NPASS Compound

Structure

CID193906 OpenBabel06191715582D 30 34 0 0 1 0 0 0 0 0999 V2000 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -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 0.8660 -1.5000 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 -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 0.0000 -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 0.8660 -0.5000 0.0000 C 0 0 1 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 -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 1.7321 0.0000 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 2.5981 -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 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 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 13 1 0 0 0 0 2 25 1 0 0 0 0 3 27 1 0 0 0 0 4 28 1 0 0 0 0 5 6 2 0 0 0 0 5 14 1 0 0 0 0 6 16 1 0 0 0 0 7 8 2 0 0 0 0 7 15 1 0 0 0 0 8 19 1 0 0 0 0 9 13 1 0 0 0 0 10 14 2 0 0 0 0 10 20 1 0 0 0 0 11 17 2 0 0 0 0 11 21 1 0 0 0 0 12 29 1 0 0 0 0 12 30 1 0 0 0 0 13 26 2 0 0 0 0 14 17 1 0 0 0 0 15 16 1 0 0 0 0 15 22 2 0 0 0 0 16 23 2 0 0 0 0 17 23 1 0 0 0 0 18 9 1 6 0 0 0 18 22 1 0 0 0 0 18 25 1 0 0 0 0 19 24 2 0 0 0 0 19 27 1 0 0 0 0 20 21 2 0 0 0 0 20 29 1 0 0 0 0 21 30 1 0 0 0 0 22 24 1 0 0 0 0 23 25 1 0 0 0 0 24 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	405.16
Volume:	412.098
LogP:	4.442
LogD:	3.544
LogS:	-6.571
# Rotatable Bonds:	4
TPSA:	57.23
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.626
Synthetic Accessibility Score:	3.263
Fsp3:	0.292
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:	-4.841
MDCK Permeability:	6.653877790085971e-05
Pgp-inhibitor:	0.197
Pgp-substrate:	0.595
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.897

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.143
Plasma Protein Binding (PPB):	91.98332977294922%
Volume Distribution (VD):	0.741
Pgp-substrate:	2.6408870220184326%

ADMET: Metabolism

CYP1A2-inhibitor:	0.889
CYP1A2-substrate:	0.931
CYP2C19-inhibitor:	0.975
CYP2C19-substrate:	0.845
CYP2C9-inhibitor:	0.867
CYP2C9-substrate:	0.916
CYP2D6-inhibitor:	0.938
CYP2D6-substrate:	0.931
CYP3A4-inhibitor:	0.904
CYP3A4-substrate:	0.889

ADMET: Excretion

Clearance (CL):	12.585
Half-life (T1/2):	0.151

ADMET: Toxicity

hERG Blockers:	0.045
Human Hepatotoxicity (H-HT):	0.213
Drug-inuced Liver Injury (DILI):	0.894
AMES Toxicity:	0.679
Rat Oral Acute Toxicity:	0.263
Maximum Recommended Daily Dose:	0.972
Skin Sensitization:	0.29
Carcinogencity:	0.921
Eye Corrosion:	0.003
Eye Irritation:	0.054
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC193906

Natural Product ID:	NPC193906
*Common Name:**	6-Acetonyldihydrochelerythrine
IUPAC Name:	1-[(13S)-1,2-dimethoxy-12-methyl-13H-[1,3]benzodioxolo[5,6-c]phenanthridin-13-yl]propan-2-one
Synonyms:	6-Acetonyldihydrochelerythrine
Standard InCHIKey:	VGTQLFWIJIABSU-SFHVURJKSA-N
Standard InCHI:	InChI=1S/C24H23NO5/c1-13(26)9-18-22-15(7-8-19(27-3)24(22)28-4)16-6-5-14-10-20-21(30-12-29-20)11-17(14)23(16)25(18)2/h5-8,10-11,18H,9,12H2,1-4H3/t18-/m0/s1
SMILES:	COc1c(OC)ccc2c1[C@H](CC(=O)C)N(C)c1c2ccc2c1cc1OCOc1c2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL250267
PubChem CID:	185516
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002665] Benzophenanthridine alkaloids [CHEMONTID:0002667] Dihydrobenzophenanthridine alkaloids

