NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	293.11
Volume:	301.934
LogP:	3.871
LogD:	2.721
LogS:	-5.672
# Rotatable Bonds:	2
TPSA:	45.4
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.679
Synthetic Accessibility Score:	3.161
Fsp3:	0.167
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:	-4.704
MDCK Permeability:	3.392709550098516e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.083
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.842
Plasma Protein Binding (PPB):	94.989013671875%
Volume Distribution (VD):	1.806
Pgp-substrate:	3.937722682952881%

ADMET: Metabolism

CYP1A2-inhibitor:	0.769
CYP1A2-substrate:	0.579
CYP2C19-inhibitor:	0.604
CYP2C19-substrate:	0.864
CYP2C9-inhibitor:	0.14
CYP2C9-substrate:	0.529
CYP2D6-inhibitor:	0.982
CYP2D6-substrate:	0.726
CYP3A4-inhibitor:	0.756
CYP3A4-substrate:	0.519

ADMET: Excretion

Clearance (CL):	14.008
Half-life (T1/2):	0.747

ADMET: Toxicity

hERG Blockers:	0.098
Human Hepatotoxicity (H-HT):	0.747
Drug-inuced Liver Injury (DILI):	0.718
AMES Toxicity:	0.913
Rat Oral Acute Toxicity:	0.049
Maximum Recommended Daily Dose:	0.886
Skin Sensitization:	0.318
Carcinogencity:	0.949
Eye Corrosion:	0.003
Eye Irritation:	0.665
Respiratory Toxicity:	0.855

Download Data

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

Natural Product: NPC477019

Natural Product ID:	NPC477019
*Common Name:**	4-[(6-Methyl-[1,3]dioxolo[4,5-g]isoquinolin-6-ium-5-yl)methyl]phenol;2,2,2-trifluoroacetate
IUPAC Name:	4-[(6-methyl-[1,3]dioxolo[4,5-g]isoquinolin-6-ium-5-yl)methyl]phenol;2,2,2-trifluoroacetate
Synonyms:
Standard InCHIKey:	FHICXRSAKZEHGE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H15NO3.C2HF3O2/c1-19-7-6-13-9-17-18(22-11-21-17)10-15(13)16(19)8-12-2-4-14(20)5-3-12;3-2(4,5)1(6)7/h2-7,9-10H,8,11H2,1H3;(H,6,7)
SMILES:	C[N+]1=C(C2=CC3=C(C=C2C=C1)OCO3)CC4=CC=C(C=C4)O.C(=O)(C(F)(F)F)[O-]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44254794
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002566] Isoquinolines and derivatives [CHEMONTID:0000054] Benzylisoquinolines

*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
NPO23314	Doryphora sassafras	Species	Atherospermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11754616]
NPO23314	Doryphora sassafras	Species	Atherospermataceae	Eukaryota	leaves	The Head, 1.5 km NW of Wilsons Peak, Darling Downs, Queensland, Australia	1994-AUG	PMID[19637893]
NPO23314	Doryphora sassafras	Species	Atherospermataceae	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	1

Activity Type	# Activity
Cell Line	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT71	Cell Line	HEK293	Homo sapiens	Activity	=	0	%	PMID[19637893]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	4400	nM	PMID[19637893]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	3000	nM	PMID[19637893]

