NPASS Compound

Structure

NPC107258 OpenBabel07101718322D 22 23 0 0 1 0 0 0 0 0999 V2000 -2.5981 3.5000 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 1.3660 -2.3660 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 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 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 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 -0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 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 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 15 2 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 6 11 1 0 0 0 0 6 12 1 0 0 0 0 7 9 1 0 0 0 0 7 14 1 0 0 0 0 8 10 1 0 0 0 0 8 15 1 0 0 0 0 9 16 1 0 0 0 0 10 17 1 0 0 0 0 11 19 1 0 0 0 0 12 20 1 0 0 0 0 13 14 2 0 0 0 0 13 18 1 0 0 0 0 15 16 1 0 0 0 0 16 20 1 1 0 0 0 17 19 1 0 0 0 0 17 20 1 1 0 0 0 18 21 2 0 0 0 0 18 22 1 0 0 0 0 20 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	338.06
Volume:	311.757
LogP:	2.276
LogD:	1.253
LogS:	-4.108
# Rotatable Bonds:	2
TPSA:	82.06
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.892
Synthetic Accessibility Score:	4.309
Fsp3:	0.375
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.636
MDCK Permeability:	1.8834778529708274e-05
Pgp-inhibitor:	0.022
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.116
Plasma Protein Binding (PPB):	89.14827728271484%
Volume Distribution (VD):	0.95
Pgp-substrate:	9.60030460357666%

ADMET: Metabolism

CYP1A2-inhibitor:	0.317
CYP1A2-substrate:	0.951
CYP2C19-inhibitor:	0.185
CYP2C19-substrate:	0.872
CYP2C9-inhibitor:	0.458
CYP2C9-substrate:	0.251
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.163
CYP3A4-inhibitor:	0.362
CYP3A4-substrate:	0.749

ADMET: Excretion

Clearance (CL):	12.239
Half-life (T1/2):	0.281

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.878
Drug-inuced Liver Injury (DILI):	0.927
AMES Toxicity:	0.034
Rat Oral Acute Toxicity:	0.755
Maximum Recommended Daily Dose:	0.732
Skin Sensitization:	0.871
Carcinogencity:	0.829
Eye Corrosion:	0.003
Eye Irritation:	0.099
Respiratory Toxicity:	0.875

Download Data

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

Natural Product: NPC107258

Natural Product ID:	NPC107258
*Common Name:**	Copalic Acid
IUPAC Name:	(E)-5-[(1R,4aR,8aR)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpent-2-enoic acid
Synonyms:	Copalic Acid
Standard InCHIKey:	JFQBNOIJWROZGE-HPMXROJMSA-N
Standard InCHI:	InChI=1S/C20H32O2/c1-14(13-18(21)22)7-9-16-15(2)8-10-17-19(3,4)11-6-12-20(16,17)5/h13,16-17H,2,6-12H2,1,3-5H3,(H,21,22)/b14-13+/t16-,17-,20+/m1/s1
SMILES:	C/C(=CC(=O)O)/CC[C@@H]1C(=C)CC[C@@H]2C(C)(C)CCC[C@@]12C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL102201
PubChem CID:	11162521
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
NPO2430	Detarium microcarpum	Species	Fabaceae	Eukaryota	fruits	n.a.	n.a.	PMID[16724838]
NPO32774	Copaifera	Genus	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22440015]
NPO2430	Detarium microcarpum	Species	Fabaceae	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
EC50	1
IC50	2
Others	18

