NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	306.22
Volume:	344.449
LogP:	6.362
LogD:	4.482
LogS:	-3.556
# Rotatable Bonds:	11
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.426
Synthetic Accessibility Score:	2.232
Fsp3:	0.632
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.838
MDCK Permeability:	1.5839774277992547e-05
Pgp-inhibitor:	0.135
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.215
Plasma Protein Binding (PPB):	98.80972290039062%
Volume Distribution (VD):	1.627
Pgp-substrate:	1.4038424491882324%

ADMET: Metabolism

CYP1A2-inhibitor:	0.957
CYP1A2-substrate:	0.225
CYP2C19-inhibitor:	0.882
CYP2C19-substrate:	0.081
CYP2C9-inhibitor:	0.445
CYP2C9-substrate:	0.966
CYP2D6-inhibitor:	0.912
CYP2D6-substrate:	0.242
CYP3A4-inhibitor:	0.531
CYP3A4-substrate:	0.078

ADMET: Excretion

Clearance (CL):	5.313
Half-life (T1/2):	0.514

ADMET: Toxicity

hERG Blockers:	0.095
Human Hepatotoxicity (H-HT):	0.034
Drug-inuced Liver Injury (DILI):	0.299
AMES Toxicity:	0.379
Rat Oral Acute Toxicity:	0.1
Maximum Recommended Daily Dose:	0.538
Skin Sensitization:	0.939
Carcinogencity:	0.06
Eye Corrosion:	0.489
Eye Irritation:	0.986
Respiratory Toxicity:	0.859

Download Data

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

Natural Product: NPC477454

Natural Product ID:	NPC477454
*Common Name:**	GBKPEEONRMUYJY-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GBKPEEONRMUYJY-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H30O3/c1-3-4-5-6-7-8-9-10-11-12-16-13-17(21)14-18(22)19(16)15(2)20/h13-14,21-22H,3-12H2,1-2H3
SMILES:	CCCCCCCCCCCc1cc(O)cc(c1C(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3590506
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0004296] Phenylketones [CHEMONTID:0004298] Alkyl-phenylketones

*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
NPO11898	Lobophora variegata	Species	Dictyotaceae	Eukaryota	n.a.	at depths of 630 m at El Mdano (Tenerife, Canary Islands)	n.a.	PMID[26126835]
NPO40175	Knema hookeriana	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27008174]
NPO11898	Lobophora variegata	Species	Dictyotaceae	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
Ki	2
Others	3

Activity Type	# Activity
Organism	3
PROTEIN-PROTEIN INTERACTION	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1204	Organism	Enterococcus faecalis ATCC 29212	Enterococcus faecalis ATCC 29212	Inhibition	=	-9.8	%	PMID[528095]
NPT19	Organism	Escherichia coli	Escherichia coli	Inhibition	=	-1.0	%	PMID[528095]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	Inhibition	=	17.0	%	PMID[528095]
NPT21617	PROTEIN-PROTEIN INTERACTION	Induced myeloid leukemia cell differentiation protein Mcl-1/BH3-interacting domain death agonist	Homo sapiens	Ki	>	33000.0	nM	PMID[528096]
NPT21616	PROTEIN-PROTEIN INTERACTION	Bcl-xL/BAK	Homo sapiens	Ki	>	23000.0	nM	PMID[528096]

