NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	280.17
Volume:	289.511
LogP:	3.003
LogD:	2.92
LogS:	-3.149
# Rotatable Bonds:	1
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.564
Synthetic Accessibility Score:	4.784
Fsp3:	0.812
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.777
MDCK Permeability:	4.134206392336637e-05
Pgp-inhibitor:	0.123
Pgp-substrate:	0.038
Human Intestinal Absorption (HIA):	0.029
20% Bioavailability (F20%):	0.059
30% Bioavailability (F30%):	0.065

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.96
Plasma Protein Binding (PPB):	56.04584503173828%
Volume Distribution (VD):	0.781
Pgp-substrate:	26.965717315673828%

ADMET: Metabolism

CYP1A2-inhibitor:	0.493
CYP1A2-substrate:	0.366
CYP2C19-inhibitor:	0.226
CYP2C19-substrate:	0.767
CYP2C9-inhibitor:	0.054
CYP2C9-substrate:	0.051
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.121
CYP3A4-inhibitor:	0.721
CYP3A4-substrate:	0.29

ADMET: Excretion

Clearance (CL):	8.232
Half-life (T1/2):	0.604

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.103
Drug-inuced Liver Injury (DILI):	0.096
AMES Toxicity:	0.115
Rat Oral Acute Toxicity:	0.52
Maximum Recommended Daily Dose:	0.109
Skin Sensitization:	0.895
Carcinogencity:	0.32
Eye Corrosion:	0.314
Eye Irritation:	0.792
Respiratory Toxicity:	0.695

Download Data

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

Natural Product: NPC469368

Natural Product ID:	NPC469368
*Common Name:**	QMSDSSJNVXCRON-WTGWBGFISA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QMSDSSJNVXCRON-WTGWBGFISA-N
Standard InCHI:	InChI=1S/C16H22O4/c1-8-6-12-13(9(2)15(19)20-12)14(18)10-7-16(10,3)5-4-11(8)17/h6,10-14,17-18H,2,4-5,7H2,1,3H3/b8-6+/t10-,11+,12+,13-,14+,16+/m1/s1
SMILES:	CC1=CC2C(C(C3CC3(CCC1O)C)O)C(=C)C(=O)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1076926
PubChem CID:	46881089
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

*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
NPO8759	Anthemis melanolepis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20112996]

☑ 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
MIC	9

Activity Type	# Activity
Organism	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	12.5	ug.mL-1	PMID[514877]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	12.5	ug.mL-1	PMID[514877]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	1.25	ug.mL-1	PMID[514877]
NPT141	Organism	Agrobacterium tumefaciens	Agrobacterium tumefaciens	MIC	=	25.0	ug.mL-1	PMID[514877]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	50.0	ug.mL-1	PMID[514877]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	25.0	ug.mL-1	PMID[514877]
NPT3729	Organism	Pseudomonas tolaasii	Pseudomonas tolaasii	MIC	=	25.0	ug.mL-1	PMID[514877]
NPT1190	Organism	Salmonella enterica	Salmonella enterica	MIC	=	25.0	ug.mL-1	PMID[514877]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	6.25	ug.mL-1	PMID[514877]

