NPASS Compound

Structure

CID196026 OpenBabel06191715582D 26 28 0 0 0 0 0 0 0 0999 V2000 8.2942 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4282 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4282 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -5.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2942 -5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -6.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5451 -3.3107 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 5 2 0 0 0 0 4 12 1 0 0 0 0 5 18 1 0 0 0 0 6 7 1 0 0 0 0 6 13 1 0 0 0 0 7 21 1 0 0 0 0 8 12 2 0 0 0 0 8 16 1 0 0 0 0 9 13 2 0 0 0 0 9 17 1 0 0 0 0 10 14 1 0 0 0 0 10 19 2 0 0 0 0 11 15 2 0 0 0 0 11 21 1 0 0 0 0 12 15 1 0 0 0 0 13 14 1 0 0 0 0 14 16 2 0 0 0 0 15 20 1 0 0 0 0 16 21 1 0 0 0 0 17 19 1 0 0 0 0 17 22 2 0 0 0 0 18 20 2 0 0 0 0 18 23 1 0 0 0 0 19 24 1 0 0 0 0 20 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	337.13
Volume:	345.316
LogP:	3.104
LogD:	3.469
LogS:	-3.909
# Rotatable Bonds:	3
TPSA:	51.16
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.845
Synthetic Accessibility Score:	3.542
Fsp3:	0.2
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.915
MDCK Permeability:	2.1251506041153334e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.562
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.05

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.532
Plasma Protein Binding (PPB):	90.9361343383789%
Volume Distribution (VD):	1.146
Pgp-substrate:	14.91225814819336%

ADMET: Metabolism

CYP1A2-inhibitor:	0.969
CYP1A2-substrate:	0.858
CYP2C19-inhibitor:	0.162
CYP2C19-substrate:	0.857
CYP2C9-inhibitor:	0.079
CYP2C9-substrate:	0.913
CYP2D6-inhibitor:	0.673
CYP2D6-substrate:	0.886
CYP3A4-inhibitor:	0.37
CYP3A4-substrate:	0.393

ADMET: Excretion

Clearance (CL):	5.499
Half-life (T1/2):	0.822

ADMET: Toxicity

hERG Blockers:	0.53
Human Hepatotoxicity (H-HT):	0.639
Drug-inuced Liver Injury (DILI):	0.563
AMES Toxicity:	0.707
Rat Oral Acute Toxicity:	0.436
Maximum Recommended Daily Dose:	0.744
Skin Sensitization:	0.955
Carcinogencity:	0.446
Eye Corrosion:	0.01
Eye Irritation:	0.224
Respiratory Toxicity:	0.953

Download Data

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

Natural Product: NPC196026

Natural Product ID:	NPC196026
*Common Name:**	Jatrorrhizine Chloride
IUPAC Name:	2,9,10-trimethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-3-one;hydrochloride
Synonyms:	GNF-Pf-220
Standard InCHIKey:	JKMUUZMCSNHBAX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H19NO4.ClH/c1-23-18-5-4-12-8-16-14-10-19(24-2)17(22)9-13(14)6-7-21(16)11-15(12)20(18)25-3;/h4-5,8-11H,6-7H2,1-3H3;1H
SMILES:	COc1ccc2=CC3=C4C=C(C(=O)C=C4CCN3C=c2c1OC)OC.Cl
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL274346
PubChem CID:	71730841 371256
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001909] Protoberberine alkaloids 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
NPO13757	Coptis japonica	Species	Ranunculaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[11000020]
NPO13757	Coptis japonica	Species	Ranunculaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[21401114]
NPO22622	Coptis deltoidea	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13757	Coptis japonica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5649	Coptis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22622	Coptis deltoidea	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5649	Coptis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13757	Coptis japonica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5649	Coptis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13757	Coptis japonica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22622	Coptis deltoidea	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5649	Coptis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29008	Coptis teeta	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13757	Coptis japonica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5649	Coptis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29008	Coptis teeta	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22622	Coptis deltoidea	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
EC50	2
IC50	7
Others	18

