NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	352.15
Volume:	363.931
LogP:	3.785
LogD:	3.562
LogS:	-5.366
# Rotatable Bonds:	4
TPSA:	40.8
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.675
Synthetic Accessibility Score:	2.62
Fsp3:	0.286
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:	-5.132
MDCK Permeability:	3.6821224057348445e-05
Pgp-inhibitor:	0.051
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.299
30% Bioavailability (F30%):	0.813

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.923
Plasma Protein Binding (PPB):	74.56986236572266%
Volume Distribution (VD):	1.199
Pgp-substrate:	7.242462635040283%

ADMET: Metabolism

CYP1A2-inhibitor:	0.177
CYP1A2-substrate:	0.967
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.92
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.826
CYP2D6-inhibitor:	0.241
CYP2D6-substrate:	0.936
CYP3A4-inhibitor:	0.036
CYP3A4-substrate:	0.723

ADMET: Excretion

Clearance (CL):	9.265
Half-life (T1/2):	0.373

ADMET: Toxicity

hERG Blockers:	0.304
Human Hepatotoxicity (H-HT):	0.094
Drug-inuced Liver Injury (DILI):	0.809
AMES Toxicity:	0.234
Rat Oral Acute Toxicity:	0.166
Maximum Recommended Daily Dose:	0.617
Skin Sensitization:	0.882
Carcinogencity:	0.074
Eye Corrosion:	0.003
Eye Irritation:	0.02
Respiratory Toxicity:	0.503

