NPASS Compound

Structure

CID83511 OpenBabel06191715422D 25 30 0 0 0 0 0 0 0 0999 V2000 -0.0000 3.0000 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 0.8660 -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 0.8660 1.5000 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 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0029 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 2.5000 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 -0.0000 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 0.8660 0.5000 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 3.4641 -1.0000 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 -1.7321 2.0000 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 -0.0000 -0.0000 0.0000 N 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 -2.6831 3.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 1.6910 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 14 1 0 0 0 0 3 4 1 0 0 0 0 3 10 1 0 0 0 0 4 20 1 0 0 0 0 5 11 1 0 0 0 0 5 13 2 0 0 0 0 6 10 2 0 0 0 0 6 15 1 0 0 0 0 7 12 2 0 0 0 0 7 16 1 0 0 0 0 8 23 1 0 0 0 0 8 24 1 0 0 0 0 9 22 1 0 0 0 0 9 25 1 0 0 0 0 10 12 1 0 0 0 0 11 17 2 0 0 0 0 12 13 1 0 0 0 0 13 20 1 0 0 0 0 14 18 2 0 0 0 0 14 22 1 0 0 0 0 15 16 2 0 0 0 0 15 23 1 0 0 0 0 16 24 1 0 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 18 25 1 0 0 0 0 19 20 1 0 0 0 0 19 21 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	335.08
Volume:	319.698
LogP:	4.066
LogD:	3.274
LogS:	-6.652
# Rotatable Bonds:	0
TPSA:	58.92
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.632
Synthetic Accessibility Score:	2.772
Fsp3:	0.211
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.021
MDCK Permeability:	3.547200685716234e-05
Pgp-inhibitor:	0.043
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.398
Plasma Protein Binding (PPB):	97.61888885498047%
Volume Distribution (VD):	0.65
Pgp-substrate:	1.381550669670105%

ADMET: Metabolism

CYP1A2-inhibitor:	0.988
CYP1A2-substrate:	0.155
CYP2C19-inhibitor:	0.969
CYP2C19-substrate:	0.08
CYP2C9-inhibitor:	0.881
CYP2C9-substrate:	0.923
CYP2D6-inhibitor:	0.928
CYP2D6-substrate:	0.933
CYP3A4-inhibitor:	0.959
CYP3A4-substrate:	0.13

ADMET: Excretion

Clearance (CL):	14.795
Half-life (T1/2):	0.142

ADMET: Toxicity

hERG Blockers:	0.049
Human Hepatotoxicity (H-HT):	0.088
Drug-inuced Liver Injury (DILI):	0.574
AMES Toxicity:	0.89
Rat Oral Acute Toxicity:	0.049
Maximum Recommended Daily Dose:	0.919
Skin Sensitization:	0.626
Carcinogencity:	0.968
Eye Corrosion:	0.003
Eye Irritation:	0.127
Respiratory Toxicity:	0.807

Download Data

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

Natural Product: NPC83511

Natural Product ID:	NPC83511
*Common Name:**	UCAFJBSQKXVPDX-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	UCAFJBSQKXVPDX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H13NO5/c21-19-17-11(1-2-14-18(17)25-9-22-14)5-13-12-7-16-15(23-8-24-16)6-10(12)3-4-20(13)19/h1-2,5-7H,3-4,8-9H2
SMILES:	O=c1c2c(ccc3c2OCO3)cc2n1CCc1c2cc2c(c1)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3612189
PubChem CID:	5245667
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002566] Isoquinolines and derivatives [CHEMONTID:0002054] Isoquinolones 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]
NPO25345	Corydalis ternata	Species	Papaveraceae	Eukaryota	tubers	n.a.	n.a.	PMID[20594848]
NPO13757	Coptis japonica	Species	Ranunculaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[21401114]
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]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32058719]
NPO5649	Coptis chinensis	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]
NPO2341	Fibraurea recisa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22622	Coptis deltoidea	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2341	Fibraurea recisa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5649	Coptis chinensis	Species	Ranunculaceae	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]
NPO5649	Coptis chinensis	Species	Ranunculaceae	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]
NPO13962	Corydalis turtschaninovii	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2341	Fibraurea recisa	Species	Menispermaceae	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]
NPO13757	Coptis japonica	Species	Ranunculaceae	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]
NPO22622	Coptis deltoidea	Species	Ranunculaceae	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]
NPO13962	Corydalis turtschaninovii	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22622	Coptis deltoidea	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO827	Corydalis yanhusuo	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]
NPO13757	Coptis japonica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5649	Coptis chinensis	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]

