NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	276.25
Volume:	329.505
LogP:	7.706
LogD:	4.63
LogS:	-5.894
# Rotatable Bonds:	12
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.448
Synthetic Accessibility Score:	1.763
Fsp3:	0.684
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.851
MDCK Permeability:	1.0677652426238637e-05
Pgp-inhibitor:	0.033
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.851
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.126
Plasma Protein Binding (PPB):	98.68914794921875%
Volume Distribution (VD):	3.215
Pgp-substrate:	0.6483617424964905%

ADMET: Metabolism

CYP1A2-inhibitor:	0.612
CYP1A2-substrate:	0.198
CYP2C19-inhibitor:	0.71
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.21
CYP2C9-substrate:	0.973
CYP2D6-inhibitor:	0.74
CYP2D6-substrate:	0.151
CYP3A4-inhibitor:	0.565
CYP3A4-substrate:	0.099

ADMET: Excretion

Clearance (CL):	6.708
Half-life (T1/2):	0.258

ADMET: Toxicity

hERG Blockers:	0.26
Human Hepatotoxicity (H-HT):	0.021
Drug-inuced Liver Injury (DILI):	0.045
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.037
Maximum Recommended Daily Dose:	0.088
Skin Sensitization:	0.958
Carcinogencity:	0.035
Eye Corrosion:	0.978
Eye Irritation:	0.97
Respiratory Toxicity:	0.639

Download Data

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

Natural Product: NPC306884

Natural Product ID:	NPC306884
*Common Name:**	3-Tridecylphenol
IUPAC Name:	3-tridecylphenol
Synonyms:	3-Tridecyl Phenol
Standard InCHIKey:	IFGRPNIAGKTMCH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H32O/c1-2-3-4-5-6-7-8-9-10-11-12-14-18-15-13-16-19(20)17-18/h13,15-17,20H,2-12,14H2,1H3
SMILES:	CCCCCCCCCCCCCc1cccc(c1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL448270
PubChem CID:	155892
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0004647] 1-hydroxy-4-unsubstituted benzenoids

*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
NPO40175	Knema hookeriana	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27008174]
NPO29719	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[27140807]
NPO29719	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	leaves	n.a.	n.a.	PMID[33127538]
NPO29719	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	fresh sarcotestas	Kwanak Campus of Seoul National University, Seoul, Korea	1996-Sep	PMID[9677265]
NPO29719	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	leaves	St. Louis	1996-SEP	PMID[9834151]
NPO29719	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9834158]
NPO29719	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO29719	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO29719	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO29719	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	Wood	n.a.	n.a.	Database[FooDB]
NPO29719	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota		n.a.	n.a.	Database[FooDB]

☑ 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	8
Ki	2

Activity Type	# Activity
Cell Line	5
Individual Protein	2
Others	1
PROTEIN-PROTEIN INTERACTION	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT657	Individual Protein	1-phosphatidylinositol-4,5-bisphosphate phosphodiesterase gamma-1	Bos taurus	IC50	=	57850.0	nM	PMID[448807]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	7.04	ug.mL-1	PMID[448807]
NPT658	Cell Line	HT1197	Homo sapiens	IC50	=	14.56	ug.mL-1	PMID[448807]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	25.9	ug.mL-1	PMID[448807]
NPT148	Cell Line	HCT-15	Homo sapiens	IC50	=	29.7	ug.mL-1	PMID[448807]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	>	50.0	ug.mL-1	PMID[448807]
NPT657	Individual Protein	1-phosphatidylinositol-4,5-bisphosphate phosphodiesterase gamma-1	Bos taurus	IC50	=	87950.0	nM	PMID[448807]
NPT27	Others	Unspecified		IC50	=	73.24	ug.mL-1	PMID[448807]
NPT21616	PROTEIN-PROTEIN INTERACTION	Bcl-xL/BAK	Homo sapiens	Ki	>	23000.0	nM	PMID[448808]
NPT21617	PROTEIN-PROTEIN INTERACTION	Induced myeloid leukemia cell differentiation protein Mcl-1/BH3-interacting domain death agonist	Homo sapiens	Ki	>	33000.0	nM	PMID[448808]

