NPASS Compound

Structure

CID302275 OpenBabel06191716112D 51 57 0 0 1 0 0 0 0 0999 V2000 6.8637 -2.9028 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4011 2.9564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0143 -5.7865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.8337 -3.3160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6045 -3.4616 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8160 1.3187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1599 -2.9324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6054 -2.0842 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3436 -1.3290 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8507 -1.9191 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6832 -0.4322 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9923 -1.4384 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8247 0.0484 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5935 -4.8478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8549 2.4607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7351 -4.3672 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7028 2.9493 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5546 -1.8966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2974 -4.8253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4151 0.9826 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2714 -2.8578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5723 -1.4907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6961 -1.4159 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4390 -4.3447 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9793 -0.4547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8498 1.4720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4260 -3.3609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5592 -0.4998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4108 0.0069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5676 -2.8803 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5617 1.4753 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 11.1429 -4.3222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1299 -3.3384 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4369 -1.9748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6982 0.9822 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7058 -0.0071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0009 0.9783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2754 -0.4772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2885 -1.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8483 -0.4898 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 7.7221 -3.3834 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5511 2.4595 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 12.0013 -4.8028 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.9753 -2.8353 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4499 -2.9585 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8489 1.4661 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1469 -1.9487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8430 -1.4693 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8499 -0.4845 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1209 0.0259 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 42 1 0 0 0 0 2 43 1 0 0 0 0 3 44 1 0 0 0 0 4 45 1 0 0 0 0 5 46 1 0 0 0 0 6 47 1 0 0 0 0 7 48 1 0 0 0 0 8 49 1 0 0 0 0 9 50 1 0 0 0 0 10 12 1 0 0 0 0 10 23 2 0 0 0 0 11 13 2 0 0 0 0 11 23 1 0 0 0 0 12 25 2 0 0 0 0 13 25 1 0 0 0 0 14 16 1 0 0 0 0 14 24 1 0 0 0 0 15 17 1 0 0 0 0 15 26 1 0 0 0 0 16 42 1 0 0 0 0 17 43 1 0 0 0 0 18 23 1 0 0 0 0 19 24 2 0 0 0 0 19 32 1 0 0 0 0 20 29 1 0 0 0 0 21 27 2 0 0 0 0 21 33 1 0 0 0 0 22 28 2 0 0 0 0 22 34 1 0 0 0 0 24 27 1 0 0 0 0 25 51 1 0 0 0 0 26 35 2 0 0 0 0 26 37 1 0 0 0 0 27 30 1 0 0 0 0 28 29 1 0 0 0 0 28 36 1 0 0 0 0 29 38 2 0 0 0 0 30 18 1 1 0 0 0 30 42 1 0 0 0 0 31 20 1 1 0 0 0 31 35 1 0 0 0 0 31 43 1 0 0 0 0 32 33 2 0 0 0 0 32 44 1 0 0 0 0 33 45 1 0 0 0 0 34 39 2 0 0 0 0 34 46 1 0 0 0 0 35 36 1 0 0 0 0 36 40 2 0 0 0 0 37 41 2 0 0 0 0 37 47 1 0 0 0 0 38 39 1 0 0 0 0 38 51 1 0 0 0 0 39 48 1 0 0 0 0 40 41 1 0 0 0 0 40 49 1 0 0 0 0 41 50 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	696.34
Volume:	718.474
LogP:	5.688
LogD:	3.818
LogS:	-4.451
# Rotatable Bonds:	11
TPSA:	80.32
# H-Bond Aceptor:	10
# H-Bond Donor:	0
# Rings:	7
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.163
Synthetic Accessibility Score:	4.029
Fsp3:	0.415
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.615
MDCK Permeability:	2.7906900868401863e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.971
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.019
30% Bioavailability (F30%):	0.469

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.077
Plasma Protein Binding (PPB):	42.98048400878906%
Volume Distribution (VD):	1.426
Pgp-substrate:	70.15750122070312%

ADMET: Metabolism

CYP1A2-inhibitor:	0.021
CYP1A2-substrate:	0.993
CYP2C19-inhibitor:	0.055
CYP2C19-substrate:	0.983
CYP2C9-inhibitor:	0.021
CYP2C9-substrate:	0.828
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.958
CYP3A4-inhibitor:	0.13
CYP3A4-substrate:	0.966

