NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	262.19
Volume:	301.066
LogP:	5.769
LogD:	4.377
LogS:	-5.252
# Rotatable Bonds:	10
TPSA:	33.37
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.476
Synthetic Accessibility Score:	2.679
Fsp3:	0.647
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.754
MDCK Permeability:	1.667254946369212e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.375
30% Bioavailability (F30%):	0.975

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.262
Plasma Protein Binding (PPB):	97.98888397216797%
Volume Distribution (VD):	3.724
Pgp-substrate:	0.948420524597168%

ADMET: Metabolism

CYP1A2-inhibitor:	0.866
CYP1A2-substrate:	0.519
CYP2C19-inhibitor:	0.765
CYP2C19-substrate:	0.307
CYP2C9-inhibitor:	0.547
CYP2C9-substrate:	0.956
CYP2D6-inhibitor:	0.628
CYP2D6-substrate:	0.458
CYP3A4-inhibitor:	0.332
CYP3A4-substrate:	0.101

ADMET: Excretion

Clearance (CL):	3.613
Half-life (T1/2):	0.327

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.127
Drug-inuced Liver Injury (DILI):	0.067
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.098
Maximum Recommended Daily Dose:	0.157
Skin Sensitization:	0.914
Carcinogencity:	0.424
Eye Corrosion:	0.138
Eye Irritation:	0.659
Respiratory Toxicity:	0.857

Download Data

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

Natural Product: NPC186531

Natural Product ID:	NPC186531
*Common Name:**	(2S)-4-Dodec-11-Ynyl-2-Methyl-2H-Furan-5-One
IUPAC Name:	(2S)-4-dodec-11-ynyl-2-methyl-2H-furan-5-one
Synonyms:
Standard InCHIKey:	KCYNQKJAQXHQLE-HNNXBMFYSA-N
Standard InCHI:	InChI=1S/C17H26O2/c1-3-4-5-6-7-8-9-10-11-12-13-16-14-15(2)19-17(16)18/h1,14-15H,4-13H2,2H3/t15-/m0/s1
SMILES:	C#CCCCCCCCCCCC1=C[C@@H](OC1=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL477913
PubChem CID:	10801466
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols [CHEMONTID:0002518] Annonaceous acetogenins

*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
NPO32807	Hortonia	Genus	Monimiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11277762]

☑ 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

Activity Type	# Activity
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1381	Organism	Aedes aegypti	Aedes aegypti	LC50	=	0.41	ppm	PMID[552761]

