NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	206.09
Volume:	214.82
LogP:	1.814
LogD:	1.318
LogS:	-2.36
# Rotatable Bonds:	1
TPSA:	43.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.372
Synthetic Accessibility Score:	4.323
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	3
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.714
MDCK Permeability:	3.711134195327759e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.258
20% Bioavailability (F20%):	0.907
30% Bioavailability (F30%):	0.944

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.205
Plasma Protein Binding (PPB):	74.11908721923828%
Volume Distribution (VD):	1.158
Pgp-substrate:	26.751808166503906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.344
CYP1A2-substrate:	0.099
CYP2C19-inhibitor:	0.07
CYP2C19-substrate:	0.442
CYP2C9-inhibitor:	0.06
CYP2C9-substrate:	0.091
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.122
CYP3A4-inhibitor:	0.17
CYP3A4-substrate:	0.247

ADMET: Excretion

Clearance (CL):	7.942
Half-life (T1/2):	0.732

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.748
Drug-inuced Liver Injury (DILI):	0.233
AMES Toxicity:	0.871
Rat Oral Acute Toxicity:	0.9
Maximum Recommended Daily Dose:	0.959
Skin Sensitization:	0.95
Carcinogencity:	0.937
Eye Corrosion:	0.97
Eye Irritation:	0.987
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC472960

Natural Product ID:	NPC472960
*Common Name:**	BUGXCAHSFQQFOX-XROYCOCOSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BUGXCAHSFQQFOX-XROYCOCOSA-N
Standard InCHI:	InChI=1S/C12H14O3/c1-7-5-11-10(4-3-9(7)6-13)8(2)12(14)15-11/h3,6-7,10-11H,2,4-5H2,1H3/t7-,10+,11-/m0/s1
SMILES:	O=CC1=CC[C@H]2[C@H](C[C@@H]1C)OC(=O)C2=C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3594192
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001245] Gamma butyrolactones

*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
Others	5

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	2
Organism	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	TC50	=	69.3	uM	PMID[558972]
NPT616	Cell Line	MDCK	Canis lupus familiaris	TC50	=	48.1	uM	PMID[558972]
NPT3119	Organism	Human coxsackievirus B3	Human coxsackievirus B3	IC50	=	19200.0	nM	PMID[558972]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3000.0	nM	PMID[558972]
NPT2	Others	Unspecified		Selectivity Index	=	3.6	n.a.	PMID[558972]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	6400.0	nM	PMID[558972]
NPT2	Others	Unspecified		Selectivity Index	=	7.5	n.a.	PMID[558972]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	<	20.0	%	PMID[558972]

