NPASS Compound

Structure

CID248068 OpenBabel06191716052D 24 26 0 0 1 0 0 0 0 0999 V2000 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 10 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 19 1 0 0 0 0 8 20 1 0 0 0 0 9 11 2 0 0 0 0 9 12 1 0 0 0 0 10 11 1 0 0 0 0 11 14 1 0 0 0 0 12 13 2 0 0 0 0 12 15 1 0 0 0 0 13 16 1 0 0 0 0 13 20 1 0 0 0 0 14 16 2 0 0 0 0 14 21 1 0 0 0 0 15 17 1 0 0 0 0 15 22 2 0 0 0 0 16 23 1 0 0 0 0 17 18 1 0 0 0 0 17 24 1 1 0 0 0 18 19 1 0 0 0 0 18 20 1 6 0 0 0 20 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	332.2
Volume:	353.422
LogP:	3.627
LogD:	1.372
LogS:	-3.206
# Rotatable Bonds:	1
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.681
Synthetic Accessibility Score:	4.26
Fsp3:	0.65
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.721
MDCK Permeability:	1.5988714949344285e-05
Pgp-inhibitor:	0.07
Pgp-substrate:	0.546
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.91
30% Bioavailability (F30%):	0.595

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.512
Plasma Protein Binding (PPB):	94.95548248291016%
Volume Distribution (VD):	3.566
Pgp-substrate:	7.080443382263184%

ADMET: Metabolism

CYP1A2-inhibitor:	0.055
CYP1A2-substrate:	0.767
CYP2C19-inhibitor:	0.05
CYP2C19-substrate:	0.834
CYP2C9-inhibitor:	0.273
CYP2C9-substrate:	0.867
CYP2D6-inhibitor:	0.045
CYP2D6-substrate:	0.256
CYP3A4-inhibitor:	0.138
CYP3A4-substrate:	0.463

ADMET: Excretion

Clearance (CL):	3.525
Half-life (T1/2):	0.271

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.187
Drug-inuced Liver Injury (DILI):	0.499
AMES Toxicity:	0.033
Rat Oral Acute Toxicity:	0.16
Maximum Recommended Daily Dose:	0.563
Skin Sensitization:	0.92
Carcinogencity:	0.021
Eye Corrosion:	0.003
Eye Irritation:	0.791
Respiratory Toxicity:	0.959

