NPASS Compound

Structure

NPC199273 OpenBabel07101718192D 23 25 0 0 1 0 0 0 0 0999 V2000 4.1586 -2.2515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0246 -0.7515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5605 -3.7515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9036 -0.7515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1708 0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2926 -0.7515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4265 -2.2515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0376 -2.2515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1586 -1.2515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5605 -2.7515 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0376 -1.2515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3890 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4265 -1.2515 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1715 -2.7515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6945 -2.2515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1715 -0.7515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5605 -0.7515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6945 -1.2515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6945 0.3345 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 -0.1715 -3.7515 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6945 1.3345 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7818 0.6235 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 9 1 0 0 0 0 4 11 1 0 0 0 0 5 12 1 0 0 0 0 6 9 2 0 0 0 0 7 10 1 0 0 0 0 7 13 1 0 0 0 0 8 11 2 0 0 0 0 8 14 1 0 0 0 0 10 3 1 6 0 0 0 10 15 1 0 0 0 0 11 16 1 0 0 0 0 12 17 2 0 0 0 0 12 19 1 0 0 0 0 13 6 1 6 0 0 0 13 17 1 0 0 0 0 14 15 2 0 0 0 0 14 21 1 0 0 0 0 15 18 1 0 0 0 0 16 18 2 0 0 0 0 16 20 1 0 0 0 0 17 18 1 0 0 0 0 19 20 1 0 0 0 0 19 22 2 0 0 0 0 20 23 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	310.16
Volume:	336.722
LogP:	6.132
LogD:	3.828
LogS:	-3.627
# Rotatable Bonds:	1
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.591
Synthetic Accessibility Score:	3.325
Fsp3:	0.3
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	3
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.045
MDCK Permeability:	6.416563337552361e-06
Pgp-inhibitor:	0.005
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.158
20% Bioavailability (F20%):	0.644
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	98.23747253417969%
Volume Distribution (VD):	0.631
Pgp-substrate:	2.6251344680786133%

ADMET: Metabolism

CYP1A2-inhibitor:	0.909
CYP1A2-substrate:	0.89
CYP2C19-inhibitor:	0.221
CYP2C19-substrate:	0.37
CYP2C9-inhibitor:	0.739
CYP2C9-substrate:	0.839
CYP2D6-inhibitor:	0.585
CYP2D6-substrate:	0.305
CYP3A4-inhibitor:	0.087
CYP3A4-substrate:	0.21

ADMET: Excretion

Clearance (CL):	7.983
Half-life (T1/2):	0.616

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.094
Drug-inuced Liver Injury (DILI):	0.825
AMES Toxicity:	0.502
Rat Oral Acute Toxicity:	0.477
Maximum Recommended Daily Dose:	0.943
Skin Sensitization:	0.951
Carcinogencity:	0.531
Eye Corrosion:	0.356
Eye Irritation:	0.967
Respiratory Toxicity:	0.642

Download Data

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

Natural Product: NPC199273

Natural Product ID:	NPC199273
*Common Name:**	Elisabatin A
IUPAC Name:	(4S,6S)-7-hydroxy-3,6,9-trimethyl-4-(2-methylprop-1-enyl)-5,6-dihydro-4H-phenalene-1,2-dione
Synonyms:
Standard InCHIKey:	JVQJPMIBFYBOEO-GXFFZTMASA-N
Standard InCHI:	InChI=1S/C20H22O3/c1-9(2)6-13-7-10(3)15-14(21)8-11(4)16-18(15)17(13)12(5)19(22)20(16)23/h6,8,10,13,21H,7H2,1-5H3/t10-,13+/m0/s1
SMILES:	CC(=C[C@@H]1C[C@H](C)c2c(cc(C)c3c2C1=C(C)C(=O)C3=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL494655
PubChem CID:	397069
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003398] Amphilectane, neoamphilectane, cycloamphilectane, and adociane diterpenoids