☑ 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 NPC472960 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	194
0.1-0.2	1421
0.2-0.3	6892
0.3-0.4	15317
0.4-0.5	10161
0.5-0.6	5956
0.6-0.7	2199
0.7-0.8	472
0.8-0.85	56
0.85-0.9	22
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9189	High Similarity	NPC472959
0.9054	High Similarity	NPC138408
0.9054	High Similarity	NPC226669
0.9054	High Similarity	NPC193351
0.8846	High Similarity	NPC35089
0.8846	High Similarity	NPC10276
0.8831	High Similarity	NPC264227
0.8831	High Similarity	NPC472965
0.8831	High Similarity	NPC63649
0.8816	High Similarity	NPC470240
0.8816	High Similarity	NPC65603
0.8816	High Similarity	NPC476794
0.8718	High Similarity	NPC302426
0.8625	High Similarity	NPC39588
0.859	High Similarity	NPC470244
0.859	High Similarity	NPC470239
0.859	High Similarity	NPC182550
0.8571	High Similarity	NPC41780
0.8571	High Similarity	NPC187568
0.8553	High Similarity	NPC155587
0.8533	High Similarity	NPC472956
0.8481	Intermediate Similarity	NPC223904
0.8442	Intermediate Similarity	NPC235906
0.8421	Intermediate Similarity	NPC476355
0.8415	Intermediate Similarity	NPC161957
0.84	Intermediate Similarity	NPC163003
0.8375	Intermediate Similarity	NPC281949
0.8375	Intermediate Similarity	NPC301477
0.8375	Intermediate Similarity	NPC25684
0.8293	Intermediate Similarity	NPC115786
0.8289	Intermediate Similarity	NPC295633
0.8289	Intermediate Similarity	NPC269206
0.8289	Intermediate Similarity	NPC58956
0.8272	Intermediate Similarity	NPC173609
0.8267	Intermediate Similarity	NPC472955
0.825	Intermediate Similarity	NPC281132
0.825	Intermediate Similarity	NPC69271
0.825	Intermediate Similarity	NPC74673
0.825	Intermediate Similarity	NPC276356
0.8228	Intermediate Similarity	NPC299235
0.8205	Intermediate Similarity	NPC123360
0.8205	Intermediate Similarity	NPC472967
0.8205	Intermediate Similarity	NPC266159
0.8182	Intermediate Similarity	NPC140287
0.8171	Intermediate Similarity	NPC318468
0.8171	Intermediate Similarity	NPC272814
0.8133	Intermediate Similarity	NPC296522
0.8133	Intermediate Similarity	NPC144511
0.8125	Intermediate Similarity	NPC617
0.8101	Intermediate Similarity	NPC195785
0.8101	Intermediate Similarity	NPC15975
0.8095	Intermediate Similarity	NPC150755
0.8095	Intermediate Similarity	NPC107787
0.8095	Intermediate Similarity	NPC284902
0.8072	Intermediate Similarity	NPC472957
0.8072	Intermediate Similarity	NPC472958
0.8023	Intermediate Similarity	NPC268298
0.8	Intermediate Similarity	NPC108816
0.8	Intermediate Similarity	NPC475703
0.8	Intermediate Similarity	NPC128276
0.8	Intermediate Similarity	NPC93763
0.7976	Intermediate Similarity	NPC165162
0.7976	Intermediate Similarity	NPC21471
0.7976	Intermediate Similarity	NPC33570
0.7976	Intermediate Similarity	NPC110405
0.7976	Intermediate Similarity	NPC38468
0.7976	Intermediate Similarity	NPC50362
0.7976	Intermediate Similarity	NPC319795
0.7976	Intermediate Similarity	NPC78089
0.7952	Intermediate Similarity	NPC59097
0.7952	Intermediate Similarity	NPC215294
0.7931	Intermediate Similarity	NPC129419
0.7931	Intermediate Similarity	NPC62815
0.7927	Intermediate Similarity	NPC141810
0.7927	Intermediate Similarity	NPC471325
0.7922	Intermediate Similarity	NPC129665
0.7901	Intermediate Similarity	NPC469690
0.7901	Intermediate Similarity	NPC178277
0.7901	Intermediate Similarity	NPC270126
0.7875	Intermediate Similarity	NPC7563
0.7875	Intermediate Similarity	NPC320630
0.7875	Intermediate Similarity	NPC171204
0.7875	Intermediate Similarity	NPC116177
0.7875	Intermediate Similarity	NPC476028
0.7875	Intermediate Similarity	NPC57744
0.7875	Intermediate Similarity	NPC141789
0.7875	Intermediate Similarity	NPC97516
0.7875	Intermediate Similarity	NPC208223
0.7857	Intermediate Similarity	NPC156485
0.7841	Intermediate Similarity	NPC74103
0.7841	Intermediate Similarity	NPC70595
0.7841	Intermediate Similarity	NPC150978
0.7841	Intermediate Similarity	NPC123177
0.7831	Intermediate Similarity	NPC89555
0.7831	Intermediate Similarity	NPC178676
0.7816	Intermediate Similarity	NPC166919
0.7816	Intermediate Similarity	NPC295312
0.7805	Intermediate Similarity	NPC290508
