NPASS Compound

Structure

NPC62546 OpenBabel07101719252D 30 30 0 0 0 0 0 0 0 0999 V2000 8.6603 16.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 16.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 16.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 15.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 14.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 13.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 13.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 12.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 11.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 10.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 10.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 8.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 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 -0.0000 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 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 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 3 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 15 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 19 25 1 0 0 0 0 20 24 1 0 0 0 0 20 25 1 0 0 0 0 21 24 2 0 0 0 0 21 26 1 0 0 0 0 22 24 1 0 0 0 0 22 27 2 0 0 0 0 23 26 2 0 0 0 0 23 27 1 0 0 0 0 25 28 2 0 0 0 0 26 29 1 0 0 0 0 27 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	418.34
Volume:	482.816
LogP:	8.864
LogD:	4.997
LogS:	-3.834
# Rotatable Bonds:	20
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.21
Synthetic Accessibility Score:	2.288
Fsp3:	0.741
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:	-5.327
MDCK Permeability:	1.0026848030975088e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013
Plasma Protein Binding (PPB):	99.42261505126953%
Volume Distribution (VD):	2.412
Pgp-substrate:	0.4213421940803528%

ADMET: Metabolism

CYP1A2-inhibitor:	0.126
CYP1A2-substrate:	0.182
CYP2C19-inhibitor:	0.548
CYP2C19-substrate:	0.053
CYP2C9-inhibitor:	0.107
CYP2C9-substrate:	0.993
CYP2D6-inhibitor:	0.886
CYP2D6-substrate:	0.107
CYP3A4-inhibitor:	0.619
CYP3A4-substrate:	0.044

ADMET: Excretion

Clearance (CL):	7.612
Half-life (T1/2):	0.652

ADMET: Toxicity

hERG Blockers:	0.299
Human Hepatotoxicity (H-HT):	0.053
Drug-inuced Liver Injury (DILI):	0.039
AMES Toxicity:	0.03
Rat Oral Acute Toxicity:	0.048
Maximum Recommended Daily Dose:	0.22
Skin Sensitization:	0.953
Carcinogencity:	0.024
Eye Corrosion:	0.343
Eye Irritation:	0.941
Respiratory Toxicity:	0.891

Download Data

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

Natural Product: NPC62546

Natural Product ID:	NPC62546
*Common Name:**	5-(2'-Oxoheneicosyl)Resorcinol
IUPAC Name:	1-(3,5-dihydroxyphenyl)henicosan-2-one
Synonyms:	5-(2'-Oxoheneicosyl)Resorcinol
Standard InCHIKey:	BENPXLIQKFYNHW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C27H46O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-25(28)20-24-21-26(29)23-27(30)22-24/h21-23,29-30H,2-20H2,1H3
SMILES:	CCCCCCCCCCCCCCCCCCCC(=O)Cc1cc(cc(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1795556
PubChem CID:	56683379
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0001286] Benzenediols [CHEMONTID:0000137] Resorcinols

*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
NPO33268	wheat	n.a.	n.a.	n.a.	wheat germ	n.a.	n.a.	PMID[19284743]
NPO33268	wheat	n.a.	n.a.	n.a.	wheat bran	n.a.	n.a.	PMID[21658963]

☑ 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
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	16.63	ug.mL-1	PMID[494574]

