NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	199.06
Volume:	203.197
LogP:	2.288
LogD:	2.238
LogS:	-3.616
# Rotatable Bonds:	0
TPSA:	35.14
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.556
Synthetic Accessibility Score:	2.421
Fsp3:	0.083
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.744
MDCK Permeability:	3.20205872412771e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.825
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.022
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.857
Plasma Protein Binding (PPB):	89.3831787109375%
Volume Distribution (VD):	0.789
Pgp-substrate:	9.11650276184082%

ADMET: Metabolism

CYP1A2-inhibitor:	0.982
CYP1A2-substrate:	0.885
CYP2C19-inhibitor:	0.853
CYP2C19-substrate:	0.343
CYP2C9-inhibitor:	0.412
CYP2C9-substrate:	0.765
CYP2D6-inhibitor:	0.451
CYP2D6-substrate:	0.72
CYP3A4-inhibitor:	0.068
CYP3A4-substrate:	0.251

ADMET: Excretion

Clearance (CL):	3.46
Half-life (T1/2):	0.334

ADMET: Toxicity

hERG Blockers:	0.036
Human Hepatotoxicity (H-HT):	0.137
Drug-inuced Liver Injury (DILI):	0.842
AMES Toxicity:	0.899
Rat Oral Acute Toxicity:	0.174
Maximum Recommended Daily Dose:	0.304
Skin Sensitization:	0.125
Carcinogencity:	0.926
Eye Corrosion:	0.016
Eye Irritation:	0.947
Respiratory Toxicity:	0.904

Download Data

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

Natural Product: NPC45389

Natural Product ID:	NPC45389
*Common Name:**	Isodictamnine
IUPAC Name:	9-methylfuro[2,3-b]quinolin-4-one
Synonyms:	Isodictamnine
Standard InCHIKey:	FUVCJKNEOUWLPI-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H9NO2/c1-13-10-5-3-2-4-8(10)11(14)9-6-7-15-12(9)13/h2-7H,1H3
SMILES:	Cn1c2ccccc2c(=O)c2c1occ2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL509839
PubChem CID:	442913
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0002374] Furanoquinolines

*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
NPO17936	Glycosmis arborea	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15387647]
NPO10791	Uvaria grandiflora	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16643056]
NPO18723	Zanthoxylum avicennae	Species	Rutaceae	Eukaryota	stem wood	Pakuashan, Changhua County, Taiwan	2006-Jun	PMID[18211005]
NPO15142	Echium plantagineum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19166	Helianthus niveus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18997	Hernandia sonora	Species	Hernandiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18723	Zanthoxylum avicennae	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29208	Dictamnus albus	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19166	Helianthus niveus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15142	Echium plantagineum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18723	Zanthoxylum avicennae	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18997	Hernandia sonora	Species	Hernandiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29208	Dictamnus albus	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10791	Uvaria grandiflora	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29208	Dictamnus albus	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18723	Zanthoxylum avicennae	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21284	Cynoglossum viridiflorum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20279	Parmelia damaziana	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19166	Helianthus niveus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15142	Echium plantagineum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16406	Leptospermum recurvum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29208	Dictamnus albus	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16000	Cetorhinus maximus	Species	Alopiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10791	Uvaria grandiflora	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17936	Glycosmis arborea	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18997	Hernandia sonora	Species	Hernandiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13941	Aeollanthus buchnerianus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18723	Zanthoxylum avicennae	Species	Rutaceae	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
IC50	2
Others	8

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	2
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	>	80.0	%	PMID[548782]
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	60.0	%	PMID[548782]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[548781]
NPT2	Others	Unspecified		Activity	=	18.4	%	PMID[548782]
NPT2	Others	Unspecified		Activity	=	40.3	%	PMID[548782]
NPT2	Others	Unspecified		Activity	=	72.2	%	PMID[548782]
NPT2	Others	Unspecified		Activity	=	100.0	%	PMID[548782]

