Structure

Physi-Chem Properties

Molecular Weight:  204.19
Volume:  251.53
LogP:  4.94
LogD:  4.15
LogS:  -4.525
# Rotatable Bonds:  3
TPSA:  0.0
# H-Bond Aceptor:  0
# H-Bond Donor:  0
# Rings:  1
# Heavy Atoms:  0

MedChem Properties

QED Drug-Likeness Score:  0.582
Synthetic Accessibility Score:  4.188
Fsp3:  0.6
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.559
MDCK Permeability:  2.1573114281636663e-05
Pgp-inhibitor:  0.213
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.887
30% Bioavailability (F30%):  0.019

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.083
Plasma Protein Binding (PPB):  78.09551239013672%
Volume Distribution (VD):  2.315
Pgp-substrate:  18.83026123046875%

ADMET: Metabolism

CYP1A2-inhibitor:  0.18
CYP1A2-substrate:  0.575
CYP2C19-inhibitor:  0.276
CYP2C19-substrate:  0.917
CYP2C9-inhibitor:  0.124
CYP2C9-substrate:  0.416
CYP2D6-inhibitor:  0.196
CYP2D6-substrate:  0.798
CYP3A4-inhibitor:  0.876
CYP3A4-substrate:  0.367

ADMET: Excretion

Clearance (CL):  7.887
Half-life (T1/2):  0.102

ADMET: Toxicity

hERG Blockers:  0.041
Human Hepatotoxicity (H-HT):  0.242
Drug-inuced Liver Injury (DILI):  0.031
AMES Toxicity:  0.004
Rat Oral Acute Toxicity:  0.052
Maximum Recommended Daily Dose:  0.648
Skin Sensitization:  0.327
Carcinogencity:  0.263
Eye Corrosion:  0.983
Eye Irritation:  0.971
Respiratory Toxicity:  0.214

Download Data

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

  Natural Product: NPC190232

Natural Product ID:  NPC190232
Common Name*:   (-)-Beta-Elemene
IUPAC Name:   (1S,2R,4S)-1-ethenyl-1-methyl-2,4-bis(prop-1-en-2-yl)cyclohexane
Synonyms:  
Standard InCHIKey:  OPFTUNCRGUEPRZ-RRFJBIMHSA-N
Standard InCHI:  InChI=1S/C15H24/c1-7-15(6)9-8-13(11(2)3)10-14(15)12(4)5/h7,13-14H,1-2,4,8-10H2,3,5-6H3/t13-,14+,15+/m0/s1
SMILES:  C=C[C@]1(C)CC[C@@H](C[C@@H]1C(=C)C)C(=C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL479707
PubChem CID:   6431151
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001550] Sesquiterpenoids
          • [CHEMONTID:0002872] Elemane sesquiterpenoids

*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
NPO27288 Citrus maxima Species Rutaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0031-9422(99)00119-3]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0040-4039(01)90945-1]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. rhizome n.a. DOI[10.1021/np100392m]
NPO24464 Nephthea brassica Species Nephtheidae Eukaryota n.a. Formosan soft coral n.a. PMID[10579864]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. fruit n.a. PMID[10606547]
NPO28256 Platycladus orientalis Species Cupressaceae Eukaryota Leaves and branches Soorkesh Valley, Gollestan, Iran n.a. PMID[15104493]
NPO28256 Platycladus orientalis Species Cupressaceae Eukaryota leaves Soorkesh Valley, Gollestan, Iran n.a. PMID[15104493]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota Rhizomes n.a. n.a. PMID[20879743]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[21807513]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota n.a. root n.a. PMID[23738470]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota n.a. rhizome n.a. PMID[23738470]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. PMID[24704449]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota Rhizomes n.a. n.a. PMID[25275213]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. PMID[26967731]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. Database[FooDB]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO27288 Citrus maxima Species Rutaceae Eukaryota n.a. n.a. Database[FooDB]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. Database[FooDB]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10082 Citrus unshiu Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO31073 Ligusticum chuanxiong Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota Fruits n.a. Database[Phenol-Explorer]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO27288 Citrus maxima Species Rutaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28256 Platycladus orientalis Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10082 Citrus unshiu Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27288 Citrus maxima Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10082 Citrus unshiu Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28256 Platycladus orientalis Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO31073 Ligusticum chuanxiong Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO27288 Citrus maxima Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28256 Platycladus orientalis Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO10082 Citrus unshiu Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27288 Citrus maxima Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25443 Citrus reticulata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24464 Nephthea brassica Species Nephtheidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10082 Citrus unshiu Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28256 Platycladus orientalis Species Cupressaceae 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
NPT139 Cell Line HT-29 Homo sapiens ED50 > 50.0 ug ml-1 PMID[552742]
NPT81 Cell Line A549 Homo sapiens ED50 > 50.0 ug ml-1 PMID[552742]
NPT91 Cell Line KB Homo sapiens ED50 > 50.0 ug ml-1 PMID[552742]
NPT168 Cell Line P388 Mus musculus ED50 = 0.92 ug ml-1 PMID[552742]