☑ 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 NPC477019 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	395
0.1-0.2	2480
0.2-0.3	12796
0.3-0.4	5168
0.4-0.5	14350
0.5-0.6	5042
0.6-0.7	2180
0.7-0.8	214
0.8-0.85	40
0.85-0.9	18
0.9-0.95	12
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9565	High Similarity	NPC313189
0.9558	High Similarity	NPC234197
0.9459	High Similarity	NPC135549
0.9415	High Similarity	NPC296482
0.9415	High Similarity	NPC53069
0.9415	High Similarity	NPC202768
0.9385	High Similarity	NPC195268
0.9385	High Similarity	NPC133140
0.9312	High Similarity	NPC96405
0.9312	High Similarity	NPC171409
0.9211	High Similarity	NPC251160
0.9185	High Similarity	NPC4071
0.9185	High Similarity	NPC476582
0.9185	High Similarity	NPC476578
0.9062	High Similarity	NPC149471
0.9062	High Similarity	NPC271215
0.9043	High Similarity	NPC476581
0.9043	High Similarity	NPC16452
0.9043	High Similarity	NPC36229
0.9005	High Similarity	NPC188420
0.8883	High Similarity	NPC31930
0.8878	High Similarity	NPC23614
0.8878	High Similarity	NPC100079
0.8832	High Similarity	NPC46451
0.8821	High Similarity	NPC235076
0.8808	High Similarity	NPC290689
0.8718	High Similarity	NPC112206
0.8718	High Similarity	NPC202605
0.8687	High Similarity	NPC204446
0.8674	High Similarity	NPC206201
0.8587	High Similarity	NPC204385
0.8515	High Similarity	NPC118121
0.8485	Intermediate Similarity	NPC236668
0.8462	Intermediate Similarity	NPC253675
0.8447	Intermediate Similarity	NPC278525
0.8442	Intermediate Similarity	NPC146976
0.8413	Intermediate Similarity	NPC22481
0.8333	Intermediate Similarity	NPC108342
0.8325	Intermediate Similarity	NPC174049
0.8317	Intermediate Similarity	NPC473822
0.8297	Intermediate Similarity	NPC312872
0.8294	Intermediate Similarity	NPC189903
0.8294	Intermediate Similarity	NPC182907
0.829	Intermediate Similarity	NPC287437
0.8255	Intermediate Similarity	NPC166722
0.8167	Intermediate Similarity	NPC24954
0.8155	Intermediate Similarity	NPC122463
0.8155	Intermediate Similarity	NPC210434
0.8131	Intermediate Similarity	NPC323345
0.8131	Intermediate Similarity	NPC470164
0.8119	Intermediate Similarity	NPC266931
0.8119	Intermediate Similarity	NPC162530
0.8093	Intermediate Similarity	NPC210296
0.8088	Intermediate Similarity	NPC473513
0.8065	Intermediate Similarity	NPC124313
0.8056	Intermediate Similarity	NPC84164
0.8056	Intermediate Similarity	NPC207283
0.8049	Intermediate Similarity	NPC173080
0.7991	Intermediate Similarity	NPC295228
0.7972	Intermediate Similarity	NPC201508
0.797	Intermediate Similarity	NPC470020
0.796	Intermediate Similarity	NPC82548
0.7931	Intermediate Similarity	NPC208284
0.7925	Intermediate Similarity	NPC24019
0.7908	Intermediate Similarity	NPC224928
0.79	Intermediate Similarity	NPC285558
