NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	341.13
Volume:	333.527
LogP:	1.76
LogD:	2.313
LogS:	-1.902
# Rotatable Bonds:	2
TPSA:	69.18
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.875
Synthetic Accessibility Score:	3.376
Fsp3:	0.368
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.077
MDCK Permeability:	1.8176529920310713e-05
Pgp-inhibitor:	0.033
Pgp-substrate:	0.615
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.786
Plasma Protein Binding (PPB):	91.89566040039062%
Volume Distribution (VD):	1.566
Pgp-substrate:	11.484986305236816%

ADMET: Metabolism

CYP1A2-inhibitor:	0.564
CYP1A2-substrate:	0.921
CYP2C19-inhibitor:	0.186
CYP2C19-substrate:	0.814
CYP2C9-inhibitor:	0.013
CYP2C9-substrate:	0.68
CYP2D6-inhibitor:	0.369
CYP2D6-substrate:	0.893
CYP3A4-inhibitor:	0.389
CYP3A4-substrate:	0.827

ADMET: Excretion

Clearance (CL):	12.051
Half-life (T1/2):	0.274

ADMET: Toxicity

hERG Blockers:	0.215
Human Hepatotoxicity (H-HT):	0.251
Drug-inuced Liver Injury (DILI):	0.319
AMES Toxicity:	0.153
Rat Oral Acute Toxicity:	0.711
Maximum Recommended Daily Dose:	0.974
Skin Sensitization:	0.549
Carcinogencity:	0.292
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.946

