NPASS Compound

Structure

CID234392 OpenBabel06191716032D 24 29 0 0 1 0 0 0 0 0999 V2000 2.6831 1.3090 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 3.5491 -3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -2.6910 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 5.2812 -3.1910 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 1.8171 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6861 -2.1910 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 2.6831 0.3090 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 4.4152 -1.6910 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 3.5491 -1.1910 0.0000 C 0 0 3 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 6.1472 -2.6910 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 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.6910 0.0000 N 0 0 3 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 7.0983 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0983 -1.3820 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 2 2 0 0 0 0 1 11 1 0 0 0 0 2 16 1 0 0 0 0 3 4 1 0 0 0 0 3 12 1 0 0 0 0 4 20 1 0 0 0 0 5 11 1 0 0 0 0 5 15 1 0 0 0 0 6 12 2 0 0 0 0 6 17 1 0 0 0 0 7 13 2 0 0 0 0 7 18 1 0 0 0 0 8 14 1 0 0 0 0 8 20 1 0 0 0 0 9 22 1 0 0 0 0 9 23 1 0 0 0 0 10 21 1 0 0 0 0 10 24 1 0 0 0 0 11 14 2 0 0 0 0 12 13 1 0 0 0 0 13 15 1 0 0 0 0 14 19 1 0 0 0 0 15 20 1 0 0 0 0 16 19 2 0 0 0 0 16 21 1 0 0 0 0 17 18 2 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	323.12
Volume:	316.18
LogP:	3.297
LogD:	2.829
LogS:	-2.547
# Rotatable Bonds:	0
TPSA:	40.16
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.745
Synthetic Accessibility Score:	3.166
Fsp3:	0.368
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:	-5.21
MDCK Permeability:	3.117930464213714e-05
Pgp-inhibitor:	0.012
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.921
Plasma Protein Binding (PPB):	96.5119857788086%
Volume Distribution (VD):	1.395
Pgp-substrate:	2.7349791526794434%

ADMET: Metabolism

CYP1A2-inhibitor:	0.959
CYP1A2-substrate:	0.205
CYP2C19-inhibitor:	0.969
CYP2C19-substrate:	0.7
CYP2C9-inhibitor:	0.047
CYP2C9-substrate:	0.688
CYP2D6-inhibitor:	0.987
CYP2D6-substrate:	0.929
CYP3A4-inhibitor:	0.956
CYP3A4-substrate:	0.838

ADMET: Excretion

Clearance (CL):	19.776
Half-life (T1/2):	0.233

ADMET: Toxicity

hERG Blockers:	0.174
Human Hepatotoxicity (H-HT):	0.127
Drug-inuced Liver Injury (DILI):	0.246
AMES Toxicity:	0.649
Rat Oral Acute Toxicity:	0.367
Maximum Recommended Daily Dose:	0.928
Skin Sensitization:	0.305
Carcinogencity:	0.957
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.844

