NPASS Compound

Natural Product: NPC21781

Natural Product ID	NPC21781
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	N-Methypachysamine A
IUPAC Name	(3S,5S,8R,9S,10S,13S,14S,17S)-17-[(1S)-1-(dimethylamino)ethyl]-N,N,10,13-tetramethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-amine
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL496255
PubChem CID	44587246
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002340] Azasteroids and derivatives

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 73 76 0 0 0 0 0 0 0 0999 V2000 -4.8440 0.5316 -1.8490 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8007 0.2094 -0.3929 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6749 -0.6374 0.0581 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7105 -1.9727 -0.6535 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2743 -2.1636 -1.1623 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5071 -1.4282 -0.1292 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1144 -1.0780 -0.4628 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6841 -2.3823 -0.6257 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0450 -1.9663 -1.1306 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6979 -1.1690 -0.0417 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0425 -0.6878 -0.4785 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7748 0.0949 0.5585 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9468 1.0553 1.3390 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5471 0.5988 1.6112 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8768 0.0403 0.3607 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9530 1.0443 -0.7428 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4913 -0.3765 0.7268 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3361 0.7132 1.2897 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8020 0.5050 1.2727 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3038 -0.1162 -0.0208 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9438 0.7458 -1.1750 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8839 0.7719 -0.0879 N 0 0 0 0 0 0 0 0 0 0 0 0 6.7908 -0.1683 -0.7013 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5362 1.7193 0.7656 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9814 1.3959 0.4566 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.2570 2.0455 0.0881 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2457 0.8940 1.8179 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8140 0.1912 -2.3298 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8559 1.6411 -2.0639 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0656 0.0949 -2.4706 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7395 -0.3910 -0.1736 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8753 -0.8814 1.1463 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4357 -2.0176 -1.4668 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9015 -2.8251 0.0289 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1506 -1.8217 -2.1876 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9903 -3.2532 -1.0905 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5283 -1.9792 0.8196 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0487 -0.5232 -1.3894 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1698 -3.0994 -1.2654 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8396 -2.8328 0.3980 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8957 -1.3978 -2.0640 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6945 -2.8189 -1.3664 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8559 -1.8618 0.8208 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0050 -0.1775 -1.4795 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6581 -1.6132 -0.6837 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2487 -0.6455 1.2675 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9672 2.1026 0.9170 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4445 1.1727 2.3471 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6052 -0.2433 2.3482 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9902 1.4213 2.0616 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0085 1.4459 -0.7591 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3203 1.9363 -0.5860 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7525 0.6491 -1.7374 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5988 -1.1682 1.5251 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0339 0.8287 2.3749 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1040 1.7322 0.8598 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0960 -0.1610 2.1168 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3177 1.4825 1.3742 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7152 0.1837 -2.1192 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9339 1.1976 -0.9207 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5875 1.6057 -1.3506 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1845 -0.9246 -0.0126 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6284 0.4416 -1.1336 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2395 -0.6493 -1.5389 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5993 1.7888 0.4365 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1228 2.7441 0.6530 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5578 1.3921 1.8261 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6661 2.5804 0.9690 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0044 2.8137 -0.6716 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9951 1.3117 -0.2392 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6757 -0.1440 1.7523 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0460 1.4958 2.3000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3778 0.9573 2.4717 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 6 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 6 12 22 1 0 22 23 1 0 22 24 1 0 2 25 1 0 25 26 1 0 25 27 1 0 20 3 1 0 20 6 1 0 17 7 1 0 15 10 1 0 1 28 1 0 1 29 1 0 1 30 1 0 2 31 1 6 3 32 1 1 4 33 1 0 4 34 1 0 5 35 1 0 5 36 1 0 6 37 1 1 7 38 1 6 8 39 1 0 8 40 1 0 9 41 1 0 9 42 1 0 10 43 1 1 11 44 1 0 11 45 1 0 12 46 1 1 13 47 1 0 13 48 1 0 14 49 1 0 14 50 1 0 16 51 1 0 16 52 1 0 16 53 1 0 17 54 1 1 18 55 1 0 18 56 1 0 19 57 1 0 19 58 1 0 21 59 1 0 21 60 1 0 21 61 1 0 23 62 1 0 23 63 1 0 23 64 1 0 24 65 1 0 24 66 1 0 24 67 1 0 26 68 1 0 26 69 1 0 26 70 1 0 27 71 1 0 27 72 1 0 27 73 1 0 M END

