NPASS Compound

Structure

CID39818 OpenBabel06191715372D 28 29 0 0 0 0 0 0 0 0999 V2000 -6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 20 1 0 0 0 0 5 21 1 0 0 0 0 6 7 2 0 0 0 0 6 14 1 0 0 0 0 7 15 1 0 0 0 0 8 10 1 0 0 0 0 8 11 1 0 0 0 0 9 12 1 0 0 0 0 9 13 1 0 0 0 0 10 18 2 0 0 0 0 11 19 1 0 0 0 0 12 19 2 0 0 0 0 13 20 1 0 0 0 0 14 23 2 0 0 0 0 15 24 2 0 0 0 0 16 17 1 0 0 0 0 16 20 2 0 0 0 0 17 22 1 0 0 0 0 21 22 2 0 0 0 0 21 26 1 0 0 0 0 22 25 1 0 0 0 0 23 24 1 0 0 0 0 23 25 1 0 0 0 0 24 26 1 0 0 0 0 25 27 2 0 0 0 0 26 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	379.25
Volume:	431.329
LogP:	5.694
LogD:	4.517
LogS:	-2.997
# Rotatable Bonds:	8
TPSA:	42.23
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.42
Synthetic Accessibility Score:	2.948
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.732
MDCK Permeability:	2.586355731182266e-05
Pgp-inhibitor:	0.709
Pgp-substrate:	0.031
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.043

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.203
Plasma Protein Binding (PPB):	100.09075164794922%
Volume Distribution (VD):	0.933
Pgp-substrate:	0.726355254650116%

ADMET: Metabolism

CYP1A2-inhibitor:	0.945
CYP1A2-substrate:	0.475
CYP2C19-inhibitor:	0.867
CYP2C19-substrate:	0.132
CYP2C9-inhibitor:	0.934
CYP2C9-substrate:	0.953
CYP2D6-inhibitor:	0.682
CYP2D6-substrate:	0.277
CYP3A4-inhibitor:	0.65
CYP3A4-substrate:	0.167

ADMET: Excretion

Clearance (CL):	3.253
Half-life (T1/2):	0.202

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.247
Drug-inuced Liver Injury (DILI):	0.014
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.001
Maximum Recommended Daily Dose:	0.955
Skin Sensitization:	0.95
Carcinogencity:	0.075
Eye Corrosion:	0.003
Eye Irritation:	0.288
Respiratory Toxicity:	0.12

Download Data

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

Natural Product: NPC39818

Natural Product ID:	NPC39818
*Common Name:**	Aurachin C
IUPAC Name:	1-hydroxy-2-methyl-3-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl]quinolin-4-one
Synonyms:	Aurachin C
Standard InCHIKey:	FIHXCHBEHLCXEG-YEFHWUCQSA-N
Standard InCHI:	InChI=1S/C25H33NO2/c1-18(2)10-8-11-19(3)12-9-13-20(4)16-17-22-21(5)26(28)24-15-7-6-14-23(24)25(22)27/h6-7,10,12,14-16,28H,8-9,11,13,17H2,1-5H3/b19-12+,20-16+
SMILES:	C/C(=CCc1c(C)n(O)c2c(c1=O)cccc2)/CC/C=C(/CCC=C(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL572434
PubChem CID:	6439171
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO4290	Stigmatella aurantiaca	Species	Archangiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18701458]
NPO33510	stigmatella sp.	Species	Archangiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18922036]
NPO4290	Stigmatella aurantiaca	Species	Archangiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18989924]
NPO4290	Stigmatella aurantiaca	Species	Archangiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21979787]
NPO4290	Stigmatella aurantiaca	Species	Archangiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22741921]
NPO4290	Stigmatella aurantiaca	Species	Archangiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22907798]
NPO4290	Stigmatella aurantiaca	Species	Archangiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24367422]
NPO4290	Stigmatella aurantiaca	Species	Archangiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[3106289]
NPO4290	Stigmatella aurantiaca	Species	Archangiaceae	Bacteria	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	4

Activity Type	# Activity
Cell Line	1
Organism	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1460	Cell Line	L929	Mus musculus	IC50	=	1.8	ug.mL-1	PMID[535662]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.026	ug.mL-1	PMID[535662]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.0009	ug.mL-1	PMID[535662]
NPT2	Others	Unspecified		IC50	=	16.0	ug.mL-1	PMID[535662]

