYP3A4-inhibitor:  0.089
CYP3A4-substrate:  0.551

ADMET: Excretion

Clearance (CL):  10.736
Half-life (T1/2):  0.517

ADMET: Toxicity

hERG Blockers:  0.074
Human Hepatotoxicity (H-HT):  0.056
Drug-inuced Liver Injury (DILI):  0.099
AMES Toxicity:  0.023
Rat Oral Acute Toxicity:  0.037
Maximum Recommended Daily Dose:  0.041
Skin Sensitization:  0.371
Carcinogencity:  0.405
Eye Corrosion:  0.975
Eye Irritation:  0.994
Respiratory Toxicity:  0.066

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

  Natural Product: NPC248705

Natural Product ID:  NPC248705
Common Name*:   1-Ethyl-4-Methylbenzene
IUPAC Name:   1-ethyl-4-methylbenzene
Synonyms:  
Standard InCHIKey:  JRLPEMVDPFPYPJ-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C9H12/c1-3-9-6-4-8(2)5-7-9/h4-7H,3H2,1-2H3
SMILES:  CCc1ccc(cc1)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL195384
PubChem CID:   12160
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002279] Benzene and substituted derivatives
        • [CHEMONTID:0001091] Toluenes

*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
NPO9445 Crocus sativus Species Iridaceae Eukaryota n.a. n.a. n.a. DOI[10.1002/hlca.19270100148]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. cone n.a. PMID[10336650]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[10654410]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. root n.a. PMID[10843587]
NPO9445 Crocus sativus Species Iridaceae Eukaryota Petals n.a. n.a. PMID[15043425]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota Roots n.a. n.a. PMID[15568770]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[15679315]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[16252923]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. root n.a. PMID[16392664]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota roots Hualien Hsien, Taiwan 2003-JUL PMID[16933887]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. root n.a. PMID[16933887]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. cone n.a. PMID[17624889]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. root n.a. PMID[17951038]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[18175961]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[18611049]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[18768384]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[19476340]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[21912858]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. cone n.a. PMID[22111577]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. flower n.a. PMID[22166201]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[23790907]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[24295087]
NPO9445 Crocus sativus Species Iridaceae Eukaryota n.a. n.a. n.a. PMID[24338885]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[24948953]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[25564559]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[27575476]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[29154541]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota Roots n.a. n.a. PMID[30298740]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota Roots n.a. n.a. PMID[9868163]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. root n.a. Database[Article]
NPO9445 Crocus sativus Species Iridaceae Eukaryota n.a. n.a. Database[FooDB]
NPO9445 Crocus sativus Species Iridaceae Eukaryota n.a. n.a. Database[FooDB]