*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
NPO31261	Pseudopterogorgia elisabethae	Species	Gorgoniidae	Eukaryota	n.a.	West Indian sea	n.a.	PMID[10425124]
NPO31261	Pseudopterogorgia elisabethae	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10822593]
NPO31261	Pseudopterogorgia elisabethae	Species	Gorgoniidae	Eukaryota	n.a.	West Indian sea	n.a.	PMID[11170678]
NPO31261	Pseudopterogorgia elisabethae	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12828474]
NPO31261	Pseudopterogorgia elisabethae	Species	Gorgoniidae	Eukaryota	n.a.	Colombian	n.a.	PMID[15497938]
NPO31261	Pseudopterogorgia elisabethae	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17715964]
NPO31261	Pseudopterogorgia elisabethae	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21978379]

☑ 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
GI50	55
IC50	6
LD50	2
Others	4

Activity Type	# Activity
Cell Line	57
Individual Protein	4
Organism	1
Others	1
SINGLE PROTEIN	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	16292.96	nM	PMID[524070]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	15031.42	nM	PMID[524070]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	13458.6	nM	PMID[524070]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	17619.76	nM	PMID[524070]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	21928.05	nM	PMID[524070]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	13427.65	nM	PMID[524070]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	15310.87	nM	PMID[524070]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	17947.34	nM	PMID[524070]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	13614.45	nM	PMID[524070]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	15958.79	nM	PMID[524070]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	19098.53	nM	PMID[524070]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	17179.08	nM	PMID[524070]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	14454.4	nM	PMID[524070]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	28641.78	nM	PMID[524070]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	17378.01	nM	PMID[524070]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	18923.44	nM	PMID[524070]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	13803.84	nM	PMID[524070]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	16865.53	nM	PMID[524070]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	24660.39	nM	PMID[524070]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	14421.15	nM	PMID[524070]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	15631.48	nM	PMID[524070]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	22284.35	nM	PMID[524070]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	16069.41	nM	PMID[524070]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	15310.87	nM	PMID[524070]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	15631.48	nM	PMID[524070]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	13995.87	nM	PMID[524070]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	18197.01	nM	PMID[524070]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	12912.19	nM	PMID[524070]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	16255.49	nM	PMID[524070]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	10939.56	nM	PMID[524070]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	13740.42	nM	PMID[524070]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	10139.11	nM	PMID[524070]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	21827.3	nM	PMID[524070]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	17378.01	nM	PMID[524070]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	15240.53	nM	PMID[524070]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	13551.89	nM	PMID[524070]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	14996.85	nM	PMID[524070]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	14256.08	nM	PMID[524070]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	22750.97	nM	PMID[524070]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	10519.62	nM	PMID[524070]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	16672.47	nM	PMID[524070]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	18030.18	nM	PMID[524070]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	14723.13	nM	PMID[524070]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	15595.53	nM	PMID[524070]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	16557.7	nM	PMID[524070]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	16710.91	nM	PMID[524070]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	14689.26	nM	PMID[524070]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	19588.45	nM	PMID[524070]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	15922.09	nM	PMID[524070]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	17579.24	nM	PMID[524070]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	22387.21	nM	PMID[524070]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	16292.96	nM	PMID[524070]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	19364.22	nM	PMID[524070]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	15523.87	nM	PMID[524070]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	17660.38	nM	PMID[524070]
NPT4582	Individual Protein	Transitional endoplasmic reticulum ATPase	Homo sapiens	IC50	>	100000.0	nM	PMID[524071]
NPT4848	Individual Protein	Heat shock 70 kDa protein 1	Homo sapiens	IC50	>	100000.0	nM	PMID[524071]
NPT3820	Individual Protein	Eukaryotic initiation factor 4A-I	Homo sapiens	Kis	=	55.04	uM	PMID[524071]
NPT3820	Individual Protein	Eukaryotic initiation factor 4A-I	Homo sapiens	Inhibition	=	34.0	%	PMID[524071]
NPT81	Cell Line	A549	Homo sapiens	LD50	=	40.2	uM	PMID[524071]
NPT784	Cell Line	MDA-MB-468	Homo sapiens	LD50	=	35.2	uM	PMID[524071]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	Activity	=	21.0	%	PMID[524069]
NPT24277	SINGLE PROTEIN	ATP-dependent RNA helicase DDX3X	Homo sapiens	IC50	>	100000.0	nM	PMID[524071]
NPT2	Others	Unspecified		Ratio IC50	=	20.0	n.a.	PMID[524071]
NPT27113	SINGLE PROTEIN	ATP-dependent RNA helicase DDX39A	Homo sapiens	IC50	>	100000.0	nM	PMID[524071]
NPT27114	SINGLE PROTEIN	Probable ATP-dependent RNA helicase DDX17	Homo sapiens	IC50	>	100000.0	nM	PMID[524071]
NPT27115	SINGLE PROTEIN	Heat shock protein HSP 60	Homo sapiens	IC50	>	100000.0	nM	PMID[524071]

