Structure

Physi-Chem Properties

Molecular Weight:  278.19
Volume:  298.017
LogP:  3.795
LogD:  3.341
LogS:  -3.867
# Rotatable Bonds:  2
TPSA:  35.53
# H-Bond Aceptor:  3
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.679
Synthetic Accessibility Score:  4.233
Fsp3:  0.824
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.584
MDCK Permeability:  2.0886707716272213e-05
Pgp-inhibitor:  0.991
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.598
30% Bioavailability (F30%):  0.971

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.395
Plasma Protein Binding (PPB):  71.91065216064453%
Volume Distribution (VD):  1.787
Pgp-substrate:  34.459373474121094%

ADMET: Metabolism

CYP1A2-inhibitor:  0.261
CYP1A2-substrate:  0.112
CYP2C19-inhibitor:  0.194
CYP2C19-substrate:  0.795
CYP2C9-inhibitor:  0.181
CYP2C9-substrate:  0.096
CYP2D6-inhibitor:  0.835
CYP2D6-substrate:  0.234
CYP3A4-inhibitor:  0.655
CYP3A4-substrate:  0.409

ADMET: Excretion

Clearance (CL):  3.768
Half-life (T1/2):  0.263

ADMET: Toxicity

hERG Blockers:  0.065
Human Hepatotoxicity (H-HT):  0.696
Drug-inuced Liver Injury (DILI):  0.205
AMES Toxicity:  0.823
Rat Oral Acute Toxicity:  0.833
Maximum Recommended Daily Dose:  0.535
Skin Sensitization:  0.811
Carcinogencity:  0.975
Eye Corrosion:  0.935
Eye Irritation:  0.655
Respiratory Toxicity:  0.974

Download Data

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

  Natural Product: NPC12680

Natural Product ID:  NPC12680
Common Name*:   7-Deacetoxyolepupuane
IUPAC Name:   [(1S,5aS,9aS,9bR)-6,6,9a-trimethyl-1,4,5,5a,7,8,9,9b-octahydrobenzo[g][2]benzofuran-1-yl] acetate
Synonyms:   7-Deacetoxy-Olepupuane; 7-Deacetoxyolepupuane
Standard InCHIKey:  VTWFKCAENOAYPA-IVSAIRAKSA-N
Standard InCHI:  InChI=1S/C17H26O3/c1-11(18)20-15-14-12(10-19-15)6-7-13-16(2,3)8-5-9-17(13,14)4/h10,13-15H,5-9H2,1-4H3/t13-,14+,15-,17-/m0/s1
SMILES:  CC(=O)O[C@@H]1OC=C2[C@H]1[C@@]1(C)CCCC([C@@H]1CC2)(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL464204
PubChem CID:   126180
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001634] Naphthofurans

*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
NPO32617 dysidea sp. Species Dysideidae Eukaryota n.a. n.a. n.a. PMID[11374954]
NPO30670 Dysidea Genus Dysideidae Eukaryota n.a. n.a. n.a. PMID[11374954]
NPO32617 dysidea sp. Species Dysideidae Eukaryota n.a. n.a. n.a. PMID[15921404]
NPO32617 dysidea sp. Species Dysideidae Eukaryota n.a. n.a. n.a. PMID[1593283]
NPO32617 dysidea sp. Species Dysideidae Eukaryota n.a. n.a. n.a. PMID[18198840]
NPO32617 dysidea sp. Species Dysideidae Eukaryota n.a. at 1020 m depth from Chuuk Atoll, Federated States of Micronesia n.a. PMID[18824352]
NPO32617 dysidea sp. Species Dysideidae Eukaryota n.a. n.a. n.a. PMID[20230038]
NPO30670 Dysidea Genus Dysideidae Eukaryota n.a. n.a. n.a. PMID[21214221]
NPO32617 dysidea sp. Species Dysideidae Eukaryota n.a. n.a. n.a. PMID[26551342]
NPO32617 dysidea sp. Species Dysideidae Eukaryota n.a. n.a. n.a. PMID[26863083]
NPO32617 dysidea sp. Species Dysideidae Eukaryota n.a. n.a. n.a. PMID[27336796]
NPO32617 dysidea sp. Species Dysideidae Eukaryota n.a. n.a. n.a. PMID[32243140]
NPO32617 dysidea sp. Species Dysideidae Eukaryota n.a. Indo-Pacific n.a. PMID[7494145]
NPO30670 Dysidea Genus Dysideidae Eukaryota n.a. n.a. n.a. PMID[9392880]
NPO32617 dysidea sp. Species Dysideidae Eukaryota n.a. n.a. n.a. PMID[9748373]