ADMET: Excretion

Clearance (CL):	9.707
Half-life (T1/2):	0.109

ADMET: Toxicity

hERG Blockers:	0.982
Human Hepatotoxicity (H-HT):	0.033
Drug-inuced Liver Injury (DILI):	0.834
AMES Toxicity:	0.061
Rat Oral Acute Toxicity:	0.893
Maximum Recommended Daily Dose:	0.989
Skin Sensitization:	0.569
Carcinogencity:	0.014
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.687

Download Data

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

Natural Product: NPC302275

Natural Product ID:	NPC302275
*Common Name:**	Thalifaberine
IUPAC Name:	(6aS)-8-[4-[[(1S)-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-1-yl]methyl]phenoxy]-1,2,3,9,10-pentamethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline
Synonyms:	Thalifaberine
Standard InCHIKey:	RRKYSGHTIGWTJQ-CONSDPRKSA-N
Standard InCHI:	InChI=1S/C41H48N2O8/c1-42-16-14-24-19-32(44-3)33(45-4)21-27(24)30(42)18-23-10-12-25(13-11-23)51-38-29-20-31-35-26(15-17-43(31)2)37(47-6)41(50-9)40(49-8)36(35)28(29)22-34(46-5)39(38)48-7/h10-13,19,21-22,30-31H,14-18,20H2,1-9H3/t30-,31-/m0/s1
SMILES:	COc1c(OC)cc2c(c1Oc1ccc(cc1)C[C@@H]1N(C)CCc3c1cc(OC)c(c3)OC)C[C@H]1c3c2c(OC)c(c(c3CCN1C)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL498913
PubChem CID:	159246
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]
NPO24447	Thalictrum cultratum	Species	Ranunculaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29131616]
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]
NPO24447	Thalictrum cultratum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24447	Thalictrum cultratum	Species	Ranunculaceae	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
ED50	14
IC50	2
Others	2

Activity Type	# Activity
Cell Line	10
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	=	2.6	ug ml-1	PMID[494762]
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	=	16.3	ug ml-1	PMID[494762]
NPT1851	Cell Line	Col2	Homo sapiens	ED50	=	1.6	ug ml-1	PMID[494762]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	15.5	ug ml-1	PMID[494762]
NPT168	Cell Line	P388	Mus musculus	ED50	=	1.3	ug ml-1	PMID[494762]
NPT762	Cell Line	A-431	Homo sapiens	ED50	=	4.9	ug ml-1	PMID[494762]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	=	5.7	ug ml-1	PMID[494762]
NPT133	Cell Line	ZR-75-1	Homo sapiens	ED50	=	3.7	ug ml-1	PMID[494762]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	7270.0	nM	PMID[494763]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	1580.0	nM	PMID[494763]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	5.4	ug ml-1	PMID[494762]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	4.6	ug ml-1	PMID[494762]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	1.2	ug ml-1	PMID[494762]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	4.1	ug ml-1	PMID[494762]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	ED50	=	5090.0	ng/ml	PMID[494762]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	ED50	=	441.0	ng/ml	PMID[494762]
NPT2	Others	Unspecified		Selectivity Index	=	3.0	n.a.	PMID[494762]
NPT2	Others	Unspecified		Selectivity Index	=	35.0	n.a.	PMID[494762]

