NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	250.16
Volume:	263.425
LogP:	2.487
LogD:	2.51
LogS:	-2.488
# Rotatable Bonds:	3
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.617
Synthetic Accessibility Score:	4.648
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.705
MDCK Permeability:	4.25624311901629e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.073

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.278
Plasma Protein Binding (PPB):	72.95897674560547%
Volume Distribution (VD):	0.846
Pgp-substrate:	28.652202606201172%

ADMET: Metabolism

CYP1A2-inhibitor:	0.293
CYP1A2-substrate:	0.202
CYP2C19-inhibitor:	0.159
CYP2C19-substrate:	0.583
CYP2C9-inhibitor:	0.264
CYP2C9-substrate:	0.24
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.241
CYP3A4-inhibitor:	0.199
CYP3A4-substrate:	0.326

ADMET: Excretion

Clearance (CL):	9.141
Half-life (T1/2):	0.536

ADMET: Toxicity

hERG Blockers:	0.059
Human Hepatotoxicity (H-HT):	0.268
Drug-inuced Liver Injury (DILI):	0.71
AMES Toxicity:	0.079
Rat Oral Acute Toxicity:	0.379
Maximum Recommended Daily Dose:	0.215
Skin Sensitization:	0.944
Carcinogencity:	0.764
Eye Corrosion:	0.631
Eye Irritation:	0.943
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC477920

Natural Product ID:	NPC477920
*Common Name:**	Carabrol
IUPAC Name:	(3aR,4aS,5S,5aR,6aR)-5-(3-hydroxybutyl)-5a-methyl-3-methylidene-3a,4,4a,5,6,6a-hexahydrocyclopropa[f][1]benzofuran-2-one
Synonyms:
Standard InCHIKey:	MTIXBBDFRVGBOQ-WQFFSLPPSA-N
Standard InCHI:	InChI=1S/C15H22O3/c1-8(16)4-5-11-12-6-10-9(2)14(17)18-13(10)7-15(11,12)3/h8,10-13,16H,2,4-7H2,1,3H3/t8?,10-,11+,12+,13-,15-/m1/s1
SMILES:	CC(CC[C@H]1[C@H]2[C@@]1(C[C@@H]3[C@H](C2)C(=C)C(=O)O3)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	15690483
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0000502] Xanthanolides

*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
NPO30031	Siegesbeckia pubescens	Species	Asteraceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[19928884]
NPO30031	Siegesbeckia pubescens	Species	Asteraceae	Eukaryota	aerial part	n.a.	n.a.	PMID[24997688]
NPO30031	Siegesbeckia pubescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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	3
Others	2

Activity Type	# Activity
Cell Line	1
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	18900	nM	PMID[24997688]
NPT2	Others	Unspecified		Inhibition	=	11.61	%	PMID[24997688]
NPT2	Others	Unspecified		IC50	>	10	ug/ml	PMID[24997688]
NPT2	Others	Unspecified		Inhibition	=	39	%	PMID[24997688]