Download Data

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

Natural Product: NPC248068

Natural Product ID:	NPC248068
*Common Name:**	6-Alpha-Hydroxydemethyl-Cryptojaponol
IUPAC Name:	(4aS,10R,10aS)-5,6,10-trihydroxy-1,1,4a-trimethyl-7-propan-2-yl-3,4,10,10a-tetrahydro-2H-phenanthren-9-one
Synonyms:
Standard InCHIKey:	DLFBGJCOHIZRGA-CMKODMSKSA-N
Standard InCHI:	InChI=1S/C20H28O4/c1-10(2)11-9-12-13(16(23)14(11)21)20(5)8-6-7-19(3,4)18(20)17(24)15(12)22/h9-10,17-18,21,23-24H,6-8H2,1-5H3/t17-,18-,20+/m0/s1
SMILES:	O[C@H]1C(=O)c2cc(C(C)C)c(c(c2[C@@]2([C@@H]1C(C)(C)CCC2)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2252749
PubChem CID:	76326386
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO17119	Dalea versicolor	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043439]
NPO18606	Achyrocline bogotensis	Species	Asteraceae	Eukaryota	n.a.	Colombian	n.a.	PMID[15844937]
NPO13465	Salvia broussonetii	Species	Lamiaceae	Eukaryota	roots	n.a.	n.a.	PMID[15969497]
NPO3291	Cynanchum auriculatum	Species	Apocynaceae	Eukaryota	n.a.	root	n.a.	PMID[18401845]
NPO13135	Campylotropis hirtella	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19481938]
NPO17362	Alstonia yunnanensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19775092]
NPO18055	Isodon adenolomus	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21534539]
NPO18055	Isodon adenolomus	Species	Lamiaceae	Eukaryota	aerial parts	Shangrila, Yunnan Province, China	2008-AUG	PMID[21534539]
NPO33568	Caryopteris mongolica	Species	Lamiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[25958242]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28294615]
NPO18676	Clerodendrum trichotomum	Species	Lamiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29924604]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31291099]
NPO12148.2	Acer pictum subsp. okamotoanum	Subspecies	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461665]
NPO17362	Alstonia yunnanensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6731	Ononis spinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7773	Crinum moorei	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3291	Cynanchum auriculatum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18356	Stachys tuberifera	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13135	Campylotropis hirtella	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18435	Tylophora atrofolliculata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17362	Alstonia yunnanensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18435	Tylophora atrofolliculata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6731	Ononis spinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13135	Campylotropis hirtella	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7773	Crinum moorei	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18676	Clerodendrum trichotomum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18356	Stachys tuberifera	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3291	Cynanchum auriculatum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17362	Alstonia yunnanensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6731	Ononis spinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3291	Cynanchum auriculatum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19580	Chamaemelum fuscatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10638	Plectranthus myrianthus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10605	Tristania conferta	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17911	Blepharisma japonicum	Species	Blepharismidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18606	Achyrocline bogotensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3873	Crotalaria candicans	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15497	Caria ino	Species	Riodinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19777	Pholiota adiposa	Species	Strophariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11843	Stephania zippeliana	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22691	Mentha cardiaca	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1257	Distephanus angulifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12565	Hypericum polyanthemum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4984	Salvia cana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2377	Cetraria ciliaris	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11190	Veronica polita	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10922	Pentaclethra macrophylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16997	Talaromyces aculeatus	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19638	Scutellaria albida	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13465	Salvia broussonetii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5043	Eria japonica	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17643	Penicillium pedemontanum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4230	Protoparmeliopsis peltata	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9319	Pterocaulon virgatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12148.2	Acer pictum subsp. okamotoanum	Subspecies	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10852	Felimare midatlantica	Species	Chromodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16990	Verbesina virgata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21720	Talaromyces variabilis	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17119	Dalea versicolor	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18055	Isodon adenolomus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18676	Clerodendrum trichotomum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19522	Arthropsis truncata	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7822.1	Eucalyptus globulus subsp. bicostata	Subspecies	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13832	Aspilia hispida	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8934	Gypsophila perfoliata	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19311	Dasymaschalon blumei	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9532	Vernonia cistifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12091	Martensia denticulata	Species	Delesseriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3291	Cynanchum auriculatum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17783	Sideritis cystosiphon	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13414	Senecio fuertesii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13135	Campylotropis hirtella	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18356	Stachys tuberifera	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1815	Breonia chinensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO526	Salvia sessei	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6289	Ceropegia dichotoma	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16567	Doriopsilla areolata	Species	Dendrodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17362	Alstonia yunnanensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9704	Sonneratia caseolaris	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6731	Ononis spinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12205	Eucalyptus apodophylla	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5456	Juniperus drupacea	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23384	Rhodiola semenovii	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11576	Glycosmis macrophylla	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7773	Crinum moorei	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18435	Tylophora atrofolliculata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	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
IC50	1
LD50	2
Others	8

Activity Type	# Activity
Cell Line	2
Organism	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1161	Cell Line	CHO	Cricetulus griseus	LD50	>	100.0	ug ml-1	PMID[479060]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	9400.0	nM	PMID[479062]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	LD50	=	0.98	ug ml-1	PMID[479060]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	11.0	mm	PMID[479061]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	IZ	=	21.2	mm	PMID[479061]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	IZ	=	11.5	mm	PMID[479061]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	IZ	=	13.8	mm	PMID[479061]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	22.5	mm	PMID[479061]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	IZ	=	17.7	mm	PMID[479061]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	IZ	=	20.2	mm	PMID[479061]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	IZ	=	9.1	mm	PMID[479061]

