NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	278.15
Volume:	298.714
LogP:	4.066
LogD:	4.55
LogS:	-4.465
# Rotatable Bonds:	8
TPSA:	52.6
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.749
Synthetic Accessibility Score:	1.908
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.425
MDCK Permeability:	3.400003333808854e-05
Pgp-inhibitor:	0.579
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.799
30% Bioavailability (F30%):	0.951

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.039
Plasma Protein Binding (PPB):	91.89574432373047%
Volume Distribution (VD):	1.326
Pgp-substrate:	3.3517189025878906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.306
CYP1A2-substrate:	0.196
CYP2C19-inhibitor:	0.861
CYP2C19-substrate:	0.123
CYP2C9-inhibitor:	0.86
CYP2C9-substrate:	0.677
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.043
CYP3A4-inhibitor:	0.064
CYP3A4-substrate:	0.16

ADMET: Excretion

Clearance (CL):	11.028
Half-life (T1/2):	0.583

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.008
Drug-inuced Liver Injury (DILI):	0.421
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.007
Maximum Recommended Daily Dose:	0.005
Skin Sensitization:	0.635
Carcinogencity:	0.096
Eye Corrosion:	0.037
Eye Irritation:	0.982
Respiratory Toxicity:	0.038

Download Data

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

Natural Product: NPC214067

Natural Product ID:	NPC214067
*Common Name:**	Bis(2-Methylpropyl) Benzene-1,2-Dicarboxylate
IUPAC Name:	bis(2-methylpropyl) benzene-1,2-dicarboxylate
Synonyms:
Standard InCHIKey:	MGWAVDBGNNKXQV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H22O4/c1-11(2)9-19-15(17)13-7-5-6-8-14(13)16(18)20-10-12(3)4/h5-8,11-12H,9-10H2,1-4H3
SMILES:	CC(C)COC(=O)c1ccccc1C(=O)OCC(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1370662
PubChem CID:	6782
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001350] Benzoic acid esters

*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
NPO7576	NPC214067	Other	Stem	0.01	0.01	0.01	mg/100g	Database [DUKE]

