NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	230.17
Volume:	272.344
LogP:	5.521
LogD:	4.324
LogS:	-5.294
# Rotatable Bonds:	4
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.762
Synthetic Accessibility Score:	2.761
Fsp3:	0.375
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:	-4.63
MDCK Permeability:	2.1779551389045082e-05
Pgp-inhibitor:	0.775
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.876
30% Bioavailability (F30%):	0.692

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.113
Plasma Protein Binding (PPB):	99.21324920654297%
Volume Distribution (VD):	5.131
Pgp-substrate:	3.377493143081665%

ADMET: Metabolism

CYP1A2-inhibitor:	0.948
CYP1A2-substrate:	0.446
CYP2C19-inhibitor:	0.917
CYP2C19-substrate:	0.446
CYP2C9-inhibitor:	0.706
CYP2C9-substrate:	0.922
CYP2D6-inhibitor:	0.918
CYP2D6-substrate:	0.863
CYP3A4-inhibitor:	0.646
CYP3A4-substrate:	0.334

ADMET: Excretion

Clearance (CL):	5.283
Half-life (T1/2):	0.18

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.169
Drug-inuced Liver Injury (DILI):	0.024
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.057
Maximum Recommended Daily Dose:	0.154
Skin Sensitization:	0.628
Carcinogencity:	0.103
Eye Corrosion:	0.795
Eye Irritation:	0.979
Respiratory Toxicity:	0.164

Download Data

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

Natural Product: NPC225506

Natural Product ID:	NPC225506
*Common Name:**	4-(2-Methylbut-3-En-2-Yl)-2-(3-Methylbut-2-Enyl)Phenol
IUPAC Name:	4-(2-methylbut-3-en-2-yl)-2-(3-methylbut-2-enyl)phenol
Synonyms:
Standard InCHIKey:	VOZHPGWGKPWOGA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H22O/c1-6-16(4,5)14-9-10-15(17)13(11-14)8-7-12(2)3/h6-7,9-11,17H,1,8H2,2-5H3
SMILES:	C=CC(c1ccc(c(c1)CC=C(C)C)O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL251493
PubChem CID:	333664
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0002811] Phenylpropanes

*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
NPO30938	Perithalia capillaris	Species	Sporochnaceae	Eukaryota	n.a.	New Zealand	n.a.	PMID[18052030]
NPO30938	Perithalia capillaris	Species	Sporochnaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21348445]
NPO16734	Perithalia caudata	Species	Sporochnaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21348445]
NPO16286	Sporochnus comosus	Species	Sporochnaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21348445]
NPO30967	Sporochnus pedunculatus	Species	Sporochnaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21348445]
NPO5730	Lactuca canadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17827	Scutellaria przewalskii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5730	Lactuca canadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17845	Rhynchotechum vestitum	Species	Gesneriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17827	Scutellaria przewalskii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17714	Blepharispermum zanguebaricum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16734	Perithalia caudata	Species	Sporochnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17950	Siphonoglossa ramosa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO5730	Lactuca canadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1266	Trigonella polycerata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14726	Alnus subcordata	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13576	Cordylanthus tenuis	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13944	Parkia speciosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17183	Chaetomium coarctatum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17845	Rhynchotechum vestitum	Species	Gesneriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17827	Scutellaria przewalskii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16286	Sporochnus comosus	Species	Sporochnaceae	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	5
IC50	2

Activity Type	# Activity
Cell Line	6
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	2700.0	nM	PMID[476676]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	=	39000.0	nM	PMID[476677]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	27000.0	nM	PMID[476677]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	=	37000.0	nM	PMID[476677]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	=	57000.0	nM	PMID[476677]
NPT913	Cell Line	CHO-K1	Cricetulus griseus	GI50	=	29000.0	nM	PMID[476677]
NPT2	Others	Unspecified		IC50	=	29000.0	nM	PMID[476676]

