NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	337.13
Volume:	345.316
LogP:	3.485
LogD:	3.442
LogS:	-5.866
# Rotatable Bonds:	3
TPSA:	54.63
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.689
Synthetic Accessibility Score:	3.172
Fsp3:	0.25
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:	-5.102
MDCK Permeability:	2.321202919119969e-05
Pgp-inhibitor:	0.013
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.052
30% Bioavailability (F30%):	0.289

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.745
Plasma Protein Binding (PPB):	85.4808120727539%
Volume Distribution (VD):	1.269
Pgp-substrate:	5.70773458480835%

ADMET: Metabolism

CYP1A2-inhibitor:	0.25
CYP1A2-substrate:	0.949
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.883
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.734
CYP2D6-inhibitor:	0.09
CYP2D6-substrate:	0.867
CYP3A4-inhibitor:	0.015
CYP3A4-substrate:	0.422

ADMET: Excretion

Clearance (CL):	8.9
Half-life (T1/2):	0.543

ADMET: Toxicity

hERG Blockers:	0.214
Human Hepatotoxicity (H-HT):	0.249
Drug-inuced Liver Injury (DILI):	0.889
AMES Toxicity:	0.354
Rat Oral Acute Toxicity:	0.142
Maximum Recommended Daily Dose:	0.9
Skin Sensitization:	0.9
Carcinogencity:	0.121
Eye Corrosion:	0.003
Eye Irritation:	0.025
Respiratory Toxicity:	0.773

Download Data

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

Natural Product: NPC476578

Natural Product ID:	NPC476578
*Common Name:**	Pseudocolumbamine trifluoroacetate
IUPAC Name:	2,2,2-trifluoroacetate;3,10,11-trimethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium-2-ol
Synonyms:	Pseudocolumbamine Trifluoroacetate
Standard InCHIKey:	NJSNVNFFIBGGAE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H19NO4.C2HF3O2/c1-23-18-7-12-4-5-21-11-14-9-20(25-3)19(24-2)8-13(14)6-16(21)15(12)10-17(18)22;3-2(4,5)1(6)7/h6-11H,4-5H2,1-3H3;(H,6,7)
SMILES:	COC1=C(C=C2C(=C1)CC[N+]3=CC4=CC(=C(C=C4C=C23)OC)OC)O.C(=O)(C(F)(F)F)[O-]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	49850520
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001909] Protoberberine alkaloids and derivatives

*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
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	stem wood	n.a.	DOI[10.1021/np100247r]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10395501]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10425140]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[15568797]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	stem	Taipei Botanical Garden, Taipei, Taiwan, China	2006-MAR	PMID[20828184]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	fruits	n.a.	n.a.	PMID[25499882]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9584397]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9599260]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6333	Annona glabra	Species	Annonaceae	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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	IC50	=	5000	nM	PMID[20828184]

