NPASS Compound

Structure

CID104861 OpenBabel06191715452D 28 31 0 0 1 0 0 0 0 0999 V2000 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2084 1.8750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.0860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 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 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4265 1.2515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 1 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 -1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0376 1.2515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.5860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 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 -1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2557 1.8750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.5860 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 11 1 0 0 0 0 5 26 1 0 0 0 0 6 27 1 0 0 0 0 7 10 1 0 0 0 0 7 14 2 0 0 0 0 8 12 1 0 0 0 0 8 15 1 0 0 0 0 9 13 1 0 0 0 0 9 16 1 0 0 0 0 10 1 1 1 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 11 18 2 0 0 0 0 12 22 1 6 0 0 0 13 21 1 1 0 0 0 14 20 1 0 0 0 0 14 26 1 0 0 0 0 15 21 1 1 0 0 0 15 28 1 0 0 0 0 16 23 2 0 0 0 0 16 28 1 0 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 17 24 2 0 0 0 0 18 27 1 0 0 0 0 19 21 1 6 0 0 0 19 22 1 0 0 0 0 20 22 1 0 0 0 0 20 25 2 0 0 0 0 21 3 1 6 0 0 0 22 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	388.19
Volume:	394.401
LogP:	2.245
LogD:	1.872
LogS:	-3.206
# Rotatable Bonds:	2
TPSA:	78.9
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.534
Synthetic Accessibility Score:	5.19
Fsp3:	0.682
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:	-4.935
MDCK Permeability:	5.170334407011978e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.329
30% Bioavailability (F30%):	0.925

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.94
Plasma Protein Binding (PPB):	54.596832275390625%
Volume Distribution (VD):	1.204
Pgp-substrate:	39.9036865234375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.062
CYP1A2-substrate:	0.936
CYP2C19-inhibitor:	0.154
CYP2C19-substrate:	0.693
CYP2C9-inhibitor:	0.044
CYP2C9-substrate:	0.02
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.091
CYP3A4-inhibitor:	0.759
CYP3A4-substrate:	0.545

ADMET: Excretion

Clearance (CL):	10.943
Half-life (T1/2):	0.067

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.755
Drug-inuced Liver Injury (DILI):	0.743
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.653
Maximum Recommended Daily Dose:	0.112
Skin Sensitization:	0.273
Carcinogencity:	0.05
Eye Corrosion:	0.665
Eye Irritation:	0.026
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC104861

Natural Product ID:	NPC104861
*Common Name:**	Quassin
IUPAC Name:	n.a.
Synonyms:	Quassin
Standard InCHIKey:	IOSXSVZRTUWBHC-LBTVDEKVSA-N
Standard InCHI:	InChI=1S/C22H28O6/c1-10-7-14(26-5)20(25)22(4)12(10)8-15-21(3)13(9-16(23)28-15)11(2)18(27-6)17(24)19(21)22/h7,10,12-13,15,19H,8-9H2,1-6H3/t10-,12+,13+,15-,19+,21-,22+/m1/s1
SMILES:	C[C@@H]1C=C(C(=O)[C@@]2(C)[C@H]1C[C@@H]1[C@@]3(C)[C@@H](CC(=O)O1)C(=C(C(=O)[C@H]23)OC)C)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517016
PubChem CID:	65571
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0002119] Quassinoids

*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
NPO704	Quassia amara	Species	Simaroubaceae	Eukaryota	n.a.	leaf	n.a.	PMID[16730421]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19586051]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	stems	n.a.	n.a.	PMID[20095629]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25506718]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27494664]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30917277]
NPO2349	Picrasma excelsa	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO704	Quassia amara	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO704	Quassia amara	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2349	Picrasma excelsa	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO704	Quassia amara	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2349	Picrasma excelsa	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO704	Quassia amara	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2349	Picrasma excelsa	Species	Simaroubaceae	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	4
Others	9