*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
NPO2842	Garcinia lucida	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17880175]
NPO3504	Argemone mexicana	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21094631]
NPO3504	Argemone mexicana	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3504	Argemone mexicana	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3504	Argemone mexicana	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5348	Colletotrichum acutatum	Species	Glomerellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6338	Chilo auricilius	Species	Crambidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5515	Cephalocroton cordofanus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20801	Antrodia sinuosa	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2842	Garcinia lucida	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9944	Salisaeta longa	Species	Rhodothermaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO3504	Argemone mexicana	Species	Papaveraceae	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	5
Others	15

Activity Type	# Activity
Cell Line	9
NON-MOLECULAR	5
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	15300.0	nM	PMID[575437]
NPT323	Cell Line	SW-620	Homo sapiens	Activity	=	27.0	%	PMID[575438]
NPT393	Cell Line	HCT-116	Homo sapiens	Activity	=	22.0	%	PMID[575438]
NPT323	Cell Line	SW-620	Homo sapiens	Activity	=	22.0	%	PMID[575438]
NPT393	Cell Line	HCT-116	Homo sapiens	Activity	=	19.0	%	PMID[575438]
NPT323	Cell Line	SW-620	Homo sapiens	Activity	=	65.0	%	PMID[575438]
NPT323	Cell Line	SW-620	Homo sapiens	Activity	=	34.0	%	PMID[575438]
NPT323	Cell Line	SW-620	Homo sapiens	FC	=	1.1	n.a.	PMID[575438]
NPT323	Cell Line	SW-620	Homo sapiens	IC50	=	3800.0	nM	PMID[575438]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	=	3900.0	nM	PMID[575437]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	6600.0	nM	PMID[575437]
NPT633	Organism	Leishmania donovani	Leishmania donovani	Inhibition	=	100.0	%	PMID[575437]
NPT633	Organism	Leishmania donovani	Leishmania donovani	Inhibition	=	87.0	%	PMID[575437]
NPT633	Organism	Leishmania donovani	Leishmania donovani	Inhibition	=	23.0	%	PMID[575437]
NPT633	Organism	Leishmania donovani	Leishmania donovani	Activity	=	57.4	%	PMID[575437]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	65.0	%	PMID[575438]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	25.0	%	PMID[575438]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	FC	=	1.3	n.a.	PMID[575438]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	FC	=	1.2	n.a.	PMID[575438]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	2400.0	nM	PMID[575438]

