NPASS Compound

Structure

NPC30182 OpenBabel07101719132D 51 57 0 0 1 0 0 0 0 0999 V2000 6.5696 -3.2070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1055 2.7930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.6318 -3.7070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2395 -3.7070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.7658 -6.2070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8376 -3.2070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2697 -2.0465 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 6.5696 -2.2070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4357 -0.7070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7036 -1.7070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5696 -0.2070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3017 -5.2070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5075 2.2930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4357 -4.7070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3735 2.7930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3017 -2.2070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1055 0.7930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0337 -3.2070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2395 -1.7070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4357 -1.7070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7036 -0.7070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1677 -4.7070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5075 1.2930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1677 -3.7070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2395 -0.7070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1055 -0.2070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3017 -3.2070 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2395 1.2930 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 10.8998 -3.7070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1055 -2.2070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3735 0.7930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3735 -0.2070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0337 -5.2070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0576 0.7687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9716 -0.7070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8998 -4.7070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9716 -1.7070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6369 -0.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4357 -3.7070 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.2395 2.2930 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 10.0337 -6.2070 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9885 1.1340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.7658 -3.2070 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1055 -3.2070 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.7658 -5.2070 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8376 -2.2070 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4879 -1.4231 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8376 -0.2070 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 41 1 0 0 0 0 2 42 1 0 0 0 0 3 45 1 0 0 0 0 4 46 1 0 0 0 0 5 47 1 0 0 0 0 6 48 1 0 0 0 0 7 49 1 0 0 0 0 8 50 1 0 0 0 0 9 11 1 0 0 0 0 9 21 2 0 0 0 0 10 12 2 0 0 0 0 10 21 1 0 0 0 0 11 22 2 0 0 0 0 12 22 1 0 0 0 0 13 15 1 0 0 0 0 13 23 1 0 0 0 0 14 16 1 0 0 0 0 14 24 1 0 0 0 0 15 41 1 0 0 0 0 16 42 1 0 0 0 0 17 21 1 0 0 0 0 18 27 1 0 0 0 0 19 25 2 0 0 0 0 19 30 1 0 0 0 0 20 26 2 0 0 0 0 20 31 1 0 0 0 0 22 51 1 0 0 0 0 23 25 1 0 0 0 0 23 34 2 0 0 0 0 24 32 2 0 0 0 0 24 35 1 0 0 0 0 25 28 1 0 0 0 0 26 27 1 0 0 0 0 26 33 1 0 0 0 0 27 36 2 0 0 0 0 28 17 1 1 0 0 0 28 41 1 0 0 0 0 29 18 1 1 0 0 0 29 32 1 0 0 0 0 29 42 1 0 0 0 0 30 37 2 0 0 0 0 30 45 1 0 0 0 0 31 38 2 0 0 0 0 31 46 1 0 0 0 0 32 33 1 0 0 0 0 33 39 2 0 0 0 0 34 37 1 0 0 0 0 34 43 1 0 0 0 0 35 40 2 0 0 0 0 35 44 1 0 0 0 0 36 38 1 0 0 0 0 36 51 1 0 0 0 0 37 47 1 0 0 0 0 38 48 1 0 0 0 0 39 40 1 0 0 0 0 39 49 1 0 0 0 0 40 50 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	698.32
Volume:	709.969
LogP:	5.078
LogD:	3.253
LogS:	-3.892
# Rotatable Bonds:	10
TPSA:	111.55
# H-Bond Aceptor:	11
# H-Bond Donor:	2
# Rings:	7
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.19
Synthetic Accessibility Score:	4.201
Fsp3:	0.4
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.468
MDCK Permeability:	2.8739606932504103e-05
Pgp-inhibitor:	0.99
Pgp-substrate:	0.863
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.116

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.055
Plasma Protein Binding (PPB):	54.82004928588867%
Volume Distribution (VD):	1.248
Pgp-substrate:	58.187339782714844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.023
CYP1A2-substrate:	0.992
CYP2C19-inhibitor:	0.038
CYP2C19-substrate:	0.969
CYP2C9-inhibitor:	0.024
CYP2C9-substrate:	0.782
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.936
CYP3A4-inhibitor:	0.06
CYP3A4-substrate:	0.963

