NPASS Compound

Structure

CID211296 OpenBabel06191716002D 26 29 0 0 0 0 0 0 0 0999 V2000 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 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 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 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 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 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 4.1369 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -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 -0.8660 -1.5000 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 2.5981 -2.5000 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 -0.8660 0.5000 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 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 24 1 0 0 0 0 5 6 2 0 0 0 0 5 13 1 0 0 0 0 6 15 1 0 0 0 0 7 8 1 0 0 0 0 7 14 1 0 0 0 0 8 22 1 0 0 0 0 9 13 2 0 0 0 0 9 17 1 0 0 0 0 10 14 2 0 0 0 0 10 19 1 0 0 0 0 11 16 2 0 0 0 0 11 18 1 0 0 0 0 12 25 1 0 0 0 0 12 26 1 0 0 0 0 13 16 1 0 0 0 0 14 15 1 0 0 0 0 15 20 2 0 0 0 0 16 20 1 0 0 0 0 17 18 2 0 0 0 0 17 25 1 0 0 0 0 18 26 1 0 0 0 0 19 21 2 0 0 0 0 19 23 1 0 0 0 0 20 21 1 0 0 0 0 21 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	353.16
Volume:	365.249
LogP:	4.337
LogD:	3.296
LogS:	-5.378
# Rotatable Bonds:	5
TPSA:	40.16
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.652
Synthetic Accessibility Score:	2.458
Fsp3:	0.333
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:	-4.612
MDCK Permeability:	2.991606561408844e-05
Pgp-inhibitor:	0.494
Pgp-substrate:	0.816
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.064

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.972
Plasma Protein Binding (PPB):	83.73490142822266%
Volume Distribution (VD):	1.882
Pgp-substrate:	4.669255256652832%

ADMET: Metabolism

CYP1A2-inhibitor:	0.959
CYP1A2-substrate:	0.971
CYP2C19-inhibitor:	0.078
CYP2C19-substrate:	0.963
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.893
CYP2D6-inhibitor:	0.907
CYP2D6-substrate:	0.959
CYP3A4-inhibitor:	0.69
CYP3A4-substrate:	0.903

ADMET: Excretion

Clearance (CL):	12.576
Half-life (T1/2):	0.169

ADMET: Toxicity

hERG Blockers:	0.955
Human Hepatotoxicity (H-HT):	0.556
Drug-inuced Liver Injury (DILI):	0.93
AMES Toxicity:	0.688
Rat Oral Acute Toxicity:	0.646
Maximum Recommended Daily Dose:	0.813
Skin Sensitization:	0.927
Carcinogencity:	0.777
Eye Corrosion:	0.004
Eye Irritation:	0.014
Respiratory Toxicity:	0.961

Download Data

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

Natural Product: NPC211296

Natural Product ID:	NPC211296
*Common Name:**	Thalicthuberinec
IUPAC Name:	2-(1,2-dimethoxynaphtho[2,1-f][1,3]benzodioxol-4-yl)-N,N-dimethylethanamine
Synonyms:	Thalicthuberinec
Standard InCHIKey:	DDCILWXYWBKXKC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H23NO4/c1-22(2)8-7-14-10-19(23-3)21(24-4)20-15(14)6-5-13-9-17-18(11-16(13)20)26-12-25-17/h5-6,9-11H,7-8,12H2,1-4H3
SMILES:	COc1cc(CCN(C)C)c2c(c1OC)c1cc3OCOc3cc1cc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518852
PubChem CID:	11245138
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0003332] 6,6a-secoaporphines

*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
NPO20891	Coleonema pulchellum	Species	Rutaceae	Eukaryota	n.a.	Costa Rica; Bartica, Guyana	n.a.	PMID[16124770]
NPO22044	Tamarix chinensis	Species	Tamaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22044	Tamarix chinensis	Species	Tamaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20891	Coleonema pulchellum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22044	Tamarix chinensis	Species	Tamaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22044	Tamarix chinensis	Species	Tamaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20320	Cryptostegia madagascariensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21985	Koenigia coriaria	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20451	Vitex scabra	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20891	Coleonema pulchellum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22625	Copris tripartitus	Species	Scarabaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22044	Tamarix chinensis	Species	Tamaricaceae	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	5