☑ 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 NPC193906 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	378
0.1-0.2	1829
0.2-0.3	7790
0.3-0.4	9608
0.4-0.5	6758
0.5-0.6	13896
0.6-0.7	1824
0.7-0.8	568
0.8-0.85	28
0.85-0.9	11
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC23080
0.9314	High Similarity	NPC179704
0.9231	High Similarity	NPC17677
0.9143	High Similarity	NPC287588
0.8978	High Similarity	NPC471489
0.8939	High Similarity	NPC249405
0.8907	High Similarity	NPC302001
0.8846	High Similarity	NPC312531
0.8846	High Similarity	NPC474904
0.8718	High Similarity	NPC55470
0.871	High Similarity	NPC162653
0.8603	High Similarity	NPC285941
0.8474	Intermediate Similarity	NPC212163
0.8474	Intermediate Similarity	NPC5374
0.8462	Intermediate Similarity	NPC190461
0.8409	Intermediate Similarity	NPC477559
0.8409	Intermediate Similarity	NPC160298
0.8409	Intermediate Similarity	NPC306902
0.8409	Intermediate Similarity	NPC266753
0.8409	Intermediate Similarity	NPC232924
0.8385	Intermediate Similarity	NPC295676
0.8362	Intermediate Similarity	NPC24954
0.8359	Intermediate Similarity	NPC308943
0.8351	Intermediate Similarity	NPC268077
0.8333	Intermediate Similarity	NPC241055
0.8325	Intermediate Similarity	NPC71124
0.8324	Intermediate Similarity	NPC24264
0.8324	Intermediate Similarity	NPC476432
0.828	Intermediate Similarity	NPC276674
0.828	Intermediate Similarity	NPC33902
0.8278	Intermediate Similarity	NPC247389
0.8268	Intermediate Similarity	NPC225774
0.8268	Intermediate Similarity	NPC302527
0.8268	Intermediate Similarity	NPC16805
0.8268	Intermediate Similarity	NPC167546
0.8256	Intermediate Similarity	NPC156728
0.8256	Intermediate Similarity	NPC244606
0.8222	Intermediate Similarity	NPC219341
0.8211	Intermediate Similarity	NPC254957
0.8205	Intermediate Similarity	NPC207971
0.8191	Intermediate Similarity	NPC320088
0.8177	Intermediate Similarity	NPC210918
0.8177	Intermediate Similarity	NPC298979
0.8167	Intermediate Similarity	NPC168409
0.8122	Intermediate Similarity	NPC86144
0.8122	Intermediate Similarity	NPC304659
0.8081	Intermediate Similarity	NPC222561
0.8079	Intermediate Similarity	NPC41178
0.8079	Intermediate Similarity	NPC216459
0.8079	Intermediate Similarity	NPC138487
0.8043	Intermediate Similarity	NPC19520
0.8043	Intermediate Similarity	NPC149090
0.804	Intermediate Similarity	NPC207873
0.804	Intermediate Similarity	NPC100573
0.8034	Intermediate Similarity	NPC146288
0.8021	Intermediate Similarity	NPC78284
0.8011	Intermediate Similarity	NPC326316
0.8011	Intermediate Similarity	NPC189470
0.8011	Intermediate Similarity	NPC81733
0.7989	Intermediate Similarity	NPC6152
0.7978	Intermediate Similarity	NPC93593
0.7978	Intermediate Similarity	NPC76079
0.7968	Intermediate Similarity	NPC114364
0.7968	Intermediate Similarity	NPC320223
0.7957	Intermediate Similarity	NPC229166
0.7957	Intermediate Similarity	NPC128560
0.7957	Intermediate Similarity	NPC199465
0.7951	Intermediate Similarity	NPC100079
0.7951	Intermediate Similarity	NPC23614
0.7943	Intermediate Similarity	NPC475959
0.7933	Intermediate Similarity	NPC31311
0.7933	Intermediate Similarity	NPC234392
0.7914	Intermediate Similarity	NPC85613
0.7914	Intermediate Similarity	NPC5167
0.7898	Intermediate Similarity	NPC219162
0.7892	Intermediate Similarity	NPC235076
0.7889	Intermediate Similarity	NPC476572
0.7877	Intermediate Similarity	NPC244112
0.7877	Intermediate Similarity	NPC99659
0.7877	Intermediate Similarity	NPC325871
0.7872	Intermediate Similarity	NPC118633
0.7872	Intermediate Similarity	NPC294790
0.7872	Intermediate Similarity	NPC148693
0.7865	Intermediate Similarity	NPC237579
0.7861	Intermediate Similarity	NPC90185
0.7849	Intermediate Similarity	NPC67978
0.7849	Intermediate Similarity	NPC303581
0.7845	Intermediate Similarity	NPC477080
0.7843	Intermediate Similarity	NPC271215
0.7843	Intermediate Similarity	NPC149471
0.7842	Intermediate Similarity	NPC248642
0.7842	Intermediate Similarity	NPC116284
0.7841	Intermediate Similarity	NPC130941
0.7831	Intermediate Similarity	NPC27887
0.7831	Intermediate Similarity	NPC126284
0.7826	Intermediate Similarity	NPC46451
0.7812	Intermediate Similarity	NPC477259
0.7812	Intermediate Similarity	NPC169387
