NPASS Compound

Structure

CID21638 OpenBabel06191715342D 28 32 0 0 1 0 0 0 0 0999 V2000 -5.0838 -0.9451 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0106 0.7203 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1222 -2.9346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5214 1.4554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6813 1.9408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6810 1.9414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5213 1.4565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6809 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6816 -0.9699 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3618 0.0008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3626 -2.9098 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2024 -1.4543 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5212 0.4846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8405 1.4558 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8404 1.4561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5220 -1.4547 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3621 -0.9694 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5222 -2.4249 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8403 0.4850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6814 0.0003 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8406 0.4853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6408 -2.9341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5215 0.4857 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -1.6411 -3.9520 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3613 -0.0006 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7592 -2.4254 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2027 -2.4245 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 26 1 0 0 0 0 3 27 1 0 0 0 0 4 5 2 0 0 0 0 4 13 1 0 0 0 0 5 14 1 0 0 0 0 6 7 1 0 0 0 0 6 15 1 0 0 0 0 7 24 1 0 0 0 0 8 13 2 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 24 1 0 0 0 0 11 18 2 0 0 0 0 11 28 1 0 0 0 0 12 1 1 1 0 0 0 12 17 1 0 0 0 0 12 28 1 0 0 0 0 13 26 1 0 0 0 0 14 15 1 0 0 0 0 14 19 2 0 0 0 0 15 21 2 0 0 0 0 16 9 1 6 0 0 0 16 17 1 0 0 0 0 16 18 1 0 0 0 0 17 10 1 6 0 0 0 18 22 1 0 0 0 0 19 23 1 0 0 0 0 20 21 1 0 0 0 0 20 24 1 6 0 0 0 21 23 1 0 0 0 0 22 25 2 0 0 0 0 22 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	382.19
Volume:	387.622
LogP:	3.832
LogD:	3.389
LogS:	-3.158
# Rotatable Bonds:	3
TPSA:	63.79
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.809
Synthetic Accessibility Score:	3.992
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.925
MDCK Permeability:	5.4033684136811644e-05
Pgp-inhibitor:	0.015
Pgp-substrate:	0.28
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.113
30% Bioavailability (F30%):	0.403

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.993
Plasma Protein Binding (PPB):	76.6368179321289%
Volume Distribution (VD):	1.687
Pgp-substrate:	16.334012985229492%

ADMET: Metabolism

CYP1A2-inhibitor:	0.937
CYP1A2-substrate:	0.884
CYP2C19-inhibitor:	0.781
CYP2C19-substrate:	0.879
CYP2C9-inhibitor:	0.612
CYP2C9-substrate:	0.636
CYP2D6-inhibitor:	0.93
CYP2D6-substrate:	0.9
CYP3A4-inhibitor:	0.95
CYP3A4-substrate:	0.891

ADMET: Excretion

Clearance (CL):	7.546
Half-life (T1/2):	0.292

ADMET: Toxicity

hERG Blockers:	0.924
Human Hepatotoxicity (H-HT):	0.567
Drug-inuced Liver Injury (DILI):	0.68
AMES Toxicity:	0.951
Rat Oral Acute Toxicity:	0.985
Maximum Recommended Daily Dose:	0.984
Skin Sensitization:	0.909
Carcinogencity:	0.97
Eye Corrosion:	0.004
Eye Irritation:	0.037
Respiratory Toxicity:	0.986

Download Data

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

Natural Product: NPC21638

Natural Product ID:	NPC21638
*Common Name:**	KXEMQEGRZWUKJS-RURTYGRKSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KXEMQEGRZWUKJS-RURTYGRKSA-N
Standard InCHI:	InChI=1S/C22H26N2O4/c1-12-17-10-24-7-6-15-14-5-4-13(26-2)8-19(14)23-21(15)20(24)9-16(17)18(11-28-12)22(25)27-3/h4-5,8,11-12,16-17,20,23H,6-7,9-10H2,1-3H3/t12-,16-,17-,20-/m0/s1
SMILES:	COc1ccc2c(c1)[nH]c1c2CCN2[C@H]1C[C@H]1[C@@H](C2)[C@H](C)OC=C1C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1329821
PubChem CID:	72313
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001786] Yohimbine alkaloids