☑ 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 NPC190232 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 NPC105246
0.9024 High Similarity NPC193180
0.8864 High Similarity NPC124851
0.878 High Similarity NPC103290
0.8537 High Similarity NPC227632
0.8537 High Similarity NPC78551
0.8537 High Similarity NPC62086
0.8409 Intermediate Similarity NPC86683
0.8261 Intermediate Similarity NPC22765
0.8261 Intermediate Similarity NPC17518
0.8 Intermediate Similarity NPC114239
0.8 Intermediate Similarity NPC296337
0.8 Intermediate Similarity NPC241784
0.8 Intermediate Similarity NPC13991
0.7955 Intermediate Similarity NPC192529
0.7778 Intermediate Similarity NPC202189
0.7778 Intermediate Similarity NPC248411
0.7647 Intermediate Similarity NPC200258
0.7556 Intermediate Similarity NPC227670
0.7556 Intermediate Similarity NPC141777
0.7556 Intermediate Similarity NPC166362
0.75 Intermediate Similarity NPC39068
0.7347 Intermediate Similarity NPC200129
0.7347 Intermediate Similarity NPC476681
0.7333 Intermediate Similarity NPC177470
0.7308 Intermediate Similarity NPC469770
0.7273 Intermediate Similarity NPC246165
0.7255 Intermediate Similarity NPC474416
0.7255 Intermediate Similarity NPC127944
0.7234 Intermediate Similarity NPC229403
0.7222 Intermediate Similarity NPC469769
0.7209 Intermediate Similarity NPC229262
0.7209 Intermediate Similarity NPC139717
0.7209 Intermediate Similarity NPC297643
0.7174 Intermediate Similarity NPC86538
0.7174 Intermediate Similarity NPC109813
0.7174 Intermediate Similarity NPC60556
0.7111 Intermediate Similarity NPC144023
0.7083 Intermediate Similarity NPC323445
0.7059 Intermediate Similarity NPC473728
0.7037 Intermediate Similarity NPC474415
0.7037 Intermediate Similarity NPC474457
0.7037 Intermediate Similarity NPC474528
0.7037 Intermediate Similarity NPC475696
0.6981 Remote Similarity NPC123194
0.6977 Remote Similarity NPC76145
0.6977 Remote Similarity NPC34764
0.6977 Remote Similarity NPC190810
0.6964 Remote Similarity NPC176621
0.6923 Remote Similarity NPC476679
0.6909 Remote Similarity NPC60772
0.6889 Remote Similarity NPC183670
0.6875 Remote Similarity NPC49088
0.6863 Remote Similarity NPC236623
0.6852 Remote Similarity NPC264779
0.6842 Remote Similarity NPC469728
0.6809 Remote Similarity NPC23145
0.6809 Remote Similarity NPC474118
0.6809 Remote Similarity NPC90506
0.6809 Remote Similarity NPC51762
0.6809 Remote Similarity NPC90803
0.68 Remote Similarity NPC17810
0.6792 Remote Similarity NPC476683
0.6792 Remote Similarity NPC5626
0.6786 Remote Similarity NPC474420
0.6786 Remote Similarity NPC474454
0.6786 Remote Similarity NPC475716
0.6786 Remote Similarity NPC474455
0.6739 Remote Similarity NPC218918
0.6739 Remote Similarity NPC120926
0.6727 Remote Similarity NPC11130
0.6724 Remote Similarity NPC283247
0.6724 Remote Similarity NPC474086
0.6667 Remote Similarity NPC470893
0.661 Remote Similarity NPC469662
0.6607 Remote Similarity NPC189290
0.6607 Remote Similarity NPC474769
0.6604 Remote Similarity NPC14002
0.66 Remote Similarity NPC178644
0.6596 Remote Similarity NPC473912
0.6552 Remote Similarity NPC60565
0.6552 Remote Similarity NPC219621
0.6552 Remote Similarity NPC41160
0.65 Remote Similarity NPC64123
0.6491 Remote Similarity NPC309825
0.6491 Remote Similarity NPC152211
0.6491 Remote Similarity NPC28755
0.6444 Remote Similarity NPC48638
0.6444 Remote Similarity NPC239039
0.6444 Remote Similarity NPC45727
0.6441 Remote Similarity NPC202118
0.6441 Remote Similarity NPC197238
0.6429 Remote Similarity NPC470369
0.6429 Remote Similarity NPC115385
0.6429 Remote Similarity NPC470370
0.641 Remote Similarity NPC10183
0.6393 Remote Similarity NPC250977
0.6393 Remote Similarity NPC176171
0.6393 Remote Similarity NPC222366
0.6393 Remote Similarity NPC476039
0.6393 Remote Similarity NPC92327
0.6393 Remote Similarity NPC279434
0.6393 Remote Similarity NPC286669
0.6383 Remote Similarity NPC473614
0.6379 Remote Similarity NPC311809
0.6379 Remote Similarity NPC127582
0.6364 Remote Similarity NPC282119
0.6364 Remote Similarity NPC92224