☑ 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 NPC199273 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	295
0.1-0.2	1553
0.2-0.3	3343
0.3-0.4	9960
0.4-0.5	9336
0.5-0.6	6520
0.6-0.7	8112
0.7-0.8	3055
0.8-0.85	379
0.85-0.9	114
0.9-0.95	25
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.975	High Similarity	NPC72667
0.9669	High Similarity	NPC96024
0.9667	High Similarity	NPC254492
0.9661	High Similarity	NPC282577
0.959	High Similarity	NPC171460
0.9587	High Similarity	NPC69424
0.9587	High Similarity	NPC84672
0.9587	High Similarity	NPC176130
0.9587	High Similarity	NPC78364
0.9431	High Similarity	NPC276238
0.9421	High Similarity	NPC123506
0.9412	High Similarity	NPC154696
0.9355	High Similarity	NPC108129
0.928	High Similarity	NPC471851
0.9274	High Similarity	NPC303910
0.9256	High Similarity	NPC273683
0.9194	High Similarity	NPC3009
0.9167	High Similarity	NPC259703
0.9167	High Similarity	NPC32322
0.9134	High Similarity	NPC477139
0.9134	High Similarity	NPC138472
0.9134	High Similarity	NPC78307
0.9062	High Similarity	NPC202225
0.8984	High Similarity	NPC111845
0.8952	High Similarity	NPC137750
0.8943	High Similarity	NPC275145
0.8915	High Similarity	NPC50924
0.8898	High Similarity	NPC253488
0.888	High Similarity	NPC15837
0.8862	High Similarity	NPC176208
0.8855	High Similarity	NPC53001
0.8855	High Similarity	NPC36868
0.8855	High Similarity	NPC475957
0.8852	High Similarity	NPC190971
0.8846	High Similarity	NPC153088
0.8837	High Similarity	NPC59459
0.8828	High Similarity	NPC41847
0.8819	High Similarity	NPC117899
0.879	High Similarity	NPC471187
0.8788	High Similarity	NPC230811
0.8788	High Similarity	NPC87723
0.878	High Similarity	NPC162935
0.878	High Similarity	NPC120545
0.878	High Similarity	NPC249340
0.8779	High Similarity	NPC191976
0.8779	High Similarity	NPC471670
0.877	High Similarity	NPC478121
0.8769	High Similarity	NPC12070
0.874	High Similarity	NPC48248
0.874	High Similarity	NPC193203
0.873	High Similarity	NPC160499
0.873	High Similarity	NPC71610
0.872	High Similarity	NPC181334
0.872	High Similarity	NPC173978
0.8712	High Similarity	NPC277559
0.871	High Similarity	NPC11250
0.871	High Similarity	NPC307174
0.871	High Similarity	NPC91478
0.8702	High Similarity	NPC249272
0.8702	High Similarity	NPC290803
0.8702	High Similarity	NPC283088
0.8699	High Similarity	NPC241001
0.8692	High Similarity	NPC114183
0.8692	High Similarity	NPC267205
0.8692	High Similarity	NPC53896
0.8682	High Similarity	NPC239134
0.8682	High Similarity	NPC244699
0.8682	High Similarity	NPC72669
