NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	339.15
Volume:	347.953
LogP:	2.067
LogD:	2.963
LogS:	-3.562
# Rotatable Bonds:	3
TPSA:	53.76
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.804
Synthetic Accessibility Score:	3.956
Fsp3:	0.35
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.067
MDCK Permeability:	2.9420971259241924e-05
Pgp-inhibitor:	0.537
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.353

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.733
Plasma Protein Binding (PPB):	83.96666717529297%
Volume Distribution (VD):	1.351
Pgp-substrate:	11.661476135253906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.266
CYP1A2-substrate:	0.62
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.874
CYP2C9-inhibitor:	0.008
CYP2C9-substrate:	0.431
CYP2D6-inhibitor:	0.041
CYP2D6-substrate:	0.753
CYP3A4-inhibitor:	0.023
CYP3A4-substrate:	0.758

ADMET: Excretion

Clearance (CL):	8.566
Half-life (T1/2):	0.464

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.2
Drug-inuced Liver Injury (DILI):	0.309
AMES Toxicity:	0.192
Rat Oral Acute Toxicity:	0.268
Maximum Recommended Daily Dose:	0.985
Skin Sensitization:	0.116
Carcinogencity:	0.195
Eye Corrosion:	0.005
Eye Irritation:	0.157
Respiratory Toxicity:	0.956

Download Data

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

Natural Product: NPC476568

Natural Product ID:	NPC476568
*Common Name:**	(13aS)-2,3,11-trimethoxy-5,6,13,13a-tetrahydroisoquinolino[2,1-b]isoquinolin-7-ium-10-ol;2,2,2-trifluoroacetate
IUPAC Name:	(13aS)-2,3,11-trimethoxy-5,6,13,13a-tetrahydroisoquinolino[2,1-b]isoquinolin-7-ium-10-ol;2,2,2-trifluoroacetate
Synonyms:
Standard InCHIKey:	VFNBODWIXIYCJN-NTISSMGPSA-N
Standard InCHI:	InChI=1S/C20H21NO4.C2HF3O2/c1-23-18-9-13-6-16-15-10-20(25-3)19(24-2)8-12(15)4-5-21(16)11-14(13)7-17(18)22;3-2(4,5)1(6)7/h7-11,16H,4-6H2,1-3H3;(H,6,7)/t16-;/m0./s1
SMILES:	COC1=C(C=C2[C@@H]3CC4=CC(=C(C=C4C=[N+]3CCC2=C1)O)OC)OC.C(=O)(C(F)(F)F)[O-]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	49831394
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002955] Tetrahydroisoquinolines

