NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	355.18
Volume:	367.885
LogP:	0.594
LogD:	1.981
LogS:	0.078
# Rotatable Bonds:	3
TPSA:	50.75
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.795
Synthetic Accessibility Score:	3.789
Fsp3:	0.429
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:	-5.409
MDCK Permeability:	2.5612673198338598e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.845
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.194
Plasma Protein Binding (PPB):	54.61500549316406%
Volume Distribution (VD):	2.328
Pgp-substrate:	33.74459457397461%

ADMET: Metabolism

CYP1A2-inhibitor:	0.061
CYP1A2-substrate:	0.977
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.808
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.654
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.923
CYP3A4-inhibitor:	0.058
CYP3A4-substrate:	0.877

ADMET: Excretion

Clearance (CL):	3.599
Half-life (T1/2):	0.77

ADMET: Toxicity

hERG Blockers:	0.071
Human Hepatotoxicity (H-HT):	0.106
Drug-inuced Liver Injury (DILI):	0.023
AMES Toxicity:	0.263
Rat Oral Acute Toxicity:	0.958
Maximum Recommended Daily Dose:	0.969
Skin Sensitization:	0.043
Carcinogencity:	0.041
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.829

Download Data

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

Natural Product: NPC476572

Natural Product ID:	NPC476572
*Common Name:**	(6aS)-2,10,11-trimethoxy-6,6-dimethyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-6-ium-1-ol;2,2,2-trifluoroacetate
IUPAC Name:	(6aS)-2,10,11-trimethoxy-6,6-dimethyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-6-ium-1-ol;2,2,2-trifluoroacetate
Synonyms:
Standard InCHIKey:	OTTPPKAGAOPYOF-UQKRIMTDSA-N
Standard InCHI:	InChI=1S/C21H25NO4.C2HF3O2/c1-22(2)9-8-13-11-16(25-4)20(23)19-17(13)14(22)10-12-6-7-15(24-3)21(26-5)18(12)19;3-2(4,5)1(6)7/h6-7,11,14H,8-10H2,1-5H3;(H,6,7)/t14-;/m0./s1
SMILES:	C[N+]1(CCC2=CC(=C(C3=C2[C@@H]1CC4=C3C(=C(C=C4)OC)OC)O)OC)C.C(=O)(C(F)(F)F)[O-]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	52949573
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0000381] Aporphines

