NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	281.11
Volume:	281.355
LogP:	1.184
LogD:	2.065
LogS:	-2.852
# Rotatable Bonds:	0
TPSA:	50.72
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.778
Synthetic Accessibility Score:	3.553
Fsp3:	0.294
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:	-4.989
MDCK Permeability:	1.6010708350222558e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.987
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.953
Plasma Protein Binding (PPB):	86.96985626220703%
Volume Distribution (VD):	2.604
Pgp-substrate:	5.5006513595581055%

ADMET: Metabolism

CYP1A2-inhibitor:	0.834
CYP1A2-substrate:	0.334
CYP2C19-inhibitor:	0.38
CYP2C19-substrate:	0.764
CYP2C9-inhibitor:	0.033
CYP2C9-substrate:	0.489
CYP2D6-inhibitor:	0.958
CYP2D6-substrate:	0.869
CYP3A4-inhibitor:	0.781
CYP3A4-substrate:	0.468

ADMET: Excretion

Clearance (CL):	6.709
Half-life (T1/2):	0.159

ADMET: Toxicity

hERG Blockers:	0.261
Human Hepatotoxicity (H-HT):	0.484
Drug-inuced Liver Injury (DILI):	0.101
AMES Toxicity:	0.871
Rat Oral Acute Toxicity:	0.426
Maximum Recommended Daily Dose:	0.958
Skin Sensitization:	0.134
Carcinogencity:	0.16
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.838

