NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	238.12
Volume:	249.463
LogP:	2.323
LogD:	2.542
LogS:	-2.542
# Rotatable Bonds:	6
TPSA:	36.92
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.713
Synthetic Accessibility Score:	2.178
Fsp3:	0.385
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:	-4.482
MDCK Permeability:	1.942854214576073e-05
Pgp-inhibitor:	0.099
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.544
Plasma Protein Binding (PPB):	80.64354705810547%
Volume Distribution (VD):	0.846
Pgp-substrate:	12.821703910827637%

ADMET: Metabolism

CYP1A2-inhibitor:	0.775
CYP1A2-substrate:	0.973
CYP2C19-inhibitor:	0.481
CYP2C19-substrate:	0.923
CYP2C9-inhibitor:	0.047
CYP2C9-substrate:	0.87
CYP2D6-inhibitor:	0.035
CYP2D6-substrate:	0.916
CYP3A4-inhibitor:	0.269
CYP3A4-substrate:	0.706

ADMET: Excretion

Clearance (CL):	7.686
Half-life (T1/2):	0.717

ADMET: Toxicity

hERG Blockers:	0.091
Human Hepatotoxicity (H-HT):	0.043
Drug-inuced Liver Injury (DILI):	0.031
AMES Toxicity:	0.06
Rat Oral Acute Toxicity:	0.097
Maximum Recommended Daily Dose:	0.036
Skin Sensitization:	0.874
Carcinogencity:	0.391
Eye Corrosion:	0.027
Eye Irritation:	0.731
Respiratory Toxicity:	0.051

Download Data

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

Natural Product: NPC308217

Natural Product ID:	NPC308217
*Common Name:**	1,2,3,4-Tetramethoxy-5-Prop-2-Enylbenzene
IUPAC Name:	1,2,3,4-tetramethoxy-5-prop-2-enylbenzene
Synonyms:
Standard InCHIKey:	HRAXJWRHSUTMCS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H18O4/c1-6-7-9-8-10(14-2)12(16-4)13(17-5)11(9)15-3/h6,8H,1,7H2,2-5H3
SMILES:	C=CCc1cc(c(c(c1OC)OC)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464585
PubChem CID:	617233
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002341] Phenol ethers [CHEMONTID:0000138] Anisoles

*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
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	callus	n.a.	PMID[10552648]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18214349]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	seed	n.a.	PMID[21049975]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21800857]
NPO1838	Malmea depressa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8991955]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1838	Malmea depressa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5954	Petroselinum crispum	Species	Apiaceae	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
NPO5954	NPC308217	Raw	Seed	1330.25	0.5	2660	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
ED50	3
IC50	2
MIC	2
Others	1

Activity Type	# Activity
Cell Line	3
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	29.0	ug ml-1	PMID[491850]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	46.0	ug ml-1	PMID[491850]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	71.0	ug ml-1	PMID[491850]
NPT117	Organism	Echinochloa crus-galli	Echinochloa crus-galli	IC50	=	810.0	ug.mL-1	PMID[491850]
NPT965	Organism	Amaranthus hypochondriacus	Amaranthus hypochondriacus	IC50	=	43.0	ug.mL-1	PMID[491850]
NPT140	Organism	Artemia	Artemia	LC50	=	144.0	ug.mL-1	PMID[491850]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MIC	=	500.0	ug.mL-1	PMID[491850]
NPT637	Organism	Fusarium oxysporum	Fusarium oxysporum	MIC	=	250.0	ug.mL-1	PMID[491850]