*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	>	140000	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 NPC476572 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	265
0.1-0.2	1418
0.2-0.3	6006
0.3-0.4	12000
0.4-0.5	5237
0.5-0.6	12676
0.6-0.7	4257
0.7-0.8	577
0.8-0.85	171
0.85-0.9	68
0.9-0.95	20
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9864	High Similarity	NPC99659
0.9864	High Similarity	NPC325871
0.966	High Similarity	NPC81733
0.966	High Similarity	NPC326316
0.9545	High Similarity	NPC158376
0.9545	High Similarity	NPC474931
0.9545	High Similarity	NPC306555
0.9545	High Similarity	NPC81218
0.9545	High Similarity	NPC145832
0.9545	High Similarity	NPC247389
0.9545	High Similarity	NPC117188
0.9545	High Similarity	NPC205421
0.9545	High Similarity	NPC12053
0.9481	High Similarity	NPC24264
0.9481	High Similarity	NPC476432
0.9481	High Similarity	NPC219341
0.9416	High Similarity	NPC78222
0.9416	High Similarity	NPC212794
0.9416	High Similarity	NPC96603
0.9416	High Similarity	NPC302527
0.9416	High Similarity	NPC477563
0.9416	High Similarity	NPC13504
0.9416	High Similarity	NPC136508
0.9416	High Similarity	NPC225774
0.9416	High Similarity	NPC306843
0.9416	High Similarity	NPC253043
0.9416	High Similarity	NPC167546
0.9416	High Similarity	NPC196447
0.9416	High Similarity	NPC16805
0.9351	High Similarity	NPC1229
0.9351	High Similarity	NPC324144
0.9295	High Similarity	NPC210918
0.9276	High Similarity	NPC203784
0.9276	High Similarity	NPC126519
0.9276	High Similarity	NPC170503
0.9221	High Similarity	NPC160298
0.9221	High Similarity	NPC306902
0.9221	High Similarity	NPC27410
0.9221	High Similarity	NPC477559
0.9221	High Similarity	NPC266753
0.9221	High Similarity	NPC232924
0.9221	High Similarity	NPC166014
0.9211	High Similarity	NPC244112
0.9182	High Similarity	NPC66341
0.9182	High Similarity	NPC477020
0.9182	High Similarity	NPC192135
0.9172	High Similarity	NPC204947
0.913	High Similarity	NPC320223
0.913	High Similarity	NPC114364
0.9119	High Similarity	NPC149090
0.9119	High Similarity	NPC239775
0.9119	High Similarity	NPC19520
0.9057	High Similarity	NPC69712
0.9057	High Similarity	NPC26240
0.9057	High Similarity	NPC118274
0.9057	High Similarity	NPC477562
0.9057	High Similarity	NPC168753
0.9057	High Similarity	NPC6152
0.9006	High Similarity	NPC128560
0.9006	High Similarity	NPC199465
0.9006	High Similarity	NPC229166
0.9	High Similarity	NPC106295
0.9	High Similarity	NPC51957
0.9	High Similarity	NPC16107
0.9	High Similarity	NPC210437
0.9	High Similarity	NPC476144
0.898	High Similarity	NPC474915
0.898	High Similarity	NPC470925
0.898	High Similarity	NPC213206
0.898	High Similarity	NPC328750
0.898	High Similarity	NPC188163
0.8963	High Similarity	NPC248642
0.8957	High Similarity	NPC220961
0.894	High Similarity	NPC7467
0.8931	High Similarity	NPC298979
0.8917	High Similarity	NPC60186
0.8912	High Similarity	NPC314682
0.8909	High Similarity	NPC156576
0.8902	High Similarity	NPC32413
0.8902	High Similarity	NPC474506
0.8882	High Similarity	NPC92541
0.8882	High Similarity	NPC219162
0.8875	High Similarity	NPC241055
0.8868	High Similarity	NPC86144
0.8868	High Similarity	NPC476573
0.8868	High Similarity	NPC304659
0.8868	High Similarity	NPC35627
0.8868	High Similarity	NPC81247
0.8859	High Similarity	NPC128019
0.8859	High Similarity	NPC476567
0.8859	High Similarity	NPC136860
0.8841	High Similarity	NPC470879
0.8841	High Similarity	NPC126284
0.8841	High Similarity	NPC474507
0.8841	High Similarity	NPC258695
0.8831	High Similarity	NPC470924
0.8816	High Similarity	NPC130941
