NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	160.05
Volume:	168.802
LogP:	2.422
LogD:	2.322
LogS:	-2.625
# Rotatable Bonds:	0
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.58
Synthetic Accessibility Score:	1.652
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.57
MDCK Permeability:	1.9224558855057694e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.173
20% Bioavailability (F20%):	0.972
30% Bioavailability (F30%):	0.979

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.205
Plasma Protein Binding (PPB):	94.8035659790039%
Volume Distribution (VD):	0.599
Pgp-substrate:	3.4168004989624023%

ADMET: Metabolism

CYP1A2-inhibitor:	0.974
CYP1A2-substrate:	0.426
CYP2C19-inhibitor:	0.352
CYP2C19-substrate:	0.112
CYP2C9-inhibitor:	0.372
CYP2C9-substrate:	0.885
CYP2D6-inhibitor:	0.723
CYP2D6-substrate:	0.888
CYP3A4-inhibitor:	0.25
CYP3A4-substrate:	0.197

ADMET: Excretion

Clearance (CL):	16.192
Half-life (T1/2):	0.871

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.014
Drug-inuced Liver Injury (DILI):	0.366
AMES Toxicity:	0.71
Rat Oral Acute Toxicity:	0.757
Maximum Recommended Daily Dose:	0.252
Skin Sensitization:	0.945
Carcinogencity:	0.835
Eye Corrosion:	0.724
Eye Irritation:	0.994
Respiratory Toxicity:	0.933

Download Data

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

Natural Product: NPC233827

Natural Product ID:	NPC233827
*Common Name:**	Naphthalene-1,4-Diol
IUPAC Name:	naphthalene-1,4-diol
Synonyms:	1,4-Dihydroxynaphthalene; Naphthalene-1,4-Diol
Standard InCHIKey:	PCILLCXFKWDRMK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H8O2/c11-9-5-6-10(12)8-4-2-1-3-7(8)9/h1-6,11-12H
SMILES:	Oc1ccc(c2c1cccc2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL206816
PubChem CID:	11305
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes [CHEMONTID:0002441] Naphthols and derivatives

*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
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	leaf	n.a.	PMID[14727919]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	xylem	n.a.	PMID[14727919]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	bark	n.a.	PMID[14727919]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	root	n.a.	PMID[14727919]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	pericarp	n.a.	PMID[18496782]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25466114]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[28737396]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	leaf	n.a.	Database[Article]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Embryo	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Stem Bark	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	Testa	n.a.	n.a.	Database[FooDB]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO22736.1	Drosera peltata var. lunata	Varieties	Droseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22736.1	Drosera peltata var. lunata	Varieties	Droseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18674	Juglans regia	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18674	Juglans regia	Species	Juglandaceae	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
ED50	2
IC50	4
LD50	3

Activity Type	# Activity
Cell Line	3
Individual Protein	4
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1855	Cell Line	HFL1	Homo sapiens	ED50	=	1.0	uM	PMID[565103]
NPT550	Cell Line	T-24	Homo sapiens	ED50	=	0.7	uM	PMID[565103]
NPT1078	Individual Protein	Indoleamine 2,3-dioxygenase	Homo sapiens	IC50	=	1500.0	nM	PMID[565104]
NPT5070	Individual Protein	Indoleamine 2,3-dioxygenase 1	Mus musculus	IC50	=	10000.0	nM	PMID[565104]
NPT1078	Individual Protein	Indoleamine 2,3-dioxygenase	Homo sapiens	IC50	=	10000.0	nM	PMID[565104]
NPT5069	Individual Protein	Tryptophan 2,3-dioxygenase	Mus musculus	IC50	>	10000.0	nM	PMID[565104]
NPT71	Cell Line	HEK293	Homo sapiens	LD50	=	40.0	uM	PMID[565104]
NPT27	Others	Unspecified		LD50	=	40.0	uM	PMID[565104]
NPT27	Others	Unspecified		LD50	=	10.0	uM	PMID[565104]

