Structure

Physi-Chem Properties

Molecular Weight:  414.36
Volume:  466.833
LogP:  4.985
LogD:  3.727
LogS:  -5.169
# Rotatable Bonds:  3
TPSA:  35.5
# H-Bond Aceptor:  3
# H-Bond Donor:  2
# Rings:  4
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.68
Synthetic Accessibility Score:  5.145
Fsp3:  0.852
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:  -5.022
MDCK Permeability:  1.4426265806832816e-05
Pgp-inhibitor:  0.999
Pgp-substrate:  0.35
Human Intestinal Absorption (HIA):  0.032
20% Bioavailability (F20%):  0.892
30% Bioavailability (F30%):  0.625

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.101
Plasma Protein Binding (PPB):  64.03089141845703%
Volume Distribution (VD):  1.732
Pgp-substrate:  40.249908447265625%

ADMET: Metabolism

CYP1A2-inhibitor:  0.017
CYP1A2-substrate:  0.148
CYP2C19-inhibitor:  0.049
CYP2C19-substrate:  0.973
CYP2C9-inhibitor:  0.06
CYP2C9-substrate:  0.148
CYP2D6-inhibitor:  0.68
CYP2D6-substrate:  0.907
CYP3A4-inhibitor:  0.609
CYP3A4-substrate:  0.873

ADMET: Excretion

Clearance (CL):  6.06
Half-life (T1/2):  0.19

ADMET: Toxicity

hERG Blockers:  0.077
Human Hepatotoxicity (H-HT):  0.661
Drug-inuced Liver Injury (DILI):  0.012
AMES Toxicity:  0.003
Rat Oral Acute Toxicity:  0.737
Maximum Recommended Daily Dose:  0.975
Skin Sensitization:  0.873
Carcinogencity:  0.145
Eye Corrosion:  0.003
Eye Irritation:  0.011
Respiratory Toxicity:  0.981

Download Data

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

  Natural Product: NPC118275

Natural Product ID:  NPC118275
Common Name*:   Buxaminol C
IUPAC Name:   n.a.
Synonyms:   Buxaminol C
Standard InCHIKey:  UFOMWAWIEKKLJS-KBVVDYDXSA-N
Standard InCHI:  InChI=1S/C27H46N2O/c1-17(29(7)8)24-22(30)16-27(5)21-11-10-20-18(9-12-23(28-6)25(20,2)3)15-19(21)13-14-26(24,27)4/h13,15,17,20-24,28,30H,9-12,14,16H2,1-8H3/t17-,20+,21+,22+,23-,24-,26+,27-/m0/s1
SMILES:  C[C@@H]([C@H]1[C@@H](C[C@@]2(C)[C@@H]3CC[C@@H]4C(=CC3=CC[C@]12C)CC[C@@H](C4(C)C)NC)O)N(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1651038
PubChem CID:   10811757
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000258] Steroids and steroid derivatives
        • [CHEMONTID:0002724] Steroidal alkaloids
          • [CHEMONTID:0002726] Buxus alkaloids

*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
NPO27255 Macaranga alnifolia Species Euphorbiaceae Eukaryota n.a. leaf n.a. DOI[10.1016/0031-9422(92)80315-6]
NPO27255 Macaranga alnifolia Species Euphorbiaceae Eukaryota n.a. Madagascar rainforest n.a. PMID[17326683]
NPO27255 Macaranga alnifolia Species Euphorbiaceae Eukaryota n.a. fruit n.a. PMID[17326683]
NPO26132 Buxus natalensis Species Buxaceae Eukaryota n.a. uMhalanga Rocks nature reserve, Durban, South Africa 2007-FEB PMID[20954721]
NPO26132 Buxus natalensis Species Buxaceae Eukaryota n.a. bark n.a. PMID[20954721]
NPO27700 Alphitonia excelsa Species Rhamnaceae Eukaryota n.a. xylem n.a. PMID[21992235]
NPO4617 Tanacetum cinerariifolium Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[24253739]
NPO27999 Aconitum nagarum Species Ranunculaceae Eukaryota n.a. root n.a. Europe PMC[335013]
NPO5507 Eubotryoides grayana Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4617 Tanacetum cinerariifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27700 Alphitonia excelsa Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5507 Eubotryoides grayana Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27615 Ambrosia deltoidea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26132 Buxus natalensis Species Buxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27999 Aconitum nagarum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27765 Bryopsis plumosa Species Bryopsidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27255 Macaranga alnifolia Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4617 Tanacetum cinerariifolium Species Asteraceae 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
NPT204 Individual Protein Acetylcholinesterase Homo sapiens IC50 = 40000.0 nM PMID[527724]