☑ 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
NPT168 Cell Line P388 Mus musculus IC50 = 16.4 ug.mL-1 PMID[510021]
NPT773 Organism Photobacterium leiognathi Photobacterium leiognathi IC50 = 90000.0 nM PMID[510022]

☑ 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 NPC12680 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
0.8272 Intermediate Similarity NPC288952
0.8171 Intermediate Similarity NPC144069
0.7949 Intermediate Similarity NPC170561
0.7882 Intermediate Similarity NPC120539
0.7848 Intermediate Similarity NPC473685
0.7791 Intermediate Similarity NPC246860
0.7791 Intermediate Similarity NPC163902
0.7778 Intermediate Similarity NPC472440
0.7711 Intermediate Similarity NPC118266
0.7683 Intermediate Similarity NPC471367
0.7639 Intermediate Similarity NPC474768
0.759 Intermediate Similarity NPC472442
0.7586 Intermediate Similarity NPC12297
0.7528 Intermediate Similarity NPC164750
0.75 Intermediate Similarity NPC471369
0.7444 Intermediate Similarity NPC97867
0.7442 Intermediate Similarity NPC293044
0.7381 Intermediate Similarity NPC42586
0.7381 Intermediate Similarity NPC473251
0.7349 Intermediate Similarity NPC324243
0.7342 Intermediate Similarity NPC476601
0.7326 Intermediate Similarity NPC263079
0.7326 Intermediate Similarity NPC472809
0.7326 Intermediate Similarity NPC472810
0.7294 Intermediate Similarity NPC471368
0.7286 Intermediate Similarity NPC132998
0.7284 Intermediate Similarity NPC44083
0.7284 Intermediate Similarity NPC153987
0.7273 Intermediate Similarity NPC472811
0.7262 Intermediate Similarity NPC71626
0.7253 Intermediate Similarity NPC198549
0.7253 Intermediate Similarity NPC113976
0.7241 Intermediate Similarity NPC251528
0.7209 Intermediate Similarity NPC265580
0.7191 Intermediate Similarity NPC472812
0.7179 Intermediate Similarity NPC279241
0.7159 Intermediate Similarity NPC471370
0.7159 Intermediate Similarity NPC477782
0.7159 Intermediate Similarity NPC471371
0.7143 Intermediate Similarity NPC469
0.7143 Intermediate Similarity NPC325960
0.7143 Intermediate Similarity NPC91369
0.7143 Intermediate Similarity NPC319692
0.7125 Intermediate Similarity NPC92489
0.7111 Intermediate Similarity NPC469697
0.7111 Intermediate Similarity NPC470255
0.7111 Intermediate Similarity NPC324078
0.7111 Intermediate Similarity NPC477722
0.7108 Intermediate Similarity NPC475951
0.7093 Intermediate Similarity NPC244174
0.7089 Intermediate Similarity NPC474524
0.7089 Intermediate Similarity NPC475517
0.7079 Intermediate Similarity NPC65513
0.7079 Intermediate Similarity NPC477783
0.7073 Intermediate Similarity NPC100906
0.7073 Intermediate Similarity NPC305835
0.7073 Intermediate Similarity NPC471475
0.7073 Intermediate Similarity NPC47808
0.7059 Intermediate Similarity NPC96055
0.7059 Intermediate Similarity NPC318515
0.7051 Intermediate Similarity NPC72343
0.7045 Intermediate Similarity NPC470734
0.7045 Intermediate Similarity NPC50070
0.7037 Intermediate Similarity NPC283619
0.7037 Intermediate Similarity NPC189206
0.7037 Intermediate Similarity NPC84868
0.7033 Intermediate Similarity NPC230347
0.7033 Intermediate Similarity NPC286612
0.7033 Intermediate Similarity NPC275310
0.7024 Intermediate Similarity NPC200513
0.7 Intermediate Similarity NPC277721
0.7 Intermediate Similarity NPC267266
0.6989 Remote Similarity NPC474440
0.6988 Remote Similarity NPC206735
0.6988 Remote Similarity NPC170038
0.6988 Remote Similarity NPC304194
0.6988 Remote Similarity NPC475946
0.6977 Remote Similarity NPC300985
0.6974 Remote Similarity NPC469868
0.6966 Remote Similarity NPC469403
0.6962 Remote Similarity NPC476490
0.6962 Remote Similarity NPC476489
0.6957 Remote Similarity NPC94905
0.6957 Remote Similarity NPC8954
0.6957 Remote Similarity NPC162346
0.6951 Remote Similarity NPC35574
0.6941 Remote Similarity NPC311070
0.6932 Remote Similarity NPC474629
0.6923 Remote Similarity NPC104925