☑ 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 NPC248068 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	343
0.1-0.2	1273
0.2-0.3	2864
0.3-0.4	6895
0.4-0.5	11233
0.5-0.6	6303
0.6-0.7	9361
0.7-0.8	4129
0.8-0.85	236
0.85-0.9	46
0.9-0.95	9
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9706	High Similarity	NPC471853
0.9559	High Similarity	NPC230811
0.9333	High Similarity	NPC111845
0.9203	High Similarity	NPC475957
0.9191	High Similarity	NPC138472
0.9191	High Similarity	NPC78307
0.9058	High Similarity	NPC153088
0.9051	High Similarity	NPC4170
0.8986	High Similarity	NPC202225
0.8905	High Similarity	NPC291001
0.8905	High Similarity	NPC471851
0.8873	High Similarity	NPC476534
0.8849	High Similarity	NPC293454
0.8794	High Similarity	NPC277559
0.8794	High Similarity	NPC49911
0.8759	High Similarity	NPC171460
0.8759	High Similarity	NPC196941
0.8759	High Similarity	NPC126707
0.8759	High Similarity	NPC309169
0.875	High Similarity	NPC78364
0.875	High Similarity	NPC176130
0.875	High Similarity	NPC69424
0.875	High Similarity	NPC84672
0.8732	High Similarity	NPC61398
0.8732	High Similarity	NPC416
0.8707	High Similarity	NPC52692
0.8707	High Similarity	NPC5568
0.8699	High Similarity	NPC75295
0.8696	High Similarity	NPC108129
0.8652	High Similarity	NPC258502
0.8652	High Similarity	NPC103082
0.8643	High Similarity	NPC477139
0.8639	High Similarity	NPC136878
0.8639	High Similarity	NPC474991
0.8633	High Similarity	NPC476847
0.863	High Similarity	NPC29932
0.8621	High Similarity	NPC471971
0.8621	High Similarity	NPC471972
0.8621	High Similarity	NPC469855
0.8621	High Similarity	NPC30846
0.8621	High Similarity	NPC184935
0.8621	High Similarity	NPC308572
0.8613	High Similarity	NPC72667
0.8571	High Similarity	NPC258856
0.8552	High Similarity	NPC272907
0.8552	High Similarity	NPC2681
0.8551	High Similarity	NPC3009
0.854	High Similarity	NPC254492
0.8529	High Similarity	NPC181334
0.8514	High Similarity	NPC246229
0.8514	High Similarity	NPC191899
0.8503	High Similarity	NPC469856
0.8503	High Similarity	NPC471906
0.8503	High Similarity	NPC79627
0.8503	High Similarity	NPC244691
0.8503	High Similarity	NPC469854
0.8493	Intermediate Similarity	NPC135524
0.8489	Intermediate Similarity	NPC276238
0.8489	Intermediate Similarity	NPC303910
0.8487	Intermediate Similarity	NPC62051
0.8483	Intermediate Similarity	NPC470035
0.8478	Intermediate Similarity	NPC324209
0.8472	Intermediate Similarity	NPC141368
0.8472	Intermediate Similarity	NPC469680
0.8472	Intermediate Similarity	NPC469681
0.8472	Intermediate Similarity	NPC471974
0.8467	Intermediate Similarity	NPC142654
0.8467	Intermediate Similarity	NPC87985
0.8462	Intermediate Similarity	NPC7464
