NPASS Compound

Structure

CID261973 OpenBabel06191716062D 24 27 0 0 0 0 0 0 0 0999 V2000 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -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 5.1962 -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 2.5981 1.5000 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 3.4641 2.0000 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 2.5981 0.5000 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 3.4641 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 5.1962 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 4.3301 1.5000 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 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 5 1 0 0 0 0 2 4 2 0 0 0 0 2 6 1 0 0 0 0 3 13 1 0 0 0 0 4 14 1 0 0 0 0 5 15 2 0 0 0 0 6 16 2 0 0 0 0 7 9 1 0 0 0 0 7 11 2 0 0 0 0 8 10 1 0 0 0 0 8 12 2 0 0 0 0 9 17 2 0 0 0 0 10 18 2 0 0 0 0 11 12 1 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 13 19 2 0 0 0 0 14 20 2 0 0 0 0 15 19 1 0 0 0 0 15 21 1 0 0 0 0 16 20 1 0 0 0 0 16 22 1 0 0 0 0 17 19 1 0 0 0 0 17 23 1 0 0 0 0 18 20 1 0 0 0 0 18 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.09
Volume:	329.047
LogP:	5.284
LogD:	3.434
LogS:	-4.536
# Rotatable Bonds:	1
TPSA:	80.92
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.417
Synthetic Accessibility Score:	2.188
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.144
MDCK Permeability:	1.3832816875947174e-05
Pgp-inhibitor:	0.032
Pgp-substrate:	0.012
Human Intestinal Absorption (HIA):	0.979
20% Bioavailability (F20%):	0.984
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.018
Plasma Protein Binding (PPB):	98.99840545654297%
Volume Distribution (VD):	0.628
Pgp-substrate:	0.9644736647605896%

ADMET: Metabolism

CYP1A2-inhibitor:	0.989
CYP1A2-substrate:	0.175
CYP2C19-inhibitor:	0.761
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.666
CYP2C9-substrate:	0.915
CYP2D6-inhibitor:	0.663
CYP2D6-substrate:	0.896
CYP3A4-inhibitor:	0.209
CYP3A4-substrate:	0.152

ADMET: Excretion

Clearance (CL):	9.047
Half-life (T1/2):	0.366

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.012
Drug-inuced Liver Injury (DILI):	0.952
AMES Toxicity:	0.792
Rat Oral Acute Toxicity:	0.084
Maximum Recommended Daily Dose:	0.228
Skin Sensitization:	0.967
Carcinogencity:	0.871
Eye Corrosion:	0.058
Eye Irritation:	0.989
Respiratory Toxicity:	0.166

Download Data

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

Natural Product: NPC261973

Natural Product ID:	NPC261973
*Common Name:**	4:5:4':5'-Tetrahydroxy-1:1'-Binaphthyl
IUPAC Name:	4-(4,5-dihydroxynaphthalen-1-yl)naphthalene-1,8-diol
Synonyms:
Standard InCHIKey:	GNXOYKGSVQTWOE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H14O4/c21-15-5-1-3-13-11(7-9-17(23)19(13)15)12-8-10-18(24)20-14(12)4-2-6-16(20)22/h1-10,21-24H
SMILES:	Oc1ccc(c2c1c(O)ccc2)c1ccc(c2c1cccc2O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL497261
PubChem CID:	10087226
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000325] Biphenols

*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
NPO17651	Bridelia retusa	Species	Phyllanthaceae	Eukaryota	n.a.	stem	n.a.	PMID[12560039]
NPO28797	Hypoxylon carneum	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16933875]
NPO17651	Bridelia retusa	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7334	Embelia barbeyana	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7334	Embelia barbeyana	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9463	Eschenbachia blinii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17651	Bridelia retusa	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9463	Eschenbachia blinii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23262	Lonicera xylosteum	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7867	Cytisus caramanicus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9463	Eschenbachia blinii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10775	Verbascum fruticulosum	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28130	Neonotonia wightii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3596	Podocarpus milanjianus	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3007	Heliotropium bovei	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25288	Planchonia careya	Species	Lecythidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25562	Cephaelis correae	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23823	Tessaria fastigiata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28797	Hypoxylon carneum	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23528	Senecio swaziensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25413	Polyporus benzoinus	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25781	Cassinia uncata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17651	Bridelia retusa	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7334	Embelia barbeyana	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9785	Dictyota binghamiae	Species	Dictyotaceae	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
MIC	6