*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	=	153900	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 NPC476568 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	228
0.1-0.2	1415
0.2-0.3	8199
0.3-0.4	9631
0.4-0.5	8030
0.5-0.6	12440
0.6-0.7	2038
0.7-0.8	635
0.8-0.85	70
0.85-0.9	9
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9333	High Similarity	NPC216816
0.9167	High Similarity	NPC476567
0.9167	High Similarity	NPC128019
0.9167	High Similarity	NPC136860
0.9161	High Similarity	NPC213206
0.9161	High Similarity	NPC328750
0.9161	High Similarity	NPC188163
0.9161	High Similarity	NPC474915
0.9091	High Similarity	NPC314682
0.8919	High Similarity	NPC51957
0.8919	High Similarity	NPC106295
0.8919	High Similarity	NPC210437
0.8919	High Similarity	NPC16107
0.8919	High Similarity	NPC476144
0.8917	High Similarity	NPC66573
0.8859	High Similarity	NPC7467
0.8784	High Similarity	NPC185838
0.8742	High Similarity	NPC88249
0.8742	High Similarity	NPC151895
0.8742	High Similarity	NPC220858
0.8742	High Similarity	NPC192768
0.8742	High Similarity	NPC97221
0.8733	High Similarity	NPC476571
0.8733	High Similarity	NPC246587
0.8733	High Similarity	NPC428
0.8733	High Similarity	NPC475959
0.8733	High Similarity	NPC147390
0.8733	High Similarity	NPC24233
0.8733	High Similarity	NPC135538
0.8667	High Similarity	NPC179825
0.8667	High Similarity	NPC321505
0.8667	High Similarity	NPC191376
0.8662	High Similarity	NPC476570
0.8627	High Similarity	NPC210148
0.8627	High Similarity	NPC233029
0.8592	High Similarity	NPC160193
0.8562	High Similarity	NPC81733
0.8562	High Similarity	NPC326316
0.8543	High Similarity	NPC476151
0.8516	High Similarity	NPC204828
0.8516	High Similarity	NPC80129
0.8516	High Similarity	NPC276588
0.8516	High Similarity	NPC207757
0.8516	High Similarity	NPC99659
0.8516	High Similarity	NPC189266
0.8516	High Similarity	NPC127674
0.8516	High Similarity	NPC2413
0.8516	High Similarity	NPC295691
0.8516	High Similarity	NPC325871
0.8516	High Similarity	NPC54379
0.8516	High Similarity	NPC187022
0.8516	High Similarity	NPC39701
0.8516	High Similarity	NPC278799
0.8516	High Similarity	NPC41178
0.8516	High Similarity	NPC216459
0.8516	High Similarity	NPC5238
0.8516	High Similarity	NPC249797
0.8516	High Similarity	NPC469817
0.8516	High Similarity	NPC184026
0.8516	High Similarity	NPC193949
0.8516	High Similarity	NPC138487
0.8516	High Similarity	NPC110416
0.8516	High Similarity	NPC172765
0.8487	Intermediate Similarity	NPC130941
0.8462	Intermediate Similarity	NPC25084
0.8462	Intermediate Similarity	NPC146288
0.8462	Intermediate Similarity	NPC247639
0.8435	Intermediate Similarity	NPC253429
0.8434	Intermediate Similarity	NPC476202
0.8431	Intermediate Similarity	NPC477565
0.8431	Intermediate Similarity	NPC103379
0.8431	Intermediate Similarity	NPC219162
0.8431	Intermediate Similarity	NPC92541
0.8431	Intermediate Similarity	NPC60538
0.8431	Intermediate Similarity	NPC207824
0.8425	Intermediate Similarity	NPC11147
0.8411	Intermediate Similarity	NPC130926
0.8408	Intermediate Similarity	NPC476572
0.8397	Intermediate Similarity	NPC93593
0.8373	Intermediate Similarity	NPC195538
0.8354	Intermediate Similarity	NPC111485
0.8344	Intermediate Similarity	NPC31311
0.8344	Intermediate Similarity	NPC234392
0.8333	Intermediate Similarity	NPC249996
0.8323	Intermediate Similarity	NPC476579
0.8323	Intermediate Similarity	NPC277669
0.8323	Intermediate Similarity	NPC76213
0.8322	Intermediate Similarity	NPC172403
0.8301	Intermediate Similarity	NPC90844
0.8301	Intermediate Similarity	NPC253883
0.8301	Intermediate Similarity	NPC144863
0.8301	Intermediate Similarity	NPC95075
0.8269	Intermediate Similarity	NPC476580
0.8239	Intermediate Similarity	NPC477080
0.8228	Intermediate Similarity	NPC203784
0.8228	Intermediate Similarity	NPC170503
0.8228	Intermediate Similarity	NPC126519
0.8219	Intermediate Similarity	NPC118419
0.8199	Intermediate Similarity	NPC324144
0.8199	Intermediate Similarity	NPC476569
0.8199	Intermediate Similarity	NPC475393
0.8187	Intermediate Similarity	NPC27410
