NPASS Compound

Structure

CID16119 OpenBabel06191715342D 27 27 0 0 0 0 0 0 0 0999 V2000 -10.3923 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2583 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2583 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 27 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 2 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 18 21 1 0 0 0 0 19 21 2 0 0 0 0 19 22 1 0 0 0 0 20 22 1 0 0 0 0 20 23 2 0 0 0 0 21 24 1 0 0 0 0 22 25 2 0 0 0 0 23 24 1 0 0 0 0 23 27 1 0 0 0 0 24 26 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	374.28
Volume:	428.292
LogP:	7.15
LogD:	4.832
LogS:	-3.662
# Rotatable Bonds:	15
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.191
Synthetic Accessibility Score:	2.573
Fsp3:	0.583
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.904
MDCK Permeability:	1.966215313586872e-05
Pgp-inhibitor:	0.052
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.044
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.057
Plasma Protein Binding (PPB):	100.30906677246094%
Volume Distribution (VD):	8.151
Pgp-substrate:	0.5805941224098206%

ADMET: Metabolism

CYP1A2-inhibitor:	0.552
CYP1A2-substrate:	0.674
CYP2C19-inhibitor:	0.634
CYP2C19-substrate:	0.198
CYP2C9-inhibitor:	0.297
CYP2C9-substrate:	0.984
CYP2D6-inhibitor:	0.817
CYP2D6-substrate:	0.943
CYP3A4-inhibitor:	0.649
CYP3A4-substrate:	0.08

ADMET: Excretion

Clearance (CL):	5.379
Half-life (T1/2):	0.871

ADMET: Toxicity

hERG Blockers:	0.242
Human Hepatotoxicity (H-HT):	0.116
Drug-inuced Liver Injury (DILI):	0.019
AMES Toxicity:	0.058
Rat Oral Acute Toxicity:	0.046
Maximum Recommended Daily Dose:	0.449
Skin Sensitization:	0.983
Carcinogencity:	0.053
Eye Corrosion:	0.417
Eye Irritation:	0.956
Respiratory Toxicity:	0.871

Download Data

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

Natural Product: NPC16119

Natural Product ID:	NPC16119
*Common Name:**	Irisquinone A
IUPAC Name:	2-[(Z)-heptadec-10-enyl]-6-methoxycyclohexa-2,5-diene-1,4-dione
Synonyms:
Standard InCHIKey:	YYCCUFKHCNSRIA-HJWRWDBZSA-N
Standard InCHI:	InChI=1S/C24H38O3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-21-19-22(25)20-23(27-2)24(21)26/h8-9,19-20H,3-7,10-18H2,1-2H3/b9-8-
SMILES:	CCCCCC/C=CCCCCCCCCCC1=CC(=O)C=C(C1=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL461167
PubChem CID:	5318483
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003487] Cyclic ketones [CHEMONTID:0002495] Quinones [CHEMONTID:0002384] Benzoquinones [CHEMONTID:0002494] P-benzoquinones

*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
NPO23996	Iris pseudacorus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13606.1	Iris pallasii var. chinensis	Varieties	Tarachodidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25051.1	Iris lactea var. chinensis	Varieties	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23996	Iris pseudacorus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13606.1	Iris pallasii var. chinensis	Varieties	Tarachodidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25051.1	Iris lactea var. chinensis	Varieties	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23996	Iris pseudacorus	Species	Iridaceae	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
EC50	7
GI50	60
Others	2

