NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	244.11
Volume:	249.595
LogP:	2.868
LogD:	2.887
LogS:	-4.66
# Rotatable Bonds:	0
TPSA:	50.44
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.763
Synthetic Accessibility Score:	4.672
Fsp3:	0.533
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:	-4.694
MDCK Permeability:	1.99232545128325e-05
Pgp-inhibitor:	0.086
Pgp-substrate:	0.094
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.044
Plasma Protein Binding (PPB):	97.90179443359375%
Volume Distribution (VD):	1.112
Pgp-substrate:	3.639178991317749%

ADMET: Metabolism

CYP1A2-inhibitor:	0.91
CYP1A2-substrate:	0.842
CYP2C19-inhibitor:	0.175
CYP2C19-substrate:	0.596
CYP2C9-inhibitor:	0.587
CYP2C9-substrate:	0.341
CYP2D6-inhibitor:	0.312
CYP2D6-substrate:	0.344
CYP3A4-inhibitor:	0.161
CYP3A4-substrate:	0.273

ADMET: Excretion

Clearance (CL):	10.485
Half-life (T1/2):	0.287

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.763
Drug-inuced Liver Injury (DILI):	0.861
AMES Toxicity:	0.196
Rat Oral Acute Toxicity:	0.451
Maximum Recommended Daily Dose:	0.589
Skin Sensitization:	0.474
Carcinogencity:	0.889
Eye Corrosion:	0.007
Eye Irritation:	0.02
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC472954

Natural Product ID:	NPC472954
*Common Name:**	BMSHIMSHONQYAQ-WLGFQKAXSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BMSHIMSHONQYAQ-WLGFQKAXSA-N
Standard InCHI:	InChI=1S/C15H16O3/c1-6-8-4-9(8)15(3)5-10-11(13(16)12(6)15)7(2)14(17)18-10/h5,8-9,12-13,16H,1,4H2,2-3H3/t8-,9-,12-,13+,15+/m0/s1
SMILES:	C=C1[C@@H]2C[C@@H]2[C@@]2([C@@H]1[C@H](O)C1=C(C)C(=O)OC1=C2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3594186
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*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
NPO17612	Xanthium sibiricum	Species	Asteraceae	Eukaryota	Fruits	n.a.	n.a.	PMID[26110443]
NPO17612	Xanthium sibiricum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17612	Xanthium sibiricum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17612	Xanthium sibiricum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17612	Xanthium sibiricum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17612	Xanthium sibiricum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	3

Activity Type	# Activity
NON-MOLECULAR	2
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3119	Organism	Human coxsackievirus B3	Human coxsackievirus B3	IC50	>	35000.0	nM	PMID[461225]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[461225]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	35000.0	nM	PMID[461225]

☑ 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 NPC472954 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	1101
0.2-0.3	4487
0.3-0.4	12669
0.4-0.5	12837
0.5-0.6	7161
0.6-0.7	3886
0.7-0.8	360
0.8-0.85	7
0.85-0.9	2
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9432	High Similarity	NPC2882
0.8667	High Similarity	NPC471956
0.8315	Intermediate Similarity	NPC321385
0.8315	Intermediate Similarity	NPC472377
0.7957	Intermediate Similarity	NPC471657
0.7957	Intermediate Similarity	NPC45957
0.7957	Intermediate Similarity	NPC312561
0.7935	Intermediate Similarity	NPC471185
0.7912	Intermediate Similarity	NPC311070
0.7912	Intermediate Similarity	NPC474809