☑ 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 NPC302275 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	456
0.1-0.2	1880
0.2-0.3	8936
0.3-0.4	9458
0.4-0.5	5926
0.5-0.6	10585
0.6-0.7	4470
0.7-0.8	699
0.8-0.85	154
0.85-0.9	91
0.9-0.95	27
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
0.9762	High Similarity	NPC47077
0.9762	High Similarity	NPC14507
0.9593	High Similarity	NPC30182
0.9593	High Similarity	NPC478092
0.9593	High Similarity	NPC478091
0.9593	High Similarity	NPC473589
0.9535	High Similarity	NPC478093
0.9398	High Similarity	NPC63646
0.9398	High Similarity	NPC276890
0.9398	High Similarity	NPC115284
0.9398	High Similarity	NPC76682
0.9398	High Similarity	NPC317145
0.9398	High Similarity	NPC10908
0.9398	High Similarity	NPC317439
0.9398	High Similarity	NPC227060
0.9398	High Similarity	NPC198498
0.9341	High Similarity	NPC12424
0.9341	High Similarity	NPC41376
0.9341	High Similarity	NPC251580
0.9341	High Similarity	NPC129518
0.9244	High Similarity	NPC16357
0.9244	High Similarity	NPC302245
0.9244	High Similarity	NPC95426
0.9231	High Similarity	NPC293093
0.9191	High Similarity	NPC139783
0.9191	High Similarity	NPC65312
0.9138	High Similarity	NPC22115
0.9138	High Similarity	NPC275680
0.9128	High Similarity	NPC30779
0.9123	High Similarity	NPC475479
0.9123	High Similarity	NPC243454
0.907	High Similarity	NPC286119
0.907	High Similarity	NPC239584
0.9017	High Similarity	NPC222661
0.9017	High Similarity	NPC299990
0.9017	High Similarity	NPC217748
0.9017	High Similarity	NPC258657
0.9017	High Similarity	NPC279228
0.9017	High Similarity	NPC54654
0.9017	High Similarity	NPC285931
0.9017	High Similarity	NPC290582
0.9017	High Similarity	NPC229373
0.9017	High Similarity	NPC311973
0.9017	High Similarity	NPC8836
0.9017	High Similarity	NPC185639
0.9017	High Similarity	NPC290005
0.9017	High Similarity	NPC181796
0.9017	High Similarity	NPC251735
0.9017	High Similarity	NPC15414
0.9017	High Similarity	NPC104196
0.9017	High Similarity	NPC42663
0.9017	High Similarity	NPC49075
0.9017	High Similarity	NPC7715
0.9017	High Similarity	NPC223690
0.9017	High Similarity	NPC73492
0.9017	High Similarity	NPC90998
0.9017	High Similarity	NPC328155
0.9017	High Similarity	NPC271013
0.9017	High Similarity	NPC239824
0.9017	High Similarity	NPC182052
0.8977	High Similarity	NPC206900
0.8966	High Similarity	NPC167116
0.8966	High Similarity	NPC254441
0.8966	High Similarity	NPC274716
0.8933	High Similarity	NPC256124
0.8864	High Similarity	NPC212237
0.8864	High Similarity	NPC116465
0.8851	High Similarity	NPC195538
0.8848	High Similarity	NPC247639
0.8848	High Similarity	NPC25084
0.8807	High Similarity	NPC249996
0.88	High Similarity	NPC476202
0.8795	High Similarity	NPC476572
0.8788	High Similarity	NPC99659
0.8788	High Similarity	NPC325871
0.8765	High Similarity	NPC204947
0.8764	High Similarity	NPC281581
0.8764	High Similarity	NPC82457
0.8764	High Similarity	NPC48490
0.8764	High Similarity	NPC274661
0.8764	High Similarity	NPC175890
0.8764	High Similarity	NPC11296
0.8721	High Similarity	NPC239775
0.8721	High Similarity	NPC149090
0.8721	High Similarity	NPC19520
0.8715	High Similarity	NPC473716
0.8715	High Similarity	NPC475597
0.8715	High Similarity	NPC60295
0.8715	High Similarity	NPC191132
0.8667	High Similarity	NPC24260
0.8663	High Similarity	NPC168753
0.8663	High Similarity	NPC118274
0.8606	High Similarity	NPC326316
0.8606	High Similarity	NPC81733
0.8588	High Similarity	NPC475393
0.8563	High Similarity	NPC123323
0.8548	High Similarity	NPC254581
0.8508	High Similarity	NPC318805
0.8508	High Similarity	NPC41122
0.8506	High Similarity	NPC10871
0.8488	Intermediate Similarity	NPC240841
0.8488	Intermediate Similarity	NPC24264
0.8488	Intermediate Similarity	NPC42549
0.8488	Intermediate Similarity	NPC250846
0.8488	Intermediate Similarity	NPC317272
0.8488	Intermediate Similarity	NPC476432
