NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	229.07
Volume:	229.284
LogP:	3.167
LogD:	3.207
LogS:	-4.071
# Rotatable Bonds:	2
TPSA:	44.49
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.677
Synthetic Accessibility Score:	2.366
Fsp3:	0.154
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.746
MDCK Permeability:	2.8745034796884283e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.409
Plasma Protein Binding (PPB):	90.16521453857422%
Volume Distribution (VD):	0.504
Pgp-substrate:	6.333191871643066%

ADMET: Metabolism

CYP1A2-inhibitor:	0.99
CYP1A2-substrate:	0.949
CYP2C19-inhibitor:	0.897
CYP2C19-substrate:	0.451
CYP2C9-inhibitor:	0.585
CYP2C9-substrate:	0.896
CYP2D6-inhibitor:	0.761
CYP2D6-substrate:	0.918
CYP3A4-inhibitor:	0.829
CYP3A4-substrate:	0.344

ADMET: Excretion

Clearance (CL):	9.435
Half-life (T1/2):	0.303

ADMET: Toxicity

hERG Blockers:	0.113
Human Hepatotoxicity (H-HT):	0.429
Drug-inuced Liver Injury (DILI):	0.926
AMES Toxicity:	0.792
Rat Oral Acute Toxicity:	0.529
Maximum Recommended Daily Dose:	0.438
Skin Sensitization:	0.348
Carcinogencity:	0.747
Eye Corrosion:	0.003
Eye Irritation:	0.161
Respiratory Toxicity:	0.925

Download Data

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

Natural Product: NPC298436

Natural Product ID:	NPC298436
*Common Name:**	Evolitrine
IUPAC Name:	4,7-dimethoxyfuro[2,3-b]quinoline
Synonyms:	4,7-Dimethoxyfuro[2,3-B]Quinoline
Standard InCHIKey:	TWGHMXOYRUTQOL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H11NO3/c1-15-8-3-4-9-11(7-8)14-13-10(5-6-17-13)12(9)16-2/h3-7H,1-2H3
SMILES:	COc1ccc2c(c1)nc1c(cco1)c2OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL401536
PubChem CID:	196980
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
NPO26797	Laurencia glandulifera	Species	Rhodomelaceae	Eukaryota	n.a.	the island of Crete in the south Aegean Sea	n.a.	PMID[19138151]
NPO26277	Euphorbia hirta	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32141299]
NPO26277	Euphorbia hirta	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26277	Euphorbia hirta	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26277	Euphorbia hirta	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26277	Euphorbia hirta	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27010	Halosaccion ramentaceum	Species	Palmariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26797	Laurencia glandulifera	Species	Rhodomelaceae	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
Others	8

Activity Type	# Activity
Cell Line	4
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	60.0	%	PMID[537309]
NPT80	Cell Line	Raji	Homo sapiens	Activity	>	80.0	%	PMID[537309]
NPT2	Others	Unspecified		Activity	=	18.7	%	PMID[537309]
NPT2	Others	Unspecified		Activity	=	44.1	%	PMID[537309]
NPT2	Others	Unspecified		Activity	=	75.0	%	PMID[537309]
NPT2	Others	Unspecified		Activity	=	100.0	%	PMID[537309]

