NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	242.06
Volume:	247.657
LogP:	3.387
LogD:	3.798
LogS:	-4.725
# Rotatable Bonds:	5
TPSA:	52.6
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.6
Synthetic Accessibility Score:	1.676
Fsp3:	0.0
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:	-4.583
MDCK Permeability:	3.2789885153761134e-05
Pgp-inhibitor:	0.067
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.717
30% Bioavailability (F30%):	0.978

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.222
Plasma Protein Binding (PPB):	97.27664184570312%
Volume Distribution (VD):	0.854
Pgp-substrate:	1.5926340818405151%

ADMET: Metabolism

CYP1A2-inhibitor:	0.957
CYP1A2-substrate:	0.122
CYP2C19-inhibitor:	0.904
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.655
CYP2C9-substrate:	0.247
CYP2D6-inhibitor:	0.026
CYP2D6-substrate:	0.09
CYP3A4-inhibitor:	0.032
CYP3A4-substrate:	0.138

ADMET: Excretion

Clearance (CL):	9.735
Half-life (T1/2):	0.869

ADMET: Toxicity

hERG Blockers:	0.105
Human Hepatotoxicity (H-HT):	0.008
Drug-inuced Liver Injury (DILI):	0.423
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.002
Maximum Recommended Daily Dose:	0.005
Skin Sensitization:	0.893
Carcinogencity:	0.036
Eye Corrosion:	0.043
Eye Irritation:	0.994
Respiratory Toxicity:	0.369

Download Data

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

Natural Product: NPC261181

Natural Product ID:	NPC261181
*Common Name:**	Benzoyl Peroxide
IUPAC Name:	benzoyl benzenecarboperoxoate
Synonyms:	Acetoxyl 2.5; Acetoxyl 5; Acne-Aid Cream; Acnecide; Acnecide 10; Acnegel; Acnegel Fte; Acnidazil; Benoxyl; Benoxyl 10; Benoxyl 20; Benoxyl 5; Benzac; Benzac W; Benzagel 10; Benzagel 5; Benzamycin; Benzoyl Peroxide; Brevoxyl; Clear By Design; Clearasil Max 10; Dermoxyl; Dry and Clear; Dry Clear; E928; Epi-Clear; Fostex BPO Bar, Gel, and Wash; Gppe Lotio Gel; Loroxide; Mediclear; Mediclear Acne 10; Mediclear Acne 5; Nericur; Oxy-10; Oxy-10 Cover-Up; Oxy-5; PanOxyl; PanOxyl 10; PanOxyl 10 Acnegel; PanOxyl 10 Aquagel; PanOxyl 2.5 Aquagel; PanOxyl 5 Acnegel; PanOxyl 5 Aquagel; PanOxyl Crm 5; PanOxyl Lot 10; PanOxyl Lot 5; Persa-Gel; Quinoderm 5; Quinoped; Theraderm 10; Theraderm 5; Topex; Ultra Clearasil; Valderma; Vanair; Vanoxide
Standard InCHIKey:	OMPJBNCRMGITSC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H10O4/c15-13(11-7-3-1-4-8-11)17-18-14(16)12-9-5-2-6-10-12/h1-10H
SMILES:	O=C(c1ccccc1)OOC(=O)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1200370
PubChem CID:	7187
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0004112] Benzoyl peroxides

*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
NPO30900	Morinda parvifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7097296]
NPO30900	Morinda parvifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21641	Onychium lucidum	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21641	Onychium lucidum	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11242	Gynochthodes parvifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO30900	Morinda parvifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21641	Onychium lucidum	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11242	Gynochthodes parvifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21641	Onychium lucidum	Species	Pteridaceae	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
AC50	2
IC50	2
Others	23
Potency	3