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	100.0	ug.mL-1	PMID[491534]
NPT3480	Organism	Yarrowia lipolytica	Yarrowia lipolytica	MIC	>	100.0	ug.mL-1	PMID[491534]
NPT3481	Organism	Mucor hiemalis	Mucor hiemalis	MIC	=	100.0	ug.mL-1	PMID[491534]
NPT3482	Organism	Penicillium griseofulvum	Penicillium griseofulvum	MIC	>	100.0	ug.mL-1	PMID[491534]
NPT3483	Organism	Stachybotrys chartarum	Stachybotrys chartarum	MIC	>	100.0	ug.mL-1	PMID[491534]
NPT3484	Organism	Hypocrea lixii	Hypocrea lixii	MIC	>	100.0	ug.mL-1	PMID[491534]

☑ 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 NPC261973 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	610
0.1-0.2	2201
0.2-0.3	6786
0.3-0.4	12346
0.4-0.5	4985
0.5-0.6	8092
0.6-0.7	6296
0.7-0.8	1248
0.8-0.85	107
0.85-0.9	21
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9375	High Similarity	NPC299180
0.9364	High Similarity	NPC322239
0.9018	High Similarity	NPC321589
0.9009	High Similarity	NPC95716
0.9	High Similarity	NPC314187
0.8938	High Similarity	NPC249270
0.8929	High Similarity	NPC46940
0.8898	High Similarity	NPC120172
0.885	High Similarity	NPC715
0.8803	High Similarity	NPC69006
0.8796	High Similarity	NPC168393
0.8772	High Similarity	NPC107240
0.876	High Similarity	NPC9292
0.876	High Similarity	NPC145659
0.875	High Similarity	NPC97578
0.8661	High Similarity	NPC202647
0.8629	High Similarity	NPC254000
0.8624	High Similarity	NPC168829
0.8609	High Similarity	NPC195922
0.8596	High Similarity	NPC43525
0.8571	High Similarity	NPC11554
0.856	High Similarity	NPC282508
0.8559	High Similarity	NPC271274
0.8559	High Similarity	NPC67250
0.8559	High Similarity	NPC54765
0.8547	High Similarity	NPC470760
0.8545	High Similarity	NPC288411
0.8509	High Similarity	NPC225679
0.8509	High Similarity	NPC476632
0.8509	High Similarity	NPC165770
0.8509	High Similarity	NPC4493
0.8496	Intermediate Similarity	NPC58865
0.848	Intermediate Similarity	NPC472369
0.8468	Intermediate Similarity	NPC138942
0.8462	Intermediate Similarity	NPC115808
0.8443	Intermediate Similarity	NPC224342
0.8438	Intermediate Similarity	NPC258780
0.8438	Intermediate Similarity	NPC37410
0.8426	Intermediate Similarity	NPC32674
0.8426	Intermediate Similarity	NPC156313
0.8425	Intermediate Similarity	NPC473665
0.8421	Intermediate Similarity	NPC13482
0.8421	Intermediate Similarity	NPC141782
0.8407	Intermediate Similarity	NPC95344
0.8403	Intermediate Similarity	NPC151197
0.8403	Intermediate Similarity	NPC176893
0.84	Intermediate Similarity	NPC471519
0.84	Intermediate Similarity	NPC471518
0.8378	Intermediate Similarity	NPC238696
0.8376	Intermediate Similarity	NPC246760
0.8376	Intermediate Similarity	NPC84999
0.8374	Intermediate Similarity	NPC28476
0.8374	Intermediate Similarity	NPC133407
0.8372	Intermediate Similarity	NPC133463
0.8372	Intermediate Similarity	NPC206525
0.8372	Intermediate Similarity	NPC191462
0.8372	Intermediate Similarity	NPC472648
