NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	230.09
Volume:	244.139
LogP:	2.804
LogD:	3.17
LogS:	-2.087
# 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:	0.759
Synthetic Accessibility Score:	2.052
Fsp3:	0.143
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.901
MDCK Permeability:	1.5070801055117045e-05
Pgp-inhibitor:	0.281
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.077
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.06
Plasma Protein Binding (PPB):	94.64918518066406%
Volume Distribution (VD):	1.0
Pgp-substrate:	5.584904193878174%

ADMET: Metabolism

CYP1A2-inhibitor:	0.955
CYP1A2-substrate:	0.455
CYP2C19-inhibitor:	0.832
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.561
CYP2C9-substrate:	0.945
CYP2D6-inhibitor:	0.948
CYP2D6-substrate:	0.888
CYP3A4-inhibitor:	0.642
CYP3A4-substrate:	0.149

ADMET: Excretion

Clearance (CL):	15.583
Half-life (T1/2):	0.933

ADMET: Toxicity

hERG Blockers:	0.04
Human Hepatotoxicity (H-HT):	0.132
Drug-inuced Liver Injury (DILI):	0.018
AMES Toxicity:	0.15
Rat Oral Acute Toxicity:	0.505
Maximum Recommended Daily Dose:	0.516
Skin Sensitization:	0.952
Carcinogencity:	0.084
Eye Corrosion:	0.747
Eye Irritation:	0.981
Respiratory Toxicity:	0.062

Download Data

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

Natural Product: NPC102216

Natural Product ID:	NPC102216
*Common Name:**	2',3,5-Trihydroxybibenzyl
IUPAC Name:	5-[2-(2-hydroxyphenyl)ethyl]benzene-1,3-diol
Synonyms:	2',3,5-Trihydroxybibenzyl
Standard InCHIKey:	QNLYZTMYRVYPMN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H14O3/c15-12-7-10(8-13(16)9-12)5-6-11-3-1-2-4-14(11)17/h1-4,7-9,15-17H,5-6H2
SMILES:	Oc1cc(CCc2ccccc2O)cc(c1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL474628
PubChem CID:	442699
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes

*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
NPO20097	Thermobifida alba	Species	0cardiopsaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11430001]
NPO7863	Dioscorea opposita	Species	Dioscoreaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[16124773]
NPO9419	Enterobacter cloacae	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25427277]
NPO24359	Streptomyces cacaoi	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[27642865]
NPO26245	Styracaster caroli	Species	Porcellanasteridae	Eukaryota	n.a.	n.a.	n.a.	PMID[8145229]
NPO7863	Dioscorea opposita	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7863	Dioscorea opposita	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13147	Euphorbia cyparissias	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19605	Tara spinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26245	Styracaster caroli	Species	Porcellanasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6054	Sinularia brongersmai	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10024	Tylecodon wallichii	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8559	Calophyllum venulosum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11319	Laurencia hybrida	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6962	Cetraria delisei	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11181	Juniperus bermudiana	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8460	Pedicularis torta	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20097	Thermobifida alba	Species	0cardiopsaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO7863	Dioscorea opposita	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24359	Streptomyces cacaoi	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO9419	Enterobacter cloacae	Species	Enterobacteriaceae	Bacteria	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	4
Others	1

Activity Type	# Activity
Individual Protein	2
NON-MOLECULAR	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT325	Individual Protein	Cyclooxygenase-2	Ovis aries	IC50	=	19.5	ug.mL-1	PMID[484401]
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	IC50	>	100.0	ug.mL-1	PMID[484401]
NPT1	Others	Radical scavenging activity		IC50	>	100.0	ug.mL-1	PMID[484401]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100.0	ug.mL-1	PMID[484401]
NPT2	Others	Unspecified		Ratio IC50	>	5.1	n.a.	PMID[484401]