☑ 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 NPC477454 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	317
0.1-0.2	1594
0.2-0.3	3986
0.3-0.4	11518
0.4-0.5	7600
0.5-0.6	5375
0.6-0.7	6642
0.7-0.8	4718
0.8-0.85	674
0.85-0.9	218
0.9-0.95	49
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9916	High Similarity	NPC473691
0.9672	High Similarity	NPC92624
0.9593	High Similarity	NPC259942
0.9435	High Similarity	NPC17840
0.9435	High Similarity	NPC247477
0.9412	High Similarity	NPC149246
0.9344	High Similarity	NPC201728
0.9344	High Similarity	NPC262671
0.9291	High Similarity	NPC166480
0.9291	High Similarity	NPC282780
0.9274	High Similarity	NPC41263
0.9256	High Similarity	NPC91105
0.925	High Similarity	NPC146642
0.9213	High Similarity	NPC37299
0.9213	High Similarity	NPC180261
0.9187	High Similarity	NPC475733
0.918	High Similarity	NPC472029
0.918	High Similarity	NPC65761
0.9174	High Similarity	NPC215392
0.9167	High Similarity	NPC294037
0.916	High Similarity	NPC40649
0.916	High Similarity	NPC209486
0.9147	High Similarity	NPC191976
0.9127	High Similarity	NPC62219
0.9098	High Similarity	NPC309765
0.9083	High Similarity	NPC161617
0.9077	High Similarity	NPC149372
0.9077	High Similarity	NPC474849
0.9077	High Similarity	NPC178467
0.9077	High Similarity	NPC65837
0.9077	High Similarity	NPC290030
0.9077	High Similarity	NPC474771
0.9076	High Similarity	NPC121259
0.907	High Similarity	NPC290803
0.9062	High Similarity	NPC267205
0.9062	High Similarity	NPC48036
0.9032	High Similarity	NPC10926
0.9016	High Similarity	NPC303737
0.9008	High Similarity	NPC475974
0.9008	High Similarity	NPC191835
0.9	High Similarity	NPC118919
0.8992	High Similarity	NPC474519
0.8992	High Similarity	NPC477453
0.8984	High Similarity	NPC175738
0.8976	High Similarity	NPC147757
0.8968	High Similarity	NPC179898
0.896	High Similarity	NPC8745
0.896	High Similarity	NPC62952
0.896	High Similarity	NPC267846
0.8952	High Similarity	NPC13238
0.8939	High Similarity	NPC162939
0.8939	High Similarity	NPC472903
0.8939	High Similarity	NPC242994
0.8939	High Similarity	NPC138099
0.8931	High Similarity	NPC471905
0.8931	High Similarity	NPC70380
0.8931	High Similarity	NPC71256
0.8931	High Similarity	NPC194579
0.8906	High Similarity	NPC189823
0.8906	High Similarity	NPC219892
0.8898	High Similarity	NPC474998
0.8898	High Similarity	NPC109123
0.8889	High Similarity	NPC209959
0.8889	High Similarity	NPC266689
0.8889	High Similarity	NPC23126
0.8889	High Similarity	NPC116513
0.8889	High Similarity	NPC103356
0.8889	High Similarity	NPC162612
0.8889	High Similarity	NPC169250
0.8889	High Similarity	NPC100067
0.8889	High Similarity	NPC190043
0.8889	High Similarity	NPC72158
0.8889	High Similarity	NPC105157
0.8889	High Similarity	NPC98254
0.8889	High Similarity	NPC30501
0.8872	High Similarity	NPC169452
0.8872	High Similarity	NPC181560
0.8864	High Similarity	NPC472403
0.8864	High Similarity	NPC94248
0.8864	High Similarity	NPC177307
0.8864	High Similarity	NPC9121
0.8864	High Similarity	NPC212693
0.8864	High Similarity	NPC478200
0.8864	High Similarity	NPC33144
0.8862	High Similarity	NPC226275
0.8862	High Similarity	NPC242895
0.8862	High Similarity	NPC196976
0.8862	High Similarity	NPC156139
0.8855	High Similarity	NPC254847
0.8846	High Similarity	NPC44437
0.8837	High Similarity	NPC478190
0.8824	High Similarity	NPC118288
0.8824	High Similarity	NPC276111
0.8819	High Similarity	NPC221777
0.8819	High Similarity	NPC473017