Activity Type	# Activity
Cell Line	66
NON-MOLECULAR	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	3033.89	nM	PMID[508322]
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	6501.3	nM	PMID[508322]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	3372.87	nM	PMID[508322]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	3176.87	nM	PMID[508322]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	4570.88	nM	PMID[508322]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	2517.68	nM	PMID[508322]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	5623.41	nM	PMID[508322]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	1879.32	nM	PMID[508322]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	2051.16	nM	PMID[508322]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	2535.13	nM	PMID[508322]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	12302.69	nM	PMID[508322]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	5821.03	nM	PMID[508322]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	753.36	nM	PMID[508322]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	3981.07	nM	PMID[508322]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	3793.15	nM	PMID[508322]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	3801.89	nM	PMID[508322]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	3483.37	nM	PMID[508322]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	712.85	nM	PMID[508322]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	592.93	nM	PMID[508322]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	5597.58	nM	PMID[508322]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	4355.12	nM	PMID[508322]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	2890.68	nM	PMID[508322]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	6053.41	nM	PMID[508322]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	2716.44	nM	PMID[508322]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	4602.57	nM	PMID[508322]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	3749.73	nM	PMID[508322]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	1995.26	nM	PMID[508322]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	4187.94	nM	PMID[508322]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	6918.31	nM	PMID[508322]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	2208.0	nM	PMID[508322]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	4055.09	nM	PMID[508322]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	2046.44	nM	PMID[508322]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	2162.72	nM	PMID[508322]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	4335.11	nM	PMID[508322]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	4055.09	nM	PMID[508322]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	8241.38	nM	PMID[508322]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	2432.2	nM	PMID[508322]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	2098.94	nM	PMID[508322]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	3427.68	nM	PMID[508322]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	5929.25	nM	PMID[508322]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	3572.73	nM	PMID[508322]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	1807.17	nM	PMID[508322]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	4456.56	nM	PMID[508322]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	4355.12	nM	PMID[508322]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	2228.44	nM	PMID[508322]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	2716.44	nM	PMID[508322]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	3475.36	nM	PMID[508322]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	4045.76	nM	PMID[508322]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	3810.66	nM	PMID[508322]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	3597.49	nM	PMID[508322]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	2228.44	nM	PMID[508322]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	4677.35	nM	PMID[508322]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	7362.07	nM	PMID[508322]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	3280.95	nM	PMID[508322]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	1573.98	nM	PMID[508322]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	2523.48	nM	PMID[508322]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	3191.54	nM	PMID[508322]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	11481.54	nM	PMID[508322]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	3013.01	nM	PMID[508322]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	1633.05	nM	PMID[508322]
NPT1083	Cell Line	A-375	Homo sapiens	EC50	=	5520.0	nM	PMID[508323]
NPT941	Cell Line	HaCaT	Homo sapiens	EC50	=	11400.0	nM	PMID[508323]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	EC50	=	4400.0	nM	PMID[508323]
NPT81	Cell Line	A549	Homo sapiens	EC50	=	3250.0	nM	PMID[508323]
NPT81	Cell Line	A549	Homo sapiens	FC	=	4.9	n.a.	PMID[508323]
NPT81	Cell Line	A549	Homo sapiens	FC	=	7.3	n.a.	PMID[508323]
NPT27	Others	Unspecified		EC50	=	14800.0	nM	PMID[508323]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	4190.0	nM	PMID[508323]
NPT27	Others	Unspecified		EC50	=	26400.0	nM	PMID[508323]

