NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	188.12
Volume:	220.456
LogP:	4.026
LogD:	4.089
LogS:	-3.431
# Rotatable Bonds:	3
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.718
Synthetic Accessibility Score:	2.755
Fsp3:	0.231
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.553
MDCK Permeability:	2.928429421444889e-05
Pgp-inhibitor:	0.126
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.217
Plasma Protein Binding (PPB):	96.2792739868164%
Volume Distribution (VD):	1.821
Pgp-substrate:	2.176419258117676%

ADMET: Metabolism

CYP1A2-inhibitor:	0.897
CYP1A2-substrate:	0.308
CYP2C19-inhibitor:	0.736
CYP2C19-substrate:	0.323
CYP2C9-inhibitor:	0.545
CYP2C9-substrate:	0.923
CYP2D6-inhibitor:	0.911
CYP2D6-substrate:	0.815
CYP3A4-inhibitor:	0.627
CYP3A4-substrate:	0.35

ADMET: Excretion

Clearance (CL):	4.637
Half-life (T1/2):	0.769

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.136
Drug-inuced Liver Injury (DILI):	0.014
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.063
Maximum Recommended Daily Dose:	0.185
Skin Sensitization:	0.943
Carcinogencity:	0.161
Eye Corrosion:	0.926
Eye Irritation:	0.991
Respiratory Toxicity:	0.821

Download Data

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

Natural Product: NPC184169

Natural Product ID:	NPC184169
*Common Name:**	4-[(1E)-3,3-Dimethylpenta-1,4-Dienyl]Phenol
IUPAC Name:	4-[(1E)-3,3-dimethylpenta-1,4-dienyl]phenol
Synonyms:
Standard InCHIKey:	DKVQOAMBVKKPAM-MDZDMXLPSA-N
Standard InCHI:	InChI=1S/C13H16O/c1-4-13(2,3)10-9-11-5-7-12(14)8-6-11/h4-10,14H,1H2,2-3H3/b10-9+
SMILES:	C=CC(/C=C/c1ccc(cc1)O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1990546
PubChem CID:	5470819
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000037] Styrenes

*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
NPO28809	Cullen corylifolium	Species	Fabaceae	Eukaryota	n.a.	fruit	n.a.	PMID[20663508]
NPO28809	Cullen corylifolium	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24507928]
NPO28809	Cullen corylifolium	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9544566]
NPO1470	Fructus psoraleae corylifoliae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO28809	Cullen corylifolium	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28809	Cullen corylifolium	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28809	Cullen corylifolium	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
GI50	55

Activity Type	# Activity
Cell Line	55

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	34514.37	nM	PMID[546030]
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	34994.52	nM	PMID[546030]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	31841.98	nM	PMID[546030]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	28906.8	nM	PMID[546030]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	46989.41	nM	PMID[546030]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	40364.54	nM	PMID[546030]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	37583.74	nM	PMID[546030]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	38459.18	nM	PMID[546030]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	30060.76	nM	PMID[546030]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	36812.9	nM	PMID[546030]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	28313.92	nM	PMID[546030]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	28773.98	nM	PMID[546030]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	38547.84	nM	PMID[546030]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	47863.01	nM	PMID[546030]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	58210.32	nM	PMID[546030]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	29991.63	nM	PMID[546030]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	39719.15	nM	PMID[546030]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	46558.61	nM	PMID[546030]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	36391.5	nM	PMID[546030]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	44258.84	nM	PMID[546030]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	36140.99	nM	PMID[546030]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	33265.96	nM	PMID[546030]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	39264.49	nM	PMID[546030]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	34434.99	nM	PMID[546030]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	43052.66	nM	PMID[546030]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	69502.43	nM	PMID[546030]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	27542.29	nM	PMID[546030]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	21877.62	nM	PMID[546030]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	55462.57	nM	PMID[546030]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	36475.39	nM	PMID[546030]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	23388.37	nM	PMID[546030]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	29107.17	nM	PMID[546030]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	27925.44	nM	PMID[546030]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	39084.09	nM	PMID[546030]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	31332.86	nM	PMID[546030]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	33884.42	nM	PMID[546030]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	45289.76	nM	PMID[546030]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	27989.81	nM	PMID[546030]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	35727.28	nM	PMID[546030]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	49659.23	nM	PMID[546030]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	19952.62	nM	PMID[546030]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	19815.27	nM	PMID[546030]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	44668.36	nM	PMID[546030]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	42657.95	nM	PMID[546030]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	37931.5	nM	PMID[546030]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	27039.58	nM	PMID[546030]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	43954.16	nM	PMID[546030]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	27669.42	nM	PMID[546030]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	39174.19	nM	PMID[546030]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	23988.33	nM	PMID[546030]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	39264.49	nM	PMID[546030]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	38194.43	nM	PMID[546030]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	35892.19	nM	PMID[546030]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	24831.33	nM	PMID[546030]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	35481.34	nM	PMID[546030]

