NPASS Compound

Structure

CID257976 OpenBabel06191716062D 21 21 0 0 0 0 0 0 0 0999 V2000 -9.5263 2.5000 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 -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 -2.5981 -0.5000 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 -3.4641 -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 -0.8660 -0.5000 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 -3.4641 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 0.0000 -0.0000 0.0000 C 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 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 21 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 2 0 0 0 0 9 16 1 0 0 0 0 10 12 1 0 0 0 0 10 15 1 0 0 0 0 11 13 2 0 0 0 0 11 15 1 0 0 0 0 12 16 1 0 0 0 0 13 17 1 0 0 0 0 14 15 2 0 0 0 0 14 18 1 0 0 0 0 16 19 2 0 0 0 0 17 18 2 0 0 0 0 17 20 1 0 0 0 0 18 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	290.19
Volume:	324.516
LogP:	4.069
LogD:	3.802
LogS:	-3.995
# Rotatable Bonds:	10
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.512
Synthetic Accessibility Score:	2.306
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.624
MDCK Permeability:	2.2724629161530174e-05
Pgp-inhibitor:	0.833
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.187
30% Bioavailability (F30%):	0.059

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.568
Plasma Protein Binding (PPB):	97.22624969482422%
Volume Distribution (VD):	1.12
Pgp-substrate:	2.025946617126465%

ADMET: Metabolism

CYP1A2-inhibitor:	0.949
CYP1A2-substrate:	0.856
CYP2C19-inhibitor:	0.893
CYP2C19-substrate:	0.348
CYP2C9-inhibitor:	0.812
CYP2C9-substrate:	0.943
CYP2D6-inhibitor:	0.774
CYP2D6-substrate:	0.917
CYP3A4-inhibitor:	0.767
CYP3A4-substrate:	0.172

ADMET: Excretion

Clearance (CL):	12.761
Half-life (T1/2):	0.905

ADMET: Toxicity

hERG Blockers:	0.045
Human Hepatotoxicity (H-HT):	0.122
Drug-inuced Liver Injury (DILI):	0.084
AMES Toxicity:	0.052
Rat Oral Acute Toxicity:	0.029
Maximum Recommended Daily Dose:	0.116
Skin Sensitization:	0.569
Carcinogencity:	0.58
Eye Corrosion:	0.195
Eye Irritation:	0.942
Respiratory Toxicity:	0.372

Download Data

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

Natural Product: NPC257976

Natural Product ID:	NPC257976
*Common Name:**	(E)-1-(4-Hydroxy-3-Methoxyphenyl)Undec-4-En-3-One
IUPAC Name:	(E)-1-(4-hydroxy-3-methoxyphenyl)undec-4-en-3-one
Synonyms:
Standard InCHIKey:	GHBAGMWSYWCUGX-CMDGGOBGSA-N
Standard InCHI:	InChI=1S/C18H26O3/c1-3-4-5-6-7-8-9-16(19)12-10-15-11-13-17(20)18(14-15)21-2/h8-9,11,13-14,20H,3-7,10,12H2,1-2H3/b9-8+
SMILES:	CCCCCC/C=C/C(=O)CCc1ccc(c(c1)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL24056
PubChem CID:	44459413
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0000190] Methoxyphenols [CHEMONTID:0001708] Shogaols

*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
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[18177011]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19271742]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20590154]
NPO10906	Pinus koraiensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21953622]
NPO10906	Pinus koraiensis	Species	Pinaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[32520551]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[8064299]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8064299]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	Resin, Exudate, Sap	n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	Rhizome	n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO10906	Pinus koraiensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10906	Pinus koraiensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10906	Pinus koraiensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10906	Pinus koraiensis	Species	Pinaceae	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	2
Others	2