ADMET: Excretion

Clearance (CL):	9.518
Half-life (T1/2):	0.204

ADMET: Toxicity

hERG Blockers:	0.955
Human Hepatotoxicity (H-HT):	0.037
Drug-inuced Liver Injury (DILI):	0.386
AMES Toxicity:	0.056
Rat Oral Acute Toxicity:	0.841
Maximum Recommended Daily Dose:	0.985
Skin Sensitization:	0.909
Carcinogencity:	0.013
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.637

Download Data

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

Natural Product: NPC30182

Natural Product ID:	NPC30182
*Common Name:**	Thalifasine
IUPAC Name:	(6aS)-8-[4-[[(1S)-5-hydroxy-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-1-yl]methyl]phenoxy]-1,2,9,10-tetramethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-3-ol
Synonyms:	Thalifasine
Standard InCHIKey:	JKZGCTOQBIITDP-VMPREFPWSA-N
Standard InCHI:	InChI=1S/C40H46N2O9/c1-41-15-13-23-25(19-30(45-3)37(47-5)34(23)43)28(41)17-21-9-11-22(12-10-21)51-36-27-18-29-32-24(14-16-42(29)2)35(44)40(50-8)39(49-7)33(32)26(27)20-31(46-4)38(36)48-6/h9-12,19-20,28-29,43-44H,13-18H2,1-8H3/t28-,29-/m0/s1
SMILES:	COc1c(OC)cc2c(c1Oc1ccc(cc1)C[C@@H]1N(C)CCc3c1cc(OC)c(c3O)OC)C[C@H]1c3c2c(OC)c(c(c3CCN1C)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL510732
PubChem CID:	10372546
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0000381] Aporphines

*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
NPO21435	Thalictrum faberi	Species	Ranunculaceae	Eukaryota	Roots	n.a.	n.a.	PMID[19299148]
NPO21435	Thalictrum faberi	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7528786]
NPO21435	Thalictrum faberi	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21435	Thalictrum faberi	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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
ED50	14
Others	2

Activity Type	# Activity
Cell Line	8
NON-MOLECULAR	4
Organism	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT453	Cell Line	HT-1080	Homo sapiens	ED50	=	1.3	ug ml-1	PMID[470997]
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	=	2.0	ug ml-1	PMID[470997]
NPT1851	Cell Line	Col2	Homo sapiens	ED50	=	2.1	ug ml-1	PMID[470997]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	4.6	ug ml-1	PMID[470997]
NPT168	Cell Line	P388	Mus musculus	ED50	=	1.2	ug ml-1	PMID[470997]
NPT762	Cell Line	A-431	Homo sapiens	ED50	=	8.2	ug ml-1	PMID[470997]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	=	3.3	ug ml-1	PMID[470997]
NPT133	Cell Line	ZR-75-1	Homo sapiens	ED50	=	1.2	ug ml-1	PMID[470997]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	2.4	ug ml-1	PMID[470997]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	5.7	ug ml-1	PMID[470997]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	1.6	ug ml-1	PMID[470997]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	2.2	ug ml-1	PMID[470997]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	ED50	=	238.0	ng/ml	PMID[470997]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	ED50	=	49.3	ng/ml	PMID[470997]
NPT2	Others	Unspecified		Selectivity Index	=	19.0	n.a.	PMID[470997]
NPT2	Others	Unspecified		Selectivity Index	=	93.0	n.a.	PMID[470997]