0.8187	Intermediate Similarity	NPC232924
0.8187	Intermediate Similarity	NPC166014
0.8187	Intermediate Similarity	NPC477559
0.8187	Intermediate Similarity	NPC160298
0.8187	Intermediate Similarity	NPC266753
0.8187	Intermediate Similarity	NPC306902
0.8165	Intermediate Similarity	NPC244112
0.8163	Intermediate Similarity	NPC160692
0.8153	Intermediate Similarity	NPC37272
0.8148	Intermediate Similarity	NPC78222
0.8148	Intermediate Similarity	NPC121275
0.8148	Intermediate Similarity	NPC4138
0.8148	Intermediate Similarity	NPC477563
0.8148	Intermediate Similarity	NPC16805
0.8148	Intermediate Similarity	NPC276944
0.8148	Intermediate Similarity	NPC196447
0.8148	Intermediate Similarity	NPC96603
0.8148	Intermediate Similarity	NPC136508
0.8148	Intermediate Similarity	NPC238530
0.8148	Intermediate Similarity	NPC212794
0.8148	Intermediate Similarity	NPC284183
0.8148	Intermediate Similarity	NPC13504
0.8148	Intermediate Similarity	NPC302527
0.8148	Intermediate Similarity	NPC232514
0.8148	Intermediate Similarity	NPC306843
0.8148	Intermediate Similarity	NPC24465
0.8148	Intermediate Similarity	NPC167546
0.8148	Intermediate Similarity	NPC253043
0.8146	Intermediate Similarity	NPC470925
0.8141	Intermediate Similarity	NPC274026
0.8121	Intermediate Similarity	NPC7018
0.8121	Intermediate Similarity	NPC301050
0.8121	Intermediate Similarity	NPC131204
0.8113	Intermediate Similarity	NPC57512
0.8113	Intermediate Similarity	NPC186063
0.8101	Intermediate Similarity	NPC2295
0.8101	Intermediate Similarity	NPC477564
0.8098	Intermediate Similarity	NPC476432
0.8098	Intermediate Similarity	NPC13916
0.8098	Intermediate Similarity	NPC256012
0.8098	Intermediate Similarity	NPC264850
0.8098	Intermediate Similarity	NPC268503
0.8098	Intermediate Similarity	NPC24264
0.8098	Intermediate Similarity	NPC317272
0.8098	Intermediate Similarity	NPC42549
0.8098	Intermediate Similarity	NPC250846
0.8098	Intermediate Similarity	NPC240841
0.8089	Intermediate Similarity	NPC85747
0.8089	Intermediate Similarity	NPC8337
0.8086	Intermediate Similarity	NPC233650
0.805	Intermediate Similarity	NPC78733
0.8049	Intermediate Similarity	NPC306555
0.8049	Intermediate Similarity	NPC474931
0.8049	Intermediate Similarity	NPC158376
0.8049	Intermediate Similarity	NPC247389
0.8049	Intermediate Similarity	NPC145832
0.8049	Intermediate Similarity	NPC210918
0.8049	Intermediate Similarity	NPC81218
0.8049	Intermediate Similarity	NPC12053
0.8049	Intermediate Similarity	NPC117188
0.8049	Intermediate Similarity	NPC205421
0.8046	Intermediate Similarity	NPC85381
0.8038	Intermediate Similarity	NPC26601
0.8038	Intermediate Similarity	NPC82285
0.8038	Intermediate Similarity	NPC470924
0.8038	Intermediate Similarity	NPC133011
0.8038	Intermediate Similarity	NPC148898
0.8037	Intermediate Similarity	NPC225774
0.8037	Intermediate Similarity	NPC134858
0.8035	Intermediate Similarity	NPC318805
0.8035	Intermediate Similarity	NPC41122
0.8	Intermediate Similarity	NPC147091
0.7988	Intermediate Similarity	NPC219341
0.7987	Intermediate Similarity	NPC294249
0.7963	Intermediate Similarity	NPC205167
0.7952	Intermediate Similarity	NPC109925
0.7947	Intermediate Similarity	NPC193528
0.7939	Intermediate Similarity	NPC150879
0.7939	Intermediate Similarity	NPC298979
0.7939	Intermediate Similarity	NPC204947
0.7939	Intermediate Similarity	NPC210140
0.7937	Intermediate Similarity	NPC76079
0.7914	Intermediate Similarity	NPC60186
0.7911	Intermediate Similarity	NPC223125
0.7904	Intermediate Similarity	NPC317439
0.7904	Intermediate Similarity	NPC19520
0.7904	Intermediate Similarity	NPC317145
0.7904	Intermediate Similarity	NPC227060
0.7904	Intermediate Similarity	NPC10908
0.7904	Intermediate Similarity	NPC149090
0.7904	Intermediate Similarity	NPC115284
0.7904	Intermediate Similarity	NPC63646
0.7904	Intermediate Similarity	NPC276890
0.7904	Intermediate Similarity	NPC239775
0.7904	Intermediate Similarity	NPC198498
0.7904	Intermediate Similarity	NPC76682
0.7901	Intermediate Similarity	NPC59028
0.7901	Intermediate Similarity	NPC106786

