NPASS Compound

Structure

CID118154 OpenBabel06191715472D 23 26 0 0 0 0 0 0 0 0999 V2000 3.3412 0.8309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 -3.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9889 -1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9393 -1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9393 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0733 -2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0733 -0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2072 -1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2072 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4752 -1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4752 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3412 -2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 -2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 -0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 -1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3412 -0.1691 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.3412 -3.1691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 -3.1691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1229 -2.1691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 9 2 0 0 0 0 7 10 2 0 0 0 0 8 22 1 0 0 0 0 8 23 1 0 0 0 0 9 10 1 0 0 0 0 9 13 1 0 0 0 0 10 18 1 0 0 0 0 11 12 2 0 0 0 0 11 13 1 0 0 0 0 11 14 1 0 0 0 0 12 15 1 0 0 0 0 12 18 1 0 0 0 0 13 19 2 0 0 0 0 14 16 2 0 0 0 0 14 20 1 0 0 0 0 15 17 2 0 0 0 0 15 22 1 0 0 0 0 16 17 1 0 0 0 0 16 21 1 0 0 0 0 17 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	313.1
Volume:	304.855
LogP:	2.276
LogD:	2.394
LogS:	-3.776
# Rotatable Bonds:	2
TPSA:	58.92
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.68
Synthetic Accessibility Score:	2.62
Fsp3:	0.235
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.647
MDCK Permeability:	3.261627716710791e-05
Pgp-inhibitor:	0.253
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.594
Plasma Protein Binding (PPB):	92.68275451660156%
Volume Distribution (VD):	0.809
Pgp-substrate:	4.619871616363525%

ADMET: Metabolism

CYP1A2-inhibitor:	0.951
CYP1A2-substrate:	0.918
CYP2C19-inhibitor:	0.949
CYP2C19-substrate:	0.848
CYP2C9-inhibitor:	0.766
CYP2C9-substrate:	0.919
CYP2D6-inhibitor:	0.666
CYP2D6-substrate:	0.874
CYP3A4-inhibitor:	0.887
CYP3A4-substrate:	0.365

ADMET: Excretion

Clearance (CL):	3.046
Half-life (T1/2):	0.222

ADMET: Toxicity

hERG Blockers:	0.108
Human Hepatotoxicity (H-HT):	0.083
Drug-inuced Liver Injury (DILI):	0.183
AMES Toxicity:	0.836
Rat Oral Acute Toxicity:	0.059
Maximum Recommended Daily Dose:	0.15
Skin Sensitization:	0.206
Carcinogencity:	0.962
Eye Corrosion:	0.011
Eye Irritation:	0.913
Respiratory Toxicity:	0.594

Download Data

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

Natural Product: NPC118154

Natural Product ID:	NPC118154
*Common Name:**	4,5-Dimethoxy-11-Methyl-[1,3]Dioxolo[4,5-C]Acridin-6-One
IUPAC Name:	4,5-dimethoxy-11-methyl-[1,3]dioxolo[4,5-c]acridin-6-one
Synonyms:
Standard InCHIKey:	PEWWLIQAXYMMAN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H15NO5/c1-18-10-7-5-4-6-9(10)13(19)11-12(18)15-17(23-8-22-15)16(21-3)14(11)20-2/h4-7H,8H2,1-3H3
SMILES:	COc1c(OC)c2OCOc2c2c1c(=O)c1c(n2C)cccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1876999
PubChem CID:	68433
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0001908] Benzoquinolines [CHEMONTID:0000274] Acridines [CHEMONTID:0001811] Acridones

*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
NPO3659	Limonium bicolor	Species	Plumbaginaceae	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
GI50	58
IC50	2
Potency	12

