NPASS Compound

Structure

NPC473691 OpenBabel07101719122D 24 24 0 0 0 0 0 0 0 0999 V2000 -10.3923 0.0000 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 -10.3923 -1.0000 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 -8.6603 -1.0000 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 -6.9282 -1.0000 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 -5.1962 -1.0000 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 -2.5981 -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 -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 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 -1.7321 0.0000 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 3 1 0 0 0 0 2 17 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 18 1 0 0 0 0 15 18 2 0 0 0 0 15 19 1 0 0 0 0 16 19 2 0 0 0 0 16 20 1 0 0 0 0 17 21 1 0 0 0 0 17 22 2 0 0 0 0 18 21 1 0 0 0 0 19 23 1 0 0 0 0 20 21 2 0 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	334.25
Volume:	379.041
LogP:	7.262
LogD:	4.596
LogS:	-3.547
# Rotatable Bonds:	13
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.336
Synthetic Accessibility Score:	2.252
Fsp3:	0.667
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:	-4.9
MDCK Permeability:	1.4159803868096787e-05
Pgp-inhibitor:	0.132
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):	0.107
Plasma Protein Binding (PPB):	99.3720474243164%
Volume Distribution (VD):	2.308
Pgp-substrate:	1.0636107921600342%

ADMET: Metabolism

CYP1A2-inhibitor:	0.906
CYP1A2-substrate:	0.202
CYP2C19-inhibitor:	0.815
CYP2C19-substrate:	0.069
CYP2C9-inhibitor:	0.311
CYP2C9-substrate:	0.974
CYP2D6-inhibitor:	0.904
CYP2D6-substrate:	0.189
CYP3A4-inhibitor:	0.52
CYP3A4-substrate:	0.061

ADMET: Excretion

Clearance (CL):	4.89
Half-life (T1/2):	0.38

ADMET: Toxicity

hERG Blockers:	0.144
Human Hepatotoxicity (H-HT):	0.029
Drug-inuced Liver Injury (DILI):	0.284
AMES Toxicity:	0.364
Rat Oral Acute Toxicity:	0.074
Maximum Recommended Daily Dose:	0.557
Skin Sensitization:	0.945
Carcinogencity:	0.05
Eye Corrosion:	0.504
Eye Irritation:	0.985
Respiratory Toxicity:	0.879

Download Data

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

Natural Product: NPC473691

Natural Product ID:	NPC473691
*Common Name:**	Kneglomeratanone B
IUPAC Name:	1-(2,4-dihydroxy-6-tridecylphenyl)ethanone
Synonyms:
Standard InCHIKey:	LKFIFZHFSPDZEZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H34O3/c1-3-4-5-6-7-8-9-10-11-12-13-14-18-15-19(23)16-20(24)21(18)17(2)22/h15-16,23-24H,3-14H2,1-2H3
SMILES:	CCCCCCCCCCCCCC1=C(C(=CC(=C1)O)O)C(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL449313
PubChem CID:	196947
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]
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	=	2.3	ug ml-1	PMID[528960]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	1.12	ug ml-1	PMID[528960]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	6.56	ug ml-1	PMID[528960]
NPT140	Organism	Artemia	Artemia	LC50	=	1.92	ug.mL-1	PMID[528960]
NPT141	Organism	Agrobacterium tumefaciens	Agrobacterium tumefaciens	T/C	=	38.0	%	PMID[528960]