☑ 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 NPC184169 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	227
0.1-0.2	2803
0.2-0.3	7931
0.3-0.4	11610
0.4-0.5	7359
0.5-0.6	8772
0.6-0.7	3031
0.7-0.8	742
0.8-0.85	128
0.85-0.9	60
0.9-0.95	20
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
0.9762	High Similarity	NPC98772
0.9756	High Similarity	NPC248817
0.9643	High Similarity	NPC113460
0.9643	High Similarity	NPC25493
0.9639	High Similarity	NPC197783
0.9634	High Similarity	NPC265146
0.9634	High Similarity	NPC124436
0.9535	High Similarity	NPC270547
0.9529	High Similarity	NPC123273
0.9529	High Similarity	NPC242240
0.9529	High Similarity	NPC318325
0.9529	High Similarity	NPC280347
0.9529	High Similarity	NPC177420
0.9524	High Similarity	NPC23167
0.9518	High Similarity	NPC175313
0.9419	High Similarity	NPC55561
0.9318	High Similarity	NPC316301
0.9318	High Similarity	NPC27323
0.931	High Similarity	NPC155908
0.9302	High Similarity	NPC258219
0.9186	High Similarity	NPC104216
0.9091	High Similarity	NPC204210
0.9091	High Similarity	NPC304541
0.907	High Similarity	NPC407
0.907	High Similarity	NPC307235
0.9059	High Similarity	NPC286904
0.9059	High Similarity	NPC150837
0.9011	High Similarity	NPC225464
0.9	High Similarity	NPC26244
0.8989	High Similarity	NPC138117
0.8989	High Similarity	NPC325292
0.8989	High Similarity	NPC181709
0.8977	High Similarity	NPC300017
0.8966	High Similarity	NPC27974
0.8953	High Similarity	NPC155393
0.8913	High Similarity	NPC92730
0.8913	High Similarity	NPC122005
0.8913	High Similarity	NPC252821
0.8901	High Similarity	NPC473388
0.8889	High Similarity	NPC152415
0.8889	High Similarity	NPC151715
0.8876	High Similarity	NPC45040
0.8876	High Similarity	NPC306074
0.8864	High Similarity	NPC70436
0.8817	High Similarity	NPC225506
0.8804	High Similarity	NPC77492
0.8791	High Similarity	NPC8392
0.8791	High Similarity	NPC144682
0.8791	High Similarity	NPC313650
0.8778	High Similarity	NPC162314
0.8778	High Similarity	NPC210497
0.8778	High Similarity	NPC147284
0.8778	High Similarity	NPC94139
0.8778	High Similarity	NPC3358
0.8778	High Similarity	NPC306884
0.8778	High Similarity	NPC55903
0.8764	High Similarity	NPC300478
0.8764	High Similarity	NPC192
0.875	High Similarity	NPC19680
0.8723	High Similarity	NPC101025
0.8723	High Similarity	NPC472585
0.8723	High Similarity	NPC471578
0.871	High Similarity	NPC128723
0.8696	High Similarity	NPC292730
0.8696	High Similarity	NPC132271
0.8696	High Similarity	NPC216520
0.8696	High Similarity	NPC82664
0.8681	High Similarity	NPC81010
0.8681	High Similarity	NPC289769
0.8681	High Similarity	NPC32977
0.8681	High Similarity	NPC128062
0.8667	High Similarity	NPC231150
0.8632	High Similarity	NPC62351
0.8617	High Similarity	NPC211885
0.8602	High Similarity	NPC260000
0.8602	High Similarity	NPC201967
0.8587	High Similarity	NPC286006
0.8587	High Similarity	NPC107522
0.8587	High Similarity	NPC222146
0.8587	High Similarity	NPC274678
0.8556	High Similarity	NPC151764
0.8511	High Similarity	NPC299762
0.8511	High Similarity	NPC33675
0.8511	High Similarity	NPC132078
0.8511	High Similarity	NPC171843
0.8511	High Similarity	NPC51333
0.8511	High Similarity	NPC280869
0.8511	High Similarity	NPC78119
0.8511	High Similarity	NPC80027
0.8511	High Similarity	NPC216468
0.8511	High Similarity	NPC130193
0.8495	Intermediate Similarity	NPC202986
0.8478	Intermediate Similarity	NPC76938
0.8478	Intermediate Similarity	NPC245187
0.8438	Intermediate Similarity	NPC196479
0.8421	Intermediate Similarity	NPC213730
0.8421	Intermediate Similarity	NPC289381
0.8421	Intermediate Similarity	NPC155847
0.8421	Intermediate Similarity	NPC253746
0.8404	Intermediate Similarity	NPC79241
0.8404	Intermediate Similarity	NPC6597
0.8404	Intermediate Similarity	NPC152097
0.8404	Intermediate Similarity	NPC32674
0.8404	Intermediate Similarity	NPC107619
0.8404	Intermediate Similarity	NPC474073