Download Data

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

Natural Product: NPC476576

Natural Product ID:	NPC476576
*Common Name:**	(12S)-18,19-dimethoxy-5,7-dioxa-13-azapentacyclo[10.7.1.02,10.04,8.016,20]icosa-1(19),2,4(8),9,16(20),17-hexaen-17-ol;2,2,2-trifluoroacetic acid
IUPAC Name:	(12S)-18,19-dimethoxy-5,7-dioxa-13-azapentacyclo[10.7.1.02,10.04,8.016,20]icosa-1(19),2,4(8),9,16(20),17-hexaen-17-ol;2,2,2-trifluoroacetic acid
Synonyms:
Standard InCHIKey:	UDWPFWOECJFSHB-YDALLXLXSA-N
Standard InCHI:	InChI=1S/C19H19NO5.C2HF3O2/c1-22-18-16-11-7-14-13(24-8-25-14)6-9(11)5-12-15(16)10(3-4-20-12)17(21)19(18)23-2;3-2(4,5)1(6)7/h6-7,12,20-21H,3-5,8H2,1-2H3;(H,6,7)/t12-;/m0./s1
SMILES:	COC1=C2C3=CC4=C(C=C3C[C@H]5C2=C(CCN5)C(=C1OC)O)OCO4.C(=O)(C(F)(F)F)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1270450
PubChem CID:	54581978
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	=	76900	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 NPC476576 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	298
0.1-0.2	1585
0.2-0.3	7440
0.3-0.4	10937
0.4-0.5	6110
0.5-0.6	10978
0.6-0.7	4522
0.7-0.8	664
0.8-0.85	112
0.85-0.9	32
0.9-0.95	16
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC186546
0.9822	High Similarity	NPC57036
0.9702	High Similarity	NPC476574
0.9702	High Similarity	NPC312918
0.9702	High Similarity	NPC155442
0.9702	High Similarity	NPC477561
0.9588	High Similarity	NPC135772
0.9527	High Similarity	NPC258695
0.9527	High Similarity	NPC470879
0.9527	High Similarity	NPC474507
0.9471	High Similarity	NPC32413
0.9471	High Similarity	NPC474506
0.9467	High Similarity	NPC23219
0.9408	High Similarity	NPC173416
0.9408	High Similarity	NPC112575
0.9408	High Similarity	NPC476577
0.9408	High Similarity	NPC148709
0.9371	High Similarity	NPC117717
0.9368	High Similarity	NPC82763
0.9349	High Similarity	NPC477558
0.9349	High Similarity	NPC128560
0.9349	High Similarity	NPC199465
0.9349	High Similarity	NPC229166
0.9286	High Similarity	NPC26240
0.9286	High Similarity	NPC6152
0.9286	High Similarity	NPC69712
0.9286	High Similarity	NPC477562
0.924	High Similarity	NPC114364
0.924	High Similarity	NPC320223
0.9231	High Similarity	NPC239775
0.9231	High Similarity	NPC149090
0.9231	High Similarity	NPC19520
0.9176	High Similarity	NPC192135
0.9176	High Similarity	NPC66341
0.9176	High Similarity	NPC477020
0.9172	High Similarity	NPC152212
0.9167	High Similarity	NPC204947
0.908	High Similarity	NPC116284
0.9059	High Similarity	NPC168753
0.9059	High Similarity	NPC118274
0.9034	High Similarity	NPC214116
0.8994	High Similarity	NPC81247
0.8994	High Similarity	NPC35627
0.8994	High Similarity	NPC86144
0.8994	High Similarity	NPC476573
0.8994	High Similarity	NPC304659
0.8971	High Similarity	NPC476575
0.8941	High Similarity	NPC298979
0.8935	High Similarity	NPC13504
0.8935	High Similarity	NPC78222
0.8935	High Similarity	NPC302527
0.8935	High Similarity	NPC16805
0.8935	High Similarity	NPC253043
0.8935	High Similarity	NPC167546
0.8935	High Similarity	NPC136508
0.8935	High Similarity	NPC477563
0.8935	High Similarity	NPC196447
0.8935	High Similarity	NPC96603
0.8935	High Similarity	NPC212794
0.8935	High Similarity	NPC306843
0.8883	High Similarity	NPC475754
0.8882	High Similarity	NPC476432
0.8882	High Similarity	NPC24264
0.8876	High Similarity	NPC324144
0.8876	High Similarity	NPC189470
0.8857	High Similarity	NPC267408
0.883	High Similarity	NPC145832
0.883	High Similarity	NPC210918
0.883	High Similarity	NPC306555
0.883	High Similarity	NPC81218
0.883	High Similarity	NPC474931
0.883	High Similarity	NPC158376
0.883	High Similarity	NPC117188
0.883	High Similarity	NPC247389
0.883	High Similarity	NPC205421
0.883	High Similarity	NPC12053
0.8824	High Similarity	NPC225774
0.8777	High Similarity	NPC46990
0.8772	High Similarity	NPC219341
0.8757	High Similarity	NPC248642
0.8757	High Similarity	NPC275132
0.875	High Similarity	NPC126284
0.8708	High Similarity	NPC156576
0.8663	High Similarity	NPC56887
0.8663	High Similarity	NPC223077
0.8663	High Similarity	NPC193853
0.8655	High Similarity	NPC1229
0.8647	High Similarity	NPC27410
0.8647	High Similarity	NPC166014
0.8647	High Similarity	NPC477559
0.8647	High Similarity	NPC160298
0.8647	High Similarity	NPC266753
0.8647	High Similarity	NPC306902