☑ 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 NPC477920 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	181
0.1-0.2	1397
0.2-0.3	5507
0.3-0.4	13972
0.4-0.5	8467
0.5-0.6	6780
0.6-0.7	5425
0.7-0.8	908
0.8-0.85	44
0.85-0.9	11
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9877	High Similarity	NPC470012
0.9398	High Similarity	NPC305029
0.9398	High Similarity	NPC181103
0.9383	High Similarity	NPC194637
0.9277	High Similarity	NPC85698
0.9268	High Similarity	NPC219011
0.9268	High Similarity	NPC470011
0.9176	High Similarity	NPC116620
0.9048	High Similarity	NPC9231
0.9024	High Similarity	NPC226988
0.8966	High Similarity	NPC233345
0.8966	High Similarity	NPC186363
0.8902	High Similarity	NPC38642
0.8837	High Similarity	NPC277771
0.8824	High Similarity	NPC185638
0.8791	High Similarity	NPC473155
0.8764	High Similarity	NPC225474
0.8764	High Similarity	NPC148000
0.8764	High Similarity	NPC469596
0.8764	High Similarity	NPC24861
0.8681	High Similarity	NPC136781
0.8675	High Similarity	NPC209318
0.8675	High Similarity	NPC223330
0.8667	High Similarity	NPC183012
0.8667	High Similarity	NPC157686
0.8667	High Similarity	NPC259042
0.8588	High Similarity	NPC97505
0.8571	High Similarity	NPC284518
0.8571	High Similarity	NPC93245
0.8506	High Similarity	NPC175293
0.8495	Intermediate Similarity	NPC476303
0.8478	Intermediate Similarity	NPC473963
0.8462	Intermediate Similarity	NPC90014
0.8427	Intermediate Similarity	NPC158488
0.8421	Intermediate Similarity	NPC476237
0.8404	Intermediate Similarity	NPC475958
0.8391	Intermediate Similarity	NPC250981
0.8391	Intermediate Similarity	NPC6979
0.8387	Intermediate Similarity	NPC216478
0.837	Intermediate Similarity	NPC473964
0.837	Intermediate Similarity	NPC228766
0.837	Intermediate Similarity	NPC165528
0.8315	Intermediate Similarity	NPC73995
0.8315	Intermediate Similarity	NPC194642
0.8298	Intermediate Similarity	NPC47024
0.8293	Intermediate Similarity	NPC92489
0.8256	Intermediate Similarity	NPC470948
0.8229	Intermediate Similarity	NPC176883
0.8222	Intermediate Similarity	NPC475776
0.8222	Intermediate Similarity	NPC153853
0.8222	Intermediate Similarity	NPC152467
0.8214	Intermediate Similarity	NPC263951
0.8211	Intermediate Similarity	NPC308824
0.8202	Intermediate Similarity	NPC136879
0.8202	Intermediate Similarity	NPC215831
0.8202	Intermediate Similarity	NPC477302
0.8191	Intermediate Similarity	NPC476806
0.8191	Intermediate Similarity	NPC476807
0.8172	Intermediate Similarity	NPC307164
0.8152	Intermediate Similarity	NPC250075
0.814	Intermediate Similarity	NPC178676
0.8132	Intermediate Similarity	NPC72845
0.8125	Intermediate Similarity	NPC164551
0.8111	Intermediate Similarity	NPC168131
0.8111	Intermediate Similarity	NPC218927
0.8111	Intermediate Similarity	NPC288699