*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
NPO12216	Gynura elliptica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14590	Ruta oreojasme	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14590	Ruta oreojasme	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25628.1	Abrus pulchellus subsp. cantoniensis	Subspecies	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14590	Ruta oreojasme	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14210	Brugmansia arborea	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13601	Relicina connivens	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25628.1	Abrus pulchellus subsp. cantoniensis	Subspecies	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19809	Streptomyces roseoviolaceus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO3078	Gentiana pyrenaica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11862	Ostrinia nubilalis	Species	Crambidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12216	Gynura elliptica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6602	Vinca major	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25599	Gloxinia erinoides	Species	Gesneriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1409	Drymonia macrophylla	Species	Gesneriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2065	Eriostemon deserti	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21627	Bambusa chungii	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13490	Diospyros tricolor	Species	Ebenaceae	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
Potency	9

Activity Type	# Activity
Individual Protein	7
Protein-Protein Interaction	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	25118.9	nM	PMID[458848]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	15848.9	nM	PMID[458848]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	22387.2	nM	PMID[458848]
NPT55	Individual Protein	Putative fructose-1,6-bisphosphate aldolase	Giardia intestinalis	Potency	=	14091.9	nM	PMID[458848]
NPT282	Individual Protein	MAP kinase ERK2	Homo sapiens	Potency	=	22387.2	nM	PMID[458848]
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	79432.8	nM	PMID[458848]
NPT197	Protein-Protein Interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	25118.9	nM	PMID[458848]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	31622.8	nM	PMID[458848]
NPT533	Protein-Protein Interaction	Runt-related transcription factor 1/Core-binding factor subunit beta	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[458848]

