NPASS Compound

Structure

CID163365 OpenBabel06191715532D 41 48 0 0 1 0 0 0 0 0999 V2000 3.4228 -1.9761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2615 3.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0005 3.9158 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8476 4.4054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5430 2.4473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2385 5.3839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3910 2.9369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3910 5.8732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7580 -1.8102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2506 -2.6890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5757 3.0699 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8482 2.4475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6960 -1.9583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8477 1.4683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7407 4.6440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6951 1.9576 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5440 -1.4687 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0864 3.9169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0005 2.9366 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2391 4.4057 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6955 2.9366 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6955 3.9158 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8480 1.4688 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 0.9792 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.5325 3.2735 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6960 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3911 3.9161 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8475 2.4470 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5436 4.4054 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8480 -1.4688 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8480 -0.4896 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0790 -1.0560 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.4916 1.0003 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2596 2.6192 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6776 4.9054 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0308 -0.9970 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6344 4.2464 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5440 -0.4895 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6960 0.9792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7420 -2.4780 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 2 27 1 0 0 0 0 3 4 1 0 0 0 0 3 19 1 0 0 0 0 4 22 1 0 0 0 0 5 7 1 0 0 0 0 5 21 1 0 0 0 0 6 8 1 0 0 0 0 6 20 1 0 0 0 0 7 27 1 0 0 0 0 8 29 1 0 0 0 0 9 10 1 0 0 0 0 9 32 2 0 0 0 0 10 41 1 0 0 0 0 11 18 2 0 0 0 0 11 25 1 0 0 0 0 12 19 1 0 0 0 0 13 17 1 0 0 0 0 13 30 1 0 0 0 0 14 28 1 0 0 0 0 15 18 1 0 0 0 0 15 37 1 0 0 0 0 16 33 2 0 0 0 0 17 1 1 6 0 0 0 17 38 1 0 0 0 0 18 20 1 0 0 0 0 19 28 1 1 0 0 0 20 27 1 1 0 0 0 21 22 1 0 0 0 0 21 28 1 1 0 0 0 22 29 1 6 0 0 0 23 12 1 1 0 0 0 23 24 1 0 0 0 0 23 39 1 0 0 0 0 24 14 1 6 0 0 0 24 40 1 0 0 0 0 25 34 2 0 0 0 0 25 37 1 0 0 0 0 26 31 1 6 0 0 0 26 38 1 0 0 0 0 26 39 1 0 0 0 0 27 29 1 1 0 0 0 28 16 1 1 0 0 0 29 35 1 1 0 0 0 30 31 1 6 0 0 0 30 32 1 0 0 0 0 30 41 1 0 0 0 0 31 36 1 1 0 0 0 31 40 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	587.26
Volume:	565.562
LogP:	3.925
LogD:	3.487
LogS:	-4.356
# Rotatable Bonds:	2
TPSA:	130.95
# H-Bond Aceptor:	9
# H-Bond Donor:	3
# Rings:	8
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.345
Synthetic Accessibility Score:	6.553
Fsp3:	0.806
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.338
MDCK Permeability:	1.6233156202360988e-05
Pgp-inhibitor:	0.34
Pgp-substrate:	0.663
Human Intestinal Absorption (HIA):	0.03
20% Bioavailability (F20%):	0.584
30% Bioavailability (F30%):	0.557

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.999
Plasma Protein Binding (PPB):	88.68917083740234%
Volume Distribution (VD):	1.782
Pgp-substrate:	3.147796154022217%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.806
CYP2C19-inhibitor:	0.039
CYP2C19-substrate:	0.35
CYP2C9-inhibitor:	0.109
CYP2C9-substrate:	0.058
CYP2D6-inhibitor:	0.026
CYP2D6-substrate:	0.16
CYP3A4-inhibitor:	0.901
CYP3A4-substrate:	0.816

ADMET: Excretion

Clearance (CL):	5.801
Half-life (T1/2):	0.156

ADMET: Toxicity

hERG Blockers:	0.437
Human Hepatotoxicity (H-HT):	0.546
Drug-inuced Liver Injury (DILI):	0.528
AMES Toxicity:	0.957
Rat Oral Acute Toxicity:	0.944
Maximum Recommended Daily Dose:	0.98
Skin Sensitization:	0.947
Carcinogencity:	0.667
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.955

