NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	441.22
Volume:	434.253
LogP:	1.55
LogD:	1.218
LogS:	-4.817
# Rotatable Bonds:	5
TPSA:	97.72
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	8
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.533
Synthetic Accessibility Score:	7.473
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.301
MDCK Permeability:	1.7457363355788402e-05
Pgp-inhibitor:	0.244
Pgp-substrate:	0.641
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.88
30% Bioavailability (F30%):	0.903

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.838
Plasma Protein Binding (PPB):	52.4781494140625%
Volume Distribution (VD):	1.295
Pgp-substrate:	44.68795394897461%

ADMET: Metabolism

CYP1A2-inhibitor:	0.035
CYP1A2-substrate:	0.963
CYP2C19-inhibitor:	0.317
CYP2C19-substrate:	0.851
CYP2C9-inhibitor:	0.075
CYP2C9-substrate:	0.018
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.373
CYP3A4-inhibitor:	0.743
CYP3A4-substrate:	0.803

ADMET: Excretion

Clearance (CL):	3.607
Half-life (T1/2):	0.806

ADMET: Toxicity

hERG Blockers:	0.063
Human Hepatotoxicity (H-HT):	0.382
Drug-inuced Liver Injury (DILI):	0.326
AMES Toxicity:	0.791
Rat Oral Acute Toxicity:	0.636
Maximum Recommended Daily Dose:	0.852
Skin Sensitization:	0.298
Carcinogencity:	0.88
Eye Corrosion:	0.003
Eye Irritation:	0.023
Respiratory Toxicity:	0.791

Download Data

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

Natural Product: NPC476957

Natural Product ID:	NPC476957
*Common Name:**	Daphmanidins F
IUPAC Name:	methyl (1R,5S,6R,9R,10S,13R,19R,21R)-9-(acetyloxymethyl)-21-hydroxy-5-methyl-20-oxa-3-azaheptacyclo[11.5.2.16,10.01,9.02,6.013,19.016,19]henicosa-2,16-diene-17-carboxylate
Synonyms:	Daphmanidin F
Standard InCHIKey:	RMWZDXAQNNORCN-CJSPYETGSA-N
Standard InCHI:	InChI=1S/C25H31NO6/c1-13-11-26-20-23(13)9-8-21(12-31-14(2)27)17(18(23)28)5-7-22-6-4-16-15(19(29)30-3)10-24(20,21)25(16,22)32-22/h13,17-18,28H,4-12H2,1-3H3/t13-,17-,18-,21-,22+,23+,24+,25+/m1/s1
SMILES:	C[C@@H]1CN=C2[C@@]13CC[C@@]4([C@]25CC(=C6[C@]57[C@@](O7)(CC[C@@H]4[C@H]3O)CC6)C(=O)OC)COC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	11685448
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives

*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
NPO3845	Daphniphyllum teijsmannii	Species	Daphniphyllaceae	Eukaryota	leaves	n.a.	n.a.	PMID[16562849]
NPO3845	Daphniphyllum teijsmannii	Species	Daphniphyllaceae	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
Others	1

Activity Type	# Activity
Tissue	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT177	Tissue	Aorta	Rattus norvegicus	Activity	=	45.8	%	PMID[16562849]