Download Data

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

Natural Product: NPC476575

Natural Product ID:	NPC476575
*Common Name:**	(12R,13R)-3,5-dioxa-11-azapentacyclo[10.7.1.02,6.08,20.014,19]icosa-1(20),2(6),7,14,16,18-hexaen-13-ol;2,2,2-trifluoroacetic acid
IUPAC Name:	(12R,13R)-3,5-dioxa-11-azapentacyclo[10.7.1.02,6.08,20.014,19]icosa-1(20),2(6),7,14,16,18-hexaen-13-ol;2,2,2-trifluoroacetic acid
Synonyms:
Standard InCHIKey:	HPNXOYSRHLFPGQ-QNBGGDODSA-N
Standard InCHI:	InChI=1S/C17H15NO3.C2HF3O2/c19-16-11-4-2-1-3-10(11)14-13-9(5-6-18-15(13)16)7-12-17(14)21-8-20-12;3-2(4,5)1(6)7/h1-4,7,15-16,18-19H,5-6,8H2;(H,6,7)/t15-,16-;/m1./s1
SMILES:	C1CN[C@H]2[C@@H](C3=CC=CC=C3C4=C2C1=CC5=C4OCO5)O.C(=O)(C(F)(F)F)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1270449
PubChem CID:	54585824
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0000381] Aporphines [CHEMONTID:0003021] Hydroxy-7-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	>	126000	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 NPC476575 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	301
0.1-0.2	1556
0.2-0.3	6936
0.3-0.4	11066
0.4-0.5	6851
0.5-0.6	12762
0.6-0.7	2536
0.7-0.8	570
0.8-0.85	74
0.85-0.9	34
0.9-0.95	9
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9576	High Similarity	NPC477558
0.9521	High Similarity	NPC126284
0.9521	High Similarity	NPC267408
0.9477	High Similarity	NPC117717
0.9408	High Similarity	NPC248642
0.9394	High Similarity	NPC152212
0.9353	High Similarity	NPC156576
0.924	High Similarity	NPC135772
0.9235	High Similarity	NPC476574
0.9235	High Similarity	NPC477561
0.9235	High Similarity	NPC155442
0.9235	High Similarity	NPC312918
0.9207	High Similarity	NPC189470
0.9181	High Similarity	NPC275132
0.9162	High Similarity	NPC6152
0.9133	High Similarity	NPC214116
0.9096	High Similarity	NPC86144
0.9096	High Similarity	NPC304659
0.9023	High Similarity	NPC57036
0.8977	High Similarity	NPC475754
0.8971	High Similarity	NPC186546
0.8971	High Similarity	NPC476576
0.8947	High Similarity	NPC112575
0.8929	High Similarity	NPC298979
0.8922	High Similarity	NPC225774
0.8902	High Similarity	NPC474506
0.8902	High Similarity	NPC32413
0.8895	High Similarity	NPC320223
0.8895	High Similarity	NPC114364
0.8895	High Similarity	NPC23219
0.8889	High Similarity	NPC199465
0.8889	High Similarity	NPC229166
0.8889	High Similarity	NPC128560
0.8869	High Similarity	NPC476432
0.8869	High Similarity	NPC219341
0.8869	High Similarity	NPC24264
0.8844	High Similarity	NPC470879
0.8844	High Similarity	NPC258695
0.883	High Similarity	NPC192135
0.883	High Similarity	NPC477020
0.883	High Similarity	NPC66341
0.8824	High Similarity	NPC69712
0.8824	High Similarity	NPC26240
0.8824	High Similarity	NPC477562
0.8817	High Similarity	NPC247389
0.881	High Similarity	NPC16805
0.881	High Similarity	NPC302527
0.881	High Similarity	NPC167546
0.8786	High Similarity	NPC294790
0.8786	High Similarity	NPC118633
0.8786	High Similarity	NPC148693
0.8757	High Similarity	NPC81247
0.8757	High Similarity	NPC35627
0.8757	High Similarity	NPC476573
0.8743	High Similarity	NPC232924
0.8743	High Similarity	NPC306902
0.8743	High Similarity	NPC477559
0.8743	High Similarity	NPC266753
0.8743	High Similarity	NPC160298
0.8721	High Similarity	NPC2314
0.8706	High Similarity	NPC210918
0.8675	High Similarity	NPC203784
0.8675	High Similarity	NPC170503
0.8675	High Similarity	NPC126519
0.8652	High Similarity	NPC237579
0.8636	High Similarity	NPC116284
0.8636	High Similarity	NPC233718
0.8629	High Similarity	NPC474507
0.8621	High Similarity	NPC148709
0.8621	High Similarity	NPC476577
0.8621	High Similarity	NPC173416
0.8596	High Similarity	NPC150879
0.8588	High Similarity	NPC168409
0.8555	High Similarity	NPC149090
0.8555	High Similarity	NPC19520
0.8488	Intermediate Similarity	NPC12053
0.8488	Intermediate Similarity	NPC81218
0.8488	Intermediate Similarity	NPC117188
0.8488	Intermediate Similarity	NPC204947
0.8488	Intermediate Similarity	NPC205421
0.8488	Intermediate Similarity	NPC145832
0.8488	Intermediate Similarity	NPC474931
0.8488	Intermediate Similarity	NPC306555
0.8488	Intermediate Similarity	NPC158376
0.848	Intermediate Similarity	NPC306843
0.848	Intermediate Similarity	NPC253043
0.848	Intermediate Similarity	NPC78222
0.848	Intermediate Similarity	NPC212794
0.848	Intermediate Similarity	NPC96603
0.848	Intermediate Similarity	NPC196447
0.848	Intermediate Similarity	NPC136508
0.848	Intermediate Similarity	NPC477563
