NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	224.1
Volume:	226.247
LogP:	2.465
LogD:	1.52
LogS:	-2.219
# Rotatable Bonds:	1
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.687
Synthetic Accessibility Score:	4.074
Fsp3:	0.667
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:	-4.975
MDCK Permeability:	4.366465509519912e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.065
20% Bioavailability (F20%):	0.673
30% Bioavailability (F30%):	0.979

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.393
Plasma Protein Binding (PPB):	52.947105407714844%
Volume Distribution (VD):	0.275
Pgp-substrate:	51.402252197265625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.034
CYP1A2-substrate:	0.087
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.091
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.367
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.124
CYP3A4-inhibitor:	0.035
CYP3A4-substrate:	0.251

ADMET: Excretion

Clearance (CL):	5.621
Half-life (T1/2):	0.8

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.194
Drug-inuced Liver Injury (DILI):	0.787
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.626
Maximum Recommended Daily Dose:	0.885
Skin Sensitization:	0.921
Carcinogencity:	0.901
Eye Corrosion:	0.669
Eye Irritation:	0.926
Respiratory Toxicity:	0.877

Download Data

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

Natural Product: NPC472958

Natural Product ID:	NPC472958
*Common Name:**	APKHNFGELYOESS-WDQPUEAGSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	APKHNFGELYOESS-WDQPUEAGSA-N
Standard InCHI:	InChI=1S/C12H16O4/c1-6-5-10-9(7(2)12(15)16-10)4-3-8(6)11(13)14/h3,6-7,9-10H,4-5H2,1-2H3,(H,13,14)/t6-,7+,9+,10-/m0/s1
SMILES:	O=C1O[C@@H]2[C@@H]([C@H]1C)CC=C([C@H](C2)C)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3594190
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

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[476770]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[476770]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	35000.0	nM	PMID[476770]