0.8462	Intermediate Similarity	NPC315275
0.8456	Intermediate Similarity	NPC127046
0.8451	Intermediate Similarity	NPC204582
0.8446	Intermediate Similarity	NPC470038
0.8446	Intermediate Similarity	NPC84786
0.8446	Intermediate Similarity	NPC478160
0.8446	Intermediate Similarity	NPC68441
0.8435	Intermediate Similarity	NPC199936
0.8435	Intermediate Similarity	NPC100242
0.8425	Intermediate Similarity	NPC92079
0.8425	Intermediate Similarity	NPC204045
0.8425	Intermediate Similarity	NPC305845
0.8417	Intermediate Similarity	NPC234175
0.8411	Intermediate Similarity	NPC280295
0.8403	Intermediate Similarity	NPC264022
0.8394	Intermediate Similarity	NPC199273
0.8389	Intermediate Similarity	NPC476535
0.8389	Intermediate Similarity	NPC471970
0.838	Intermediate Similarity	NPC294226
0.838	Intermediate Similarity	NPC314048
0.8369	Intermediate Similarity	NPC93015
0.8367	Intermediate Similarity	NPC474961
0.8356	Intermediate Similarity	NPC3218
0.8355	Intermediate Similarity	NPC124842
0.8345	Intermediate Similarity	NPC165191
0.8345	Intermediate Similarity	NPC245760
0.8345	Intermediate Similarity	NPC157284
0.8345	Intermediate Similarity	NPC297797
0.8345	Intermediate Similarity	NPC477849
0.8345	Intermediate Similarity	NPC289358
0.8345	Intermediate Similarity	NPC42384
0.8345	Intermediate Similarity	NPC51531
0.8345	Intermediate Similarity	NPC473779
0.8345	Intermediate Similarity	NPC149773
0.8345	Intermediate Similarity	NPC46242
0.8345	Intermediate Similarity	NPC91887
0.8345	Intermediate Similarity	NPC469857
0.8345	Intermediate Similarity	NPC50615
0.8345	Intermediate Similarity	NPC114333
0.8345	Intermediate Similarity	NPC23667
0.8345	Intermediate Similarity	NPC473479
0.8345	Intermediate Similarity	NPC5014
0.8345	Intermediate Similarity	NPC28592
0.8333	Intermediate Similarity	NPC123506
0.8333	Intermediate Similarity	NPC476821
0.8333	Intermediate Similarity	NPC137750
0.8322	Intermediate Similarity	NPC225351
0.8321	Intermediate Similarity	NPC471187
0.8311	Intermediate Similarity	NPC143898
0.8311	Intermediate Similarity	NPC478164
0.8302	Intermediate Similarity	NPC263212
0.8289	Intermediate Similarity	NPC470037
0.8289	Intermediate Similarity	NPC225854
0.8288	Intermediate Similarity	NPC294330
0.8286	Intermediate Similarity	NPC96024
0.8276	Intermediate Similarity	NPC477592
0.8276	Intermediate Similarity	NPC147418
0.8267	Intermediate Similarity	NPC273798
0.8267	Intermediate Similarity	NPC143685
0.8267	Intermediate Similarity	NPC58752
0.8252	Intermediate Similarity	NPC52407
0.8248	Intermediate Similarity	NPC282577
0.8248	Intermediate Similarity	NPC471794
0.8243	Intermediate Similarity	NPC176030
0.8243	Intermediate Similarity	NPC291078
0.8243	Intermediate Similarity	NPC192597