0.8819	High Similarity	NPC21305
0.8806	High Similarity	NPC478217
0.8806	High Similarity	NPC472904
0.8806	High Similarity	NPC313123
0.8797	High Similarity	NPC474655
0.879	High Similarity	NPC133909
0.879	High Similarity	NPC32032
0.8788	High Similarity	NPC53414
0.8788	High Similarity	NPC53206
0.8788	High Similarity	NPC53001
0.878	High Similarity	NPC272454
0.878	High Similarity	NPC115188
0.878	High Similarity	NPC179092
0.878	High Similarity	NPC35856
0.878	High Similarity	NPC178395
0.878	High Similarity	NPC301987
0.878	High Similarity	NPC222876
0.878	High Similarity	NPC244994
0.878	High Similarity	NPC297186
0.878	High Similarity	NPC26433
0.878	High Similarity	NPC292665
0.878	High Similarity	NPC159760
0.8779	High Similarity	NPC278375
0.877	High Similarity	NPC233165
0.877	High Similarity	NPC184579
0.877	High Similarity	NPC195262
0.877	High Similarity	NPC188814
0.8769	High Similarity	NPC153783
0.8741	High Similarity	NPC49108
0.8741	High Similarity	NPC474961
0.8741	High Similarity	NPC96692
0.8741	High Similarity	NPC135524
0.8741	High Similarity	NPC193555
0.8739	High Similarity	NPC162113
0.8739	High Similarity	NPC62546
0.8722	High Similarity	NPC472602
0.8722	High Similarity	NPC87723
0.8712	High Similarity	NPC223836
0.8712	High Similarity	NPC242712
0.8712	High Similarity	NPC65005
0.8712	High Similarity	NPC194764
0.8712	High Similarity	NPC158481
0.8712	High Similarity	NPC264112
0.871	High Similarity	NPC267552
0.871	High Similarity	NPC143427
0.871	High Similarity	NPC45438
0.871	High Similarity	NPC115159
0.871	High Similarity	NPC224273
0.871	High Similarity	NPC73532
0.871	High Similarity	NPC19174
0.8702	High Similarity	NPC12070
0.8702	High Similarity	NPC175943
0.8702	High Similarity	NPC474394
0.8682	High Similarity	NPC233056
0.8682	High Similarity	NPC244441
0.8676	High Similarity	NPC295712
0.8676	High Similarity	NPC354984
0.8676	High Similarity	NPC478202
0.8676	High Similarity	NPC174905
0.8676	High Similarity	NPC451542
0.8676	High Similarity	NPC313047
0.8676	High Similarity	NPC293545
0.8676	High Similarity	NPC472006
0.8676	High Similarity	NPC474203
0.8672	High Similarity	NPC24869
0.8667	High Similarity	NPC472035
0.8667	High Similarity	NPC67650
0.8667	High Similarity	NPC472603
0.8667	High Similarity	NPC478201
0.8667	High Similarity	NPC246638
0.8667	High Similarity	NPC53649
0.8667	High Similarity	NPC1704
0.8667	High Similarity	NPC204045
0.8667	High Similarity	NPC305845
0.8661	High Similarity	NPC160499
0.8657	High Similarity	NPC105456
0.8657	High Similarity	NPC143438
0.8657	High Similarity	NPC139634
0.8636	High Similarity	NPC182496
0.8636	High Similarity	NPC180905
0.8636	High Similarity	NPC249272
0.8629	High Similarity	NPC248363
0.8626	High Similarity	NPC139074
0.8626	High Similarity	NPC213485
0.8626	High Similarity	NPC114183
0.8626	High Similarity	NPC40524
0.8615	High Similarity	NPC475042
0.8613	High Similarity	NPC227841
0.8607	High Similarity	NPC125252
0.8603	High Similarity	NPC137649
0.8603	High Similarity	NPC250755
0.8603	High Similarity	NPC291078
0.8593	High Similarity	NPC158472
0.8593	High Similarity	NPC472601
0.8593	High Similarity	NPC472600
0.8571	High Similarity	NPC235115
0.8571	High Similarity	NPC475955
0.8571	High Similarity	NPC50455
0.8571	High Similarity	NPC474726
0.8561	High Similarity	NPC475088
0.8561	High Similarity	NPC270899
0.8551	High Similarity	NPC12402
0.8551	High Similarity	NPC34482
0.855	High Similarity	NPC135801
0.8548	High Similarity	NPC294964

