NPASS Compound

Structure

CID59567 OpenBabel06191715392D 24 28 0 0 0 0 0 0 0 0999 V2000 -7.0132 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1472 2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1472 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -0.3090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.0132 3.1910 0.0000 O 0 3 0 0 0 0 0 0 0 0 0 0 -7.0132 1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 3 2 0 0 0 0 2 11 1 0 0 0 0 3 16 1 0 0 0 0 4 5 1 0 0 0 0 4 12 1 0 0 0 0 5 20 1 0 0 0 0 6 11 2 0 0 0 0 6 15 1 0 0 0 0 7 12 2 0 0 0 0 7 17 1 0 0 0 0 8 13 2 0 0 0 0 8 18 1 0 0 0 0 9 14 1 0 0 0 0 9 20 2 0 0 0 0 10 23 1 0 0 0 0 10 24 1 0 0 0 0 11 14 1 0 0 0 0 12 13 1 0 0 0 0 13 15 1 0 0 0 0 14 19 2 0 0 0 0 15 20 2 0 0 0 0 16 19 1 0 0 0 0 16 21 2 0 0 0 0 17 18 2 0 0 0 0 17 23 1 0 0 0 0 18 24 1 0 0 0 0 19 22 1 0 0 0 0 M CHG 1 21 1 M END $$$$

Physi-Chem Properties

Molecular Weight:	154.14
Volume:	179.114
LogP:	2.506
LogD:	2.383
LogS:	-2.458
# Rotatable Bonds:	1
TPSA:	17.07
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.567
Synthetic Accessibility Score:	3.289
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.337
MDCK Permeability:	2.4798444428597577e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.17
30% Bioavailability (F30%):	0.271

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.991
Plasma Protein Binding (PPB):	74.06603240966797%
Volume Distribution (VD):	1.252
Pgp-substrate:	19.81146240234375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.19
CYP1A2-substrate:	0.699
CYP2C19-inhibitor:	0.052
CYP2C19-substrate:	0.903
CYP2C9-inhibitor:	0.122
CYP2C9-substrate:	0.921
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.519
CYP3A4-inhibitor:	0.026
CYP3A4-substrate:	0.347

ADMET: Excretion

Clearance (CL):	15.942
Half-life (T1/2):	0.573

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.389
Drug-inuced Liver Injury (DILI):	0.424
AMES Toxicity:	0.066
Rat Oral Acute Toxicity:	0.162
Maximum Recommended Daily Dose:	0.045
Skin Sensitization:	0.208
Carcinogencity:	0.412
Eye Corrosion:	0.703
Eye Irritation:	0.927
Respiratory Toxicity:	0.151

Download Data

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

Natural Product: NPC59567

Natural Product ID:	NPC59567
*Common Name:**	Thalidendine
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	OEGWOBMNQDATKP-UHFFFAOYSA-O
Standard InCHI:	InChI=1S/C19H15NO4/c1-22-19-14-9-20-5-4-12-7-17-18(24-10-23-17)8-13(12)15(20)6-11(14)2-3-16(19)21/h2-3,6-9H,4-5,10H2,1H3/p+1
SMILES:	COC1=C2C=N3=C(C=C2C=CC1=[OH+])c1cc2c(cc1CC3)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1187148
PubChem CID:	3084288
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]
NPO13508	Thalictrum honanenae	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]
NPO22553	Thalictrum fendleri	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]
NPO24476	Phellodendron amurense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22242	Phellodendron chinense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28050	Thalictrum podocarpum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13637	Thalictrum foliolosum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22622	Coptis deltoidea	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13637	Thalictrum foliolosum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24476	Phellodendron amurense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5649	Coptis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22553	Thalictrum fendleri	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28050	Thalictrum podocarpum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22242	Phellodendron chinense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13757	Coptis japonica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22622	Coptis deltoidea	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13508	Thalictrum honanenae	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24476	Phellodendron amurense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13637	Thalictrum foliolosum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5649	Coptis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22242	Phellodendron chinense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22242	Phellodendron chinense	Species	Rutaceae	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]
NPO26538	Phellodendron chinese	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
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]
NPO24476	Phellodendron amurense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5649	Coptis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28050	Thalictrum podocarpum	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]
NPO22242	Phellodendron chinense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22622	Coptis deltoidea	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24476	Phellodendron amurense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13757	Coptis japonica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13637	Thalictrum foliolosum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22553	Thalictrum fendleri	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
IC50	2