0.848	Intermediate Similarity	NPC13504
0.8439	Intermediate Similarity	NPC241055
0.8421	Intermediate Similarity	NPC324144
0.8421	Intermediate Similarity	NPC1229
0.8421	Intermediate Similarity	NPC233650
0.8412	Intermediate Similarity	NPC166014
0.8412	Intermediate Similarity	NPC27410
0.8402	Intermediate Similarity	NPC476572
0.8398	Intermediate Similarity	NPC82763
0.8393	Intermediate Similarity	NPC99659
0.8393	Intermediate Similarity	NPC325871
0.8372	Intermediate Similarity	NPC134858
0.8352	Intermediate Similarity	NPC329969
0.8333	Intermediate Similarity	NPC58766
0.8333	Intermediate Similarity	NPC475686
0.8323	Intermediate Similarity	NPC81733
0.8323	Intermediate Similarity	NPC326316
0.8315	Intermediate Similarity	NPC220961
0.8314	Intermediate Similarity	NPC320104
0.8286	Intermediate Similarity	NPC168753
0.8286	Intermediate Similarity	NPC474475
0.8286	Intermediate Similarity	NPC118274
0.8276	Intermediate Similarity	NPC190332
0.8276	Intermediate Similarity	NPC181653
0.8276	Intermediate Similarity	NPC210140
0.8272	Intermediate Similarity	NPC46990
0.8266	Intermediate Similarity	NPC169743
0.8239	Intermediate Similarity	NPC239775
0.8239	Intermediate Similarity	NPC225597
0.8239	Intermediate Similarity	NPC477640
0.8239	Intermediate Similarity	NPC470739
0.8229	Intermediate Similarity	NPC158148
0.8229	Intermediate Similarity	NPC266176
0.8229	Intermediate Similarity	NPC290759
0.8229	Intermediate Similarity	NPC82533
0.8204	Intermediate Similarity	NPC60538
0.8204	Intermediate Similarity	NPC207824
0.8182	Intermediate Similarity	NPC311991
0.8161	Intermediate Similarity	NPC276944
0.8161	Intermediate Similarity	NPC238530
0.8161	Intermediate Similarity	NPC232514
0.8146	Intermediate Similarity	NPC187678
0.8142	Intermediate Similarity	NPC474904
0.8118	Intermediate Similarity	NPC2295
0.8118	Intermediate Similarity	NPC477564
0.8114	Intermediate Similarity	NPC195392
0.8111	Intermediate Similarity	NPC244554
0.8107	Intermediate Similarity	NPC76213
0.8107	Intermediate Similarity	NPC277669
0.8092	Intermediate Similarity	NPC215829
0.8092	Intermediate Similarity	NPC97072
0.807	Intermediate Similarity	NPC138487
0.807	Intermediate Similarity	NPC244112
0.807	Intermediate Similarity	NPC216459
0.807	Intermediate Similarity	NPC41178
0.8068	Intermediate Similarity	NPC100566
0.8057	Intermediate Similarity	NPC247972
0.8046	Intermediate Similarity	NPC60186
0.8036	Intermediate Similarity	NPC475959
0.8035	Intermediate Similarity	NPC477080
0.8035	Intermediate Similarity	NPC111485
0.8023	Intermediate Similarity	NPC31311
0.8023	Intermediate Similarity	NPC234392
0.8023	Intermediate Similarity	NPC146288
0.8021	Intermediate Similarity	NPC162653
0.8011	Intermediate Similarity	NPC124657
0.8011	Intermediate Similarity	NPC193853
0.8011	Intermediate Similarity	NPC223077
0.8011	Intermediate Similarity	NPC56887
0.8	Intermediate Similarity	NPC241704
0.8	Intermediate Similarity	NPC237044
0.8	Intermediate Similarity	NPC474470
0.7989	Intermediate Similarity	NPC249274
0.7977	Intermediate Similarity	NPC79328
0.7969	Intermediate Similarity	NPC156728
0.7969	Intermediate Similarity	NPC244606
0.7965	Intermediate Similarity	NPC76079
0.7956	Intermediate Similarity	NPC474325
0.7956	Intermediate Similarity	NPC15919
0.7955	Intermediate Similarity	NPC209377
0.7953	Intermediate Similarity	NPC26601
0.7946	Intermediate Similarity	NPC312531
0.7944	Intermediate Similarity	NPC304675
0.7931	Intermediate Similarity	NPC59028
0.7931	Intermediate Similarity	NPC92191
0.7923	Intermediate Similarity	NPC249405
0.7919	Intermediate Similarity	NPC180756
0.7919	Intermediate Similarity	NPC323443
0.7912	Intermediate Similarity	NPC32154
0.7912	Intermediate Similarity	NPC474745
0.7903	Intermediate Similarity	NPC281581
0.7898	Intermediate Similarity	NPC293871
0.7898	Intermediate Similarity	NPC124433
0.7895	Intermediate Similarity	NPC212163
0.7887	Intermediate Similarity	NPC11708
0.7886	Intermediate Similarity	NPC4304
0.7886	Intermediate Similarity	NPC205167
0.7882	Intermediate Similarity	NPC219162
0.7882	Intermediate Similarity	NPC211296
0.7877	Intermediate Similarity	NPC329911
0.787	Intermediate Similarity	NPC476151
0.7869	Intermediate Similarity	NPC179704
0.7857	Intermediate Similarity	NPC185838
0.7849	Intermediate Similarity	NPC233029
0.7849	Intermediate Similarity	NPC210148
0.7838	Intermediate Similarity	NPC9867
0.7829	Intermediate Similarity	NPC7393
0.7821	Intermediate Similarity	NPC160570