☑ 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 NPC306884 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	247
0.1-0.2	1864
0.2-0.3	5625
0.3-0.4	13102
0.4-0.5	6884
0.5-0.6	9597
0.6-0.7	3965
0.7-0.8	1050
0.8-0.85	182
0.85-0.9	106
0.9-0.95	61
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC147284
1.0	High Similarity	NPC162314
1.0	High Similarity	NPC210497
1.0	High Similarity	NPC94139
1.0	High Similarity	NPC3358
0.977	High Similarity	NPC192
0.9556	High Similarity	NPC32714
0.954	High Similarity	NPC27974
0.9444	High Similarity	NPC76938
0.9355	High Similarity	NPC48730
0.9355	High Similarity	NPC248396
0.9355	High Similarity	NPC129373
0.9333	High Similarity	NPC55903
0.9326	High Similarity	NPC55561
0.9255	High Similarity	NPC252105
0.9247	High Similarity	NPC260775
0.9213	High Similarity	NPC280347
0.9213	High Similarity	NPC123273
0.9213	High Similarity	NPC318325
0.9213	High Similarity	NPC242240
0.9213	High Similarity	NPC177420
0.9195	High Similarity	NPC150837
0.9158	High Similarity	NPC302219
0.9158	High Similarity	NPC168303
0.9158	High Similarity	NPC71002
0.9158	High Similarity	NPC249828
0.9158	High Similarity	NPC94351
0.9158	High Similarity	NPC146798
0.9158	High Similarity	NPC85479
0.9158	High Similarity	NPC53051
0.9158	High Similarity	NPC106396
0.9158	High Similarity	NPC242342
0.9158	High Similarity	NPC222522
0.9158	High Similarity	NPC313030
0.9158	High Similarity	NPC24404
0.9149	High Similarity	NPC70677
0.9149	High Similarity	NPC130756
0.9149	High Similarity	NPC12931
0.914	High Similarity	NPC6597
0.914	High Similarity	NPC79241
0.914	High Similarity	NPC152097
0.914	High Similarity	NPC474073
0.913	High Similarity	NPC222146
0.9101	High Similarity	NPC19680
0.9101	High Similarity	NPC113460
0.9101	High Similarity	NPC25493
0.9053	High Similarity	NPC477685
0.9053	High Similarity	NPC166313
0.9053	High Similarity	NPC11280
0.9053	High Similarity	NPC192032
0.9053	High Similarity	NPC24407
0.9053	High Similarity	NPC284011
0.9053	High Similarity	NPC137415
0.9053	High Similarity	NPC72947
0.9053	High Similarity	NPC147310
0.9053	High Similarity	NPC294186
0.9043	High Similarity	NPC299762
0.9043	High Similarity	NPC33675
0.9032	High Similarity	NPC312132
0.9032	High Similarity	NPC259512
0.9022	High Similarity	NPC316301
0.9022	High Similarity	NPC152415
0.9022	High Similarity	NPC245187
0.9022	High Similarity	NPC27323
0.9011	High Similarity	NPC304541
0.9011	High Similarity	NPC231150
0.9	High Similarity	NPC258219
0.8989	High Similarity	NPC407
0.8989	High Similarity	NPC307235
0.8989	High Similarity	NPC23167
0.8958	High Similarity	NPC108497
0.8958	High Similarity	NPC196479
0.8947	High Similarity	NPC72729
0.8947	High Similarity	NPC166761
0.8947	High Similarity	NPC294741
0.8947	High Similarity	NPC10588
0.8936	High Similarity	NPC475078
0.8925	High Similarity	NPC274678
0.8925	High Similarity	NPC26244
0.8878	High Similarity	NPC155072
0.8876	High Similarity	NPC197783
0.8876	High Similarity	NPC155393
0.8854	High Similarity	NPC80800
0.883	High Similarity	NPC473388
0.8817	High Similarity	NPC151715
0.8804	High Similarity	NPC155908
0.8804	High Similarity	NPC306074
0.8791	High Similarity	NPC98772
0.8788	High Similarity	NPC232523
0.8788	High Similarity	NPC158253
0.8788	High Similarity	NPC204901
0.8788	High Similarity	NPC305603
0.8788	High Similarity	NPC61033
0.8778	High Similarity	NPC184169
0.8776	High Similarity	NPC134829
0.8776	High Similarity	NPC47284
0.8764	High Similarity	NPC248817
0.8764	High Similarity	NPC175313
0.8764	High Similarity	NPC286904
0.8763	High Similarity	NPC235762
0.8763	High Similarity	NPC471228
0.875	High Similarity	NPC211885