☑ 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 NPC469368 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	198
0.1-0.2	1166
0.2-0.3	4792
0.3-0.4	12484
0.4-0.5	11112
0.5-0.6	6908
0.6-0.7	4571
0.7-0.8	1267
0.8-0.85	131
0.85-0.9	52
0.9-0.95	15
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9405	High Similarity	NPC255307
0.9294	High Similarity	NPC305475
0.9294	High Similarity	NPC475461
0.9286	High Similarity	NPC191476
0.9286	High Similarity	NPC476804
0.9286	High Similarity	NPC114979
0.9167	High Similarity	NPC473390
0.9167	High Similarity	NPC131669
0.9059	High Similarity	NPC96259
0.9059	High Similarity	NPC141193
0.9048	High Similarity	NPC229825
0.8941	High Similarity	NPC40746
0.8941	High Similarity	NPC169575
0.8929	High Similarity	NPC24417
0.8929	High Similarity	NPC52861
0.8889	High Similarity	NPC475838
0.8889	High Similarity	NPC228451
0.8889	High Similarity	NPC125674
0.8864	High Similarity	NPC476803
0.8864	High Similarity	NPC476805
0.8851	High Similarity	NPC150755
0.8837	High Similarity	NPC158756
0.8791	High Similarity	NPC474247
0.8736	High Similarity	NPC165162
0.8736	High Similarity	NPC470755
0.869	High Similarity	NPC98557
0.869	High Similarity	NPC89128
0.869	High Similarity	NPC167881
0.8667	High Similarity	NPC475855
0.8636	High Similarity	NPC469910
0.8605	High Similarity	NPC89555
0.8602	High Similarity	NPC279621
0.8602	High Similarity	NPC230800
0.8571	High Similarity	NPC471465
0.8571	High Similarity	NPC196653
0.8506	High Similarity	NPC59097
0.8488	Intermediate Similarity	NPC141810
0.8478	Intermediate Similarity	NPC475302
0.8462	Intermediate Similarity	NPC144133
0.8462	Intermediate Similarity	NPC179394
0.8452	Intermediate Similarity	NPC7563
0.8452	Intermediate Similarity	NPC320630
0.8452	Intermediate Similarity	NPC116177
0.8452	Intermediate Similarity	NPC476028
0.8452	Intermediate Similarity	NPC171204
0.8452	Intermediate Similarity	NPC141789
0.8444	Intermediate Similarity	NPC475819
0.8427	Intermediate Similarity	NPC50637
0.8421	Intermediate Similarity	NPC141191
0.8409	Intermediate Similarity	NPC82297
0.8387	Intermediate Similarity	NPC57405
0.8387	Intermediate Similarity	NPC303942
0.8353	Intermediate Similarity	NPC108816
0.8353	Intermediate Similarity	NPC93763
0.8352	Intermediate Similarity	NPC474032
0.8352	Intermediate Similarity	NPC218927
0.8352	Intermediate Similarity	NPC206001
0.8333	Intermediate Similarity	NPC68819
0.8333	Intermediate Similarity	NPC235906
0.8333	Intermediate Similarity	NPC288876
0.8316	Intermediate Similarity	NPC169205
0.8298	Intermediate Similarity	NPC14961
0.8298	Intermediate Similarity	NPC471141
0.8298	Intermediate Similarity	NPC270013
0.8298	Intermediate Similarity	NPC304886
0.8295	Intermediate Similarity	NPC474703
