NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	166.03
Volume:	160.346
LogP:	1.78
LogD:	3.525
LogS:	-2.387
# Rotatable Bonds:	2
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.689
Synthetic Accessibility Score:	1.411
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:	-5.69
MDCK Permeability:	1.383532344334526e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.082
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.716

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.406
Plasma Protein Binding (PPB):	36.37910842895508%
Volume Distribution (VD):	0.23
Pgp-substrate:	54.604087829589844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.023
CYP1A2-substrate:	0.049
CYP2C19-inhibitor:	0.036
CYP2C19-substrate:	0.033
CYP2C9-inhibitor:	0.058
CYP2C9-substrate:	0.046
CYP2D6-inhibitor:	0.039
CYP2D6-substrate:	0.038
CYP3A4-inhibitor:	0.021
CYP3A4-substrate:	0.017

ADMET: Excretion

Clearance (CL):	1.195
Half-life (T1/2):	0.937

ADMET: Toxicity

hERG Blockers:	0.036
Human Hepatotoxicity (H-HT):	0.343
Drug-inuced Liver Injury (DILI):	0.875
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.066
Maximum Recommended Daily Dose:	0.002
Skin Sensitization:	0.328
Carcinogencity:	0.008
Eye Corrosion:	0.045
Eye Irritation:	0.992
Respiratory Toxicity:	0.082

Download Data

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

Natural Product: NPC228435

Natural Product ID:	NPC228435
*Common Name:**	Isophthalic Acid
IUPAC Name:	benzene-1,3-dicarboxylate;hydron
Synonyms:	Isophthalic Acid
Standard InCHIKey:	QQVIHTHCMHWDBS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C8H6O4/c9-7(10)5-2-1-3-6(4-5)8(11)12/h1-4H,(H,9,10)(H,11,12)
SMILES:	OC(=O)c1cccc(c1)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1871181
PubChem CID:	23461093 8496
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001105] Phthalic acid and derivatives [CHEMONTID:0001106] M-phthalic acid 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
NPO23835	Swertia angustifolia	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO23835	Swertia angustifolia	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23835	Swertia angustifolia	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23835	Swertia angustifolia	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23835	Swertia angustifolia	Species	Gentianaceae	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
Ki	1
Others	3
Potency	7

Activity Type	# Activity
Individual Protein	3
Organism	4
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	15848.9	nM	PMID[545538]
NPT160	Individual Protein	TAR DNA-binding protein 43	Homo sapiens	Potency	n.a.	3548.1	nM	PMID[545537]
NPT4435	Individual Protein	Dihydrodipicolinate synthase	Escherichia coli K-12	Ki	=	5400000.0	nM	PMID[545540]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	18526.0	nM	PMID[545537]
NPT32	Organism	Mus musculus	Mus musculus	IC50	=	100.0	nM	PMID[545539]
NPT32	Organism	Mus musculus	Mus musculus	Ratio IC50	=	2.0	n.a.	PMID[545539]
NPT35	Others	n.a.		pKa	=	3.53	n.a.	PMID[545539]
NPT2	Others	Unspecified		Potency	n.a.	194.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	62649.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	10962.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	43982.2	nM	PubChem BioAssay data set