0.875	High Similarity	NPC225506
0.875	High Similarity	NPC174911
0.8737	High Similarity	NPC77492
0.8737	High Similarity	NPC225464
0.871	High Similarity	NPC29373
0.8696	High Similarity	NPC312304
0.8687	High Similarity	NPC99836
0.8687	High Similarity	NPC39097
0.8687	High Similarity	NPC39664
0.8687	High Similarity	NPC12640
0.8687	High Similarity	NPC477814
0.8687	High Similarity	NPC109691
0.8687	High Similarity	NPC469913
0.8687	High Similarity	NPC201662
0.8687	High Similarity	NPC470700
0.8687	High Similarity	NPC302681
0.8687	High Similarity	NPC53740
0.8687	High Similarity	NPC118286
0.8673	High Similarity	NPC475225
0.8673	High Similarity	NPC323810
0.8673	High Similarity	NPC241891
0.8652	High Similarity	NPC265146
0.8652	High Similarity	NPC124436
0.8646	High Similarity	NPC252821
0.8646	High Similarity	NPC92730
0.8646	High Similarity	NPC122005
0.8632	High Similarity	NPC132271
0.8632	High Similarity	NPC292730
0.8632	High Similarity	NPC216520
0.8632	High Similarity	NPC82664
0.8632	High Similarity	NPC202986
0.8617	High Similarity	NPC289769
0.8602	High Similarity	NPC270547
0.8602	High Similarity	NPC204210
0.8602	High Similarity	NPC45040
0.86	High Similarity	NPC54844
0.86	High Similarity	NPC320439
0.8586	High Similarity	NPC246056
0.8586	High Similarity	NPC117115
0.8586	High Similarity	NPC37802
0.8571	High Similarity	NPC269212
0.8542	High Similarity	NPC156313
0.8542	High Similarity	NPC109955
0.8542	High Similarity	NPC32674
0.8542	High Similarity	NPC470161
0.8526	High Similarity	NPC8392
0.8515	High Similarity	NPC11554
0.8511	High Similarity	NPC271440
0.8511	High Similarity	NPC325292
0.8511	High Similarity	NPC138117
0.85	High Similarity	NPC310456
0.8495	Intermediate Similarity	NPC300017
0.8485	Intermediate Similarity	NPC244513
0.8485	Intermediate Similarity	NPC227458
0.8485	Intermediate Similarity	NPC218879
0.8485	Intermediate Similarity	NPC475580
0.8485	Intermediate Similarity	NPC120719
0.8469	Intermediate Similarity	NPC100340
0.8469	Intermediate Similarity	NPC12221
0.8469	Intermediate Similarity	NPC143659
0.8454	Intermediate Similarity	NPC51333
0.8454	Intermediate Similarity	NPC128723
0.8454	Intermediate Similarity	NPC78119
0.8454	Intermediate Similarity	NPC216468
0.8454	Intermediate Similarity	NPC132078
0.8431	Intermediate Similarity	NPC26013
0.8431	Intermediate Similarity	NPC254833
0.8431	Intermediate Similarity	NPC282855
0.8431	Intermediate Similarity	NPC228343
0.8431	Intermediate Similarity	NPC19808
0.8431	Intermediate Similarity	NPC33728
0.8421	Intermediate Similarity	NPC128062
0.8416	Intermediate Similarity	NPC66834
0.8416	Intermediate Similarity	NPC474352
0.8416	Intermediate Similarity	NPC151477
0.84	Intermediate Similarity	NPC138942
0.8387	Intermediate Similarity	NPC70436
0.8384	Intermediate Similarity	NPC168829
0.8367	Intermediate Similarity	NPC213730
0.8367	Intermediate Similarity	NPC130103
0.8365	Intermediate Similarity	NPC62867
0.8365	Intermediate Similarity	NPC166995
0.8365	Intermediate Similarity	NPC177962
0.835	Intermediate Similarity	NPC13482
0.835	Intermediate Similarity	NPC208229
0.8333	Intermediate Similarity	NPC174981
0.8333	Intermediate Similarity	NPC68260
0.8333	Intermediate Similarity	NPC306295
0.8333	Intermediate Similarity	NPC144682
0.8333	Intermediate Similarity	NPC257182
0.8333	Intermediate Similarity	NPC313650
0.8333	Intermediate Similarity	NPC107522
0.8333	Intermediate Similarity	NPC279887
0.8333	Intermediate Similarity	NPC75440
0.8333	Intermediate Similarity	NPC64586
0.8317	Intermediate Similarity	NPC21594
0.8317	Intermediate Similarity	NPC271274
0.8316	Intermediate Similarity	NPC295295