0.8295	Intermediate Similarity	NPC116543
0.828	Intermediate Similarity	NPC295204
0.828	Intermediate Similarity	NPC288240
0.828	Intermediate Similarity	NPC475912
0.828	Intermediate Similarity	NPC273579
0.828	Intermediate Similarity	NPC162205
0.8276	Intermediate Similarity	NPC470241
0.8276	Intermediate Similarity	NPC301477
0.8276	Intermediate Similarity	NPC25684
0.8276	Intermediate Similarity	NPC281949
0.8261	Intermediate Similarity	NPC474232
0.8261	Intermediate Similarity	NPC129419
0.8256	Intermediate Similarity	NPC470239
0.8256	Intermediate Similarity	NPC470244
0.8256	Intermediate Similarity	NPC270126
0.8256	Intermediate Similarity	NPC617
0.8242	Intermediate Similarity	NPC136879
0.8242	Intermediate Similarity	NPC473715
0.8242	Intermediate Similarity	NPC477302
0.8211	Intermediate Similarity	NPC473859
0.8211	Intermediate Similarity	NPC185553
0.8211	Intermediate Similarity	NPC476315
0.8202	Intermediate Similarity	NPC472326
0.8191	Intermediate Similarity	NPC474035
0.8191	Intermediate Similarity	NPC167219
0.8191	Intermediate Similarity	NPC81386
0.8172	Intermediate Similarity	NPC473321
0.8161	Intermediate Similarity	NPC281132
0.8152	Intermediate Similarity	NPC166919
0.8152	Intermediate Similarity	NPC295312
0.8152	Intermediate Similarity	NPC268298
0.814	Intermediate Similarity	NPC267231
0.8132	Intermediate Similarity	NPC312561
0.8125	Intermediate Similarity	NPC474343
0.8111	Intermediate Similarity	NPC261380
0.8105	Intermediate Similarity	NPC275960
0.8105	Intermediate Similarity	NPC471142
0.8105	Intermediate Similarity	NPC475659
0.8105	Intermediate Similarity	NPC48803
0.8105	Intermediate Similarity	NPC90121
0.8105	Intermediate Similarity	NPC36954
0.8105	Intermediate Similarity	NPC193645
0.809	Intermediate Similarity	NPC250315
0.8085	Intermediate Similarity	NPC212486
0.8085	Intermediate Similarity	NPC469645
0.8085	Intermediate Similarity	NPC469692
0.8081	Intermediate Similarity	NPC476237
0.8068	Intermediate Similarity	NPC325031
0.8065	Intermediate Similarity	NPC281942
0.8065	Intermediate Similarity	NPC473448
0.8065	Intermediate Similarity	NPC473619
0.8065	Intermediate Similarity	NPC232426
0.8061	Intermediate Similarity	NPC469657
0.8061	Intermediate Similarity	NPC244456
0.8046	Intermediate Similarity	NPC325869
0.8043	Intermediate Similarity	NPC202672
0.8041	Intermediate Similarity	NPC473326
0.8023	Intermediate Similarity	NPC476794
0.8023	Intermediate Similarity	NPC470240
0.8023	Intermediate Similarity	NPC97516
0.8023	Intermediate Similarity	NPC474760
0.8022	Intermediate Similarity	NPC107787
0.8021	Intermediate Similarity	NPC18019
0.8021	Intermediate Similarity	NPC24956
0.8	Intermediate Similarity	NPC121825
0.8	Intermediate Similarity	NPC474338
0.8	Intermediate Similarity	NPC470013