0.8372	Intermediate Similarity	NPC170328
0.8372	Intermediate Similarity	NPC472649
0.8372	Intermediate Similarity	NPC472647
0.8362	Intermediate Similarity	NPC117846
0.8348	Intermediate Similarity	NPC151537
0.8348	Intermediate Similarity	NPC260323
0.8348	Intermediate Similarity	NPC176279
0.8347	Intermediate Similarity	NPC237667
0.832	Intermediate Similarity	NPC215300
0.8319	Intermediate Similarity	NPC151477
0.8308	Intermediate Similarity	NPC472646
0.8308	Intermediate Similarity	NPC71465
0.8305	Intermediate Similarity	NPC471668
0.8304	Intermediate Similarity	NPC292452
0.8291	Intermediate Similarity	NPC268160
0.8288	Intermediate Similarity	NPC233827
0.8279	Intermediate Similarity	NPC71094
0.8276	Intermediate Similarity	NPC250323
0.8268	Intermediate Similarity	NPC473309
0.8268	Intermediate Similarity	NPC238168
0.8268	Intermediate Similarity	NPC237424
0.8264	Intermediate Similarity	NPC71870
0.8261	Intermediate Similarity	NPC224870
0.8261	Intermediate Similarity	NPC44732
0.8261	Intermediate Similarity	NPC296683
0.825	Intermediate Similarity	NPC93071
0.825	Intermediate Similarity	NPC126002
0.8246	Intermediate Similarity	NPC262365
0.8246	Intermediate Similarity	NPC233835
0.8246	Intermediate Similarity	NPC61885
0.8246	Intermediate Similarity	NPC63698
0.8241	Intermediate Similarity	NPC274678
0.824	Intermediate Similarity	NPC53781
0.823	Intermediate Similarity	NPC248904
0.8226	Intermediate Similarity	NPC113495
0.822	Intermediate Similarity	NPC147179
0.822	Intermediate Similarity	NPC474486
0.822	Intermediate Similarity	NPC192948
0.822	Intermediate Similarity	NPC35797
0.8214	Intermediate Similarity	NPC30506
0.8214	Intermediate Similarity	NPC327811
0.8214	Intermediate Similarity	NPC254965
0.8214	Intermediate Similarity	NPC102216
0.8211	Intermediate Similarity	NPC53567
0.8205	Intermediate Similarity	NPC263753
0.8198	Intermediate Similarity	NPC51015
0.819	Intermediate Similarity	NPC308689
0.8182	Intermediate Similarity	NPC103916
0.8182	Intermediate Similarity	NPC273623
0.8175	Intermediate Similarity	NPC38017
0.8167	Intermediate Similarity	NPC63010
0.816	Intermediate Similarity	NPC170485
0.8154	Intermediate Similarity	NPC472370
0.8151	Intermediate Similarity	NPC219112
0.8151	Intermediate Similarity	NPC308828
0.8151	Intermediate Similarity	NPC477137
0.8151	Intermediate Similarity	NPC38893
0.8151	Intermediate Similarity	NPC308311
0.8148	Intermediate Similarity	NPC128062
0.8145	Intermediate Similarity	NPC228503
0.8145	Intermediate Similarity	NPC138248
0.8142	Intermediate Similarity	NPC117115
0.8142	Intermediate Similarity	NPC474839
0.8136	Intermediate Similarity	NPC473137
0.813	Intermediate Similarity	NPC176208
0.812	Intermediate Similarity	NPC166995
0.8099	Intermediate Similarity	NPC217174
0.8083	Intermediate Similarity	NPC304510
0.8083	Intermediate Similarity	NPC172219
0.8083	Intermediate Similarity	NPC16030
0.8083	Intermediate Similarity	NPC277588