Activity Type	# Activity
Individual Protein	2
ORGANISM	7
Others	5
PHENOTYPE	14
SINGLE PROTEIN	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT483	Individual Protein	Prelamin-A/C	Homo sapiens	Potency	=	6.3	nM	PMID[449479]
NPT46	Individual Protein	Thyroid hormone receptor beta-1	Homo sapiens	Potency	n.a.	158.5	nM	PMID[449481]
NPT20596	PHENOTYPE	Hepatotoxicity	n.a.	HepSE_bilirubinemia	=	0.0	n.a.	PMID[449482]
NPT20596	PHENOTYPE	Hepatotoxicity	n.a.	HepSE_cholecystitis	=	0.0	n.a.	PMID[449482]
NPT20596	PHENOTYPE	Hepatotoxicity	n.a.	HepSE_cholelithiasis	=	0.0	n.a.	PMID[449482]
NPT20596	PHENOTYPE	Hepatotoxicity	n.a.	HepSE_cirrhosis	=	0.0	n.a.	PMID[449482]
NPT20596	PHENOTYPE	Hepatotoxicity	n.a.	HepSE_elevated liver function tests	=	0.0	n.a.	PMID[449482]
NPT20596	PHENOTYPE	Hepatotoxicity	n.a.	HepSE_hepatic failure	=	0.0	n.a.	PMID[449482]
NPT20596	PHENOTYPE	Hepatotoxicity	n.a.	HepSE_hepatic necrosis	=	0.0	n.a.	PMID[449482]
NPT20596	PHENOTYPE	Hepatotoxicity	n.a.	HepSE_hepatitis	=	0.0	n.a.	PMID[449482]
NPT20596	PHENOTYPE	Hepatotoxicity	n.a.	HepSE_hepatomegaly	=	0.0	n.a.	PMID[449482]
NPT20596	PHENOTYPE	Hepatotoxicity	n.a.	HepSE_jaundice	=	0.0	n.a.	PMID[449482]
NPT20596	PHENOTYPE	Hepatotoxicity	n.a.	HepSE_liver disease	=	0.0	n.a.	PMID[449482]
NPT20596	PHENOTYPE	Hepatotoxicity	n.a.	HepSE_liver fatty	=	0.0	n.a.	PMID[449482]
NPT20596	PHENOTYPE	Hepatotoxicity	n.a.	HepSE_liver function tests abnormal	=	0.0	n.a.	PMID[449482]
NPT20596	PHENOTYPE	Hepatotoxicity	n.a.	HepSE_Combined Scores	=	0.0	n.a.	PMID[449482]
NPT2	Others	Unspecified		Ac50	n.a.	5.012	uM	PMID[449483]
NPT2	Others	Unspecified		AC50	n.a.	5011.9	nM	PMID[449483]
NPT2	Others	Unspecified		Ac50	n.a.	1.259	uM	PMID[449483]
NPT2	Others	Unspecified		AC50	n.a.	1258.9	nM	PMID[449483]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	22.47	%	PMID[449484]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	30.68	%	PMID[449485]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	4.951	%	PMID[449486]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	0.04	%	PMID[449487]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-0.18	%	PMID[449488]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	20000.0	nM	PMID[449489]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	19952.62	nM	PMID[449489]
NPT2	Others	Unspecified		Potency	n.a.	4.7	nM	PubChem BioAssay data set