☑ 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
EC50	2
Others	2

Activity Type	# Activity
Individual Protein	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3972	Individual Protein	X-box-binding protein 1	Rattus norvegicus	EC50	=	80.0	nM	PMID[545848]
NPT3972	Individual Protein	X-box-binding protein 1	Rattus norvegicus	FC	=	2.2	n.a.	PMID[545848]
NPT3972	Individual Protein	X-box-binding protein 1	Rattus norvegicus	FC	>	1.07	n.a.	PMID[545849]
NPT3972	Individual Protein	X-box-binding protein 1	Rattus norvegicus	EC50	=	79.8	nM	PMID[545849]

☑ 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 NPC83511 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	562
0.1-0.2	2815
0.2-0.3	12114
0.3-0.4	4884
0.4-0.5	11358
0.5-0.6	8636
0.6-0.7	1947
0.7-0.8	328
0.8-0.85	36
0.85-0.9	9
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.976	High Similarity	NPC116007
0.908	High Similarity	NPC169387
0.908	High Similarity	NPC477259
0.8778	High Similarity	NPC477258
0.8729	High Similarity	NPC24228
0.8686	High Similarity	NPC27887
0.8678	High Similarity	NPC222524
0.8563	High Similarity	NPC93593
0.8508	High Similarity	NPC226708
0.8409	Intermediate Similarity	NPC308267
0.8297	Intermediate Similarity	NPC208890
0.8295	Intermediate Similarity	NPC303581
0.8295	Intermediate Similarity	NPC67978
0.828	Intermediate Similarity	NPC46744
0.828	Intermediate Similarity	NPC70290
0.828	Intermediate Similarity	NPC14622
0.828	Intermediate Similarity	NPC215098
0.828	Intermediate Similarity	NPC124302
0.828	Intermediate Similarity	NPC73020
0.827	Intermediate Similarity	NPC125924
0.8235	Intermediate Similarity	NPC5374
0.8218	Intermediate Similarity	NPC306669
0.8201	Intermediate Similarity	NPC2173
0.8201	Intermediate Similarity	NPC202771
0.8201	Intermediate Similarity	NPC328700
0.8201	Intermediate Similarity	NPC119818
0.8191	Intermediate Similarity	NPC72788
0.8191	Intermediate Similarity	NPC314100
0.8191	Intermediate Similarity	NPC120671
0.8191	Intermediate Similarity	NPC226652
0.8187	Intermediate Similarity	NPC234392
0.8187	Intermediate Similarity	NPC31311
0.8182	Intermediate Similarity	NPC86469
0.8182	Intermediate Similarity	NPC71124
0.8162	Intermediate Similarity	NPC254957
0.8138	Intermediate Similarity	NPC207239
0.8118	Intermediate Similarity	NPC469816
0.8118	Intermediate Similarity	NPC469815
0.8115	Intermediate Similarity	NPC268077
0.8114	Intermediate Similarity	NPC231198
0.8063	Intermediate Similarity	NPC207971
0.8059	Intermediate Similarity	NPC119669
0.8023	Intermediate Similarity	NPC216459
0.8023	Intermediate Similarity	NPC41178
0.8023	Intermediate Similarity	NPC138487
0.8011	Intermediate Similarity	NPC121400
0.8	Intermediate Similarity	NPC223125
0.7978	Intermediate Similarity	NPC102760
0.7978	Intermediate Similarity	NPC241055
0.7977	Intermediate Similarity	NPC146288
0.7965	Intermediate Similarity	NPC470708
0.7946	Intermediate Similarity	NPC471650
0.7944	Intermediate Similarity	NPC4669
0.791	Intermediate Similarity	NPC168409
