NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	240.21
Volume:	268.464
LogP:	3.027
LogD:	3.172
LogS:	-3.042
# Rotatable Bonds:	1
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.739
Synthetic Accessibility Score:	4.063
Fsp3:	1.0
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:	-4.49
MDCK Permeability:	2.2141241061035544e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.039

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.594
Plasma Protein Binding (PPB):	89.16092681884766%
Volume Distribution (VD):	1.292
Pgp-substrate:	10.894386291503906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.033
CYP1A2-substrate:	0.478
CYP2C19-inhibitor:	0.046
CYP2C19-substrate:	0.906
CYP2C9-inhibitor:	0.117
CYP2C9-substrate:	0.634
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.274
CYP3A4-inhibitor:	0.064
CYP3A4-substrate:	0.215

ADMET: Excretion

Clearance (CL):	5.83
Half-life (T1/2):	0.399

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.019
Drug-inuced Liver Injury (DILI):	0.03
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.015
Maximum Recommended Daily Dose:	0.023
Skin Sensitization:	0.429
Carcinogencity:	0.032
Eye Corrosion:	0.978
Eye Irritation:	0.929
Respiratory Toxicity:	0.046

Download Data

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

Natural Product: NPC102336

Natural Product ID:	NPC102336
*Common Name:**	Cryptomeridiol
IUPAC Name:	(1R,4aR,8aR)-7-(2-hydroxypropan-2-yl)-1,4a-dimethyl-2,3,4,5,6,7,8,8a-octahydronaphthalen-1-ol
Synonyms:	Cryptomeridiol
Standard InCHIKey:	LKKDASYGWYYFIK-ZJPTYJIISA-N
Standard InCHI:	InChI=1S/C15H28O2/c1-13(2,16)11-6-9-14(3)7-5-8-15(4,17)12(14)10-11/h11-12,16-17H,5-10H2,1-4H3/t11?,12-,14-,15-/m1/s1
SMILES:	CC(C)(C1CC[C@@]2(C)CCC[C@](C)([C@@H]2C1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1288770
PubChem CID:	52940854
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0000101] Eudesmane, isoeudesmane or cycloeudesmane 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
NPO25518	Hedychium coronarium	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[21106458]
NPO25518	Hedychium coronarium	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4537	Blumea glomerata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25518	Hedychium coronarium	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4537	Blumea glomerata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25518	Hedychium coronarium	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4537	Blumea glomerata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25518	Hedychium coronarium	Species	Zingiberaceae	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

Activity Type	# Activity
GI50	4
Others	4

Activity Type	# Activity
Cell Line	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	GI50	=	14500.0	nM	PMID[548196]
NPT81	Cell Line	A549	Homo sapiens	LC50	=	27400.0	nM	PMID[548196]
NPT136	Cell Line	SK-N-SH	Homo sapiens	GI50	=	73600.0	nM	PMID[548196]
NPT136	Cell Line	SK-N-SH	Homo sapiens	LC50	=	90900.0	nM	PMID[548196]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	62300.0	nM	PMID[548196]
NPT83	Cell Line	MCF7	Homo sapiens	LC50	=	87000.0	nM	PMID[548196]
NPT165	Cell Line	HeLa	Homo sapiens	GI50	=	75600.0	nM	PMID[548196]
NPT165	Cell Line	HeLa	Homo sapiens	LC50	>	100000.0	nM	PMID[548196]