Activity Type	# Activity
Cell Line	58
Individual Protein	10
Others	2
PROTEIN COMPLEX	3
PROTEIN-PROTEIN INTERACTION	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT135	Individual Protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	79432.8	nM	PMID[512682]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512683]
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512683]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512683]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512683]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512683]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512683]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512683]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512683]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512683]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512683]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	81470.43	nM	PMID[512683]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512683]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512683]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512683]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512683]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512683]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512683]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512683]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512683]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512683]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512683]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512683]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512683]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512683]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512683]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512683]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512683]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512683]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512683]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	76207.9	nM	PMID[512683]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512683]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512683]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512683]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512683]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512683]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512683]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512683]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512683]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512683]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512683]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	45185.59	nM	PMID[512683]
NPT4355	Individual Protein	Polyadenylate-binding protein 1	Homo sapiens	IC50	>	66000.0	nM	PMID[512682]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512683]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512683]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512683]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	36140.99	nM	PMID[512683]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512683]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512683]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512683]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512683]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512683]
NPT4355	Individual Protein	Polyadenylate-binding protein 1	Homo sapiens	IC50	=	41750.0	nM	PMID[512682]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512683]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512683]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512683]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512683]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512683]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512683]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512683]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[512683]
NPT478	Individual Protein	Ataxin-2	Homo sapiens	Potency	n.a.	13371.4	nM	PMID[512682]
NPT101	Individual Protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	12589.3	nM	PMID[512682]
NPT11	Individual Protein	Guanine nucleotide-binding protein G(s), subunit alpha	Homo sapiens	Potency	n.a.	7079.5	nM	PMID[512682]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	18356.4	nM	PMID[512682]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	29092.9	nM	PMID[512682]
NPT21702	PROTEIN-PROTEIN INTERACTION	Importin subunit beta-1/Snurportin-1	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[512682]
NPT20798	PROTEIN COMPLEX	GTP-binding nuclear protein Ran/Importin subunit beta-1/Snurportin-1	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[512682]
NPT803	Individual Protein	Flap endonuclease 1	Homo sapiens	Potency	n.a.	44668.4	nM	PMID[512682]
NPT2	Others	Unspecified		Potency	n.a.	3981.1	nM	PMID[512682]
NPT755	Individual Protein	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	Homo sapiens	Potency	n.a.	75686.3	nM	PMID[512682]
NPT2	Others	Unspecified		Potency	n.a.	2511.9	nM	PMID[512682]