Activity Type	# Activity
Cell Line	1
Individual Protein	1
Organism	17
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	Activity	>	10.0	ug	PMID[451936]
NPT2679	Cell Line	LLC-MK2	Macaca mulatta	CC50	=	39400.0	nM	PMID[451937]
NPT32	Organism	Mus musculus	Mus musculus	Change in body weight	=	1.5	g	PMID[451935]
NPT32	Organism	Mus musculus	Mus musculus	Life span	=	14.0	day	PMID[451935]
NPT32	Organism	Mus musculus	Mus musculus	ILS	=	10.0	%	PMID[451935]
NPT985	Organism	Cladosporium cucumerinum	Cladosporium cucumerinum	Activity	>	100.0	ug	PMID[451936]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	42700.0	nM	PMID[451937]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	EC50	=	444000.0	nM	PMID[451937]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	1300.0	nM	PMID[451937]
NPT27	Others	Unspecified		HC50	=	65.7	uM	PMID[451937]
NPT27	Others	Unspecified		Ratio CC50/IC50	=	30.3	n.a.	PMID[451937]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	Activity	=	48.0	%	PMID[451937]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	Activity	=	30.0	%	PMID[451937]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	Activity	=	5.17	%	PMID[451937]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	Activity	=	0.71	%	PMID[451937]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	Activity	=	50.54	%	PMID[451937]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	Activity	=	43.58	%	PMID[451937]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	Activity	=	2.86	%	PMID[451937]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	Activity	=	0.1	%	PMID[451937]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	Activity	=	72.57	%	PMID[451937]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	Activity	=	24.47	%	PMID[451937]