☑ 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 NPC225506 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	303
0.1-0.2	1887
0.2-0.3	4494
0.3-0.4	13191
0.4-0.5	7045
0.5-0.6	9729
0.6-0.7	4704
0.7-0.8	1033
0.8-0.85	194
0.85-0.9	86
0.9-0.95	23
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9892	High Similarity	NPC122005
0.9892	High Similarity	NPC252821
0.9574	High Similarity	NPC77492
0.957	High Similarity	NPC144682
0.9462	High Similarity	NPC289769
0.9462	High Similarity	NPC27323
0.9462	High Similarity	NPC316301
0.9462	High Similarity	NPC152415
0.9362	High Similarity	NPC8392
0.9247	High Similarity	NPC306074
0.9247	High Similarity	NPC204210
0.9247	High Similarity	NPC155908
0.9192	High Similarity	NPC138942
0.9184	High Similarity	NPC168829
0.9175	High Similarity	NPC211885
0.9167	High Similarity	NPC225464
0.9158	High Similarity	NPC222146
0.9118	High Similarity	NPC13482
0.91	High Similarity	NPC271274
0.9091	High Similarity	NPC288411
0.9082	High Similarity	NPC252105
0.9072	High Similarity	NPC299762
0.9072	High Similarity	NPC33675
0.9072	High Similarity	NPC92730
0.9072	High Similarity	NPC128723
0.9043	High Similarity	NPC304541
0.9032	High Similarity	NPC280347
0.9032	High Similarity	NPC123273
0.9032	High Similarity	NPC70436
0.9032	High Similarity	NPC177420
0.9032	High Similarity	NPC318325
0.9032	High Similarity	NPC98772
0.9032	High Similarity	NPC242240
0.9	High Similarity	NPC99557
0.9	High Similarity	NPC219286
0.899	High Similarity	NPC269212
0.8947	High Similarity	NPC55903
0.8942	High Similarity	NPC250323
0.8942	High Similarity	NPC228425
0.8936	High Similarity	NPC55561
0.8932	High Similarity	NPC141782
0.8925	High Similarity	NPC25493
0.8925	High Similarity	NPC113460
0.8922	High Similarity	NPC470039
0.8846	High Similarity	NPC176279
0.8846	High Similarity	NPC260323
0.8842	High Similarity	NPC270547
0.883	High Similarity	NPC258219
0.8824	High Similarity	NPC151477
0.8817	High Similarity	NPC184169
0.8817	High Similarity	NPC23167
0.8817	High Similarity	NPC307235
0.8817	High Similarity	NPC407
0.8812	High Similarity	NPC47284
0.88	High Similarity	NPC108497
0.8776	High Similarity	NPC79241
0.8776	High Similarity	NPC6597
0.8774	High Similarity	NPC195922
0.8763	High Similarity	NPC26244
0.875	High Similarity	NPC162314
0.875	High Similarity	NPC296683
0.875	High Similarity	NPC306884
0.875	High Similarity	NPC147284
0.875	High Similarity	NPC210497
0.875	High Similarity	NPC94139
0.875	High Similarity	NPC3358
0.8738	High Similarity	NPC262365
0.8737	High Similarity	NPC192
0.8725	High Similarity	NPC21594
0.8725	High Similarity	NPC53740
0.8725	High Similarity	NPC477814
0.871	High Similarity	NPC197783
0.871	High Similarity	NPC155393
0.87	High Similarity	NPC51015
0.8673	High Similarity	NPC292730
0.8673	High Similarity	NPC216520
0.8673	High Similarity	NPC82664
0.8673	High Similarity	NPC132271
0.8673	High Similarity	NPC312132
0.8673	High Similarity	NPC473388
0.8673	High Similarity	NPC259512
0.8667	High Similarity	NPC95716
0.866	High Similarity	NPC245187
0.866	High Similarity	NPC151715
0.866	High Similarity	NPC128062
0.8654	High Similarity	NPC58865
0.8641	High Similarity	NPC320439
0.8641	High Similarity	NPC228737
0.8627	High Similarity	NPC303141
0.8627	High Similarity	NPC243677
0.8627	High Similarity	NPC117115
0.8602	High Similarity	NPC286904
0.8602	High Similarity	NPC175313
0.8602	High Similarity	NPC248817
0.86	High Similarity	NPC48730
0.86	High Similarity	NPC72729
0.86	High Similarity	NPC248396
0.86	High Similarity	NPC129373
0.8598	High Similarity	NPC268160
0.8586	High Similarity	NPC152097
0.8585	High Similarity	NPC46940
0.8571	High Similarity	NPC44732
0.8558	High Similarity	NPC61885
0.8558	High Similarity	NPC63698
0.8557	High Similarity	NPC271440
