NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	166.03
Volume:	160.346
LogP:	1.187
LogD:	3.761
LogS:	-1.234
# 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:	1.398
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:	-5.74
MDCK Permeability:	1.023844197334256e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.071
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.897

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.399
Plasma Protein Binding (PPB):	53.42133331298828%
Volume Distribution (VD):	0.204
Pgp-substrate:	34.11764907836914%

ADMET: Metabolism

CYP1A2-inhibitor:	0.039
CYP1A2-substrate:	0.043
CYP2C19-inhibitor:	0.043
CYP2C19-substrate:	0.039
CYP2C9-inhibitor:	0.111
CYP2C9-substrate:	0.058
CYP2D6-inhibitor:	0.037
CYP2D6-substrate:	0.055
CYP3A4-inhibitor:	0.022
CYP3A4-substrate:	0.025

ADMET: Excretion

Clearance (CL):	1.376
Half-life (T1/2):	0.91

ADMET: Toxicity

hERG Blockers:	0.108
Human Hepatotoxicity (H-HT):	0.361
Drug-inuced Liver Injury (DILI):	0.88
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.111
Maximum Recommended Daily Dose:	0.002
Skin Sensitization:	0.374
Carcinogencity:	0.01
Eye Corrosion:	0.02
Eye Irritation:	0.995
Respiratory Toxicity:	0.219

Download Data

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

Natural Product: NPC282895

Natural Product ID:	NPC282895
*Common Name:**	Phthalic Acid
IUPAC Name:	hydron;phthalate
Synonyms:	Phthalic acid
Standard InCHIKey:	XNGIFLGASWRNHJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C8H6O4/c9-7(10)5-3-1-2-4-6(5)8(11)12/h1-4H,(H,9,10)(H,11,12)/p-2
SMILES:	c1ccc(c(c1)C(=O)[O-])C(=O)[O-]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1045
PubChem CID:	18183610 1017
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0002565] Benzoic acids

*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

☑ 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
NPO15265	NPC282895	Naturally dried; obtain oils by crushing seeds using screw press	Seeds	0.535 ± 0.003	n.a.	n.a.	μg/g	PMID[32545196]
NPO15265	NPC282895	Naturally dried; obtain oils by crushing seeds using screw press	Seeds	0.396 ± 0.002	n.a.	n.a.	μg/g	PMID[32545196]
NPO30287	NPC282895	Naturally dried; obtain oils by crushing seeds using screw press	Seeds	1.607 ± 0.016	n.a.	n.a.	μg/g	PMID[32545196]
NPO30287	NPC282895	Naturally dried; obtain oils by crushing seeds using screw press	Seeds	1.100 ± 0.001	n.a.	n.a.	μg/g	PMID[32545196]
NPO30287	NPC282895	Naturally dried; obtain oils by crushing seeds using screw press	Seeds	1.154 ± 0.014	n.a.	n.a.	μg/g	PMID[32545196]
NPO30287	NPC282895	Naturally dried; obtain oils by crushing seeds using screw press	Seeds	0.398 ± 0.011	n.a.	n.a.	μg/g	PMID[32545196]
NPO30287	NPC282895	Naturally dried; obtain oils by crushing seeds using screw press	Seeds	1.069 ± 0.009	n.a.	n.a.	μg/g	PMID[32545196]
NPO30287	NPC282895	Naturally dried; obtain oils by crushing seeds using screw press	Seeds	0.584 ± 0.012	n.a.	n.a.	μg/g	PMID[32545196]
NPO30287	NPC282895	Naturally dried; obtain oils by crushing seeds using screw press	Seeds	0.364 ±0.005	n.a.	n.a.	μg/g	PMID[32545196]
NPO30287	NPC282895	Naturally dried; obtain oils by crushing seeds using screw press	Seeds	0.575 ± 0.008	n.a.	n.a.	μg/g	PMID[32545196]
NPO9798	NPC282895	Naturally dried; obtain oils by crushing seeds using screw press	Seeds	0.724 ± 0.002	n.a.	n.a.	μg/g	PMID[32545196]
NPO9798	NPC282895	Naturally dried; obtain oils by crushing seeds using screw press	Seeds	0.808 ± 0.006	n.a.	n.a.	μg/g	PMID[32545196]