☑ 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 NPC476957 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	159
0.1-0.2	1054
0.2-0.3	4392
0.3-0.4	16546
0.4-0.5	9236
0.5-0.6	8659
0.6-0.7	2590
0.7-0.8	58
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8595	High Similarity	NPC476956
0.8197	Intermediate Similarity	NPC470540
0.7664	Intermediate Similarity	NPC246209
0.7482	Intermediate Similarity	NPC476558
0.7442	Intermediate Similarity	NPC470276
0.7308	Intermediate Similarity	NPC9714
0.7266	Intermediate Similarity	NPC106479
0.7252	Intermediate Similarity	NPC469380
0.7231	Intermediate Similarity	NPC470275
0.7213	Intermediate Similarity	NPC471412
0.7209	Intermediate Similarity	NPC123117
0.7188	Intermediate Similarity	NPC476163
0.7165	Intermediate Similarity	NPC179642
0.7154	Intermediate Similarity	NPC162973
0.7154	Intermediate Similarity	NPC106228
0.7154	Intermediate Similarity	NPC196931
0.7154	Intermediate Similarity	NPC72772
0.7154	Intermediate Similarity	NPC469794
0.7154	Intermediate Similarity	NPC138372
0.7154	Intermediate Similarity	NPC295791
0.7132	Intermediate Similarity	NPC204556
0.7131	Intermediate Similarity	NPC471413
0.7121	Intermediate Similarity	NPC42673
0.7109	Intermediate Similarity	NPC474846
0.7109	Intermediate Similarity	NPC469656
0.7109	Intermediate Similarity	NPC469655
0.7099	Intermediate Similarity	NPC473656
0.7077	Intermediate Similarity	NPC178289
0.7068	Intermediate Similarity	NPC17938
0.7068	Intermediate Similarity	NPC154491
0.7068	Intermediate Similarity	NPC251226
0.7068	Intermediate Similarity	NPC268530
0.7068	Intermediate Similarity	NPC143755
0.7059	Intermediate Similarity	NPC63186
0.7054	Intermediate Similarity	NPC470063
0.7045	Intermediate Similarity	NPC113448
0.7045	Intermediate Similarity	NPC475372
0.7037	Intermediate Similarity	NPC469382
0.7037	Intermediate Similarity	NPC471392
0.7016	Intermediate Similarity	NPC476081
0.7016	Intermediate Similarity	NPC165250
0.7015	Intermediate Similarity	NPC4021
0.7015	Intermediate Similarity	NPC159456
0.7007	Intermediate Similarity	NPC287423
0.7007	Intermediate Similarity	NPC280903
0.7007	Intermediate Similarity	NPC470537
0.6992	Remote Similarity	NPC472667
0.6992	Remote Similarity	NPC9674
0.6992	Remote Similarity	NPC19028
0.6992	Remote Similarity	NPC475041
0.6992	Remote Similarity	NPC312536
0.6985	Remote Similarity	NPC75856
0.6985	Remote Similarity	NPC86346
0.6985	Remote Similarity	NPC469379
0.6985	Remote Similarity	NPC469790
0.6984	Remote Similarity	NPC119855
0.6984	Remote Similarity	NPC220217
0.697	Remote Similarity	NPC284068
0.697	Remote Similarity	NPC475323
0.696	Remote Similarity	NPC36688
0.696	Remote Similarity	NPC112009
0.696	Remote Similarity	NPC472821
0.696	Remote Similarity	NPC160583
0.6953	Remote Similarity	NPC299590
0.6953	Remote Similarity	NPC273433
0.6947	Remote Similarity	NPC90472
0.6942	Remote Similarity	NPC37408
0.6942	Remote Similarity	NPC329435
0.694	Remote Similarity	NPC4548
0.694	Remote Similarity	NPC472004
0.6935	Remote Similarity	NPC25177
0.6935	Remote Similarity	NPC295110
0.6935	Remote Similarity	NPC268829
0.6935	Remote Similarity	NPC247701
0.6935	Remote Similarity	NPC222875
0.6934	Remote Similarity	NPC15095
0.6929	Remote Similarity	NPC473173
0.6929	Remote Similarity	NPC469318
0.6923	Remote Similarity	NPC23967
0.6917	Remote Similarity	NPC470420
0.6912	Remote Similarity	NPC473979
0.6912	Remote Similarity	NPC129992
0.6912	Remote Similarity	NPC27363
0.6912	Remote Similarity	NPC469789
0.6906	Remote Similarity	NPC470851
0.6905	Remote Similarity	NPC28656
0.6899	Remote Similarity	NPC474923
0.6899	Remote Similarity	NPC272898
0.6899	Remote Similarity	NPC48305
0.6899	Remote Similarity	NPC473036
0.6899	Remote Similarity	NPC475134
0.6899	Remote Similarity	NPC475563