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT681	Cell Line	PC-12	Rattus norvegicus	ED50	=	8.6	uM	PMID[535970]
NPT744	Cell Line	IMR-32	Homo sapiens	ED50	=	12.0	uM	PMID[535970]
NPT76	Cell Line	C6	Rattus norvegicus	Activity	=	108.8	%	PMID[535971]
NPT76	Cell Line	C6	Rattus norvegicus	Activity	=	150.9	%	PMID[535971]

☑ 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 NPC257976 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	269
0.1-0.2	1494
0.2-0.3	4290
0.3-0.4	11164
0.4-0.5	6880
0.5-0.6	4465
0.6-0.7	9258
0.7-0.8	4390
0.8-0.85	310
0.85-0.9	113
0.9-0.95	45
0.95-1	19

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC164778
1.0	High Similarity	NPC242372
1.0	High Similarity	NPC4181
0.9915	High Similarity	NPC312404
0.9915	High Similarity	NPC273686
0.9914	High Similarity	NPC114298
0.9748	High Similarity	NPC179777
0.9667	High Similarity	NPC276466
0.9667	High Similarity	NPC123722
0.9667	High Similarity	NPC151167
0.9667	High Similarity	NPC123228
0.9667	High Similarity	NPC5018
0.9658	High Similarity	NPC201777
0.9583	High Similarity	NPC84076
0.9583	High Similarity	NPC90128
0.9583	High Similarity	NPC303680
0.9573	High Similarity	NPC158949
0.9569	High Similarity	NPC299406
0.9508	High Similarity	NPC304622
0.9496	High Similarity	NPC163083
0.9431	High Similarity	NPC172673
0.9344	High Similarity	NPC32163
0.9344	High Similarity	NPC16651
0.9339	High Similarity	NPC53305
0.9339	High Similarity	NPC257589
0.928	High Similarity	NPC239302
0.9262	High Similarity	NPC92207
0.9262	High Similarity	NPC276014
0.9262	High Similarity	NPC127937
0.925	High Similarity	NPC286573
0.9206	High Similarity	NPC327410
0.9187	High Similarity	NPC20404
0.9187	High Similarity	NPC293641
0.9187	High Similarity	NPC20287
0.9187	High Similarity	NPC12022
0.918	High Similarity	NPC280767
0.9174	High Similarity	NPC229084
0.9174	High Similarity	NPC106659
0.9174	High Similarity	NPC160900
0.9174	High Similarity	NPC18984
0.9167	High Similarity	NPC177291
0.9167	High Similarity	NPC194416
0.9134	High Similarity	NPC471110
0.912	High Similarity	NPC66905
0.9113	High Similarity	NPC278308
0.9113	High Similarity	NPC226661
0.9083	High Similarity	NPC109083
0.9083	High Similarity	NPC14007
0.9083	High Similarity	NPC269843
0.9083	High Similarity	NPC189844
0.9083	High Similarity	NPC60962
0.9083	High Similarity	NPC224814
0.9062	High Similarity	NPC204592
0.9055	High Similarity	NPC475468
0.9024	High Similarity	NPC3221
0.8976	High Similarity	NPC50763
0.8968	High Similarity	NPC65935
0.8968	High Similarity	NPC215941
0.8968	High Similarity	NPC244246
0.8968	High Similarity	NPC319282
0.8968	High Similarity	NPC275724
0.8968	High Similarity	NPC123196
0.8968	High Similarity	NPC137427
0.8968	High Similarity	NPC311419
0.8943	High Similarity	NPC20443
0.8943	High Similarity	NPC60517
0.8943	High Similarity	NPC146886
0.8908	High Similarity	NPC39793
0.888	High Similarity	NPC117237
0.888	High Similarity	NPC203719
0.8879	High Similarity	NPC257124
0.8879	High Similarity	NPC156840
0.8879	High Similarity	NPC8547
0.8879	High Similarity	NPC173746
0.8862	High Similarity	NPC244876
0.8855	High Similarity	NPC284409
0.8846	High Similarity	NPC90431
0.8833	High Similarity	NPC137537
0.8833	High Similarity	NPC70744
0.8833	High Similarity	NPC164706
0.8833	High Similarity	NPC205502
0.8833	High Similarity	NPC272471
0.8833	High Similarity	NPC107588
0.8824	High Similarity	NPC19290
0.8819	High Similarity	NPC195292
0.8819	High Similarity	NPC142985
0.88	High Similarity	NPC213552
0.88	High Similarity	NPC120225
0.8788	High Similarity	NPC474784
0.8788	High Similarity	NPC322021
0.877	High Similarity	NPC204466
0.877	High Similarity	NPC225245
0.8769	High Similarity	NPC139519
0.875	High Similarity	NPC164386