0.6333 Remote Similarity NPC285371
0.6333 Remote Similarity NPC475124
0.6296 Remote Similarity NPC23117
0.629 Remote Similarity NPC176107
0.629 Remote Similarity NPC197805
0.6275 Remote Similarity NPC100445
0.6271 Remote Similarity NPC147524
0.625 Remote Similarity NPC318036
0.623 Remote Similarity NPC268039
0.623 Remote Similarity NPC163678
0.6207 Remote Similarity NPC472827
0.6207 Remote Similarity NPC276764
0.6207 Remote Similarity NPC472304
0.619 Remote Similarity NPC66577
0.619 Remote Similarity NPC188292
0.619 Remote Similarity NPC206088
0.619 Remote Similarity NPC260474
0.619 Remote Similarity NPC139785
0.6167 Remote Similarity NPC174956
0.6154 Remote Similarity NPC266539
0.6154 Remote Similarity NPC287191
0.6154 Remote Similarity NPC266144
0.6154 Remote Similarity NPC31891
0.614 Remote Similarity NPC173815
0.6129 Remote Similarity NPC476406
0.6129 Remote Similarity NPC259156
0.6129 Remote Similarity NPC149680
0.6129 Remote Similarity NPC37792
0.6129 Remote Similarity NPC242945
0.6129 Remote Similarity NPC323005
0.6111 Remote Similarity NPC179169
0.6111 Remote Similarity NPC181255
0.6111 Remote Similarity NPC35519
0.6111 Remote Similarity NPC306195
0.6111 Remote Similarity NPC157781
0.6102 Remote Similarity NPC270042
0.6102 Remote Similarity NPC317778
0.6102 Remote Similarity NPC135648
0.6094 Remote Similarity NPC182815
0.6094 Remote Similarity NPC476431
0.6087 Remote Similarity NPC266298
0.6066 Remote Similarity NPC6697
0.6066 Remote Similarity NPC68656
0.6066 Remote Similarity NPC52449
0.6066 Remote Similarity NPC169275
0.6066 Remote Similarity NPC329698
0.6066 Remote Similarity NPC101128
0.6066 Remote Similarity NPC473959
0.6047 Remote Similarity NPC213749
0.6034 Remote Similarity NPC56905
0.6034 Remote Similarity NPC308108
0.6034 Remote Similarity NPC324944
0.6034 Remote Similarity NPC170799
0.6034 Remote Similarity NPC27610
0.6034 Remote Similarity NPC311852
0.6032 Remote Similarity NPC171225
0.6032 Remote Similarity NPC193770
0.6032 Remote Similarity NPC290350
0.6032 Remote Similarity NPC4370
0.6 Remote Similarity NPC295777
0.6 Remote Similarity NPC79576
0.6 Remote Similarity NPC194208
0.6 Remote Similarity NPC69898
0.6 Remote Similarity NPC475728
0.6 Remote Similarity NPC213152
0.6 Remote Similarity NPC282694
0.5968 Remote Similarity NPC476737
0.5968 Remote Similarity NPC474768
0.5968 Remote Similarity NPC258595
0.5968 Remote Similarity NPC251118
0.5968 Remote Similarity NPC282619
0.5968 Remote Similarity NPC172613
0.5968 Remote Similarity NPC60837
0.5968 Remote Similarity NPC208198
0.5968 Remote Similarity NPC2728
0.5968 Remote Similarity NPC107258
0.5968 Remote Similarity NPC11555
0.5968 Remote Similarity NPC27243
0.5965 Remote Similarity NPC179024
0.5965 Remote Similarity NPC249645
0.5965 Remote Similarity NPC55412
0.5938 Remote Similarity NPC476945
0.5938 Remote Similarity NPC82477
0.5938 Remote Similarity NPC310992
0.5938 Remote Similarity NPC160209
0.5938 Remote Similarity NPC296697
0.5938 Remote Similarity NPC20610
0.5938 Remote Similarity NPC32055
0.5938 Remote Similarity NPC94192
0.5938 Remote Similarity NPC142754
0.5938 Remote Similarity NPC208999
0.5938 Remote Similarity NPC87141

  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 NPC190232 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
1.0 High Similarity NPD1799 Clinical (unspecified phase)
0.6977 Remote Similarity NPD319 Phase 1
0.68 Remote Similarity NPD8262 Approved
0.6034 Remote Similarity NPD287 Approved
0.5965 Remote Similarity NPD4219 Approved
0.5938 Remote Similarity NPD3621 Clinical (unspecified phase)
0.5846 Remote Similarity NPD4137 Phase 3
0.5758 Remote Similarity NPD4691 Approved
0.5758 Remote Similarity NPD4747 Approved
0.5758 Remote Similarity NPD6938 Clinical (unspecified phase)
0.5758 Remote Similarity NPD6939 Phase 2
0.5735 Remote Similarity NPD4785 Approved
0.5735 Remote Similarity NPD4784 Approved
0.5735 Remote Similarity NPD4058 Approved
0.5735 Remote Similarity NPD4687 Approved
0.5672 Remote Similarity NPD4243 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