NPO9445 Crocus sativus Species Iridaceae Eukaryota Silk Stigma Style n.a. n.a. Database[FooDB]
NPO9445 Crocus sativus Species Iridaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9445 Crocus sativus Species Iridaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9445 Crocus sativus Species Iridaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9445 Crocus sativus Species Iridaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9445 Crocus sativus Species Iridaceae 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
NPT1066 Individual Protein Lysozyme Enterobacteria phage T4 Kd = 120000.0 nM PMID[470521]
NPT2 Others Unspecified Potency n.a. 67892.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 76176.9 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 10849.6 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 NPC248705 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
1.0 High Similarity NPC54368
0.9661 High Similarity NPC88566
0.9649 High Similarity NPC8235
0.95 High Similarity NPC198023
0.9474 High Similarity NPC120441
0.9474 High Similarity NPC212114
0.9474 High Similarity NPC65873
0.9474 High Similarity NPC300345
0.9344 High Similarity NPC178527
0.9322 High Similarity NPC210849
0.9322 High Similarity NPC135924
0.9322 High Similarity NPC150196
0.9298 High Similarity NPC198841
0.9298 High Similarity NPC269586
0.9194 High Similarity NPC267443
0.9194 High Similarity NPC6107
0.9167 High Similarity NPC29680
0.9153 High Similarity NPC147062
0.9123 High Similarity NPC149436
0.9123 High Similarity NPC277704
0.9032 High Similarity NPC289915
0.9032 High Similarity NPC113837
0.9 High Similarity NPC246588
0.9 High Similarity NPC310758
0.9 High Similarity NPC238023
0.8983 High Similarity NPC64270
0.8871 High Similarity NPC155172
0.8871 High Similarity NPC32312
0.8833 High Similarity NPC169110
0.871 High Similarity NPC45756
0.871 High Similarity NPC113670
0.8667 High Similarity NPC114327
0.8667 High Similarity NPC36357
0.8636 High Similarity NPC158028
0.8636 High Similarity NPC135433
0.8636 High Similarity NPC87099
0.8636 High Similarity NPC1008
0.8636 High Similarity NPC39799
0.8636 High Similarity NPC226999
0.8636 High Similarity NPC193578
0.8636 High Similarity NPC280135
0.8548 High Similarity NPC66517
0.8548 High Similarity NPC22786
0.8548 High Similarity NPC71009
0.8507 High Similarity NPC54269
0.8413 Intermediate Similarity NPC21211
0.8333 Intermediate Similarity NPC213570
0.8333 Intermediate Similarity NPC246822
0.8333 Intermediate Similarity NPC139416
0.8281 Intermediate Similarity NPC291066
0.8261 Intermediate Similarity NPC307195
0.8261 Intermediate Similarity NPC276699
0.8254 Intermediate Similarity NPC200745
0.8209 Intermediate Similarity NPC72670
0.8143 Intermediate Similarity NPC110264
0.8125 Intermediate Similarity NPC50266
0.8116 Intermediate Similarity NPC96835
0.8116 Intermediate Similarity NPC258492
0.8095 Intermediate Similarity NPC45255
0.806 Intermediate Similarity NPC473206
0.8028 Intermediate Similarity NPC249018
0.8028 Intermediate Similarity NPC3190
0.8028 Intermediate Similarity NPC290638
0.8 Intermediate Similarity NPC264470
0.7971 Intermediate Similarity NPC212463
0.7941 Intermediate Similarity NPC263385
0.7941 Intermediate Similarity NPC251490
0.7937 Intermediate Similarity NPC147578
0.7917 Intermediate Similarity NPC103488
0.791 Intermediate Similarity NPC22760
0.791 Intermediate Similarity NPC311343
0.7879 Intermediate Similarity NPC36440
0.7826 Intermediate Similarity NPC74458
0.7812 Intermediate Similarity NPC200624