☑ 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 NPC62546 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	248
0.1-0.2	1326
0.2-0.3	3634
0.3-0.4	11637
0.4-0.5	8246
0.5-0.6	6479
0.6-0.7	8796
0.7-0.8	2145
0.8-0.85	143
0.85-0.9	41
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC162113
0.8952	High Similarity	NPC192032
0.8952	High Similarity	NPC147310
0.8952	High Similarity	NPC11280
0.8952	High Similarity	NPC294186
0.8952	High Similarity	NPC166313
0.8952	High Similarity	NPC24407
0.8952	High Similarity	NPC137415
0.8868	High Similarity	NPC24404
0.8868	High Similarity	NPC53051
0.8868	High Similarity	NPC249828
0.8868	High Similarity	NPC313030
0.8868	High Similarity	NPC146798
0.8868	High Similarity	NPC168303
0.8868	High Similarity	NPC71002
0.8868	High Similarity	NPC106396
0.8868	High Similarity	NPC302219
0.8868	High Similarity	NPC222522
0.8868	High Similarity	NPC85479
0.8868	High Similarity	NPC242342
0.8868	High Similarity	NPC94351
0.8824	High Similarity	NPC473691
0.8774	High Similarity	NPC72947
0.8774	High Similarity	NPC284011
0.8739	High Similarity	NPC477454
0.8718	High Similarity	NPC472892
0.8679	High Similarity	NPC10588
0.8679	High Similarity	NPC166761
0.8632	High Similarity	NPC248363
0.8632	High Similarity	NPC149246
0.8624	High Similarity	NPC99836
0.8624	High Similarity	NPC12640
0.8624	High Similarity	NPC317592
0.8624	High Similarity	NPC201662
0.8609	High Similarity	NPC121259
0.8545	High Similarity	NPC158253
0.8545	High Similarity	NPC232523
0.8545	High Similarity	NPC61033
0.8545	High Similarity	NPC305603
0.8545	High Similarity	NPC204901
0.8537	High Similarity	NPC259942
0.8532	High Similarity	NPC246056
0.8532	High Similarity	NPC37802
0.8532	High Similarity	NPC134829
0.8487	Intermediate Similarity	NPC91105
0.8475	Intermediate Similarity	NPC146642
0.8455	Intermediate Similarity	NPC470700
0.8455	Intermediate Similarity	NPC39097
0.8455	Intermediate Similarity	NPC302681
0.8455	Intermediate Similarity	NPC109123
0.8455	Intermediate Similarity	NPC118286
0.8455	Intermediate Similarity	NPC92624
0.8455	Intermediate Similarity	NPC109691
0.8455	Intermediate Similarity	NPC39664
0.844	Intermediate Similarity	NPC227458
0.844	Intermediate Similarity	NPC241891
0.844	Intermediate Similarity	NPC218879
0.844	Intermediate Similarity	NPC244513
0.843	Intermediate Similarity	NPC475733
0.8417	Intermediate Similarity	NPC472029
0.8417	Intermediate Similarity	NPC65761
0.8403	Intermediate Similarity	NPC215392
0.839	Intermediate Similarity	NPC294037
0.8387	Intermediate Similarity	NPC17840
0.8387	Intermediate Similarity	NPC247477
0.8378	Intermediate Similarity	NPC54844
0.8376	Intermediate Similarity	NPC40649
0.8376	Intermediate Similarity	NPC209486
0.8374	Intermediate Similarity	NPC24869
0.8348	Intermediate Similarity	NPC276111
0.8348	Intermediate Similarity	NPC118288
0.8333	Intermediate Similarity	NPC309765
0.8305	Intermediate Similarity	NPC195262
0.8305	Intermediate Similarity	NPC188814
0.8305	Intermediate Similarity	NPC161617
0.8293	Intermediate Similarity	NPC116513
0.8293	Intermediate Similarity	NPC209959
0.8286	Intermediate Similarity	NPC295295
0.8279	Intermediate Similarity	NPC10926
0.8257	Intermediate Similarity	NPC143659
0.8257	Intermediate Similarity	NPC100340
0.825	Intermediate Similarity	NPC303737
0.8241	Intermediate Similarity	NPC280869
0.8235	Intermediate Similarity	NPC159525
0.823	Intermediate Similarity	NPC19808
0.823	Intermediate Similarity	NPC95172
0.823	Intermediate Similarity	NPC33728
0.823	Intermediate Similarity	NPC186385
0.823	Intermediate Similarity	NPC299568
0.8214	Intermediate Similarity	NPC34715
0.8211	Intermediate Similarity	NPC62952
0.8211	Intermediate Similarity	NPC8745
0.8211	Intermediate Similarity	NPC267846
0.8205	Intermediate Similarity	NPC123559
0.8197	Intermediate Similarity	NPC13238
0.8189	Intermediate Similarity	NPC180261
0.8189	Intermediate Similarity	NPC37299
0.8174	Intermediate Similarity	NPC166995
0.816	Intermediate Similarity	NPC474998
0.8158	Intermediate Similarity	NPC242178
0.8151	Intermediate Similarity	NPC158222