☑ 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 NPC45389 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	706
0.1-0.2	4675
0.2-0.3	12334
0.3-0.4	6228
0.4-0.5	13415
0.5-0.6	3630
0.6-0.7	1442
0.7-0.8	247
0.8-0.85	14
0.85-0.9	2
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9379	High Similarity	NPC112937
0.9333	High Similarity	NPC41216
0.84	Intermediate Similarity	NPC471648
0.8023	Intermediate Similarity	NPC471652
0.797	Intermediate Similarity	NPC269367
0.7811	Intermediate Similarity	NPC16066
0.7745	Intermediate Similarity	NPC298436
0.7727	Intermediate Similarity	NPC471649
0.7697	Intermediate Similarity	NPC93653
0.768	Intermediate Similarity	NPC471651
0.7656	Intermediate Similarity	NPC254957
0.7638	Intermediate Similarity	NPC198160
0.7576	Intermediate Similarity	NPC207971
0.756	Intermediate Similarity	NPC97746
0.7538	Intermediate Similarity	NPC268077
0.7524	Intermediate Similarity	NPC131885
0.75	Intermediate Similarity	NPC71124
0.75	Intermediate Similarity	NPC234933
0.7473	Intermediate Similarity	NPC299582
0.7451	Intermediate Similarity	NPC116178
0.7423	Intermediate Similarity	NPC206109
0.7423	Intermediate Similarity	NPC114039
0.7423	Intermediate Similarity	NPC473004
0.7418	Intermediate Similarity	NPC204867
0.7415	Intermediate Similarity	NPC217903
0.7415	Intermediate Similarity	NPC321166
0.7374	Intermediate Similarity	NPC5374
0.7371	Intermediate Similarity	NPC471647
0.7371	Intermediate Similarity	NPC471646
0.7354	Intermediate Similarity	NPC5167
0.7346	Intermediate Similarity	NPC205372
0.7323	Intermediate Similarity	NPC100863
0.7302	Intermediate Similarity	NPC217176
0.7291	Intermediate Similarity	NPC478075
0.7282	Intermediate Similarity	NPC1820
0.7264	Intermediate Similarity	NPC15987
0.7263	Intermediate Similarity	NPC85613
0.7243	Intermediate Similarity	NPC140296
0.7241	Intermediate Similarity	NPC477161
0.723	Intermediate Similarity	NPC122886
0.7206	Intermediate Similarity	NPC308943
0.7202	Intermediate Similarity	NPC473007
0.72	Intermediate Similarity	NPC241263
0.7179	Intermediate Similarity	NPC471650
0.717	Intermediate Similarity	NPC329830
0.7129	Intermediate Similarity	NPC55470
0.7095	Intermediate Similarity	NPC242000
0.7085	Intermediate Similarity	NPC230313
0.7081	Intermediate Similarity	NPC257763
0.7079	Intermediate Similarity	NPC138830
0.7077	Intermediate Similarity	NPC87391
0.7072	Intermediate Similarity	NPC168922
0.7067	Intermediate Similarity	NPC220241
0.7067	Intermediate Similarity	NPC295479
0.7056	Intermediate Similarity	NPC473008
0.7047	Intermediate Similarity	NPC197335
0.7045	Intermediate Similarity	NPC34770
0.7028	Intermediate Similarity	NPC195120
0.701	Intermediate Similarity	NPC314659
0.701	Intermediate Similarity	NPC288759
0.7	Intermediate Similarity	NPC243626
0.7	Intermediate Similarity	NPC198401
0.7	Intermediate Similarity	NPC30749
0.6995	Remote Similarity	NPC298320
0.6995	Remote Similarity	NPC67904
0.6978	Remote Similarity	NPC188400
0.6973	Remote Similarity	NPC301163
0.6971	Remote Similarity	NPC208170
0.6971	Remote Similarity	NPC216149
0.6961	Remote Similarity	NPC144691
0.6959	Remote Similarity	NPC270301
0.6957	Remote Similarity	NPC212123
0.6952	Remote Similarity	NPC305542
0.6952	Remote Similarity	NPC10732
0.6948	Remote Similarity	NPC87560
0.6923	Remote Similarity	NPC329567
0.6923	Remote Similarity	NPC207873
0.6923	Remote Similarity	NPC100573
0.6923	Remote Similarity	NPC330683
0.6919	Remote Similarity	NPC268223
0.691	Remote Similarity	NPC308197
0.6907	Remote Similarity	NPC283810
0.6906	Remote Similarity	NPC223873
0.6905	Remote Similarity	NPC220337
0.6886	Remote Similarity	NPC1608
0.6884	Remote Similarity	NPC118154
0.6884	Remote Similarity	NPC157983
0.6882	Remote Similarity	NPC133817
0.6882	Remote Similarity	NPC476443
0.6881	Remote Similarity	NPC308895
0.6875	Remote Similarity	NPC222561