Download Data

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

Natural Product: NPC234392

Natural Product ID:	NPC234392
*Common Name:**	UXYJCYXWJGAKQY-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	UXYJCYXWJGAKQY-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H17NO4/c1-2-16-19(24-10-21-16)14-8-20-4-3-12-6-17-18(23-9-22-17)7-13(12)15(20)5-11(1)14/h1-2,6-7,15H,3-5,8-10H2
SMILES:	C1Oc2c(O1)cc1c(c2)CCN2C1Cc1ccc3c(c1C2)OCO3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3343660
PubChem CID:	6770
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
NPO223	Rhaponticum carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15730237]
NPO25345	Corydalis ternata	Species	Papaveraceae	Eukaryota	tubers	n.a.	n.a.	PMID[20594848]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22737858]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23194502]
NPO13962	Corydalis turtschaninovii	Species	Papaveraceae	Eukaryota	n.a.	rhizome	n.a.	PMID[25277281]
NPO13962	Corydalis turtschaninovii	Species	Papaveraceae	Eukaryota	n.a.	tuber	n.a.	PMID[25670016]
NPO41713	Escherichia coli UR6 [genes in the pyrimidine operon(Ptrc-pyrB pyrC pyrAA pyrAB pyrK pyrD pyrF pyrE); genes involved in uridine catabolism (udk udp rihA rihB rihC)]	Strain	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[30189293]
NPO14045	Corydalis decumbens	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31599578]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32058719]
NPO41408	Escherichia coli + Pichia pastoris	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[34663314]
NPO2341	Fibraurea recisa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14045	Corydalis decumbens	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28372	Corydalis pallida	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22043	Hylomecon japonica	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11457	Chelidonium majus	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28698	Corydalis remota	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28372	Corydalis pallida	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14045	Corydalis decumbens	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2341	Fibraurea recisa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28698	Corydalis remota	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22043	Hylomecon japonica	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11457	Chelidonium majus	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28372	Corydalis pallida	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28698	Corydalis remota	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11457	Chelidonium majus	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14045	Corydalis decumbens	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22043	Hylomecon japonica	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2341	Fibraurea recisa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11457	Chelidonium majus	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13962	Corydalis turtschaninovii	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25345	Corydalis ternata	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14045	Corydalis decumbens	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13962	Corydalis turtschaninovii	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28698	Corydalis remota	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28372	Corydalis pallida	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22043	Hylomecon japonica	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14045	Corydalis decumbens	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25345	Corydalis ternata	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	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
Others	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Inhibition	=	4.7	%	PMID[575645]