0.8111	Intermediate Similarity	NPC206001
0.8111	Intermediate Similarity	NPC50488
0.8111	Intermediate Similarity	NPC474396
0.8085	Intermediate Similarity	NPC474343
0.8085	Intermediate Similarity	NPC474395
0.8068	Intermediate Similarity	NPC52628
0.8065	Intermediate Similarity	NPC56369
0.8046	Intermediate Similarity	NPC243347
0.8043	Intermediate Similarity	NPC139692
0.8043	Intermediate Similarity	NPC147272
0.8041	Intermediate Similarity	NPC156681
0.8041	Intermediate Similarity	NPC61442
0.8021	Intermediate Similarity	NPC242666
0.8	Intermediate Similarity	NPC252295
0.7978	Intermediate Similarity	NPC329692
0.7957	Intermediate Similarity	NPC471446
0.7957	Intermediate Similarity	NPC473434
0.7957	Intermediate Similarity	NPC57117
0.7957	Intermediate Similarity	NPC474841
0.7955	Intermediate Similarity	NPC130966
0.7935	Intermediate Similarity	NPC49420
0.7931	Intermediate Similarity	NPC123880
0.7931	Intermediate Similarity	NPC471159
0.7917	Intermediate Similarity	NPC474012
0.7917	Intermediate Similarity	NPC476299
0.7917	Intermediate Similarity	NPC470906
0.7895	Intermediate Similarity	NPC474921
0.7889	Intermediate Similarity	NPC312561
0.7872	Intermediate Similarity	NPC210214
0.7865	Intermediate Similarity	NPC110405
0.7857	Intermediate Similarity	NPC72842
0.7857	Intermediate Similarity	NPC476601
0.7849	Intermediate Similarity	NPC166346
0.7849	Intermediate Similarity	NPC294263
0.7841	Intermediate Similarity	NPC22611
0.7835	Intermediate Similarity	NPC111292
0.7826	Intermediate Similarity	NPC469368
0.7816	Intermediate Similarity	NPC473420
0.7816	Intermediate Similarity	NPC475951
0.7812	Intermediate Similarity	NPC23364
0.7802	Intermediate Similarity	NPC473229
0.7802	Intermediate Similarity	NPC477128
0.78	Intermediate Similarity	NPC78966
0.78	Intermediate Similarity	NPC284732
0.78	Intermediate Similarity	NPC110496
0.7791	Intermediate Similarity	NPC470239
0.7791	Intermediate Similarity	NPC470244
0.7789	Intermediate Similarity	NPC242848
0.7789	Intermediate Similarity	NPC472362
0.7789	Intermediate Similarity	NPC13949
0.7789	Intermediate Similarity	NPC154526
0.7789	Intermediate Similarity	NPC134072
0.7789	Intermediate Similarity	NPC104568
0.7789	Intermediate Similarity	NPC234993
0.7789	Intermediate Similarity	NPC472363
0.7778	Intermediate Similarity	NPC283850
0.7778	Intermediate Similarity	NPC56593
0.7766	Intermediate Similarity	NPC471720
0.7766	Intermediate Similarity	NPC477129
0.7766	Intermediate Similarity	NPC66581
0.7766	Intermediate Similarity	NPC477130
0.7765	Intermediate Similarity	NPC474433
0.7755	Intermediate Similarity	NPC31058
0.7755	Intermediate Similarity	NPC469606
0.7755	Intermediate Similarity	NPC273005
0.7755	Intermediate Similarity	NPC476081
0.7753	Intermediate Similarity	NPC159635