Download Data

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

Natural Product: NPC476580

Natural Product ID:	NPC476580
*Common Name:**	Dehydrocorytenchine Trifluoroacetate
IUPAC Name:	2,2,2-trifluoroacetate;2,3,10-trimethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium-11-ol
Synonyms:	Dehydrocorytenchine Trifluoroacetate
Standard InCHIKey:	ZMWCVHBJNQCFCL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H19NO4.C2HF3O2/c1-23-18-9-14-11-21-5-4-12-8-19(24-2)20(25-3)10-15(12)16(21)6-13(14)7-17(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)O)OC)OC.C(=O)(C(F)(F)F)[O-]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	52943272
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	=	97600	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 NPC476580 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	394
0.1-0.2	2859
0.2-0.3	11807
0.3-0.4	5113
0.4-0.5	13728
0.5-0.6	6831
0.6-0.7	1699
0.7-0.8	242
0.8-0.85	17
0.85-0.9	4
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9795	High Similarity	NPC57512
0.9281	High Similarity	NPC306669
0.9257	High Similarity	NPC476579
0.9091	High Similarity	NPC476569
0.9051	High Similarity	NPC4669
0.8774	High Similarity	NPC106786
0.875	High Similarity	NPC85747
0.875	High Similarity	NPC8337
0.8726	High Similarity	NPC59567
0.8531	High Similarity	NPC160193
0.8467	Intermediate Similarity	NPC476567
0.8467	Intermediate Similarity	NPC128019
0.8467	Intermediate Similarity	NPC136860
0.8462	Intermediate Similarity	NPC93593
0.8456	Intermediate Similarity	NPC474915
0.8456	Intermediate Similarity	NPC213206
0.8456	Intermediate Similarity	NPC188163
0.8456	Intermediate Similarity	NPC328750
0.8447	Intermediate Similarity	NPC471604
0.8389	Intermediate Similarity	NPC314682
0.8365	Intermediate Similarity	NPC226428
0.8323	Intermediate Similarity	NPC223125
0.8302	Intermediate Similarity	NPC118804
0.8269	Intermediate Similarity	NPC476568
0.8247	Intermediate Similarity	NPC476144
0.8247	Intermediate Similarity	NPC51957
0.8247	Intermediate Similarity	NPC106295
0.8247	Intermediate Similarity	NPC16107
0.8247	Intermediate Similarity	NPC210437
0.8235	Intermediate Similarity	NPC130926
0.8217	Intermediate Similarity	NPC223124
0.821	Intermediate Similarity	NPC255607
0.821	Intermediate Similarity	NPC3375
0.8194	Intermediate Similarity	NPC7467
0.8151	Intermediate Similarity	NPC200555
0.8151	Intermediate Similarity	NPC196026
0.8133	Intermediate Similarity	NPC253429
0.8117	Intermediate Similarity	NPC185838
0.8108	Intermediate Similarity	NPC160692
0.8089	Intermediate Similarity	NPC220858
0.8089	Intermediate Similarity	NPC97221
0.8089	Intermediate Similarity	NPC88249
0.8089	Intermediate Similarity	NPC192768
0.8089	Intermediate Similarity	NPC151895
0.8077	Intermediate Similarity	NPC428
0.8077	Intermediate Similarity	NPC476571
0.8077	Intermediate Similarity	NPC147390
0.8077	Intermediate Similarity	NPC24233
0.8077	Intermediate Similarity	NPC475959
0.8077	Intermediate Similarity	NPC246587
0.8077	Intermediate Similarity	NPC135538
0.8067	Intermediate Similarity	NPC7018
0.8067	Intermediate Similarity	NPC131204
0.8067	Intermediate Similarity	NPC301050
0.8014	Intermediate Similarity	NPC172403
0.8013	Intermediate Similarity	NPC179825
0.8013	Intermediate Similarity	NPC191376
0.8013	Intermediate Similarity	NPC476151
0.8013	Intermediate Similarity	NPC321505
0.7988	Intermediate Similarity	NPC231198
0.7988	Intermediate Similarity	NPC39103
0.7988	Intermediate Similarity	NPC2770
0.7987	Intermediate Similarity	NPC210148
0.7987	Intermediate Similarity	NPC233029
0.7975	Intermediate Similarity	NPC274026
0.7963	Intermediate Similarity	NPC216816
0.7962	Intermediate Similarity	NPC130941
0.7952	Intermediate Similarity	NPC470324
0.7933	Intermediate Similarity	NPC274441
0.7925	Intermediate Similarity	NPC326316
0.7925	Intermediate Similarity	NPC119669
0.7925	Intermediate Similarity	NPC81733
0.7911	Intermediate Similarity	NPC103379
0.7911	Intermediate Similarity	NPC219162
0.7911	Intermediate Similarity	NPC92541
0.7911	Intermediate Similarity	NPC477565
0.7907	Intermediate Similarity	NPC116007
0.7888	Intermediate Similarity	NPC127674
0.7888	Intermediate Similarity	NPC80129
0.7888	Intermediate Similarity	NPC216459
0.7888	Intermediate Similarity	NPC469817
0.7888	Intermediate Similarity	NPC295691
0.7888	Intermediate Similarity	NPC278799
0.7888	Intermediate Similarity	NPC172765
0.7888	Intermediate Similarity	NPC41178
0.7888	Intermediate Similarity	NPC204828
0.7888	Intermediate Similarity	NPC138487
0.7888	Intermediate Similarity	NPC276588