Download Data

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

Natural Product: NPC163365

Natural Product ID:	NPC163365
*Common Name:**	Uscharin
IUPAC Name:	n.a.
Synonyms:	Uscharin
Standard InCHIKey:	DONIPVCAKBPJLH-IGACXKNBSA-N
Standard InCHI:	InChI=1S/C31H41NO8S/c1-17-13-30(32-9-10-41-30)31(36)26(38-17)39-23-12-19-3-4-22-21(28(19,16-33)14-24(23)40-31)5-7-27(2)20(6-8-29(22,27)35)18-11-25(34)37-15-18/h9,11,16-17,19-24,26,35-36H,3-8,10,12-15H2,1-2H3/t17-,19+,20-,21+,22-,23-,24-,26+,27-,28-,29+,30+,31-/m1/s1
SMILES:	C[C@@H]1C[C@]2([C@]3([C@@H](O1)O[C@@H]1C[C@@H]4CC[C@@H]5[C@H](CC[C@]6(C)[C@H](CC[C@]56O)C5=CC(=O)OC5)[C@]4(C[C@H]1O3)C=O)O)N=CCS2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL500585
PubChem CID:	11261800
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001555] Cardenolides and derivatives [CHEMONTID:0001559] Cardenolide glycosides and derivatives

*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
NPO9165	Asclepias curassavica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16252914]
NPO30295	Calotropis gigantea	Species	Apocynaceae	Eukaryota	leaves	n.a.	n.a.	PMID[16933890]
NPO30295	Calotropis gigantea	Species	Apocynaceae	Eukaryota	n.a.	root	n.a.	PMID[19052526]
NPO9165	Asclepias curassavica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19251412]
NPO30295	Calotropis gigantea	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28817274]
NPO30295	Calotropis gigantea	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31967821]
NPO30295	Calotropis gigantea	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32649211]
NPO30295	Calotropis gigantea	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9548837]
NPO9165	Asclepias curassavica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9165	Asclepias curassavica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3369	Anemone narcissiflora	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2175	Hyperbaena columbica	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8349	Uga sinensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO26375	Viburnum grandifolium	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9165	Asclepias curassavica	Species	Apocynaceae	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
EC50	1
IC50	10
MIC	5
Others	4

Activity Type	# Activity
Cell Line	9
CELL-LINE	3
Organism	5
Others	2
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	0.01	ug.mL-1	PMID[570198]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	0.1	ug.mL-1	PMID[570198]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	0.04	ug.mL-1	PMID[570198]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	1.1	ug.mL-1	PMID[570198]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	275.0	nM	PMID[570199]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	104.0	nM	PMID[570199]
NPT457	Cell Line	BT-549	Homo sapiens	IC50	=	14.6	nM	PMID[570201]
NPT402	Cell Line	Hs-578T	Homo sapiens	IC50	=	34.0	nM	PMID[570201]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	102.0	nM	PMID[570201]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	100.0	ug.mL-1	PMID[570199]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[570199]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[570199]
NPT1108	Organism	Mycobacterium bovis BCG	Mycobacterium bovis BCG	MIC	>	80.0	ug.mL-1	PMID[570199]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	100.0	ug.mL-1	PMID[570199]
NPT22491	CELL-LINE	MEB5	Mus musculus	Activity	=	36.0	%	PMID[570200]
NPT22491	CELL-LINE	MEB5	Mus musculus	Activity	=	19.5	um	PMID[570200]
NPT22491	CELL-LINE	MEB5	Mus musculus	Activity	=	20.8	%	PMID[570200]
NPT25172	SINGLE PROTEIN	Neurogenic locus notch homolog protein 1	Homo sapiens	IC50	=	400.0	nM	PMID[570200]
NPT2	Others	Unspecified		Ratio IC50	=	7.0	n.a.	PMID[570201]
NPT2	Others	Unspecified		EC50	=	910.0	nM	PMID[570201]