0.8647	High Similarity	NPC232924
0.8605	High Similarity	NPC209377
0.8605	High Similarity	NPC24465
0.858	High Similarity	NPC126519
0.858	High Similarity	NPC203784
0.858	High Similarity	NPC170503
0.858	High Similarity	NPC329969
0.8555	High Similarity	NPC13916
0.8555	High Similarity	NPC264850
0.8525	High Similarity	NPC24260
0.8525	High Similarity	NPC478093
0.8521	High Similarity	NPC325871
0.8521	High Similarity	NPC99659
0.8497	Intermediate Similarity	NPC276944
0.8497	Intermediate Similarity	NPC238530
0.8497	Intermediate Similarity	NPC232514
0.8483	Intermediate Similarity	NPC148693
0.8483	Intermediate Similarity	NPC118633
0.8483	Intermediate Similarity	NPC294790
0.848	Intermediate Similarity	NPC111485
0.8478	Intermediate Similarity	NPC478091
0.8478	Intermediate Similarity	NPC473589
0.8478	Intermediate Similarity	NPC30182
0.8478	Intermediate Similarity	NPC478092
0.8421	Intermediate Similarity	NPC476572
0.8415	Intermediate Similarity	NPC175890
0.8415	Intermediate Similarity	NPC274661
0.8415	Intermediate Similarity	NPC82457
0.8415	Intermediate Similarity	NPC11296
0.8415	Intermediate Similarity	NPC48490
0.8415	Intermediate Similarity	NPC281581
0.8382	Intermediate Similarity	NPC60186
0.8378	Intermediate Similarity	NPC256124
0.8372	Intermediate Similarity	NPC7393
0.837	Intermediate Similarity	NPC60295
0.837	Intermediate Similarity	NPC191132
0.8362	Intermediate Similarity	NPC231371
0.8353	Intermediate Similarity	NPC2295
0.8353	Intermediate Similarity	NPC477564
0.8352	Intermediate Similarity	NPC83198
0.8352	Intermediate Similarity	NPC204908
0.8352	Intermediate Similarity	NPC241055
0.8343	Intermediate Similarity	NPC76213
0.8343	Intermediate Similarity	NPC195392
0.8343	Intermediate Similarity	NPC277669
0.8324	Intermediate Similarity	NPC230956
0.8324	Intermediate Similarity	NPC271388
0.8324	Intermediate Similarity	NPC235143
0.8324	Intermediate Similarity	NPC119649
0.8324	Intermediate Similarity	NPC205255
0.8314	Intermediate Similarity	NPC79328
0.8286	Intermediate Similarity	NPC168409
0.8276	Intermediate Similarity	NPC80759
0.8276	Intermediate Similarity	NPC79402
0.8268	Intermediate Similarity	NPC187678
0.8266	Intermediate Similarity	NPC221864
0.8261	Intermediate Similarity	NPC22115
0.8261	Intermediate Similarity	NPC275680
0.8256	Intermediate Similarity	NPC186063
0.8254	Intermediate Similarity	NPC475654
0.8235	Intermediate Similarity	NPC326316
0.8235	Intermediate Similarity	NPC81733
0.8225	Intermediate Similarity	NPC60538
0.8225	Intermediate Similarity	NPC207824
0.8212	Intermediate Similarity	NPC2314
0.8212	Intermediate Similarity	NPC232386
0.8212	Intermediate Similarity	NPC190783
0.8212	Intermediate Similarity	NPC152680
0.8187	Intermediate Similarity	NPC286119
0.8187	Intermediate Similarity	NPC257269
0.8187	Intermediate Similarity	NPC114124
0.8162	Intermediate Similarity	NPC237579
0.8162	Intermediate Similarity	NPC474904
0.8152	Intermediate Similarity	NPC16357
0.8152	Intermediate Similarity	NPC302245
0.8152	Intermediate Similarity	NPC95426
0.8152	Intermediate Similarity	NPC9867
0.815	Intermediate Similarity	NPC29647
0.8142	Intermediate Similarity	NPC279228
0.8142	Intermediate Similarity	NPC15414
0.8142	Intermediate Similarity	NPC42663
0.8142	Intermediate Similarity	NPC49075
0.8142	Intermediate Similarity	NPC90998
0.8142	Intermediate Similarity	NPC271013
0.8142	Intermediate Similarity	NPC328155
0.8142	Intermediate Similarity	NPC7715
0.8142	Intermediate Similarity	NPC229373
0.8142	Intermediate Similarity	NPC104196
0.8142	Intermediate Similarity	NPC239824
0.8142	Intermediate Similarity	NPC54654
0.8142	Intermediate Similarity	NPC73492
0.8142	Intermediate Similarity	NPC8836
0.8142	Intermediate Similarity	NPC222661
0.8142	Intermediate Similarity	NPC290005
0.8142	Intermediate Similarity	NPC251735
0.8142	Intermediate Similarity	NPC217748
0.8142	Intermediate Similarity	NPC185639
0.8142	Intermediate Similarity	NPC182052
0.8142	Intermediate Similarity	NPC258657
0.8142	Intermediate Similarity	NPC311973
0.8142	Intermediate Similarity	NPC299990
0.8142	Intermediate Similarity	NPC290582
0.8142	Intermediate Similarity	NPC30779
0.8142	Intermediate Similarity	NPC285931
0.8142	Intermediate Similarity	NPC181796
0.8142	Intermediate Similarity	NPC223690
0.8136	Intermediate Similarity	NPC68328