☑ 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 NPC233827 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	502
0.1-0.2	2292
0.2-0.3	7670
0.3-0.4	11851
0.4-0.5	5490
0.5-0.6	9982
0.6-0.7	3850
0.7-0.8	882
0.8-0.85	132
0.85-0.9	38
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9694	High Similarity	NPC67250
0.9579	High Similarity	NPC156313
0.9485	High Similarity	NPC12221
0.9388	High Similarity	NPC168393
0.93	High Similarity	NPC54765
0.9175	High Similarity	NPC32674
0.9118	High Similarity	NPC95344
0.91	High Similarity	NPC475580
0.9062	High Similarity	NPC245187
0.902	High Similarity	NPC320439
0.898	High Similarity	NPC152097
0.8958	High Similarity	NPC29373
0.8958	High Similarity	NPC271440
0.8932	High Similarity	NPC233835
0.8911	High Similarity	NPC272029
0.8911	High Similarity	NPC238696
0.8889	High Similarity	NPC260775
0.8846	High Similarity	NPC202647
0.88	High Similarity	NPC70677
0.88	High Similarity	NPC130103
0.88	High Similarity	NPC48730
0.88	High Similarity	NPC130756
0.88	High Similarity	NPC12931
0.88	High Similarity	NPC248396
0.88	High Similarity	NPC129373
0.8788	High Similarity	NPC475078
0.8776	High Similarity	NPC274678
0.8738	High Similarity	NPC155072
0.8725	High Similarity	NPC254965
0.8725	High Similarity	NPC288411
0.8725	High Similarity	NPC327811
0.8679	High Similarity	NPC266937
0.8679	High Similarity	NPC470770
0.8679	High Similarity	NPC77772
0.8679	High Similarity	NPC95716
0.8673	High Similarity	NPC76938
0.8673	High Similarity	NPC128062
0.8667	High Similarity	NPC314187
0.8667	High Similarity	NPC58865
0.8641	High Similarity	NPC138942
0.8641	High Similarity	NPC47284
0.8627	High Similarity	NPC108497
0.8627	High Similarity	NPC168829
0.8627	High Similarity	NPC269212
0.86	High Similarity	NPC88420
0.8598	High Similarity	NPC177962
0.8598	High Similarity	NPC46940
0.8598	High Similarity	NPC62867
0.8586	High Similarity	NPC32714
0.8571	High Similarity	NPC169450
0.8558	High Similarity	NPC53740
0.8544	High Similarity	NPC102216
0.8544	High Similarity	NPC323810
0.8542	High Similarity	NPC27974
0.8529	High Similarity	NPC477685
0.8529	High Similarity	NPC80800
0.8526	High Similarity	NPC155393
0.8505	High Similarity	NPC151537
0.85	High Similarity	NPC259512
0.85	High Similarity	NPC202986
0.85	High Similarity	NPC312132
0.8469	Intermediate Similarity	NPC231150
0.8469	Intermediate Similarity	NPC45040
0.8462	Intermediate Similarity	NPC471350
0.8462	Intermediate Similarity	NPC117115
0.844	Intermediate Similarity	NPC471534
0.844	Intermediate Similarity	NPC249270
0.8438	Intermediate Similarity	NPC307235
0.8438	Intermediate Similarity	NPC407
0.8431	Intermediate Similarity	NPC174911
