NPASS Compound

Structure

CID92624 OpenBabel06191715432D 25 26 0 0 0 0 0 0 0 0999 V2000 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 7 1 0 0 0 0 5 10 1 0 0 0 0 6 8 2 0 0 0 0 6 9 1 0 0 0 0 7 11 1 0 0 0 0 8 12 1 0 0 0 0 9 13 2 0 0 0 0 10 14 1 0 0 0 0 11 18 1 0 0 0 0 12 18 2 0 0 0 0 13 18 1 0 0 0 0 14 19 1 0 0 0 0 15 19 2 0 0 0 0 15 20 1 0 0 0 0 16 20 2 0 0 0 0 16 21 1 0 0 0 0 17 22 1 0 0 0 0 17 23 2 0 0 0 0 19 22 1 0 0 0 0 20 24 1 0 0 0 0 21 22 2 0 0 0 0 21 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	340.2
Volume:	379.871
LogP:	6.022
LogD:	4.374
LogS:	-3.655
# Rotatable Bonds:	10
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.448
Synthetic Accessibility Score:	2.141
Fsp3:	0.409
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.939
MDCK Permeability:	1.3637780284625478e-05
Pgp-inhibitor:	0.96
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.122
Plasma Protein Binding (PPB):	99.22020721435547%
Volume Distribution (VD):	1.114
Pgp-substrate:	0.4805305004119873%

ADMET: Metabolism

CYP1A2-inhibitor:	0.97
CYP1A2-substrate:	0.206
CYP2C19-inhibitor:	0.955
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.699
CYP2C9-substrate:	0.956
CYP2D6-inhibitor:	0.948
CYP2D6-substrate:	0.318
CYP3A4-inhibitor:	0.62
CYP3A4-substrate:	0.136

ADMET: Excretion

Clearance (CL):	6.112
Half-life (T1/2):	0.606

ADMET: Toxicity

hERG Blockers:	0.25
Human Hepatotoxicity (H-HT):	0.051
Drug-inuced Liver Injury (DILI):	0.122
AMES Toxicity:	0.525
Rat Oral Acute Toxicity:	0.063
Maximum Recommended Daily Dose:	0.569
Skin Sensitization:	0.95
Carcinogencity:	0.068
Eye Corrosion:	0.063
Eye Irritation:	0.982
Respiratory Toxicity:	0.604

Download Data

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

Natural Product: NPC92624

Natural Product ID:	NPC92624
*Common Name:**	Kneglomeratanone A
IUPAC Name:	1-[2,4-dihydroxy-6-(8-phenyloctyl)phenyl]ethanone
Synonyms:
Standard InCHIKey:	IMXQBUNJVMBJFG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C22H28O3/c1-17(23)22-19(15-20(24)16-21(22)25)14-10-5-3-2-4-7-11-18-12-8-6-9-13-18/h6,8-9,12-13,15-16,24-25H,2-5,7,10-11,14H2,1H3
SMILES:	Oc1cc(CCCCCCCCc2ccccc2)c(c(c1)O)C(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL472643
PubChem CID:	196946
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
NPO11253	Knema glomerata	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8201311]
NPO5999	Schinopsis balansae	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7853	Baphia racemosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11253	Knema glomerata	Species	Myristicaceae	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
ED50	3
Others	2

Activity Type	# Activity
Cell Line	3
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	3.89	ug ml-1	PMID[459626]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	3.44	ug ml-1	PMID[459626]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	18.84	ug ml-1	PMID[459626]
NPT140	Organism	Artemia	Artemia	LC50	=	0.37	ug.mL-1	PMID[459626]
NPT141	Organism	Agrobacterium tumefaciens	Agrobacterium tumefaciens	T/C	=	38.0	%	PMID[459626]