Standard InCHIKey	IHGKQRLXUYWOQB-SYILLIHQSA-N
Standard InCHI	InChI=1S/C25H46N2/c1-17(26(4)5)21-10-11-22-20-9-8-18-16-19(27(6)7)12-14-24(18,2)23(20)13-15-25(21,22)3/h17-23H,8-16H2,1-7H3/t17-,18-,19-,20-,21+,22-,23-,24-,25+/m0/s1
SMILES	C[C@@H]([C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)N(C)C)N(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	374.37	Volume:	428.724 ? Van der Waals volume.
Dense:	0.873	LogP:	4.851 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.868 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.071 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	20.0
TPSA:	6.48 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	0.0	Rings:	4.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.641	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.386	Fsp³:	1.0
MCE-18:	72.36 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.45	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.024 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.08	Promiscuous compounds:	0.322

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.142	MDCK Permeability:	-4.931
Pgp-inhibitor:	0.001	Pgp-substrate:	0.029
PAMPA:	0.007 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.0
20% Bioavailability (F20%):	0.0	30% Bioavailability (F30%):	0.001
50% Bioavailability (F50%):	0.812

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	1.0	MRP1:	0.027
Plasma Protein Binding (PPB):	46.692%	Volume Distribution (VD):	0.481
Fu:	48.624% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.758
OATP1B3 inhibitor:	0.702	BCRP inhibitor:	0.793
BSEP inhibitor:	0.001

ADMET: Metabolism

CYP1A2-inhibitor:	0.061	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.043
CYP2D6-inhibitor:	1.0	CYP2D6-substrate:	0.012
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
HLM stability:	0.0 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

20.037

Half-life (T1/2):

2.482

ADMET: Toxicity

hERG Blockers:	0.831	hERG Blockers (10um):	0.652
Human Hepatotoxicity (H-HT):	0.919	Drug-induced Liver Injury (DILI):	0.218
AMES Toxicity:	0.102	Rat Oral Acute Toxicity:	0.192
Maximum Recommended Daily Dose:	0.82	Skin Sensitization:	0.997
Carcinogencity:	0.756	Eye Corrosion:	0.428
Eye Irritation:	0.356	Respiratory Toxicity:	0.996
Drug-induced Neurotoxicity:	0.292	Ototoxicity:	0.817
Hematotoxicity:	0.756	Drug-induced Nephrotoxicity:	0.855
Genotoxicity:	0.158	RPMI-8226 Immunitoxicity:	0.067
A549 Cytotoxicity:	0.142	Hek293 Cytotoxicity:	0.615
BCF:	2.522 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	4.02 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.746 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.619 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO12900	Sarcococca hookeriana	Species	Buxaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[17827771]
NPO12900	Sarcococca hookeriana	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18681480]
NPO12900	Sarcococca hookeriana	Species	Buxaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[18681480]
NPO12900	Sarcococca hookeriana	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12900	Sarcococca hookeriana	Species	Buxaceae	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	Organism Name	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
IC50	2
IZ	4
MIC	3

Activity Type	# Activity
Individual protein	2
Organism	7

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT204	Individual protein	Acetylcholinesterase	Homo sapiens	IC50	=	22100.0	nM	PMID[20100877]
NPT439	Individual protein	Butyrylcholinesterase	Homo sapiens	IC50	=	1600.0	nM	PMID[11430012]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	19.0	mm	PMID[22652254]
NPT2921	Organism	Pseudomonas	Pseudomonas	IZ	=	14.5	mm	DrugMatrix in vivo data: Pathology
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	83500.0	nM	PMID[3236005]
NPT2921	Organism	Pseudomonas	Pseudomonas	MIC	=	167100.0	nM	DrugMatrix in vitro pharmacology data
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	IZ	=	11.0	mm	PubChem BioAssay data set
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	IZ	=	8.0	mm	PubChem BioAssay data set
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	167100.0	nM	DrugMatrix in vivo data: Hematology

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

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 toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC21781 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	35069
0.1-0.2	14294
0.2-0.3	416
0.3-0.4	49
0.4-0.5	14
0.5-0.6	9
0.6-0.7	4
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	Natural Product ID
0.7021	Intermediate Similarity	NPC120167
0.6981	Remote Similarity	NPC474695
0.6607	Remote Similarity	NPC474582
0.6154	Remote Similarity	NPC124384
0.6122	Remote Similarity	NPC473442
0.5882	Remote Similarity	NPC469970
0.5556	Remote Similarity	NPC182106
0.5556	Remote Similarity	NPC245223
0.5556	Remote Similarity	NPC311769
0.5455	Remote Similarity	NPC90150
0.5294	Remote Similarity	NPC109533
0.5263	Remote Similarity	NPC147513
0.5185	Remote Similarity	NPC21773
0.5082	Remote Similarity	NPC152684

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC21781 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7215
0.1-0.2	1867
0.2-0.3	61
0.3-0.4	7
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
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
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by 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