NPASS Compound

Structure

CID271808 OpenBabel06191716082D 38 39 0 0 0 0 0 0 0 0999 V2000 -10.3923 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.8564 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -18.1865 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -17.3205 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -19.0526 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -16.4545 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2583 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.9904 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.7224 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -19.0526 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -18.1865 2.5000 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 -19.9186 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -19.9186 2.5000 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 -16.4545 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1244 1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -15.5885 1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -20.7846 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -20.7846 3.0000 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 -17.3205 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 1 13 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 3 17 1 0 0 0 0 4 16 1 0 0 0 0 4 18 1 0 0 0 0 5 9 2 0 0 0 0 5 21 1 0 0 0 0 6 10 2 0 0 0 0 6 22 1 0 0 0 0 7 11 1 0 0 0 0 7 21 1 0 0 0 0 8 12 1 0 0 0 0 8 22 1 0 0 0 0 9 23 1 0 0 0 0 10 24 1 0 0 0 0 11 27 1 0 0 0 0 12 28 1 0 0 0 0 13 29 1 0 0 0 0 14 30 1 0 0 0 0 15 29 1 0 0 0 0 16 30 1 0 0 0 0 17 31 1 0 0 0 0 18 32 1 0 0 0 0 19 21 2 0 0 0 0 19 25 1 0 0 0 0 20 22 2 0 0 0 0 20 26 1 0 0 0 0 23 25 2 0 0 0 0 23 33 1 0 0 0 0 24 26 2 0 0 0 0 24 34 1 0 0 0 0 25 35 1 0 0 0 0 26 36 1 0 0 0 0 27 31 2 3 0 0 0 27 37 1 0 0 0 0 28 32 2 3 0 0 0 28 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	530.31
Volume:	551.368
LogP:	-0.712
LogD:	0.478
LogS:	-2.183
# Rotatable Bonds:	21
TPSA:	163.18
# H-Bond Aceptor:	10
# H-Bond Donor:	8
# Rings:	2
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.101
Synthetic Accessibility Score:	2.558
Fsp3:	0.5
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.884
MDCK Permeability:	4.312209057388827e-06
Pgp-inhibitor:	0.2
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.979
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.025
Plasma Protein Binding (PPB):	54.828636169433594%
Volume Distribution (VD):	1.741
Pgp-substrate:	50.410377502441406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.055
CYP2C19-inhibitor:	0.036
CYP2C19-substrate:	0.05
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.069
CYP2D6-inhibitor:	0.03
CYP2D6-substrate:	0.302
CYP3A4-inhibitor:	0.047
CYP3A4-substrate:	0.125

ADMET: Excretion

Clearance (CL):	17.009
Half-life (T1/2):	0.908

ADMET: Toxicity

hERG Blockers:	0.336
Human Hepatotoxicity (H-HT):	0.128
Drug-inuced Liver Injury (DILI):	0.012
AMES Toxicity:	0.327
Rat Oral Acute Toxicity:	0.075
Maximum Recommended Daily Dose:	0.76
Skin Sensitization:	0.971
Carcinogencity:	0.013
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.073

Download Data

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

Natural Product: NPC271808

Natural Product ID:	NPC271808
*Common Name:**	Kukoamine A
IUPAC Name:	3-(3,4-dihydroxyphenyl)-N-[3-[4-[3-[3-(3,4-dihydroxyphenyl)propanoylamino]propylamino]butylamino]propyl]propanamide
Synonyms:	Kukoamine A
Standard InCHIKey:	IOLDDENZPBFBHV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C28H42N4O6/c33-23-9-5-21(19-25(23)35)7-11-27(37)31-17-3-15-29-13-1-2-14-30-16-4-18-32-28(38)12-8-22-6-10-24(34)26(36)20-22/h5-6,9-10,19-20,29-30,33-36H,1-4,7-8,11-18H2,(H,31,37)(H,32,38)
SMILES:	C(CCNCCCN=C(CCc1ccc(c(c1)O)O)O)CNCCCN=C(CCc1ccc(c(c1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL79129
PubChem CID:	5318865
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0001286] Benzenediols [CHEMONTID:0000135] Catechols

*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
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	fruits	n.a.	n.a.	PMID[12467621]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	root	n.a.	PMID[16212233]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	root bark	n.a.	n.a.	PMID[23282106]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	Root Bark	n.a.	n.a.	PMID[26982999]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	fruits	n.a.	n.a.	PMID[9090870]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8251	Cortex lycii radicis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2
Ki	3
Others	5

