NPASS Compound

Structure

CID205167 OpenBabel06191715592D 21 24 0 0 1 0 0 0 0 0999 V2000 -4.9234 0.0004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6128 0.9312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8064 -0.4656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8062 2.3282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4197 -0.4656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4195 1.3970 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8067 -0.4656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8064 1.3967 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6131 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6130 0.9313 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2260 0.9314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0001 2.7937 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2261 0.0002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8067 1.3967 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0003 0.9312 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8066 2.3280 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -4.0746 1.4215 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0002 3.7626 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6456 2.8124 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0748 -0.4897 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 3 1 0 0 0 0 2 8 1 0 0 0 0 3 17 1 0 0 0 0 4 8 2 0 0 0 0 4 12 1 0 0 0 0 5 9 2 0 0 0 0 5 13 1 0 0 0 0 6 10 2 0 0 0 0 6 11 1 0 0 0 0 7 9 1 0 0 0 0 7 17 1 0 0 0 0 8 15 1 0 0 0 0 9 10 1 0 0 0 0 11 13 2 0 0 0 0 11 18 1 0 0 0 0 12 16 1 0 0 0 0 12 19 1 1 0 0 0 13 21 1 0 0 0 0 14 10 1 6 0 0 0 14 15 1 0 0 0 0 14 16 1 0 0 0 0 15 17 1 1 0 0 0 16 20 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	289.13
Volume:	286.678
LogP:	0.702
LogD:	1.019
LogS:	-1.416
# Rotatable Bonds:	1
TPSA:	73.16
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.665
Synthetic Accessibility Score:	4.128
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.864
MDCK Permeability:	1.1495208127598744e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.724
Human Intestinal Absorption (HIA):	0.248
20% Bioavailability (F20%):	0.673
30% Bioavailability (F30%):	0.197

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.962
Plasma Protein Binding (PPB):	61.47563171386719%
Volume Distribution (VD):	2.182
Pgp-substrate:	38.51517868041992%

ADMET: Metabolism

CYP1A2-inhibitor:	0.234
CYP1A2-substrate:	0.533
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.732
CYP2C9-inhibitor:	0.012
CYP2C9-substrate:	0.375
CYP2D6-inhibitor:	0.458
CYP2D6-substrate:	0.771
CYP3A4-inhibitor:	0.004
CYP3A4-substrate:	0.324

ADMET: Excretion

Clearance (CL):	14.867
Half-life (T1/2):	0.79

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.051
Drug-inuced Liver Injury (DILI):	0.098
AMES Toxicity:	0.081
Rat Oral Acute Toxicity:	0.823
Maximum Recommended Daily Dose:	0.927
Skin Sensitization:	0.099
Carcinogencity:	0.873
Eye Corrosion:	0.004
Eye Irritation:	0.018
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC205167

Natural Product ID:	NPC205167
*Common Name:**	Pseudolycorine
IUPAC Name:	n.a.
Synonyms:	TCMDC-132036
Standard InCHIKey:	CKAHWDNDUGDSLE-ARLBYUKCSA-N
Standard InCHI:	InChI=1S/C16H19NO4/c1-21-13-5-9-7-17-3-2-8-4-12(19)16(20)14(15(8)17)10(9)6-11(13)18/h4-6,12,14-16,18-20H,2-3,7H2,1H3/t12-,14-,15+,16+/m0/s1
SMILES:	COc1cc2CN3CCC4=C[C@@H]([C@H]([C@@H](c2cc1O)[C@H]34)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL586091
PubChem CID:	443689
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0001908] Benzoquinolines [CHEMONTID:0000100] Phenanthridines 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
NPO33168	amaryllidaceae isoquinoline	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1336040]
NPO27843	Lycoris radiata	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21510636]
NPO23000	Zephyranthes carinata	Species	Amaryllidaceae	Eukaryota	Whole Plants	n.a.	n.a.	PMID[28898076]
NPO5400	Lycoris aurea	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27843	Lycoris radiata	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27843	Lycoris radiata	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5400	Lycoris aurea	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17954.1	Narcissus tazetta l var. chinensis roem.	Varieties	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5400	Lycoris aurea	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27843	Lycoris radiata	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27843	Lycoris radiata	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23000	Zephyranthes carinata	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5400	Lycoris aurea	Species	Amaryllidaceae	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	23
Others	14