0.875	High Similarity	NPC280001
0.875	High Similarity	NPC469480
0.874	High Similarity	NPC241354
0.873	High Similarity	NPC281020
0.872	High Similarity	NPC289459
0.872	High Similarity	NPC87113
0.871	High Similarity	NPC474691
0.8707	High Similarity	NPC246358
0.8707	High Similarity	NPC36108
0.8707	High Similarity	NPC7097
0.8707	High Similarity	NPC233731
0.8699	High Similarity	NPC70752
0.8689	High Similarity	NPC202474
0.8682	High Similarity	NPC111888
0.8678	High Similarity	NPC470626
0.8678	High Similarity	NPC212743
0.8672	High Similarity	NPC298268
0.8667	High Similarity	NPC277394
0.8667	High Similarity	NPC299252
0.8667	High Similarity	NPC61062
0.8667	High Similarity	NPC268317
0.8657	High Similarity	NPC472410
0.8647	High Similarity	NPC289690
0.8647	High Similarity	NPC288452
0.864	High Similarity	NPC246704
0.8626	High Similarity	NPC152209
0.8626	High Similarity	NPC208760
0.8615	High Similarity	NPC283823
0.8615	High Similarity	NPC159418
0.8607	High Similarity	NPC24474
0.8607	High Similarity	NPC310338
0.8607	High Similarity	NPC281298
0.8607	High Similarity	NPC311595
0.8595	High Similarity	NPC293619
0.8595	High Similarity	NPC185738
0.8594	High Similarity	NPC83062
0.8594	High Similarity	NPC261759
0.8593	High Similarity	NPC176030
0.8593	High Similarity	NPC229218
0.8593	High Similarity	NPC169214
0.8593	High Similarity	NPC141817
0.8593	High Similarity	NPC192597
0.8582	High Similarity	NPC82336
0.8582	High Similarity	NPC78987
0.8582	High Similarity	NPC908
0.8582	High Similarity	NPC138438
0.8571	High Similarity	NPC325625
0.856	High Similarity	NPC238810
0.8559	High Similarity	NPC78918
0.8559	High Similarity	NPC195873
0.8559	High Similarity	NPC139617
0.855	High Similarity	NPC300776
0.855	High Similarity	NPC5310
0.855	High Similarity	NPC4982
0.855	High Similarity	NPC144662
0.855	High Similarity	NPC176814
0.855	High Similarity	NPC68779
0.8537	High Similarity	NPC117780
0.8537	High Similarity	NPC165133
0.8537	High Similarity	NPC2058
0.8537	High Similarity	NPC227217
0.8537	High Similarity	NPC232316
0.8537	High Similarity	NPC95614
0.8537	High Similarity	NPC56214
0.8537	High Similarity	NPC242885
0.8529	High Similarity	NPC46161
0.8529	High Similarity	NPC46880
0.8529	High Similarity	NPC239608
0.8529	High Similarity	NPC16353
0.8527	High Similarity	NPC477694
0.8527	High Similarity	NPC477705
0.8519	High Similarity	NPC110419
0.8516	High Similarity	NPC478215
0.8516	High Similarity	NPC110313
0.8512	High Similarity	NPC221049
0.85	High Similarity	NPC294941
0.8485	Intermediate Similarity	NPC113295
0.8485	Intermediate Similarity	NPC252343
0.8475	Intermediate Similarity	NPC137685
0.8468	Intermediate Similarity	NPC207613
0.8467	Intermediate Similarity	NPC207732
0.8462	Intermediate Similarity	NPC477706
0.8456	Intermediate Similarity	NPC312256
0.8444	Intermediate Similarity	NPC28398
0.8443	Intermediate Similarity	NPC150919
0.8443	Intermediate Similarity	NPC86947
0.8417	Intermediate Similarity	NPC148969
0.8406	Intermediate Similarity	NPC157133
0.84	Intermediate Similarity	NPC262156
0.84	Intermediate Similarity	NPC312675
0.84	Intermediate Similarity	NPC470212
0.84	Intermediate Similarity	NPC54872
0.84	Intermediate Similarity	NPC184651
0.84	Intermediate Similarity	NPC473853
0.84	Intermediate Similarity	NPC343720
0.84	Intermediate Similarity	NPC38996
0.84	Intermediate Similarity	NPC324571
0.84	Intermediate Similarity	NPC160380
0.84	Intermediate Similarity	NPC113865
0.8394	Intermediate Similarity	NPC254659
0.8394	Intermediate Similarity	NPC469615
0.8394	Intermediate Similarity	NPC209085
0.8394	Intermediate Similarity	NPC50954
0.8394	Intermediate Similarity	NPC224884
0.8385	Intermediate Similarity	NPC285776
0.8382	Intermediate Similarity	NPC84273