0.8488	Intermediate Similarity	NPC268503
0.8488	Intermediate Similarity	NPC256012
0.8475	Intermediate Similarity	NPC474507
0.8439	Intermediate Similarity	NPC474931
0.8439	Intermediate Similarity	NPC306555
0.8439	Intermediate Similarity	NPC247389
0.8439	Intermediate Similarity	NPC158376
0.8439	Intermediate Similarity	NPC117188
0.8439	Intermediate Similarity	NPC205421
0.8439	Intermediate Similarity	NPC12053
0.8439	Intermediate Similarity	NPC81218
0.8439	Intermediate Similarity	NPC145832
0.843	Intermediate Similarity	NPC16805
0.843	Intermediate Similarity	NPC253043
0.843	Intermediate Similarity	NPC306843
0.843	Intermediate Similarity	NPC302527
0.843	Intermediate Similarity	NPC78222
0.843	Intermediate Similarity	NPC212794
0.843	Intermediate Similarity	NPC167546
0.843	Intermediate Similarity	NPC96603
0.843	Intermediate Similarity	NPC225774
0.843	Intermediate Similarity	NPC196447
0.843	Intermediate Similarity	NPC136508
0.843	Intermediate Similarity	NPC13504
0.843	Intermediate Similarity	NPC477563
0.8427	Intermediate Similarity	NPC32413
0.8427	Intermediate Similarity	NPC230276
0.8427	Intermediate Similarity	NPC474506
0.8427	Intermediate Similarity	NPC257269
0.8424	Intermediate Similarity	NPC234318
0.8418	Intermediate Similarity	NPC23219
0.8415	Intermediate Similarity	NPC85381
0.8387	Intermediate Similarity	NPC475654
0.8382	Intermediate Similarity	NPC13916
0.8382	Intermediate Similarity	NPC264850
0.8382	Intermediate Similarity	NPC219341
0.8373	Intermediate Similarity	NPC92541
0.8372	Intermediate Similarity	NPC324144
0.8371	Intermediate Similarity	NPC119068
0.8371	Intermediate Similarity	NPC470879
0.8371	Intermediate Similarity	NPC40496
0.8371	Intermediate Similarity	NPC258695
0.8362	Intermediate Similarity	NPC173416
0.8362	Intermediate Similarity	NPC112575
0.8362	Intermediate Similarity	NPC148709
0.8362	Intermediate Similarity	NPC476577
0.8343	Intermediate Similarity	NPC244112
0.8333	Intermediate Similarity	NPC210918
0.8324	Intermediate Similarity	NPC24465
0.8294	Intermediate Similarity	NPC170503
0.8294	Intermediate Similarity	NPC126519
0.8294	Intermediate Similarity	NPC203784
0.8286	Intermediate Similarity	NPC83198
0.8286	Intermediate Similarity	NPC204908
0.8266	Intermediate Similarity	NPC1229
0.8256	Intermediate Similarity	NPC166014
0.8256	Intermediate Similarity	NPC205255
0.8256	Intermediate Similarity	NPC232924
0.8256	Intermediate Similarity	NPC27410
0.8256	Intermediate Similarity	NPC266753
0.8256	Intermediate Similarity	NPC230956
0.8256	Intermediate Similarity	NPC119649
0.8256	Intermediate Similarity	NPC235143
0.8256	Intermediate Similarity	NPC271388
0.8256	Intermediate Similarity	NPC160298
0.8256	Intermediate Similarity	NPC477559
0.8256	Intermediate Similarity	NPC306902
0.8253	Intermediate Similarity	NPC106295
0.8253	Intermediate Similarity	NPC16107
0.8253	Intermediate Similarity	NPC210437
0.8253	Intermediate Similarity	NPC476144
0.8253	Intermediate Similarity	NPC51957
0.8253	Intermediate Similarity	NPC144863
0.8242	Intermediate Similarity	NPC214116
0.8208	Intermediate Similarity	NPC80759
0.8208	Intermediate Similarity	NPC79402
0.8207	Intermediate Similarity	NPC475754
0.8204	Intermediate Similarity	NPC7467
0.8198	Intermediate Similarity	NPC7393
0.8198	Intermediate Similarity	NPC221864
0.8192	Intermediate Similarity	NPC475215
0.8192	Intermediate Similarity	NPC108434
0.8167	Intermediate Similarity	NPC220961
0.8152	Intermediate Similarity	NPC82763
0.8146	Intermediate Similarity	NPC66341
0.8146	Intermediate Similarity	NPC232386
0.8146	Intermediate Similarity	NPC477020
0.8146	Intermediate Similarity	NPC192135
0.8146	Intermediate Similarity	NPC152680
0.8146	Intermediate Similarity	NPC190783
0.8142	Intermediate Similarity	NPC57036
0.8136	Intermediate Similarity	NPC26240
0.8136	Intermediate Similarity	NPC6152
0.8136	Intermediate Similarity	NPC69712