Activity Type	# Activity
Cell Line	8
Individual Protein	4
NON-MOLECULAR	6
Organism	11
Others	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	Inhibition	=	18.0	%	PMID[541675]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	7500.0	nM	PMID[541676]
NPT169	Cell Line	B16-F10	Mus musculus	IC50	=	7500.0	nM	PMID[541676]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	IC50	>	10000.0	nM	PMID[541676]
NPT3190	Cell Line	NHDF	Homo sapiens	IC50	=	66900.0	nM	PMID[541676]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	7400.0	nM	PMID[541677]
NPT916	Cell Line	SK-MEL	Homo sapiens	IC50	>	10000.0	nM	PMID[541677]
NPT169	Cell Line	B16-F10	Mus musculus	IC50	=	7500.0	nM	PMID[541677]
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	IC50	=	187630.0	nM	PMID[541680]
NPT33	Organism	Japanese encephalitis virus	Japanese encephalitis virus	IC50	=	0.28	ug.mL-1	PMID[541674]
NPT4327	Organism	Yellow fever virus	Yellow fever virus	IC50	=	0.35	ug.mL-1	PMID[541674]
NPT4328	Organism	Dengue virus type 4	Dengue virus 4	IC50	=	0.39	ug.mL-1	PMID[541674]
NPT27	Others	Unspecified		TI	=	5.0	n.a.	PMID[541674]
NPT27	Others	Unspecified		TI	=	3.7	n.a.	PMID[541674]
NPT27	Others	Unspecified		TI	=	2.6	n.a.	PMID[541674]
NPT341	Organism	Punta Toro virus	Punta Toro virus	IC50	=	0.6	ug.mL-1	PMID[541674]
NPT4329	Organism	Rift Valley fever virus	Rift Valley fever virus	IC50	=	0.63	ug.mL-1	PMID[541674]
NPT27	Others	Unspecified		TI	=	3.9	n.a.	PMID[541674]
NPT27	Others	Unspecified		TI	=	6.0	n.a.	PMID[541674]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Inhibition	=	90.0	%	PMID[541675]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Inhibition	=	31.0	%	PMID[541675]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Inhibition	=	3.0	%	PMID[541675]
NPT2	Others	Unspecified		IFI	=	4.14	%	PMID[541675]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	XC50	=	990.84	nM	PMID[541675]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	7700.0	nM	PMID[541676]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	7800.0	nM	PMID[541676]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	7900.0	nM	PMID[541676]
NPT27	Others	Unspecified		IC50	=	44000.0	nM	PMID[541676]
NPT27	Others	Unspecified		IC50	=	79100.0	nM	PMID[541676]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	7900.0	nM	PMID[541677]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	7800.0	nM	PMID[541677]
NPT942	Individual Protein	Glucose transporter	Homo sapiens	Inhibition	=	4.04	%	PMID[541679]
NPT943	Individual Protein	Hexose transporter 1	Plasmodium falciparum	Inhibition	=	3.79	%	PMID[541679]
NPT944	Individual Protein	Glucose transporter	Leishmania mexicana	Inhibition	=	1.58	%	PMID[541679]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	>	30.0	ug.mL-1	PMID[541681]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	>	30.0	ug.mL-1	PMID[541681]