☑ 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 NPC163365 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	188
0.1-0.2	1365
0.2-0.3	5944
0.3-0.4	16283
0.4-0.5	11119
0.5-0.6	5558
0.6-0.7	2002
0.7-0.8	231
0.8-0.85	1
0.85-0.9	2
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9329	High Similarity	NPC473208
0.8797	High Similarity	NPC473040
0.8589	High Similarity	NPC470094
0.7905	Intermediate Similarity	NPC91
0.7852	Intermediate Similarity	NPC16569
0.7852	Intermediate Similarity	NPC159338
0.7852	Intermediate Similarity	NPC253456
0.78	Intermediate Similarity	NPC42670
0.78	Intermediate Similarity	NPC19124
0.78	Intermediate Similarity	NPC93416
0.7748	Intermediate Similarity	NPC225385
0.7748	Intermediate Similarity	NPC142756
0.7748	Intermediate Similarity	NPC477709
0.7748	Intermediate Similarity	NPC298783
0.7748	Intermediate Similarity	NPC104585
0.7748	Intermediate Similarity	NPC476221
0.7748	Intermediate Similarity	NPC157817
0.7667	Intermediate Similarity	NPC232785
0.7667	Intermediate Similarity	NPC125077
0.7667	Intermediate Similarity	NPC188234
0.7667	Intermediate Similarity	NPC276838
0.7667	Intermediate Similarity	NPC140092
0.7667	Intermediate Similarity	NPC329986
0.7647	Intermediate Similarity	NPC171619
0.7584	Intermediate Similarity	NPC469750
0.7584	Intermediate Similarity	NPC250556
0.7533	Intermediate Similarity	NPC240070
0.7533	Intermediate Similarity	NPC471356
0.7533	Intermediate Similarity	NPC179412
0.7533	Intermediate Similarity	NPC329784
0.7516	Intermediate Similarity	NPC32793
0.7516	Intermediate Similarity	NPC116075
0.7516	Intermediate Similarity	NPC469749
0.7516	Intermediate Similarity	NPC146857
0.7516	Intermediate Similarity	NPC247190
0.7484	Intermediate Similarity	NPC59288
0.7468	Intermediate Similarity	NPC329636
0.745	Intermediate Similarity	NPC27363
0.7434	Intermediate Similarity	NPC471359
0.7434	Intermediate Similarity	NPC469755
0.7434	Intermediate Similarity	NPC197707
0.7434	Intermediate Similarity	NPC471360
0.7434	Intermediate Similarity	NPC471352
0.7434	Intermediate Similarity	NPC86159
0.7434	Intermediate Similarity	NPC471361
0.7434	Intermediate Similarity	NPC469751
0.7434	Intermediate Similarity	NPC219085
0.7434	Intermediate Similarity	NPC9499
0.7434	Intermediate Similarity	NPC469753
0.7434	Intermediate Similarity	NPC284406
0.7434	Intermediate Similarity	NPC180079
0.7434	Intermediate Similarity	NPC6108
0.7434	Intermediate Similarity	NPC469752
0.7434	Intermediate Similarity	NPC10823
0.7434	Intermediate Similarity	NPC89514
0.7434	Intermediate Similarity	NPC469754
0.7434	Intermediate Similarity	NPC251866
0.7434	Intermediate Similarity	NPC471358
0.7434	Intermediate Similarity	NPC70542
0.7434	Intermediate Similarity	NPC17896
0.7419	Intermediate Similarity	NPC194716
0.7403	Intermediate Similarity	NPC88668
0.7372	Intermediate Similarity	NPC329675
0.7303	Intermediate Similarity	NPC117702
0.7303	Intermediate Similarity	NPC146456
0.7303	Intermediate Similarity	NPC471357
0.7303	Intermediate Similarity	NPC469757
0.7239	Intermediate Similarity	NPC244380
0.7239	Intermediate Similarity	NPC61717
0.7229	Intermediate Similarity	NPC265699
0.7186	Intermediate Similarity	NPC475599
0.7186	Intermediate Similarity	NPC187497
0.7186	Intermediate Similarity	NPC100612
0.7186	Intermediate Similarity	NPC174336
0.7186	Intermediate Similarity	NPC113620
0.7181	Intermediate Similarity	NPC329905
0.7143	Intermediate Similarity	NPC311534
0.7133	Intermediate Similarity	NPC475136
0.7133	Intermediate Similarity	NPC474466
0.7126	Intermediate Similarity	NPC475527
0.7117	Intermediate Similarity	NPC214821
0.7117	Intermediate Similarity	NPC298067
0.7095	Intermediate Similarity	NPC196931
0.707	Intermediate Similarity	NPC119794
0.707	Intermediate Similarity	NPC73829
0.7067	Intermediate Similarity	NPC469756
0.7067	Intermediate Similarity	NPC292467
0.7067	Intermediate Similarity	NPC32177
0.7067	Intermediate Similarity	NPC30483
0.7067	Intermediate Similarity	NPC236973