0.8544	High Similarity	NPC155072
0.8544	High Similarity	NPC54765
0.8544	High Similarity	NPC310456
0.8532	High Similarity	NPC477136
0.8529	High Similarity	NPC120719
0.8526	High Similarity	NPC27974
0.8526	High Similarity	NPC19680
0.8519	High Similarity	NPC192948
0.8519	High Similarity	NPC147179
0.8519	High Similarity	NPC35797
0.8515	High Similarity	NPC101025
0.8515	High Similarity	NPC471578
0.8505	High Similarity	NPC141003
0.8505	High Similarity	NPC35344
0.8505	High Similarity	NPC715
0.85	High Similarity	NPC260775
0.8495	Intermediate Similarity	NPC265146
0.8495	Intermediate Similarity	NPC124436
0.8491	Intermediate Similarity	NPC476632
0.8491	Intermediate Similarity	NPC322753
0.8491	Intermediate Similarity	NPC165770
0.8491	Intermediate Similarity	NPC308689
0.8491	Intermediate Similarity	NPC266937
0.8491	Intermediate Similarity	NPC225679
0.8491	Intermediate Similarity	NPC4493
0.8491	Intermediate Similarity	NPC77772
0.8491	Intermediate Similarity	NPC470770
0.8469	Intermediate Similarity	NPC76938
0.8454	Intermediate Similarity	NPC231150
0.8454	Intermediate Similarity	NPC45040
0.844	Intermediate Similarity	NPC308311
0.844	Intermediate Similarity	NPC38893
0.844	Intermediate Similarity	NPC471668
0.844	Intermediate Similarity	NPC477137
0.844	Intermediate Similarity	NPC219112
0.844	Intermediate Similarity	NPC308828
0.8431	Intermediate Similarity	NPC62351
0.8431	Intermediate Similarity	NPC470202
0.8426	Intermediate Similarity	NPC107240
0.8426	Intermediate Similarity	NPC12656
0.8416	Intermediate Similarity	NPC130756
0.8416	Intermediate Similarity	NPC12931
0.8416	Intermediate Similarity	NPC70677
0.8411	Intermediate Similarity	NPC43525
0.8411	Intermediate Similarity	NPC228988
0.8411	Intermediate Similarity	NPC62867
0.8411	Intermediate Similarity	NPC286222
0.8411	Intermediate Similarity	NPC177962
0.84	Intermediate Similarity	NPC475078
0.8384	Intermediate Similarity	NPC274678
0.8384	Intermediate Similarity	NPC32714
0.8381	Intermediate Similarity	NPC95344
0.8381	Intermediate Similarity	NPC306295
0.8381	Intermediate Similarity	NPC64586
0.8381	Intermediate Similarity	NPC11554
0.8367	Intermediate Similarity	NPC138117
0.8367	Intermediate Similarity	NPC325292
0.8365	Intermediate Similarity	NPC469913
0.8364	Intermediate Similarity	NPC16030
0.8364	Intermediate Similarity	NPC304510
0.8364	Intermediate Similarity	NPC172219
0.8351	Intermediate Similarity	NPC300017
0.835	Intermediate Similarity	NPC272029
0.835	Intermediate Similarity	NPC475225
0.835	Intermediate Similarity	NPC238696
0.8349	Intermediate Similarity	NPC474486
0.8333	Intermediate Similarity	NPC472585
0.8333	Intermediate Similarity	NPC263753
0.8333	Intermediate Similarity	NPC477685
0.8333	Intermediate Similarity	NPC117846
0.8318	Intermediate Similarity	NPC151537
0.8317	Intermediate Similarity	NPC80027
0.8317	Intermediate Similarity	NPC216468
0.8317	Intermediate Similarity	NPC78119
0.8317	Intermediate Similarity	NPC132078
0.8317	Intermediate Similarity	NPC51333
0.8304	Intermediate Similarity	NPC475245
0.8302	Intermediate Similarity	NPC314187
0.8302	Intermediate Similarity	NPC75272
0.8302	Intermediate Similarity	NPC471954
0.83	Intermediate Similarity	NPC202986
0.8288	Intermediate Similarity	NPC471671
0.8288	Intermediate Similarity	NPC469609
0.8288	Intermediate Similarity	NPC154030
0.8273	Intermediate Similarity	NPC137496
0.8273	Intermediate Similarity	NPC92
0.8273	Intermediate Similarity	NPC247858
0.8273	Intermediate Similarity	NPC141001
0.8273	Intermediate Similarity	NPC257540
0.8273	Intermediate Similarity	NPC474358
0.8273	Intermediate Similarity	NPC474387
0.8273	Intermediate Similarity	NPC154511
0.8273	Intermediate Similarity	NPC469663
0.8269	Intermediate Similarity	NPC474839
0.8257	Intermediate Similarity	NPC473137