☑ 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 NPC107258 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	142
0.1-0.2	1578
0.2-0.3	10495
0.3-0.4	15095
0.4-0.5	8405
0.5-0.6	5222
0.6-0.7	1500
0.7-0.8	225
0.8-0.85	24
0.85-0.9	6
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9516	High Similarity	NPC259156
0.9516	High Similarity	NPC242945
0.8906	High Similarity	NPC185587
0.8806	High Similarity	NPC133253
0.8529	High Similarity	NPC21944
0.8451	Intermediate Similarity	NPC132542
0.8406	Intermediate Similarity	NPC56747
0.8406	Intermediate Similarity	NPC180015
0.8406	Intermediate Similarity	NPC130016
0.8406	Intermediate Similarity	NPC109576
0.8333	Intermediate Similarity	NPC255781
0.8281	Intermediate Similarity	NPC317177
0.8281	Intermediate Similarity	NPC317025
0.8281	Intermediate Similarity	NPC326645
0.8281	Intermediate Similarity	NPC329416
0.8194	Intermediate Similarity	NPC61952
0.8169	Intermediate Similarity	NPC476346
0.8108	Intermediate Similarity	NPC281880
0.8082	Intermediate Similarity	NPC198240
0.806	Intermediate Similarity	NPC81907
0.8056	Intermediate Similarity	NPC19907
0.803	Intermediate Similarity	NPC329698
0.8	Intermediate Similarity	NPC159148
0.8	Intermediate Similarity	NPC170303
0.7941	Intermediate Similarity	NPC254886
0.7937	Intermediate Similarity	NPC11130
0.7895	Intermediate Similarity	NPC469805
0.7895	Intermediate Similarity	NPC472867
0.7895	Intermediate Similarity	NPC469804
0.7895	Intermediate Similarity	NPC472239
0.7895	Intermediate Similarity	NPC2524
0.7838	Intermediate Similarity	NPC239098
0.7812	Intermediate Similarity	NPC60772
0.7792	Intermediate Similarity	NPC476927
0.7792	Intermediate Similarity	NPC3856
0.7792	Intermediate Similarity	NPC279639
0.7792	Intermediate Similarity	NPC42476
0.7778	Intermediate Similarity	NPC168975
0.7778	Intermediate Similarity	NPC20025
0.7778	Intermediate Similarity	NPC75485
0.7763	Intermediate Similarity	NPC40228
0.7692	Intermediate Similarity	NPC16287
0.7692	Intermediate Similarity	NPC19849
0.7692	Intermediate Similarity	NPC181743
0.7692	Intermediate Similarity	NPC178025
0.7692	Intermediate Similarity	NPC472864
0.7692	Intermediate Similarity	NPC306951
0.7681	Intermediate Similarity	NPC68703
0.7681	Intermediate Similarity	NPC69649
0.7671	Intermediate Similarity	NPC469803
0.7671	Intermediate Similarity	NPC65650
0.7662	Intermediate Similarity	NPC256112
0.7662	Intermediate Similarity	NPC469806
0.7662	Intermediate Similarity	NPC3511
0.7662	Intermediate Similarity	NPC469799
0.7662	Intermediate Similarity	NPC142253
0.7639	Intermediate Similarity	NPC144947
0.7632	Intermediate Similarity	NPC469797
0.7632	Intermediate Similarity	NPC469798
0.76	Intermediate Similarity	NPC105197
0.7595	Intermediate Similarity	NPC329630
0.7595	Intermediate Similarity	NPC60350
0.7576	Intermediate Similarity	NPC176621
0.7568	Intermediate Similarity	NPC4509
0.7564	Intermediate Similarity	NPC311070
0.7564	Intermediate Similarity	NPC79945
0.7564	Intermediate Similarity	NPC97913
0.75	Intermediate Similarity	NPC190211
0.75	Intermediate Similarity	NPC472869
0.75	Intermediate Similarity	NPC181587
0.75	Intermediate Similarity	NPC242767
0.75	Intermediate Similarity	NPC52449
0.75	Intermediate Similarity	NPC169275
0.75	Intermediate Similarity	NPC160817
0.75	Intermediate Similarity	NPC475069
0.75	Intermediate Similarity	NPC186975
0.75	Intermediate Similarity	NPC175145
0.7468	Intermediate Similarity	NPC87552
0.7468	Intermediate Similarity	NPC248758
0.7468	Intermediate Similarity	NPC472865
0.7468	Intermediate Similarity	NPC164577
0.7467	Intermediate Similarity	NPC97377
0.7467	Intermediate Similarity	NPC165711
0.7463	Intermediate Similarity	NPC469728
0.7436	Intermediate Similarity	NPC16321
0.7432	Intermediate Similarity	NPC476795
0.7432	Intermediate Similarity	NPC476844
0.7407	Intermediate Similarity	NPC476409
0.7407	Intermediate Similarity	NPC476293
0.7407	Intermediate Similarity	NPC236618
0.7375	Intermediate Similarity	NPC8571
0.7375	Intermediate Similarity	NPC109528
0.7375	Intermediate Similarity	NPC30984
0.7368	Intermediate Similarity	NPC179028
0.7368	Intermediate Similarity	NPC59436
0.7361	Intermediate Similarity	NPC189745
0.7333	Intermediate Similarity	NPC180886