☑ 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 NPC261181 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	344
0.1-0.2	2106
0.2-0.3	4833
0.3-0.4	12876
0.4-0.5	10283
0.5-0.6	9850
0.6-0.7	2057
0.7-0.8	301
0.8-0.85	34
0.85-0.9	10
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9195	High Similarity	NPC318107
0.9043	High Similarity	NPC118343
0.8947	High Similarity	NPC42211
0.8817	High Similarity	NPC130398
0.8791	High Similarity	NPC62765
0.8776	High Similarity	NPC269457
0.8763	High Similarity	NPC255676
0.8723	High Similarity	NPC61944
0.8646	High Similarity	NPC203925
0.8632	High Similarity	NPC253423
0.8632	High Similarity	NPC276775
0.8632	High Similarity	NPC249912
0.8632	High Similarity	NPC92754
0.8586	High Similarity	NPC105899
0.8542	High Similarity	NPC229242
0.8542	High Similarity	NPC78701
0.8542	High Similarity	NPC35448
0.8542	High Similarity	NPC225060
0.8469	Intermediate Similarity	NPC284477
0.8454	Intermediate Similarity	NPC146351
0.8454	Intermediate Similarity	NPC228435
0.8454	Intermediate Similarity	NPC325497
0.8454	Intermediate Similarity	NPC217621
0.8384	Intermediate Similarity	NPC474365
0.8384	Intermediate Similarity	NPC301943
0.8367	Intermediate Similarity	NPC70624
0.8367	Intermediate Similarity	NPC282895
0.8333	Intermediate Similarity	NPC318327
0.83	Intermediate Similarity	NPC114594
0.83	Intermediate Similarity	NPC31786
0.8283	Intermediate Similarity	NPC25458
0.8283	Intermediate Similarity	NPC304873
0.8283	Intermediate Similarity	NPC188895
0.8247	Intermediate Similarity	NPC270654
0.8218	Intermediate Similarity	NPC209632
0.82	Intermediate Similarity	NPC60679
0.8137	Intermediate Similarity	NPC119271
0.8119	Intermediate Similarity	NPC249067
0.8105	Intermediate Similarity	NPC119631
0.8105	Intermediate Similarity	NPC110704
0.81	Intermediate Similarity	NPC45613
0.8095	Intermediate Similarity	NPC158282
0.8095	Intermediate Similarity	NPC79496
0.8095	Intermediate Similarity	NPC66208
0.8085	Intermediate Similarity	NPC9822
0.8058	Intermediate Similarity	NPC56493
0.8022	Intermediate Similarity	NPC288903
0.8022	Intermediate Similarity	NPC285773
0.802	Intermediate Similarity	NPC89886
0.802	Intermediate Similarity	NPC329556
0.7981	Intermediate Similarity	NPC10251
0.7981	Intermediate Similarity	NPC469636
0.7981	Intermediate Similarity	NPC269023
0.7981	Intermediate Similarity	NPC474364
0.7981	Intermediate Similarity	NPC99846
0.7981	Intermediate Similarity	NPC85493
0.7981	Intermediate Similarity	NPC17417
0.7961	Intermediate Similarity	NPC30594
0.7961	Intermediate Similarity	NPC37622
0.7941	Intermediate Similarity	NPC269644
0.7905	Intermediate Similarity	NPC93084
0.7905	Intermediate Similarity	NPC196246
0.7905	Intermediate Similarity	NPC251854
0.7905	Intermediate Similarity	NPC174099