0.7907	Intermediate Similarity	NPC223124
0.7907	Intermediate Similarity	NPC233029
0.7907	Intermediate Similarity	NPC210148
0.7903	Intermediate Similarity	NPC166979
0.7898	Intermediate Similarity	NPC153631
0.7882	Intermediate Similarity	NPC475959
0.7857	Intermediate Similarity	NPC5167
0.7839	Intermediate Similarity	NPC55470
0.7784	Intermediate Similarity	NPC106786
0.7771	Intermediate Similarity	NPC57512
0.774	Intermediate Similarity	NPC135006
0.7733	Intermediate Similarity	NPC470088
0.7725	Intermediate Similarity	NPC63152
0.7711	Intermediate Similarity	NPC225745
0.7709	Intermediate Similarity	NPC232514
0.7709	Intermediate Similarity	NPC276944
0.7709	Intermediate Similarity	NPC238530
0.7705	Intermediate Similarity	NPC207721
0.7701	Intermediate Similarity	NPC476580
0.7663	Intermediate Similarity	NPC85613
0.7654	Intermediate Similarity	NPC59567
0.7654	Intermediate Similarity	NPC476569
0.7651	Intermediate Similarity	NPC7018
0.764	Intermediate Similarity	NPC160298
0.764	Intermediate Similarity	NPC477559
0.764	Intermediate Similarity	NPC266753
0.764	Intermediate Similarity	NPC232924
0.764	Intermediate Similarity	NPC306902
0.7624	Intermediate Similarity	NPC210918
0.7617	Intermediate Similarity	NPC23080
0.7617	Intermediate Similarity	NPC193906
0.7616	Intermediate Similarity	NPC106295
0.7616	Intermediate Similarity	NPC16107
0.7616	Intermediate Similarity	NPC51957
0.7616	Intermediate Similarity	NPC210437
0.7616	Intermediate Similarity	NPC476144
0.7614	Intermediate Similarity	NPC78733
0.7605	Intermediate Similarity	NPC252107
0.7605	Intermediate Similarity	NPC194359
0.7605	Intermediate Similarity	NPC28641
0.7604	Intermediate Similarity	NPC470646
0.7602	Intermediate Similarity	NPC469978
0.76	Intermediate Similarity	NPC148898
0.759	Intermediate Similarity	NPC180647
0.7588	Intermediate Similarity	NPC46990
0.7584	Intermediate Similarity	NPC477080
0.7572	Intermediate Similarity	NPC7467
0.7569	Intermediate Similarity	NPC24264
0.7569	Intermediate Similarity	NPC476432
0.7545	Intermediate Similarity	NPC99078
0.7541	Intermediate Similarity	NPC474708
0.7539	Intermediate Similarity	NPC475597
0.7539	Intermediate Similarity	NPC473716
0.7527	Intermediate Similarity	NPC247389
0.7527	Intermediate Similarity	NPC118633
0.7527	Intermediate Similarity	NPC294790
0.7527	Intermediate Similarity	NPC148693
0.7526	Intermediate Similarity	NPC237579
0.7514	Intermediate Similarity	NPC302527
0.7514	Intermediate Similarity	NPC167546
0.7514	Intermediate Similarity	NPC225774
0.7514	Intermediate Similarity	NPC16805
0.7514	Intermediate Similarity	NPC247972
0.7514	Intermediate Similarity	NPC76079
0.7514	Intermediate Similarity	NPC169742
0.7513	Intermediate Similarity	NPC18306
0.75	Intermediate Similarity	NPC24954
0.75	Intermediate Similarity	NPC220923
0.7487	Intermediate Similarity	NPC308943
0.7486	Intermediate Similarity	NPC111485
0.7486	Intermediate Similarity	NPC475845
0.7485	Intermediate Similarity	NPC205178
0.7485	Intermediate Similarity	NPC73883