☑ 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	3
Kd	1
Ki	2
Others	10
Potency	17

Activity Type	# Activity
Individual Protein	11
Organism	5
Others	16
PROTEIN-PROTEIN INTERACTION	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT13	Individual Protein	Tyrosine-protein kinase LCK	Homo sapiens	Kd	=	1700000.0	nM	PMID[488971]
NPT443	Individual Protein	Histone acetyltransferase GCN5	Homo sapiens	Potency	n.a.	14125.4	nM	PMID[488975]
NPT63	Individual Protein	Bromodomain adjacent to zinc finger domain protein 2B	Homo sapiens	Potency	n.a.	89125.1	nM	PMID[488975]
NPT135	Individual Protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	89125.1	nM	PMID[488975]
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[488974]
NPT622	Individual Protein	Solute carrier organic anion transporter family member 2B1	Homo sapiens	Activity	=	42.7	%	PMID[488977]
NPT103	Individual Protein	Nuclear receptor ROR-gamma	Homo sapiens	Potency	n.a.	16785.5	nM	PMID[488974]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	6513.1	nM	PMID[488975]
NPT2	Others	Unspecified		IC50	>	100000.0	nM	PMID[488972]
NPT35	Others	n.a.		Solubility	=	4130.0	ug.mL-1	PMID[488973]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	28183.8	nM	PMID[488974]
NPT2	Others	Unspecified		Potency	=	65.1	nM	PMID[488975]
NPT792	Individual Protein	Arachidonate 15-lipoxygenase	Homo sapiens	Potency	=	39810.7	nM	PMID[488974]
NPT21702	PROTEIN-PROTEIN INTERACTION	Importin subunit beta-1/Snurportin-1	Homo sapiens	Potency	n.a.	100000.0	nM	PMID[488975]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	2078.7	nM	PMID[488975]
NPT99	Individual Protein	Peroxisome proliferator-activated receptor gamma	Homo sapiens	Potency	n.a.	44668.4	nM	PMID[488974]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	4147.5	nM	PMID[488975]
NPT32	Organism	Mus musculus	Mus musculus	IC50	=	100.0	nM	PMID[488976]
NPT32	Organism	Mus musculus	Mus musculus	Ratio IC50	=	2.0	n.a.	PMID[488976]
NPT35	Others	n.a.		pKa	=	2.95	n.a.	PMID[488976]
NPT2	Others	Unspecified		Ki	=	65840000.0	nM	PMID[488978]
NPT2	Others	Unspecified		Ki	=	100000.0	nM	PMID[488978]
NPT2	Others	Unspecified		IC50	=	271790.0	nM	PMID[488978]
NPT2	Others	Unspecified		K	=	67.25	uM	PMID[488978]
NPT2	Others	Unspecified		Vmax	=	14.47	microM/min	PMID[488978]
NPT2	Others	Unspecified		KA	=	10.95	uM	PMID[488978]
NPT2	Others	Unspecified		Ka	=	91.32	/mM	PMID[488978]
NPT2	Others	Unspecified		Activity	=	11.0	%	PMID[488978]
NPT2	Others	Unspecified		Potency	n.a.	14.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	22575.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	28420.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	44645	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 NPC282895 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	277
