NPASS Compound

Structure

CID184702 OpenBabel06191715562D 24 26 0 0 1 0 0 0 0 0999 V2000 -5.3007 2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0525 2.9761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7579 4.0465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4347 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5686 2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4563 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8366 2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0962 2.5602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8366 0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7653 1.8171 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4781 0.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1180 2.3523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 1.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1045 0.9945 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9781 -0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1045 2.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3849 -1.1215 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7435 2.0250 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4489 3.0955 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 1.4945 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 4 1 0 0 0 0 2 21 1 0 0 0 0 3 22 1 0 0 0 0 4 5 2 0 0 0 0 5 10 1 0 0 0 0 6 11 2 0 0 0 0 6 12 1 0 0 0 0 7 10 2 0 0 0 0 7 14 1 0 0 0 0 8 11 1 0 0 0 0 8 15 2 0 0 0 0 9 13 2 0 0 0 0 9 23 1 0 0 0 0 10 23 1 0 0 0 0 11 21 1 0 0 0 0 12 16 2 0 0 0 0 12 18 1 0 0 0 0 13 14 1 0 0 0 0 14 19 2 0 0 0 0 15 16 1 0 0 0 0 15 22 1 0 0 0 0 16 17 1 0 0 0 0 17 13 1 1 0 0 0 17 24 1 0 0 0 0 18 20 2 0 0 0 0 18 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	328.09
Volume:	325.865
LogP:	2.169
LogD:	1.613
LogS:	-3.179
# Rotatable Bonds:	4
TPSA:	74.97
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.803
Synthetic Accessibility Score:	3.58
Fsp3:	0.222
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:	-4.687
MDCK Permeability:	1.759549013513606e-05
Pgp-inhibitor:	0.974
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.447

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.223
Plasma Protein Binding (PPB):	89.17290496826172%
Volume Distribution (VD):	1.077
Pgp-substrate:	10.47951889038086%

ADMET: Metabolism

CYP1A2-inhibitor:	0.57
CYP1A2-substrate:	0.867
CYP2C19-inhibitor:	0.915
CYP2C19-substrate:	0.819
CYP2C9-inhibitor:	0.884
CYP2C9-substrate:	0.899
CYP2D6-inhibitor:	0.05
CYP2D6-substrate:	0.898
CYP3A4-inhibitor:	0.794
CYP3A4-substrate:	0.359

ADMET: Excretion

Clearance (CL):	2.839
Half-life (T1/2):	0.643

ADMET: Toxicity

hERG Blockers:	0.183
Human Hepatotoxicity (H-HT):	0.653
Drug-inuced Liver Injury (DILI):	0.562
AMES Toxicity:	0.074
Rat Oral Acute Toxicity:	0.725
Maximum Recommended Daily Dose:	0.972
Skin Sensitization:	0.226
Carcinogencity:	0.254
Eye Corrosion:	0.003
Eye Irritation:	0.136
Respiratory Toxicity:	0.918

Download Data

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

Natural Product: NPC184702

Natural Product ID:	NPC184702
*Common Name:**	Vermistatin
IUPAC Name:	(3R)-4,6-dimethoxy-3-[4-oxo-6-[(E)-prop-1-enyl]pyran-3-yl]-3H-2-benzofuran-1-one
Synonyms:	Vermistatin
Standard InCHIKey:	YORFGPDHNOBVBM-BDUNBXCCSA-N
Standard InCHI:	InChI=1S/C18H16O6/c1-4-5-10-7-14(19)13(9-23-10)17-16-12(18(20)24-17)6-11(21-2)8-15(16)22-3/h4-9,17H,1-3H3/b5-4+/t17-/m0/s1
SMILES:	C/C=C/c1occ(c(=O)c1)[C@@H]1OC(=O)c2c1c(OC)cc(c2)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1997854
PubChem CID:	5467588
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans [CHEMONTID:0001578] Benzofuranones