0.8148	Intermediate Similarity	NPC260000
0.8145	Intermediate Similarity	NPC23126
0.8145	Intermediate Similarity	NPC72158
0.8145	Intermediate Similarity	NPC266689
0.8145	Intermediate Similarity	NPC162612
0.8145	Intermediate Similarity	NPC107672
0.8145	Intermediate Similarity	NPC30501
0.8145	Intermediate Similarity	NPC105157
0.8145	Intermediate Similarity	NPC98254
0.8145	Intermediate Similarity	NPC169250
0.8145	Intermediate Similarity	NPC103356
0.8145	Intermediate Similarity	NPC190043
0.8145	Intermediate Similarity	NPC156539
0.8145	Intermediate Similarity	NPC100067
0.8142	Intermediate Similarity	NPC174981
0.814	Intermediate Similarity	NPC191976
0.813	Intermediate Similarity	NPC201728
0.813	Intermediate Similarity	NPC262671
0.8125	Intermediate Similarity	NPC282780
0.8125	Intermediate Similarity	NPC166480
0.8113	Intermediate Similarity	NPC3358
0.8113	Intermediate Similarity	NPC162314
0.8113	Intermediate Similarity	NPC306884
0.8113	Intermediate Similarity	NPC94139
0.8113	Intermediate Similarity	NPC147284
0.8113	Intermediate Similarity	NPC210497
0.811	Intermediate Similarity	NPC476389
0.8108	Intermediate Similarity	NPC8931
0.8108	Intermediate Similarity	NPC30506
0.8108	Intermediate Similarity	NPC102216
0.8108	Intermediate Similarity	NPC261573
0.8108	Intermediate Similarity	NPC120693
0.8103	Intermediate Similarity	NPC23804
0.8103	Intermediate Similarity	NPC98543
0.8103	Intermediate Similarity	NPC263753
0.8099	Intermediate Similarity	NPC242895
0.8099	Intermediate Similarity	NPC226275
0.8099	Intermediate Similarity	NPC156139
0.8099	Intermediate Similarity	NPC196976
0.8087	Intermediate Similarity	NPC165770
0.8087	Intermediate Similarity	NPC476632
0.8087	Intermediate Similarity	NPC224527
0.8087	Intermediate Similarity	NPC4493
0.8087	Intermediate Similarity	NPC225679
0.8083	Intermediate Similarity	NPC294964
0.808	Intermediate Similarity	NPC473017
0.808	Intermediate Similarity	NPC41263
0.808	Intermediate Similarity	NPC21305
0.808	Intermediate Similarity	NPC221777
0.807	Intermediate Similarity	NPC26013
0.807	Intermediate Similarity	NPC282855
0.8065	Intermediate Similarity	NPC474944
0.8053	Intermediate Similarity	NPC226699
0.8051	Intermediate Similarity	NPC477453
0.8033	Intermediate Similarity	NPC32032
0.8033	Intermediate Similarity	NPC133909
0.8018	Intermediate Similarity	NPC315022
0.8017	Intermediate Similarity	NPC159760
0.8017	Intermediate Similarity	NPC178395
0.8017	Intermediate Similarity	NPC301987
0.8017	Intermediate Similarity	NPC179092
0.8017	Intermediate Similarity	NPC244994
0.8017	Intermediate Similarity	NPC272454
0.8017	Intermediate Similarity	NPC26433
0.8017	Intermediate Similarity	NPC35856
0.8017	Intermediate Similarity	NPC115188
0.8017	Intermediate Similarity	NPC292665
0.8017	Intermediate Similarity	NPC222876
0.8017	Intermediate Similarity	NPC231717
0.8017	Intermediate Similarity	NPC43525
0.8017	Intermediate Similarity	NPC297186
0.8	Intermediate Similarity	NPC264112
0.8	Intermediate Similarity	NPC208229
0.8	Intermediate Similarity	NPC194764
0.8	Intermediate Similarity	NPC65005
0.8	Intermediate Similarity	NPC168657
0.7982	Intermediate Similarity	NPC291789
0.7982	Intermediate Similarity	NPC279887
0.7982	Intermediate Similarity	NPC317305
0.7982	Intermediate Similarity	NPC68260
0.7969	Intermediate Similarity	NPC175738
0.7966	Intermediate Similarity	NPC4665
0.7966	Intermediate Similarity	NPC322197
0.7965	Intermediate Similarity	NPC188677
0.7965	Intermediate Similarity	NPC6984
0.7955	Intermediate Similarity	NPC472903
0.7953	Intermediate Similarity	NPC62219
0.7953	Intermediate Similarity	NPC233056
0.7953	Intermediate Similarity	NPC244441
0.7951	Intermediate Similarity	NPC45438
0.7951	Intermediate Similarity	NPC115159
0.7951	Intermediate Similarity	NPC19174
0.7951	Intermediate Similarity	NPC73532
0.7951	Intermediate Similarity	NPC143427
0.7951	Intermediate Similarity	NPC224273
0.7951	Intermediate Similarity	NPC267552
0.7949	Intermediate Similarity	NPC242136
0.7949	Intermediate Similarity	NPC319803
0.7949	Intermediate Similarity	NPC117846

