NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	262.16
Volume:	289.924
LogP:	3.696
LogD:	3.245
LogS:	-3.202
# Rotatable Bonds:	4
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.576
Synthetic Accessibility Score:	3.23
Fsp3:	0.375
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.632
MDCK Permeability:	1.8718896171776578e-05
Pgp-inhibitor:	0.453
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.951
30% Bioavailability (F30%):	0.719

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.025
Plasma Protein Binding (PPB):	93.75659942626953%
Volume Distribution (VD):	1.034
Pgp-substrate:	4.4649763107299805%

ADMET: Metabolism

CYP1A2-inhibitor:	0.548
CYP1A2-substrate:	0.481
CYP2C19-inhibitor:	0.137
CYP2C19-substrate:	0.213
CYP2C9-inhibitor:	0.146
CYP2C9-substrate:	0.685
CYP2D6-inhibitor:	0.737
CYP2D6-substrate:	0.217
CYP3A4-inhibitor:	0.433
CYP3A4-substrate:	0.281

ADMET: Excretion

Clearance (CL):	5.484
Half-life (T1/2):	0.528

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.091
Drug-inuced Liver Injury (DILI):	0.029
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.139
Maximum Recommended Daily Dose:	0.401
Skin Sensitization:	0.65
Carcinogencity:	0.273
Eye Corrosion:	0.111
Eye Irritation:	0.935
Respiratory Toxicity:	0.291

Download Data

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

Natural Product: NPC53740

Natural Product ID:	NPC53740
*Common Name:**	Comosusol B
IUPAC Name:	2-[(Z)-3-hydroxy-3-methylbut-1-enyl]-5-(2-methylbut-3-en-2-yl)benzene-1,4-diol
Synonyms:	Comosusol B
Standard InCHIKey:	LXQUYFOONKATDQ-FPLPWBNLSA-N
Standard InCHI:	InChI=1S/C16H22O3/c1-6-15(2,3)12-10-13(17)11(9-14(12)18)7-8-16(4,5)19/h6-10,17-19H,1H2,2-5H3/b8-7-
SMILES:	C=CC(C)(C)c1cc(c(/C=CC(C)(C)O)cc1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1773906
PubChem CID:	52952527
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001534] Quinone and hydroquinone lipids [CHEMONTID:0002801] Prenylated hydroquinones

*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
NPO16286	Sporochnus comosus	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]
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]
NPO17714	Blepharispermum zanguebaricum	Species	Asteraceae	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]

☑ 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

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT395	Cell Line	SF-268	Homo sapiens	GI50	=	5000.0	nM	PMID[575721]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	6000.0	nM	PMID[575721]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	=	6000.0	nM	PMID[575721]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	=	6000.0	nM	PMID[575721]
NPT913	Cell Line	CHO-K1	Cricetulus griseus	GI50	=	6000.0	nM	PMID[575721]