☑ 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 NPC473691 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	NPC477454
0.9675	High Similarity	NPC259942
0.9593	High Similarity	NPC92624
0.9516	High Similarity	NPC247477
0.9516	High Similarity	NPC17840
0.9333	High Similarity	NPC149246
0.9291	High Similarity	NPC37299
0.9291	High Similarity	NPC180261
0.9268	High Similarity	NPC201728
0.9268	High Similarity	NPC262671
0.9225	High Similarity	NPC191976
0.9219	High Similarity	NPC282780
0.9219	High Similarity	NPC166480
0.92	High Similarity	NPC41263
0.918	High Similarity	NPC91105
0.9174	High Similarity	NPC146642
0.9113	High Similarity	NPC475733
0.9106	High Similarity	NPC472029
0.9106	High Similarity	NPC65761
0.9098	High Similarity	NPC215392
0.9091	High Similarity	NPC294037
0.9083	High Similarity	NPC40649
0.9083	High Similarity	NPC209486
0.9055	High Similarity	NPC62219
0.9024	High Similarity	NPC309765
0.9015	High Similarity	NPC472903
0.9008	High Similarity	NPC65837
0.9008	High Similarity	NPC178467
0.9008	High Similarity	NPC71256
0.9008	High Similarity	NPC194579
0.9008	High Similarity	NPC161617
0.9008	High Similarity	NPC474771
0.9008	High Similarity	NPC149372
0.9008	High Similarity	NPC290030
0.9008	High Similarity	NPC474849
0.9	High Similarity	NPC290803
0.9	High Similarity	NPC121259
0.8992	High Similarity	NPC48036
0.8992	High Similarity	NPC267205
0.8968	High Similarity	NPC209959
0.8968	High Similarity	NPC116513
0.896	High Similarity	NPC10926
0.8943	High Similarity	NPC303737
0.8939	High Similarity	NPC475974
0.8939	High Similarity	NPC191835
0.8931	High Similarity	NPC118919
0.8923	High Similarity	NPC474519
0.8917	High Similarity	NPC477453
0.8915	High Similarity	NPC175738
0.8906	High Similarity	NPC147757
0.8898	High Similarity	NPC179898
0.8889	High Similarity	NPC62952
0.8889	High Similarity	NPC267846
0.8889	High Similarity	NPC8745
0.8881	High Similarity	NPC472904
0.888	High Similarity	NPC13238
0.8872	High Similarity	NPC242994
0.8872	High Similarity	NPC162939
0.8872	High Similarity	NPC138099
0.8864	High Similarity	NPC53001
0.8864	High Similarity	NPC471905
0.8864	High Similarity	NPC70380
0.8862	High Similarity	NPC178395
0.8862	High Similarity	NPC179092
0.8862	High Similarity	NPC159760
0.8862	High Similarity	NPC272454
0.8862	High Similarity	NPC301987
0.8862	High Similarity	NPC26433
0.8862	High Similarity	NPC292665
0.8862	High Similarity	NPC222876
0.8862	High Similarity	NPC115188
0.8862	High Similarity	NPC35856
0.8862	High Similarity	NPC244994
0.8837	High Similarity	NPC219892
0.8837	High Similarity	NPC189823
0.8828	High Similarity	NPC474998
0.8828	High Similarity	NPC109123
0.8824	High Similarity	NPC162113
0.8824	High Similarity	NPC62546
0.8819	High Similarity	NPC23126
0.8819	High Similarity	NPC100067
0.8819	High Similarity	NPC30501
0.8819	High Similarity	NPC98254
0.8819	High Similarity	NPC105157
0.8819	High Similarity	NPC72158
0.8819	High Similarity	NPC162612
0.8819	High Similarity	NPC103356
0.8819	High Similarity	NPC266689
0.8819	High Similarity	NPC190043
0.8819	High Similarity	NPC169250
0.8815	High Similarity	NPC474961
0.8806	High Similarity	NPC169452
0.8806	High Similarity	NPC181560
0.8797	High Similarity	NPC33144
0.8797	High Similarity	NPC177307
0.8797	High Similarity	NPC87723
0.8797	High Similarity	NPC472403
0.8797	High Similarity	NPC478200