☑ 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
Potency	41

Activity Type	# Activity
Cell Line	5
Individual Protein	18
Organism	2
Others	16

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT347	Cell Line	Lymphoblastoid cells	Homo sapiens	Potency	=	39810.7	nM	PMID[572946]
NPT347	Cell Line	Lymphoblastoid cells	Homo sapiens	Potency	=	50118.7	nM	PMID[572946]
NPT210	Individual Protein	Thyroid stimulating hormone receptor	Homo sapiens	Potency	=	39810.7	nM	PMID[572946]
NPT347	Cell Line	Lymphoblastoid cells	Homo sapiens	Potency	=	79432.8	nM	PMID[572946]
NPT532	Individual Protein	Lysine-specific demethylase 4A	Homo sapiens	Potency	n.a.	56234.1	nM	PMID[572947]
NPT63	Individual Protein	Bromodomain adjacent to zinc finger domain protein 2B	Homo sapiens	Potency	n.a.	89125.1	nM	PMID[572948]
NPT135	Individual Protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	79432.8	nM	PMID[572947]
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[572946]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	33491.5	nM	PMID[572946]
NPT101	Individual Protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	28183.8	nM	PMID[572947]
NPT11	Individual Protein	Guanine nucleotide-binding protein G(s), subunit alpha	Homo sapiens	Potency	n.a.	11220.2	nM	PMID[572947]
NPT102	Individual Protein	Interleukin-8	Homo sapiens	Potency	n.a.	74978.0	nM	PMID[572946]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	23109.3	nM	PMID[572947]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	14581.0	nM	PMID[572947]
NPT161	Individual Protein	Rap guanine nucleotide exchange factor 4	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[572947]
NPT163	Individual Protein	Nuclear factor NF-kappa-B p105 subunit	Homo sapiens	Potency	n.a.	61690.1	nM	PubChem BioAssay data set
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	39810.7	nM	PMID[572946]
NPT2	Others	Unspecified		Potency	=	25118.9	nM	PMID[572946]
NPT2	Others	Unspecified		Potency	n.a.	398.1	nM	PMID[572948]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	13115.4	nM	PMID[572948]
NPT98	Individual Protein	HERG	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[572946]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	10417.9	nM	PMID[572948]
NPT2	Others	Unspecified		Potency	n.a.	13.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	21689.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	13685.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	54941	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	68589.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	27306	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	48557.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	61690.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	611.3	nM	PubChem BioAssay data set
NPT74	Individual Protein	Proto-oncogene c-JUN	Homo sapiens	Potency	n.a.	54941	nM	PubChem BioAssay data set
NPT74	Individual Protein	Proto-oncogene c-JUN	Homo sapiens	Potency	n.a.	54981.3	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 NPC214067 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	245
0.1-0.2	1211
0.2-0.3	3215
0.3-0.4	8498
0.4-0.5	11589
0.5-0.6	12063
0.6-0.7	5124
0.7-0.8	654
0.8-0.85	49
0.85-0.9	23
0.9-0.95	10
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC196246
0.9902	High Similarity	NPC1082
0.9902	High Similarity	NPC305912
0.9901	High Similarity	NPC10251
0.9901	High Similarity	NPC17417
0.9806	High Similarity	NPC82899
0.9806	High Similarity	NPC270699
0.9804	High Similarity	NPC93084
0.9804	High Similarity	NPC251854
0.9802	High Similarity	NPC56493
0.9703	High Similarity	NPC119271
0.9619	High Similarity	NPC153053
0.9612	High Similarity	NPC174099
