NPASS Compound

Natural Product: NPC299488

Natural Product ID	NPC299488
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	YIMHGPSYDOGBPI-IQQSWPBXSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	6918114
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 80 84 0 0 0 0 0 0 0 0999 V2000 -4.2337 -2.5802 -0.7923 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7885 -1.6706 0.3088 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.6948 -0.6263 -0.2275 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1886 0.7508 -0.2882 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7390 0.9719 -0.0760 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6063 2.4255 0.4325 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0521 1.0710 -1.4476 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6060 1.4524 -1.2204 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9229 0.1774 -0.7019 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9542 -0.7748 -1.8279 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6317 -0.2247 0.5176 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9794 -0.9531 1.4360 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4126 -1.3471 1.2376 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8843 -2.2766 1.9202 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2086 -0.6241 0.2297 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6381 -0.3477 0.6504 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6887 -0.0326 2.1152 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3885 -1.6848 0.5045 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8376 -1.5141 0.8774 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4665 -0.6553 -0.1432 C 0 0 2 0 0 0 0 0 0 0 0 0 4.7396 0.5988 -0.4447 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0717 0.8735 -1.9429 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2681 0.6294 -0.2731 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5701 0.5076 -1.6409 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1898 1.1101 -1.4760 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4774 0.6020 -0.2715 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2645 1.6623 0.7691 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3817 1.7558 0.2434 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7234 2.4748 0.9977 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7176 2.0081 0.0242 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7323 -1.4093 -1.2908 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0489 0.0943 0.8693 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7212 -1.1936 1.2280 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3190 -1.1557 2.6457 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1456 -1.9586 -1.7057 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2719 -3.0233 -0.5282 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9391 -3.3954 -1.0466 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4192 -2.3976 0.9122 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0190 -0.9941 -1.2512 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6674 -0.6615 0.3496 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4605 1.1880 -1.2965 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7869 1.3953 0.4254 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6372 3.1511 -0.3789 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5250 2.6352 1.0568 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7703 2.5338 1.1330 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5309 1.9588 -1.9380 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2226 0.2164 -2.0787 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6023 2.2741 -0.5145 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1834 1.7667 -2.1749 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6049 -1.6392 -1.5522 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0029 -1.2095 -2.1668 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4185 -0.3749 -2.7795 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4424 -1.2807 2.3587 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2905 -1.3143 -0.6350 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0999 0.9251 2.4028 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2785 -0.7877 2.7213 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6508 -0.1963 2.5576 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3235 -1.9476 -0.5502 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9986 -2.4775 1.1299 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0398 -1.1207 1.8660 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2632 -2.5503 0.8679 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4810 -0.3611 0.2720 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6687 0.0752 -2.5821 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1956 0.6892 -1.9753 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8690 1.9006 -2.2213 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0052 1.6899 0.0336 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5434 -0.5176 -2.0082 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0560 1.1937 -2.3989 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2743 2.2348 -1.4770 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6322 0.8835 -2.4309 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2195 2.6498 0.2110 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6372 1.4910 1.3918 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0974 1.8155 1.4738 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2949 2.5178 0.6897 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2155 -2.2515 -1.2454 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9269 0.6375 1.8608 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9829 -2.0518 1.2881 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3757 -0.8161 2.6180 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7706 -0.4330 3.2792 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3289 -2.1577 3.0948 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 1 5 7 1 0 7 8 1 0 8 9 1 0 9 10 1 6 9 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 13 15 1 0 15 16 1 0 16 17 1 1 16 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 6 21 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 1 21 28 1 0 28 29 2 0 28 30 1 0 20 31 1 0 11 32 1 0 32 33 1 0 33 34 1 0 33 2 1 0 32 5 1 0 26 9 1 0 26 15 1 0 23 16 1 0 1 35 1 0 1 36 1 0 1 37 1 0 2 38 1 1 3 39 1 0 3 40 1 0 4 41 1 0 4 42 1 0 6 43 1 0 6 44 1 0 6 45 1 0 7 46 1 0 7 47 1 0 8 48 1 0 8 49 1 0 10 50 1 0 10 51 1 0 10 52 1 0 12 53 1 0 15 54 1 0 17 55 1 0 17 56 1 0 17 57 1 0 18 58 1 0 18 59 1 0 19 60 1 0 19 61 1 0 20 62 1 1 22 63 1 0 22 64 1 0 22 65 1 0 23 66 1 0 24 67 1 0 24 68 1 0 25 69 1 0 25 70 1 0 27 71 1 0 27 72 1 0 27 73 1 0 30 74 1 0 31 75 1 0 32 76 1 0 33 77 1 1 34 78 1 0 34 79 1 0 34 80 1 0 M END