☑ 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 NPC205167 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	252
0.1-0.2	1229
0.2-0.3	4361
0.3-0.4	12873
0.4-0.5	6399
0.5-0.6	12229
0.6-0.7	4164
0.7-0.8	882
0.8-0.85	168
0.85-0.9	119
0.9-0.95	14
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9867	High Similarity	NPC249274
0.9408	High Similarity	NPC147091
0.9299	High Similarity	NPC181653
0.9299	High Similarity	NPC190332
0.9177	High Similarity	NPC100566
0.9108	High Similarity	NPC320104
0.9085	High Similarity	NPC133011
0.9085	High Similarity	NPC82285
0.9074	High Similarity	NPC237044
0.9018	High Similarity	NPC474325
0.9012	High Similarity	NPC304675
0.8981	High Similarity	NPC4304
0.8963	High Similarity	NPC474745
0.8954	High Similarity	NPC274026
0.8947	High Similarity	NPC135538
0.8947	High Similarity	NPC476571
0.8947	High Similarity	NPC147390
0.8947	High Similarity	NPC24233
0.8947	High Similarity	NPC246587
0.8947	High Similarity	NPC428
0.8917	High Similarity	NPC59028
0.8917	High Similarity	NPC92191
0.8882	High Similarity	NPC321505
0.8882	High Similarity	NPC191376
0.8882	High Similarity	NPC179825
0.8831	High Similarity	NPC151895
0.8831	High Similarity	NPC97221
0.8831	High Similarity	NPC220858
0.8831	High Similarity	NPC192768
0.8831	High Similarity	NPC88249
0.882	High Similarity	NPC210140
0.8802	High Similarity	NPC475981
0.8802	High Similarity	NPC474746
0.878	High Similarity	NPC187678
0.8773	High Similarity	NPC225597
0.8773	High Similarity	NPC477640
0.8773	High Similarity	NPC470739
0.8766	High Similarity	NPC103379
0.8766	High Similarity	NPC477565
0.8765	High Similarity	NPC82533
0.8765	High Similarity	NPC475686
0.8765	High Similarity	NPC58766
0.8765	High Similarity	NPC266176
0.8765	High Similarity	NPC158148
0.8765	High Similarity	NPC290759
0.875	High Similarity	NPC324144
0.875	High Similarity	NPC185838
0.8742	High Similarity	NPC97072
0.8742	High Similarity	NPC215829
0.8734	High Similarity	NPC475326
0.8726	High Similarity	NPC110416
0.8726	High Similarity	NPC276588
0.8726	High Similarity	NPC2413
0.8726	High Similarity	NPC204828
0.8726	High Similarity	NPC295691
0.8726	High Similarity	NPC207757
0.8726	High Similarity	NPC469817
0.8726	High Similarity	NPC39701
0.8726	High Similarity	NPC189266
0.8726	High Similarity	NPC278799
0.8726	High Similarity	NPC249797
0.8726	High Similarity	NPC54379
0.8726	High Similarity	NPC184026
0.8726	High Similarity	NPC172765
0.8726	High Similarity	NPC5238
0.8726	High Similarity	NPC193949
0.8726	High Similarity	NPC127674
0.8712	High Similarity	NPC311991
0.8712	High Similarity	NPC474475
0.8704	High Similarity	NPC57812
0.8704	High Similarity	NPC474324
0.8704	High Similarity	NPC150879
0.8698	High Similarity	NPC230098
0.8696	High Similarity	NPC477563
0.8696	High Similarity	NPC136508
0.8696	High Similarity	NPC212794
0.8696	High Similarity	NPC134858
0.8696	High Similarity	NPC196447
0.8696	High Similarity	NPC13504
0.8696	High Similarity	NPC253043
0.8696	High Similarity	NPC306843
0.8696	High Similarity	NPC96603
0.8696	High Similarity	NPC78222
0.8679	High Similarity	NPC111485
0.8671	High Similarity	NPC186063
0.865	High Similarity	NPC475845
0.8642	High Similarity	NPC476002
0.8642	High Similarity	NPC124657
0.8636	High Similarity	NPC476151
0.8634	High Similarity	NPC233650
0.8627	High Similarity	NPC130926
0.8599	High Similarity	NPC37272
0.8598	High Similarity	NPC474708
0.8591	High Similarity	NPC131204
0.8591	High Similarity	NPC301050
0.8589	High Similarity	NPC145832
0.8589	High Similarity	NPC158376
0.8589	High Similarity	NPC12053
0.8589	High Similarity	NPC117188
0.8589	High Similarity	NPC205421
0.8589	High Similarity	NPC474931
0.8589	High Similarity	NPC306555
0.8589	High Similarity	NPC81218
0.858	High Similarity	NPC24465
0.858	High Similarity	NPC276944