☑ 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 NPC39818 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	358
0.1-0.2	3123
0.2-0.3	13277
0.3-0.4	16688
0.4-0.5	5267
0.5-0.6	2439
0.6-0.7	1356
0.7-0.8	170
0.8-0.85	3
0.85-0.9	3
0.9-0.95	12
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9316	High Similarity	NPC161956
0.9316	High Similarity	NPC112373
0.9316	High Similarity	NPC258531
0.9237	High Similarity	NPC103292
0.9231	High Similarity	NPC291962
0.9231	High Similarity	NPC177684
0.9153	High Similarity	NPC179605
0.9153	High Similarity	NPC279385
0.8917	High Similarity	NPC257490
0.824	Intermediate Similarity	NPC268534
0.8217	Intermediate Similarity	NPC194562
0.8205	Intermediate Similarity	NPC172170
0.814	Intermediate Similarity	NPC209389
0.8031	Intermediate Similarity	NPC254698
0.8	Intermediate Similarity	NPC226143
0.7879	Intermediate Similarity	NPC316746
0.7829	Intermediate Similarity	NPC192533
0.7803	Intermediate Similarity	NPC280807
0.7803	Intermediate Similarity	NPC314431
0.7778	Intermediate Similarity	NPC300299
0.7769	Intermediate Similarity	NPC470343
0.7769	Intermediate Similarity	NPC472244
0.7681	Intermediate Similarity	NPC207554
0.7626	Intermediate Similarity	NPC471574
0.7626	Intermediate Similarity	NPC471164
0.7609	Intermediate Similarity	NPC83214
0.7594	Intermediate Similarity	NPC150863
0.7589	Intermediate Similarity	NPC470822
0.7569	Intermediate Similarity	NPC144691
0.7537	Intermediate Similarity	NPC472245
0.752	Intermediate Similarity	NPC57051
0.7465	Intermediate Similarity	NPC130797
0.7465	Intermediate Similarity	NPC136002
0.7407	Intermediate Similarity	NPC187231
0.7319	Intermediate Similarity	NPC316104
0.7319	Intermediate Similarity	NPC253476
0.7319	Intermediate Similarity	NPC162417
0.726	Intermediate Similarity	NPC300596
0.726	Intermediate Similarity	NPC237649
0.7254	Intermediate Similarity	NPC2823
0.7183	Intermediate Similarity	NPC315051
0.7181	Intermediate Similarity	NPC295021
0.7174	Intermediate Similarity	NPC207428
0.7171	Intermediate Similarity	NPC27904
0.7153	Intermediate Similarity	NPC477432
0.7143	Intermediate Similarity	NPC173295
0.7133	Intermediate Similarity	NPC316202
0.7132	Intermediate Similarity	NPC72473
0.7132	Intermediate Similarity	NPC307437
0.7132	Intermediate Similarity	NPC58827
0.708	Intermediate Similarity	NPC122235
0.7063	Intermediate Similarity	NPC472243
0.7059	Intermediate Similarity	NPC93653
0.7055	Intermediate Similarity	NPC472242
0.7034	Intermediate Similarity	NPC314287
0.7014	Intermediate Similarity	NPC43477
0.7	Intermediate Similarity	NPC117032
0.698	Remote Similarity	NPC13526
0.6966	Remote Similarity	NPC472241
0.6962	Remote Similarity	NPC318183
0.6929	Remote Similarity	NPC53044
0.6929	Remote Similarity	NPC40364
0.6923	Remote Similarity	NPC299582
0.6918	Remote Similarity	NPC478040
0.6918	Remote Similarity	NPC308197
0.6912	Remote Similarity	NPC226794
0.6892	Remote Similarity	NPC324445
0.6885	Remote Similarity	NPC75496
0.688	Remote Similarity	NPC167336
0.6871	Remote Similarity	NPC314186
0.6866	Remote Similarity	NPC130931
0.6857	Remote Similarity	NPC314098
0.6832	Remote Similarity	NPC475607
0.6806	Remote Similarity	NPC122553
0.68	Remote Similarity	NPC38262
0.68	Remote Similarity	NPC242000
0.6794	Remote Similarity	NPC472164
0.6792	Remote Similarity	NPC472118
0.679	Remote Similarity	NPC474081
0.6779	Remote Similarity	NPC470579
0.6779	Remote Similarity	NPC478039
0.6774	Remote Similarity	NPC154478
0.677	Remote Similarity	NPC475594
0.6759	Remote Similarity	NPC469560
0.6753	Remote Similarity	NPC84317
0.6752	Remote Similarity	NPC138293
0.6752	Remote Similarity	NPC204867
0.6752	Remote Similarity	NPC113056
0.6712	Remote Similarity	NPC130251
0.6709	Remote Similarity	NPC471130
0.6691	Remote Similarity	NPC250476
0.6691	Remote Similarity	NPC322433
