NPASS Compound

Structure

NPC5462 OpenBabel07101718222D 44 46 0 0 0 0 0 0 0 0999 V2000 -5.1962 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 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 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 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 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 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 0.8660 -1.5000 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 -5.1962 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 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 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 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 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 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 0.0000 -0.0000 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 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -4.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 44 1 0 0 0 0 3 4 1 0 0 0 0 3 14 1 0 0 0 0 4 15 1 0 0 0 0 5 9 1 0 0 0 0 5 22 2 0 0 0 0 6 10 2 0 0 0 0 6 22 1 0 0 0 0 7 11 2 0 0 0 0 7 23 1 0 0 0 0 8 12 1 0 0 0 0 8 24 1 0 0 0 0 9 25 2 0 0 0 0 10 25 1 0 0 0 0 11 28 1 0 0 0 0 12 32 1 0 0 0 0 13 16 1 0 0 0 0 13 22 1 0 0 0 0 14 34 1 0 0 0 0 15 36 1 0 0 0 0 16 35 1 0 0 0 0 17 23 1 0 0 0 0 17 27 2 0 0 0 0 18 23 2 0 0 0 0 18 31 1 0 0 0 0 19 24 2 0 0 0 0 19 29 1 0 0 0 0 20 26 2 0 0 0 0 20 30 1 0 0 0 0 21 34 2 3 0 0 0 21 37 1 0 0 0 0 24 26 1 0 0 0 0 25 38 1 0 0 0 0 26 27 1 0 0 0 0 27 33 1 0 0 0 0 28 31 2 0 0 0 0 28 39 1 0 0 0 0 29 30 2 0 0 0 0 29 40 1 0 0 0 0 30 41 1 0 0 0 0 31 44 1 0 0 0 0 32 35 2 3 0 0 0 32 42 1 0 0 0 0 33 36 2 3 0 0 0 33 43 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	605.27
Volume:	622.693
LogP:	1.603
LogD:	2.308
LogS:	-4.235
# Rotatable Bonds:	18
TPSA:	177.45
# H-Bond Aceptor:	11
# H-Bond Donor:	7
# Rings:	3
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.06
Synthetic Accessibility Score:	2.905
Fsp3:	0.303
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.908
MDCK Permeability:	1.2904853065265343e-05
Pgp-inhibitor:	0.988
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.904
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013
Plasma Protein Binding (PPB):	95.27362823486328%
Volume Distribution (VD):	1.015
Pgp-substrate:	1.8359402418136597%

ADMET: Metabolism

CYP1A2-inhibitor:	0.257
CYP1A2-substrate:	0.274
CYP2C19-inhibitor:	0.221
CYP2C19-substrate:	0.051
CYP2C9-inhibitor:	0.58
CYP2C9-substrate:	0.83
CYP2D6-inhibitor:	0.564
CYP2D6-substrate:	0.539
CYP3A4-inhibitor:	0.823
CYP3A4-substrate:	0.11

ADMET: Excretion

Clearance (CL):	7.381
Half-life (T1/2):	0.94

ADMET: Toxicity

hERG Blockers:	0.155
Human Hepatotoxicity (H-HT):	0.351
Drug-inuced Liver Injury (DILI):	0.279
AMES Toxicity:	0.357
Rat Oral Acute Toxicity:	0.174
Maximum Recommended Daily Dose:	0.935
Skin Sensitization:	0.74
Carcinogencity:	0.019
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.015