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 NPC302275 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	243
0.1-0.2	859
0.2-0.3	1092
0.3-0.4	2347
0.4-0.5	2390
0.5-0.6	1544
0.6-0.7	538
0.7-0.8	122
0.8-0.85	9
0.85-0.9	2
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9398	High Similarity	NPD8252	Approved
0.9398	High Similarity	NPD8099	Discontinued
0.9398	High Similarity	NPD8251	Approved
0.9341	High Similarity	NPD8156	Discontinued
0.9017	High Similarity	NPD8054	Approved
0.9017	High Similarity	NPD8053	Approved
0.8432	Intermediate Similarity	NPD8095	Phase 1
0.8371	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD4584	Approved
0.8198	Intermediate Similarity	NPD6788	Approved
0.8043	Intermediate Similarity	NPD7906	Approved
0.8	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7966	Intermediate Similarity	NPD3051	Approved
0.7919	Intermediate Similarity	NPD7298	Approved
0.7877	Intermediate Similarity	NPD4481	Phase 3
0.7849	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD2970	Approved
0.7821	Intermediate Similarity	NPD2969	Approved
0.773	Intermediate Similarity	NPD7312	Approved
0.773	Intermediate Similarity	NPD7313	Approved
0.773	Intermediate Similarity	NPD7311	Approved
0.773	Intermediate Similarity	NPD7310	Approved
0.7696	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD7309	Approved
0.768	Intermediate Similarity	NPD2489	Approved
0.768	Intermediate Similarity	NPD27	Approved
0.7657	Intermediate Similarity	NPD4772	Phase 2
0.7657	Intermediate Similarity	NPD4773	Phase 2
0.764	Intermediate Similarity	NPD7833	Phase 2
0.764	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD7831	Phase 2
0.7634	Intermediate Similarity	NPD4578	Approved
0.7634	Intermediate Similarity	NPD4577	Approved
0.7606	Intermediate Similarity	NPD4663	Approved
0.7605	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD6071	Discontinued
0.7558	Intermediate Similarity	NPD2421	Approved
0.7558	Intermediate Similarity	NPD2420	Approved
0.7556	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD4055	Discovery
0.754	Intermediate Similarity	NPD2971	Approved
0.754	Intermediate Similarity	NPD2968	Approved
0.7529	Intermediate Similarity	NPD6031	Approved
0.7529	Intermediate Similarity	NPD6030	Approved
0.7514	Intermediate Similarity	NPD1424	Approved
0.75	Intermediate Similarity	NPD7124	Phase 2
0.7459	Intermediate Similarity	NPD5677	Discontinued
0.7443	Intermediate Similarity	NPD4017	Approved
0.7429	Intermediate Similarity	NPD3640	Phase 3
0.7429	Intermediate Similarity	NPD3639	Approved
0.7429	Intermediate Similarity	NPD3641	Approved
0.7418	Intermediate Similarity	NPD7802	Discontinued
0.7389	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD2975	Approved
0.7385	Intermediate Similarity	NPD2974	Approved
0.7385	Intermediate Similarity	NPD2973	Approved
0.7356	Intermediate Similarity	NPD7598	Phase 2
0.7333	Intermediate Similarity	NPD2560	Approved
0.7333	Intermediate Similarity	NPD2563	Approved
0.7322	Intermediate Similarity	NPD6107	Approved
0.7314	Intermediate Similarity	NPD7447	Phase 1
0.7305	Intermediate Similarity	NPD4474	Approved
0.7305	Intermediate Similarity	NPD4475	Approved
0.7287	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4580	Approved
0.7262	Intermediate Similarity	NPD3110	Approved
0.7262	Intermediate Similarity	NPD3109	Approved
0.7246	Intermediate Similarity	NPD5718	Phase 2
0.7241	Intermediate Similarity	NPD5241	Discontinued
0.7236	Intermediate Similarity	NPD3450	Approved
0.7236	Intermediate Similarity	NPD3452	Approved
0.7236	Intermediate Similarity	NPD2494	Approved
0.7236	Intermediate Similarity	NPD2493	Approved
0.7235	Intermediate Similarity	NPD2200	Suspended
0.7229	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD2488	Approved
0.7216	Intermediate Similarity	NPD2490	Approved
0.7211	Intermediate Similarity	NPD7549	Discontinued
0.7184	Intermediate Similarity	NPD7466	Approved
0.7184	Intermediate Similarity	NPD6748	Discontinued
0.7159	Intermediate Similarity	NPD3124	Discontinued
0.7159	Intermediate Similarity	NPD7213	Phase 3
0.7159	Intermediate Similarity	NPD7212	Phase 2
0.7156	Intermediate Similarity	NPD6997	Phase 2
0.7151	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD4583	Approved
0.7129	Intermediate Similarity	NPD4582	Approved
0.7119	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD7047	Phase 3