☑ 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 NPC308217 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	489
0.1-0.2	2139
0.2-0.3	7679
0.3-0.4	12076
0.4-0.5	3395
0.5-0.6	5420
0.6-0.7	7949
0.7-0.8	2848
0.8-0.85	488
0.85-0.9	181
0.9-0.95	29
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.982	High Similarity	NPC304208
0.982	High Similarity	NPC52464
0.9558	High Similarity	NPC474612
0.9483	High Similarity	NPC270326
0.9459	High Similarity	NPC204120
0.9397	High Similarity	NPC285289
0.9322	High Similarity	NPC191768
0.9322	High Similarity	NPC92869
0.9322	High Similarity	NPC283170
0.9322	High Similarity	NPC183446
0.9316	High Similarity	NPC194626
0.9316	High Similarity	NPC264885
0.9279	High Similarity	NPC203924
0.9153	High Similarity	NPC211231
0.9138	High Similarity	NPC254625
0.9138	High Similarity	NPC475961
0.9099	High Similarity	NPC165386
0.9098	High Similarity	NPC10225
0.9098	High Similarity	NPC58164
0.9091	High Similarity	NPC189248
0.9091	High Similarity	NPC202904
0.9083	High Similarity	NPC64391
0.9052	High Similarity	NPC63083
0.9043	High Similarity	NPC123948
0.9024	High Similarity	NPC299221
0.9024	High Similarity	NPC224157
0.9024	High Similarity	NPC192687
0.9024	High Similarity	NPC311680
0.9024	High Similarity	NPC51840
0.9024	High Similarity	NPC234488
0.9008	High Similarity	NPC112596
0.8983	High Similarity	NPC472596
0.8974	High Similarity	NPC15805
0.8943	High Similarity	NPC190144
0.8943	High Similarity	NPC150809
0.8943	High Similarity	NPC153547
0.8934	High Similarity	NPC242032
0.8934	High Similarity	NPC474670
0.8926	High Similarity	NPC105925
0.8908	High Similarity	NPC477886
0.888	High Similarity	NPC6451
0.8871	High Similarity	NPC470624
0.8871	High Similarity	NPC237169
0.8862	High Similarity	NPC266691
0.8862	High Similarity	NPC31707
0.8852	High Similarity	NPC214406
0.8852	High Similarity	NPC18924
0.8852	High Similarity	NPC223136
0.8852	High Similarity	NPC44748
0.8852	High Similarity	NPC78974
0.8852	High Similarity	NPC103823
0.8852	High Similarity	NPC223953
0.8852	High Similarity	NPC28730
0.8833	High Similarity	NPC474864
0.8833	High Similarity	NPC261661
0.8833	High Similarity	NPC246967
0.8833	High Similarity	NPC135414
0.8814	High Similarity	NPC119949
0.8814	High Similarity	NPC20674
0.88	High Similarity	NPC12275
0.88	High Similarity	NPC45715
0.88	High Similarity	NPC232275
0.88	High Similarity	NPC474356
0.879	High Similarity	NPC45824
0.878	High Similarity	NPC74817
0.878	High Similarity	NPC246620
0.878	High Similarity	NPC169474
0.878	High Similarity	NPC82679
0.878	High Similarity	NPC124452
0.878	High Similarity	NPC324112
0.878	High Similarity	NPC293054
0.878	High Similarity	NPC236791
0.878	High Similarity	NPC474821
0.878	High Similarity	NPC282000
0.878	High Similarity	NPC159968
0.877	High Similarity	NPC299584
0.877	High Similarity	NPC82483
0.877	High Similarity	NPC234400
0.877	High Similarity	NPC60885
0.877	High Similarity	NPC265483
0.876	High Similarity	NPC282496
0.876	High Similarity	NPC165375
0.876	High Similarity	NPC233526
0.876	High Similarity	NPC220598
0.875	High Similarity	NPC49341
0.875	High Similarity	NPC75713
0.874	High Similarity	NPC474600
0.874	High Similarity	NPC474478
0.8739	High Similarity	NPC222175
0.873	High Similarity	NPC137669
0.873	High Similarity	NPC319969
0.872	High Similarity	NPC244799
0.872	High Similarity	NPC240722
0.872	High Similarity	NPC214860
0.872	High Similarity	NPC476399
0.872	High Similarity	NPC220935