☑ 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 NPC476578 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	389
0.1-0.2	2598
0.2-0.3	13545
0.3-0.4	4402
0.4-0.5	14488
0.5-0.6	4842
0.6-0.7	2144
0.7-0.8	232
0.8-0.85	31
0.85-0.9	15
0.9-0.95	7
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476582
1.0	High Similarity	NPC4071
0.9724	High Similarity	NPC16452
0.9724	High Similarity	NPC476581
0.9724	High Similarity	NPC36229
0.9617	High Similarity	NPC313189
0.9558	High Similarity	NPC31930
0.9548	High Similarity	NPC195268
0.9548	High Similarity	NPC133140
0.9405	High Similarity	NPC135549
0.9362	High Similarity	NPC112206
0.9362	High Similarity	NPC296482
0.9362	High Similarity	NPC202768
0.9362	High Similarity	NPC53069
0.9362	High Similarity	NPC202605
0.9255	High Similarity	NPC290689
0.9185	High Similarity	NPC477019
0.9158	High Similarity	NPC171409
0.9158	High Similarity	NPC96405
0.8978	High Similarity	NPC234197
0.8814	High Similarity	NPC271215
0.8814	High Similarity	NPC149471
0.8667	High Similarity	NPC251160
0.866	High Similarity	NPC188420
0.8636	High Similarity	NPC23614
0.8636	High Similarity	NPC100079
0.8622	High Similarity	NPC236668
0.8579	High Similarity	NPC146976
0.8547	High Similarity	NPC312872
0.8526	High Similarity	NPC287437
0.85	High Similarity	NPC46451
0.8485	Intermediate Similarity	NPC235076
0.8458	Intermediate Similarity	NPC174049
0.8374	Intermediate Similarity	NPC122463
0.8359	Intermediate Similarity	NPC470164
0.8359	Intermediate Similarity	NPC323345
0.8358	Intermediate Similarity	NPC473822
0.8358	Intermediate Similarity	NPC204446
0.8357	Intermediate Similarity	NPC201508
0.8286	Intermediate Similarity	NPC295228
0.8278	Intermediate Similarity	NPC96584
0.8278	Intermediate Similarity	NPC255800
0.825	Intermediate Similarity	NPC266931
0.8218	Intermediate Similarity	NPC473513
0.8195	Intermediate Similarity	NPC118121
0.8195	Intermediate Similarity	NPC210434
0.8191	Intermediate Similarity	NPC470020
0.8159	Intermediate Similarity	NPC162530
0.8138	Intermediate Similarity	NPC204385
0.8134	Intermediate Similarity	NPC24019
0.8118	Intermediate Similarity	NPC206201
0.8107	Intermediate Similarity	NPC280272
0.8088	Intermediate Similarity	NPC173080
0.803	Intermediate Similarity	NPC47059
0.803	Intermediate Similarity	NPC165349
0.803	Intermediate Similarity	NPC264166
0.803	Intermediate Similarity	NPC118832
0.803	Intermediate Similarity	NPC329708
0.803	Intermediate Similarity	NPC285558
0.803	Intermediate Similarity	NPC274291
0.7981	Intermediate Similarity	NPC253675
0.797	Intermediate Similarity	NPC208284
0.7949	Intermediate Similarity	NPC224928
0.7934	Intermediate Similarity	NPC22481
0.7931	Intermediate Similarity	NPC316981
0.7921	Intermediate Similarity	NPC167860