0.8083	Intermediate Similarity	NPC477136
0.808	Intermediate Similarity	NPC278955
0.808	Intermediate Similarity	NPC105718
0.807	Intermediate Similarity	NPC470700
0.807	Intermediate Similarity	NPC39664
0.807	Intermediate Similarity	NPC118286
0.807	Intermediate Similarity	NPC109691
0.807	Intermediate Similarity	NPC21594
0.807	Intermediate Similarity	NPC39097
0.807	Intermediate Similarity	NPC302681
0.8067	Intermediate Similarity	NPC472893
0.8065	Intermediate Similarity	NPC12824
0.8062	Intermediate Similarity	NPC303144
0.806	Intermediate Similarity	NPC183709
0.8056	Intermediate Similarity	NPC271440
0.8053	Intermediate Similarity	NPC241891
0.8053	Intermediate Similarity	NPC119860
0.8049	Intermediate Similarity	NPC39029
0.8047	Intermediate Similarity	NPC315769
0.8036	Intermediate Similarity	NPC100340
0.8036	Intermediate Similarity	NPC12221
0.8036	Intermediate Similarity	NPC143659
0.8034	Intermediate Similarity	NPC224527
0.8034	Intermediate Similarity	NPC322753
0.8034	Intermediate Similarity	NPC77772
0.8033	Intermediate Similarity	NPC472071
0.8033	Intermediate Similarity	NPC223451
0.803	Intermediate Similarity	NPC62272
0.8017	Intermediate Similarity	NPC33728
0.8017	Intermediate Similarity	NPC471671
0.8017	Intermediate Similarity	NPC469609
0.8017	Intermediate Similarity	NPC206
0.8017	Intermediate Similarity	NPC19808
0.8016	Intermediate Similarity	NPC283508
0.8016	Intermediate Similarity	NPC35341
0.8015	Intermediate Similarity	NPC11727
0.8015	Intermediate Similarity	NPC15109
0.8015	Intermediate Similarity	NPC125579
0.8	Intermediate Similarity	NPC216520
0.8	Intermediate Similarity	NPC469663
0.8	Intermediate Similarity	NPC54844
0.8	Intermediate Similarity	NPC292730
0.8	Intermediate Similarity	NPC92
0.8	Intermediate Similarity	NPC132271
0.8	Intermediate Similarity	NPC82664
0.7984	Intermediate Similarity	NPC471517
0.7984	Intermediate Similarity	NPC474517
0.7984	Intermediate Similarity	NPC191395
0.7984	Intermediate Similarity	NPC72669
0.7983	Intermediate Similarity	NPC12656
0.7982	Intermediate Similarity	NPC151715
0.7982	Intermediate Similarity	NPC134829
0.7982	Intermediate Similarity	NPC246056
0.7982	Intermediate Similarity	NPC245187
0.7982	Intermediate Similarity	NPC76938
0.7967	Intermediate Similarity	NPC100108
0.7967	Intermediate Similarity	NPC277798
0.7967	Intermediate Similarity	NPC24125
0.7966	Intermediate Similarity	NPC302371
0.7966	Intermediate Similarity	NPC228988
0.7966	Intermediate Similarity	NPC228425
0.7966	Intermediate Similarity	NPC286222
0.7963	Intermediate Similarity	NPC45040
0.7951	Intermediate Similarity	NPC469644
0.7951	Intermediate Similarity	NPC191866
0.7949	Intermediate Similarity	NPC132720
0.7949	Intermediate Similarity	NPC475018
0.7946	Intermediate Similarity	NPC248573
0.7946	Intermediate Similarity	NPC225506
0.7946	Intermediate Similarity	NPC211885
0.7946	Intermediate Similarity	NPC275053
0.7946	Intermediate Similarity	NPC161571