0.7805	Intermediate Similarity	NPC73052
0.7805	Intermediate Similarity	NPC293418
0.7791	Intermediate Similarity	NPC231889
0.7778	Intermediate Similarity	NPC471465
0.7778	Intermediate Similarity	NPC196653
0.7778	Intermediate Similarity	NPC267231
0.7765	Intermediate Similarity	NPC235792
0.7763	Intermediate Similarity	NPC470256
0.7738	Intermediate Similarity	NPC1761
0.7738	Intermediate Similarity	NPC52609
0.7738	Intermediate Similarity	NPC475947
0.7727	Intermediate Similarity	NPC251385
0.7727	Intermediate Similarity	NPC49342
0.7727	Intermediate Similarity	NPC152467
0.7727	Intermediate Similarity	NPC253144
0.7722	Intermediate Similarity	NPC469643
0.7722	Intermediate Similarity	NPC469641
0.7722	Intermediate Similarity	NPC472966
0.7722	Intermediate Similarity	NPC320537
0.7722	Intermediate Similarity	NPC143979
0.7711	Intermediate Similarity	NPC39411
0.7711	Intermediate Similarity	NPC255580
0.7701	Intermediate Similarity	NPC202672
0.7692	Intermediate Similarity	NPC476275
0.7683	Intermediate Similarity	NPC469620
0.7683	Intermediate Similarity	NPC167881
0.7683	Intermediate Similarity	NPC98557
0.7674	Intermediate Similarity	NPC475461
0.7674	Intermediate Similarity	NPC67493
0.7674	Intermediate Similarity	NPC305475
0.7662	Intermediate Similarity	NPC261398
0.7662	Intermediate Similarity	NPC199557
0.7647	Intermediate Similarity	NPC96259
0.7647	Intermediate Similarity	NPC191476
0.7647	Intermediate Similarity	NPC141193
0.7647	Intermediate Similarity	NPC114979
0.764	Intermediate Similarity	NPC300312
0.764	Intermediate Similarity	NPC111114
0.764	Intermediate Similarity	NPC284185
0.764	Intermediate Similarity	NPC261607
0.7632	Intermediate Similarity	NPC194871
0.7614	Intermediate Similarity	NPC474032
0.7614	Intermediate Similarity	NPC307411
0.7614	Intermediate Similarity	NPC151770
0.759	Intermediate Similarity	NPC233377
0.759	Intermediate Similarity	NPC474510
0.7586	Intermediate Similarity	NPC237540
0.7582	Intermediate Similarity	NPC48803
0.7582	Intermediate Similarity	NPC193645
0.7582	Intermediate Similarity	NPC275960
0.7582	Intermediate Similarity	NPC90121
0.7568	Intermediate Similarity	NPC474658
0.7561	Intermediate Similarity	NPC471220
0.7558	Intermediate Similarity	NPC474547
0.7558	Intermediate Similarity	NPC99395
0.7558	Intermediate Similarity	NPC21469
0.7558	Intermediate Similarity	NPC197903
0.7558	Intermediate Similarity	NPC215364
0.7558	Intermediate Similarity	NPC255307
0.7556	Intermediate Similarity	NPC135776
0.7532	Intermediate Similarity	NPC218477
0.7529	Intermediate Similarity	NPC169575
0.7529	Intermediate Similarity	NPC22611
0.7529	Intermediate Similarity	NPC53867
0.7529	Intermediate Similarity	NPC170377
0.7529	Intermediate Similarity	NPC54468
0.7529	Intermediate Similarity	NPC40746
0.7529	Intermediate Similarity	NPC250315
0.7528	Intermediate Similarity	NPC312042
0.7528	Intermediate Similarity	NPC475748
0.7528	Intermediate Similarity	NPC469718
0.7528	Intermediate Similarity	NPC71533
0.7528	Intermediate Similarity	NPC106510
0.7528	Intermediate Similarity	NPC37607
0.7528	Intermediate Similarity	NPC301969
0.7528	Intermediate Similarity	NPC329857
0.7528	Intermediate Similarity	NPC51004
0.75	Intermediate Similarity	NPC469653
0.75	Intermediate Similarity	NPC259599
0.75	Intermediate Similarity	NPC47635
0.75	Intermediate Similarity	NPC471047
0.75	Intermediate Similarity	NPC294434
0.75	Intermediate Similarity	NPC469631
0.75	Intermediate Similarity	NPC117746
0.75	Intermediate Similarity	NPC42470
0.75	Intermediate Similarity	NPC24417
0.75	Intermediate Similarity	NPC91248
0.75	Intermediate Similarity	NPC469628
0.75	Intermediate Similarity	NPC15499
0.75	Intermediate Similarity	NPC224652
0.75	Intermediate Similarity	NPC325031
0.75	Intermediate Similarity	NPC475906
0.75	Intermediate Similarity	NPC215831
0.7473	Intermediate Similarity	NPC473330
0.7473	Intermediate Similarity	NPC140543
0.7473	Intermediate Similarity	NPC473316
0.7471	Intermediate Similarity	NPC50637
0.7471	Intermediate Similarity	NPC64153
0.7471	Intermediate Similarity	NPC38576
0.7471	Intermediate Similarity	NPC279859
0.747	Intermediate Similarity	NPC89128
0.7444	Intermediate Similarity	NPC208886