☑ 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 NPC118275 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
0.9462 High Similarity NPC311164
0.9462 High Similarity NPC272732
0.8687 High Similarity NPC135799
0.8155 Intermediate Similarity NPC176012
0.8119 Intermediate Similarity NPC474164
0.8113 Intermediate Similarity NPC159367
0.7905 Intermediate Similarity NPC241879
0.7843 Intermediate Similarity NPC476903
0.77 Intermediate Similarity NPC84171
0.7576 Intermediate Similarity NPC21035
0.7551 Intermediate Similarity NPC75810
0.7545 Intermediate Similarity NPC85001
0.7545 Intermediate Similarity NPC147835
0.7545 Intermediate Similarity NPC253645
0.7545 Intermediate Similarity NPC95920
0.7419 Intermediate Similarity NPC125828
0.7407 Intermediate Similarity NPC98765
0.7358 Intermediate Similarity NPC91604
0.7315 Intermediate Similarity NPC50815
0.7315 Intermediate Similarity NPC471083
0.729 Intermediate Similarity NPC275686
0.7264 Intermediate Similarity NPC140300
0.7207 Intermediate Similarity NPC244982
0.7207 Intermediate Similarity NPC25340
0.7207 Intermediate Similarity NPC476756
0.7182 Intermediate Similarity NPC212874
0.7156 Intermediate Similarity NPC247060
0.7155 Intermediate Similarity NPC304646
0.7155 Intermediate Similarity NPC28280
0.7105 Intermediate Similarity NPC79238
0.7091 Intermediate Similarity NPC90538
0.7018 Intermediate Similarity NPC472313
0.7009 Intermediate Similarity NPC289140
0.6981 Remote Similarity NPC280710
0.6981 Remote Similarity NPC243985
0.6964 Remote Similarity NPC233256
0.6964 Remote Similarity NPC55462
0.6964 Remote Similarity NPC195841
0.6957 Remote Similarity NPC474459
0.6937 Remote Similarity NPC474583
0.6903 Remote Similarity NPC46981
0.69 Remote Similarity NPC201852
0.6897 Remote Similarity NPC56796
0.6897 Remote Similarity NPC474452
0.6887 Remote Similarity NPC93027
0.6847 Remote Similarity NPC476755
0.6842 Remote Similarity NPC474140
0.6837 Remote Similarity NPC186191
0.6837 Remote Similarity NPC477514
0.6837 Remote Similarity NPC205455
0.6837 Remote Similarity NPC307965
0.6837 Remote Similarity NPC477522
0.6837 Remote Similarity NPC18603
0.6837 Remote Similarity NPC76931
0.6833 Remote Similarity NPC35037
0.6829 Remote Similarity NPC296686
0.68 Remote Similarity NPC118329
0.68 Remote Similarity NPC152039
0.68 Remote Similarity NPC329782
0.6789 Remote Similarity NPC240650
0.6768 Remote Similarity NPC211322
0.6768 Remote Similarity NPC1319
0.6752 Remote Similarity NPC124358
0.6733 Remote Similarity NPC472312
0.6733 Remote Similarity NPC20853
0.6724 Remote Similarity NPC472359
0.6701 Remote Similarity NPC471723
0.6701 Remote Similarity NPC285893
0.6701 Remote Similarity NPC141071
0.6701 Remote Similarity NPC22105
0.6701 Remote Similarity NPC288035
0.6701 Remote Similarity NPC230301
0.6701 Remote Similarity NPC257347
0.6701 Remote Similarity NPC134847
0.6701 Remote Similarity NPC162742
0.6701 Remote Similarity NPC304309
0.6701 Remote Similarity NPC28657
0.6701 Remote Similarity NPC136188
0.6701 Remote Similarity NPC471468
0.67 Remote Similarity NPC26117
0.67 Remote Similarity NPC12035
0.6696 Remote Similarity NPC58200
0.6667 Remote Similarity NPC478138
0.6667 Remote Similarity NPC318136
0.6667 Remote Similarity NPC86906
0.6637 Remote Similarity NPC473254
0.6634 Remote Similarity NPC474122
0.6633 Remote Similarity NPC134330
0.6633 Remote Similarity NPC189883
0.6633 Remote Similarity NPC321381
0.6633 Remote Similarity NPC321016
0.6633 Remote Similarity NPC46160
0.6633 Remote Similarity NPC96319
0.6633 Remote Similarity NPC247325
0.6633 Remote Similarity NPC107059
0.6633 Remote Similarity NPC202642