Activity Type	# Activity
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	Activity	=	100.0	ug ml-1	PMID[447934]
NPT871	Organism	Salmonella enterica subsp. enterica serovar Gallinarum	Salmonella enterica subsp. enterica serovar Gallinarum	Activity	=	1000.0	ug ml-1	PMID[447934]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	Activity	=	1000.0	ug ml-1	PMID[447934]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	Activity	=	25.0	ug ml-1	PMID[447934]
NPT20	Organism	Candida albicans	Candida albicans	Activity	=	50.0	ug ml-1	PMID[447934]

☑ 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 NPC211296 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	336
0.1-0.2	1783
0.2-0.3	6705
0.3-0.4	11657
0.4-0.5	5186
0.5-0.6	10141
0.6-0.7	5397
0.7-0.8	1364
0.8-0.85	108
0.85-0.9	15
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9714	High Similarity	NPC145304
0.8903	High Similarity	NPC24264
0.8903	High Similarity	NPC476432
0.8874	High Similarity	NPC244112
0.8846	High Similarity	NPC247389
0.8839	High Similarity	NPC302527
0.8839	High Similarity	NPC16805
0.8839	High Similarity	NPC167546
0.8839	High Similarity	NPC225774
0.8782	High Similarity	NPC219341
0.8742	High Similarity	NPC114124
0.8726	High Similarity	NPC210918
0.8645	High Similarity	NPC477559
0.8645	High Similarity	NPC160298
0.8645	High Similarity	NPC306902
0.8645	High Similarity	NPC232924
0.8645	High Similarity	NPC266753
0.8627	High Similarity	NPC76079
0.8571	High Similarity	NPC100129
0.8562	High Similarity	NPC19520
0.8562	High Similarity	NPC149090
0.8543	High Similarity	NPC219162
0.85	High Similarity	NPC6152
0.8477	Intermediate Similarity	NPC475959
0.8477	Intermediate Similarity	NPC130941
0.8471	Intermediate Similarity	NPC60186
0.8466	Intermediate Similarity	NPC114364
0.8466	Intermediate Similarity	NPC320223
0.8457	Intermediate Similarity	NPC229166
0.8457	Intermediate Similarity	NPC128560
0.8457	Intermediate Similarity	NPC199465
0.8421	Intermediate Similarity	NPC77359
0.8411	Intermediate Similarity	NPC90844
0.8411	Intermediate Similarity	NPC253883
0.8411	Intermediate Similarity	NPC95075
0.8397	Intermediate Similarity	NPC476572
0.8387	Intermediate Similarity	NPC216459
0.8387	Intermediate Similarity	NPC41178
0.8387	Intermediate Similarity	NPC325871
0.8387	Intermediate Similarity	NPC138487
0.8387	Intermediate Similarity	NPC99659
0.8375	Intermediate Similarity	NPC298979
0.8367	Intermediate Similarity	NPC210086
0.8333	Intermediate Similarity	NPC146288
0.8323	Intermediate Similarity	NPC241055
0.8313	Intermediate Similarity	NPC86144
0.8313	Intermediate Similarity	NPC248642
0.8313	Intermediate Similarity	NPC304659
0.8303	Intermediate Similarity	NPC126284
0.8301	Intermediate Similarity	NPC92541
0.8298	Intermediate Similarity	NPC17348
0.8289	Intermediate Similarity	NPC16436
0.8269	Intermediate Similarity	NPC93593
0.8263	Intermediate Similarity	NPC156576
0.8261	Intermediate Similarity	NPC150879
0.8253	Intermediate Similarity	NPC474506