☑ 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 NPC186531 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	191
0.1-0.2	2016
0.2-0.3	9452
0.3-0.4	17236
0.4-0.5	7970
0.5-0.6	4192
0.6-0.7	1343
0.7-0.8	284
0.8-0.85	5
0.85-0.9	5
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9254	High Similarity	NPC218477
0.8857	High Similarity	NPC84038
0.8732	High Similarity	NPC474705
0.8493	Intermediate Similarity	NPC469414
0.8493	Intermediate Similarity	NPC329826
0.8406	Intermediate Similarity	NPC248125
0.8286	Intermediate Similarity	NPC225272
0.8158	Intermediate Similarity	NPC128276
0.8133	Intermediate Similarity	NPC123360
0.8108	Intermediate Similarity	NPC476355
0.8088	Intermediate Similarity	NPC151648
0.8082	Intermediate Similarity	NPC163003
0.8026	Intermediate Similarity	NPC57744
0.7867	Intermediate Similarity	NPC140287
0.7848	Intermediate Similarity	NPC471325
0.7821	Intermediate Similarity	NPC178277
0.7794	Intermediate Similarity	NPC474267
0.7792	Intermediate Similarity	NPC41780
0.7792	Intermediate Similarity	NPC187568
0.7778	Intermediate Similarity	NPC203335
0.7778	Intermediate Similarity	NPC472266
0.775	Intermediate Similarity	NPC329829
0.775	Intermediate Similarity	NPC475159
0.775	Intermediate Similarity	NPC65930
0.775	Intermediate Similarity	NPC94875
0.775	Intermediate Similarity	NPC473780
0.775	Intermediate Similarity	NPC11332
0.775	Intermediate Similarity	NPC145914
0.775	Intermediate Similarity	NPC180363
0.775	Intermediate Similarity	NPC173609
0.775	Intermediate Similarity	NPC73310
0.775	Intermediate Similarity	NPC473712
0.775	Intermediate Similarity	NPC131002
0.775	Intermediate Similarity	NPC473529
0.7746	Intermediate Similarity	NPC133904
0.7733	Intermediate Similarity	NPC144419
0.7733	Intermediate Similarity	NPC269206
0.7733	Intermediate Similarity	NPC58956
0.7733	Intermediate Similarity	NPC295633
0.7714	Intermediate Similarity	NPC44343
0.7714	Intermediate Similarity	NPC179087
0.7714	Intermediate Similarity	NPC210303
0.7703	Intermediate Similarity	NPC67183
0.7692	Intermediate Similarity	NPC471220
0.7692	Intermediate Similarity	NPC108816
0.7692	Intermediate Similarity	NPC93763
0.7692	Intermediate Similarity	NPC299235
0.7681	Intermediate Similarity	NPC143857
0.7681	Intermediate Similarity	NPC229252
0.7671	Intermediate Similarity	NPC470256
0.7671	Intermediate Similarity	NPC276290
0.7662	Intermediate Similarity	NPC27205
0.7662	Intermediate Similarity	NPC235906
0.7654	Intermediate Similarity	NPC475947
0.7654	Intermediate Similarity	NPC144415
0.7654	Intermediate Similarity	NPC253801
0.7632	Intermediate Similarity	NPC474758
0.7632	Intermediate Similarity	NPC117746
0.7632	Intermediate Similarity	NPC15499
0.7632	Intermediate Similarity	NPC259599
0.7632	Intermediate Similarity	NPC294434
0.7625	Intermediate Similarity	NPC325031
0.7625	Intermediate Similarity	NPC150502
0.7625	Intermediate Similarity	NPC42470
0.7595	Intermediate Similarity	NPC270126
0.7568	Intermediate Similarity	NPC265574
0.7568	Intermediate Similarity	NPC475004
0.7564	Intermediate Similarity	NPC65603
0.7564	Intermediate Similarity	NPC141789
0.7564	Intermediate Similarity	NPC97516
0.7564	Intermediate Similarity	NPC7563
0.7564	Intermediate Similarity	NPC171204
0.7564	Intermediate Similarity	NPC470240
0.7564	Intermediate Similarity	NPC320630
0.7564	Intermediate Similarity	NPC116177
0.7564	Intermediate Similarity	NPC476794
0.7564	Intermediate Similarity	NPC476028
0.7561	Intermediate Similarity	NPC156804
0.7561	Intermediate Similarity	NPC163093
0.7536	Intermediate Similarity	NPC286189
0.7534	Intermediate Similarity	NPC194871
0.7532	Intermediate Similarity	NPC138408
0.7532	Intermediate Similarity	NPC155587
0.7532	Intermediate Similarity	NPC193351
0.7532	Intermediate Similarity	NPC226669
0.7532	Intermediate Similarity	NPC329852
0.7531	Intermediate Similarity	NPC35556
0.75	Intermediate Similarity	NPC182794
0.75	Intermediate Similarity	NPC281132
0.75	Intermediate Similarity	NPC474510
0.747	Intermediate Similarity	NPC120398
0.747	Intermediate Similarity	NPC473671
0.747	Intermediate Similarity	NPC182383
0.747	Intermediate Similarity	NPC202055
0.747	Intermediate Similarity	NPC110710
0.747	Intermediate Similarity	NPC475268
0.747	Intermediate Similarity	NPC283085