Standard InCHIKey	YIMHGPSYDOGBPI-IQQSWPBXSA-N
Standard InCHI	InChI=1S/C30H46O4/c1-17-8-11-26(3)14-15-28(5)19(23(26)18(17)2)16-20(31)24-27(4)12-10-22(32)30(7,25(33)34)21(27)9-13-29(24,28)6/h16-18,21-24,32H,8-15H2,1-7H3,(H,33,34)/t17-,18+,21?,22-,23?,24?,26-,27+,28-,29-,30-/m1/s1
SMILES	C[C@@H]1CC[C@]2(C)CC[C@]3(C)C(=CC(=O)C4[C@@]5(C)CC[C@H]([C@@](C)(C5CC[C@@]34C)C(=O)O)O)C2[C@H]1C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	470.34	Volume:	511.905 ? Van der Waals volume.
Dense:	0.919	LogP:	3.51 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.011 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.248 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	28.0
TPSA:	74.6 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.474	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.939	Fsp³:	0.867
MCE-18:	104.464 ? 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:	0.486	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.189 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.035 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.254	Promiscuous compounds:	0.17

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.561	MDCK Permeability:	-5.028
Pgp-inhibitor:	0.34	Pgp-substrate:	0.028
PAMPA:	0.986 ? 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%):	0.161	30% Bioavailability (F30%):	0.017
50% Bioavailability (F50%):	0.873

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.379	MRP1:	0.996
Plasma Protein Binding (PPB):	96.627%	Volume Distribution (VD):	-0.477
Fu:	4.123% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.996	BCRP inhibitor:	0.091
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.005	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.087	CYP2C19-substrate:	0.003
CYP2C9-inhibitor:	0.187	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.999	CYP3A4-substrate:	0.005
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.07
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):

6.074

Half-life (T1/2):

0.965

ADMET: Toxicity

hERG Blockers:	0.031	hERG Blockers (10um):	0.114
Human Hepatotoxicity (H-HT):	0.83	Drug-induced Liver Injury (DILI):	0.298
AMES Toxicity:	0.148	Rat Oral Acute Toxicity:	0.415
Maximum Recommended Daily Dose:	0.441	Skin Sensitization:	0.715
Carcinogencity:	0.949	Eye Corrosion:	0.007
Eye Irritation:	0.674	Respiratory Toxicity:	0.75
Drug-induced Neurotoxicity:	0.04	Ototoxicity:	0.658
Hematotoxicity:	0.156	Drug-induced Nephrotoxicity:	0.584
Genotoxicity:	0.557	RPMI-8226 Immunitoxicity:	0.044
A549 Cytotoxicity:	0.056	Hek293 Cytotoxicity:	0.27
BCF:	0.998 ? 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:	4.099 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.604 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.947 ? 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
NPO15315	Boswellia carterii	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24195447]
NPO15315	Boswellia carterii	Species	Burseraceae	Eukaryota	Gum resin	n.a.	n.a.	PMID[26457560]
NPO15315	Boswellia carterii	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15315	Boswellia carterii	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15315	Boswellia carterii	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15315	Boswellia carterii	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15315	Boswellia carterii	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15315	Boswellia carterii	Species	Burseraceae	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

Molecular-level activity

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

In vitro activity

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

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 NPC299488 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	20777
0.1-0.2	25456
0.2-0.3	3238
0.3-0.4	331
0.4-0.5	38
0.5-0.6	13
0.6-0.7	3
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC148523
0.7121	Intermediate Similarity	NPC86372
0.6714	Remote Similarity	NPC26413
0.6515	Remote Similarity	NPC602872
0.6087	Remote Similarity	NPC471898
0.589	Remote Similarity	NPC98874
0.5479	Remote Similarity	NPC272075
0.5395	Remote Similarity	NPC4036
0.5395	Remote Similarity	NPC65120
0.5395	Remote Similarity	NPC145067
0.5395	Remote Similarity	NPC233455
0.5395	Remote Similarity	NPC158030
0.5395	Remote Similarity	NPC610635
0.5342	Remote Similarity	NPC479748
0.5333	Remote Similarity	NPC167193
0.5263	Remote Similarity	NPC155120
0.5263	Remote Similarity	NPC288833
0.5132	Remote Similarity	NPC472806

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC299488 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5809
0.1-0.2	3235
0.2-0.3	100
0.3-0.4	3
0.4-0.5	2
0.5-0.6	1
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
0.5395	Remote Similarity	NPD7515	Phase 2

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