0.7067	Intermediate Similarity	NPC55532
0.7067	Intermediate Similarity	NPC470897
0.7055	Intermediate Similarity	NPC141669
0.7048	Intermediate Similarity	NPC298005
0.7048	Intermediate Similarity	NPC36463
0.7047	Intermediate Similarity	NPC152615
0.7044	Intermediate Similarity	NPC289700
0.7044	Intermediate Similarity	NPC62172
0.7044	Intermediate Similarity	NPC145899
0.7025	Intermediate Similarity	NPC477072
0.702	Intermediate Similarity	NPC475629
0.702	Intermediate Similarity	NPC72260
0.702	Intermediate Similarity	NPC470312
0.702	Intermediate Similarity	NPC475556
0.7019	Intermediate Similarity	NPC302276
0.7019	Intermediate Similarity	NPC180770
0.7006	Intermediate Similarity	NPC155529
0.7006	Intermediate Similarity	NPC475472
0.7006	Intermediate Similarity	NPC471855
0.7	Intermediate Similarity	NPC218093
0.6994	Remote Similarity	NPC803
0.6981	Remote Similarity	NPC75318
0.6981	Remote Similarity	NPC235772
0.6981	Remote Similarity	NPC280941
0.698	Remote Similarity	NPC99620
0.698	Remote Similarity	NPC5311
0.698	Remote Similarity	NPC193382
0.698	Remote Similarity	NPC199428
0.698	Remote Similarity	NPC310341
0.6975	Remote Similarity	NPC172365
0.6975	Remote Similarity	NPC210729
0.6975	Remote Similarity	NPC82931
0.6974	Remote Similarity	NPC475419
0.6974	Remote Similarity	NPC474908
0.6974	Remote Similarity	NPC475590
0.6974	Remote Similarity	NPC40749
0.6974	Remote Similarity	NPC120390
0.6974	Remote Similarity	NPC314535
0.6974	Remote Similarity	NPC231518
0.6974	Remote Similarity	NPC173555
0.6974	Remote Similarity	NPC475219
0.6957	Remote Similarity	NPC200788
0.6957	Remote Similarity	NPC290746
0.6957	Remote Similarity	NPC75616
0.6957	Remote Similarity	NPC79250
0.6957	Remote Similarity	NPC243680
0.6954	Remote Similarity	NPC291820
0.6954	Remote Similarity	NPC81222
0.6951	Remote Similarity	NPC475892
0.6943	Remote Similarity	NPC173347
0.6937	Remote Similarity	NPC127656
0.6933	Remote Similarity	NPC471354
0.6933	Remote Similarity	NPC309034
0.6933	Remote Similarity	NPC99728
0.6933	Remote Similarity	NPC243196
0.6933	Remote Similarity	NPC34390
0.6933	Remote Similarity	NPC87250
0.6933	Remote Similarity	NPC157376
0.6933	Remote Similarity	NPC196429
0.6933	Remote Similarity	NPC158344
0.6933	Remote Similarity	NPC50305
0.6933	Remote Similarity	NPC471355
0.6933	Remote Similarity	NPC471353
0.6933	Remote Similarity	NPC474418
0.6933	Remote Similarity	NPC162910
0.6933	Remote Similarity	NPC473852
0.6933	Remote Similarity	NPC27507
0.6933	Remote Similarity	NPC84987
0.6933	Remote Similarity	NPC93883
0.6933	Remote Similarity	NPC142066
0.6933	Remote Similarity	NPC77319
0.6933	Remote Similarity	NPC471351
0.6933	Remote Similarity	NPC244402
0.6928	Remote Similarity	NPC193893
0.6928	Remote Similarity	NPC264336
0.6928	Remote Similarity	NPC474423
0.6928	Remote Similarity	NPC28532
0.6928	Remote Similarity	NPC74259
0.6923	Remote Similarity	NPC114306
0.6923	Remote Similarity	NPC477490
0.6918	Remote Similarity	NPC76999
0.6913	Remote Similarity	NPC31354
0.6913	Remote Similarity	NPC471633
0.6913	Remote Similarity	NPC84949
0.6913	Remote Similarity	NPC69576
0.6908	Remote Similarity	NPC107607
0.6899	Remote Similarity	NPC139585
0.689	Remote Similarity	NPC475152
0.689	Remote Similarity	NPC475394
0.689	Remote Similarity	NPC475584
0.6887	Remote Similarity	NPC83287
0.6883	Remote Similarity	NPC208193
0.6883	Remote Similarity	NPC117445
0.6883	Remote Similarity	NPC308262
0.6879	Remote Similarity	NPC471407
0.6875	Remote Similarity	NPC158350
0.6867	Remote Similarity	NPC106228
0.6867	Remote Similarity	NPC138372
0.6848	Remote Similarity	NPC298469
0.6842	Remote Similarity	NPC9674
0.6842	Remote Similarity	NPC19028
0.6842	Remote Similarity	NPC44899
0.6842	Remote Similarity	NPC29639
0.6842	Remote Similarity	NPC5883
0.6842	Remote Similarity	NPC304260
0.6835	Remote Similarity	NPC477493
0.6832	Remote Similarity	NPC477236
0.6821	Remote Similarity	NPC203862
0.6821	Remote Similarity	NPC290693
0.6813	Remote Similarity	NPC248703