☑ 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 NPC53740 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	283
0.1-0.2	1788
0.2-0.3	4147
0.3-0.4	13540
0.4-0.5	7013
0.5-0.6	10775
0.6-0.7	3972
0.7-0.8	874
0.8-0.85	203
0.85-0.9	69
0.9-0.95	30
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9898	High Similarity	NPC47284
0.9394	High Similarity	NPC252105
0.9394	High Similarity	NPC80800
0.9394	High Similarity	NPC477685
0.9388	High Similarity	NPC299762
0.9388	High Similarity	NPC33675
0.9314	High Similarity	NPC320439
0.93	High Similarity	NPC269212
0.93	High Similarity	NPC108497
0.9293	High Similarity	NPC129373
0.9293	High Similarity	NPC248396
0.9293	High Similarity	NPC72729
0.9293	High Similarity	NPC48730
0.9286	High Similarity	NPC475078
0.9286	High Similarity	NPC152097
0.9216	High Similarity	NPC155072
0.9216	High Similarity	NPC310456
0.9192	High Similarity	NPC260775
0.9143	High Similarity	NPC77772
0.9143	High Similarity	NPC266937
0.9143	High Similarity	NPC470770
0.91	High Similarity	NPC12931
0.91	High Similarity	NPC70677
0.91	High Similarity	NPC130756
0.9091	High Similarity	NPC6597
0.9091	High Similarity	NPC79241
0.9057	High Similarity	NPC62867
0.9057	High Similarity	NPC177962
0.9038	High Similarity	NPC306295
0.902	High Similarity	NPC272029
0.902	High Similarity	NPC475225
0.8991	High Similarity	NPC320864
0.899	High Similarity	NPC312132
0.899	High Similarity	NPC259512
0.898	High Similarity	NPC152415
0.8962	High Similarity	NPC54373
0.8962	High Similarity	NPC469912
0.8942	High Similarity	NPC66834
0.8942	High Similarity	NPC474352
0.8922	High Similarity	NPC235762
0.8922	High Similarity	NPC471228
0.8911	High Similarity	NPC174911
0.8899	High Similarity	NPC141001
0.8889	High Similarity	NPC471534
0.8879	High Similarity	NPC302371
0.8878	High Similarity	NPC55903
0.8878	High Similarity	NPC29373
0.8846	High Similarity	NPC469913
0.8835	High Similarity	NPC475580
0.8829	High Similarity	NPC471449
0.8824	High Similarity	NPC12221
0.8785	High Similarity	NPC275627
0.8776	High Similarity	NPC306074
0.8776	High Similarity	NPC231150
0.8725	High Similarity	NPC225506
0.8704	High Similarity	NPC228452
0.87	High Similarity	NPC222146
0.8687	High Similarity	NPC94139
0.8687	High Similarity	NPC306884
0.8687	High Similarity	NPC147284
0.8687	High Similarity	NPC162314
0.8687	High Similarity	NPC210497
0.8687	High Similarity	NPC3358
0.8679	High Similarity	NPC64586
0.8673	High Similarity	NPC192
0.8627	High Similarity	NPC252821
0.8627	High Similarity	NPC122005
0.86	High Similarity	NPC245187
0.86	High Similarity	NPC316301
0.86	High Similarity	NPC27323
0.86	High Similarity	NPC289769
0.8598	High Similarity	NPC473524
0.8585	High Similarity	NPC232523
0.8585	High Similarity	NPC158253
0.8585	High Similarity	NPC204901
0.8571	High Similarity	NPC117115
0.8571	High Similarity	NPC37802
0.8558	High Similarity	NPC233827
0.8544	High Similarity	NPC130103
0.8532	High Similarity	NPC250323
0.8532	High Similarity	NPC98372
0.8529	High Similarity	NPC474073
0.8519	High Similarity	NPC132720
0.8505	High Similarity	NPC68260
0.8505	High Similarity	NPC279887
0.8491	Intermediate Similarity	NPC99836
0.8491	Intermediate Similarity	NPC12640
0.8491	Intermediate Similarity	NPC201662
0.8491	Intermediate Similarity	NPC477814
0.8491	Intermediate Similarity	NPC54765
0.8476	Intermediate Similarity	NPC227458
0.8476	Intermediate Similarity	NPC244513
0.8476	Intermediate Similarity	NPC218879
0.8469	Intermediate Similarity	NPC27974
0.8468	Intermediate Similarity	NPC469719
0.8447	Intermediate Similarity	NPC92730
0.844	Intermediate Similarity	NPC224527
0.844	Intermediate Similarity	NPC260323
0.844	Intermediate Similarity	NPC176279
0.8426	Intermediate Similarity	NPC282855
0.8426	Intermediate Similarity	NPC98392
0.8426	Intermediate Similarity	NPC19808
0.8426	Intermediate Similarity	NPC299568
0.8426	Intermediate Similarity	NPC186385
0.8426	Intermediate Similarity	NPC33728