0.8805	High Similarity	NPC168409
0.8795	High Similarity	NPC135772
0.8795	High Similarity	NPC302275
0.878	High Similarity	NPC190461
0.878	High Similarity	NPC23219
0.875	High Similarity	NPC95075
0.875	High Similarity	NPC253883
0.875	High Similarity	NPC144863
0.875	High Similarity	NPC90844
0.8742	High Similarity	NPC189470
0.8735	High Similarity	NPC116284
0.8727	High Similarity	NPC267408
0.872	High Similarity	NPC476577
0.872	High Similarity	NPC112575
0.872	High Similarity	NPC173416
0.872	High Similarity	NPC148709
0.8718	High Similarity	NPC123323
0.8696	High Similarity	NPC150879
0.869	High Similarity	NPC47077
0.869	High Similarity	NPC14507
0.8675	High Similarity	NPC312918
0.8675	High Similarity	NPC477561
0.8675	High Similarity	NPC155442
0.8675	High Similarity	NPC476574
0.8667	High Similarity	NPC118633
0.8667	High Similarity	NPC148693
0.8667	High Similarity	NPC294790
0.8662	High Similarity	NPC180756
0.8662	High Similarity	NPC323443
0.8659	High Similarity	NPC477558
0.8639	High Similarity	NPC237579
0.8627	High Similarity	NPC476151
0.8618	High Similarity	NPC185838
0.8599	High Similarity	NPC5238
0.8599	High Similarity	NPC204828
0.8599	High Similarity	NPC110416
0.8599	High Similarity	NPC469817
0.8599	High Similarity	NPC276588
0.8599	High Similarity	NPC249797
0.8599	High Similarity	NPC138487
0.8599	High Similarity	NPC127674
0.8599	High Similarity	NPC54379
0.8599	High Similarity	NPC207757
0.8599	High Similarity	NPC295691
0.8599	High Similarity	NPC39701
0.8599	High Similarity	NPC184026
0.8599	High Similarity	NPC193949
0.8599	High Similarity	NPC189266
0.8599	High Similarity	NPC172765
0.8599	High Similarity	NPC2413
0.8599	High Similarity	NPC278799
0.8599	High Similarity	NPC41178
0.8599	High Similarity	NPC216459
0.8598	High Similarity	NPC285941
0.858	High Similarity	NPC57036
0.858	High Similarity	NPC214116
0.8571	High Similarity	NPC475959
0.8571	High Similarity	NPC428
0.8571	High Similarity	NPC476571
0.8571	High Similarity	NPC24233
0.8571	High Similarity	NPC147390
0.8571	High Similarity	NPC169743
0.8571	High Similarity	NPC135538
0.8571	High Similarity	NPC246587
0.8562	High Similarity	NPC79402
0.8562	High Similarity	NPC80759
0.8544	High Similarity	NPC146288
0.8538	High Similarity	NPC475754
0.8519	High Similarity	NPC68328
0.8519	High Similarity	NPC13916
0.8519	High Similarity	NPC264850
0.8516	High Similarity	NPC477565
0.8516	High Similarity	NPC103379
0.8509	High Similarity	NPC233650
0.8506	High Similarity	NPC321505
0.8506	High Similarity	NPC179825
0.8506	High Similarity	NPC191376
0.85	High Similarity	NPC230956
0.85	High Similarity	NPC119649
0.85	High Similarity	NPC235143
0.85	High Similarity	NPC271388
0.85	High Similarity	NPC205255
0.8494	Intermediate Similarity	NPC241704
0.8488	Intermediate Similarity	NPC478093
0.848	Intermediate Similarity	NPC82763
0.8476	Intermediate Similarity	NPC152212
0.8471	Intermediate Similarity	NPC26601
0.8462	Intermediate Similarity	NPC151895
0.8462	Intermediate Similarity	NPC88249
0.8462	Intermediate Similarity	NPC97221
0.8462	Intermediate Similarity	NPC220858
0.8462	Intermediate Similarity	NPC192768
0.8457	Intermediate Similarity	NPC134858
0.8457	Intermediate Similarity	NPC24465
0.8439	Intermediate Similarity	NPC478091
0.8439	Intermediate Similarity	NPC473589
0.8439	Intermediate Similarity	NPC478092
0.8439	Intermediate Similarity	NPC30182
0.8438	Intermediate Similarity	NPC221864
0.8438	Intermediate Similarity	NPC7393
0.8428	Intermediate Similarity	NPC247639
0.8428	Intermediate Similarity	NPC25084
0.8428	Intermediate Similarity	NPC234392