*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
NPO29761	Penicillium rubrum	Species	Trichocomaceae	Eukaryota	n.a.	Berkeley Pit Lake, Butte, Montana	n.a.	PMID[18330993]
NPO29761	Penicillium rubrum	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21916432]
NPO29761	Penicillium rubrum	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22295871]
NPO41500	Streptomyces fradiae 007 + Penicillium sp. WC-29-5	Strain	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[24714124]
NPO28978	Zanthoxylum ovalifolium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28978	Zanthoxylum ovalifolium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28978	Zanthoxylum ovalifolium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1981	Fusarium cerealis	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1031	Eremanthus glomerulatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21132	Talaromyces verruculosus	Species	Trichocomaceae	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	43

Activity Type	# Activity
Cell Line	43

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	29648.31	nM	PMID[531551]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	45289.76	nM	PMID[531551]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	24434.31	nM	PMID[531551]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	48977.88	nM	PMID[531551]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	27352.69	nM	PMID[531551]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	26730.06	nM	PMID[531551]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	50466.13	nM	PMID[531551]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	33806.48	nM	PMID[531551]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	20749.14	nM	PMID[531551]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	38636.7	nM	PMID[531551]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	52966.34	nM	PMID[531551]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	46773.51	nM	PMID[531551]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[531551]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	57543.99	nM	PMID[531551]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	27605.78	nM	PMID[531551]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	55462.57	nM	PMID[531551]
NPT573	Cell Line	M19-MEL	Homo sapiens	GI50	n.a.	35075.19	nM	PMID[531551]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	31622.78	nM	PMID[531551]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	58748.94	nM	PMID[531551]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	35399.73	nM	PMID[531551]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	54325.03	nM	PMID[531551]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	28510.18	nM	PMID[531551]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	58613.82	nM	PMID[531551]
NPT575	Cell Line	KM-20L2	Homo sapiens	GI50	n.a.	67452.8	nM	PMID[531551]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	6486.34	nM	PMID[531551]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	26001.6	nM	PMID[531551]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	23713.74	nM	PMID[531551]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	43451.02	nM	PMID[531551]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	65463.62	nM	PMID[531551]
NPT731	Cell Line	LXFL 529	Homo sapiens	GI50	n.a.	24547.09	nM	PMID[531551]
NPT576	Cell Line	DMS-114	Homo sapiens	GI50	n.a.	21677.04	nM	PMID[531551]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	58344.51	nM	PMID[531551]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	25882.13	nM	PMID[531551]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	42072.66	nM	PMID[531551]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	36982.82	nM	PMID[531551]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	39536.66	nM	PMID[531551]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	29107.17	nM	PMID[531551]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	24099.05	nM	PMID[531551]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	60394.86	nM	PMID[531551]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	25292.98	nM	PMID[531551]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	34593.94	nM	PMID[531551]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	42169.65	nM	PMID[531551]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	22029.26	nM	PMID[531551]