0.7895	Intermediate Similarity	NPC221111
0.7895	Intermediate Similarity	NPC182136
0.7895	Intermediate Similarity	NPC280149
0.7889	Intermediate Similarity	NPC475944
0.7879	Intermediate Similarity	NPC181147
0.7872	Intermediate Similarity	NPC472378
0.7857	Intermediate Similarity	NPC16967
0.7843	Intermediate Similarity	NPC472822
0.7843	Intermediate Similarity	NPC200861
0.7841	Intermediate Similarity	NPC54996
0.7841	Intermediate Similarity	NPC262747
0.7841	Intermediate Similarity	NPC315394
0.7835	Intermediate Similarity	NPC191521
0.78	Intermediate Similarity	NPC227865
0.7767	Intermediate Similarity	NPC81630
0.7753	Intermediate Similarity	NPC209135
0.7753	Intermediate Similarity	NPC474816
0.7732	Intermediate Similarity	NPC162615
0.7732	Intermediate Similarity	NPC152778
0.7732	Intermediate Similarity	NPC205034
0.7708	Intermediate Similarity	NPC281942
0.7708	Intermediate Similarity	NPC232426
0.7708	Intermediate Similarity	NPC310479
0.7677	Intermediate Similarity	NPC320231
0.7677	Intermediate Similarity	NPC319861
0.7677	Intermediate Similarity	NPC165632
0.767	Intermediate Similarity	NPC121099
0.7634	Intermediate Similarity	NPC474693
0.7629	Intermediate Similarity	NPC141831
0.7624	Intermediate Similarity	NPC469864
0.7624	Intermediate Similarity	NPC469872
0.7619	Intermediate Similarity	NPC220155
0.7604	Intermediate Similarity	NPC470734
0.7604	Intermediate Similarity	NPC212664
0.7604	Intermediate Similarity	NPC225283
0.76	Intermediate Similarity	NPC205143
0.76	Intermediate Similarity	NPC53844
0.76	Intermediate Similarity	NPC202705
0.76	Intermediate Similarity	NPC141401
0.76	Intermediate Similarity	NPC208094
0.7582	Intermediate Similarity	NPC268827
0.7573	Intermediate Similarity	NPC183570
0.7556	Intermediate Similarity	NPC184737
0.7553	Intermediate Similarity	NPC471795
0.7553	Intermediate Similarity	NPC474694
0.7553	Intermediate Similarity	NPC473659
0.7553	Intermediate Similarity	NPC475860
0.7551	Intermediate Similarity	NPC59646
0.7551	Intermediate Similarity	NPC115021
0.7527	Intermediate Similarity	NPC12283
0.7527	Intermediate Similarity	NPC474193
0.7527	Intermediate Similarity	NPC472473
0.7527	Intermediate Similarity	NPC42476
0.7526	Intermediate Similarity	NPC3436
0.7526	Intermediate Similarity	NPC78973
0.7525	Intermediate Similarity	NPC278673
0.7523	Intermediate Similarity	NPC106446
0.75	Intermediate Similarity	NPC260796
0.75	Intermediate Similarity	NPC78677
0.75	Intermediate Similarity	NPC472810
0.75	Intermediate Similarity	NPC260343
0.75	Intermediate Similarity	NPC473153
0.75	Intermediate Similarity	NPC162346
0.75	Intermediate Similarity	NPC59994
0.75	Intermediate Similarity	NPC190713
0.75	Intermediate Similarity	NPC472809
0.7475	Intermediate Similarity	NPC470521
0.7475	Intermediate Similarity	NPC53685
0.7475	Intermediate Similarity	NPC470255
0.7475	Intermediate Similarity	NPC298973
0.7475	Intermediate Similarity	NPC104925
0.7474	Intermediate Similarity	NPC131813
0.7474	Intermediate Similarity	NPC477668
0.7451	Intermediate Similarity	NPC290802
0.7449	Intermediate Similarity	NPC472953
0.7449	Intermediate Similarity	NPC472814
0.7449	Intermediate Similarity	NPC212948
0.7449	Intermediate Similarity	NPC177037
0.7449	Intermediate Similarity	NPC470520
0.7447	Intermediate Similarity	NPC31086