0.6688	Remote Similarity	NPC114808
0.6688	Remote Similarity	NPC88970
0.6688	Remote Similarity	NPC35510
0.6688	Remote Similarity	NPC253667
0.6688	Remote Similarity	NPC242116
0.6687	Remote Similarity	NPC471943
0.6667	Remote Similarity	NPC301760
0.6647	Remote Similarity	NPC476341
0.6646	Remote Similarity	NPC475761
0.6646	Remote Similarity	NPC474041
0.6646	Remote Similarity	NPC292265
0.6644	Remote Similarity	NPC190945
0.6639	Remote Similarity	NPC78154
0.6626	Remote Similarity	NPC471743
0.662	Remote Similarity	NPC231382
0.6606	Remote Similarity	NPC85613
0.6606	Remote Similarity	NPC475685
0.6604	Remote Similarity	NPC115232
0.6599	Remote Similarity	NPC242933
0.6582	Remote Similarity	NPC293458
0.6577	Remote Similarity	NPC469537
0.6564	Remote Similarity	NPC469529
0.6543	Remote Similarity	NPC355
0.6528	Remote Similarity	NPC130655
0.6519	Remote Similarity	NPC313449
0.6508	Remote Similarity	NPC291610
0.6507	Remote Similarity	NPC471123
0.6506	Remote Similarity	NPC5167
0.6506	Remote Similarity	NPC283810
0.65	Remote Similarity	NPC205946
0.65	Remote Similarity	NPC474926
0.6494	Remote Similarity	NPC314223
0.6478	Remote Similarity	NPC214106
0.6475	Remote Similarity	NPC246757
0.6475	Remote Similarity	NPC291070
0.6471	Remote Similarity	NPC228515
0.6467	Remote Similarity	NPC277157
0.6463	Remote Similarity	NPC159722
0.6457	Remote Similarity	NPC202613
0.6446	Remote Similarity	NPC475094
0.6438	Remote Similarity	NPC189116
0.6433	Remote Similarity	NPC29285
0.6429	Remote Similarity	NPC470317
0.6423	Remote Similarity	NPC256452
0.6419	Remote Similarity	NPC181527
0.6415	Remote Similarity	NPC315368
0.6404	Remote Similarity	NPC300205
0.6397	Remote Similarity	NPC192209
0.6392	Remote Similarity	NPC123241
0.6387	Remote Similarity	NPC69057
0.6387	Remote Similarity	NPC154602
0.6385	Remote Similarity	NPC55529
0.6385	Remote Similarity	NPC79618
0.6383	Remote Similarity	NPC472165
0.6375	Remote Similarity	NPC472117
0.6375	Remote Similarity	NPC469741
0.637	Remote Similarity	NPC288232
0.6364	Remote Similarity	NPC470548
0.6358	Remote Similarity	NPC214960
0.6358	Remote Similarity	NPC279527
0.6357	Remote Similarity	NPC2982
0.6353	Remote Similarity	NPC49184
0.635	Remote Similarity	NPC229353
0.6348	Remote Similarity	NPC164086
0.6346	Remote Similarity	NPC285381
0.6343	Remote Similarity	NPC296163
0.6343	Remote Similarity	NPC187036
0.6338	Remote Similarity	NPC314278
0.6335	Remote Similarity	NPC265100
0.6333	Remote Similarity	NPC470301
0.6328	Remote Similarity	NPC471317
0.6325	Remote Similarity	NPC151635
0.6323	Remote Similarity	NPC473329
0.6319	Remote Similarity	NPC63047
0.6319	Remote Similarity	NPC70949
0.6319	Remote Similarity	NPC179224
0.6319	Remote Similarity	NPC475248
0.6316	Remote Similarity	NPC285470
0.6316	Remote Similarity	NPC36342
0.6316	Remote Similarity	NPC2785
0.6312	Remote Similarity	NPC143457
0.6311	Remote Similarity	NPC284475
0.631	Remote Similarity	NPC73994
0.631	Remote Similarity	NPC298320
0.6301	Remote Similarity	NPC313293
0.6299	Remote Similarity	NPC326792
0.6289	Remote Similarity	NPC104345
0.6289	Remote Similarity	NPC113946
0.6287	Remote Similarity	NPC83774
0.6282	Remote Similarity	NPC243756
0.6279	Remote Similarity	NPC473815
0.6273	Remote Similarity	NPC286871
0.6273	Remote Similarity	NPC176983
0.6273	Remote Similarity	NPC476231
0.6272	Remote Similarity	NPC472163
0.6264	Remote Similarity	NPC1820
0.626	Remote Similarity	NPC1682
0.626	Remote Similarity	NPC188844
0.6259	Remote Similarity	NPC150323
0.6259	Remote Similarity	NPC316582
0.6258	Remote Similarity	NPC114637
0.6258	Remote Similarity	NPC182131
0.625	Remote Similarity	NPC36495
0.6242	Remote Similarity	NPC70406
0.6242	Remote Similarity	NPC287358
0.6242	Remote Similarity	NPC122106
0.6235	Remote Similarity	NPC243058
0.6235	Remote Similarity	NPC117027