Download Data

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

Natural Product: NPC5462

Natural Product ID:	NPC5462
*Common Name:**	(E)-2-(4,5-Dihydroxy-2-{3-[(4-Hydroxyphenethyl)Amino]-3-Oxopropyl}Phenyl)-3-(4-Hydroxy-3-Methoxyphenyl)-N-(4-Acetamidobutyl)Acrylamide
IUPAC Name:	(E)-N-(4-acetamidobutyl)-2-[4,5-dihydroxy-2-[3-[2-(4-hydroxyphenyl)ethylamino]-3-oxopropyl]phenyl]-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamide
Synonyms:
Standard InCHIKey:	WZTWRBBZCZLFSH-WPWMEQJKSA-N
Standard InCHI:	InChI=1S/C33H39N3O8/c1-21(37)34-14-3-4-15-36-33(43)27(17-23-7-11-28(39)31(18-23)44-2)26-20-30(41)29(40)19-24(26)8-12-32(42)35-16-13-22-5-9-25(38)10-6-22/h5-7,9-11,17-20,38-41H,3-4,8,12-16H2,1-2H3,(H,34,37)(H,35,42)(H,36,43)/b27-17+
SMILES:	COc1cc(ccc1O)/C=C(c1cc(O)c(cc1CCC(=NCCc1ccc(cc1)O)O)O)/C(=NCCCCN=C(O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2337118
PubChem CID:	71524309
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes

*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]
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

Activity Type	# Activity
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	56500.0	nM	PMID[494634]
NPT1	Others	Radical scavenging activity		IC50	=	65200.0	nM	PMID[494634]