0.858	High Similarity	NPC232514
0.858	High Similarity	NPC238530
0.8563	High Similarity	NPC294790
0.8563	High Similarity	NPC148693
0.8563	High Similarity	NPC118633
0.8554	High Similarity	NPC199465
0.8554	High Similarity	NPC229166
0.8554	High Similarity	NPC128560
0.8553	High Similarity	NPC160931
0.8553	High Similarity	NPC37205
0.8545	High Similarity	NPC476331
0.8535	High Similarity	NPC76213
0.8535	High Similarity	NPC277669
0.8528	High Similarity	NPC13916
0.8528	High Similarity	NPC264850
0.8509	High Similarity	NPC18402
0.8509	High Similarity	NPC166014
0.8509	High Similarity	NPC27410
0.8503	High Similarity	NPC474470
0.8494	Intermediate Similarity	NPC2314
0.8491	Intermediate Similarity	NPC78733
0.8487	Intermediate Similarity	NPC328750
0.8487	Intermediate Similarity	NPC188163
0.8487	Intermediate Similarity	NPC474915
0.8487	Intermediate Similarity	NPC213206
0.8457	Intermediate Similarity	NPC60186
0.8452	Intermediate Similarity	NPC114364
0.8452	Intermediate Similarity	NPC320223
0.8452	Intermediate Similarity	NPC15919
0.8442	Intermediate Similarity	NPC294249
0.8434	Intermediate Similarity	NPC239775
0.8428	Intermediate Similarity	NPC2295
0.8428	Intermediate Similarity	NPC477564
0.8424	Intermediate Similarity	NPC83198
0.8424	Intermediate Similarity	NPC164429
0.8424	Intermediate Similarity	NPC204908
0.8421	Intermediate Similarity	NPC314682
0.8408	Intermediate Similarity	NPC207824
0.8408	Intermediate Similarity	NPC60538
0.8405	Intermediate Similarity	NPC1229
0.8402	Intermediate Similarity	NPC244554
0.8402	Intermediate Similarity	NPC32154
0.8377	Intermediate Similarity	NPC136860
0.8377	Intermediate Similarity	NPC476567
0.8377	Intermediate Similarity	NPC128019
0.8373	Intermediate Similarity	NPC477562
0.8373	Intermediate Similarity	NPC26240
0.8373	Intermediate Similarity	NPC69712
0.8373	Intermediate Similarity	NPC109925
0.8365	Intermediate Similarity	NPC148898
0.8365	Intermediate Similarity	NPC26601
0.8354	Intermediate Similarity	NPC121275
0.8354	Intermediate Similarity	NPC284183
0.8354	Intermediate Similarity	NPC4138
0.8344	Intermediate Similarity	NPC475959
0.8344	Intermediate Similarity	NPC7467
0.8333	Intermediate Similarity	NPC329969
0.8333	Intermediate Similarity	NPC49353
0.8313	Intermediate Similarity	NPC160570
0.8313	Intermediate Similarity	NPC470324
0.8304	Intermediate Similarity	NPC248642
0.8304	Intermediate Similarity	NPC116284
0.8294	Intermediate Similarity	NPC126284
0.8284	Intermediate Similarity	NPC241704
0.828	Intermediate Similarity	NPC51957
0.828	Intermediate Similarity	NPC106295
0.828	Intermediate Similarity	NPC16107
0.828	Intermediate Similarity	NPC210437
0.828	Intermediate Similarity	NPC476144
0.8274	Intermediate Similarity	NPC152680
0.8274	Intermediate Similarity	NPC66341
0.8274	Intermediate Similarity	NPC192135
0.8274	Intermediate Similarity	NPC232386
0.8274	Intermediate Similarity	NPC190783
0.8274	Intermediate Similarity	NPC477020
0.8272	Intermediate Similarity	NPC78359
0.8272	Intermediate Similarity	NPC65490
0.8272	Intermediate Similarity	NPC40389
0.8272	Intermediate Similarity	NPC315707
0.8272	Intermediate Similarity	NPC148014
0.8266	Intermediate Similarity	NPC162694
0.8263	Intermediate Similarity	NPC168753
0.8263	Intermediate Similarity	NPC75958
0.8263	Intermediate Similarity	NPC118274
0.8261	Intermediate Similarity	NPC325871
0.8261	Intermediate Similarity	NPC99659
0.8256	Intermediate Similarity	NPC156576
0.8253	Intermediate Similarity	NPC252960
0.8253	Intermediate Similarity	NPC298979
0.8246	Intermediate Similarity	NPC312918
0.8246	Intermediate Similarity	NPC155442
0.8246	Intermediate Similarity	NPC477561
0.8246	Intermediate Similarity	NPC305847
0.8246	Intermediate Similarity	NPC476574
0.8242	Intermediate Similarity	NPC180306

