NPASS Compound

Structure

CID259942 OpenBabel06191716062D 27 28 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 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 6.0622 -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 6.9282 -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 11.2583 -2.5000 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 10.3923 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2583 -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 8.6603 -1.0000 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 10.3923 -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 9.5263 -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 19 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 6 1 0 0 0 0 5 7 1 0 0 0 0 6 9 1 0 0 0 0 7 12 1 0 0 0 0 8 10 2 0 0 0 0 8 11 1 0 0 0 0 9 13 1 0 0 0 0 10 14 1 0 0 0 0 11 15 2 0 0 0 0 12 16 1 0 0 0 0 13 20 1 0 0 0 0 14 20 2 0 0 0 0 15 20 1 0 0 0 0 16 21 1 0 0 0 0 17 21 2 0 0 0 0 17 22 1 0 0 0 0 18 22 2 0 0 0 0 18 23 1 0 0 0 0 19 24 1 0 0 0 0 19 25 2 0 0 0 0 21 24 1 0 0 0 0 22 26 1 0 0 0 0 23 24 2 0 0 0 0 23 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	368.24
Volume:	414.463
LogP:	6.947
LogD:	4.561
LogS:	-3.557
# Rotatable Bonds:	12
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.346
Synthetic Accessibility Score:	2.182
Fsp3:	0.458
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:	-4.987
MDCK Permeability:	1.2356787919998169e-05
Pgp-inhibitor:	0.967
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):	0.076
Plasma Protein Binding (PPB):	99.60456848144531%
Volume Distribution (VD):	1.382
Pgp-substrate:	0.3644765615463257%

ADMET: Metabolism

CYP1A2-inhibitor:	0.947
CYP1A2-substrate:	0.197
CYP2C19-inhibitor:	0.916
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.52
CYP2C9-substrate:	0.965
CYP2D6-inhibitor:	0.938
CYP2D6-substrate:	0.222
CYP3A4-inhibitor:	0.617
CYP3A4-substrate:	0.119

ADMET: Excretion

Clearance (CL):	5.535
Half-life (T1/2):	0.467

ADMET: Toxicity

hERG Blockers:	0.332
Human Hepatotoxicity (H-HT):	0.044
Drug-inuced Liver Injury (DILI):	0.101
AMES Toxicity:	0.492
Rat Oral Acute Toxicity:	0.048
Maximum Recommended Daily Dose:	0.557
Skin Sensitization:	0.955
Carcinogencity:	0.054
Eye Corrosion:	0.074
Eye Irritation:	0.982
Respiratory Toxicity:	0.685

Download Data

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

Natural Product: NPC259942

Natural Product ID:	NPC259942
*Common Name:**	2,4-Dihydroxy-6-(10'-Phenyldecyl)-Acetophenone
IUPAC Name:	1-[2,4-dihydroxy-6-(10-phenyldecyl)phenyl]ethanone
Synonyms:
Standard InCHIKey:	GBNNUJZVXOCNQU-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C24H32O3/c1-19(25)24-21(17-22(26)18-23(24)27)16-12-7-5-3-2-4-6-9-13-20-14-10-8-11-15-20/h8,10-11,14-15,17-18,26-27H,2-7,9,12-13,16H2,1H3
SMILES:	CC(=O)c1c(CCCCCCCCCCc2ccccc2)cc(cc1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL479900
PubChem CID:	44575638
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	=	3.22	ug ml-1	PMID[518796]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	2.87	ug ml-1	PMID[518796]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	4.47	ug ml-1	PMID[518796]
NPT140	Organism	Artemia	Artemia	LC50	=	0.18	ug.mL-1	PMID[518796]
NPT141	Organism	Agrobacterium tumefaciens	Agrobacterium tumefaciens	T/C	=	30.0	%	PMID[518796]