0.6894	Remote Similarity	NPC266728
0.6894	Remote Similarity	NPC49492
0.6885	Remote Similarity	NPC29952
0.6884	Remote Similarity	NPC42399
0.6884	Remote Similarity	NPC298841
0.6875	Remote Similarity	NPC275539
0.6875	Remote Similarity	NPC189075
0.687	Remote Similarity	NPC962
0.687	Remote Similarity	NPC312017
0.687	Remote Similarity	NPC9848
0.6866	Remote Similarity	NPC476960
0.6866	Remote Similarity	NPC230513
0.6861	Remote Similarity	NPC8369
0.6857	Remote Similarity	NPC241935
0.6857	Remote Similarity	NPC279478
0.6855	Remote Similarity	NPC470074
0.6855	Remote Similarity	NPC201406
0.685	Remote Similarity	NPC252234
0.685	Remote Similarity	NPC469607
0.685	Remote Similarity	NPC478208
0.6846	Remote Similarity	NPC475480
0.6846	Remote Similarity	NPC475668
0.6846	Remote Similarity	NPC473921
0.6842	Remote Similarity	NPC13713
0.6842	Remote Similarity	NPC55296
0.6842	Remote Similarity	NPC58662
0.6838	Remote Similarity	NPC269642
0.6835	Remote Similarity	NPC470850
0.6835	Remote Similarity	NPC311534
0.6829	Remote Similarity	NPC132753
0.6829	Remote Similarity	NPC224356
0.6829	Remote Similarity	NPC151681
0.6829	Remote Similarity	NPC121402
0.6829	Remote Similarity	NPC175351
0.6825	Remote Similarity	NPC55872
0.6825	Remote Similarity	NPC10232
0.6825	Remote Similarity	NPC120321
0.6825	Remote Similarity	NPC474775
0.6825	Remote Similarity	NPC471208
0.6825	Remote Similarity	NPC189588
0.6825	Remote Similarity	NPC196471
0.6825	Remote Similarity	NPC180204
0.6825	Remote Similarity	NPC97487
0.6825	Remote Similarity	NPC159533
0.6825	Remote Similarity	NPC187302
0.6825	Remote Similarity	NPC476237
0.6822	Remote Similarity	NPC218602
0.6822	Remote Similarity	NPC474901
0.6822	Remote Similarity	NPC475941
0.6818	Remote Similarity	NPC284915
0.6818	Remote Similarity	NPC238667
0.6812	Remote Similarity	NPC469750
0.6812	Remote Similarity	NPC293112
0.6812	Remote Similarity	NPC250556
0.6812	Remote Similarity	NPC120994
0.6812	Remote Similarity	NPC203702
0.6809	Remote Similarity	NPC34963
0.6803	Remote Similarity	NPC471915
0.6803	Remote Similarity	NPC111273
0.68	Remote Similarity	NPC475958
0.68	Remote Similarity	NPC469327
0.68	Remote Similarity	NPC475099
0.6797	Remote Similarity	NPC187435
0.6797	Remote Similarity	NPC67321
0.6797	Remote Similarity	NPC110496
0.6797	Remote Similarity	NPC471783
0.6797	Remote Similarity	NPC473037
0.6797	Remote Similarity	NPC9457
0.6797	Remote Similarity	NPC473165
0.6797	Remote Similarity	NPC180744
0.6794	Remote Similarity	NPC152117
0.6794	Remote Similarity	NPC4573
0.6794	Remote Similarity	NPC234042
0.6794	Remote Similarity	NPC277769
0.6794	Remote Similarity	NPC42658
0.6791	Remote Similarity	NPC471121
0.6791	Remote Similarity	NPC471118
0.6788	Remote Similarity	NPC204812
0.6788	Remote Similarity	NPC11895
0.6788	Remote Similarity	NPC120724
0.6786	Remote Similarity	NPC231529
0.6786	Remote Similarity	NPC104382
0.6786	Remote Similarity	NPC35109
0.6786	Remote Similarity	NPC175186
0.6774	Remote Similarity	NPC222303
0.6772	Remote Similarity	NPC294259
0.6769	Remote Similarity	NPC328052
0.6769	Remote Similarity	NPC470496
0.6769	Remote Similarity	NPC206595
0.6769	Remote Similarity	NPC197428
0.6769	Remote Similarity	NPC472214
0.6769	Remote Similarity	NPC76084
0.6769	Remote Similarity	NPC472215
0.6767	Remote Similarity	NPC471127
0.6767	Remote Similarity	NPC234858
0.6767	Remote Similarity	NPC190286
0.6767	Remote Similarity	NPC470793
0.6767	Remote Similarity	NPC154363
0.6767	Remote Similarity	NPC298278
0.6765	Remote Similarity	NPC310511
0.6765	Remote Similarity	NPC67569
0.6763	Remote Similarity	NPC117702
0.6763	Remote Similarity	NPC179412
0.6763	Remote Similarity	NPC240070
0.6763	Remote Similarity	NPC469757
0.6763	Remote Similarity	NPC471357
0.6763	Remote Similarity	NPC146456
0.6763	Remote Similarity	NPC471356