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 NPC205167 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	166
0.1-0.2	615
0.2-0.3	926
0.3-0.4	2219
0.4-0.5	2697
0.5-0.6	1683
0.6-0.7	657
0.7-0.8	169
0.8-0.85	16
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8765	High Similarity	NPD2489	Approved
0.8765	High Similarity	NPD27	Approved
0.8662	High Similarity	NPD4773	Phase 2
0.8662	High Similarity	NPD4772	Phase 2
0.8589	High Similarity	NPD2969	Approved
0.8589	High Similarity	NPD2970	Approved
0.8487	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.8415	Intermediate Similarity	NPD3051	Approved
0.8313	Intermediate Similarity	NPD2898	Approved
0.8303	Intermediate Similarity	NPD6071	Discontinued
0.828	Intermediate Similarity	NPD4584	Approved
0.8272	Intermediate Similarity	NPD2560	Approved
0.8272	Intermediate Similarity	NPD2563	Approved
0.8246	Intermediate Similarity	NPD7313	Approved
0.8246	Intermediate Similarity	NPD7312	Approved
0.8246	Intermediate Similarity	NPD7310	Approved
0.8246	Intermediate Similarity	NPD7311	Approved
0.8198	Intermediate Similarity	NPD7309	Approved
0.8193	Intermediate Similarity	NPD4010	Discontinued
0.8103	Intermediate Similarity	NPD4663	Approved
0.8098	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD5241	Discontinued
0.8063	Intermediate Similarity	NPD3641	Approved
0.8063	Intermediate Similarity	NPD3640	Phase 3
0.8063	Intermediate Similarity	NPD3639	Approved
0.8057	Intermediate Similarity	NPD7906	Approved
0.805	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.8035	Intermediate Similarity	NPD4578	Approved
0.8035	Intermediate Similarity	NPD4577	Approved
0.7989	Intermediate Similarity	NPD8054	Approved
0.7989	Intermediate Similarity	NPD8053	Approved
0.7988	Intermediate Similarity	NPD4481	Phase 3
0.7962	Intermediate Similarity	NPD4236	Phase 3
0.7962	Intermediate Similarity	NPD4237	Approved
0.7952	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD7833	Phase 2
0.7952	Intermediate Similarity	NPD7831	Phase 2
0.7927	Intermediate Similarity	NPD7298	Approved
0.7917	Intermediate Similarity	NPD6107	Approved
0.7879	Intermediate Similarity	NPD5772	Approved
0.7879	Intermediate Similarity	NPD2978	Approved
0.7879	Intermediate Similarity	NPD2977	Approved
0.7879	Intermediate Similarity	NPD5773	Approved
0.7865	Intermediate Similarity	NPD2490	Approved
0.7865	Intermediate Similarity	NPD2488	Approved
0.7853	Intermediate Similarity	NPD4017	Approved
0.7829	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD4166	Phase 2
0.7764	Intermediate Similarity	NPD2420	Approved
0.7764	Intermediate Similarity	NPD2421	Approved
0.7751	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD3060	Approved
0.773	Intermediate Similarity	NPD6030	Approved
0.773	Intermediate Similarity	NPD6031	Approved
0.7702	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD8156	Discontinued
0.7644	Intermediate Similarity	NPD5312	Approved
0.7644	Intermediate Similarity	NPD5313	Approved
0.7627	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD5177	Phase 3
0.7613	Intermediate Similarity	NPD2674	Phase 3