0.6869	Remote Similarity	NPC21425
0.6869	Remote Similarity	NPC182853
0.686	Remote Similarity	NPC313112
0.686	Remote Similarity	NPC301292
0.6858	Remote Similarity	NPC166712
0.6837	Remote Similarity	NPC27887
0.6828	Remote Similarity	NPC160100
0.6828	Remote Similarity	NPC208364
0.6827	Remote Similarity	NPC45190
0.6825	Remote Similarity	NPC146418
0.6821	Remote Similarity	NPC222524
0.68	Remote Similarity	NPC473569
0.6798	Remote Similarity	NPC477258
0.6792	Remote Similarity	NPC310211
0.6792	Remote Similarity	NPC308137
0.6791	Remote Similarity	NPC134702
0.6791	Remote Similarity	NPC77777
0.6788	Remote Similarity	NPC470548
0.6786	Remote Similarity	NPC288305
0.6774	Remote Similarity	NPC198503
0.6773	Remote Similarity	NPC157931
0.6769	Remote Similarity	NPC58209
0.6768	Remote Similarity	NPC49184
0.6763	Remote Similarity	NPC473005
0.6761	Remote Similarity	NPC473006
0.6757	Remote Similarity	NPC119669
0.675	Remote Similarity	NPC169387
0.675	Remote Similarity	NPC477259
0.6745	Remote Similarity	NPC218303
0.6744	Remote Similarity	NPC313327
0.6743	Remote Similarity	NPC266425
0.6738	Remote Similarity	NPC113946
0.6736	Remote Similarity	NPC96901
0.6734	Remote Similarity	NPC262725
0.6734	Remote Similarity	NPC116007
0.6734	Remote Similarity	NPC194040
0.6734	Remote Similarity	NPC150308
0.6729	Remote Similarity	NPC148391
0.6729	Remote Similarity	NPC2905
0.6727	Remote Similarity	NPC476436
0.6725	Remote Similarity	NPC250476
0.6714	Remote Similarity	NPC249583
0.6714	Remote Similarity	NPC264176
0.6713	Remote Similarity	NPC46561
0.671	Remote Similarity	NPC173250
0.6702	Remote Similarity	NPC279527
0.6702	Remote Similarity	NPC214960
0.67	Remote Similarity	NPC471825
0.6699	Remote Similarity	NPC14339
0.6698	Remote Similarity	NPC25961
0.6697	Remote Similarity	NPC478078
0.6697	Remote Similarity	NPC118189
0.6684	Remote Similarity	NPC29285
0.6683	Remote Similarity	NPC22476
0.6682	Remote Similarity	NPC288987
0.6682	Remote Similarity	NPC114468
0.6681	Remote Similarity	NPC203373
0.6667	Remote Similarity	NPC26589
0.6667	Remote Similarity	NPC471762
0.6667	Remote Similarity	NPC473444
0.6667	Remote Similarity	NPC231382
0.6651	Remote Similarity	NPC298449
0.6651	Remote Similarity	NPC176113
0.6651	Remote Similarity	NPC477160
0.6651	Remote Similarity	NPC323969
0.665	Remote Similarity	NPC204970
0.665	Remote Similarity	NPC83511
0.6649	Remote Similarity	NPC73280
0.6649	Remote Similarity	NPC24954
0.6636	Remote Similarity	NPC159815
0.6636	Remote Similarity	NPC247803
0.6636	Remote Similarity	NPC472098
0.6634	Remote Similarity	NPC174629
0.6622	Remote Similarity	NPC13249
0.6621	Remote Similarity	NPC76478
0.662	Remote Similarity	NPC474366
0.6617	Remote Similarity	NPC473815
0.6616	Remote Similarity	NPC472163
0.6612	Remote Similarity	NPC286692
0.661	Remote Similarity	NPC173295
0.6604	Remote Similarity	NPC90185
0.66	Remote Similarity	NPC322621
0.6593	Remote Similarity	NPC160113
0.6593	Remote Similarity	NPC476220
0.6591	Remote Similarity	NPC148124
0.6589	Remote Similarity	NPC187501
0.6588	Remote Similarity	NPC300156
0.6582	Remote Similarity	NPC129624
0.6578	Remote Similarity	NPC476429
0.6575	Remote Similarity	NPC150239
0.6571	Remote Similarity	NPC317572
0.6566	Remote Similarity	NPC166169
0.6564	Remote Similarity	NPC154922
0.6564	Remote Similarity	NPC177261
0.6562	Remote Similarity	NPC70172
0.6561	Remote Similarity	NPC314633
0.6558	Remote Similarity	NPC470481
0.6558	Remote Similarity	NPC470482
0.6553	Remote Similarity	NPC170333
0.6552	Remote Similarity	NPC474059
0.6552	Remote Similarity	NPC208890
0.6549	Remote Similarity	NPC329631
0.6547	Remote Similarity	NPC257851
0.6545	Remote Similarity	NPC99724
0.6545	Remote Similarity	NPC7560
0.6544	Remote Similarity	NPC234772
0.6542	Remote Similarity	NPC470020
0.654	Remote Similarity	NPC120513
0.6533	Remote Similarity	NPC28368