☑ 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 NPC228435 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	272
0.1-0.2	1709
0.2-0.3	4053
0.3-0.4	11423
0.4-0.5	10968
0.5-0.6	10103
0.6-0.7	3688
0.7-0.8	439
0.8-0.85	30
0.85-0.9	8
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9175	High Similarity	NPC284477
0.913	High Similarity	NPC62765
0.9053	High Similarity	NPC61944
0.8776	High Similarity	NPC217621
0.8763	High Similarity	NPC253423
0.8696	High Similarity	NPC318107
0.8687	High Similarity	NPC282895
0.8673	High Similarity	NPC229242
0.86	High Similarity	NPC304873
0.86	High Similarity	NPC25458
0.8515	High Similarity	NPC255676
0.8462	Intermediate Similarity	NPC318327
0.8454	Intermediate Similarity	NPC261181
0.835	Intermediate Similarity	NPC105899
0.8349	Intermediate Similarity	NPC158157
0.8333	Intermediate Similarity	NPC306740
0.8269	Intermediate Similarity	NPC184658
0.8247	Intermediate Similarity	NPC110704
0.8224	Intermediate Similarity	NPC66208
0.819	Intermediate Similarity	NPC249811
0.819	Intermediate Similarity	NPC29883
0.8182	Intermediate Similarity	NPC130398
0.8165	Intermediate Similarity	NPC476357
0.8155	Intermediate Similarity	NPC291426
0.8125	Intermediate Similarity	NPC329064
0.8113	Intermediate Similarity	NPC85493
0.8077	Intermediate Similarity	NPC324786
0.8073	Intermediate Similarity	NPC211421
0.8039	Intermediate Similarity	NPC203925
0.8036	Intermediate Similarity	NPC273282
0.8036	Intermediate Similarity	NPC474890
0.8036	Intermediate Similarity	NPC161943
0.802	Intermediate Similarity	NPC249912
0.802	Intermediate Similarity	NPC92754
0.802	Intermediate Similarity	NPC276775
0.8018	Intermediate Similarity	NPC83718
0.8	Intermediate Similarity	NPC186933
0.7981	Intermediate Similarity	NPC329556
0.7979	Intermediate Similarity	NPC285773
0.7963	Intermediate Similarity	NPC260818
0.7963	Intermediate Similarity	NPC167504
0.7941	Intermediate Similarity	NPC225060
0.7941	Intermediate Similarity	NPC35448
0.7941	Intermediate Similarity	NPC78701
0.7925	Intermediate Similarity	NPC187913
0.7913	Intermediate Similarity	NPC167323
0.7913	Intermediate Similarity	NPC269923
0.7905	Intermediate Similarity	NPC249067
0.789	Intermediate Similarity	NPC321852
0.7864	Intermediate Similarity	NPC118343
0.7864	Intermediate Similarity	NPC325497
0.7864	Intermediate Similarity	NPC146351
0.7845	Intermediate Similarity	NPC223351
0.7835	Intermediate Similarity	NPC322387
0.781	Intermediate Similarity	NPC301943
0.781	Intermediate Similarity	NPC474365
0.7798	Intermediate Similarity	NPC474057
0.7798	Intermediate Similarity	NPC210089
0.7798	Intermediate Similarity	NPC476003
0.7788	Intermediate Similarity	NPC70624
0.7788	Intermediate Similarity	NPC42211
0.7778	Intermediate Similarity	NPC85511
0.7778	Intermediate Similarity	NPC100551