Activity Type	# Activity
Cell Line	2
Individual Protein	5
Organism	6
Others	14

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	IC50	=	71.0	ug.mL-1	PMID[494677]
NPT91	Cell Line	KB	Homo sapiens	IC50	>	335000.0	nM	PMID[494678]
NPT1229	Cell Line	Huh-7	Homo sapiens	CC50	=	8940.0	nM	PMID[494679]
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	IC50	=	71.0	ug.mL-1	PMID[494680]
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	Activity	=	71.19	%	PMID[494681]
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	Activity	=	52.2	%	PMID[494681]
NPT589	Individual Protein	Serum albumin	Bos taurus	Kb	=	1.73	10'3L/mol	PMID[494682]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.422	ug.mL-1	PMID[494676]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1.607	ug.mL-1	PMID[494676]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	3150.0	nM	PMID[494678]
NPT992	Organism	Entamoeba histolytica	Entamoeba histolytica	IC50	=	82700.0	nM	PMID[494678]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	EC50	=	939.0	nM	PMID[494679]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	EC50	=	1655.0	nM	PMID[494679]
NPT2	Others	Unspecified		IFI	=	0.0	%	PMID[494679]
NPT35	Others	n.a.		Solubility	=	12200000.0	nM	PMID[494682]
NPT35	Others	n.a.		Solubility	=	12400000.0	nM	PMID[494682]
NPT35	Others	n.a.		Solubility	=	1300000.0	nM	PMID[494682]
NPT35	Others	n.a.		Solubility	=	1500000.0	nM	PMID[494682]
NPT35	Others	n.a.		LogP	=	0.1	n.a.	PMID[494682]
NPT35	Others	n.a.		LogP	=	-1.2	n.a.	PMID[494682]
NPT35	Others	n.a.		LogP	=	-1.5	n.a.	PMID[494682]
NPT35	Others	n.a.		LogD	=	0.6	n.a.	PMID[494682]
NPT35	Others	n.a.		LogD	=	-1.2	n.a.	PMID[494682]
NPT35	Others	n.a.		LogD	=	-1.5	n.a.	PMID[494682]
NPT35	Others	n.a.		pKa	=	9.6	n.a.	PMID[494682]