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 NPC476575 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	180
0.1-0.2	655
0.2-0.3	1140
0.3-0.4	2173
0.4-0.5	2672
0.5-0.6	1686
0.6-0.7	545
0.7-0.8	99
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
0.8218	Intermediate Similarity	NPD3051	Approved
0.8171	Intermediate Similarity	NPD2970	Approved
0.8171	Intermediate Similarity	NPD2969	Approved
0.8129	Intermediate Similarity	NPD2977	Approved
0.8129	Intermediate Similarity	NPD2978	Approved
0.8066	Intermediate Similarity	NPD4578	Approved
0.8066	Intermediate Similarity	NPD4577	Approved
0.8033	Intermediate Similarity	NPD4663	Approved
0.8023	Intermediate Similarity	NPD27	Approved
0.8023	Intermediate Similarity	NPD2489	Approved
0.7989	Intermediate Similarity	NPD7906	Approved
0.7919	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD5241	Discontinued
0.7829	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD3845	Phase 1
0.7722	Intermediate Similarity	NPD4481	Phase 3
0.7706	Intermediate Similarity	NPD2420	Approved
0.7706	Intermediate Similarity	NPD2421	Approved
0.7679	Intermediate Similarity	NPD3060	Approved
0.7674	Intermediate Similarity	NPD4727	Phase 1
0.7661	Intermediate Similarity	NPD4584	Approved
0.7619	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD6071	Discontinued
0.7598	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD5160	Discontinued
0.7588	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD7313	Approved
0.7581	Intermediate Similarity	NPD7312	Approved
0.7581	Intermediate Similarity	NPD7311	Approved
0.7581	Intermediate Similarity	NPD7310	Approved
0.7572	Intermediate Similarity	NPD6030	Approved
0.7572	Intermediate Similarity	NPD5976	Discontinued
0.7572	Intermediate Similarity	NPD6031	Approved
0.7571	Intermediate Similarity	NPD2560	Approved
0.7571	Intermediate Similarity	NPD2563	Approved
0.7557	Intermediate Similarity	NPD7298	Approved
0.7542	Intermediate Similarity	NPD5709	Phase 3
0.754	Intermediate Similarity	NPD7309	Approved
0.7538	Intermediate Similarity	NPD3452	Approved
0.7538	Intermediate Similarity	NPD3450	Approved
0.7513	Intermediate Similarity	NPD2974	Approved
0.7513	Intermediate Similarity	NPD2973	Approved
0.7513	Intermediate Similarity	NPD2975	Approved
0.7512	Intermediate Similarity	NPD7827	Phase 1
0.75	Intermediate Similarity	NPD4666	Phase 3
0.75	Intermediate Similarity	NPD6042	Phase 2
0.75	Intermediate Similarity	NPD42	Phase 2
0.7455	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD2493	Approved
0.7449	Intermediate Similarity	NPD2494	Approved
0.7435	Intermediate Similarity	NPD2488	Approved
0.7435	Intermediate Similarity	NPD2490	Approved
0.7433	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD6297	Approved
0.7401	Intermediate Similarity	NPD4772	Phase 2
0.7401	Intermediate Similarity	NPD4773	Phase 2
0.7398	Intermediate Similarity	NPD4580	Approved
0.7394	Intermediate Similarity	NPD2971	Approved
0.7394	Intermediate Similarity	NPD2968	Approved
0.7389	Intermediate Similarity	NPD7831	Phase 2
0.7389	Intermediate Similarity	NPD7833	Phase 2
0.7389	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD4420	Approved
0.7374	Intermediate Similarity	NPD4002	Approved
0.7374	Intermediate Similarity	NPD4004	Approved
0.7354	Intermediate Similarity	NPD8053	Approved
0.7354	Intermediate Similarity	NPD6853	Approved
0.7354	Intermediate Similarity	NPD8054	Approved
0.7354	Intermediate Similarity	NPD6851	Approved
0.7337	Intermediate Similarity	NPD4582	Approved
0.7337	Intermediate Similarity	NPD2898	Approved
0.7337	Intermediate Similarity	NPD4583	Approved
0.7312	Intermediate Similarity	NPD8156	Discontinued
0.7294	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD6107	Approved
0.7267	Intermediate Similarity	NPD4162	Approved
0.7267	Intermediate Similarity	NPD4237	Approved
0.7267	Intermediate Similarity	NPD4236	Phase 3
0.7259	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD8252	Approved
0.7258	Intermediate Similarity	NPD8251	Approved
0.7258	Intermediate Similarity	NPD8099	Discontinued
0.7251	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD4040	Phase 1
0.7238	Intermediate Similarity	NPD6788	Approved
0.7236	Intermediate Similarity	NPD5005	Approved
0.7236	Intermediate Similarity	NPD5006	Approved
0.7219	Intermediate Similarity	NPD823	Approved
0.7219	Intermediate Similarity	NPD817	Approved
0.7198	Intermediate Similarity	NPD5604	Discontinued
0.7191	Intermediate Similarity	NPD4017	Approved
0.719	Intermediate Similarity	NPD6997	Phase 2
