NPASS Compound

Natural Product: NPC287839

Natural Product ID	NPC287839
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	YAIGDKVCMQAHRK-WLZQLHOFSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	24893886
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0002207] O-glycosyl compounds

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 61 64 0 0 0 0 0 0 0 0999 V2000 2.8732 -2.2277 3.3961 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7942 -1.5558 2.0155 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1576 -1.8326 1.3669 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7766 -2.1779 1.3387 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4185 -1.5387 0.1741 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8848 -0.1655 0.5768 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8864 0.5175 1.4447 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6403 1.4839 0.5115 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4764 1.9977 -0.2631 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8122 2.6220 -1.5582 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9070 2.5039 -2.5186 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3086 1.8256 -2.3303 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5207 1.0064 -1.1684 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8175 0.6605 -0.6485 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3843 -0.0228 -1.3874 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5675 0.0440 -0.6979 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6944 0.1486 -1.7000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2572 -1.2197 -2.0204 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8296 -1.8234 -0.7563 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0347 -1.3588 0.4214 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0013 -2.5089 1.4326 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3169 -2.1364 2.5897 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7112 -1.0665 0.1293 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1582 -1.4368 -0.5820 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2525 -2.0483 -2.4742 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6849 1.0296 -1.2839 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0455 3.3260 -1.7954 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2702 3.8347 -2.9220 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0317 3.4855 -0.8360 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2342 4.1648 -1.0468 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6832 -0.2293 2.2078 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1349 -3.2949 3.3014 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5040 -1.6628 4.0894 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8314 -2.2039 3.8052 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3463 -2.9075 1.2604 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9239 -1.4516 2.0921 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2581 -1.2636 0.4190 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6872 -2.1352 -0.3681 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3116 -1.3229 -0.4831 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1052 -0.2911 1.0898 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2978 1.2151 2.1153 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2700 0.8853 -0.1472 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1752 2.2590 1.0918 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7296 2.5440 0.3218 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0540 2.9251 -3.5065 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0097 1.7083 -0.4309 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4216 0.2405 -1.5026 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6290 0.9521 -0.0563 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2773 0.5614 -2.6386 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0344 -1.0840 -2.8022 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8371 -2.9395 -0.7980 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5644 -0.5372 0.9136 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0407 -2.7690 1.7543 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5436 -3.4171 1.0166 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8055 -1.4412 3.0804 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7112 -1.5612 -1.3835 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0460 -2.7816 -1.8156 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1714 1.3778 -2.0670 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2108 4.8295 -1.9372 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1039 3.4653 -1.2193 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5275 4.7997 -0.1904 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 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 2 0 11 12 1 0 12 13 1 0 13 14 1 0 13 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 20 23 1 0 19 24 1 0 18 25 1 0 17 26 1 0 10 27 1 0 27 28 2 0 27 29 1 0 29 30 1 0 7 31 1 0 31 2 1 0 14 6 1 0 23 16 1 0 14 9 1 0 1 32 1 0 1 33 1 0 1 34 1 0 3 35 1 0 3 36 1 0 3 37 1 0 5 38 1 0 5 39 1 0 6 40 1 1 7 41 1 1 8 42 1 0 8 43 1 0 9 44 1 0 11 45 1 0 13 46 1 0 14 47 1 0 16 48 1 1 17 49 1 6 18 50 1 6 19 51 1 6 20 52 1 1 21 53 1 0 21 54 1 0 22 55 1 0 24 56 1 0 25 57 1 0 26 58 1 0 30 59 1 0 30 60 1 0 30 61 1 0 M END

Standard InCHIKey	YAIGDKVCMQAHRK-WLZQLHOFSA-N
Standard InCHI	InChI=1S/C20H30O11/c1-20(2)28-7-10-11(31-20)4-8-9(17(25)26-3)6-27-18(13(8)10)30-19-16(24)15(23)14(22)12(5-21)29-19/h6,8,10-16,18-19,21-24H,4-5,7H2,1-3H3/t8?,10-,11-,12+,13?,14+,15-,16+,18?,19-/m0/s1
SMILES	CC1(C)OC[C@H]2[C@H](CC3C(=COC(C23)O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)C(=O)OC)O1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	446.18	Volume:	411.67 ? Van der Waals volume.
Dense:	1.084	LogP:	-0.501 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.003 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.197 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	22.0
TPSA:	153.37 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	4.0	Rings:	4.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.378	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.926	Fsp³:	0.85
MCE-18:	72.973 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.175	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.03 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.034 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.104	Promiscuous compounds:	0.017

