NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	242.09
Volume:	252.879
LogP:	2.64
LogD:	2.221
LogS:	-4.201
# Rotatable Bonds:	0
TPSA:	43.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.701
Synthetic Accessibility Score:	3.353
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.625
MDCK Permeability:	3.4072796552209184e-05
Pgp-inhibitor:	0.569
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.16
Plasma Protein Binding (PPB):	89.87845611572266%
Volume Distribution (VD):	1.047
Pgp-substrate:	5.904287815093994%

ADMET: Metabolism

CYP1A2-inhibitor:	0.632
CYP1A2-substrate:	0.536
CYP2C19-inhibitor:	0.761
CYP2C19-substrate:	0.354
CYP2C9-inhibitor:	0.404
CYP2C9-substrate:	0.148
CYP2D6-inhibitor:	0.032
CYP2D6-substrate:	0.374
CYP3A4-inhibitor:	0.062
CYP3A4-substrate:	0.263

ADMET: Excretion

Clearance (CL):	0.547
Half-life (T1/2):	0.101

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.242
Drug-inuced Liver Injury (DILI):	0.911
AMES Toxicity:	0.952
Rat Oral Acute Toxicity:	0.688
Maximum Recommended Daily Dose:	0.875
Skin Sensitization:	0.575
Carcinogencity:	0.794
Eye Corrosion:	0.008
Eye Irritation:	0.396
Respiratory Toxicity:	0.909

Download Data

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

Natural Product: NPC137315

Natural Product ID:	NPC137315
*Common Name:**	3,3-Dimethyl-2,4-Dihydrobenzo[G]Chromene-5,10-Dione
IUPAC Name:	3,3-dimethyl-2,4-dihydrobenzo[g]chromene-5,10-dione
Synonyms:
Standard InCHIKey:	ULXYWPKYMYLJBG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H14O3/c1-15(2)7-11-12(16)9-5-3-4-6-10(9)13(17)14(11)18-8-15/h3-6H,7-8H2,1-2H3
SMILES:	O=C1C2=C(OCC(C2)(C)C)C(=O)c2c1cccc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL511007
PubChem CID:	178515
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans [CHEMONTID:0001641] Naphthopyranones

*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
NPO3049	Rhinacanthus nasutus	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8463799]
NPO3049	Rhinacanthus nasutus	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8792629]
NPO3049	Rhinacanthus nasutus	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9214738]
NPO3049	Rhinacanthus nasutus	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3049	Rhinacanthus nasutus	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11678	Aeonium cuneatum	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13891	Scolytus multistriatus	Species	Curculionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11855	Streptomyces xanthocidicus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO14480	Tornabea scutellifera	Species	Physciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12707	Lithospermum canescens	Species	Boraginaceae	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
ED50	1
GI50	60

Activity Type	# Activity
Cell Line	60
Organism	1

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.	181.55	nM	PMID[453494]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	1355.19	nM	PMID[453494]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	1541.7	nM	PMID[453494]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	1039.92	nM	PMID[453494]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	1552.39	nM	PMID[453494]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	583.45	nM	PMID[453494]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	2301.44	nM	PMID[453494]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	1538.15	nM	PMID[453494]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	1644.37	nM	PMID[453494]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	709.58	nM	PMID[453494]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	1879.32	nM	PMID[453494]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	2098.94	nM	PMID[453494]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	101.62	nM	PMID[453494]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	749.89	nM	PMID[453494]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	1496.24	nM	PMID[453494]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	1986.09	nM	PMID[453494]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	1428.89	nM	PMID[453494]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	451.86	nM	PMID[453494]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	493.17	nM	PMID[453494]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	1690.44	nM	PMID[453494]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	1967.89	nM	PMID[453494]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	2037.04	nM	PMID[453494]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	2660.73	nM	PMID[453494]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	1698.24	nM	PMID[453494]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	1686.55	nM	PMID[453494]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	1853.53	nM	PMID[453494]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	1761.98	nM	PMID[453494]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	1606.94	nM	PMID[453494]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	1667.25	nM	PMID[453494]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	1321.3	nM	PMID[453494]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	1527.57	nM	PMID[453494]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	1883.65	nM	PMID[453494]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	1845.02	nM	PMID[453494]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	1905.46	nM	PMID[453494]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	2264.64	nM	PMID[453494]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	1702.16	nM	PMID[453494]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	1625.55	nM	PMID[453494]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	448.75	nM	PMID[453494]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	701.46	nM	PMID[453494]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	1648.16	nM	PMID[453494]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	1207.81	nM	PMID[453494]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	1901.08	nM	PMID[453494]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	1545.25	nM	PMID[453494]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	1914.26	nM	PMID[453494]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	558.47	nM	PMID[453494]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	1879.32	nM	PMID[453494]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	1091.44	nM	PMID[453494]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	194.54	nM	PMID[453494]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	2233.57	nM	PMID[453494]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	1648.16	nM	PMID[453494]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	1625.55	nM	PMID[453494]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	2884.03	nM	PMID[453494]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	827.94	nM	PMID[453494]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	1840.77	nM	PMID[453494]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	2365.92	nM	PMID[453494]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	2243.88	nM	PMID[453494]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	1644.37	nM	PMID[453494]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	2529.3	nM	PMID[453494]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	2197.86	nM	PMID[453494]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	2023.02	nM	PMID[453494]
NPT826	Organism	Magnaporthe oryzae	Magnaporthe oryzae	ED50	=	0.4	ppm	PMID[453493]