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 NPC476576 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	181
0.1-0.2	695
0.2-0.3	1221
0.3-0.4	2292
0.4-0.5	2696
0.5-0.6	1498
0.6-0.7	478
0.7-0.8	88
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8142	Intermediate Similarity	NPD8053	Approved
0.8142	Intermediate Similarity	NPD8054	Approved
0.8132	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.8071	Intermediate Similarity	NPD7827	Phase 1
0.8011	Intermediate Similarity	NPD7906	Approved
0.7944	Intermediate Similarity	NPD27	Approved
0.7944	Intermediate Similarity	NPD2489	Approved
0.7943	Intermediate Similarity	NPD2978	Approved
0.7943	Intermediate Similarity	NPD2977	Approved
0.7941	Intermediate Similarity	NPD2420	Approved
0.7941	Intermediate Similarity	NPD2421	Approved
0.7933	Intermediate Similarity	NPD3051	Approved
0.7892	Intermediate Similarity	NPD4577	Approved
0.7892	Intermediate Similarity	NPD4578	Approved
0.7889	Intermediate Similarity	NPD2969	Approved
0.7889	Intermediate Similarity	NPD2970	Approved
0.7882	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD3845	Phase 1
0.7861	Intermediate Similarity	NPD4663	Approved
0.7796	Intermediate Similarity	NPD7313	Approved
0.7796	Intermediate Similarity	NPD7312	Approved
0.7796	Intermediate Similarity	NPD7310	Approved
0.7796	Intermediate Similarity	NPD7311	Approved
0.776	Intermediate Similarity	NPD8099	Discontinued
0.776	Intermediate Similarity	NPD8252	Approved
0.776	Intermediate Similarity	NPD8251	Approved
0.7754	Intermediate Similarity	NPD7309	Approved
0.7732	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD8156	Discontinued
0.7688	Intermediate Similarity	NPD4584	Approved
0.7684	Intermediate Similarity	NPD7298	Approved
0.766	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD6788	Approved
0.7647	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD6723	Discontinued
0.7586	Intermediate Similarity	NPD1424	Approved
0.7554	Intermediate Similarity	NPD4481	Phase 3
0.7554	Intermediate Similarity	NPD2898	Approved
0.75	Intermediate Similarity	NPD6031	Approved
0.75	Intermediate Similarity	NPD6030	Approved
0.75	Intermediate Similarity	NPD4727	Phase 1
0.7475	Intermediate Similarity	NPD2493	Approved
0.7475	Intermediate Similarity	NPD3452	Approved
0.7475	Intermediate Similarity	NPD2494	Approved
0.7475	Intermediate Similarity	NPD3450	Approved
0.7461	Intermediate Similarity	NPD2488	Approved
0.7461	Intermediate Similarity	NPD2490	Approved
0.7446	Intermediate Similarity	NPD4010	Discontinued
0.7427	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD4055	Discovery
0.7414	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD4582	Approved
0.7363	Intermediate Similarity	NPD4583	Approved
0.7354	Intermediate Similarity	NPD8153	Approved
0.7354	Intermediate Similarity	NPD8152	Approved
0.7351	Intermediate Similarity	NPD6071	Discontinued
0.735	Intermediate Similarity	NPD5005	Approved
0.735	Intermediate Similarity	NPD5006	Approved
0.7348	Intermediate Similarity	NPD4585	Approved
0.7348	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD7831	Phase 2
0.7322	Intermediate Similarity	NPD7833	Phase 2
0.7314	Intermediate Similarity	NPD5241	Discontinued
0.7313	Intermediate Similarity	NPD4002	Approved
0.7313	Intermediate Similarity	NPD4004	Approved
0.7308	Intermediate Similarity	NPD2560	Approved
0.7308	Intermediate Similarity	NPD2563	Approved
0.7299	Intermediate Similarity	NPD3060	Approved
0.7293	Intermediate Similarity	NPD3384	Approved
0.7293	Intermediate Similarity	NPD3382	Approved
0.7293	Intermediate Similarity	NPD3383	Approved
0.7278	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2974	Approved
0.7273	Intermediate Similarity	NPD2975	Approved
0.7273	Intermediate Similarity	NPD2973	Approved
0.7263	Intermediate Similarity	NPD6297	Approved
0.7254	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD4666	Phase 3
0.724	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD4420	Approved
0.7222	Intermediate Similarity	NPD4005	Discontinued
0.7222	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD5976	Discontinued
0.7192	Intermediate Similarity	NPD4040	Phase 1
0.7189	Intermediate Similarity	NPD5709	Phase 3
0.7177	Intermediate Similarity	NPD7047	Phase 3
0.7175	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD4580	Approved
0.7158	Intermediate Similarity	NPD42	Phase 2
0.7158	Intermediate Similarity	NPD6042	Phase 2
0.7151	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD2971	Approved