0.8426	Intermediate Similarity	NPC26013
0.8421	Intermediate Similarity	NPC325544
0.8421	Intermediate Similarity	NPC477037
0.8421	Intermediate Similarity	NPC318581
0.8416	Intermediate Similarity	NPC76938
0.8411	Intermediate Similarity	NPC151477
0.8411	Intermediate Similarity	NPC233320
0.8407	Intermediate Similarity	NPC206205
0.84	Intermediate Similarity	NPC270547
0.84	Intermediate Similarity	NPC155908
0.8396	Intermediate Similarity	NPC138942
0.8393	Intermediate Similarity	NPC92
0.8393	Intermediate Similarity	NPC469663
0.8393	Intermediate Similarity	NPC471668
0.8378	Intermediate Similarity	NPC195922
0.8367	Intermediate Similarity	NPC407
0.8367	Intermediate Similarity	NPC307235
0.8365	Intermediate Similarity	NPC211885
0.8364	Intermediate Similarity	NPC46940
0.835	Intermediate Similarity	NPC77492
0.835	Intermediate Similarity	NPC225464
0.835	Intermediate Similarity	NPC88420
0.8349	Intermediate Similarity	NPC471535
0.8349	Intermediate Similarity	NPC208229
0.8349	Intermediate Similarity	NPC141782
0.8349	Intermediate Similarity	NPC13482
0.8333	Intermediate Similarity	NPC144682
0.8333	Intermediate Similarity	NPC323074
0.8333	Intermediate Similarity	NPC32714
0.8333	Intermediate Similarity	NPC174981
0.8333	Intermediate Similarity	NPC51341
0.8333	Intermediate Similarity	NPC95344
0.8319	Intermediate Similarity	NPC477136
0.8318	Intermediate Similarity	NPC21594
0.8318	Intermediate Similarity	NPC67250
0.8304	Intermediate Similarity	NPC35797
0.8304	Intermediate Similarity	NPC192948
0.8304	Intermediate Similarity	NPC232165
0.8302	Intermediate Similarity	NPC288411
0.8302	Intermediate Similarity	NPC120719
0.8302	Intermediate Similarity	NPC130817
0.8302	Intermediate Similarity	NPC238696
0.8302	Intermediate Similarity	NPC323810
0.8273	Intermediate Similarity	NPC95716
0.8273	Intermediate Similarity	NPC228609
0.8265	Intermediate Similarity	NPC155393
0.8257	Intermediate Similarity	NPC58865
0.8246	Intermediate Similarity	NPC206
0.823	Intermediate Similarity	NPC308311
0.823	Intermediate Similarity	NPC219112
0.823	Intermediate Similarity	NPC38893
0.823	Intermediate Similarity	NPC477137
0.823	Intermediate Similarity	NPC308828
0.822	Intermediate Similarity	NPC248557
0.8218	Intermediate Similarity	NPC304541
0.8214	Intermediate Similarity	NPC268160
0.8208	Intermediate Similarity	NPC302219
0.8208	Intermediate Similarity	NPC242342
0.8208	Intermediate Similarity	NPC71002
0.8208	Intermediate Similarity	NPC94351
0.8208	Intermediate Similarity	NPC249828
0.8208	Intermediate Similarity	NPC146798
0.8208	Intermediate Similarity	NPC313030
0.8208	Intermediate Similarity	NPC168829
0.8208	Intermediate Similarity	NPC53051
0.8208	Intermediate Similarity	NPC85479
0.8208	Intermediate Similarity	NPC24404
0.8208	Intermediate Similarity	NPC106396
0.8208	Intermediate Similarity	NPC222522
0.8208	Intermediate Similarity	NPC168303
0.82	Intermediate Similarity	NPC280347
0.82	Intermediate Similarity	NPC98772
0.82	Intermediate Similarity	NPC177420
0.82	Intermediate Similarity	NPC242240
0.82	Intermediate Similarity	NPC123273
0.82	Intermediate Similarity	NPC318325
0.8198	Intermediate Similarity	NPC26615
0.8198	Intermediate Similarity	NPC228425
0.8198	Intermediate Similarity	NPC166995
0.8198	Intermediate Similarity	NPC474920
0.819	Intermediate Similarity	NPC129176
0.819	Intermediate Similarity	NPC45663
0.819	Intermediate Similarity	NPC294741
0.819	Intermediate Similarity	NPC166761
0.819	Intermediate Similarity	NPC10588
0.8182	Intermediate Similarity	NPC296683
0.8174	Intermediate Similarity	NPC469644
0.8174	Intermediate Similarity	NPC121866
0.8174	Intermediate Similarity	NPC93071
0.8174	Intermediate Similarity	NPC126002
0.8174	Intermediate Similarity	NPC160235
0.8174	Intermediate Similarity	NPC151197
0.8173	Intermediate Similarity	NPC156313
0.8165	Intermediate Similarity	NPC11554
0.8163	Intermediate Similarity	NPC286904