0.8253	Intermediate Similarity	NPC179704
0.8253	Intermediate Similarity	NPC32413
0.825	Intermediate Similarity	NPC168409
0.8243	Intermediate Similarity	NPC196420
0.8242	Intermediate Similarity	NPC118633
0.8242	Intermediate Similarity	NPC23219
0.8242	Intermediate Similarity	NPC148693
0.8242	Intermediate Similarity	NPC294790
0.8228	Intermediate Similarity	NPC477080
0.8225	Intermediate Similarity	NPC312531
0.8217	Intermediate Similarity	NPC234392
0.8217	Intermediate Similarity	NPC31311
0.8207	Intermediate Similarity	NPC149337
0.8207	Intermediate Similarity	NPC471983
0.8204	Intermediate Similarity	NPC116284
0.8194	Intermediate Similarity	NPC81733
0.8194	Intermediate Similarity	NPC326316
0.8193	Intermediate Similarity	NPC470879
0.8193	Intermediate Similarity	NPC258695
0.8193	Intermediate Similarity	NPC267408
0.8187	Intermediate Similarity	NPC189470
0.8182	Intermediate Similarity	NPC112575
0.8182	Intermediate Similarity	NPC287588
0.8182	Intermediate Similarity	NPC177167
0.8171	Intermediate Similarity	NPC474051
0.817	Intermediate Similarity	NPC144863
0.8163	Intermediate Similarity	NPC11147
0.8155	Intermediate Similarity	NPC135772
0.8144	Intermediate Similarity	NPC476574
0.8144	Intermediate Similarity	NPC312918
0.8144	Intermediate Similarity	NPC477561
0.8144	Intermediate Similarity	NPC155442
0.8141	Intermediate Similarity	NPC26601
0.8141	Intermediate Similarity	NPC233029
0.8141	Intermediate Similarity	NPC210148
0.8137	Intermediate Similarity	NPC180306
0.8121	Intermediate Similarity	NPC477558
0.8118	Intermediate Similarity	NPC237579
0.8117	Intermediate Similarity	NPC59907
0.8117	Intermediate Similarity	NPC37144
0.8108	Intermediate Similarity	NPC7018
0.8105	Intermediate Similarity	NPC473934
0.8101	Intermediate Similarity	NPC477133
0.8101	Intermediate Similarity	NPC477132
0.8101	Intermediate Similarity	NPC186063
0.8075	Intermediate Similarity	NPC233650
0.8061	Intermediate Similarity	NPC2314
0.8059	Intermediate Similarity	NPC214116
0.8038	Intermediate Similarity	NPC123323
0.8037	Intermediate Similarity	NPC474931
0.8037	Intermediate Similarity	NPC158376
0.8037	Intermediate Similarity	NPC117188
0.8037	Intermediate Similarity	NPC205421
0.8037	Intermediate Similarity	NPC145832
0.8037	Intermediate Similarity	NPC12053
0.8037	Intermediate Similarity	NPC306555
0.8037	Intermediate Similarity	NPC81218
0.8027	Intermediate Similarity	NPC228843
0.8025	Intermediate Similarity	NPC78222
0.8025	Intermediate Similarity	NPC134858
0.8025	Intermediate Similarity	NPC276944
0.8025	Intermediate Similarity	NPC196447
0.8025	Intermediate Similarity	NPC232514
0.8025	Intermediate Similarity	NPC477563
0.8025	Intermediate Similarity	NPC306843
0.8025	Intermediate Similarity	NPC212794
0.8025	Intermediate Similarity	NPC96603
0.8025	Intermediate Similarity	NPC238530
0.8025	Intermediate Similarity	NPC13504
0.8025	Intermediate Similarity	NPC136508
0.8025	Intermediate Similarity	NPC253043
0.8013	Intermediate Similarity	NPC328750