☑ 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 NPC184702 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	415
0.1-0.2	1791
0.2-0.3	4186
0.3-0.4	9720
0.4-0.5	8629
0.5-0.6	3948
0.6-0.7	5778
0.7-0.8	6205
0.8-0.85	1795
0.85-0.9	221
0.9-0.95	7
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9854	High Similarity	NPC297985
0.9571	High Similarity	NPC470932
0.9236	High Similarity	NPC52106
0.9155	High Similarity	NPC471644
0.9155	High Similarity	NPC471640
0.9091	High Similarity	NPC471639
0.9091	High Similarity	NPC215451
0.9091	High Similarity	NPC471643
0.9091	High Similarity	NPC472006
0.9091	High Similarity	NPC277369
0.9034	High Similarity	NPC472033
0.9034	High Similarity	NPC107625
0.9028	High Similarity	NPC27106
0.9021	High Similarity	NPC469579
0.8986	High Similarity	NPC240768
0.8986	High Similarity	NPC473732
0.8986	High Similarity	NPC200773
0.8973	High Similarity	NPC472036
0.8966	High Similarity	NPC472034
0.8958	High Similarity	NPC51106
0.8951	High Similarity	NPC67650
0.8951	High Similarity	NPC470856
0.8951	High Similarity	NPC1704
0.8951	High Similarity	NPC90411
0.8926	High Similarity	NPC475116
0.8912	High Similarity	NPC153417
0.8889	High Similarity	NPC474385
0.8881	High Similarity	NPC109007
0.8859	High Similarity	NPC215921
0.8859	High Similarity	NPC70016
0.8857	High Similarity	NPC311339
0.8844	High Similarity	NPC137296
0.8828	High Similarity	NPC478202
0.8828	High Similarity	NPC469542
0.8819	High Similarity	NPC475730
0.8819	High Similarity	NPC158634
0.8808	High Similarity	NPC99381
0.8808	High Similarity	NPC79998
0.88	High Similarity	NPC271681
0.8794	High Similarity	NPC470844
0.8792	High Similarity	NPC469670
0.8792	High Similarity	NPC469619
0.8792	High Similarity	NPC295036
0.8792	High Similarity	NPC191104
0.8784	High Similarity	NPC240253
0.8784	High Similarity	NPC471642
0.8784	High Similarity	NPC240622
0.8784	High Similarity	NPC2569
0.8784	High Similarity	NPC215711
0.8784	High Similarity	NPC471641
0.8784	High Similarity	NPC172329
0.8784	High Similarity	NPC73411
0.8776	High Similarity	NPC470357
0.8767	High Similarity	NPC277426
0.8767	High Similarity	NPC280404
0.8767	High Similarity	NPC86373
0.8767	High Similarity	NPC210425
0.8759	High Similarity	NPC49108
0.8759	High Similarity	NPC250755
0.875	High Similarity	NPC150227
0.875	High Similarity	NPC470625
0.875	High Similarity	NPC136095
0.875	High Similarity	NPC472515
0.875	High Similarity	NPC301897
0.8741	High Similarity	NPC478200
0.8741	High Similarity	NPC191835
0.8741	High Similarity	NPC253616
0.8741	High Similarity	NPC33144
0.8725	High Similarity	NPC88445
0.8723	High Similarity	NPC223354
0.8716	High Similarity	NPC210320
0.8716	High Similarity	NPC8817
0.8707	High Similarity	NPC312789
0.8707	High Similarity	NPC75694
0.8707	High Similarity	NPC171656
0.8707	High Similarity	NPC213482
0.8707	High Similarity	NPC49282
0.8705	High Similarity	NPC473271
0.8693	High Similarity	NPC77679
0.8693	High Similarity	NPC190020
0.8693	High Similarity	NPC84935
0.869	High Similarity	NPC472035
0.869	High Similarity	NPC478217
0.869	High Similarity	NPC478201
0.869	High Similarity	NPC313123
0.8684	High Similarity	NPC199926
0.8681	High Similarity	NPC268052
0.8681	High Similarity	NPC36414
0.8681	High Similarity	NPC32360
0.8675	High Similarity	NPC207624
0.8671	High Similarity	NPC70380
0.8671	High Similarity	NPC135837
0.8671	High Similarity	NPC268081
0.8671	High Similarity	NPC254741
0.8667	High Similarity	NPC474660
0.8667	High Similarity	NPC179178
0.8667	High Similarity	NPC119929