0.7921	Intermediate Similarity	NPC123976
0.7915	Intermediate Similarity	NPC476994
0.7915	Intermediate Similarity	NPC476997
0.791	Intermediate Similarity	NPC82548
0.7897	Intermediate Similarity	NPC90875
0.7889	Intermediate Similarity	NPC475774
0.7887	Intermediate Similarity	NPC233334
0.7877	Intermediate Similarity	NPC278525
0.7877	Intermediate Similarity	NPC476998
0.7877	Intermediate Similarity	NPC476996
0.7876	Intermediate Similarity	NPC92111
0.786	Intermediate Similarity	NPC108342
0.784	Intermediate Similarity	NPC476999
0.7828	Intermediate Similarity	NPC176538
0.7824	Intermediate Similarity	NPC182907
0.7824	Intermediate Similarity	NPC189903
0.7824	Intermediate Similarity	NPC76748
0.782	Intermediate Similarity	NPC214980
0.7811	Intermediate Similarity	NPC472111
0.7795	Intermediate Similarity	NPC307963
0.7795	Intermediate Similarity	NPC329541
0.7788	Intermediate Similarity	NPC213530
0.7788	Intermediate Similarity	NPC166722
0.7788	Intermediate Similarity	NPC193267
0.7783	Intermediate Similarity	NPC174758
0.7772	Intermediate Similarity	NPC296527
0.7765	Intermediate Similarity	NPC476568
0.7748	Intermediate Similarity	NPC270515
0.7744	Intermediate Similarity	NPC280964
0.7744	Intermediate Similarity	NPC141915
0.7744	Intermediate Similarity	NPC114335
0.7735	Intermediate Similarity	NPC26850
0.7725	Intermediate Similarity	NPC322482
0.7716	Intermediate Similarity	NPC251090
0.771	Intermediate Similarity	NPC469792
0.7705	Intermediate Similarity	NPC177404
0.7705	Intermediate Similarity	NPC216816
0.77	Intermediate Similarity	NPC232727
0.7696	Intermediate Similarity	NPC469589
0.7661	Intermediate Similarity	NPC476995
0.7656	Intermediate Similarity	NPC284559
0.7653	Intermediate Similarity	NPC470018
0.765	Intermediate Similarity	NPC329793
0.765	Intermediate Similarity	NPC315957
0.7647	Intermediate Similarity	NPC15406
0.7638	Intermediate Similarity	NPC127085
0.7636	Intermediate Similarity	NPC119134
0.7636	Intermediate Similarity	NPC210296
0.7617	Intermediate Similarity	NPC74575
0.7613	Intermediate Similarity	NPC124313
0.761	Intermediate Similarity	NPC174672
0.7602	Intermediate Similarity	NPC84164
0.7602	Intermediate Similarity	NPC207283
0.7579	Intermediate Similarity	NPC285941
0.7574	Intermediate Similarity	NPC199277
0.7574	Intermediate Similarity	NPC135887
0.7569	Intermediate Similarity	NPC26872
0.7562	Intermediate Similarity	NPC11017
0.756	Intermediate Similarity	NPC274982
0.7558	Intermediate Similarity	NPC49547
0.7557	Intermediate Similarity	NPC217554
0.7552	Intermediate Similarity	NPC470474
0.7552	Intermediate Similarity	NPC190461
0.7538	Intermediate Similarity	NPC473053
0.7537	Intermediate Similarity	NPC245816
0.7537	Intermediate Similarity	NPC469440
0.7537	Intermediate Similarity	NPC476138