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 NPC472960 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	184
0.1-0.2	1985
0.2-0.3	4092
0.3-0.4	1979
0.4-0.5	635
0.5-0.6	225
0.6-0.7	45
0.7-0.8	5
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
0.7976	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD1695	Approved
0.7356	Intermediate Similarity	NPD1694	Approved
0.7011	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD5785	Approved
0.6629	Remote Similarity	NPD5209	Approved
0.6596	Remote Similarity	NPD46	Approved
0.6596	Remote Similarity	NPD6698	Approved
0.6593	Remote Similarity	NPD5363	Approved
0.6588	Remote Similarity	NPD8039	Approved
0.6556	Remote Similarity	NPD7154	Phase 3
0.6522	Remote Similarity	NPD5786	Approved
0.6505	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD6435	Approved
0.6374	Remote Similarity	NPD5362	Discontinued
0.6344	Remote Similarity	NPD7334	Approved
0.6344	Remote Similarity	NPD7146	Approved
0.6344	Remote Similarity	NPD5330	Approved
0.6344	Remote Similarity	NPD6684	Approved
0.6344	Remote Similarity	NPD6409	Approved
0.6344	Remote Similarity	NPD7521	Approved
0.6333	Remote Similarity	NPD5369	Approved
0.6321	Remote Similarity	NPD6371	Approved
0.63	Remote Similarity	NPD4225	Approved
0.6264	Remote Similarity	NPD4269	Approved
0.6264	Remote Similarity	NPD4270	Approved
0.6237	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD5368	Approved
0.622	Remote Similarity	NPD7331	Phase 2
0.6211	Remote Similarity	NPD6903	Approved
0.6211	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD7983	Approved
0.617	Remote Similarity	NPD6422	Discontinued
0.6146	Remote Similarity	NPD6101	Approved
0.6146	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD5778	Approved
0.6122	Remote Similarity	NPD5779	Approved
0.6105	Remote Similarity	NPD3573	Approved
0.6095	Remote Similarity	NPD6008	Approved
0.6082	Remote Similarity	NPD7838	Discovery
0.6055	Remote Similarity	NPD6053	Discontinued
0.6044	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD4252	Approved
0.6042	Remote Similarity	NPD6672	Approved
0.6042	Remote Similarity	NPD5737	Approved
0.602	Remote Similarity	NPD6411	Approved
0.602	Remote Similarity	NPD5693	Phase 1
0.6	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.598	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.596	Remote Similarity	NPD6399	Phase 3
0.5941	Remote Similarity	NPD7839	Suspended
0.5918	Remote Similarity	NPD5207	Approved
0.5904	Remote Similarity	NPD7341	Phase 2
0.59	Remote Similarity	NPD5282	Discontinued
0.59	Remote Similarity	NPD7900	Approved
0.59	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5889	Remote Similarity	NPD4756	Discovery
0.587	Remote Similarity	NPD4821	Approved
0.587	Remote Similarity	NPD4819	Approved
0.587	Remote Similarity	NPD4820	Approved
0.587	Remote Similarity	NPD4822	Approved
0.5851	Remote Similarity	NPD5332	Approved
0.5851	Remote Similarity	NPD5331	Approved
0.5844	Remote Similarity	NPD9298	Approved
0.5842	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD4249	Approved
0.5833	Remote Similarity	NPD6686	Approved
0.5833	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD7638	Approved
0.5824	Remote Similarity	NPD4268	Approved
0.5824	Remote Similarity	NPD4271	Approved
0.5806	Remote Similarity	NPD4790	Discontinued
0.5789	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5784	Remote Similarity	NPD4697	Phase 3
0.5773	Remote Similarity	NPD4250	Approved
0.5773	Remote Similarity	NPD4251	Approved
0.5769	Remote Similarity	NPD7640	Approved
0.5769	Remote Similarity	NPD7639	Approved
0.5743	Remote Similarity	NPD6001	Approved
0.5743	Remote Similarity	NPD7748	Approved
0.5741	Remote Similarity	NPD5697	Approved
0.5728	Remote Similarity	NPD7902	Approved
0.5727	Remote Similarity	NPD2067	Discontinued
0.5714	Remote Similarity	NPD5208	Approved
0.5702	Remote Similarity	NPD7115	Discovery
0.57	Remote Similarity	NPD6079	Approved
0.5688	Remote Similarity	NPD6881	Approved
0.5688	Remote Similarity	NPD6899	Approved
0.5688	Remote Similarity	NPD6011	Approved
0.5686	Remote Similarity	NPD5695	Phase 3
0.5676	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD6650	Approved
0.5676	Remote Similarity	NPD6649	Approved
0.5673	Remote Similarity	NPD5696	Approved
0.567	Remote Similarity	NPD3618	Phase 1
0.5658	Remote Similarity	NPD6927	Phase 3
0.5658	Remote Similarity	NPD28	Approved
0.5658	Remote Similarity	NPD29	Approved
0.5657	Remote Similarity	NPD6673	Approved
0.5657	Remote Similarity	NPD6080	Approved
0.5657	Remote Similarity	NPD6904	Approved
0.5657	Remote Similarity	NPD5328	Approved
0.5657	Remote Similarity	NPD5370	Suspended
0.5652	Remote Similarity	NPD7641	Discontinued
0.5648	Remote Similarity	NPD7128	Approved
0.5648	Remote Similarity	NPD6675	Approved
0.5648	Remote Similarity	NPD5739	Approved
0.5648	Remote Similarity	NPD6402	Approved
0.5636	Remote Similarity	NPD6372	Approved
0.5636	Remote Similarity	NPD6012	Approved
0.5636	Remote Similarity	NPD6013	Approved
0.5636	Remote Similarity	NPD6373	Approved
0.5636	Remote Similarity	NPD6014	Approved
0.5631	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD3666	Approved
0.5625	Remote Similarity	NPD3665	Phase 1
0.5625	Remote Similarity	NPD3133	Approved
0.56	Remote Similarity	NPD5692	Phase 3

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