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 NPC306884 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	259
0.1-0.2	1077
0.2-0.3	1293
0.3-0.4	2878
0.4-0.5	1967
0.5-0.6	1121
0.6-0.7	458
0.7-0.8	75
0.8-0.85	10
0.85-0.9	9
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9341	High Similarity	NPD844	Approved
0.9032	High Similarity	NPD288	Approved
0.9022	High Similarity	NPD1432	Clinical (unspecified phase)
0.8925	High Similarity	NPD2860	Approved
0.8925	High Similarity	NPD2859	Approved
0.8842	High Similarity	NPD3020	Approved
0.8817	High Similarity	NPD2933	Approved
0.8817	High Similarity	NPD2934	Approved
0.875	High Similarity	NPD289	Clinical (unspecified phase)
0.871	High Similarity	NPD845	Approved
0.8652	High Similarity	NPD111	Approved
0.85	High Similarity	NPD1444	Approved
0.85	High Similarity	NPD1445	Approved
0.8431	Intermediate Similarity	NPD3021	Approved
0.8431	Intermediate Similarity	NPD3022	Approved
0.8333	Intermediate Similarity	NPD1809	Phase 2
0.8283	Intermediate Similarity	NPD940	Approved
0.8283	Intermediate Similarity	NPD846	Approved
0.8252	Intermediate Similarity	NPD4750	Phase 3
0.8252	Intermediate Similarity	NPD1792	Phase 2
0.819	Intermediate Similarity	NPD7635	Approved
0.8131	Intermediate Similarity	NPD6671	Approved
0.8058	Intermediate Similarity	NPD2342	Discontinued
0.802	Intermediate Similarity	NPD9500	Approved
0.8	Intermediate Similarity	NPD1242	Phase 1
0.787	Intermediate Similarity	NPD1793	Approved
0.787	Intermediate Similarity	NPD1791	Approved
0.7816	Intermediate Similarity	NPD9087	Approved
0.7778	Intermediate Similarity	NPD2228	Approved
0.7778	Intermediate Similarity	NPD2234	Approved
0.7778	Intermediate Similarity	NPD2229	Approved
0.7767	Intermediate Similarity	NPD9608	Approved
0.7767	Intermediate Similarity	NPD9610	Approved
0.7757	Intermediate Similarity	NPD228	Approved
0.7748	Intermediate Similarity	NPD3091	Approved
0.7679	Intermediate Similarity	NPD4093	Discontinued
0.7647	Intermediate Similarity	NPD3028	Approved
0.7632	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD4059	Approved
0.7611	Intermediate Similarity	NPD2932	Approved
0.7611	Intermediate Similarity	NPD3019	Approved
0.7593	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD9294	Approved
0.7545	Intermediate Similarity	NPD9614	Approved
0.7545	Intermediate Similarity	NPD9618	Approved
0.7523	Intermediate Similarity	NPD9377	Approved
0.7523	Intermediate Similarity	NPD9379	Approved
0.7478	Intermediate Similarity	NPD3092	Approved
0.7477	Intermediate Similarity	NPD2684	Approved
0.7473	Intermediate Similarity	NPD9088	Approved
0.7456	Intermediate Similarity	NPD1751	Approved
0.7455	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD9273	Approved
0.7364	Intermediate Similarity	NPD7843	Approved
0.735	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD9615	Approved
0.7345	Intermediate Similarity	NPD9613	Approved
0.7345	Intermediate Similarity	NPD9616	Approved
0.7321	Intermediate Similarity	NPD7157	Approved