☑ 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 NPC30182 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	382
0.1-0.2	1688
0.2-0.3	7861
0.3-0.4	10548
0.4-0.5	5280
0.5-0.6	8822
0.6-0.7	6628
0.7-0.8	1156
0.8-0.85	169
0.85-0.9	99
0.9-0.95	48
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC478092
1.0	High Similarity	NPC478091
1.0	High Similarity	NPC473589
0.9942	High Similarity	NPC478093
0.9593	High Similarity	NPC302275
0.954	High Similarity	NPC275680
0.954	High Similarity	NPC22115
0.9535	High Similarity	NPC30779
0.9477	High Similarity	NPC286119
0.9425	High Similarity	NPC16357
0.9425	High Similarity	NPC95426
0.9425	High Similarity	NPC302245
0.9422	High Similarity	NPC15414
0.9422	High Similarity	NPC290005
0.9422	High Similarity	NPC222661
0.9422	High Similarity	NPC42663
0.9422	High Similarity	NPC104196
0.9422	High Similarity	NPC90998
0.9422	High Similarity	NPC290582
0.9422	High Similarity	NPC49075
0.9422	High Similarity	NPC217748
0.9422	High Similarity	NPC182052
0.9422	High Similarity	NPC311973
0.9422	High Similarity	NPC271013
0.9422	High Similarity	NPC8836
0.9422	High Similarity	NPC7715
0.9422	High Similarity	NPC181796
0.9422	High Similarity	NPC328155
0.9422	High Similarity	NPC279228
0.9422	High Similarity	NPC251735
0.9422	High Similarity	NPC239824
0.9422	High Similarity	NPC229373
0.9422	High Similarity	NPC223690
0.9422	High Similarity	NPC185639
0.9422	High Similarity	NPC54654
0.9422	High Similarity	NPC258657
0.9422	High Similarity	NPC285931
0.9375	High Similarity	NPC206900
0.9371	High Similarity	NPC47077
0.9371	High Similarity	NPC65312
0.9371	High Similarity	NPC139783
0.9371	High Similarity	NPC14507
0.9368	High Similarity	NPC254441
0.9368	High Similarity	NPC274716
0.9368	High Similarity	NPC167116
0.9261	High Similarity	NPC212237
0.9261	High Similarity	NPC116465
0.9157	High Similarity	NPC175890
0.9157	High Similarity	NPC82457
0.9157	High Similarity	NPC11296
0.9157	High Similarity	NPC274661
0.9157	High Similarity	NPC48490
0.9128	High Similarity	NPC239775
0.9111	High Similarity	NPC256124
0.9106	High Similarity	NPC191132
0.9106	High Similarity	NPC60295
0.907	High Similarity	NPC168753
0.907	High Similarity	NPC118274
0.9056	High Similarity	NPC24260
0.9017	High Similarity	NPC76682
0.9017	High Similarity	NPC317145
0.9017	High Similarity	NPC276890
0.9017	High Similarity	NPC198498
0.9017	High Similarity	NPC317439
0.9017	High Similarity	NPC10908
0.9017	High Similarity	NPC63646
0.9017	High Similarity	NPC115284
0.9017	High Similarity	NPC227060
0.8966	High Similarity	NPC251580
0.8966	High Similarity	NPC41376
0.8966	High Similarity	NPC129518
0.8966	High Similarity	NPC12424
0.8895	High Similarity	NPC250846
0.8895	High Similarity	NPC42549
0.8895	High Similarity	NPC318805
0.8895	High Similarity	NPC240841
0.8895	High Similarity	NPC256012
0.8895	High Similarity	NPC268503
0.8895	High Similarity	NPC41122
0.8895	High Similarity	NPC317272
0.887	High Similarity	NPC474507
0.8864	High Similarity	NPC293093
0.8844	High Similarity	NPC306555
0.8844	High Similarity	NPC145832
0.8844	High Similarity	NPC81218
0.8844	High Similarity	NPC158376
0.8844	High Similarity	NPC117188
0.8844	High Similarity	NPC205421
0.8844	High Similarity	NPC12053
0.8844	High Similarity	NPC474931
0.8837	High Similarity	NPC477563
0.8837	High Similarity	NPC96603
0.8837	High Similarity	NPC212794
0.8837	High Similarity	NPC13504
0.8837	High Similarity	NPC136508
0.8837	High Similarity	NPC306843
0.8837	High Similarity	NPC253043
0.8837	High Similarity	NPC196447
0.8837	High Similarity	NPC78222
0.8804	High Similarity	NPC234318
0.8798	High Similarity	NPC85381
0.8786	High Similarity	NPC264850
0.8786	High Similarity	NPC13916