☑ 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 NPC5462 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	231
0.1-0.2	1317
0.2-0.3	6263
0.3-0.4	12135
0.4-0.5	4937
0.5-0.6	9371
0.6-0.7	6361
0.7-0.8	1988
0.8-0.85	51
0.85-0.9	30
0.9-0.95	12
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9577	High Similarity	NPC127402
0.9379	High Similarity	NPC107602
0.9214	High Similarity	NPC222039
0.9214	High Similarity	NPC100478
0.9044	High Similarity	NPC114102
0.8978	High Similarity	NPC214869
0.8971	High Similarity	NPC52029
0.8971	High Similarity	NPC35961
0.8971	High Similarity	NPC195749
0.8929	High Similarity	NPC312770
0.8929	High Similarity	NPC14600
0.8929	High Similarity	NPC41473
0.8929	High Similarity	NPC160607
0.8929	High Similarity	NPC204848
0.8897	High Similarity	NPC155838
0.8865	High Similarity	NPC299583
0.8824	High Similarity	NPC186898
0.8824	High Similarity	NPC251571
0.8732	High Similarity	NPC296898
0.8707	High Similarity	NPC470935
0.8707	High Similarity	NPC471032
0.8686	High Similarity	NPC153990
0.8658	High Similarity	NPC52475
0.8645	High Similarity	NPC90984
0.8613	High Similarity	NPC301713
0.86	High Similarity	NPC275027
0.86	High Similarity	NPC18614
0.8571	High Similarity	NPC179250
0.8571	High Similarity	NPC50380
0.8514	High Similarity	NPC115144
0.8514	High Similarity	NPC277857
0.8511	High Similarity	NPC6854
0.8511	High Similarity	NPC285078
0.8511	High Similarity	NPC313737
0.844	Intermediate Similarity	NPC93882
0.844	Intermediate Similarity	NPC130595
0.8322	Intermediate Similarity	NPC218530
0.8239	Intermediate Similarity	NPC255550
0.8239	Intermediate Similarity	NPC308885
0.8163	Intermediate Similarity	NPC477838
0.8163	Intermediate Similarity	NPC477837
0.8162	Intermediate Similarity	NPC268572
0.8158	Intermediate Similarity	NPC182119
0.8151	Intermediate Similarity	NPC254610
0.8143	Intermediate Similarity	NPC266705
0.8143	Intermediate Similarity	NPC228771
0.8143	Intermediate Similarity	NPC29008
0.8108	Intermediate Similarity	NPC472090
0.8108	Intermediate Similarity	NPC472091
0.8108	Intermediate Similarity	NPC472092
0.8089	Intermediate Similarity	NPC329837
0.8088	Intermediate Similarity	NPC122009
0.8043	Intermediate Similarity	NPC284078
0.8029	Intermediate Similarity	NPC43275
0.8028	Intermediate Similarity	NPC106511
0.8015	Intermediate Similarity	NPC283468
0.8014	Intermediate Similarity	NPC9067
0.8	Intermediate Similarity	NPC228843
0.8	Intermediate Similarity	NPC472088
0.8	Intermediate Similarity	NPC472087
0.7987	Intermediate Similarity	NPC478189
0.7974	Intermediate Similarity	NPC147390
0.7974	Intermediate Similarity	NPC24233
0.7974	Intermediate Similarity	NPC428
0.7974	Intermediate Similarity	NPC153644
0.7974	Intermediate Similarity	NPC135538
0.7974	Intermediate Similarity	NPC246587
0.7974	Intermediate Similarity	NPC476571
0.7972	Intermediate Similarity	NPC277458
0.7972	Intermediate Similarity	NPC307050
0.7971	Intermediate Similarity	NPC117780
0.7971	Intermediate Similarity	NPC242885
0.7971	Intermediate Similarity	NPC232316
0.7971	Intermediate Similarity	NPC227217
0.7971	Intermediate Similarity	NPC56214
0.7971	Intermediate Similarity	NPC95614
0.7971	Intermediate Similarity	NPC165133
0.7963	Intermediate Similarity	NPC66573
0.7956	Intermediate Similarity	NPC470626
0.7943	Intermediate Similarity	NPC95733
0.7943	Intermediate Similarity	NPC62101
0.7933	Intermediate Similarity	NPC472089
0.7919	Intermediate Similarity	NPC77572
0.7908	Intermediate Similarity	NPC191376
0.7908	Intermediate Similarity	NPC321505
0.7908	Intermediate Similarity	NPC179825
0.7905	Intermediate Similarity	NPC77861
0.7899	Intermediate Similarity	NPC281298
0.7899	Intermediate Similarity	NPC310338
0.7895	Intermediate Similarity	NPC318805
0.7895	Intermediate Similarity	NPC41122
0.7891	Intermediate Similarity	NPC311256
0.7891	Intermediate Similarity	NPC471942
0.7887	Intermediate Similarity	NPC29477
0.7887	Intermediate Similarity	NPC148627
0.7883	Intermediate Similarity	NPC293619
0.7877	Intermediate Similarity	NPC14224
0.7877	Intermediate Similarity	NPC161958
0.7875	Intermediate Similarity	NPC60186
0.7872	Intermediate Similarity	NPC140359