0.7888	Intermediate Similarity	NPC54379
0.7888	Intermediate Similarity	NPC325871
0.7888	Intermediate Similarity	NPC2413
0.7888	Intermediate Similarity	NPC110416
0.7888	Intermediate Similarity	NPC187022
0.7888	Intermediate Similarity	NPC193949
0.7888	Intermediate Similarity	NPC189266
0.7888	Intermediate Similarity	NPC99659
0.7888	Intermediate Similarity	NPC207757
0.7888	Intermediate Similarity	NPC249797
0.7888	Intermediate Similarity	NPC184026
0.7888	Intermediate Similarity	NPC5238
0.7888	Intermediate Similarity	NPC39701
0.7881	Intermediate Similarity	NPC209195
0.7881	Intermediate Similarity	NPC13826
0.7881	Intermediate Similarity	NPC11147
0.7875	Intermediate Similarity	NPC82285
0.7875	Intermediate Similarity	NPC37272
0.7875	Intermediate Similarity	NPC148898
0.7875	Intermediate Similarity	NPC133011
0.784	Intermediate Similarity	NPC247639
0.784	Intermediate Similarity	NPC146288
0.784	Intermediate Similarity	NPC25084
0.7812	Intermediate Similarity	NPC218575
0.7805	Intermediate Similarity	NPC475780
0.7799	Intermediate Similarity	NPC60538
0.7799	Intermediate Similarity	NPC207824
0.7791	Intermediate Similarity	NPC476572
0.7785	Intermediate Similarity	NPC144863
0.7785	Intermediate Similarity	NPC253883
0.7785	Intermediate Similarity	NPC90844
0.7785	Intermediate Similarity	NPC95075
0.7778	Intermediate Similarity	NPC78733
0.7764	Intermediate Similarity	NPC470924
0.7758	Intermediate Similarity	NPC153631
0.7744	Intermediate Similarity	NPC59028
0.7744	Intermediate Similarity	NPC92191
0.7744	Intermediate Similarity	NPC111485
0.773	Intermediate Similarity	NPC147091
0.773	Intermediate Similarity	NPC31311
0.773	Intermediate Similarity	NPC234392
0.7719	Intermediate Similarity	NPC241704
0.7707	Intermediate Similarity	NPC294249
0.7702	Intermediate Similarity	NPC277669
0.7702	Intermediate Similarity	NPC76213
0.7701	Intermediate Similarity	NPC83511
0.7697	Intermediate Similarity	NPC205167
0.7688	Intermediate Similarity	NPC44869
0.7682	Intermediate Similarity	NPC118419
0.7679	Intermediate Similarity	NPC474324
0.7679	Intermediate Similarity	NPC57812
0.7674	Intermediate Similarity	NPC21885
0.7669	Intermediate Similarity	NPC244112
0.7636	Intermediate Similarity	NPC477080
0.7633	Intermediate Similarity	NPC66573
0.7633	Intermediate Similarity	NPC475845
0.763	Intermediate Similarity	NPC32154
0.7622	Intermediate Similarity	NPC126519
0.7622	Intermediate Similarity	NPC203784
0.7622	Intermediate Similarity	NPC170503
0.7622	Intermediate Similarity	NPC186063
0.7616	Intermediate Similarity	NPC476570
0.7616	Intermediate Similarity	NPC222524
0.7613	Intermediate Similarity	NPC231572
0.7607	Intermediate Similarity	NPC2295
0.7607	Intermediate Similarity	NPC477564
0.7605	Intermediate Similarity	NPC324144
0.7605	Intermediate Similarity	NPC475393
0.7605	Intermediate Similarity	NPC233650
0.759	Intermediate Similarity	NPC249274
0.759	Intermediate Similarity	NPC266753
0.759	Intermediate Similarity	NPC232924
0.759	Intermediate Similarity	NPC306902
0.759	Intermediate Similarity	NPC160298
0.759	Intermediate Similarity	NPC135006
0.759	Intermediate Similarity	NPC477559
0.759	Intermediate Similarity	NPC166014
0.759	Intermediate Similarity	NPC27410
0.7588	Intermediate Similarity	NPC474708
0.7586	Intermediate Similarity	NPC298339
0.7576	Intermediate Similarity	NPC475326
0.7574	Intermediate Similarity	NPC284842
0.756	Intermediate Similarity	NPC284183
0.756	Intermediate Similarity	NPC306843
0.756	Intermediate Similarity	NPC477563
0.756	Intermediate Similarity	NPC24465
0.756	Intermediate Similarity	NPC13504
0.756	Intermediate Similarity	NPC136508
0.756	Intermediate Similarity	NPC16805
0.756	Intermediate Similarity	NPC4138
0.756	Intermediate Similarity	NPC167546
0.756	Intermediate Similarity	NPC96603
0.756	Intermediate Similarity	NPC253043
0.756	Intermediate Similarity	NPC238530
0.756	Intermediate Similarity	NPC134858
0.756	Intermediate Similarity	NPC78222
0.756	Intermediate Similarity	NPC302527
0.756	Intermediate Similarity	NPC212794
0.756	Intermediate Similarity	NPC196447
0.756	Intermediate Similarity	NPC121275
0.756	Intermediate Similarity	NPC232514
0.756	Intermediate Similarity	NPC276944
0.7548	Intermediate Similarity	NPC252107
0.7546	Intermediate Similarity	NPC26601
0.7545	Intermediate Similarity	NPC60186
0.7545	Intermediate Similarity	NPC24954
0.7532	Intermediate Similarity	NPC475828
0.7529	Intermediate Similarity	NPC241055
0.7529	Intermediate Similarity	NPC86469
0.7516	Intermediate Similarity	NPC470925
0.7516	Intermediate Similarity	NPC37144
0.7516	Intermediate Similarity	NPC59907

