NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	191.09
Volume:	199.731
LogP:	0.434
LogD:	1.415
LogS:	0.136
# Rotatable Bonds:	1
TPSA:	35.3
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.602
Synthetic Accessibility Score:	3.77
Fsp3:	0.364
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.525
MDCK Permeability:	2.7734409741242416e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.994
Human Intestinal Absorption (HIA):	0.031
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.088

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.935
Plasma Protein Binding (PPB):	19.947917938232422%
Volume Distribution (VD):	2.376
Pgp-substrate:	67.35401916503906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.613
CYP1A2-substrate:	0.49
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.729
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.209
CYP2D6-inhibitor:	0.112
CYP2D6-substrate:	0.813
CYP3A4-inhibitor:	0.003
CYP3A4-substrate:	0.279

ADMET: Excretion

Clearance (CL):	7.557
Half-life (T1/2):	0.711

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.587
Drug-inuced Liver Injury (DILI):	0.182
AMES Toxicity:	0.361
Rat Oral Acute Toxicity:	0.044
Maximum Recommended Daily Dose:	0.737
Skin Sensitization:	0.306
Carcinogencity:	0.81
Eye Corrosion:	0.522
Eye Irritation:	0.969
Respiratory Toxicity:	0.937

Download Data

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

Natural Product: NPC476570

Natural Product ID:	NPC476570
*Common Name:**	6-Methoxy-2-methyl-3,4-dihydroisoquinolin-2-ium-7-ol;2,2,2-trifluoroacetate
IUPAC Name:	6-methoxy-2-methyl-3,4-dihydroisoquinolin-2-ium-7-ol;2,2,2-trifluoroacetate
Synonyms:
Standard InCHIKey:	IHTJCZUOTYGPJX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H13NO2.C2HF3O2/c1-12-4-3-8-6-11(14-2)10(13)5-9(8)7-12;3-2(4,5)1(6)7/h5-7H,3-4H2,1-2H3;(H,6,7)
SMILES:	C[N+]1=CC2=CC(=C(C=C2CC1)OC)O.C(=O)(C(F)(F)F)[O-]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	52943408
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002958] Dihydroisoquinolines