0.7753	Intermediate Similarity	NPC472326
0.7742	Intermediate Similarity	NPC250753
0.7738	Intermediate Similarity	NPC39362
0.7732	Intermediate Similarity	NPC201406
0.7723	Intermediate Similarity	NPC37628
0.7723	Intermediate Similarity	NPC275539
0.7723	Intermediate Similarity	NPC189075
0.7717	Intermediate Similarity	NPC128496
0.7717	Intermediate Similarity	NPC253618
0.7717	Intermediate Similarity	NPC77001
0.7717	Intermediate Similarity	NPC5509
0.7708	Intermediate Similarity	NPC132753
0.7708	Intermediate Similarity	NPC175351
0.7708	Intermediate Similarity	NPC121402
0.7708	Intermediate Similarity	NPC73911
0.7708	Intermediate Similarity	NPC151681
0.7708	Intermediate Similarity	NPC224356
0.7701	Intermediate Similarity	NPC195424
0.77	Intermediate Similarity	NPC469607
0.7692	Intermediate Similarity	NPC476932
0.7684	Intermediate Similarity	NPC98639
0.7684	Intermediate Similarity	NPC316215
0.7677	Intermediate Similarity	NPC120321
0.7677	Intermediate Similarity	NPC470310
0.7677	Intermediate Similarity	NPC99510
0.7677	Intermediate Similarity	NPC36688
0.7674	Intermediate Similarity	NPC35574
0.7667	Intermediate Similarity	NPC76518
0.7667	Intermediate Similarity	NPC177932
0.7667	Intermediate Similarity	NPC86316
0.7667	Intermediate Similarity	NPC106416
0.7667	Intermediate Similarity	NPC476602
0.766	Intermediate Similarity	NPC199543
0.766	Intermediate Similarity	NPC470224
0.766	Intermediate Similarity	NPC63118
0.766	Intermediate Similarity	NPC115021
0.766	Intermediate Similarity	NPC49776
0.766	Intermediate Similarity	NPC474436
0.7653	Intermediate Similarity	NPC81530
0.7653	Intermediate Similarity	NPC471412
0.7653	Intermediate Similarity	NPC303559
0.7647	Intermediate Similarity	NPC474243
0.764	Intermediate Similarity	NPC471037
0.7634	Intermediate Similarity	NPC232426
0.7634	Intermediate Similarity	NPC281942
0.7634	Intermediate Similarity	NPC310479
0.7629	Intermediate Similarity	NPC278386
0.7629	Intermediate Similarity	NPC473154
0.7629	Intermediate Similarity	NPC57079
0.7629	Intermediate Similarity	NPC124512
0.7629	Intermediate Similarity	NPC478056
0.7629	Intermediate Similarity	NPC316598
0.7629	Intermediate Similarity	NPC234617
0.7629	Intermediate Similarity	NPC98868
0.7629	Intermediate Similarity	NPC108368
0.7629	Intermediate Similarity	NPC159763
0.7629	Intermediate Similarity	NPC16911
0.7629	Intermediate Similarity	NPC124703
0.7629	Intermediate Similarity	NPC78427
0.7624	Intermediate Similarity	NPC470952
0.7619	Intermediate Similarity	NPC199316
0.7619	Intermediate Similarity	NPC102313
0.7614	Intermediate Similarity	NPC47635
0.7614	Intermediate Similarity	NPC475665
0.7609	Intermediate Similarity	NPC226863
0.7609	Intermediate Similarity	NPC146937
0.7604	Intermediate Similarity	NPC200054