☑ 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 NPC137315 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	271
0.1-0.2	1325
0.2-0.3	3040
0.3-0.4	9978
0.4-0.5	13494
0.5-0.6	11597
0.6-0.7	2670
0.7-0.8	278
0.8-0.85	30
0.85-0.9	8
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9423	High Similarity	NPC192577
0.9346	High Similarity	NPC241851
0.9167	High Similarity	NPC326664
0.9118	High Similarity	NPC112552
0.9065	High Similarity	NPC291799
0.8962	High Similarity	NPC470391
0.8909	High Similarity	NPC470764
0.8818	High Similarity	NPC196075
0.8785	High Similarity	NPC203732
0.8762	High Similarity	NPC274443
0.8667	High Similarity	NPC244427
0.8667	High Similarity	NPC222390
0.8598	High Similarity	NPC172483
0.8547	High Similarity	NPC65627
0.8522	High Similarity	NPC204784
0.8482	Intermediate Similarity	NPC67377
0.8448	Intermediate Similarity	NPC105709
0.8393	Intermediate Similarity	NPC13784
0.8393	Intermediate Similarity	NPC143768
0.8348	Intermediate Similarity	NPC222968
0.8348	Intermediate Similarity	NPC80605
0.8348	Intermediate Similarity	NPC323440
0.8333	Intermediate Similarity	NPC62138
0.8333	Intermediate Similarity	NPC226093
0.8319	Intermediate Similarity	NPC328107
0.8304	Intermediate Similarity	NPC212415
0.8286	Intermediate Similarity	NPC156021
0.825	Intermediate Similarity	NPC295664
0.8246	Intermediate Similarity	NPC228936
0.819	Intermediate Similarity	NPC12695
0.8174	Intermediate Similarity	NPC135730
0.8158	Intermediate Similarity	NPC477411
0.8155	Intermediate Similarity	NPC476484
0.8142	Intermediate Similarity	NPC292834
0.812	Intermediate Similarity	NPC318173
0.8108	Intermediate Similarity	NPC470007
0.8103	Intermediate Similarity	NPC469843
0.8091	Intermediate Similarity	NPC134120
0.8087	Intermediate Similarity	NPC474408
0.8049	Intermediate Similarity	NPC478162
0.8049	Intermediate Similarity	NPC478165
0.8039	Intermediate Similarity	NPC157778
0.8037	Intermediate Similarity	NPC145052
0.8034	Intermediate Similarity	NPC61651
0.8033	Intermediate Similarity	NPC236405
0.8017	Intermediate Similarity	NPC318067
0.7983	Intermediate Similarity	NPC77000
0.7983	Intermediate Similarity	NPC238861
0.7967	Intermediate Similarity	NPC81135
0.7944	Intermediate Similarity	NPC103048
0.7941	Intermediate Similarity	NPC43945
0.7917	Intermediate Similarity	NPC144547
0.7913	Intermediate Similarity	NPC470253
0.7913	Intermediate Similarity	NPC469547
0.7905	Intermediate Similarity	NPC59677
0.7895	Intermediate Similarity	NPC210089
0.7895	Intermediate Similarity	NPC265513
0.7885	Intermediate Similarity	NPC303967
0.7885	Intermediate Similarity	NPC173413
0.7885	Intermediate Similarity	NPC67585
0.7885	Intermediate Similarity	NPC110420
0.787	Intermediate Similarity	NPC134882
0.787	Intermediate Similarity	NPC75724
0.7869	Intermediate Similarity	NPC51079