☑ 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 NPC298436 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	594
0.1-0.2	3441
0.2-0.3	12360
0.3-0.4	4454
0.4-0.5	11344
0.5-0.6	8840
0.6-0.7	1365
0.7-0.8	265
0.8-0.85	15
0.85-0.9	12
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9749	High Similarity	NPC97746
0.9588	High Similarity	NPC269367
0.9415	High Similarity	NPC217176
0.9394	High Similarity	NPC16066
0.9104	High Similarity	NPC168922
0.9005	High Similarity	NPC34770
0.8977	High Similarity	NPC188400
0.8971	High Similarity	NPC131885
0.89	High Similarity	NPC140296
0.8853	High Similarity	NPC1608
0.8756	High Similarity	NPC205372
0.8756	High Similarity	NPC166712
0.8716	High Similarity	NPC160100
0.8716	High Similarity	NPC208364
0.8636	High Similarity	NPC58209
0.8559	High Similarity	NPC173250
0.852	High Similarity	NPC203373
0.8333	Intermediate Similarity	NPC120513
0.819	Intermediate Similarity	NPC308137
0.819	Intermediate Similarity	NPC310211
0.814	Intermediate Similarity	NPC198503
0.8125	Intermediate Similarity	NPC249583
0.8084	Intermediate Similarity	NPC46561
0.8057	Intermediate Similarity	NPC146418
0.8028	Intermediate Similarity	NPC116238
0.8025	Intermediate Similarity	NPC101312
0.8	Intermediate Similarity	NPC247803
0.7953	Intermediate Similarity	NPC169402
0.7926	Intermediate Similarity	NPC150239
0.7895	Intermediate Similarity	NPC41216
0.7867	Intermediate Similarity	NPC4687
0.7844	Intermediate Similarity	NPC174760
0.7805	Intermediate Similarity	NPC279401
0.7805	Intermediate Similarity	NPC79293
0.7798	Intermediate Similarity	NPC208084
0.7767	Intermediate Similarity	NPC264176
0.7761	Intermediate Similarity	NPC62069
0.7753	Intermediate Similarity	NPC6786
0.7745	Intermediate Similarity	NPC45389
0.7736	Intermediate Similarity	NPC45190
0.7721	Intermediate Similarity	NPC87413
0.7661	Intermediate Similarity	NPC3207
0.7625	Intermediate Similarity	NPC230683
0.7623	Intermediate Similarity	NPC179287
0.7598	Intermediate Similarity	NPC194040
0.7581	Intermediate Similarity	NPC210828
0.7581	Intermediate Similarity	NPC86834
0.7558	Intermediate Similarity	NPC23294
0.7536	Intermediate Similarity	NPC280714
0.7512	Intermediate Similarity	NPC303951
0.75	Intermediate Similarity	NPC39679
0.7488	Intermediate Similarity	NPC300156
0.7478	Intermediate Similarity	NPC473187
0.7477	Intermediate Similarity	NPC187501
0.7465	Intermediate Similarity	NPC174758
0.7445	Intermediate Similarity	NPC471762
0.7444	Intermediate Similarity	NPC469439
0.7426	Intermediate Similarity	NPC283152
0.7425	Intermediate Similarity	NPC119134
0.7422	Intermediate Similarity	NPC314633
0.7418	Intermediate Similarity	NPC315634
0.7418	Intermediate Similarity	NPC100734
0.7418	Intermediate Similarity	NPC88923
0.7406	Intermediate Similarity	NPC112937
0.7404	Intermediate Similarity	NPC78609
0.7397	Intermediate Similarity	NPC185197
0.7395	Intermediate Similarity	NPC317572
0.7391	Intermediate Similarity	NPC66083
0.7389	Intermediate Similarity	NPC473449
0.7389	Intermediate Similarity	NPC21638
0.7387	Intermediate Similarity	NPC305984
0.7366	Intermediate Similarity	NPC225279
0.7355	Intermediate Similarity	NPC284685
0.7352	Intermediate Similarity	NPC219664
0.7352	Intermediate Similarity	NPC470020
0.7349	Intermediate Similarity	NPC295898
0.7345	Intermediate Similarity	NPC122436
0.7333	Intermediate Similarity	NPC60621
0.733	Intermediate Similarity	NPC39500
0.7325	Intermediate Similarity	NPC89549
0.7306	Intermediate Similarity	NPC174672
0.7294	Intermediate Similarity	NPC193238
0.7293	Intermediate Similarity	NPC194740
0.7293	Intermediate Similarity	NPC66777
0.7291	Intermediate Similarity	NPC288943
0.7291	Intermediate Similarity	NPC84347
0.7285	Intermediate Similarity	NPC203168
0.7285	Intermediate Similarity	NPC472098
0.7265	Intermediate Similarity	NPC148183
0.7265	Intermediate Similarity	NPC152768
0.7265	Intermediate Similarity	NPC274982
0.7257	Intermediate Similarity	NPC280799
0.7254	Intermediate Similarity	NPC191489
0.7231	Intermediate Similarity	NPC26872
0.7229	Intermediate Similarity	NPC474688
0.7225	Intermediate Similarity	NPC144452