0.6923 Remote Similarity NPC128488
0.6923 Remote Similarity NPC298973
0.6923 Remote Similarity NPC41649
0.6923 Remote Similarity NPC88507
0.6923 Remote Similarity NPC304968
0.6914 Remote Similarity NPC41017
0.6905 Remote Similarity NPC209318
0.6905 Remote Similarity NPC223330
0.6905 Remote Similarity NPC149237
0.6905 Remote Similarity NPC142163
0.6905 Remote Similarity NPC108476
0.6897 Remote Similarity NPC173917
0.6889 Remote Similarity NPC477122
0.6883 Remote Similarity NPC36616
0.6883 Remote Similarity NPC290445
0.6882 Remote Similarity NPC204054
0.6882 Remote Similarity NPC257726
0.6875 Remote Similarity NPC238146
0.6875 Remote Similarity NPC166797
0.6875 Remote Similarity NPC71152
0.6867 Remote Similarity NPC476438
0.6867 Remote Similarity NPC118987
0.6867 Remote Similarity NPC17550
0.6867 Remote Similarity NPC192999
0.6866 Remote Similarity NPC142103
0.686 Remote Similarity NPC139566
0.6848 Remote Similarity NPC471372
0.6848 Remote Similarity NPC472441
0.6848 Remote Similarity NPC471362
0.6848 Remote Similarity NPC472189
0.6829 Remote Similarity NPC54996
0.6829 Remote Similarity NPC219809
0.6829 Remote Similarity NPC238227
0.6824 Remote Similarity NPC471218
0.6824 Remote Similarity NPC226988
0.6824 Remote Similarity NPC472504
0.6824 Remote Similarity NPC109938
0.6824 Remote Similarity NPC123880
0.6824 Remote Similarity NPC471159
0.6824 Remote Similarity NPC122945
0.6813 Remote Similarity NPC474835
0.6813 Remote Similarity NPC470656
0.6809 Remote Similarity NPC473154
0.6809 Remote Similarity NPC241657
0.6806 Remote Similarity NPC240206
0.68 Remote Similarity NPC469723
0.6786 Remote Similarity NPC469802
0.6786 Remote Similarity NPC10636
0.6786 Remote Similarity NPC233332
0.6786 Remote Similarity NPC195424
0.6782 Remote Similarity NPC217394
0.6782 Remote Similarity NPC106416
0.6782 Remote Similarity NPC65661
0.6782 Remote Similarity NPC329630
0.6782 Remote Similarity NPC30984
0.6782 Remote Similarity NPC476602
0.6782 Remote Similarity NPC86316
0.6782 Remote Similarity NPC474013
0.6774 Remote Similarity NPC112654
0.6774 Remote Similarity NPC311166
0.6774 Remote Similarity NPC171598
0.675 Remote Similarity NPC161187
0.675 Remote Similarity NPC330659
0.675 Remote Similarity NPC244708
0.6747 Remote Similarity NPC269543
0.6747 Remote Similarity NPC4827
0.6747 Remote Similarity NPC184737
0.6747 Remote Similarity NPC247783
0.6747 Remote Similarity NPC63020
0.6744 Remote Similarity NPC30502
0.6744 Remote Similarity NPC473742
0.6744 Remote Similarity NPC471037
0.6744 Remote Similarity NPC170862
0.6744 Remote Similarity NPC477124
0.6744 Remote Similarity NPC132386
0.6744 Remote Similarity NPC139206
0.6744 Remote Similarity NPC5280
0.6742 Remote Similarity NPC472378
0.6742 Remote Similarity NPC472302
0.6742 Remote Similarity NPC319030
0.6739 Remote Similarity NPC211238
0.6737 Remote Similarity NPC477716
0.6737 Remote Similarity NPC477720
0.6737 Remote Similarity NPC477721
0.6735 Remote Similarity NPC291414
0.6707 Remote Similarity NPC4509
0.6706 Remote Similarity NPC290495
0.6706 Remote Similarity NPC14203
0.6706 Remote Similarity NPC170303
0.6706 Remote Similarity NPC195334
0.6706 Remote Similarity NPC229584
0.6705 Remote Similarity NPC131813
0.6705 Remote Similarity NPC264127
0.6705 Remote Similarity NPC286153
0.6705 Remote Similarity NPC474062
0.6705 Remote Similarity NPC474970
0.6705 Remote Similarity NPC471219
0.6705 Remote Similarity NPC329692
0.6703 Remote Similarity NPC179517
0.6703 Remote Similarity NPC329842
0.6703 Remote Similarity NPC474631
0.6703 Remote Similarity NPC165904
0.6702 Remote Similarity NPC472188
0.6702 Remote Similarity NPC98112
0.6702 Remote Similarity NPC477719
0.6702 Remote Similarity NPC475709
0.6702 Remote Similarity NPC477718
0.6701 Remote Similarity NPC120009
0.6667 Remote Similarity NPC21064
0.6667 Remote Similarity NPC477717
0.6667 Remote Similarity NPC121072