0.8013	Intermediate Similarity	NPC188163
0.8013	Intermediate Similarity	NPC213206
0.8013	Intermediate Similarity	NPC474915
0.7988	Intermediate Similarity	NPC299990
0.7988	Intermediate Similarity	NPC249405
0.7988	Intermediate Similarity	NPC73492
0.7987	Intermediate Similarity	NPC180756
0.7987	Intermediate Similarity	NPC323443
0.7975	Intermediate Similarity	NPC474442
0.7965	Intermediate Similarity	NPC82763
0.7963	Intermediate Similarity	NPC324144
0.7963	Intermediate Similarity	NPC218614
0.7959	Intermediate Similarity	NPC118419
0.7953	Intermediate Similarity	NPC57036
0.795	Intermediate Similarity	NPC4304
0.7947	Intermediate Similarity	NPC314682
0.7939	Intermediate Similarity	NPC152212
0.7939	Intermediate Similarity	NPC75958
0.7935	Intermediate Similarity	NPC210437
0.7935	Intermediate Similarity	NPC51957
0.7935	Intermediate Similarity	NPC476144
0.7935	Intermediate Similarity	NPC106295
0.7935	Intermediate Similarity	NPC16107
0.7931	Intermediate Similarity	NPC471986
0.7927	Intermediate Similarity	NPC210140
0.7919	Intermediate Similarity	NPC170779
0.7919	Intermediate Similarity	NPC185680
0.7919	Intermediate Similarity	NPC90083
0.7919	Intermediate Similarity	NPC145722
0.7919	Intermediate Similarity	NPC256776
0.7914	Intermediate Similarity	NPC169743
0.7911	Intermediate Similarity	NPC148898
0.7908	Intermediate Similarity	NPC191231
0.7907	Intermediate Similarity	NPC186546
0.7907	Intermediate Similarity	NPC474904
0.7907	Intermediate Similarity	NPC476576
0.7905	Intermediate Similarity	NPC97316
0.7905	Intermediate Similarity	NPC227002
0.7888	Intermediate Similarity	NPC111485
0.7885	Intermediate Similarity	NPC7467
0.7882	Intermediate Similarity	NPC476575
0.7882	Intermediate Similarity	NPC275132
0.7881	Intermediate Similarity	NPC266006
0.7875	Intermediate Similarity	NPC170503
0.7875	Intermediate Similarity	NPC126519
0.7875	Intermediate Similarity	NPC203784
0.7874	Intermediate Similarity	NPC302001
0.7872	Intermediate Similarity	NPC344161
0.7867	Intermediate Similarity	NPC474139
0.7867	Intermediate Similarity	NPC231884
0.7867	Intermediate Similarity	NPC167944
0.7867	Intermediate Similarity	NPC42793
0.7862	Intermediate Similarity	NPC118332
0.7853	Intermediate Similarity	NPC1229
0.7848	Intermediate Similarity	NPC52475
0.7844	Intermediate Similarity	NPC228040
0.784	Intermediate Similarity	NPC166014
0.784	Intermediate Similarity	NPC271388
0.784	Intermediate Similarity	NPC27410
0.784	Intermediate Similarity	NPC205255
0.784	Intermediate Similarity	NPC235143
0.784	Intermediate Similarity	NPC230956
0.784	Intermediate Similarity	NPC119649
0.7829	Intermediate Similarity	NPC220344
0.7829	Intermediate Similarity	NPC243996
0.7829	Intermediate Similarity	NPC132804
0.7829	Intermediate Similarity	NPC275061
0.7821	Intermediate Similarity	NPC33832
0.7821	Intermediate Similarity	NPC476151
0.7818	Intermediate Similarity	NPC474324
0.7818	Intermediate Similarity	NPC252960
0.7818	Intermediate Similarity	NPC57812