0.7447	Intermediate Similarity	NPC82297
0.7447	Intermediate Similarity	NPC474865
0.7423	Intermediate Similarity	NPC474396
0.7423	Intermediate Similarity	NPC50488
0.7423	Intermediate Similarity	NPC146554
0.7419	Intermediate Similarity	NPC471298
0.7419	Intermediate Similarity	NPC323251
0.7404	Intermediate Similarity	NPC280566
0.7404	Intermediate Similarity	NPC476237
0.7404	Intermediate Similarity	NPC297617
0.74	Intermediate Similarity	NPC295347
0.74	Intermediate Similarity	NPC220221
0.74	Intermediate Similarity	NPC329435
0.7396	Intermediate Similarity	NPC191283
0.7396	Intermediate Similarity	NPC475678
0.7396	Intermediate Similarity	NPC473891
0.7374	Intermediate Similarity	NPC32862
0.7374	Intermediate Similarity	NPC472812
0.7374	Intermediate Similarity	NPC156553
0.7374	Intermediate Similarity	NPC40821
0.7374	Intermediate Similarity	NPC214697
0.7374	Intermediate Similarity	NPC272293
0.7368	Intermediate Similarity	NPC473251
0.7368	Intermediate Similarity	NPC42586
0.7368	Intermediate Similarity	NPC245434
0.7356	Intermediate Similarity	NPC316029
0.7353	Intermediate Similarity	NPC92275
0.7353	Intermediate Similarity	NPC98868
0.7353	Intermediate Similarity	NPC474440
0.7347	Intermediate Similarity	NPC469368
0.734	Intermediate Similarity	NPC471297
0.734	Intermediate Similarity	NPC477667
0.734	Intermediate Similarity	NPC193198
0.7333	Intermediate Similarity	NPC309190
0.7333	Intermediate Similarity	NPC161775
0.7333	Intermediate Similarity	NPC476317
0.7333	Intermediate Similarity	NPC272632
0.7308	Intermediate Similarity	NPC32577
0.7308	Intermediate Similarity	NPC114540
0.7308	Intermediate Similarity	NPC155332
0.73	Intermediate Similarity	NPC476186
0.73	Intermediate Similarity	NPC96541
0.73	Intermediate Similarity	NPC166143
0.73	Intermediate Similarity	NPC471994
0.73	Intermediate Similarity	NPC469697
0.73	Intermediate Similarity	NPC120351
0.7292	Intermediate Similarity	NPC471219
0.7292	Intermediate Similarity	NPC329692
0.7283	Intermediate Similarity	NPC242767
0.7282	Intermediate Similarity	NPC201406
0.7273	Intermediate Similarity	NPC74296
0.7273	Intermediate Similarity	NPC32494
0.7273	Intermediate Similarity	NPC175842
0.7273	Intermediate Similarity	NPC110923
0.7273	Intermediate Similarity	NPC234335
0.7273	Intermediate Similarity	NPC72845
0.7273	Intermediate Similarity	NPC472811
0.7264	Intermediate Similarity	NPC34768
0.7264	Intermediate Similarity	NPC266570
0.7264	Intermediate Similarity	NPC85670
0.7263	Intermediate Similarity	NPC472326
0.7263	Intermediate Similarity	NPC126518
0.7263	Intermediate Similarity	NPC471301
0.7255	Intermediate Similarity	NPC69385
0.7255	Intermediate Similarity	NPC231751
0.7253	Intermediate Similarity	NPC473825
0.7253	Intermediate Similarity	NPC476439
0.7253	Intermediate Similarity	NPC189206
0.7248	Intermediate Similarity	NPC474315
0.7245	Intermediate Similarity	NPC177141
0.7245	Intermediate Similarity	NPC262858
0.7245	Intermediate Similarity	NPC472240
0.7245	Intermediate Similarity	NPC5509
0.7241	Intermediate Similarity	NPC475004
0.7238	Intermediate Similarity	NPC97487
0.7238	Intermediate Similarity	NPC10232
0.7238	Intermediate Similarity	NPC112009
0.7238	Intermediate Similarity	NPC23584
0.7238	Intermediate Similarity	NPC187302
0.7238	Intermediate Similarity	NPC196471