Activity Type	# Activity
Individual Protein	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1604	Individual Protein	Cytochrome P450 1B1	Homo sapiens	IC50	=	4100.0	nM	PMID[448506]
NPT992	Organism	Entamoeba histolytica	Entamoeba histolytica	IC50	=	37.35	ug.mL-1	PMID[448505]

☑ 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 NPC59567 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score	Similarity Level	Natural Product ID
0.9801	High Similarity	NPC106786
0.9404	High Similarity	NPC476579
0.9091	High Similarity	NPC223124
0.8961	High Similarity	NPC223125
0.8938	High Similarity	NPC306669
0.8854	High Similarity	NPC41178
0.8854	High Similarity	NPC216459
0.8854	High Similarity	NPC138487
0.8846	High Similarity	NPC210148
0.8846	High Similarity	NPC233029
0.8831	High Similarity	NPC475959
0.8805	High Similarity	NPC111485
0.8797	High Similarity	NPC146288
0.8727	High Similarity	NPC4669
0.8726	High Similarity	NPC476580
0.8704	High Similarity	NPC231198
0.8704	High Similarity	NPC238530
0.8704	High Similarity	NPC232514
0.8704	High Similarity	NPC276944
0.8679	High Similarity	NPC234392
0.8679	High Similarity	NPC31311
0.8608	High Similarity	NPC148898
0.8562	High Similarity	NPC57512
0.8544	High Similarity	NPC8337
0.8544	High Similarity	NPC85747
0.8506	High Similarity	NPC136860
0.8506	High Similarity	NPC128019
0.8506	High Similarity	NPC476567
0.85	High Similarity	NPC78733
0.8477	Intermediate Similarity	NPC7018
0.8457	Intermediate Similarity	NPC477080
0.8415	Intermediate Similarity	NPC476569
0.8408	Intermediate Similarity	NPC476144
0.8408	Intermediate Similarity	NPC210437
0.8408	Intermediate Similarity	NPC16107
0.8408	Intermediate Similarity	NPC51957
0.8408	Intermediate Similarity	NPC106295
0.8405	Intermediate Similarity	NPC97072
0.8405	Intermediate Similarity	NPC215829
0.8405	Intermediate Similarity	NPC226428
0.8393	Intermediate Similarity	NPC2314
0.8385	Intermediate Similarity	NPC93593
0.8377	Intermediate Similarity	NPC474915
0.8377	Intermediate Similarity	NPC328750
0.8377	Intermediate Similarity	NPC213206
0.8377	Intermediate Similarity	NPC188163
0.8365	Intermediate Similarity	NPC151895
0.8365	Intermediate Similarity	NPC97221
0.8365	Intermediate Similarity	NPC192768
0.8365	Intermediate Similarity	NPC220858
0.8365	Intermediate Similarity	NPC88249
0.8364	Intermediate Similarity	NPC3375
0.8364	Intermediate Similarity	NPC255607
0.8354	Intermediate Similarity	NPC7467
0.8344	Intermediate Similarity	NPC118804
0.8323	Intermediate Similarity	NPC82533
0.8323	Intermediate Similarity	NPC266176
0.8323	Intermediate Similarity	NPC290759
0.8323	Intermediate Similarity	NPC158148
0.8312	Intermediate Similarity	NPC314682
0.8294	Intermediate Similarity	NPC474470
0.8293	Intermediate Similarity	NPC160298
0.8293	Intermediate Similarity	NPC232924