0.1-0.2	1549
0.2-0.3	3935
0.3-0.4	10888
0.4-0.5	11491
0.5-0.6	10939
0.6-0.7	3070
0.7-0.8	486
0.8-0.85	33
0.85-0.9	21
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9368	High Similarity	NPC229242
0.93	High Similarity	NPC85493
0.9278	High Similarity	NPC284477
0.9118	High Similarity	NPC260818
0.9032	High Similarity	NPC62765
0.9029	High Similarity	NPC321852
0.899	High Similarity	NPC255676
0.8958	High Similarity	NPC61944
0.89	High Similarity	NPC31786
0.8857	High Similarity	NPC153053
0.8725	High Similarity	NPC119271
0.87	High Similarity	NPC45613
0.87	High Similarity	NPC304873
0.8687	High Similarity	NPC228435
0.8687	High Similarity	NPC217621
0.8673	High Similarity	NPC253423
0.8641	High Similarity	NPC56493
0.8602	High Similarity	NPC318107
0.8558	High Similarity	NPC318327
0.8558	High Similarity	NPC17417
0.8558	High Similarity	NPC10251
0.8515	High Similarity	NPC25458
0.8505	High Similarity	NPC237366
0.8476	Intermediate Similarity	NPC174099
0.8476	Intermediate Similarity	NPC196246
0.8476	Intermediate Similarity	NPC214067
0.8476	Intermediate Similarity	NPC93084
0.8476	Intermediate Similarity	NPC251854
0.8447	Intermediate Similarity	NPC105899
0.8431	Intermediate Similarity	NPC89886
0.8396	Intermediate Similarity	NPC1082
0.8396	Intermediate Similarity	NPC305912
0.8367	Intermediate Similarity	NPC261181
0.8351	Intermediate Similarity	NPC110704
0.8318	Intermediate Similarity	NPC270699
0.8318	Intermediate Similarity	NPC66208
0.8318	Intermediate Similarity	NPC82899
0.8286	Intermediate Similarity	NPC249811
0.8286	Intermediate Similarity	NPC211439
0.8273	Intermediate Similarity	NPC158157
0.8252	Intermediate Similarity	NPC60679
0.8191	Intermediate Similarity	NPC44546
0.819	Intermediate Similarity	NPC187913
0.819	Intermediate Similarity	NPC30594
0.819	Intermediate Similarity	NPC37622
0.8173	Intermediate Similarity	NPC114594
0.8155	Intermediate Similarity	NPC320891
0.8119	Intermediate Similarity	NPC156021
0.81	Intermediate Similarity	NPC130398
0.8095	Intermediate Similarity	NPC209632
0.8091	Intermediate Similarity	NPC186933
0.8091	Intermediate Similarity	NPC306740
0.8085	Intermediate Similarity	NPC285773
0.8077	Intermediate Similarity	NPC291426
0.8073	Intermediate Similarity	NPC272524
0.8056	Intermediate Similarity	NPC474057
0.8037	Intermediate Similarity	NPC265407
0.8037	Intermediate Similarity	NPC83628
0.8	Intermediate Similarity	NPC329282
0.8	Intermediate Similarity	NPC324786
0.8	Intermediate Similarity	NPC307651
0.7961	Intermediate Similarity	NPC203925
0.7941	Intermediate Similarity	NPC276775
0.7941	Intermediate Similarity	NPC249912
0.7941	Intermediate Similarity	NPC92754
0.7938	Intermediate Similarity	NPC322387