0.7905	Intermediate Similarity	NPC214067
0.7895	Intermediate Similarity	NPC173443
0.789	Intermediate Similarity	NPC158157
0.7889	Intermediate Similarity	NPC71664
0.7885	Intermediate Similarity	NPC141523
0.7885	Intermediate Similarity	NPC249811
0.785	Intermediate Similarity	NPC128368
0.785	Intermediate Similarity	NPC474176
0.7849	Intermediate Similarity	NPC294134
0.7843	Intermediate Similarity	NPC291426
0.783	Intermediate Similarity	NPC474157
0.783	Intermediate Similarity	NPC167504
0.783	Intermediate Similarity	NPC1082
0.783	Intermediate Similarity	NPC210089
0.783	Intermediate Similarity	NPC260818
0.783	Intermediate Similarity	NPC305912
0.7826	Intermediate Similarity	NPC273758
0.7818	Intermediate Similarity	NPC469574
0.7812	Intermediate Similarity	NPC240108
0.7812	Intermediate Similarity	NPC213156
0.781	Intermediate Similarity	NPC265407
0.781	Intermediate Similarity	NPC83628
0.7802	Intermediate Similarity	NPC12936
0.7802	Intermediate Similarity	NPC273033
0.7767	Intermediate Similarity	NPC324786
0.7757	Intermediate Similarity	NPC82899
0.7757	Intermediate Similarity	NPC474314
0.7757	Intermediate Similarity	NPC321852
0.7757	Intermediate Similarity	NPC270699
0.7714	Intermediate Similarity	NPC156648
0.7714	Intermediate Similarity	NPC211439
0.7706	Intermediate Similarity	NPC186933
0.7706	Intermediate Similarity	NPC210092
0.77	Intermediate Similarity	NPC289201
0.7692	Intermediate Similarity	NPC127343
0.7685	Intermediate Similarity	NPC161611
0.7685	Intermediate Similarity	NPC272524
0.7684	Intermediate Similarity	NPC89377
0.7684	Intermediate Similarity	NPC322387
0.7677	Intermediate Similarity	NPC172925
0.7664	Intermediate Similarity	NPC476003
0.7664	Intermediate Similarity	NPC243355
0.7658	Intermediate Similarity	NPC45104
0.7658	Intermediate Similarity	NPC228318
0.7647	Intermediate Similarity	NPC473325
0.7642	Intermediate Similarity	NPC17525
0.7642	Intermediate Similarity	NPC281604
0.7636	Intermediate Similarity	NPC149691
0.7624	Intermediate Similarity	NPC160548
0.7624	Intermediate Similarity	NPC175852
0.7624	Intermediate Similarity	NPC210529
0.7619	Intermediate Similarity	NPC184658
0.7619	Intermediate Similarity	NPC187913
0.7615	Intermediate Similarity	NPC474363
0.7615	Intermediate Similarity	NPC307651
0.7615	Intermediate Similarity	NPC153053
0.7615	Intermediate Similarity	NPC308744
0.7604	Intermediate Similarity	NPC329064
0.7582	Intermediate Similarity	NPC300205
0.7576	Intermediate Similarity	NPC34243
0.7556	Intermediate Similarity	NPC245966
0.7553	Intermediate Similarity	NPC44546
0.7547	Intermediate Similarity	NPC29883
0.7545	Intermediate Similarity	NPC474685
0.7545	Intermediate Similarity	NPC306740
0.7526	Intermediate Similarity	NPC220893
0.75	Intermediate Similarity	NPC69057
0.75	Intermediate Similarity	NPC164086