0.8682	High Similarity	NPC18798
0.8682	High Similarity	NPC93015
0.8682	High Similarity	NPC474517
0.8672	High Similarity	NPC34414
0.8672	High Similarity	NPC146647
0.8667	High Similarity	NPC322197
0.8657	High Similarity	NPC181560
0.8657	High Similarity	NPC169452
0.8655	High Similarity	NPC242136
0.8626	High Similarity	NPC270899
0.8615	High Similarity	NPC312560
0.8615	High Similarity	NPC58685
0.8615	High Similarity	NPC165612
0.8615	High Similarity	NPC175738
0.8615	High Similarity	NPC183103
0.8605	High Similarity	NPC27659
0.8595	High Similarity	NPC477453
0.8594	High Similarity	NPC229894
0.8583	High Similarity	NPC474737
0.8583	High Similarity	NPC3224
0.8582	High Similarity	NPC242994
0.8582	High Similarity	NPC138099
0.8571	High Similarity	NPC68756
0.8571	High Similarity	NPC142956
0.8571	High Similarity	NPC152525
0.8571	High Similarity	NPC471905
0.8571	High Similarity	NPC164014
0.8571	High Similarity	NPC49911
0.8571	High Similarity	NPC231717
0.8561	High Similarity	NPC22644
0.8561	High Similarity	NPC80035
0.856	High Similarity	NPC121168
0.855	High Similarity	NPC263817
0.855	High Similarity	NPC115458
0.855	High Similarity	NPC52407
0.855	High Similarity	NPC225051
0.8538	High Similarity	NPC164295
0.8538	High Similarity	NPC476847
0.8538	High Similarity	NPC85342
0.8529	High Similarity	NPC193555
0.8527	High Similarity	NPC92624
0.8527	High Similarity	NPC99731
0.8519	High Similarity	NPC471853
0.8516	High Similarity	NPC471530
0.8516	High Similarity	NPC19432
0.8507	High Similarity	NPC4214
0.8507	High Similarity	NPC13715
0.8504	High Similarity	NPC477454
0.8496	Intermediate Similarity	NPC472308
0.8496	Intermediate Similarity	NPC474311
0.8496	Intermediate Similarity	NPC254847
0.8496	Intermediate Similarity	NPC86524
0.8496	Intermediate Similarity	NPC118919
0.8492	Intermediate Similarity	NPC198014
0.8485	Intermediate Similarity	NPC282780
0.8485	Intermediate Similarity	NPC161964
0.8485	Intermediate Similarity	NPC287604
0.8485	Intermediate Similarity	NPC166480
0.8485	Intermediate Similarity	NPC472262
0.848	Intermediate Similarity	NPC253627
0.8468	Intermediate Similarity	NPC318552
0.8468	Intermediate Similarity	NPC285829
0.8468	Intermediate Similarity	NPC206778
0.8468	Intermediate Similarity	NPC190501
0.8467	Intermediate Similarity	NPC451542
0.8467	Intermediate Similarity	NPC295712
0.8467	Intermediate Similarity	NPC313047
0.8467	Intermediate Similarity	NPC100242
0.8467	Intermediate Similarity	NPC293545
0.8467	Intermediate Similarity	NPC474203
0.8467	Intermediate Similarity	NPC174905