☑ 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 NPC16119 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	163
0.1-0.2	2056
0.2-0.3	10249
0.3-0.4	18434
0.4-0.5	7823
0.5-0.6	3352
0.6-0.7	550
0.7-0.8	41
0.8-0.85	9
0.85-0.9	5
0.9-0.95	8
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9839	High Similarity	NPC474619
0.9836	High Similarity	NPC98897
0.9672	High Similarity	NPC34622
0.9672	High Similarity	NPC474400
0.9508	High Similarity	NPC151728
0.9508	High Similarity	NPC57463
0.9385	High Similarity	NPC291062
0.9385	High Similarity	NPC94743
0.9231	High Similarity	NPC262673
0.9077	High Similarity	NPC146376
0.9077	High Similarity	NPC125578
0.9077	High Similarity	NPC263382
0.9016	High Similarity	NPC473494
0.8971	High Similarity	NPC264178
0.8923	High Similarity	NPC243272
0.8788	High Similarity	NPC134385
0.8657	High Similarity	NPC94488
0.8594	High Similarity	NPC477830
0.8462	Intermediate Similarity	NPC7029
0.8308	Intermediate Similarity	NPC143168
0.8308	Intermediate Similarity	NPC53109
0.8095	Intermediate Similarity	NPC299369
0.8095	Intermediate Similarity	NPC200831
0.8095	Intermediate Similarity	NPC224103
0.8033	Intermediate Similarity	NPC474805
0.803	Intermediate Similarity	NPC477707
0.7969	Intermediate Similarity	NPC139056
0.7903	Intermediate Similarity	NPC317796
0.7838	Intermediate Similarity	NPC473536
0.7727	Intermediate Similarity	NPC229252
0.7727	Intermediate Similarity	NPC143857
0.7703	Intermediate Similarity	NPC477708
0.7692	Intermediate Similarity	NPC320421
0.7662	Intermediate Similarity	NPC474085
0.7639	Intermediate Similarity	NPC474539
0.76	Intermediate Similarity	NPC283087
0.7541	Intermediate Similarity	NPC220191
0.7419	Intermediate Similarity	NPC22329
0.7313	Intermediate Similarity	NPC106851
0.7313	Intermediate Similarity	NPC274927
0.7284	Intermediate Similarity	NPC133652
0.7284	Intermediate Similarity	NPC241512
0.7284	Intermediate Similarity	NPC263997
0.7284	Intermediate Similarity	NPC6185
0.7284	Intermediate Similarity	NPC132228
0.7284	Intermediate Similarity	NPC8518
0.7273	Intermediate Similarity	NPC231739
0.7215	Intermediate Similarity	NPC474353
0.72	Intermediate Similarity	NPC147438
0.7188	Intermediate Similarity	NPC309606
0.7188	Intermediate Similarity	NPC139545
0.7188	Intermediate Similarity	NPC39633
0.7143	Intermediate Similarity	NPC477458
0.7123	Intermediate Similarity	NPC469914
0.7083	Intermediate Similarity	NPC251429
0.7083	Intermediate Similarity	NPC298249
0.7077	Intermediate Similarity	NPC129710
0.7051	Intermediate Similarity	NPC478247
0.7051	Intermediate Similarity	NPC23778
0.7051	Intermediate Similarity	NPC478246
0.7027	Intermediate Similarity	NPC477455
0.7015	Intermediate Similarity	NPC192843
0.7015	Intermediate Similarity	NPC281230
0.7013	Intermediate Similarity	NPC26504
0.7013	Intermediate Similarity	NPC40353
0.7	Intermediate Similarity	NPC286229
0.6986	Remote Similarity	NPC134593
0.6986	Remote Similarity	NPC218477
0.6984	Remote Similarity	NPC15325
0.6977	Remote Similarity	NPC193396
0.6977	Remote Similarity	NPC32944
0.697	Remote Similarity	NPC128061
0.697	Remote Similarity	NPC10316
0.697	Remote Similarity	NPC200845
0.697	Remote Similarity	NPC223677
0.697	Remote Similarity	NPC28779
0.697	Remote Similarity	NPC228473
0.6962	Remote Similarity	NPC471740
0.6957	Remote Similarity	NPC235242
0.6957	Remote Similarity	NPC251042
0.6957	Remote Similarity	NPC122521
0.6957	Remote Similarity	NPC174447
0.6923	Remote Similarity	NPC471061
0.6901	Remote Similarity	NPC477457
0.6901	Remote Similarity	NPC477456
0.6885	Remote Similarity	NPC191337
0.6875	Remote Similarity	NPC262968
0.6875	Remote Similarity	NPC108955
0.6875	Remote Similarity	NPC234829
0.6875	Remote Similarity	NPC304795
0.6867	Remote Similarity	NPC77971
0.6866	Remote Similarity	NPC477201