*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	=	16000	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 NPC476570 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	174
0.1-0.2	1359
0.2-0.3	7752
0.3-0.4	10791
0.4-0.5	7226
0.5-0.6	11922
0.6-0.7	3113
0.7-0.8	353
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8662	High Similarity	NPC476568
0.8561	High Similarity	NPC160193
0.8406	Intermediate Similarity	NPC77572
0.8333	Intermediate Similarity	NPC301713
0.8308	Intermediate Similarity	NPC298486
0.8235	Intermediate Similarity	NPC160692
0.8188	Intermediate Similarity	NPC131204
0.8188	Intermediate Similarity	NPC7018
0.8188	Intermediate Similarity	NPC301050
0.8134	Intermediate Similarity	NPC153990
0.8134	Intermediate Similarity	NPC172403
0.8125	Intermediate Similarity	NPC120075
0.8116	Intermediate Similarity	NPC11147
0.8067	Intermediate Similarity	NPC216816
0.8029	Intermediate Similarity	NPC118419
0.8029	Intermediate Similarity	NPC214869
0.8014	Intermediate Similarity	NPC314682
0.8	Intermediate Similarity	NPC253429
0.7958	Intermediate Similarity	NPC328750
0.7958	Intermediate Similarity	NPC213206
0.7958	Intermediate Similarity	NPC474915
0.7958	Intermediate Similarity	NPC188163
0.7956	Intermediate Similarity	NPC114102
0.7941	Intermediate Similarity	NPC155838
0.7929	Intermediate Similarity	NPC167944
0.7929	Intermediate Similarity	NPC231884
0.7929	Intermediate Similarity	NPC42793
0.7899	Intermediate Similarity	NPC93882
0.7899	Intermediate Similarity	NPC130595
0.7883	Intermediate Similarity	NPC52029
0.7883	Intermediate Similarity	NPC35961
0.7883	Intermediate Similarity	NPC195749
0.7883	Intermediate Similarity	NPC262641
0.7852	Intermediate Similarity	NPC58661
0.7847	Intermediate Similarity	NPC128019
0.7847	Intermediate Similarity	NPC136860
0.7847	Intermediate Similarity	NPC476567
0.7842	Intermediate Similarity	NPC285078
0.7842	Intermediate Similarity	NPC6854
0.7842	Intermediate Similarity	NPC313737
0.7817	Intermediate Similarity	NPC210086
0.7786	Intermediate Similarity	NPC218530
0.7746	Intermediate Similarity	NPC254610
0.7746	Intermediate Similarity	NPC193528
0.774	Intermediate Similarity	NPC185838
0.774	Intermediate Similarity	NPC145304
0.774	Intermediate Similarity	NPC130926
0.774	Intermediate Similarity	NPC5462
0.7737	Intermediate Similarity	NPC251571
0.7727	Intermediate Similarity	NPC43275
0.7707	Intermediate Similarity	NPC66573
0.7704	Intermediate Similarity	NPC140359
0.7704	Intermediate Similarity	NPC13020
0.7698	Intermediate Similarity	NPC308885
0.7698	Intermediate Similarity	NPC255550
0.7687	Intermediate Similarity	NPC473934
0.7671	Intermediate Similarity	NPC294249
0.7661	Intermediate Similarity	NPC292792
0.7647	Intermediate Similarity	NPC105513
0.7635	Intermediate Similarity	NPC210437
0.7635	Intermediate Similarity	NPC106295
0.7635	Intermediate Similarity	NPC16107
0.7635	Intermediate Similarity	NPC476144
0.7635	Intermediate Similarity	NPC179825
0.7635	Intermediate Similarity	NPC51957
0.7635	Intermediate Similarity	NPC191376
0.7635	Intermediate Similarity	NPC476151
0.7635	Intermediate Similarity	NPC321505
0.7622	Intermediate Similarity	NPC204848
0.7622	Intermediate Similarity	NPC41473
0.7622	Intermediate Similarity	NPC14600
0.7622	Intermediate Similarity	NPC160607
0.7622	Intermediate Similarity	NPC312770
0.7616	Intermediate Similarity	NPC476580
0.7612	Intermediate Similarity	NPC183262
0.7609	Intermediate Similarity	NPC191302
0.7609	Intermediate Similarity	NPC99798
0.7609	Intermediate Similarity	NPC186898
0.7609	Intermediate Similarity	NPC157740
0.7606	Intermediate Similarity	NPC475828
0.7586	Intermediate Similarity	NPC323204
0.7584	Intermediate Similarity	NPC246587
0.7584	Intermediate Similarity	NPC476571
0.7584	Intermediate Similarity	NPC475959
0.7584	Intermediate Similarity	NPC428
0.7584	Intermediate Similarity	NPC147390
0.7584	Intermediate Similarity	NPC59907
0.7584	Intermediate Similarity	NPC37144
0.7584	Intermediate Similarity	NPC135538
0.7584	Intermediate Similarity	NPC24233
0.7584	Intermediate Similarity	NPC7467
0.7569	Intermediate Similarity	NPC299583
0.7559	Intermediate Similarity	NPC309982
0.7556	Intermediate Similarity	NPC211992
0.7554	Intermediate Similarity	NPC147247
0.7554	Intermediate Similarity	NPC246974