0.7928	Intermediate Similarity	NPC476357
0.7905	Intermediate Similarity	NPC13426
0.7885	Intermediate Similarity	NPC42211
0.787	Intermediate Similarity	NPC269023
0.787	Intermediate Similarity	NPC99846
0.7864	Intermediate Similarity	NPC78701
0.7864	Intermediate Similarity	NPC210529
0.7864	Intermediate Similarity	NPC35448
0.7864	Intermediate Similarity	NPC175852
0.7864	Intermediate Similarity	NPC225060
0.7864	Intermediate Similarity	NPC160548
0.785	Intermediate Similarity	NPC184658
0.7838	Intermediate Similarity	NPC196673
0.783	Intermediate Similarity	NPC249067
0.7818	Intermediate Similarity	NPC158282
0.781	Intermediate Similarity	NPC222390
0.781	Intermediate Similarity	NPC244427
0.7788	Intermediate Similarity	NPC118343
0.7788	Intermediate Similarity	NPC108288
0.7788	Intermediate Similarity	NPC325497
0.7788	Intermediate Similarity	NPC146351
0.7778	Intermediate Similarity	NPC29883
0.7778	Intermediate Similarity	NPC34715
0.7778	Intermediate Similarity	NPC46634
0.7768	Intermediate Similarity	NPC81808
0.7768	Intermediate Similarity	NPC474685
0.7766	Intermediate Similarity	NPC127343
0.7759	Intermediate Similarity	NPC165197
0.775	Intermediate Similarity	NPC115797
0.775	Intermediate Similarity	NPC51448
0.7745	Intermediate Similarity	NPC172925
0.7739	Intermediate Similarity	NPC232178
0.7736	Intermediate Similarity	NPC301943
0.7736	Intermediate Similarity	NPC329556
0.7736	Intermediate Similarity	NPC274443
0.7736	Intermediate Similarity	NPC474365
0.7727	Intermediate Similarity	NPC476003
0.7727	Intermediate Similarity	NPC167504
0.7727	Intermediate Similarity	NPC474157
0.7727	Intermediate Similarity	NPC243355
0.7727	Intermediate Similarity	NPC210089
0.7719	Intermediate Similarity	NPC160199
0.7719	Intermediate Similarity	NPC125252
0.7714	Intermediate Similarity	NPC70624
0.7714	Intermediate Similarity	NPC52472
0.7706	Intermediate Similarity	NPC100551
0.77	Intermediate Similarity	NPC274455
0.77	Intermediate Similarity	NPC70940
0.77	Intermediate Similarity	NPC86670
0.7699	Intermediate Similarity	NPC149691
0.7692	Intermediate Similarity	NPC167323
0.7692	Intermediate Similarity	NPC25168
0.7692	Intermediate Similarity	NPC269923
0.7679	Intermediate Similarity	NPC474363
0.7679	Intermediate Similarity	NPC98543
0.7677	Intermediate Similarity	NPC329064
0.7658	Intermediate Similarity	NPC474314
0.7658	Intermediate Similarity	NPC79496
0.7647	Intermediate Similarity	NPC246166
0.7642	Intermediate Similarity	NPC188895
0.7636	Intermediate Similarity	NPC216122
0.7632	Intermediate Similarity	NPC312800
0.7627	Intermediate Similarity	NPC223351
0.7627	Intermediate Similarity	NPC297193
0.7627	Intermediate Similarity	NPC68167
0.7619	Intermediate Similarity	NPC245561
0.7615	Intermediate Similarity	NPC141523