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 NPC477454 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	324
0.1-0.2	1001
0.2-0.3	1592
0.3-0.4	2892
0.4-0.5	1864
0.5-0.6	1040
0.6-0.7	333
0.7-0.8	94
0.8-0.85	9
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8855	High Similarity	NPD1509	Clinical (unspecified phase)
0.8613	High Similarity	NPD7390	Discontinued
0.8571	High Similarity	NPD651	Clinical (unspecified phase)
0.855	High Similarity	NPD943	Approved
0.8413	Intermediate Similarity	NPD1201	Approved
0.8382	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8271	Intermediate Similarity	NPD1240	Approved
0.8226	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8154	Intermediate Similarity	NPD1470	Approved
0.8148	Intermediate Similarity	NPD1607	Approved
0.8031	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.8029	Intermediate Similarity	NPD1510	Phase 2
0.8028	Intermediate Similarity	NPD2532	Approved
0.8028	Intermediate Similarity	NPD2534	Approved
0.8028	Intermediate Similarity	NPD2533	Approved
0.7971	Intermediate Similarity	NPD5404	Approved
0.7971	Intermediate Similarity	NPD5406	Approved
0.7971	Intermediate Similarity	NPD5405	Approved
0.7971	Intermediate Similarity	NPD5408	Approved
0.7902	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD7819	Suspended
0.7815	Intermediate Similarity	NPD940	Approved
0.7815	Intermediate Similarity	NPD846	Approved
0.7805	Intermediate Similarity	NPD4750	Phase 3
0.7786	Intermediate Similarity	NPD9269	Phase 2
0.7786	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7752	Intermediate Similarity	NPD9268	Approved
0.7744	Intermediate Similarity	NPD1164	Approved
0.773	Intermediate Similarity	NPD1549	Phase 2
0.7724	Intermediate Similarity	NPD74	Approved
0.7724	Intermediate Similarity	NPD9266	Approved
0.7718	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD2796	Approved
0.7708	Intermediate Similarity	NPD1511	Approved
0.7676	Intermediate Similarity	NPD2800	Approved
0.7656	Intermediate Similarity	NPD9493	Approved
0.7655	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD1934	Approved
0.7647	Intermediate Similarity	NPD6959	Discontinued
0.7642	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD9267	Approved
0.7642	Intermediate Similarity	NPD9263	Approved
0.7642	Intermediate Similarity	NPD9264	Approved
0.7626	Intermediate Similarity	NPD6651	Approved
0.7622	Intermediate Similarity	NPD3750	Approved
0.7603	Intermediate Similarity	NPD1512	Approved
0.76	Intermediate Similarity	NPD2801	Approved
0.7597	Intermediate Similarity	NPD6232	Discontinued
0.7589	Intermediate Similarity	NPD2935	Discontinued
0.7589	Intermediate Similarity	NPD6100	Approved
0.7589	Intermediate Similarity	NPD6099	Approved
0.7564	Intermediate Similarity	NPD7473	Discontinued
0.7557	Intermediate Similarity	NPD2932	Approved
0.7557	Intermediate Similarity	NPD3019	Approved
0.7554	Intermediate Similarity	NPD230	Phase 1
0.755	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD4380	Phase 2
0.75	Intermediate Similarity	NPD3882	Suspended
0.7451	Intermediate Similarity	NPD3749	Approved
0.7415	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD2344	Approved
0.7405	Intermediate Similarity	NPD9545	Approved
0.7397	Intermediate Similarity	NPD3300	Phase 2
0.7379	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD7411	Suspended
0.7347	Intermediate Similarity	NPD6799	Approved
0.7338	Intermediate Similarity	NPD7075	Discontinued
0.7317	Intermediate Similarity	NPD9261	Approved
0.731	Intermediate Similarity	NPD1243	Approved
0.731	Intermediate Similarity	NPD2654	Approved
0.7299	Intermediate Similarity	NPD2798	Approved
0.7295	Intermediate Similarity	NPD1242	Phase 1
0.7285	Intermediate Similarity	NPD6599	Discontinued
0.7278	Intermediate Similarity	NPD6166	Phase 2
0.7278	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3748	Approved
0.7261	Intermediate Similarity	NPD5710	Approved
0.7261	Intermediate Similarity	NPD5711	Approved
0.7255	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD9281	Approved
0.7226	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD3764	Approved
0.7211	Intermediate Similarity	NPD2309	Approved
0.7208	Intermediate Similarity	NPD3817	Phase 2
0.717	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD7768	Phase 2
0.7153	Intermediate Similarity	NPD2799	Discontinued
0.7153	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6020	Phase 2