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 NPC476572 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	175
0.1-0.2	726
0.2-0.3	1023
0.3-0.4	1970
0.4-0.5	2613
0.5-0.6	1841
0.6-0.7	645
0.7-0.8	149
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9	High Similarity	NPD4584	Approved
0.898	High Similarity	NPD4664	Clinical (unspecified phase)
0.8519	High Similarity	NPD3051	Approved
0.8442	Intermediate Similarity	NPD2421	Approved
0.8442	Intermediate Similarity	NPD2420	Approved
0.8424	Intermediate Similarity	NPD8099	Discontinued
0.8424	Intermediate Similarity	NPD8252	Approved
0.8424	Intermediate Similarity	NPD8251	Approved
0.8415	Intermediate Similarity	NPD4481	Phase 3
0.8373	Intermediate Similarity	NPD8156	Discontinued
0.8354	Intermediate Similarity	NPD2970	Approved
0.8354	Intermediate Similarity	NPD2969	Approved
0.8323	Intermediate Similarity	NPD6788	Approved
0.8291	Intermediate Similarity	NPD4017	Approved
0.825	Intermediate Similarity	NPD7298	Approved
0.8199	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD2489	Approved
0.8193	Intermediate Similarity	NPD27	Approved
0.8171	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.815	Intermediate Similarity	NPD7906	Approved
0.8133	Intermediate Similarity	NPD3110	Approved
0.8133	Intermediate Similarity	NPD3109	Approved
0.8081	Intermediate Similarity	NPD8053	Approved
0.8081	Intermediate Similarity	NPD8054	Approved
0.8077	Intermediate Similarity	NPD5241	Discontinued
0.805	Intermediate Similarity	NPD3640	Phase 3
0.805	Intermediate Similarity	NPD3641	Approved
0.805	Intermediate Similarity	NPD6030	Approved
0.805	Intermediate Similarity	NPD6031	Approved
0.805	Intermediate Similarity	NPD3639	Approved
0.8039	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD2971	Approved
0.8023	Intermediate Similarity	NPD7312	Approved
0.8023	Intermediate Similarity	NPD4578	Approved
0.8023	Intermediate Similarity	NPD7313	Approved
0.8023	Intermediate Similarity	NPD4577	Approved
0.8023	Intermediate Similarity	NPD7311	Approved
0.8023	Intermediate Similarity	NPD7310	Approved
0.8023	Intermediate Similarity	NPD2968	Approved
0.7989	Intermediate Similarity	NPD4663	Approved
0.7977	Intermediate Similarity	NPD7309	Approved
0.7881	Intermediate Similarity	NPD5718	Phase 2
0.787	Intermediate Similarity	NPD2898	Approved
0.7853	Intermediate Similarity	NPD4773	Phase 2
0.7853	Intermediate Similarity	NPD4772	Phase 2
0.7848	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD7831	Phase 2
0.7831	Intermediate Similarity	NPD7833	Phase 2
0.7831	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD7802	Discontinued
0.7751	Intermediate Similarity	NPD4010	Discontinued
0.7751	Intermediate Similarity	NPD6071	Discontinued
0.7735	Intermediate Similarity	NPD2974	Approved
0.7735	Intermediate Similarity	NPD2975	Approved
0.7735	Intermediate Similarity	NPD2973	Approved
0.7725	Intermediate Similarity	NPD4055	Discovery
0.7712	Intermediate Similarity	NPD4474	Approved
0.7712	Intermediate Similarity	NPD4475	Approved
0.7711	Intermediate Similarity	NPD2563	Approved
0.7711	Intermediate Similarity	NPD2560	Approved
0.7702	Intermediate Similarity	NPD1424	Approved
0.7688	Intermediate Similarity	NPD3845	Phase 1
0.7688	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD2488	Approved
0.7654	Intermediate Similarity	NPD2490	Approved
0.764	Intermediate Similarity	NPD3124	Discontinued
0.7632	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD6896	Approved
0.7628	Intermediate Similarity	NPD6895	Approved
0.7616	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD4580	Approved
0.7588	Intermediate Similarity	NPD6107	Approved
0.7578	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD7124	Phase 2
0.7568	Intermediate Similarity	NPD3450	Approved
0.7568	Intermediate Similarity	NPD2493	Approved
0.7568	Intermediate Similarity	NPD2494	Approved
0.7568	Intermediate Similarity	NPD3452	Approved
0.7562	Intermediate Similarity	NPD5754	Discontinued
0.7554	Intermediate Similarity	NPD8095	Phase 1
0.7546	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD7598	Phase 2
0.7514	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4727	Phase 1
0.75	Intermediate Similarity	NPD5177	Phase 3
0.75	Intermediate Similarity	NPD4420	Approved
0.75	Intermediate Similarity	NPD5976	Discontinued
0.7485	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD6748	Discontinued
0.7447	Intermediate Similarity	NPD4583	Approved
0.7447	Intermediate Similarity	NPD4582	Approved
0.7443	Intermediate Similarity	NPD6297	Approved
0.7442	Intermediate Similarity	NPD4166	Phase 2