Activity Type	# Activity
Cell Line	6
Individual Protein	3
Organism	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	911000.0	nM	PMID[541298]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	2000.0	nM	PMID[541299]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	24.69	%	PMID[541300]
NPT519	Cell Line	SH-SY5Y	Homo sapiens	Activity	=	73.1	%	PMID[541303]
NPT519	Cell Line	SH-SY5Y	Homo sapiens	Activity	=	10.7	%	PMID[541303]
NPT519	Cell Line	SH-SY5Y	Homo sapiens	Activity	=	13.7	%	PMID[541303]
NPT519	Cell Line	SH-SY5Y	Homo sapiens	Activity	=	2.45	%	PMID[541303]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	>	1000000.0	nM	PMID[541298]
NPT2	Others	Unspecified		Selectivity Index	>	1.0	n.a.	PMID[541298]
NPT2	Others	Unspecified		INH	>	30.0	uM	PMID[541299]
NPT67	Individual Protein	Cholinesterase	Equus caballus	Inhibition	=	4.69	%	PMID[541300]
NPT992	Organism	Entamoeba histolytica	Entamoeba histolytica	IC50	=	0.5	ug.mL-1	PMID[541301]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	100.46	%	PMID[541302]

☑ 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 NPC104861 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	267
0.1-0.2	1681
0.2-0.3	5269
0.3-0.4	9057
0.4-0.5	13202
0.5-0.6	7181
0.6-0.7	4980
0.7-0.8	1013
0.8-0.85	30
0.85-0.9	8
0.9-0.95	5
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.8641	High Similarity	NPC27814
0.8627	High Similarity	NPC202524
0.8586	High Similarity	NPC472972
0.8515	High Similarity	NPC275583
0.8462	Intermediate Similarity	NPC250018
0.8367	Intermediate Similarity	NPC274417
0.8333	Intermediate Similarity	NPC282233
0.8333	Intermediate Similarity	NPC179208
0.8333	Intermediate Similarity	NPC95585
0.8265	Intermediate Similarity	NPC269729
0.8182	Intermediate Similarity	NPC176005
0.8144	Intermediate Similarity	NPC223093
0.8131	Intermediate Similarity	NPC34315
0.8113	Intermediate Similarity	NPC474242
0.81	Intermediate Similarity	NPC111684
0.81	Intermediate Similarity	NPC58052
0.8039	Intermediate Similarity	NPC475385
0.8039	Intermediate Similarity	NPC475392
0.8039	Intermediate Similarity	NPC475202
0.8037	Intermediate Similarity	NPC210005
0.8021	Intermediate Similarity	NPC30421
0.802	Intermediate Similarity	NPC216904
0.802	Intermediate Similarity	NPC226986
0.8019	Intermediate Similarity	NPC277017
0.8019	Intermediate Similarity	NPC154608
0.8019	Intermediate Similarity	NPC192813
0.8019	Intermediate Similarity	NPC293850
0.8	Intermediate Similarity	NPC133652
0.7981	Intermediate Similarity	NPC254202
0.798	Intermediate Similarity	NPC79117
0.7959	Intermediate Similarity	NPC328141
0.7946	Intermediate Similarity	NPC127530
0.7946	Intermediate Similarity	NPC470777
0.7941	Intermediate Similarity	NPC112753
0.7941	Intermediate Similarity	NPC275439
0.7925	Intermediate Similarity	NPC144854
0.7925	Intermediate Similarity	NPC133422
0.7925	Intermediate Similarity	NPC3316
0.7909	Intermediate Similarity	NPC473798
0.7905	Intermediate Similarity	NPC40170
0.7843	Intermediate Similarity	NPC292133
0.7843	Intermediate Similarity	NPC23680
0.7843	Intermediate Similarity	NPC473456
0.7838	Intermediate Similarity	NPC328374
0.7838	Intermediate Similarity	NPC96312