0.8797	High Similarity	NPC94248
0.8797	High Similarity	NPC212693
0.8797	High Similarity	NPC9121
0.879	High Similarity	NPC196976
0.879	High Similarity	NPC156139
0.879	High Similarity	NPC242895
0.879	High Similarity	NPC226275
0.8788	High Similarity	NPC254847
0.8779	High Similarity	NPC44437
0.8769	High Similarity	NPC478190
0.875	High Similarity	NPC21305
0.875	High Similarity	NPC221777
0.875	High Similarity	NPC118288
0.875	High Similarity	NPC473017
0.875	High Similarity	NPC24869
0.875	High Similarity	NPC276111
0.8741	High Similarity	NPC313123
0.8741	High Similarity	NPC478217
0.8731	High Similarity	NPC474655
0.8722	High Similarity	NPC53206
0.8722	High Similarity	NPC53414
0.872	High Similarity	NPC133909
0.872	High Similarity	NPC32032
0.8712	High Similarity	NPC278375
0.8712	High Similarity	NPC249272
0.871	High Similarity	NPC297186
0.8702	High Similarity	NPC153783
0.8699	High Similarity	NPC195262
0.8699	High Similarity	NPC233165
0.8699	High Similarity	NPC188814
0.8699	High Similarity	NPC184579
0.8676	High Similarity	NPC96692
0.8676	High Similarity	NPC193555
0.8676	High Similarity	NPC135524
0.8676	High Similarity	NPC49108
0.8657	High Similarity	NPC472602
0.8647	High Similarity	NPC223836
0.8647	High Similarity	NPC158481
0.8647	High Similarity	NPC264112
0.8647	High Similarity	NPC242712
0.8647	High Similarity	NPC65005
0.8647	High Similarity	NPC194764
0.864	High Similarity	NPC224273
0.864	High Similarity	NPC73532
0.864	High Similarity	NPC143427
0.864	High Similarity	NPC19174
0.864	High Similarity	NPC267552
0.864	High Similarity	NPC45438
0.864	High Similarity	NPC115159
0.8636	High Similarity	NPC175943
0.8636	High Similarity	NPC474394
0.8636	High Similarity	NPC475088
0.8636	High Similarity	NPC12070
0.8636	High Similarity	NPC270899
0.8615	High Similarity	NPC233056
0.8615	High Similarity	NPC244441
0.8613	High Similarity	NPC295712
0.8613	High Similarity	NPC451542
0.8613	High Similarity	NPC354984
0.8613	High Similarity	NPC174905
0.8613	High Similarity	NPC478202
0.8613	High Similarity	NPC472006
0.8613	High Similarity	NPC313047
0.8613	High Similarity	NPC293545
0.8613	High Similarity	NPC474203
0.8603	High Similarity	NPC478201
0.8603	High Similarity	NPC67650
0.8603	High Similarity	NPC472603
0.8603	High Similarity	NPC246638
0.8603	High Similarity	NPC1704
0.8603	High Similarity	NPC204045
0.8603	High Similarity	NPC472035
0.8603	High Similarity	NPC305845
0.8603	High Similarity	NPC53649
0.8594	High Similarity	NPC328983
0.8594	High Similarity	NPC160499
0.8593	High Similarity	NPC139634
0.8593	High Similarity	NPC105456
0.8593	High Similarity	NPC143438
0.8571	High Similarity	NPC180905
0.8571	High Similarity	NPC182496
0.8571	High Similarity	NPC244351
0.8561	High Similarity	NPC114183
0.8561	High Similarity	NPC139074
0.8561	High Similarity	NPC213485
0.8561	High Similarity	NPC40524
0.856	High Similarity	NPC248363
0.8551	High Similarity	NPC227841
0.855	High Similarity	NPC475042
0.854	High Similarity	NPC250755
0.854	High Similarity	NPC137649
0.854	High Similarity	NPC291078
0.8537	High Similarity	NPC125252
0.8529	High Similarity	NPC472601
0.8529	High Similarity	NPC472600
0.8529	High Similarity	NPC158472
0.8527	High Similarity	NPC316625
0.8527	High Similarity	NPC329205
0.8516	High Similarity	NPC167055
0.8516	High Similarity	NPC240744
0.8507	High Similarity	NPC50455
0.8507	High Similarity	NPC474726