0.7805	Intermediate Similarity	NPC298449
0.7801	Intermediate Similarity	NPC156576
0.7801	Intermediate Similarity	NPC116007
0.7796	Intermediate Similarity	NPC152212
0.7789	Intermediate Similarity	NPC32413
0.7789	Intermediate Similarity	NPC474506
0.7784	Intermediate Similarity	NPC471604
0.7784	Intermediate Similarity	NPC253883
0.7784	Intermediate Similarity	NPC90844
0.7784	Intermediate Similarity	NPC95075
0.7783	Intermediate Similarity	NPC188420
0.7778	Intermediate Similarity	NPC23219
0.7772	Intermediate Similarity	NPC238530
0.7772	Intermediate Similarity	NPC276944
0.7772	Intermediate Similarity	NPC232514
0.7771	Intermediate Similarity	NPC145304
0.7766	Intermediate Similarity	NPC308267
0.7765	Intermediate Similarity	NPC210148
0.7765	Intermediate Similarity	NPC233029
0.7737	Intermediate Similarity	NPC267408
0.7737	Intermediate Similarity	NPC470879
0.7737	Intermediate Similarity	NPC258695
0.7735	Intermediate Similarity	NPC126519
0.7735	Intermediate Similarity	NPC170503
0.7735	Intermediate Similarity	NPC203784
0.7734	Intermediate Similarity	NPC46990
0.7725	Intermediate Similarity	NPC112575
0.7721	Intermediate Similarity	NPC22481
0.772	Intermediate Similarity	NPC477186
0.7711	Intermediate Similarity	NPC38961
0.7708	Intermediate Similarity	NPC135772
0.7707	Intermediate Similarity	NPC10732
0.7705	Intermediate Similarity	NPC27410
0.7705	Intermediate Similarity	NPC166014
0.7697	Intermediate Similarity	NPC211296
0.7697	Intermediate Similarity	NPC92541
0.7696	Intermediate Similarity	NPC476574
0.7696	Intermediate Similarity	NPC155442
0.7696	Intermediate Similarity	NPC477561
0.7696	Intermediate Similarity	NPC312918
0.7692	Intermediate Similarity	NPC63152
0.7684	Intermediate Similarity	NPC16107
0.7684	Intermediate Similarity	NPC210437
0.7684	Intermediate Similarity	NPC476144
0.7684	Intermediate Similarity	NPC106295
0.7684	Intermediate Similarity	NPC51957
0.7672	Intermediate Similarity	NPC477558
0.7664	Intermediate Similarity	NPC278525
0.765	Intermediate Similarity	NPC108342
0.7641	Intermediate Similarity	NPC82763
0.764	Intermediate Similarity	NPC7467
0.763	Intermediate Similarity	NPC118121
0.7629	Intermediate Similarity	NPC214116
0.7622	Intermediate Similarity	NPC324144
0.7622	Intermediate Similarity	NPC233650
0.7617	Intermediate Similarity	NPC83511
0.7615	Intermediate Similarity	NPC182907
0.7615	Intermediate Similarity	NPC189903
0.7608	Intermediate Similarity	NPC195120
0.7608	Intermediate Similarity	NPC87560
0.7606	Intermediate Similarity	NPC474708
0.7604	Intermediate Similarity	NPC115906
0.7594	Intermediate Similarity	NPC474931
0.7594	Intermediate Similarity	NPC306555
0.7594	Intermediate Similarity	NPC81218
0.7594	Intermediate Similarity	NPC158376
0.7594	Intermediate Similarity	NPC12053
0.7594	Intermediate Similarity	NPC117188
0.7594	Intermediate Similarity	NPC205421
0.7594	Intermediate Similarity	NPC145832
0.7592	Intermediate Similarity	NPC121400
0.7584	Intermediate Similarity	NPC144863
0.7581	Intermediate Similarity	NPC96603
0.7581	Intermediate Similarity	NPC212794
0.7581	Intermediate Similarity	NPC13504
0.7581	Intermediate Similarity	NPC78222
0.7581	Intermediate Similarity	NPC477563
0.7581	Intermediate Similarity	NPC196447
0.7581	Intermediate Similarity	NPC253043
0.7581	Intermediate Similarity	NPC136508
0.7581	Intermediate Similarity	NPC134858
0.7581	Intermediate Similarity	NPC306843
0.758	Intermediate Similarity	NPC166722
0.7576	Intermediate Similarity	NPC477258
0.7573	Intermediate Similarity	NPC61731
0.7573	Intermediate Similarity	NPC186569
0.7569	Intermediate Similarity	NPC26601
0.7568	Intermediate Similarity	NPC60186
0.7565	Intermediate Similarity	NPC275132
0.7561	Intermediate Similarity	NPC85661
0.7554	Intermediate Similarity	NPC111485
0.7554	Intermediate Similarity	NPC106786
0.7553	Intermediate Similarity	NPC86469
0.7553	Intermediate Similarity	NPC475845
0.7552	Intermediate Similarity	NPC220961
0.7543	Intermediate Similarity	NPC188163
0.7543	Intermediate Similarity	NPC213206
0.7543	Intermediate Similarity	NPC474915
0.7543	Intermediate Similarity	NPC328750
0.7541	Intermediate Similarity	NPC186063
0.7539	Intermediate Similarity	NPC283810
0.7538	Intermediate Similarity	NPC24228