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 NPC261973 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	514
0.1-0.2	1010
0.2-0.3	1404
0.3-0.4	3078
0.4-0.5	1717
0.5-0.6	1048
0.6-0.7	332
0.7-0.8	44
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8818	High Similarity	NPD2342	Discontinued
0.8182	Intermediate Similarity	NPD2286	Discontinued
0.812	Intermediate Similarity	NPD7635	Approved
0.803	Intermediate Similarity	NPD5406	Approved
0.803	Intermediate Similarity	NPD5405	Approved
0.803	Intermediate Similarity	NPD5404	Approved
0.803	Intermediate Similarity	NPD5408	Approved
0.8018	Intermediate Similarity	NPD3020	Approved
0.7946	Intermediate Similarity	NPD1242	Phase 1
0.7909	Intermediate Similarity	NPD2859	Approved
0.7909	Intermediate Similarity	NPD2860	Approved
0.7863	Intermediate Similarity	NPD3022	Approved
0.7863	Intermediate Similarity	NPD3021	Approved
0.7818	Intermediate Similarity	NPD2933	Approved
0.7818	Intermediate Similarity	NPD2934	Approved
0.7778	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7769	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7754	Intermediate Similarity	NPD7390	Discontinued
0.775	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD3091	Approved
0.7719	Intermediate Similarity	NPD846	Approved
0.7719	Intermediate Similarity	NPD940	Approved
0.7712	Intermediate Similarity	NPD4750	Phase 3
0.7692	Intermediate Similarity	NPD4625	Phase 3
0.7679	Intermediate Similarity	NPD288	Approved
0.7661	Intermediate Similarity	NPD4093	Discontinued
0.7632	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD4908	Phase 1
0.76	Intermediate Similarity	NPD3019	Approved
0.76	Intermediate Similarity	NPD4059	Approved
0.7589	Intermediate Similarity	NPD1809	Phase 2
0.7589	Intermediate Similarity	NPD844	Approved
0.7568	Intermediate Similarity	NPD845	Approved
0.7541	Intermediate Similarity	NPD497	Approved
0.7519	Intermediate Similarity	NPD3094	Phase 2
0.7519	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD3092	Approved
0.748	Intermediate Similarity	NPD1201	Approved
0.746	Intermediate Similarity	NPD2932	Approved
0.746	Intermediate Similarity	NPD3095	Discontinued
0.7459	Intermediate Similarity	NPD495	Approved
0.7459	Intermediate Similarity	NPD498	Approved
0.7459	Intermediate Similarity	NPD496	Approved
0.7426	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD1470	Approved
0.7344	Intermediate Similarity	NPD1610	Phase 2
0.7299	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD4097	Suspended
0.7259	Intermediate Similarity	NPD4060	Phase 1
0.7254	Intermediate Similarity	NPD7041	Phase 2
0.7254	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD1164	Approved
0.7218	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4626	Approved
0.7188	Intermediate Similarity	NPD4589	Approved
0.7165	Intermediate Similarity	NPD1548	Phase 1
0.7165	Intermediate Similarity	NPD5303	Approved
0.7165	Intermediate Similarity	NPD5304	Approved
0.7164	Intermediate Similarity	NPD5155	Approved
0.7164	Intermediate Similarity	NPD5156	Approved
0.7156	Intermediate Similarity	NPD111	Approved
0.7154	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5736	Approved
0.7132	Intermediate Similarity	NPD3026	Approved
0.7132	Intermediate Similarity	NPD3023	Approved
0.7131	Intermediate Similarity	NPD1792	Phase 2
0.7109	Intermediate Similarity	NPD3025	Approved
0.7109	Intermediate Similarity	NPD3024	Approved
0.709	Intermediate Similarity	NPD3594	Approved
0.709	Intermediate Similarity	NPD2605	Approved
0.709	Intermediate Similarity	NPD2606	Approved
0.709	Intermediate Similarity	NPD3595	Approved
0.7063	Intermediate Similarity	NPD709	Approved
0.7054	Intermediate Similarity	NPD1751	Approved
0.7045	Intermediate Similarity	NPD1283	Approved
0.7042	Intermediate Similarity	NPD7003	Approved
0.704	Intermediate Similarity	NPD2234	Approved
0.704	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD2228	Approved
0.704	Intermediate Similarity	NPD2229	Approved
0.7034	Intermediate Similarity	NPD3028	Approved
0.7031	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD7037	Approved
0.7015	Intermediate Similarity	NPD2861	Phase 2
0.7014	Intermediate Similarity	NPD2420	Approved
0.7014	Intermediate Similarity	NPD2421	Approved
0.7007	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD1613	Approved