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 NPC163365 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	134
0.1-0.2	926
0.2-0.3	4005
0.3-0.4	3070
0.4-0.5	742
0.5-0.6	236
0.6-0.7	26
0.7-0.8	10
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8986	High Similarity	NPD7625	Phase 1
0.7584	Intermediate Similarity	NPD7507	Approved
0.7434	Intermediate Similarity	NPD7319	Approved
0.702	Intermediate Similarity	NPD8294	Approved
0.702	Intermediate Similarity	NPD8377	Approved
0.6974	Remote Similarity	NPD8380	Approved
0.6974	Remote Similarity	NPD8379	Approved
0.6974	Remote Similarity	NPD8033	Approved
0.6974	Remote Similarity	NPD8296	Approved
0.6974	Remote Similarity	NPD8335	Approved
0.6974	Remote Similarity	NPD8378	Approved
0.6954	Remote Similarity	NPD7516	Approved
0.6887	Remote Similarity	NPD7327	Approved
0.6887	Remote Similarity	NPD7328	Approved
0.6513	Remote Similarity	NPD8133	Approved
0.6456	Remote Similarity	NPD6067	Discontinued
0.6446	Remote Similarity	NPD6334	Approved
0.6446	Remote Similarity	NPD6333	Approved
0.6433	Remote Similarity	NPD7503	Approved
0.64	Remote Similarity	NPD6686	Approved
0.6398	Remote Similarity	NPD7736	Approved
0.6352	Remote Similarity	NPD8328	Phase 3
0.6329	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD6914	Discontinued
0.6273	Remote Similarity	NPD8451	Approved
0.6235	Remote Similarity	NPD8293	Discontinued
0.6235	Remote Similarity	NPD8448	Approved
0.6225	Remote Similarity	NPD6412	Phase 2
0.622	Remote Similarity	NPD8390	Approved
0.622	Remote Similarity	NPD8392	Approved
0.622	Remote Similarity	NPD8391	Approved
0.6196	Remote Similarity	NPD8336	Approved
0.6196	Remote Similarity	NPD8337	Approved
0.6188	Remote Similarity	NPD6370	Approved
0.6169	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD8338	Approved
0.6135	Remote Similarity	NPD7078	Approved
0.6135	Remote Similarity	NPD8074	Phase 3
0.6125	Remote Similarity	NPD6909	Approved
0.6125	Remote Similarity	NPD6908	Approved
0.6111	Remote Similarity	NPD7492	Approved
0.6111	Remote Similarity	NPD8342	Approved
0.6111	Remote Similarity	NPD8340	Approved
0.6111	Remote Similarity	NPD8299	Approved
0.6111	Remote Similarity	NPD8341	Approved
0.6081	Remote Similarity	NPD7638	Approved
0.6076	Remote Similarity	NPD6317	Approved
0.6076	Remote Similarity	NPD6009	Approved
0.6076	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6074	Remote Similarity	NPD6616	Approved
0.6062	Remote Similarity	NPD6054	Approved
0.6062	Remote Similarity	NPD6059	Approved
0.6049	Remote Similarity	NPD7604	Phase 2
0.6049	Remote Similarity	NPD7122	Discontinued
0.6049	Remote Similarity	NPD7642	Approved
0.604	Remote Similarity	NPD7639	Approved
0.604	Remote Similarity	NPD7640	Approved
0.6039	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6026	Remote Similarity	NPD6882	Approved
0.6025	Remote Similarity	NPD8517	Approved
0.6025	Remote Similarity	NPD8516	Approved
0.6025	Remote Similarity	NPD8515	Approved
0.6025	Remote Similarity	NPD6921	Approved
0.6025	Remote Similarity	NPD8513	Phase 3
0.5988	Remote Similarity	NPD7260	Phase 2
0.5987	Remote Similarity	NPD4632	Approved