0.8779	High Similarity	NPC324144
0.8764	High Similarity	NPC243454
0.8764	High Similarity	NPC475479
0.8763	High Similarity	NPC475654
0.8757	High Similarity	NPC173416
0.8757	High Similarity	NPC476577
0.8757	High Similarity	NPC148709
0.8728	High Similarity	NPC24465
0.8723	High Similarity	NPC254581
0.8715	High Similarity	NPC239584
0.8686	High Similarity	NPC83198
0.8686	High Similarity	NPC204908
0.8671	High Similarity	NPC1229
0.8667	High Similarity	NPC73492
0.8667	High Similarity	NPC299990
0.8663	High Similarity	NPC27410
0.8663	High Similarity	NPC166014
0.8611	High Similarity	NPC257269
0.8611	High Similarity	NPC230276
0.8588	High Similarity	NPC475215
0.8588	High Similarity	NPC108434
0.8556	High Similarity	NPC119068
0.8556	High Similarity	NPC40496
0.8539	High Similarity	NPC190783
0.8539	High Similarity	NPC192135
0.8539	High Similarity	NPC66341
0.8539	High Similarity	NPC232386
0.8539	High Similarity	NPC152680
0.8539	High Similarity	NPC477020
0.8533	High Similarity	NPC82763
0.8531	High Similarity	NPC69712
0.8531	High Similarity	NPC477562
0.8531	High Similarity	NPC26240
0.8508	High Similarity	NPC195538
0.8506	High Similarity	NPC60186
0.85	High Similarity	NPC320223
0.85	High Similarity	NPC114364
0.8492	Intermediate Similarity	NPC128560
0.8492	Intermediate Similarity	NPC199465
0.8492	Intermediate Similarity	NPC229166
0.8488	Intermediate Similarity	NPC247639
0.8488	Intermediate Similarity	NPC25084
0.8478	Intermediate Similarity	NPC476576
0.8478	Intermediate Similarity	NPC186546
0.847	Intermediate Similarity	NPC249996
0.8462	Intermediate Similarity	NPC476202
0.8448	Intermediate Similarity	NPC205255
0.8448	Intermediate Similarity	NPC271388
0.8448	Intermediate Similarity	NPC235143
0.8448	Intermediate Similarity	NPC119649
0.8448	Intermediate Similarity	NPC230956
0.8439	Intermediate Similarity	NPC476572
0.8434	Intermediate Similarity	NPC82056
0.8432	Intermediate Similarity	NPC281581
0.843	Intermediate Similarity	NPC325871
0.843	Intermediate Similarity	NPC99659
0.8418	Intermediate Similarity	NPC204947
0.84	Intermediate Similarity	NPC79402
0.84	Intermediate Similarity	NPC80759
0.8391	Intermediate Similarity	NPC221864
0.8387	Intermediate Similarity	NPC473716
0.8387	Intermediate Similarity	NPC475597
0.838	Intermediate Similarity	NPC149090
0.838	Intermediate Similarity	NPC19520
0.8362	Intermediate Similarity	NPC476573
0.8362	Intermediate Similarity	NPC35627
0.8362	Intermediate Similarity	NPC81247
0.8324	Intermediate Similarity	NPC276588
0.8324	Intermediate Similarity	NPC193949
0.8324	Intermediate Similarity	NPC207757
0.8324	Intermediate Similarity	NPC5238
0.8324	Intermediate Similarity	NPC214116
0.8324	Intermediate Similarity	NPC469817
0.8324	Intermediate Similarity	NPC39701
0.8324	Intermediate Similarity	NPC172765
0.8324	Intermediate Similarity	NPC110416
0.8324	Intermediate Similarity	NPC189266
0.8324	Intermediate Similarity	NPC54379
0.8324	Intermediate Similarity	NPC2413
0.8324	Intermediate Similarity	NPC204828
0.8324	Intermediate Similarity	NPC278799
0.8324	Intermediate Similarity	NPC57036
0.8324	Intermediate Similarity	NPC127674
0.8324	Intermediate Similarity	NPC184026
0.8324	Intermediate Similarity	NPC249797
0.8324	Intermediate Similarity	NPC295691
0.8289	Intermediate Similarity	NPC475754
0.8278	Intermediate Similarity	NPC231371
0.8261	Intermediate Similarity	NPC116284
0.8256	Intermediate Similarity	NPC81733
0.8256	Intermediate Similarity	NPC326316
0.8251	Intermediate Similarity	NPC32154
0.8249	Intermediate Similarity	NPC475393
0.8241	Intermediate Similarity	NPC38964
0.8218	Intermediate Similarity	NPC123323
0.8216	Intermediate Similarity	NPC135772
0.8212	Intermediate Similarity	NPC298979