0.871	High Similarity	NPC207702
0.871	High Similarity	NPC283114
0.871	High Similarity	NPC149008
0.871	High Similarity	NPC154866
0.8699	High Similarity	NPC112571
0.8699	High Similarity	NPC50683
0.8699	High Similarity	NPC244364
0.8699	High Similarity	NPC245060
0.8699	High Similarity	NPC474632
0.8699	High Similarity	NPC285725
0.8672	High Similarity	NPC195022
0.8672	High Similarity	NPC472337
0.8672	High Similarity	NPC111655
0.8667	High Similarity	NPC199023
0.8667	High Similarity	NPC166759
0.8661	High Similarity	NPC241341
0.8661	High Similarity	NPC233018
0.8661	High Similarity	NPC36437
0.8655	High Similarity	NPC135961
0.8649	High Similarity	NPC292792
0.8644	High Similarity	NPC259638
0.8644	High Similarity	NPC33271
0.864	High Similarity	NPC469951
0.864	High Similarity	NPC158477
0.864	High Similarity	NPC27239
0.864	High Similarity	NPC123127
0.864	High Similarity	NPC469963
0.864	High Similarity	NPC474227
0.8629	High Similarity	NPC266555
0.8629	High Similarity	NPC471986
0.8629	High Similarity	NPC216836
0.8618	High Similarity	NPC116907
0.8618	High Similarity	NPC203133
0.8618	High Similarity	NPC298757
0.8618	High Similarity	NPC221077
0.8618	High Similarity	NPC193544
0.8618	High Similarity	NPC117214
0.8618	High Similarity	NPC57490
0.8618	High Similarity	NPC475169
0.8618	High Similarity	NPC208950
0.8618	High Similarity	NPC472093
0.8618	High Similarity	NPC17943
0.8618	High Similarity	NPC251855
0.8618	High Similarity	NPC233410
0.8607	High Similarity	NPC197757
0.8607	High Similarity	NPC95168
0.8607	High Similarity	NPC228922
0.8607	High Similarity	NPC121115
0.8605	High Similarity	NPC286843
0.8605	High Similarity	NPC205442
0.8605	High Similarity	NPC173660
0.8605	High Similarity	NPC472336
0.8605	High Similarity	NPC472334
0.8583	High Similarity	NPC474565
0.8583	High Similarity	NPC229401
0.8571	High Similarity	NPC126836
0.856	High Similarity	NPC474636
0.856	High Similarity	NPC82862
0.856	High Similarity	NPC474616
0.856	High Similarity	NPC474623
0.856	High Similarity	NPC222127
0.856	High Similarity	NPC63179
0.856	High Similarity	NPC19694
0.856	High Similarity	NPC474651
0.856	High Similarity	NPC210674
0.856	High Similarity	NPC28765
0.8559	High Similarity	NPC193067
0.8548	High Similarity	NPC88297
0.8548	High Similarity	NPC9891
0.8548	High Similarity	NPC52593
0.8548	High Similarity	NPC186845
0.8538	High Similarity	NPC326797
0.8538	High Similarity	NPC474282
0.8538	High Similarity	NPC201145
0.8538	High Similarity	NPC276490
0.8538	High Similarity	NPC6262
0.8538	High Similarity	NPC73535
0.8538	High Similarity	NPC90615
0.8538	High Similarity	NPC102904
0.8538	High Similarity	NPC176051
0.8538	High Similarity	NPC107551
0.8538	High Similarity	NPC25111
0.8538	High Similarity	NPC103976
0.8538	High Similarity	NPC272157
0.8527	High Similarity	NPC234865
0.8525	High Similarity	NPC71579
0.8525	High Similarity	NPC262253
0.8525	High Similarity	NPC288238
0.8525	High Similarity	NPC41562
0.8525	High Similarity	NPC473411
0.8516	High Similarity	NPC269528
0.8516	High Similarity	NPC168059
0.8516	High Similarity	NPC229442
0.8516	High Similarity	NPC263064
0.8504	High Similarity	NPC474238
0.8504	High Similarity	NPC471983
0.8504	High Similarity	NPC141493
0.8504	High Similarity	NPC149337
0.8504	High Similarity	NPC184928
0.8492	Intermediate Similarity	NPC218856
0.8492	Intermediate Similarity	NPC470258
0.8492	Intermediate Similarity	NPC285339
0.8492	Intermediate Similarity	NPC212015
0.8492	Intermediate Similarity	NPC476968