0.7897	Intermediate Similarity	NPC255800
0.7897	Intermediate Similarity	NPC96584
0.7883	Intermediate Similarity	NPC183537
0.7879	Intermediate Similarity	NPC176538
0.785	Intermediate Similarity	NPC475774
0.7835	Intermediate Similarity	NPC92111
0.7833	Intermediate Similarity	NPC174758
0.7824	Intermediate Similarity	NPC296527
0.7822	Intermediate Similarity	NPC474595
0.781	Intermediate Similarity	NPC280272
0.7805	Intermediate Similarity	NPC316981
0.7803	Intermediate Similarity	NPC77878
0.7784	Intermediate Similarity	NPC76748
0.7767	Intermediate Similarity	NPC233334
0.7766	Intermediate Similarity	NPC251090
0.776	Intermediate Similarity	NPC249405
0.7755	Intermediate Similarity	NPC307963
0.775	Intermediate Similarity	NPC232727
0.7737	Intermediate Similarity	NPC287588
0.7707	Intermediate Similarity	NPC167860
0.7707	Intermediate Similarity	NPC123976
0.7696	Intermediate Similarity	NPC90875
0.7688	Intermediate Similarity	NPC127085
0.7659	Intermediate Similarity	NPC174672
0.7639	Intermediate Similarity	NPC476999
0.7628	Intermediate Similarity	NPC476997
0.7624	Intermediate Similarity	NPC199277
0.7624	Intermediate Similarity	NPC135887
0.7617	Intermediate Similarity	NPC179704
0.7617	Intermediate Similarity	NPC284559
0.7614	Intermediate Similarity	NPC280964
0.7614	Intermediate Similarity	NPC141915
0.7614	Intermediate Similarity	NPC114335
0.7608	Intermediate Similarity	NPC274982
0.7602	Intermediate Similarity	NPC119134
0.7596	Intermediate Similarity	NPC26850
0.7593	Intermediate Similarity	NPC476998
0.7593	Intermediate Similarity	NPC476996
0.7586	Intermediate Similarity	NPC245816
0.7586	Intermediate Similarity	NPC476138
0.7583	Intermediate Similarity	NPC148409
0.7583	Intermediate Similarity	NPC193267
0.7583	Intermediate Similarity	NPC213530
0.7576	Intermediate Similarity	NPC329541
0.7568	Intermediate Similarity	NPC177404
0.7556	Intermediate Similarity	NPC475959
0.755	Intermediate Similarity	NPC267928
0.7549	Intermediate Similarity	NPC118832
0.7549	Intermediate Similarity	NPC47059
0.7549	Intermediate Similarity	NPC165349
0.7549	Intermediate Similarity	NPC274291
0.7549	Intermediate Similarity	NPC264166
0.7549	Intermediate Similarity	NPC329708
0.7547	Intermediate Similarity	NPC54066
0.7546	Intermediate Similarity	NPC476994
0.7534	Intermediate Similarity	NPC15406
0.7523	Intermediate Similarity	NPC217554
0.7513	Intermediate Similarity	NPC312531
0.7512	Intermediate Similarity	NPC474594
0.7512	Intermediate Similarity	NPC475841
0.7512	Intermediate Similarity	NPC469792
0.7512	Intermediate Similarity	NPC474145
0.7512	Intermediate Similarity	NPC472111
0.7488	Intermediate Similarity	NPC469589
0.7474	Intermediate Similarity	NPC176127
0.7465	Intermediate Similarity	NPC246381
0.7454	Intermediate Similarity	NPC214980