0.7778	Intermediate Similarity	NPC228739
0.7767	Intermediate Similarity	NPC160548
0.7767	Intermediate Similarity	NPC210529
0.7767	Intermediate Similarity	NPC175852
0.7748	Intermediate Similarity	NPC242136
0.7748	Intermediate Similarity	NPC196673
0.7748	Intermediate Similarity	NPC153053
0.7736	Intermediate Similarity	NPC31786
0.7731	Intermediate Similarity	NPC473751
0.7727	Intermediate Similarity	NPC158282
0.7727	Intermediate Similarity	NPC474314
0.7727	Intermediate Similarity	NPC79496
0.7714	Intermediate Similarity	NPC188895
0.7714	Intermediate Similarity	NPC45613
0.7708	Intermediate Similarity	NPC44546
0.7706	Intermediate Similarity	NPC95172
0.7706	Intermediate Similarity	NPC216122
0.7699	Intermediate Similarity	NPC131192
0.7692	Intermediate Similarity	NPC67300
0.7692	Intermediate Similarity	NPC475192
0.7685	Intermediate Similarity	NPC226699
0.7664	Intermediate Similarity	NPC269457
0.766	Intermediate Similarity	NPC127343
0.7652	Intermediate Similarity	NPC472708
0.7647	Intermediate Similarity	NPC172925
0.7642	Intermediate Similarity	NPC60679
0.7642	Intermediate Similarity	NPC89886
0.7627	Intermediate Similarity	NPC174991
0.7619	Intermediate Similarity	NPC52472
0.7615	Intermediate Similarity	NPC469636
0.7604	Intermediate Similarity	NPC44830
0.76	Intermediate Similarity	NPC274455
0.76	Intermediate Similarity	NPC70940
0.76	Intermediate Similarity	NPC86670
0.7593	Intermediate Similarity	NPC119271
0.7593	Intermediate Similarity	NPC317592
0.7593	Intermediate Similarity	NPC6984
0.7589	Intermediate Similarity	NPC474363
0.7589	Intermediate Similarity	NPC471721
0.7589	Intermediate Similarity	NPC98543
0.7589	Intermediate Similarity	NPC223004
0.7589	Intermediate Similarity	NPC237366
0.757	Intermediate Similarity	NPC329282
0.757	Intermediate Similarity	NPC114594
0.7565	Intermediate Similarity	NPC241089
0.7565	Intermediate Similarity	NPC94298
0.7565	Intermediate Similarity	NPC27633
0.7563	Intermediate Similarity	NPC184219
0.7547	Intermediate Similarity	NPC320891
0.7524	Intermediate Similarity	NPC245561
0.7523	Intermediate Similarity	NPC211439
0.7523	Intermediate Similarity	NPC34715
0.7523	Intermediate Similarity	NPC141523
0.7523	Intermediate Similarity	NPC56493
0.7522	Intermediate Similarity	NPC274839
0.7522	Intermediate Similarity	NPC81808
0.7521	Intermediate Similarity	NPC121104
0.75	Intermediate Similarity	NPC272524
0.75	Intermediate Similarity	NPC219913
0.75	Intermediate Similarity	NPC209632
0.75	Intermediate Similarity	NPC13495
0.75	Intermediate Similarity	NPC172483
0.75	Intermediate Similarity	NPC156021
0.75	Intermediate Similarity	NPC156654
0.75	Intermediate Similarity	NPC61779
0.7478	Intermediate Similarity	NPC160199
0.7478	Intermediate Similarity	NPC228318
0.7477	Intermediate Similarity	NPC470202
0.7477	Intermediate Similarity	NPC160382