0.8	Intermediate Similarity	NPC295799
0.8	Intermediate Similarity	NPC220964
0.8	Intermediate Similarity	NPC470010
0.8	Intermediate Similarity	NPC477131
0.8	Intermediate Similarity	NPC323008
0.8	Intermediate Similarity	NPC262133
0.8	Intermediate Similarity	NPC155587
0.8	Intermediate Similarity	NPC475676
0.8	Intermediate Similarity	NPC198853
0.798	Intermediate Similarity	NPC118405
0.798	Intermediate Similarity	NPC471148
0.7979	Intermediate Similarity	NPC261607
0.7979	Intermediate Similarity	NPC177037
0.7979	Intermediate Similarity	NPC186363
0.7979	Intermediate Similarity	NPC141831
0.7979	Intermediate Similarity	NPC131209
0.7979	Intermediate Similarity	NPC184463
0.7979	Intermediate Similarity	NPC30515
0.7979	Intermediate Similarity	NPC111114
0.7979	Intermediate Similarity	NPC300312
0.7979	Intermediate Similarity	NPC475925
0.7979	Intermediate Similarity	NPC472814
0.7979	Intermediate Similarity	NPC133698
0.7979	Intermediate Similarity	NPC72845
0.7979	Intermediate Similarity	NPC233345
0.7978	Intermediate Similarity	NPC35556
0.7976	Intermediate Similarity	NPC295633
0.7976	Intermediate Similarity	NPC58956
0.7976	Intermediate Similarity	NPC269206
0.7957	Intermediate Similarity	NPC474396
0.7957	Intermediate Similarity	NPC168131
0.7957	Intermediate Similarity	NPC212664
0.7957	Intermediate Similarity	NPC151770
0.7957	Intermediate Similarity	NPC50488
0.7941	Intermediate Similarity	NPC474664
0.7941	Intermediate Similarity	NPC233379
0.7941	Intermediate Similarity	NPC14862
0.7938	Intermediate Similarity	NPC161493
0.7935	Intermediate Similarity	NPC160138
0.7935	Intermediate Similarity	NPC470012
0.7935	Intermediate Similarity	NPC237540
0.7921	Intermediate Similarity	NPC475802
0.7917	Intermediate Similarity	NPC67584
0.7917	Intermediate Similarity	NPC170120
0.7917	Intermediate Similarity	NPC52044
0.7917	Intermediate Similarity	NPC477922
0.7917	Intermediate Similarity	NPC213698
0.7917	Intermediate Similarity	NPC183012
0.7912	Intermediate Similarity	NPC21469
0.7912	Intermediate Similarity	NPC78089
0.79	Intermediate Similarity	NPC4620
0.79	Intermediate Similarity	NPC69171
0.79	Intermediate Similarity	NPC474165
0.7895	Intermediate Similarity	NPC81419
0.7895	Intermediate Similarity	NPC139692
0.7895	Intermediate Similarity	NPC115021
0.7895	Intermediate Similarity	NPC179746
0.7895	Intermediate Similarity	NPC476300
0.7882	Intermediate Similarity	NPC476355
0.7882	Intermediate Similarity	NPC140287
0.7879	Intermediate Similarity	NPC474339
0.7879	Intermediate Similarity	NPC164598
0.7879	Intermediate Similarity	NPC150923
0.7879	Intermediate Similarity	NPC473332
0.7872	Intermediate Similarity	NPC474761
0.7872	Intermediate Similarity	NPC476004
0.7872	Intermediate Similarity	NPC297474