☑ 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 NPC196026 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	198
0.1-0.2	3143
0.2-0.3	11437
0.3-0.4	6278
0.4-0.5	11148
0.5-0.6	9532
0.6-0.7	919
0.7-0.8	40
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC200555
0.9606	High Similarity	NPC13826
0.9606	High Similarity	NPC209195
0.9528	High Similarity	NPC274441
0.8151	Intermediate Similarity	NPC476580
0.7987	Intermediate Similarity	NPC57512
0.7718	Intermediate Similarity	NPC476579
0.76	Intermediate Similarity	NPC85747
0.76	Intermediate Similarity	NPC8337
0.758	Intermediate Similarity	NPC471604
0.7564	Intermediate Similarity	NPC306669
0.75	Intermediate Similarity	NPC476569
0.7447	Intermediate Similarity	NPC118419
0.7431	Intermediate Similarity	NPC214036
0.7431	Intermediate Similarity	NPC113236
0.7413	Intermediate Similarity	NPC11147
0.7391	Intermediate Similarity	NPC4669
0.731	Intermediate Similarity	NPC470707
0.7308	Intermediate Similarity	NPC106786
0.7292	Intermediate Similarity	NPC475828
0.7292	Intermediate Similarity	NPC230698
0.7292	Intermediate Similarity	NPC205178
0.7292	Intermediate Similarity	NPC255817
0.7292	Intermediate Similarity	NPC73883
0.7292	Intermediate Similarity	NPC136330
0.7292	Intermediate Similarity	NPC196609
0.7292	Intermediate Similarity	NPC277042
0.7292	Intermediate Similarity	NPC251454
0.7278	Intermediate Similarity	NPC59567
0.7261	Intermediate Similarity	NPC226428
0.726	Intermediate Similarity	NPC231572
0.7241	Intermediate Similarity	NPC99078
0.7233	Intermediate Similarity	NPC3375
0.7233	Intermediate Similarity	NPC255607
0.7222	Intermediate Similarity	NPC167096
0.7192	Intermediate Similarity	NPC193528
0.7192	Intermediate Similarity	NPC252107
0.7192	Intermediate Similarity	NPC220923
0.7164	Intermediate Similarity	NPC268317
0.7163	Intermediate Similarity	NPC172403
0.7103	Intermediate Similarity	NPC94280
0.7103	Intermediate Similarity	NPC159150
0.7103	Intermediate Similarity	NPC103947
0.7103	Intermediate Similarity	NPC328419
0.7103	Intermediate Similarity	NPC193673
0.7103	Intermediate Similarity	NPC45783
0.7092	Intermediate Similarity	NPC218323
0.7055	Intermediate Similarity	NPC138365
0.7055	Intermediate Similarity	NPC96406
0.7032	Intermediate Similarity	NPC218575
0.702	Intermediate Similarity	NPC244338
0.7007	Intermediate Similarity	NPC145446
0.7007	Intermediate Similarity	NPC137172
0.6986	Remote Similarity	NPC29650
0.6985	Remote Similarity	NPC185738
0.6985	Remote Similarity	NPC280001
0.6966	Remote Similarity	NPC217574
0.6959	Remote Similarity	NPC95366
0.6959	Remote Similarity	NPC248505
0.6933	Remote Similarity	NPC188163
0.6933	Remote Similarity	NPC328750
0.6933	Remote Similarity	NPC213206
0.6933	Remote Similarity	NPC474915
0.6899	Remote Similarity	NPC169742
0.6899	Remote Similarity	NPC93593
0.689	Remote Similarity	NPC473748
0.6875	Remote Similarity	NPC118804
0.6867	Remote Similarity	NPC314682
0.6842	Remote Similarity	NPC476567
0.6842	Remote Similarity	NPC136860
0.6842	Remote Similarity	NPC128019
0.6828	Remote Similarity	NPC160193
0.6824	Remote Similarity	NPC180647
0.6812	Remote Similarity	NPC277460
0.6809	Remote Similarity	NPC286573
0.6809	Remote Similarity	NPC256167
0.6809	Remote Similarity	NPC298486
0.6803	Remote Similarity	NPC266425
0.6795	Remote Similarity	NPC44869
0.6786	Remote Similarity	NPC269843
0.6786	Remote Similarity	NPC14007
0.6786	Remote Similarity	NPC109083
0.6786	Remote Similarity	NPC224814
0.6786	Remote Similarity	NPC60962
0.6786	Remote Similarity	NPC189844
0.6781	Remote Similarity	NPC172673
0.6779	Remote Similarity	NPC42793
0.6779	Remote Similarity	NPC307682
0.6779	Remote Similarity	NPC167944
0.6779	Remote Similarity	NPC231884
0.6779	Remote Similarity	NPC469808
0.6776	Remote Similarity	NPC908