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 NPC211296 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	211
0.1-0.2	916
0.2-0.3	1037
0.3-0.4	2547
0.4-0.5	2325
0.5-0.6	1307
0.6-0.7	657
0.7-0.8	147
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8966	High Similarity	NPD5084	Clinical (unspecified phase)
0.8278	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD4584	Approved
0.7933	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD5718	Phase 2
0.7879	Intermediate Similarity	NPD4481	Phase 3
0.7877	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD6895	Approved
0.7867	Intermediate Similarity	NPD6896	Approved
0.7866	Intermediate Similarity	NPD3051	Approved
0.7838	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD7124	Phase 2
0.7762	Intermediate Similarity	NPD3705	Approved
0.7742	Intermediate Similarity	NPD5241	Discontinued
0.7711	Intermediate Similarity	NPD2969	Approved
0.7711	Intermediate Similarity	NPD2970	Approved
0.7674	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD2977	Approved
0.7654	Intermediate Similarity	NPD2978	Approved
0.7625	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD2563	Approved
0.7607	Intermediate Similarity	NPD2560	Approved
0.7597	Intermediate Similarity	NPD1375	Discontinued
0.7582	Intermediate Similarity	NPD4108	Discontinued
0.7574	Intermediate Similarity	NPD8251	Approved
0.7574	Intermediate Similarity	NPD8252	Approved
0.7574	Intermediate Similarity	NPD8099	Discontinued
0.7566	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD4210	Discontinued
0.7561	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD6788	Approved
0.756	Intermediate Similarity	NPD2489	Approved
0.756	Intermediate Similarity	NPD27	Approved
0.7547	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD1669	Approved
0.7529	Intermediate Similarity	NPD8156	Discontinued
0.7516	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7831	Phase 2
0.7515	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7833	Phase 2
0.75	Intermediate Similarity	NPD4237	Approved
0.75	Intermediate Similarity	NPD3060	Approved
0.75	Intermediate Similarity	NPD5976	Discontinued
0.75	Intermediate Similarity	NPD4236	Phase 3
0.7483	Intermediate Similarity	NPD4475	Approved
0.7483	Intermediate Similarity	NPD4474	Approved
0.747	Intermediate Similarity	NPD7400	Phase 3
0.7452	Intermediate Similarity	NPD6331	Phase 2
0.7452	Intermediate Similarity	NPD5754	Discontinued
0.7452	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD2492	Phase 1
0.744	Intermediate Similarity	NPD6071	Discontinued
0.7439	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD3110	Approved
0.7434	Intermediate Similarity	NPD3109	Approved
0.7425	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD2971	Approved
0.7414	Intermediate Similarity	NPD2968	Approved
0.7407	Intermediate Similarity	NPD4017	Approved
0.7394	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6031	Approved
0.7391	Intermediate Similarity	NPD6030	Approved
0.7391	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD4727	Phase 1
0.7389	Intermediate Similarity	NPD6674	Discontinued
0.7378	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD5283	Phase 1
0.7345	Intermediate Similarity	NPD7906	Approved
0.7325	Intermediate Similarity	NPD7037	Approved
0.732	Intermediate Similarity	NPD2238	Phase 2
0.7317	Intermediate Similarity	NPD7110	Phase 1
0.7317	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD7310	Approved
0.7314	Intermediate Similarity	NPD4578	Approved
0.7314	Intermediate Similarity	NPD4577	Approved
0.7314	Intermediate Similarity	NPD7312	Approved
0.7314	Intermediate Similarity	NPD7311	Approved
0.7314	Intermediate Similarity	NPD7313	Approved
0.7308	Intermediate Similarity	NPD4420	Approved
0.7305	Intermediate Similarity	NPD4055	Discovery
0.7305	Intermediate Similarity	NPD5604	Discontinued
0.7301	Intermediate Similarity	NPD4005	Discontinued
0.729	Intermediate Similarity	NPD6111	Discontinued
0.7288	Intermediate Similarity	NPD4663	Approved
0.7278	Intermediate Similarity	NPD5177	Phase 3
0.7278	Intermediate Similarity	NPD7802	Discontinued
0.7278	Intermediate Similarity	NPD4162	Approved
0.7273	Intermediate Similarity	NPD7298	Approved
0.7273	Intermediate Similarity	NPD8054	Approved
0.7273	Intermediate Similarity	NPD3384	Approved
0.7273	Intermediate Similarity	NPD3383	Approved
0.7273	Intermediate Similarity	NPD7309	Approved
0.7273	Intermediate Similarity	NPD8053	Approved
0.7273	Intermediate Similarity	NPD37	Approved
0.7273	Intermediate Similarity	NPD3382	Approved