0.7485	Intermediate Similarity	NPC136330
0.7485	Intermediate Similarity	NPC196609
0.7485	Intermediate Similarity	NPC255817
0.7485	Intermediate Similarity	NPC230698
0.7485	Intermediate Similarity	NPC277042
0.7485	Intermediate Similarity	NPC251454
0.7473	Intermediate Similarity	NPC219341
0.7471	Intermediate Similarity	NPC188163
0.7471	Intermediate Similarity	NPC474915
0.7471	Intermediate Similarity	NPC37144
0.7471	Intermediate Similarity	NPC328750
0.7471	Intermediate Similarity	NPC59907
0.7471	Intermediate Similarity	NPC213206
0.7459	Intermediate Similarity	NPC2314
0.7459	Intermediate Similarity	NPC189470
0.7447	Intermediate Similarity	NPC179704
0.7446	Intermediate Similarity	NPC75958
0.7444	Intermediate Similarity	NPC215829
0.7444	Intermediate Similarity	NPC97072
0.744	Intermediate Similarity	NPC145446
0.744	Intermediate Similarity	NPC137172
0.7437	Intermediate Similarity	NPC80472
0.7435	Intermediate Similarity	NPC141440
0.7432	Intermediate Similarity	NPC474324
0.7432	Intermediate Similarity	NPC57812
0.7432	Intermediate Similarity	NPC298979
0.7425	Intermediate Similarity	NPC167096
0.7414	Intermediate Similarity	NPC476151
0.7412	Intermediate Similarity	NPC314682
0.7407	Intermediate Similarity	NPC116284
0.7396	Intermediate Similarity	NPC95366
0.7396	Intermediate Similarity	NPC248505
0.7396	Intermediate Similarity	NPC470707
0.7384	Intermediate Similarity	NPC128019
0.7384	Intermediate Similarity	NPC476567
0.7384	Intermediate Similarity	NPC136860
0.7382	Intermediate Similarity	NPC230098
0.7382	Intermediate Similarity	NPC474009
0.7381	Intermediate Similarity	NPC96406
0.738	Intermediate Similarity	NPC283810
0.7379	Intermediate Similarity	NPC195120
0.7377	Intermediate Similarity	NPC304659
0.7377	Intermediate Similarity	NPC86144
0.7368	Intermediate Similarity	NPC474746
0.7368	Intermediate Similarity	NPC475981
0.7356	Intermediate Similarity	NPC229787
0.7351	Intermediate Similarity	NPC311991
0.7345	Intermediate Similarity	NPC476579
0.7337	Intermediate Similarity	NPC284842
0.7333	Intermediate Similarity	NPC33256
0.733	Intermediate Similarity	NPC103379
0.733	Intermediate Similarity	NPC477565
0.7321	Intermediate Similarity	NPC45783
0.7321	Intermediate Similarity	NPC103947
0.7321	Intermediate Similarity	NPC94280
0.7321	Intermediate Similarity	NPC159150
0.7321	Intermediate Similarity	NPC193673
0.7321	Intermediate Similarity	NPC328419
0.732	Intermediate Similarity	NPC302001
0.7318	Intermediate Similarity	NPC276588
0.7318	Intermediate Similarity	NPC127674
0.7318	Intermediate Similarity	NPC54379
0.7318	Intermediate Similarity	NPC184026
0.7318	Intermediate Similarity	NPC204828
0.7318	Intermediate Similarity	NPC39701
0.7318	Intermediate Similarity	NPC193949
0.7318	Intermediate Similarity	NPC295691
0.7318	Intermediate Similarity	NPC469817
0.7318	Intermediate Similarity	NPC189266
0.7318	Intermediate Similarity	NPC172765
0.7318	Intermediate Similarity	NPC249797
0.7318	Intermediate Similarity	NPC278799
0.7318	Intermediate Similarity	NPC207757