0.9505	High Similarity	NPC31786
0.9429	High Similarity	NPC321852
0.9333	High Similarity	NPC260818
0.9252	High Similarity	NPC307651
0.9143	High Similarity	NPC85493
0.9109	High Similarity	NPC146351
0.9029	High Similarity	NPC89886
0.9029	High Similarity	NPC301943
0.9029	High Similarity	NPC474365
0.901	High Similarity	NPC225060
0.901	High Similarity	NPC78701
0.901	High Similarity	NPC35448
0.8991	High Similarity	NPC210092
0.8962	High Similarity	NPC83628
0.8962	High Similarity	NPC265407
0.8932	High Similarity	NPC45613
0.8911	High Similarity	NPC249912
0.8911	High Similarity	NPC276775
0.8911	High Similarity	NPC92754
0.8796	High Similarity	NPC474157
0.8785	High Similarity	NPC469636
0.8774	High Similarity	NPC30594
0.8774	High Similarity	NPC37622
0.8738	High Similarity	NPC325497
0.8713	High Similarity	NPC130398
0.8679	High Similarity	NPC269457
0.8679	High Similarity	NPC209632
0.8667	High Similarity	NPC60679
0.8654	High Similarity	NPC70624
0.8654	High Similarity	NPC42211
0.8636	High Similarity	NPC128368
0.8624	High Similarity	NPC210089
0.8585	High Similarity	NPC114594
0.8571	High Similarity	NPC149691
0.8558	High Similarity	NPC118343
0.8558	High Similarity	NPC203925
0.8476	Intermediate Similarity	NPC282895
0.8468	Intermediate Similarity	NPC272524
0.8455	Intermediate Similarity	NPC167504
0.844	Intermediate Similarity	NPC269023
0.844	Intermediate Similarity	NPC99846
0.844	Intermediate Similarity	NPC474364
0.8396	Intermediate Similarity	NPC188895
0.8393	Intermediate Similarity	NPC308744
0.8393	Intermediate Similarity	NPC237366
0.8378	Intermediate Similarity	NPC79496
0.8362	Intermediate Similarity	NPC473243
0.8319	Intermediate Similarity	NPC474685
0.8319	Intermediate Similarity	NPC246166
0.8304	Intermediate Similarity	NPC161611
0.8291	Intermediate Similarity	NPC50872
0.8288	Intermediate Similarity	NPC476003
0.8286	Intermediate Similarity	NPC229242
0.823	Intermediate Similarity	NPC474363
0.8218	Intermediate Similarity	NPC173443
0.8218	Intermediate Similarity	NPC220893
0.8182	Intermediate Similarity	NPC169913
0.8167	Intermediate Similarity	NPC295664
0.8158	Intermediate Similarity	NPC306740
0.8158	Intermediate Similarity	NPC474095
0.812	Intermediate Similarity	NPC204784
0.8099	Intermediate Similarity	NPC121272
0.8099	Intermediate Similarity	NPC476599
0.8099	Intermediate Similarity	NPC275576
0.8087	Intermediate Similarity	NPC100353
0.807	Intermediate Similarity	NPC477411
0.807	Intermediate Similarity	NPC196075
0.8056	Intermediate Similarity	NPC284477
0.8033	Intermediate Similarity	NPC51292
0.802	Intermediate Similarity	NPC89377
0.8019	Intermediate Similarity	NPC270654
0.8018	Intermediate Similarity	NPC470391
0.8	Intermediate Similarity	NPC228936
0.7982	Intermediate Similarity	NPC474176
0.7967	Intermediate Similarity	NPC51448
0.7967	Intermediate Similarity	NPC115797
0.7965	Intermediate Similarity	NPC243355
0.7963	Intermediate Similarity	NPC473325
0.7949	Intermediate Similarity	NPC469574
0.7931	Intermediate Similarity	NPC226093
0.7931	Intermediate Similarity	NPC135730
0.7921	Intermediate Similarity	NPC318107
0.7905	Intermediate Similarity	NPC261181
0.7895	Intermediate Similarity	NPC212415
0.7895	Intermediate Similarity	NPC158282
0.7895	Intermediate Similarity	NPC474314
0.789	Intermediate Similarity	NPC304873
0.7885	Intermediate Similarity	NPC119631
0.7857	Intermediate Similarity	NPC472394
0.7851	Intermediate Similarity	NPC223351
0.7851	Intermediate Similarity	NPC472703
0.784	Intermediate Similarity	NPC147561
0.784	Intermediate Similarity	NPC42234
0.784	Intermediate Similarity	NPC272946
0.7833	Intermediate Similarity	NPC144547
0.7826	Intermediate Similarity	NPC13784
0.7822	Intermediate Similarity	NPC58616