☑ 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 NPC92624 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	340
0.1-0.2	1586
0.2-0.3	3659
0.3-0.4	11030
0.4-0.5	7975
0.5-0.6	4840
0.6-0.7	6606
0.7-0.8	5276
0.8-0.85	1017
0.85-0.9	283
0.9-0.95	77
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9919	High Similarity	NPC259942
0.9672	High Similarity	NPC477454
0.9606	High Similarity	NPC166480
0.9606	High Similarity	NPC282780
0.9593	High Similarity	NPC473691
0.9385	High Similarity	NPC290030
0.9308	High Similarity	NPC118919
0.9308	High Similarity	NPC191976
0.9297	High Similarity	NPC175738
0.9291	High Similarity	NPC17840
0.9291	High Similarity	NPC247477
0.928	High Similarity	NPC8745
0.928	High Similarity	NPC62952
0.928	High Similarity	NPC267846
0.9274	High Similarity	NPC13238
0.9242	High Similarity	NPC242994
0.9242	High Similarity	NPC138099
0.9242	High Similarity	NPC472903
0.9225	High Similarity	NPC267205
0.9213	High Similarity	NPC474998
0.9213	High Similarity	NPC109123
0.9206	High Similarity	NPC116513
0.9206	High Similarity	NPC100067
0.9206	High Similarity	NPC72158
0.9206	High Similarity	NPC190043
0.9206	High Similarity	NPC169250
0.9206	High Similarity	NPC105157
0.9206	High Similarity	NPC103356
0.9206	High Similarity	NPC23126
0.9206	High Similarity	NPC30501
0.9206	High Similarity	NPC162612
0.9206	High Similarity	NPC98254
0.9206	High Similarity	NPC266689
0.92	High Similarity	NPC10926
0.9187	High Similarity	NPC156139
0.9187	High Similarity	NPC196976
0.9187	High Similarity	NPC242895
0.9173	High Similarity	NPC169452
0.9173	High Similarity	NPC181560
0.9154	High Similarity	NPC44437
0.9134	High Similarity	NPC473017
0.9134	High Similarity	NPC21305
0.9134	High Similarity	NPC221777
0.9113	High Similarity	NPC32032
0.9113	High Similarity	NPC133909
0.9106	High Similarity	NPC297186
0.9106	High Similarity	NPC149246
0.9104	High Similarity	NPC472904
0.9098	High Similarity	NPC195262
0.9098	High Similarity	NPC188814
0.9091	High Similarity	NPC471905
0.9091	High Similarity	NPC53414
0.9091	High Similarity	NPC53206
0.9048	High Similarity	NPC201728
0.9048	High Similarity	NPC262671
0.9037	High Similarity	NPC193555
0.9037	High Similarity	NPC49108
0.9032	High Similarity	NPC143427
0.9032	High Similarity	NPC224273
0.9032	High Similarity	NPC19174
0.9032	High Similarity	NPC45438
0.9032	High Similarity	NPC115159
0.9032	High Similarity	NPC73532
0.9032	High Similarity	NPC267552
0.9015	High Similarity	NPC264112
0.9015	High Similarity	NPC254847
0.9015	High Similarity	NPC65005
0.9015	High Similarity	NPC194764
0.8992	High Similarity	NPC147757
0.8992	High Similarity	NPC233056
0.8992	High Similarity	NPC244441
0.8984	High Similarity	NPC41263
0.8976	High Similarity	NPC160499
0.8971	High Similarity	NPC313047
0.8971	High Similarity	NPC295712
0.8971	High Similarity	NPC474203
0.8971	High Similarity	NPC451542
0.896	High Similarity	NPC91105
0.896	High Similarity	NPC309765
0.8952	High Similarity	NPC146642
0.8952	High Similarity	NPC248363
0.8947	High Similarity	NPC53001
0.8943	High Similarity	NPC161617
0.8939	High Similarity	NPC290803
0.8934	High Similarity	NPC121259
0.8931	High Similarity	NPC37299
0.8931	High Similarity	NPC213485
0.8931	High Similarity	NPC40524
0.8931	High Similarity	NPC139074
0.8931	High Similarity	NPC180261
0.8923	High Similarity	NPC475042
0.8898	High Similarity	NPC475733
0.8897	High Similarity	NPC137649
0.8897	High Similarity	NPC474961
0.8897	High Similarity	NPC135524