0.7333	Intermediate Similarity	NPC474463
0.7317	Intermediate Similarity	NPC104560
0.7317	Intermediate Similarity	NPC472870
0.7317	Intermediate Similarity	NPC474629
0.7317	Intermediate Similarity	NPC117122
0.7308	Intermediate Similarity	NPC278459
0.7308	Intermediate Similarity	NPC229584
0.7308	Intermediate Similarity	NPC14203
0.7308	Intermediate Similarity	NPC471898
0.7297	Intermediate Similarity	NPC241854
0.7297	Intermediate Similarity	NPC283908
0.7297	Intermediate Similarity	NPC476046
0.7297	Intermediate Similarity	NPC161923
0.7297	Intermediate Similarity	NPC103958
0.7297	Intermediate Similarity	NPC237591
0.7297	Intermediate Similarity	NPC46610
0.7297	Intermediate Similarity	NPC18819
0.7297	Intermediate Similarity	NPC3753
0.7297	Intermediate Similarity	NPC183503
0.7297	Intermediate Similarity	NPC251970
0.7273	Intermediate Similarity	NPC170394
0.725	Intermediate Similarity	NPC470800
0.725	Intermediate Similarity	NPC102048
0.7237	Intermediate Similarity	NPC107039
0.7237	Intermediate Similarity	NPC471897
0.7237	Intermediate Similarity	NPC91665
0.7237	Intermediate Similarity	NPC471899
0.7229	Intermediate Similarity	NPC66344
0.7229	Intermediate Similarity	NPC146554
0.7229	Intermediate Similarity	NPC472240
0.7229	Intermediate Similarity	NPC262858
0.7215	Intermediate Similarity	NPC320514
0.7213	Intermediate Similarity	NPC22765
0.72	Intermediate Similarity	NPC192540
0.72	Intermediate Similarity	NPC279666
0.7195	Intermediate Similarity	NPC136948
0.7183	Intermediate Similarity	NPC176107
0.7179	Intermediate Similarity	NPC10636
0.7167	Intermediate Similarity	NPC308331
0.7164	Intermediate Similarity	NPC309825
0.7162	Intermediate Similarity	NPC35656
0.716	Intermediate Similarity	NPC217394
0.716	Intermediate Similarity	NPC65661
0.716	Intermediate Similarity	NPC86316
0.716	Intermediate Similarity	NPC106416
0.716	Intermediate Similarity	NPC42586
0.716	Intermediate Similarity	NPC473251
0.716	Intermediate Similarity	NPC269638
0.7143	Intermediate Similarity	NPC472866
0.7143	Intermediate Similarity	NPC280654
0.7143	Intermediate Similarity	NPC275494
0.7143	Intermediate Similarity	NPC260385
0.7143	Intermediate Similarity	NPC471409
0.7143	Intermediate Similarity	NPC110094
0.7143	Intermediate Similarity	NPC78973
0.7125	Intermediate Similarity	NPC474976
0.7125	Intermediate Similarity	NPC477124
0.7125	Intermediate Similarity	NPC49019
0.7125	Intermediate Similarity	NPC474790
0.7125	Intermediate Similarity	NPC469
0.7125	Intermediate Similarity	NPC215893
0.7123	Intermediate Similarity	NPC235586
0.7123	Intermediate Similarity	NPC34834
0.7108	Intermediate Similarity	NPC291665
0.7108	Intermediate Similarity	NPC48107
0.7108	Intermediate Similarity	NPC472809
0.7108	Intermediate Similarity	NPC472810
0.7105	Intermediate Similarity	NPC89294
0.7105	Intermediate Similarity	NPC112680
0.7105	Intermediate Similarity	NPC292589
0.7105	Intermediate Similarity	NPC69143
0.7089	Intermediate Similarity	NPC90055
0.7089	Intermediate Similarity	NPC477372
0.7083	Intermediate Similarity	NPC290445
0.7083	Intermediate Similarity	NPC36616
0.7073	Intermediate Similarity	NPC131813
0.7067	Intermediate Similarity	NPC201048
0.7067	Intermediate Similarity	NPC238146
0.7067	Intermediate Similarity	NPC166797
0.7067	Intermediate Similarity	NPC104644
0.7067	Intermediate Similarity	NPC213223
0.7067	Intermediate Similarity	NPC306727
0.7067	Intermediate Similarity	NPC476366
0.7059	Intermediate Similarity	NPC23217
0.7059	Intermediate Similarity	NPC110923
0.7059	Intermediate Similarity	NPC329842
0.7059	Intermediate Similarity	NPC473986
0.7059	Intermediate Similarity	NPC474018
0.7059	Intermediate Similarity	NPC470113
0.7059	Intermediate Similarity	NPC74296
0.7059	Intermediate Similarity	NPC127582
0.7051	Intermediate Similarity	NPC16394
0.7051	Intermediate Similarity	NPC100906
0.7051	Intermediate Similarity	NPC158846
0.7051	Intermediate Similarity	NPC231431
0.7051	Intermediate Similarity	NPC199595
0.7042	Intermediate Similarity	NPC279434
0.7042	Intermediate Similarity	NPC92327
0.7037	Intermediate Similarity	NPC318515
0.7037	Intermediate Similarity	NPC96055
0.7037	Intermediate Similarity	NPC194937
0.7037	Intermediate Similarity	NPC476412
0.7037	Intermediate Similarity	NPC476038