0.8293	Intermediate Similarity	NPC266753
0.8293	Intermediate Similarity	NPC306902
0.8293	Intermediate Similarity	NPC477559
0.828	Intermediate Similarity	NPC185838
0.828	Intermediate Similarity	NPC130926
0.8272	Intermediate Similarity	NPC39701
0.8272	Intermediate Similarity	NPC172765
0.8272	Intermediate Similarity	NPC54379
0.8272	Intermediate Similarity	NPC189266
0.8272	Intermediate Similarity	NPC193949
0.8272	Intermediate Similarity	NPC2413
0.8272	Intermediate Similarity	NPC204828
0.8272	Intermediate Similarity	NPC207757
0.8272	Intermediate Similarity	NPC249797
0.8272	Intermediate Similarity	NPC184026
0.8272	Intermediate Similarity	NPC469817
0.8272	Intermediate Similarity	NPC276588
0.8272	Intermediate Similarity	NPC110416
0.8272	Intermediate Similarity	NPC295691
0.8272	Intermediate Similarity	NPC278799
0.8272	Intermediate Similarity	NPC5238
0.8272	Intermediate Similarity	NPC127674
0.8263	Intermediate Similarity	NPC298979
0.8263	Intermediate Similarity	NPC57812
0.8263	Intermediate Similarity	NPC474324
0.8263	Intermediate Similarity	NPC100566
0.825	Intermediate Similarity	NPC274026
0.8239	Intermediate Similarity	NPC147390
0.8239	Intermediate Similarity	NPC476571
0.8239	Intermediate Similarity	NPC246587
0.8239	Intermediate Similarity	NPC428
0.8239	Intermediate Similarity	NPC135538
0.8239	Intermediate Similarity	NPC24233
0.8235	Intermediate Similarity	NPC49353
0.8235	Intermediate Similarity	NPC304675
0.8225	Intermediate Similarity	NPC470739
0.8225	Intermediate Similarity	NPC477640
0.8225	Intermediate Similarity	NPC225597
0.8214	Intermediate Similarity	NPC58766
0.8214	Intermediate Similarity	NPC475845
0.8214	Intermediate Similarity	NPC475686
0.8214	Intermediate Similarity	NPC470324
0.8214	Intermediate Similarity	NPC241055
0.8204	Intermediate Similarity	NPC24264
0.8204	Intermediate Similarity	NPC476432
0.8193	Intermediate Similarity	NPC320104
0.8187	Intermediate Similarity	NPC241704
0.8187	Intermediate Similarity	NPC237044
0.8176	Intermediate Similarity	NPC191376
0.8176	Intermediate Similarity	NPC179825
0.8176	Intermediate Similarity	NPC321505
0.8171	Intermediate Similarity	NPC477259
0.8171	Intermediate Similarity	NPC169387
0.8166	Intermediate Similarity	NPC474708
0.8166	Intermediate Similarity	NPC474475
0.8155	Intermediate Similarity	NPC181653
0.8155	Intermediate Similarity	NPC247389
0.8155	Intermediate Similarity	NPC190332
0.8148	Intermediate Similarity	NPC37272
0.8148	Intermediate Similarity	NPC82285
0.8148	Intermediate Similarity	NPC133011
0.8144	Intermediate Similarity	NPC167546
0.8144	Intermediate Similarity	NPC16805
0.8144	Intermediate Similarity	NPC302527
0.8144	Intermediate Similarity	NPC225774
0.814	Intermediate Similarity	NPC474325
0.811	Intermediate Similarity	NPC147091
0.8095	Intermediate Similarity	NPC219341