0.8897	High Similarity	NPC250755
0.8889	High Similarity	NPC472029
0.8889	High Similarity	NPC65761
0.8881	High Similarity	NPC87723
0.888	High Similarity	NPC303737
0.888	High Similarity	NPC215392
0.8872	High Similarity	NPC223836
0.8871	High Similarity	NPC159525
0.8871	High Similarity	NPC294037
0.8864	High Similarity	NPC12070
0.8864	High Similarity	NPC475088
0.8862	High Similarity	NPC40649
0.8862	High Similarity	NPC209486
0.8855	High Similarity	NPC478190
0.8855	High Similarity	NPC135801
0.8852	High Similarity	NPC477453
0.8846	High Similarity	NPC62219
0.8846	High Similarity	NPC26697
0.8837	High Similarity	NPC95537
0.8837	High Similarity	NPC179898
0.8832	High Similarity	NPC174905
0.8832	High Similarity	NPC293545
0.8824	High Similarity	NPC204045
0.8824	High Similarity	NPC305845
0.8824	High Similarity	NPC246638
0.8824	High Similarity	NPC187843
0.8815	High Similarity	NPC162939
0.8815	High Similarity	NPC472368
0.8815	High Similarity	NPC143438
0.881	High Similarity	NPC283514
0.881	High Similarity	NPC244351
0.8806	High Similarity	NPC65837
0.8806	High Similarity	NPC213603
0.8806	High Similarity	NPC71256
0.8806	High Similarity	NPC474771
0.8806	High Similarity	NPC474849
0.8806	High Similarity	NPC472364
0.8806	High Similarity	NPC178467
0.8806	High Similarity	NPC472367
0.8806	High Similarity	NPC476333
0.8806	High Similarity	NPC473391
0.8806	High Similarity	NPC149372
0.8797	High Similarity	NPC130899
0.8797	High Similarity	NPC283590
0.8797	High Similarity	NPC249272
0.8797	High Similarity	NPC70859
0.8797	High Similarity	NPC61153
0.879	High Similarity	NPC158222
0.8788	High Similarity	NPC114183
0.8788	High Similarity	NPC48036
0.8779	High Similarity	NPC469526
0.8779	High Similarity	NPC34070
0.8779	High Similarity	NPC275504
0.8769	High Similarity	NPC476119
0.8768	High Similarity	NPC193703
0.8768	High Similarity	NPC227841
0.8768	High Similarity	NPC21599
0.875	High Similarity	NPC109232
0.875	High Similarity	NPC203063
0.875	High Similarity	NPC472366
0.8741	High Similarity	NPC478200
0.8741	High Similarity	NPC9121
0.8741	High Similarity	NPC191835
0.8741	High Similarity	NPC177307
0.8741	High Similarity	NPC33144
0.8741	High Similarity	NPC475974
0.8741	High Similarity	NPC20210
0.873	High Similarity	NPC198336
0.8722	High Similarity	NPC144051
0.8722	High Similarity	NPC20560
0.8722	High Similarity	NPC28753
0.8722	High Similarity	NPC18877
0.8722	High Similarity	NPC270899
0.8722	High Similarity	NPC294593
0.8722	High Similarity	NPC474519
0.8722	High Similarity	NPC159623
0.8722	High Similarity	NPC204960
0.8722	High Similarity	NPC82225
0.8705	High Similarity	NPC34482
0.8705	High Similarity	NPC12402
0.8696	High Similarity	NPC296752
0.8696	High Similarity	NPC310340
0.8696	High Similarity	NPC84266
0.8696	High Similarity	NPC478202
0.8689	High Similarity	NPC276111
0.8689	High Similarity	NPC118288
0.8686	High Similarity	NPC478217
0.8686	High Similarity	NPC313123
0.8686	High Similarity	NPC275734
0.8686	High Similarity	NPC110810
0.8676	High Similarity	NPC190457
0.8672	High Similarity	NPC173978
0.8667	High Similarity	NPC194579
0.8667	High Similarity	NPC44960
0.8667	High Similarity	NPC474110
0.8667	High Similarity	NPC70380
0.8657	High Similarity	NPC470210
0.8657	High Similarity	NPC286336
0.8657	High Similarity	NPC161632
0.8651	High Similarity	NPC301987
0.8651	High Similarity	NPC292665
0.8651	High Similarity	NPC35856
0.8651	High Similarity	NPC178395
0.8651	High Similarity	NPC115188
0.8651	High Similarity	NPC159760