0.7132	Intermediate Similarity	NPD9717	Approved
0.7107	Intermediate Similarity	NPD844	Approved
0.7105	Intermediate Similarity	NPD3226	Approved
0.7103	Intermediate Similarity	NPD1551	Phase 2
0.7099	Intermediate Similarity	NPD7074	Phase 3
0.7092	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD3818	Discontinued
0.708	Intermediate Similarity	NPD1755	Approved
0.7078	Intermediate Similarity	NPD6801	Discontinued
0.7073	Intermediate Similarity	NPD3020	Approved
0.7055	Intermediate Similarity	NPD2346	Discontinued
0.7051	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD288	Approved
0.7037	Intermediate Similarity	NPD7054	Approved
0.7037	Intermediate Similarity	NPD4626	Approved
0.7032	Intermediate Similarity	NPD1465	Phase 2
0.7025	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD5494	Approved
0.7016	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD3972	Approved
0.6994	Remote Similarity	NPD7472	Approved
0.6985	Remote Similarity	NPD3026	Approved
0.6985	Remote Similarity	NPD3023	Approved
0.6978	Remote Similarity	NPD1203	Approved
0.6972	Remote Similarity	NPD411	Approved
0.6967	Remote Similarity	NPD2860	Approved
0.6967	Remote Similarity	NPD2859	Approved
0.6967	Remote Similarity	NPD1809	Phase 2
0.6963	Remote Similarity	NPD3024	Approved
0.6963	Remote Similarity	NPD3025	Approved
0.6959	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4749	Approved
0.6951	Remote Similarity	NPD6797	Phase 2
0.6944	Remote Similarity	NPD447	Suspended
0.6934	Remote Similarity	NPD422	Phase 1
0.6933	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD5844	Phase 1
0.6933	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD7251	Discontinued
0.6906	Remote Similarity	NPD1876	Approved
0.6901	Remote Similarity	NPD4625	Phase 3
0.6894	Remote Similarity	NPD3926	Phase 2
0.6885	Remote Similarity	NPD2933	Approved
0.6885	Remote Similarity	NPD2934	Approved
0.6884	Remote Similarity	NPD1608	Approved
0.6879	Remote Similarity	NPD9494	Approved
0.6867	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD7808	Phase 3
0.6863	Remote Similarity	NPD920	Approved
0.6863	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD2797	Approved
0.6853	Remote Similarity	NPD3268	Approved
0.6848	Remote Similarity	NPD5953	Discontinued
0.6846	Remote Similarity	NPD3021	Approved
0.6846	Remote Similarity	NPD3022	Approved
0.6842	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD1651	Approved
0.6818	Remote Similarity	NPD7635	Approved
0.6809	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD6559	Discontinued
0.6806	Remote Similarity	NPD6663	Approved
0.6803	Remote Similarity	NPD845	Approved
0.68	Remote Similarity	NPD7003	Approved
0.68	Remote Similarity	NPD4628	Phase 3
0.6786	Remote Similarity	NPD1283	Approved
0.6772	Remote Similarity	NPD5402	Approved
0.6766	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD5736	Approved
0.6753	Remote Similarity	NPD5403	Approved
0.675	Remote Similarity	NPD919	Approved
0.6736	Remote Similarity	NPD2313	Discontinued
0.6727	Remote Similarity	NPD7286	Phase 2
0.6716	Remote Similarity	NPD5951	Approved
0.6715	Remote Similarity	NPD5691	Approved
0.6713	Remote Similarity	NPD4908	Phase 1
0.6713	Remote Similarity	NPD6832	Phase 2
0.6711	Remote Similarity	NPD1471	Phase 3
0.6692	Remote Similarity	NPD2342	Discontinued
0.6691	Remote Similarity	NPD1610	Phase 2
0.6691	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.669	Remote Similarity	NPD520	Approved
0.6667	Remote Similarity	NPD2296	Approved
0.6667	Remote Similarity	NPD256	Approved
0.6667	Remote Similarity	NPD1247	Approved
0.6667	Remote Similarity	NPD4288	Approved
0.6667	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD17	Approved
0.6667	Remote Similarity	NPD255	Approved
0.6647	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD37	Approved
0.6642	Remote Similarity	NPD3091	Approved
0.6642	Remote Similarity	NPD1759	Phase 1
0.6641	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD5401	Approved
0.6621	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD8150	Discontinued
0.6599	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD1237	Approved
0.6587	Remote Similarity	NPD1729	Discontinued
0.6579	Remote Similarity	NPD8166	Discontinued
0.6579	Remote Similarity	NPD3400	Discontinued
0.6577	Remote Similarity	NPD4308	Phase 3
0.6571	Remote Similarity	NPD3092	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