0.8092	Intermediate Similarity	NPC27887
0.8092	Intermediate Similarity	NPC474745
0.8092	Intermediate Similarity	NPC32154
0.8079	Intermediate Similarity	NPC160193
0.8065	Intermediate Similarity	NPC252107
0.8063	Intermediate Similarity	NPC476151
0.8059	Intermediate Similarity	NPC75958
0.8056	Intermediate Similarity	NPC24228
0.8049	Intermediate Similarity	NPC76079
0.8047	Intermediate Similarity	NPC210918
0.8036	Intermediate Similarity	NPC168409
0.8036	Intermediate Similarity	NPC39103
0.8036	Intermediate Similarity	NPC2770
0.8036	Intermediate Similarity	NPC247972
0.8035	Intermediate Similarity	NPC477560
0.8035	Intermediate Similarity	NPC118633
0.8035	Intermediate Similarity	NPC148693
0.8035	Intermediate Similarity	NPC320223
0.8035	Intermediate Similarity	NPC114364
0.8035	Intermediate Similarity	NPC294790
0.8023	Intermediate Similarity	NPC128560
0.8023	Intermediate Similarity	NPC199465
0.8023	Intermediate Similarity	NPC229166
0.8012	Intermediate Similarity	NPC67978
0.8012	Intermediate Similarity	NPC59028
0.8012	Intermediate Similarity	NPC303581
0.8012	Intermediate Similarity	NPC92191
0.8	Intermediate Similarity	NPC86469
0.8	Intermediate Similarity	NPC25084
0.8	Intermediate Similarity	NPC247639
0.8	Intermediate Similarity	NPC99078
0.7989	Intermediate Similarity	NPC244554
0.7988	Intermediate Similarity	NPC304659
0.7988	Intermediate Similarity	NPC86144
0.7988	Intermediate Similarity	NPC476002
0.7964	Intermediate Similarity	NPC205167
0.7963	Intermediate Similarity	NPC92541
0.7963	Intermediate Similarity	NPC207824
0.7963	Intermediate Similarity	NPC60538
0.7963	Intermediate Similarity	NPC477565
0.7963	Intermediate Similarity	NPC103379
0.7963	Intermediate Similarity	NPC219162
0.7955	Intermediate Similarity	NPC474746
0.7955	Intermediate Similarity	NPC475981
0.7953	Intermediate Similarity	NPC311991
0.7949	Intermediate Similarity	NPC220923
0.7949	Intermediate Similarity	NPC470707
0.7939	Intermediate Similarity	NPC187022
0.7939	Intermediate Similarity	NPC80129
0.7935	Intermediate Similarity	NPC255817
0.7935	Intermediate Similarity	NPC277042
0.7935	Intermediate Similarity	NPC73883
0.7935	Intermediate Similarity	NPC196609
0.7935	Intermediate Similarity	NPC136330
0.7935	Intermediate Similarity	NPC251454
0.7935	Intermediate Similarity	NPC230698
0.7935	Intermediate Similarity	NPC205178
0.7933	Intermediate Similarity	NPC226708
0.7919	Intermediate Similarity	NPC187678
0.7919	Intermediate Similarity	NPC308267
0.7917	Intermediate Similarity	NPC24954
0.7907	Intermediate Similarity	NPC149090
0.7907	Intermediate Similarity	NPC19520
0.7901	Intermediate Similarity	NPC130941
0.7901	Intermediate Similarity	NPC59907
0.7901	Intermediate Similarity	NPC477258
0.7901	Intermediate Similarity	NPC37144
0.7898	Intermediate Similarity	NPC299990
0.7898	Intermediate Similarity	NPC248642