0.5963	Remote Similarity	NPD6319	Approved
0.5952	Remote Similarity	NPD6845	Suspended
0.5948	Remote Similarity	NPD4211	Phase 1
0.5948	Remote Similarity	NPD6008	Approved
0.5938	Remote Similarity	NPD7641	Discontinued
0.5935	Remote Similarity	NPD6372	Approved
0.5935	Remote Similarity	NPD6373	Approved
0.5926	Remote Similarity	NPD6015	Approved
0.5926	Remote Similarity	NPD6016	Approved
0.5924	Remote Similarity	NPD8297	Approved
0.5897	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.589	Remote Similarity	NPD5988	Approved
0.5885	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.5875	Remote Similarity	NPD7115	Discovery
0.5871	Remote Similarity	NPD7320	Approved
0.586	Remote Similarity	NPD6649	Approved
0.586	Remote Similarity	NPD6650	Approved
0.5858	Remote Similarity	NPD8449	Approved
0.5854	Remote Similarity	NPD7830	Approved
0.5854	Remote Similarity	NPD7829	Approved
0.5848	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5844	Remote Similarity	NPD6402	Approved
0.5844	Remote Similarity	NPD7128	Approved
0.5844	Remote Similarity	NPD6675	Approved
0.5844	Remote Similarity	NPD5739	Approved
0.5833	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5824	Remote Similarity	NPD8450	Suspended
0.5817	Remote Similarity	NPD4754	Approved
0.5817	Remote Similarity	NPD6052	Approved
0.5808	Remote Similarity	NPD6033	Approved
0.5802	Remote Similarity	NPD7518	Approved
0.5802	Remote Similarity	NPD7519	Approved
0.5802	Remote Similarity	NPD8462	Phase 1
0.5802	Remote Similarity	NPD7517	Approved
0.5796	Remote Similarity	NPD5135	Approved
0.5796	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5793	Remote Similarity	NPD8080	Discontinued
0.5789	Remote Similarity	NPD8415	Approved
0.5776	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD6881	Approved
0.5769	Remote Similarity	NPD6899	Approved
0.5732	Remote Similarity	NPD5983	Phase 2
0.5723	Remote Similarity	NPD6053	Discontinued
0.5707	Remote Similarity	NPD8407	Phase 2
0.5705	Remote Similarity	NPD5697	Approved
0.5705	Remote Similarity	NPD5701	Approved
0.5705	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5696	Remote Similarity	NPD7102	Approved
0.5696	Remote Similarity	NPD6883	Approved
0.5696	Remote Similarity	NPD7290	Approved
0.5689	Remote Similarity	NPD6336	Discontinued
0.5679	Remote Similarity	NPD7505	Discontinued
0.5671	Remote Similarity	NPD7147	Phase 3
0.5671	Remote Similarity	NPD7148	Clinical (unspecified phase)
0.5669	Remote Similarity	NPD6011	Approved
0.5669	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.566	Remote Similarity	NPD8130	Phase 1
0.566	Remote Similarity	NPD6869	Approved
0.566	Remote Similarity	NPD6617	Approved
0.566	Remote Similarity	NPD6847	Approved
0.565	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.5649	Remote Similarity	NPD7632	Discontinued
0.5636	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5635	Remote Similarity	NPD8368	Discontinued
0.5633	Remote Similarity	NPD6014	Approved
0.5633	Remote Similarity	NPD6012	Approved
0.5633	Remote Similarity	NPD6013	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