0.7537	Intermediate Similarity	NPC321133
0.7536	Intermediate Similarity	NPC251466
0.7536	Intermediate Similarity	NPC156944
0.7533	Intermediate Similarity	NPC103379
0.7533	Intermediate Similarity	NPC219162
0.7533	Intermediate Similarity	NPC211296
0.7533	Intermediate Similarity	NPC477565
0.7533	Intermediate Similarity	NPC92541
0.7518	Intermediate Similarity	NPC300955
0.7516	Intermediate Similarity	NPC93593
0.75	Intermediate Similarity	NPC310905
0.75	Intermediate Similarity	NPC18614
0.75	Intermediate Similarity	NPC470706
0.75	Intermediate Similarity	NPC12714
0.7484	Intermediate Similarity	NPC69360
0.7483	Intermediate Similarity	NPC88249
0.7483	Intermediate Similarity	NPC274026
0.7483	Intermediate Similarity	NPC220858
0.7483	Intermediate Similarity	NPC151895
0.7483	Intermediate Similarity	NPC192768
0.7483	Intermediate Similarity	NPC97221
0.7482	Intermediate Similarity	NPC291847
0.7482	Intermediate Similarity	NPC291449
0.7482	Intermediate Similarity	NPC41331
0.7468	Intermediate Similarity	NPC57512
0.7467	Intermediate Similarity	NPC130941
0.7464	Intermediate Similarity	NPC152186
0.7464	Intermediate Similarity	NPC207541
0.7464	Intermediate Similarity	NPC71105
0.7464	Intermediate Similarity	NPC170583
0.7464	Intermediate Similarity	NPC246133
0.7464	Intermediate Similarity	NPC182147
0.745	Intermediate Similarity	NPC290404
0.7448	Intermediate Similarity	NPC296898
0.7445	Intermediate Similarity	NPC217277
0.7434	Intermediate Similarity	NPC476579
0.7434	Intermediate Similarity	NPC81733
0.7434	Intermediate Similarity	NPC52475
0.7434	Intermediate Similarity	NPC85747
0.7434	Intermediate Similarity	NPC326316
0.7434	Intermediate Similarity	NPC8337
0.7434	Intermediate Similarity	NPC127402
0.7434	Intermediate Similarity	NPC119669
0.7431	Intermediate Similarity	NPC416184
0.7429	Intermediate Similarity	NPC469977
0.7417	Intermediate Similarity	NPC207824
0.7417	Intermediate Similarity	NPC60538
0.7415	Intermediate Similarity	NPC222039
0.7415	Intermediate Similarity	NPC100478
0.7407	Intermediate Similarity	NPC207721
0.7407	Intermediate Similarity	NPC17388
0.7407	Intermediate Similarity	NPC289330
0.7407	Intermediate Similarity	NPC160120
0.7407	Intermediate Similarity	NPC471308
0.7407	Intermediate Similarity	NPC53596
0.7405	Intermediate Similarity	NPC165106
0.74	Intermediate Similarity	NPC95075
0.74	Intermediate Similarity	NPC144863
0.74	Intermediate Similarity	NPC253883
0.74	Intermediate Similarity	NPC90844
0.7386	Intermediate Similarity	NPC233029
0.7386	Intermediate Similarity	NPC210148
0.7386	Intermediate Similarity	NPC133011
0.7386	Intermediate Similarity	NPC148898
0.7386	Intermediate Similarity	NPC82285
0.7372	Intermediate Similarity	NPC471314
0.7372	Intermediate Similarity	NPC471315
0.7368	Intermediate Similarity	NPC223125
0.7351	Intermediate Similarity	NPC470019
0.7348	Intermediate Similarity	NPC142599
0.7338	Intermediate Similarity	NPC475557
0.7338	Intermediate Similarity	NPC29477
0.7329	Intermediate Similarity	NPC231572
0.7324	Intermediate Similarity	NPC329595
0.7324	Intermediate Similarity	NPC326599
0.732	Intermediate Similarity	NPC277669
0.732	Intermediate Similarity	NPC76213
0.7308	Intermediate Similarity	NPC137685
0.7303	Intermediate Similarity	NPC44869
0.7297	Intermediate Similarity	NPC475698
0.7296	Intermediate Similarity	NPC89199
0.7296	Intermediate Similarity	NPC54125
0.7293	Intermediate Similarity	NPC475815
0.7293	Intermediate Similarity	NPC473264
0.7293	Intermediate Similarity	NPC47194
0.729	Intermediate Similarity	NPC107602
0.729	Intermediate Similarity	NPC39701
0.729	Intermediate Similarity	NPC216459
0.729	Intermediate Similarity	NPC127674
0.729	Intermediate Similarity	NPC138487
0.729	Intermediate Similarity	NPC5238
0.729	Intermediate Similarity	NPC41178
0.729	Intermediate Similarity	NPC172765
0.729	Intermediate Similarity	NPC80129
0.729	Intermediate Similarity	NPC78733
0.729	Intermediate Similarity	NPC184026
0.729	Intermediate Similarity	NPC278799
0.729	Intermediate Similarity	NPC276588
0.729	Intermediate Similarity	NPC2413
0.729	Intermediate Similarity	NPC193949
0.729	Intermediate Similarity	NPC187022
0.729	Intermediate Similarity	NPC54379
0.729	Intermediate Similarity	NPC204828
0.729	Intermediate Similarity	NPC249797