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 NPC59567 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8408	Intermediate Similarity	NPD4584	Approved
0.8377	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.8302	Intermediate Similarity	NPD3640	Phase 3
0.8302	Intermediate Similarity	NPD3641	Approved
0.8302	Intermediate Similarity	NPD3639	Approved
0.8214	Intermediate Similarity	NPD2898	Approved
0.7988	Intermediate Similarity	NPD4772	Phase 2
0.7988	Intermediate Similarity	NPD4773	Phase 2
0.7939	Intermediate Similarity	NPD7298	Approved
0.7935	Intermediate Similarity	NPD2492	Phase 1
0.7826	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD6107	Approved
0.7778	Intermediate Similarity	NPD4166	Phase 2
0.7764	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD4017	Approved
0.774	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD5978	Approved
0.7738	Intermediate Similarity	NPD5977	Approved
0.7661	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD6030	Approved
0.7636	Intermediate Similarity	NPD6031	Approved
0.7632	Intermediate Similarity	NPD4859	Phase 1
0.7613	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD4481	Phase 3
0.7572	Intermediate Similarity	NPD6071	Discontinued
0.7561	Intermediate Similarity	NPD3124	Discontinued
0.7557	Intermediate Similarity	NPD5312	Approved
0.7557	Intermediate Similarity	NPD5313	Approved
0.7542	Intermediate Similarity	NPD7280	Phase 3
0.7542	Intermediate Similarity	NPD7281	Phase 3
0.7529	Intermediate Similarity	NPD2560	Approved
0.7529	Intermediate Similarity	NPD2563	Approved
0.7527	Intermediate Similarity	NPD4420	Approved
0.7516	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8252	Approved
0.75	Intermediate Similarity	NPD8251	Approved
0.75	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8099	Discontinued
0.7472	Intermediate Similarity	NPD6297	Approved
0.7471	Intermediate Similarity	NPD4010	Discontinued
0.7458	Intermediate Similarity	NPD8156	Discontinued
0.7452	Intermediate Similarity	NPD5718	Phase 2
0.7447	Intermediate Similarity	NPD5457	Discontinued
0.7442	Intermediate Similarity	NPD7831	Phase 2
0.7442	Intermediate Similarity	NPD7833	Phase 2
0.7442	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD5241	Discontinued
0.7429	Intermediate Similarity	NPD2970	Approved
0.7429	Intermediate Similarity	NPD2969	Approved
0.7416	Intermediate Similarity	NPD3885	Approved
0.7403	Intermediate Similarity	NPD8054	Approved
0.7403	Intermediate Similarity	NPD8053	Approved
0.7403	Intermediate Similarity	NPD6618	Phase 2
0.7386	Intermediate Similarity	NPD2489	Approved
0.7386	Intermediate Similarity	NPD27	Approved
0.7371	Intermediate Similarity	NPD3051	Approved
0.7368	Intermediate Similarity	NPD5006	Approved
0.7368	Intermediate Similarity	NPD4585	Approved
0.7368	Intermediate Similarity	NPD5005	Approved
0.7368	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD5089	Approved
0.7353	Intermediate Similarity	NPD5090	Approved
0.7348	Intermediate Similarity	NPD2971	Approved
0.7348	Intermediate Similarity	NPD2968	Approved
0.7314	Intermediate Similarity	NPD7802	Discontinued
0.7308	Intermediate Similarity	NPD6851	Approved
0.7308	Intermediate Similarity	NPD6853	Approved
0.7305	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD2488	Approved
0.7297	Intermediate Similarity	NPD2490	Approved
0.7294	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2977	Approved
0.7267	Intermediate Similarity	NPD2978	Approved
0.7263	Intermediate Similarity	NPD4107	Approved
0.7247	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5604	Discontinued
0.7222	Intermediate Similarity	NPD6895	Approved
0.7222	Intermediate Similarity	NPD6896	Approved
0.7215	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD2974	Approved
0.7196	Intermediate Similarity	NPD2975	Approved
0.7196	Intermediate Similarity	NPD2973	Approved
0.7189	Intermediate Similarity	NPD7291	Discontinued
0.7188	Intermediate Similarity	NPD3057	Approved
0.7184	Intermediate Similarity	NPD6788	Approved
0.7166	Intermediate Similarity	NPD7296	Approved
0.7165	Intermediate Similarity	NPD7607	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7110	Phase 1
0.7143	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD824	Approved
0.7135	Intermediate Similarity	NPD4482	Phase 3
0.7118	Intermediate Similarity	NPD4727	Phase 1
0.7098	Intermediate Similarity	NPD3533	Approved