0.8243	Intermediate Similarity	NPC229218
0.8243	Intermediate Similarity	NPC169214
0.8243	Intermediate Similarity	NPC141817
0.8235	Intermediate Similarity	NPC472838
0.8235	Intermediate Similarity	NPC306011
0.8235	Intermediate Similarity	NPC473201
0.8235	Intermediate Similarity	NPC302783
0.8231	Intermediate Similarity	NPC169452
0.8231	Intermediate Similarity	NPC181560
0.8231	Intermediate Similarity	NPC203063
0.8231	Intermediate Similarity	NPC473527
0.8224	Intermediate Similarity	NPC474310
0.8219	Intermediate Similarity	NPC206207
0.8212	Intermediate Similarity	NPC470757
0.8212	Intermediate Similarity	NPC10842
0.8207	Intermediate Similarity	NPC475111
0.8207	Intermediate Similarity	NPC471670
0.8207	Intermediate Similarity	NPC86524
0.8207	Intermediate Similarity	NPC474311
0.82	Intermediate Similarity	NPC34482
0.82	Intermediate Similarity	NPC170055
0.8194	Intermediate Similarity	NPC314257
0.8194	Intermediate Similarity	NPC23894
0.8182	Intermediate Similarity	NPC17843
0.8182	Intermediate Similarity	NPC165612
0.8182	Intermediate Similarity	NPC180944
0.8182	Intermediate Similarity	NPC70622
0.8182	Intermediate Similarity	NPC164912
0.8175	Intermediate Similarity	NPC154696
0.817	Intermediate Similarity	NPC476532
0.817	Intermediate Similarity	NPC48949
0.8169	Intermediate Similarity	NPC117609
0.8163	Intermediate Similarity	NPC242994
0.8163	Intermediate Similarity	NPC138099
0.8163	Intermediate Similarity	NPC190457
0.8158	Intermediate Similarity	NPC112816
0.8158	Intermediate Similarity	NPC264229
0.8158	Intermediate Similarity	NPC132810
0.8158	Intermediate Similarity	NPC46549
0.8158	Intermediate Similarity	NPC94781
0.8156	Intermediate Similarity	NPC767
0.8156	Intermediate Similarity	NPC247250
0.8156	Intermediate Similarity	NPC229894
0.8151	Intermediate Similarity	NPC290030
0.8151	Intermediate Similarity	NPC471905
0.8151	Intermediate Similarity	NPC53001
0.8151	Intermediate Similarity	NPC119542
0.8146	Intermediate Similarity	NPC285122
0.8146	Intermediate Similarity	NPC470570
0.8143	Intermediate Similarity	NPC71610
0.8143	Intermediate Similarity	NPC15837
0.8138	Intermediate Similarity	NPC477596
0.8138	Intermediate Similarity	NPC283088
0.8133	Intermediate Similarity	NPC48130
0.8133	Intermediate Similarity	NPC48762
0.8133	Intermediate Similarity	NPC218866
0.8133	Intermediate Similarity	NPC84568
0.8133	Intermediate Similarity	NPC300684
0.8129	Intermediate Similarity	NPC472211
0.8129	Intermediate Similarity	NPC15127
0.8129	Intermediate Similarity	NPC12818
0.8129	Intermediate Similarity	NPC125487
0.8129	Intermediate Similarity	NPC93552
0.8129	Intermediate Similarity	NPC107109
0.8129	Intermediate Similarity	NPC281703