☑ 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 NPC21638 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	362
0.1-0.2	1833
0.2-0.3	8994
0.3-0.4	8823
0.4-0.5	15552
0.5-0.6	4180
0.6-0.7	2229
0.7-0.8	633
0.8-0.85	70
0.85-0.9	17
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9307	High Similarity	NPC152768
0.9307	High Similarity	NPC148183
0.9014	High Similarity	NPC473105
0.8894	High Similarity	NPC312870
0.8894	High Similarity	NPC199851
0.8894	High Similarity	NPC128265
0.8894	High Similarity	NPC294909
0.8894	High Similarity	NPC254240
0.8878	High Similarity	NPC264176
0.8798	High Similarity	NPC305984
0.8762	High Similarity	NPC472099
0.8667	High Similarity	NPC473041
0.8559	High Similarity	NPC284685
0.8534	High Similarity	NPC88923
0.8534	High Similarity	NPC100734
0.8534	High Similarity	NPC315634
0.8447	Intermediate Similarity	NPC474192
0.8447	Intermediate Similarity	NPC475720
0.8404	Intermediate Similarity	NPC303658
0.8404	Intermediate Similarity	NPC469594
0.8392	Intermediate Similarity	NPC111602
0.8392	Intermediate Similarity	NPC196251
0.8392	Intermediate Similarity	NPC63199
0.8392	Intermediate Similarity	NPC102338
0.8378	Intermediate Similarity	NPC184680
0.8362	Intermediate Similarity	NPC191489
0.835	Intermediate Similarity	NPC472112
0.8341	Intermediate Similarity	NPC472098
0.8341	Intermediate Similarity	NPC470785
0.8341	Intermediate Similarity	NPC470784
0.8325	Intermediate Similarity	NPC475910
0.8311	Intermediate Similarity	NPC311906
0.8304	Intermediate Similarity	NPC475816
0.8302	Intermediate Similarity	NPC469592
0.8302	Intermediate Similarity	NPC234078
0.8302	Intermediate Similarity	NPC221100
0.8302	Intermediate Similarity	NPC471080
0.8287	Intermediate Similarity	NPC60621
0.8278	Intermediate Similarity	NPC4687
0.8252	Intermediate Similarity	NPC329747
0.8233	Intermediate Similarity	NPC96321
0.8227	Intermediate Similarity	NPC66777
0.8227	Intermediate Similarity	NPC194740
0.8227	Intermediate Similarity	NPC471762
0.8177	Intermediate Similarity	NPC472113
0.8158	Intermediate Similarity	NPC81939
0.8146	Intermediate Similarity	NPC245916
0.814	Intermediate Similarity	NPC330009
0.8122	Intermediate Similarity	NPC87413
0.8122	Intermediate Similarity	NPC475666
0.8104	Intermediate Similarity	NPC249583
0.8102	Intermediate Similarity	NPC169402
0.81	Intermediate Similarity	NPC478078
0.81	Intermediate Similarity	NPC84478
0.8075	Intermediate Similarity	NPC471304
0.8068	Intermediate Similarity	NPC306376
0.8065	Intermediate Similarity	NPC82070
0.8028	Intermediate Similarity	NPC52254
0.801	Intermediate Similarity	NPC220151
0.801	Intermediate Similarity	NPC19692
0.8009	Intermediate Similarity	NPC116238
0.8009	Intermediate Similarity	NPC285558
0.7991	Intermediate Similarity	NPC123976
0.7991	Intermediate Similarity	NPC167860
0.7972	Intermediate Similarity	NPC238457
0.7964	Intermediate Similarity	NPC475271
0.7955	Intermediate Similarity	NPC198503
0.7921	Intermediate Similarity	NPC258480
0.7917	Intermediate Similarity	NPC310211
0.7917	Intermediate Similarity	NPC308137
0.7911	Intermediate Similarity	NPC260434
0.791	Intermediate Similarity	NPC471303
0.7909	Intermediate Similarity	NPC174760
0.7905	Intermediate Similarity	NPC329793
0.7902	Intermediate Similarity	NPC33949
0.7897	Intermediate Similarity	NPC39679
0.789	Intermediate Similarity	NPC476114
0.7887	Intermediate Similarity	NPC472111
0.7883	Intermediate Similarity	NPC122436
0.7867	Intermediate Similarity	NPC232727
0.786	Intermediate Similarity	NPC469589
0.7832	Intermediate Similarity	NPC474688
0.783	Intermediate Similarity	NPC295898
0.7828	Intermediate Similarity	NPC150239
0.782	Intermediate Similarity	NPC249150
0.782	Intermediate Similarity	NPC79129
0.782	Intermediate Similarity	NPC195461
0.782	Intermediate Similarity	NPC49196
0.782	Intermediate Similarity	NPC81654
0.782	Intermediate Similarity	NPC313985
0.7806	Intermediate Similarity	NPC303374
0.7804	Intermediate Similarity	NPC300156
0.7792	Intermediate Similarity	NPC477066
0.7783	Intermediate Similarity	NPC213530
0.7783	Intermediate Similarity	NPC101350
0.7783	Intermediate Similarity	NPC474183
0.7783	Intermediate Similarity	NPC193267
0.7778	Intermediate Similarity	NPC157931