0.7869	Intermediate Similarity	NPC325740
0.7863	Intermediate Similarity	NPC260886
0.7833	Intermediate Similarity	NPC289432
0.7833	Intermediate Similarity	NPC988
0.7833	Intermediate Similarity	NPC476225
0.7826	Intermediate Similarity	NPC280789
0.7826	Intermediate Similarity	NPC186128
0.781	Intermediate Similarity	NPC284475
0.7778	Intermediate Similarity	NPC474095
0.7778	Intermediate Similarity	NPC265220
0.7778	Intermediate Similarity	NPC239185
0.7768	Intermediate Similarity	NPC209632
0.775	Intermediate Similarity	NPC202015
0.775	Intermediate Similarity	NPC476645
0.7739	Intermediate Similarity	NPC474157
0.7736	Intermediate Similarity	NPC155232
0.7736	Intermediate Similarity	NPC188844
0.7736	Intermediate Similarity	NPC1682
0.7731	Intermediate Similarity	NPC268930
0.7727	Intermediate Similarity	NPC476993
0.7727	Intermediate Similarity	NPC109514
0.7714	Intermediate Similarity	NPC19256
0.7699	Intermediate Similarity	NPC100767
0.7692	Intermediate Similarity	NPC196673
0.7692	Intermediate Similarity	NPC471721
0.7686	Intermediate Similarity	NPC232958
0.7679	Intermediate Similarity	NPC329282
0.7679	Intermediate Similarity	NPC114594
0.7672	Intermediate Similarity	NPC218855
0.7664	Intermediate Similarity	NPC238219
0.7664	Intermediate Similarity	NPC289883
0.7642	Intermediate Similarity	NPC133461
0.7638	Intermediate Similarity	NPC471832
0.7634	Intermediate Similarity	NPC38158
0.7632	Intermediate Similarity	NPC112903
0.7627	Intermediate Similarity	NPC215419
0.7623	Intermediate Similarity	NPC472981
0.7615	Intermediate Similarity	NPC23894
0.7607	Intermediate Similarity	NPC471481
0.7607	Intermediate Similarity	NPC272524
0.76	Intermediate Similarity	NPC294050
0.76	Intermediate Similarity	NPC328997
0.7593	Intermediate Similarity	NPC260233
0.7589	Intermediate Similarity	NPC247976
0.7589	Intermediate Similarity	NPC60679
0.7578	Intermediate Similarity	NPC27659
0.757	Intermediate Similarity	NPC153885
0.7565	Intermediate Similarity	NPC99846
0.7565	Intermediate Similarity	NPC269023
0.7565	Intermediate Similarity	NPC470252
0.7549	Intermediate Similarity	NPC215008
0.7545	Intermediate Similarity	NPC49994
0.7542	Intermediate Similarity	NPC308744
0.7542	Intermediate Similarity	NPC130591
0.7542	Intermediate Similarity	NPC234637
0.7541	Intermediate Similarity	NPC473243
0.7538	Intermediate Similarity	NPC171968
0.7524	Intermediate Similarity	NPC267262
0.7523	Intermediate Similarity	NPC219573
0.7523	Intermediate Similarity	NPC185208
0.7521	Intermediate Similarity	NPC79496
0.7519	Intermediate Similarity	NPC173980
0.75	Intermediate Similarity	NPC320891
0.75	Intermediate Similarity	NPC160339
0.75	Intermediate Similarity	NPC307
0.75	Intermediate Similarity	NPC164947
0.7481	Intermediate Similarity	NPC474659
0.748	Intermediate Similarity	NPC51448