☑ 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 NPC102336 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	413
0.1-0.2	5347
0.2-0.3	18802
0.3-0.4	8305
0.4-0.5	6134
0.5-0.6	3003
0.6-0.7	582
0.7-0.8	93
0.8-0.85	8
0.85-0.9	7
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC36002
0.8776	High Similarity	NPC14552
0.8545	High Similarity	NPC135438
0.8545	High Similarity	NPC236588
0.8364	Intermediate Similarity	NPC3025
0.82	Intermediate Similarity	NPC77550
0.82	Intermediate Similarity	NPC108441
0.8077	Intermediate Similarity	NPC316035
0.807	Intermediate Similarity	NPC474769
0.807	Intermediate Similarity	NPC189290
0.7931	Intermediate Similarity	NPC95958
0.7903	Intermediate Similarity	NPC101307
0.7903	Intermediate Similarity	NPC269077
0.7903	Intermediate Similarity	NPC88454
0.7903	Intermediate Similarity	NPC117607
0.7903	Intermediate Similarity	NPC253303
0.7857	Intermediate Similarity	NPC471269
0.7833	Intermediate Similarity	NPC209686
0.7833	Intermediate Similarity	NPC249078
0.7833	Intermediate Similarity	NPC236099
0.7778	Intermediate Similarity	NPC474756
0.7759	Intermediate Similarity	NPC47663
0.7736	Intermediate Similarity	NPC294858
0.7719	Intermediate Similarity	NPC264779
0.7705	Intermediate Similarity	NPC94897
0.7705	Intermediate Similarity	NPC101128
0.7679	Intermediate Similarity	NPC202146
0.7679	Intermediate Similarity	NPC53209
0.7679	Intermediate Similarity	NPC32222
0.7656	Intermediate Similarity	NPC66407
0.7656	Intermediate Similarity	NPC129829
0.7656	Intermediate Similarity	NPC254037
0.7656	Intermediate Similarity	NPC470833
0.7647	Intermediate Similarity	NPC313795
0.7581	Intermediate Similarity	NPC80463
0.7581	Intermediate Similarity	NPC230047
0.7581	Intermediate Similarity	NPC258595
0.7581	Intermediate Similarity	NPC19311
0.7581	Intermediate Similarity	NPC260116
0.7538	Intermediate Similarity	NPC283316
0.7538	Intermediate Similarity	NPC192192
0.75	Intermediate Similarity	NPC245795
0.75	Intermediate Similarity	NPC469987
0.7458	Intermediate Similarity	NPC162685
0.7424	Intermediate Similarity	NPC470071
0.7424	Intermediate Similarity	NPC1340
0.7424	Intermediate Similarity	NPC127094
0.7424	Intermediate Similarity	NPC187471
0.7424	Intermediate Similarity	NPC252182
0.7385	Intermediate Similarity	NPC477820
0.7377	Intermediate Similarity	NPC185547
0.7377	Intermediate Similarity	NPC95804
0.7358	Intermediate Similarity	NPC223468
0.7358	Intermediate Similarity	NPC198540
0.7358	Intermediate Similarity	NPC147343
0.7358	Intermediate Similarity	NPC287550
0.7358	Intermediate Similarity	NPC176309
0.7358	Intermediate Similarity	NPC84030
0.7344	Intermediate Similarity	NPC48079
0.7344	Intermediate Similarity	NPC185874
0.7344	Intermediate Similarity	NPC139207
0.7344	Intermediate Similarity	NPC476928
0.7344	Intermediate Similarity	NPC63190
0.7344	Intermediate Similarity	NPC41542
0.7313	Intermediate Similarity	NPC95165
0.7313	Intermediate Similarity	NPC153719
0.7302	Intermediate Similarity	NPC208198
0.7302	Intermediate Similarity	NPC11555
0.7302	Intermediate Similarity	NPC64123
0.7302	Intermediate Similarity	NPC60837
0.7302	Intermediate Similarity	NPC2728
0.7302	Intermediate Similarity	NPC282619
0.7302	Intermediate Similarity	NPC172613
0.7273	Intermediate Similarity	NPC232925
0.7273	Intermediate Similarity	NPC251201
0.7273	Intermediate Similarity	NPC63588
0.7258	Intermediate Similarity	NPC290791
0.7258	Intermediate Similarity	NPC114891
0.7258	Intermediate Similarity	NPC292419
0.7231	Intermediate Similarity	NPC244790
0.7231	Intermediate Similarity	NPC475893
0.7231	Intermediate Similarity	NPC472741
0.7231	Intermediate Similarity	NPC266578
0.7231	Intermediate Similarity	NPC2648
0.7206	Intermediate Similarity	NPC192501
0.7206	Intermediate Similarity	NPC10476
0.7206	Intermediate Similarity	NPC470151
0.7206	Intermediate Similarity	NPC475458
0.7206	Intermediate Similarity	NPC228994
0.7206	Intermediate Similarity	NPC304499
0.7188	Intermediate Similarity	NPC142712
0.7188	Intermediate Similarity	NPC44122
0.7167	Intermediate Similarity	NPC475515