0.7838	Intermediate Similarity	NPC40632
0.7838	Intermediate Similarity	NPC251236
0.783	Intermediate Similarity	NPC475571
0.783	Intermediate Similarity	NPC102352
0.7818	Intermediate Similarity	NPC198539
0.7818	Intermediate Similarity	NPC472926
0.7818	Intermediate Similarity	NPC49451
0.781	Intermediate Similarity	NPC33973
0.781	Intermediate Similarity	NPC478057
0.781	Intermediate Similarity	NPC70967
0.781	Intermediate Similarity	NPC159442
0.7807	Intermediate Similarity	NPC275675
0.7798	Intermediate Similarity	NPC171888
0.7798	Intermediate Similarity	NPC201992
0.7798	Intermediate Similarity	NPC146945
0.7798	Intermediate Similarity	NPC115303
0.7788	Intermediate Similarity	NPC124211
0.7778	Intermediate Similarity	NPC286174
0.7778	Intermediate Similarity	NPC304495
0.7778	Intermediate Similarity	NPC152467
0.7778	Intermediate Similarity	NPC77947
0.7768	Intermediate Similarity	NPC472927
0.7767	Intermediate Similarity	NPC264378
0.7767	Intermediate Similarity	NPC478056
0.7766	Intermediate Similarity	NPC474085
0.7748	Intermediate Similarity	NPC323821
0.7748	Intermediate Similarity	NPC45218
0.7748	Intermediate Similarity	NPC268238
0.7748	Intermediate Similarity	NPC474906
0.7748	Intermediate Similarity	NPC143268
0.7748	Intermediate Similarity	NPC18547
0.7745	Intermediate Similarity	NPC5532
0.7745	Intermediate Similarity	NPC61369
0.7745	Intermediate Similarity	NPC469545
0.7736	Intermediate Similarity	NPC470251
0.7736	Intermediate Similarity	NPC216245
0.7736	Intermediate Similarity	NPC213366
0.7736	Intermediate Similarity	NPC96268
0.7736	Intermediate Similarity	NPC470297
0.7736	Intermediate Similarity	NPC135854
0.7736	Intermediate Similarity	NPC2436
0.7727	Intermediate Similarity	NPC90769
0.7727	Intermediate Similarity	NPC193948
0.7727	Intermediate Similarity	NPC11252
0.7727	Intermediate Similarity	NPC289312
0.7723	Intermediate Similarity	NPC470697
0.7723	Intermediate Similarity	NPC477439
0.7714	Intermediate Similarity	NPC80781
0.7714	Intermediate Similarity	NPC53222
0.7706	Intermediate Similarity	NPC197428
0.7706	Intermediate Similarity	NPC129689
0.77	Intermediate Similarity	NPC476934
0.77	Intermediate Similarity	NPC473944
0.77	Intermediate Similarity	NPC218301
0.7699	Intermediate Similarity	NPC17772
0.7692	Intermediate Similarity	NPC476933
0.7692	Intermediate Similarity	NPC88198
0.7692	Intermediate Similarity	NPC471727
0.7685	Intermediate Similarity	NPC470269
0.7685	Intermediate Similarity	NPC275539
0.7685	Intermediate Similarity	NPC189075
0.7684	Intermediate Similarity	NPC470813
0.7679	Intermediate Similarity	NPC16081
0.7679	Intermediate Similarity	NPC235539
0.7679	Intermediate Similarity	NPC152199
0.7679	Intermediate Similarity	NPC173686
0.7679	Intermediate Similarity	NPC134869
0.7679	Intermediate Similarity	NPC270958
0.7677	Intermediate Similarity	NPC280833
0.7677	Intermediate Similarity	NPC50070
0.7672	Intermediate Similarity	NPC227397
0.767	Intermediate Similarity	NPC84335
0.767	Intermediate Similarity	NPC170131
0.767	Intermediate Similarity	NPC38530
0.7664	Intermediate Similarity	NPC292588
0.7664	Intermediate Similarity	NPC181357
0.7658	Intermediate Similarity	NPC208998
0.7658	Intermediate Similarity	NPC194100