0.7477	Intermediate Similarity	NPC13426
0.7477	Intermediate Similarity	NPC274443
0.7459	Intermediate Similarity	NPC473744
0.7455	Intermediate Similarity	NPC10251
0.7455	Intermediate Similarity	NPC83628
0.7455	Intermediate Similarity	NPC17417
0.7455	Intermediate Similarity	NPC265407
0.7455	Intermediate Similarity	NPC474364
0.7455	Intermediate Similarity	NPC17525
0.7455	Intermediate Similarity	NPC224584
0.7449	Intermediate Similarity	NPC95965
0.7431	Intermediate Similarity	NPC37914
0.7431	Intermediate Similarity	NPC30594
0.7431	Intermediate Similarity	NPC37622
0.7429	Intermediate Similarity	NPC179411
0.7423	Intermediate Similarity	NPC288903
0.7411	Intermediate Similarity	NPC212718
0.7411	Intermediate Similarity	NPC270699
0.7411	Intermediate Similarity	NPC114682
0.7411	Intermediate Similarity	NPC82899
0.7404	Intermediate Similarity	NPC246679
0.7395	Intermediate Similarity	NPC297193
0.7395	Intermediate Similarity	NPC472703
0.7395	Intermediate Similarity	NPC68167
0.7391	Intermediate Similarity	NPC312800
0.7391	Intermediate Similarity	NPC128825
0.7387	Intermediate Similarity	NPC93084
0.7387	Intermediate Similarity	NPC174099
0.7387	Intermediate Similarity	NPC214067
0.7387	Intermediate Similarity	NPC251854
0.7387	Intermediate Similarity	NPC196246
0.7383	Intermediate Similarity	NPC244427
0.7383	Intermediate Similarity	NPC222390
0.7377	Intermediate Similarity	NPC115797
0.7377	Intermediate Similarity	NPC51448
0.7373	Intermediate Similarity	NPC165197
0.7364	Intermediate Similarity	NPC156648
0.7364	Intermediate Similarity	NPC303264
0.735	Intermediate Similarity	NPC204784
0.735	Intermediate Similarity	NPC473767
0.7345	Intermediate Similarity	NPC17693
0.7345	Intermediate Similarity	NPC93287
0.7339	Intermediate Similarity	NPC163734
0.7339	Intermediate Similarity	NPC134120
0.7339	Intermediate Similarity	NPC303141
0.7339	Intermediate Similarity	NPC243677
0.7333	Intermediate Similarity	NPC289201
0.7333	Intermediate Similarity	NPC472704
0.7328	Intermediate Similarity	NPC174087
0.7328	Intermediate Similarity	NPC240664
0.7327	Intermediate Similarity	NPC173443
0.7321	Intermediate Similarity	NPC1082
0.7321	Intermediate Similarity	NPC116842
0.7321	Intermediate Similarity	NPC305912
0.7321	Intermediate Similarity	NPC95126
0.7321	Intermediate Similarity	NPC475002
0.7317	Intermediate Similarity	NPC2401
0.7317	Intermediate Similarity	NPC229894
0.7317	Intermediate Similarity	NPC193203
0.7312	Intermediate Similarity	NPC32203
0.7312	Intermediate Similarity	NPC206800
0.7311	Intermediate Similarity	NPC303737
0.7311	Intermediate Similarity	NPC25168
0.7308	Intermediate Similarity	NPC32977
0.7308	Intermediate Similarity	NPC81010
0.7304	Intermediate Similarity	NPC322197
0.73	Intermediate Similarity	NPC194326
0.7297	Intermediate Similarity	NPC99846