0.7615	Intermediate Similarity	NPC226699
0.7611	Intermediate Similarity	NPC210092
0.7593	Intermediate Similarity	NPC172483
0.7593	Intermediate Similarity	NPC13495
0.7593	Intermediate Similarity	NPC269457
0.7589	Intermediate Similarity	NPC231717
0.7586	Intermediate Similarity	NPC204784
0.7586	Intermediate Similarity	NPC472708
0.7586	Intermediate Similarity	NPC184579
0.7586	Intermediate Similarity	NPC233165
0.757	Intermediate Similarity	NPC160382
0.7565	Intermediate Similarity	NPC240664
0.7563	Intermediate Similarity	NPC85511
0.7563	Intermediate Similarity	NPC275145
0.7563	Intermediate Similarity	NPC477153
0.7551	Intermediate Similarity	NPC95965
0.7547	Intermediate Similarity	NPC473325
0.7545	Intermediate Similarity	NPC469636
0.7545	Intermediate Similarity	NPC224584
0.7542	Intermediate Similarity	NPC198336
0.7526	Intermediate Similarity	NPC215008
0.7526	Intermediate Similarity	NPC288903
0.7526	Intermediate Similarity	NPC44830
0.7523	Intermediate Similarity	NPC6984
0.7523	Intermediate Similarity	NPC37914
0.7522	Intermediate Similarity	NPC211421
0.7522	Intermediate Similarity	NPC308744
0.7521	Intermediate Similarity	NPC169913
0.7521	Intermediate Similarity	NPC206778
0.7521	Intermediate Similarity	NPC285829
0.75	Intermediate Similarity	NPC117794
0.75	Intermediate Similarity	NPC310540
0.75	Intermediate Similarity	NPC295664
0.7479	Intermediate Similarity	NPC283514
0.7479	Intermediate Similarity	NPC91478
0.7477	Intermediate Similarity	NPC95172
0.7459	Intermediate Similarity	NPC209959
0.7458	Intermediate Similarity	NPC35856
0.7458	Intermediate Similarity	NPC301987
0.7458	Intermediate Similarity	NPC115188
0.7458	Intermediate Similarity	NPC178395
0.7458	Intermediate Similarity	NPC179092
0.7458	Intermediate Similarity	NPC26433
0.7458	Intermediate Similarity	NPC222876
0.7458	Intermediate Similarity	NPC292665
0.7458	Intermediate Similarity	NPC244994
0.7458	Intermediate Similarity	NPC159760
0.7458	Intermediate Similarity	NPC272454
0.7456	Intermediate Similarity	NPC274839
0.7455	Intermediate Similarity	NPC156648
0.7438	Intermediate Similarity	NPC472592
0.7438	Intermediate Similarity	NPC275576
0.7436	Intermediate Similarity	NPC156654
0.7434	Intermediate Similarity	NPC17693
0.7431	Intermediate Similarity	NPC134120
0.7431	Intermediate Similarity	NPC163734
0.7429	Intermediate Similarity	NPC289201
0.7419	Intermediate Similarity	NPC31539
0.7417	Intermediate Similarity	NPC228739
0.7417	Intermediate Similarity	NPC375356
0.7411	Intermediate Similarity	NPC95126
0.7411	Intermediate Similarity	NPC475002
0.74	Intermediate Similarity	NPC194326
0.7395	Intermediate Similarity	NPC120545
0.7391	Intermediate Similarity	NPC100353
0.7391	Intermediate Similarity	NPC240163
0.7387	Intermediate Similarity	NPC17525

