NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	242.09
Volume:	258.799
LogP:	3.689
LogD:	3.307
LogS:	-2.964
# Rotatable Bonds:	3
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.572
Synthetic Accessibility Score:	2.338
Fsp3:	0.067
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.653
MDCK Permeability:	1.758849793986883e-05
Pgp-inhibitor:	0.067
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.983
30% Bioavailability (F30%):	0.981

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.05
Plasma Protein Binding (PPB):	99.29759216308594%
Volume Distribution (VD):	0.441
Pgp-substrate:	1.2067123651504517%

ADMET: Metabolism

CYP1A2-inhibitor:	0.939
CYP1A2-substrate:	0.266
CYP2C19-inhibitor:	0.785
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.598
CYP2C9-substrate:	0.931
CYP2D6-inhibitor:	0.937
CYP2D6-substrate:	0.924
CYP3A4-inhibitor:	0.635
CYP3A4-substrate:	0.199

ADMET: Excretion

Clearance (CL):	15.114
Half-life (T1/2):	0.856

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.039
Drug-inuced Liver Injury (DILI):	0.043
AMES Toxicity:	0.572
Rat Oral Acute Toxicity:	0.245
Maximum Recommended Daily Dose:	0.328
Skin Sensitization:	0.941
Carcinogencity:	0.383
Eye Corrosion:	0.05
Eye Irritation:	0.955
Respiratory Toxicity:	0.119

Download Data

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

Natural Product: NPC95344

Natural Product ID:	NPC95344
*Common Name:**	Randaiol
IUPAC Name:	2-(2-hydroxy-5-prop-2-enylphenyl)benzene-1,4-diol
Synonyms:	Randaiol
Standard InCHIKey:	KIQCVMGDSBIIGW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H14O3/c1-2-3-10-4-6-14(17)12(8-10)13-9-11(16)5-7-15(13)18/h2,4-9,16-18H,1,3H2
SMILES:	C=CCc1ccc(c(c1)c1cc(ccc1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL555924
PubChem CID:	13337243
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000325] Biphenols

*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
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1659613]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[17918910]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	Stems; Barks	n.a.	n.a.	PMID[19086868]
NPO28043	Streblus asper	Species	Moraceae	Eukaryota	Roots	n.a.	n.a.	PMID[23434030]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	bark	n.a.	PMID[23823874]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28485933]
NPO28043	Streblus asper	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[4093781]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3091	Sassafras randainense	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3091	Sassafras randainense	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO31493	Sassafras randalnense	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28043	Streblus asper	Species	Moraceae	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
IC50	8
Others	3

Activity Type	# Activity
Cell Line	3
CELL-LINE	1
Organism	3
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	1.2	ug.mL-1	PMID[541939]
NPT2341	Cell Line	NCI-H1975	Homo sapiens	IC50	>	40000.0	nM	PMID[541941]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	>	40000.0	nM	PMID[541941]
NPT1	Others	Radical scavenging activity		IC50	=	21.6	ug.mL-1	PMID[541939]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	>	1000000.0	nM	PMID[541940]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	6.63	n.a.	PMID[541940]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	=	30240.0	nM	PMID[541940]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	1.23	n.a.	PMID[541940]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	=	162430.0	nM	PMID[541940]
NPT27	Others	Unspecified		CC50	=	200570.0	nM	PMID[541940]
NPT22158	CELL-LINE	HCC827	Homo sapiens	IC50	>	40000.0	nM	PMID[541941]