0.7872	Intermediate Similarity	NPC471693
0.7872	Intermediate Similarity	NPC211218
0.7872	Intermediate Similarity	NPC13020
0.7866	Intermediate Similarity	NPC231371
0.7862	Intermediate Similarity	NPC126836
0.7857	Intermediate Similarity	NPC38996
0.7857	Intermediate Similarity	NPC160380
0.784	Intermediate Similarity	NPC317272
0.784	Intermediate Similarity	NPC42549
0.784	Intermediate Similarity	NPC268503
0.784	Intermediate Similarity	NPC256012
0.784	Intermediate Similarity	NPC240841
0.784	Intermediate Similarity	NPC250846
0.7838	Intermediate Similarity	NPC313081
0.7838	Intermediate Similarity	NPC200557
0.7838	Intermediate Similarity	NPC93783
0.7838	Intermediate Similarity	NPC69029
0.7838	Intermediate Similarity	NPC108198
0.7838	Intermediate Similarity	NPC158142
0.7838	Intermediate Similarity	NPC10314
0.7838	Intermediate Similarity	NPC294884
0.7834	Intermediate Similarity	NPC475557
0.7832	Intermediate Similarity	NPC17837
0.7832	Intermediate Similarity	NPC304630
0.7831	Intermediate Similarity	NPC32064
0.7824	Intermediate Similarity	NPC124626
0.7815	Intermediate Similarity	NPC470372
0.7806	Intermediate Similarity	NPC103379
0.7806	Intermediate Similarity	NPC477565
0.7805	Intermediate Similarity	NPC476751
0.7801	Intermediate Similarity	NPC471315
0.7801	Intermediate Similarity	NPC471314
0.7801	Intermediate Similarity	NPC30462
0.7801	Intermediate Similarity	NPC85488
0.78	Intermediate Similarity	NPC132804
0.78	Intermediate Similarity	NPC220344
0.78	Intermediate Similarity	NPC243996
0.78	Intermediate Similarity	NPC55947
0.78	Intermediate Similarity	NPC275061
0.7799	Intermediate Similarity	NPC195766
0.7799	Intermediate Similarity	NPC206736
0.7793	Intermediate Similarity	NPC470706
0.7786	Intermediate Similarity	NPC207613
0.7786	Intermediate Similarity	NPC83279
0.7785	Intermediate Similarity	NPC143139
0.7785	Intermediate Similarity	NPC193528
0.7785	Intermediate Similarity	NPC202846
0.7778	Intermediate Similarity	NPC21563
0.7778	Intermediate Similarity	NPC157740
0.7778	Intermediate Similarity	NPC191302
0.7778	Intermediate Similarity	NPC41331
0.7778	Intermediate Similarity	NPC118533
0.7778	Intermediate Similarity	NPC127587
0.7778	Intermediate Similarity	NPC165045
0.7778	Intermediate Similarity	NPC5428
0.7778	Intermediate Similarity	NPC99798
0.7778	Intermediate Similarity	NPC291449
0.7778	Intermediate Similarity	NPC185838
0.777	Intermediate Similarity	NPC125649
0.777	Intermediate Similarity	NPC141023
0.7763	Intermediate Similarity	NPC63628
0.7763	Intermediate Similarity	NPC277784
0.7763	Intermediate Similarity	NPC178466
0.7762	Intermediate Similarity	NPC193544
0.7762	Intermediate Similarity	NPC208950
0.7762	Intermediate Similarity	NPC472093
0.7762	Intermediate Similarity	NPC116907
0.7762	Intermediate Similarity	NPC298757
0.7762	Intermediate Similarity	NPC251855
0.7762	Intermediate Similarity	NPC203133
0.7762	Intermediate Similarity	NPC233410
0.7762	Intermediate Similarity	NPC194519
0.7762	Intermediate Similarity	NPC57490
0.7762	Intermediate Similarity	NPC17943
0.7762	Intermediate Similarity	NPC117214
0.7762	Intermediate Similarity	NPC475169
0.7762	Intermediate Similarity	NPC221077
0.7756	Intermediate Similarity	NPC151895
0.7756	Intermediate Similarity	NPC192768
0.7756	Intermediate Similarity	NPC220858
0.7756	Intermediate Similarity	NPC88249
0.7756	Intermediate Similarity	NPC97221
0.7755	Intermediate Similarity	NPC303144
0.7755	Intermediate Similarity	NPC227002
0.7748	Intermediate Similarity	NPC266197
0.7748	Intermediate Similarity	NPC12668
0.7748	Intermediate Similarity	NPC308768
0.7748	Intermediate Similarity	NPC291101
0.7746	Intermediate Similarity	NPC31344
0.7746	Intermediate Similarity	NPC280704
0.7746	Intermediate Similarity	NPC197757
0.7746	Intermediate Similarity	NPC317769
0.7746	Intermediate Similarity	NPC228922
0.7742	Intermediate Similarity	NPC262297
0.774	Intermediate Similarity	NPC326599
0.774	Intermediate Similarity	NPC476570
0.774	Intermediate Similarity	NPC329595
0.7733	Intermediate Similarity	NPC200935
0.7733	Intermediate Similarity	NPC242715
0.7733	Intermediate Similarity	NPC22902