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 NPC282895 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	257
0.1-0.2	915
0.2-0.3	1475
0.3-0.4	2865
0.4-0.5	2311
0.5-0.6	1020
0.6-0.7	231
0.7-0.8	66
0.8-0.85	5
0.85-0.9	4
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9032	High Similarity	NPD9258	Approved
0.9032	High Similarity	NPD9256	Approved
0.89	High Similarity	NPD164	Approved
0.8602	High Similarity	NPD9257	Approved
0.8602	High Similarity	NPD9259	Approved
0.8558	High Similarity	NPD2182	Approved
0.8381	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.8367	Intermediate Similarity	NPD1202	Approved
0.8091	Intermediate Similarity	NPD5951	Approved
0.8085	Intermediate Similarity	NPD9491	Approved
0.7921	Intermediate Similarity	NPD9260	Approved
0.789	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7864	Intermediate Similarity	NPD9495	Approved
0.7849	Intermediate Similarity	NPD9490	Approved
0.783	Intermediate Similarity	NPD1237	Approved
0.781	Intermediate Similarity	NPD1932	Approved
0.7788	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7788	Intermediate Similarity	NPD1238	Approved
0.7778	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD9263	Approved
0.7778	Intermediate Similarity	NPD9264	Approved
0.7778	Intermediate Similarity	NPD9267	Approved
0.7745	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD1930	Approved
0.7736	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD1929	Approved
0.7706	Intermediate Similarity	NPD9266	Approved
0.7706	Intermediate Similarity	NPD74	Approved
0.77	Intermediate Similarity	NPD1090	Approved
0.77	Intermediate Similarity	NPD1086	Approved
0.77	Intermediate Similarity	NPD1089	Approved
0.7684	Intermediate Similarity	NPD226	Approved
0.7672	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD9508	Approved
0.7624	Intermediate Similarity	NPD1239	Approved
0.7619	Intermediate Similarity	NPD2066	Phase 3
0.76	Intermediate Similarity	NPD800	Approved
0.7589	Intermediate Similarity	NPD5277	Phase 2
0.7563	Intermediate Similarity	NPD182	Clinical (unspecified phase)
0.7549	Intermediate Similarity	NPD1088	Approved
0.7476	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD9281	Approved
0.7407	Intermediate Similarity	NPD9261	Approved
0.7404	Intermediate Similarity	NPD1693	Approved
0.74	Intermediate Similarity	NPD1087	Approved
0.7387	Intermediate Similarity	NPD2329	Discontinued
0.7368	Intermediate Similarity	NPD227	Approved
0.7368	Intermediate Similarity	NPD225	Approved
0.7345	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD9493	Approved
0.7321	Intermediate Similarity	NPD1317	Discontinued
0.7295	Intermediate Similarity	NPD1470	Approved
0.728	Intermediate Similarity	NPD3764	Approved
0.7264	Intermediate Similarity	NPD1564	Approved
0.7264	Intermediate Similarity	NPD1565	Approved
0.7264	Intermediate Similarity	NPD1566	Phase 3
0.725	Intermediate Similarity	NPD518	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD6647	Phase 2
0.7236	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD9716	Approved
0.7228	Intermediate Similarity	NPD4793	Discontinued
0.7228	Intermediate Similarity	NPD650	Approved
0.7227	Intermediate Similarity	NPD1104	Approved
0.7203	Intermediate Similarity	NPD9545	Approved
0.72	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD4878	Approved
0.7172	Intermediate Similarity	NPD3971	Phase 1
0.7143	Intermediate Similarity	NPD9268	Approved
0.7091	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD5346	Phase 2
0.7087	Intermediate Similarity	NPD5347	Phase 2
0.7083	Intermediate Similarity	NPD1362	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD7008	Discontinued
0.7049	Intermediate Similarity	NPD9269	Phase 2
0.7049	Intermediate Similarity	NPD9717	Approved
0.7027	Intermediate Similarity	NPD5909	Discontinued
0.7016	Intermediate Similarity	NPD1164	Approved
0.6981	Remote Similarity	NPD1563	Approved
0.6967	Remote Similarity	NPD1201	Approved
0.6957	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD7609	Phase 3
0.6942	Remote Similarity	NPD9272	Approved
0.6935	Remote Similarity	NPD1888	Phase 1
0.6907	Remote Similarity	NPD9294	Approved
0.6887	Remote Similarity	NPD7631	Approved
0.6887	Remote Similarity	NPD1508	Approved
0.688	Remote Similarity	NPD1203	Approved
0.6875	Remote Similarity	NPD2313	Discontinued
0.687	Remote Similarity	NPD2067	Discontinued
0.6864	Remote Similarity	NPD1246	Approved
0.6864	Remote Similarity	NPD2629	Approved
0.686	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD1989	Approved