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 NPC225506 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	316
0.1-0.2	1060
0.2-0.3	1366
0.3-0.4	2890
0.4-0.5	1897
0.5-0.6	1116
0.6-0.7	410
0.7-0.8	78
0.8-0.85	8
0.85-0.9	6
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.957	High Similarity	NPD1809	Phase 2
0.9462	High Similarity	NPD1432	Clinical (unspecified phase)
0.9149	High Similarity	NPD845	Approved
0.8878	High Similarity	NPD3020	Approved
0.8788	High Similarity	NPD289	Clinical (unspecified phase)
0.8763	High Similarity	NPD2859	Approved
0.8763	High Similarity	NPD844	Approved
0.8763	High Similarity	NPD2860	Approved
0.8673	High Similarity	NPD288	Approved
0.866	High Similarity	NPD2933	Approved
0.866	High Similarity	NPD2934	Approved
0.8515	High Similarity	NPD940	Approved
0.8515	High Similarity	NPD846	Approved
0.8495	Intermediate Similarity	NPD111	Approved
0.8491	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.8304	Intermediate Similarity	NPD4589	Approved
0.8131	Intermediate Similarity	NPD3022	Approved
0.8131	Intermediate Similarity	NPD3021	Approved
0.8113	Intermediate Similarity	NPD2342	Discontinued
0.8073	Intermediate Similarity	NPD7635	Approved
0.7965	Intermediate Similarity	NPD3091	Approved
0.7965	Intermediate Similarity	NPD5303	Approved
0.7965	Intermediate Similarity	NPD5304	Approved
0.7963	Intermediate Similarity	NPD4750	Phase 3
0.7895	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.785	Intermediate Similarity	NPD1445	Approved
0.785	Intermediate Similarity	NPD1444	Approved
0.7838	Intermediate Similarity	NPD2229	Approved
0.7838	Intermediate Similarity	NPD2228	Approved
0.7838	Intermediate Similarity	NPD2234	Approved
0.7826	Intermediate Similarity	NPD3019	Approved
0.7826	Intermediate Similarity	NPD2932	Approved
0.7826	Intermediate Similarity	NPD4059	Approved
0.7759	Intermediate Similarity	NPD2688	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD3143	Discontinued
0.7712	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD3092	Approved
0.7672	Intermediate Similarity	NPD4626	Approved
0.7672	Intermediate Similarity	NPD1751	Approved
0.7664	Intermediate Similarity	NPD9608	Approved
0.7664	Intermediate Similarity	NPD9610	Approved
0.7652	Intermediate Similarity	NPD7330	Discontinued
0.7636	Intermediate Similarity	NPD1792	Phase 2
0.7627	Intermediate Similarity	NPD3070	Discontinued
0.7611	Intermediate Similarity	NPD1793	Approved
0.7611	Intermediate Similarity	NPD1791	Approved
0.7586	Intermediate Similarity	NPD4093	Discontinued
0.757	Intermediate Similarity	NPD9500	Approved
0.7547	Intermediate Similarity	NPD3028	Approved
0.7547	Intermediate Similarity	NPD1242	Phase 1
0.7544	Intermediate Similarity	NPD7157	Approved
0.7544	Intermediate Similarity	NPD6671	Approved
0.7521	Intermediate Similarity	NPD3095	Discontinued
0.7478	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7478	Intermediate Similarity	NPD7636	Approved
0.7438	Intermediate Similarity	NPD3094	Phase 2
0.7387	Intermediate Similarity	NPD2684	Approved
0.7377	Intermediate Similarity	NPD2195	Approved