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 NPC92624 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	340
0.1-0.2	954
0.2-0.3	1356
0.3-0.4	2730
0.4-0.5	2079
0.5-0.6	1185
0.6-0.7	375
0.7-0.8	116
0.8-0.85	10
0.85-0.9	4
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9015	High Similarity	NPD1509	Clinical (unspecified phase)
0.8855	High Similarity	NPD943	Approved
0.8768	High Similarity	NPD7390	Discontinued
0.873	High Similarity	NPD1201	Approved
0.8571	High Similarity	NPD1240	Approved
0.8462	Intermediate Similarity	NPD1470	Approved
0.8456	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8444	Intermediate Similarity	NPD1607	Approved
0.8321	Intermediate Similarity	NPD1510	Phase 2
0.8273	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD5408	Approved
0.8261	Intermediate Similarity	NPD5404	Approved
0.8261	Intermediate Similarity	NPD5406	Approved
0.8261	Intermediate Similarity	NPD5405	Approved
0.8254	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD7819	Suspended
0.8071	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8071	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8045	Intermediate Similarity	NPD1164	Approved
0.8014	Intermediate Similarity	NPD1549	Phase 2
0.8	Intermediate Similarity	NPD2796	Approved
0.7987	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD1511	Approved
0.7931	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD1934	Approved
0.7902	Intermediate Similarity	NPD3750	Approved
0.7877	Intermediate Similarity	NPD1512	Approved
0.7872	Intermediate Similarity	NPD2935	Discontinued
0.7867	Intermediate Similarity	NPD2801	Approved
0.7857	Intermediate Similarity	NPD6232	Discontinued
0.7821	Intermediate Similarity	NPD7473	Discontinued
0.7815	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD2533	Approved
0.7808	Intermediate Similarity	NPD2532	Approved
0.7808	Intermediate Similarity	NPD2534	Approved
0.7792	Intermediate Similarity	NPD6959	Discontinued
0.7786	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD4380	Phase 2
0.7763	Intermediate Similarity	NPD3882	Suspended
0.7727	Intermediate Similarity	NPD3019	Approved
0.7727	Intermediate Similarity	NPD2932	Approved
0.7712	Intermediate Similarity	NPD3749	Approved
0.7705	Intermediate Similarity	NPD940	Approved
0.7705	Intermediate Similarity	NPD846	Approved
0.7698	Intermediate Similarity	NPD4750	Phase 3
0.7692	Intermediate Similarity	NPD2344	Approved
0.7623	Intermediate Similarity	NPD1242	Phase 1
0.7622	Intermediate Similarity	NPD6099	Approved
0.7622	Intermediate Similarity	NPD6100	Approved
0.7619	Intermediate Similarity	NPD9266	Approved
0.7619	Intermediate Similarity	NPD74	Approved
0.7619	Intermediate Similarity	NPD6799	Approved
0.7616	Intermediate Similarity	NPD7411	Suspended
0.7597	Intermediate Similarity	NPD7075	Discontinued
0.7591	Intermediate Similarity	NPD2798	Approved
0.7586	Intermediate Similarity	NPD2800	Approved
0.7568	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD9493	Approved
0.7556	Intermediate Similarity	NPD9269	Phase 2
0.7552	Intermediate Similarity	NPD3748	Approved
0.7551	Intermediate Similarity	NPD3300	Phase 2
0.755	Intermediate Similarity	NPD6599	Discontinued
0.754	Intermediate Similarity	NPD9264	Approved
0.754	Intermediate Similarity	NPD9267	Approved
0.754	Intermediate Similarity	NPD9263	Approved
0.754	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD6651	Approved
0.7532	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6166	Phase 2
0.7532	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD9268	Approved
0.7516	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3764	Approved
0.7484	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD2309	Approved
0.7468	Intermediate Similarity	NPD3817	Phase 2
0.7431	Intermediate Similarity	NPD2799	Discontinued
0.7421	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD7768	Phase 2
0.7415	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD3020	Approved
0.7391	Intermediate Similarity	NPD6020	Phase 2
0.7379	Intermediate Similarity	NPD1551	Phase 2
0.7376	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD3226	Approved
0.7347	Intermediate Similarity	NPD1243	Approved
0.7346	Intermediate Similarity	NPD7074	Phase 3
0.7343	Intermediate Similarity	NPD230	Phase 1
0.7338	Intermediate Similarity	NPD6801	Discontinued
0.7329	Intermediate Similarity	NPD2346	Discontinued
0.7329	Intermediate Similarity	NPD3818	Discontinued
0.7313	Intermediate Similarity	NPD9545	Approved