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 NPC476957 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	109
0.1-0.2	822
0.2-0.3	3444
0.3-0.4	3539
0.4-0.5	835
0.5-0.6	324
0.6-0.7	77
0.7-0.8	0
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
0.7113	Intermediate Similarity	NPD6333	Approved
0.7113	Intermediate Similarity	NPD6334	Approved
0.6984	Remote Similarity	NPD6008	Approved
0.6953	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD7507	Approved
0.6774	Remote Similarity	NPD7638	Approved
0.6769	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD6420	Discontinued
0.672	Remote Similarity	NPD7640	Approved
0.672	Remote Similarity	NPD7639	Approved
0.6667	Remote Similarity	NPD7604	Phase 2
0.6667	Remote Similarity	NPD6053	Discontinued
0.6667	Remote Similarity	NPD7319	Approved
0.6642	Remote Similarity	NPD6909	Approved
0.6642	Remote Similarity	NPD6908	Approved
0.6615	Remote Similarity	NPD7320	Approved
0.6614	Remote Similarity	NPD7632	Discontinued
0.6589	Remote Similarity	NPD6675	Approved
0.6589	Remote Similarity	NPD7128	Approved
0.6589	Remote Similarity	NPD6402	Approved
0.6589	Remote Similarity	NPD5739	Approved
0.6538	Remote Similarity	NPD5697	Approved
0.6538	Remote Similarity	NPD5701	Approved
0.6538	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD4632	Approved
0.6489	Remote Similarity	NPD6881	Approved
0.6489	Remote Similarity	NPD6899	Approved
0.6489	Remote Similarity	NPD6011	Approved
0.6471	Remote Similarity	NPD7115	Discovery
0.6457	Remote Similarity	NPD8418	Phase 2
0.6439	Remote Similarity	NPD6014	Approved
0.6439	Remote Similarity	NPD6012	Approved
0.6439	Remote Similarity	NPD6373	Approved
0.6439	Remote Similarity	NPD6013	Approved
0.6439	Remote Similarity	NPD6372	Approved
0.6414	Remote Similarity	NPD6845	Suspended
0.6405	Remote Similarity	NPD7625	Phase 1
0.6391	Remote Similarity	NPD7102	Approved
0.6391	Remote Similarity	NPD7290	Approved
0.6391	Remote Similarity	NPD6883	Approved
0.6389	Remote Similarity	NPD6914	Discontinued
0.635	Remote Similarity	NPD6009	Approved
0.6343	Remote Similarity	NPD6847	Approved
0.6343	Remote Similarity	NPD6649	Approved
0.6343	Remote Similarity	NPD8130	Phase 1
0.6343	Remote Similarity	NPD6869	Approved
0.6343	Remote Similarity	NPD6617	Approved
0.6343	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD6650	Approved
0.6331	Remote Similarity	NPD6319	Approved
0.6304	Remote Similarity	NPD7328	Approved
0.6304	Remote Similarity	NPD7327	Approved
0.6299	Remote Similarity	NPD4755	Approved
0.6296	Remote Similarity	NPD6882	Approved
0.6296	Remote Similarity	NPD8297	Approved
0.6294	Remote Similarity	NPD7078	Approved
0.6286	Remote Similarity	NPD5983	Phase 2
0.6286	Remote Similarity	NPD8033	Approved
0.6268	Remote Similarity	NPD7492	Approved
0.6259	Remote Similarity	NPD7516	Approved
0.6233	Remote Similarity	NPD7260	Phase 2
0.6231	Remote Similarity	NPD5211	Phase 2
0.6224	Remote Similarity	NPD6616	Approved