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 NPC39818 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	233
0.1-0.2	727
0.2-0.3	904
0.3-0.4	1829
0.4-0.5	2724
0.5-0.6	2051
0.6-0.7	637
0.7-0.8	43
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8154	Intermediate Similarity	NPD486	Clinical (unspecified phase)
0.803	Intermediate Similarity	NPD441	Approved
0.7939	Intermediate Similarity	NPD2918	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD2919	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD6017	Discontinued
0.7895	Intermediate Similarity	NPD1541	Approved
0.7895	Intermediate Similarity	NPD1527	Phase 2
0.7846	Intermediate Similarity	NPD797	Clinical (unspecified phase)
0.782	Intermediate Similarity	NPD1919	Approved
0.782	Intermediate Similarity	NPD1920	Approved
0.7778	Intermediate Similarity	NPD1668	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD1175	Approved
0.763	Intermediate Similarity	NPD2950	Approved
0.763	Intermediate Similarity	NPD2949	Approved
0.7557	Intermediate Similarity	NPD1640	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6740	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD6342	Discontinued
0.7391	Intermediate Similarity	NPD2331	Discontinued
0.7377	Intermediate Similarity	NPD1065	Approved
0.7377	Intermediate Similarity	NPD1064	Approved
0.7372	Intermediate Similarity	NPD1874	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD1626	Approved
0.7353	Intermediate Similarity	NPD1190	Approved
0.7273	Intermediate Similarity	NPD4775	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1625	Approved
0.726	Intermediate Similarity	NPD4942	Approved
0.726	Intermediate Similarity	NPD4888	Discontinued
0.7211	Intermediate Similarity	NPD2737	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD6513	Approved
0.7203	Intermediate Similarity	NPD6512	Approved
0.7197	Intermediate Similarity	NPD1079	Discontinued
0.7133	Intermediate Similarity	NPD3434	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD1854	Approved
0.7111	Intermediate Similarity	NPD1574	Approved
0.7103	Intermediate Similarity	NPD5918	Discontinued
0.7101	Intermediate Similarity	NPD1619	Phase 3
0.7092	Intermediate Similarity	NPD5227	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6414	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1189	Approved
0.7083	Intermediate Similarity	NPD6768	Approved
0.7059	Intermediate Similarity	NPD1593	Approved
0.7059	Intermediate Similarity	NPD2506	Approved
0.7055	Intermediate Similarity	NPD5933	Phase 3
0.7055	Intermediate Similarity	NPD5932	Phase 3
0.7055	Intermediate Similarity	NPD5931	Phase 3
0.7027	Intermediate Similarity	NPD4939	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD2470	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD4045	Phase 2
0.702	Intermediate Similarity	NPD4042	Phase 2
0.7	Intermediate Similarity	NPD3248	Phase 1
0.6993	Remote Similarity	NPD7142	Discontinued
0.6966	Remote Similarity	NPD3482	Approved
0.6966	Remote Similarity	NPD6566	Discontinued
0.6954	Remote Similarity	NPD2790	Discontinued
0.694	Remote Similarity	NPD1123	Approved
0.694	Remote Similarity	NPD1124	Approved
0.6918	Remote Similarity	NPD2820	Phase 3