☑ 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 NPC259942 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	NPC92624
0.9675	High Similarity	NPC473691
0.9593	High Similarity	NPC477454
0.9531	High Similarity	NPC282780
0.9531	High Similarity	NPC166480
0.9385	High Similarity	NPC191976
0.937	High Similarity	NPC17840
0.937	High Similarity	NPC247477
0.9318	High Similarity	NPC472903
0.9313	High Similarity	NPC290030
0.9286	High Similarity	NPC116513
0.9237	High Similarity	NPC118919
0.9225	High Similarity	NPC175738
0.9206	High Similarity	NPC267846
0.9206	High Similarity	NPC8745
0.9206	High Similarity	NPC62952
0.92	High Similarity	NPC13238
0.9179	High Similarity	NPC472904
0.9173	High Similarity	NPC242994
0.9173	High Similarity	NPC138099
0.9154	High Similarity	NPC267205
0.9141	High Similarity	NPC109123
0.9141	High Similarity	NPC474998
0.9134	High Similarity	NPC266689
0.9134	High Similarity	NPC105157
0.9134	High Similarity	NPC98254
0.9134	High Similarity	NPC162612
0.9134	High Similarity	NPC72158
0.9134	High Similarity	NPC169250
0.9134	High Similarity	NPC190043
0.9134	High Similarity	NPC103356
0.9134	High Similarity	NPC100067
0.9134	High Similarity	NPC30501
0.9134	High Similarity	NPC23126
0.9127	High Similarity	NPC10926
0.9113	High Similarity	NPC196976
0.9113	High Similarity	NPC242895
0.9113	High Similarity	NPC156139
0.9104	High Similarity	NPC169452
0.9104	High Similarity	NPC181560
0.9084	High Similarity	NPC44437
0.9062	High Similarity	NPC21305
0.9062	High Similarity	NPC221777
0.9062	High Similarity	NPC473017
0.904	High Similarity	NPC32032
0.904	High Similarity	NPC133909
0.9032	High Similarity	NPC149246
0.9032	High Similarity	NPC297186
0.9024	High Similarity	NPC195262
0.9024	High Similarity	NPC188814
0.9023	High Similarity	NPC53001
0.9023	High Similarity	NPC53414
0.9023	High Similarity	NPC471905
0.9023	High Similarity	NPC53206
0.9008	High Similarity	NPC180261
0.9008	High Similarity	NPC37299
0.8976	High Similarity	NPC201728
0.8976	High Similarity	NPC262671
0.8971	High Similarity	NPC49108
0.8971	High Similarity	NPC474961
0.8971	High Similarity	NPC193555
0.896	High Similarity	NPC267552
0.896	High Similarity	NPC19174
0.896	High Similarity	NPC45438
0.896	High Similarity	NPC115159
0.896	High Similarity	NPC224273
0.896	High Similarity	NPC73532
0.896	High Similarity	NPC143427
0.8955	High Similarity	NPC87723
0.8947	High Similarity	NPC264112
0.8947	High Similarity	NPC65005
0.8947	High Similarity	NPC254847
0.8947	High Similarity	NPC194764
0.8939	High Similarity	NPC475088
0.8923	High Similarity	NPC244441
0.8923	High Similarity	NPC147757
0.8923	High Similarity	NPC233056
0.8915	High Similarity	NPC41263
0.8906	High Similarity	NPC160499
0.8905	High Similarity	NPC474203
0.8905	High Similarity	NPC451542
0.8905	High Similarity	NPC313047
0.8905	High Similarity	NPC295712
0.8889	High Similarity	NPC309765
0.8889	High Similarity	NPC91105
0.8889	High Similarity	NPC244351
0.8881	High Similarity	NPC71256
0.888	High Similarity	NPC146642
0.888	High Similarity	NPC248363
0.8872	High Similarity	NPC290803
0.8872	High Similarity	NPC249272
0.8871	High Similarity	NPC161617
0.8864	High Similarity	NPC40524
0.8864	High Similarity	NPC213485
0.8864	High Similarity	NPC139074
0.8862	High Similarity	NPC121259
0.8855	High Similarity	NPC475042
0.8832	High Similarity	NPC135524