0.7184	Intermediate Similarity	NPD2677	Approved
0.7159	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD1424	Approved
0.7159	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD7047	Phase 3
0.7135	Intermediate Similarity	NPD3687	Approved
0.7135	Intermediate Similarity	NPD3686	Approved
0.7135	Intermediate Similarity	NPD2154	Approved
0.7135	Intermediate Similarity	NPD2155	Approved
0.7135	Intermediate Similarity	NPD1753	Discontinued
0.7135	Intermediate Similarity	NPD2156	Approved
0.7135	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD5095	Phase 3
0.7128	Intermediate Similarity	NPD3933	Discontinued
0.7128	Intermediate Similarity	NPD5096	Phase 3
0.7119	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD2845	Phase 2
0.7113	Intermediate Similarity	NPD2843	Phase 2
0.7107	Intermediate Similarity	NPD5582	Discontinued
0.7105	Intermediate Similarity	NPD7039	Approved
0.7105	Intermediate Similarity	NPD7038	Approved
0.7072	Intermediate Similarity	NPD3382	Approved
0.7072	Intermediate Similarity	NPD3384	Approved
0.7072	Intermediate Similarity	NPD3383	Approved
0.7069	Intermediate Similarity	NPD5177	Phase 3
0.7065	Intermediate Similarity	NPD7400	Phase 3
0.7065	Intermediate Similarity	NPD3057	Approved
0.7062	Intermediate Similarity	NPD2874	Phase 2
0.7059	Intermediate Similarity	NPD4859	Phase 1
0.7052	Intermediate Similarity	NPD4725	Approved
0.7052	Intermediate Similarity	NPD4721	Approved
0.7052	Intermediate Similarity	NPD4726	Approved
0.7051	Intermediate Similarity	NPD6723	Discontinued
0.7043	Intermediate Similarity	NPD4166	Phase 2
0.7043	Intermediate Similarity	NPD4010	Discontinued
0.7037	Intermediate Similarity	NPD4873	Discontinued
0.7035	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD7235	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD3054	Approved
0.7018	Intermediate Similarity	NPD3052	Approved
0.701	Intermediate Similarity	NPD3857	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7598	Phase 2
0.7	Intermediate Similarity	NPD3109	Approved
0.7	Intermediate Similarity	NPD3059	Approved
0.7	Intermediate Similarity	NPD3061	Approved
0.7	Intermediate Similarity	NPD3110	Approved
0.7	Intermediate Similarity	NPD3062	Approved
0.6983	Remote Similarity	NPD3640	Phase 3
0.6983	Remote Similarity	NPD3639	Approved
0.6983	Remote Similarity	NPD3641	Approved
0.698	Remote Similarity	NPD3448	Approved
0.698	Remote Similarity	NPD3533	Approved
0.698	Remote Similarity	NPD2972	Approved
0.6966	Remote Similarity	NPD3645	Discontinued
0.6965	Remote Similarity	NPD5457	Discontinued
0.6947	Remote Similarity	NPD8153	Approved
0.6947	Remote Similarity	NPD8152	Approved
0.6943	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD1132	Approved
0.6941	Remote Similarity	NPD1136	Approved
0.6941	Remote Similarity	NPD1130	Approved
0.694	Remote Similarity	NPD5773	Approved
0.694	Remote Similarity	NPD5772	Approved
0.6919	Remote Similarity	NPD7262	Phase 1
0.6919	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD4055	Discovery
0.6919	Remote Similarity	NPD5314	Approved
0.6915	Remote Similarity	NPD4083	Discontinued
0.6914	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7037	Approved
0.6911	Remote Similarity	NPD7479	Phase 2
0.691	Remote Similarity	NPD1774	Approved
0.6907	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD4005	Discontinued
0.6906	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD2491	Approved
0.6893	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD3936	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD4227	Discontinued
0.6882	Remote Similarity	NPD598	Approved
0.6882	Remote Similarity	NPD601	Approved
0.6882	Remote Similarity	NPD597	Approved
0.6878	Remote Similarity	NPD7999	Approved
0.6875	Remote Similarity	NPD5676	Approved
0.6875	Remote Similarity	NPD5062	Approved
0.6875	Remote Similarity	NPD3638	Discontinued
0.6875	Remote Similarity	NPD5061	Approved
0.6872	Remote Similarity	NPD3536	Discontinued
0.6856	Remote Similarity	NPD5895	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD7281	Phase 3
0.6856	Remote Similarity	NPD7280	Phase 3
0.6854	Remote Similarity	NPD3122	Phase 3
0.6854	Remote Similarity	NPD6667	Approved
0.6854	Remote Similarity	NPD6666	Approved
0.6853	Remote Similarity	NPD3408	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD6037	Discontinued
0.6842	Remote Similarity	NPD3530	Approved
0.6842	Remote Similarity	NPD3532	Approved
0.6842	Remote Similarity	NPD3531	Approved
0.6842	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6407	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