0.75	Intermediate Similarity	NPC116842
0.7477	Intermediate Similarity	NPC100551
0.7477	Intermediate Similarity	NPC100353
0.7476	Intermediate Similarity	NPC52472
0.7474	Intermediate Similarity	NPC58616
0.7474	Intermediate Similarity	NPC95965
0.7473	Intermediate Similarity	NPC285470
0.7473	Intermediate Similarity	NPC36342
0.7473	Intermediate Similarity	NPC2785
0.7456	Intermediate Similarity	NPC473243
0.7456	Intermediate Similarity	NPC233282
0.7455	Intermediate Similarity	NPC211421
0.7455	Intermediate Similarity	NPC196673
0.7453	Intermediate Similarity	NPC29989
0.7453	Intermediate Similarity	NPC95178
0.7453	Intermediate Similarity	NPC70843
0.7453	Intermediate Similarity	NPC69332
0.7449	Intermediate Similarity	NPC274455
0.7449	Intermediate Similarity	NPC86670
0.7449	Intermediate Similarity	NPC70940
0.7447	Intermediate Similarity	NPC44830
0.7431	Intermediate Similarity	NPC268388
0.7429	Intermediate Similarity	NPC329282
0.7426	Intermediate Similarity	NPC12695
0.7414	Intermediate Similarity	NPC68167
0.7411	Intermediate Similarity	NPC128249
0.7407	Intermediate Similarity	NPC216122
0.7407	Intermediate Similarity	NPC88141
0.7391	Intermediate Similarity	NPC151405
0.7391	Intermediate Similarity	NPC139901
0.7387	Intermediate Similarity	NPC81808
0.7383	Intermediate Similarity	NPC226699
0.7383	Intermediate Similarity	NPC34715
0.7379	Intermediate Similarity	NPC245561
0.7368	Intermediate Similarity	NPC95429
0.7358	Intermediate Similarity	NPC134120
0.7358	Intermediate Similarity	NPC13495
0.7353	Intermediate Similarity	NPC103048
0.7353	Intermediate Similarity	NPC156021
0.734	Intermediate Similarity	NPC323103
0.7339	Intermediate Similarity	NPC474057
0.7339	Intermediate Similarity	NPC21162
0.7333	Intermediate Similarity	NPC160382
0.7333	Intermediate Similarity	NPC206800
0.7333	Intermediate Similarity	NPC13426
0.7333	Intermediate Similarity	NPC32203
0.7328	Intermediate Similarity	NPC167323
0.7328	Intermediate Similarity	NPC198336
0.7328	Intermediate Similarity	NPC269923
0.7321	Intermediate Similarity	NPC188907
0.7321	Intermediate Similarity	NPC322197
0.7321	Intermediate Similarity	NPC220540
0.732	Intermediate Similarity	NPC194326
0.7315	Intermediate Similarity	NPC224584
0.7312	Intermediate Similarity	NPC95868
0.7312	Intermediate Similarity	NPC121800
0.7312	Intermediate Similarity	NPC190567
0.7308	Intermediate Similarity	NPC112552
0.73	Intermediate Similarity	NPC77273
0.7297	Intermediate Similarity	NPC237366
0.7292	Intermediate Similarity	NPC123476
0.729	Intermediate Similarity	NPC6984
0.7288	Intermediate Similarity	NPC295664
0.7282	Intermediate Similarity	NPC179411
0.7281	Intermediate Similarity	NPC311091
0.7281	Intermediate Similarity	NPC471033
0.7273	Intermediate Similarity	NPC212415
0.7273	Intermediate Similarity	NPC19256