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 NPC476568 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	149
0.1-0.2	584
0.2-0.3	1087
0.3-0.4	1458
0.4-0.5	2846
0.5-0.6	2255
0.6-0.7	664
0.7-0.8	102
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9161	High Similarity	NPD4664	Clinical (unspecified phase)
0.8919	High Similarity	NPD4584	Approved
0.8544	High Similarity	NPD7201	Clinical (unspecified phase)
0.8516	High Similarity	NPD7298	Approved
0.8509	High Similarity	NPD5602	Clinical (unspecified phase)
0.8442	Intermediate Similarity	NPD4017	Approved
0.8312	Intermediate Similarity	NPD3639	Approved
0.8312	Intermediate Similarity	NPD3641	Approved
0.8312	Intermediate Similarity	NPD3640	Phase 3
0.8278	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD6030	Approved
0.8194	Intermediate Similarity	NPD6031	Approved
0.8101	Intermediate Similarity	NPD4773	Phase 2
0.8101	Intermediate Similarity	NPD4772	Phase 2
0.8089	Intermediate Similarity	NPD4005	Discontinued
0.8082	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD7291	Discontinued
0.8027	Intermediate Similarity	NPD5718	Phase 2
0.7988	Intermediate Similarity	NPD4010	Discontinued
0.7947	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD8251	Approved
0.7904	Intermediate Similarity	NPD8099	Discontinued
0.7904	Intermediate Similarity	NPD8252	Approved
0.7871	Intermediate Similarity	NPD5241	Discontinued
0.7857	Intermediate Similarity	NPD8156	Discontinued
0.7829	Intermediate Similarity	NPD3922	Approved
0.7829	Intermediate Similarity	NPD3921	Approved
0.7829	Intermediate Similarity	NPD3924	Approved
0.7829	Intermediate Similarity	NPD3923	Approved
0.7818	Intermediate Similarity	NPD7802	Discontinued
0.7818	Intermediate Similarity	NPD6107	Approved
0.7791	Intermediate Similarity	NPD6788	Approved
0.7778	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD3124	Discontinued
0.777	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD6895	Approved
0.7763	Intermediate Similarity	NPD6896	Approved
0.7753	Intermediate Similarity	NPD7034	Discontinued
0.7706	Intermediate Similarity	NPD3920	Phase 2
0.7665	Intermediate Similarity	NPD4166	Phase 2
0.7636	Intermediate Similarity	NPD7833	Phase 2
0.7636	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD7831	Phase 2
0.7619	Intermediate Similarity	NPD2922	Phase 1
0.7616	Intermediate Similarity	NPD2674	Phase 3
0.761	Intermediate Similarity	NPD4123	Phase 3
0.7595	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD8053	Approved
0.7586	Intermediate Similarity	NPD8054	Approved
0.758	Intermediate Similarity	NPD6331	Phase 2
0.7574	Intermediate Similarity	NPD2898	Approved
0.7572	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD3110	Approved
0.7566	Intermediate Similarity	NPD3109	Approved
0.7558	Intermediate Similarity	NPD6297	Approved
0.755	Intermediate Similarity	NPD5111	Phase 2
0.755	Intermediate Similarity	NPD5109	Approved
0.755	Intermediate Similarity	NPD5110	Phase 2
0.7544	Intermediate Similarity	NPD5312	Approved
0.7544	Intermediate Similarity	NPD5313	Approved
0.7532	Intermediate Similarity	NPD3692	Discontinued
0.7532	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD4055	Discovery
0.7515	Intermediate Similarity	NPD5977	Approved
0.7515	Intermediate Similarity	NPD5978	Approved
0.7471	Intermediate Similarity	NPD4481	Phase 3
0.7456	Intermediate Similarity	NPD3051	Approved
0.7439	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD7110	Phase 1
0.7438	Intermediate Similarity	NPD2421	Approved
0.7438	Intermediate Similarity	NPD2420	Approved
0.7434	Intermediate Similarity	NPD3145	Approved
0.7434	Intermediate Similarity	NPD3144	Approved
0.7432	Intermediate Similarity	NPD6612	Phase 2
0.7427	Intermediate Similarity	NPD5966	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD5604	Discontinued
0.7412	Intermediate Similarity	NPD4083	Discontinued
0.7412	Intermediate Similarity	NPD6687	Approved
0.7412	Intermediate Similarity	NPD6688	Approved
0.7412	Intermediate Similarity	NPD2970	Approved
0.7412	Intermediate Similarity	NPD2969	Approved
0.7407	Intermediate Similarity	NPD2122	Discontinued
0.7394	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4474	Approved
0.7386	Intermediate Similarity	NPD6851	Approved
0.7386	Intermediate Similarity	NPD4475	Approved
0.7386	Intermediate Similarity	NPD6853	Approved
0.7378	Intermediate Similarity	NPD4678	Approved
0.7378	Intermediate Similarity	NPD4675	Approved
0.7375	Intermediate Similarity	NPD3845	Phase 1
0.7375	Intermediate Similarity	NPD7124	Phase 2