0.7098	Intermediate Similarity	NPD2972	Approved
0.7091	Intermediate Similarity	NPD3656	Approved
0.7083	Intermediate Similarity	NPD4580	Approved
0.7081	Intermediate Similarity	NPD2674	Phase 3
0.7071	Intermediate Similarity	NPD5676	Approved
0.7065	Intermediate Similarity	NPD7310	Approved
0.7065	Intermediate Similarity	NPD7312	Approved
0.7065	Intermediate Similarity	NPD7313	Approved
0.7065	Intermediate Similarity	NPD7311	Approved
0.7059	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD5582	Discontinued
0.7047	Intermediate Similarity	NPD3452	Approved
0.7047	Intermediate Similarity	NPD3450	Approved
0.7047	Intermediate Similarity	NPD2493	Approved
0.7047	Intermediate Similarity	NPD2494	Approved
0.7041	Intermediate Similarity	NPD2420	Approved
0.7041	Intermediate Similarity	NPD2421	Approved
0.7041	Intermediate Similarity	NPD5297	Approved
0.7037	Intermediate Similarity	NPD3110	Approved
0.7037	Intermediate Similarity	NPD3109	Approved
0.7035	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD7309	Approved
0.7024	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD5564	Approved
0.7011	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD2491	Approved
0.701	Intermediate Similarity	NPD3448	Approved
0.7006	Intermediate Similarity	NPD4237	Approved
0.7006	Intermediate Similarity	NPD5177	Phase 3
0.7006	Intermediate Similarity	NPD4236	Phase 3
0.7005	Intermediate Similarity	NPD3349	Phase 2
0.7005	Intermediate Similarity	NPD7906	Approved
0.7	Intermediate Similarity	NPD1424	Approved
0.6989	Remote Similarity	NPD5087	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD1375	Discontinued
0.6982	Remote Similarity	NPD3845	Phase 1
0.6977	Remote Similarity	NPD4210	Discontinued
0.697	Remote Similarity	NPD4108	Discontinued
0.6966	Remote Similarity	NPD5677	Discontinued
0.6954	Remote Similarity	NPD6873	Phase 2
0.6954	Remote Similarity	NPD6386	Approved
0.6954	Remote Similarity	NPD6385	Approved
0.6951	Remote Similarity	NPD2653	Approved
0.695	Remote Similarity	NPD3815	Phase 1
0.695	Remote Similarity	NPD3816	Phase 1
0.6944	Remote Similarity	NPD6688	Approved
0.6944	Remote Similarity	NPD6687	Approved
0.6939	Remote Similarity	NPD4583	Approved
0.6939	Remote Similarity	NPD4582	Approved
0.6936	Remote Similarity	NPD3866	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD1670	Discontinued
0.6914	Remote Similarity	NPD3145	Approved
0.6914	Remote Similarity	NPD3144	Approved
0.6911	Remote Similarity	NPD6493	Phase 3
0.6905	Remote Similarity	NPD3060	Approved
0.6905	Remote Similarity	NPD4162	Approved
0.6897	Remote Similarity	NPD7028	Phase 2
0.6897	Remote Similarity	NPD6876	Approved
0.6897	Remote Similarity	NPD6875	Approved
0.6888	Remote Similarity	NPD4002	Approved
0.6888	Remote Similarity	NPD4004	Approved
0.6885	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD4578	Approved
0.6882	Remote Similarity	NPD7124	Phase 2
0.6882	Remote Similarity	NPD4577	Approved
0.6882	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD3705	Approved
0.6878	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD3408	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5772	Approved
0.6875	Remote Similarity	NPD5773	Approved
0.6864	Remote Similarity	NPD5754	Discontinued
0.6864	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD3857	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD4663	Approved
0.6859	Remote Similarity	NPD2667	Approved
0.6859	Remote Similarity	NPD2668	Approved
0.6854	Remote Similarity	NPD4055	Discovery
0.6851	Remote Similarity	NPD5242	Approved
0.6836	Remote Similarity	NPD5967	Approved
0.6829	Remote Similarity	NPD8318	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD7549	Discontinued
0.6826	Remote Similarity	NPD2161	Phase 2
0.6826	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD6842	Approved
0.6825	Remote Similarity	NPD6843	Phase 3
0.6825	Remote Similarity	NPD6841	Approved
0.6823	Remote Similarity	NPD4413	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD2122	Discontinued
0.6821	Remote Similarity	NPD1914	Approved
0.6802	Remote Similarity	NPD4739	Approved
0.6798	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD1420	Approved
0.6792	Remote Similarity	NPD1421	Approved
0.6784	Remote Similarity	NPD2120	Phase 2
0.6769	Remote Similarity	NPD8095	Phase 1
0.6768	Remote Similarity	NPD4474	Approved
0.6768	Remote Similarity	NPD4475	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