0.6776	Remote Similarity	NPC138438
0.6774	Remote Similarity	NPC210437
0.6774	Remote Similarity	NPC16107
0.6774	Remote Similarity	NPC51957
0.6774	Remote Similarity	NPC476144
0.6774	Remote Similarity	NPC106295
0.6772	Remote Similarity	NPC58661
0.6759	Remote Similarity	NPC110313
0.6753	Remote Similarity	NPC130926
0.6753	Remote Similarity	NPC469978
0.6752	Remote Similarity	NPC223125
0.675	Remote Similarity	NPC190931
0.6735	Remote Similarity	NPC318862
0.6733	Remote Similarity	NPC225745
0.6731	Remote Similarity	NPC7467
0.6728	Remote Similarity	NPC475780
0.6721	Remote Similarity	NPC206876
0.6716	Remote Similarity	NPC179309
0.6709	Remote Similarity	NPC476568
0.6689	Remote Similarity	NPC239302
0.6689	Remote Similarity	NPC153453
0.6688	Remote Similarity	NPC469540
0.6688	Remote Similarity	NPC469539
0.6667	Remote Similarity	NPC90844
0.6667	Remote Similarity	NPC471073
0.6667	Remote Similarity	NPC270811
0.6667	Remote Similarity	NPC476570
0.6667	Remote Similarity	NPC95075
0.6667	Remote Similarity	NPC144863
0.6667	Remote Similarity	NPC223124
0.6667	Remote Similarity	NPC253883
0.6667	Remote Similarity	NPC471877
0.6667	Remote Similarity	NPC298339
0.6667	Remote Similarity	NPC329640
0.6645	Remote Similarity	NPC185838
0.6643	Remote Similarity	NPC229084
0.6643	Remote Similarity	NPC160900
0.6643	Remote Similarity	NPC106659
0.6643	Remote Similarity	NPC18984
0.6643	Remote Similarity	NPC69670
0.6642	Remote Similarity	NPC294941
0.6641	Remote Similarity	NPC175298
0.6625	Remote Similarity	NPC226941
0.6625	Remote Similarity	NPC14005
0.6625	Remote Similarity	NPC44642
0.6625	Remote Similarity	NPC108957
0.6624	Remote Similarity	NPC428
0.6624	Remote Similarity	NPC135538
0.6624	Remote Similarity	NPC147390
0.6624	Remote Similarity	NPC24233
0.6624	Remote Similarity	NPC475959
0.6624	Remote Similarity	NPC246587
0.6624	Remote Similarity	NPC476571
0.6623	Remote Similarity	NPC28641
0.6623	Remote Similarity	NPC194359
0.6621	Remote Similarity	NPC276014
0.6621	Remote Similarity	NPC301713
0.662	Remote Similarity	NPC211992
0.6619	Remote Similarity	NPC120075
0.6619	Remote Similarity	NPC323948
0.6606	Remote Similarity	NPC39103
0.6606	Remote Similarity	NPC2770
0.6606	Remote Similarity	NPC231198
0.6599	Remote Similarity	NPC35961
0.6599	Remote Similarity	NPC195749
0.6599	Remote Similarity	NPC52029
0.6596	Remote Similarity	NPC321133
0.6594	Remote Similarity	NPC47194
0.6593	Remote Similarity	NPC95977
0.6588	Remote Similarity	NPC85613
0.6587	Remote Similarity	NPC470324
0.6585	Remote Similarity	NPC153631
0.6582	Remote Similarity	NPC92541
0.6582	Remote Similarity	NPC470088
0.6582	Remote Similarity	NPC219162
0.6575	Remote Similarity	NPC186898
0.6575	Remote Similarity	NPC64948
0.6561	Remote Similarity	NPC321505
0.6561	Remote Similarity	NPC476151
0.6561	Remote Similarity	NPC191376
0.6561	Remote Similarity	NPC179825
0.6554	Remote Similarity	NPC114102
0.6549	Remote Similarity	NPC158949
0.6549	Remote Similarity	NPC83279
0.6547	Remote Similarity	NPC258992
0.6541	Remote Similarity	NPC151895
0.6541	Remote Similarity	NPC220858
0.6541	Remote Similarity	NPC192768
0.6541	Remote Similarity	NPC13397
0.6541	Remote Similarity	NPC88249
0.6541	Remote Similarity	NPC274026
0.6541	Remote Similarity	NPC478189
0.6541	Remote Similarity	NPC97221
0.6538	Remote Similarity	NPC9373
0.6536	Remote Similarity	NPC178290
0.6533	Remote Similarity	NPC470441
0.6533	Remote Similarity	NPC473463
0.6531	Remote Similarity	NPC155838
0.6531	Remote Similarity	NPC283079
0.6529	Remote Similarity	NPC207721
0.6525	Remote Similarity	NPC37858
0.6524	Remote Similarity	NPC158900
0.6519	Remote Similarity	NPC130941
0.6519	Remote Similarity	NPC153644
0.6515	Remote Similarity	NPC109637
0.6513	Remote Similarity	NPC253429
0.6512	Remote Similarity	NPC149285
0.6512	Remote Similarity	NPC313918