0.7238	Intermediate Similarity	NPC189588
0.7234	Intermediate Similarity	NPC324170
0.7228	Intermediate Similarity	NPC469873
0.7228	Intermediate Similarity	NPC209355
0.7228	Intermediate Similarity	NPC293052
0.7228	Intermediate Similarity	NPC276110
0.7222	Intermediate Similarity	NPC137911
0.7222	Intermediate Similarity	NPC228477
0.7222	Intermediate Similarity	NPC75389
0.7222	Intermediate Similarity	NPC257853
0.7216	Intermediate Similarity	NPC471796
0.7216	Intermediate Similarity	NPC476600
0.7212	Intermediate Similarity	NPC99411
0.7212	Intermediate Similarity	NPC244456
0.7212	Intermediate Similarity	NPC115899
0.7212	Intermediate Similarity	NPC469657
0.7204	Intermediate Similarity	NPC10636
0.72	Intermediate Similarity	NPC476304
0.72	Intermediate Similarity	NPC38232
0.72	Intermediate Similarity	NPC53555
0.72	Intermediate Similarity	NPC139692
0.7196	Intermediate Similarity	NPC302788
0.7196	Intermediate Similarity	NPC179380
0.7196	Intermediate Similarity	NPC79298
0.7196	Intermediate Similarity	NPC91034
0.7196	Intermediate Similarity	NPC475074
0.7196	Intermediate Similarity	NPC43063
0.7191	Intermediate Similarity	NPC222244
0.7191	Intermediate Similarity	NPC16349
0.7188	Intermediate Similarity	NPC106416

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 NPC472954 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	156
0.1-0.2	1438
0.2-0.3	3876
0.3-0.4	2582
0.4-0.5	709
0.5-0.6	280
0.6-0.7	109
0.7-0.8	0
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
0.7449	Intermediate Similarity	NPD7637	Suspended
0.7263	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD6695	Phase 3
0.7128	Intermediate Similarity	NPD6902	Approved
0.7097	Intermediate Similarity	NPD6929	Approved
0.7083	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD6930	Phase 2
0.7021	Intermediate Similarity	NPD6931	Approved
0.7019	Intermediate Similarity	NPD4225	Approved
0.6952	Remote Similarity	NPD7639	Approved
0.6952	Remote Similarity	NPD7640	Approved
0.6882	Remote Similarity	NPD6925	Approved
0.6882	Remote Similarity	NPD5776	Phase 2
0.6875	Remote Similarity	NPD6053	Discontinued
0.6869	Remote Similarity	NPD7524	Approved
0.6869	Remote Similarity	NPD7750	Discontinued
0.6857	Remote Similarity	NPD7638	Approved
0.6842	Remote Similarity	NPD7514	Phase 3
0.6837	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7838	Discovery
0.6832	Remote Similarity	NPD5785	Approved
0.6809	Remote Similarity	NPD7145	Approved
0.6804	Remote Similarity	NPD5362	Discontinued
0.6804	Remote Similarity	NPD7154	Phase 3
0.6783	Remote Similarity	NPD7115	Discovery
0.6768	Remote Similarity	NPD5279	Phase 3
0.6768	Remote Similarity	NPD4249	Approved
0.6739	Remote Similarity	NPD6924	Approved
0.6739	Remote Similarity	NPD6926	Approved
0.6731	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD5209	Approved
0.67	Remote Similarity	NPD4251	Approved
0.67	Remote Similarity	NPD4250	Approved
0.6699	Remote Similarity	NPD5779	Approved
0.6699	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD6893	Approved
0.6667	Remote Similarity	NPD1696	Phase 3
0.6667	Remote Similarity	NPD7332	Phase 2
0.6667	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6648	Approved
0.6633	Remote Similarity	NPD5332	Approved
0.6633	Remote Similarity	NPD5331	Approved