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 NPC30182 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	217
0.1-0.2	792
0.2-0.3	1163
0.3-0.4	2302
0.4-0.5	2393
0.5-0.6	1520
0.6-0.7	622
0.7-0.8	116
0.8-0.85	19
0.85-0.9	4
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9422	High Similarity	NPD8053	Approved
0.9422	High Similarity	NPD8054	Approved
0.9017	High Similarity	NPD8251	Approved
0.9017	High Similarity	NPD8252	Approved
0.9017	High Similarity	NPD8099	Discontinued
0.8966	High Similarity	NPD8156	Discontinued
0.8556	High Similarity	NPD8453	Clinical (unspecified phase)
0.8424	Intermediate Similarity	NPD7906	Approved
0.8125	Intermediate Similarity	NPD8095	Phase 1
0.8108	Intermediate Similarity	NPD7313	Approved
0.8108	Intermediate Similarity	NPD7312	Approved
0.8108	Intermediate Similarity	NPD7311	Approved
0.8108	Intermediate Similarity	NPD7310	Approved
0.8066	Intermediate Similarity	NPD27	Approved
0.8066	Intermediate Similarity	NPD2489	Approved
0.8065	Intermediate Similarity	NPD7309	Approved
0.8056	Intermediate Similarity	NPD3051	Approved
0.8011	Intermediate Similarity	NPD4577	Approved
0.8011	Intermediate Similarity	NPD4578	Approved
0.8011	Intermediate Similarity	NPD2969	Approved
0.8011	Intermediate Similarity	NPD2970	Approved
0.7979	Intermediate Similarity	NPD4663	Approved
0.7965	Intermediate Similarity	NPD2421	Approved
0.7965	Intermediate Similarity	NPD2420	Approved
0.7919	Intermediate Similarity	NPD4584	Approved
0.7877	Intermediate Similarity	NPD6788	Approved
0.7833	Intermediate Similarity	NPD7833	Phase 2
0.7833	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7833	Intermediate Similarity	NPD7831	Phase 2
0.7692	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7663	Intermediate Similarity	NPD6071	Discontinued
0.7654	Intermediate Similarity	NPD4773	Phase 2
0.7654	Intermediate Similarity	NPD4772	Phase 2
0.7611	Intermediate Similarity	NPD7298	Approved
0.7588	Intermediate Similarity	NPD3450	Approved
0.7588	Intermediate Similarity	NPD3452	Approved
0.7588	Intermediate Similarity	NPD2494	Approved
0.7588	Intermediate Similarity	NPD2493	Approved
0.7581	Intermediate Similarity	NPD4481	Phase 3
0.7577	Intermediate Similarity	NPD2488	Approved
0.7577	Intermediate Similarity	NPD2490	Approved
0.7554	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7447	Phase 1
0.7514	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7488	Intermediate Similarity	NPD6997	Phase 2
0.7487	Intermediate Similarity	NPD2898	Approved
0.7486	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD4583	Approved
0.7475	Intermediate Similarity	NPD4582	Approved
0.7452	Intermediate Similarity	NPD7047	Phase 3
0.7446	Intermediate Similarity	NPD4055	Discovery
0.7432	Intermediate Similarity	NPD2560	Approved
0.7432	Intermediate Similarity	NPD2563	Approved
0.7426	Intermediate Similarity	NPD4002	Approved
0.7426	Intermediate Similarity	NPD4004	Approved
0.7401	Intermediate Similarity	NPD3845	Phase 1
0.7387	Intermediate Similarity	NPD2975	Approved
0.7387	Intermediate Similarity	NPD2973	Approved
0.7387	Intermediate Similarity	NPD2974	Approved
0.738	Intermediate Similarity	NPD4010	Discontinued
0.736	Intermediate Similarity	NPD7212	Phase 2
0.736	Intermediate Similarity	NPD7213	Phase 3
0.7345	Intermediate Similarity	NPD5241	Discontinued
0.7308	Intermediate Similarity	NPD7827	Phase 1
0.7306	Intermediate Similarity	NPD7549	Discontinued
0.7303	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD4580	Approved
0.7268	Intermediate Similarity	NPD2971	Approved
0.7268	Intermediate Similarity	NPD2968	Approved
0.7268	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD6031	Approved
0.7238	Intermediate Similarity	NPD6030	Approved
0.7231	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD8153	Approved
0.7225	Intermediate Similarity	NPD8152	Approved
0.7222	Intermediate Similarity	NPD1424	Approved
0.7213	Intermediate Similarity	NPD4675	Approved
0.7213	Intermediate Similarity	NPD4678	Approved
0.7207	Intermediate Similarity	NPD7124	Phase 2
0.7196	Intermediate Similarity	NPD7907	Approved
0.7192	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6042	Phase 2
0.7188	Intermediate Similarity	NPD42	Phase 2
0.7181	Intermediate Similarity	NPD5677	Discontinued
0.7174	Intermediate Similarity	NPD6072	Discontinued
0.7158	Intermediate Similarity	NPD4017	Approved