0.6633 Remote Similarity NPC240604
0.6633 Remote Similarity NPC470362
0.6633 Remote Similarity NPC300324
0.6633 Remote Similarity NPC113733
0.6633 Remote Similarity NPC244488
0.6633 Remote Similarity NPC129165
0.6612 Remote Similarity NPC474006
0.6606 Remote Similarity NPC476261
0.6606 Remote Similarity NPC119225
0.6606 Remote Similarity NPC25033
0.6606 Remote Similarity NPC471635
0.6606 Remote Similarity NPC470382
0.6598 Remote Similarity NPC27395
0.6598 Remote Similarity NPC329090
0.6598 Remote Similarity NPC476904
0.6596 Remote Similarity NPC160209
0.6587 Remote Similarity NPC317654
0.6587 Remote Similarity NPC96010
0.6579 Remote Similarity NPC475239
0.6571 Remote Similarity NPC271967
0.6569 Remote Similarity NPC202389
0.6569 Remote Similarity NPC1272
0.6569 Remote Similarity NPC470614
0.6566 Remote Similarity NPC198968
0.6566 Remote Similarity NPC34019
0.6566 Remote Similarity NPC214570
0.6566 Remote Similarity NPC318495
0.6566 Remote Similarity NPC155986
0.6562 Remote Similarity NPC21773
0.6555 Remote Similarity NPC478137
0.6531 Remote Similarity NPC121744
0.6531 Remote Similarity NPC319090
0.6531 Remote Similarity NPC328104
0.6531 Remote Similarity NPC322353
0.6531 Remote Similarity NPC118508
0.6526 Remote Similarity NPC269877
0.6526 Remote Similarity NPC167272
0.6525 Remote Similarity NPC66862
0.6522 Remote Similarity NPC477292
0.6518 Remote Similarity NPC239768
0.6518 Remote Similarity NPC128698
0.6512 Remote Similarity NPC40488
0.6509 Remote Similarity NPC470542
0.6509 Remote Similarity NPC2158
0.6509 Remote Similarity NPC34754
0.6505 Remote Similarity NPC470384
0.65 Remote Similarity NPC87604
0.65 Remote Similarity NPC474216
0.65 Remote Similarity NPC473943
0.65 Remote Similarity NPC275910
0.65 Remote Similarity NPC473971
0.65 Remote Similarity NPC475363
0.65 Remote Similarity NPC473972
0.6491 Remote Similarity NPC293299
0.6491 Remote Similarity NPC45365
0.6486 Remote Similarity NPC167419
0.6476 Remote Similarity NPC166458
0.6471 Remote Similarity NPC6707
0.6465 Remote Similarity NPC73875
0.6465 Remote Similarity NPC237460
0.6465 Remote Similarity NPC315261
0.6458 Remote Similarity NPC9161
0.6458 Remote Similarity NPC49422
0.6452 Remote Similarity NPC238352
0.6452 Remote Similarity NPC477009
0.6442 Remote Similarity NPC82902
0.6442 Remote Similarity NPC124172
0.6442 Remote Similarity NPC231310
0.6442 Remote Similarity NPC209802
0.6442 Remote Similarity NPC238485
0.6441 Remote Similarity NPC287764
0.6441 Remote Similarity NPC63511
0.6441 Remote Similarity NPC72753
0.6436 Remote Similarity NPC109546
0.6436 Remote Similarity NPC143182
0.6436 Remote Similarity NPC30986
0.6436 Remote Similarity NPC84694
0.6436 Remote Similarity NPC328714
0.6436 Remote Similarity NPC28862
0.6436 Remote Similarity NPC81306
0.6436 Remote Similarity NPC209430
0.6436 Remote Similarity NPC47982
0.6421 Remote Similarity NPC216460
0.6421 Remote Similarity NPC208999
0.6408 Remote Similarity NPC215474
0.6392 Remote Similarity NPC265789
0.6389 Remote Similarity NPC69622
0.6389 Remote Similarity NPC107189
0.6385 Remote Similarity NPC15249
0.6385 Remote Similarity NPC25455
0.6381 Remote Similarity NPC474349
0.6381 Remote Similarity NPC152684
0.6381 Remote Similarity NPC24733
0.6381 Remote Similarity NPC474189
0.6381 Remote Similarity NPC474218
0.6381 Remote Similarity NPC318390
0.6378 Remote Similarity NPC237286
0.6373 Remote Similarity NPC164840
0.6373 Remote Similarity NPC236112
0.6373 Remote Similarity NPC209944
0.6373 Remote Similarity NPC241290
0.6373 Remote Similarity NPC234193
0.6346 Remote Similarity NPC477818
0.6346 Remote Similarity NPC21667