☑ 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 NPC95344 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	448
0.1-0.2	2047
0.2-0.3	5600
0.3-0.4	13267
0.4-0.5	4976
0.5-0.6	8091
0.6-0.7	6284
0.7-0.8	1687
0.8-0.85	217
0.85-0.9	74
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.98	High Similarity	NPC54765
0.9216	High Similarity	NPC288411
0.9208	High Similarity	NPC12221
0.9126	High Similarity	NPC138942
0.9118	High Similarity	NPC233827
0.9118	High Similarity	NPC168829
0.8972	High Similarity	NPC151537
0.89	High Similarity	NPC274678
0.8868	High Similarity	NPC262365
0.8857	High Similarity	NPC67250
0.88	High Similarity	NPC128062
0.8796	High Similarity	NPC476632
0.8796	High Similarity	NPC95716
0.8796	High Similarity	NPC225679
0.8796	High Similarity	NPC4493
0.8796	High Similarity	NPC165770
0.8785	High Similarity	NPC202647
0.8785	High Similarity	NPC314187
0.8785	High Similarity	NPC58865
0.875	High Similarity	NPC269212
0.875	High Similarity	NPC108497
0.8738	High Similarity	NPC130103
0.8727	High Similarity	NPC12656
0.8727	High Similarity	NPC473137
0.8727	High Similarity	NPC107240
0.8725	High Similarity	NPC156313
0.8725	High Similarity	NPC32674
0.8716	High Similarity	NPC43525
0.8716	High Similarity	NPC46940
0.8704	High Similarity	NPC296683
0.87	High Similarity	NPC271440
0.8679	High Similarity	NPC469913
0.8679	High Similarity	NPC248904
0.8667	High Similarity	NPC238696
0.8667	High Similarity	NPC30506
0.8667	High Similarity	NPC272029
0.8667	High Similarity	NPC102216
0.8636	High Similarity	NPC117846
0.8624	High Similarity	NPC308689
0.86	High Similarity	NPC45040
0.8598	High Similarity	NPC320439
0.8596	High Similarity	NPC475245
0.8585	High Similarity	NPC99557
0.8585	High Similarity	NPC219286
0.8585	High Similarity	NPC292452
0.8571	High Similarity	NPC141001
0.8571	High Similarity	NPC168393
0.8559	High Similarity	NPC249270
0.8558	High Similarity	NPC248396
0.8558	High Similarity	NPC129373
0.8558	High Similarity	NPC48730
0.8545	High Similarity	NPC286222
0.8544	High Similarity	NPC152097
0.8544	High Similarity	NPC77492
0.8532	High Similarity	NPC44732
0.8529	High Similarity	NPC8392
0.8519	High Similarity	NPC233835
0.8519	High Similarity	NPC61885
0.8519	High Similarity	NPC63698
0.8515	High Similarity	NPC29373
0.8509	High Similarity	NPC176893
0.8505	High Similarity	NPC271274
0.8496	Intermediate Similarity	NPC299180
0.8496	Intermediate Similarity	NPC470760
0.8491	Intermediate Similarity	NPC254965
0.8491	Intermediate Similarity	NPC475580
0.8491	Intermediate Similarity	NPC119860
0.8491	Intermediate Similarity	NPC327811
0.8476	Intermediate Similarity	NPC100340
0.8476	Intermediate Similarity	NPC143659