0.7808 Intermediate Similarity NPC159661
0.7794 Intermediate Similarity NPC98880
0.7794 Intermediate Similarity NPC297358
0.7794 Intermediate Similarity NPC200936
0.7746 Intermediate Similarity NPC189371
0.7714 Intermediate Similarity NPC285679
0.7714 Intermediate Similarity NPC1901
0.7703 Intermediate Similarity NPC315216
0.7703 Intermediate Similarity NPC157055
0.7703 Intermediate Similarity NPC17408
0.7703 Intermediate Similarity NPC285716
0.7681 Intermediate Similarity NPC95289
0.7681 Intermediate Similarity NPC229235
0.7671 Intermediate Similarity NPC66270
0.7671 Intermediate Similarity NPC245896
0.7647 Intermediate Similarity NPC82770
0.7647 Intermediate Similarity NPC78954
0.7647 Intermediate Similarity NPC239931
0.7606 Intermediate Similarity NPC112609
0.7606 Intermediate Similarity NPC122327
0.7606 Intermediate Similarity NPC113000
0.76 Intermediate Similarity NPC145053
0.76 Intermediate Similarity NPC242628
0.7571 Intermediate Similarity NPC326200
0.7571 Intermediate Similarity NPC208302
0.7544 Intermediate Similarity NPC11150
0.7536 Intermediate Similarity NPC5324
0.7536 Intermediate Similarity NPC16190
0.7536 Intermediate Similarity NPC235059
0.7536 Intermediate Similarity NPC169222
0.7534 Intermediate Similarity NPC298023
0.75 Intermediate Similarity NPC230068
0.75 Intermediate Similarity NPC52330
0.7467 Intermediate Similarity NPC50063
0.7465 Intermediate Similarity NPC271437
0.7465 Intermediate Similarity NPC244738
0.7432 Intermediate Similarity NPC50192
0.7432 Intermediate Similarity NPC224544
0.7403 Intermediate Similarity NPC197581
0.7397 Intermediate Similarity NPC139658
0.7361 Intermediate Similarity NPC108218
0.7361 Intermediate Similarity NPC208075
0.7324 Intermediate Similarity NPC155429
0.7308 Intermediate Similarity NPC267704
0.7308 Intermediate Similarity NPC168855
0.7297 Intermediate Similarity NPC325662
0.7297 Intermediate Similarity NPC9796
0.7297 Intermediate Similarity NPC98269
0.726 Intermediate Similarity NPC98976
0.7237 Intermediate Similarity NPC328178
0.7237 Intermediate Similarity NPC190567
0.7215 Intermediate Similarity NPC474354
0.7215 Intermediate Similarity NPC252067
0.72 Intermediate Similarity NPC255345
0.72 Intermediate Similarity NPC137847
0.72 Intermediate Similarity NPC36342
0.72 Intermediate Similarity NPC2785
0.72 Intermediate Similarity NPC285470
0.72 Intermediate Similarity NPC76455
0.7183 Intermediate Similarity NPC219246
0.7162 Intermediate Similarity NPC175393
0.7162 Intermediate Similarity NPC271642
0.7143 Intermediate Similarity NPC231986
0.7143 Intermediate Similarity NPC100039
0.7143 Intermediate Similarity NPC181786
0.7143 Intermediate Similarity NPC133050
0.7125 Intermediate Similarity NPC160339
0.7125 Intermediate Similarity NPC474211
0.7125 Intermediate Similarity NPC93843
0.7125 Intermediate Similarity NPC243166
0.7125 Intermediate Similarity NPC307
0.7105 Intermediate Similarity NPC170484
0.7105 Intermediate Similarity NPC272260
0.7105 Intermediate Similarity NPC300205
0.7067 Intermediate Similarity NPC329318
0.7067 Intermediate Similarity NPC3672
0.7067 Intermediate Similarity NPC287790
0.7067 Intermediate Similarity NPC245966
0.7051 Intermediate Similarity NPC106313
0.7037 Intermediate Similarity NPC69057
0.7037 Intermediate Similarity NPC60408
0.7027 Intermediate Similarity NPC206800
0.7027 Intermediate Similarity NPC32203
0.7013 Intermediate Similarity NPC184030
0.7013 Intermediate Similarity NPC95868
0.7013 Intermediate Similarity NPC164086
0.7013 Intermediate Similarity NPC477703