0.7377	Intermediate Similarity	NPD2194	Approved
0.7373	Intermediate Similarity	NPD2286	Discontinued
0.7358	Intermediate Similarity	NPD9273	Approved
0.7355	Intermediate Similarity	NPD6696	Suspended
0.735	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD228	Approved
0.7317	Intermediate Similarity	NPD4208	Discontinued
0.7317	Intermediate Similarity	NPD3636	Approved
0.7317	Intermediate Similarity	NPD3635	Approved
0.7317	Intermediate Similarity	NPD4212	Discontinued
0.7317	Intermediate Similarity	NPD3637	Approved
0.7317	Intermediate Similarity	NPD5736	Approved
0.7312	Intermediate Similarity	NPD9087	Approved
0.7288	Intermediate Similarity	NPD5691	Approved
0.728	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD2606	Approved
0.7258	Intermediate Similarity	NPD2605	Approved
0.7258	Intermediate Similarity	NPD4207	Discontinued
0.725	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD8651	Approved
0.72	Intermediate Similarity	NPD5156	Approved
0.72	Intermediate Similarity	NPD5155	Approved
0.7188	Intermediate Similarity	NPD4097	Suspended
0.7168	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD3023	Approved
0.7167	Intermediate Similarity	NPD3026	Approved
0.7165	Intermediate Similarity	NPD4060	Phase 1
0.7155	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD475	Phase 2
0.7155	Intermediate Similarity	NPD497	Approved
0.7154	Intermediate Similarity	NPD1164	Approved
0.7154	Intermediate Similarity	NPD1133	Approved
0.7154	Intermediate Similarity	NPD1135	Approved
0.7154	Intermediate Similarity	NPD1129	Approved
0.7154	Intermediate Similarity	NPD1131	Approved
0.7154	Intermediate Similarity	NPD1134	Approved
0.7143	Intermediate Similarity	NPD3024	Approved
0.7143	Intermediate Similarity	NPD3025	Approved
0.713	Intermediate Similarity	NPD9379	Approved
0.713	Intermediate Similarity	NPD1138	Approved
0.713	Intermediate Similarity	NPD7843	Approved
0.713	Intermediate Similarity	NPD9377	Approved
0.712	Intermediate Similarity	NPD4908	Phase 1
0.712	Intermediate Similarity	NPD3594	Approved
0.712	Intermediate Similarity	NPD3595	Approved
0.7107	Intermediate Similarity	NPD1610	Phase 2
0.7097	Intermediate Similarity	NPD4624	Approved
0.7097	Intermediate Similarity	NPD3690	Phase 2
0.7097	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD3691	Phase 2
0.7094	Intermediate Similarity	NPD255	Approved
0.7094	Intermediate Similarity	NPD256	Approved
0.7087	Intermediate Similarity	NPD6663	Approved
0.7083	Intermediate Similarity	NPD2668	Approved
0.7083	Intermediate Similarity	NPD2667	Approved
0.7083	Intermediate Similarity	NPD9294	Approved
0.7083	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD5283	Phase 1
0.7069	Intermediate Similarity	NPD496	Approved
0.7069	Intermediate Similarity	NPD495	Approved
0.7069	Intermediate Similarity	NPD498	Approved
0.7063	Intermediate Similarity	NPD4625	Phase 3
0.7043	Intermediate Similarity	NPD1139	Approved
0.7043	Intermediate Similarity	NPD1137	Approved
0.704	Intermediate Similarity	NPD2861	Phase 2
0.7018	Intermediate Similarity	NPD5451	Approved