0.7454	Intermediate Similarity	NPC470018
0.7444	Intermediate Similarity	NPC99891
0.7441	Intermediate Similarity	NPC170114
0.744	Intermediate Similarity	NPC287208
0.7438	Intermediate Similarity	NPC329747
0.7438	Intermediate Similarity	NPC329793
0.7438	Intermediate Similarity	NPC315957
0.7437	Intermediate Similarity	NPC99666
0.7432	Intermediate Similarity	NPC11408
0.7432	Intermediate Similarity	NPC476568
0.7424	Intermediate Similarity	NPC474904
0.7422	Intermediate Similarity	NPC284141
0.7419	Intermediate Similarity	NPC74575
0.7418	Intermediate Similarity	NPC308906
0.7418	Intermediate Similarity	NPC17565
0.7415	Intermediate Similarity	NPC223427
0.7413	Intermediate Similarity	NPC13880
0.7405	Intermediate Similarity	NPC93593
0.7404	Intermediate Similarity	NPC185782
0.7401	Intermediate Similarity	NPC270515
0.7393	Intermediate Similarity	NPC470549
0.7387	Intermediate Similarity	NPC476995
0.7381	Intermediate Similarity	NPC26679
0.7381	Intermediate Similarity	NPC472098
0.7379	Intermediate Similarity	NPC210256
0.7368	Intermediate Similarity	NPC11464
0.7366	Intermediate Similarity	NPC295898
0.7363	Intermediate Similarity	NPC131017
0.7361	Intermediate Similarity	NPC322482
0.7358	Intermediate Similarity	NPC285941
0.7353	Intermediate Similarity	NPC11017
0.7353	Intermediate Similarity	NPC19872
0.7349	Intermediate Similarity	NPC60621
0.7347	Intermediate Similarity	NPC84478
0.7346	Intermediate Similarity	NPC476287
0.7337	Intermediate Similarity	NPC26872
0.7333	Intermediate Similarity	NPC470474
0.7327	Intermediate Similarity	NPC473053
0.7313	Intermediate Similarity	NPC302001
0.7312	Intermediate Similarity	NPC138487
0.7312	Intermediate Similarity	NPC216459
0.7312	Intermediate Similarity	NPC41178
0.7308	Intermediate Similarity	NPC193238
0.73	Intermediate Similarity	NPC469390
0.7299	Intermediate Similarity	NPC94157
0.7297	Intermediate Similarity	NPC233029
0.7297	Intermediate Similarity	NPC210148
0.7295	Intermediate Similarity	NPC475070
0.7286	Intermediate Similarity	NPC471304
0.7285	Intermediate Similarity	NPC49547
0.7282	Intermediate Similarity	NPC211813
0.7281	Intermediate Similarity	NPC65277
0.7273	Intermediate Similarity	NPC61350
0.7273	Intermediate Similarity	NPC476465
0.7273	Intermediate Similarity	NPC470931
0.7273	Intermediate Similarity	NPC18348
0.7273	Intermediate Similarity	NPC146288
0.7255	Intermediate Similarity	NPC71124
0.7249	Intermediate Similarity	NPC477559
0.7249	Intermediate Similarity	NPC118511
0.7249	Intermediate Similarity	NPC232924
0.7249	Intermediate Similarity	NPC306902
0.7249	Intermediate Similarity	NPC160298
0.7249	Intermediate Similarity	NPC266753
0.7246	Intermediate Similarity	NPC162484
0.7243	Intermediate Similarity	NPC12100
0.7241	Intermediate Similarity	NPC162653