0.7013 Intermediate Similarity NPC121800
0.7013 Intermediate Similarity NPC164449
0.6974 Remote Similarity NPC12857
0.6962 Remote Similarity NPC477770
0.6951 Remote Similarity NPC153308
0.6933 Remote Similarity NPC302129
0.6923 Remote Similarity NPC273033
0.6923 Remote Similarity NPC12936
0.6914 Remote Similarity NPC164526
0.6892 Remote Similarity NPC299134
0.6883 Remote Similarity NPC139901
0.6883 Remote Similarity NPC78517
0.6883 Remote Similarity NPC469894
0.6883 Remote Similarity NPC167577
0.6883 Remote Similarity NPC151405
0.6875 Remote Similarity NPC95429
0.6875 Remote Similarity NPC304538
0.6875 Remote Similarity NPC133162
0.6867 Remote Similarity NPC298115
0.6867 Remote Similarity NPC1793
0.6849 Remote Similarity NPC125144
0.6849 Remote Similarity NPC121708
0.6842 Remote Similarity NPC179726
0.6835 Remote Similarity NPC121478
0.6835 Remote Similarity NPC329319
0.6835 Remote Similarity NPC14326
0.6835 Remote Similarity NPC99394
0.6835 Remote Similarity NPC73637
0.6835 Remote Similarity NPC103326
0.6835 Remote Similarity NPC87299
0.6835 Remote Similarity NPC103387
0.6835 Remote Similarity NPC323103
0.6818 Remote Similarity NPC469807
0.6795 Remote Similarity NPC127343
0.6795 Remote Similarity NPC192623
0.6795 Remote Similarity NPC309279
0.6795 Remote Similarity NPC475289
0.6795 Remote Similarity NPC475573
0.6795 Remote Similarity NPC71664

  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 NPC248705 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
0.871 High Similarity NPD675 Discontinued
0.8281 Intermediate Similarity NPD173 Clinical (unspecified phase)
0.8088 Intermediate Similarity NPD294 Approved
0.8088 Intermediate Similarity NPD292 Approved
0.7794 Intermediate Similarity NPD9497 Clinical (unspecified phase)
0.7794 Intermediate Similarity NPD1673 Approved
0.7606 Intermediate Similarity NPD80 Approved
0.7606 Intermediate Similarity NPD9591 Approved
0.7606 Intermediate Similarity NPD9588 Approved
0.7606 Intermediate Similarity NPD9592 Approved
0.7606 Intermediate Similarity NPD9594 Approved
0.7606 Intermediate Similarity NPD9593 Approved
0.7606 Intermediate Similarity NPD9590 Approved
0.7606 Intermediate Similarity NPD9589 Approved
0.7465 Intermediate Similarity NPD9728 Phase 1
0.7361 Intermediate Similarity NPD505 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD590 Approved
0.7333 Intermediate Similarity NPD589 Approved
0.7297 Intermediate Similarity NPD4144 Approved
0.7297 Intermediate Similarity NPD4147 Approved
0.7237 Intermediate Similarity NPD3981 Approved
0.7237 Intermediate Similarity NPD3979 Approved
0.7237 Intermediate Similarity NPD260 Discontinued
0.7237 Intermediate Similarity NPD3904 Approved
0.7237 Intermediate Similarity NPD3903 Approved
0.72 Intermediate Similarity NPD79 Approved
0.72 Intermediate Similarity NPD9563 Approved
0.72 Intermediate Similarity NPD293 Approved
0.72 Intermediate Similarity NPD295 Approved
0.72 Intermediate Similarity NPD296 Approved
0.72 Intermediate Similarity NPD9564 Approved
0.7179 Intermediate Similarity NPD5288 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD3035 Approved
0.7143 Intermediate Similarity NPD4027 Approved
0.7143 Intermediate Similarity NPD4026 Approved
0.7105 Intermediate Similarity NPD1053 Approved
0.7105 Intermediate Similarity NPD1052 Approved
0.7105 Intermediate Similarity NPD1475 Approved
0.7105 Intermediate Similarity NPD1051 Approved
0.7089 Intermediate Similarity NPD4544 Approved
0.7067 Intermediate Similarity NPD603 Approved
0.7051 Intermediate Similarity NPD4701 Clinical (unspecified phase)