0.6918	Remote Similarity	NPD4464	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD1306	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD708	Approved
0.6901	Remote Similarity	NPD1410	Phase 1
0.6901	Remote Similarity	NPD2791	Discontinued
0.6883	Remote Similarity	NPD2427	Approved
0.6875	Remote Similarity	NPD6655	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD4046	Approved
0.6871	Remote Similarity	NPD4043	Approved
0.6871	Remote Similarity	NPD3481	Approved
0.686	Remote Similarity	NPD1100	Approved
0.686	Remote Similarity	NPD1099	Approved
0.6849	Remote Similarity	NPD2365	Approved
0.6846	Remote Similarity	NPD5181	Approved
0.6846	Remote Similarity	NPD5180	Approved
0.6846	Remote Similarity	NPD5179	Approved
0.6846	Remote Similarity	NPD3387	Approved
0.6835	Remote Similarity	NPD1781	Discontinued
0.6835	Remote Similarity	NPD2037	Approved
0.6821	Remote Similarity	NPD1230	Approved
0.6815	Remote Similarity	NPD678	Discontinued
0.6792	Remote Similarity	NPD2369	Discontinued
0.6792	Remote Similarity	NPD3376	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD2648	Phase 3
0.6774	Remote Similarity	NPD33	Approved
0.6774	Remote Similarity	NPD4393	Approved
0.6774	Remote Similarity	NPD2193	Phase 2
0.6772	Remote Similarity	NPD4645	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD2836	Approved
0.6748	Remote Similarity	NPD3782	Discontinued
0.6733	Remote Similarity	NPD7088	Discontinued
0.6719	Remote Similarity	NPD1342	Approved
0.6716	Remote Similarity	NPD922	Approved
0.6715	Remote Similarity	NPD1360	Approved
0.6714	Remote Similarity	NPD4549	Discontinued
0.6707	Remote Similarity	NPD4329	Approved
0.6707	Remote Similarity	NPD4330	Approved
0.6693	Remote Similarity	NPD3546	Approved
0.6693	Remote Similarity	NPD3545	Approved
0.6692	Remote Similarity	NPD3865	Approved
0.6691	Remote Similarity	NPD9540	Approved
0.669	Remote Similarity	NPD4077	Clinical (unspecified phase)
0.669	Remote Similarity	NPD2670	Approved
0.6689	Remote Similarity	NPD4430	Phase 2
0.6689	Remote Similarity	NPD7082	Approved
0.6688	Remote Similarity	NPD7072	Phase 2
0.6687	Remote Similarity	NPD3792	Approved
0.6667	Remote Similarity	NPD3548	Approved
0.6667	Remote Similarity	NPD5131	Approved
0.6667	Remote Similarity	NPD4461	Discontinued
0.6667	Remote Similarity	NPD9539	Approved
0.6667	Remote Similarity	NPD9541	Approved
0.6646	Remote Similarity	NPD2431	Approved
0.6646	Remote Similarity	NPD2432	Approved
0.6645	Remote Similarity	NPD5748	Phase 2
0.6645	Remote Similarity	NPD2351	Discontinued
0.6644	Remote Similarity	NPD7259	Approved
0.6644	Remote Similarity	NPD2435	Approved
0.6644	Remote Similarity	NPD7254	Discontinued
0.6641	Remote Similarity	NPD4115	Approved
0.6641	Remote Similarity	NPD4114	Approved
0.6641	Remote Similarity	NPD181	Approved
0.664	Remote Similarity	NPD2196	Discontinued
0.664	Remote Similarity	NPD2171	Approved
0.664	Remote Similarity	NPD813	Approved
0.6626	Remote Similarity	NPD2083	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD2454	Approved
0.6625	Remote Similarity	NPD2455	Approved
0.662	Remote Similarity	NPD4300	Clinical (unspecified phase)
0.662	Remote Similarity	NPD2754	Discontinued
0.6614	Remote Similarity	NPD2197	Approved
0.6614	Remote Similarity	NPD2192	Approved