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 NPC469368 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	186
0.1-0.2	1729
0.2-0.3	3690
0.3-0.4	2435
0.4-0.5	650
0.5-0.6	334
0.6-0.7	101
0.7-0.8	25
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
0.8105	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD5785	Approved
0.7788	Intermediate Similarity	NPD6371	Approved
0.7677	Intermediate Similarity	NPD4225	Approved
0.7527	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD46	Approved
0.75	Intermediate Similarity	NPD6698	Approved
0.75	Intermediate Similarity	NPD7154	Phase 3
0.7396	Intermediate Similarity	NPD1695	Approved
0.7391	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD5363	Approved
0.734	Intermediate Similarity	NPD1694	Approved
0.7333	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5362	Discontinued
0.7204	Intermediate Similarity	NPD4270	Approved
0.7204	Intermediate Similarity	NPD4269	Approved
0.7204	Intermediate Similarity	NPD5209	Approved
0.7174	Intermediate Similarity	NPD4822	Approved
0.7174	Intermediate Similarity	NPD4819	Approved
0.7174	Intermediate Similarity	NPD4821	Approved
0.7174	Intermediate Similarity	NPD4820	Approved
0.717	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7838	Discovery
0.7143	Intermediate Similarity	NPD4271	Approved
0.7143	Intermediate Similarity	NPD4268	Approved
0.7103	Intermediate Similarity	NPD6686	Approved
0.7083	Intermediate Similarity	NPD4249	Approved
0.7083	Intermediate Similarity	NPD5786	Approved
0.7054	Intermediate Similarity	NPD7115	Discovery
0.7021	Intermediate Similarity	NPD6435	Approved
0.701	Intermediate Similarity	NPD4250	Approved
0.701	Intermediate Similarity	NPD4251	Approved
0.7	Intermediate Similarity	NPD5778	Approved
0.7	Intermediate Similarity	NPD5779	Approved
0.7	Intermediate Similarity	NPD6399	Phase 3
0.6989	Remote Similarity	NPD4252	Approved
0.6931	Remote Similarity	NPD5282	Discontinued
0.6923	Remote Similarity	NPD7640	Approved
0.6923	Remote Similarity	NPD7639	Approved
0.6915	Remote Similarity	NPD5369	Approved
0.69	Remote Similarity	NPD7983	Approved
0.69	Remote Similarity	NPD6411	Approved
0.6875	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD7638	Approved
0.6809	Remote Similarity	NPD5368	Approved
0.6771	Remote Similarity	NPD5331	Approved
0.6771	Remote Similarity	NPD5332	Approved
0.6757	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD4790	Discontinued
0.6733	Remote Similarity	NPD7637	Suspended
0.67	Remote Similarity	NPD6101	Approved
0.67	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD5344	Discontinued
0.6667	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.663	Remote Similarity	NPD8039	Approved
0.6577	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6083	Phase 2
0.6571	Remote Similarity	NPD6084	Phase 2
0.6571	Remote Similarity	NPD7902	Approved
0.6552	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD6053	Discontinued
0.6545	Remote Similarity	NPD5697	Approved
0.6538	Remote Similarity	NPD5695	Phase 3
0.6518	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD5696	Approved
0.6495	Remote Similarity	NPD3667	Approved
0.6486	Remote Similarity	NPD6899	Approved
0.6486	Remote Similarity	NPD6881	Approved
0.6476	Remote Similarity	NPD7839	Suspended
0.646	Remote Similarity	NPD6650	Approved
0.646	Remote Similarity	NPD6649	Approved
0.6455	Remote Similarity	NPD6675	Approved
0.6455	Remote Similarity	NPD6402	Approved
0.6455	Remote Similarity	NPD7128	Approved
0.6455	Remote Similarity	NPD5739	Approved
0.6449	Remote Similarity	NPD6648	Approved
0.6442	Remote Similarity	NPD7748	Approved
0.6429	Remote Similarity	NPD6012	Approved
0.6429	Remote Similarity	NPD6014	Approved
0.6429	Remote Similarity	NPD6372	Approved
0.6429	Remote Similarity	NPD6013	Approved
0.6429	Remote Similarity	NPD6373	Approved
0.6408	Remote Similarity	NPD7515	Phase 2
0.64	Remote Similarity	NPD7146	Approved
0.64	Remote Similarity	NPD6409	Approved
0.64	Remote Similarity	NPD7334	Approved
0.64	Remote Similarity	NPD7521	Approved
0.64	Remote Similarity	NPD3618	Phase 1
0.64	Remote Similarity	NPD5330	Approved
0.64	Remote Similarity	NPD6684	Approved
0.6396	Remote Similarity	NPD5701	Approved
0.6381	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD5370	Suspended
0.6372	Remote Similarity	NPD7102	Approved
0.6372	Remote Similarity	NPD7290	Approved