0.7767	Intermediate Similarity	NPC175474
0.7759	Intermediate Similarity	NPC478082
0.7759	Intermediate Similarity	NPC478081
0.7759	Intermediate Similarity	NPC477067
0.7756	Intermediate Similarity	NPC66210
0.7748	Intermediate Similarity	NPC323969
0.7748	Intermediate Similarity	NPC128115
0.7739	Intermediate Similarity	NPC235685
0.7738	Intermediate Similarity	NPC247803
0.7738	Intermediate Similarity	NPC174788
0.7738	Intermediate Similarity	NPC46561
0.7736	Intermediate Similarity	NPC249040
0.7735	Intermediate Similarity	NPC469734
0.7727	Intermediate Similarity	NPC469928
0.7725	Intermediate Similarity	NPC72211
0.7725	Intermediate Similarity	NPC50503
0.7725	Intermediate Similarity	NPC52557
0.771	Intermediate Similarity	NPC476098
0.7706	Intermediate Similarity	NPC146418
0.7703	Intermediate Similarity	NPC208084
0.7702	Intermediate Similarity	NPC17437
0.7696	Intermediate Similarity	NPC174758
0.7689	Intermediate Similarity	NPC329982
0.7686	Intermediate Similarity	NPC284888
0.7682	Intermediate Similarity	NPC473540
0.7679	Intermediate Similarity	NPC473800
0.7679	Intermediate Similarity	NPC280272
0.7656	Intermediate Similarity	NPC55493
0.7655	Intermediate Similarity	NPC24370
0.7655	Intermediate Similarity	NPC319232
0.7647	Intermediate Similarity	NPC74969
0.7647	Intermediate Similarity	NPC3207
0.7642	Intermediate Similarity	NPC321592
0.7642	Intermediate Similarity	NPC54803
0.7639	Intermediate Similarity	NPC148889
0.7639	Intermediate Similarity	NPC45190
0.7639	Intermediate Similarity	NPC475844
0.7634	Intermediate Similarity	NPC280799
0.7632	Intermediate Similarity	NPC223409
0.763	Intermediate Similarity	NPC70259
0.7625	Intermediate Similarity	NPC478083
0.7621	Intermediate Similarity	NPC118559
0.7621	Intermediate Similarity	NPC34580
0.7621	Intermediate Similarity	NPC124920
0.7621	Intermediate Similarity	NPC261251
0.7621	Intermediate Similarity	NPC304307
0.7619	Intermediate Similarity	NPC57453
0.761	Intermediate Similarity	NPC176127
0.7605	Intermediate Similarity	NPC133609
0.7604	Intermediate Similarity	NPC53344
0.76	Intermediate Similarity	NPC220851
0.76	Intermediate Similarity	NPC144452
0.7594	Intermediate Similarity	NPC70956
0.7594	Intermediate Similarity	NPC243834
0.7593	Intermediate Similarity	NPC87714
0.7588	Intermediate Similarity	NPC100547
0.7583	Intermediate Similarity	NPC43787
0.7583	Intermediate Similarity	NPC478080
0.7583	Intermediate Similarity	NPC205934
0.7582	Intermediate Similarity	NPC152620
0.7577	Intermediate Similarity	NPC214142
0.7573	Intermediate Similarity	NPC189079
0.7565	Intermediate Similarity	NPC469554
0.7564	Intermediate Similarity	NPC99891
0.756	Intermediate Similarity	NPC314333
0.7558	Intermediate Similarity	NPC476106
0.7557	Intermediate Similarity	NPC39500
0.7556	Intermediate Similarity	NPC310118
0.7555	Intermediate Similarity	NPC322135
0.7555	Intermediate Similarity	NPC95240
0.7548	Intermediate Similarity	NPC472323
0.7546	Intermediate Similarity	NPC162484
0.7546	Intermediate Similarity	NPC223427
0.7544	Intermediate Similarity	NPC110151
0.7543	Intermediate Similarity	NPC477549
0.7536	Intermediate Similarity	NPC472107
0.7536	Intermediate Similarity	NPC79062
0.7535	Intermediate Similarity	NPC267423
0.7533	Intermediate Similarity	NPC179287
0.7533	Intermediate Similarity	NPC473449
0.7524	Intermediate Similarity	NPC472108
0.7524	Intermediate Similarity	NPC472097
0.7524	Intermediate Similarity	NPC139291
0.7523	Intermediate Similarity	NPC477979
0.7523	Intermediate Similarity	NPC474905
0.7523	Intermediate Similarity	NPC321428
0.7522	Intermediate Similarity	NPC14288
0.7512	Intermediate Similarity	NPC469896
0.7511	Intermediate Similarity	NPC274640
0.75	Intermediate Similarity	NPC39370
0.75	Intermediate Similarity	NPC475112
0.75	Intermediate Similarity	NPC475085
0.75	Intermediate Similarity	NPC131017
0.75	Intermediate Similarity	NPC291535
0.749	Intermediate Similarity	NPC195788
0.749	Intermediate Similarity	NPC237901
0.749	Intermediate Similarity	NPC165964
0.7489	Intermediate Similarity	NPC274982
0.7489	Intermediate Similarity	NPC473186
0.7488	Intermediate Similarity	NPC472119
0.7479	Intermediate Similarity	NPC53534
0.7479	Intermediate Similarity	NPC131486