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 NPC53740 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	271
0.1-0.2	1077
0.2-0.3	1437
0.3-0.4	2968
0.4-0.5	1839
0.5-0.6	1144
0.6-0.7	341
0.7-0.8	62
0.8-0.85	6
0.85-0.9	2
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.949	High Similarity	NPD289	Clinical (unspecified phase)
0.9082	High Similarity	NPD844	Approved
0.899	High Similarity	NPD288	Approved
0.8704	High Similarity	NPD7635	Approved
0.86	High Similarity	NPD1432	Clinical (unspecified phase)
0.8426	Intermediate Similarity	NPD4750	Phase 3
0.8333	Intermediate Similarity	NPD1809	Phase 2
0.8317	Intermediate Similarity	NPD845	Approved
0.8304	Intermediate Similarity	NPD6671	Approved
0.8269	Intermediate Similarity	NPD3020	Approved
0.8155	Intermediate Similarity	NPD2860	Approved
0.8155	Intermediate Similarity	NPD2859	Approved
0.8073	Intermediate Similarity	NPD2342	Discontinued
0.8067	Intermediate Similarity	NPD6696	Suspended
0.8058	Intermediate Similarity	NPD2933	Approved
0.8058	Intermediate Similarity	NPD2934	Approved
0.7944	Intermediate Similarity	NPD846	Approved
0.7944	Intermediate Similarity	NPD940	Approved
0.7928	Intermediate Similarity	NPD3021	Approved
0.7928	Intermediate Similarity	NPD3022	Approved
0.7818	Intermediate Similarity	NPD1444	Approved
0.7818	Intermediate Similarity	NPD1445	Approved
0.7797	Intermediate Similarity	NPD4059	Approved
0.7778	Intermediate Similarity	NPD3091	Approved
0.7739	Intermediate Similarity	NPD497	Approved
0.77	Intermediate Similarity	NPD111	Approved
0.7652	Intermediate Similarity	NPD1398	Phase 1
0.7652	Intermediate Similarity	NPD496	Approved
0.7652	Intermediate Similarity	NPD498	Approved
0.7652	Intermediate Similarity	NPD495	Approved
0.7647	Intermediate Similarity	NPD3019	Approved
0.7647	Intermediate Similarity	NPD2932	Approved
0.7632	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD1792	Phase 2
0.7607	Intermediate Similarity	NPD7340	Approved
0.7586	Intermediate Similarity	NPD1793	Approved
0.7586	Intermediate Similarity	NPD1791	Approved
0.7541	Intermediate Similarity	NPD4749	Approved
0.7521	Intermediate Similarity	NPD3092	Approved
0.75	Intermediate Similarity	NPD4626	Approved
0.75	Intermediate Similarity	NPD2229	Approved
0.75	Intermediate Similarity	NPD2234	Approved
0.75	Intermediate Similarity	NPD2228	Approved
0.75	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD3496	Discontinued
0.7419	Intermediate Similarity	NPD3094	Phase 2
0.7402	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD1242	Phase 1
0.736	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD3095	Discontinued
0.7355	Intermediate Similarity	NPD1751	Approved
0.7355	Intermediate Similarity	NPD4589	Approved
0.7347	Intermediate Similarity	NPD9088	Approved
0.7333	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD4625	Phase 3
0.7317	Intermediate Similarity	NPD2233	Approved
0.7317	Intermediate Similarity	NPD2230	Approved
0.7317	Intermediate Similarity	NPD2232	Approved