☑ 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 NPC234392 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	389
0.1-0.2	1828
0.2-0.3	9803
0.3-0.4	8052
0.4-0.5	7398
0.5-0.6	11400
0.6-0.7	2884
0.7-0.8	591
0.8-0.85	209
0.85-0.9	108
0.9-0.95	27
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC31311
0.9796	High Similarity	NPC41178
0.9796	High Similarity	NPC216459
0.9796	High Similarity	NPC138487
0.973	High Similarity	NPC146288
0.966	High Similarity	NPC233029
0.966	High Similarity	NPC210148
0.9388	High Similarity	NPC475959
0.9351	High Similarity	NPC276944
0.9351	High Similarity	NPC232514
0.9351	High Similarity	NPC238530
0.932	High Similarity	NPC476144
0.932	High Similarity	NPC16107
0.932	High Similarity	NPC210437
0.932	High Similarity	NPC106295
0.932	High Similarity	NPC51957
0.9257	High Similarity	NPC7467
0.9216	High Similarity	NPC477080
0.9145	High Similarity	NPC93593
0.9091	High Similarity	NPC111485
0.9048	High Similarity	NPC136860
0.9048	High Similarity	NPC476567
0.9048	High Similarity	NPC128019
0.9032	High Similarity	NPC232924
0.9032	High Similarity	NPC477559
0.9032	High Similarity	NPC266753
0.9032	High Similarity	NPC160298
0.9032	High Similarity	NPC306902
0.902	High Similarity	NPC78733
0.9	High Similarity	NPC2314
0.8987	High Similarity	NPC210918
0.8924	High Similarity	NPC476432
0.8924	High Similarity	NPC24264
0.8912	High Similarity	NPC188163
0.8912	High Similarity	NPC328750
0.8912	High Similarity	NPC213206
0.8912	High Similarity	NPC474915
0.8896	High Similarity	NPC172765
0.8896	High Similarity	NPC5238
0.8896	High Similarity	NPC2413
0.8896	High Similarity	NPC193949
0.8896	High Similarity	NPC295691
0.8896	High Similarity	NPC54379
0.8896	High Similarity	NPC189266
0.8896	High Similarity	NPC278799
0.8896	High Similarity	NPC39701
0.8896	High Similarity	NPC110416
0.8896	High Similarity	NPC249797
0.8896	High Similarity	NPC469817
0.8896	High Similarity	NPC127674
0.8896	High Similarity	NPC204828
0.8896	High Similarity	NPC184026
0.8896	High Similarity	NPC207757
0.8896	High Similarity	NPC276588
0.8889	High Similarity	NPC148898
0.8868	High Similarity	NPC247389
0.8861	High Similarity	NPC225774
0.8861	High Similarity	NPC302527
0.8861	High Similarity	NPC167546
0.8861	High Similarity	NPC16805
0.8844	High Similarity	NPC314682
0.8834	High Similarity	NPC148693
0.8834	High Similarity	NPC118633
0.8834	High Similarity	NPC294790
0.8805	High Similarity	NPC219341
0.879	High Similarity	NPC97072
0.879	High Similarity	NPC215829
0.8774	High Similarity	NPC76079
0.8758	High Similarity	NPC223125
0.8758	High Similarity	NPC75958
0.875	High Similarity	NPC298979
0.8742	High Similarity	NPC168409
0.8726	High Similarity	NPC106786
0.8696	High Similarity	NPC241055
0.8688	High Similarity	NPC86144
0.8688	High Similarity	NPC304659
0.8684	High Similarity	NPC476151
0.8679	High Similarity	NPC189470
0.8679	High Similarity	NPC59567
0.8675	High Similarity	NPC299990
0.8675	High Similarity	NPC73492
0.8645	High Similarity	NPC223124
0.8642	High Similarity	NPC311991
0.8639	High Similarity	NPC7018
0.8636	High Similarity	NPC151895
0.8636	High Similarity	NPC88249
0.8636	High Similarity	NPC192768
0.8636	High Similarity	NPC220858
0.8636	High Similarity	NPC97221
0.8625	High Similarity	NPC247972
0.8589	High Similarity	NPC19520
0.8589	High Similarity	NPC65403
0.8589	High Similarity	NPC149090
0.8581	High Similarity	NPC326316
0.8581	High Similarity	NPC81733
0.858	High Similarity	NPC158148
0.858	High Similarity	NPC58766
0.858	High Similarity	NPC290759
0.858	High Similarity	NPC266176
0.858	High Similarity	NPC82533
0.858	High Similarity	NPC475686
0.8571	High Similarity	NPC103379
0.8571	High Similarity	NPC477565
0.8563	High Similarity	NPC275132
0.8562	High Similarity	NPC320104
0.8553	High Similarity	NPC185838