0.7658	Intermediate Similarity	NPC7921
0.7658	Intermediate Similarity	NPC202889
0.7658	Intermediate Similarity	NPC51978
0.7647	Intermediate Similarity	NPC477437
0.7647	Intermediate Similarity	NPC477438
0.7642	Intermediate Similarity	NPC95899
0.7636	Intermediate Similarity	NPC188738
0.7632	Intermediate Similarity	NPC472933
0.7632	Intermediate Similarity	NPC473920
0.7632	Intermediate Similarity	NPC279143
0.7629	Intermediate Similarity	NPC474680
0.7629	Intermediate Similarity	NPC2709
0.7629	Intermediate Similarity	NPC8518
0.7629	Intermediate Similarity	NPC263997
0.7629	Intermediate Similarity	NPC132228
0.7624	Intermediate Similarity	NPC477435
0.7624	Intermediate Similarity	NPC477436
0.7615	Intermediate Similarity	NPC141350
0.7615	Intermediate Similarity	NPC20192
0.7615	Intermediate Similarity	NPC112457
0.7615	Intermediate Similarity	NPC310546
0.7611	Intermediate Similarity	NPC97908
0.7611	Intermediate Similarity	NPC470854
0.7611	Intermediate Similarity	NPC122033
0.7611	Intermediate Similarity	NPC474654
0.7611	Intermediate Similarity	NPC287343
0.7607	Intermediate Similarity	NPC24651
0.76	Intermediate Similarity	NPC475823
0.76	Intermediate Similarity	NPC474209
0.7596	Intermediate Similarity	NPC475876
0.7596	Intermediate Similarity	NPC114274
0.7593	Intermediate Similarity	NPC472925
0.7593	Intermediate Similarity	NPC110496
0.7593	Intermediate Similarity	NPC44063
0.7589	Intermediate Similarity	NPC470953
0.7589	Intermediate Similarity	NPC247069
0.7586	Intermediate Similarity	NPC312833
0.7579	Intermediate Similarity	NPC475833
0.7579	Intermediate Similarity	NPC475665
0.7573	Intermediate Similarity	NPC219353
0.7573	Intermediate Similarity	NPC305483
0.7573	Intermediate Similarity	NPC328162
0.7573	Intermediate Similarity	NPC96859
0.757	Intermediate Similarity	NPC65523
0.757	Intermediate Similarity	NPC189616
0.7568	Intermediate Similarity	NPC71348
0.7565	Intermediate Similarity	NPC107338
0.7565	Intermediate Similarity	NPC109607
0.7549	Intermediate Similarity	NPC23170
0.7549	Intermediate Similarity	NPC74751
0.7547	Intermediate Similarity	NPC163249
0.7545	Intermediate Similarity	NPC286880
0.7545	Intermediate Similarity	NPC253906
0.7544	Intermediate Similarity	NPC297179
0.7544	Intermediate Similarity	NPC118638
0.7544	Intermediate Similarity	NPC21326
0.7544	Intermediate Similarity	NPC251310
0.7526	Intermediate Similarity	NPC109512
0.7525	Intermediate Similarity	NPC470230
0.7525	Intermediate Similarity	NPC248913
0.7525	Intermediate Similarity	NPC297265
0.7525	Intermediate Similarity	NPC99380
0.7524	Intermediate Similarity	NPC471041
0.7524	Intermediate Similarity	NPC157787
0.7524	Intermediate Similarity	NPC471413
0.7523	Intermediate Similarity	NPC272576
0.7523	Intermediate Similarity	NPC94529
0.7523	Intermediate Similarity	NPC476479
0.7523	Intermediate Similarity	NPC476802
0.7523	Intermediate Similarity	NPC89171
0.7523	Intermediate Similarity	NPC295244
0.7522	Intermediate Similarity	NPC478216
0.7522	Intermediate Similarity	NPC207217
0.7521	Intermediate Similarity	NPC18945
0.7521	Intermediate Similarity	NPC105926
0.7521	Intermediate Similarity	NPC265557
0.7521	Intermediate Similarity	NPC476193