0.7311	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD2861	Phase 2
0.7258	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD9500	Approved
0.7213	Intermediate Similarity	NPD2286	Discontinued
0.7213	Intermediate Similarity	NPD1778	Approved
0.7193	Intermediate Similarity	NPD968	Approved
0.719	Intermediate Similarity	NPD7330	Discontinued
0.7182	Intermediate Similarity	NPD9273	Approved
0.7179	Intermediate Similarity	NPD228	Approved
0.7165	Intermediate Similarity	NPD5736	Approved
0.7143	Intermediate Similarity	NPD9618	Approved
0.7143	Intermediate Similarity	NPD9614	Approved
0.7131	Intermediate Similarity	NPD4093	Discontinued
0.7131	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD5691	Approved
0.712	Intermediate Similarity	NPD1755	Approved
0.7097	Intermediate Similarity	NPD1201	Approved
0.7097	Intermediate Similarity	NPD1611	Approved
0.7087	Intermediate Similarity	NPD2194	Approved
0.7087	Intermediate Similarity	NPD4624	Approved
0.7087	Intermediate Similarity	NPD2195	Approved
0.7083	Intermediate Similarity	NPD7157	Approved
0.7054	Intermediate Similarity	NPD3028	Approved
0.7049	Intermediate Similarity	NPD5304	Approved
0.7049	Intermediate Similarity	NPD5303	Approved
0.7045	Intermediate Similarity	NPD4097	Suspended
0.7031	Intermediate Similarity	NPD3635	Approved
0.7031	Intermediate Similarity	NPD3636	Approved
0.7031	Intermediate Similarity	NPD3637	Approved
0.7025	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD7636	Approved
0.7018	Intermediate Similarity	NPD9610	Approved
0.7018	Intermediate Similarity	NPD9608	Approved
0.7016	Intermediate Similarity	NPD1980	Approved
0.7016	Intermediate Similarity	NPD1981	Approved
0.7016	Intermediate Similarity	NPD3143	Discontinued
0.7016	Intermediate Similarity	NPD3026	Approved
0.7016	Intermediate Similarity	NPD3023	Approved
0.7016	Intermediate Similarity	NPD1983	Approved
0.7015	Intermediate Similarity	NPD6099	Approved
0.7015	Intermediate Similarity	NPD6100	Approved
0.7008	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD3025	Approved
0.6992	Remote Similarity	NPD3024	Approved
0.6977	Remote Similarity	NPD2606	Approved
0.6977	Remote Similarity	NPD2605	Approved
0.6975	Remote Similarity	NPD9379	Approved
0.6975	Remote Similarity	NPD9377	Approved
0.6967	Remote Similarity	NPD9613	Approved
0.6967	Remote Similarity	NPD9616	Approved
0.6967	Remote Similarity	NPD9615	Approved
0.6947	Remote Similarity	NPD6663	Approved
0.6942	Remote Similarity	NPD709	Approved
0.6939	Remote Similarity	NPD9087	Approved
0.693	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5156	Approved
0.6923	Remote Similarity	NPD5155	Approved
0.6923	Remote Similarity	NPD2684	Approved
0.6917	Remote Similarity	NPD5283	Phase 1
0.6916	Remote Similarity	NPD9295	Approved
0.6911	Remote Similarity	NPD316	Approved
0.6905	Remote Similarity	NPD3070	Discontinued
0.6903	Remote Similarity	NPD1616	Discontinued
0.6899	Remote Similarity	NPD2237	Approved
0.688	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1470	Approved