0.7051 Intermediate Similarity NPD4169 Approved
0.7051 Intermediate Similarity NPD4170 Approved
0.7037 Intermediate Similarity NPD1087 Approved
0.7027 Intermediate Similarity NPD9716 Approved
0.7013 Intermediate Similarity NPD5372 Approved
0.7013 Intermediate Similarity NPD5371 Approved
0.7013 Intermediate Similarity NPD1617 Discontinued
0.7013 Intermediate Similarity NPD1507 Clinical (unspecified phase)
0.6974 Remote Similarity NPD225 Approved
0.6974 Remote Similarity NPD9397 Approved
0.6974 Remote Similarity NPD9393 Approved
0.6974 Remote Similarity NPD227 Approved
0.6962 Remote Similarity NPD2001 Discontinued
0.6962 Remote Similarity NPD4635 Approved
0.6962 Remote Similarity NPD262 Approved
0.6962 Remote Similarity NPD263 Approved
0.6951 Remote Similarity NPD1101 Approved
0.6923 Remote Similarity NPD942 Approved
0.6923 Remote Similarity NPD472 Approved
0.6914 Remote Similarity NPD3099 Discontinued
0.6883 Remote Similarity NPD507 Approved
0.6883 Remote Similarity NPD508 Approved
0.6875 Remote Similarity NPD3429 Approved
0.6875 Remote Similarity NPD3427 Approved
0.6875 Remote Similarity NPD5178 Approved
0.6867 Remote Similarity NPD771 Phase 3
0.6867 Remote Similarity NPD800 Approved
0.6795 Remote Similarity NPD914 Suspended
0.679 Remote Similarity NPD2205 Approved
0.679 Remote Similarity NPD5734 Clinical (unspecified phase)
0.679 Remote Similarity NPD2208 Approved
0.6786 Remote Similarity NPD1090 Approved
0.6786 Remote Similarity NPD1089 Approved
0.6786 Remote Similarity NPD1086 Approved
0.675 Remote Similarity NPD3971 Phase 1
0.675 Remote Similarity NPD831 Approved
0.675 Remote Similarity NPD1185 Approved
0.675 Remote Similarity NPD830 Approved
0.6709 Remote Similarity NPD226 Approved
0.6707 Remote Similarity NPD4409 Approved
0.6707 Remote Similarity NPD4406 Approved
0.6707 Remote Similarity NPD4636 Approved
0.6667 Remote Similarity NPD9490 Approved
0.6667 Remote Similarity NPD9395 Approved
0.6667 Remote Similarity NPD785 Approved
0.6667 Remote Similarity NPD2538 Approved
0.6667 Remote Similarity NPD2539 Approved
0.6628 Remote Similarity NPD1088 Approved
0.6627 Remote Similarity NPD782 Approved
0.6627 Remote Similarity NPD4146 Approved
0.6627 Remote Similarity NPD2002 Discontinued
0.6627 Remote Similarity NPD650 Approved
0.6627 Remote Similarity NPD4145 Approved
0.6627 Remote Similarity NPD783 Approved
0.6627 Remote Similarity NPD781 Approved
0.6627 Remote Similarity NPD3426 Approved
0.6627 Remote Similarity NPD780 Approved
0.6627 Remote Similarity NPD3428 Approved
0.6623 Remote Similarity NPD9294 Approved
0.6585 Remote Similarity NPD5916 Discontinued
0.6552 Remote Similarity NPD1409 Phase 3
0.6552 Remote Similarity NPD1563 Approved
0.6552 Remote Similarity NPD3719 Approved
0.6552 Remote Similarity NPD3718 Approved
0.6548 Remote Similarity NPD5675 Discontinued
0.6548 Remote Similarity NPD3345 Approved
0.6543 Remote Similarity NPD4000 Phase 3
0.6543 Remote Similarity NPD1800 Clinical (unspecified phase)
0.6543 Remote Similarity NPD9491 Approved
0.6512 Remote Similarity NPD1239 Approved
0.6512 Remote Similarity NPD7609 Phase 3
0.6508 Remote Similarity NPD9072 Clinical (unspecified phase)
0.6506 Remote Similarity NPD5252 Clinical (unspecified phase)
0.6477 Remote Similarity NPD4814 Discontinued
0.6477 Remote Similarity NPD1693 Approved
0.6477 Remote Similarity NPD6049 Phase 2
0.6477 Remote Similarity NPD6048 Clinical (unspecified phase)
0.6471 Remote Similarity NPD5347 Phase 2
0.6471 Remote Similarity NPD5346 Phase 2