0.8832	High Similarity	NPC250755
0.8832	High Similarity	NPC137649
0.8828	High Similarity	NPC475733
0.8819	High Similarity	NPC472029
0.8819	High Similarity	NPC65761
0.881	High Similarity	NPC215392
0.881	High Similarity	NPC303737
0.8806	High Similarity	NPC223836
0.88	High Similarity	NPC159525
0.88	High Similarity	NPC294037
0.8797	High Similarity	NPC12070
0.8797	High Similarity	NPC270899
0.879	High Similarity	NPC40649
0.879	High Similarity	NPC209486
0.8788	High Similarity	NPC135801
0.8788	High Similarity	NPC478190
0.878	High Similarity	NPC477453
0.8779	High Similarity	NPC62219
0.8779	High Similarity	NPC26697
0.8769	High Similarity	NPC179898
0.8769	High Similarity	NPC95537
0.8768	High Similarity	NPC174905
0.8768	High Similarity	NPC293545
0.8759	High Similarity	NPC246638
0.8759	High Similarity	NPC204045
0.8759	High Similarity	NPC305845
0.8759	High Similarity	NPC187843
0.875	High Similarity	NPC143438
0.875	High Similarity	NPC162939
0.875	High Similarity	NPC472368
0.8741	High Similarity	NPC194579
0.8741	High Similarity	NPC474849
0.8741	High Similarity	NPC178467
0.8741	High Similarity	NPC473391
0.8741	High Similarity	NPC472367
0.8741	High Similarity	NPC65837
0.8741	High Similarity	NPC472364
0.8741	High Similarity	NPC476333
0.8741	High Similarity	NPC474771
0.8741	High Similarity	NPC149372
0.8741	High Similarity	NPC213603
0.874	High Similarity	NPC283514
0.8731	High Similarity	NPC283590
0.8731	High Similarity	NPC130899
0.8731	High Similarity	NPC70859
0.8731	High Similarity	NPC61153
0.873	High Similarity	NPC179092
0.873	High Similarity	NPC35856
0.873	High Similarity	NPC159760
0.873	High Similarity	NPC178395
0.873	High Similarity	NPC301987
0.873	High Similarity	NPC222876
0.873	High Similarity	NPC244994
0.873	High Similarity	NPC272454
0.873	High Similarity	NPC115188
0.873	High Similarity	NPC26433
0.873	High Similarity	NPC292665
0.8722	High Similarity	NPC48036
0.8722	High Similarity	NPC114183
0.872	High Similarity	NPC158222
0.8712	High Similarity	NPC275504
0.8712	High Similarity	NPC469526
0.8712	High Similarity	NPC34070
0.8705	High Similarity	NPC21599
0.8705	High Similarity	NPC193703
0.8705	High Similarity	NPC227841
0.8702	High Similarity	NPC476119
0.8692	High Similarity	NPC209959
0.8686	High Similarity	NPC109232
0.8686	High Similarity	NPC472366
0.8686	High Similarity	NPC203063
0.8676	High Similarity	NPC33144
0.8676	High Similarity	NPC475974
0.8676	High Similarity	NPC20210
0.8676	High Similarity	NPC478200
0.8676	High Similarity	NPC473622
0.8676	High Similarity	NPC9121
0.8676	High Similarity	NPC191835
0.8676	High Similarity	NPC177307
0.8661	High Similarity	NPC198336
0.8657	High Similarity	NPC294593
0.8657	High Similarity	NPC159623
0.8657	High Similarity	NPC474519
0.8657	High Similarity	NPC82225
0.8657	High Similarity	NPC144051
0.8657	High Similarity	NPC28753
0.8657	High Similarity	NPC204960
0.8657	High Similarity	NPC20560
0.8657	High Similarity	NPC18877
0.8652	High Similarity	NPC125801
0.8643	High Similarity	NPC34482
0.8643	High Similarity	NPC29577
0.8643	High Similarity	NPC12402
0.8633	High Similarity	NPC296752
0.8633	High Similarity	NPC310340
0.8633	High Similarity	NPC84266
0.8633	High Similarity	NPC478202
0.8626	High Similarity	NPC24869
0.8623	High Similarity	NPC110810
0.8623	High Similarity	NPC478217
0.8623	High Similarity	NPC313123
0.8623	High Similarity	NPC275734