0.6846	Remote Similarity	NPD3595	Approved
0.6846	Remote Similarity	NPD600	Approved
0.6846	Remote Similarity	NPD3594	Approved
0.6846	Remote Similarity	NPD596	Approved
0.6838	Remote Similarity	NPD290	Approved
0.6829	Remote Similarity	NPD7644	Approved
0.6812	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.68	Remote Similarity	NPD2668	Approved
0.68	Remote Similarity	NPD2667	Approved
0.6794	Remote Similarity	NPD7095	Approved
0.6767	Remote Similarity	NPD6346	Approved
0.6767	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD2238	Phase 2
0.6767	Remote Similarity	NPD3620	Phase 2
0.6767	Remote Similarity	NPD4060	Phase 1
0.6765	Remote Similarity	NPD2935	Discontinued
0.6733	Remote Similarity	NPD9294	Approved
0.6727	Remote Similarity	NPD1088	Approved
0.6723	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD475	Phase 2
0.672	Remote Similarity	NPD1651	Approved
0.672	Remote Similarity	NPD1357	Approved
0.672	Remote Similarity	NPD5585	Approved
0.6719	Remote Similarity	NPD5327	Phase 3
0.6718	Remote Similarity	NPD4908	Phase 1
0.6715	Remote Similarity	NPD4725	Approved
0.6715	Remote Similarity	NPD4726	Approved
0.6715	Remote Similarity	NPD4721	Approved
0.6696	Remote Similarity	NPD4818	Approved
0.6696	Remote Similarity	NPD4817	Approved
0.6694	Remote Similarity	NPD7843	Approved
0.6694	Remote Similarity	NPD1138	Approved
0.6693	Remote Similarity	NPD1610	Phase 2
0.6692	Remote Similarity	NPD839	Approved
0.6692	Remote Similarity	NPD6584	Phase 3
0.6692	Remote Similarity	NPD840	Approved
0.6691	Remote Similarity	NPD7743	Approved
0.6691	Remote Similarity	NPD7742	Approved
0.6691	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9384	Approved
0.6667	Remote Similarity	NPD4198	Discontinued
0.6667	Remote Similarity	NPD256	Approved
0.6667	Remote Similarity	NPD1283	Approved
0.6667	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1101	Approved
0.6667	Remote Similarity	NPD3027	Phase 3
0.6667	Remote Similarity	NPD9381	Approved
0.6667	Remote Similarity	NPD6353	Approved
0.6667	Remote Similarity	NPD255	Approved
0.6642	Remote Similarity	NPD4140	Approved
0.6641	Remote Similarity	NPD4208	Discontinued
0.6641	Remote Similarity	NPD2231	Phase 2
0.6641	Remote Similarity	NPD2235	Phase 2
0.6641	Remote Similarity	NPD4212	Discontinued
0.6641	Remote Similarity	NPD1712	Approved
0.664	Remote Similarity	NPD1759	Phase 1
0.6639	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD74	Approved
0.6639	Remote Similarity	NPD9266	Approved
0.6617	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD2797	Approved
0.6615	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD3055	Approved
0.6615	Remote Similarity	NPD3053	Approved
0.6615	Remote Similarity	NPD4103	Phase 2
0.6613	Remote Similarity	NPD9493	Approved
0.6612	Remote Similarity	NPD1139	Approved
0.6612	Remote Similarity	NPD1137	Approved
0.6596	Remote Similarity	NPD3300	Phase 2
0.6593	Remote Similarity	NPD5735	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