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 NPC257976 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	283
0.1-0.2	961
0.2-0.3	1524
0.3-0.4	2632
0.4-0.5	1865
0.5-0.6	1124
0.6-0.7	643
0.7-0.8	113
0.8-0.85	1
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9174	High Similarity	NPD4379	Clinical (unspecified phase)
0.888	High Similarity	NPD9494	Approved
0.8879	High Similarity	NPD228	Approved
0.8595	High Similarity	NPD5536	Phase 2
0.7967	Intermediate Similarity	NPD1241	Discontinued
0.7967	Intermediate Similarity	NPD5283	Phase 1
0.7895	Intermediate Similarity	NPD3027	Phase 3
0.7838	Intermediate Similarity	NPD3882	Suspended
0.7823	Intermediate Similarity	NPD2801	Approved
0.7817	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7794	Intermediate Similarity	NPD447	Suspended
0.7778	Intermediate Similarity	NPD2674	Phase 3
0.7755	Intermediate Similarity	NPD1934	Approved
0.7734	Intermediate Similarity	NPD1651	Approved
0.7734	Intermediate Similarity	NPD1357	Approved
0.773	Intermediate Similarity	NPD8166	Discontinued
0.7705	Intermediate Similarity	NPD2684	Approved
0.7698	Intermediate Similarity	NPD2935	Discontinued
0.7674	Intermediate Similarity	NPD4626	Approved
0.7671	Intermediate Similarity	NPD824	Approved
0.7664	Intermediate Similarity	NPD230	Phase 1
0.7642	Intermediate Similarity	NPD3021	Approved
0.7642	Intermediate Similarity	NPD3022	Approved
0.7634	Intermediate Similarity	NPD3972	Approved
0.7623	Intermediate Similarity	NPD1358	Approved
0.7606	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD4110	Phase 3
0.7591	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7591	Intermediate Similarity	NPD3620	Phase 2
0.7586	Intermediate Similarity	NPD9296	Approved
0.7584	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD3145	Approved
0.7574	Intermediate Similarity	NPD3144	Approved
0.7569	Intermediate Similarity	NPD1511	Approved
0.7541	Intermediate Similarity	NPD3134	Approved
0.7519	Intermediate Similarity	NPD1876	Approved
0.7519	Intermediate Similarity	NPD9545	Approved
0.7519	Intermediate Similarity	NPD1283	Approved
0.75	Intermediate Similarity	NPD7028	Phase 2
0.7483	Intermediate Similarity	NPD4628	Phase 3
0.7466	Intermediate Similarity	NPD1512	Approved
0.7464	Intermediate Similarity	NPD1240	Approved
0.746	Intermediate Similarity	NPD7843	Approved
0.7445	Intermediate Similarity	NPD6798	Discontinued
0.7432	Intermediate Similarity	NPD3455	Phase 2
0.7431	Intermediate Similarity	NPD6190	Approved
0.7422	Intermediate Similarity	NPD7157	Approved
0.7415	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD6355	Discontinued
0.7407	Intermediate Similarity	NPD2798	Approved
0.7391	Intermediate Similarity	NPD4062	Phase 3
0.7391	Intermediate Similarity	NPD6233	Phase 2
0.7385	Intermediate Similarity	NPD1894	Discontinued
0.7372	Intermediate Similarity	NPD6166	Phase 2
0.7372	Intermediate Similarity	NPD7095	Approved
0.7372	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD9493	Approved
0.7357	Intermediate Similarity	NPD1607	Approved
0.7348	Intermediate Similarity	NPD3496	Discontinued