0.8431	Intermediate Similarity	NPC294741
0.8431	Intermediate Similarity	NPC72729
0.8426	Intermediate Similarity	NPC302371
0.8416	Intermediate Similarity	NPC79241
0.8416	Intermediate Similarity	NPC6597
0.8411	Intermediate Similarity	NPC132720
0.8407	Intermediate Similarity	NPC277798
0.8407	Intermediate Similarity	NPC100108
0.8396	Intermediate Similarity	NPC11554
0.8396	Intermediate Similarity	NPC262365
0.8384	Intermediate Similarity	NPC55903
0.8378	Intermediate Similarity	NPC470760
0.8378	Intermediate Similarity	NPC299180
0.8367	Intermediate Similarity	NPC312304
0.8367	Intermediate Similarity	NPC192
0.8365	Intermediate Similarity	NPC93831
0.8365	Intermediate Similarity	NPC130817
0.8365	Intermediate Similarity	NPC475225
0.835	Intermediate Similarity	NPC143659
0.835	Intermediate Similarity	NPC100340
0.8349	Intermediate Similarity	NPC322239
0.8349	Intermediate Similarity	NPC715
0.8333	Intermediate Similarity	NPC54373
0.8333	Intermediate Similarity	NPC469912
0.8333	Intermediate Similarity	NPC33675
0.8333	Intermediate Similarity	NPC92730
0.8333	Intermediate Similarity	NPC299762
0.8317	Intermediate Similarity	NPC292730
0.8317	Intermediate Similarity	NPC82664
0.8317	Intermediate Similarity	NPC216520
0.8317	Intermediate Similarity	NPC132271
0.8302	Intermediate Similarity	NPC233320
0.8302	Intermediate Similarity	NPC151477
0.83	Intermediate Similarity	NPC151715
0.83	Intermediate Similarity	NPC152415
0.8288	Intermediate Similarity	NPC261973
0.8288	Intermediate Similarity	NPC141001
0.8288	Intermediate Similarity	NPC115808
0.8286	Intermediate Similarity	NPC239291
0.8286	Intermediate Similarity	NPC292452
0.8283	Intermediate Similarity	NPC306074
0.8273	Intermediate Similarity	NPC195922
0.8273	Intermediate Similarity	NPC470837
0.8273	Intermediate Similarity	NPC107240
0.8269	Intermediate Similarity	NPC235762
0.8269	Intermediate Similarity	NPC471228
0.8246	Intermediate Similarity	NPC129176
0.8241	Intermediate Similarity	NPC296683
0.8241	Intermediate Similarity	NPC13482
0.8235	Intermediate Similarity	NPC474073
0.8235	Intermediate Similarity	NPC225464
0.8235	Intermediate Similarity	NPC291789
0.8229	Intermediate Similarity	NPC286904
0.8229	Intermediate Similarity	NPC150837
0.8224	Intermediate Similarity	NPC174981
0.8218	Intermediate Similarity	NPC26244
0.8208	Intermediate Similarity	NPC21594
0.8208	Intermediate Similarity	NPC469913
0.8208	Intermediate Similarity	NPC248904
0.82	Intermediate Similarity	NPC210497
0.82	Intermediate Similarity	NPC306884
0.82	Intermediate Similarity	NPC147284
0.82	Intermediate Similarity	NPC94139
0.82	Intermediate Similarity	NPC162314
0.82	Intermediate Similarity	NPC3358