  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 NPC118275 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
0.6752 Remote Similarity NPD7337 Clinical (unspecified phase)
0.6752 Remote Similarity NPD7336 Phase 2
0.6752 Remote Similarity NPD7335 Phase 2
0.6701 Remote Similarity NPD7339 Approved
0.6701 Remote Similarity NPD6942 Approved
0.6633 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6598 Remote Similarity NPD6926 Approved
0.6598 Remote Similarity NPD6924 Approved
0.6562 Remote Similarity NPD4243 Approved
0.6526 Remote Similarity NPD6922 Approved
0.6526 Remote Similarity NPD6923 Approved
0.6465 Remote Similarity NPD6933 Approved
0.6458 Remote Similarity NPD7143 Approved
0.6458 Remote Similarity NPD7144 Approved
0.6429 Remote Similarity NPD4784 Approved
0.6429 Remote Similarity NPD4785 Approved
0.6392 Remote Similarity NPD7151 Approved
0.6392 Remote Similarity NPD7152 Approved
0.6392 Remote Similarity NPD7150 Approved
0.6364 Remote Similarity NPD5771 Approved
0.6339 Remote Similarity NPD7920 Phase 3
0.6339 Remote Similarity NPD7919 Phase 3
0.6336 Remote Similarity NPD8449 Approved
0.6288 Remote Similarity NPD8450 Suspended
0.6283 Remote Similarity NPD8088 Phase 1
0.6275 Remote Similarity NPD6929 Approved
0.6239 Remote Similarity NPD7333 Discontinued
0.6214 Remote Similarity NPD6931 Approved
0.6214 Remote Similarity NPD7525 Registered
0.6214 Remote Similarity NPD6930 Phase 2
0.62 Remote Similarity NPD4190 Phase 3
0.62 Remote Similarity NPD5275 Approved
0.6132 Remote Similarity NPD3665 Phase 1
0.6132 Remote Similarity NPD3133 Approved
0.6132 Remote Similarity NPD3666 Approved
0.6132 Remote Similarity NPD4786 Approved
0.6111 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6078 Remote Similarity NPD5776 Phase 2
0.6078 Remote Similarity NPD6932 Approved
0.6078 Remote Similarity NPD6925 Approved
0.6058 Remote Similarity NPD4748 Discontinued
0.6058 Remote Similarity NPD7509 Discontinued
0.6055 Remote Similarity NPD4723 Approved
0.6055 Remote Similarity NPD4722 Approved
0.6038 Remote Similarity NPD6695 Phase 3
0.6019 Remote Similarity NPD8308 Discontinued
0.6019 Remote Similarity NPD5279 Phase 3
0.6019 Remote Similarity NPD7145 Approved
0.6 Remote Similarity NPD4031 Approved