0.715	Intermediate Similarity	NPD2968	Approved
0.7143	Intermediate Similarity	NPD4772	Phase 2
0.7143	Intermediate Similarity	NPD4773	Phase 2
0.7136	Intermediate Similarity	NPD6997	Phase 2
0.7127	Intermediate Similarity	NPD4017	Approved
0.7119	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD6853	Approved
0.7113	Intermediate Similarity	NPD6851	Approved
0.7112	Intermediate Similarity	NPD6107	Approved
0.7097	Intermediate Similarity	NPD6234	Discontinued
0.7095	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD4859	Phase 1
0.7086	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD4166	Phase 2
0.7068	Intermediate Similarity	NPD4873	Discontinued
0.705	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD5604	Discontinued
0.7043	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD8095	Phase 1
0.7022	Intermediate Similarity	NPD5160	Discontinued
0.7017	Intermediate Similarity	NPD3641	Approved
0.7017	Intermediate Similarity	NPD3640	Phase 3
0.7017	Intermediate Similarity	NPD3639	Approved
0.7016	Intermediate Similarity	NPD7228	Approved
0.7011	Intermediate Similarity	NPD37	Approved
0.7	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD7124	Phase 2
0.6944	Remote Similarity	NPD7598	Phase 2
0.6943	Remote Similarity	NPD7479	Phase 2
0.6936	Remote Similarity	NPD3109	Approved
0.6936	Remote Similarity	NPD3110	Approved
0.693	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3055	Approved
0.6923	Remote Similarity	NPD3053	Approved
0.6923	Remote Similarity	NPD7549	Discontinued
0.691	Remote Similarity	NPD5177	Phase 3
0.691	Remote Similarity	NPD4162	Approved
0.6907	Remote Similarity	NPD6996	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD7447	Phase 1
0.6898	Remote Similarity	NPD4967	Phase 2
0.6898	Remote Similarity	NPD4965	Approved
0.6898	Remote Similarity	NPD4966	Approved
0.6888	Remote Similarity	NPD7281	Phase 3
0.6888	Remote Similarity	NPD7280	Phase 3
0.6878	Remote Similarity	NPD5677	Discontinued
0.6875	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD6072	Discontinued
0.6865	Remote Similarity	NPD5089	Approved
0.6865	Remote Similarity	NPD5090	Approved
0.686	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD817	Approved
0.6857	Remote Similarity	NPD2568	Approved
0.6857	Remote Similarity	NPD823	Approved
0.6854	Remote Similarity	NPD4257	Approved
0.6854	Remote Similarity	NPD4256	Phase 2
0.6852	Remote Similarity	NPD7907	Approved
0.6851	Remote Similarity	NPD7212	Phase 2
0.6851	Remote Similarity	NPD7213	Phase 3
0.6848	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD7922	Phase 1
0.6845	Remote Similarity	NPD2491	Approved
0.6845	Remote Similarity	NPD3448	Approved
0.6845	Remote Similarity	NPD3057	Approved
0.6837	Remote Similarity	NPD8318	Clinical (unspecified phase)
0.6834	Remote Similarity	NPD6841	Approved
0.6834	Remote Similarity	NPD6842	Approved
0.6834	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6834	Remote Similarity	NPD6843	Phase 3
0.6833	Remote Similarity	NPD2677	Approved
0.6829	Remote Similarity	NPD6612	Phase 2
0.6821	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD6674	Discontinued
0.6813	Remote Similarity	NPD3645	Discontinued
0.6811	Remote Similarity	NPD4675	Approved
0.6811	Remote Similarity	NPD4678	Approved
0.68	Remote Similarity	NPD3408	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD5582	Discontinued
0.6794	Remote Similarity	NPD7584	Approved
0.6788	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD3857	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD2674	Phase 3
0.678	Remote Similarity	NPD4108	Discontinued
0.6778	Remote Similarity	NPD5754	Discontinued
0.6778	Remote Similarity	NPD3977	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD6090	Discontinued
0.6771	Remote Similarity	NPD6625	Approved
0.6771	Remote Similarity	NPD4083	Discontinued
0.6763	Remote Similarity	NPD3027	Phase 3
0.6763	Remote Similarity	NPD3516	Approved
0.6763	Remote Similarity	NPD2972	Approved
0.6763	Remote Similarity	NPD3515	Approved
0.6763	Remote Similarity	NPD5156	Approved
0.6763	Remote Similarity	NPD3533	Approved
0.6763	Remote Similarity	NPD5155	Approved
0.6759	Remote Similarity	NPD4111	Phase 1
0.6759	Remote Similarity	NPD4665	Approved
0.6754	Remote Similarity	NPD7802	Discontinued
0.675	Remote Similarity	NPD3349	Phase 2
0.6748	Remote Similarity	NPD5457	Discontinued
0.6744	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD3061	Approved
0.6743	Remote Similarity	NPD3059	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