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 NPC21638 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	208
0.1-0.2	581
0.2-0.3	734
0.3-0.4	1368
0.4-0.5	2470
0.5-0.6	2572
0.6-0.7	1042
0.7-0.8	165
0.8-0.85	8
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8894	High Similarity	NPD4501	Approved
0.8894	High Similarity	NPD4500	Approved
0.8559	High Similarity	NPD7956	Approved
0.8559	High Similarity	NPD7955	Approved
0.8534	High Similarity	NPD7803	Approved
0.8362	Intermediate Similarity	NPD7708	Approved
0.8198	Intermediate Similarity	NPD4885	Approved
0.8066	Intermediate Similarity	NPD5658	Approved
0.8017	Intermediate Similarity	NPD5482	Discontinued
0.7982	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7982	Intermediate Similarity	NPD5632	Approved
0.782	Intermediate Similarity	NPD4601	Approved
0.782	Intermediate Similarity	NPD4600	Approved
0.7773	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7709	Intermediate Similarity	NPD4952	Phase 3
0.7706	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD8358	Approved
0.7696	Intermediate Similarity	NPD3006	Discontinued
0.7695	Intermediate Similarity	NPD5450	Discontinued
0.7692	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7689	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD3003	Approved
0.763	Intermediate Similarity	NPD6550	Discontinued
0.7623	Intermediate Similarity	NPD6770	Approved
0.7623	Intermediate Similarity	NPD7194	Discontinued
0.7615	Intermediate Similarity	NPD4506	Discontinued
0.7609	Intermediate Similarity	NPD4373	Phase 2
0.7602	Intermediate Similarity	NPD8364	Approved
0.7602	Intermediate Similarity	NPD8363	Approved
0.7602	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD6242	Discontinued
0.7583	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD3393	Approved
0.7568	Intermediate Similarity	NPD3389	Approved
0.7568	Intermediate Similarity	NPD3394	Approved
0.7563	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD4499	Approved
0.754	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6716	Phase 1
0.7523	Intermediate Similarity	NPD1768	Approved
0.7522	Intermediate Similarity	NPD6962	Phase 2
0.7521	Intermediate Similarity	NPD7025	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD3946	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4418	Discontinued
0.749	Intermediate Similarity	NPD8466	Approved
0.749	Intermediate Similarity	NPD8465	Approved
0.749	Intermediate Similarity	NPD8467	Approved
0.7489	Intermediate Similarity	NPD2916	Discontinued
0.7479	Intermediate Similarity	NPD8255	Phase 2
0.7467	Intermediate Similarity	NPD7994	Phase 2
0.7467	Intermediate Similarity	NPD3259	Approved
0.7465	Intermediate Similarity	NPD5512	Phase 3
0.7457	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD7558	Phase 2
0.7444	Intermediate Similarity	NPD5902	Approved
0.7444	Intermediate Similarity	NPD5293	Phase 2
0.7444	Intermediate Similarity	NPD5903	Approved
0.7437	Intermediate Similarity	NPD8359	Phase 2
0.7432	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD7426	Phase 1
0.7418	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD7417	Discontinued
0.7415	Intermediate Similarity	NPD6790	Phase 1
0.7409	Intermediate Similarity	NPD2509	Approved
0.7409	Intermediate Similarity	NPD2510	Approved
0.7403	Intermediate Similarity	NPD5479	Discontinued
0.7391	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD8459	Approved
0.7373	Intermediate Similarity	NPD8425	Approved
0.7373	Intermediate Similarity	NPD8426	Approved
0.7373	Intermediate Similarity	NPD8460	Approved
0.7371	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7352	Intermediate Similarity	NPD8428	Approved
0.7352	Intermediate Similarity	NPD8427	Approved
0.7352	Intermediate Similarity	NPD8429	Approved
0.7352	Intermediate Similarity	NPD4795	Phase 2
0.7349	Intermediate Similarity	NPD5003	Discontinued
0.7339	Intermediate Similarity	NPD7796	Approved
0.7339	Intermediate Similarity	NPD7797	Approved
0.7328	Intermediate Similarity	NPD7589	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD8463	Approved
0.7315	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD4558	Phase 2
0.7292	Intermediate Similarity	NPD5488	Discontinued
0.729	Intermediate Similarity	NPD1038	Approved
0.7285	Intermediate Similarity	NPD1392	Approved
0.7281	Intermediate Similarity	NPD5930	Phase 3
0.7277	Intermediate Similarity	NPD7069	Discontinued
0.7273	Intermediate Similarity	NPD4034	Approved
0.7273	Intermediate Similarity	NPD32	Approved
0.7273	Intermediate Similarity	NPD4035	Approved
0.7273	Intermediate Similarity	NPD4038	Approved
0.7273	Intermediate Similarity	NPD4036	Approved
0.7273	Intermediate Similarity	NPD4039	Approved
0.7273	Intermediate Similarity	NPD4122	Approved
0.7273	Intermediate Similarity	NPD4037	Approved
0.7273	Intermediate Similarity	NPD4033	Approved
0.7273	Intermediate Similarity	NPD31	Approved