☑ 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 NPC472958 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	175
0.1-0.2	1089
0.2-0.3	5110
0.3-0.4	11029
0.4-0.5	13275
0.5-0.6	7004
0.6-0.7	3893
0.7-0.8	1041
0.8-0.85	74
0.85-0.9	5
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472957
0.8721	High Similarity	NPC295312
0.8506	High Similarity	NPC474032
0.85	High Similarity	NPC472959
0.8488	Intermediate Similarity	NPC237540
0.8434	Intermediate Similarity	NPC470241
0.8427	Intermediate Similarity	NPC135776
0.8409	Intermediate Similarity	NPC106510
0.8409	Intermediate Similarity	NPC71533
0.8372	Intermediate Similarity	NPC284902
0.8372	Intermediate Similarity	NPC122502
0.8295	Intermediate Similarity	NPC268298
0.8293	Intermediate Similarity	NPC108816
0.8293	Intermediate Similarity	NPC93763
0.8276	Intermediate Similarity	NPC160138
0.8256	Intermediate Similarity	NPC165162
0.8256	Intermediate Similarity	NPC21469
0.825	Intermediate Similarity	NPC472966
0.8242	Intermediate Similarity	NPC304886
0.8235	Intermediate Similarity	NPC250315
0.8235	Intermediate Similarity	NPC318468
0.8222	Intermediate Similarity	NPC475912
0.8202	Intermediate Similarity	NPC51004
0.8202	Intermediate Similarity	NPC129419
0.8202	Intermediate Similarity	NPC301969
0.8202	Intermediate Similarity	NPC37607
0.8202	Intermediate Similarity	NPC474761
0.8202	Intermediate Similarity	NPC62815
0.8202	Intermediate Similarity	NPC476004
0.8193	Intermediate Similarity	NPC470244
0.8193	Intermediate Similarity	NPC470239
0.8182	Intermediate Similarity	NPC227379
0.8182	Intermediate Similarity	NPC202672
0.8182	Intermediate Similarity	NPC474471
0.8182	Intermediate Similarity	NPC153805
0.8182	Intermediate Similarity	NPC473715
0.8172	Intermediate Similarity	NPC23364
0.8161	Intermediate Similarity	NPC67493
0.8132	Intermediate Similarity	NPC81386
0.8132	Intermediate Similarity	NPC470010
0.8132	Intermediate Similarity	NPC323008
0.8132	Intermediate Similarity	NPC474035
0.8132	Intermediate Similarity	NPC470013
0.8132	Intermediate Similarity	NPC303942
0.8132	Intermediate Similarity	NPC477131
0.8132	Intermediate Similarity	NPC262133
0.8132	Intermediate Similarity	NPC90453
0.8132	Intermediate Similarity	NPC57405
0.8118	Intermediate Similarity	NPC89555
0.8111	Intermediate Similarity	NPC261607
0.8111	Intermediate Similarity	NPC473321
0.8111	Intermediate Similarity	NPC111114
0.8111	Intermediate Similarity	NPC300312
0.8111	Intermediate Similarity	NPC30515
0.8101	Intermediate Similarity	NPC472955
0.809	Intermediate Similarity	NPC32922
0.809	Intermediate Similarity	NPC307411
0.8072	Intermediate Similarity	NPC472960
0.8068	Intermediate Similarity	NPC475703
0.8049	Intermediate Similarity	NPC472967
0.8049	Intermediate Similarity	NPC266159
0.8046	Intermediate Similarity	NPC125290
0.8046	Intermediate Similarity	NPC137033
0.8043	Intermediate Similarity	NPC67584
0.8043	Intermediate Similarity	NPC14961
0.8043	Intermediate Similarity	NPC270013
0.8043	Intermediate Similarity	NPC52044
0.8043	Intermediate Similarity	NPC36954
0.8043	Intermediate Similarity	NPC170120
0.8022	Intermediate Similarity	NPC179746
0.8022	Intermediate Similarity	NPC288240
0.8022	Intermediate Similarity	NPC475838
0.8022	Intermediate Similarity	NPC273579
0.8022	Intermediate Similarity	NPC162205
0.8022	Intermediate Similarity	NPC476300
0.8022	Intermediate Similarity	NPC295204
0.8022	Intermediate Similarity	NPC81419
0.8022	Intermediate Similarity	NPC228451
0.8022	Intermediate Similarity	NPC125674
0.8	Intermediate Similarity	NPC144133
0.8	Intermediate Similarity	NPC475855
0.8	Intermediate Similarity	NPC150923
0.8	Intermediate Similarity	NPC312042
0.8	Intermediate Similarity	NPC474742
0.8	Intermediate Similarity	NPC179394
0.8	Intermediate Similarity	NPC473619
0.7979	Intermediate Similarity	NPC221615
0.7978	Intermediate Similarity	NPC91248
0.7976	Intermediate Similarity	NPC89128
0.7975	Intermediate Similarity	NPC296522
0.7975	Intermediate Similarity	NPC144511
0.7957	Intermediate Similarity	NPC476315
0.7957	Intermediate Similarity	NPC213078
0.7955	Intermediate Similarity	NPC164393
0.7955	Intermediate Similarity	NPC470242
0.7955	Intermediate Similarity	NPC305475
0.7955	Intermediate Similarity	NPC475461