Activity Type	# Activity
Individual Protein	4
NON-MOLECULAR	2
Organism	1
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT5632	Individual Protein	Trypanothione reductase	Crithidia fasciculata	Ki	=	1800.0	nM	PMID[554383]
NPT5632	Individual Protein	Trypanothione reductase	Crithidia fasciculata	Ki	=	13000.0	nM	PMID[554383]
NPT991	Individual Protein	Trypanothione reductase	Trypanosoma cruzi	Ki	=	76.0	nM	PMID[554381]
NPT991	Individual Protein	Trypanothione reductase	Trypanosoma cruzi	Inhibition constant	=	0.59	n.a.	PMID[554382]
NPT27	Others	Unspecified		IC50	=	3500.0	nM	PMID[554384]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	100.0	%	PMID[554384]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	96.0	%	PMID[554384]
NPT35	Others	n.a.		Inhibition	=	72.0	%	PMID[554384]
NPT2	Others	Unspecified		IC50	=	9500.0	nM	PMID[554384]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	43.0	%	PMID[554384]

☑ 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 NPC271808 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	218
0.1-0.2	1431
0.2-0.3	9902
0.3-0.4	8518
0.4-0.5	10537
0.5-0.6	9047
0.6-0.7	2760
0.7-0.8	265
0.8-0.85	14
0.85-0.9	4
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8862	High Similarity	NPC268572
0.8629	High Similarity	NPC122009
0.8548	High Similarity	NPC283468
0.8385	Intermediate Similarity	NPC318965
0.8333	Intermediate Similarity	NPC85276
0.8281	Intermediate Similarity	NPC284078
0.816	Intermediate Similarity	NPC142599
0.8145	Intermediate Similarity	NPC146422
0.8125	Intermediate Similarity	NPC283760
0.8088	Intermediate Similarity	NPC267237
0.8074	Intermediate Similarity	NPC114102
0.8	Intermediate Similarity	NPC168861
0.8	Intermediate Similarity	NPC323123
0.7985	Intermediate Similarity	NPC186898
0.7985	Intermediate Similarity	NPC251571
0.7929	Intermediate Similarity	NPC211468
0.7929	Intermediate Similarity	NPC219233
0.7929	Intermediate Similarity	NPC170170
0.7923	Intermediate Similarity	NPC252817
0.7883	Intermediate Similarity	NPC214869
0.7868	Intermediate Similarity	NPC52029
0.7868	Intermediate Similarity	NPC35961
0.7868	Intermediate Similarity	NPC195749
0.7857	Intermediate Similarity	NPC214988
0.7852	Intermediate Similarity	NPC477839
0.7829	Intermediate Similarity	NPC38458
0.7829	Intermediate Similarity	NPC311737
0.7823	Intermediate Similarity	NPC24101
0.7823	Intermediate Similarity	NPC96224
0.7812	Intermediate Similarity	NPC317254
0.781	Intermediate Similarity	NPC326966
0.7794	Intermediate Similarity	NPC155838
0.7787	Intermediate Similarity	NPC471511
0.7778	Intermediate Similarity	NPC323775
0.7778	Intermediate Similarity	NPC236347
0.776	Intermediate Similarity	NPC258056
0.776	Intermediate Similarity	NPC254833
0.776	Intermediate Similarity	NPC228343
0.7752	Intermediate Similarity	NPC82963
0.7714	Intermediate Similarity	NPC6913
0.7705	Intermediate Similarity	NPC196479
0.7698	Intermediate Similarity	NPC147634
0.7698	Intermediate Similarity	NPC474149
0.7698	Intermediate Similarity	NPC226401
0.7698	Intermediate Similarity	NPC174096
0.7698	Intermediate Similarity	NPC79793
0.7698	Intermediate Similarity	NPC120982