0.7215	Intermediate Similarity	NPC198160
0.7215	Intermediate Similarity	NPC321428
0.7212	Intermediate Similarity	NPC323969
0.721	Intermediate Similarity	NPC253675
0.7208	Intermediate Similarity	NPC134637
0.7208	Intermediate Similarity	NPC26850
0.7204	Intermediate Similarity	NPC469390
0.7203	Intermediate Similarity	NPC99891
0.72	Intermediate Similarity	NPC184408
0.72	Intermediate Similarity	NPC303658
0.7178	Intermediate Similarity	NPC67401
0.7163	Intermediate Similarity	NPC72211
0.7163	Intermediate Similarity	NPC84478
0.7157	Intermediate Similarity	NPC303225
0.7155	Intermediate Similarity	NPC260434
0.7149	Intermediate Similarity	NPC235685
0.7149	Intermediate Similarity	NPC184680
0.7149	Intermediate Similarity	NPC477587
0.7149	Intermediate Similarity	NPC477589
0.7137	Intermediate Similarity	NPC128115
0.7137	Intermediate Similarity	NPC472099
0.713	Intermediate Similarity	NPC470018
0.7126	Intermediate Similarity	NPC471978
0.7126	Intermediate Similarity	NPC209981
0.7124	Intermediate Similarity	NPC473041
0.7119	Intermediate Similarity	NPC470784
0.7119	Intermediate Similarity	NPC101350
0.7119	Intermediate Similarity	NPC470785
0.7119	Intermediate Similarity	NPC474183
0.7108	Intermediate Similarity	NPC471979
0.7104	Intermediate Similarity	NPC82548
0.7103	Intermediate Similarity	NPC131017
0.7101	Intermediate Similarity	NPC124300
0.71	Intermediate Similarity	NPC157931
0.7095	Intermediate Similarity	NPC61350
0.7095	Intermediate Similarity	NPC91868
0.7095	Intermediate Similarity	NPC63971
0.7089	Intermediate Similarity	NPC477585
0.7089	Intermediate Similarity	NPC477586
0.7089	Intermediate Similarity	NPC477588
0.7089	Intermediate Similarity	NPC477590
0.7085	Intermediate Similarity	NPC220337
0.7083	Intermediate Similarity	NPC234933
0.7078	Intermediate Similarity	NPC162484
0.7078	Intermediate Similarity	NPC134848
0.7071	Intermediate Similarity	NPC291609
0.707	Intermediate Similarity	NPC70259
0.7069	Intermediate Similarity	NPC274640
0.7066	Intermediate Similarity	NPC165964
0.7064	Intermediate Similarity	NPC39370
0.7054	Intermediate Similarity	NPC161801
0.7054	Intermediate Similarity	NPC116178
0.7051	Intermediate Similarity	NPC196718
0.7051	Intermediate Similarity	NPC102593
0.7051	Intermediate Similarity	NPC241263
0.7048	Intermediate Similarity	NPC42591
0.7043	Intermediate Similarity	NPC322482
0.704	Intermediate Similarity	NPC314834
0.7032	Intermediate Similarity	NPC66815
0.7023	Intermediate Similarity	NPC43787
0.7023	Intermediate Similarity	NPC205934
0.7022	Intermediate Similarity	NPC321166
0.7022	Intermediate Similarity	NPC217903
0.7021	Intermediate Similarity	NPC473105
0.7018	Intermediate Similarity	NPC11017
0.7018	Intermediate Similarity	NPC288987
0.7014	Intermediate Similarity	NPC476106
0.7014	Intermediate Similarity	NPC204385
0.7014	Intermediate Similarity	NPC472287
0.7014	Intermediate Similarity	NPC160381
0.7014	Intermediate Similarity	NPC472286
0.7012	Intermediate Similarity	NPC310618
0.7012	Intermediate Similarity	NPC107123
0.7009	Intermediate Similarity	NPC206109
0.7009	Intermediate Similarity	NPC114039
0.6991	Remote Similarity	NPC118228
0.6991	Remote Similarity	NPC146976
0.699	Remote Similarity	NPC312872
0.6987	Remote Similarity	NPC475844
0.6986	Remote Similarity	NPC232727
0.6982	Remote Similarity	NPC53344
0.6982	Remote Similarity	NPC314297
0.6982	Remote Similarity	NPC315545
0.6982	Remote Similarity	NPC183777
0.6979	Remote Similarity	NPC473186
0.6976	Remote Similarity	NPC473833
0.6972	Remote Similarity	NPC470042
0.6971	Remote Similarity	NPC124313
0.6959	Remote Similarity	NPC243834
0.6959	Remote Similarity	NPC70956
0.6955	Remote Similarity	NPC475112
0.6955	Remote Similarity	NPC475085
0.6955	Remote Similarity	NPC291535
0.6953	Remote Similarity	NPC74575
0.6953	Remote Similarity	NPC478078
0.6951	Remote Similarity	NPC287208
0.6951	Remote Similarity	NPC470931
0.6949	Remote Similarity	NPC329631
0.6947	Remote Similarity	NPC236668
0.6942	Remote Similarity	NPC191310
0.6942	Remote Similarity	NPC72715
0.6937	Remote Similarity	NPC313796
0.6937	Remote Similarity	NPC314855
0.6937	Remote Similarity	NPC313345