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 NPC107258 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	127
0.1-0.2	1818
0.2-0.3	4618
0.3-0.4	1927
0.4-0.5	371
0.5-0.6	199
0.6-0.7	85
0.7-0.8	5
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8281	Intermediate Similarity	NPD4194	Approved
0.8281	Intermediate Similarity	NPD4191	Approved
0.8281	Intermediate Similarity	NPD4193	Approved
0.8281	Intermediate Similarity	NPD4192	Approved
0.7	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5325	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD4137	Phase 3
0.6892	Remote Similarity	NPD4691	Approved
0.6892	Remote Similarity	NPD4747	Approved
0.6818	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6049	Phase 2
0.6747	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD4219	Approved
0.6667	Remote Similarity	NPD4623	Approved
0.6667	Remote Similarity	NPD4220	Pre-registration
0.6667	Remote Similarity	NPD4519	Discontinued
0.6627	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD4195	Approved
0.6623	Remote Similarity	NPD4058	Approved
0.6623	Remote Similarity	NPD5733	Approved
0.6579	Remote Similarity	NPD5276	Approved
0.6543	Remote Similarity	NPD4695	Discontinued
0.6538	Remote Similarity	NPD8264	Approved
0.6522	Remote Similarity	NPD7639	Approved
0.6522	Remote Similarity	NPD7640	Approved
0.6506	Remote Similarity	NPD3971	Phase 1
0.65	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD7515	Phase 2
0.6477	Remote Similarity	NPD7637	Suspended
0.6471	Remote Similarity	NPD7146	Approved
0.6471	Remote Similarity	NPD5330	Approved
0.6471	Remote Similarity	NPD6684	Approved
0.6471	Remote Similarity	NPD7521	Approved
0.6471	Remote Similarity	NPD7334	Approved
0.6471	Remote Similarity	NPD6409	Approved
0.6437	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD7638	Approved
0.6413	Remote Similarity	NPD4225	Approved
0.641	Remote Similarity	NPD4687	Approved
0.64	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD4223	Phase 3
0.6386	Remote Similarity	NPD4221	Approved
0.6375	Remote Similarity	NPD5776	Phase 2
0.6375	Remote Similarity	NPD6925	Approved
0.6364	Remote Similarity	NPD4243	Approved
0.6353	Remote Similarity	NPD5329	Approved
0.6344	Remote Similarity	NPD6404	Discontinued
0.6341	Remote Similarity	NPD7514	Phase 3
0.6341	Remote Similarity	NPD7332	Phase 2
0.6333	Remote Similarity	NPD7748	Approved
0.6322	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD6903	Approved
0.6322	Remote Similarity	NPD6672	Approved
0.6322	Remote Similarity	NPD5737	Approved
0.6316	Remote Similarity	NPD6922	Approved
0.6316	Remote Similarity	NPD6923	Approved
0.6296	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD7145	Approved
0.6286	Remote Similarity	NPD287	Approved
0.6265	Remote Similarity	NPD6902	Approved
0.625	Remote Similarity	NPD6673	Approved
0.625	Remote Similarity	NPD6904	Approved
0.625	Remote Similarity	NPD6080	Approved
0.625	Remote Similarity	NPD6051	Approved
0.6235	Remote Similarity	NPD4197	Approved
0.6235	Remote Similarity	NPD3665	Phase 1
0.6235	Remote Similarity	NPD3133	Approved
0.6235	Remote Similarity	NPD3666	Approved
0.6234	Remote Similarity	NPD7144	Approved
0.6234	Remote Similarity	NPD7143	Approved
0.622	Remote Similarity	NPD6929	Approved
0.6216	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD3573	Approved
0.6203	Remote Similarity	NPD6926	Approved
0.6203	Remote Similarity	NPD6924	Approved
0.6203	Remote Similarity	NPD4785	Approved
0.6203	Remote Similarity	NPD4784	Approved
0.6154	Remote Similarity	NPD7152	Approved
0.6154	Remote Similarity	NPD7151	Approved
0.6154	Remote Similarity	NPD7150	Approved
0.6145	Remote Similarity	NPD6931	Approved
0.6145	Remote Similarity	NPD6930	Phase 2
0.6136	Remote Similarity	NPD5208	Approved
0.6129	Remote Similarity	NPD6084	Phase 2
0.6129	Remote Similarity	NPD7902	Approved
0.6129	Remote Similarity	NPD6083	Phase 2
0.6125	Remote Similarity	NPD6942	Approved
0.6125	Remote Similarity	NPD7339	Approved
0.6125	Remote Similarity	NPD8039	Approved
0.6111	Remote Similarity	NPD5281	Approved
0.6111	Remote Similarity	NPD5284	Approved