0.7304	Intermediate Similarity	NPD4589	Approved
0.7304	Intermediate Similarity	NPD2286	Discontinued
0.7304	Intermediate Similarity	NPD4626	Approved
0.7304	Intermediate Similarity	NPD3095	Discontinued
0.7297	Intermediate Similarity	NPD5283	Phase 1
0.729	Intermediate Similarity	NPD968	Approved
0.7281	Intermediate Similarity	NPD5304	Approved
0.7281	Intermediate Similarity	NPD316	Approved
0.7281	Intermediate Similarity	NPD5303	Approved
0.7265	Intermediate Similarity	NPD2233	Approved
0.7265	Intermediate Similarity	NPD2232	Approved
0.7265	Intermediate Similarity	NPD2230	Approved
0.7257	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD5736	Approved
0.7248	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD4818	Approved
0.7238	Intermediate Similarity	NPD4817	Approved
0.7227	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD3094	Phase 2
0.7203	Intermediate Similarity	NPD1755	Approved
0.7203	Intermediate Similarity	NPD4749	Approved
0.7182	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD256	Approved
0.7168	Intermediate Similarity	NPD255	Approved
0.7167	Intermediate Similarity	NPD2195	Approved
0.7167	Intermediate Similarity	NPD6584	Phase 3
0.7167	Intermediate Similarity	NPD2194	Approved
0.7158	Intermediate Similarity	NPD9089	Approved
0.7155	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5310	Approved
0.7143	Intermediate Similarity	NPD6696	Suspended
0.7143	Intermediate Similarity	NPD5311	Approved
0.713	Intermediate Similarity	NPD7330	Discontinued
0.7107	Intermediate Similarity	NPD3636	Approved
0.7107	Intermediate Similarity	NPD3637	Approved
0.7107	Intermediate Similarity	NPD3635	Approved
0.7105	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD9244	Approved
0.7094	Intermediate Similarity	NPD1983	Approved
0.7094	Intermediate Similarity	NPD3496	Discontinued
0.7094	Intermediate Similarity	NPD1981	Approved
0.7094	Intermediate Similarity	NPD1980	Approved
0.7091	Intermediate Similarity	NPD5451	Approved
0.7083	Intermediate Similarity	NPD3053	Approved
0.7083	Intermediate Similarity	NPD3055	Approved
0.708	Intermediate Similarity	NPD497	Approved
0.708	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD475	Phase 2
0.7064	Intermediate Similarity	NPD290	Approved
0.7054	Intermediate Similarity	NPD821	Approved
0.7053	Intermediate Similarity	NPD9093	Approved
0.7049	Intermediate Similarity	NPD2606	Approved
0.7049	Intermediate Similarity	NPD2605	Approved
0.7043	Intermediate Similarity	NPD16	Approved
0.7043	Intermediate Similarity	NPD856	Approved
0.7034	Intermediate Similarity	NPD1201	Approved
0.7025	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD709	Approved
0.7016	Intermediate Similarity	NPD6663	Approved
0.7009	Intermediate Similarity	NPD9381	Approved
0.7009	Intermediate Similarity	NPD2667	Approved
0.7009	Intermediate Similarity	NPD2668	Approved
0.7009	Intermediate Similarity	NPD9384	Approved
0.7	Intermediate Similarity	NPD9295	Approved
0.6992	Remote Similarity	NPD4625	Phase 3
0.6992	Remote Similarity	NPD5155	Approved