0.6372	Remote Similarity	NPD6883	Approved
0.6364	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3133	Approved
0.6364	Remote Similarity	NPD3665	Phase 1
0.6364	Remote Similarity	NPD4786	Approved
0.6364	Remote Similarity	NPD3666	Approved
0.6339	Remote Similarity	NPD6011	Approved
0.6339	Remote Similarity	NPD7320	Approved
0.633	Remote Similarity	NPD7632	Discontinued
0.633	Remote Similarity	NPD5211	Phase 2
0.6316	Remote Similarity	NPD6617	Approved
0.6316	Remote Similarity	NPD8130	Phase 1
0.6316	Remote Similarity	NPD4756	Discovery
0.6316	Remote Similarity	NPD6847	Approved
0.6316	Remote Similarity	NPD6869	Approved
0.6306	Remote Similarity	NPD6008	Approved
0.63	Remote Similarity	NPD1696	Phase 3
0.6289	Remote Similarity	NPD4695	Discontinued
0.6286	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD7900	Approved
0.6275	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD6672	Approved
0.6275	Remote Similarity	NPD5737	Approved
0.6275	Remote Similarity	NPD6903	Approved
0.6263	Remote Similarity	NPD6695	Phase 3
0.6261	Remote Similarity	NPD6882	Approved
0.6261	Remote Similarity	NPD8297	Approved
0.625	Remote Similarity	NPD8034	Phase 2
0.625	Remote Similarity	NPD8516	Approved
0.625	Remote Similarity	NPD5284	Approved
0.625	Remote Similarity	NPD5693	Phase 1
0.625	Remote Similarity	NPD8035	Phase 2
0.625	Remote Similarity	NPD8513	Phase 3
0.625	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.625	Remote Similarity	NPD8517	Approved
0.625	Remote Similarity	NPD5281	Approved
0.625	Remote Similarity	NPD8515	Approved
0.625	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD5279	Phase 3
0.6226	Remote Similarity	NPD4629	Approved
0.6226	Remote Similarity	NPD5210	Approved
0.6216	Remote Similarity	NPD5141	Approved
0.6214	Remote Similarity	NPD4753	Phase 2
0.6147	Remote Similarity	NPD5286	Approved
0.6147	Remote Similarity	NPD4696	Approved
0.6147	Remote Similarity	NPD5285	Approved
0.6132	Remote Similarity	NPD6001	Approved
0.6111	Remote Similarity	NPD4755	Approved
0.6106	Remote Similarity	NPD6412	Phase 2
0.6102	Remote Similarity	NPD6274	Approved
0.6095	Remote Similarity	NPD6079	Approved
0.6078	Remote Similarity	NPD4519	Discontinued
0.6078	Remote Similarity	NPD4623	Approved
0.6061	Remote Similarity	NPD6902	Approved
0.6058	Remote Similarity	NPD5328	Approved
0.6058	Remote Similarity	NPD6051	Approved
0.6048	Remote Similarity	NPD7507	Approved
0.604	Remote Similarity	NPD3668	Phase 3
0.6038	Remote Similarity	NPD4202	Approved
0.6036	Remote Similarity	NPD5224	Approved
0.6036	Remote Similarity	NPD5226	Approved
0.6036	Remote Similarity	NPD4633	Approved
0.6036	Remote Similarity	NPD5225	Approved
0.6034	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.602	Remote Similarity	NPD6929	Approved
0.6019	Remote Similarity	NPD5222	Approved
0.6019	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD5221	Approved
0.6019	Remote Similarity	NPD4697	Phase 3
0.6019	Remote Similarity	NPD7524	Approved
0.6019	Remote Similarity	NPD7750	Discontinued
0.6	Remote Similarity	NPD5207	Approved
0.6	Remote Similarity	NPD4700	Approved
0.6	Remote Similarity	NPD8074	Phase 3
0.5984	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD5175	Approved
0.5982	Remote Similarity	NPD6647	Phase 2
0.5982	Remote Similarity	NPD5174	Approved
0.598	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD5173	Approved
0.596	Remote Similarity	NPD6931	Approved
0.596	Remote Similarity	NPD6930	Phase 2
0.595	Remote Similarity	NPD7100	Approved
0.595	Remote Similarity	NPD7101	Approved
0.5946	Remote Similarity	NPD5223	Approved
0.5938	Remote Similarity	NPD7260	Phase 2
0.5932	Remote Similarity	NPD4632	Approved
0.5922	Remote Similarity	NPD6422	Discontinued
0.5922	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD6317	Approved
0.5913	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5906	Remote Similarity	NPD7319	Approved
0.5905	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD6080	Approved
0.5905	Remote Similarity	NPD6904	Approved
0.5905	Remote Similarity	NPD6673	Approved
0.5902	Remote Similarity	NPD6319	Approved
0.59	Remote Similarity	NPD857	Phase 3
0.5889	Remote Similarity	NPD3197	Phase 1
0.5887	Remote Similarity	NPD7604	Phase 2
0.5882	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD4792	Clinical (unspecified phase)

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