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 NPC476570 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	123
0.1-0.2	639
0.2-0.3	1167
0.3-0.4	2017
0.4-0.5	2792
0.5-0.6	1736
0.6-0.7	598
0.7-0.8	78
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8421	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.8357	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.8209	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.8088	Intermediate Similarity	NPD5718	Phase 2
0.8045	Intermediate Similarity	NPD2922	Phase 1
0.7958	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD6895	Approved
0.7929	Intermediate Similarity	NPD6896	Approved
0.7905	Intermediate Similarity	NPD4005	Discontinued
0.7899	Intermediate Similarity	NPD2674	Phase 3
0.7847	Intermediate Similarity	NPD6331	Phase 2
0.7836	Intermediate Similarity	NPD1669	Approved
0.7832	Intermediate Similarity	NPD1044	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD5241	Discontinued
0.777	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD5109	Approved
0.7698	Intermediate Similarity	NPD3145	Approved
0.7698	Intermediate Similarity	NPD5110	Phase 2
0.7698	Intermediate Similarity	NPD3144	Approved
0.7698	Intermediate Similarity	NPD5111	Phase 2
0.7692	Intermediate Similarity	NPD2161	Phase 2
0.7671	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD4584	Approved
0.7635	Intermediate Similarity	NPD4123	Phase 3
0.7551	Intermediate Similarity	NPD3692	Discontinued
0.7537	Intermediate Similarity	NPD2667	Approved
0.7537	Intermediate Similarity	NPD2668	Approved
0.7533	Intermediate Similarity	NPD3640	Phase 3
0.7533	Intermediate Similarity	NPD3639	Approved
0.7533	Intermediate Similarity	NPD3641	Approved
0.7533	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7124	Phase 2
0.7483	Intermediate Similarity	NPD2653	Approved
0.7467	Intermediate Similarity	NPD1349	Approved
0.7467	Intermediate Similarity	NPD1350	Approved
0.7467	Intermediate Similarity	NPD1351	Approved
0.7466	Intermediate Similarity	NPD7153	Discontinued
0.7452	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD4017	Approved
0.7431	Intermediate Similarity	NPD6111	Discontinued
0.7417	Intermediate Similarity	NPD6031	Approved
0.7417	Intermediate Similarity	NPD6030	Approved
0.7415	Intermediate Similarity	NPD4162	Approved
0.7415	Intermediate Similarity	NPD3060	Approved
0.741	Intermediate Similarity	NPD7905	Discontinued
0.7405	Intermediate Similarity	NPD5283	Phase 1
0.7397	Intermediate Similarity	NPD1375	Discontinued
0.7386	Intermediate Similarity	NPD6876	Approved
0.7386	Intermediate Similarity	NPD6875	Approved
0.7386	Intermediate Similarity	NPD4678	Approved
0.7386	Intermediate Similarity	NPD4675	Approved
0.7372	Intermediate Similarity	NPD2233	Approved
0.7372	Intermediate Similarity	NPD2230	Approved
0.7372	Intermediate Similarity	NPD2232	Approved
0.7351	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD3655	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD4772	Phase 2
0.7338	Intermediate Similarity	NPD4773	Phase 2
0.7338	Intermediate Similarity	NPD7110	Phase 1
0.7338	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD1039	Discontinued
0.7303	Intermediate Similarity	NPD2122	Discontinued
0.729	Intermediate Similarity	NPD7298	Approved
0.7285	Intermediate Similarity	NPD1771	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD1024	Discontinued
0.7252	Intermediate Similarity	NPD228	Approved
0.7244	Intermediate Similarity	NPD5772	Approved
0.7244	Intermediate Similarity	NPD5773	Approved
0.7234	Intermediate Similarity	NPD1712	Approved
0.723	Intermediate Similarity	NPD2808	Discontinued
0.723	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD2238	Phase 2
0.7222	Intermediate Similarity	NPD3110	Approved
0.7222	Intermediate Similarity	NPD3109	Approved
0.7203	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD2219	Phase 1
0.72	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD2563	Approved
0.7197	Intermediate Similarity	NPD2560	Approved
0.7194	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD4236	Phase 3
0.7181	Intermediate Similarity	NPD4237	Approved
0.7171	Intermediate Similarity	NPD1424	Approved
0.7171	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD4739	Approved
0.7164	Intermediate Similarity	NPD709	Approved
0.716	Intermediate Similarity	NPD7291	Discontinued
0.7153	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4210	Discontinued
0.7143	Intermediate Similarity	NPD2883	Discontinued