☑ 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 NPC118154 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	635
0.1-0.2	3480
0.2-0.3	11961
0.3-0.4	5707
0.4-0.5	10026
0.5-0.6	9257
0.6-0.7	1333
0.7-0.8	251
0.8-0.85	26
0.85-0.9	11
0.9-0.95	5
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC157983
0.9796	High Similarity	NPC195120
0.9695	High Similarity	NPC87560
0.9592	High Similarity	NPC268223
0.9261	High Similarity	NPC118189
0.9113	High Similarity	NPC134702
0.9073	High Similarity	NPC76478
0.9059	High Similarity	NPC148391
0.902	High Similarity	NPC182853
0.8916	High Similarity	NPC114468
0.8873	High Similarity	NPC2905
0.8818	High Similarity	NPC220241
0.8818	High Similarity	NPC295479
0.8708	High Similarity	NPC7560
0.8592	High Similarity	NPC13249
0.8458	Intermediate Similarity	NPC285254
0.8439	Intermediate Similarity	NPC212123
0.8286	Intermediate Similarity	NPC30749
0.8159	Intermediate Similarity	NPC114039
0.8159	Intermediate Similarity	NPC206109
0.8152	Intermediate Similarity	NPC116178
0.8152	Intermediate Similarity	NPC305542
0.8113	Intermediate Similarity	NPC321166
0.8113	Intermediate Similarity	NPC217903
0.8109	Intermediate Similarity	NPC1820
0.8086	Intermediate Similarity	NPC198160
0.8057	Intermediate Similarity	NPC474366
0.8049	Intermediate Similarity	NPC234933
0.7951	Intermediate Similarity	NPC170333
0.7934	Intermediate Similarity	NPC218303
0.7929	Intermediate Similarity	NPC5167
0.7854	Intermediate Similarity	NPC329830
0.7839	Intermediate Similarity	NPC85613
0.7824	Intermediate Similarity	NPC176113
0.781	Intermediate Similarity	NPC15987
0.7767	Intermediate Similarity	NPC254957
0.7751	Intermediate Similarity	NPC241263
0.7736	Intermediate Similarity	NPC268077
0.7736	Intermediate Similarity	NPC133156
0.7725	Intermediate Similarity	NPC202771
0.7725	Intermediate Similarity	NPC2173
0.7725	Intermediate Similarity	NPC119818
0.7725	Intermediate Similarity	NPC328700
0.7703	Intermediate Similarity	NPC71124
0.7679	Intermediate Similarity	NPC120513
0.7662	Intermediate Similarity	NPC298320
0.7652	Intermediate Similarity	NPC476258
0.7652	Intermediate Similarity	NPC304837
0.7606	Intermediate Similarity	NPC207971
0.7583	Intermediate Similarity	NPC5374
0.7559	Intermediate Similarity	NPC288759
0.7542	Intermediate Similarity	NPC203373
0.7536	Intermediate Similarity	NPC14622
0.7536	Intermediate Similarity	NPC73020
0.7536	Intermediate Similarity	NPC70290
0.7536	Intermediate Similarity	NPC124302
0.7536	Intermediate Similarity	NPC215098
0.7536	Intermediate Similarity	NPC46744
0.7525	Intermediate Similarity	NPC287152
0.75	Intermediate Similarity	NPC55470
0.7489	Intermediate Similarity	NPC120239
0.7488	Intermediate Similarity	NPC283810
0.7488	Intermediate Similarity	NPC313112
0.7488	Intermediate Similarity	NPC301292
0.7478	Intermediate Similarity	NPC160113
0.7478	Intermediate Similarity	NPC476220
0.7467	Intermediate Similarity	NPC476429
0.7465	Intermediate Similarity	NPC72788
0.7465	Intermediate Similarity	NPC314100
0.7465	Intermediate Similarity	NPC120671
0.7465	Intermediate Similarity	NPC226652
0.7458	Intermediate Similarity	NPC1608
0.7453	Intermediate Similarity	NPC23080
0.7453	Intermediate Similarity	NPC193906
0.7436	Intermediate Similarity	NPC113455
0.7426	Intermediate Similarity	NPC173250
0.7424	Intermediate Similarity	NPC299582
0.7422	Intermediate Similarity	NPC148124
0.7381	Intermediate Similarity	NPC63152
0.7378	Intermediate Similarity	NPC99724
0.7352	Intermediate Similarity	NPC477825
0.7325	Intermediate Similarity	NPC476436
0.7308	Intermediate Similarity	NPC116007
0.7296	Intermediate Similarity	NPC154922
0.7293	Intermediate Similarity	NPC248903
0.7281	Intermediate Similarity	NPC41216
0.7273	Intermediate Similarity	NPC18306
0.7273	Intermediate Similarity	NPC93653
0.7257	Intermediate Similarity	NPC208364
0.7252	Intermediate Similarity	NPC477826
0.7252	Intermediate Similarity	NPC477827
0.7249	Intermediate Similarity	NPC26928
0.7246	Intermediate Similarity	NPC119134
0.7246	Intermediate Similarity	NPC27887
0.7238	Intermediate Similarity	NPC477396