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 NPC308217 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	447
0.1-0.2	1045
0.2-0.3	2242
0.3-0.4	2563
0.4-0.5	1451
0.5-0.6	849
0.6-0.7	478
0.7-0.8	66
0.8-0.85	7
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8629	High Similarity	NPD3018	Phase 2
0.8525	High Similarity	NPD2981	Phase 2
0.8492	Intermediate Similarity	NPD3027	Phase 3
0.8455	Intermediate Similarity	NPD2982	Phase 2
0.8455	Intermediate Similarity	NPD2983	Phase 2
0.8305	Intermediate Similarity	NPD5283	Phase 1
0.8268	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8189	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8154	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8154	Intermediate Similarity	NPD1613	Approved
0.8145	Intermediate Similarity	NPD3705	Approved
0.8136	Intermediate Similarity	NPD228	Approved
0.7985	Intermediate Similarity	NPD3539	Phase 1
0.7926	Intermediate Similarity	NPD3540	Phase 1
0.7742	Intermediate Similarity	NPD5536	Phase 2
0.773	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7704	Intermediate Similarity	NPD6111	Discontinued
0.7698	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD1548	Phase 1
0.7622	Intermediate Similarity	NPD1653	Approved
0.7603	Intermediate Similarity	NPD2801	Approved
0.7578	Intermediate Similarity	NPD1610	Phase 2
0.7576	Intermediate Similarity	NPD4908	Phase 1
0.7521	Intermediate Similarity	NPD846	Approved
0.7521	Intermediate Similarity	NPD940	Approved
0.7518	Intermediate Similarity	NPD7124	Phase 2
0.748	Intermediate Similarity	NPD1357	Approved
0.7463	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD4749	Approved
0.7447	Intermediate Similarity	NPD2219	Phase 1
0.7442	Intermediate Similarity	NPD422	Phase 1
0.744	Intermediate Similarity	NPD6671	Approved
0.7438	Intermediate Similarity	NPD2684	Approved
0.7424	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD1424	Approved
0.7405	Intermediate Similarity	NPD2922	Phase 1
0.7368	Intermediate Similarity	NPD2861	Phase 2
0.7364	Intermediate Similarity	NPD3496	Discontinued
0.7355	Intermediate Similarity	NPD290	Approved
0.7355	Intermediate Similarity	NPD1358	Approved
0.7351	Intermediate Similarity	NPD5494	Approved
0.7339	Intermediate Similarity	NPD7843	Approved
0.7333	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD3817	Phase 2
0.731	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD1091	Approved
0.7302	Intermediate Similarity	NPD7157	Approved
0.7297	Intermediate Similarity	NPD1934	Approved
0.7286	Intermediate Similarity	NPD1375	Discontinued
0.7259	Intermediate Similarity	NPD4625	Phase 3
0.723	Intermediate Similarity	NPD5090	Approved
0.723	Intermediate Similarity	NPD5089	Approved
0.7222	Intermediate Similarity	NPD1511	Approved
0.7222	Intermediate Similarity	NPD5297	Approved
0.7222	Intermediate Similarity	NPD4357	Discontinued
0.7219	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD5691	Approved
0.7206	Intermediate Similarity	NPD5111	Phase 2
0.7206	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD5110	Phase 2
0.7206	Intermediate Similarity	NPD5109	Approved
0.719	Intermediate Similarity	NPD1247	Approved
0.7185	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD1652	Phase 2
0.7181	Intermediate Similarity	NPD37	Approved
0.7162	Intermediate Similarity	NPD4675	Approved
0.7162	Intermediate Similarity	NPD4678	Approved
0.7154	Intermediate Similarity	NPD4626	Approved
0.7153	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3882	Suspended
0.7143	Intermediate Similarity	NPD1242	Phase 1
0.7143	Intermediate Similarity	NPD8651	Approved
0.7133	Intermediate Similarity	NPD4585	Approved
0.7133	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD1350	Approved
0.7123	Intermediate Similarity	NPD1512	Approved
0.7123	Intermediate Similarity	NPD1349	Approved
0.7123	Intermediate Similarity	NPD1351	Approved
0.7122	Intermediate Similarity	NPD1772	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD4055	Discovery
0.7101	Intermediate Similarity	NPD1558	Phase 1
0.7097	Intermediate Similarity	NPD4750	Phase 3
0.7097	Intermediate Similarity	NPD5451	Approved
0.7095	Intermediate Similarity	NPD4005	Discontinued
0.708	Intermediate Similarity	NPD5718	Phase 2
0.7068	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD4237	Approved
0.7063	Intermediate Similarity	NPD4236	Phase 3
0.7059	Intermediate Similarity	NPD596	Approved