0.8462	Intermediate Similarity	NPC55949
0.8462	Intermediate Similarity	NPC470725
0.8462	Intermediate Similarity	NPC259942
0.8462	Intermediate Similarity	NPC151477
0.8455	Intermediate Similarity	NPC328694
0.845	Intermediate Similarity	NPC282923
0.8438	Intermediate Similarity	NPC473691
0.8438	Intermediate Similarity	NPC306765
0.8433	Intermediate Similarity	NPC53414
0.8433	Intermediate Similarity	NPC471452
0.8433	Intermediate Similarity	NPC53206
0.8425	Intermediate Similarity	NPC474766
0.8425	Intermediate Similarity	NPC234890
0.8425	Intermediate Similarity	NPC74507
0.8421	Intermediate Similarity	NPC258502
0.8421	Intermediate Similarity	NPC477596
0.8417	Intermediate Similarity	NPC250323
0.8413	Intermediate Similarity	NPC300274
0.8409	Intermediate Similarity	NPC37299
0.8409	Intermediate Similarity	NPC314048
0.8409	Intermediate Similarity	NPC49742
0.8409	Intermediate Similarity	NPC180261
0.8409	Intermediate Similarity	NPC4170
0.84	Intermediate Similarity	NPC216216
0.8397	Intermediate Similarity	NPC17083
0.8397	Intermediate Similarity	NPC291001
0.8394	Intermediate Similarity	NPC248068
0.8394	Intermediate Similarity	NPC477209
0.8394	Intermediate Similarity	NPC474961
0.8394	Intermediate Similarity	NPC239136
0.8394	Intermediate Similarity	NPC308572
0.8394	Intermediate Similarity	NPC135524
0.8394	Intermediate Similarity	NPC19631
0.8394	Intermediate Similarity	NPC184935
0.8387	Intermediate Similarity	NPC473767
0.8387	Intermediate Similarity	NPC42657
0.8385	Intermediate Similarity	NPC25736
0.8385	Intermediate Similarity	NPC278928
0.8382	Intermediate Similarity	NPC168471
0.8376	Intermediate Similarity	NPC21594
0.837	Intermediate Similarity	NPC416
0.837	Intermediate Similarity	NPC61398
0.8359	Intermediate Similarity	NPC131799
0.8359	Intermediate Similarity	NPC87985
0.8358	Intermediate Similarity	NPC272268
0.8358	Intermediate Similarity	NPC7464
0.8358	Intermediate Similarity	NPC315275
0.8358	Intermediate Similarity	NPC155211
0.8346	Intermediate Similarity	NPC174991
0.8346	Intermediate Similarity	NPC375356
0.8346	Intermediate Similarity	NPC477594
0.8345	Intermediate Similarity	NPC478160
0.8333	Intermediate Similarity	NPC176279
0.8333	Intermediate Similarity	NPC260323
0.8333	Intermediate Similarity	NPC295034
0.8333	Intermediate Similarity	NPC296752
0.8321	Intermediate Similarity	NPC136588
0.8321	Intermediate Similarity	NPC477275
0.8321	Intermediate Similarity	NPC199253
0.8321	Intermediate Similarity	NPC305845
0.8321	Intermediate Similarity	NPC198305