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 NPC228435 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	251
0.1-0.2	939
0.2-0.3	1528
0.3-0.4	2926
0.4-0.5	2243
0.5-0.6	958
0.6-0.7	237
0.7-0.8	56
0.8-0.85	7
0.85-0.9	4
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.913	High Similarity	NPD9258	Approved
0.913	High Similarity	NPD9256	Approved
0.8696	High Similarity	NPD9257	Approved
0.8696	High Similarity	NPD9259	Approved
0.8641	High Similarity	NPD6831	Clinical (unspecified phase)
0.8454	Intermediate Similarity	NPD1202	Approved
0.819	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD9260	Approved
0.8	Intermediate Similarity	NPD5951	Approved
0.7981	Intermediate Similarity	NPD1930	Approved
0.7981	Intermediate Similarity	NPD1929	Approved
0.7981	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7979	Intermediate Similarity	NPD9491	Approved
0.7905	Intermediate Similarity	NPD1237	Approved
0.7864	Intermediate Similarity	NPD1238	Approved
0.785	Intermediate Similarity	NPD9263	Approved
0.785	Intermediate Similarity	NPD9267	Approved
0.785	Intermediate Similarity	NPD9264	Approved
0.7778	Intermediate Similarity	NPD74	Approved
0.7778	Intermediate Similarity	NPD9266	Approved
0.7767	Intermediate Similarity	NPD9495	Approved
0.7742	Intermediate Similarity	NPD9490	Approved
0.7736	Intermediate Similarity	NPD164	Approved
0.7727	Intermediate Similarity	NPD9508	Approved
0.7677	Intermediate Similarity	NPD800	Approved
0.7658	Intermediate Similarity	NPD5277	Phase 2
0.7647	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD1090	Approved
0.76	Intermediate Similarity	NPD1086	Approved
0.76	Intermediate Similarity	NPD1089	Approved
0.7586	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD226	Approved
0.7565	Intermediate Similarity	NPD9545	Approved
0.7525	Intermediate Similarity	NPD1239	Approved
0.7524	Intermediate Similarity	NPD2066	Phase 3
0.7522	Intermediate Similarity	NPD9281	Approved
0.7479	Intermediate Similarity	NPD182	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD9261	Approved
0.7455	Intermediate Similarity	NPD2182	Approved
0.7451	Intermediate Similarity	NPD1088	Approved
0.7438	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD9493	Approved
0.7383	Intermediate Similarity	NPD1932	Approved
0.7379	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD9716	Approved
0.7308	Intermediate Similarity	NPD1693	Approved
0.73	Intermediate Similarity	NPD1087	Approved
0.73	Intermediate Similarity	NPD4793	Discontinued
0.7288	Intermediate Similarity	NPD1104	Approved
0.7263	Intermediate Similarity	NPD225	Approved
0.7263	Intermediate Similarity	NPD227	Approved
0.7213	Intermediate Similarity	NPD1164	Approved
0.7203	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD9268	Approved
0.717	Intermediate Similarity	NPD1566	Phase 3
0.717	Intermediate Similarity	NPD1565	Approved
0.717	Intermediate Similarity	NPD1564	Approved
0.7157	Intermediate Similarity	NPD5347	Phase 2
0.7157	Intermediate Similarity	NPD5346	Phase 2
0.7143	Intermediate Similarity	NPD1362	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD9269	Phase 2
0.7107	Intermediate Similarity	NPD9717	Approved
0.708	Intermediate Similarity	NPD1317	Discontinued
0.7069	Intermediate Similarity	NPD2629	Approved
0.7	Intermediate Similarity	NPD6647	Phase 2
0.7	Intermediate Similarity	NPD9272	Approved
0.6992	Remote Similarity	NPD1888	Phase 1
0.6991	Remote Similarity	NPD2329	Discontinued
0.6984	Remote Similarity	NPD7008	Discontinued
0.6984	Remote Similarity	NPD6966	Discovery
0.6979	Remote Similarity	NPD9294	Approved
0.6957	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD159	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD5909	Discontinued
0.6935	Remote Similarity	NPD1203	Approved
0.6935	Remote Similarity	NPD1470	Approved
0.6931	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD2313	Discontinued
0.6929	Remote Similarity	NPD3764	Approved
0.6923	Remote Similarity	NPD1246	Approved
0.6917	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD1563	Approved
0.6885	Remote Similarity	NPD1201	Approved
0.6875	Remote Similarity	NPD5048	Discontinued
0.687	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD942	Approved
0.686	Remote Similarity	NPD2345	Approved
0.6829	Remote Similarity	NPD4878	Approved
0.6818	Remote Similarity	NPD5408	Approved
0.6818	Remote Similarity	NPD5405	Approved
0.6818	Remote Similarity	NPD5404	Approved
0.6818	Remote Similarity	NPD5406	Approved