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 NPC477920 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	178
0.1-0.2	1916
0.2-0.3	3917
0.3-0.4	2144
0.4-0.5	575
0.5-0.6	250
0.6-0.7	160
0.7-0.8	10
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7667	Intermediate Similarity	NPD1694	Approved
0.7629	Intermediate Similarity	NPD4225	Approved
0.7473	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD8035	Phase 2
0.7368	Intermediate Similarity	NPD8034	Phase 2
0.7273	Intermediate Similarity	NPD7638	Approved
0.7204	Intermediate Similarity	NPD3618	Phase 1
0.72	Intermediate Similarity	NPD7640	Approved
0.72	Intermediate Similarity	NPD7639	Approved
0.7156	Intermediate Similarity	NPD7115	Discovery
0.7143	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD6399	Phase 3
0.7041	Intermediate Similarity	NPD7748	Approved
0.701	Intermediate Similarity	NPD7515	Phase 2
0.7	Intermediate Similarity	NPD7902	Approved
0.6957	Remote Similarity	NPD3667	Approved
0.6837	Remote Similarity	NPD6079	Approved
0.6822	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD4786	Approved
0.6804	Remote Similarity	NPD5328	Approved
0.68	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD5697	Approved
0.6759	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD5785	Approved
0.6731	Remote Similarity	NPD7632	Discontinued
0.6729	Remote Similarity	NPD6881	Approved
0.6729	Remote Similarity	NPD6899	Approved
0.6729	Remote Similarity	NPD6011	Approved
0.6702	Remote Similarity	NPD4788	Approved
0.67	Remote Similarity	NPD6001	Approved
0.67	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.67	Remote Similarity	NPD7900	Approved
0.6698	Remote Similarity	NPD6675	Approved
0.6698	Remote Similarity	NPD6008	Approved
0.6698	Remote Similarity	NPD7128	Approved
0.6698	Remote Similarity	NPD6402	Approved
0.6698	Remote Similarity	NPD5739	Approved
0.6697	Remote Similarity	NPD6649	Approved
0.6697	Remote Similarity	NPD6650	Approved
0.6667	Remote Similarity	NPD6684	Approved
0.6667	Remote Similarity	NPD6372	Approved
0.6667	Remote Similarity	NPD7146	Approved
0.6667	Remote Similarity	NPD6117	Approved
0.6667	Remote Similarity	NPD6014	Approved
0.6667	Remote Similarity	NPD6013	Approved
0.6667	Remote Similarity	NPD6373	Approved
0.6667	Remote Similarity	NPD6012	Approved
0.6667	Remote Similarity	NPD5330	Approved
0.6667	Remote Similarity	NPD6409	Approved
0.6667	Remote Similarity	NPD7521	Approved
0.6667	Remote Similarity	NPD7334	Approved
0.6636	Remote Similarity	NPD5701	Approved
0.6633	Remote Similarity	NPD1695	Approved
0.6632	Remote Similarity	NPD3665	Phase 1
0.6632	Remote Similarity	NPD3666	Approved
0.6632	Remote Similarity	NPD3133	Approved
0.6629	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD7290	Approved
0.6606	Remote Similarity	NPD6883	Approved
0.6606	Remote Similarity	NPD7102	Approved
0.66	Remote Similarity	NPD4202	Approved
0.6598	Remote Similarity	NPD3573	Approved
0.6593	Remote Similarity	NPD6116	Phase 1
0.6574	Remote Similarity	NPD7320	Approved
0.6574	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD6686	Approved
0.6569	Remote Similarity	NPD5222	Approved
0.6569	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD4697	Phase 3
0.6569	Remote Similarity	NPD5221	Approved
0.6562	Remote Similarity	NPD1696	Phase 3
0.6562	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD8130	Phase 1
0.6545	Remote Similarity	NPD6847	Approved
0.6545	Remote Similarity	NPD6869	Approved
0.6545	Remote Similarity	NPD6617	Approved
0.6531	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD6903	Approved
0.6522	Remote Similarity	NPD6697	Approved
0.6522	Remote Similarity	NPD6118	Approved
0.6522	Remote Similarity	NPD6115	Approved
0.6522	Remote Similarity	NPD6114	Approved
0.6505	Remote Similarity	NPD6083	Phase 2
0.6505	Remote Similarity	NPD6084	Phase 2
0.6505	Remote Similarity	NPD5173	Approved
0.65	Remote Similarity	NPD6411	Approved
0.6486	Remote Similarity	NPD8297	Approved
0.6486	Remote Similarity	NPD6882	Approved
0.6481	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5695	Phase 3
0.6455	Remote Similarity	NPD6371	Approved
0.6442	Remote Similarity	NPD5696	Approved
0.6429	Remote Similarity	NPD8133	Approved
0.6415	Remote Similarity	NPD5211	Phase 2
0.64	Remote Similarity	NPD6698	Approved