0.7536	Intermediate Similarity	NPC17565
0.7534	Intermediate Similarity	NPC284141
0.7527	Intermediate Similarity	NPC24954
0.7514	Intermediate Similarity	NPC476567
0.7514	Intermediate Similarity	NPC128019
0.7514	Intermediate Similarity	NPC136860
0.75	Intermediate Similarity	NPC472098
0.75	Intermediate Similarity	NPC476518
0.75	Intermediate Similarity	NPC267928
0.75	Intermediate Similarity	NPC246381
0.75	Intermediate Similarity	NPC264176
0.75	Intermediate Similarity	NPC314954
0.7477	Intermediate Similarity	NPC469554
0.7476	Intermediate Similarity	NPC470931
0.7476	Intermediate Similarity	NPC170114
0.7475	Intermediate Similarity	NPC329747
0.7475	Intermediate Similarity	NPC99666
0.7466	Intermediate Similarity	NPC11408
0.746	Intermediate Similarity	NPC14651
0.746	Intermediate Similarity	NPC121658
0.7455	Intermediate Similarity	NPC470017
0.7451	Intermediate Similarity	NPC223427
0.7445	Intermediate Similarity	NPC183537
0.7436	Intermediate Similarity	NPC20249
0.7433	Intermediate Similarity	NPC471178
0.743	Intermediate Similarity	NPC216612
0.7429	Intermediate Similarity	NPC470549
0.7424	Intermediate Similarity	NPC469390
0.7423	Intermediate Similarity	NPC176127
0.7421	Intermediate Similarity	NPC470022
0.7421	Intermediate Similarity	NPC66573
0.7418	Intermediate Similarity	NPC54066
0.7416	Intermediate Similarity	NPC26679
0.7416	Intermediate Similarity	NPC94157
0.7415	Intermediate Similarity	NPC164374
0.7415	Intermediate Similarity	NPC137929
0.7411	Intermediate Similarity	NPC477186
0.7409	Intermediate Similarity	NPC287588
0.7407	Intermediate Similarity	NPC200888
0.7404	Intermediate Similarity	NPC11464
0.7402	Intermediate Similarity	NPC66815
0.7397	Intermediate Similarity	NPC101543
0.7395	Intermediate Similarity	NPC65277
0.7391	Intermediate Similarity	NPC475910
0.7391	Intermediate Similarity	NPC287208
0.7381	Intermediate Similarity	NPC471080
0.7381	Intermediate Similarity	NPC469592
0.738	Intermediate Similarity	NPC118511
0.7379	Intermediate Similarity	NPC304183
0.7371	Intermediate Similarity	NPC308906
0.7368	Intermediate Similarity	NPC77878
0.7363	Intermediate Similarity	NPC13880
0.7356	Intermediate Similarity	NPC185782
0.735	Intermediate Similarity	NPC132385
0.7348	Intermediate Similarity	NPC16107
0.7348	Intermediate Similarity	NPC476144
0.7348	Intermediate Similarity	NPC106295
0.7348	Intermediate Similarity	NPC51957
0.7348	Intermediate Similarity	NPC210437
0.7343	Intermediate Similarity	NPC474595
0.7343	Intermediate Similarity	NPC193238
0.7342	Intermediate Similarity	NPC473183
0.7336	Intermediate Similarity	NPC472099
0.733	Intermediate Similarity	NPC475070
0.733	Intermediate Similarity	NPC111624
0.733	Intermediate Similarity	NPC210256
0.7324	Intermediate Similarity	NPC469594