0.8404	Intermediate Similarity	NPC109955
0.8404	Intermediate Similarity	NPC475078
0.8387	Intermediate Similarity	NPC32714
0.837	Intermediate Similarity	NPC271440
0.837	Intermediate Similarity	NPC29373
0.8367	Intermediate Similarity	NPC477814
0.8352	Intermediate Similarity	NPC47950
0.8352	Intermediate Similarity	NPC312304
0.8351	Intermediate Similarity	NPC120719
0.8333	Intermediate Similarity	NPC7686
0.8333	Intermediate Similarity	NPC252105
0.8333	Intermediate Similarity	NPC40258
0.8333	Intermediate Similarity	NPC91461
0.8316	Intermediate Similarity	NPC275104
0.8316	Intermediate Similarity	NPC131587
0.8316	Intermediate Similarity	NPC260775
0.8316	Intermediate Similarity	NPC245561
0.8316	Intermediate Similarity	NPC125732
0.8298	Intermediate Similarity	NPC312132
0.8298	Intermediate Similarity	NPC259512
0.8293	Intermediate Similarity	NPC100980
0.828	Intermediate Similarity	NPC471581
0.8265	Intermediate Similarity	NPC303141
0.8265	Intermediate Similarity	NPC154899
0.8265	Intermediate Similarity	NPC233396
0.8265	Intermediate Similarity	NPC138942
0.8247	Intermediate Similarity	NPC304638
0.8247	Intermediate Similarity	NPC168829
0.8247	Intermediate Similarity	NPC68269
0.8247	Intermediate Similarity	NPC178902
0.8242	Intermediate Similarity	NPC177844
0.8242	Intermediate Similarity	NPC259134
0.8242	Intermediate Similarity	NPC8002
0.8242	Intermediate Similarity	NPC99886
0.8229	Intermediate Similarity	NPC248573
0.8229	Intermediate Similarity	NPC223393
0.8229	Intermediate Similarity	NPC12931
0.8229	Intermediate Similarity	NPC129373
0.8229	Intermediate Similarity	NPC161571
0.8229	Intermediate Similarity	NPC48730
0.8229	Intermediate Similarity	NPC166761
0.8229	Intermediate Similarity	NPC275053
0.8229	Intermediate Similarity	NPC72729
0.8229	Intermediate Similarity	NPC52472
0.8229	Intermediate Similarity	NPC248396
0.8229	Intermediate Similarity	NPC70677
0.8229	Intermediate Similarity	NPC130756
0.8191	Intermediate Similarity	NPC246679
0.8191	Intermediate Similarity	NPC257182
0.8182	Intermediate Similarity	NPC271274
0.8182	Intermediate Similarity	NPC135464
0.8182	Intermediate Similarity	NPC113457
0.8182	Intermediate Similarity	NPC231705
0.8182	Intermediate Similarity	NPC92623
0.8172	Intermediate Similarity	NPC295295
0.8163	Intermediate Similarity	NPC474603
0.8163	Intermediate Similarity	NPC8931
0.8163	Intermediate Similarity	NPC288411
0.8163	Intermediate Similarity	NPC12987
0.8163	Intermediate Similarity	NPC261573
0.8163	Intermediate Similarity	NPC52087
0.8163	Intermediate Similarity	NPC119860
0.8163	Intermediate Similarity	NPC79672
0.8163	Intermediate Similarity	NPC120693
0.8152	Intermediate Similarity	NPC71853
0.8144	Intermediate Similarity	NPC80800
0.8144	Intermediate Similarity	NPC51633
0.8144	Intermediate Similarity	NPC110764
0.8125	Intermediate Similarity	NPC100870
0.8105	Intermediate Similarity	NPC283711
0.81	Intermediate Similarity	NPC142297
0.81	Intermediate Similarity	NPC228737
0.8081	Intermediate Similarity	NPC474839
0.8081	Intermediate Similarity	NPC47284
0.8081	Intermediate Similarity	NPC219286
0.8081	Intermediate Similarity	NPC99557
0.8081	Intermediate Similarity	NPC243677
0.8081	Intermediate Similarity	NPC127676
0.8065	Intermediate Similarity	NPC321956
0.8061	Intermediate Similarity	NPC235762
0.8061	Intermediate Similarity	NPC470202
0.8061	Intermediate Similarity	NPC135784
0.8061	Intermediate Similarity	NPC249828
0.8061	Intermediate Similarity	NPC108497
0.8061	Intermediate Similarity	NPC222522
0.8061	Intermediate Similarity	NPC305205
0.8061	Intermediate Similarity	NPC85479
0.8061	Intermediate Similarity	NPC242342
0.8061	Intermediate Similarity	NPC313030
0.8061	Intermediate Similarity	NPC471228
0.8061	Intermediate Similarity	NPC302219
0.8061	Intermediate Similarity	NPC53051
0.8061	Intermediate Similarity	NPC106396
0.8061	Intermediate Similarity	NPC94351
0.8061	Intermediate Similarity	NPC71002