0.7227	Intermediate Similarity	NPC124313
0.7225	Intermediate Similarity	NPC83511
0.7217	Intermediate Similarity	NPC226708
0.7209	Intermediate Similarity	NPC112937
0.7204	Intermediate Similarity	NPC208890
0.7203	Intermediate Similarity	NPC168922
0.72	Intermediate Similarity	NPC195636
0.7195	Intermediate Similarity	NPC46990
0.7182	Intermediate Similarity	NPC308943
0.7172	Intermediate Similarity	NPC148497
0.7172	Intermediate Similarity	NPC153008
0.7171	Intermediate Similarity	NPC67978
0.7171	Intermediate Similarity	NPC303581
0.7164	Intermediate Similarity	NPC24954
0.7157	Intermediate Similarity	NPC73280
0.7156	Intermediate Similarity	NPC477259
0.7156	Intermediate Similarity	NPC169387
0.7155	Intermediate Similarity	NPC477393
0.7149	Intermediate Similarity	NPC470042
0.7143	Intermediate Similarity	NPC84164
0.7143	Intermediate Similarity	NPC207283
0.7136	Intermediate Similarity	NPC478213
0.7136	Intermediate Similarity	NPC244371
0.7131	Intermediate Similarity	NPC101312
0.713	Intermediate Similarity	NPC231924
0.7124	Intermediate Similarity	NPC477828
0.7114	Intermediate Similarity	NPC204867
0.7107	Intermediate Similarity	NPC134637
0.7106	Intermediate Similarity	NPC34770
0.7105	Intermediate Similarity	NPC476069
0.7101	Intermediate Similarity	NPC308267
0.7098	Intermediate Similarity	NPC10732
0.7078	Intermediate Similarity	NPC183537
0.707	Intermediate Similarity	NPC469816
0.707	Intermediate Similarity	NPC469815
0.7067	Intermediate Similarity	NPC98416
0.7059	Intermediate Similarity	NPC80472
0.7054	Intermediate Similarity	NPC107123
0.7053	Intermediate Similarity	NPC329992
0.7051	Intermediate Similarity	NPC83019
0.7051	Intermediate Similarity	NPC217176
0.705	Intermediate Similarity	NPC57211
0.7043	Intermediate Similarity	NPC251071
0.7042	Intermediate Similarity	NPC312531
0.7035	Intermediate Similarity	NPC279061
0.7035	Intermediate Similarity	NPC290227
0.703	Intermediate Similarity	NPC258644
0.7028	Intermediate Similarity	NPC209981
0.7022	Intermediate Similarity	NPC470481
0.7022	Intermediate Similarity	NPC470482
0.7018	Intermediate Similarity	NPC207239
0.7017	Intermediate Similarity	NPC166722
0.7015	Intermediate Similarity	NPC478238
0.7014	Intermediate Similarity	NPC38961
0.7005	Intermediate Similarity	NPC204580
0.7004	Intermediate Similarity	NPC240684
0.7	Intermediate Similarity	NPC292460
0.7	Intermediate Similarity	NPC52623
0.7	Intermediate Similarity	NPC166712
0.6996	Remote Similarity	NPC100573
0.6996	Remote Similarity	NPC207873
0.6996	Remote Similarity	NPC270515
0.6995	Remote Similarity	NPC62518
0.6995	Remote Similarity	NPC215375
0.699	Remote Similarity	NPC224687
0.6988	Remote Similarity	NPC282346
0.6983	Remote Similarity	NPC19175
0.6979	Remote Similarity	NPC227033
0.6976	Remote Similarity	NPC478199
0.6975	Remote Similarity	NPC189903
0.6975	Remote Similarity	NPC182907
0.6972	Remote Similarity	NPC88923
0.6972	Remote Similarity	NPC100734
0.6972	Remote Similarity	NPC315634
0.6967	Remote Similarity	NPC179704
0.6964	Remote Similarity	NPC168250
0.6959	Remote Similarity	NPC125924
0.6959	Remote Similarity	NPC477258
0.6952	Remote Similarity	NPC121400
0.6951	Remote Similarity	NPC222561
0.6951	Remote Similarity	NPC478075
0.6946	Remote Similarity	NPC167595
0.6944	Remote Similarity	NPC302001
0.6939	Remote Similarity	NPC77878
0.6937	Remote Similarity	NPC475147
0.6934	Remote Similarity	NPC249405
0.6933	Remote Similarity	NPC108342
0.6933	Remote Similarity	NPC25961
0.6929	Remote Similarity	NPC477395
0.6927	Remote Similarity	NPC272706
0.6927	Remote Similarity	NPC260640
0.6927	Remote Similarity	NPC295009
0.6927	Remote Similarity	NPC24228
0.6923	Remote Similarity	NPC473458
0.6923	Remote Similarity	NPC286135
0.6923	Remote Similarity	NPC471513
0.6923	Remote Similarity	NPC303374
0.6916	Remote Similarity	NPC474009
0.6914	Remote Similarity	NPC58209
0.6908	Remote Similarity	NPC86469
0.6904	Remote Similarity	NPC314702
0.6904	Remote Similarity	NPC296575
0.6901	Remote Similarity	NPC188400
0.6901	Remote Similarity	NPC160100
0.69	Remote Similarity	NPC313327