0.7059	Intermediate Similarity	NPD600	Approved
0.7054	Intermediate Similarity	NPD1408	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD447	Suspended
0.705	Intermediate Similarity	NPD230	Phase 1
0.7045	Intermediate Similarity	NPD1611	Approved
0.7039	Intermediate Similarity	NPD6788	Approved
0.7039	Intermediate Similarity	NPD4965	Approved
0.7039	Intermediate Similarity	NPD4966	Approved
0.7039	Intermediate Similarity	NPD4967	Phase 2
0.7032	Intermediate Similarity	NPD6232	Discontinued
0.7029	Intermediate Similarity	NPD2674	Phase 3
0.7029	Intermediate Similarity	NPD840	Approved
0.7029	Intermediate Similarity	NPD839	Approved
0.7025	Intermediate Similarity	NPD5844	Phase 1
0.7023	Intermediate Similarity	NPD1778	Approved
0.7021	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD6696	Suspended
0.7007	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7534	Approved
0.7	Intermediate Similarity	NPD7533	Approved
0.6993	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD3134	Approved
0.6992	Remote Similarity	NPD968	Approved
0.6986	Remote Similarity	NPD1774	Approved
0.6984	Remote Similarity	NPD1139	Approved
0.6984	Remote Similarity	NPD1137	Approved
0.698	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD1240	Approved
0.6974	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD2796	Approved
0.6972	Remote Similarity	NPD2935	Discontinued
0.6968	Remote Similarity	NPD7199	Phase 2
0.696	Remote Similarity	NPD3021	Approved
0.696	Remote Similarity	NPD3022	Approved
0.6957	Remote Similarity	NPD1296	Phase 2
0.695	Remote Similarity	NPD6896	Approved
0.695	Remote Similarity	NPD6895	Approved
0.6948	Remote Similarity	NPD919	Approved
0.6948	Remote Similarity	NPD6234	Discontinued
0.6947	Remote Similarity	NPD1651	Approved
0.6944	Remote Similarity	NPD6674	Discontinued
0.6944	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD5177	Phase 3
0.6944	Remote Similarity	NPD3060	Approved
0.6943	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD6166	Phase 2
0.6942	Remote Similarity	NPD291	Approved
0.6929	Remote Similarity	NPD3657	Discovery
0.6929	Remote Similarity	NPD5535	Approved
0.6929	Remote Similarity	NPD1138	Approved
0.6929	Remote Similarity	NPD821	Approved
0.6928	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD5677	Discontinued
0.6901	Remote Similarity	NPD1510	Phase 2
0.6899	Remote Similarity	NPD7473	Discontinued
0.6899	Remote Similarity	NPD709	Approved
0.6892	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD1607	Approved
0.6879	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD3926	Phase 2
0.6879	Remote Similarity	NPD2653	Approved
0.6875	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD6799	Approved
0.6871	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD9296	Approved
0.6863	Remote Similarity	NPD5353	Approved
0.6861	Remote Similarity	NPD9494	Approved
0.6857	Remote Similarity	NPD2238	Phase 2
0.6857	Remote Similarity	NPD3620	Phase 2
0.6857	Remote Similarity	NPD4060	Phase 1
0.6857	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD7549	Discontinued
0.6849	Remote Similarity	NPD2677	Approved
0.6835	Remote Similarity	NPD3145	Approved
0.6835	Remote Similarity	NPD3144	Approved
0.6824	Remote Similarity	NPD3146	Approved
0.6824	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD4123	Phase 3
0.6824	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD7054	Approved
0.6809	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD5124	Phase 1
0.6807	Remote Similarity	NPD844	Approved
0.68	Remote Similarity	NPD3687	Approved
0.68	Remote Similarity	NPD3686	Approved
0.6786	Remote Similarity	NPD6233	Phase 2
0.6783	Remote Similarity	NPD3748	Approved
0.6781	Remote Similarity	NPD7466	Approved
0.6781	Remote Similarity	NPD3892	Phase 2
0.6772	Remote Similarity	NPD5242	Approved
0.677	Remote Similarity	NPD7074	Phase 3
0.677	Remote Similarity	NPD7472	Approved
0.6767	Remote Similarity	NPD17	Approved
0.6759	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD5402	Approved
0.675	Remote Similarity	NPD8252	Approved
0.675	Remote Similarity	NPD3818	Discontinued
0.675	Remote Similarity	NPD8099	Discontinued
0.675	Remote Similarity	NPD8251	Approved
0.6748	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD1241	Discontinued
0.6742	Remote Similarity	NPD1182	Approved
0.6741	Remote Similarity	NPD2230	Approved
0.6741	Remote Similarity	NPD2233	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