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 NPC298436 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	376
0.1-0.2	705
0.2-0.3	1062
0.3-0.4	1647
0.4-0.5	2792
0.5-0.6	1937
0.6-0.7	556
0.7-0.8	75
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7957	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7721	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD1505	Phase 2
0.7576	Intermediate Similarity	NPD6790	Phase 1
0.7566	Intermediate Similarity	NPD4952	Phase 3
0.7557	Intermediate Similarity	NPD6974	Phase 3
0.7536	Intermediate Similarity	NPD2778	Approved
0.7534	Intermediate Similarity	NPD3257	Approved
0.7534	Intermediate Similarity	NPD5293	Phase 2
0.7467	Intermediate Similarity	NPD4373	Phase 2
0.7455	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD5632	Approved
0.743	Intermediate Similarity	NPD2779	Approved
0.7426	Intermediate Similarity	NPD5482	Discontinued
0.7425	Intermediate Similarity	NPD7417	Discontinued
0.7418	Intermediate Similarity	NPD7803	Approved
0.7399	Intermediate Similarity	NPD3258	Approved
0.7393	Intermediate Similarity	NPD5512	Phase 3
0.738	Intermediate Similarity	NPD6962	Phase 2
0.7355	Intermediate Similarity	NPD7955	Approved
0.7355	Intermediate Similarity	NPD7956	Approved
0.7352	Intermediate Similarity	NPD1166	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD3507	Phase 2
0.7325	Intermediate Similarity	NPD4328	Approved
0.7319	Intermediate Similarity	NPD6716	Phase 1
0.7313	Intermediate Similarity	NPD3925	Approved
0.7308	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD1867	Approved
0.7301	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD648	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD4724	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD5924	Discontinued
0.7254	Intermediate Similarity	NPD7708	Approved
0.723	Intermediate Similarity	NPD6550	Discontinued
0.7212	Intermediate Similarity	NPD7180	Phase 3
0.7186	Intermediate Similarity	NPD4898	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7853	Phase 2
0.7175	Intermediate Similarity	NPD3945	Discontinued
0.7174	Intermediate Similarity	NPD3259	Approved
0.7167	Intermediate Similarity	NPD8102	Discontinued
0.7162	Intermediate Similarity	NPD6247	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD5416	Discontinued
0.7155	Intermediate Similarity	NPD5488	Discontinued
0.7123	Intermediate Similarity	NPD3946	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD7547	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD5479	Discontinued
0.7103	Intermediate Similarity	NPD4418	Discontinued
0.7095	Intermediate Similarity	NPD4369	Phase 2
0.7068	Intermediate Similarity	NPD5450	Discontinued
0.7067	Intermediate Similarity	NPD4203	Approved
0.7067	Intermediate Similarity	NPD4204	Approved
0.7059	Intermediate Similarity	NPD5429	Discontinued
0.7048	Intermediate Similarity	NPD7395	Discontinued
0.7029	Intermediate Similarity	NPD1483	Discontinued
0.7026	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD8359	Phase 2
0.7009	Intermediate Similarity	NPD1466	Phase 3
0.7009	Intermediate Similarity	NPD1467	Approved
0.7	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5513	Phase 2
0.7	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD6964	Approved
0.6992	Remote Similarity	NPD6963	Approved
0.6991	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD3263	Phase 3
0.6983	Remote Similarity	NPD7426	Phase 1
0.698	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD3842	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD4305	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD5922	Phase 3
0.692	Remote Similarity	NPD2951	Discontinued
0.6913	Remote Similarity	NPD6242	Discontinued
0.6911	Remote Similarity	NPD8463	Approved
0.6908	Remote Similarity	NPD6228	Discontinued
0.6907	Remote Similarity	NPD7031	Phase 1
0.6906	Remote Similarity	NPD7222	Phase 2
0.6903	Remote Similarity	NPD7069	Discontinued
0.6894	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.689	Remote Similarity	NPD3920	Phase 2
0.6875	Remote Similarity	NPD5658	Approved
0.6869	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD5139	Phase 1
0.6862	Remote Similarity	NPD5805	Approved
0.6861	Remote Similarity	NPD3003	Approved
0.6856	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD5256	Discontinued
0.6853	Remote Similarity	NPD2285	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD4885	Approved
0.6828	Remote Similarity	NPD5866	Approved