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 NPC184169 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	255
0.1-0.2	1178
0.2-0.3	1479
0.3-0.4	2952
0.4-0.5	1884
0.5-0.6	987
0.6-0.7	340
0.7-0.8	58
0.8-0.85	8
0.85-0.9	4
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9634	High Similarity	NPD111	Approved
0.9318	High Similarity	NPD1432	Clinical (unspecified phase)
0.9101	High Similarity	NPD2933	Approved
0.9101	High Similarity	NPD2934	Approved
0.9	High Similarity	NPD2860	Approved
0.9	High Similarity	NPD2859	Approved
0.8791	High Similarity	NPD1809	Phase 2
0.871	High Similarity	NPD3020	Approved
0.8587	High Similarity	NPD844	Approved
0.8571	High Similarity	NPD845	Approved
0.8526	High Similarity	NPD846	Approved
0.8526	High Similarity	NPD940	Approved
0.8298	Intermediate Similarity	NPD288	Approved
0.8293	Intermediate Similarity	NPD9087	Approved
0.8229	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.8229	Intermediate Similarity	NPD1242	Phase 1
0.8163	Intermediate Similarity	NPD9608	Approved
0.8163	Intermediate Similarity	NPD9610	Approved
0.7941	Intermediate Similarity	NPD3021	Approved
0.7941	Intermediate Similarity	NPD3022	Approved
0.7907	Intermediate Similarity	NPD9088	Approved
0.7857	Intermediate Similarity	NPD3028	Approved
0.7822	Intermediate Similarity	NPD1444	Approved
0.7822	Intermediate Similarity	NPD1445	Approved
0.7791	Intermediate Similarity	NPD9294	Approved
0.77	Intermediate Similarity	NPD9500	Approved
0.7653	Intermediate Similarity	NPD9273	Approved
0.7642	Intermediate Similarity	NPD2234	Approved
0.7642	Intermediate Similarity	NPD2228	Approved
0.7642	Intermediate Similarity	NPD2229	Approved
0.7619	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD228	Approved
0.7596	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD1792	Phase 2
0.7556	Intermediate Similarity	NPD9089	Approved
0.75	Intermediate Similarity	NPD2684	Approved
0.7477	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD968	Approved
0.7455	Intermediate Similarity	NPD3091	Approved
0.7444	Intermediate Similarity	NPD9093	Approved
0.7429	Intermediate Similarity	NPD4750	Phase 3
0.7407	Intermediate Similarity	NPD1791	Approved
0.7407	Intermediate Similarity	NPD1793	Approved
0.7404	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD821	Approved
0.7383	Intermediate Similarity	NPD9377	Approved
0.7383	Intermediate Similarity	NPD9379	Approved
0.7368	Intermediate Similarity	NPD9295	Approved
0.7364	Intermediate Similarity	NPD856	Approved
0.7364	Intermediate Similarity	NPD16	Approved
0.7339	Intermediate Similarity	NPD255	Approved
0.7339	Intermediate Similarity	NPD256	Approved
0.7321	Intermediate Similarity	NPD1751	Approved
0.7321	Intermediate Similarity	NPD2932	Approved
0.7321	Intermediate Similarity	NPD4059	Approved
0.7321	Intermediate Similarity	NPD3019	Approved
0.7321	Intermediate Similarity	NPD4589	Approved
0.7312	Intermediate Similarity	NPD9073	Approved
0.7308	Intermediate Similarity	NPD3134	Approved