0.7348	Intermediate Similarity	NPD3847	Discontinued
0.7338	Intermediate Similarity	NPD1558	Phase 1
0.7338	Intermediate Similarity	NPD943	Approved
0.7338	Intermediate Similarity	NPD826	Approved
0.7338	Intermediate Similarity	NPD4060	Phase 1
0.7338	Intermediate Similarity	NPD825	Approved
0.7333	Intermediate Similarity	NPD2797	Approved
0.7329	Intermediate Similarity	NPD4357	Discontinued
0.7328	Intermediate Similarity	NPD5691	Approved
0.7303	Intermediate Similarity	NPD3817	Phase 2
0.7299	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD1535	Discovery
0.7293	Intermediate Similarity	NPD1281	Approved
0.7293	Intermediate Similarity	NPD3705	Approved
0.7287	Intermediate Similarity	NPD6671	Approved
0.7279	Intermediate Similarity	NPD258	Approved
0.7279	Intermediate Similarity	NPD5647	Approved
0.7279	Intermediate Similarity	NPD257	Approved
0.7278	Intermediate Similarity	NPD3818	Discontinued
0.7273	Intermediate Similarity	NPD2932	Approved
0.7273	Intermediate Similarity	NPD2344	Approved
0.7273	Intermediate Similarity	NPD3019	Approved
0.7273	Intermediate Similarity	NPD1778	Approved
0.7273	Intermediate Similarity	NPD7266	Discontinued
0.7266	Intermediate Similarity	NPD259	Phase 1
0.7254	Intermediate Similarity	NPD1510	Phase 2
0.7254	Intermediate Similarity	NPD2799	Discontinued
0.7239	Intermediate Similarity	NPD9717	Approved
0.7239	Intermediate Similarity	NPD9269	Phase 2
0.7239	Intermediate Similarity	NPD1608	Approved
0.7239	Intermediate Similarity	NPD1481	Phase 2
0.7234	Intermediate Similarity	NPD6653	Approved
0.7233	Intermediate Similarity	NPD7054	Approved
0.7226	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD1613	Approved
0.7214	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD290	Approved
0.72	Intermediate Similarity	NPD3866	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD3268	Approved
0.7188	Intermediate Similarity	NPD7074	Phase 3
0.7188	Intermediate Similarity	NPD7472	Approved
0.7185	Intermediate Similarity	NPD2982	Phase 2
0.7185	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD2983	Phase 2
0.7172	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD1933	Approved
0.7163	Intermediate Similarity	NPD555	Phase 2
0.7161	Intermediate Similarity	NPD6234	Discontinued
0.7152	Intermediate Similarity	NPD4380	Phase 2
0.7143	Intermediate Similarity	NPD2933	Approved
0.7143	Intermediate Similarity	NPD2934	Approved
0.7134	Intermediate Similarity	NPD6232	Discontinued
0.7133	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1653	Approved
0.7124	Intermediate Similarity	NPD1006	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD7003	Approved
0.7117	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD2981	Phase 2
0.7107	Intermediate Similarity	NPD7473	Discontinued
0.7105	Intermediate Similarity	NPD6386	Approved
0.7105	Intermediate Similarity	NPD6385	Approved
0.7105	Intermediate Similarity	NPD6873	Phase 2
0.7103	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD4534	Discontinued
0.7103	Intermediate Similarity	NPD2424	Discontinued
0.7101	Intermediate Similarity	NPD3018	Phase 2