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 NPC118154 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	365
0.1-0.2	704
0.2-0.3	1124
0.3-0.4	2027
0.4-0.5	2725
0.5-0.6	1724
0.6-0.7	437
0.7-0.8	42
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9069	High Similarity	NPD2899	Discontinued
0.8227	Intermediate Similarity	NPD6625	Approved
0.7895	Intermediate Similarity	NPD956	Clinical (unspecified phase)
0.7876	Intermediate Similarity	NPD4846	Phase 2
0.7725	Intermediate Similarity	NPD5006	Approved
0.7725	Intermediate Similarity	NPD5005	Approved
0.7536	Intermediate Similarity	NPD4420	Approved
0.7523	Intermediate Similarity	NPD683	Approved
0.7488	Intermediate Similarity	NPD6621	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD7223	Discontinued
0.7401	Intermediate Similarity	NPD7224	Discontinued
0.7192	Intermediate Similarity	NPD5242	Approved
0.7181	Intermediate Similarity	NPD7858	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8461	Discontinued
0.7123	Intermediate Similarity	NPD7064	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD3297	Approved
0.7037	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD5582	Discontinued
0.6996	Remote Similarity	NPD3899	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD8067	Phase 3
0.6972	Remote Similarity	NPD7803	Approved
0.6972	Remote Similarity	NPD5071	Phase 2
0.694	Remote Similarity	NPD7279	Phase 2
0.694	Remote Similarity	NPD7278	Phase 2
0.6937	Remote Similarity	NPD3298	Approved
0.6933	Remote Similarity	NPD5860	Discontinued
0.6929	Remote Similarity	NPD1483	Discontinued
0.69	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD8367	Approved
0.6886	Remote Similarity	NPD7559	Phase 2
0.6864	Remote Similarity	NPD6874	Approved
0.6855	Remote Similarity	NPD8492	Approved
0.6847	Remote Similarity	NPD7071	Clinical (unspecified phase)
0.6844	Remote Similarity	NPD4859	Phase 1
0.684	Remote Similarity	NPD5519	Discontinued
0.6833	Remote Similarity	NPD5457	Discontinued
0.6813	Remote Similarity	NPD7708	Approved
0.6812	Remote Similarity	NPD5186	Approved
0.6812	Remote Similarity	NPD5183	Approved
0.6773	Remote Similarity	NPD7956	Approved
0.6773	Remote Similarity	NPD7955	Approved
0.677	Remote Similarity	NPD4082	Approved
0.6767	Remote Similarity	NPD5496	Approved
0.6757	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD1945	Phase 1
0.6746	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD5353	Approved
0.6683	Remote Similarity	NPD5978	Approved
0.6683	Remote Similarity	NPD2821	Approved
0.6683	Remote Similarity	NPD5977	Approved
0.6682	Remote Similarity	NPD2339	Phase 3
0.668	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3437	Discontinued
0.6667	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6654	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD7584	Approved
0.6639	Remote Similarity	NPD7885	Phase 2
0.6639	Remote Similarity	NPD7886	Phase 2
0.6639	Remote Similarity	NPD7922	Phase 1
0.6638	Remote Similarity	NPD5914	Approved
0.6637	Remote Similarity	NPD4456	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6104	Discontinued
0.6636	Remote Similarity	NPD7125	Discontinued
0.6635	Remote Similarity	NPD5494	Approved
0.6618	Remote Similarity	NPD6386	Approved
0.6618	Remote Similarity	NPD6385	Approved
0.6609	Remote Similarity	NPD4493	Discontinued
0.6608	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD6199	Discontinued
0.6583	Remote Similarity	NPD4981	Phase 2
0.6582	Remote Similarity	NPD3912	Discontinued
0.658	Remote Similarity	NPD7225	Discontinued
0.658	Remote Similarity	NPD4492	Approved
0.658	Remote Similarity	NPD4494	Approved
0.6579	Remote Similarity	NPD7263	Phase 2
0.6579	Remote Similarity	NPD4596	Phase 1
0.6578	Remote Similarity	NPD6321	Discontinued
0.6575	Remote Similarity	NPD2843	Phase 2
0.6575	Remote Similarity	NPD2845	Phase 2
0.657	Remote Similarity	NPD6723	Discontinued
0.6564	Remote Similarity	NPD6644	Discontinued
0.6555	Remote Similarity	NPD4505	Phase 1
0.6555	Remote Similarity	NPD5677	Discontinued
0.655	Remote Similarity	NPD7701	Phase 2
0.655	Remote Similarity	NPD5950	Discontinued
0.655	Remote Similarity	NPD3472	Approved
0.655	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.655	Remote Similarity	NPD2906	Approved
0.655	Remote Similarity	NPD4022	Approved