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 NPC259942 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
0.8947	High Similarity	NPD1509	Clinical (unspecified phase)
0.8788	High Similarity	NPD943	Approved
0.8705	High Similarity	NPD7390	Discontinued
0.8661	High Similarity	NPD1201	Approved
0.8507	High Similarity	NPD1240	Approved
0.8397	Intermediate Similarity	NPD1470	Approved
0.8394	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8382	Intermediate Similarity	NPD1607	Approved
0.8261	Intermediate Similarity	NPD1510	Phase 2
0.8214	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8201	Intermediate Similarity	NPD5405	Approved
0.8201	Intermediate Similarity	NPD5406	Approved
0.8201	Intermediate Similarity	NPD5404	Approved
0.8201	Intermediate Similarity	NPD5408	Approved
0.8189	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD7819	Suspended
0.8125	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7985	Intermediate Similarity	NPD1164	Approved
0.7958	Intermediate Similarity	NPD1549	Phase 2
0.7943	Intermediate Similarity	NPD2796	Approved
0.7933	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD1511	Approved
0.7885	Intermediate Similarity	NPD7473	Discontinued
0.7881	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD1934	Approved
0.7847	Intermediate Similarity	NPD3750	Approved
0.7823	Intermediate Similarity	NPD1512	Approved
0.7817	Intermediate Similarity	NPD2935	Discontinued
0.7815	Intermediate Similarity	NPD2801	Approved
0.7806	Intermediate Similarity	NPD6232	Discontinued
0.7755	Intermediate Similarity	NPD2532	Approved
0.7755	Intermediate Similarity	NPD2534	Approved
0.7755	Intermediate Similarity	NPD2533	Approved
0.7742	Intermediate Similarity	NPD6959	Discontinued
0.7733	Intermediate Similarity	NPD4380	Phase 2
0.7727	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD3882	Suspended
0.7692	Intermediate Similarity	NPD6099	Approved
0.7692	Intermediate Similarity	NPD6100	Approved
0.7669	Intermediate Similarity	NPD3019	Approved
0.7669	Intermediate Similarity	NPD2932	Approved
0.7662	Intermediate Similarity	NPD7075	Discontinued
0.7662	Intermediate Similarity	NPD3749	Approved
0.7642	Intermediate Similarity	NPD940	Approved
0.7642	Intermediate Similarity	NPD846	Approved
0.7639	Intermediate Similarity	NPD2344	Approved
0.7638	Intermediate Similarity	NPD4750	Phase 3
0.7606	Intermediate Similarity	NPD6651	Approved
0.7582	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD6799	Approved
0.7566	Intermediate Similarity	NPD7411	Suspended
0.7561	Intermediate Similarity	NPD1242	Phase 1
0.7559	Intermediate Similarity	NPD74	Approved
0.7559	Intermediate Similarity	NPD9266	Approved
0.7536	Intermediate Similarity	NPD2798	Approved
0.7534	Intermediate Similarity	NPD2800	Approved
0.7517	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3748	Approved
0.75	Intermediate Similarity	NPD6599	Discontinued
0.75	Intermediate Similarity	NPD3300	Phase 2
0.75	Intermediate Similarity	NPD9493	Approved
0.75	Intermediate Similarity	NPD9269	Phase 2
0.7484	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6166	Phase 2
0.7484	Intermediate Similarity	NPD7768	Phase 2
0.748	Intermediate Similarity	NPD9263	Approved
0.748	Intermediate Similarity	NPD9267	Approved
0.748	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD9264	Approved
0.7463	Intermediate Similarity	NPD9268	Approved
0.7447	Intermediate Similarity	NPD3764	Approved
0.7447	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD2309	Approved
0.7419	Intermediate Similarity	NPD3817	Phase 2
0.7407	Intermediate Similarity	NPD7074	Phase 3
0.7379	Intermediate Similarity	NPD2799	Discontinued
0.7375	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD6020	Phase 2
0.7346	Intermediate Similarity	NPD7054	Approved
0.7339	Intermediate Similarity	NPD3020	Approved
0.7329	Intermediate Similarity	NPD1551	Phase 2
0.732	Intermediate Similarity	NPD3226	Approved
0.7301	Intermediate Similarity	NPD7472	Approved
0.7297	Intermediate Similarity	NPD1243	Approved
0.7292	Intermediate Similarity	NPD230	Phase 1
0.729	Intermediate Similarity	NPD6801	Discontinued
0.7284	Intermediate Similarity	NPD3818	Discontinued
0.7279	Intermediate Similarity	NPD2346	Discontinued
0.726	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD9545	Approved
0.7246	Intermediate Similarity	NPD3972	Approved