☑ 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 NPC102216 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	418
0.1-0.2	1996
0.2-0.3	6390
0.3-0.4	13139
0.4-0.5	4618
0.5-0.6	7653
0.6-0.7	6402
0.7-0.8	1700
0.8-0.85	233
0.85-0.9	74
0.9-0.95	66
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9792	High Similarity	NPC100340
0.9792	High Similarity	NPC143659
0.96	High Similarity	NPC174981
0.9592	High Similarity	NPC241891
0.9592	High Similarity	NPC30506
0.9505	High Similarity	NPC33728
0.9505	High Similarity	NPC19808
0.9495	High Similarity	NPC134829
0.9495	High Similarity	NPC292452
0.9479	High Similarity	NPC291789
0.94	High Similarity	NPC109691
0.94	High Similarity	NPC118286
0.94	High Similarity	NPC39664
0.94	High Similarity	NPC302681
0.94	High Similarity	NPC248904
0.94	High Similarity	NPC470700
0.94	High Similarity	NPC39097
0.9394	High Similarity	NPC119860
0.932	High Similarity	NPC224527
0.932	High Similarity	NPC225679
0.932	High Similarity	NPC4493
0.932	High Similarity	NPC476632
0.932	High Similarity	NPC165770
0.9314	High Similarity	NPC202647
0.9307	High Similarity	NPC54844
0.93	High Similarity	NPC246056
0.93	High Similarity	NPC474839
0.9286	High Similarity	NPC161571
0.9286	High Similarity	NPC275053
0.9286	High Similarity	NPC248573
0.9286	High Similarity	NPC10588
0.9231	High Similarity	NPC166995
0.9231	High Similarity	NPC43525
0.92	High Similarity	NPC244513
0.92	High Similarity	NPC227458
0.92	High Similarity	NPC218879
0.9192	High Similarity	NPC284011
0.9192	High Similarity	NPC72947
0.9143	High Similarity	NPC261343
0.9143	High Similarity	NPC117846
0.9118	High Similarity	NPC204901
0.9118	High Similarity	NPC232523
0.9118	High Similarity	NPC158253
0.9109	High Similarity	NPC37802
0.91	High Similarity	NPC85479
0.91	High Similarity	NPC106396
0.91	High Similarity	NPC146798
0.91	High Similarity	NPC94351
0.91	High Similarity	NPC249828
0.91	High Similarity	NPC24404
0.91	High Similarity	NPC168393
0.91	High Similarity	NPC302219
0.91	High Similarity	NPC222522
0.91	High Similarity	NPC71002
0.91	High Similarity	NPC168303
0.91	High Similarity	NPC313030
0.91	High Similarity	NPC53051
0.91	High Similarity	NPC242342
0.9091	High Similarity	NPC166761
0.9057	High Similarity	NPC107240
0.9029	High Similarity	NPC61885
0.9029	High Similarity	NPC63698
0.902	High Similarity	NPC99836
0.902	High Similarity	NPC12640
0.902	High Similarity	NPC201662
0.9	High Similarity	NPC166313
0.9	High Similarity	NPC137415
0.9	High Similarity	NPC192032
0.9	High Similarity	NPC24407
0.9	High Similarity	NPC294186
0.9	High Similarity	NPC147310
0.9	High Similarity	NPC11280
0.899	High Similarity	NPC80027
0.8972	High Similarity	NPC84999
0.8972	High Similarity	NPC808
0.8972	High Similarity	NPC246760
0.8962	High Similarity	NPC23804
0.8952	High Similarity	NPC268032
0.8942	High Similarity	NPC186385
0.8942	High Similarity	NPC299568
0.8889	High Similarity	NPC150624
0.8878	High Similarity	NPC274678
0.8866	High Similarity	NPC295295
0.8857	High Similarity	NPC475018
0.8835	High Similarity	NPC67250
0.8812	High Similarity	NPC12221
0.8807	High Similarity	NPC69261
0.8807	High Similarity	NPC244816
0.8807	High Similarity	NPC50521
0.8807	High Similarity	NPC221549
0.8807	High Similarity	NPC33270
0.8807	High Similarity	NPC470760
0.8776	High Similarity	NPC76938
0.8776	High Similarity	NPC128062
0.875	High Similarity	NPC305603
0.875	High Similarity	NPC61033
0.875	High Similarity	NPC176527
0.8727	High Similarity	NPC144343
0.8727	High Similarity	NPC190514
0.8716	High Similarity	NPC115808
0.8704	High Similarity	NPC276737
0.8704	High Similarity	NPC249270
0.8704	High Similarity	NPC22610
0.87	High Similarity	NPC156313
0.8687	High Similarity	NPC32714