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 NPC104861 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	242
0.1-0.2	1991
0.2-0.3	3882
0.3-0.4	1917
0.4-0.5	731
0.5-0.6	175
0.6-0.7	126
0.7-0.8	86
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
0.8021	Intermediate Similarity	NPD3573	Approved
0.79	Intermediate Similarity	NPD7900	Approved
0.79	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD7902	Approved
0.7664	Intermediate Similarity	NPD6008	Approved
0.7636	Intermediate Similarity	NPD6649	Approved
0.7636	Intermediate Similarity	NPD6650	Approved
0.7615	Intermediate Similarity	NPD6372	Approved
0.7615	Intermediate Similarity	NPD6373	Approved
0.7593	Intermediate Similarity	NPD5697	Approved
0.7576	Intermediate Similarity	NPD5737	Approved
0.7576	Intermediate Similarity	NPD6672	Approved
0.7549	Intermediate Similarity	NPD7748	Approved
0.7523	Intermediate Similarity	NPD6881	Approved
0.7523	Intermediate Similarity	NPD6011	Approved
0.7523	Intermediate Similarity	NPD6899	Approved
0.75	Intermediate Similarity	NPD5739	Approved
0.75	Intermediate Similarity	NPD6402	Approved
0.75	Intermediate Similarity	NPD7128	Approved
0.75	Intermediate Similarity	NPD6675	Approved
0.7455	Intermediate Similarity	NPD6013	Approved
0.7455	Intermediate Similarity	NPD6014	Approved
0.7455	Intermediate Similarity	NPD6012	Approved
0.7431	Intermediate Similarity	NPD5701	Approved
0.7404	Intermediate Similarity	NPD4697	Phase 3
0.7387	Intermediate Similarity	NPD7102	Approved
0.7387	Intermediate Similarity	NPD7290	Approved
0.7387	Intermediate Similarity	NPD6883	Approved
0.7373	Intermediate Similarity	NPD8328	Phase 3
0.7364	Intermediate Similarity	NPD7320	Approved
0.7353	Intermediate Similarity	NPD7515	Phase 2
0.7345	Intermediate Similarity	NPD4632	Approved
0.7321	Intermediate Similarity	NPD6617	Approved
0.7321	Intermediate Similarity	NPD8130	Phase 1
0.7321	Intermediate Similarity	NPD6847	Approved
0.7321	Intermediate Similarity	NPD6869	Approved
0.7308	Intermediate Similarity	NPD5695	Phase 3
0.7304	Intermediate Similarity	NPD6009	Approved
0.7273	Intermediate Similarity	NPD1694	Approved
0.7265	Intermediate Similarity	NPD6319	Approved
0.7257	Intermediate Similarity	NPD8297	Approved
0.7257	Intermediate Similarity	NPD6882	Approved
0.7255	Intermediate Similarity	NPD5692	Phase 3
0.7238	Intermediate Similarity	NPD5221	Approved
0.7238	Intermediate Similarity	NPD5222	Approved
0.7238	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD5983	Phase 2
0.72	Intermediate Similarity	NPD6409	Approved
0.72	Intermediate Similarity	NPD7334	Approved
0.72	Intermediate Similarity	NPD6684	Approved
0.72	Intermediate Similarity	NPD7146	Approved
0.72	Intermediate Similarity	NPD7521	Approved
0.72	Intermediate Similarity	NPD5330	Approved
0.7184	Intermediate Similarity	NPD5694	Approved
0.7184	Intermediate Similarity	NPD6050	Approved
0.717	Intermediate Similarity	NPD5173	Approved
0.7168	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD6904	Approved
0.7157	Intermediate Similarity	NPD6080	Approved
0.7157	Intermediate Similarity	NPD6673	Approved
0.7143	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6399	Phase 3
0.7103	Intermediate Similarity	NPD5696	Approved
0.7083	Intermediate Similarity	NPD7604	Phase 2
0.7069	Intermediate Similarity	NPD6868	Approved
0.7069	Intermediate Similarity	NPD6274	Approved
0.7059	Intermediate Similarity	NPD6903	Approved
0.7037	Intermediate Similarity	NPD4696	Approved
0.7037	Intermediate Similarity	NPD5285	Approved
0.7037	Intermediate Similarity	NPD5286	Approved
0.703	Intermediate Similarity	NPD3618	Phase 1
0.7025	Intermediate Similarity	NPD7492	Approved
0.7019	Intermediate Similarity	NPD5693	Phase 1
0.7019	Intermediate Similarity	NPD6079	Approved
0.7009	Intermediate Similarity	NPD4755	Approved
0.7009	Intermediate Similarity	NPD6083	Phase 2
0.7009	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6084	Phase 2
0.7009	Intermediate Similarity	NPD6317	Approved
0.6992	Remote Similarity	NPD7736	Approved
0.699	Remote Similarity	NPD5328	Approved
0.6981	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD5654	Approved
0.6975	Remote Similarity	NPD6054	Approved
0.6972	Remote Similarity	NPD5223	Approved
0.6967	Remote Similarity	NPD6616	Approved
0.6967	Remote Similarity	NPD6336	Discontinued
0.6964	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD6335	Approved
0.6949	Remote Similarity	NPD6313	Approved
0.6949	Remote Similarity	NPD6314	Approved