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 NPC476580 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	245
0.1-0.2	695
0.2-0.3	944
0.3-0.4	1436
0.4-0.5	2732
0.5-0.6	2272
0.6-0.7	748
0.7-0.8	75
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8456	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD6030	Approved
0.8258	Intermediate Similarity	NPD3639	Approved
0.8258	Intermediate Similarity	NPD3640	Phase 3
0.8258	Intermediate Similarity	NPD6031	Approved
0.8258	Intermediate Similarity	NPD3641	Approved
0.8247	Intermediate Similarity	NPD4584	Approved
0.7952	Intermediate Similarity	NPD2898	Approved
0.7888	Intermediate Similarity	NPD7298	Approved
0.7812	Intermediate Similarity	NPD4017	Approved
0.7791	Intermediate Similarity	NPD5978	Approved
0.7791	Intermediate Similarity	NPD5977	Approved
0.7785	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD5718	Phase 2
0.7716	Intermediate Similarity	NPD4773	Phase 2
0.7716	Intermediate Similarity	NPD4772	Phase 2
0.7665	Intermediate Similarity	NPD6107	Approved
0.7588	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD4166	Phase 2
0.7515	Intermediate Similarity	NPD4585	Approved
0.75	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD7802	Discontinued
0.7443	Intermediate Similarity	NPD6618	Phase 2
0.7439	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD2492	Phase 1
0.7416	Intermediate Similarity	NPD7291	Discontinued
0.7412	Intermediate Similarity	NPD4010	Discontinued
0.7399	Intermediate Similarity	NPD5313	Approved
0.7399	Intermediate Similarity	NPD5312	Approved
0.7394	Intermediate Similarity	NPD4859	Phase 1
0.7394	Intermediate Similarity	NPD7110	Phase 1
0.7394	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD3124	Discontinued
0.7375	Intermediate Similarity	NPD5241	Discontinued
0.7372	Intermediate Similarity	NPD6895	Approved
0.7372	Intermediate Similarity	NPD6896	Approved
0.7341	Intermediate Similarity	NPD8251	Approved
0.7341	Intermediate Similarity	NPD8099	Discontinued
0.7341	Intermediate Similarity	NPD8252	Approved
0.7326	Intermediate Similarity	NPD4481	Phase 3
0.7321	Intermediate Similarity	NPD6788	Approved
0.7314	Intermediate Similarity	NPD6297	Approved
0.731	Intermediate Similarity	NPD6071	Discontinued
0.7305	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD8156	Discontinued
0.7289	Intermediate Similarity	NPD5090	Approved
0.7289	Intermediate Similarity	NPD5089	Approved
0.7278	Intermediate Similarity	NPD7833	Phase 2
0.7278	Intermediate Similarity	NPD1307	Phase 2
0.7278	Intermediate Similarity	NPD7831	Phase 2
0.7278	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD1309	Phase 2
0.7262	Intermediate Similarity	NPD2563	Approved
0.7262	Intermediate Similarity	NPD2560	Approved
0.7256	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD1424	Approved
0.7222	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD2971	Approved
0.7191	Intermediate Similarity	NPD2968	Approved
0.7179	Intermediate Similarity	NPD3110	Approved
0.7179	Intermediate Similarity	NPD3109	Approved
0.7169	Intermediate Similarity	NPD824	Approved
0.7169	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD6688	Approved
0.7168	Intermediate Similarity	NPD6687	Approved
0.716	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD6851	Approved
0.7151	Intermediate Similarity	NPD6853	Approved
0.7135	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD6876	Approved
0.7126	Intermediate Similarity	NPD6875	Approved
0.7119	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD2674	Phase 3
0.7112	Intermediate Similarity	NPD5457	Discontinued
0.7112	Intermediate Similarity	NPD6612	Phase 2
0.7093	Intermediate Similarity	NPD5677	Discontinued
0.7091	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD2653	Approved
0.7086	Intermediate Similarity	NPD5966	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6385	Approved
0.7083	Intermediate Similarity	NPD6386	Approved
0.7073	Intermediate Similarity	NPD5297	Approved
0.7069	Intermediate Similarity	NPD2969	Approved
0.7069	Intermediate Similarity	NPD2970	Approved
0.7066	Intermediate Similarity	NPD3866	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD5900	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD8053	Approved
0.7056	Intermediate Similarity	NPD8054	Approved
0.703	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD2335	Discontinued