0.7593	Intermediate Similarity	NPD3845	Phase 1
0.7586	Intermediate Similarity	NPD8251	Approved
0.7586	Intermediate Similarity	NPD8099	Discontinued
0.7586	Intermediate Similarity	NPD8252	Approved
0.7564	Intermediate Similarity	NPD2238	Phase 2
0.7548	Intermediate Similarity	NPD3145	Approved
0.7548	Intermediate Similarity	NPD3144	Approved
0.7547	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD2494	Approved
0.7487	Intermediate Similarity	NPD3452	Approved
0.7487	Intermediate Similarity	NPD3450	Approved
0.7487	Intermediate Similarity	NPD2493	Approved
0.7484	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD6788	Approved
0.747	Intermediate Similarity	NPD4210	Discontinued
0.7468	Intermediate Similarity	NPD817	Approved
0.7468	Intermediate Similarity	NPD823	Approved
0.746	Intermediate Similarity	NPD4583	Approved
0.746	Intermediate Similarity	NPD4582	Approved
0.7447	Intermediate Similarity	NPD3448	Approved
0.7447	Intermediate Similarity	NPD2491	Approved
0.7439	Intermediate Similarity	NPD3124	Discontinued
0.7436	Intermediate Similarity	NPD5718	Phase 2
0.743	Intermediate Similarity	NPD2971	Approved
0.743	Intermediate Similarity	NPD2968	Approved
0.7425	Intermediate Similarity	NPD4005	Discontinued
0.7407	Intermediate Similarity	NPD4162	Approved
0.7407	Intermediate Similarity	NPD4002	Approved
0.7407	Intermediate Similarity	NPD4004	Approved
0.7378	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD1753	Discontinued
0.7368	Intermediate Similarity	NPD4040	Phase 1
0.736	Intermediate Similarity	NPD6297	Approved
0.7354	Intermediate Similarity	NPD3057	Approved
0.7349	Intermediate Similarity	NPD6090	Discontinued
0.7342	Intermediate Similarity	NPD3110	Approved
0.7342	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD3109	Approved
0.7342	Intermediate Similarity	NPD3620	Phase 2
0.7333	Intermediate Similarity	NPD7281	Phase 3
0.7333	Intermediate Similarity	NPD7280	Phase 3
0.733	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD6688	Approved
0.7314	Intermediate Similarity	NPD6687	Approved
0.7312	Intermediate Similarity	NPD6896	Approved
0.7312	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD6895	Approved
0.7308	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD6851	Approved
0.7293	Intermediate Similarity	NPD6853	Approved
0.7289	Intermediate Similarity	NPD1424	Approved
0.7283	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD1136	Approved
0.7278	Intermediate Similarity	NPD1130	Approved
0.7278	Intermediate Similarity	NPD1132	Approved
0.7273	Intermediate Similarity	NPD2974	Approved
0.7273	Intermediate Similarity	NPD2973	Approved
0.7273	Intermediate Similarity	NPD2975	Approved
0.7267	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD3533	Approved
0.7263	Intermediate Similarity	NPD2972	Approved
0.7256	Intermediate Similarity	NPD6331	Phase 2
0.7249	Intermediate Similarity	NPD4580	Approved
0.7244	Intermediate Similarity	NPD3636	Approved
0.7244	Intermediate Similarity	NPD3635	Approved
0.7244	Intermediate Similarity	NPD3637	Approved
0.7243	Intermediate Similarity	NPD7296	Approved