0.7952	Intermediate Similarity	NPC65603
0.7952	Intermediate Similarity	NPC476794
0.7952	Intermediate Similarity	NPC320630
0.7952	Intermediate Similarity	NPC470240
0.7952	Intermediate Similarity	NPC116177
0.7952	Intermediate Similarity	NPC7563
0.7938	Intermediate Similarity	NPC100487
0.7935	Intermediate Similarity	NPC198853
0.7935	Intermediate Similarity	NPC474338
0.7935	Intermediate Similarity	NPC474247
0.7935	Intermediate Similarity	NPC127019
0.7931	Intermediate Similarity	NPC141193
0.7931	Intermediate Similarity	NPC114979
0.7931	Intermediate Similarity	NPC96259
0.7931	Intermediate Similarity	NPC476804
0.7931	Intermediate Similarity	NPC191476
0.7931	Intermediate Similarity	NPC165287
0.7927	Intermediate Similarity	NPC226669
0.7927	Intermediate Similarity	NPC193351
0.7927	Intermediate Similarity	NPC138408
0.7912	Intermediate Similarity	NPC184463
0.7912	Intermediate Similarity	NPC12172
0.7912	Intermediate Similarity	NPC475925
0.7912	Intermediate Similarity	NPC208886
0.7912	Intermediate Similarity	NPC131209
0.7912	Intermediate Similarity	NPC133698
0.7901	Intermediate Similarity	NPC472956
0.7895	Intermediate Similarity	NPC288876
0.7889	Intermediate Similarity	NPC166919
0.7882	Intermediate Similarity	NPC474510
0.7872	Intermediate Similarity	NPC161493
0.7865	Intermediate Similarity	NPC179659
0.7865	Intermediate Similarity	NPC248602
0.7865	Intermediate Similarity	NPC118601
0.7865	Intermediate Similarity	NPC231889
0.7857	Intermediate Similarity	NPC128276
0.7857	Intermediate Similarity	NPC196653
0.7857	Intermediate Similarity	NPC192006
0.7857	Intermediate Similarity	NPC223450
0.7857	Intermediate Similarity	NPC267231
0.7857	Intermediate Similarity	NPC243998
0.7857	Intermediate Similarity	NPC471465
0.7849	Intermediate Similarity	NPC475659
0.7849	Intermediate Similarity	NPC213698
0.7849	Intermediate Similarity	NPC471142
0.7849	Intermediate Similarity	NPC477922
0.7841	Intermediate Similarity	NPC476628
0.7841	Intermediate Similarity	NPC474547
0.7841	Intermediate Similarity	NPC28887
0.7841	Intermediate Similarity	NPC197903
0.7841	Intermediate Similarity	NPC215364
0.7841	Intermediate Similarity	NPC99395
0.7841	Intermediate Similarity	NPC235792
0.7841	Intermediate Similarity	NPC255307
0.7835	Intermediate Similarity	NPC475871
0.7835	Intermediate Similarity	NPC110989
0.7835	Intermediate Similarity	NPC475945
0.7826	Intermediate Similarity	NPC212486
0.7826	Intermediate Similarity	NPC476049
0.7816	Intermediate Similarity	NPC39588
0.7816	Intermediate Similarity	NPC52609
0.7816	Intermediate Similarity	NPC40746
0.7816	Intermediate Similarity	NPC170377
0.7816	Intermediate Similarity	NPC169575
0.7816	Intermediate Similarity	NPC11620
0.7816	Intermediate Similarity	NPC1761
0.7816	Intermediate Similarity	NPC272814
0.7805	Intermediate Similarity	NPC476355
0.7802	Intermediate Similarity	NPC473448
0.7802	Intermediate Similarity	NPC77337
0.7791	Intermediate Similarity	NPC281949
0.7791	Intermediate Similarity	NPC25684
0.7791	Intermediate Similarity	NPC24417
0.7791	Intermediate Similarity	NPC301477
0.7791	Intermediate Similarity	NPC35089
0.7791	Intermediate Similarity	NPC325031
0.7791	Intermediate Similarity	NPC52861
0.7791	Intermediate Similarity	NPC10276
0.7789	Intermediate Similarity	NPC141191
0.7789	Intermediate Similarity	NPC473326
0.7778	Intermediate Similarity	NPC178875
0.7778	Intermediate Similarity	NPC281516
0.7778	Intermediate Similarity	NPC476805
0.7766	Intermediate Similarity	NPC279621
0.7766	Intermediate Similarity	NPC477921
0.7766	Intermediate Similarity	NPC473859
0.7766	Intermediate Similarity	NPC230800
0.7766	Intermediate Similarity	NPC185553
0.7765	Intermediate Similarity	NPC63649
0.7765	Intermediate Similarity	NPC264227
0.7765	Intermediate Similarity	NPC182550
0.7765	Intermediate Similarity	NPC472965
0.7755	Intermediate Similarity	NPC203659
0.7755	Intermediate Similarity	NPC474741
0.7753	Intermediate Similarity	NPC107787
0.7753	Intermediate Similarity	NPC64153
0.7742	Intermediate Similarity	NPC476267
0.7742	Intermediate Similarity	NPC167219
0.7738	Intermediate Similarity	NPC15975
0.7738	Intermediate Similarity	NPC41780
0.7738	Intermediate Similarity	NPC57744
0.7738	Intermediate Similarity	NPC187568
0.7738	Intermediate Similarity	NPC195785