0.7686	Intermediate Similarity	NPC223393
0.768	Intermediate Similarity	NPC153690
0.7664	Intermediate Similarity	NPC325651
0.7661	Intermediate Similarity	NPC231705
0.7652	Intermediate Similarity	NPC169207
0.7652	Intermediate Similarity	NPC115627
0.7652	Intermediate Similarity	NPC118522
0.7638	Intermediate Similarity	NPC179002
0.7638	Intermediate Similarity	NPC257430
0.7638	Intermediate Similarity	NPC297657
0.7638	Intermediate Similarity	NPC187583
0.7626	Intermediate Similarity	NPC302171
0.7626	Intermediate Similarity	NPC33338
0.7626	Intermediate Similarity	NPC300020
0.7619	Intermediate Similarity	NPC71266
0.7619	Intermediate Similarity	NPC55617
0.7619	Intermediate Similarity	NPC62258
0.7606	Intermediate Similarity	NPC14600
0.7606	Intermediate Similarity	NPC160607
0.7606	Intermediate Similarity	NPC204848
0.7606	Intermediate Similarity	NPC41473
0.7606	Intermediate Similarity	NPC312770
0.7603	Intermediate Similarity	NPC5462
0.76	Intermediate Similarity	NPC142297
0.7591	Intermediate Similarity	NPC153990
0.7581	Intermediate Similarity	NPC239291
0.7571	Intermediate Similarity	NPC6854
0.7571	Intermediate Similarity	NPC313737
0.7571	Intermediate Similarity	NPC285078
0.7552	Intermediate Similarity	NPC299583
0.7521	Intermediate Similarity	NPC109955
0.7521	Intermediate Similarity	NPC107619
0.7518	Intermediate Similarity	NPC301713
0.7517	Intermediate Similarity	NPC222039
0.7517	Intermediate Similarity	NPC100478
0.75	Intermediate Similarity	NPC130595
0.75	Intermediate Similarity	NPC93882
0.7462	Intermediate Similarity	NPC120280
0.7462	Intermediate Similarity	NPC118202
0.7431	Intermediate Similarity	NPC296898
0.7426	Intermediate Similarity	NPC140359
0.7426	Intermediate Similarity	NPC13020
0.7419	Intermediate Similarity	NPC178902
0.7419	Intermediate Similarity	NPC68055
0.7405	Intermediate Similarity	NPC37302
0.7402	Intermediate Similarity	NPC233835
0.7394	Intermediate Similarity	NPC218530
0.7381	Intermediate Similarity	NPC477814
0.7364	Intermediate Similarity	NPC268032
0.7348	Intermediate Similarity	NPC61062
0.7348	Intermediate Similarity	NPC277394
0.7348	Intermediate Similarity	NPC299252
0.7339	Intermediate Similarity	NPC110764
0.7338	Intermediate Similarity	NPC161593
0.7338	Intermediate Similarity	NPC145888
0.7338	Intermediate Similarity	NPC16031
0.7329	Intermediate Similarity	NPC323204
0.7329	Intermediate Similarity	NPC326241
0.7317	Intermediate Similarity	NPC125732
0.7313	Intermediate Similarity	NPC217174
0.731	Intermediate Similarity	NPC476989
0.7308	Intermediate Similarity	NPC51698
0.7305	Intermediate Similarity	NPC255550
0.7305	Intermediate Similarity	NPC308885
0.7303	Intermediate Similarity	NPC76213
0.7303	Intermediate Similarity	NPC277669
0.7303	Intermediate Similarity	NPC127402
0.7299	Intermediate Similarity	NPC318777
0.7293	Intermediate Similarity	NPC175799
0.7293	Intermediate Similarity	NPC610
0.7293	Intermediate Similarity	NPC145023
0.7293	Intermediate Similarity	NPC137096
0.7293	Intermediate Similarity	NPC200988
0.7273	Intermediate Similarity	NPC213
0.7273	Intermediate Similarity	NPC10286
0.7267	Intermediate Similarity	NPC115144
0.7267	Intermediate Similarity	NPC277857