0.6944	Remote Similarity	NPD7638	Approved
0.6939	Remote Similarity	NPD4695	Discontinued
0.6917	Remote Similarity	NPD6015	Approved
0.6917	Remote Similarity	NPD6016	Approved
0.6916	Remote Similarity	NPD7732	Phase 3
0.6911	Remote Similarity	NPD7078	Approved
0.6909	Remote Similarity	NPD5225	Approved
0.6909	Remote Similarity	NPD5211	Phase 2
0.6909	Remote Similarity	NPD5224	Approved
0.6909	Remote Similarity	NPD4633	Approved
0.6909	Remote Similarity	NPD5226	Approved
0.6903	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD7101	Approved
0.6891	Remote Similarity	NPD7100	Approved
0.6881	Remote Similarity	NPD7640	Approved
0.6881	Remote Similarity	NPD4700	Approved
0.6881	Remote Similarity	NPD7639	Approved
0.6863	Remote Similarity	NPD6098	Approved
0.686	Remote Similarity	NPD5988	Approved
0.686	Remote Similarity	NPD6370	Approved
0.6857	Remote Similarity	NPD6411	Approved
0.6852	Remote Similarity	NPD5959	Approved
0.6847	Remote Similarity	NPD5174	Approved
0.6847	Remote Similarity	NPD5175	Approved
0.6833	Remote Similarity	NPD6059	Approved
0.68	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5141	Approved
0.6783	Remote Similarity	NPD4634	Approved
0.6783	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD8293	Discontinued
0.6762	Remote Similarity	NPD5207	Approved
0.6729	Remote Similarity	NPD6001	Approved
0.6729	Remote Similarity	NPD5282	Discontinued
0.6699	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD5279	Phase 3
0.6698	Remote Similarity	NPD8034	Phase 2
0.6698	Remote Similarity	NPD8035	Phase 2
0.6696	Remote Similarity	NPD4754	Approved
0.6693	Remote Similarity	NPD7260	Phase 2
0.6667	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6101	Approved
0.6667	Remote Similarity	NPD6412	Phase 2
0.6639	Remote Similarity	NPD6909	Approved
0.6639	Remote Similarity	NPD6908	Approved
0.6609	Remote Similarity	NPD4729	Approved
0.6609	Remote Similarity	NPD5168	Approved
0.6609	Remote Similarity	NPD4730	Approved
0.6609	Remote Similarity	NPD5128	Approved
0.6606	Remote Similarity	NPD7614	Phase 1
0.6583	Remote Similarity	NPD7115	Discovery
0.6579	Remote Similarity	NPD4768	Approved
0.6579	Remote Similarity	NPD4767	Approved
0.6571	Remote Similarity	NPD5208	Approved
0.6566	Remote Similarity	NPD3617	Approved
0.6552	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD5284	Approved
0.6542	Remote Similarity	NPD5281	Approved
0.6538	Remote Similarity	NPD5690	Phase 2
0.6522	Remote Similarity	NPD6614	Approved
0.6514	Remote Similarity	NPD5210	Approved
0.6514	Remote Similarity	NPD4629	Approved
0.6512	Remote Similarity	NPD6845	Suspended
0.6509	Remote Similarity	NPD4753	Phase 2
0.6505	Remote Similarity	NPD3668	Phase 3
0.6505	Remote Similarity	NPD3665	Phase 1
0.6505	Remote Similarity	NPD3666	Approved
0.6505	Remote Similarity	NPD3133	Approved
0.6496	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD5251	Approved
0.6496	Remote Similarity	NPD5169	Approved
0.6496	Remote Similarity	NPD5248	Approved
0.6496	Remote Similarity	NPD5135	Approved
0.6496	Remote Similarity	NPD5249	Phase 3
0.6496	Remote Similarity	NPD5247	Approved
0.6496	Remote Similarity	NPD5250	Approved
0.6481	Remote Similarity	NPD4202	Approved
0.6481	Remote Similarity	NPD5778	Approved
0.6481	Remote Similarity	NPD5779	Approved
0.6471	Remote Similarity	NPD3667	Approved
0.6466	Remote Similarity	NPD6686	Approved
0.646	Remote Similarity	NPD7632	Discontinued
0.6457	Remote Similarity	NPD6033	Approved
0.6441	Remote Similarity	NPD5216	Approved
0.6441	Remote Similarity	NPD5215	Approved
0.6441	Remote Similarity	NPD5217	Approved
0.6441	Remote Similarity	NPD5127	Approved
0.6429	Remote Similarity	NPD7507	Approved
0.6391	Remote Similarity	NPD6333	Approved
0.6391	Remote Similarity	NPD6334	Approved
0.6387	Remote Similarity	NPD6053	Discontinued
0.6381	Remote Similarity	NPD4694	Approved
0.6381	Remote Similarity	NPD5280	Approved
0.6346	Remote Similarity	NPD4786	Approved
0.6346	Remote Similarity	NPD4197	Approved
0.6339	Remote Similarity	NPD4225	Approved
0.6286	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD5329	Approved
0.6281	Remote Similarity	NPD5167	Approved
0.6279	Remote Similarity	NPD7319	Approved
0.624	Remote Similarity	NPD6921	Approved
0.6186	Remote Similarity	NPD4691	Approved
0.6154	Remote Similarity	NPD4223	Phase 3
0.6154	Remote Similarity	NPD4221	Approved
0.6121	Remote Similarity	NPD6052	Approved
0.6117	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD7503	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