0.8198	Intermediate Similarity	NPC232165
0.819	Intermediate Similarity	NPC30506
0.819	Intermediate Similarity	NPC241891
0.819	Intermediate Similarity	NPC471511
0.8182	Intermediate Similarity	NPC471485
0.8173	Intermediate Similarity	NPC252105
0.8165	Intermediate Similarity	NPC308689
0.8165	Intermediate Similarity	NPC224527
0.8165	Intermediate Similarity	NPC275627
0.8148	Intermediate Similarity	NPC98392
0.8148	Intermediate Similarity	NPC19808
0.8148	Intermediate Similarity	NPC473524
0.8148	Intermediate Similarity	NPC33728
0.8142	Intermediate Similarity	NPC63010
0.8137	Intermediate Similarity	NPC473388
0.8131	Intermediate Similarity	NPC474352
0.8131	Intermediate Similarity	NPC66834
0.812	Intermediate Similarity	NPC61685
0.8113	Intermediate Similarity	NPC134829
0.81	Intermediate Similarity	NPC304541
0.8091	Intermediate Similarity	NPC286222
0.8091	Intermediate Similarity	NPC250323
0.8077	Intermediate Similarity	NPC161571
0.8077	Intermediate Similarity	NPC248573
0.8077	Intermediate Similarity	NPC275053
0.8077	Intermediate Similarity	NPC223393
0.8077	Intermediate Similarity	NPC211885
0.8073	Intermediate Similarity	NPC44732
0.8073	Intermediate Similarity	NPC141782
0.807	Intermediate Similarity	NPC323074
0.807	Intermediate Similarity	NPC151197
0.807	Intermediate Similarity	NPC176893
0.8061	Intermediate Similarity	NPC23167
0.8058	Intermediate Similarity	NPC109955
0.8058	Intermediate Similarity	NPC77492
0.8056	Intermediate Similarity	NPC68260
0.8056	Intermediate Similarity	NPC279887
0.8053	Intermediate Similarity	NPC278652
0.8041	Intermediate Similarity	NPC175313
0.8039	Intermediate Similarity	NPC8392
0.8039	Intermediate Similarity	NPC222146
0.8037	Intermediate Similarity	NPC271274
0.8037	Intermediate Similarity	NPC109691
0.8037	Intermediate Similarity	NPC39664
0.8037	Intermediate Similarity	NPC310456
0.8037	Intermediate Similarity	NPC302681
0.8037	Intermediate Similarity	NPC118286
0.8037	Intermediate Similarity	NPC470700
0.8037	Intermediate Similarity	NPC39097
0.8036	Intermediate Similarity	NPC84999
0.8036	Intermediate Similarity	NPC301321
0.8036	Intermediate Similarity	NPC246760
0.8036	Intermediate Similarity	NPC283169
0.8019	Intermediate Similarity	NPC119860
0.8018	Intermediate Similarity	NPC261343
0.8018	Intermediate Similarity	NPC321589
0.8	Intermediate Similarity	NPC47950
0.8	Intermediate Similarity	NPC51015
0.8	Intermediate Similarity	NPC325544
0.8	Intermediate Similarity	NPC4493
0.8	Intermediate Similarity	NPC260323
0.8	Intermediate Similarity	NPC477037
0.8	Intermediate Similarity	NPC476632
0.8	Intermediate Similarity	NPC318581
0.8	Intermediate Similarity	NPC228609