0.7266	Intermediate Similarity	NPC58427
0.7266	Intermediate Similarity	NPC105727
0.7266	Intermediate Similarity	NPC34864
0.7266	Intermediate Similarity	NPC114392
0.726	Intermediate Similarity	NPC477838
0.726	Intermediate Similarity	NPC477837
0.7259	Intermediate Similarity	NPC475245
0.7255	Intermediate Similarity	NPC275027
0.7254	Intermediate Similarity	NPC244866
0.7254	Intermediate Similarity	NPC149379
0.7252	Intermediate Similarity	NPC471485
0.7241	Intermediate Similarity	NPC48202
0.7239	Intermediate Similarity	NPC144343
0.7239	Intermediate Similarity	NPC470626
0.7239	Intermediate Similarity	NPC86198
0.7231	Intermediate Similarity	NPC280382
0.7226	Intermediate Similarity	NPC298486
0.7226	Intermediate Similarity	NPC475544
0.7222	Intermediate Similarity	NPC12278
0.7222	Intermediate Similarity	NPC64205
0.7222	Intermediate Similarity	NPC120719
0.7213	Intermediate Similarity	NPC274678
0.7213	Intermediate Similarity	NPC107522
0.7213	Intermediate Similarity	NPC32714
0.7208	Intermediate Similarity	NPC477564
0.7208	Intermediate Similarity	NPC2295
0.7206	Intermediate Similarity	NPC24125
0.7188	Intermediate Similarity	NPC176527
0.7185	Intermediate Similarity	NPC263386
0.7185	Intermediate Similarity	NPC141791
0.7185	Intermediate Similarity	NPC70084
0.7185	Intermediate Similarity	NPC470214
0.7185	Intermediate Similarity	NPC470215
0.7185	Intermediate Similarity	NPC109371
0.7185	Intermediate Similarity	NPC43275
0.7183	Intermediate Similarity	NPC473724
0.7177	Intermediate Similarity	NPC131587
0.7171	Intermediate Similarity	NPC60538
0.7171	Intermediate Similarity	NPC207824
0.7164	Intermediate Similarity	NPC277588
0.7164	Intermediate Similarity	NPC278652
0.7164	Intermediate Similarity	NPC86947
0.7164	Intermediate Similarity	NPC293619
0.7161	Intermediate Similarity	NPC107602
0.7154	Intermediate Similarity	NPC33168
0.7153	Intermediate Similarity	NPC27581
0.7153	Intermediate Similarity	NPC237667
0.7133	Intermediate Similarity	NPC307123
0.7133	Intermediate Similarity	NPC88667
0.7133	Intermediate Similarity	NPC97870
0.7133	Intermediate Similarity	NPC247018
0.7132	Intermediate Similarity	NPC95614
0.7132	Intermediate Similarity	NPC265454
0.7132	Intermediate Similarity	NPC56214
0.7132	Intermediate Similarity	NPC34634
0.7132	Intermediate Similarity	NPC165133
0.7132	Intermediate Similarity	NPC242885
0.7132	Intermediate Similarity	NPC227217
0.7132	Intermediate Similarity	NPC232316
0.7132	Intermediate Similarity	NPC117780
0.7131	Intermediate Similarity	NPC151715
0.7131	Intermediate Similarity	NPC76938
0.7123	Intermediate Similarity	NPC471283
0.7123	Intermediate Similarity	NPC193528
0.7123	Intermediate Similarity	NPC197045
0.712	Intermediate Similarity	NPC155847
0.712	Intermediate Similarity	NPC289381
0.7115	Intermediate Similarity	NPC469243
0.7114	Intermediate Similarity	NPC470472
0.7113	Intermediate Similarity	NPC474091
0.7105	Intermediate Similarity	NPC471032
0.7105	Intermediate Similarity	NPC470935
0.7101	Intermediate Similarity	NPC471314
0.7101	Intermediate Similarity	NPC471315
0.7099	Intermediate Similarity	NPC163674
0.7092	Intermediate Similarity	NPC191302