0.7016	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD9088	Approved
0.7008	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD4749	Approved
0.6992	Remote Similarity	NPD1755	Approved
0.6991	Remote Similarity	NPD290	Approved
0.6983	Remote Similarity	NPD821	Approved
0.6975	Remote Similarity	NPD16	Approved
0.6975	Remote Similarity	NPD856	Approved
0.6967	Remote Similarity	NPD1201	Approved
0.6953	Remote Similarity	NPD6405	Approved
0.6953	Remote Similarity	NPD6407	Approved
0.6949	Remote Similarity	NPD6387	Discontinued
0.6923	Remote Similarity	NPD1398	Phase 1
0.6917	Remote Similarity	NPD1548	Phase 1
0.6911	Remote Similarity	NPD2230	Approved
0.6911	Remote Similarity	NPD2233	Approved
0.6911	Remote Similarity	NPD2232	Approved
0.6903	Remote Similarity	NPD968	Approved
0.6899	Remote Similarity	NPD3620	Phase 2
0.6899	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD7340	Approved
0.6891	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD3496	Discontinued
0.688	Remote Similarity	NPD4103	Phase 2
0.688	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD9618	Approved
0.6864	Remote Similarity	NPD9614	Approved
0.6863	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.686	Remote Similarity	NPD1651	Approved
0.686	Remote Similarity	NPD1357	Approved
0.6855	Remote Similarity	NPD4659	Approved
0.6855	Remote Similarity	NPD1669	Approved
0.6855	Remote Similarity	NPD6583	Phase 3
0.6855	Remote Similarity	NPD6582	Phase 2
0.6855	Remote Similarity	NPD5327	Phase 3
0.6847	Remote Similarity	NPD4817	Approved
0.6847	Remote Similarity	NPD4818	Approved
0.6842	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD5535	Approved
0.6833	Remote Similarity	NPD317	Approved
0.6833	Remote Similarity	NPD318	Approved
0.6829	Remote Similarity	NPD422	Phase 1
0.6825	Remote Similarity	NPD6584	Phase 3
0.6822	Remote Similarity	NPD4248	Discontinued
0.6818	Remote Similarity	NPD7743	Approved
0.6818	Remote Similarity	NPD7742	Approved
0.6815	Remote Similarity	NPD7003	Approved
0.681	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD709	Approved
0.6803	Remote Similarity	NPD1778	Approved
0.68	Remote Similarity	NPD1283	Approved
0.6797	Remote Similarity	NPD7095	Approved
0.6794	Remote Similarity	NPD2157	Approved
0.6783	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD74	Approved
0.6783	Remote Similarity	NPD9266	Approved
0.678	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD1759	Phase 1
0.6774	Remote Similarity	NPD2562	Approved
0.6774	Remote Similarity	NPD2561	Approved
0.6769	Remote Similarity	NPD4140	Approved
0.6767	Remote Similarity	NPD2935	Discontinued
0.6757	Remote Similarity	NPD1616	Discontinued
0.6754	Remote Similarity	NPD3134	Approved
0.675	Remote Similarity	NPD9493	Approved
0.675	Remote Similarity	NPD9568	Approved
0.6748	Remote Similarity	NPD1981	Approved
0.6748	Remote Similarity	NPD3847	Discontinued
0.6748	Remote Similarity	NPD3421	Phase 3
0.6748	Remote Similarity	NPD1983	Approved
0.6748	Remote Similarity	NPD1980	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