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 NPC261181 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	337
0.1-0.2	952
0.2-0.3	1267
0.3-0.4	3047
0.4-0.5	2296
0.5-0.6	950
0.6-0.7	236
0.7-0.8	54
0.8-0.85	5
0.85-0.9	2
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD1202	Approved
0.9195	High Similarity	NPD9257	Approved
0.9195	High Similarity	NPD9259	Approved
0.9043	High Similarity	NPD1238	Approved
0.8791	High Similarity	NPD9258	Approved
0.8791	High Similarity	NPD9256	Approved
0.8421	Intermediate Similarity	NPD9260	Approved
0.83	Intermediate Similarity	NPD164	Approved
0.8182	Intermediate Similarity	NPD9490	Approved
0.8155	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.8119	Intermediate Similarity	NPD1237	Approved
0.8022	Intermediate Similarity	NPD9491	Approved
0.802	Intermediate Similarity	NPD1930	Approved
0.802	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.802	Intermediate Similarity	NPD1929	Approved
0.7981	Intermediate Similarity	NPD2182	Approved
0.7917	Intermediate Similarity	NPD1239	Approved
0.787	Intermediate Similarity	NPD5951	Approved
0.7865	Intermediate Similarity	NPD225	Approved
0.7865	Intermediate Similarity	NPD227	Approved
0.7843	Intermediate Similarity	NPD9261	Approved
0.7802	Intermediate Similarity	NPD942	Approved
0.7755	Intermediate Similarity	NPD1563	Approved
0.7745	Intermediate Similarity	NPD1932	Approved
0.7723	Intermediate Similarity	NPD2066	Phase 3
0.7684	Intermediate Similarity	NPD1087	Approved
0.7677	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD9495	Approved
0.7609	Intermediate Similarity	NPD226	Approved
0.76	Intermediate Similarity	NPD1989	Approved
0.7593	Intermediate Similarity	NPD9508	Approved
0.7547	Intermediate Similarity	NPD9264	Approved
0.7547	Intermediate Similarity	NPD9267	Approved
0.7547	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD9263	Approved
0.7544	Intermediate Similarity	NPD1889	Phase 1
0.7526	Intermediate Similarity	NPD800	Approved
0.7525	Intermediate Similarity	NPD1566	Phase 3
0.7525	Intermediate Similarity	NPD1564	Approved
0.7525	Intermediate Similarity	NPD1565	Approved
0.7523	Intermediate Similarity	NPD5277	Phase 2
0.7478	Intermediate Similarity	NPD6287	Discontinued
0.7477	Intermediate Similarity	NPD9266	Approved
0.7477	Intermediate Similarity	NPD74	Approved
0.7456	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD1086	Approved
0.7449	Intermediate Similarity	NPD1090	Approved
0.7449	Intermediate Similarity	NPD1089	Approved
0.74	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD9716	Approved
0.7315	Intermediate Similarity	NPD2329	Discontinued
0.7312	Intermediate Similarity	NPD1507	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD1088	Approved
0.7288	Intermediate Similarity	NPD1888	Phase 1
0.7273	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD5909	Discontinued
0.7257	Intermediate Similarity	NPD9493	Approved
0.7232	Intermediate Similarity	NPD9281	Approved
0.7232	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD1203	Approved
0.7157	Intermediate Similarity	NPD1693	Approved
0.7155	Intermediate Similarity	NPD1104	Approved
0.7143	Intermediate Similarity	NPD4793	Discontinued
0.7143	Intermediate Similarity	NPD650	Approved
0.713	Intermediate Similarity	NPD9545	Approved
0.7129	Intermediate Similarity	NPD1508	Approved
0.7087	Intermediate Similarity	NPD5206	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1164	Approved
0.7049	Intermediate Similarity	NPD6832	Phase 2
0.7048	Intermediate Similarity	NPD7798	Approved
0.7043	Intermediate Similarity	NPD2347	Approved
0.7025	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD1362	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5347	Phase 2
0.7	Intermediate Similarity	NPD2198	Approved
0.7	Intermediate Similarity	NPD5346	Phase 2
0.7	Intermediate Similarity	NPD2199	Approved
0.6992	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD9717	Approved
0.6937	Remote Similarity	NPD2067	Discontinued
0.6937	Remote Similarity	NPD1317	Discontinued
0.6935	Remote Similarity	NPD3764	Approved
0.6935	Remote Similarity	NPD2313	Discontinued
0.6931	Remote Similarity	NPD3673	Approved
0.6931	Remote Similarity	NPD3672	Approved
0.693	Remote Similarity	NPD1246	Approved
0.693	Remote Similarity	NPD2629	Approved
0.6923	Remote Similarity	NPD1843	Approved
0.6917	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD3971	Phase 1
0.6891	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD518	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD2345	Approved