0.7368	Intermediate Similarity	NPD2489	Approved
0.7368	Intermediate Similarity	NPD27	Approved
0.7353	Intermediate Similarity	NPD6071	Discontinued
0.7315	Intermediate Similarity	NPD1669	Approved
0.7305	Intermediate Similarity	NPD2560	Approved
0.7305	Intermediate Similarity	NPD2563	Approved
0.7301	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD5177	Phase 3
0.7293	Intermediate Similarity	NPD6046	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD5720	Discontinued
0.7284	Intermediate Similarity	NPD1424	Approved
0.7277	Intermediate Similarity	NPD3815	Phase 1
0.7277	Intermediate Similarity	NPD3816	Phase 1
0.7273	Intermediate Similarity	NPD6876	Approved
0.7273	Intermediate Similarity	NPD6875	Approved
0.7267	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD2883	Discontinued
0.725	Intermediate Similarity	NPD6748	Discontinued
0.7246	Intermediate Similarity	NPD5772	Approved
0.7246	Intermediate Similarity	NPD5773	Approved
0.7239	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD7153	Discontinued
0.7215	Intermediate Similarity	NPD2161	Phase 2
0.7213	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD6257	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD6618	Phase 2
0.7188	Intermediate Similarity	NPD3060	Approved
0.7188	Intermediate Similarity	NPD4162	Approved
0.7182	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD7905	Discontinued
0.717	Intermediate Similarity	NPD3656	Approved
0.7167	Intermediate Similarity	NPD3349	Phase 2
0.7161	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD5283	Phase 1
0.7152	Intermediate Similarity	NPD6380	Phase 1
0.7151	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD5677	Discontinued
0.7127	Intermediate Similarity	NPD3408	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD1044	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD7598	Phase 2
0.7108	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD4098	Discontinued
0.7097	Intermediate Similarity	NPD8095	Phase 1
0.7097	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD5708	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD4236	Phase 3
0.7081	Intermediate Similarity	NPD6364	Approved
0.7081	Intermediate Similarity	NPD4237	Approved
0.7081	Intermediate Similarity	NPD44	Approved
0.7072	Intermediate Similarity	NPD7906	Approved
0.7059	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5267	Discontinued
0.7047	Intermediate Similarity	NPD2667	Approved
0.7047	Intermediate Similarity	NPD2668	Approved
0.7044	Intermediate Similarity	NPD1753	Discontinued
0.7044	Intermediate Similarity	NPD4108	Discontinued
0.7043	Intermediate Similarity	NPD4420	Approved
0.7039	Intermediate Similarity	NPD7311	Approved
0.7039	Intermediate Similarity	NPD2971	Approved
0.7039	Intermediate Similarity	NPD7313	Approved
0.7039	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7281	Phase 3
0.7039	Intermediate Similarity	NPD7312	Approved
0.7039	Intermediate Similarity	NPD7280	Phase 3
0.7039	Intermediate Similarity	NPD7310	Approved
0.7039	Intermediate Similarity	NPD2968	Approved
0.703	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD52	Approved
0.703	Intermediate Similarity	NPD7526	Approved
0.7025	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD7438	Suspended
0.7024	Intermediate Similarity	NPD5089	Approved
0.7024	Intermediate Similarity	NPD5090	Approved
0.7019	Intermediate Similarity	NPD2808	Discontinued
0.7019	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD7225	Discontinued
0.7	Intermediate Similarity	NPD7309	Approved
0.7	Intermediate Similarity	NPD5967	Approved
0.6995	Remote Similarity	NPD5641	Discontinued
0.6988	Remote Similarity	NPD4727	Phase 1
0.6981	Remote Similarity	NPD6111	Discontinued
0.6975	Remote Similarity	NPD2459	Approved
0.6975	Remote Similarity	NPD2458	Approved
0.6975	Remote Similarity	NPD2460	Phase 3
0.6974	Remote Similarity	NPD1421	Approved
0.6974	Remote Similarity	NPD1420	Approved
0.6971	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.697	Remote Similarity	NPD3763	Approved
0.697	Remote Similarity	NPD2874	Phase 2
0.6964	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD4577	Approved
0.6944	Remote Similarity	NPD4578	Approved
0.6943	Remote Similarity	NPD3531	Approved
0.6943	Remote Similarity	NPD7477	Discontinued
0.6943	Remote Similarity	NPD3532	Approved
0.6943	Remote Similarity	NPD3530	Approved
0.6941	Remote Similarity	NPD2978	Approved
0.6941	Remote Similarity	NPD6738	Phase 2
0.6941	Remote Similarity	NPD4585	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