0.7822	Intermediate Similarity	NPC294134
0.7818	Intermediate Similarity	NPC255676
0.7805	Intermediate Similarity	NPC470765
0.7797	Intermediate Similarity	NPC228318
0.7788	Intermediate Similarity	NPC240108
0.7788	Intermediate Similarity	NPC213156
0.7787	Intermediate Similarity	NPC51079
0.7787	Intermediate Similarity	NPC472704
0.7787	Intermediate Similarity	NPC471466
0.7778	Intermediate Similarity	NPC470278
0.7767	Intermediate Similarity	NPC304760
0.775	Intermediate Similarity	NPC289432
0.775	Intermediate Similarity	NPC988
0.775	Intermediate Similarity	NPC238861
0.775	Intermediate Similarity	NPC77000
0.7748	Intermediate Similarity	NPC329282
0.7742	Intermediate Similarity	NPC470753
0.7742	Intermediate Similarity	NPC473220
0.7739	Intermediate Similarity	NPC66208
0.7734	Intermediate Similarity	NPC329913
0.7731	Intermediate Similarity	NPC293424
0.7731	Intermediate Similarity	NPC254233
0.7717	Intermediate Similarity	NPC477360
0.7717	Intermediate Similarity	NPC238370
0.7706	Intermediate Similarity	NPC217621
0.7705	Intermediate Similarity	NPC46634
0.7698	Intermediate Similarity	NPC473247
0.7698	Intermediate Similarity	NPC475508
0.7692	Intermediate Similarity	NPC474408
0.7692	Intermediate Similarity	NPC9822
0.7692	Intermediate Similarity	NPC81808
0.7685	Intermediate Similarity	NPC253423
0.7674	Intermediate Similarity	NPC477893
0.7674	Intermediate Similarity	NPC477896
0.7674	Intermediate Similarity	NPC311339
0.7667	Intermediate Similarity	NPC202015
0.7656	Intermediate Similarity	NPC477364
0.7647	Intermediate Similarity	NPC152812
0.7647	Intermediate Similarity	NPC45794
0.7642	Intermediate Similarity	NPC228739
0.7642	Intermediate Similarity	NPC77273
0.7638	Intermediate Similarity	NPC475478
0.7638	Intermediate Similarity	NPC469519
0.7624	Intermediate Similarity	NPC288903
0.7624	Intermediate Similarity	NPC270507
0.7619	Intermediate Similarity	NPC62765
0.7603	Intermediate Similarity	NPC72977
0.7603	Intermediate Similarity	NPC232958
0.76	Intermediate Similarity	NPC472706
0.7597	Intermediate Similarity	NPC477368
0.7597	Intermediate Similarity	NPC477359
0.7597	Intermediate Similarity	NPC474608
0.7597	Intermediate Similarity	NPC472591
0.7597	Intermediate Similarity	NPC48929
0.7597	Intermediate Similarity	NPC126516
0.7597	Intermediate Similarity	NPC203486
0.7593	Intermediate Similarity	NPC61944
0.7589	Intermediate Similarity	NPC85977
0.7581	Intermediate Similarity	NPC125053
0.7578	Intermediate Similarity	NPC7012
0.7578	Intermediate Similarity	NPC239358
0.7578	Intermediate Similarity	NPC233860
0.7578	Intermediate Similarity	NPC233692
0.7578	Intermediate Similarity	NPC475569
0.7568	Intermediate Similarity	NPC25458
0.7565	Intermediate Similarity	NPC273837
0.7563	Intermediate Similarity	NPC190298
0.7559	Intermediate Similarity	NPC27712
0.7559	Intermediate Similarity	NPC471832
0.7544	Intermediate Similarity	NPC211439
0.7544	Intermediate Similarity	NPC249811
0.7542	Intermediate Similarity	NPC470764
0.7542	Intermediate Similarity	NPC221275
0.7542	Intermediate Similarity	NPC186933
0.754	Intermediate Similarity	NPC472707
0.7538	Intermediate Similarity	NPC291638
0.7538	Intermediate Similarity	NPC232888
0.7538	Intermediate Similarity	NPC473399
0.7538	Intermediate Similarity	NPC265459
0.7538	Intermediate Similarity	NPC195647
0.7538	Intermediate Similarity	NPC270364
0.7538	Intermediate Similarity	NPC475262
0.7538	Intermediate Similarity	NPC17877
0.7538	Intermediate Similarity	NPC66761
0.7538	Intermediate Similarity	NPC290833
0.7538	Intermediate Similarity	NPC473216
0.7538	Intermediate Similarity	NPC472577
0.7538	Intermediate Similarity	NPC477367
0.7525	Intermediate Similarity	NPC323103
0.7525	Intermediate Similarity	NPC103387