0.64	Remote Similarity	NPD46	Approved
0.6396	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD5286	Approved
0.6381	Remote Similarity	NPD5285	Approved
0.6381	Remote Similarity	NPD4696	Approved
0.6364	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5737	Approved
0.6364	Remote Similarity	NPD6672	Approved
0.6364	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD4755	Approved
0.6337	Remote Similarity	NPD5693	Phase 1
0.6327	Remote Similarity	NPD5279	Phase 3
0.6327	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD5344	Discontinued
0.6321	Remote Similarity	NPD5223	Approved
0.6316	Remote Similarity	NPD6274	Approved
0.6316	Remote Similarity	NPD6868	Approved
0.63	Remote Similarity	NPD6101	Approved
0.63	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD5141	Approved
0.6289	Remote Similarity	NPD3668	Phase 3
0.6283	Remote Similarity	NPD4632	Approved
0.6275	Remote Similarity	NPD5778	Approved
0.6275	Remote Similarity	NPD5779	Approved
0.6262	Remote Similarity	NPD5225	Approved
0.6262	Remote Similarity	NPD4633	Approved
0.6262	Remote Similarity	NPD5224	Approved
0.6262	Remote Similarity	NPD5226	Approved
0.6261	Remote Similarity	NPD6317	Approved
0.625	Remote Similarity	NPD5209	Approved
0.6238	Remote Similarity	NPD5207	Approved
0.6226	Remote Similarity	NPD4700	Approved
0.6224	Remote Similarity	NPD5363	Approved
0.6222	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD7604	Phase 2
0.6211	Remote Similarity	NPD4695	Discontinued
0.6207	Remote Similarity	NPD6313	Approved
0.6207	Remote Similarity	NPD6335	Approved
0.6207	Remote Similarity	NPD6314	Approved
0.6204	Remote Similarity	NPD5174	Approved
0.6204	Remote Similarity	NPD5175	Approved
0.6196	Remote Similarity	NPD3703	Phase 2
0.6196	Remote Similarity	NPD8039	Approved
0.6196	Remote Similarity	NPD3702	Approved
0.6186	Remote Similarity	NPD7154	Phase 3
0.6186	Remote Similarity	NPD5362	Discontinued
0.6176	Remote Similarity	NPD5284	Approved
0.6176	Remote Similarity	NPD5281	Approved
0.617	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7100	Approved
0.6154	Remote Similarity	NPD7101	Approved
0.6154	Remote Similarity	NPD4629	Approved
0.6154	Remote Similarity	NPD5210	Approved
0.6146	Remote Similarity	NPD5369	Approved
0.6139	Remote Similarity	NPD4753	Phase 2
0.6129	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD6009	Approved
0.6116	Remote Similarity	NPD7507	Approved
0.6105	Remote Similarity	NPD7645	Phase 2
0.6102	Remote Similarity	NPD6319	Approved
0.6092	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD4270	Approved
0.6082	Remote Similarity	NPD4223	Phase 3
0.6082	Remote Similarity	NPD4269	Approved
0.6082	Remote Similarity	NPD4221	Approved
0.6075	Remote Similarity	NPD6648	Approved
0.6071	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD5282	Discontinued
0.6055	Remote Similarity	NPD4754	Approved
0.6053	Remote Similarity	NPD6053	Discontinued
0.605	Remote Similarity	NPD5983	Phase 2
0.6044	Remote Similarity	NPD5777	Approved
0.6042	Remote Similarity	NPD7525	Registered
0.604	Remote Similarity	NPD5208	Approved
0.6036	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD7492	Approved
0.6023	Remote Similarity	NPD4224	Phase 2
0.6022	Remote Similarity	NPD7339	Approved
0.6022	Remote Similarity	NPD6942	Approved
0.6019	Remote Similarity	NPD7637	Suspended
0.6	Remote Similarity	NPD3698	Phase 2
0.6	Remote Similarity	NPD6098	Approved
0.6	Remote Similarity	NPD5786	Approved
0.6	Remote Similarity	NPD4519	Discontinued
0.6	Remote Similarity	NPD4623	Approved
0.6	Remote Similarity	NPD5690	Phase 2
0.6	Remote Similarity	NPD3617	Approved
0.5984	Remote Similarity	NPD6616	Approved
0.5982	Remote Similarity	NPD5168	Approved
0.5982	Remote Similarity	NPD5128	Approved
0.5982	Remote Similarity	NPD4729	Approved
0.5982	Remote Similarity	NPD4730	Approved
0.598	Remote Similarity	NPD6051	Approved
0.598	Remote Similarity	NPD6904	Approved
0.598	Remote Similarity	NPD6673	Approved
0.598	Remote Similarity	NPD6080	Approved
0.598	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5968	Remote Similarity	NPD7319	Approved
0.5966	Remote Similarity	NPD6054	Approved
0.596	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.596	Remote Similarity	NPD4197	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