0.748	Intermediate Similarity	NPC115797
0.748	Intermediate Similarity	NPC316553
0.7479	Intermediate Similarity	NPC474685
0.7479	Intermediate Similarity	NPC210092
0.7479	Intermediate Similarity	NPC93181
0.7479	Intermediate Similarity	NPC217111
0.7477	Intermediate Similarity	NPC476042
0.746	Intermediate Similarity	NPC476599
0.7458	Intermediate Similarity	NPC93287
0.7456	Intermediate Similarity	NPC471186
0.7453	Intermediate Similarity	NPC418308
0.7444	Intermediate Similarity	NPC284184
0.7444	Intermediate Similarity	NPC301341
0.744	Intermediate Similarity	NPC135062
0.7438	Intermediate Similarity	NPC471553
0.7436	Intermediate Similarity	NPC167504
0.7436	Intermediate Similarity	NPC474057
0.7422	Intermediate Similarity	NPC237225
0.7414	Intermediate Similarity	NPC83628
0.7414	Intermediate Similarity	NPC265407
0.7411	Intermediate Similarity	NPC473325
0.7407	Intermediate Similarity	NPC323420
0.7402	Intermediate Similarity	NPC146239
0.7391	Intermediate Similarity	NPC83409
0.7391	Intermediate Similarity	NPC185763
0.7391	Intermediate Similarity	NPC30594
0.7391	Intermediate Similarity	NPC119271
0.7391	Intermediate Similarity	NPC37622
0.7383	Intermediate Similarity	NPC277277
0.7373	Intermediate Similarity	NPC471189
0.7368	Intermediate Similarity	NPC249067
0.7368	Intermediate Similarity	NPC232996
0.7358	Intermediate Similarity	NPC153308
0.7339	Intermediate Similarity	NPC34243
0.7328	Intermediate Similarity	NPC56493
0.7315	Intermediate Similarity	NPC110704
0.7311	Intermediate Similarity	NPC161611
0.7308	Intermediate Similarity	NPC198305
0.7302	Intermediate Similarity	NPC85511
0.7295	Intermediate Similarity	NPC152812
0.7293	Intermediate Similarity	NPC217914
0.7281	Intermediate Similarity	NPC329556
0.7273	Intermediate Similarity	NPC472880
0.7273	Intermediate Similarity	NPC471616
0.7266	Intermediate Similarity	NPC48992
0.7266	Intermediate Similarity	NPC177925
0.7266	Intermediate Similarity	NPC51037
0.7266	Intermediate Similarity	NPC51292
0.7265	Intermediate Similarity	NPC469636
0.7265	Intermediate Similarity	NPC17417
0.7265	Intermediate Similarity	NPC10251
0.7258	Intermediate Similarity	NPC475827
0.7258	Intermediate Similarity	NPC474223
0.725	Intermediate Similarity	NPC11824
0.7244	Intermediate Similarity	NPC474766
0.7238	Intermediate Similarity	NPC294134
0.7227	Intermediate Similarity	NPC82899
0.7227	Intermediate Similarity	NPC270699
0.7218	Intermediate Similarity	NPC212207
0.7217	Intermediate Similarity	NPC31786
0.7213	Intermediate Similarity	NPC158157
0.7212	Intermediate Similarity	NPC39600
0.7203	Intermediate Similarity	NPC174099
0.7203	Intermediate Similarity	NPC214067
0.7203	Intermediate Similarity	NPC93084
0.7203	Intermediate Similarity	NPC251854
0.7203	Intermediate Similarity	NPC196246
0.72	Intermediate Similarity	NPC50872