0.7029	Intermediate Similarity	NPD27	Approved
0.7029	Intermediate Similarity	NPD2489	Approved
0.7021	Intermediate Similarity	NPD4107	Approved
0.7019	Intermediate Similarity	NPD3656	Approved
0.7012	Intermediate Similarity	NPD7124	Phase 2
0.7011	Intermediate Similarity	NPD3922	Approved
0.7011	Intermediate Similarity	NPD3921	Approved
0.7011	Intermediate Similarity	NPD3051	Approved
0.7011	Intermediate Similarity	NPD3923	Approved
0.7011	Intermediate Similarity	NPD3924	Approved
0.7006	Intermediate Similarity	NPD4474	Approved
0.7006	Intermediate Similarity	NPD4475	Approved
0.7006	Intermediate Similarity	NPD5521	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD5071	Phase 2
0.6982	Remote Similarity	NPD6873	Phase 2
0.6974	Remote Similarity	NPD7225	Discontinued
0.6971	Remote Similarity	NPD2388	Discontinued
0.6966	Remote Similarity	NPD3885	Approved
0.6966	Remote Similarity	NPD3920	Phase 2
0.6957	Remote Similarity	NPD2488	Approved
0.6957	Remote Similarity	NPD2490	Approved
0.6957	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD8149	Discontinued
0.6952	Remote Similarity	NPD7034	Discontinued
0.6943	Remote Similarity	NPD3145	Approved
0.6943	Remote Similarity	NPD3144	Approved
0.6933	Remote Similarity	NPD4162	Approved
0.6933	Remote Similarity	NPD3060	Approved
0.6933	Remote Similarity	NPD5177	Phase 3
0.6928	Remote Similarity	NPD1421	Approved
0.6928	Remote Similarity	NPD1420	Approved
0.6915	Remote Similarity	NPD4420	Approved
0.6913	Remote Similarity	NPD5536	Phase 2
0.6899	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD4482	Phase 3
0.6885	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5242	Approved
0.6875	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4083	Discontinued
0.6871	Remote Similarity	NPD1044	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD2421	Approved
0.6867	Remote Similarity	NPD2420	Approved
0.6864	Remote Similarity	NPD4005	Discontinued
0.6862	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD5564	Approved
0.6862	Remote Similarity	NPD2973	Approved
0.6862	Remote Similarity	NPD2974	Approved
0.6862	Remote Similarity	NPD2975	Approved
0.6859	Remote Similarity	NPD3057	Approved
0.6855	Remote Similarity	NPD3140	Approved
0.6855	Remote Similarity	NPD3142	Approved
0.6848	Remote Similarity	NPD3301	Approved
0.6832	Remote Similarity	NPD6111	Discontinued
0.6831	Remote Similarity	NPD5087	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD4237	Approved
0.6829	Remote Similarity	NPD4236	Phase 3
0.6811	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD2120	Phase 2
0.6807	Remote Similarity	NPD3845	Phase 1
0.6805	Remote Similarity	NPD4210	Discontinued
0.6795	Remote Similarity	NPD7905	Discontinued
0.6788	Remote Similarity	NPD6748	Discontinued
0.6788	Remote Similarity	NPD6331	Phase 2
0.6786	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD2667	Approved
0.6776	Remote Similarity	NPD2668	Approved
0.6771	Remote Similarity	NPD3106	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD2972	Approved
0.6771	Remote Similarity	NPD5006	Approved
0.6771	Remote Similarity	NPD5005	Approved
0.6771	Remote Similarity	NPD3533	Approved
0.6768	Remote Similarity	NPD7153	Discontinued
0.6765	Remote Similarity	NPD6357	Discontinued
0.676	Remote Similarity	NPD2822	Clinical (unspecified phase)
0.676	Remote Similarity	NPD4498	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD7549	Discontinued
0.6757	Remote Similarity	NPD5283	Phase 1
0.6755	Remote Similarity	NPD4413	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD4580	Approved
0.6754	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD4727	Phase 1
0.6744	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD5720	Discontinued
0.674	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD4098	Discontinued
0.673	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD4123	Phase 3
0.6724	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD5186	Approved
0.6723	Remote Similarity	NPD5183	Approved
0.6721	Remote Similarity	NPD7312	Approved
0.6721	Remote Similarity	NPD7281	Phase 3
0.6721	Remote Similarity	NPD7313	Approved
0.6721	Remote Similarity	NPD7311	Approved
0.6721	Remote Similarity	NPD7280	Phase 3
0.6721	Remote Similarity	NPD7310	Approved
0.672	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD3452	Approved
0.6719	Remote Similarity	NPD2494	Approved

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