0.8679	High Similarity	NPC224870
0.8673	High Similarity	NPC271440
0.8667	High Similarity	NPC95344
0.8667	High Similarity	NPC34864
0.8667	High Similarity	NPC105727
0.8667	High Similarity	NPC58427
0.8667	High Similarity	NPC114392
0.8649	High Similarity	NPC184302
0.8636	High Similarity	NPC277588
0.8624	High Similarity	NPC53906
0.8624	High Similarity	NPC167934
0.8611	High Similarity	NPC319803
0.8571	High Similarity	NPC223451
0.8571	High Similarity	NPC45040
0.8571	High Similarity	NPC69006
0.8571	High Similarity	NPC472071
0.8559	High Similarity	NPC48781
0.8559	High Similarity	NPC9592
0.8558	High Similarity	NPC471350
0.8545	High Similarity	NPC141090
0.8545	High Similarity	NPC203113
0.8544	High Similarity	NPC233827
0.8529	High Similarity	NPC130103
0.8529	High Similarity	NPC294741
0.8519	High Similarity	NPC473521
0.8505	High Similarity	NPC94045
0.8496	Intermediate Similarity	NPC24125
0.8482	Intermediate Similarity	NPC191866
0.8482	Intermediate Similarity	NPC217174
0.8476	Intermediate Similarity	NPC54765
0.8469	Intermediate Similarity	NPC192
0.8468	Intermediate Similarity	NPC15860
0.8468	Intermediate Similarity	NPC470759
0.8468	Intermediate Similarity	NPC474933
0.8468	Intermediate Similarity	NPC219070
0.8468	Intermediate Similarity	NPC195466
0.8468	Intermediate Similarity	NPC127894
0.8455	Intermediate Similarity	NPC472893
0.8455	Intermediate Similarity	NPC232165
0.8454	Intermediate Similarity	NPC27974
0.844	Intermediate Similarity	NPC263753
0.8438	Intermediate Similarity	NPC155393
0.8426	Intermediate Similarity	NPC296920
0.8426	Intermediate Similarity	NPC90520
0.8421	Intermediate Similarity	NPC237667
0.8421	Intermediate Similarity	NPC476633
0.8416	Intermediate Similarity	NPC259512
0.8416	Intermediate Similarity	NPC312132
0.84	Intermediate Similarity	NPC245187
0.84	Intermediate Similarity	NPC151715
0.8393	Intermediate Similarity	NPC206
0.8384	Intermediate Similarity	NPC231150
0.8378	Intermediate Similarity	NPC54507
0.8378	Intermediate Similarity	NPC85292
0.8378	Intermediate Similarity	NPC229147
0.8378	Intermediate Similarity	NPC114064
0.8365	Intermediate Similarity	NPC168829
0.8351	Intermediate Similarity	NPC407
0.8351	Intermediate Similarity	NPC307235
0.835	Intermediate Similarity	NPC72729
0.835	Intermediate Similarity	NPC248396
0.835	Intermediate Similarity	NPC48730
0.835	Intermediate Similarity	NPC174911
0.835	Intermediate Similarity	NPC129373
0.8349	Intermediate Similarity	NPC280606
0.8348	Intermediate Similarity	NPC77789
0.8348	Intermediate Similarity	NPC120172
0.8348	Intermediate Similarity	NPC18128
0.8333	Intermediate Similarity	NPC32674
0.8333	Intermediate Similarity	NPC152097
0.8333	Intermediate Similarity	NPC79241
0.8333	Intermediate Similarity	NPC6597
0.8333	Intermediate Similarity	NPC88420
0.8333	Intermediate Similarity	NPC168657
0.8333	Intermediate Similarity	NPC242178
0.8333	Intermediate Similarity	NPC102639
0.8318	Intermediate Similarity	NPC169450
0.8317	Intermediate Similarity	NPC26244
0.83	Intermediate Similarity	NPC3358
0.83	Intermediate Similarity	NPC29373
0.83	Intermediate Similarity	NPC55903
0.83	Intermediate Similarity	NPC306884
0.83	Intermediate Similarity	NPC147284
0.83	Intermediate Similarity	NPC94139
0.83	Intermediate Similarity	NPC162314
0.83	Intermediate Similarity	NPC210497
0.8288	Intermediate Similarity	NPC185541
0.8288	Intermediate Similarity	NPC464
0.8286	Intermediate Similarity	NPC471511
0.8286	Intermediate Similarity	NPC288411
0.8286	Intermediate Similarity	NPC323810
0.8286	Intermediate Similarity	NPC238696
0.8283	Intermediate Similarity	NPC47950
0.8276	Intermediate Similarity	NPC121115
0.8276	Intermediate Similarity	NPC53567