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 NPC248068 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	303
0.1-0.2	867
0.2-0.3	1560
0.3-0.4	2767
0.4-0.5	2081
0.5-0.6	1070
0.6-0.7	443
0.7-0.8	58
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8446	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.8082	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD1470	Approved
0.7815	Intermediate Similarity	NPD8166	Discontinued
0.7808	Intermediate Similarity	NPD943	Approved
0.7698	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD5406	Approved
0.7667	Intermediate Similarity	NPD5404	Approved
0.7667	Intermediate Similarity	NPD5408	Approved
0.7667	Intermediate Similarity	NPD5405	Approved
0.7662	Intermediate Similarity	NPD7390	Discontinued
0.766	Intermediate Similarity	NPD1201	Approved
0.7643	Intermediate Similarity	NPD3019	Approved
0.7562	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6190	Approved
0.753	Intermediate Similarity	NPD7473	Discontinued
0.7518	Intermediate Similarity	NPD2932	Approved
0.7484	Intermediate Similarity	NPD3300	Phase 2
0.7468	Intermediate Similarity	NPD4628	Phase 3
0.7455	Intermediate Similarity	NPD6232	Discontinued
0.744	Intermediate Similarity	NPD5844	Phase 1
0.7421	Intermediate Similarity	NPD7458	Discontinued
0.7413	Intermediate Similarity	NPD3092	Approved
0.7399	Intermediate Similarity	NPD8150	Discontinued
0.7365	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD6166	Phase 2
0.7365	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD3882	Suspended
0.7362	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD7003	Approved
0.7329	Intermediate Similarity	NPD3094	Phase 2
0.7314	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD230	Phase 1
0.7284	Intermediate Similarity	NPD1934	Approved
0.7267	Intermediate Similarity	NPD6663	Approved
0.7255	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD3091	Approved
0.7251	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD9269	Phase 2
0.7241	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD5736	Approved
0.7222	Intermediate Similarity	NPD3026	Approved
0.7222	Intermediate Similarity	NPD3023	Approved
0.7219	Intermediate Similarity	NPD3620	Phase 2
0.7219	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD5951	Approved
0.7203	Intermediate Similarity	NPD3025	Approved
0.7203	Intermediate Similarity	NPD3024	Approved
0.7186	Intermediate Similarity	NPD6959	Discontinued
0.7179	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD2533	Approved
0.717	Intermediate Similarity	NPD2532	Approved
0.717	Intermediate Similarity	NPD2534	Approved
0.716	Intermediate Similarity	NPD4380	Phase 2
0.7135	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2801	Approved
0.7125	Intermediate Similarity	NPD6273	Approved
0.7125	Intermediate Similarity	NPD1512	Approved
0.7114	Intermediate Similarity	NPD9494	Approved
0.7113	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD7075	Discontinued
0.7101	Intermediate Similarity	NPD3022	Approved
0.7101	Intermediate Similarity	NPD3021	Approved
0.7099	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD3226	Approved
0.7086	Intermediate Similarity	NPD3764	Approved
0.7076	Intermediate Similarity	NPD3818	Discontinued
0.7073	Intermediate Similarity	NPD37	Approved
0.7066	Intermediate Similarity	NPD6234	Discontinued
0.7063	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD6535	Approved
0.7056	Intermediate Similarity	NPD6534	Approved
0.7055	Intermediate Similarity	NPD6599	Discontinued
0.7051	Intermediate Similarity	NPD2346	Discontinued
0.7044	Intermediate Similarity	NPD7236	Approved
0.7034	Intermediate Similarity	NPD3095	Discontinued
0.7034	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD7819	Suspended
0.7029	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD5494	Approved
0.702	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD3972	Approved
0.7	Intermediate Similarity	NPD1511	Approved
0.6988	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD6099	Approved
0.6987	Remote Similarity	NPD6100	Approved
0.6982	Remote Similarity	NPD8127	Discontinued
0.6972	Remote Similarity	NPD2629	Approved
0.6971	Remote Similarity	NPD5034	Approved
0.6971	Remote Similarity	NPD4954	Approved