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 NPC45389 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	419
0.1-0.2	690
0.2-0.3	933
0.3-0.4	1585
0.4-0.5	2841
0.5-0.6	1945
0.6-0.7	643
0.7-0.8	93
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
0.7744	Intermediate Similarity	NPD6321	Discontinued
0.75	Intermediate Similarity	NPD4981	Phase 2
0.7448	Intermediate Similarity	NPD6608	Clinical (unspecified phase)
0.7446	Intermediate Similarity	NPD5186	Approved
0.7446	Intermediate Similarity	NPD5183	Approved
0.7374	Intermediate Similarity	NPD1880	Phase 3
0.7363	Intermediate Similarity	NPD4465	Phase 2
0.7363	Intermediate Similarity	NPD4467	Phase 2
0.735	Intermediate Similarity	NPD7626	Approved
0.735	Intermediate Similarity	NPD7627	Approved
0.7295	Intermediate Similarity	NPD5293	Phase 2
0.7287	Intermediate Similarity	NPD5603	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD6654	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD3050	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD7186	Phase 3
0.7158	Intermediate Similarity	NPD5521	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD3507	Phase 2
0.7143	Intermediate Similarity	NPD7064	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD6533	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD5900	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD6021	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD6457	Approved
0.7094	Intermediate Similarity	NPD956	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3899	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD5071	Phase 2
0.7059	Intermediate Similarity	NPD6478	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD3783	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD5860	Discontinued
0.7015	Intermediate Similarity	NPD5515	Phase 2
0.6974	Remote Similarity	NPD4078	Clinical (unspecified phase)
0.697	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD4515	Suspended
0.6946	Remote Similarity	NPD6874	Approved
0.6941	Remote Similarity	NPD4952	Phase 3
0.6934	Remote Similarity	NPD5025	Approved
0.6923	Remote Similarity	NPD2906	Approved
0.6923	Remote Similarity	NPD2907	Approved
0.692	Remote Similarity	NPD7560	Approved
0.6905	Remote Similarity	NPD1945	Phase 1
0.6889	Remote Similarity	NPD6790	Phase 1
0.6881	Remote Similarity	NPD3964	Approved
0.6864	Remote Similarity	NPD6199	Discontinued
0.6863	Remote Similarity	NPD3297	Approved
0.6847	Remote Similarity	NPD4373	Phase 2
0.6842	Remote Similarity	NPD2681	Approved
0.6842	Remote Similarity	NPD2680	Approved
0.6842	Remote Similarity	NPD4082	Approved
0.683	Remote Similarity	NPD4846	Phase 2
0.6823	Remote Similarity	NPD2248	Approved
0.6823	Remote Similarity	NPD2246	Approved
0.6822	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD743	Approved
0.6818	Remote Similarity	NPD2670	Approved
0.6811	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD1212	Approved
0.6796	Remote Similarity	NPD160	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD710	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD3912	Discontinued
0.6776	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.675	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6745	Remote Similarity	NPD4493	Discontinued
0.6745	Remote Similarity	NPD683	Approved
0.6729	Remote Similarity	NPD3257	Approved
0.6728	Remote Similarity	NPD3437	Discontinued
0.6714	Remote Similarity	NPD7225	Discontinued
0.6701	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD4456	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD2778	Approved
0.6699	Remote Similarity	NPD3298	Approved
0.6685	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD8027	Approved
0.6682	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4496	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD7031	Phase 1
0.6651	Remote Similarity	NPD7559	Phase 2
0.6651	Remote Similarity	NPD3802	Phase 3
0.6651	Remote Similarity	NPD3874	Discontinued
0.6649	Remote Similarity	NPD5997	Discontinued
0.6649	Remote Similarity	NPD1670	Discontinued
0.6648	Remote Similarity	NPD3142	Approved
0.6648	Remote Similarity	NPD3140	Approved
0.6636	Remote Similarity	NPD4492	Approved
0.6636	Remote Similarity	NPD4494	Approved
0.6635	Remote Similarity	NPD4596	Phase 1
0.6635	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD7043	Discontinued
0.6634	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD3793	Phase 3
0.6633	Remote Similarity	NPD5600	Discontinued
0.662	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD3446	Phase 1