0.8528	High Similarity	NPC474475
0.8528	High Similarity	NPC6152
0.8521	High Similarity	NPC477259
0.8521	High Similarity	NPC169387
0.8519	High Similarity	NPC100566
0.8519	High Similarity	NPC57812
0.8519	High Similarity	NPC181653
0.8519	High Similarity	NPC190332
0.8519	High Similarity	NPC474324
0.8509	High Similarity	NPC231198
0.8506	High Similarity	NPC147390
0.8506	High Similarity	NPC135538
0.8506	High Similarity	NPC476571
0.8506	High Similarity	NPC246587
0.8506	High Similarity	NPC428
0.8506	High Similarity	NPC24233
0.8494	Intermediate Similarity	NPC320223
0.8494	Intermediate Similarity	NPC114364
0.8485	Intermediate Similarity	NPC128560
0.8485	Intermediate Similarity	NPC229166
0.8485	Intermediate Similarity	NPC199465
0.8481	Intermediate Similarity	NPC247639
0.8481	Intermediate Similarity	NPC25084
0.8476	Intermediate Similarity	NPC225597
0.8476	Intermediate Similarity	NPC477640
0.8476	Intermediate Similarity	NPC470739
0.8466	Intermediate Similarity	NPC475845
0.8457	Intermediate Similarity	NPC13916
0.8457	Intermediate Similarity	NPC264850
0.8452	Intermediate Similarity	NPC219162
0.8452	Intermediate Similarity	NPC92541
0.8443	Intermediate Similarity	NPC244554
0.8442	Intermediate Similarity	NPC321505
0.8442	Intermediate Similarity	NPC179825
0.8442	Intermediate Similarity	NPC191376
0.8431	Intermediate Similarity	NPC130926
0.8428	Intermediate Similarity	NPC476572
0.8421	Intermediate Similarity	NPC281581
0.8418	Intermediate Similarity	NPC244112
0.8418	Intermediate Similarity	NPC325871
0.8418	Intermediate Similarity	NPC80129
0.8418	Intermediate Similarity	NPC99659
0.8418	Intermediate Similarity	NPC187022
0.8415	Intermediate Similarity	NPC474708
0.8415	Intermediate Similarity	NPC152212
0.8395	Intermediate Similarity	NPC24465
0.8393	Intermediate Similarity	NPC179704
0.8387	Intermediate Similarity	NPC37144
0.8387	Intermediate Similarity	NPC130941
0.8387	Intermediate Similarity	NPC59907
0.8383	Intermediate Similarity	NPC15919
0.8373	Intermediate Similarity	NPC187678
0.8372	Intermediate Similarity	NPC473716
0.8372	Intermediate Similarity	NPC475597
0.8344	Intermediate Similarity	NPC476568
0.8344	Intermediate Similarity	NPC476579
0.8343	Intermediate Similarity	NPC248642
0.8333	Intermediate Similarity	NPC27887
0.8333	Intermediate Similarity	NPC126284
0.8324	Intermediate Similarity	NPC24260
0.8323	Intermediate Similarity	NPC144863
0.8323	Intermediate Similarity	NPC474470
0.8323	Intermediate Similarity	NPC253883
0.8323	Intermediate Similarity	NPC95075
0.8323	Intermediate Similarity	NPC90844
0.8312	Intermediate Similarity	NPC145304
0.8294	Intermediate Similarity	NPC156576
0.8284	Intermediate Similarity	NPC32413
0.8284	Intermediate Similarity	NPC474506
0.8274	Intermediate Similarity	NPC23219
0.8272	Intermediate Similarity	NPC24954
0.8263	Intermediate Similarity	NPC304675
0.8263	Intermediate Similarity	NPC477558
0.8261	Intermediate Similarity	NPC216816
0.8253	Intermediate Similarity	NPC198498
0.8253	Intermediate Similarity	NPC276890
0.8253	Intermediate Similarity	NPC10908
0.8253	Intermediate Similarity	NPC63646
0.8253	Intermediate Similarity	NPC317145
0.8253	Intermediate Similarity	NPC227060
0.8253	Intermediate Similarity	NPC76682
0.8253	Intermediate Similarity	NPC115284
0.8253	Intermediate Similarity	NPC317439
0.825	Intermediate Similarity	NPC126519
0.825	Intermediate Similarity	NPC203784
0.825	Intermediate Similarity	NPC170503
0.8239	Intermediate Similarity	NPC477564
0.8239	Intermediate Similarity	NPC2295
0.8235	Intermediate Similarity	NPC116284
0.8231	Intermediate Similarity	NPC160193
0.8229	Intermediate Similarity	NPC477258
0.8225	Intermediate Similarity	NPC258695
0.8225	Intermediate Similarity	NPC470879
0.8225	Intermediate Similarity	NPC267408