0.686	Remote Similarity	NPC223093
0.6857	Remote Similarity	NPC201939
0.6857	Remote Similarity	NPC40082
0.6842	Remote Similarity	NPC474705
0.6829	Remote Similarity	NPC477784
0.6829	Remote Similarity	NPC477785
0.6829	Remote Similarity	NPC477786
0.6829	Remote Similarity	NPC288281
0.6825	Remote Similarity	NPC145311
0.6795	Remote Similarity	NPC110725
0.679	Remote Similarity	NPC55869
0.679	Remote Similarity	NPC475833
0.679	Remote Similarity	NPC478262
0.679	Remote Similarity	NPC99308
0.679	Remote Similarity	NPC225515
0.6786	Remote Similarity	NPC203795
0.6786	Remote Similarity	NPC472009
0.6769	Remote Similarity	NPC137396
0.6757	Remote Similarity	NPC477452
0.675	Remote Similarity	NPC476177
0.6744	Remote Similarity	NPC95364
0.6744	Remote Similarity	NPC142159
0.6721	Remote Similarity	NPC477686
0.6721	Remote Similarity	NPC25771
0.6719	Remote Similarity	NPC474391
0.6719	Remote Similarity	NPC224227
0.6714	Remote Similarity	NPC243532
0.6714	Remote Similarity	NPC45097
0.6712	Remote Similarity	NPC197089
0.6711	Remote Similarity	NPC84038
0.6711	Remote Similarity	NPC66365
0.6709	Remote Similarity	NPC180290
0.6707	Remote Similarity	NPC47450
0.6707	Remote Similarity	NPC103486
0.6706	Remote Similarity	NPC472007
0.6706	Remote Similarity	NPC471739
0.6705	Remote Similarity	NPC248193
0.6667	Remote Similarity	NPC477449
0.6667	Remote Similarity	NPC91332
0.6667	Remote Similarity	NPC471399
0.6667	Remote Similarity	NPC96621
0.6667	Remote Similarity	NPC32037
0.6667	Remote Similarity	NPC474680
0.6667	Remote Similarity	NPC162741
0.6667	Remote Similarity	NPC329826
0.6667	Remote Similarity	NPC250928
0.6667	Remote Similarity	NPC474209
0.6667	Remote Similarity	NPC68343
0.6667	Remote Similarity	NPC244166
0.6667	Remote Similarity	NPC10758
0.6667	Remote Similarity	NPC475823
0.6667	Remote Similarity	NPC474060
0.6667	Remote Similarity	NPC470177
0.6667	Remote Similarity	NPC71761
0.6667	Remote Similarity	NPC328089
0.6667	Remote Similarity	NPC477448
0.6667	Remote Similarity	NPC469414
0.6667	Remote Similarity	NPC168521
0.6628	Remote Similarity	NPC53454
0.6628	Remote Similarity	NPC472008
0.6627	Remote Similarity	NPC8091
0.6625	Remote Similarity	NPC469996
0.6625	Remote Similarity	NPC475994
0.6622	Remote Similarity	NPC203335
0.6622	Remote Similarity	NPC473213
0.6591	Remote Similarity	NPC146852
0.6591	Remote Similarity	NPC476484
0.6591	Remote Similarity	NPC166110
0.6588	Remote Similarity	NPC472136
0.6585	Remote Similarity	NPC149237
0.6582	Remote Similarity	NPC471726
0.6582	Remote Similarity	NPC473223
0.6582	Remote Similarity	NPC470525
0.6582	Remote Similarity	NPC27205
0.6582	Remote Similarity	NPC266119
0.6582	Remote Similarity	NPC1254
0.6582	Remote Similarity	NPC474527
0.6579	Remote Similarity	NPC173321
0.6575	Remote Similarity	NPC251118
0.6575	Remote Similarity	NPC176215
0.6575	Remote Similarity	NPC61473
0.6575	Remote Similarity	NPC296436
0.6567	Remote Similarity	NPC6095
0.6567	Remote Similarity	NPC290563
0.6567	Remote Similarity	NPC32467
0.6567	Remote Similarity	NPC424
0.6567	Remote Similarity	NPC281972
0.6567	Remote Similarity	NPC85813
0.6567	Remote Similarity	NPC87564
0.6567	Remote Similarity	NPC25417
0.6567	Remote Similarity	NPC261831
0.6567	Remote Similarity	NPC88966
0.6567	Remote Similarity	NPC154245
0.6557	Remote Similarity	NPC292463
0.6552	Remote Similarity	NPC280833
0.6548	Remote Similarity	NPC474359
0.6543	Remote Similarity	NPC27817
0.6543	Remote Similarity	NPC475681
0.6538	Remote Similarity	NPC474321
0.6538	Remote Similarity	NPC227396
0.6533	Remote Similarity	NPC476614
0.6528	Remote Similarity	NPC288253
0.6528	Remote Similarity	NPC54925
0.6522	Remote Similarity	NPC145052
0.6522	Remote Similarity	NPC268185
0.6517	Remote Similarity	NPC61275
0.6508	Remote Similarity	NPC100380
0.6506	Remote Similarity	NPC471326