0.7269	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7269	Intermediate Similarity	NPD6985	Discontinued
0.7261	Intermediate Similarity	NPD6276	Discontinued
0.7248	Intermediate Similarity	NPD1740	Approved
0.7248	Intermediate Similarity	NPD1739	Approved
0.7236	Intermediate Similarity	NPD8091	Phase 3
0.7232	Intermediate Similarity	NPD4502	Phase 2
0.7232	Intermediate Similarity	NPD5416	Discontinued
0.7232	Intermediate Similarity	NPD7470	Discontinued
0.7227	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD4203	Approved
0.7225	Intermediate Similarity	NPD4204	Approved
0.7215	Intermediate Similarity	NPD4958	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD4368	Phase 2
0.7212	Intermediate Similarity	NPD4897	Phase 2
0.7212	Intermediate Similarity	NPD3257	Approved
0.7207	Intermediate Similarity	NPD7222	Phase 2
0.7207	Intermediate Similarity	NPD5429	Discontinued
0.7193	Intermediate Similarity	NPD7395	Discontinued
0.7188	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.718	Intermediate Similarity	NPD7690	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD6228	Discontinued
0.7173	Intermediate Similarity	NPD7853	Phase 2
0.7169	Intermediate Similarity	NPD484	Approved
0.7167	Intermediate Similarity	NPD6517	Phase 3
0.7162	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD8403	Phase 1
0.7162	Intermediate Similarity	NPD3258	Approved
0.716	Intermediate Similarity	NPD8102	Discontinued
0.7155	Intermediate Similarity	NPD8016	Phase 3
0.7155	Intermediate Similarity	NPD8017	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD6964	Approved
0.7131	Intermediate Similarity	NPD6963	Approved
0.713	Intermediate Similarity	NPD5070	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD3815	Phase 1
0.7124	Intermediate Similarity	NPD3816	Phase 1
0.7123	Intermediate Similarity	NPD4889	Approved
0.7117	Intermediate Similarity	NPD5901	Discontinued
0.7113	Intermediate Similarity	NPD7729	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD6769	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD5612	Discontinued
0.7103	Intermediate Similarity	NPD6608	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD4642	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD7571	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD5256	Discontinued
0.7085	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD7174	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD7778	Approved
0.7078	Intermediate Similarity	NPD7777	Approved
0.7078	Intermediate Similarity	NPD53	Approved
0.7076	Intermediate Similarity	NPD7284	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD6176	Phase 1
0.707	Intermediate Similarity	NPD2564	Approved
0.707	Intermediate Similarity	NPD2565	Phase 2
0.7068	Intermediate Similarity	NPD8489	Phase 1
0.7064	Intermediate Similarity	NPD5559	Phase 2
0.7061	Intermediate Similarity	NPD7538	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD802	Phase 2
0.7051	Intermediate Similarity	NPD7603	Discontinued
0.7043	Intermediate Similarity	NPD4429	Discontinued
0.7043	Intermediate Similarity	NPD3354	Phase 2
0.704	Intermediate Similarity	NPD6531	Approved
0.704	Intermediate Similarity	NPD6530	Approved
0.7039	Intermediate Similarity	NPD7547	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7548	Discontinued
0.7037	Intermediate Similarity	NPD5913	Phase 3
0.7037	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD5507	Approved
0.7026	Intermediate Similarity	NPD5506	Approved
0.7021	Intermediate Similarity	NPD4328	Approved
0.7018	Intermediate Similarity	NPD4602	Approved
0.7017	Intermediate Similarity	NPD6494	Phase 2
0.7014	Intermediate Similarity	NPD4396	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD3402	Phase 1
0.7012	Intermediate Similarity	NPD7885	Phase 2
0.7012	Intermediate Similarity	NPD7886	Phase 2
0.7009	Intermediate Similarity	NPD5530	Phase 1
0.7008	Intermediate Similarity	NPD8100	Phase 3
0.7005	Intermediate Similarity	NPD5186	Approved
0.7005	Intermediate Similarity	NPD6569	Phase 2
0.7005	Intermediate Similarity	NPD5183	Approved
0.7004	Intermediate Similarity	NPD7859	Phase 2
0.7	Intermediate Similarity	NPD5805	Approved
0.6979	Remote Similarity	NPD7674	Phase 3
0.6979	Remote Similarity	NPD7676	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD7675	Phase 3
0.6979	Remote Similarity	NPD3263	Phase 3
0.6978	Remote Similarity	NPD7453	Approved
0.6978	Remote Similarity	NPD7452	Approved
0.6974	Remote Similarity	NPD5866	Approved
0.697	Remote Similarity	NPD6568	Discontinued
0.6968	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD3825	Phase 3
0.6968	Remote Similarity	NPD6248	Phase 2
0.6968	Remote Similarity	NPD6249	Phase 2
0.6964	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD3947	Discontinued
0.6962	Remote Similarity	NPD8052	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