0.6863	Remote Similarity	NPD7609	Phase 3
0.6855	Remote Similarity	NPD6966	Discovery
0.6855	Remote Similarity	NPD7008	Discontinued
0.6852	Remote Similarity	NPD6647	Phase 2
0.6842	Remote Similarity	NPD1241	Discontinued
0.6833	Remote Similarity	NPD4878	Approved
0.6833	Remote Similarity	NPD3972	Approved
0.6825	Remote Similarity	NPD4307	Phase 2
0.681	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD9294	Approved
0.6803	Remote Similarity	NPD1470	Approved
0.68	Remote Similarity	NPD506	Clinical (unspecified phase)
0.68	Remote Similarity	NPD1282	Approved
0.6796	Remote Similarity	NPD7631	Approved
0.6792	Remote Similarity	NPD5926	Approved
0.678	Remote Similarity	NPD4105	Approved
0.678	Remote Similarity	NPD4102	Approved
0.6777	Remote Similarity	NPD5159	Phase 2
0.6777	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD5157	Phase 1
0.6772	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD1933	Approved
0.675	Remote Similarity	NPD1201	Approved
0.6748	Remote Similarity	NPD2798	Approved
0.6748	Remote Similarity	NPD1019	Discontinued
0.6727	Remote Similarity	NPD5048	Discontinued
0.6727	Remote Similarity	NPD9697	Approved
0.6723	Remote Similarity	NPD17	Approved
0.6723	Remote Similarity	NPD9272	Approved
0.6721	Remote Similarity	NPD1876	Approved
0.6698	Remote Similarity	NPD3495	Discontinued
0.6695	Remote Similarity	NPD1894	Discontinued
0.6694	Remote Similarity	NPD1481	Phase 2
0.6693	Remote Similarity	NPD3373	Approved
0.6667	Remote Similarity	NPD3266	Approved
0.6667	Remote Similarity	NPD9567	Approved
0.6667	Remote Similarity	NPD4136	Approved
0.6667	Remote Similarity	NPD3267	Approved
0.6667	Remote Similarity	NPD4106	Approved
0.6667	Remote Similarity	NPD4135	Approved
0.6667	Remote Similarity	NPD553	Approved
0.6667	Remote Similarity	NPD552	Approved
0.6639	Remote Similarity	NPD1245	Approved
0.6639	Remote Similarity	NPD9268	Approved
0.6637	Remote Similarity	NPD5235	Approved
0.6637	Remote Similarity	NPD5236	Approved
0.6637	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD5240	Approved
0.6637	Remote Similarity	NPD5237	Approved
0.6637	Remote Similarity	NPD5239	Approved
0.6615	Remote Similarity	NPD3748	Approved
0.6615	Remote Similarity	NPD4308	Phase 3
0.6615	Remote Similarity	NPD2799	Discontinued
0.6614	Remote Similarity	NPD520	Approved
0.6613	Remote Similarity	NPD4980	Approved
0.6612	Remote Similarity	NPD1281	Approved
0.6612	Remote Similarity	NPD1535	Discovery
0.6607	Remote Similarity	NPD1358	Approved
0.6589	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD1574	Approved
0.6583	Remote Similarity	NPD5305	Approved
0.6583	Remote Similarity	NPD5306	Approved
0.6583	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD9712	Approved
0.6565	Remote Similarity	NPD5408	Approved
0.6565	Remote Similarity	NPD2935	Discontinued
0.6565	Remote Similarity	NPD5406	Approved
0.6565	Remote Similarity	NPD5404	Approved
0.6565	Remote Similarity	NPD5405	Approved
0.6565	Remote Similarity	NPD1551	Phase 2
0.6557	Remote Similarity	NPD9269	Phase 2
0.6557	Remote Similarity	NPD1608	Approved
0.6545	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD9566	Approved
0.6532	Remote Similarity	NPD2797	Approved
0.6531	Remote Similarity	NPD9250	Approved
0.6518	Remote Similarity	NPD3134	Approved
0.6515	Remote Similarity	NPD2353	Approved
0.6515	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD2346	Discontinued
0.6515	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD2933	Approved
0.6509	Remote Similarity	NPD2934	Approved
0.65	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD1752	Approved
0.6491	Remote Similarity	NPD1756	Approved
0.6489	Remote Similarity	NPD1626	Approved
0.6481	Remote Similarity	NPD253	Approved
0.6481	Remote Similarity	NPD9710	Approved
0.6481	Remote Similarity	NPD9711	Approved
0.6475	Remote Similarity	NPD4807	Approved
0.6475	Remote Similarity	NPD4806	Approved
0.6471	Remote Similarity	NPD1758	Phase 1
0.6466	Remote Similarity	NPD5535	Approved
0.6457	Remote Similarity	NPD6039	Approved
0.6452	Remote Similarity	NPD1283	Approved
0.6452	Remote Similarity	NPD5667	Approved
0.6452	Remote Similarity	NPD3225	Approved
0.6449	Remote Similarity	NPD2859	Approved
0.6449	Remote Similarity	NPD2860	Approved
0.6441	Remote Similarity	NPD255	Approved
0.6441	Remote Similarity	NPD256	Approved
0.6436	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD943	Approved
0.6422	Remote Similarity	NPD3097	Clinical (unspecified phase)

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