0.6214	Remote Similarity	NPD8377	Approved
0.6214	Remote Similarity	NPD6059	Approved
0.6214	Remote Similarity	NPD6054	Approved
0.6214	Remote Similarity	NPD8294	Approved
0.6202	Remote Similarity	NPD4700	Approved
0.6202	Remote Similarity	NPD5286	Approved
0.6202	Remote Similarity	NPD4696	Approved
0.6202	Remote Similarity	NPD5285	Approved
0.6181	Remote Similarity	NPD8293	Discontinued
0.617	Remote Similarity	NPD8296	Approved
0.617	Remote Similarity	NPD8335	Approved
0.617	Remote Similarity	NPD8378	Approved
0.617	Remote Similarity	NPD8379	Approved
0.617	Remote Similarity	NPD6016	Approved
0.617	Remote Similarity	NPD6015	Approved
0.617	Remote Similarity	NPD8380	Approved
0.6159	Remote Similarity	NPD6274	Approved
0.6154	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5223	Approved
0.6148	Remote Similarity	NPD6371	Approved
0.6138	Remote Similarity	NPD7736	Approved
0.6136	Remote Similarity	NPD5141	Approved
0.6129	Remote Similarity	NPD5328	Approved
0.6127	Remote Similarity	NPD6370	Approved
0.6127	Remote Similarity	NPD5988	Approved
0.6119	Remote Similarity	NPD6686	Approved
0.6115	Remote Similarity	NPD6317	Approved
0.6111	Remote Similarity	NPD6399	Phase 3
0.6111	Remote Similarity	NPD6336	Discontinued
0.6111	Remote Similarity	NPD4202	Approved
0.6107	Remote Similarity	NPD5224	Approved
0.6107	Remote Similarity	NPD5225	Approved
0.6107	Remote Similarity	NPD4633	Approved
0.6107	Remote Similarity	NPD5226	Approved
0.6077	Remote Similarity	NPD6404	Discontinued
0.6071	Remote Similarity	NPD6313	Approved
0.6071	Remote Similarity	NPD6335	Approved
0.6071	Remote Similarity	NPD6314	Approved
0.6069	Remote Similarity	NPD8074	Phase 3
0.6061	Remote Similarity	NPD5174	Approved
0.6061	Remote Similarity	NPD5175	Approved
0.6061	Remote Similarity	NPD4754	Approved
0.6056	Remote Similarity	NPD6921	Approved
0.6056	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD6083	Phase 2
0.6047	Remote Similarity	NPD6084	Phase 2
0.6032	Remote Similarity	NPD6079	Approved
0.6029	Remote Similarity	NPD4634	Approved
0.6029	Remote Similarity	NPD6421	Discontinued
0.6028	Remote Similarity	NPD7101	Approved
0.6028	Remote Similarity	NPD7100	Approved
0.6016	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6014	Remote Similarity	NPD8298	Phase 2
0.6	Remote Similarity	NPD1695	Approved
0.6	Remote Similarity	NPD4225	Approved
0.597	Remote Similarity	NPD4768	Approved
0.597	Remote Similarity	NPD4767	Approved
0.5969	Remote Similarity	NPD5221	Approved
0.5969	Remote Similarity	NPD5222	Approved
0.5969	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5969	Remote Similarity	NPD4697	Phase 3
0.595	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5923	Remote Similarity	NPD5173	Approved
0.5918	Remote Similarity	NPD6033	Approved
0.5909	Remote Similarity	NPD4159	Approved
0.5906	Remote Similarity	NPD8035	Phase 2
0.5906	Remote Similarity	NPD5693	Phase 1
0.5906	Remote Similarity	NPD8034	Phase 2