0.7297	Intermediate Similarity	NPD5303	Approved
0.7297	Intermediate Similarity	NPD5304	Approved
0.7238	Intermediate Similarity	NPD1358	Approved
0.7238	Intermediate Similarity	NPD2342	Discontinued
0.7238	Intermediate Similarity	NPD290	Approved
0.7232	Intermediate Similarity	NPD4093	Discontinued
0.7232	Intermediate Similarity	NPD1357	Approved
0.7222	Intermediate Similarity	NPD7635	Approved
0.7222	Intermediate Similarity	NPD7843	Approved
0.7207	Intermediate Similarity	NPD317	Approved
0.7207	Intermediate Similarity	NPD318	Approved
0.7196	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD3092	Approved
0.7182	Intermediate Similarity	NPD6671	Approved
0.7182	Intermediate Similarity	NPD7157	Approved
0.7168	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD9545	Approved
0.7117	Intermediate Similarity	NPD9568	Approved
0.7105	Intermediate Similarity	NPD3421	Phase 3
0.7103	Intermediate Similarity	NPD5451	Approved
0.7091	Intermediate Similarity	NPD475	Phase 2
0.7091	Intermediate Similarity	NPD9614	Approved
0.7091	Intermediate Similarity	NPD9618	Approved
0.7083	Intermediate Similarity	NPD9094	Approved
0.708	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD3095	Discontinued
0.7009	Intermediate Similarity	NPD74	Approved
0.7009	Intermediate Similarity	NPD9266	Approved
0.7	Intermediate Similarity	NPD9296	Approved
0.6991	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD1548	Phase 1
0.6983	Remote Similarity	NPD2562	Approved
0.6983	Remote Similarity	NPD2561	Approved
0.6964	Remote Similarity	NPD9493	Approved
0.6957	Remote Similarity	NPD3143	Discontinued
0.6957	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD9244	Approved
0.6949	Remote Similarity	NPD3094	Phase 2
0.6937	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4659	Approved
0.6923	Remote Similarity	NPD6582	Phase 2
0.6923	Remote Similarity	NPD6583	Phase 3
0.6923	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD9264	Approved
0.6916	Remote Similarity	NPD9263	Approved
0.6916	Remote Similarity	NPD9267	Approved
0.6909	Remote Similarity	NPD5535	Approved
0.6903	Remote Similarity	NPD9616	Approved
0.6903	Remote Similarity	NPD9615	Approved
0.6903	Remote Similarity	NPD9613	Approved
0.6897	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD422	Phase 1
0.6891	Remote Similarity	NPD2194	Approved
0.6891	Remote Similarity	NPD2195	Approved
0.687	Remote Similarity	NPD2286	Discontinued
0.687	Remote Similarity	NPD2667	Approved
0.687	Remote Similarity	NPD4626	Approved
0.687	Remote Similarity	NPD9381	Approved
0.687	Remote Similarity	NPD2668	Approved
0.687	Remote Similarity	NPD9384	Approved
0.6847	Remote Similarity	NPD5283	Phase 1
0.6842	Remote Similarity	NPD7330	Discontinued
0.6842	Remote Similarity	NPD1759	Phase 1
0.6842	Remote Similarity	NPD316	Approved
0.6838	Remote Similarity	NPD3070	Discontinued
0.6833	Remote Similarity	NPD5736	Approved
0.6833	Remote Similarity	NPD3637	Approved
0.6833	Remote Similarity	NPD3636	Approved