0.6 Remote Similarity NPD4032 Approved
0.5981 Remote Similarity NPD7338 Clinical (unspecified phase)
0.5962 Remote Similarity NPD4195 Approved
0.5962 Remote Similarity NPD6683 Phase 2
0.5946 Remote Similarity NPD4096 Approved
0.5944 Remote Similarity NPD8131 Suspended
0.5943 Remote Similarity NPD3667 Approved
0.5926 Remote Similarity NPD6893 Approved
0.5905 Remote Similarity NPD7514 Phase 3
0.5872 Remote Similarity NPD4694 Approved
0.5872 Remote Similarity NPD5280 Approved
0.5865 Remote Similarity NPD7322 Clinical (unspecified phase)
0.5859 Remote Similarity NPD2227 Clinical (unspecified phase)
0.5856 Remote Similarity NPD4753 Phase 2
0.5856 Remote Similarity NPD5328 Approved
0.5849 Remote Similarity NPD6902 Approved
0.5847 Remote Similarity NPD4719 Phase 2
0.5841 Remote Similarity NPD4202 Approved
0.5826 Remote Similarity NPD5349 Clinical (unspecified phase)
0.5818 Remote Similarity NPD7750 Discontinued
0.5818 Remote Similarity NPD7524 Approved
0.5814 Remote Similarity NPD6908 Approved
0.5814 Remote Similarity NPD6909 Approved
0.581 Remote Similarity NPD7645 Phase 2
0.5804 Remote Similarity NPD4001 Clinical (unspecified phase)
0.5794 Remote Similarity NPD4221 Approved
0.5794 Remote Similarity NPD7755 Approved
0.5794 Remote Similarity NPD4223 Phase 3
0.5794 Remote Similarity NPD7754 Approved
0.578 Remote Similarity NPD5329 Approved
0.5755 Remote Similarity NPD7332 Phase 2
0.5752 Remote Similarity NPD6079 Approved
0.5743 Remote Similarity NPD5365 Phase 2
0.5728 Remote Similarity NPD8264 Approved
0.5727 Remote Similarity NPD3618 Phase 1
0.5701 Remote Similarity NPD6898 Phase 1
0.5694 Remote Similarity NPD3638 Discontinued
0.5692 Remote Similarity NPD1710 Approved
0.5688 Remote Similarity NPD4197 Approved
0.5678 Remote Similarity NPD6404 Discontinued
0.5659 Remote Similarity NPD7522 Discontinued
0.5645 Remote Similarity NPD6420 Discontinued
0.5641 Remote Similarity NPD6083 Phase 2
0.5641 Remote Similarity NPD6084 Phase 2
0.5641 Remote Similarity NPD4755 Approved
0.5614 Remote Similarity NPD7087 Discontinued
0.5614 Remote Similarity NPD5281 Approved
0.5614 Remote Similarity NPD5284 Approved
0.5603 Remote Similarity NPD5210 Approved
0.5603 Remote Similarity NPD4629 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