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 NPC193906 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	240
0.1-0.2	726
0.2-0.3	893
0.3-0.4	1600
0.4-0.5	2846
0.5-0.6	2218
0.6-0.7	567
0.7-0.8	60
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.841	Intermediate Similarity	NPD4859	Phase 1
0.7826	Intermediate Similarity	NPD3763	Approved
0.7697	Intermediate Similarity	NPD3641	Approved
0.7697	Intermediate Similarity	NPD3639	Approved
0.7697	Intermediate Similarity	NPD3640	Phase 3
0.7684	Intermediate Similarity	NPD4584	Approved
0.7604	Intermediate Similarity	NPD2968	Approved
0.7604	Intermediate Similarity	NPD2971	Approved
0.7543	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD5071	Phase 2
0.7397	Intermediate Similarity	NPD6625	Approved
0.7374	Intermediate Similarity	NPD2490	Approved
0.7374	Intermediate Similarity	NPD2488	Approved
0.7368	Intermediate Similarity	NPD3815	Phase 1
0.7368	Intermediate Similarity	NPD3816	Phase 1
0.7363	Intermediate Similarity	NPD7238	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7281	Phase 3
0.7333	Intermediate Similarity	NPD7280	Phase 3
0.7333	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD4420	Approved
0.7326	Intermediate Similarity	NPD6533	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD5896	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD7922	Phase 1
0.7318	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD6723	Discontinued
0.7313	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5978	Approved
0.7312	Intermediate Similarity	NPD5977	Approved
0.729	Intermediate Similarity	NPD7858	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD2974	Approved
0.7277	Intermediate Similarity	NPD4481	Phase 3
0.7277	Intermediate Similarity	NPD2973	Approved
0.7277	Intermediate Similarity	NPD2975	Approved
0.7269	Intermediate Similarity	NPD7279	Phase 2
0.7269	Intermediate Similarity	NPD7278	Phase 2
0.7268	Intermediate Similarity	NPD5006	Approved
0.7268	Intermediate Similarity	NPD956	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD5005	Approved
0.7249	Intermediate Similarity	NPD6037	Discontinued
0.7216	Intermediate Similarity	NPD7479	Phase 2
0.7214	Intermediate Similarity	NPD7262	Phase 1
0.7195	Intermediate Similarity	NPD4885	Approved
0.7182	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD5183	Approved
0.7173	Intermediate Similarity	NPD5186	Approved
0.7171	Intermediate Similarity	NPD4580	Approved
0.7165	Intermediate Similarity	NPD5313	Approved
0.7165	Intermediate Similarity	NPD5312	Approved
0.7158	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5582	Discontinued
0.7136	Intermediate Similarity	NPD3452	Approved
0.7136	Intermediate Similarity	NPD2494	Approved
0.7136	Intermediate Similarity	NPD2493	Approved
0.7136	Intermediate Similarity	NPD3450	Approved
0.7123	Intermediate Similarity	NPD7223	Discontinued
0.7123	Intermediate Similarity	NPD7224	Discontinued
0.7123	Intermediate Similarity	NPD7225	Discontinued
0.7113	Intermediate Similarity	NPD8251	Approved
0.7113	Intermediate Similarity	NPD8099	Discontinued
0.7113	Intermediate Similarity	NPD8252	Approved
0.7109	Intermediate Similarity	NPD4997	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD8149	Discontinued
0.7098	Intermediate Similarity	NPD2898	Approved
0.7094	Intermediate Similarity	NPD6493	Phase 3
0.7092	Intermediate Similarity	NPD6297	Approved
0.7089	Intermediate Similarity	NPD7571	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD4107	Approved
0.7083	Intermediate Similarity	NPD3051	Approved
0.7077	Intermediate Similarity	NPD8156	Discontinued
0.7062	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7110	Phase 1
0.7059	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD5433	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD2420	Approved
0.7049	Intermediate Similarity	NPD2421	Approved
0.7043	Intermediate Similarity	NPD4017	Approved
0.7035	Intermediate Similarity	NPD6021	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD4582	Approved
0.7033	Intermediate Similarity	NPD4583	Approved
0.7033	Intermediate Similarity	NPD3301	Approved
0.7031	Intermediate Similarity	NPD6457	Approved
0.7031	Intermediate Similarity	NPD6107	Approved
0.703	Intermediate Similarity	NPD6656	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6031	Approved
0.7027	Intermediate Similarity	NPD6030	Approved
0.7021	Intermediate Similarity	NPD7298	Approved
0.7015	Intermediate Similarity	NPD3349	Phase 2
0.7005	Intermediate Similarity	NPD2899	Discontinued