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 NPC472958 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	160
0.1-0.2	1688
0.2-0.3	3854
0.3-0.4	2285
0.4-0.5	738
0.5-0.6	316
0.6-0.7	89
0.7-0.8	20
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
0.766	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD5363	Approved
0.7363	Intermediate Similarity	NPD5786	Approved
0.734	Intermediate Similarity	NPD7983	Approved
0.7312	Intermediate Similarity	NPD1695	Approved
0.7263	Intermediate Similarity	NPD5779	Approved
0.7263	Intermediate Similarity	NPD5778	Approved
0.7255	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD46	Approved
0.7234	Intermediate Similarity	NPD5785	Approved
0.7234	Intermediate Similarity	NPD6698	Approved
0.7222	Intermediate Similarity	NPD5362	Discontinued
0.7222	Intermediate Similarity	NPD7154	Phase 3
0.7212	Intermediate Similarity	NPD6371	Approved
0.7174	Intermediate Similarity	NPD4249	Approved
0.7111	Intermediate Similarity	NPD6435	Approved
0.7111	Intermediate Similarity	NPD4270	Approved
0.7111	Intermediate Similarity	NPD4269	Approved
0.7097	Intermediate Similarity	NPD4250	Approved
0.7097	Intermediate Similarity	NPD4251	Approved
0.7065	Intermediate Similarity	NPD1694	Approved
0.7045	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD4252	Approved
0.6889	Remote Similarity	NPD5368	Approved
0.6869	Remote Similarity	NPD7839	Suspended
0.6837	Remote Similarity	NPD5282	Discontinued
0.6832	Remote Similarity	NPD7640	Approved
0.6832	Remote Similarity	NPD7639	Approved
0.6813	Remote Similarity	NPD5369	Approved
0.6759	Remote Similarity	NPD6053	Discontinued
0.6733	Remote Similarity	NPD7638	Approved
0.6733	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD4225	Approved
0.6703	Remote Similarity	NPD4820	Approved
0.6703	Remote Similarity	NPD4821	Approved
0.6703	Remote Similarity	NPD4822	Approved
0.6703	Remote Similarity	NPD4819	Approved
0.6702	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD7838	Discovery
0.6698	Remote Similarity	NPD6686	Approved
0.6667	Remote Similarity	NPD6110	Phase 1
0.6667	Remote Similarity	NPD4271	Approved
0.6667	Remote Similarity	NPD5331	Approved
0.6667	Remote Similarity	NPD5332	Approved
0.6667	Remote Similarity	NPD4268	Approved
0.663	Remote Similarity	NPD4790	Discontinued
0.6598	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD6101	Approved
0.6559	Remote Similarity	NPD5209	Approved
0.6556	Remote Similarity	NPD4756	Discovery
0.6548	Remote Similarity	NPD7331	Phase 2
0.6509	Remote Similarity	NPD6008	Approved
0.6471	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD6411	Approved
0.6465	Remote Similarity	NPD7637	Suspended
0.6429	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6399	Phase 3
0.6364	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD7748	Approved
0.6311	Remote Similarity	NPD7902	Approved
0.6296	Remote Similarity	NPD5697	Approved
0.6293	Remote Similarity	NPD8515	Approved
0.6293	Remote Similarity	NPD8513	Phase 3
0.6293	Remote Similarity	NPD8516	Approved
0.6293	Remote Similarity	NPD8517	Approved
0.6289	Remote Similarity	NPD6409	Approved
0.6289	Remote Similarity	NPD6422	Discontinued
0.6289	Remote Similarity	NPD7334	Approved
0.6289	Remote Similarity	NPD7146	Approved
0.6289	Remote Similarity	NPD5330	Approved
0.6289	Remote Similarity	NPD6684	Approved
0.6289	Remote Similarity	NPD7521	Approved
0.6286	Remote Similarity	NPD5344	Discontinued
0.6275	Remote Similarity	NPD5695	Phase 3
0.6263	Remote Similarity	NPD5370	Suspended
0.625	Remote Similarity	NPD5696	Approved
0.625	Remote Similarity	NPD4632	Approved
0.6239	Remote Similarity	NPD6011	Approved
0.6239	Remote Similarity	NPD6881	Approved
0.6239	Remote Similarity	NPD6899	Approved
0.6235	Remote Similarity	NPD7341	Phase 2
0.6226	Remote Similarity	NPD7632	Discontinued
0.6216	Remote Similarity	NPD6649	Approved
0.6216	Remote Similarity	NPD6650	Approved
0.6211	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD7128	Approved
0.6204	Remote Similarity	NPD6675	Approved
0.6204	Remote Similarity	NPD5739	Approved
0.6204	Remote Similarity	NPD6402	Approved
0.619	Remote Similarity	NPD6648	Approved
0.6182	Remote Similarity	NPD6372	Approved
0.6182	Remote Similarity	NPD6013	Approved
0.6182	Remote Similarity	NPD6014	Approved
0.6182	Remote Similarity	NPD6373	Approved
0.6182	Remote Similarity	NPD6012	Approved