0.8667	High Similarity	NPC470107
0.8652	High Similarity	NPC182428
0.8649	High Similarity	NPC473927
0.8639	High Similarity	NPC210966
0.8639	High Similarity	NPC478203
0.8639	High Similarity	NPC126882
0.8636	High Similarity	NPC325122
0.8627	High Similarity	NPC472050
0.8627	High Similarity	NPC474983
0.8618	High Similarity	NPC186507
0.8611	High Similarity	NPC103001
0.8611	High Similarity	NPC94248
0.8611	High Similarity	NPC472602
0.8611	High Similarity	NPC212693
0.8611	High Similarity	NPC233780
0.8609	High Similarity	NPC23668
0.8609	High Similarity	NPC115324
0.8609	High Similarity	NPC106372
0.8609	High Similarity	NPC58668
0.8609	High Similarity	NPC193976
0.86	High Similarity	NPC4423
0.86	High Similarity	NPC77325
0.86	High Similarity	NPC270160
0.86	High Similarity	NPC317492
0.86	High Similarity	NPC237440
0.86	High Similarity	NPC476684
0.8592	High Similarity	NPC247743
0.8591	High Similarity	NPC304443
0.8591	High Similarity	NPC77903
0.8591	High Similarity	NPC74539
0.8591	High Similarity	NPC474999
0.8591	High Similarity	NPC17101
0.8581	High Similarity	NPC208584
0.8581	High Similarity	NPC83272
0.8581	High Similarity	NPC134621
0.8581	High Similarity	NPC294365
0.8581	High Similarity	NPC257558
0.8571	High Similarity	NPC263483
0.8571	High Similarity	NPC313036
0.8571	High Similarity	NPC167663
0.8571	High Similarity	NPC269495
0.8562	High Similarity	NPC82592
0.8562	High Similarity	NPC99199
0.8562	High Similarity	NPC16082
0.8562	High Similarity	NPC148938
0.8562	High Similarity	NPC53649
0.8562	High Similarity	NPC472603
0.8553	High Similarity	NPC474843
0.8553	High Similarity	NPC142308
0.8552	High Similarity	NPC275356
0.8552	High Similarity	NPC92655
0.8544	High Similarity	NPC472895
0.8543	High Similarity	NPC475460
0.8543	High Similarity	NPC158866
0.8543	High Similarity	NPC216917
0.8543	High Similarity	NPC56204
0.8543	High Similarity	NPC473466
0.8543	High Similarity	NPC62354
0.8543	High Similarity	NPC96501
0.8542	High Similarity	NPC71256
0.8542	High Similarity	NPC472516
0.8533	High Similarity	NPC168085
0.8533	High Similarity	NPC37139
0.8531	High Similarity	NPC180905
0.8531	High Similarity	NPC182496
0.8526	High Similarity	NPC117985
0.8523	High Similarity	NPC163846
0.8523	High Similarity	NPC225173
0.8523	High Similarity	NPC195919
0.8523	High Similarity	NPC120924
0.8523	High Similarity	NPC237208
0.8523	High Similarity	NPC216314
0.8516	High Similarity	NPC470339
0.8516	High Similarity	NPC279732
0.8514	High Similarity	NPC151607
0.8514	High Similarity	NPC66404
0.8514	High Similarity	NPC95123
0.8514	High Similarity	NPC189650
0.8514	High Similarity	NPC475201
0.8514	High Similarity	NPC471451
0.8514	High Similarity	NPC42540
0.8511	High Similarity	NPC477412
0.8503	High Similarity	NPC96692
0.8503	High Similarity	NPC185607
0.8503	High Similarity	NPC24075
0.85	High Similarity	NPC211120
0.8497	Intermediate Similarity	NPC235333
0.8497	Intermediate Similarity	NPC478213
0.8497	Intermediate Similarity	NPC281477
0.8493	Intermediate Similarity	NPC472600
0.8493	Intermediate Similarity	NPC472601
0.8493	Intermediate Similarity	NPC158472
0.8487	Intermediate Similarity	NPC290671
0.8487	Intermediate Similarity	NPC228662
0.8487	Intermediate Similarity	NPC151425
0.8483	Intermediate Similarity	NPC470962
0.8483	Intermediate Similarity	NPC177307
0.8483	Intermediate Similarity	NPC9121
0.8478	Intermediate Similarity	NPC65041
0.8477	Intermediate Similarity	NPC65775
0.8477	Intermediate Similarity	NPC198927
0.8477	Intermediate Similarity	NPC84142
0.8477	Intermediate Similarity	NPC10027