0.8468	Intermediate Similarity	NPC715
0.8468	Intermediate Similarity	NPC322239
0.8462	Intermediate Similarity	NPC122005
0.8462	Intermediate Similarity	NPC260775
0.8462	Intermediate Similarity	NPC92730
0.8462	Intermediate Similarity	NPC252821
0.8455	Intermediate Similarity	NPC470770
0.8455	Intermediate Similarity	NPC469912
0.8455	Intermediate Similarity	NPC266937
0.8455	Intermediate Similarity	NPC54373
0.8455	Intermediate Similarity	NPC77772
0.8447	Intermediate Similarity	NPC132271
0.8447	Intermediate Similarity	NPC216520
0.8447	Intermediate Similarity	NPC82664
0.8447	Intermediate Similarity	NPC292730
0.8431	Intermediate Similarity	NPC76938
0.8431	Intermediate Similarity	NPC151715
0.8426	Intermediate Similarity	NPC151477
0.8416	Intermediate Similarity	NPC204210
0.8411	Intermediate Similarity	NPC47284
0.8411	Intermediate Similarity	NPC239291
0.8411	Intermediate Similarity	NPC474839
0.8407	Intermediate Similarity	NPC115808
0.8407	Intermediate Similarity	NPC261973
0.8393	Intermediate Similarity	NPC195922
0.8393	Intermediate Similarity	NPC471534
0.8381	Intermediate Similarity	NPC70677
0.8381	Intermediate Similarity	NPC225506
0.8381	Intermediate Similarity	NPC275053
0.8381	Intermediate Similarity	NPC248573
0.8381	Intermediate Similarity	NPC161571
0.8381	Intermediate Similarity	NPC130756
0.8381	Intermediate Similarity	NPC12931
0.8378	Intermediate Similarity	NPC228988
0.8378	Intermediate Similarity	NPC62867
0.8378	Intermediate Similarity	NPC166995
0.8378	Intermediate Similarity	NPC177962
0.8365	Intermediate Similarity	NPC475078
0.8365	Intermediate Similarity	NPC225464
0.8364	Intermediate Similarity	NPC224870
0.8364	Intermediate Similarity	NPC13482
0.8362	Intermediate Similarity	NPC129176
0.835	Intermediate Similarity	NPC32714
0.835	Intermediate Similarity	NPC26244
0.8349	Intermediate Similarity	NPC174981
0.8349	Intermediate Similarity	NPC11554
0.8333	Intermediate Similarity	NPC155072
0.8333	Intermediate Similarity	NPC53740
0.8333	Intermediate Similarity	NPC21594
0.8319	Intermediate Similarity	NPC232165
0.8318	Intermediate Similarity	NPC241891
0.8318	Intermediate Similarity	NPC323810
0.8318	Intermediate Similarity	NPC471511
0.8304	Intermediate Similarity	NPC141003
0.8304	Intermediate Similarity	NPC35344
0.8304	Intermediate Similarity	NPC471485
0.8302	Intermediate Similarity	NPC477685
0.8288	Intermediate Similarity	NPC224527
0.8286	Intermediate Similarity	NPC128723
0.8276	Intermediate Similarity	NPC223451
0.8273	Intermediate Similarity	NPC473524
0.8273	Intermediate Similarity	NPC33728
0.8273	Intermediate Similarity	NPC19808
0.8269	Intermediate Similarity	NPC312132
0.8269	Intermediate Similarity	NPC259512