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 NPC476578 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	212
0.1-0.2	711
0.2-0.3	917
0.3-0.4	1241
0.4-0.5	2690
0.5-0.6	2262
0.6-0.7	960
0.7-0.8	147
0.8-0.85	5
0.85-0.9	3
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9548	High Similarity	NPD3921	Approved
0.9548	High Similarity	NPD3923	Approved
0.9548	High Similarity	NPD3922	Approved
0.9548	High Similarity	NPD3924	Approved
0.9362	High Similarity	NPD3816	Phase 1
0.9362	High Similarity	NPD3815	Phase 1
0.8927	High Similarity	NPD3920	Phase 2
0.85	High Similarity	NPD3763	Approved
0.8486	Intermediate Similarity	NPD6257	Clinical (unspecified phase)
0.8315	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.8307	Intermediate Similarity	NPD6569	Phase 2
0.819	Intermediate Similarity	NPD6494	Phase 2
0.8186	Intermediate Similarity	NPD5070	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD5658	Approved
0.8182	Intermediate Similarity	NPD4889	Approved
0.8142	Intermediate Similarity	NPD1923	Clinical (unspecified phase)
0.8102	Intermediate Similarity	NPD6230	Discontinued
0.8031	Intermediate Similarity	NPD4418	Discontinued
0.803	Intermediate Similarity	NPD4122	Approved
0.803	Intermediate Similarity	NPD4039	Approved
0.803	Intermediate Similarity	NPD4034	Approved
0.803	Intermediate Similarity	NPD4037	Approved
0.803	Intermediate Similarity	NPD4036	Approved
0.803	Intermediate Similarity	NPD4033	Approved
0.803	Intermediate Similarity	NPD32	Approved
0.803	Intermediate Similarity	NPD31	Approved
0.803	Intermediate Similarity	NPD4038	Approved
0.803	Intermediate Similarity	NPD4035	Approved
0.801	Intermediate Similarity	NPD6219	Discontinued
0.8	Intermediate Similarity	NPD5863	Clinical (unspecified phase)
0.799	Intermediate Similarity	NPD3477	Phase 2
0.799	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD7729	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD7222	Phase 2
0.7931	Intermediate Similarity	NPD7069	Discontinued
0.7923	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.785	Intermediate Similarity	NPD4795	Phase 2
0.7846	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7839	Intermediate Similarity	NPD6477	Clinical (unspecified phase)
0.7814	Intermediate Similarity	NPD2782	Approved
0.7814	Intermediate Similarity	NPD2780	Approved
0.7814	Intermediate Similarity	NPD6963	Approved
0.7814	Intermediate Similarity	NPD6964	Approved
0.7795	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7795	Intermediate Similarity	NPD4551	Phase 2
0.7795	Intermediate Similarity	NPD1038	Approved
0.7768	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7767	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.7761	Intermediate Similarity	NPD3397	Phase 2
0.7754	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7743	Intermediate Similarity	NPD8091	Phase 3
0.7737	Intermediate Similarity	NPD3386	Phase 2
0.773	Intermediate Similarity	NPD2781	Approved
0.7729	Intermediate Similarity	NPD5612	Discontinued
0.7723	Intermediate Similarity	NPD5530	Phase 1
0.7721	Intermediate Similarity	NPD4885	Approved
0.7685	Intermediate Similarity	NPD7452	Approved
0.7685	Intermediate Similarity	NPD7453	Approved
0.7653	Intermediate Similarity	NPD7675	Phase 3
0.7653	Intermediate Similarity	NPD7674	Phase 3
0.7653	Intermediate Similarity	NPD7676	Clinical (unspecified phase)
0.765	Intermediate Similarity	NPD4396	Clinical (unspecified phase)
0.765	Intermediate Similarity	NPD1740	Approved
0.765	Intermediate Similarity	NPD1739	Approved
0.7647	Intermediate Similarity	NPD1078	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD7571	Clinical (unspecified phase)
0.7621	Intermediate Similarity	NPD4131	Phase 3
0.76	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7577	Intermediate Similarity	NPD4375	Approved
0.7571	Intermediate Similarity	NPD6568	Discontinued
0.7566	Intermediate Similarity	NPD7859	Phase 2
0.7552	Intermediate Similarity	NPD4203	Approved
0.7552	Intermediate Similarity	NPD4204	Approved
0.7549	Intermediate Similarity	NPD5601	Phase 2
0.7546	Intermediate Similarity	NPD8052	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD6501	Approved
0.7536	Intermediate Similarity	NPD6500	Approved
0.7536	Intermediate Similarity	NPD4502	Phase 2
0.7535	Intermediate Similarity	NPD6553	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7523	Intermediate Similarity	NPD7719	Discontinued
0.7523	Intermediate Similarity	NPD4876	Phase 3
0.7523	Intermediate Similarity	NPD4875	Phase 3
0.7513	Intermediate Similarity	NPD2334	Discontinued
0.7512	Intermediate Similarity	NPD3825	Phase 3
0.7512	Intermediate Similarity	NPD1856	Discontinued
0.75	Intermediate Similarity	NPD5930	Phase 3
0.7488	Intermediate Similarity	NPD7426	Phase 1
0.7487	Intermediate Similarity	NPD1032	Phase 2
0.7487	Intermediate Similarity	NPD2917	Approved
0.7476	Intermediate Similarity	NPD5529	Phase 1
0.7476	Intermediate Similarity	NPD2739	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD5528	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD5147	Discontinued