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 NPC199273 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	320
0.1-0.2	970
0.2-0.3	1346
0.3-0.4	2618
0.4-0.5	2144
0.5-0.6	1187
0.6-0.7	466
0.7-0.8	91
0.8-0.85	7
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8618	High Similarity	NPD2932	Approved
0.8496	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.848	Intermediate Similarity	NPD1201	Approved
0.8468	Intermediate Similarity	NPD3019	Approved
0.8387	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.8273	Intermediate Similarity	NPD7390	Discontinued
0.8217	Intermediate Similarity	NPD1470	Approved
0.8145	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8029	Intermediate Similarity	NPD5406	Approved
0.8029	Intermediate Similarity	NPD5408	Approved
0.8029	Intermediate Similarity	NPD5404	Approved
0.8029	Intermediate Similarity	NPD5405	Approved
0.7832	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD3026	Approved
0.7829	Intermediate Similarity	NPD3023	Approved
0.7826	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD7635	Approved
0.7817	Intermediate Similarity	NPD3300	Phase 2
0.7812	Intermediate Similarity	NPD3024	Approved
0.7812	Intermediate Similarity	NPD3025	Approved
0.7801	Intermediate Similarity	NPD7003	Approved
0.7727	Intermediate Similarity	NPD1283	Approved
0.7705	Intermediate Similarity	NPD2342	Discontinued
0.7698	Intermediate Similarity	NPD5951	Approved
0.7674	Intermediate Similarity	NPD1651	Approved
0.7669	Intermediate Similarity	NPD1164	Approved
0.7615	Intermediate Similarity	NPD4626	Approved
0.7591	Intermediate Similarity	NPD6663	Approved
0.7589	Intermediate Similarity	NPD2346	Discontinued
0.7581	Intermediate Similarity	NPD4750	Phase 3
0.7576	Intermediate Similarity	NPD3972	Approved
0.7563	Intermediate Similarity	NPD3020	Approved
0.7556	Intermediate Similarity	NPD5736	Approved
0.7542	Intermediate Similarity	NPD288	Approved
0.7536	Intermediate Similarity	NPD943	Approved
0.7518	Intermediate Similarity	NPD6099	Approved
0.7518	Intermediate Similarity	NPD6100	Approved
0.7518	Intermediate Similarity	NPD2935	Discontinued
0.75	Intermediate Similarity	NPD1281	Approved
0.75	Intermediate Similarity	NPD7458	Discontinued
0.7481	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD2798	Approved
0.7481	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD3091	Approved
0.7458	Intermediate Similarity	NPD844	Approved
0.7447	Intermediate Similarity	NPD2799	Discontinued
0.7431	Intermediate Similarity	NPD8166	Discontinued
0.7429	Intermediate Similarity	NPD1607	Approved
0.7419	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD3764	Approved
0.7389	Intermediate Similarity	NPD7473	Discontinued
0.7383	Intermediate Similarity	NPD3226	Approved
0.7361	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD6959	Discontinued
0.7348	Intermediate Similarity	NPD4059	Approved
0.7347	Intermediate Similarity	NPD2534	Approved
0.7347	Intermediate Similarity	NPD2532	Approved
0.7347	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD2533	Approved
0.7343	Intermediate Similarity	NPD2344	Approved
0.7333	Intermediate Similarity	NPD1876	Approved
0.7324	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD4878	Approved
0.7311	Intermediate Similarity	NPD2860	Approved
0.7311	Intermediate Similarity	NPD2859	Approved
0.7311	Intermediate Similarity	NPD1809	Phase 2
0.731	Intermediate Similarity	NPD3750	Approved
0.7308	Intermediate Similarity	NPD6232	Discontinued
0.7303	Intermediate Similarity	NPD7819	Suspended
0.7302	Intermediate Similarity	NPD3021	Approved
0.7302	Intermediate Similarity	NPD3022	Approved
0.7288	Intermediate Similarity	NPD845	Approved
0.7286	Intermediate Similarity	NPD1240	Approved
0.7273	Intermediate Similarity	NPD5691	Approved
0.7267	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD1755	Approved
0.7259	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD3092	Approved
0.7236	Intermediate Similarity	NPD1930	Approved
0.7236	Intermediate Similarity	NPD1929	Approved
0.7236	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD2933	Approved
0.7227	Intermediate Similarity	NPD2934	Approved
0.7222	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD2286	Discontinued
0.7203	Intermediate Similarity	NPD1510	Phase 2
0.7197	Intermediate Similarity	NPD9545	Approved
0.7192	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD6273	Approved
0.7163	Intermediate Similarity	NPD2979	Phase 3