0.7167	Intermediate Similarity	NPC215671
0.7167	Intermediate Similarity	NPC476735
0.7167	Intermediate Similarity	NPC87296
0.7143	Intermediate Similarity	NPC118937
0.7143	Intermediate Similarity	NPC159654
0.7143	Intermediate Similarity	NPC167995
0.7143	Intermediate Similarity	NPC144650
0.7143	Intermediate Similarity	NPC307022
0.7143	Intermediate Similarity	NPC281540
0.7121	Intermediate Similarity	NPC470830
0.7121	Intermediate Similarity	NPC107919
0.7121	Intermediate Similarity	NPC241085
0.7121	Intermediate Similarity	NPC299948
0.7121	Intermediate Similarity	NPC234511
0.7121	Intermediate Similarity	NPC196197
0.7121	Intermediate Similarity	NPC210323
0.7119	Intermediate Similarity	NPC39068
0.7119	Intermediate Similarity	NPC179024
0.7101	Intermediate Similarity	NPC317242
0.7101	Intermediate Similarity	NPC158208
0.7101	Intermediate Similarity	NPC186851
0.7101	Intermediate Similarity	NPC476424
0.7101	Intermediate Similarity	NPC472952
0.7101	Intermediate Similarity	NPC243027
0.7101	Intermediate Similarity	NPC32832
0.7101	Intermediate Similarity	NPC231680
0.7101	Intermediate Similarity	NPC196136
0.7101	Intermediate Similarity	NPC91387
0.7101	Intermediate Similarity	NPC270306
0.7101	Intermediate Similarity	NPC472950
0.7097	Intermediate Similarity	NPC218585
0.7097	Intermediate Similarity	NPC148174
0.7097	Intermediate Similarity	NPC71460
0.7077	Intermediate Similarity	NPC475884
0.7077	Intermediate Similarity	NPC204233
0.7077	Intermediate Similarity	NPC473230
0.7059	Intermediate Similarity	NPC470610
0.7031	Intermediate Similarity	NPC472946
0.7031	Intermediate Similarity	NPC473276
0.7031	Intermediate Similarity	NPC190827
0.7031	Intermediate Similarity	NPC243469
0.7031	Intermediate Similarity	NPC474380
0.7031	Intermediate Similarity	NPC41577
0.7031	Intermediate Similarity	NPC475943
0.7015	Intermediate Similarity	NPC282454
0.7015	Intermediate Similarity	NPC231945
0.7	Intermediate Similarity	NPC63958
0.7	Intermediate Similarity	NPC163597
0.7	Intermediate Similarity	NPC107963
0.697	Remote Similarity	NPC94192
0.697	Remote Similarity	NPC276616
0.6957	Remote Similarity	NPC472503
0.6957	Remote Similarity	NPC48795
0.6957	Remote Similarity	NPC308440
0.6949	Remote Similarity	NPC300189
0.6923	Remote Similarity	NPC473929
0.6923	Remote Similarity	NPC103734
0.6912	Remote Similarity	NPC167706
0.6912	Remote Similarity	NPC247195
0.6912	Remote Similarity	NPC131506
0.6912	Remote Similarity	NPC157422
0.6912	Remote Similarity	NPC195530
0.6912	Remote Similarity	NPC157777
0.6912	Remote Similarity	NPC109457
0.6912	Remote Similarity	NPC473279
0.6912	Remote Similarity	NPC100586
0.6912	Remote Similarity	NPC127283
0.6912	Remote Similarity	NPC8004
0.6901	Remote Similarity	NPC185915
0.6901	Remote Similarity	NPC11907
0.6901	Remote Similarity	NPC477227
0.6901	Remote Similarity	NPC192046
0.6901	Remote Similarity	NPC64081
0.6901	Remote Similarity	NPC133596
0.6901	Remote Similarity	NPC212453
0.6901	Remote Similarity	NPC474574
0.6901	Remote Similarity	NPC302578
0.6901	Remote Similarity	NPC105208
0.6901	Remote Similarity	NPC128951
0.6901	Remote Similarity	NPC476233
0.6875	Remote Similarity	NPC69149
0.6875	Remote Similarity	NPC68656
0.6866	Remote Similarity	NPC476431
0.6857	Remote Similarity	NPC159789
0.6825	Remote Similarity	NPC41160
0.6825	Remote Similarity	NPC282694
0.6825	Remote Similarity	NPC194208
0.6825	Remote Similarity	NPC79576
0.6818	Remote Similarity	NPC472984
0.6812	Remote Similarity	NPC81759
0.6812	Remote Similarity	NPC473238
0.6812	Remote Similarity	NPC253805
0.6812	Remote Similarity	NPC472341
0.6806	Remote Similarity	NPC31828
0.6806	Remote Similarity	NPC471769
0.6806	Remote Similarity	NPC471045
0.6806	Remote Similarity	NPC67657
0.6806	Remote Similarity	NPC18857
0.6806	Remote Similarity	NPC477577
0.6806	Remote Similarity	NPC177343
0.6806	Remote Similarity	NPC147993
0.6774	Remote Similarity	NPC185116
0.6769	Remote Similarity	NPC300442
0.6769	Remote Similarity	NPC474768
0.6769	Remote Similarity	NPC469791
0.6765	Remote Similarity	NPC163020
0.6761	Remote Similarity	NPC477602