0.747	Intermediate Similarity	NPC77871
0.747	Intermediate Similarity	NPC231009
0.747	Intermediate Similarity	NPC477013
0.747	Intermediate Similarity	NPC473651
0.747	Intermediate Similarity	NPC132496
0.747	Intermediate Similarity	NPC473156
0.747	Intermediate Similarity	NPC286338
0.747	Intermediate Similarity	NPC66346
0.747	Intermediate Similarity	NPC319036
0.747	Intermediate Similarity	NPC1083
0.747	Intermediate Similarity	NPC39279
0.747	Intermediate Similarity	NPC471567
0.747	Intermediate Similarity	NPC107986
0.747	Intermediate Similarity	NPC473478
0.747	Intermediate Similarity	NPC103284
0.747	Intermediate Similarity	NPC477018
0.747	Intermediate Similarity	NPC235809
0.747	Intermediate Similarity	NPC82795
0.747	Intermediate Similarity	NPC100921
0.747	Intermediate Similarity	NPC329615
0.747	Intermediate Similarity	NPC322529
0.747	Intermediate Similarity	NPC25764
0.747	Intermediate Similarity	NPC470400
0.747	Intermediate Similarity	NPC473669
0.747	Intermediate Similarity	NPC477014
0.747	Intermediate Similarity	NPC329838
0.747	Intermediate Similarity	NPC223871
0.747	Intermediate Similarity	NPC9678
0.747	Intermediate Similarity	NPC39167
0.747	Intermediate Similarity	NPC292809
0.7468	Intermediate Similarity	NPC267231
0.7467	Intermediate Similarity	NPC469660
0.7465	Intermediate Similarity	NPC68110
0.7439	Intermediate Similarity	NPC193198
0.7432	Intermediate Similarity	NPC474823
0.7407	Intermediate Similarity	NPC25684
0.7407	Intermediate Similarity	NPC281949
0.7407	Intermediate Similarity	NPC141810
0.7407	Intermediate Similarity	NPC301477
0.7381	Intermediate Similarity	NPC473840
0.7381	Intermediate Similarity	NPC69082
0.7381	Intermediate Similarity	NPC475581
0.7381	Intermediate Similarity	NPC477010
0.7381	Intermediate Similarity	NPC473687
0.7381	Intermediate Similarity	NPC112685
0.7381	Intermediate Similarity	NPC284902
0.7381	Intermediate Similarity	NPC107717
0.7381	Intermediate Similarity	NPC134885
0.7381	Intermediate Similarity	NPC142117
0.7381	Intermediate Similarity	NPC469483
0.7381	Intermediate Similarity	NPC47937
0.7381	Intermediate Similarity	NPC231096
0.7381	Intermediate Similarity	NPC308412
0.7381	Intermediate Similarity	NPC477015
0.7381	Intermediate Similarity	NPC261721
0.7381	Intermediate Similarity	NPC134865
0.7381	Intermediate Similarity	NPC232555
0.7381	Intermediate Similarity	NPC293136
0.7381	Intermediate Similarity	NPC219498
0.7381	Intermediate Similarity	NPC240695
0.7381	Intermediate Similarity	NPC25703
0.7381	Intermediate Similarity	NPC241360
0.7381	Intermediate Similarity	NPC279267
0.7381	Intermediate Similarity	NPC103523
0.7381	Intermediate Similarity	NPC132940
0.7381	Intermediate Similarity	NPC114694
0.7381	Intermediate Similarity	NPC171174
0.7381	Intermediate Similarity	NPC309211
0.7381	Intermediate Similarity	NPC210218
0.7381	Intermediate Similarity	NPC282815
0.7381	Intermediate Similarity	NPC219652
0.7381	Intermediate Similarity	NPC62118
0.7381	Intermediate Similarity	NPC134807
0.7381	Intermediate Similarity	NPC204686
0.7375	Intermediate Similarity	NPC471299
0.7375	Intermediate Similarity	NPC264227
0.7375	Intermediate Similarity	NPC472965
0.7375	Intermediate Similarity	NPC469690
0.7375	Intermediate Similarity	NPC617
0.7375	Intermediate Similarity	NPC63649
0.7368	Intermediate Similarity	NPC129665
0.7368	Intermediate Similarity	NPC257618
0.7361	Intermediate Similarity	NPC226592
0.7361	Intermediate Similarity	NPC470320
0.7349	Intermediate Similarity	NPC475100
0.7349	Intermediate Similarity	NPC30486
0.7349	Intermediate Similarity	NPC82297
0.7349	Intermediate Similarity	NPC149869
0.7342	Intermediate Similarity	NPC10572
0.7342	Intermediate Similarity	NPC68156
0.7317	Intermediate Similarity	NPC85772
0.7317	Intermediate Similarity	NPC474291
0.7317	Intermediate Similarity	NPC200513
0.7308	Intermediate Similarity	NPC244166
0.7294	Intermediate Similarity	NPC154097
0.7294	Intermediate Similarity	NPC473649
0.7294	Intermediate Similarity	NPC20533
0.7294	Intermediate Similarity	NPC159750
0.7294	Intermediate Similarity	NPC475703
0.7294	Intermediate Similarity	NPC476583
0.7294	Intermediate Similarity	NPC470401
0.7294	Intermediate Similarity	NPC473995
0.7294	Intermediate Similarity	NPC477012