0.6471 Remote Similarity NPD5656 Clinical (unspecified phase)
0.6437 Remote Similarity NPD7631 Approved
0.6429 Remote Similarity NPD506 Clinical (unspecified phase)
0.6429 Remote Similarity NPD4793 Discontinued
0.6404 Remote Similarity NPD1989 Approved
0.6404 Remote Similarity NPD844 Approved
0.6404 Remote Similarity NPD3093 Approved
0.6395 Remote Similarity NPD5915 Approved
0.6395 Remote Similarity NPD3344 Approved
0.6395 Remote Similarity NPD3672 Approved
0.6395 Remote Similarity NPD2811 Clinical (unspecified phase)
0.6395 Remote Similarity NPD3673 Approved
0.6395 Remote Similarity NPD4728 Approved
0.6395 Remote Similarity NPD3346 Approved
0.6386 Remote Similarity NPD9505 Clinical (unspecified phase)
0.6364 Remote Similarity NPD2878 Approved
0.6364 Remote Similarity NPD3980 Approved
0.6364 Remote Similarity NPD3982 Approved
0.6353 Remote Similarity NPD531 Approved
0.6341 Remote Similarity NPD423 Phase 3
0.6333 Remote Similarity NPD1564 Approved
0.6333 Remote Similarity NPD1565 Approved
0.6333 Remote Similarity NPD1566 Phase 3
0.6333 Remote Similarity NPD288 Approved
0.6333 Remote Similarity NPD5597 Approved
0.6333 Remote Similarity NPD3495 Discontinued
0.6333 Remote Similarity NPD5598 Approved
0.6322 Remote Similarity NPD3000 Approved
0.6322 Remote Similarity NPD2997 Approved
0.6322 Remote Similarity NPD530 Approved
0.6322 Remote Similarity NPD517 Discontinued
0.6322 Remote Similarity NPD4543 Discontinued
0.6322 Remote Similarity NPD2998 Approved
0.631 Remote Similarity NPD1697 Approved
0.631 Remote Similarity NPD305 Approved
0.631 Remote Similarity NPD304 Approved
0.6279 Remote Similarity NPD1628 Approved
0.6279 Remote Similarity NPD1629 Approved
0.6264 Remote Similarity NPD4813 Approved
0.6264 Remote Similarity NPD4263 Approved
0.625 Remote Similarity NPD752 Approved
0.625 Remote Similarity NPD4408 Approved
0.625 Remote Similarity NPD4405 Approved
0.625 Remote Similarity NPD4407 Approved
0.6235 Remote Similarity NPD9538 Approved
0.6235 Remote Similarity NPD1282 Approved
0.6222 Remote Similarity NPD6472 Discontinued
0.6196 Remote Similarity NPD2066 Phase 3
0.6196 Remote Similarity NPD4737 Phase 2
0.619 Remote Similarity NPD111 Approved
0.618 Remote Similarity NPD5122 Clinical (unspecified phase)
0.618 Remote Similarity NPD4545 Approved
0.618 Remote Similarity NPD719 Approved
0.618 Remote Similarity NPD4542 Approved
0.618 Remote Similarity NPD720 Approved
0.618 Remote Similarity NPD845 Approved
0.6163 Remote Similarity NPD588 Approved
0.6163 Remote Similarity NPD587 Approved
0.6154 Remote Similarity NPD713 Clinical (unspecified phase)
0.6136 Remote Similarity NPD7160 Approved
0.6129 Remote Similarity NPD6354 Discontinued
0.6129 Remote Similarity NPD1616 Discontinued
0.6111 Remote Similarity NPD1432 Clinical (unspecified phase)
0.6111 Remote Similarity NPD4094 Approved
0.6111 Remote Similarity NPD5554 Approved
0.6111 Remote Similarity NPD2655 Approved
0.6111 Remote Similarity NPD7344 Phase 1
0.6111 Remote Similarity NPD2656 Approved
0.6111 Remote Similarity NPD7343 Discovery
0.6098 Remote Similarity NPD9250 Approved
0.6092 Remote Similarity NPD9 Approved
0.6092 Remote Similarity NPD297 Approved
0.6087 Remote Similarity NPD5832 Phase 3
0.6067 Remote Similarity NPD6690 Approved
0.6067 Remote Similarity NPD1508 Approved
0.6067 Remote Similarity NPD1812 Approved
0.6067 Remote Similarity NPD1814 Approved
0.6064 Remote Similarity NPD2193 Phase 2
0.6064 Remote Similarity NPD4734 Approved

  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