0.6971	Remote Similarity	NPD36	Approved
0.6971	Remote Similarity	NPD5028	Approved
0.6971	Remote Similarity	NPD4955	Approved
0.6971	Remote Similarity	NPD5026	Approved
0.697	Remote Similarity	NPD6801	Discontinued
0.6966	Remote Similarity	NPD9268	Approved
0.6957	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6797	Phase 2
0.6946	Remote Similarity	NPD4967	Phase 2
0.6946	Remote Similarity	NPD4966	Approved
0.6946	Remote Similarity	NPD4965	Approved
0.694	Remote Similarity	NPD7699	Phase 2
0.694	Remote Similarity	NPD7700	Phase 2
0.6933	Remote Similarity	NPD7239	Suspended
0.6932	Remote Similarity	NPD8313	Approved
0.6932	Remote Similarity	NPD8312	Approved
0.6928	Remote Similarity	NPD1465	Phase 2
0.6923	Remote Similarity	NPD1510	Phase 2
0.6918	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7251	Discontinued
0.6914	Remote Similarity	NPD5030	Phase 2
0.691	Remote Similarity	NPD8434	Phase 2
0.691	Remote Similarity	NPD5038	Approved
0.691	Remote Similarity	NPD5037	Approved
0.6908	Remote Similarity	NPD7008	Discontinued
0.6903	Remote Similarity	NPD1607	Approved
0.6899	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7074	Phase 3
0.6889	Remote Similarity	NPD2490	Approved
0.6889	Remote Similarity	NPD2488	Approved
0.6886	Remote Similarity	NPD3817	Phase 2
0.6883	Remote Similarity	NPD4060	Phase 1
0.6879	Remote Similarity	NPD2935	Discontinued
0.6879	Remote Similarity	NPD7228	Approved
0.6875	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD6782	Approved
0.6865	Remote Similarity	NPD6780	Approved
0.6865	Remote Similarity	NPD6778	Approved
0.6865	Remote Similarity	NPD6781	Approved
0.6865	Remote Similarity	NPD6779	Approved
0.6865	Remote Similarity	NPD6776	Approved
0.6865	Remote Similarity	NPD6777	Approved
0.6861	Remote Similarity	NPD1237	Approved
0.6854	Remote Similarity	NPD5036	Approved
0.6852	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7054	Approved
0.6836	Remote Similarity	NPD5035	Approved
0.6835	Remote Similarity	NPD2342	Discontinued
0.6831	Remote Similarity	NPD7635	Approved
0.6815	Remote Similarity	NPD2799	Discontinued
0.6813	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD8320	Phase 1
0.6809	Remote Similarity	NPD8319	Approved
0.68	Remote Similarity	NPD7472	Approved
0.68	Remote Similarity	NPD1283	Approved
0.6795	Remote Similarity	NPD6651	Approved
0.6792	Remote Similarity	NPD1549	Phase 2
0.6791	Remote Similarity	NPD2491	Approved
0.679	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD9545	Approved
0.678	Remote Similarity	NPD7808	Phase 3
0.6774	Remote Similarity	NPD1240	Approved
0.6755	Remote Similarity	NPD7435	Discontinued
0.6755	Remote Similarity	NPD1164	Approved
0.675	Remote Similarity	NPD2800	Approved
0.675	Remote Similarity	NPD6674	Discontinued
0.6748	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD1651	Approved
0.673	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.673	Remote Similarity	NPD7266	Discontinued
0.673	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD5027	Approved
0.6723	Remote Similarity	NPD6559	Discontinued
0.6723	Remote Similarity	NPD5031	Approved
0.6723	Remote Similarity	NPD5029	Approved
0.6723	Remote Similarity	NPD7685	Pre-registration
0.6721	Remote Similarity	NPD6213	Phase 3
0.6721	Remote Similarity	NPD6212	Phase 3
0.6721	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD3750	Approved
0.6707	Remote Similarity	NPD7411	Suspended
0.6706	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD4956	Approved
0.6705	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD3057	Approved
0.6702	Remote Similarity	NPD3448	Approved
0.6689	Remote Similarity	NPD4059	Approved
0.6689	Remote Similarity	NPD4626	Approved
0.6687	Remote Similarity	NPD6799	Approved
0.6687	Remote Similarity	NPD3455	Phase 2
0.6686	Remote Similarity	NPD7199	Phase 2
0.6686	Remote Similarity	NPD3751	Discontinued
0.6686	Remote Similarity	NPD7177	Discontinued
0.6667	Remote Similarity	NPD7696	Phase 3
0.6667	Remote Similarity	NPD7697	Approved
0.6667	Remote Similarity	NPD4208	Discontinued
0.6667	Remote Similarity	NPD7698	Approved
0.6667	Remote Similarity	NPD4878	Approved
0.6667	Remote Similarity	NPD2796	Approved
0.6667	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD2494	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