0.8269	Intermediate Similarity	NPC473388
0.8261	Intermediate Similarity	NPC469609
0.8252	Intermediate Similarity	NPC245187
0.8241	Intermediate Similarity	NPC117115
0.8241	Intermediate Similarity	NPC134829
0.8235	Intermediate Similarity	NPC304541
0.8218	Intermediate Similarity	NPC70436
0.8214	Intermediate Similarity	NPC250323
0.8214	Intermediate Similarity	NPC302371
0.8214	Intermediate Similarity	NPC228425
0.8208	Intermediate Similarity	NPC211885
0.8208	Intermediate Similarity	NPC294741
0.8208	Intermediate Similarity	NPC72729
0.8208	Intermediate Similarity	NPC174911
0.8205	Intermediate Similarity	NPC277798
0.8205	Intermediate Similarity	NPC100108
0.8198	Intermediate Similarity	NPC141782
0.8198	Intermediate Similarity	NPC132720
0.819	Intermediate Similarity	NPC88420
0.819	Intermediate Similarity	NPC291789
0.819	Intermediate Similarity	NPC6597
0.819	Intermediate Similarity	NPC79241
0.819	Intermediate Similarity	NPC469644
0.819	Intermediate Similarity	NPC151197
0.8182	Intermediate Similarity	NPC279887
0.8182	Intermediate Similarity	NPC169450
0.8182	Intermediate Similarity	NPC68260
0.8174	Intermediate Similarity	NPC304510
0.8174	Intermediate Similarity	NPC172219
0.8174	Intermediate Similarity	NPC277588
0.8173	Intermediate Similarity	NPC144682
0.8173	Intermediate Similarity	NPC222146
0.8167	Intermediate Similarity	NPC28476
0.8167	Intermediate Similarity	NPC133407
0.8165	Intermediate Similarity	NPC39664
0.8165	Intermediate Similarity	NPC39097
0.8165	Intermediate Similarity	NPC118286
0.8165	Intermediate Similarity	NPC470700
0.8165	Intermediate Similarity	NPC109691
0.8165	Intermediate Similarity	NPC302681
0.8158	Intermediate Similarity	NPC246760
0.8158	Intermediate Similarity	NPC84999
0.8155	Intermediate Similarity	NPC55903
0.8148	Intermediate Similarity	NPC475225
0.8142	Intermediate Similarity	NPC321589
0.8142	Intermediate Similarity	NPC263753
0.8142	Intermediate Similarity	NPC261343
0.8137	Intermediate Similarity	NPC192
0.8136	Intermediate Similarity	NPC237667
0.8136	Intermediate Similarity	NPC31936
0.8131	Intermediate Similarity	NPC51015
0.8131	Intermediate Similarity	NPC80800
0.8125	Intermediate Similarity	NPC176279
0.8125	Intermediate Similarity	NPC268032
0.8125	Intermediate Similarity	NPC260323
0.812	Intermediate Similarity	NPC472071
0.8119	Intermediate Similarity	NPC27974
0.8119	Intermediate Similarity	NPC19680
0.8113	Intermediate Similarity	NPC78119
0.8113	Intermediate Similarity	NPC33675
0.8113	Intermediate Similarity	NPC132078
0.8113	Intermediate Similarity	NPC216468
0.8113	Intermediate Similarity	NPC299762
0.8113	Intermediate Similarity	NPC51333
0.8113	Intermediate Similarity	NPC80027