0.7005	Intermediate Similarity	NPD7255	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD8318	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6788	Approved
0.7	Intermediate Similarity	NPD7174	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD6747	Phase 1
0.6986	Remote Similarity	NPD4004	Approved
0.6986	Remote Similarity	NPD4002	Approved
0.698	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD5938	Phase 3
0.6971	Remote Similarity	NPD4482	Phase 3
0.6959	Remote Similarity	NPD2970	Approved
0.6959	Remote Similarity	NPD2969	Approved
0.6954	Remote Similarity	NPD3920	Phase 2
0.6952	Remote Similarity	NPD4040	Phase 1
0.695	Remote Similarity	NPD6851	Approved
0.695	Remote Similarity	NPD6853	Approved
0.6935	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD7291	Discontinued
0.6923	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD27	Approved
0.6923	Remote Similarity	NPD5457	Discontinued
0.6923	Remote Similarity	NPD2489	Approved
0.6919	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD4846	Phase 2
0.6916	Remote Similarity	NPD683	Approved
0.6912	Remote Similarity	NPD3924	Approved
0.6912	Remote Similarity	NPD3923	Approved
0.6912	Remote Similarity	NPD3922	Approved
0.6912	Remote Similarity	NPD3921	Approved
0.6907	Remote Similarity	NPD4166	Phase 2
0.6905	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD5600	Discontinued
0.689	Remote Similarity	NPD6238	Discontinued
0.689	Remote Similarity	NPD6321	Discontinued
0.6869	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD5914	Approved
0.6866	Remote Similarity	NPD8053	Approved
0.6866	Remote Similarity	NPD5025	Approved
0.6866	Remote Similarity	NPD8054	Approved
0.6859	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD3057	Approved
0.6854	Remote Similarity	NPD5950	Discontinued
0.6853	Remote Similarity	NPD4498	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD4727	Phase 1
0.6839	Remote Similarity	NPD7400	Phase 3
0.6837	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.6834	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6834	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD6875	Approved
0.6825	Remote Similarity	NPD6876	Approved
0.6822	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD5966	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD5610	Approved
0.6789	Remote Similarity	NPD4772	Phase 2
0.6789	Remote Similarity	NPD4773	Phase 2
0.6788	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD7831	Phase 2
0.6788	Remote Similarity	NPD7833	Phase 2
0.6786	Remote Similarity	NPD4083	Discontinued
0.6784	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD8016	Phase 3
0.6783	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD6618	Phase 2
0.6782	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD5564	Approved
0.6777	Remote Similarity	NPD2972	Approved
0.6777	Remote Similarity	NPD2491	Approved
0.6777	Remote Similarity	NPD3448	Approved
0.6777	Remote Similarity	NPD3533	Approved
0.6776	Remote Similarity	NPD5658	Approved
0.6769	Remote Similarity	NPD7802	Discontinued
0.6769	Remote Similarity	NPD3983	Phase 3
0.6769	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7906	Approved
0.6762	Remote Similarity	NPD6612	Phase 2
0.676	Remote Similarity	NPD3110	Approved
0.676	Remote Similarity	NPD3109	Approved
0.6757	Remote Similarity	NPD5241	Discontinued
0.6755	Remote Similarity	NPD7427	Discontinued
0.6736	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD5810	Discontinued
0.6732	Remote Similarity	NPD3408	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD5429	Discontinued
0.6728	Remote Similarity	NPD7827	Phase 1
0.6724	Remote Similarity	NPD6517	Phase 3
0.6719	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD6874	Approved
0.6714	Remote Similarity	NPD6250	Discontinued
0.6704	Remote Similarity	NPD4474	Approved
0.6704	Remote Similarity	NPD4475	Approved
0.6703	Remote Similarity	NPD5754	Discontinued
0.6702	Remote Similarity	NPD6386	Approved
0.6702	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD6385	Approved
0.6699	Remote Similarity	NPD5641	Discontinued
0.6699	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD7034	Discontinued
0.6698	Remote Similarity	NPD7627	Approved
0.6698	Remote Similarity	NPD7626	Approved
0.6697	Remote Similarity	NPD5519	Discontinued
0.6685	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD6357	Discontinued
0.6684	Remote Similarity	NPD2821	Approved
0.6683	Remote Similarity	NPD7190	Clinical (unspecified phase)

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