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 NPC473691 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
0.8788	High Similarity	NPD1509	Clinical (unspecified phase)
0.8551	High Similarity	NPD7390	Discontinued
0.8507	High Similarity	NPD651	Clinical (unspecified phase)
0.8485	Intermediate Similarity	NPD943	Approved
0.8346	Intermediate Similarity	NPD1201	Approved
0.8321	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8209	Intermediate Similarity	NPD1240	Approved
0.816	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD1470	Approved
0.8088	Intermediate Similarity	NPD1607	Approved
0.7972	Intermediate Similarity	NPD2532	Approved
0.7972	Intermediate Similarity	NPD2534	Approved
0.7972	Intermediate Similarity	NPD2533	Approved
0.7971	Intermediate Similarity	NPD1510	Phase 2
0.7969	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD5408	Approved
0.7914	Intermediate Similarity	NPD5404	Approved
0.7914	Intermediate Similarity	NPD5405	Approved
0.7914	Intermediate Similarity	NPD5406	Approved
0.7905	Intermediate Similarity	NPD7819	Suspended
0.7847	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD940	Approved
0.775	Intermediate Similarity	NPD846	Approved
0.7742	Intermediate Similarity	NPD4750	Phase 3
0.773	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD9269	Phase 2
0.7698	Intermediate Similarity	NPD6651	Approved
0.7692	Intermediate Similarity	NPD9268	Approved
0.7687	Intermediate Similarity	NPD1164	Approved
0.7676	Intermediate Similarity	NPD1549	Phase 2
0.7667	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD9266	Approved
0.7661	Intermediate Similarity	NPD74	Approved
0.766	Intermediate Similarity	NPD6100	Approved
0.766	Intermediate Similarity	NPD6099	Approved
0.766	Intermediate Similarity	NPD2796	Approved
0.7655	Intermediate Similarity	NPD1511	Approved
0.7628	Intermediate Similarity	NPD7473	Discontinued
0.7622	Intermediate Similarity	NPD2800	Approved
0.7616	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD1934	Approved
0.7597	Intermediate Similarity	NPD6959	Discontinued
0.7597	Intermediate Similarity	NPD9493	Approved
0.7581	Intermediate Similarity	NPD9264	Approved
0.7581	Intermediate Similarity	NPD9267	Approved
0.7581	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD9263	Approved
0.7569	Intermediate Similarity	NPD3750	Approved
0.7551	Intermediate Similarity	NPD1512	Approved
0.755	Intermediate Similarity	NPD2801	Approved
0.7548	Intermediate Similarity	NPD6232	Discontinued
0.7535	Intermediate Similarity	NPD2935	Discontinued
0.75	Intermediate Similarity	NPD3019	Approved
0.75	Intermediate Similarity	NPD2932	Approved
0.75	Intermediate Similarity	NPD230	Phase 1
0.7467	Intermediate Similarity	NPD4380	Phase 2
0.7451	Intermediate Similarity	NPD3882	Suspended
0.7403	Intermediate Similarity	NPD3749	Approved
0.7403	Intermediate Similarity	NPD7075	Discontinued
0.7365	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD2344	Approved
0.7348	Intermediate Similarity	NPD9545	Approved
0.7347	Intermediate Similarity	NPD3300	Phase 2
0.7329	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD7411	Suspended
0.7297	Intermediate Similarity	NPD6799	Approved
0.726	Intermediate Similarity	NPD1243	Approved
0.726	Intermediate Similarity	NPD2654	Approved
0.7258	Intermediate Similarity	NPD9261	Approved
0.7246	Intermediate Similarity	NPD2798	Approved
0.7237	Intermediate Similarity	NPD6599	Discontinued
0.7236	Intermediate Similarity	NPD1242	Phase 1
0.7233	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD6166	Phase 2
0.7226	Intermediate Similarity	NPD7768	Phase 2
0.7222	Intermediate Similarity	NPD3748	Approved
0.7215	Intermediate Similarity	NPD5711	Approved
0.7215	Intermediate Similarity	NPD5710	Approved
0.7211	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD9281	Approved
0.7163	Intermediate Similarity	NPD3764	Approved
0.7163	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD2309	Approved
0.7161	Intermediate Similarity	NPD3817	Phase 2
0.716	Intermediate Similarity	NPD7074	Phase 3
0.7125	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD2799	Discontinued
0.7099	Intermediate Similarity	NPD6020	Phase 2
0.7099	Intermediate Similarity	NPD7054	Approved