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 NPC95344 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	430
0.1-0.2	1014
0.2-0.3	1396
0.3-0.4	3002
0.4-0.5	1755
0.5-0.6	1076
0.6-0.7	391
0.7-0.8	68
0.8-0.85	14
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8738	High Similarity	NPD289	Clinical (unspecified phase)
0.8716	High Similarity	NPD7635	Approved
0.8462	Intermediate Similarity	NPD3020	Approved
0.8426	Intermediate Similarity	NPD2342	Discontinued
0.8381	Intermediate Similarity	NPD1242	Phase 1
0.835	Intermediate Similarity	NPD2859	Approved
0.835	Intermediate Similarity	NPD2860	Approved
0.8269	Intermediate Similarity	NPD288	Approved
0.8252	Intermediate Similarity	NPD2933	Approved
0.8252	Intermediate Similarity	NPD2934	Approved
0.8173	Intermediate Similarity	NPD844	Approved
0.8173	Intermediate Similarity	NPD1809	Phase 2
0.8155	Intermediate Similarity	NPD845	Approved
0.8131	Intermediate Similarity	NPD846	Approved
0.8131	Intermediate Similarity	NPD940	Approved
0.8108	Intermediate Similarity	NPD3021	Approved
0.8108	Intermediate Similarity	NPD3022	Approved
0.8077	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD497	Approved
0.7982	Intermediate Similarity	NPD496	Approved
0.7982	Intermediate Similarity	NPD498	Approved
0.7982	Intermediate Similarity	NPD495	Approved
0.7946	Intermediate Similarity	NPD4750	Phase 3
0.7886	Intermediate Similarity	NPD2861	Phase 2
0.7815	Intermediate Similarity	NPD2286	Discontinued
0.7723	Intermediate Similarity	NPD111	Approved
0.7705	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6671	Approved
0.7686	Intermediate Similarity	NPD1201	Approved
0.7607	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD1610	Phase 2
0.7522	Intermediate Similarity	NPD968	Approved
0.7521	Intermediate Similarity	NPD4589	Approved
0.75	Intermediate Similarity	NPD5304	Approved
0.75	Intermediate Similarity	NPD5303	Approved
0.75	Intermediate Similarity	NPD3091	Approved
0.748	Intermediate Similarity	NPD4625	Phase 3
0.7478	Intermediate Similarity	NPD1792	Phase 2
0.744	Intermediate Similarity	NPD1470	Approved
0.744	Intermediate Similarity	NPD1164	Approved
0.7438	Intermediate Similarity	NPD4093	Discontinued
0.7402	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD3092	Approved
0.7398	Intermediate Similarity	NPD1611	Approved
0.7377	Intermediate Similarity	NPD3019	Approved
0.7377	Intermediate Similarity	NPD2932	Approved
0.7377	Intermediate Similarity	NPD4059	Approved
0.7373	Intermediate Similarity	NPD2229	Approved
0.7373	Intermediate Similarity	NPD2228	Approved
0.7373	Intermediate Similarity	NPD2234	Approved
0.7368	Intermediate Similarity	NPD1444	Approved
0.7368	Intermediate Similarity	NPD1445	Approved
0.736	Intermediate Similarity	NPD6696	Suspended
0.7355	Intermediate Similarity	NPD1548	Phase 1
0.735	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD3094	Phase 2
0.7302	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD9500	Approved
0.725	Intermediate Similarity	NPD709	Approved
0.7236	Intermediate Similarity	NPD4626	Approved
0.7236	Intermediate Similarity	NPD1751	Approved
0.7232	Intermediate Similarity	NPD3028	Approved
0.7227	Intermediate Similarity	NPD1398	Phase 1
0.7227	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1283	Approved
0.7203	Intermediate Similarity	NPD228	Approved
0.72	Intermediate Similarity	NPD9088	Approved
0.719	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD4060	Phase 1
0.7176	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD1613	Approved
0.7164	Intermediate Similarity	NPD5405	Approved
0.7164	Intermediate Similarity	NPD5406	Approved
0.7164	Intermediate Similarity	NPD5404	Approved
0.7164	Intermediate Similarity	NPD2935	Discontinued
0.7164	Intermediate Similarity	NPD5408	Approved
0.7154	Intermediate Similarity	NPD1651	Approved
0.7143	Intermediate Similarity	NPD1669	Approved
0.7143	Intermediate Similarity	NPD9379	Approved
0.7143	Intermediate Similarity	NPD9377	Approved
0.7132	Intermediate Similarity	NPD4908	Phase 1
0.7099	Intermediate Similarity	NPD6407	Approved
0.7099	Intermediate Similarity	NPD6405	Approved
0.7097	Intermediate Similarity	NPD3095	Discontinued
0.7097	Intermediate Similarity	NPD9381	Approved
0.7097	Intermediate Similarity	NPD9384	Approved
0.7097	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5283	Phase 1
0.7077	Intermediate Similarity	NPD3027	Phase 3
0.7073	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7330	Discontinued