0.7101	Intermediate Similarity	NPD9569	Approved
0.7099	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD6799	Approved
0.7092	Intermediate Similarity	NPD3142	Approved
0.7092	Intermediate Similarity	NPD3140	Approved
0.7086	Intermediate Similarity	NPD7458	Discontinued
0.7083	Intermediate Similarity	NPD2860	Approved
0.7083	Intermediate Similarity	NPD2859	Approved
0.708	Intermediate Similarity	NPD1203	Approved
0.7078	Intermediate Similarity	NPD5978	Approved
0.7078	Intermediate Similarity	NPD5977	Approved
0.7077	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD2354	Approved
0.7075	Intermediate Similarity	NPD2309	Approved
0.7071	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD411	Approved
0.707	Intermediate Similarity	NPD8127	Discontinued
0.707	Intermediate Similarity	NPD2821	Approved
0.7068	Intermediate Similarity	NPD5585	Approved
0.7068	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD37	Approved
0.7055	Intermediate Similarity	NPD3060	Approved
0.7054	Intermediate Similarity	NPD821	Approved
0.7054	Intermediate Similarity	NPD9377	Approved
0.7054	Intermediate Similarity	NPD9379	Approved
0.705	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD2614	Approved
0.7049	Intermediate Similarity	NPD3020	Approved
0.7047	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD3146	Approved
0.7037	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6797	Phase 2
0.7037	Intermediate Similarity	NPD422	Phase 1
0.703	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD6584	Phase 3
0.7021	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD8032	Phase 2
0.7015	Intermediate Similarity	NPD17	Approved
0.7013	Intermediate Similarity	NPD1465	Phase 2
0.7007	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD3750	Approved
0.7007	Intermediate Similarity	NPD196	Phase 1
0.7007	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6273	Approved
0.7	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7251	Discontinued
0.6994	Remote Similarity	NPD7685	Pre-registration
0.6993	Remote Similarity	NPD2492	Phase 1
0.6993	Remote Similarity	NPD2653	Approved
0.6987	Remote Similarity	NPD7075	Discontinued
0.6986	Remote Similarity	NPD1549	Phase 2
0.6986	Remote Similarity	NPD5958	Discontinued
0.6984	Remote Similarity	NPD968	Approved
0.6974	Remote Similarity	NPD2649	Approved
0.6974	Remote Similarity	NPD2651	Approved
0.6972	Remote Similarity	NPD2979	Phase 3
0.6966	Remote Similarity	NPD2796	Approved
0.6966	Remote Similarity	NPD6099	Approved
0.6966	Remote Similarity	NPD6100	Approved
0.6966	Remote Similarity	NPD2240	Approved
0.6966	Remote Similarity	NPD2438	Suspended
0.6966	Remote Similarity	NPD2239	Approved
0.6966	Remote Similarity	NPD2161	Phase 2
0.6957	Remote Similarity	NPD987	Approved
0.6954	Remote Similarity	NPD3640	Phase 3
0.6954	Remote Similarity	NPD3641	Approved
0.6954	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD3639	Approved
0.6953	Remote Similarity	NPD5451	Approved
0.6951	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD7808	Phase 3

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