0.7267	Intermediate Similarity	NPD7019	Approved
0.7267	Intermediate Similarity	NPD7020	Approved
0.7267	Intermediate Similarity	NPD7905	Discontinued
0.7262	Intermediate Similarity	NPD5709	Phase 3
0.726	Intermediate Similarity	NPD2667	Approved
0.726	Intermediate Similarity	NPD2668	Approved
0.7256	Intermediate Similarity	NPD6876	Approved
0.7256	Intermediate Similarity	NPD6875	Approved
0.725	Intermediate Similarity	NPD6666	Approved
0.725	Intermediate Similarity	NPD6667	Approved
0.7247	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD6747	Phase 1
0.7233	Intermediate Similarity	NPD7466	Approved
0.723	Intermediate Similarity	NPD2233	Approved
0.723	Intermediate Similarity	NPD2232	Approved
0.723	Intermediate Similarity	NPD2230	Approved
0.7226	Intermediate Similarity	NPD2653	Approved
0.7219	Intermediate Similarity	NPD4666	Phase 3
0.7212	Intermediate Similarity	NPD6873	Phase 2
0.7205	Intermediate Similarity	NPD2421	Approved
0.7205	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD2420	Approved
0.7202	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD3443	Approved
0.7192	Intermediate Similarity	NPD3445	Approved
0.7192	Intermediate Similarity	NPD3444	Approved
0.7178	Intermediate Similarity	NPD3640	Phase 3
0.7178	Intermediate Similarity	NPD3641	Approved
0.7178	Intermediate Similarity	NPD3639	Approved
0.7168	Intermediate Similarity	NPD7177	Discontinued
0.716	Intermediate Similarity	NPD1424	Approved
0.716	Intermediate Similarity	NPD4123	Phase 3
0.7153	Intermediate Similarity	NPD709	Approved
0.7152	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD2898	Approved
0.7151	Intermediate Similarity	NPD5005	Approved
0.7151	Intermediate Similarity	NPD5006	Approved
0.7143	Intermediate Similarity	NPD4966	Approved
0.7143	Intermediate Similarity	NPD4967	Phase 2
0.7143	Intermediate Similarity	NPD4965	Approved
0.7133	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD2922	Phase 1
0.7126	Intermediate Similarity	NPD4585	Approved
0.7108	Intermediate Similarity	NPD6386	Approved
0.7108	Intermediate Similarity	NPD6385	Approved
0.7107	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5977	Approved
0.7083	Intermediate Similarity	NPD5978	Approved
0.7078	Intermediate Similarity	NPD5109	Approved
0.7078	Intermediate Similarity	NPD5111	Phase 2
0.7078	Intermediate Similarity	NPD7294	Phase 1
0.7078	Intermediate Similarity	NPD5110	Phase 2
0.7076	Intermediate Similarity	NPD7199	Phase 2
0.7075	Intermediate Similarity	NPD4093	Discontinued
0.7073	Intermediate Similarity	NPD1914	Approved
0.7073	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD2490	Approved
0.7072	Intermediate Similarity	NPD2488	Approved
0.707	Intermediate Similarity	NPD7119	Phase 2
0.7065	Intermediate Similarity	NPD2973	Approved
0.7065	Intermediate Similarity	NPD2974	Approved
0.7065	Intermediate Similarity	NPD2975	Approved
0.7059	Intermediate Similarity	NPD6234	Discontinued
0.7055	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD3657	Discovery
0.7039	Intermediate Similarity	NPD6584	Phase 3
0.7039	Intermediate Similarity	NPD7018	Phase 2
0.703	Intermediate Similarity	NPD3686	Approved
0.703	Intermediate Similarity	NPD3687	Approved
0.7024	Intermediate Similarity	NPD5772	Approved
0.7024	Intermediate Similarity	NPD5773	Approved
0.7022	Intermediate Similarity	NPD7281	Phase 3
0.7022	Intermediate Similarity	NPD7280	Phase 3
0.7017	Intermediate Similarity	NPD7235	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD6090	Discontinued
0.7011	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD6580	Approved
0.7007	Intermediate Similarity	NPD6581	Approved
0.7006	Intermediate Similarity	NPD4097	Suspended
0.7006	Intermediate Similarity	NPD7038	Approved
0.7006	Intermediate Similarity	NPD4773	Phase 2
0.7006	Intermediate Similarity	NPD2157	Approved
0.7006	Intermediate Similarity	NPD7039	Approved
0.7006	Intermediate Similarity	NPD6072	Discontinued
0.7006	Intermediate Similarity	NPD4772	Phase 2
0.6994	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD2161	Phase 2
0.6981	Remote Similarity	NPD4477	Approved
0.6981	Remote Similarity	NPD4476	Approved
0.6975	Remote Similarity	NPD2677	Approved
0.6974	Remote Similarity	NPD4098	Discontinued
0.697	Remote Similarity	NPD7427	Discontinued
0.6966	Remote Similarity	NPD7549	Discontinued
0.6966	Remote Similarity	NPD8453	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD7248	Discontinued
0.6964	Remote Similarity	NPD5720	Discontinued
0.6963	Remote Similarity	NPD4859	Phase 1
0.6959	Remote Similarity	NPD5691	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