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 NPC62546 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	266
0.1-0.2	925
0.2-0.3	1499
0.3-0.4	2877
0.4-0.5	2013
0.5-0.6	1160
0.6-0.7	357
0.7-0.8	51
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.823	Intermediate Similarity	NPD4750	Phase 3
0.8091	Intermediate Similarity	NPD940	Approved
0.8091	Intermediate Similarity	NPD846	Approved
0.7939	Intermediate Similarity	NPD6099	Approved
0.7939	Intermediate Similarity	NPD6100	Approved
0.7838	Intermediate Similarity	NPD1242	Phase 1
0.7829	Intermediate Similarity	NPD943	Approved
0.7742	Intermediate Similarity	NPD9269	Phase 2
0.7727	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7705	Intermediate Similarity	NPD9268	Approved
0.768	Intermediate Similarity	NPD1755	Approved
0.7642	Intermediate Similarity	NPD3019	Approved
0.7642	Intermediate Similarity	NPD2932	Approved
0.7636	Intermediate Similarity	NPD844	Approved
0.7586	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD1240	Approved
0.7536	Intermediate Similarity	NPD7390	Discontinued
0.752	Intermediate Similarity	NPD1201	Approved
0.75	Intermediate Similarity	NPD230	Phase 1
0.7477	Intermediate Similarity	NPD2859	Approved
0.7477	Intermediate Similarity	NPD2860	Approved
0.7463	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD1608	Approved
0.7444	Intermediate Similarity	NPD1607	Approved
0.7434	Intermediate Similarity	NPD3020	Approved
0.7411	Intermediate Similarity	NPD288	Approved
0.7405	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD2934	Approved
0.7387	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD2933	Approved
0.7368	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD9545	Approved
0.7333	Intermediate Similarity	NPD1510	Phase 2
0.7319	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD1470	Approved
0.7266	Intermediate Similarity	NPD4749	Approved
0.7234	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD74	Approved
0.7227	Intermediate Similarity	NPD9266	Approved
0.7222	Intermediate Similarity	NPD17	Approved
0.7177	Intermediate Similarity	NPD9493	Approved
0.7167	Intermediate Similarity	NPD3021	Approved
0.7167	Intermediate Similarity	NPD3022	Approved
0.7143	Intermediate Similarity	NPD9264	Approved
0.7143	Intermediate Similarity	NPD845	Approved
0.7143	Intermediate Similarity	NPD9093	Approved
0.7143	Intermediate Similarity	NPD9267	Approved
0.7143	Intermediate Similarity	NPD9263	Approved
0.7101	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD255	Approved
0.7097	Intermediate Similarity	NPD256	Approved
0.7075	Intermediate Similarity	NPD9089	Approved
0.7075	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1759	Phase 1
0.7059	Intermediate Similarity	NPD1445	Approved
0.7059	Intermediate Similarity	NPD1444	Approved
0.7059	Intermediate Similarity	NPD6651	Approved
0.705	Intermediate Similarity	NPD1549	Phase 2
0.7042	Intermediate Similarity	NPD1511	Approved
0.7037	Intermediate Similarity	NPD111	Approved
0.7031	Intermediate Similarity	NPD3026	Approved
0.7031	Intermediate Similarity	NPD3023	Approved
0.7029	Intermediate Similarity	NPD2796	Approved
0.7018	Intermediate Similarity	NPD1809	Phase 2
0.7015	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD3025	Approved
0.7008	Intermediate Similarity	NPD3024	Approved
0.7007	Intermediate Similarity	NPD1934	Approved
0.6993	Remote Similarity	NPD2533	Approved
0.6993	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD2532	Approved
0.6993	Remote Similarity	NPD2534	Approved
0.6992	Remote Similarity	NPD7635	Approved
0.6984	Remote Similarity	NPD1758	Phase 1
0.6963	Remote Similarity	NPD6663	Approved
0.696	Remote Similarity	NPD6671	Approved
0.6959	Remote Similarity	NPD2801	Approved
0.6959	Remote Similarity	NPD7819	Suspended
0.695	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.695	Remote Similarity	NPD3750	Approved
0.6944	Remote Similarity	NPD1512	Approved
0.694	Remote Similarity	NPD4625	Phase 3
0.694	Remote Similarity	NPD3027	Phase 3
0.6917	Remote Similarity	NPD5736	Approved
0.6913	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD2935	Discontinued
0.6906	Remote Similarity	NPD5404	Approved
0.6906	Remote Similarity	NPD5405	Approved
0.6906	Remote Similarity	NPD5406	Approved
0.6906	Remote Similarity	NPD5408	Approved
0.6894	Remote Similarity	NPD1164	Approved