0.7239	Intermediate Similarity	NPD7037	Approved
0.7226	Intermediate Similarity	NPD4103	Phase 2
0.7226	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD5604	Discontinued
0.7222	Intermediate Similarity	NPD2161	Phase 2
0.7219	Intermediate Similarity	NPD5582	Discontinued
0.7215	Intermediate Similarity	NPD597	Approved
0.7215	Intermediate Similarity	NPD601	Approved
0.7215	Intermediate Similarity	NPD598	Approved
0.7214	Intermediate Similarity	NPD6997	Phase 2
0.7209	Intermediate Similarity	NPD5977	Approved
0.7209	Intermediate Similarity	NPD5978	Approved
0.7208	Intermediate Similarity	NPD4659	Approved
0.7202	Intermediate Similarity	NPD2122	Discontinued
0.72	Intermediate Similarity	NPD7802	Discontinued
0.7186	Intermediate Similarity	NPD4123	Phase 3
0.7186	Intermediate Similarity	NPD3645	Discontinued
0.7182	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD7047	Phase 3
0.7171	Intermediate Similarity	NPD2667	Approved
0.7171	Intermediate Similarity	NPD2668	Approved
0.7171	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD7124	Phase 2
0.7158	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD5754	Discontinued
0.7143	Intermediate Similarity	NPD2232	Approved
0.7143	Intermediate Similarity	NPD4420	Approved
0.7143	Intermediate Similarity	NPD2042	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4666	Phase 3
0.7143	Intermediate Similarity	NPD7526	Approved
0.7143	Intermediate Similarity	NPD2041	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2233	Approved
0.7143	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2230	Approved
0.7143	Intermediate Similarity	NPD52	Approved
0.7126	Intermediate Similarity	NPD4055	Discovery
0.7125	Intermediate Similarity	NPD3059	Approved
0.7125	Intermediate Similarity	NPD3061	Approved
0.7125	Intermediate Similarity	NPD3062	Approved
0.7118	Intermediate Similarity	NPD824	Approved
0.7118	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD3692	Discontinued
0.7108	Intermediate Similarity	NPD5160	Discontinued
0.7108	Intermediate Similarity	NPD2677	Approved
0.7107	Intermediate Similarity	NPD7827	Phase 1
0.7097	Intermediate Similarity	NPD3808	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD3595	Approved
0.7089	Intermediate Similarity	NPD2606	Approved
0.7089	Intermediate Similarity	NPD2605	Approved
0.7089	Intermediate Similarity	NPD3594	Approved
0.7086	Intermediate Similarity	NPD5709	Phase 3
0.7083	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5006	Approved
0.7083	Intermediate Similarity	NPD5005	Approved
0.7078	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD3656	Approved
0.7066	Intermediate Similarity	NPD6666	Approved
0.7066	Intermediate Similarity	NPD6667	Approved
0.7063	Intermediate Similarity	NPD4475	Approved
0.7063	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD4474	Approved
0.7059	Intermediate Similarity	NPD3686	Approved
0.7059	Intermediate Similarity	NPD3687	Approved
0.7056	Intermediate Similarity	NPD4873	Discontinued
0.7056	Intermediate Similarity	NPD6042	Phase 2

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