0.731	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD3972	Approved
0.7295	Intermediate Similarity	NPD2859	Approved
0.7295	Intermediate Similarity	NPD2860	Approved
0.7284	Intermediate Similarity	NPD7054	Approved
0.7278	Intermediate Similarity	NPD5494	Approved
0.7266	Intermediate Similarity	NPD1203	Approved
0.7239	Intermediate Similarity	NPD7472	Approved
0.723	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD9261	Approved
0.7213	Intermediate Similarity	NPD2934	Approved
0.7213	Intermediate Similarity	NPD2933	Approved
0.7197	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD6797	Phase 2
0.7194	Intermediate Similarity	NPD1876	Approved
0.7188	Intermediate Similarity	NPD5710	Approved
0.7188	Intermediate Similarity	NPD5711	Approved
0.7183	Intermediate Similarity	NPD4625	Phase 3
0.7179	Intermediate Similarity	NPD1465	Phase 2
0.7178	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD5844	Phase 1
0.7174	Intermediate Similarity	NPD1608	Approved
0.7154	Intermediate Similarity	NPD3022	Approved
0.7154	Intermediate Similarity	NPD3021	Approved
0.7153	Intermediate Similarity	NPD3026	Approved
0.7153	Intermediate Similarity	NPD3023	Approved
0.7152	Intermediate Similarity	NPD7251	Discontinued
0.7143	Intermediate Similarity	NPD3926	Phase 2
0.7143	Intermediate Similarity	NPD9281	Approved
0.7143	Intermediate Similarity	NPD2797	Approved
0.7133	Intermediate Similarity	NPD3268	Approved
0.7132	Intermediate Similarity	NPD3025	Approved
0.7132	Intermediate Similarity	NPD1651	Approved
0.7132	Intermediate Similarity	NPD3024	Approved
0.7124	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD1755	Approved
0.7121	Intermediate Similarity	NPD7635	Approved
0.7114	Intermediate Similarity	NPD2654	Approved
0.7108	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD7808	Phase 3
0.7091	Intermediate Similarity	NPD5953	Discontinued
0.7086	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD1283	Approved
0.7067	Intermediate Similarity	NPD4628	Phase 3
0.7067	Intermediate Similarity	NPD7003	Approved
0.7067	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD9717	Approved
0.7048	Intermediate Similarity	NPD6559	Discontinued
0.7025	Intermediate Similarity	NPD5402	Approved
0.7016	Intermediate Similarity	NPD844	Approved
0.7015	Intermediate Similarity	NPD5951	Approved
0.7014	Intermediate Similarity	NPD2313	Discontinued
0.7013	Intermediate Similarity	NPD5403	Approved
0.7013	Intermediate Similarity	NPD920	Approved
0.7006	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2342	Discontinued
0.6993	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD6832	Phase 2
0.6993	Remote Similarity	NPD4908	Phase 1
0.698	Remote Similarity	NPD1471	Phase 3
0.6978	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD1610	Phase 2
0.6978	Remote Similarity	NPD422	Phase 1
0.697	Remote Similarity	NPD7286	Phase 2
0.6966	Remote Similarity	NPD6663	Approved
0.696	Remote Similarity	NPD288	Approved
0.6957	Remote Similarity	NPD17	Approved
0.6957	Remote Similarity	NPD4626	Approved
0.6935	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5736	Approved
0.6918	Remote Similarity	NPD2296	Approved
0.6918	Remote Similarity	NPD4288	Approved
0.6899	Remote Similarity	NPD1237	Approved
0.6897	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD411	Approved
0.6894	Remote Similarity	NPD919	Approved
0.6893	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD5401	Approved
0.6879	Remote Similarity	NPD4749	Approved
0.6879	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD447	Suspended
0.6871	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD1281	Approved
0.6846	Remote Similarity	NPD4308	Phase 3
0.6842	Remote Similarity	NPD8150	Discontinued
0.6842	Remote Similarity	NPD3400	Discontinued
0.6828	Remote Similarity	NPD3027	Phase 3
0.6822	Remote Similarity	NPD1929	Approved
0.6822	Remote Similarity	NPD1930	Approved
0.6822	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD7458	Discontinued
0.6815	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD3091	Approved
0.6812	Remote Similarity	NPD1548	Phase 1
0.681	Remote Similarity	NPD1247	Approved
0.681	Remote Similarity	NPD7199	Phase 2
0.6809	Remote Similarity	NPD4878	Approved
0.6806	Remote Similarity	NPD9494	Approved
0.6797	Remote Similarity	NPD6190	Approved
0.6792	Remote Similarity	NPD37	Approved
0.6786	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD3266	Approved
0.6783	Remote Similarity	NPD3267	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