0.7126	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD52	Approved
0.7124	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD7526	Approved
0.7123	Intermediate Similarity	NPD2157	Approved
0.7123	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD2492	Phase 1
0.7107	Intermediate Similarity	NPD7833	Phase 2
0.7107	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD7831	Phase 2
0.7103	Intermediate Similarity	NPD1558	Phase 1
0.7097	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD3445	Approved
0.708	Intermediate Similarity	NPD3444	Approved
0.708	Intermediate Similarity	NPD3443	Approved
0.707	Intermediate Similarity	NPD5720	Discontinued
0.707	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD5177	Phase 3
0.705	Intermediate Similarity	NPD3705	Approved
0.7034	Intermediate Similarity	NPD4474	Approved
0.7034	Intermediate Similarity	NPD4475	Approved
0.7012	Intermediate Similarity	NPD3489	Phase 3
0.7006	Intermediate Similarity	NPD5089	Approved
0.7006	Intermediate Similarity	NPD5090	Approved
0.7	Intermediate Similarity	NPD4055	Discovery
0.7	Intermediate Similarity	NPD5604	Discontinued
0.6994	Remote Similarity	NPD4083	Discontinued
0.6993	Remote Similarity	NPD3124	Discontinued
0.6986	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD5977	Approved
0.6981	Remote Similarity	NPD5978	Approved
0.6975	Remote Similarity	NPD7802	Discontinued
0.6975	Remote Similarity	NPD6107	Approved
0.6972	Remote Similarity	NPD4098	Discontinued
0.6963	Remote Similarity	NPD593	Approved
0.6963	Remote Similarity	NPD595	Approved
0.695	Remote Similarity	NPD1420	Approved
0.695	Remote Similarity	NPD1421	Approved
0.6936	Remote Similarity	NPD3923	Approved
0.6936	Remote Similarity	NPD3922	Approved
0.6936	Remote Similarity	NPD3921	Approved
0.6936	Remote Similarity	NPD3924	Approved
0.6933	Remote Similarity	NPD3051	Approved
0.6933	Remote Similarity	NPD4166	Phase 2
0.6933	Remote Similarity	NPD4010	Discontinued
0.6933	Remote Similarity	NPD6071	Discontinued
0.6923	Remote Similarity	NPD3686	Approved
0.6923	Remote Similarity	NPD3687	Approved
0.6918	Remote Similarity	NPD2245	Discovery
0.6918	Remote Similarity	NPD3531	Approved
0.6918	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD3532	Approved
0.6918	Remote Similarity	NPD3530	Approved
0.6918	Remote Similarity	NPD4585	Approved
0.6913	Remote Similarity	NPD4108	Discontinued
0.6913	Remote Similarity	NPD1753	Discontinued
0.6909	Remote Similarity	NPD5966	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD6873	Phase 2
0.689	Remote Similarity	NPD2969	Approved
0.689	Remote Similarity	NPD2970	Approved
0.6886	Remote Similarity	NPD3920	Phase 2
0.6884	Remote Similarity	NPD2486	Discontinued
0.6875	Remote Similarity	NPD4993	Discontinued
0.6875	Remote Similarity	NPD2358	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7034	Discontinued
0.6875	Remote Similarity	NPD2040	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD3596	Phase 2
0.6859	Remote Similarity	NPD3033	Phase 2
0.6853	Remote Similarity	NPD3055	Approved
0.6853	Remote Similarity	NPD3053	Approved
0.6849	Remote Similarity	NPD1336	Approved
0.6849	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD27	Approved
0.6848	Remote Similarity	NPD4481	Phase 3
0.6848	Remote Similarity	NPD2489	Approved
0.6848	Remote Similarity	NPD2898	Approved
0.6842	Remote Similarity	NPD1792	Phase 2
0.6835	Remote Similarity	NPD4093	Discontinued
0.6832	Remote Similarity	NPD6788	Approved
0.6821	Remote Similarity	NPD3656	Approved
0.6821	Remote Similarity	NPD3408	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD821	Approved
0.6815	Remote Similarity	NPD9377	Approved
0.6815	Remote Similarity	NPD9379	Approved
0.6813	Remote Similarity	NPD2978	Approved
0.6813	Remote Similarity	NPD2977	Approved
0.6812	Remote Similarity	NPD5536	Phase 2
0.6807	Remote Similarity	NPD1923	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD6584	Phase 3
0.6806	Remote Similarity	NPD9621	Approved
0.6806	Remote Similarity	NPD9620	Approved
0.6806	Remote Similarity	NPD9619	Approved
0.6803	Remote Similarity	NPD840	Approved
0.6803	Remote Similarity	NPD839	Approved
0.68	Remote Similarity	NPD6380	Phase 1
0.6797	Remote Similarity	NPD5754	Discontinued
0.6792	Remote Similarity	NPD6386	Approved
0.6792	Remote Similarity	NPD6385	Approved
0.679	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD6688	Approved
0.6788	Remote Similarity	NPD6687	Approved
0.6783	Remote Similarity	NPD5311	Approved
0.6783	Remote Similarity	NPD9634	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