0.6614	Remote Similarity	NPD5294	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD814	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD2899	Discontinued
0.6606	Remote Similarity	NPD3258	Approved
0.6606	Remote Similarity	NPD5496	Approved
0.6604	Remote Similarity	NPD3472	Approved
0.6604	Remote Similarity	NPD4154	Approved
0.6604	Remote Similarity	NPD4022	Approved
0.6603	Remote Similarity	NPD2779	Approved
0.6602	Remote Similarity	NPD5564	Approved
0.6596	Remote Similarity	NPD2366	Approved
0.6591	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD6040	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD6357	Discontinued
0.6576	Remote Similarity	NPD1802	Approved
0.6576	Remote Similarity	NPD1801	Approved
0.6575	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD5513	Phase 2
0.6567	Remote Similarity	NPD4369	Phase 2
0.6564	Remote Similarity	NPD7853	Phase 2
0.6561	Remote Similarity	NPD6279	Approved
0.6561	Remote Similarity	NPD6280	Approved
0.6557	Remote Similarity	NPD5143	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD6238	Discontinued
0.6549	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD3965	Phase 1
0.6547	Remote Similarity	NPD4328	Approved
0.6542	Remote Similarity	NPD3372	Discontinued
0.6542	Remote Similarity	NPD1166	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD3893	Discontinued
0.654	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.654	Remote Similarity	NPD3947	Discontinued
0.6532	Remote Similarity	NPD3925	Approved
0.6526	Remote Similarity	NPD7467	Discontinued
0.652	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD3239	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD6719	Approved
0.651	Remote Similarity	NPD955	Approved
0.651	Remote Similarity	NPD1307	Phase 2
0.651	Remote Similarity	NPD1309	Phase 2
0.6508	Remote Similarity	NPD2672	Discontinued
0.6507	Remote Similarity	NPD4491	Clinical (unspecified phase)
0.65	Remote Similarity	NPD692	Approved
0.65	Remote Similarity	NPD7180	Phase 3
0.6498	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD8102	Discontinued
0.6495	Remote Similarity	NPD2249	Approved
0.6495	Remote Similarity	NPD2247	Approved
0.6494	Remote Similarity	NPD6716	Phase 1
0.6493	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.649	Remote Similarity	NPD1198	Approved
0.6489	Remote Similarity	NPD5479	Discontinued
0.6489	Remote Similarity	NPD1659	Phase 1
0.6489	Remote Similarity	NPD5022	Discontinued
0.6485	Remote Similarity	NPD3154	Approved
0.6485	Remote Similarity	NPD3153	Approved
0.6484	Remote Similarity	NPD4429	Discontinued
0.6482	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD3888	Discontinued
0.6476	Remote Similarity	NPD3416	Discontinued
0.6471	Remote Similarity	NPD4259	Approved
0.6471	Remote Similarity	NPD4258	Approved
0.6462	Remote Similarity	NPD5847	Phase 1
0.6462	Remote Similarity	NPD6250	Discontinued
0.646	Remote Similarity	NPD3442	Approved
0.646	Remote Similarity	NPD6962	Phase 2
0.646	Remote Similarity	NPD3441	Approved
0.6456	Remote Similarity	NPD4539	Phase 1
0.6453	Remote Similarity	NPD6891	Phase 2
0.6452	Remote Similarity	NPD7528	Approved
0.6452	Remote Similarity	NPD4455	Discontinued
0.6452	Remote Similarity	NPD3945	Discontinued
0.645	Remote Similarity	NPD4204	Approved
0.645	Remote Similarity	NPD4203	Approved
0.6449	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6445	Remote Similarity	NPD7316	Discontinued
0.6443	Remote Similarity	NPD1559	Discontinued
0.6435	Remote Similarity	NPD5416	Discontinued
0.6432	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD1200	Approved
0.6429	Remote Similarity	NPD2339	Phase 3
0.6429	Remote Similarity	NPD6805	Discontinued
0.6429	Remote Similarity	NPD1199	Approved
0.6425	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD4679	Discontinued
0.6422	Remote Similarity	NPD7291	Discontinued
0.6421	Remote Similarity	NPD4201	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD7190	Clinical (unspecified phase)
0.6416	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6411	Remote Similarity	NPD5194	Approved
0.6411	Remote Similarity	NPD5196	Approved
0.6411	Remote Similarity	NPD5197	Approved
0.641	Remote Similarity	NPD5262	Discontinued
0.6409	Remote Similarity	NPD5632	Approved
0.6409	Remote Similarity	NPD3170	Approved
0.6402	Remote Similarity	NPD3229	Phase 2
0.64	Remote Similarity	NPD3259	Approved
0.6398	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD8157	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