0.7427	Intermediate Similarity	NPD5677	Discontinued
0.7419	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD6687	Approved
0.7399	Intermediate Similarity	NPD6688	Approved
0.7396	Intermediate Similarity	NPD5978	Approved
0.7396	Intermediate Similarity	NPD5977	Approved
0.7394	Intermediate Similarity	NPD4004	Approved
0.7394	Intermediate Similarity	NPD4002	Approved
0.7368	Intermediate Similarity	NPD7400	Phase 3
0.7358	Intermediate Similarity	NPD1753	Discontinued
0.7355	Intermediate Similarity	NPD5156	Approved
0.7355	Intermediate Similarity	NPD5155	Approved
0.7346	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD5005	Approved
0.734	Intermediate Similarity	NPD5006	Approved
0.7333	Intermediate Similarity	NPD6090	Discontinued
0.7333	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD5312	Approved
0.733	Intermediate Similarity	NPD6042	Phase 2
0.733	Intermediate Similarity	NPD5313	Approved
0.733	Intermediate Similarity	NPD42	Phase 2
0.7326	Intermediate Similarity	NPD4107	Approved
0.7321	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD7110	Phase 1
0.7305	Intermediate Similarity	NPD4005	Discontinued
0.729	Intermediate Similarity	NPD3595	Approved
0.729	Intermediate Similarity	NPD2605	Approved
0.729	Intermediate Similarity	NPD3594	Approved
0.729	Intermediate Similarity	NPD2606	Approved
0.7284	Intermediate Similarity	NPD4236	Phase 3
0.7284	Intermediate Similarity	NPD4237	Approved
0.7284	Intermediate Similarity	NPD3060	Approved
0.7278	Intermediate Similarity	NPD6853	Approved
0.7278	Intermediate Similarity	NPD6851	Approved
0.7273	Intermediate Similarity	NPD4123	Phase 3
0.7267	Intermediate Similarity	NPD4726	Approved
0.7267	Intermediate Similarity	NPD4725	Approved
0.7267	Intermediate Similarity	NPD4721	Approved
0.7255	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD7291	Discontinued
0.7245	Intermediate Similarity	NPD7047	Phase 3
0.7239	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD4585	Approved
0.7233	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD3635	Approved
0.7226	Intermediate Similarity	NPD3636	Approved
0.7226	Intermediate Similarity	NPD3637	Approved
0.7225	Intermediate Similarity	NPD6037	Discontinued
0.7222	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6386	Approved
0.7219	Intermediate Similarity	NPD6385	Approved
0.7205	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6997	Phase 2
0.7196	Intermediate Similarity	NPD4482	Phase 3
0.7195	Intermediate Similarity	NPD5160	Discontinued
0.719	Intermediate Similarity	NPD1669	Approved
0.7186	Intermediate Similarity	NPD1914	Approved
0.7186	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD3057	Approved
0.7152	Intermediate Similarity	NPD6666	Approved
0.7152	Intermediate Similarity	NPD6667	Approved
0.7143	Intermediate Similarity	NPD6747	Phase 1
0.7135	Intermediate Similarity	NPD2977	Approved
0.7135	Intermediate Similarity	NPD2978	Approved
0.7135	Intermediate Similarity	NPD5772	Approved
0.7135	Intermediate Similarity	NPD5773	Approved
0.7126	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD5966	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD5604	Discontinued
0.7107	Intermediate Similarity	NPD2238	Phase 2
0.7101	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4098	Discontinued
0.7095	Intermediate Similarity	NPD3920	Phase 2
0.7091	Intermediate Similarity	NPD3692	Discontinued
0.7089	Intermediate Similarity	NPD7294	Phase 1
0.7088	Intermediate Similarity	NPD6618	Phase 2
0.7083	Intermediate Similarity	NPD2122	Discontinued
0.7083	Intermediate Similarity	NPD4040	Phase 1
0.7081	Intermediate Similarity	NPD2200	Suspended
0.7081	Intermediate Similarity	NPD6111	Discontinued
0.7076	Intermediate Similarity	NPD5720	Discontinued
0.7074	Intermediate Similarity	NPD7034	Discontinued
0.7073	Intermediate Similarity	NPD4162	Approved
0.7072	Intermediate Similarity	NPD7549	Discontinued
0.7069	Intermediate Similarity	NPD5709	Phase 3
0.7068	Intermediate Similarity	NPD2972	Approved
0.7068	Intermediate Similarity	NPD3533	Approved
0.7059	Intermediate Similarity	NPD4675	Approved
0.7059	Intermediate Similarity	NPD6876	Approved
0.7059	Intermediate Similarity	NPD4678	Approved
0.7059	Intermediate Similarity	NPD6875	Approved
0.7055	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD6612	Phase 2
0.7051	Intermediate Similarity	NPD7905	Discontinued
0.7044	Intermediate Similarity	NPD2674	Phase 3
0.7044	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD3921	Approved
0.7043	Intermediate Similarity	NPD3922	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