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 NPC186531 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	182
0.1-0.2	2677
0.2-0.3	4074
0.3-0.4	1591
0.4-0.5	478
0.5-0.6	121
0.6-0.7	27
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7317	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD5209	Approved
0.6875	Remote Similarity	NPD8039	Approved
0.6866	Remote Similarity	NPD6927	Phase 3
0.686	Remote Similarity	NPD1694	Approved
0.6707	Remote Similarity	NPD4756	Discovery
0.6667	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD29	Approved
0.6618	Remote Similarity	NPD28	Approved
0.6494	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD46	Approved
0.6484	Remote Similarity	NPD5785	Approved
0.6484	Remote Similarity	NPD6698	Approved
0.6447	Remote Similarity	NPD3197	Phase 1
0.6437	Remote Similarity	NPD7154	Phase 3
0.6429	Remote Similarity	NPD3172	Approved
0.6374	Remote Similarity	NPD1695	Approved
0.6338	Remote Similarity	NPD4266	Approved
0.6338	Remote Similarity	NPD3194	Approved
0.6338	Remote Similarity	NPD3196	Approved
0.6338	Remote Similarity	NPD3195	Phase 2
0.6292	Remote Similarity	NPD5363	Approved
0.6267	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD5208	Approved
0.625	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5332	Approved
0.625	Remote Similarity	NPD5331	Approved
0.625	Remote Similarity	NPD5362	Discontinued
0.6222	Remote Similarity	NPD7521	Approved
0.6222	Remote Similarity	NPD6684	Approved
0.6222	Remote Similarity	NPD6409	Approved
0.6222	Remote Similarity	NPD7146	Approved
0.6222	Remote Similarity	NPD5330	Approved
0.6222	Remote Similarity	NPD7334	Approved
0.6211	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD6051	Approved
0.6176	Remote Similarity	NPD5343	Approved
0.6119	Remote Similarity	NPD3174	Discontinued
0.6104	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD6903	Approved
0.6047	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD6686	Approved
0.6	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.597	Remote Similarity	NPD2699	Approved
0.5957	Remote Similarity	NPD7838	Discovery
0.5955	Remote Similarity	NPD6435	Approved
0.5955	Remote Similarity	NPD4269	Approved
0.5955	Remote Similarity	NPD4270	Approved
0.5922	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD5737	Approved
0.5914	Remote Similarity	NPD6672	Approved
0.5909	Remote Similarity	NPD4252	Approved
0.5895	Remote Similarity	NPD5693	Phase 1
0.5882	Remote Similarity	NPD1452	Discontinued
0.5875	Remote Similarity	NPD7331	Phase 2
0.5875	Remote Similarity	NPD3704	Approved
0.587	Remote Similarity	NPD5786	Approved
0.587	Remote Similarity	NPD4519	Discontinued
0.587	Remote Similarity	NPD4623	Approved
0.5862	Remote Similarity	NPD4268	Approved
0.5862	Remote Similarity	NPD4271	Approved
0.5859	Remote Similarity	NPD4225	Approved
0.5859	Remote Similarity	NPD7638	Approved
0.5857	Remote Similarity	NPD3173	Approved
0.5843	Remote Similarity	NPD5369	Approved
0.5823	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5802	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.58	Remote Similarity	NPD7640	Approved
0.58	Remote Similarity	NPD7639	Approved
0.5784	Remote Similarity	NPD2259	Approved
0.5784	Remote Similarity	NPD2258	Approved
0.5769	Remote Similarity	NPD3205	Discontinued
0.5755	Remote Similarity	NPD6371	Approved
0.5755	Remote Similarity	NPD2067	Discontinued
0.5735	Remote Similarity	NPD6096	Approved
0.5735	Remote Similarity	NPD6097	Approved
0.573	Remote Similarity	NPD5368	Approved
0.573	Remote Similarity	NPD4821	Approved
0.573	Remote Similarity	NPD4822	Approved
0.573	Remote Similarity	NPD4819	Approved
0.573	Remote Similarity	NPD4820	Approved
0.5729	Remote Similarity	NPD7983	Approved
0.5714	Remote Similarity	NPD622	Approved
0.5701	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.57	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5699	Remote Similarity	NPD6422	Discontinued
0.5699	Remote Similarity	NPD4249	Approved
0.567	Remote Similarity	NPD5778	Approved
0.567	Remote Similarity	NPD5779	Approved
0.5667	Remote Similarity	NPD4790	Discontinued
0.5638	Remote Similarity	NPD3573	Approved
0.5638	Remote Similarity	NPD4250	Approved
0.5638	Remote Similarity	NPD4251	Approved
0.5612	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5612	Remote Similarity	NPD7748	Approved
0.5612	Remote Similarity	NPD7900	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