  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 NPC12680 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
0.7024 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.6622 Remote Similarity NPD1145 Discontinued
0.6517 Remote Similarity NPD7334 Approved
0.6517 Remote Similarity NPD6409 Approved
0.6517 Remote Similarity NPD7146 Approved
0.6517 Remote Similarity NPD5330 Approved
0.6517 Remote Similarity NPD6684 Approved
0.6517 Remote Similarity NPD7521 Approved
0.6374 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6374 Remote Similarity NPD5737 Approved
0.6374 Remote Similarity NPD6672 Approved
0.6374 Remote Similarity NPD6903 Approved
0.6304 Remote Similarity NPD6051 Approved
0.6292 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6277 Remote Similarity NPD6399 Phase 3
0.6275 Remote Similarity NPD6686 Approved
0.6222 Remote Similarity NPD7520 Clinical (unspecified phase)
0.617 Remote Similarity NPD8034 Phase 2
0.617 Remote Similarity NPD8035 Phase 2
0.6154 Remote Similarity NPD6098 Approved
0.6118 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6071 Remote Similarity NPD6926 Approved
0.6071 Remote Similarity NPD6924 Approved
0.6067 Remote Similarity NPD3667 Approved
0.6024 Remote Similarity NPD5777 Approved
0.6022 Remote Similarity NPD5208 Approved
0.6 Remote Similarity NPD4788 Approved
0.6 Remote Similarity NPD6942 Approved
0.6 Remote Similarity NPD7339 Approved
0.596 Remote Similarity NPD4225 Approved
0.5957 Remote Similarity NPD6080 Approved
0.5957 Remote Similarity NPD6904 Approved
0.5957 Remote Similarity NPD6673 Approved
0.5934 Remote Similarity NPD3668 Phase 3
0.5934 Remote Similarity NPD4786 Approved
0.593 Remote Similarity NPD6933 Approved
0.5914 Remote Similarity NPD3573 Approved
0.5876 Remote Similarity NPD7901 Clinical (unspecified phase)
0.5876 Remote Similarity NPD7748 Approved
0.5876 Remote Similarity NPD7900 Approved
0.5865 Remote Similarity NPD6412 Phase 2
0.5859 Remote Similarity NPD6084 Phase 2
0.5859 Remote Similarity NPD6083 Phase 2
0.5843 Remote Similarity NPD4695 Discontinued
0.5833 Remote Similarity NPD7637 Suspended
0.5833 Remote Similarity NPD8133 Approved
0.5833 Remote Similarity NPD5693 Phase 1
0.5824 Remote Similarity NPD6695 Phase 3
0.5816 Remote Similarity NPD5695 Phase 3
0.5816 Remote Similarity NPD6356 Clinical (unspecified phase)
0.5814 Remote Similarity NPD3702 Approved