0.655	Remote Similarity	NPD2907	Approved
0.6549	Remote Similarity	NPD7626	Approved
0.6549	Remote Similarity	NPD7627	Approved
0.6542	Remote Similarity	NPD7654	Discontinued
0.654	Remote Similarity	NPD4049	Phase 2
0.653	Remote Similarity	NPD1898	Discontinued
0.6527	Remote Similarity	NPD7186	Phase 3
0.6526	Remote Similarity	NPD3818	Discontinued
0.6512	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD2246	Approved
0.6509	Remote Similarity	NPD2248	Approved
0.6507	Remote Similarity	NPD7583	Approved
0.6498	Remote Similarity	NPD7907	Approved
0.6494	Remote Similarity	NPD3372	Discontinued
0.6494	Remote Similarity	NPD5726	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD4467	Phase 2
0.6491	Remote Similarity	NPD4465	Phase 2
0.6489	Remote Similarity	NPD1880	Phase 3
0.6484	Remote Similarity	NPD4515	Suspended
0.6478	Remote Similarity	NPD7585	Approved
0.6478	Remote Similarity	NPD7417	Discontinued
0.6473	Remote Similarity	NPD2975	Approved
0.6473	Remote Similarity	NPD2973	Approved
0.6473	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD2974	Approved
0.6471	Remote Similarity	NPD8091	Phase 3
0.6468	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6459	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD4498	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD4952	Phase 3
0.6445	Remote Similarity	NPD2247	Approved
0.6445	Remote Similarity	NPD2249	Approved
0.6441	Remote Similarity	NPD6198	Phase 1
0.6429	Remote Similarity	NPD7805	Phase 3
0.6429	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6426	Remote Similarity	NPD8149	Discontinued
0.6423	Remote Similarity	NPD7048	Phase 3
0.6422	Remote Similarity	NPD3893	Discontinued
0.642	Remote Similarity	NPD3441	Approved
0.642	Remote Similarity	NPD3442	Approved
0.642	Remote Similarity	NPD1505	Phase 2
0.6418	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD5847	Phase 1
0.6414	Remote Similarity	NPD4665	Approved
0.6414	Remote Similarity	NPD4111	Phase 1
0.6411	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6411	Remote Similarity	NPD6788	Approved
0.6411	Remote Similarity	NPD6790	Phase 1
0.6404	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD6997	Phase 2
0.64	Remote Similarity	NPD2654	Approved
0.6394	Remote Similarity	NPD2801	Approved
0.6388	Remote Similarity	NPD4580	Approved
0.6376	Remote Similarity	NPD3253	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD5197	Approved
0.6372	Remote Similarity	NPD5196	Approved
0.6372	Remote Similarity	NPD6877	Discontinued
0.6372	Remote Similarity	NPD5194	Approved
0.6368	Remote Similarity	NPD3815	Phase 1
0.6368	Remote Similarity	NPD3888	Discontinued
0.6368	Remote Similarity	NPD3816	Phase 1
0.6368	Remote Similarity	NPD2681	Approved
0.6368	Remote Similarity	NPD2680	Approved
0.6367	Remote Similarity	NPD4373	Phase 2
0.6367	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7043	Discontinued
0.6364	Remote Similarity	NPD3259	Approved
0.636	Remote Similarity	NPD2494	Approved
0.636	Remote Similarity	NPD2493	Approved
0.636	Remote Similarity	NPD3450	Approved
0.636	Remote Similarity	NPD3452	Approved
0.6359	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD5025	Approved
0.6356	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD2300	Clinical (unspecified phase)
0.6352	Remote Similarity	NPD6962	Phase 2
0.6351	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD1934	Approved
0.6344	Remote Similarity	NPD5608	Approved
0.6344	Remote Similarity	NPD5609	Approved
0.6344	Remote Similarity	NPD8285	Discontinued
0.6343	Remote Similarity	NPD3793	Phase 3
0.6343	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD3641	Approved
0.6341	Remote Similarity	NPD3640	Phase 3
0.6341	Remote Similarity	NPD3639	Approved
0.634	Remote Similarity	NPD4455	Discontinued
0.6338	Remote Similarity	NPD5711	Approved
0.6338	Remote Similarity	NPD5710	Approved
0.6336	Remote Similarity	NPD5658	Approved
0.6335	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.6332	Remote Similarity	NPD3516	Approved
0.6332	Remote Similarity	NPD3515	Approved
0.6329	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD4605	Approved
0.6327	Remote Similarity	NPD4604	Approved
0.6327	Remote Similarity	NPD4979	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD4206	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