0.6789	Remote Similarity	NPD9711	Approved
0.6789	Remote Similarity	NPD9710	Approved
0.6759	Remote Similarity	NPD1989	Approved
0.6748	Remote Similarity	NPD6287	Discontinued
0.6746	Remote Similarity	NPD4980	Approved
0.6727	Remote Similarity	NPD9712	Approved
0.6723	Remote Similarity	NPD255	Approved
0.6723	Remote Similarity	NPD256	Approved
0.6696	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD2935	Discontinued
0.6667	Remote Similarity	NPD9693	Approved
0.6667	Remote Similarity	NPD411	Approved
0.6667	Remote Similarity	NPD1889	Phase 1
0.6667	Remote Similarity	NPD9692	Approved
0.6641	Remote Similarity	NPD230	Phase 1
0.664	Remote Similarity	NPD5157	Phase 1
0.664	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.664	Remote Similarity	NPD5159	Phase 2
0.6639	Remote Similarity	NPD1245	Approved
0.6639	Remote Similarity	NPD4105	Approved
0.6639	Remote Similarity	NPD4102	Approved
0.6638	Remote Similarity	NPD2067	Discontinued
0.6636	Remote Similarity	NPD253	Approved
0.6635	Remote Similarity	NPD650	Approved
0.6617	Remote Similarity	NPD2799	Discontinued
0.6615	Remote Similarity	NPD520	Approved
0.6612	Remote Similarity	NPD1758	Phase 1
0.6606	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD3673	Approved
0.6604	Remote Similarity	NPD3672	Approved
0.6587	Remote Similarity	NPD3225	Approved
0.6587	Remote Similarity	NPD1574	Approved
0.6585	Remote Similarity	NPD5305	Approved
0.6585	Remote Similarity	NPD5306	Approved
0.6579	Remote Similarity	NPD1040	Phase 2
0.6577	Remote Similarity	NPD3097	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD845	Approved
0.6569	Remote Similarity	NPD3971	Phase 1
0.6565	Remote Similarity	NPD943	Approved
0.6562	Remote Similarity	NPD662	Approved
0.6562	Remote Similarity	NPD658	Approved
0.6562	Remote Similarity	NPD659	Approved
0.6562	Remote Similarity	NPD663	Approved
0.6562	Remote Similarity	NPD656	Approved
0.656	Remote Similarity	NPD1608	Approved
0.6557	Remote Similarity	NPD1759	Phase 1
0.6545	Remote Similarity	NPD9566	Approved
0.6542	Remote Similarity	NPD7609	Phase 3
0.6538	Remote Similarity	NPD3268	Approved
0.6532	Remote Similarity	NPD4106	Approved
0.6532	Remote Similarity	NPD4135	Approved
0.6532	Remote Similarity	NPD4136	Approved
0.6529	Remote Similarity	NPD9568	Approved
0.6519	Remote Similarity	NPD2346	Discontinued
0.6515	Remote Similarity	NPD447	Suspended
0.6509	Remote Similarity	NPD689	Discontinued
0.6496	Remote Similarity	NPD4628	Phase 3
0.6493	Remote Similarity	NPD4308	Phase 3
0.6493	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD6085	Phase 2
0.6484	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD7631	Approved
0.648	Remote Similarity	NPD518	Clinical (unspecified phase)
0.648	Remote Similarity	NPD4806	Approved
0.648	Remote Similarity	NPD4807	Approved
0.6479	Remote Similarity	NPD3226	Approved
0.6466	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD1283	Approved
0.6452	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD1551	Phase 2
0.6439	Remote Similarity	NPD1240	Approved
0.6436	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD1481	Phase 2
0.6406	Remote Similarity	NPD2797	Approved
0.6404	Remote Similarity	NPD5765	Approved
0.64	Remote Similarity	NPD4879	Approved
0.6397	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD3495	Discontinued
0.6389	Remote Similarity	NPD7411	Suspended
0.6387	Remote Similarity	NPD969	Suspended
0.6377	Remote Similarity	NPD7003	Approved
0.6377	Remote Similarity	NPD3750	Approved
0.6373	Remote Similarity	NPD9250	Approved
0.637	Remote Similarity	NPD1510	Phase 2
0.6364	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6049	Phase 2
0.6357	Remote Similarity	NPD701	Approved
0.6357	Remote Similarity	NPD1019	Discontinued
0.6357	Remote Similarity	NPD2798	Approved
0.6357	Remote Similarity	NPD698	Approved
0.6349	Remote Similarity	NPD1535	Discovery
0.6343	Remote Similarity	NPD1607	Approved
0.633	Remote Similarity	NPD1508	Approved
0.6328	Remote Similarity	NPD2199	Approved
0.6328	Remote Similarity	NPD2198	Approved
0.6321	Remote Similarity	NPD506	Clinical (unspecified phase)
0.632	Remote Similarity	NPD17	Approved
0.6316	Remote Similarity	NPD3373	Approved
0.6308	Remote Similarity	NPD9494	Approved
0.6306	Remote Similarity	NPD2859	Approved
0.6306	Remote Similarity	NPD2860	Approved
0.6306	Remote Similarity	NPD1809	Phase 2
0.6299	Remote Similarity	NPD3972	Approved
0.6293	Remote Similarity	NPD9697	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