0.6992	Remote Similarity	NPD5156	Approved
0.6992	Remote Similarity	NPD3027	Phase 3
0.6991	Remote Similarity	NPD496	Approved
0.6991	Remote Similarity	NPD495	Approved
0.6991	Remote Similarity	NPD498	Approved
0.6981	Remote Similarity	NPD1616	Discontinued
0.6975	Remote Similarity	NPD2231	Phase 2
0.6975	Remote Similarity	NPD2235	Phase 2
0.6967	Remote Similarity	NPD2861	Phase 2
0.696	Remote Similarity	NPD6346	Approved
0.6957	Remote Similarity	NPD7340	Approved
0.6957	Remote Similarity	NPD7636	Approved
0.6949	Remote Similarity	NPD3023	Approved
0.6949	Remote Similarity	NPD3026	Approved
0.6939	Remote Similarity	NPD9073	Approved
0.6935	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1357	Approved
0.6923	Remote Similarity	NPD3025	Approved
0.6923	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3024	Approved
0.6923	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5691	Approved
0.6917	Remote Similarity	NPD6583	Phase 3
0.6917	Remote Similarity	NPD4659	Approved
0.6917	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD9622	Approved
0.6917	Remote Similarity	NPD6582	Phase 2
0.6911	Remote Similarity	NPD3594	Approved
0.6911	Remote Similarity	NPD3595	Approved
0.6909	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD5535	Approved
0.6897	Remote Similarity	NPD317	Approved
0.6897	Remote Similarity	NPD318	Approved
0.6885	Remote Similarity	NPD258	Approved
0.6885	Remote Similarity	NPD257	Approved
0.6885	Remote Similarity	NPD4624	Approved
0.6864	Remote Similarity	NPD1778	Approved
0.686	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD7095	Approved
0.6852	Remote Similarity	NPD3680	Approved
0.6852	Remote Similarity	NPD3682	Approved
0.6852	Remote Similarity	NPD3683	Approved
0.6852	Remote Similarity	NPD3681	Approved
0.6852	Remote Similarity	NPD4656	Approved
0.6852	Remote Similarity	NPD4231	Approved
0.6852	Remote Similarity	NPD4229	Approved
0.6852	Remote Similarity	NPD4658	Approved
0.6847	Remote Similarity	NPD9266	Approved
0.6847	Remote Similarity	NPD74	Approved
0.6842	Remote Similarity	NPD1398	Phase 1
0.6838	Remote Similarity	NPD1759	Phase 1
0.6833	Remote Similarity	NPD2562	Approved
0.6833	Remote Similarity	NPD1608	Approved
0.6833	Remote Similarity	NPD2561	Approved
0.6825	Remote Similarity	NPD4060	Phase 1
0.6818	Remote Similarity	NPD3134	Approved
0.681	Remote Similarity	NPD9568	Approved
0.681	Remote Similarity	NPD9493	Approved
0.6807	Remote Similarity	NPD3847	Discontinued
0.6807	Remote Similarity	NPD3421	Phase 3
0.6807	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD3143	Discontinued
0.6803	Remote Similarity	NPD1470	Approved
0.6803	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD4103	Phase 2
0.68	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD159	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD9611	Approved
0.6792	Remote Similarity	NPD9609	Approved
0.6792	Remote Similarity	NPD9612	Approved
0.678	Remote Similarity	NPD1651	Approved
0.6777	Remote Similarity	NPD1669	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