0.5814 Remote Similarity NPD8039 Approved
0.58 Remote Similarity NPD7638 Approved
0.58 Remote Similarity NPD5696 Approved
0.5783 Remote Similarity NPD6923 Approved
0.5783 Remote Similarity NPD6922 Approved
0.5766 Remote Similarity NPD7328 Approved
0.5766 Remote Similarity NPD7327 Approved
0.5761 Remote Similarity NPD3133 Approved
0.5761 Remote Similarity NPD3666 Approved
0.5761 Remote Similarity NPD7338 Clinical (unspecified phase)
0.5761 Remote Similarity NPD3665 Phase 1
0.5752 Remote Similarity NPD7503 Approved
0.5752 Remote Similarity NPD8033 Approved
0.575 Remote Similarity NPD5325 Clinical (unspecified phase)
0.5743 Remote Similarity NPD7640 Approved
0.5743 Remote Similarity NPD7639 Approved
0.573 Remote Similarity NPD4195 Approved
0.573 Remote Similarity NPD6929 Approved
0.573 Remote Similarity NPD7645 Phase 2
0.5729 Remote Similarity NPD5692 Phase 3
0.5729 Remote Similarity NPD5207 Approved
0.5714 Remote Similarity NPD7516 Approved
0.5714 Remote Similarity NPD7144 Approved
0.5714 Remote Similarity NPD6001 Approved
0.5714 Remote Similarity NPD7143 Approved
0.5714 Remote Similarity NPD5707 Approved
0.57 Remote Similarity NPD7902 Approved
0.5699 Remote Similarity NPD1694 Approved
0.5698 Remote Similarity NPD4785 Approved
0.5698 Remote Similarity NPD4784 Approved
0.567 Remote Similarity NPD5694 Approved
0.567 Remote Similarity NPD6411 Approved
0.567 Remote Similarity NPD7515 Phase 2
0.567 Remote Similarity NPD6050 Approved
0.5667 Remote Similarity NPD7525 Registered
0.5667 Remote Similarity NPD7509 Discontinued
0.5667 Remote Similarity NPD6931 Approved
0.5667 Remote Similarity NPD6930 Phase 2
0.5664 Remote Similarity NPD8294 Approved
0.5664 Remote Similarity NPD8377 Approved
0.5647 Remote Similarity NPD4243 Approved
0.5647 Remote Similarity NPD7151 Approved
0.5647 Remote Similarity NPD7152 Approved
0.5647 Remote Similarity NPD7150 Approved
0.5638 Remote Similarity NPD3618 Phase 1
0.5625 Remote Similarity NPD7285 Clinical (unspecified phase)
0.5619 Remote Similarity NPD6008 Approved
0.5618 Remote Similarity NPD3617 Approved
0.5614 Remote Similarity NPD8378 Approved
0.5614 Remote Similarity NPD8380 Approved
0.5614 Remote Similarity NPD8296 Approved
0.5614 Remote Similarity NPD8379 Approved
0.5614 Remote Similarity NPD8335 Approved
0.561 Remote Similarity NPD4224 Phase 2
0.5607 Remote Similarity NPD8132 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