0.7153	Intermediate Similarity	NPD2797	Approved
0.7143	Intermediate Similarity	NPD4093	Discontinued
0.7143	Intermediate Similarity	NPD2309	Approved
0.7143	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3268	Approved
0.7131	Intermediate Similarity	NPD2066	Phase 3
0.7114	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD3495	Discontinued
0.7092	Intermediate Similarity	NPD8032	Phase 2
0.709	Intermediate Similarity	NPD3095	Discontinued
0.7087	Intermediate Similarity	NPD9266	Approved
0.7087	Intermediate Similarity	NPD74	Approved
0.7083	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD4628	Phase 3
0.7073	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6651	Approved
0.7059	Intermediate Similarity	NPD1608	Approved
0.7045	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD9493	Approved
0.7042	Intermediate Similarity	NPD4060	Phase 1
0.7029	Intermediate Similarity	NPD3094	Phase 2
0.7027	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD2313	Discontinued
0.7008	Intermediate Similarity	NPD9267	Approved
0.7008	Intermediate Similarity	NPD9263	Approved
0.7008	Intermediate Similarity	NPD9264	Approved
0.7007	Intermediate Similarity	NPD2800	Approved
0.6993	Remote Similarity	NPD4380	Phase 2
0.6992	Remote Similarity	NPD7610	Discontinued
0.6986	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6020	Phase 2
0.6975	Remote Similarity	NPD5844	Phase 1
0.6966	Remote Similarity	NPD4308	Phase 3
0.6966	Remote Similarity	NPD3748	Approved
0.6963	Remote Similarity	NPD1751	Approved
0.695	Remote Similarity	NPD4625	Phase 3
0.695	Remote Similarity	NPD7008	Discontinued
0.695	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD4097	Suspended
0.6939	Remote Similarity	NPD1549	Phase 2
0.6934	Remote Similarity	NPD9269	Phase 2
0.6933	Remote Similarity	NPD1511	Approved
0.6929	Remote Similarity	NPD9494	Approved
0.6918	Remote Similarity	NPD4477	Approved
0.6918	Remote Similarity	NPD4476	Approved
0.6918	Remote Similarity	NPD2531	Phase 2
0.6918	Remote Similarity	NPD2796	Approved
0.6918	Remote Similarity	NPD2438	Suspended
0.6912	Remote Similarity	NPD4879	Approved
0.6905	Remote Similarity	NPD1237	Approved
0.6903	Remote Similarity	NPD1934	Approved
0.6899	Remote Similarity	NPD1792	Phase 2
0.6894	Remote Similarity	NPD497	Approved
0.6889	Remote Similarity	NPD9268	Approved
0.6884	Remote Similarity	NPD4749	Approved
0.688	Remote Similarity	NPD940	Approved
0.688	Remote Similarity	NPD846	Approved
0.6871	Remote Similarity	NPD1471	Phase 3
0.6871	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD2801	Approved
0.6845	Remote Similarity	NPD8150	Discontinued
0.6842	Remote Similarity	NPD3317	Approved
0.6842	Remote Similarity	NPD1512	Approved
0.6839	Remote Similarity	NPD7411	Suspended
0.6838	Remote Similarity	NPD17	Approved
0.6835	Remote Similarity	NPD7075	Discontinued
0.6818	Remote Similarity	NPD496	Approved
0.6818	Remote Similarity	NPD1241	Discontinued
0.6818	Remote Similarity	NPD2228	Approved
0.6818	Remote Similarity	NPD498	Approved
0.6818	Remote Similarity	NPD2229	Approved
0.6818	Remote Similarity	NPD495	Approved
0.6818	Remote Similarity	NPD2234	Approved
0.6815	Remote Similarity	NPD5303	Approved
0.6815	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD7009	Phase 2
0.6815	Remote Similarity	NPD5304	Approved
0.681	Remote Similarity	NPD7177	Discontinued
0.6809	Remote Similarity	NPD3635	Approved
0.6809	Remote Similarity	NPD3637	Approved
0.6809	Remote Similarity	NPD4208	Discontinued
0.6809	Remote Similarity	NPD3636	Approved
0.6794	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD7340	Approved
0.6786	Remote Similarity	NPD3266	Approved
0.6786	Remote Similarity	NPD3267	Approved
0.6777	Remote Similarity	NPD7631	Approved
0.6776	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD7028	Phase 2
0.677	Remote Similarity	NPD5711	Approved
0.677	Remote Similarity	NPD5710	Approved
0.6765	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD2605	Approved
0.6761	Remote Similarity	NPD2606	Approved
0.6759	Remote Similarity	NPD230	Phase 1
0.6755	Remote Similarity	NPD7236	Approved
0.6752	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD5031	Approved
0.6747	Remote Similarity	NPD5027	Approved
0.6747	Remote Similarity	NPD5029	Approved
0.6746	Remote Similarity	NPD1932	Approved
0.6739	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD2195	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