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 NPC477019 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	218
0.1-0.2	679
0.2-0.3	914
0.3-0.4	1287
0.4-0.5	2702
0.5-0.6	2279
0.6-0.7	953
0.7-0.8	110
0.8-0.85	4
0.85-0.9	1
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9415	High Similarity	NPD3815	Phase 1
0.9415	High Similarity	NPD3816	Phase 1
0.9385	High Similarity	NPD3924	Approved
0.9385	High Similarity	NPD3922	Approved
0.9385	High Similarity	NPD3923	Approved
0.9385	High Similarity	NPD3921	Approved
0.8876	High Similarity	NPD3920	Phase 2
0.8832	High Similarity	NPD3763	Approved
0.8541	High Similarity	NPD6257	Clinical (unspecified phase)
0.8197	Intermediate Similarity	NPD1923	Clinical (unspecified phase)
0.8172	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD5658	Approved
0.8138	Intermediate Similarity	NPD4889	Approved
0.8119	Intermediate Similarity	NPD7571	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD6219	Discontinued
0.799	Intermediate Similarity	NPD4418	Discontinued
0.7979	Intermediate Similarity	NPD6569	Phase 2
0.788	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD2060	Approved
0.7822	Intermediate Similarity	NPD7222	Phase 2
0.7814	Intermediate Similarity	NPD6494	Phase 2
0.7772	Intermediate Similarity	NPD2780	Approved
0.7772	Intermediate Similarity	NPD2782	Approved
0.7767	Intermediate Similarity	NPD4885	Approved
0.7755	Intermediate Similarity	NPD4551	Phase 2
0.7755	Intermediate Similarity	NPD1038	Approved
0.7755	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7723	Intermediate Similarity	NPD3397	Phase 2
0.7718	Intermediate Similarity	NPD7069	Discontinued
0.7711	Intermediate Similarity	NPD6477	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD1078	Clinical (unspecified phase)
0.7696	Intermediate Similarity	NPD3386	Phase 2
0.7688	Intermediate Similarity	NPD2781	Approved
0.7647	Intermediate Similarity	NPD7453	Approved
0.7647	Intermediate Similarity	NPD7452	Approved
0.7635	Intermediate Similarity	NPD4795	Phase 2
0.761	Intermediate Similarity	NPD5863	Clinical (unspecified phase)
0.7608	Intermediate Similarity	NPD5612	Discontinued
0.7598	Intermediate Similarity	NPD5601	Phase 2
0.7578	Intermediate Similarity	NPD6230	Discontinued
0.7563	Intermediate Similarity	NPD2334	Discontinued
0.7562	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7549	Intermediate Similarity	NPD4038	Approved
0.7549	Intermediate Similarity	NPD4037	Approved
0.7549	Intermediate Similarity	NPD4033	Approved
0.7549	Intermediate Similarity	NPD4039	Approved
0.7549	Intermediate Similarity	NPD32	Approved
0.7549	Intermediate Similarity	NPD4035	Approved
0.7549	Intermediate Similarity	NPD4034	Approved
0.7549	Intermediate Similarity	NPD31	Approved
0.7549	Intermediate Similarity	NPD4036	Approved
0.7549	Intermediate Similarity	NPD4122	Approved
0.7547	Intermediate Similarity	NPD5070	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD4396	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD6281	Approved
0.75	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3477	Phase 2
0.7487	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD3825	Phase 3
0.7455	Intermediate Similarity	NPD6964	Approved
0.7455	Intermediate Similarity	NPD6963	Approved
0.745	Intermediate Similarity	NPD3395	Approved
0.745	Intermediate Similarity	NPD3396	Approved
0.7449	Intermediate Similarity	NPD2917	Approved
0.7448	Intermediate Similarity	NPD1032	Phase 2
0.744	Intermediate Similarity	NPD2739	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD1740	Approved
0.7438	Intermediate Similarity	NPD1739	Approved
0.7432	Intermediate Similarity	NPD7729	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD5530	Phase 1
0.7419	Intermediate Similarity	NPD6553	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD4131	Phase 3
0.7411	Intermediate Similarity	NPD1033	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD1034	Phase 3
0.7407	Intermediate Similarity	NPD7719	Discontinued
0.7383	Intermediate Similarity	NPD6242	Discontinued
0.7371	Intermediate Similarity	NPD2600	Approved
0.7371	Intermediate Similarity	NPD6568	Discontinued
0.7371	Intermediate Similarity	NPD3354	Phase 2
0.7371	Intermediate Similarity	NPD2599	Approved
0.7371	Intermediate Similarity	NPD2601	Approved
0.7363	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD4375	Approved
0.7358	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7352	Intermediate Similarity	NPD8052	Clinical (unspecified phase)
0.7352	Intermediate Similarity	NPD7567	Approved
0.7333	Intermediate Similarity	NPD4876	Phase 3
0.7333	Intermediate Similarity	NPD4875	Phase 3
0.7333	Intermediate Similarity	NPD4203	Approved
0.7333	Intermediate Similarity	NPD4204	Approved
0.732	Intermediate Similarity	NPD1620	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD1954	Phase 1
0.7313	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD2581	Approved
0.7312	Intermediate Similarity	NPD2582	Approved