0.6985	Remote Similarity	NPD3764	Approved
0.6978	Remote Similarity	NPD7718	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD1651	Approved
0.697	Remote Similarity	NPD1669	Approved
0.697	Remote Similarity	NPD4749	Approved
0.6947	Remote Similarity	NPD1611	Approved
0.6944	Remote Similarity	NPD3845	Phase 1
0.694	Remote Similarity	NPD4624	Approved
0.694	Remote Similarity	NPD6584	Phase 3
0.6934	Remote Similarity	NPD6663	Approved
0.6934	Remote Similarity	NPD6407	Approved
0.6934	Remote Similarity	NPD6405	Approved
0.6929	Remote Similarity	NPD6671	Approved
0.6923	Remote Similarity	NPD3750	Approved
0.6917	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD3027	Phase 3
0.6905	Remote Similarity	NPD5283	Phase 1
0.6892	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD3637	Approved
0.6889	Remote Similarity	NPD3636	Approved
0.6889	Remote Similarity	NPD3635	Approved
0.6885	Remote Similarity	NPD1445	Approved
0.6885	Remote Similarity	NPD1444	Approved
0.6884	Remote Similarity	NPD943	Approved
0.6883	Remote Similarity	NPD6959	Discontinued
0.6879	Remote Similarity	NPD2935	Discontinued
0.6875	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD9273	Approved
0.6861	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD5451	Approved
0.6853	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.685	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD5691	Approved
0.6842	Remote Similarity	NPD7768	Phase 2
0.6831	Remote Similarity	NPD4726	Approved
0.6831	Remote Similarity	NPD4725	Approved
0.6831	Remote Similarity	NPD4721	Approved
0.6818	Remote Similarity	NPD1281	Approved
0.6815	Remote Similarity	NPD2194	Approved
0.6815	Remote Similarity	NPD2195	Approved
0.6815	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD4108	Discontinued
0.6806	Remote Similarity	NPD5819	Phase 2
0.6777	Remote Similarity	NPD9500	Approved
0.6769	Remote Similarity	NPD7330	Discontinued
0.6763	Remote Similarity	NPD3620	Phase 2
0.6763	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD228	Approved
0.6739	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD6232	Discontinued
0.6716	Remote Similarity	NPD6582	Phase 2
0.6716	Remote Similarity	NPD5327	Phase 3
0.6716	Remote Similarity	NPD6583	Phase 3
0.6713	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD9377	Approved
0.6693	Remote Similarity	NPD5535	Approved
0.6693	Remote Similarity	NPD9379	Approved
0.6692	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.669	Remote Similarity	NPD7743	Approved
0.669	Remote Similarity	NPD8166	Discontinued
0.669	Remote Similarity	NPD7742	Approved
0.6688	Remote Similarity	NPD3749	Approved
0.6667	Remote Similarity	NPD7095	Approved
0.6667	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6696	Suspended
0.6643	Remote Similarity	NPD1555	Discontinued
0.6643	Remote Similarity	NPD4140	Approved
0.6642	Remote Similarity	NPD2233	Approved
0.6642	Remote Similarity	NPD2232	Approved
0.6642	Remote Similarity	NPD2230	Approved
0.6641	Remote Similarity	NPD1398	Phase 1
0.6622	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD7447	Phase 1
0.6618	Remote Similarity	NPD2797	Approved
0.6615	Remote Similarity	NPD7340	Approved
0.6613	Remote Similarity	NPD968	Approved
0.6604	Remote Similarity	NPD7473	Discontinued
0.6599	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD5735	Approved
0.6591	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD9610	Approved
0.6585	Remote Similarity	NPD9608	Approved
0.6575	Remote Similarity	NPD3400	Discontinued
0.6573	Remote Similarity	NPD3748	Approved
0.6573	Remote Similarity	NPD1510	Phase 2
0.6573	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD7451	Discontinued
0.6567	Remote Similarity	NPD422	Phase 1
0.6564	Remote Similarity	NPD8453	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD7213	Phase 3
0.6554	Remote Similarity	NPD7212	Phase 2
0.6549	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD6353	Approved
0.6549	Remote Similarity	NPD2568	Approved
0.6544	Remote Similarity	NPD5311	Approved
0.6544	Remote Similarity	NPD3225	Approved
0.6544	Remote Similarity	NPD5310	Approved
0.6541	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD6516	Phase 2
0.6541	Remote Similarity	NPD5846	Approved
0.6538	Remote Similarity	NPD6387	Discontinued

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