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 NPC83511 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	311
0.1-0.2	669
0.2-0.3	977
0.3-0.4	1398
0.4-0.5	2736
0.5-0.6	2251
0.6-0.7	704
0.7-0.8	99
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.828	Intermediate Similarity	NPD4420	Approved
0.8201	Intermediate Similarity	NPD5006	Approved
0.8201	Intermediate Similarity	NPD5005	Approved
0.8191	Intermediate Similarity	NPD5457	Discontinued
0.773	Intermediate Similarity	NPD7280	Phase 3
0.773	Intermediate Similarity	NPD7281	Phase 3
0.7727	Intermediate Similarity	NPD5977	Approved
0.7727	Intermediate Similarity	NPD5978	Approved
0.7701	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD6618	Phase 2
0.766	Intermediate Similarity	NPD7291	Discontinued
0.7616	Intermediate Similarity	NPD4584	Approved
0.7614	Intermediate Similarity	NPD7607	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD7110	Phase 1
0.7554	Intermediate Similarity	NPD5313	Approved
0.7554	Intermediate Similarity	NPD5312	Approved
0.7544	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD2492	Phase 1
0.7473	Intermediate Similarity	NPD6297	Approved
0.7471	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD3640	Phase 3
0.7429	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD3639	Approved
0.7429	Intermediate Similarity	NPD3641	Approved
0.7363	Intermediate Similarity	NPD4859	Phase 1
0.7348	Intermediate Similarity	NPD1307	Phase 2
0.7348	Intermediate Similarity	NPD1309	Phase 2
0.7347	Intermediate Similarity	NPD5071	Phase 2
0.7345	Intermediate Similarity	NPD824	Approved
0.7333	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD6030	Approved
0.733	Intermediate Similarity	NPD6031	Approved
0.7316	Intermediate Similarity	NPD6851	Approved
0.7316	Intermediate Similarity	NPD6853	Approved
0.7254	Intermediate Similarity	NPD7235	Clinical (unspecified phase)
0.722	Intermediate Similarity	NPD7225	Discontinued
0.7208	Intermediate Similarity	NPD5564	Approved
0.7207	Intermediate Similarity	NPD6875	Approved
0.7207	Intermediate Similarity	NPD6876	Approved
0.72	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD160	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD956	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD8149	Discontinued
0.7189	Intermediate Similarity	NPD4166	Phase 2
0.7186	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD6146	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD6385	Approved
0.7167	Intermediate Similarity	NPD6386	Approved
0.7156	Intermediate Similarity	NPD4846	Phase 2
0.715	Intermediate Similarity	NPD4084	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5441	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD3808	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD4997	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD7255	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD5896	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD6997	Phase 2
0.7071	Intermediate Similarity	NPD5582	Discontinued
0.7053	Intermediate Similarity	NPD3885	Approved
0.7039	Intermediate Similarity	NPD1670	Discontinued
0.7035	Intermediate Similarity	NPD743	Approved
0.7033	Intermediate Similarity	NPD7248	Discontinued
0.7033	Intermediate Similarity	NPD6844	Discontinued
0.7031	Intermediate Similarity	NPD7190	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6625	Approved
0.6995	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD6873	Phase 2
0.6968	Remote Similarity	NPD5242	Approved
0.6961	Remote Similarity	NPD4017	Approved
0.6954	Remote Similarity	NPD7668	Phase 2
0.6952	Remote Similarity	NPD6107	Approved
0.6947	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD5950	Discontinued
0.694	Remote Similarity	NPD7298	Approved
0.6939	Remote Similarity	NPD3349	Phase 2
0.6931	Remote Similarity	NPD2898	Approved
0.6919	Remote Similarity	NPD7296	Approved
0.6915	Remote Similarity	NPD5186	Approved
0.6915	Remote Similarity	NPD5183	Approved
0.6904	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD7224	Discontinued
0.6898	Remote Similarity	NPD7223	Discontinued
0.6897	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD6720	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD7584	Approved
0.6878	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD5025	Approved
0.6865	Remote Similarity	NPD5967	Approved
0.6859	Remote Similarity	NPD8251	Approved