0.7114	Intermediate Similarity	NPD5005	Approved
0.7114	Intermediate Similarity	NPD5006	Approved
0.7112	Intermediate Similarity	NPD2898	Approved
0.7111	Intermediate Similarity	NPD4678	Approved
0.7111	Intermediate Similarity	NPD4675	Approved
0.709	Intermediate Similarity	NPD5313	Approved
0.709	Intermediate Similarity	NPD5312	Approved
0.7079	Intermediate Similarity	NPD4004	Approved
0.7079	Intermediate Similarity	NPD4002	Approved
0.7079	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD4005	Discontinued
0.7045	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD5976	Discontinued
0.7035	Intermediate Similarity	NPD6896	Approved
0.7035	Intermediate Similarity	NPD6895	Approved
0.7035	Intermediate Similarity	NPD6111	Discontinued
0.7026	Intermediate Similarity	NPD7291	Discontinued
0.7015	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD3845	Phase 1
0.7006	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD4166	Phase 2
0.7005	Intermediate Similarity	NPD4010	Discontinued
0.7	Intermediate Similarity	NPD6042	Phase 2
0.7	Intermediate Similarity	NPD4420	Approved
0.7	Intermediate Similarity	NPD42	Phase 2
0.6995	Remote Similarity	NPD4585	Approved
0.6989	Remote Similarity	NPD6037	Discontinued
0.6989	Remote Similarity	NPD5754	Discontinued
0.6984	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD6072	Discontinued
0.6971	Remote Similarity	NPD7827	Phase 1
0.695	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD4107	Approved
0.6923	Remote Similarity	NPD5087	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD8152	Approved
0.6916	Remote Similarity	NPD8153	Approved
0.691	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD6090	Discontinued
0.6884	Remote Similarity	NPD7262	Phase 1
0.6878	Remote Similarity	NPD6687	Approved
0.6878	Remote Similarity	NPD6688	Approved
0.6872	Remote Similarity	NPD6851	Approved
0.6872	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD6853	Approved
0.6869	Remote Similarity	NPD7907	Approved
0.6868	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD7493	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD2122	Discontinued
0.6848	Remote Similarity	NPD5720	Discontinued
0.6842	Remote Similarity	NPD5676	Approved
0.6839	Remote Similarity	NPD6297	Approved
0.6836	Remote Similarity	NPD5177	Phase 3
0.6833	Remote Similarity	NPD4123	Phase 3
0.6816	Remote Similarity	NPD6666	Approved
0.6816	Remote Similarity	NPD6667	Approved
0.6814	Remote Similarity	NPD4482	Phase 3
0.6811	Remote Similarity	NPD5773	Approved
0.6811	Remote Similarity	NPD5772	Approved
0.6796	Remote Similarity	NPD4040	Phase 1
0.6796	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD7110	Phase 1
0.6793	Remote Similarity	NPD5090	Approved
0.6793	Remote Similarity	NPD5089	Approved
0.6793	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD5242	Approved
0.6786	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6618	Phase 2
0.6782	Remote Similarity	NPD6284	Clinical (unspecified phase)
0.678	Remote Similarity	NPD7590	Clinical (unspecified phase)
0.678	Remote Similarity	NPD3057	Approved
0.6778	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.676	Remote Similarity	NPD5160	Discontinued
0.6758	Remote Similarity	NPD4727	Phase 1
0.6757	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD7400	Phase 3
0.6744	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD7294	Phase 1
0.6744	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.672	Remote Similarity	NPD7046	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD5938	Phase 3
0.6716	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD7125	Discontinued
0.6712	Remote Similarity	NPD6625	Approved
0.6712	Remote Similarity	NPD6723	Discontinued
0.6703	Remote Similarity	NPD7438	Suspended
0.6702	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD7479	Phase 2
0.67	Remote Similarity	NPD7034	Discontinued
0.6699	Remote Similarity	NPD3533	Approved
0.6699	Remote Similarity	NPD2972	Approved
0.6686	Remote Similarity	NPD4625	Phase 3
0.6685	Remote Similarity	NPD7037	Approved
0.6685	Remote Similarity	NPD5297	Approved
0.6684	Remote Similarity	NPD7177	Discontinued
0.6684	Remote Similarity	NPD5978	Approved
0.6684	Remote Similarity	NPD5977	Approved
0.6667	Remote Similarity	NPD3384	Approved
0.6667	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6496	Clinical (unspecified phase)

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