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 NPC184702 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	362
0.1-0.2	982
0.2-0.3	1743
0.3-0.4	2619
0.4-0.5	1900
0.5-0.6	1019
0.6-0.7	363
0.7-0.8	126
0.8-0.85	31
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8707	High Similarity	NPD2533	Approved
0.8707	High Similarity	NPD2534	Approved
0.8707	High Similarity	NPD2532	Approved
0.8681	High Similarity	NPD970	Clinical (unspecified phase)
0.8671	High Similarity	NPD2796	Approved
0.8618	High Similarity	NPD7819	Suspended
0.8591	High Similarity	NPD920	Approved
0.8472	Intermediate Similarity	NPD3748	Approved
0.8456	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8367	Intermediate Similarity	NPD1243	Approved
0.8344	Intermediate Similarity	NPD5494	Approved
0.8322	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8267	Intermediate Similarity	NPD6799	Approved
0.8219	Intermediate Similarity	NPD1510	Phase 2
0.8205	Intermediate Similarity	NPD3817	Phase 2
0.8188	Intermediate Similarity	NPD3750	Approved
0.8182	Intermediate Similarity	NPD6599	Discontinued
0.8165	Intermediate Similarity	NPD919	Approved
0.8141	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD3749	Approved
0.8092	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD6801	Discontinued
0.8069	Intermediate Similarity	NPD1240	Approved
0.8067	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD4380	Phase 2
0.8054	Intermediate Similarity	NPD1549	Phase 2
0.8038	Intermediate Similarity	NPD3882	Suspended
0.8037	Intermediate Similarity	NPD3818	Discontinued
0.8025	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD7411	Suspended
0.8012	Intermediate Similarity	NPD5710	Approved
0.8012	Intermediate Similarity	NPD5711	Approved
0.8012	Intermediate Similarity	NPD6232	Discontinued
0.7987	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD7075	Discontinued
0.7987	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD7473	Discontinued
0.7975	Intermediate Similarity	NPD5402	Approved
0.7962	Intermediate Similarity	NPD1934	Approved
0.7959	Intermediate Similarity	NPD1607	Approved
0.795	Intermediate Similarity	NPD1247	Approved
0.7931	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD2935	Discontinued
0.7911	Intermediate Similarity	NPD2801	Approved
0.7881	Intermediate Similarity	NPD2800	Approved
0.7879	Intermediate Similarity	NPD5844	Phase 1
0.7875	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD3926	Phase 2
0.784	Intermediate Similarity	NPD6959	Discontinued
0.7793	Intermediate Similarity	NPD6832	Phase 2
0.7792	Intermediate Similarity	NPD1511	Approved
0.7771	Intermediate Similarity	NPD3226	Approved
0.777	Intermediate Similarity	NPD230	Phase 1
0.777	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD2654	Approved
0.7763	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD5403	Approved
0.775	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD2346	Discontinued
0.7742	Intermediate Similarity	NPD5401	Approved
0.7742	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD2799	Discontinued
0.7712	Intermediate Similarity	NPD4628	Phase 3
0.7702	Intermediate Similarity	NPD7768	Phase 2
0.7697	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1512	Approved
0.7683	Intermediate Similarity	NPD7229	Phase 3
0.7682	Intermediate Similarity	NPD1551	Phase 2
0.764	Intermediate Similarity	NPD5353	Approved
0.7636	Intermediate Similarity	NPD5242	Approved
0.7633	Intermediate Similarity	NPD6559	Discontinued
0.7625	Intermediate Similarity	NPD37	Approved
0.7593	Intermediate Similarity	NPD4967	Phase 2
0.7593	Intermediate Similarity	NPD4965	Approved
0.7593	Intermediate Similarity	NPD4966	Approved
0.759	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD6166	Phase 2
0.759	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD5691	Approved
0.7588	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD1465	Phase 2
0.7568	Intermediate Similarity	NPD1296	Phase 2
0.7568	Intermediate Similarity	NPD3764	Approved
0.7568	Intermediate Similarity	NPD2313	Discontinued
0.756	Intermediate Similarity	NPD7054	Approved
0.7535	Intermediate Similarity	NPD17	Approved
0.7534	Intermediate Similarity	NPD2798	Approved
0.7534	Intermediate Similarity	NPD1019	Discontinued
0.7517	Intermediate Similarity	NPD1876	Approved
0.7516	Intermediate Similarity	NPD2344	Approved
0.7516	Intermediate Similarity	NPD1471	Phase 3
0.7515	Intermediate Similarity	NPD7199	Phase 2
0.7515	Intermediate Similarity	NPD7472	Approved