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 NPC234392 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	218
0.1-0.2	790
0.2-0.3	1081
0.3-0.4	1907
0.4-0.5	2663
0.5-0.6	1733
0.6-0.7	604
0.7-0.8	136
0.8-0.85	15
0.85-0.9	1
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.932	High Similarity	NPD4584	Approved
0.8912	High Similarity	NPD4664	Clinical (unspecified phase)
0.8733	High Similarity	NPD5084	Clinical (unspecified phase)
0.8418	Intermediate Similarity	NPD7298	Approved
0.8312	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD8252	Approved
0.8253	Intermediate Similarity	NPD8099	Discontinued
0.8253	Intermediate Similarity	NPD8251	Approved
0.8228	Intermediate Similarity	NPD4017	Approved
0.8217	Intermediate Similarity	NPD3639	Approved
0.8217	Intermediate Similarity	NPD3640	Phase 3
0.8217	Intermediate Similarity	NPD3641	Approved
0.8204	Intermediate Similarity	NPD8156	Discontinued
0.8125	Intermediate Similarity	NPD4773	Phase 2
0.8125	Intermediate Similarity	NPD4772	Phase 2
0.8092	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD6030	Approved
0.7987	Intermediate Similarity	NPD6031	Approved
0.7952	Intermediate Similarity	NPD6107	Approved
0.7933	Intermediate Similarity	NPD4420	Approved
0.7927	Intermediate Similarity	NPD6788	Approved
0.7919	Intermediate Similarity	NPD8053	Approved
0.7919	Intermediate Similarity	NPD8054	Approved
0.7892	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD7280	Phase 3
0.7861	Intermediate Similarity	NPD7281	Phase 3
0.7857	Intermediate Similarity	NPD5005	Approved
0.7857	Intermediate Similarity	NPD5006	Approved
0.7815	Intermediate Similarity	NPD5718	Phase 2
0.7811	Intermediate Similarity	NPD4481	Phase 3
0.7799	Intermediate Similarity	NPD3124	Discontinued
0.7798	Intermediate Similarity	NPD4166	Phase 2
0.7763	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD2898	Approved
0.7692	Intermediate Similarity	NPD3051	Approved
0.7692	Intermediate Similarity	NPD4010	Discontinued
0.7674	Intermediate Similarity	NPD5312	Approved
0.7674	Intermediate Similarity	NPD5313	Approved
0.7673	Intermediate Similarity	NPD5241	Discontinued
0.7647	Intermediate Similarity	NPD2970	Approved
0.7647	Intermediate Similarity	NPD2969	Approved
0.7633	Intermediate Similarity	NPD7802	Discontinued
0.7613	Intermediate Similarity	NPD2492	Phase 1
0.7602	Intermediate Similarity	NPD2489	Approved
0.7602	Intermediate Similarity	NPD27	Approved
0.759	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD6071	Discontinued
0.7566	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD6895	Approved
0.7564	Intermediate Similarity	NPD6896	Approved
0.756	Intermediate Similarity	NPD7833	Phase 2
0.756	Intermediate Similarity	NPD7831	Phase 2
0.756	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD2560	Approved
0.7545	Intermediate Similarity	NPD2563	Approved
0.7532	Intermediate Similarity	NPD4474	Approved
0.7532	Intermediate Similarity	NPD4475	Approved
0.7531	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6748	Discontinued
0.7487	Intermediate Similarity	NPD3816	Phase 1
0.7487	Intermediate Similarity	NPD3815	Phase 1
0.7486	Intermediate Similarity	NPD6297	Approved
0.7485	Intermediate Similarity	NPD2978	Approved
0.7485	Intermediate Similarity	NPD2977	Approved
0.7469	Intermediate Similarity	NPD7598	Phase 2
0.7469	Intermediate Similarity	NPD2420	Approved
0.7469	Intermediate Similarity	NPD2421	Approved
0.7457	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD5604	Discontinued
0.744	Intermediate Similarity	NPD5977	Approved
0.744	Intermediate Similarity	NPD5978	Approved
0.7423	Intermediate Similarity	NPD1424	Approved
0.7405	Intermediate Similarity	NPD8095	Phase 1
0.7378	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD3110	Approved
0.7372	Intermediate Similarity	NPD3109	Approved
0.7358	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD5582	Discontinued
0.7333	Intermediate Similarity	NPD4727	Phase 1
0.733	Intermediate Similarity	NPD3885	Approved
0.7329	Intermediate Similarity	NPD5177	Phase 3
0.7321	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD6851	Approved
0.7318	Intermediate Similarity	NPD6853	Approved
0.7301	Intermediate Similarity	NPD3845	Phase 1
0.7293	Intermediate Similarity	NPD7906	Approved
0.7284	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD5754	Discontinued
0.7273	Intermediate Similarity	NPD5457	Discontinued
0.7263	Intermediate Similarity	NPD4577	Approved