0.6632	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD6084	Phase 2
0.6604	Remote Similarity	NPD6083	Phase 2
0.6602	Remote Similarity	NPD6411	Approved
0.6602	Remote Similarity	NPD7087	Discontinued
0.6598	Remote Similarity	NPD4790	Discontinued
0.6596	Remote Similarity	NPD6933	Approved
0.6574	Remote Similarity	NPD5344	Discontinued
0.6571	Remote Similarity	NPD5695	Phase 3
0.6569	Remote Similarity	NPD6051	Approved
0.6555	Remote Similarity	NPD7503	Approved
0.6549	Remote Similarity	NPD6371	Approved
0.6538	Remote Similarity	NPD6399	Phase 3
0.6526	Remote Similarity	NPD6932	Approved
0.6505	Remote Similarity	NPD6698	Approved
0.6505	Remote Similarity	NPD46	Approved
0.65	Remote Similarity	NPD1694	Approved
0.6495	Remote Similarity	NPD4820	Approved
0.6495	Remote Similarity	NPD4819	Approved
0.6495	Remote Similarity	NPD4821	Approved
0.6495	Remote Similarity	NPD4822	Approved
0.6489	Remote Similarity	NPD8039	Approved
0.6484	Remote Similarity	NPD6923	Approved
0.6484	Remote Similarity	NPD6922	Approved
0.6471	Remote Similarity	NPD6903	Approved
0.6458	Remote Similarity	NPD4268	Approved
0.6458	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD4271	Approved
0.6441	Remote Similarity	NPD7328	Approved
0.6441	Remote Similarity	NPD7327	Approved
0.6436	Remote Similarity	NPD5330	Approved
0.6436	Remote Similarity	NPD6684	Approved
0.6436	Remote Similarity	NPD7521	Approved
0.6436	Remote Similarity	NPD7334	Approved
0.6436	Remote Similarity	NPD6409	Approved
0.6436	Remote Similarity	NPD7146	Approved
0.6429	Remote Similarity	NPD6898	Phase 1
0.6413	Remote Similarity	NPD7143	Approved
0.6413	Remote Similarity	NPD7144	Approved
0.6408	Remote Similarity	NPD6101	Approved
0.6408	Remote Similarity	NPD1695	Approved
0.6408	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.64	Remote Similarity	NPD3133	Approved
0.64	Remote Similarity	NPD3666	Approved
0.64	Remote Similarity	NPD4786	Approved
0.64	Remote Similarity	NPD3665	Phase 1
0.6392	Remote Similarity	NPD6683	Phase 2
0.6389	Remote Similarity	NPD5696	Approved
0.6387	Remote Similarity	NPD7516	Approved
0.6372	Remote Similarity	NPD7320	Approved
0.6372	Remote Similarity	NPD6686	Approved
0.6364	Remote Similarity	NPD7632	Discontinued
0.6364	Remote Similarity	NPD3667	Approved
0.6346	Remote Similarity	NPD5207	Approved
0.6344	Remote Similarity	NPD7152	Approved
0.6344	Remote Similarity	NPD7150	Approved
0.6344	Remote Similarity	NPD7151	Approved
0.6339	Remote Similarity	NPD6675	Approved
0.6339	Remote Similarity	NPD5739	Approved
0.6339	Remote Similarity	NPD7128	Approved
0.6339	Remote Similarity	NPD6402	Approved
0.6337	Remote Similarity	NPD5363	Approved
0.6316	Remote Similarity	NPD8264	Approved
0.6316	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6942	Approved
0.6316	Remote Similarity	NPD7339	Approved
0.6311	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD6672	Approved
0.6311	Remote Similarity	NPD5737	Approved
0.6292	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD5281	Approved
0.6286	Remote Similarity	NPD5693	Phase 1
0.6286	Remote Similarity	NPD5284	Approved
0.6283	Remote Similarity	NPD5697	Approved
0.6283	Remote Similarity	NPD5701	Approved
0.6281	Remote Similarity	NPD8380	Approved
0.6281	Remote Similarity	NPD8378	Approved
0.6281	Remote Similarity	NPD8379	Approved