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 NPC233827 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	472
0.1-0.2	1043
0.2-0.3	1384
0.3-0.4	3048
0.4-0.5	1751
0.5-0.6	1067
0.6-0.7	330
0.7-0.8	41
0.8-0.85	11
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.899	High Similarity	NPD289	Clinical (unspecified phase)
0.8952	High Similarity	NPD7635	Approved
0.8654	High Similarity	NPD2342	Discontinued
0.85	High Similarity	NPD288	Approved
0.84	Intermediate Similarity	NPD844	Approved
0.8333	Intermediate Similarity	NPD3020	Approved
0.83	Intermediate Similarity	NPD2933	Approved
0.83	Intermediate Similarity	NPD2934	Approved
0.8273	Intermediate Similarity	NPD497	Approved
0.8218	Intermediate Similarity	NPD2859	Approved
0.8218	Intermediate Similarity	NPD2860	Approved
0.8182	Intermediate Similarity	NPD496	Approved
0.8182	Intermediate Similarity	NPD495	Approved
0.8182	Intermediate Similarity	NPD498	Approved
0.8077	Intermediate Similarity	NPD1242	Phase 1
0.802	Intermediate Similarity	NPD845	Approved
0.7982	Intermediate Similarity	NPD3021	Approved
0.7982	Intermediate Similarity	NPD3022	Approved
0.7941	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7876	Intermediate Similarity	NPD6671	Approved
0.7876	Intermediate Similarity	NPD709	Approved
0.787	Intermediate Similarity	NPD968	Approved
0.7818	Intermediate Similarity	NPD4750	Phase 3
0.7818	Intermediate Similarity	NPD1792	Phase 2
0.7755	Intermediate Similarity	NPD111	Approved
0.7712	Intermediate Similarity	NPD1201	Approved
0.7692	Intermediate Similarity	NPD1809	Phase 2
0.7692	Intermediate Similarity	NPD2286	Discontinued
0.7672	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD940	Approved
0.7664	Intermediate Similarity	NPD846	Approved
0.7652	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7583	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD9088	Approved
0.7563	Intermediate Similarity	NPD1611	Approved
0.7545	Intermediate Similarity	NPD1445	Approved
0.7545	Intermediate Similarity	NPD1444	Approved
0.7521	Intermediate Similarity	NPD3091	Approved
0.748	Intermediate Similarity	NPD2861	Phase 2
0.7478	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD1470	Approved
0.7458	Intermediate Similarity	NPD4093	Discontinued
0.7395	Intermediate Similarity	NPD2932	Approved
0.7395	Intermediate Similarity	NPD4059	Approved
0.7395	Intermediate Similarity	NPD3019	Approved
0.7391	Intermediate Similarity	NPD1398	Phase 1
0.7383	Intermediate Similarity	NPD9273	Approved
0.736	Intermediate Similarity	NPD4625	Phase 3
0.735	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3092	Approved
0.725	Intermediate Similarity	NPD1751	Approved
0.7248	Intermediate Similarity	NPD3028	Approved
0.7241	Intermediate Similarity	NPD2234	Approved
0.7241	Intermediate Similarity	NPD2228	Approved
0.7241	Intermediate Similarity	NPD2229	Approved
0.7236	Intermediate Similarity	NPD6696	Suspended
0.7217	Intermediate Similarity	NPD228	Approved
0.7213	Intermediate Similarity	NPD2230	Approved
0.7213	Intermediate Similarity	NPD2232	Approved
0.7213	Intermediate Similarity	NPD2233	Approved
0.7203	Intermediate Similarity	NPD7340	Approved
0.7179	Intermediate Similarity	NPD9618	Approved
0.7179	Intermediate Similarity	NPD9614	Approved
0.7177	Intermediate Similarity	NPD3094	Phase 2
0.7177	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD9087	Approved
0.7155	Intermediate Similarity	NPD9379	Approved
0.7155	Intermediate Similarity	NPD9377	Approved
0.7131	Intermediate Similarity	NPD1610	Phase 2
0.7117	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD9500	Approved
0.7107	Intermediate Similarity	NPD4589	Approved
0.7107	Intermediate Similarity	NPD3095	Discontinued
0.7107	Intermediate Similarity	NPD4626	Approved
0.7097	Intermediate Similarity	NPD1283	Approved
0.7083	Intermediate Similarity	NPD5304	Approved
0.7083	Intermediate Similarity	NPD1548	Phase 1
0.7083	Intermediate Similarity	NPD5303	Approved
0.7054	Intermediate Similarity	NPD4060	Phase 1
0.7054	Intermediate Similarity	NPD9610	Approved
0.7054	Intermediate Similarity	NPD9608	Approved
0.7049	Intermediate Similarity	NPD1980	Approved
0.7049	Intermediate Similarity	NPD1981	Approved
0.7049	Intermediate Similarity	NPD3496	Discontinued
0.7049	Intermediate Similarity	NPD1983	Approved
0.704	Intermediate Similarity	NPD1164	Approved
0.7034	Intermediate Similarity	NPD1793	Approved
0.7034	Intermediate Similarity	NPD1791	Approved
0.7025	Intermediate Similarity	NPD1651	Approved