0.7054	Intermediate Similarity	NPD9273	Approved
0.7049	Intermediate Similarity	NPD7340	Approved
0.7049	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD943	Approved
0.7043	Intermediate Similarity	NPD9608	Approved
0.7043	Intermediate Similarity	NPD9610	Approved
0.7008	Intermediate Similarity	NPD4749	Approved
0.6985	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD1535	Discovery
0.6984	Remote Similarity	NPD1281	Approved
0.6957	Remote Similarity	NPD3400	Discontinued
0.6957	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD2233	Approved
0.6929	Remote Similarity	NPD7390	Discontinued
0.6929	Remote Similarity	NPD1481	Phase 2
0.6929	Remote Similarity	NPD2232	Approved
0.6929	Remote Similarity	NPD1608	Approved
0.6929	Remote Similarity	NPD2230	Approved
0.6923	Remote Similarity	NPD5736	Approved
0.6899	Remote Similarity	NPD1135	Approved
0.6899	Remote Similarity	NPD1134	Approved
0.6899	Remote Similarity	NPD1131	Approved
0.6899	Remote Similarity	NPD4103	Phase 2
0.6899	Remote Similarity	NPD1133	Approved
0.6899	Remote Similarity	NPD1129	Approved
0.6899	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD9614	Approved
0.6885	Remote Similarity	NPD1791	Approved
0.6885	Remote Similarity	NPD1793	Approved
0.6885	Remote Similarity	NPD9618	Approved
0.6884	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.688	Remote Similarity	NPD5691	Approved
0.688	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.688	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD9622	Approved
0.6875	Remote Similarity	NPD4659	Approved
0.6864	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.685	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.685	Remote Similarity	NPD422	Phase 1
0.685	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD2195	Approved
0.6846	Remote Similarity	NPD2194	Approved
0.6846	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD6584	Phase 3
0.6822	Remote Similarity	NPD5311	Approved
0.6822	Remote Similarity	NPD5310	Approved
0.6818	Remote Similarity	NPD5156	Approved
0.6818	Remote Similarity	NPD5155	Approved
0.6815	Remote Similarity	NPD4097	Suspended
0.68	Remote Similarity	NPD9087	Approved
0.6797	Remote Similarity	NPD2562	Approved
0.6797	Remote Similarity	NPD2561	Approved
0.6794	Remote Similarity	NPD3637	Approved
0.6794	Remote Similarity	NPD3635	Approved
0.6794	Remote Similarity	NPD3636	Approved
0.6791	Remote Similarity	NPD2238	Phase 2
0.6791	Remote Similarity	NPD1555	Discontinued
0.6791	Remote Similarity	NPD3059	Approved
0.6791	Remote Similarity	NPD3061	Approved
0.6791	Remote Similarity	NPD3062	Approved
0.6783	Remote Similarity	NPD1616	Discontinued
0.6772	Remote Similarity	NPD3496	Discontinued
0.6772	Remote Similarity	NPD3026	Approved
0.6772	Remote Similarity	NPD1981	Approved
0.6772	Remote Similarity	NPD1983	Approved
0.6772	Remote Similarity	NPD3143	Discontinued
0.6772	Remote Similarity	NPD3023	Approved
0.6772	Remote Similarity	NPD1980	Approved
0.6769	Remote Similarity	NPD3055	Approved
0.6769	Remote Similarity	NPD3053	Approved
0.6767	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD3764	Approved
0.6767	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD3553	Approved
0.6765	Remote Similarity	NPD3555	Approved
0.6765	Remote Similarity	NPD3552	Approved
0.6765	Remote Similarity	NPD3554	Approved
0.6762	Remote Similarity	NPD9089	Approved
0.6761	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.675	Remote Similarity	NPD5451	Approved
0.6748	Remote Similarity	NPD475	Phase 2
0.6746	Remote Similarity	NPD3025	Approved
0.6746	Remote Similarity	NPD3024	Approved
0.6742	Remote Similarity	NPD2606	Approved
0.6742	Remote Similarity	NPD3594	Approved
0.6742	Remote Similarity	NPD3595	Approved
0.6742	Remote Similarity	NPD2605	Approved
0.6739	Remote Similarity	NPD4721	Approved
0.6739	Remote Similarity	NPD4725	Approved
0.6739	Remote Similarity	NPD4726	Approved
0.672	Remote Similarity	NPD9613	Approved
0.672	Remote Similarity	NPD16	Approved
0.672	Remote Similarity	NPD318	Approved
0.672	Remote Similarity	NPD856	Approved
0.672	Remote Similarity	NPD9616	Approved
0.672	Remote Similarity	NPD317	Approved
0.672	Remote Similarity	NPD9615	Approved
0.6718	Remote Similarity	NPD9621	Approved
0.6718	Remote Similarity	NPD4624	Approved
0.6718	Remote Similarity	NPD9619	Approved
0.6718	Remote Similarity	NPD9620	Approved
0.6716	Remote Similarity	NPD6663	Approved
0.6694	Remote Similarity	NPD255	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