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.428	MDCK Permeability:	-5.13
Pgp-inhibitor:	0.004	Pgp-substrate:	0.317
PAMPA:	0.888 ? 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):	0.205
20% Bioavailability (F20%):	0.065	30% Bioavailability (F30%):	0.92
50% Bioavailability (F50%):	0.852

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.037	MRP1:	0.428
Plasma Protein Binding (PPB):	36.849%	Volume Distribution (VD):	-0.54
Fu:	58.566% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.126
BSEP inhibitor:	0.014

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.036	CYP2C19-substrate:	0.002
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.117
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.384
HLM stability:	0.601 ? 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):

1.836

Half-life (T1/2):

2.728

ADMET: Toxicity

hERG Blockers:	0.014	hERG Blockers (10um):	0.143
Human Hepatotoxicity (H-HT):	0.793	Drug-induced Liver Injury (DILI):	0.943
AMES Toxicity:	0.909	Rat Oral Acute Toxicity:	0.137
Maximum Recommended Daily Dose:	0.022	Skin Sensitization:	0.986
Carcinogencity:	0.652	Eye Corrosion:	0.0
Eye Irritation:	0.044	Respiratory Toxicity:	0.025
Drug-induced Neurotoxicity:	0.006	Ototoxicity:	0.984
Hematotoxicity:	0.093	Drug-induced Nephrotoxicity:	0.157
Genotoxicity:	0.089	RPMI-8226 Immunitoxicity:	0.013
A549 Cytotoxicity:	0.038	Hek293 Cytotoxicity:	0.311
BCF:	0.309 ? 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:	2.935 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.549 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.559 ? 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
NPO14969	Hedychium spicatum	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[19027298]
NPO14969	Hedychium spicatum	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[19332371]
NPO14969	Hedychium spicatum	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[19782567]
NPO14969	Hedychium spicatum	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[23422227]
NPO14969	Hedychium spicatum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[35481430]
NPO18739	Exallage chrysotricha	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14969	Hedychium spicatum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15897	Hedychium forrestii	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15897	Hedychium forrestii	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15897	Hedychium forrestii	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18739	Exallage chrysotricha	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14969	Hedychium spicatum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15897	Hedychium forrestii	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18739	Exallage chrysotricha	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14969	Hedychium spicatum	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	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 NPC287839 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	16652
0.1-0.2	28938
0.2-0.3	3754
0.3-0.4	406
0.4-0.5	62
0.5-0.6	38
0.6-0.7	7
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
0.6471	Remote Similarity	NPC474730
0.6377	Remote Similarity	NPC35185
0.6377	Remote Similarity	NPC4899
0.6377	Remote Similarity	NPC177013
0.6234	Remote Similarity	NPC488470
0.6197	Remote Similarity	NPC27687
0.6197	Remote Similarity	NPC106668
0.5946	Remote Similarity	NPC488472
0.5946	Remote Similarity	NPC257424
0.5915	Remote Similarity	NPC255677
0.5915	Remote Similarity	NPC22149
0.5915	Remote Similarity	NPC475928
0.5915	Remote Similarity	NPC306344
0.589	Remote Similarity	NPC470573
0.589	Remote Similarity	NPC120021
0.589	Remote Similarity	NPC216826
0.5775	Remote Similarity	NPC117596
0.5775	Remote Similarity	NPC170432
0.5753	Remote Similarity	NPC37240
0.5733	Remote Similarity	NPC222062
0.5676	Remote Similarity	NPC231710
0.5676	Remote Similarity	NPC270908
0.5676	Remote Similarity	NPC65665
0.5658	Remote Similarity	NPC41681
0.55	Remote Similarity	NPC488456
0.55	Remote Similarity	NPC488471
0.55	Remote Similarity	NPC488466
0.55	Remote Similarity	NPC488465
0.55	Remote Similarity	NPC488460
0.55	Remote Similarity	NPC488462
0.5479	Remote Similarity	NPC307699
0.5443	Remote Similarity	NPC197541
0.5443	Remote Similarity	NPC118761
0.5412	Remote Similarity	NPC488467
0.5405	Remote Similarity	NPC148270
0.5366	Remote Similarity	NPC488457
0.5366	Remote Similarity	NPC488464
0.5366	Remote Similarity	NPC488463
0.5287	Remote Similarity	NPC488468
0.527	Remote Similarity	NPC195510
0.527	Remote Similarity	NPC298255
0.527	Remote Similarity	NPC13171
0.525	Remote Similarity	NPC234304
0.5132	Remote Similarity	NPC61201
0.5128	Remote Similarity	NPC254538

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC287839 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6213
0.1-0.2	2858
0.2-0.3	71
0.3-0.4	8
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