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 NPC16119 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	173
0.1-0.2	2571
0.2-0.3	4256
0.3-0.4	1626
0.4-0.5	336
0.5-0.6	166
0.6-0.7	16
0.7-0.8	2
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD6108	Clinical (unspecified phase)
0.8308	Intermediate Similarity	NPD2664	Clinical (unspecified phase)
0.8209	Intermediate Similarity	NPD3704	Approved
0.8095	Intermediate Similarity	NPD8779	Phase 3
0.8082	Intermediate Similarity	NPD4756	Discovery
0.7183	Intermediate Similarity	NPD7331	Phase 2
0.6875	Remote Similarity	NPD4695	Discontinued
0.6875	Remote Similarity	NPD28	Approved
0.6875	Remote Similarity	NPD29	Approved
0.6667	Remote Similarity	NPD3197	Phase 1
0.6575	Remote Similarity	NPD7341	Phase 2
0.6567	Remote Similarity	NPD3194	Approved
0.6567	Remote Similarity	NPD3195	Phase 2
0.6567	Remote Similarity	NPD3196	Approved
0.6567	Remote Similarity	NPD4266	Approved
0.6471	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD6672	Approved
0.6437	Remote Similarity	NPD5737	Approved
0.6418	Remote Similarity	NPD3172	Approved
0.6264	Remote Similarity	NPD5282	Discontinued
0.625	Remote Similarity	NPD8039	Approved
0.6235	Remote Similarity	NPD6110	Phase 1
0.6207	Remote Similarity	NPD5690	Phase 2
0.618	Remote Similarity	NPD6080	Approved
0.618	Remote Similarity	NPD6904	Approved
0.618	Remote Similarity	NPD6673	Approved
0.6094	Remote Similarity	NPD3174	Discontinued
0.6092	Remote Similarity	NPD5329	Approved
0.6047	Remote Similarity	NPD7154	Phase 3
0.6044	Remote Similarity	NPD5694	Approved
0.6044	Remote Similarity	NPD6050	Approved
0.6024	Remote Similarity	NPD3617	Approved
0.6023	Remote Similarity	NPD7521	Approved
0.6023	Remote Similarity	NPD5330	Approved
0.6023	Remote Similarity	NPD6409	Approved
0.6023	Remote Similarity	NPD6684	Approved
0.6023	Remote Similarity	NPD6098	Approved
0.6023	Remote Similarity	NPD7146	Approved
0.6023	Remote Similarity	NPD5279	Phase 3
0.6023	Remote Similarity	NPD7334	Approved
0.6	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD4197	Approved
0.5955	Remote Similarity	NPD3573	Approved
0.5949	Remote Similarity	NPD4691	Approved
0.5934	Remote Similarity	NPD5692	Phase 3
0.5926	Remote Similarity	NPD4058	Approved
0.5909	Remote Similarity	NPD1694	Approved
0.5909	Remote Similarity	NPD5343	Approved
0.5909	Remote Similarity	NPD5363	Approved
0.5902	Remote Similarity	NPD5783	Phase 3
0.5895	Remote Similarity	NPD6084	Phase 2
0.5895	Remote Similarity	NPD6083	Phase 2
0.5889	Remote Similarity	NPD6903	Approved
0.5889	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5873	Remote Similarity	NPD9297	Discontinued
0.5873	Remote Similarity	NPD9091	Suspended
0.587	Remote Similarity	NPD5693	Phase 1
0.587	Remote Similarity	NPD6079	Approved
0.5851	Remote Similarity	NPD5210	Approved
0.5851	Remote Similarity	NPD5695	Phase 3
0.5851	Remote Similarity	NPD4629	Approved
0.5843	Remote Similarity	NPD5280	Approved
0.5843	Remote Similarity	NPD4694	Approved
0.5824	Remote Similarity	NPD4753	Phase 2
0.5823	Remote Similarity	NPD4137	Phase 3
0.5821	Remote Similarity	NPD3173	Approved
0.5814	Remote Similarity	NPD5369	Approved
0.5795	Remote Similarity	NPD3133	Approved
0.5795	Remote Similarity	NPD4786	Approved
0.5795	Remote Similarity	NPD3665	Phase 1
0.5795	Remote Similarity	NPD3666	Approved
0.5789	Remote Similarity	NPD5222	Approved
0.5789	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD5221	Approved
0.5761	Remote Similarity	NPD5785	Approved
0.5753	Remote Similarity	NPD6109	Phase 1
0.575	Remote Similarity	NPD4747	Approved
0.5747	Remote Similarity	NPD4223	Phase 3
0.5747	Remote Similarity	NPD3667	Approved
0.5747	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5747	Remote Similarity	NPD4221	Approved
0.5732	Remote Similarity	NPD4687	Approved
0.5732	Remote Similarity	NPD5733	Approved
0.573	Remote Similarity	NPD1696	Phase 3
0.5729	Remote Similarity	NPD5173	Approved
0.5714	Remote Similarity	NPD4518	Approved
0.5686	Remote Similarity	NPD6881	Approved
0.5686	Remote Similarity	NPD6899	Approved
0.5682	Remote Similarity	NPD5362	Discontinued
0.5679	Remote Similarity	NPD5276	Approved
0.5672	Remote Similarity	NPD622	Approved
0.567	Remote Similarity	NPD5696	Approved
0.5667	Remote Similarity	NPD3618	Phase 1
0.5667	Remote Similarity	NPD4519	Discontinued
0.5667	Remote Similarity	NPD4623	Approved
0.5652	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD6101	Approved
0.5652	Remote Similarity	NPD5328	Approved
0.5618	Remote Similarity	NPD3668	Phase 3
0.5612	Remote Similarity	NPD5286	Approved
0.5612	Remote Similarity	NPD4696	Approved
0.5612	Remote Similarity	NPD5285	Approved
0.5606	Remote Similarity	NPD9090	Phase 3
0.56	Remote Similarity	NPD4246	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data