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 NPC196026 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	135
0.1-0.2	827
0.2-0.3	1210
0.3-0.4	2341
0.4-0.5	2915
0.5-0.6	1435
0.6-0.7	285
0.7-0.8	2
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7292	Intermediate Similarity	NPD2492	Phase 1
0.7014	Intermediate Similarity	NPD5718	Phase 2
0.6993	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD5536	Phase 2
0.6954	Remote Similarity	NPD5481	Discontinued
0.6933	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD5297	Approved
0.6899	Remote Similarity	NPD3311	Phase 1
0.6899	Remote Similarity	NPD3312	Phase 1
0.6883	Remote Similarity	NPD2335	Discontinued
0.6849	Remote Similarity	NPD3530	Approved
0.6849	Remote Similarity	NPD3532	Approved
0.6849	Remote Similarity	NPD3531	Approved
0.6846	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD3142	Approved
0.6803	Remote Similarity	NPD3140	Approved
0.6779	Remote Similarity	NPD6896	Approved
0.6779	Remote Similarity	NPD6895	Approved
0.6774	Remote Similarity	NPD4584	Approved
0.6763	Remote Similarity	NPD2594	Approved
0.6763	Remote Similarity	NPD2595	Approved
0.6763	Remote Similarity	NPD6382	Discontinued
0.675	Remote Similarity	NPD4585	Approved
0.6742	Remote Similarity	NPD5373	Approved
0.6742	Remote Similarity	NPD5374	Approved
0.6739	Remote Similarity	NPD1408	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD1103	Approved
0.6739	Remote Similarity	NPD1102	Approved
0.673	Remote Similarity	NPD6386	Approved
0.673	Remote Similarity	NPD6385	Approved
0.6728	Remote Similarity	NPD3368	Phase 2
0.6713	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD1044	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD5977	Approved
0.6708	Remote Similarity	NPD5978	Approved
0.6691	Remote Similarity	NPD7534	Approved
0.6691	Remote Similarity	NPD7533	Approved
0.6688	Remote Similarity	NPD3639	Approved
0.6688	Remote Similarity	NPD3640	Phase 3
0.6688	Remote Similarity	NPD6031	Approved
0.6688	Remote Similarity	NPD6030	Approved
0.6688	Remote Similarity	NPD3641	Approved
0.6667	Remote Similarity	NPD4236	Phase 3
0.6667	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4237	Approved
0.6643	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD1798	Approved
0.6643	Remote Similarity	NPD1797	Approved
0.6625	Remote Similarity	NPD5089	Approved
0.6625	Remote Similarity	NPD5090	Approved
0.6625	Remote Similarity	NPD6873	Phase 2
0.6623	Remote Similarity	NPD2086	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD2085	Suspended
0.6617	Remote Similarity	NPD1358	Approved
0.6604	Remote Similarity	NPD3866	Clinical (unspecified phase)
0.66	Remote Similarity	NPD2653	Approved
0.6599	Remote Similarity	NPD5746	Approved
0.6597	Remote Similarity	NPD2922	Phase 1
0.6596	Remote Similarity	NPD2667	Approved
0.6596	Remote Similarity	NPD2668	Approved
0.6593	Remote Similarity	NPD2671	Approved
0.6593	Remote Similarity	NPD2673	Approved
0.6587	Remote Similarity	NPD2898	Approved
0.6581	Remote Similarity	NPD5241	Discontinued
0.6575	Remote Similarity	NPD2250	Discontinued
0.6575	Remote Similarity	NPD4993	Discontinued
0.6571	Remote Similarity	NPD2486	Discontinued
0.6564	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD5177	Phase 3
0.6552	Remote Similarity	NPD4098	Discontinued
0.6549	Remote Similarity	NPD3447	Discontinued
0.6549	Remote Similarity	NPD3294	Phase 2
0.6536	Remote Similarity	NPD3656	Approved
0.6531	Remote Similarity	NPD3537	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD593	Approved
0.6522	Remote Similarity	NPD595	Approved
0.6516	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.651	Remote Similarity	NPD5745	Approved
0.6507	Remote Similarity	NPD2987	Approved
0.6507	Remote Similarity	NPD2990	Approved
0.6503	Remote Similarity	NPD6063	Approved
0.65	Remote Similarity	NPD824	Approved
0.6479	Remote Similarity	NPD2423	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD1725	Approved
0.6458	Remote Similarity	NPD2230	Approved
0.6458	Remote Similarity	NPD2232	Approved
0.6458	Remote Similarity	NPD2233	Approved
0.6456	Remote Similarity	NPD3536	Discontinued
0.6456	Remote Similarity	NPD3146	Approved
0.6456	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD4162	Approved
0.6452	Remote Similarity	NPD3060	Approved
0.6449	Remote Similarity	NPD5283	Phase 1
0.6447	Remote Similarity	NPD6111	Discontinued
0.6443	Remote Similarity	NPD3374	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD3145	Approved