0.6833	Remote Similarity	NPD3635	Approved
0.681	Remote Similarity	NPD3847	Discontinued
0.681	Remote Similarity	NPD1671	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD1131	Approved
0.6807	Remote Similarity	NPD3053	Approved
0.6807	Remote Similarity	NPD1135	Approved
0.6807	Remote Similarity	NPD1134	Approved
0.6807	Remote Similarity	NPD1133	Approved
0.6807	Remote Similarity	NPD1129	Approved
0.6807	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD3055	Approved
0.6807	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD4103	Phase 2
0.68	Remote Similarity	NPD159	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD9609	Approved
0.6796	Remote Similarity	NPD9612	Approved
0.6796	Remote Similarity	NPD9611	Approved
0.678	Remote Similarity	NPD9622	Approved
0.678	Remote Similarity	NPD1755	Approved
0.6777	Remote Similarity	NPD2606	Approved
0.6777	Remote Similarity	NPD2605	Approved
0.6762	Remote Similarity	NPD4818	Approved
0.6762	Remote Similarity	NPD855	Approved
0.6762	Remote Similarity	NPD854	Approved
0.6762	Remote Similarity	NPD4817	Approved
0.6754	Remote Similarity	NPD1758	Phase 1
0.6752	Remote Similarity	NPD1535	Discovery
0.6752	Remote Similarity	NPD1610	Phase 2
0.675	Remote Similarity	NPD6584	Phase 3
0.675	Remote Similarity	NPD7451	Discontinued
0.6724	Remote Similarity	NPD1778	Approved
0.6723	Remote Similarity	NPD5311	Approved
0.6723	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD5310	Approved
0.6721	Remote Similarity	NPD5155	Approved
0.6721	Remote Similarity	NPD5156	Approved
0.6702	Remote Similarity	NPD9250	Approved
0.67	Remote Similarity	NPD9365	Approved
0.6698	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD1241	Discontinued
0.6695	Remote Similarity	NPD1481	Phase 2
0.6695	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3596	Phase 2
0.6667	Remote Similarity	NPD3496	Discontinued
0.6667	Remote Similarity	NPD3026	Approved
0.6667	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7636	Approved
0.6667	Remote Similarity	NPD3023	Approved
0.6667	Remote Similarity	NPD1616	Discontinued
0.6667	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1981	Approved
0.6667	Remote Similarity	NPD1983	Approved
0.6667	Remote Similarity	NPD1980	Approved
0.6639	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD3685	Discontinued
0.6639	Remote Similarity	NPD4908	Phase 1
0.6639	Remote Similarity	NPD3594	Approved
0.6639	Remote Similarity	NPD3595	Approved
0.6638	Remote Similarity	NPD3025	Approved
0.6638	Remote Similarity	NPD3024	Approved
0.6635	Remote Similarity	NPD9495	Approved
0.6613	Remote Similarity	NPD6663	Approved
0.6612	Remote Similarity	NPD9621	Approved
0.6612	Remote Similarity	NPD4624	Approved
0.6612	Remote Similarity	NPD257	Approved
0.6612	Remote Similarity	NPD258	Approved
0.6612	Remote Similarity	NPD9619	Approved
0.6612	Remote Similarity	NPD9620	Approved
0.6609	Remote Similarity	NPD5536	Phase 2
0.6607	Remote Similarity	NPD1138	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