0.6894	Remote Similarity	NPD2797	Approved
0.6889	Remote Similarity	NPD3268	Approved
0.6885	Remote Similarity	NPD1792	Phase 2
0.6879	Remote Similarity	NPD2800	Approved
0.6875	Remote Similarity	NPD1651	Approved
0.6871	Remote Similarity	NPD4380	Phase 2
0.6867	Remote Similarity	NPD3882	Suspended
0.6846	Remote Similarity	NPD422	Phase 1
0.6842	Remote Similarity	NPD858	Approved
0.6842	Remote Similarity	NPD599	Approved
0.6842	Remote Similarity	NPD258	Approved
0.6842	Remote Similarity	NPD602	Approved
0.6842	Remote Similarity	NPD859	Approved
0.6842	Remote Similarity	NPD257	Approved
0.6835	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD1778	Approved
0.6821	Remote Similarity	NPD7075	Discontinued
0.6818	Remote Similarity	NPD1283	Approved
0.6807	Remote Similarity	NPD9500	Approved
0.6807	Remote Similarity	NPD9261	Approved
0.6803	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD3972	Approved
0.6791	Remote Similarity	NPD9494	Approved
0.6786	Remote Similarity	NPD800	Approved
0.6783	Remote Similarity	NPD1693	Approved
0.6781	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD9568	Approved
0.6765	Remote Similarity	NPD3764	Approved
0.6759	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD9495	Approved
0.675	Remote Similarity	NPD1237	Approved
0.6746	Remote Similarity	NPD2629	Approved
0.6746	Remote Similarity	NPD9281	Approved
0.6741	Remote Similarity	NPD4908	Phase 1
0.6733	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD7473	Discontinued
0.6726	Remote Similarity	NPD1089	Approved
0.6726	Remote Similarity	NPD1086	Approved
0.6726	Remote Similarity	NPD1090	Approved
0.6721	Remote Similarity	NPD2342	Discontinued
0.6718	Remote Similarity	NPD1610	Phase 2
0.6716	Remote Similarity	NPD2798	Approved
0.6711	Remote Similarity	NPD7411	Suspended
0.6697	Remote Similarity	NPD9491	Approved
0.6696	Remote Similarity	NPD9094	Approved
0.6695	Remote Similarity	NPD2066	Phase 3
0.6694	Remote Similarity	NPD5048	Discontinued
0.669	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.669	Remote Similarity	NPD6799	Approved
0.6688	Remote Similarity	NPD6959	Discontinued
0.6667	Remote Similarity	NPD9717	Approved
0.6667	Remote Similarity	NPD1548	Phase 1
0.6667	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD826	Approved
0.6667	Remote Similarity	NPD2228	Approved
0.6667	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD825	Approved
0.6667	Remote Similarity	NPD3091	Approved
0.6667	Remote Similarity	NPD2229	Approved
0.6667	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1241	Discontinued
0.6667	Remote Similarity	NPD1551	Phase 2
0.6667	Remote Similarity	NPD2234	Approved
0.6667	Remote Similarity	NPD6166	Phase 2
0.6667	Remote Similarity	NPD6190	Approved
0.6645	Remote Similarity	NPD6232	Discontinued
0.6643	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD1243	Approved
0.6643	Remote Similarity	NPD2654	Approved
0.6642	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.664	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.664	Remote Similarity	NPD228	Approved
0.6637	Remote Similarity	NPD5347	Phase 2
0.6637	Remote Similarity	NPD5346	Phase 2
0.6621	Remote Similarity	NPD3300	Phase 2
0.662	Remote Similarity	NPD2344	Approved
0.6618	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD1791	Approved
0.6614	Remote Similarity	NPD1793	Approved
0.661	Remote Similarity	NPD9273	Approved
0.6609	Remote Similarity	NPD1088	Approved
0.6607	Remote Similarity	NPD4793	Discontinued
0.6604	Remote Similarity	NPD7074	Phase 3
0.6601	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD4628	Phase 3
0.6597	Remote Similarity	NPD8166	Discontinued
0.6596	Remote Similarity	NPD7033	Discontinued
0.6596	Remote Similarity	NPD3748	Approved
0.6591	Remote Similarity	NPD3092	Approved
0.6591	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD1281	Approved
0.6591	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD3817	Phase 2
0.6579	Remote Similarity	NPD9258	Approved
0.6579	Remote Similarity	NPD9256	Approved
0.6573	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD2568	Approved
0.6567	Remote Similarity	NPD6696	Suspended
0.6565	Remote Similarity	NPD4626	Approved
0.6565	Remote Similarity	NPD4059	Approved
0.6556	Remote Similarity	NPD37	Approved
0.6552	Remote Similarity	NPD5122	Clinical (unspecified phase)

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