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 NPC102216 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	399
0.1-0.2	1037
0.2-0.3	1423
0.3-0.4	2962
0.4-0.5	1801
0.5-0.6	1081
0.6-0.7	381
0.7-0.8	52
0.8-0.85	11
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9286	High Similarity	NPD1242	Phase 1
0.9	High Similarity	NPD846	Approved
0.9	High Similarity	NPD940	Approved
0.8942	High Similarity	NPD4750	Phase 3
0.85	High Similarity	NPD844	Approved
0.8416	Intermediate Similarity	NPD288	Approved
0.835	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.8317	Intermediate Similarity	NPD2859	Approved
0.8317	Intermediate Similarity	NPD2860	Approved
0.8252	Intermediate Similarity	NPD3020	Approved
0.8218	Intermediate Similarity	NPD2934	Approved
0.8218	Intermediate Similarity	NPD2933	Approved
0.8103	Intermediate Similarity	NPD1610	Phase 2
0.807	Intermediate Similarity	NPD1548	Phase 1
0.8056	Intermediate Similarity	NPD2342	Discontinued
0.7941	Intermediate Similarity	NPD845	Approved
0.7934	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD9089	Approved
0.7909	Intermediate Similarity	NPD3021	Approved
0.7909	Intermediate Similarity	NPD3022	Approved
0.7869	Intermediate Similarity	NPD4625	Phase 3
0.7864	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD7635	Approved
0.7851	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD4749	Approved
0.7812	Intermediate Similarity	NPD9093	Approved
0.7719	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD1613	Approved
0.768	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD943	Approved
0.7677	Intermediate Similarity	NPD111	Approved
0.7647	Intermediate Similarity	NPD1201	Approved
0.7642	Intermediate Similarity	NPD9273	Approved
0.7642	Intermediate Similarity	NPD4908	Phase 1
0.7619	Intermediate Similarity	NPD1809	Phase 2
0.7589	Intermediate Similarity	NPD1792	Phase 2
0.7581	Intermediate Similarity	NPD3027	Phase 3
0.752	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD422	Phase 1
0.75	Intermediate Similarity	NPD6671	Approved
0.748	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD1444	Approved
0.7477	Intermediate Similarity	NPD1445	Approved
0.7451	Intermediate Similarity	NPD9094	Approved
0.7398	Intermediate Similarity	NPD1470	Approved
0.7381	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD968	Approved
0.7308	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD2861	Phase 2
0.7266	Intermediate Similarity	NPD1240	Approved
0.7265	Intermediate Similarity	NPD497	Approved
0.7236	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD9500	Approved
0.7203	Intermediate Similarity	NPD709	Approved
0.719	Intermediate Similarity	NPD2286	Discontinued
0.7182	Intermediate Similarity	NPD3028	Approved
0.7179	Intermediate Similarity	NPD2228	Approved
0.7179	Intermediate Similarity	NPD2229	Approved
0.7179	Intermediate Similarity	NPD498	Approved
0.7179	Intermediate Similarity	NPD495	Approved
0.7179	Intermediate Similarity	NPD496	Approved
0.7179	Intermediate Similarity	NPD2234	Approved
0.7176	Intermediate Similarity	NPD1510	Phase 2
0.7167	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD3091	Approved
0.7155	Intermediate Similarity	NPD228	Approved
0.7154	Intermediate Similarity	NPD1607	Approved
0.7154	Intermediate Similarity	NPD2568	Approved
0.7143	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3018	Phase 2
0.7132	Intermediate Similarity	NPD1555	Discontinued
0.713	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD6099	Approved
0.7121	Intermediate Similarity	NPD6100	Approved
0.712	Intermediate Similarity	NPD1164	Approved
0.712	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD4093	Discontinued
0.7094	Intermediate Similarity	NPD9377	Approved
0.7094	Intermediate Similarity	NPD9379	Approved
0.7083	Intermediate Similarity	NPD9087	Approved
0.7073	Intermediate Similarity	NPD3092	Approved
0.7069	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD599	Approved
0.7063	Intermediate Similarity	NPD859	Approved
0.7063	Intermediate Similarity	NPD602	Approved
0.7063	Intermediate Similarity	NPD858	Approved
0.7054	Intermediate Similarity	NPD6405	Approved
0.7054	Intermediate Similarity	NPD6407	Approved
0.7049	Intermediate Similarity	NPD4589	Approved
0.7049	Intermediate Similarity	NPD2932	Approved
0.7049	Intermediate Similarity	NPD3019	Approved
0.7049	Intermediate Similarity	NPD4059	Approved