0.6168	Remote Similarity	NPD6647	Phase 2
0.6162	Remote Similarity	NPD6672	Approved
0.6162	Remote Similarity	NPD5737	Approved
0.6162	Remote Similarity	NPD6903	Approved
0.6162	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD8039	Approved
0.6154	Remote Similarity	NPD6083	Phase 2
0.6154	Remote Similarity	NPD6084	Phase 2
0.6147	Remote Similarity	NPD5701	Approved
0.6139	Remote Similarity	NPD6079	Approved
0.6139	Remote Similarity	NPD7515	Phase 2
0.6139	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD6883	Approved
0.6126	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD7102	Approved
0.6126	Remote Similarity	NPD7290	Approved
0.6122	Remote Similarity	NPD3618	Phase 1
0.61	Remote Similarity	NPD5328	Approved
0.6091	Remote Similarity	NPD7320	Approved
0.6087	Remote Similarity	NPD6009	Approved
0.6087	Remote Similarity	NPD7115	Discovery
0.6082	Remote Similarity	NPD3133	Approved
0.6082	Remote Similarity	NPD3665	Phase 1
0.6082	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD3666	Approved
0.6075	Remote Similarity	NPD5211	Phase 2
0.6071	Remote Similarity	NPD6847	Approved
0.6071	Remote Similarity	NPD6617	Approved
0.6071	Remote Similarity	NPD6869	Approved
0.6071	Remote Similarity	NPD8130	Phase 1
0.6068	Remote Similarity	NPD6319	Approved
0.6061	Remote Similarity	NPD3573	Approved
0.6058	Remote Similarity	NPD4697	Phase 3
0.6058	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD5222	Approved
0.6058	Remote Similarity	NPD5221	Approved
0.6036	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD7641	Discontinued
0.6033	Remote Similarity	NPD8074	Phase 3
0.602	Remote Similarity	NPD1696	Phase 3
0.6019	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD7900	Approved
0.6018	Remote Similarity	NPD8297	Approved
0.6018	Remote Similarity	NPD6882	Approved
0.6017	Remote Similarity	NPD5983	Phase 2
0.6	Remote Similarity	NPD6412	Phase 2
0.6	Remote Similarity	NPD7492	Approved
0.6	Remote Similarity	NPD5173	Approved
0.6	Remote Similarity	NPD4695	Discontinued
0.598	Remote Similarity	NPD5284	Approved
0.598	Remote Similarity	NPD5281	Approved
0.5968	Remote Similarity	NPD7260	Phase 2
0.5963	Remote Similarity	NPD5141	Approved
0.5962	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.596	Remote Similarity	NPD4519	Discontinued
0.596	Remote Similarity	NPD4623	Approved
0.596	Remote Similarity	NPD5279	Phase 3
0.5952	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.595	Remote Similarity	NPD6616	Approved
0.595	Remote Similarity	NPD7507	Approved
0.5932	Remote Similarity	NPD6054	Approved
0.593	Remote Similarity	NPD3197	Phase 1
0.5929	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD7604	Phase 2
0.5909	Remote Similarity	NPD5048	Discontinued
0.5902	Remote Similarity	NPD7078	Approved
0.5888	Remote Similarity	NPD5285	Approved
0.5888	Remote Similarity	NPD4696	Approved
0.5888	Remote Similarity	NPD5286	Approved
0.5882	Remote Similarity	NPD368	Approved
0.5882	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD5207	Approved
0.5882	Remote Similarity	NPD6016	Approved
0.5882	Remote Similarity	NPD6015	Approved
0.5876	Remote Similarity	NPD3667	Approved
0.5875	Remote Similarity	NPD3172	Approved
0.5862	Remote Similarity	NPD6868	Approved
0.5862	Remote Similarity	NPD6274	Approved
0.5859	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD7736	Approved
0.5849	Remote Similarity	NPD4755	Approved
0.5833	Remote Similarity	NPD6370	Approved
0.5833	Remote Similarity	NPD5988	Approved
0.5833	Remote Similarity	NPD5223	Approved
0.5825	Remote Similarity	NPD5693	Phase 1
0.5825	Remote Similarity	NPD8035	Phase 2
0.5825	Remote Similarity	NPD8034	Phase 2
0.582	Remote Similarity	NPD6336	Discontinued
0.5816	Remote Similarity	NPD6695	Phase 3
0.5814	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5812	Remote Similarity	NPD6317	Approved
0.581	Remote Similarity	NPD4629	Approved
0.581	Remote Similarity	NPD5210	Approved
0.5806	Remote Similarity	NPD7319	Approved
0.5802	Remote Similarity	NPD3194	Approved
0.5802	Remote Similarity	NPD3195	Phase 2
0.5802	Remote Similarity	NPD3196	Approved
0.5802	Remote Similarity	NPD4266	Approved
0.58	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5798	Remote Similarity	NPD6059	Approved
0.5794	Remote Similarity	NPD6845	Suspended

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