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 NPC102336 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	491
0.1-0.2	4670
0.2-0.3	2903
0.3-0.4	646
0.4-0.5	304
0.5-0.6	99
0.6-0.7	33
0.7-0.8	4
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
0.82	Intermediate Similarity	NPD386	Approved
0.82	Intermediate Similarity	NPD388	Approved
0.7358	Intermediate Similarity	NPD385	Approved
0.7358	Intermediate Similarity	NPD384	Approved
0.7121	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.697	Remote Similarity	NPD5360	Phase 3
0.697	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD371	Approved
0.6857	Remote Similarity	NPD3703	Phase 2
0.6769	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD4787	Phase 1
0.6667	Remote Similarity	NPD4224	Phase 2
0.6667	Remote Similarity	NPD4758	Discontinued
0.6618	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD6114	Approved
0.6575	Remote Similarity	NPD6697	Approved
0.6575	Remote Similarity	NPD6115	Approved
0.6575	Remote Similarity	NPD6118	Approved
0.6481	Remote Similarity	NPD367	Approved
0.6479	Remote Similarity	NPD1811	Approved
0.6479	Remote Similarity	NPD1810	Approved
0.6429	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD3698	Phase 2
0.6301	Remote Similarity	NPD6117	Approved
0.6286	Remote Similarity	NPD4789	Approved
0.6286	Remote Similarity	NPD4244	Approved
0.6286	Remote Similarity	NPD4245	Approved
0.625	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6232	Remote Similarity	NPD6705	Phase 1
0.6216	Remote Similarity	NPD6116	Phase 1
0.6197	Remote Similarity	NPD6081	Approved
0.6197	Remote Similarity	NPD4243	Approved
0.6184	Remote Similarity	NPD7525	Registered
0.6184	Remote Similarity	NPD6928	Phase 2
0.6164	Remote Similarity	NPD3702	Approved
0.6133	Remote Similarity	NPD5364	Discontinued
0.6056	Remote Similarity	NPD2687	Approved
0.6056	Remote Similarity	NPD2686	Approved
0.6056	Remote Similarity	NPD2254	Approved
0.6053	Remote Similarity	NPD7645	Phase 2
0.6027	Remote Similarity	NPD4784	Approved
0.6027	Remote Similarity	NPD4785	Approved
0.5968	Remote Similarity	NPD615	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD4190	Phase 3
0.5946	Remote Similarity	NPD5275	Approved
0.5921	Remote Similarity	NPD3671	Phase 1
0.5867	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5844	Remote Similarity	NPD4195	Approved
0.5811	Remote Similarity	NPD6926	Approved
0.5811	Remote Similarity	NPD6924	Approved
0.5769	Remote Similarity	NPD6930	Phase 2
0.5769	Remote Similarity	NPD6931	Approved
0.5769	Remote Similarity	NPD4748	Discontinued
0.575	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.575	Remote Similarity	NPD3669	Approved
0.5733	Remote Similarity	NPD7339	Approved
0.5733	Remote Similarity	NPD6942	Approved
0.5732	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD3617	Approved
0.5663	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5658	Remote Similarity	NPD6933	Approved
0.5647	Remote Similarity	NPD6700	Approved
0.5647	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD6929	Approved
0.5625	Remote Similarity	NPD4223	Phase 3
0.5625	Remote Similarity	NPD4221	Approved
0.561	Remote Similarity	NPD7520	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