0.6842	Remote Similarity	NPD2346	Discontinued
0.68	Remote Similarity	NPD942	Approved
0.6767	Remote Similarity	NPD5406	Approved
0.6767	Remote Similarity	NPD5404	Approved
0.6767	Remote Similarity	NPD5405	Approved
0.6767	Remote Similarity	NPD5408	Approved
0.6727	Remote Similarity	NPD9710	Approved
0.6727	Remote Similarity	NPD253	Approved
0.6727	Remote Similarity	NPD9711	Approved
0.6721	Remote Similarity	NPD1245	Approved
0.6721	Remote Similarity	NPD4102	Approved
0.6721	Remote Similarity	NPD4105	Approved
0.6718	Remote Similarity	NPD447	Suspended
0.6699	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD3673	Approved
0.6698	Remote Similarity	NPD3672	Approved
0.6697	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD1843	Approved
0.6694	Remote Similarity	NPD6287	Discontinued
0.6694	Remote Similarity	NPD1758	Phase 1
0.6692	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5305	Approved
0.6667	Remote Similarity	NPD9712	Approved
0.6667	Remote Similarity	NPD256	Approved
0.6667	Remote Similarity	NPD6966	Discovery
0.6667	Remote Similarity	NPD2345	Approved
0.6667	Remote Similarity	NPD255	Approved
0.6667	Remote Similarity	NPD5306	Approved
0.664	Remote Similarity	NPD1481	Phase 2
0.6639	Remote Similarity	NPD1759	Phase 1
0.6636	Remote Similarity	NPD9566	Approved
0.6615	Remote Similarity	NPD411	Approved
0.6613	Remote Similarity	NPD9692	Approved
0.6613	Remote Similarity	NPD1889	Phase 1
0.6613	Remote Similarity	NPD4135	Approved
0.6613	Remote Similarity	NPD4879	Approved
0.6613	Remote Similarity	NPD4106	Approved
0.6613	Remote Similarity	NPD4136	Approved
0.6613	Remote Similarity	NPD9693	Approved
0.6612	Remote Similarity	NPD9568	Approved
0.6593	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD230	Phase 1
0.6587	Remote Similarity	NPD5159	Phase 2
0.6587	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD5157	Phase 1
0.6569	Remote Similarity	NPD3750	Approved
0.6567	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD2799	Discontinued
0.6565	Remote Similarity	NPD520	Approved
0.6562	Remote Similarity	NPD4980	Approved
0.656	Remote Similarity	NPD4807	Approved
0.656	Remote Similarity	NPD1535	Discovery
0.656	Remote Similarity	NPD4806	Approved
0.6549	Remote Similarity	NPD3226	Approved
0.6535	Remote Similarity	NPD1283	Approved
0.6535	Remote Similarity	NPD1876	Approved
0.6532	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5048	Discontinued
0.6519	Remote Similarity	NPD2935	Discontinued
0.6518	Remote Similarity	NPD3097	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD1625	Approved
0.6491	Remote Similarity	NPD5765	Approved
0.6486	Remote Similarity	NPD3495	Discontinued
0.6484	Remote Similarity	NPD2797	Approved
0.6471	Remote Similarity	NPD969	Suspended
0.6455	Remote Similarity	NPD6049	Phase 2
0.6455	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD689	Discontinued
0.6449	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD7003	Approved
0.6444	Remote Similarity	NPD4308	Phase 3
0.6439	Remote Similarity	NPD7961	Discontinued
0.6434	Remote Similarity	NPD6085	Phase 2
0.6434	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD1019	Discontinued
0.6434	Remote Similarity	NPD2798	Approved
0.6423	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD159	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD506	Clinical (unspecified phase)
0.64	Remote Similarity	NPD2932	Approved
0.64	Remote Similarity	NPD3019	Approved
0.6391	Remote Similarity	NPD943	Approved
0.6379	Remote Similarity	NPD1040	Phase 2
0.6378	Remote Similarity	NPD1608	Approved
0.6373	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD1894	Discontinued
0.6364	Remote Similarity	NPD845	Approved
0.6364	Remote Similarity	NPD2650	Approved
0.6364	Remote Similarity	NPD1280	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3268	Approved
0.6364	Remote Similarity	NPD2652	Approved
0.6364	Remote Similarity	NPD1241	Discontinued
0.6364	Remote Similarity	NPD1066	Discontinued
0.6364	Remote Similarity	NPD3598	Phase 3
0.6357	Remote Similarity	NPD7236	Approved
0.635	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.635	Remote Similarity	NPD9477	Approved
0.6341	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6336	Remote Similarity	NPD6832	Phase 2
0.6331	Remote Similarity	NPD4628	Phase 3
0.6325	Remote Similarity	NPD6685	Approved
0.6324	Remote Similarity	NPD3748	Approved
0.6319	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD9250	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