0.7016	Intermediate Similarity	NPD1669	Approved
0.7008	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD9615	Approved
0.7	Intermediate Similarity	NPD9616	Approved
0.7	Intermediate Similarity	NPD9613	Approved
0.6992	Remote Similarity	NPD1535	Discovery
0.6992	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD9295	Approved
0.6949	Remote Similarity	NPD5283	Phase 1
0.6949	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD7330	Discontinued
0.6942	Remote Similarity	NPD316	Approved
0.6939	Remote Similarity	NPD9294	Approved
0.6937	Remote Similarity	NPD1616	Discontinued
0.6935	Remote Similarity	NPD1481	Phase 2
0.6935	Remote Similarity	NPD1840	Phase 2
0.6929	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD5736	Approved
0.6923	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.688	Remote Similarity	NPD4749	Approved
0.687	Remote Similarity	NPD290	Approved
0.6866	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD1281	Approved
0.685	Remote Similarity	NPD2194	Approved
0.685	Remote Similarity	NPD2195	Approved
0.6829	Remote Similarity	NPD9381	Approved
0.6829	Remote Similarity	NPD9384	Approved
0.6825	Remote Similarity	NPD5311	Approved
0.6825	Remote Similarity	NPD5310	Approved
0.6822	Remote Similarity	NPD5155	Approved
0.6822	Remote Similarity	NPD5156	Approved
0.681	Remote Similarity	NPD74	Approved
0.681	Remote Similarity	NPD9266	Approved
0.6807	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.68	Remote Similarity	NPD2231	Phase 2
0.68	Remote Similarity	NPD2235	Phase 2
0.68	Remote Similarity	NPD1608	Approved
0.6797	Remote Similarity	NPD3637	Approved
0.6797	Remote Similarity	NPD3635	Approved
0.6797	Remote Similarity	NPD3636	Approved
0.6794	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD1613	Approved
0.6791	Remote Similarity	NPD5404	Approved
0.6791	Remote Similarity	NPD2935	Discontinued
0.6791	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD5405	Approved
0.6791	Remote Similarity	NPD5406	Approved
0.6791	Remote Similarity	NPD5408	Approved
0.6789	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD3026	Approved
0.6774	Remote Similarity	NPD3023	Approved
0.6772	Remote Similarity	NPD3053	Approved
0.6772	Remote Similarity	NPD3055	Approved
0.6765	Remote Similarity	NPD9089	Approved
0.6748	Remote Similarity	NPD3444	Approved
0.6748	Remote Similarity	NPD3443	Approved
0.6748	Remote Similarity	NPD5691	Approved
0.6748	Remote Similarity	NPD3025	Approved
0.6748	Remote Similarity	NPD3445	Approved
0.6748	Remote Similarity	NPD3024	Approved
0.6746	Remote Similarity	NPD1755	Approved
0.6744	Remote Similarity	NPD596	Approved
0.6744	Remote Similarity	NPD600	Approved
0.6744	Remote Similarity	NPD2606	Approved
0.6744	Remote Similarity	NPD3594	Approved
0.6744	Remote Similarity	NPD4908	Phase 1
0.6744	Remote Similarity	NPD2605	Approved
0.6744	Remote Similarity	NPD3595	Approved
0.6724	Remote Similarity	NPD9267	Approved
0.6724	Remote Similarity	NPD9264	Approved
0.6724	Remote Similarity	NPD9263	Approved
0.6719	Remote Similarity	NPD4624	Approved
0.6719	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD6584	Phase 3
0.6718	Remote Similarity	NPD6663	Approved
0.6716	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD1753	Discontinued
0.6694	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD1024	Discontinued
0.6692	Remote Similarity	NPD4097	Suspended
0.6692	Remote Similarity	NPD3027	Phase 3
0.6667	Remote Similarity	NPD1759	Phase 1
0.6667	Remote Similarity	NPD943	Approved
0.6667	Remote Similarity	NPD2238	Phase 2
0.6667	Remote Similarity	NPD9093	Approved
0.6667	Remote Similarity	NPD1182	Approved
0.6667	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1712	Approved
0.6642	Remote Similarity	NPD7718	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD2797	Approved
0.6641	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD3764	Approved
0.6639	Remote Similarity	NPD9493	Approved
0.6619	Remote Similarity	NPD3300	Phase 2
0.6614	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD9622	Approved
0.6613	Remote Similarity	NPD5585	Approved
0.6612	Remote Similarity	NPD475	Phase 2
0.661	Remote Similarity	NPD5451	Approved
0.6596	Remote Similarity	NPD6090	Discontinued
0.6593	Remote Similarity	NPD2156	Approved
0.6593	Remote Similarity	NPD2154	Approved
0.6593	Remote Similarity	NPD2155	Approved
0.6593	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD839	Approved
0.6591	Remote Similarity	NPD840	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