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 NPC271808 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	132
0.1-0.2	559
0.2-0.3	1136
0.3-0.4	1856
0.4-0.5	3135
0.5-0.6	1740
0.6-0.7	498
0.7-0.8	83
0.8-0.85	8
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.904	High Similarity	NPD5311	Approved
0.904	High Similarity	NPD5310	Approved
0.8672	High Similarity	NPD3053	Approved
0.8672	High Similarity	NPD3055	Approved
0.8507	High Similarity	NPD5314	Approved
0.8358	Intermediate Similarity	NPD3059	Approved
0.8358	Intermediate Similarity	NPD3062	Approved
0.8358	Intermediate Similarity	NPD3061	Approved
0.8346	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.8145	Intermediate Similarity	NPD9377	Approved
0.8145	Intermediate Similarity	NPD9379	Approved
0.8045	Intermediate Similarity	NPD7451	Discontinued
0.803	Intermediate Similarity	NPD9634	Clinical (unspecified phase)
0.8015	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD597	Approved
0.781	Intermediate Similarity	NPD598	Approved
0.781	Intermediate Similarity	NPD601	Approved
0.7801	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD9619	Approved
0.7778	Intermediate Similarity	NPD9621	Approved
0.7778	Intermediate Similarity	NPD9620	Approved
0.776	Intermediate Similarity	NPD3022	Approved
0.776	Intermediate Similarity	NPD3021	Approved
0.7754	Intermediate Similarity	NPD1136	Approved
0.7754	Intermediate Similarity	NPD1132	Approved
0.7754	Intermediate Similarity	NPD1130	Approved
0.7714	Intermediate Similarity	NPD823	Approved
0.7714	Intermediate Similarity	NPD817	Approved
0.7652	Intermediate Similarity	NPD9384	Approved
0.7652	Intermediate Similarity	NPD9381	Approved
0.7639	Intermediate Similarity	NPD3060	Approved
0.7612	Intermediate Similarity	NPD2562	Approved
0.7612	Intermediate Similarity	NPD2561	Approved
0.7603	Intermediate Similarity	NPD3845	Phase 1
0.7603	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD6346	Approved
0.75	Intermediate Similarity	NPD6809	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2674	Phase 3
0.75	Intermediate Similarity	NPD6405	Approved
0.75	Intermediate Similarity	NPD6407	Approved
0.7483	Intermediate Similarity	NPD6867	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD6866	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD7066	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD2568	Approved
0.7444	Intermediate Similarity	NPD4093	Discontinued
0.7431	Intermediate Similarity	NPD7450	Phase 2
0.7426	Intermediate Similarity	NPD9622	Approved
0.7424	Intermediate Similarity	NPD16	Approved
0.7424	Intermediate Similarity	NPD856	Approved
0.7422	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD3555	Approved
0.7413	Intermediate Similarity	NPD3552	Approved
0.7413	Intermediate Similarity	NPD3554	Approved
0.7413	Intermediate Similarity	NPD3553	Approved
0.7397	Intermediate Similarity	NPD4162	Approved
0.7385	Intermediate Similarity	NPD2228	Approved
0.7385	Intermediate Similarity	NPD2234	Approved
0.7385	Intermediate Similarity	NPD2229	Approved
0.7383	Intermediate Similarity	NPD3985	Discontinued
0.7368	Intermediate Similarity	NPD316	Approved
0.7351	Intermediate Similarity	NPD1973	Approved
0.7351	Intermediate Similarity	NPD1969	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD1972	Approved
0.7344	Intermediate Similarity	NPD1792	Phase 2
0.7338	Intermediate Similarity	NPD9569	Approved
0.7333	Intermediate Similarity	NPD7303	Discontinued
0.7329	Intermediate Similarity	NPD7153	Discontinued
0.7315	Intermediate Similarity	NPD6087	Phase 1
0.7305	Intermediate Similarity	NPD3145	Approved
0.7305	Intermediate Similarity	NPD3144	Approved
0.7293	Intermediate Similarity	NPD9615	Approved
0.7293	Intermediate Similarity	NPD9613	Approved
0.7293	Intermediate Similarity	NPD9616	Approved
0.726	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD1445	Approved
0.7244	Intermediate Similarity	NPD1444	Approved
0.7234	Intermediate Similarity	NPD3136	Phase 2
0.7226	Intermediate Similarity	NPD2977	Approved
0.7226	Intermediate Similarity	NPD2978	Approved
0.7222	Intermediate Similarity	NPD9608	Approved
0.7222	Intermediate Similarity	NPD9610	Approved
0.7219	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD3421	Phase 3
0.7188	Intermediate Similarity	NPD4083	Discontinued
0.7164	Intermediate Similarity	NPD318	Approved
0.7164	Intermediate Similarity	NPD317	Approved
0.7153	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3645	Discontinued
0.7133	Intermediate Similarity	NPD1423	Approved
0.7133	Intermediate Similarity	NPD259	Phase 1
0.7132	Intermediate Similarity	NPD1751	Approved