0.6111	Remote Similarity	NPD5693	Phase 1
0.6098	Remote Similarity	NPD3617	Approved
0.6092	Remote Similarity	NPD4690	Approved
0.6092	Remote Similarity	NPD4693	Phase 3
0.6092	Remote Similarity	NPD4138	Approved
0.6092	Remote Similarity	NPD4688	Approved
0.6092	Remote Similarity	NPD4689	Approved
0.6092	Remote Similarity	NPD3618	Phase 1
0.6092	Remote Similarity	NPD5205	Approved
0.6092	Remote Similarity	NPD6098	Approved
0.6071	Remote Similarity	NPD8028	Phase 2
0.6071	Remote Similarity	NPD6898	Phase 1
0.6067	Remote Similarity	NPD5328	Approved
0.6049	Remote Similarity	NPD6933	Approved
0.6049	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD4786	Approved
0.6044	Remote Similarity	NPD6399	Phase 3
0.6024	Remote Similarity	NPD7645	Phase 2
0.6022	Remote Similarity	NPD7614	Phase 1
0.6	Remote Similarity	NPD3667	Approved
0.5978	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD7900	Approved
0.5976	Remote Similarity	NPD6932	Approved
0.5968	Remote Similarity	NPD1799	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD7525	Registered
0.5934	Remote Similarity	NPD6050	Approved
0.5934	Remote Similarity	NPD6079	Approved
0.593	Remote Similarity	NPD6695	Phase 3
0.5926	Remote Similarity	NPD4190	Phase 3
0.5926	Remote Similarity	NPD5275	Approved
0.5921	Remote Similarity	NPD7331	Phase 2
0.5914	Remote Similarity	NPD5695	Phase 3
0.5914	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD4694	Approved
0.5909	Remote Similarity	NPD5279	Phase 3
0.5909	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD8262	Approved
0.5909	Remote Similarity	NPD5280	Approved
0.5909	Remote Similarity	NPD5690	Phase 2
0.59	Remote Similarity	NPD6686	Approved
0.5895	Remote Similarity	NPD5696	Approved
0.5889	Remote Similarity	NPD4753	Phase 2
0.5876	Remote Similarity	NPD7632	Discontinued
0.5862	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5843	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD6683	Phase 2
0.5824	Remote Similarity	NPD5207	Approved
0.5824	Remote Similarity	NPD5692	Phase 3
0.5824	Remote Similarity	NPD5785	Approved
0.5823	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.5823	Remote Similarity	NPD6939	Phase 2
0.5811	Remote Similarity	NPD368	Approved
0.5806	Remote Similarity	NPD6001	Approved
0.5795	Remote Similarity	NPD6893	Approved
0.5795	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5795	Remote Similarity	NPD1694	Approved
0.5795	Remote Similarity	NPD5363	Approved
0.5765	Remote Similarity	NPD4819	Approved
0.5765	Remote Similarity	NPD4821	Approved
0.5765	Remote Similarity	NPD7509	Discontinued
0.5765	Remote Similarity	NPD4820	Approved
0.5765	Remote Similarity	NPD4822	Approved
0.5765	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5761	Remote Similarity	NPD5694	Approved
0.5747	Remote Similarity	NPD5362	Discontinued
0.5747	Remote Similarity	NPD5331	Approved
0.5747	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.5747	Remote Similarity	NPD5332	Approved
0.5714	Remote Similarity	NPD4271	Approved
0.5714	Remote Similarity	NPD4268	Approved
0.57	Remote Similarity	NPD7128	Approved
0.57	Remote Similarity	NPD5739	Approved
0.57	Remote Similarity	NPD6402	Approved
0.57	Remote Similarity	NPD6675	Approved
0.5699	Remote Similarity	NPD5779	Approved
0.5699	Remote Similarity	NPD5778	Approved
0.5699	Remote Similarity	NPD4202	Approved
0.5698	Remote Similarity	NPD4790	Discontinued
0.5692	Remote Similarity	NPD39	Approved
0.5684	Remote Similarity	NPD7732	Phase 3
0.5682	Remote Similarity	NPD3668	Phase 3
0.567	Remote Similarity	NPD6648	Approved
0.5667	Remote Similarity	NPD7750	Discontinued
0.5667	Remote Similarity	NPD7524	Approved
0.5652	Remote Similarity	NPD4096	Approved
0.5638	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.5638	Remote Similarity	NPD5707	Approved
0.5634	Remote Similarity	NPD342	Phase 1
0.5632	Remote Similarity	NPD4269	Approved
0.5632	Remote Similarity	NPD5209	Approved
0.5632	Remote Similarity	NPD4270	Approved
0.5618	Remote Similarity	NPD1696	Phase 3
0.5612	Remote Similarity	NPD5344	Discontinued
0.5607	Remote Similarity	NPD7115	Discovery

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