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 NPC214067 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	217
0.1-0.2	872
0.2-0.3	1316
0.3-0.4	2761
0.4-0.5	2351
0.5-0.6	1210
0.6-0.7	365
0.7-0.8	53
0.8-0.85	1
0.85-0.9	1
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9901	High Similarity	NPD2182	Approved
0.9505	High Similarity	NPD164	Approved
0.9151	High Similarity	NPD2181	Clinical (unspecified phase)
0.8558	High Similarity	NPD1238	Approved
0.7921	Intermediate Similarity	NPD9257	Approved
0.7921	Intermediate Similarity	NPD9259	Approved
0.7905	Intermediate Similarity	NPD1202	Approved
0.7895	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7876	Intermediate Similarity	NPD2067	Discontinued
0.7788	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7769	Intermediate Similarity	NPD518	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7623	Intermediate Similarity	NPD6287	Discontinued
0.7619	Intermediate Similarity	NPD3672	Approved
0.7619	Intermediate Similarity	NPD9256	Approved
0.7619	Intermediate Similarity	NPD9258	Approved
0.7619	Intermediate Similarity	NPD3673	Approved
0.7593	Intermediate Similarity	NPD1989	Approved
0.7542	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD5951	Approved
0.75	Intermediate Similarity	NPD6647	Phase 2
0.75	Intermediate Similarity	NPD1087	Approved
0.7438	Intermediate Similarity	NPD9545	Approved
0.7434	Intermediate Similarity	NPD5909	Discontinued
0.7422	Intermediate Similarity	NPD7008	Discontinued
0.7387	Intermediate Similarity	NPD2066	Phase 3
0.7345	Intermediate Similarity	NPD1930	Approved
0.7345	Intermediate Similarity	NPD1929	Approved
0.7345	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD6832	Phase 2
0.7339	Intermediate Similarity	NPD9260	Approved
0.7323	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD3134	Approved
0.7302	Intermediate Similarity	NPD1876	Approved
0.7302	Intermediate Similarity	NPD2199	Approved
0.7302	Intermediate Similarity	NPD2198	Approved
0.729	Intermediate Similarity	NPD1090	Approved
0.729	Intermediate Similarity	NPD1086	Approved
0.729	Intermediate Similarity	NPD1089	Approved
0.7273	Intermediate Similarity	NPD9493	Approved
0.7248	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD3764	Approved
0.7228	Intermediate Similarity	NPD9490	Approved
0.7196	Intermediate Similarity	NPD800	Approved
0.7188	Intermediate Similarity	NPD1019	Discontinued
0.7185	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD1241	Discontinued
0.7156	Intermediate Similarity	NPD7631	Approved
0.7156	Intermediate Similarity	NPD1088	Approved
0.7143	Intermediate Similarity	NPD6637	Approved
0.7143	Intermediate Similarity	NPD5926	Approved
0.7143	Intermediate Similarity	NPD9495	Approved
0.713	Intermediate Similarity	NPD1237	Approved
0.7121	Intermediate Similarity	NPD2979	Phase 3
0.7115	Intermediate Similarity	NPD9491	Approved
0.7107	Intermediate Similarity	NPD2629	Approved
0.7105	Intermediate Similarity	NPD1932	Approved
0.7094	Intermediate Similarity	NPD1358	Approved
0.709	Intermediate Similarity	NPD2567	Approved
0.709	Intermediate Similarity	NPD2569	Approved
0.7083	Intermediate Similarity	NPD5277	Phase 2
0.7073	Intermediate Similarity	NPD2347	Approved
0.7064	Intermediate Similarity	NPD7609	Phase 3
0.7059	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2346	Discontinued
0.705	Intermediate Similarity	NPD7236	Approved
0.7037	Intermediate Similarity	NPD2799	Discontinued
0.7034	Intermediate Similarity	NPD2329	Discontinued
0.7027	Intermediate Similarity	NPD1693	Approved
0.7009	Intermediate Similarity	NPD650	Approved
0.7008	Intermediate Similarity	NPD3972	Approved
0.7008	Intermediate Similarity	NPD9717	Approved
0.6992	Remote Similarity	NPD3373	Approved
0.6984	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD553	Approved
0.6977	Remote Similarity	NPD9567	Approved
0.6977	Remote Similarity	NPD552	Approved
0.6975	Remote Similarity	NPD5240	Approved
0.6975	Remote Similarity	NPD5237	Approved
0.6975	Remote Similarity	NPD5236	Approved
0.6975	Remote Similarity	NPD1317	Discontinued
0.6975	Remote Similarity	NPD5235	Approved
0.6975	Remote Similarity	NPD5239	Approved
0.697	Remote Similarity	NPD2313	Discontinued
0.6961	Remote Similarity	NPD225	Approved
0.6961	Remote Similarity	NPD227	Approved
0.696	Remote Similarity	NPD5585	Approved
0.696	Remote Similarity	NPD5691	Approved
0.694	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD1563	Approved