0.7239	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD2859	Approved
0.7236	Intermediate Similarity	NPD2860	Approved
0.7233	Intermediate Similarity	NPD5494	Approved
0.7214	Intermediate Similarity	NPD1203	Approved
0.7212	Intermediate Similarity	NPD7251	Discontinued
0.7197	Intermediate Similarity	NPD7635	Approved
0.7181	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD7808	Phase 3
0.7165	Intermediate Similarity	NPD9261	Approved
0.7154	Intermediate Similarity	NPD2934	Approved
0.7154	Intermediate Similarity	NPD2933	Approved
0.7152	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6797	Phase 2
0.7143	Intermediate Similarity	NPD5711	Approved
0.7143	Intermediate Similarity	NPD1876	Approved
0.7143	Intermediate Similarity	NPD5710	Approved
0.7134	Intermediate Similarity	NPD1465	Phase 2
0.7134	Intermediate Similarity	NPD5844	Phase 1
0.7133	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD4625	Phase 3
0.7122	Intermediate Similarity	NPD1608	Approved
0.7101	Intermediate Similarity	NPD3026	Approved
0.7101	Intermediate Similarity	NPD3023	Approved
0.7099	Intermediate Similarity	NPD3926	Phase 2
0.7099	Intermediate Similarity	NPD3021	Approved
0.7099	Intermediate Similarity	NPD3022	Approved
0.7092	Intermediate Similarity	NPD2797	Approved
0.709	Intermediate Similarity	NPD9281	Approved
0.7083	Intermediate Similarity	NPD3268	Approved
0.708	Intermediate Similarity	NPD3024	Approved
0.708	Intermediate Similarity	NPD3025	Approved
0.708	Intermediate Similarity	NPD1651	Approved
0.7078	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD1755	Approved
0.7067	Intermediate Similarity	NPD2654	Approved
0.7066	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6832	Phase 2
0.7048	Intermediate Similarity	NPD5953	Discontinued
0.7039	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD6663	Approved
0.703	Intermediate Similarity	NPD7286	Phase 2
0.7021	Intermediate Similarity	NPD1283	Approved
0.702	Intermediate Similarity	NPD7003	Approved
0.702	Intermediate Similarity	NPD4628	Phase 3
0.7006	Intermediate Similarity	NPD6559	Discontinued
0.7	Intermediate Similarity	NPD9717	Approved
0.6993	Remote Similarity	NPD5736	Approved
0.6981	Remote Similarity	NPD5402	Approved
0.6968	Remote Similarity	NPD5403	Approved
0.6968	Remote Similarity	NPD920	Approved
0.6966	Remote Similarity	NPD2313	Discontinued
0.6964	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD5951	Approved
0.696	Remote Similarity	NPD844	Approved
0.6949	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD2342	Discontinued
0.6944	Remote Similarity	NPD4908	Phase 1
0.6936	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD1471	Phase 3
0.6929	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD1610	Phase 2
0.6929	Remote Similarity	NPD422	Phase 1
0.6906	Remote Similarity	NPD4626	Approved
0.6906	Remote Similarity	NPD17	Approved
0.6905	Remote Similarity	NPD288	Approved
0.6901	Remote Similarity	NPD8150	Discontinued
0.688	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7458	Discontinued
0.6875	Remote Similarity	NPD4288	Approved
0.6875	Remote Similarity	NPD2296	Approved
0.6875	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD919	Approved
0.6849	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD411	Approved
0.6846	Remote Similarity	NPD1237	Approved
0.6839	Remote Similarity	NPD5401	Approved
0.6831	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD4749	Approved
0.6829	Remote Similarity	NPD7229	Phase 3
0.6824	Remote Similarity	NPD447	Suspended
0.6824	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD1281	Approved
0.6806	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.68	Remote Similarity	NPD4308	Phase 3
0.6797	Remote Similarity	NPD3400	Discontinued
0.6797	Remote Similarity	NPD8166	Discontinued
0.6781	Remote Similarity	NPD3027	Phase 3
0.6774	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.677	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD1929	Approved
0.6769	Remote Similarity	NPD1930	Approved
0.6768	Remote Similarity	NPD1247	Approved
0.6768	Remote Similarity	NPD7199	Phase 2
0.6767	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD3091	Approved
0.6763	Remote Similarity	NPD1548	Phase 1
0.6761	Remote Similarity	NPD4878	Approved
0.6759	Remote Similarity	NPD9494	Approved
0.6753	Remote Similarity	NPD6190	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