0.7143	Intermediate Similarity	NPD7802	Discontinued
0.7143	Intermediate Similarity	NPD3641	Approved
0.7143	Intermediate Similarity	NPD3640	Phase 3
0.7143	Intermediate Similarity	NPD3639	Approved
0.7136	Intermediate Similarity	NPD4040	Phase 1
0.7088	Intermediate Similarity	NPD6090	Discontinued
0.7074	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD7598	Phase 2
0.7065	Intermediate Similarity	NPD4005	Discontinued
0.7059	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD6107	Approved
0.7027	Intermediate Similarity	NPD6723	Discontinued
0.7026	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD5676	Approved
0.7011	Intermediate Similarity	NPD4474	Approved
0.7011	Intermediate Similarity	NPD4475	Approved
0.6973	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD3109	Approved
0.6971	Remote Similarity	NPD3110	Approved
0.6959	Remote Similarity	NPD7493	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD3057	Approved
0.6957	Remote Similarity	NPD2122	Discontinued
0.6957	Remote Similarity	NPD3448	Approved
0.6957	Remote Similarity	NPD2491	Approved
0.6954	Remote Similarity	NPD5718	Phase 2
0.6954	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD2200	Suspended
0.6944	Remote Similarity	NPD5177	Phase 3
0.694	Remote Similarity	NPD4123	Phase 3
0.6936	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD7048	Phase 3
0.6923	Remote Similarity	NPD6667	Approved
0.6923	Remote Similarity	NPD6666	Approved
0.6915	Remote Similarity	NPD7046	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD5772	Approved
0.6915	Remote Similarity	NPD5773	Approved
0.6911	Remote Similarity	NPD4666	Phase 3
0.6907	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD6748	Discontinued
0.6906	Remote Similarity	NPD7466	Approved
0.6897	Remote Similarity	NPD7262	Phase 1
0.6897	Remote Similarity	NPD4625	Phase 3
0.6891	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD7037	Approved
0.6888	Remote Similarity	NPD7479	Phase 2
0.6885	Remote Similarity	NPD3124	Discontinued
0.6884	Remote Similarity	NPD6853	Approved
0.6884	Remote Similarity	NPD6851	Approved
0.6882	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD6284	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5006	Approved
0.6875	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD2972	Approved
0.6875	Remote Similarity	NPD3533	Approved
0.6875	Remote Similarity	NPD5005	Approved
0.6875	Remote Similarity	NPD1613	Approved
0.6872	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD4111	Phase 1
0.6866	Remote Similarity	NPD4665	Approved
0.6859	Remote Similarity	NPD5709	Phase 3
0.6857	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD7718	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD6297	Approved
0.6848	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD4908	Phase 1
0.6837	Remote Similarity	NPD5312	Approved
0.6837	Remote Similarity	NPD5313	Approved
0.6837	Remote Similarity	NPD4873	Discontinued
0.6824	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD7169	Suspended
0.6818	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD1753	Discontinued
0.6812	Remote Similarity	NPD3837	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7922	Phase 1
0.68	Remote Similarity	NPD5155	Approved
0.68	Remote Similarity	NPD5156	Approved
0.6796	Remote Similarity	NPD7045	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7177	Discontinued
0.6784	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD7291	Discontinued
0.6776	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD5160	Discontinued
0.6776	Remote Similarity	NPD3692	Discontinued
0.6774	Remote Similarity	NPD5976	Discontinued
0.6772	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD4420	Approved
0.676	Remote Similarity	NPD6111	Discontinued
0.676	Remote Similarity	NPD6895	Approved
0.676	Remote Similarity	NPD6896	Approved
0.6758	Remote Similarity	NPD3060	Approved
0.6753	Remote Similarity	NPD4166	Phase 2
0.6743	Remote Similarity	NPD3594	Approved
0.6743	Remote Similarity	NPD2606	Approved
0.6743	Remote Similarity	NPD2605	Approved
0.6743	Remote Similarity	NPD3595	Approved
0.674	Remote Similarity	NPD4726	Approved
0.674	Remote Similarity	NPD4725	Approved
0.674	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.674	Remote Similarity	NPD4721	Approved
0.6739	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD2978	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