0.6826	Remote Similarity	NPD4429	Discontinued
0.6822	Remote Similarity	NPD1659	Phase 1
0.6822	Remote Similarity	NPD5022	Discontinued
0.6818	Remote Similarity	NPD1768	Approved
0.6805	Remote Similarity	NPD4613	Phase 2
0.6805	Remote Similarity	NPD7885	Phase 2
0.6805	Remote Similarity	NPD7886	Phase 2
0.6804	Remote Similarity	NPD6988	Phase 1
0.6804	Remote Similarity	NPD5003	Discontinued
0.6802	Remote Similarity	NPD7859	Phase 2
0.68	Remote Similarity	NPD2916	Discontinued
0.68	Remote Similarity	NPD7467	Discontinued
0.6798	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD4368	Phase 2
0.6789	Remote Similarity	NPD6590	Discontinued
0.6787	Remote Similarity	NPD8255	Phase 2
0.6783	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD5532	Phase 2
0.6773	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.677	Remote Similarity	NPD4506	Discontinued
0.6767	Remote Similarity	NPD8479	Phase 2
0.6766	Remote Similarity	NPD5640	Discontinued
0.676	Remote Similarity	NPD8091	Phase 3
0.6756	Remote Similarity	NPD7452	Approved
0.6756	Remote Similarity	NPD7453	Approved
0.6753	Remote Similarity	NPD1926	Approved
0.6751	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.675	Remote Similarity	NPD3006	Discontinued
0.6748	Remote Similarity	NPD4558	Phase 2
0.6742	Remote Similarity	NPD6874	Approved
0.6737	Remote Similarity	NPD7994	Phase 2
0.6736	Remote Similarity	NPD7558	Phase 2
0.6724	Remote Similarity	NPD2884	Phase 1
0.6723	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD6251	Discontinued
0.6712	Remote Similarity	NPD3324	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD5601	Phase 2
0.671	Remote Similarity	NPD5443	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6252	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD5930	Phase 3
0.6682	Remote Similarity	NPD2565	Phase 2
0.6682	Remote Similarity	NPD2564	Approved
0.6682	Remote Similarity	NPD6321	Discontinued
0.6681	Remote Similarity	NPD4981	Phase 2
0.6681	Remote Similarity	NPD6198	Phase 1
0.668	Remote Similarity	NPD3250	Phase 1
0.668	Remote Similarity	NPD6172	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5817	Discontinued
0.6667	Remote Similarity	NPD3392	Approved
0.6667	Remote Similarity	NPD2081	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6494	Phase 2
0.6667	Remote Similarity	NPD4923	Phase 1
0.6653	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6653	Remote Similarity	NPD6495	Clinical (unspecified phase)
0.6653	Remote Similarity	NPD946	Discontinued
0.6653	Remote Similarity	NPD2835	Phase 2
0.6652	Remote Similarity	NPD6769	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD6955	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD3875	Discontinued
0.6651	Remote Similarity	NPD4889	Approved
0.6642	Remote Similarity	NPD6745	Discontinued
0.664	Remote Similarity	NPD6530	Approved
0.664	Remote Similarity	NPD3328	Phase 2
0.664	Remote Similarity	NPD2311	Clinical (unspecified phase)
0.664	Remote Similarity	NPD6531	Approved
0.6638	Remote Similarity	NPD4989	Phase 2
0.6637	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD6150	Discontinued
0.6628	Remote Similarity	NPD8108	Approved
0.6625	Remote Similarity	NPD7797	Approved
0.6625	Remote Similarity	NPD7796	Approved
0.6623	Remote Similarity	NPD1638	Discovery
0.6623	Remote Similarity	NPD4897	Phase 2
0.6623	Remote Similarity	NPD5903	Approved
0.6623	Remote Similarity	NPD5902	Approved
0.6618	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD1392	Approved
0.66	Remote Similarity	NPD5857	Phase 3
0.6597	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD3947	Discontinued
0.6591	Remote Similarity	NPD8459	Approved
0.6591	Remote Similarity	NPD8460	Approved
0.6589	Remote Similarity	NPD3386	Phase 2
0.6586	Remote Similarity	NPD6475	Phase 2
0.6584	Remote Similarity	NPD4846	Phase 2
0.6582	Remote Similarity	NPD6246	Approved
0.6581	Remote Similarity	NPD7194	Discontinued
0.6579	Remote Similarity	NPD4642	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD8107	Approved
0.6568	Remote Similarity	NPD6995	Phase 1
0.6564	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD6245	Phase 2
0.6562	Remote Similarity	NPD1739	Approved
0.6562	Remote Similarity	NPD1740	Approved
0.6561	Remote Similarity	NPD3396	Approved
0.6561	Remote Similarity	NPD3395	Approved
0.6552	Remote Similarity	NPD6140	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD3924	Approved
0.6545	Remote Similarity	NPD6569	Phase 2

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