0.7515	Intermediate Similarity	NPD7074	Phase 3
0.75	Intermediate Similarity	NPD7033	Discontinued
0.75	Intermediate Similarity	NPD3972	Approved
0.75	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6234	Discontinued
0.75	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD5953	Discontinued
0.7471	Intermediate Similarity	NPD6797	Phase 2
0.747	Intermediate Similarity	NPD6808	Phase 2
0.7467	Intermediate Similarity	NPD2979	Phase 3
0.7466	Intermediate Similarity	NPD3266	Approved
0.7466	Intermediate Similarity	NPD3267	Approved
0.7456	Intermediate Similarity	NPD7286	Phase 2
0.7456	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD7251	Discontinued
0.7425	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD4288	Approved
0.7417	Intermediate Similarity	NPD447	Suspended
0.7405	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD9545	Approved
0.7386	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD7808	Phase 3
0.7381	Intermediate Similarity	NPD2403	Approved
0.7379	Intermediate Similarity	NPD9717	Approved
0.7379	Intermediate Similarity	NPD1608	Approved
0.7368	Intermediate Similarity	NPD6651	Approved
0.7358	Intermediate Similarity	NPD6273	Approved
0.7351	Intermediate Similarity	NPD4307	Phase 2
0.7351	Intermediate Similarity	NPD943	Approved
0.7346	Intermediate Similarity	NPD6385	Approved
0.7346	Intermediate Similarity	NPD6386	Approved
0.7342	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD6100	Approved
0.7338	Intermediate Similarity	NPD6099	Approved
0.7338	Intermediate Similarity	NPD2438	Suspended
0.7333	Intermediate Similarity	NPD3268	Approved
0.7329	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD2309	Approved
0.7314	Intermediate Similarity	NPD8434	Phase 2
0.731	Intermediate Similarity	NPD422	Phase 1
0.731	Intermediate Similarity	NPD1281	Approved
0.7294	Intermediate Similarity	NPD3751	Discontinued
0.7292	Intermediate Similarity	NPD4626	Approved
0.7289	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD1241	Discontinued
0.7283	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD3787	Discontinued
0.7257	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD7390	Discontinued
0.7232	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD1203	Approved
0.723	Intermediate Similarity	NPD2797	Approved
0.7222	Intermediate Similarity	NPD1651	Approved
0.7219	Intermediate Similarity	NPD411	Approved
0.7215	Intermediate Similarity	NPD3887	Approved
0.72	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD6280	Approved
0.7195	Intermediate Similarity	NPD6279	Approved
0.7193	Intermediate Similarity	NPD7228	Approved
0.719	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD5124	Phase 1
0.719	Intermediate Similarity	NPD1933	Approved
0.719	Intermediate Similarity	NPD6355	Discontinued
0.7179	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6005	Phase 3
0.7179	Intermediate Similarity	NPD6004	Phase 3
0.7179	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6002	Phase 3
0.7176	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD5006	Approved
0.7174	Intermediate Similarity	NPD2182	Approved
0.7174	Intermediate Similarity	NPD5005	Approved
0.7171	Intermediate Similarity	NPD8032	Phase 2
0.7162	Intermediate Similarity	NPD1283	Approved
0.7161	Intermediate Similarity	NPD4308	Phase 3
0.7152	Intermediate Similarity	NPD5760	Phase 2
0.7152	Intermediate Similarity	NPD5761	Phase 2
0.7152	Intermediate Similarity	NPD7003	Approved
0.7143	Intermediate Similarity	NPD8313	Approved
0.7143	Intermediate Similarity	NPD8312	Approved
0.7135	Intermediate Similarity	NPD4287	Approved
0.7134	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD9493	Approved
0.7126	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD7458	Discontinued
0.7115	Intermediate Similarity	NPD5404	Approved
0.7115	Intermediate Similarity	NPD5406	Approved
0.7115	Intermediate Similarity	NPD5405	Approved
0.7115	Intermediate Similarity	NPD2531	Phase 2
0.7115	Intermediate Similarity	NPD5408	Approved
0.7103	Intermediate Similarity	NPD9268	Approved
0.7089	Intermediate Similarity	NPD1652	Phase 2
0.7075	Intermediate Similarity	NPD3705	Approved
0.7063	Intermediate Similarity	NPD6652	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD1778	Approved
0.7049	Intermediate Similarity	NPD4420	Approved
0.7043	Intermediate Similarity	NPD7435	Discontinued
0.7037	Intermediate Similarity	NPD7314	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