0.6281	Remote Similarity	NPD8335	Approved
0.6281	Remote Similarity	NPD8033	Approved
0.6281	Remote Similarity	NPD8296	Approved
0.6275	Remote Similarity	NPD3618	Phase 1
0.6262	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4191	Approved
0.625	Remote Similarity	NPD4193	Approved
0.625	Remote Similarity	NPD4192	Approved
0.625	Remote Similarity	NPD5328	Approved
0.625	Remote Similarity	NPD4753	Phase 2
0.625	Remote Similarity	NPD4194	Approved
0.6239	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD6899	Approved
0.6228	Remote Similarity	NPD6881	Approved
0.6214	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.62	Remote Similarity	NPD4269	Approved
0.62	Remote Similarity	NPD4270	Approved
0.6198	Remote Similarity	NPD8377	Approved
0.6198	Remote Similarity	NPD8294	Approved
0.619	Remote Similarity	NPD5692	Phase 3
0.6186	Remote Similarity	NPD4756	Discovery
0.6182	Remote Similarity	NPD6404	Discontinued
0.6174	Remote Similarity	NPD6012	Approved
0.6174	Remote Similarity	NPD6013	Approved
0.6174	Remote Similarity	NPD6014	Approved
0.6174	Remote Similarity	NPD6373	Approved
0.6174	Remote Similarity	NPD6372	Approved
0.6168	Remote Similarity	NPD6001	Approved
0.6168	Remote Similarity	NPD5282	Discontinued
0.6162	Remote Similarity	NPD7509	Discontinued
0.6154	Remote Similarity	NPD4518	Approved
0.6132	Remote Similarity	NPD6079	Approved
0.6132	Remote Similarity	NPD6050	Approved
0.6132	Remote Similarity	NPD5694	Approved
0.6121	Remote Similarity	NPD7102	Approved
0.6121	Remote Similarity	NPD6883	Approved
0.6121	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD7290	Approved
0.6117	Remote Similarity	NPD5280	Approved
0.6117	Remote Similarity	NPD4694	Approved
0.6117	Remote Similarity	NPD5786	Approved
0.6087	Remote Similarity	NPD6011	Approved
0.608	Remote Similarity	NPD7507	Approved
0.6075	Remote Similarity	NPD4202	Approved
0.6071	Remote Similarity	NPD5211	Phase 2
0.6068	Remote Similarity	NPD6650	Approved
0.6068	Remote Similarity	NPD6649	Approved
0.6068	Remote Similarity	NPD8130	Phase 1
0.6068	Remote Similarity	NPD6847	Approved
0.6068	Remote Similarity	NPD6617	Approved
0.6068	Remote Similarity	NPD6869	Approved
0.6063	Remote Similarity	NPD7319	Approved
0.6061	Remote Similarity	NPD4195	Approved
0.6055	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD6008	Approved
0.6053	Remote Similarity	NPD6640	Phase 3
0.604	Remote Similarity	NPD6435	Approved
0.604	Remote Similarity	NPD4223	Phase 3
0.604	Remote Similarity	NPD4221	Approved
0.6019	Remote Similarity	NPD7748	Approved
0.6017	Remote Similarity	NPD8297	Approved
0.6017	Remote Similarity	NPD6882	Approved
0.6	Remote Similarity	NPD5208	Approved
0.6	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5959	Approved
0.6	Remote Similarity	NPD4252	Approved
0.6	Remote Similarity	NPD4755	Approved
0.5982	Remote Similarity	NPD4159	Approved
0.5981	Remote Similarity	NPD7983	Approved
0.5981	Remote Similarity	NPD7515	Phase 2
0.5965	Remote Similarity	NPD5141	Approved
0.5963	Remote Similarity	NPD5210	Approved
0.5963	Remote Similarity	NPD4629	Approved
0.595	Remote Similarity	NPD7505	Discontinued
0.5943	Remote Similarity	NPD6904	Approved
0.5943	Remote Similarity	NPD6080	Approved
0.5943	Remote Similarity	NPD6673	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