0.6859	Remote Similarity	NPD8252	Approved
0.6859	Remote Similarity	NPD8099	Discontinued
0.6854	Remote Similarity	NPD8318	Clinical (unspecified phase)
0.685	Remote Similarity	NPD7669	Phase 3
0.685	Remote Similarity	NPD4413	Clinical (unspecified phase)
0.685	Remote Similarity	NPD6493	Phase 3
0.6848	Remote Similarity	NPD7317	Phase 3
0.6842	Remote Similarity	NPD683	Approved
0.6842	Remote Similarity	NPD4481	Phase 3
0.6842	Remote Similarity	NPD5718	Phase 2
0.6829	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD6788	Approved
0.6823	Remote Similarity	NPD6020	Phase 2
0.6823	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6823	Remote Similarity	NPD8156	Discontinued
0.6821	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD2971	Approved
0.6821	Remote Similarity	NPD2968	Approved
0.6806	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6181	Discontinued
0.6798	Remote Similarity	NPD7810	Phase 3
0.6798	Remote Similarity	NPD7811	Phase 3
0.6792	Remote Similarity	NPD7047	Phase 3
0.6791	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD7318	Phase 3
0.6774	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD2822	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD6040	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD4107	Approved
0.676	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD6894	Phase 1
0.6745	Remote Similarity	NPD7559	Phase 2
0.6742	Remote Similarity	NPD4885	Approved
0.6734	Remote Similarity	NPD5910	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD6834	Approved
0.6724	Remote Similarity	NPD1933	Approved
0.672	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD4773	Phase 2
0.6703	Remote Similarity	NPD4772	Phase 2
0.6702	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD5519	Discontinued
0.6686	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD7802	Discontinued
0.6684	Remote Similarity	NPD7177	Discontinued
0.6684	Remote Similarity	NPD2821	Approved
0.6667	Remote Similarity	NPD7427	Discontinued
0.6651	Remote Similarity	NPD7278	Phase 2
0.6651	Remote Similarity	NPD3815	Phase 1
0.6651	Remote Similarity	NPD7279	Phase 2
0.6651	Remote Similarity	NPD3816	Phase 1
0.665	Remote Similarity	NPD4482	Phase 3
0.665	Remote Similarity	NPD4078	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD6071	Discontinued
0.6649	Remote Similarity	NPD5600	Discontinued
0.6648	Remote Similarity	NPD2335	Discontinued
0.6635	Remote Similarity	NPD5914	Approved
0.6633	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD5966	Clinical (unspecified phase)
0.663	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.663	Remote Similarity	NPD4210	Discontinued
0.6628	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD7048	Phase 3
0.662	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.662	Remote Similarity	NPD2899	Discontinued
0.6619	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD2974	Approved
0.6618	Remote Similarity	NPD2975	Approved
0.6618	Remote Similarity	NPD2973	Approved
0.6618	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD2488	Approved
0.6617	Remote Similarity	NPD2490	Approved
0.6616	Remote Similarity	NPD8053	Approved
0.6616	Remote Similarity	NPD8054	Approved
0.6615	Remote Similarity	NPD2325	Approved
0.6615	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD7831	Phase 2
0.6614	Remote Similarity	NPD5604	Discontinued
0.6614	Remote Similarity	NPD7833	Phase 2
0.6614	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD5890	Approved
0.6613	Remote Similarity	NPD5889	Approved
0.6612	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD6612	Phase 2
0.66	Remote Similarity	NPD7693	Approved
0.6598	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD2560	Approved
0.6596	Remote Similarity	NPD2563	Approved
0.6593	Remote Similarity	NPD5297	Approved
0.6579	Remote Similarity	NPD3252	Approved
0.6575	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD5241	Discontinued
0.6573	Remote Similarity	NPD6826	Discontinued
0.6571	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD7583	Approved
0.657	Remote Similarity	NPD3450	Approved
0.657	Remote Similarity	NPD3452	Approved
0.6564	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD7942	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD6747	Phase 1
0.6562	Remote Similarity	NPD3051	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