0.7463	Intermediate Similarity	NPD2060	Approved
0.7449	Intermediate Similarity	NPD1034	Phase 3
0.7449	Intermediate Similarity	NPD1033	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD7558	Phase 2
0.7441	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD1954	Phase 1
0.7426	Intermediate Similarity	NPD3541	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD6242	Discontinued
0.7409	Intermediate Similarity	NPD2600	Approved
0.7409	Intermediate Similarity	NPD2599	Approved
0.7409	Intermediate Similarity	NPD2601	Approved
0.7406	Intermediate Similarity	NPD3354	Phase 2
0.74	Intermediate Similarity	NPD3396	Approved
0.74	Intermediate Similarity	NPD3395	Approved
0.7396	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD4071	Approved
0.7396	Intermediate Similarity	NPD4072	Approved
0.7387	Intermediate Similarity	NPD4372	Phase 1
0.7374	Intermediate Similarity	NPD6281	Approved
0.7366	Intermediate Similarity	NPD112	Approved
0.7366	Intermediate Similarity	NPD9705	Discontinued
0.7352	Intermediate Similarity	NPD4995	Approved
0.7352	Intermediate Similarity	NPD4996	Approved
0.7351	Intermediate Similarity	NPD2581	Approved
0.7351	Intermediate Similarity	NPD2582	Approved
0.735	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD4584	Approved
0.7346	Intermediate Similarity	NPD5902	Approved
0.7346	Intermediate Similarity	NPD5903	Approved
0.7345	Intermediate Similarity	NPD8100	Phase 3
0.7339	Intermediate Similarity	NPD7555	Discontinued
0.7333	Intermediate Similarity	NPD7620	Phase 2
0.7313	Intermediate Similarity	NPD6590	Discontinued
0.7313	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD4921	Phase 3
0.731	Intermediate Similarity	NPD4919	Phase 3
0.731	Intermediate Similarity	NPD4920	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD2189	Approved
0.7308	Intermediate Similarity	NPD7672	Approved
0.7308	Intermediate Similarity	NPD7671	Approved
0.7308	Intermediate Similarity	NPD2187	Approved
0.7306	Intermediate Similarity	NPD4925	Approved
0.7303	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD8063	Discontinued
0.7284	Intermediate Similarity	NPD7169	Suspended
0.7282	Intermediate Similarity	NPD6991	Approved
0.7277	Intermediate Similarity	NPD2482	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD7025	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD4083	Discontinued
0.7277	Intermediate Similarity	NPD6550	Discontinued
0.7277	Intermediate Similarity	NPD7885	Phase 2
0.7277	Intermediate Similarity	NPD7886	Phase 2
0.7268	Intermediate Similarity	NPD1620	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD6361	Phase 2
0.726	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD5429	Discontinued
0.726	Intermediate Similarity	NPD5559	Phase 2
0.7255	Intermediate Similarity	NPD4548	Discontinued
0.7255	Intermediate Similarity	NPD5999	Phase 2
0.7249	Intermediate Similarity	NPD8101	Phase 3
0.7243	Intermediate Similarity	NPD4429	Discontinued
0.7241	Intermediate Similarity	NPD6769	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7948	Phase 1
0.7238	Intermediate Similarity	NPD6262	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD4021	Phase 2
0.7233	Intermediate Similarity	NPD5669	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD7112	Discontinued
0.7228	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD3810	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD1900	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD7567	Approved
0.7227	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD4724	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD5255	Approved
0.7208	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD5007	Approved
0.7204	Intermediate Similarity	NPD5067	Phase 2
0.7204	Intermediate Similarity	NPD5066	Phase 2
0.72	Intermediate Similarity	NPD8016	Phase 3
0.72	Intermediate Similarity	NPD8017	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5905	Phase 1
0.7184	Intermediate Similarity	NPD6592	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD1392	Approved
0.7168	Intermediate Similarity	NPD6790	Phase 1
0.7165	Intermediate Similarity	NPD5100	Phase 3
0.7163	Intermediate Similarity	NPD3946	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD926	Approved
0.7158	Intermediate Similarity	NPD925	Approved
0.7157	Intermediate Similarity	NPD2952	Discontinued
0.7157	Intermediate Similarity	NPD4899	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD7034	Discontinued
0.715	Intermediate Similarity	NPD6975	Discontinued
0.7143	Intermediate Similarity	NPD1602	Discontinued
0.7143	Intermediate Similarity	NPD5008	Approved
0.7137	Intermediate Similarity	NPD5051	Phase 1
0.7136	Intermediate Similarity	NPD5944	Phase 1
0.7136	Intermediate Similarity	NPD5945	Phase 1
0.7136	Intermediate Similarity	NPD1322	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD3402	Phase 1
0.713	Intermediate Similarity	NPD8350	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD3003	Approved
0.7122	Intermediate Similarity	NPD7889	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD7201	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