0.5891	Remote Similarity	NPD5695	Phase 3
0.5887	Remote Similarity	NPD3618	Phase 1
0.5882	Remote Similarity	NPD4730	Approved
0.5882	Remote Similarity	NPD5128	Approved
0.5882	Remote Similarity	NPD4729	Approved
0.5882	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5878	Remote Similarity	NPD5696	Approved
0.5862	Remote Similarity	NPD7122	Discontinued
0.5859	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD7503	Approved
0.5827	Remote Similarity	NPD46	Approved
0.5827	Remote Similarity	NPD6698	Approved
0.5816	Remote Similarity	NPD6868	Approved
0.5814	Remote Similarity	NPD6001	Approved
0.5814	Remote Similarity	NPD7748	Approved
0.5809	Remote Similarity	NPD6412	Phase 2
0.5806	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD7519	Approved
0.5804	Remote Similarity	NPD7518	Approved
0.5804	Remote Similarity	NPD7517	Approved
0.5802	Remote Similarity	NPD7902	Approved
0.5797	Remote Similarity	NPD5249	Phase 3
0.5797	Remote Similarity	NPD5247	Approved
0.5797	Remote Similarity	NPD5135	Approved
0.5797	Remote Similarity	NPD5250	Approved
0.5797	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5797	Remote Similarity	NPD5251	Approved
0.5797	Remote Similarity	NPD5248	Approved
0.5797	Remote Similarity	NPD5169	Approved
0.5794	Remote Similarity	NPD6903	Approved
0.5789	Remote Similarity	NPD5344	Discontinued
0.5789	Remote Similarity	NPD1700	Approved
0.5786	Remote Similarity	NPD8133	Approved
0.5786	Remote Similarity	NPD1376	Discontinued
0.5782	Remote Similarity	NPD8273	Phase 1
0.5781	Remote Similarity	NPD7515	Phase 2
0.576	Remote Similarity	NPD5330	Approved
0.576	Remote Similarity	NPD7146	Approved
0.576	Remote Similarity	NPD7334	Approved
0.576	Remote Similarity	NPD7521	Approved
0.576	Remote Similarity	NPD6684	Approved
0.576	Remote Similarity	NPD6409	Approved
0.5755	Remote Similarity	NPD5127	Approved
0.5755	Remote Similarity	NPD1719	Phase 1
0.5755	Remote Similarity	NPD5215	Approved
0.5755	Remote Similarity	NPD5216	Approved
0.5755	Remote Similarity	NPD5217	Approved
0.5753	Remote Similarity	NPD7642	Approved
0.575	Remote Similarity	NPD6697	Approved
0.575	Remote Similarity	NPD6114	Approved
0.575	Remote Similarity	NPD6118	Approved
0.575	Remote Similarity	NPD6115	Approved
0.5748	Remote Similarity	NPD4753	Phase 2
0.5738	Remote Similarity	NPD1448	Clinical (unspecified phase)
0.5735	Remote Similarity	NPD6640	Phase 3
0.5726	Remote Similarity	NPD3666	Approved
0.5726	Remote Similarity	NPD4786	Approved
0.5726	Remote Similarity	NPD3133	Approved
0.5726	Remote Similarity	NPD3665	Phase 1
0.5705	Remote Similarity	NPD8336	Approved
0.5705	Remote Similarity	NPD8337	Approved
0.5691	Remote Similarity	NPD3667	Approved
0.5685	Remote Similarity	NPD8080	Discontinued
0.568	Remote Similarity	NPD1694	Approved
0.5669	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5669	Remote Similarity	NPD5737	Approved
0.5669	Remote Similarity	NPD6672	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