0.731	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD4548	Discontinued
0.7302	Intermediate Similarity	NPD5930	Phase 3
0.7277	Intermediate Similarity	NPD6727	Phase 2
0.7273	Intermediate Similarity	NPD2187	Approved
0.7273	Intermediate Similarity	NPD5529	Phase 1
0.7273	Intermediate Similarity	NPD2189	Approved
0.7273	Intermediate Similarity	NPD5528	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD4071	Approved
0.7268	Intermediate Similarity	NPD4072	Approved
0.7264	Intermediate Similarity	NPD4372	Phase 1
0.7259	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD8091	Phase 3
0.7252	Intermediate Similarity	NPD7558	Phase 2
0.7251	Intermediate Similarity	NPD4502	Phase 2
0.7235	Intermediate Similarity	NPD1856	Discontinued
0.7234	Intermediate Similarity	NPD112	Approved
0.7234	Intermediate Similarity	NPD9705	Discontinued
0.7234	Intermediate Similarity	NPD2358	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD5903	Approved
0.723	Intermediate Similarity	NPD5902	Approved
0.7228	Intermediate Similarity	NPD6361	Phase 2
0.7227	Intermediate Similarity	NPD7555	Discontinued
0.7227	Intermediate Similarity	NPD5559	Phase 2
0.722	Intermediate Similarity	NPD3541	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD7674	Phase 3
0.7215	Intermediate Similarity	NPD7675	Phase 3
0.7215	Intermediate Similarity	NPD7676	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD6262	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD3349	Phase 2
0.7195	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD6298	Discontinued
0.7189	Intermediate Similarity	NPD5147	Discontinued
0.7186	Intermediate Similarity	NPD5256	Discontinued
0.7181	Intermediate Similarity	NPD6517	Phase 3
0.7179	Intermediate Similarity	NPD7169	Suspended
0.7176	Intermediate Similarity	NPD6500	Approved
0.7176	Intermediate Similarity	NPD6501	Approved
0.717	Intermediate Similarity	NPD5067	Phase 2
0.717	Intermediate Similarity	NPD5066	Phase 2
0.7167	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD8063	Discontinued
0.7164	Intermediate Similarity	NPD3408	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1392	Approved
0.7136	Intermediate Similarity	NPD5999	Phase 2
0.713	Intermediate Similarity	NPD3313	Phase 2
0.7122	Intermediate Similarity	NPD7948	Phase 1
0.7117	Intermediate Similarity	NPD1900	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6975	Discontinued
0.7114	Intermediate Similarity	NPD4021	Phase 2
0.71	Intermediate Similarity	NPD4920	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD4921	Phase 3
0.71	Intermediate Similarity	NPD4919	Phase 3
0.7098	Intermediate Similarity	NPD4724	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD3003	Approved
0.7087	Intermediate Similarity	NPD8100	Phase 3
0.7085	Intermediate Similarity	NPD4995	Approved
0.7085	Intermediate Similarity	NPD4996	Approved
0.7082	Intermediate Similarity	NPD7859	Phase 2
0.708	Intermediate Similarity	NPD5805	Approved
0.7073	Intermediate Similarity	NPD2482	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD5512	Phase 3
0.7069	Intermediate Similarity	NPD6243	Phase 3
0.7069	Intermediate Similarity	NPD6244	Phase 3
0.7064	Intermediate Similarity	NPD6856	Discontinued
0.7062	Intermediate Similarity	NPD5429	Discontinued
0.7062	Intermediate Similarity	NPD4083	Discontinued
0.7061	Intermediate Similarity	NPD6790	Phase 1
0.7059	Intermediate Similarity	NPD7426	Phase 1
0.7056	Intermediate Similarity	NPD4927	Discontinued
0.7056	Intermediate Similarity	NPD5866	Approved
0.7051	Intermediate Similarity	NPD4429	Discontinued
0.7048	Intermediate Similarity	NPD3946	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD4925	Approved
0.7039	Intermediate Similarity	NPD2952	Discontinued
0.7039	Intermediate Similarity	NPD1229	Phase 2
0.7037	Intermediate Similarity	NPD6147	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD5669	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD926	Approved
0.7031	Intermediate Similarity	NPD925	Approved
0.7028	Intermediate Similarity	NPD7672	Approved
0.7028	Intermediate Similarity	NPD7671	Approved
0.7024	Intermediate Similarity	NPD6590	Discontinued
0.7024	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD1602	Discontinued
0.7023	Intermediate Similarity	NPD5945	Phase 1
0.7023	Intermediate Similarity	NPD1322	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD5944	Phase 1
0.7022	Intermediate Similarity	NPD4080	Discontinued
0.7018	Intermediate Similarity	NPD8017	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD7886	Phase 2
0.7018	Intermediate Similarity	NPD8016	Phase 3
0.7018	Intermediate Similarity	NPD7885	Phase 2
0.7015	Intermediate Similarity	NPD7758	Approved
0.7015	Intermediate Similarity	NPD7757	Approved
0.7	Intermediate Similarity	NPD6991	Approved
0.7	Intermediate Similarity	NPD5255	Approved
0.6996	Remote Similarity	NPD8101	Phase 3
0.6995	Remote Similarity	NPD2125	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