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 NPC5462 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	162
0.1-0.2	698
0.2-0.3	1093
0.3-0.4	2109
0.4-0.5	2595
0.5-0.6	1575
0.6-0.7	755
0.7-0.8	152
0.8-0.85	10
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.844	Intermediate Similarity	NPD2674	Phase 3
0.8243	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD3145	Approved
0.8239	Intermediate Similarity	NPD3144	Approved
0.8092	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD4005	Discontinued
0.8026	Intermediate Similarity	NPD4123	Phase 3
0.8	Intermediate Similarity	NPD1669	Approved
0.8	Intermediate Similarity	NPD6331	Phase 2
0.7898	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD5111	Phase 2
0.7862	Intermediate Similarity	NPD5109	Approved
0.7862	Intermediate Similarity	NPD5110	Phase 2
0.7829	Intermediate Similarity	NPD5241	Discontinued
0.7817	Intermediate Similarity	NPD2922	Phase 1
0.7815	Intermediate Similarity	NPD3060	Approved
0.7812	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD4675	Approved
0.7771	Intermediate Similarity	NPD4678	Approved
0.7755	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD1558	Phase 1
0.7748	Intermediate Similarity	NPD7153	Discontinued
0.774	Intermediate Similarity	NPD5718	Phase 2
0.7733	Intermediate Similarity	NPD2161	Phase 2
0.7716	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD5772	Approved
0.7625	Intermediate Similarity	NPD5773	Approved
0.7622	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD6895	Approved
0.76	Intermediate Similarity	NPD6896	Approved
0.7593	Intermediate Similarity	NPD4055	Discovery
0.7574	Intermediate Similarity	NPD228	Approved
0.7566	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD4739	Approved
0.7552	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD3027	Phase 3
0.7544	Intermediate Similarity	NPD8053	Approved
0.7544	Intermediate Similarity	NPD8054	Approved
0.7516	Intermediate Similarity	NPD7526	Approved
0.7516	Intermediate Similarity	NPD52	Approved
0.7516	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7833	Phase 2
0.7485	Intermediate Similarity	NPD7831	Phase 2
0.7485	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD2122	Discontinued
0.7466	Intermediate Similarity	NPD6584	Phase 3
0.7464	Intermediate Similarity	NPD5283	Phase 1
0.7451	Intermediate Similarity	NPD1375	Discontinued
0.745	Intermediate Similarity	NPD7477	Discontinued
0.7436	Intermediate Similarity	NPD7124	Phase 2
0.7434	Intermediate Similarity	NPD4108	Discontinued
0.7407	Intermediate Similarity	NPD2977	Approved
0.7407	Intermediate Similarity	NPD2978	Approved
0.74	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD3620	Phase 2
0.7389	Intermediate Similarity	NPD4357	Discontinued
0.7379	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD5604	Discontinued
0.7372	Intermediate Similarity	NPD2219	Phase 1
0.7355	Intermediate Similarity	NPD4236	Phase 3
0.7355	Intermediate Similarity	NPD4237	Approved
0.7355	Intermediate Similarity	NPD4162	Approved
0.7347	Intermediate Similarity	NPD7451	Discontinued
0.7343	Intermediate Similarity	NPD2668	Approved
0.7343	Intermediate Similarity	NPD2667	Approved
0.7329	Intermediate Similarity	NPD5310	Approved
0.7329	Intermediate Similarity	NPD5311	Approved
0.7315	Intermediate Similarity	NPD1024	Discontinued
0.7315	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD2233	Approved
0.731	Intermediate Similarity	NPD2232	Approved
0.731	Intermediate Similarity	NPD2230	Approved
0.7303	Intermediate Similarity	NPD5314	Approved
0.7303	Intermediate Similarity	NPD2157	Approved
0.7297	Intermediate Similarity	NPD1712	Approved
0.729	Intermediate Similarity	NPD2808	Discontinued
0.729	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD6072	Discontinued
0.7284	Intermediate Similarity	NPD7438	Suspended
0.7278	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4093	Discontinued
0.7267	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD4083	Discontinued
0.7261	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD6583	Phase 3
0.726	Intermediate Similarity	NPD6582	Phase 2
0.725	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD5177	Phase 3
0.7235	Intermediate Similarity	NPD7493	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD4584	Approved
0.7219	Intermediate Similarity	NPD27	Approved
0.7219	Intermediate Similarity	NPD2489	Approved