0.7132	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD2933	Approved
0.7131	Intermediate Similarity	NPD2934	Approved
0.7113	Intermediate Similarity	NPD9537	Phase 1
0.7113	Intermediate Similarity	NPD9536	Phase 1
0.7111	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD5304	Approved
0.7111	Intermediate Similarity	NPD5303	Approved
0.7105	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD52	Approved
0.7105	Intermediate Similarity	NPD7526	Approved
0.7083	Intermediate Similarity	NPD1558	Phase 1
0.708	Intermediate Similarity	NPD1983	Approved
0.708	Intermediate Similarity	NPD1981	Approved
0.708	Intermediate Similarity	NPD1980	Approved
0.7077	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD2860	Approved
0.7073	Intermediate Similarity	NPD2859	Approved
0.7067	Intermediate Similarity	NPD302	Approved
0.7063	Intermediate Similarity	NPD5718	Phase 2
0.7051	Intermediate Similarity	NPD7495	Discontinued
0.7051	Intermediate Similarity	NPD8019	Approved
0.7047	Intermediate Similarity	NPD2209	Approved
0.7047	Intermediate Similarity	NPD2211	Approved
0.7042	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD3020	Approved
0.7034	Intermediate Similarity	NPD555	Phase 2
0.7027	Intermediate Similarity	NPD7978	Discontinued
0.7021	Intermediate Similarity	NPD257	Approved
0.7021	Intermediate Similarity	NPD258	Approved
0.7	Intermediate Similarity	NPD2922	Phase 1
0.6993	Remote Similarity	NPD2372	Approved
0.6986	Remote Similarity	NPD3052	Approved
0.6986	Remote Similarity	NPD3054	Approved
0.698	Remote Similarity	NPD1044	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD5137	Approved
0.6974	Remote Similarity	NPD2420	Approved
0.6974	Remote Similarity	NPD2421	Approved
0.6957	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.695	Remote Similarity	NPD1135	Approved
0.695	Remote Similarity	NPD1131	Approved
0.695	Remote Similarity	NPD1129	Approved
0.695	Remote Similarity	NPD1133	Approved
0.695	Remote Similarity	NPD1134	Approved
0.6948	Remote Similarity	NPD7523	Phase 3
0.6943	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD5722	Discontinued
0.694	Remote Similarity	NPD1791	Approved
0.694	Remote Similarity	NPD9614	Approved
0.694	Remote Similarity	NPD1793	Approved
0.694	Remote Similarity	NPD9618	Approved
0.6939	Remote Similarity	NPD6896	Approved
0.6939	Remote Similarity	NPD6895	Approved
0.6933	Remote Similarity	NPD2460	Phase 3
0.6933	Remote Similarity	NPD2459	Approved
0.6933	Remote Similarity	NPD2458	Approved
0.6929	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD4659	Approved
0.6929	Remote Similarity	NPD1669	Approved
0.6928	Remote Similarity	NPD4123	Phase 3
0.6901	Remote Similarity	NPD2194	Approved
0.6901	Remote Similarity	NPD2195	Approved
0.6901	Remote Similarity	NPD859	Approved
0.6901	Remote Similarity	NPD858	Approved
0.6901	Remote Similarity	NPD599	Approved
0.6901	Remote Similarity	NPD602	Approved
0.6899	Remote Similarity	NPD5773	Approved
0.6899	Remote Similarity	NPD5772	Approved
0.6897	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6331	Phase 2
0.6875	Remote Similarity	NPD5163	Phase 2
0.6875	Remote Similarity	NPD5156	Approved
0.6875	Remote Similarity	NPD5155	Approved
0.6871	Remote Similarity	NPD2653	Approved
0.6867	Remote Similarity	NPD4256	Phase 2
0.6867	Remote Similarity	NPD4257	Approved
0.6863	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD3455	Phase 2
0.6857	Remote Similarity	NPD2231	Phase 2
0.6857	Remote Similarity	NPD2235	Phase 2
0.6853	Remote Similarity	NPD3635	Approved
0.6853	Remote Similarity	NPD3637	Approved
0.6853	Remote Similarity	NPD3636	Approved
0.6849	Remote Similarity	NPD826	Approved
0.6849	Remote Similarity	NPD825	Approved
0.6846	Remote Similarity	NPD9570	Approved
0.6842	Remote Similarity	NPD228	Approved
0.6842	Remote Similarity	NPD8131	Suspended
0.6842	Remote Similarity	NPD2677	Approved
0.6831	Remote Similarity	NPD4103	Phase 2
0.6831	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD3638	Discontinued
0.6818	Remote Similarity	NPD6419	Discontinued
0.6818	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD2874	Phase 2
0.6818	Remote Similarity	NPD3536	Discontinued
0.6806	Remote Similarity	NPD2606	Approved
0.6806	Remote Similarity	NPD3594	Approved
0.6806	Remote Similarity	NPD2605	Approved
0.6806	Remote Similarity	NPD3595	Approved
0.6803	Remote Similarity	NPD275	Approved
0.6803	Remote Similarity	NPD274	Approved
0.6797	Remote Similarity	NPD7554	Discontinued
0.6783	Remote Similarity	NPD6584	Phase 3
0.6781	Remote Similarity	NPD3531	Approved
0.6781	Remote Similarity	NPD3530	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