0.6934	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD1281	Approved
0.6923	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6085	Phase 2
0.6923	Remote Similarity	NPD2798	Approved
0.6917	Remote Similarity	NPD2201	Approved
0.6911	Remote Similarity	NPD4198	Discontinued
0.6905	Remote Similarity	NPD5305	Approved
0.6905	Remote Similarity	NPD5306	Approved
0.6899	Remote Similarity	NPD5667	Approved
0.6897	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD9261	Approved
0.6894	Remote Similarity	NPD6039	Approved
0.6881	Remote Similarity	NPD5347	Phase 2
0.6881	Remote Similarity	NPD5346	Phase 2
0.6875	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD1282	Approved
0.6846	Remote Similarity	NPD3266	Approved
0.6846	Remote Similarity	NPD2797	Approved
0.6846	Remote Similarity	NPD3267	Approved
0.6838	Remote Similarity	NPD2670	Approved
0.6833	Remote Similarity	NPD4234	Approved
0.6833	Remote Similarity	NPD4233	Approved
0.6829	Remote Similarity	NPD4766	Approved
0.6822	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD4618	Approved
0.6815	Remote Similarity	NPD230	Phase 1
0.6815	Remote Similarity	NPD4622	Approved
0.6806	Remote Similarity	NPD7239	Suspended
0.6803	Remote Similarity	NPD6858	Approved
0.6803	Remote Similarity	NPD7094	Approved
0.6797	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD4807	Approved
0.6797	Remote Similarity	NPD4806	Approved
0.6792	Remote Similarity	NPD3971	Phase 1
0.6791	Remote Similarity	NPD7961	Discontinued
0.6791	Remote Similarity	NPD7713	Phase 3
0.6788	Remote Similarity	NPD3748	Approved
0.6786	Remote Similarity	NPD4628	Phase 3
0.6786	Remote Similarity	NPD7003	Approved
0.6783	Remote Similarity	NPD6273	Approved
0.6783	Remote Similarity	NPD7798	Approved
0.6772	Remote Similarity	NPD17	Approved
0.6769	Remote Similarity	NPD1283	Approved
0.6765	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD226	Approved
0.6759	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD1239	Approved
0.6754	Remote Similarity	NPD1565	Approved
0.6754	Remote Similarity	NPD1566	Phase 3
0.6754	Remote Similarity	NPD1564	Approved
0.6754	Remote Similarity	NPD3495	Discontinued
0.6748	Remote Similarity	NPD2650	Approved
0.6748	Remote Similarity	NPD2652	Approved
0.6746	Remote Similarity	NPD1894	Discontinued
0.6744	Remote Similarity	NPD4878	Approved
0.6741	Remote Similarity	NPD4307	Phase 2
0.6741	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD2531	Phase 2
0.6739	Remote Similarity	NPD2935	Discontinued
0.6739	Remote Similarity	NPD2438	Suspended
0.6723	Remote Similarity	NPD6685	Approved
0.6721	Remote Similarity	NPD969	Suspended
0.6721	Remote Similarity	NPD9508	Approved
0.672	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD4136	Approved
0.6719	Remote Similarity	NPD3496	Discontinued
0.6719	Remote Similarity	NPD4106	Approved
0.6719	Remote Similarity	NPD4135	Approved
0.6718	Remote Similarity	NPD1203	Approved
0.6716	Remote Similarity	NPD3268	Approved
0.6715	Remote Similarity	NPD5689	Approved
0.6715	Remote Similarity	NPD5688	Approved
0.6714	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD4793	Discontinued
0.6696	Remote Similarity	NPD1508	Approved
0.6695	Remote Similarity	NPD3047	Approved
0.6695	Remote Similarity	NPD3048	Approved
0.6695	Remote Similarity	NPD3046	Approved
0.6694	Remote Similarity	NPD1756	Approved
0.6694	Remote Similarity	NPD1752	Approved
0.6694	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD4359	Approved
0.6691	Remote Similarity	NPD447	Suspended
0.6691	Remote Similarity	NPD1933	Approved
0.6667	Remote Similarity	NPD6065	Approved
0.6667	Remote Similarity	NPD9267	Approved
0.6667	Remote Similarity	NPD5647	Approved
0.6667	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9263	Approved
0.6667	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9264	Approved
0.6667	Remote Similarity	NPD2607	Approved
0.6667	Remote Similarity	NPD3170	Approved
0.6644	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD3226	Approved
0.6643	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD4626	Approved
0.6641	Remote Similarity	NPD1104	Approved
0.662	Remote Similarity	NPD3887	Approved
0.6618	Remote Similarity	NPD3142	Approved
0.6618	Remote Similarity	NPD3140	Approved
0.6615	Remote Similarity	NPD1608	Approved
0.6615	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD74	Approved
0.6612	Remote Similarity	NPD9266	Approved
0.6597	Remote Similarity	NPD2532	Approved
0.6597	Remote Similarity	NPD2534	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