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 NPC137315 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	249
0.1-0.2	955
0.2-0.3	1247
0.3-0.4	3017
0.4-0.5	2444
0.5-0.6	1047
0.6-0.7	168
0.7-0.8	22
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8304	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7983	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD650	Approved
0.781	Intermediate Similarity	NPD7609	Phase 3
0.7778	Intermediate Similarity	NPD3495	Discontinued
0.7736	Intermediate Similarity	NPD7631	Approved
0.748	Intermediate Similarity	NPD4879	Approved
0.748	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1237	Approved
0.7311	Intermediate Similarity	NPD7094	Approved
0.7311	Intermediate Similarity	NPD6858	Approved
0.7288	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD1930	Approved
0.7281	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD1929	Approved
0.7265	Intermediate Similarity	NPD2182	Approved
0.7217	Intermediate Similarity	NPD164	Approved
0.7207	Intermediate Similarity	NPD1989	Approved
0.719	Intermediate Similarity	NPD5951	Approved
0.7168	Intermediate Similarity	NPD2066	Phase 3
0.7121	Intermediate Similarity	NPD7961	Discontinued
0.7119	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD1508	Approved
0.7087	Intermediate Similarity	NPD3972	Approved
0.7059	Intermediate Similarity	NPD2067	Discontinued
0.7049	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD1932	Approved
0.7019	Intermediate Similarity	NPD942	Approved
0.7018	Intermediate Similarity	NPD1238	Approved
0.6984	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.697	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD1241	Discontinued
0.696	Remote Similarity	NPD7009	Phase 2
0.6944	Remote Similarity	NPD1087	Approved
0.6937	Remote Similarity	NPD1088	Approved
0.6923	Remote Similarity	NPD5909	Discontinued
0.6903	Remote Similarity	NPD1843	Approved
0.6884	Remote Similarity	NPD1471	Phase 3
0.688	Remote Similarity	NPD7610	Discontinued
0.6879	Remote Similarity	NPD7236	Approved
0.6875	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD1876	Approved
0.6842	Remote Similarity	NPD7008	Discontinued
0.6833	Remote Similarity	NPD2329	Discontinued
0.6822	Remote Similarity	NPD4878	Approved
0.6814	Remote Similarity	NPD1693	Approved
0.6814	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD2629	Approved
0.6757	Remote Similarity	NPD1089	Approved
0.6757	Remote Similarity	NPD1090	Approved
0.6757	Remote Similarity	NPD1086	Approved
0.6757	Remote Similarity	NPD3672	Approved
0.6757	Remote Similarity	NPD3673	Approved
0.6744	Remote Similarity	NPD6287	Discontinued
0.6744	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD1202	Approved
0.6726	Remote Similarity	NPD1563	Approved
0.6713	Remote Similarity	NPD3950	Discontinued
0.6697	Remote Similarity	NPD9257	Approved
0.6697	Remote Similarity	NPD9259	Approved
0.6696	Remote Similarity	NPD1239	Approved
0.6667	Remote Similarity	NPD9490	Approved
0.6667	Remote Similarity	NPD800	Approved
0.6667	Remote Similarity	NPD1470	Approved
0.6667	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD7239	Suspended
0.6641	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD1752	Approved
0.6639	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD1756	Approved
0.6618	Remote Similarity	NPD7713	Phase 3
0.6615	Remote Similarity	NPD1201	Approved
0.6613	Remote Similarity	NPD2607	Approved
0.6604	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD2932	Approved
0.6574	Remote Similarity	NPD9491	Approved
0.656	Remote Similarity	NPD6010	Discontinued
0.6552	Remote Similarity	NPD1564	Approved
0.6552	Remote Similarity	NPD1566	Phase 3
0.6552	Remote Similarity	NPD1565	Approved
0.6512	Remote Similarity	NPD3025	Approved
0.6512	Remote Similarity	NPD1651	Approved
0.6512	Remote Similarity	NPD3024	Approved
0.6508	Remote Similarity	NPD4766	Approved
0.6504	Remote Similarity	NPD4234	Approved
0.6504	Remote Similarity	NPD4233	Approved
0.6504	Remote Similarity	NPD1317	Discontinued
0.6496	Remote Similarity	NPD9495	Approved
0.6493	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD2798	Approved
0.6486	Remote Similarity	NPD506	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD1282	Approved
0.6462	Remote Similarity	NPD3019	Approved
0.646	Remote Similarity	NPD9258	Approved
0.646	Remote Similarity	NPD9256	Approved
0.6457	Remote Similarity	NPD4198	Discontinued