0.7219	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD7906	Approved
0.7216	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7773	Phase 2
0.7209	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD2883	Discontinued
0.7202	Intermediate Similarity	NPD4010	Discontinued
0.7195	Intermediate Similarity	NPD7089	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD4097	Suspended
0.7179	Intermediate Similarity	NPD7037	Approved
0.7178	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD7110	Phase 1
0.7178	Intermediate Similarity	NPD5090	Approved
0.7178	Intermediate Similarity	NPD5089	Approved
0.7174	Intermediate Similarity	NPD3021	Approved
0.7174	Intermediate Similarity	NPD3022	Approved
0.7171	Intermediate Similarity	NPD3062	Approved
0.7171	Intermediate Similarity	NPD2238	Phase 2
0.7171	Intermediate Similarity	NPD3061	Approved
0.7171	Intermediate Similarity	NPD3059	Approved
0.7162	Intermediate Similarity	NPD3055	Approved
0.7162	Intermediate Similarity	NPD3053	Approved
0.7152	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3692	Discontinued
0.7152	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6030	Approved
0.7143	Intermediate Similarity	NPD6111	Discontinued
0.7143	Intermediate Similarity	NPD6031	Approved
0.7143	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7802	Discontinued
0.7135	Intermediate Similarity	NPD8252	Approved
0.7135	Intermediate Similarity	NPD8099	Discontinued
0.7135	Intermediate Similarity	NPD8251	Approved
0.7133	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD7905	Discontinued
0.7113	Intermediate Similarity	NPD709	Approved
0.7105	Intermediate Similarity	NPD839	Approved
0.7105	Intermediate Similarity	NPD840	Approved
0.7101	Intermediate Similarity	NPD6071	Discontinued
0.7101	Intermediate Similarity	NPD3051	Approved
0.7101	Intermediate Similarity	NPD4606	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD8156	Discontinued
0.7078	Intermediate Similarity	NPD1772	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD3778	Approved
0.707	Intermediate Similarity	NPD1044	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6087	Phase 1
0.7059	Intermediate Similarity	NPD2970	Approved
0.7059	Intermediate Similarity	NPD2969	Approved
0.7059	Intermediate Similarity	NPD1613	Approved
0.7059	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD2560	Approved
0.7048	Intermediate Similarity	NPD2563	Approved
0.7044	Intermediate Similarity	NPD2677	Approved
0.7039	Intermediate Similarity	NPD1039	Discontinued
0.703	Intermediate Similarity	NPD7298	Approved
0.7027	Intermediate Similarity	NPD2982	Phase 2
0.7027	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD2983	Phase 2
0.7021	Intermediate Similarity	NPD9379	Approved
0.7021	Intermediate Similarity	NPD9377	Approved
0.7019	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD7447	Phase 1
0.7012	Intermediate Similarity	NPD6875	Approved
0.7012	Intermediate Similarity	NPD6876	Approved
0.7011	Intermediate Similarity	NPD7007	Discovery
0.7007	Intermediate Similarity	NPD3705	Approved
0.7	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD3686	Approved
0.6994	Remote Similarity	NPD3687	Approved
0.6993	Remote Similarity	NPD4475	Approved
0.6993	Remote Similarity	NPD4474	Approved
0.6989	Remote Similarity	NPD7313	Approved
0.6989	Remote Similarity	NPD7310	Approved
0.6989	Remote Similarity	NPD7311	Approved
0.6989	Remote Similarity	NPD7312	Approved
0.6988	Remote Similarity	NPD5929	Approved
0.6988	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD9381	Approved
0.6986	Remote Similarity	NPD9384	Approved
0.6982	Remote Similarity	NPD4666	Phase 3
0.6982	Remote Similarity	NPD6746	Phase 2
0.698	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.697	Remote Similarity	NPD4772	Phase 2
0.697	Remote Similarity	NPD4773	Phase 2
0.6968	Remote Similarity	NPD3052	Approved
0.6968	Remote Similarity	NPD3054	Approved
0.6964	Remote Similarity	NPD8070	Approved
0.6962	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD2981	Phase 2
0.6954	Remote Similarity	NPD4993	Discontinued
0.6954	Remote Similarity	NPD3018	Phase 2
0.6951	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD4017	Approved
0.6949	Remote Similarity	NPD7309	Approved
0.6948	Remote Similarity	NPD6346	Approved
0.6948	Remote Similarity	NPD3109	Approved
0.6948	Remote Similarity	NPD4060	Phase 1

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