0.6603	Remote Similarity	NPD6018	Approved
0.6603	Remote Similarity	NPD6019	Approved
0.6603	Remote Similarity	NPD5659	Approved
0.6603	Remote Similarity	NPD5660	Approved
0.66	Remote Similarity	NPD7295	Approved
0.6597	Remote Similarity	NPD1531	Approved
0.6587	Remote Similarity	NPD8241	Phase 2
0.6579	Remote Similarity	NPD4161	Discontinued
0.6575	Remote Similarity	NPD1532	Approved
0.6569	Remote Similarity	NPD1517	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD993	Approved
0.6562	Remote Similarity	NPD990	Approved
0.6558	Remote Similarity	NPD3399	Approved
0.6556	Remote Similarity	NPD4041	Approved
0.6556	Remote Similarity	NPD1956	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD2010	Phase 3
0.6554	Remote Similarity	NPD1222	Discontinued
0.6552	Remote Similarity	NPD1228	Phase 2
0.6544	Remote Similarity	NPD1217	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD951	Approved
0.6538	Remote Similarity	NPD4116	Approved
0.6538	Remote Similarity	NPD1211	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD1208	Approved
0.6533	Remote Similarity	NPD7487	Discontinued
0.6525	Remote Similarity	NPD1560	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD2404	Discontinued
0.6519	Remote Similarity	NPD7481	Approved
0.6519	Remote Similarity	NPD5992	Approved
0.6519	Remote Similarity	NPD7480	Approved
0.6516	Remote Similarity	NPD7612	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD5086	Approved
0.6513	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD3420	Clinical (unspecified phase)
0.651	Remote Similarity	NPD2923	Approved
0.651	Remote Similarity	NPD167	Phase 2
0.651	Remote Similarity	NPD168	Phase 1
0.6508	Remote Similarity	NPD4734	Approved
0.6508	Remote Similarity	NPD4735	Approved
0.6503	Remote Similarity	NPD3377	Discontinued
0.65	Remote Similarity	NPD1036	Approved
0.6479	Remote Similarity	NPD766	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD1210	Approved
0.6471	Remote Similarity	NPD979	Approved
0.6471	Remote Similarity	NPD7528	Approved
0.6467	Remote Similarity	NPD3471	Approved
0.6467	Remote Similarity	NPD3470	Approved
0.6463	Remote Similarity	NPD6358	Phase 2
0.6463	Remote Similarity	NPD3423	Phase 2
0.6463	Remote Similarity	NPD3422	Phase 3
0.6456	Remote Similarity	NPD6629	Discontinued
0.6449	Remote Similarity	NPD3836	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD4607	Approved
0.6439	Remote Similarity	NPD3001	Approved
0.6439	Remote Similarity	NPD2999	Approved
0.6438	Remote Similarity	NPD2288	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD3747	Discontinued
0.6412	Remote Similarity	NPD1539	Approved
0.6412	Remote Similarity	NPD7633	Discontinued
0.6408	Remote Similarity	NPD5993	Phase 1
0.6406	Remote Similarity	NPD2577	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD3352	Approved
0.6405	Remote Similarity	NPD7478	Approved
0.6395	Remote Similarity	NPD1207	Approved
0.6395	Remote Similarity	NPD1206	Approved
0.6391	Remote Similarity	NPD4412	Phase 2
0.6389	Remote Similarity	NPD1070	Approved
0.6389	Remote Similarity	NPD1069	Approved
0.6385	Remote Similarity	NPD5253	Approved
0.6382	Remote Similarity	NPD6185	Discontinued
0.6376	Remote Similarity	NPD1205	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