0.6443	Remote Similarity	NPD3144	Approved
0.6434	Remote Similarity	NPD155	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD7124	Phase 2
0.6433	Remote Similarity	NPD3281	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD3596	Phase 2
0.6429	Remote Similarity	NPD2388	Discontinued
0.642	Remote Similarity	NPD7110	Phase 1
0.642	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD3134	Approved
0.6414	Remote Similarity	NPD1421	Approved
0.6414	Remote Similarity	NPD1420	Approved
0.6405	Remote Similarity	NPD3260	Discontinued
0.64	Remote Similarity	NPD554	Clinical (unspecified phase)
0.64	Remote Similarity	NPD2674	Phase 3
0.6398	Remote Similarity	NPD4017	Approved
0.6398	Remote Similarity	NPD2312	Discontinued
0.6395	Remote Similarity	NPD7905	Discontinued
0.6382	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.638	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.638	Remote Similarity	NPD7298	Approved
0.638	Remote Similarity	NPD6844	Discontinued
0.6375	Remote Similarity	NPD2122	Discontinued
0.6369	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD2554	Approved
0.6364	Remote Similarity	NPD4859	Phase 1
0.6364	Remote Similarity	NPD2556	Approved
0.6358	Remote Similarity	NPD3110	Approved
0.6358	Remote Similarity	NPD3109	Approved
0.6357	Remote Similarity	NPD2557	Approved
0.6353	Remote Similarity	NPD5966	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6352	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD2040	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.634	Remote Similarity	NPD743	Approved
0.6338	Remote Similarity	NPD6580	Approved
0.6338	Remote Similarity	NPD6581	Approved
0.6319	Remote Similarity	NPD5889	Approved
0.6319	Remote Similarity	NPD5890	Approved
0.6316	Remote Similarity	NPD2822	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD1350	Approved
0.6312	Remote Similarity	NPD1349	Approved
0.6312	Remote Similarity	NPD1351	Approved
0.6312	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD6331	Phase 2
0.6299	Remote Similarity	NPD2164	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD4481	Phase 3
0.6294	Remote Similarity	NPD3444	Approved
0.6294	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD3049	Approved
0.6294	Remote Similarity	NPD3443	Approved
0.6294	Remote Similarity	NPD3445	Approved
0.6292	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6291	Remote Similarity	NPD4474	Approved
0.6291	Remote Similarity	NPD2245	Discovery
0.6291	Remote Similarity	NPD4475	Approved
0.6289	Remote Similarity	NPD4357	Discontinued
0.6284	Remote Similarity	NPD7018	Phase 2
0.6282	Remote Similarity	NPD2897	Discontinued
0.6279	Remote Similarity	NPD9296	Approved
0.6273	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD3179	Approved
0.6267	Remote Similarity	NPD3180	Approved
0.6267	Remote Similarity	NPD5163	Phase 2
0.6266	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD6788	Approved
0.6258	Remote Similarity	NPD6876	Approved
0.6258	Remote Similarity	NPD6585	Discontinued
0.6258	Remote Similarity	NPD6875	Approved
0.625	Remote Similarity	NPD5677	Discontinued
0.625	Remote Similarity	NPD4123	Phase 3
0.625	Remote Similarity	NPD1424	Approved
0.6243	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD1285	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD2654	Approved
0.6241	Remote Similarity	NPD291	Approved
0.6236	Remote Similarity	NPD7291	Discontinued
0.6235	Remote Similarity	NPD4124	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD5267	Discontinued
0.6235	Remote Similarity	NPD5242	Approved
0.6235	Remote Similarity	NPD4210	Discontinued
0.6234	Remote Similarity	NPD2200	Suspended
0.6229	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6229	Remote Similarity	NPD7549	Discontinued
0.6226	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD5295	Discontinued
0.6225	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6225	Remote Similarity	NPD1048	Approved
0.6225	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6221	Remote Similarity	NPD2163	Approved
0.622	Remote Similarity	NPD4772	Phase 2
0.622	Remote Similarity	NPD4201	Clinical (unspecified phase)
0.622	Remote Similarity	NPD4773	Phase 2
0.6218	Remote Similarity	NPD5865	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD1817	Approved
0.6216	Remote Similarity	NPD1820	Approved
0.6216	Remote Similarity	NPD1818	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