0.708	Intermediate Similarity	NPD9717	Approved
0.7059	Intermediate Similarity	NPD3226	Approved
0.7055	Intermediate Similarity	NPD7472	Approved
0.7055	Intermediate Similarity	NPD1551	Phase 2
0.7049	Intermediate Similarity	NPD844	Approved
0.7037	Intermediate Similarity	NPD3818	Discontinued
0.7032	Intermediate Similarity	NPD6801	Discontinued
0.7029	Intermediate Similarity	NPD1755	Approved
0.7016	Intermediate Similarity	NPD3020	Approved
0.7007	Intermediate Similarity	NPD2346	Discontinued
0.7006	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD288	Approved
0.6987	Remote Similarity	NPD1465	Phase 2
0.6985	Remote Similarity	NPD4626	Approved
0.6981	Remote Similarity	NPD5494	Approved
0.697	Remote Similarity	NPD7251	Discontinued
0.6967	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.696	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD3972	Approved
0.6934	Remote Similarity	NPD3026	Approved
0.6934	Remote Similarity	NPD3023	Approved
0.6929	Remote Similarity	NPD1203	Approved
0.6928	Remote Similarity	NPD7808	Phase 3
0.6923	Remote Similarity	NPD411	Approved
0.6913	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD3025	Approved
0.6912	Remote Similarity	NPD3024	Approved
0.6911	Remote Similarity	NPD2859	Approved
0.6911	Remote Similarity	NPD1809	Phase 2
0.6911	Remote Similarity	NPD2860	Approved
0.6909	Remote Similarity	NPD6797	Phase 2
0.6906	Remote Similarity	NPD4749	Approved
0.6897	Remote Similarity	NPD447	Suspended
0.6894	Remote Similarity	NPD7635	Approved
0.689	Remote Similarity	NPD5844	Phase 1
0.6887	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD422	Phase 1
0.6879	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6663	Approved
0.6857	Remote Similarity	NPD1876	Approved
0.6853	Remote Similarity	NPD4625	Phase 3
0.6852	Remote Similarity	NPD3926	Phase 2
0.6835	Remote Similarity	NPD1608	Approved
0.6831	Remote Similarity	NPD9494	Approved
0.6831	Remote Similarity	NPD5736	Approved
0.6829	Remote Similarity	NPD2934	Approved
0.6829	Remote Similarity	NPD2933	Approved
0.6826	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD920	Approved
0.6818	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD2797	Approved
0.6807	Remote Similarity	NPD5953	Discontinued
0.6806	Remote Similarity	NPD3268	Approved
0.6797	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD3021	Approved
0.6794	Remote Similarity	NPD3022	Approved
0.6788	Remote Similarity	NPD1651	Approved
0.6788	Remote Similarity	NPD7286	Phase 2
0.6783	Remote Similarity	NPD6832	Phase 2
0.6766	Remote Similarity	NPD6559	Discontinued
0.6766	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD7003	Approved
0.6755	Remote Similarity	NPD4628	Phase 3
0.6748	Remote Similarity	NPD845	Approved
0.6738	Remote Similarity	NPD1283	Approved
0.673	Remote Similarity	NPD5402	Approved
0.6726	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.671	Remote Similarity	NPD5403	Approved
0.6708	Remote Similarity	NPD919	Approved
0.6705	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.669	Remote Similarity	NPD2313	Discontinued
0.669	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5691	Approved
0.6667	Remote Similarity	NPD4908	Phase 1
0.6667	Remote Similarity	NPD1471	Phase 3
0.6667	Remote Similarity	NPD8150	Discontinued
0.6667	Remote Similarity	NPD5951	Approved
0.6645	Remote Similarity	NPD8166	Discontinued
0.6644	Remote Similarity	NPD520	Approved
0.6643	Remote Similarity	NPD1610	Phase 2
0.6643	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD2342	Discontinued
0.6626	Remote Similarity	NPD1247	Approved
0.6625	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD4288	Approved
0.6625	Remote Similarity	NPD2296	Approved
0.6624	Remote Similarity	NPD7458	Discontinued
0.6619	Remote Similarity	NPD17	Approved
0.6618	Remote Similarity	NPD255	Approved
0.6618	Remote Similarity	NPD256	Approved
0.6607	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD37	Approved
0.6594	Remote Similarity	NPD3091	Approved
0.6594	Remote Similarity	NPD1759	Phase 1
0.6585	Remote Similarity	NPD7229	Phase 3
0.6581	Remote Similarity	NPD5401	Approved
0.6575	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD1729	Discontinued

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