0.7049	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD9266	Approved
0.7043	Intermediate Similarity	NPD74	Approved
0.7025	Intermediate Similarity	NPD5303	Approved
0.7025	Intermediate Similarity	NPD5304	Approved
0.7016	Intermediate Similarity	NPD1608	Approved
0.7	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD1980	Approved
0.6992	Remote Similarity	NPD1981	Approved
0.6992	Remote Similarity	NPD1983	Approved
0.6991	Remote Similarity	NPD9610	Approved
0.6991	Remote Similarity	NPD9608	Approved
0.6984	Remote Similarity	NPD3094	Phase 2
0.6977	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD9614	Approved
0.6975	Remote Similarity	NPD1793	Approved
0.6975	Remote Similarity	NPD9618	Approved
0.6975	Remote Similarity	NPD1791	Approved
0.697	Remote Similarity	NPD9088	Approved
0.696	Remote Similarity	NPD2982	Phase 2
0.696	Remote Similarity	NPD2983	Phase 2
0.6957	Remote Similarity	NPD9264	Approved
0.6957	Remote Similarity	NPD9263	Approved
0.6957	Remote Similarity	NPD9267	Approved
0.6957	Remote Similarity	NPD290	Approved
0.694	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.694	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD3892	Phase 2
0.6912	Remote Similarity	NPD3750	Approved
0.6911	Remote Similarity	NPD9384	Approved
0.6911	Remote Similarity	NPD9381	Approved
0.6911	Remote Similarity	NPD1751	Approved
0.6891	Remote Similarity	NPD5283	Phase 1
0.6889	Remote Similarity	NPD1549	Phase 2
0.6885	Remote Similarity	NPD1759	Phase 1
0.6885	Remote Similarity	NPD7330	Discontinued
0.6884	Remote Similarity	NPD7390	Discontinued
0.6884	Remote Similarity	NPD1511	Approved
0.688	Remote Similarity	NPD9269	Phase 2
0.688	Remote Similarity	NPD2230	Approved
0.688	Remote Similarity	NPD2233	Approved
0.688	Remote Similarity	NPD2981	Phase 2
0.688	Remote Similarity	NPD2232	Approved
0.687	Remote Similarity	NPD2238	Phase 2
0.6869	Remote Similarity	NPD9294	Approved
0.6866	Remote Similarity	NPD5404	Approved
0.6866	Remote Similarity	NPD5406	Approved
0.6866	Remote Similarity	NPD1551	Phase 2
0.6866	Remote Similarity	NPD5408	Approved
0.6866	Remote Similarity	NPD5405	Approved
0.6864	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.686	Remote Similarity	NPD9493	Approved
0.685	Remote Similarity	NPD1133	Approved
0.685	Remote Similarity	NPD1135	Approved
0.685	Remote Similarity	NPD1129	Approved
0.685	Remote Similarity	NPD1131	Approved
0.685	Remote Similarity	NPD2797	Approved
0.685	Remote Similarity	NPD1134	Approved
0.6829	Remote Similarity	NPD9268	Approved
0.6825	Remote Similarity	NPD4659	Approved
0.681	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD9616	Approved
0.6803	Remote Similarity	NPD1758	Phase 1
0.6803	Remote Similarity	NPD9613	Approved
0.6803	Remote Similarity	NPD9615	Approved
0.68	Remote Similarity	NPD1091	Approved
0.6797	Remote Similarity	NPD6584	Phase 3
0.6788	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD1512	Approved
0.6774	Remote Similarity	NPD17	Approved
0.6774	Remote Similarity	NPD3095	Discontinued
0.6774	Remote Similarity	NPD4626	Approved
0.6772	Remote Similarity	NPD3225	Approved
0.6772	Remote Similarity	NPD5310	Approved
0.6772	Remote Similarity	NPD6696	Suspended
0.6772	Remote Similarity	NPD5311	Approved
0.6765	Remote Similarity	NPD970	Clinical (unspecified phase)
0.675	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD316	Approved
0.6746	Remote Similarity	NPD2562	Approved
0.6746	Remote Similarity	NPD2561	Approved
0.6742	Remote Similarity	NPD4060	Phase 1
0.6741	Remote Similarity	NPD2935	Discontinued
0.6726	Remote Similarity	NPD1616	Discontinued
0.6719	Remote Similarity	NPD3053	Approved
0.6719	Remote Similarity	NPD1203	Approved
0.6719	Remote Similarity	NPD4103	Phase 2
0.6719	Remote Similarity	NPD3055	Approved
0.6719	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD3554	Approved
0.6716	Remote Similarity	NPD3552	Approved
0.6716	Remote Similarity	NPD3555	Approved
0.6716	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD3553	Approved
0.6714	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD7447	Phase 1
0.6695	Remote Similarity	NPD5451	Approved
0.6693	Remote Similarity	NPD9622	Approved
0.6693	Remote Similarity	NPD1755	Approved
0.6691	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD318	Approved
0.6667	Remote Similarity	NPD16	Approved
0.6667	Remote Similarity	NPD856	Approved
0.6667	Remote Similarity	NPD1611	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