0.6457	Remote Similarity	NPD3317	Approved
0.6434	Remote Similarity	NPD9545	Approved
0.6417	Remote Similarity	NPD6647	Phase 2
0.6415	Remote Similarity	NPD225	Approved
0.6415	Remote Similarity	NPD227	Approved
0.6412	Remote Similarity	NPD3023	Approved
0.6412	Remote Similarity	NPD3026	Approved
0.6408	Remote Similarity	NPD2346	Discontinued
0.6397	Remote Similarity	NPD7055	Discontinued
0.6395	Remote Similarity	NPD6273	Approved
0.6389	Remote Similarity	NPD7003	Approved
0.6387	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD3748	Approved
0.6364	Remote Similarity	NPD1281	Approved
0.634	Remote Similarity	NPD7057	Phase 3
0.634	Remote Similarity	NPD7058	Phase 2
0.6338	Remote Similarity	NPD2796	Approved
0.6336	Remote Similarity	NPD2345	Approved
0.6333	Remote Similarity	NPD6599	Discontinued
0.6324	Remote Similarity	NPD7084	Phase 3
0.6316	Remote Similarity	NPD6637	Approved
0.6311	Remote Similarity	NPD1018	Approved
0.6304	Remote Similarity	NPD2313	Discontinued
0.6303	Remote Similarity	NPD7798	Approved
0.6296	Remote Similarity	NPD3267	Approved
0.6296	Remote Similarity	NPD3266	Approved
0.6294	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD4574	Approved
0.6279	Remote Similarity	NPD4576	Approved
0.6276	Remote Similarity	NPD4628	Phase 3
0.6276	Remote Similarity	NPD8166	Discontinued
0.6269	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD5157	Phase 1
0.6269	Remote Similarity	NPD5159	Phase 2
0.6268	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.626	Remote Similarity	NPD1245	Approved
0.6259	Remote Similarity	NPD8032	Phase 2
0.6259	Remote Similarity	NPD6663	Approved
0.625	Remote Similarity	NPD1246	Approved
0.625	Remote Similarity	NPD2788	Approved
0.6241	Remote Similarity	NPD518	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD9260	Approved
0.6239	Remote Similarity	NPD226	Approved
0.6233	Remote Similarity	NPD3887	Approved
0.6232	Remote Similarity	NPD6039	Approved
0.6222	Remote Similarity	NPD1283	Approved
0.6222	Remote Similarity	NPD5667	Approved
0.6214	Remote Similarity	NPD4307	Phase 2
0.6214	Remote Similarity	NPD3140	Approved
0.6214	Remote Similarity	NPD3142	Approved
0.6212	Remote Similarity	NPD5305	Approved
0.6212	Remote Similarity	NPD5306	Approved
0.6207	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD5736	Approved
0.6198	Remote Similarity	NPD2648	Phase 3
0.6198	Remote Similarity	NPD2193	Phase 2
0.6187	Remote Similarity	NPD3764	Approved
0.6181	Remote Similarity	NPD2353	Approved
0.6181	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD2652	Approved
0.6172	Remote Similarity	NPD2650	Approved
0.6165	Remote Similarity	NPD4135	Approved
0.6165	Remote Similarity	NPD4136	Approved
0.6165	Remote Similarity	NPD4106	Approved
0.6164	Remote Similarity	NPD3750	Approved
0.6159	Remote Similarity	NPD7458	Discontinued
0.6159	Remote Similarity	NPD3226	Approved
0.6159	Remote Similarity	NPD6832	Phase 2
0.6154	Remote Similarity	NPD9493	Approved
0.6154	Remote Similarity	NPD1510	Phase 2
0.6148	Remote Similarity	NPD9261	Approved
0.6148	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD5691	Approved
0.6129	Remote Similarity	NPD5705	Approved
0.6129	Remote Similarity	NPD5706	Approved
0.6129	Remote Similarity	NPD5704	Approved
0.6127	Remote Similarity	NPD1607	Approved
0.6122	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6119	Remote Similarity	NPD7437	Approved
0.6119	Remote Similarity	NPD4806	Approved
0.6119	Remote Similarity	NPD7436	Approved
0.6119	Remote Similarity	NPD4807	Approved
0.6115	Remote Similarity	NPD2754	Discontinued
0.6111	Remote Similarity	NPD664	Approved
0.6107	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6107	Remote Similarity	NPD6065	Approved
0.6103	Remote Similarity	NPD6330	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD4094	Approved
0.6099	Remote Similarity	NPD2979	Phase 3
0.6099	Remote Similarity	NPD1240	Approved
0.609	Remote Similarity	NPD17	Approved
0.6087	Remote Similarity	NPD5346	Phase 2
0.6087	Remote Similarity	NPD5347	Phase 2
0.6081	Remote Similarity	NPD3300	Phase 2
0.608	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD3268	Approved
0.6069	Remote Similarity	NPD2344	Approved
0.6066	Remote Similarity	NPD2196	Discontinued
0.6058	Remote Similarity	NPD2797	Approved
0.6053	Remote Similarity	NPD4793	Discontinued
0.6042	Remote Similarity	NPD2799	Discontinued
0.6042	Remote Similarity	NPD4308	Phase 3

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