0.7263	Intermediate Similarity	NPD7310	Approved
0.7263	Intermediate Similarity	NPD7312	Approved
0.7263	Intermediate Similarity	NPD2968	Approved
0.7263	Intermediate Similarity	NPD2971	Approved
0.7263	Intermediate Similarity	NPD7313	Approved
0.7263	Intermediate Similarity	NPD7311	Approved
0.7263	Intermediate Similarity	NPD4578	Approved
0.7262	Intermediate Similarity	NPD7110	Phase 1
0.7262	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD4055	Discovery
0.7238	Intermediate Similarity	NPD4663	Approved
0.7229	Intermediate Similarity	NPD5976	Discontinued
0.7222	Intermediate Similarity	NPD4237	Approved
0.7222	Intermediate Similarity	NPD4236	Phase 3
0.7222	Intermediate Similarity	NPD6618	Phase 2
0.7222	Intermediate Similarity	NPD7309	Approved
0.7208	Intermediate Similarity	NPD7247	Discontinued
0.72	Intermediate Similarity	NPD6365	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD3349	Phase 2
0.7195	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD7124	Phase 2
0.7188	Intermediate Similarity	NPD4859	Phase 1
0.7186	Intermediate Similarity	NPD4210	Discontinued
0.7182	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD3763	Approved
0.7143	Intermediate Similarity	NPD6688	Approved
0.7143	Intermediate Similarity	NPD6687	Approved
0.7126	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD4498	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD3383	Approved
0.7118	Intermediate Similarity	NPD3384	Approved
0.7118	Intermediate Similarity	NPD3382	Approved
0.7117	Intermediate Similarity	NPD4162	Approved
0.7111	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD7400	Phase 3
0.7104	Intermediate Similarity	NPD7291	Discontinued
0.7097	Intermediate Similarity	NPD6493	Phase 3
0.7093	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD4108	Discontinued
0.7078	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD5677	Discontinued
0.7065	Intermediate Similarity	NPD3408	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD4098	Discontinued
0.703	Intermediate Similarity	NPD5160	Discontinued
0.7027	Intermediate Similarity	NPD2490	Approved
0.7027	Intermediate Similarity	NPD2488	Approved
0.7019	Intermediate Similarity	NPD7119	Phase 2
0.7012	Intermediate Similarity	NPD3060	Approved
0.7011	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7020	Approved
0.7006	Intermediate Similarity	NPD7019	Approved
0.7	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6876	Approved
0.7	Intermediate Similarity	NPD6875	Approved
0.6995	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD3705	Approved
0.6989	Remote Similarity	NPD7296	Approved
0.6987	Remote Similarity	NPD7905	Discontinued
0.6981	Remote Similarity	NPD2674	Phase 3
0.6977	Remote Similarity	NPD5773	Approved
0.6977	Remote Similarity	NPD5772	Approved
0.6975	Remote Similarity	NPD1753	Discontinued
0.6974	Remote Similarity	NPD2668	Approved
0.6974	Remote Similarity	NPD2667	Approved
0.6973	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6090	Discontinued
0.6959	Remote Similarity	NPD5283	Phase 1
0.6957	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD2232	Approved
0.6948	Remote Similarity	NPD2233	Approved
0.6948	Remote Similarity	NPD2230	Approved
0.6944	Remote Similarity	NPD3920	Phase 2
0.6941	Remote Similarity	NPD4005	Discontinued
0.6936	Remote Similarity	NPD2358	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD2974	Approved
0.6931	Remote Similarity	NPD2973	Approved
0.6931	Remote Similarity	NPD2975	Approved
0.6928	Remote Similarity	NPD3692	Discontinued
0.6927	Remote Similarity	NPD5708	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1914	Approved
0.6923	Remote Similarity	NPD2122	Discontinued
0.6923	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7248	Discontinued
0.6919	Remote Similarity	NPD5720	Discontinued
0.6918	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD8318	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD6996	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD1421	Approved
0.6903	Remote Similarity	NPD1420	Approved
0.6898	Remote Similarity	NPD3924	Approved
0.6898	Remote Similarity	NPD3921	Approved
0.6898	Remote Similarity	NPD3922	Approved
0.6898	Remote Similarity	NPD3923	Approved
0.689	Remote Similarity	NPD3656	Approved
0.689	Remote Similarity	NPD1375	Discontinued
0.6889	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD5600	Discontinued
0.6886	Remote Similarity	NPD2120	Phase 2

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