NPASS Compound

Structure

CID273686 OpenBabel06191716082D 26 26 0 0 0 0 0 0 0 0999 V2000 9.5263 10.5000 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 8.6603 11.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 10.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 9.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 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 2.5981 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 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 2.0000 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 4.3301 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 26 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 2 0 0 0 0 14 21 1 0 0 0 0 15 17 1 0 0 0 0 15 20 1 0 0 0 0 16 18 2 0 0 0 0 16 20 1 0 0 0 0 17 21 1 0 0 0 0 18 22 1 0 0 0 0 19 20 2 0 0 0 0 19 23 1 0 0 0 0 21 24 2 0 0 0 0 22 23 2 0 0 0 0 22 25 1 0 0 0 0 23 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	360.27
Volume:	410.996
LogP:	6.59
LogD:	4.754
LogS:	-5.086
# Rotatable Bonds:	15
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.291
Synthetic Accessibility Score:	2.345
Fsp3:	0.609
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.745
MDCK Permeability:	1.4465220374404453e-05
Pgp-inhibitor:	0.977
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.988
30% Bioavailability (F30%):	0.974

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.629
Plasma Protein Binding (PPB):	98.7713851928711%
Volume Distribution (VD):	2.664
Pgp-substrate:	0.8315808176994324%

ADMET: Metabolism

CYP1A2-inhibitor:	0.69
CYP1A2-substrate:	0.472
CYP2C19-inhibitor:	0.712
CYP2C19-substrate:	0.079
CYP2C9-inhibitor:	0.498
CYP2C9-substrate:	0.967
CYP2D6-inhibitor:	0.7
CYP2D6-substrate:	0.913
CYP3A4-inhibitor:	0.709
CYP3A4-substrate:	0.108

ADMET: Excretion

Clearance (CL):	9.418
Half-life (T1/2):	0.71

ADMET: Toxicity

hERG Blockers:	0.13
Human Hepatotoxicity (H-HT):	0.056
Drug-inuced Liver Injury (DILI):	0.049
AMES Toxicity:	0.042
Rat Oral Acute Toxicity:	0.019
Maximum Recommended Daily Dose:	0.103
Skin Sensitization:	0.879
Carcinogencity:	0.122
Eye Corrosion:	0.261
Eye Irritation:	0.958
Respiratory Toxicity:	0.836

Download Data

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

Natural Product: NPC273686

Natural Product ID:	NPC273686
*Common Name:**	(E)-1-(4-Hydroxy-3-Methoxyphenyl)Hexadec-4-En-3-One
IUPAC Name:	(E)-1-(4-hydroxy-3-methoxyphenyl)hexadec-4-en-3-one
Synonyms:
Standard InCHIKey:	WCQFXNQALHURHS-BUHFOSPRSA-N
Standard InCHI:	InChI=1S/C23H36O3/c1-3-4-5-6-7-8-9-10-11-12-13-14-21(24)17-15-20-16-18-22(25)23(19-20)26-2/h13-14,16,18-19,25H,3-12,15,17H2,1-2H3/b14-13+
SMILES:	CCCCCCCCCCC/C=C/C(=O)CCc1ccc(c(c1)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL24703
PubChem CID:	9975813
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]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8064299]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	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]
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]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]

☑ 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

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT681	Cell Line	PC-12	Rattus norvegicus	ED50	=	0.2	uM	PMID[542968]
NPT744	Cell Line	IMR-32	Homo sapiens	ED50	=	0.5	uM	PMID[542968]

☑ 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 NPC273686 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	265
0.1-0.2	1465
0.2-0.3	4097
0.3-0.4	10759
0.4-0.5	7470
0.5-0.6	4434
0.6-0.7	9627
0.7-0.8	4153
0.8-0.85	263
0.85-0.9	108
0.9-0.95	41
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC312404
0.9915	High Similarity	NPC257976
0.9915	High Similarity	NPC242372
0.9915	High Similarity	NPC164778
0.9915	High Similarity	NPC4181
0.9829	High Similarity	NPC114298
0.9667	High Similarity	NPC179777
0.9587	High Similarity	NPC123722
0.9587	High Similarity	NPC151167
0.9587	High Similarity	NPC276466
0.9587	High Similarity	NPC5018
0.9587	High Similarity	NPC123228
0.9576	High Similarity	NPC201777
0.9504	High Similarity	NPC84076
0.9504	High Similarity	NPC303680
0.9504	High Similarity	NPC90128
0.9492	High Similarity	NPC158949
0.9487	High Similarity	NPC299406
0.9431	High Similarity	NPC304622
0.9417	High Similarity	NPC163083
0.9355	High Similarity	NPC172673
0.9268	High Similarity	NPC32163
0.9268	High Similarity	NPC16651
0.9262	High Similarity	NPC257589
0.9262	High Similarity	NPC53305
0.9213	High Similarity	NPC471110
0.9206	High Similarity	NPC239302
0.9194	High Similarity	NPC278308
0.9187	High Similarity	NPC127937
0.9187	High Similarity	NPC276014
0.9187	High Similarity	NPC92207
0.9174	High Similarity	NPC286573
0.9134	High Similarity	NPC475468
0.9134	High Similarity	NPC327410
0.9113	High Similarity	NPC20287
0.9113	High Similarity	NPC12022
0.9113	High Similarity	NPC20404
0.9113	High Similarity	NPC293641
0.9106	High Similarity	NPC280767
0.9098	High Similarity	NPC106659
0.9098	High Similarity	NPC160900
0.9098	High Similarity	NPC18984
0.9098	High Similarity	NPC229084
0.9091	High Similarity	NPC194416
0.9091	High Similarity	NPC177291
0.9048	High Similarity	NPC66905
0.904	High Similarity	NPC226661
0.9024	High Similarity	NPC20443
0.9024	High Similarity	NPC60517
0.9024	High Similarity	NPC146886
0.9008	High Similarity	NPC224814
0.9008	High Similarity	NPC14007
0.9008	High Similarity	NPC109083
0.9008	High Similarity	NPC269843
0.9008	High Similarity	NPC189844
0.9008	High Similarity	NPC60962
0.8992	High Similarity	NPC204592
0.8952	High Similarity	NPC3221
0.8906	High Similarity	NPC50763
0.8898	High Similarity	NPC244246
0.8898	High Similarity	NPC311419
0.8898	High Similarity	NPC137427
0.8898	High Similarity	NPC123196
0.8898	High Similarity	NPC319282
0.8898	High Similarity	NPC275724
0.8898	High Similarity	NPC65935
0.8898	High Similarity	NPC215941
0.8833	High Similarity	NPC39793
0.881	High Similarity	NPC117237
0.881	High Similarity	NPC203719
0.8803	High Similarity	NPC173746
0.8803	High Similarity	NPC257124
0.8803	High Similarity	NPC156840
0.8803	High Similarity	NPC8547
0.879	High Similarity	NPC244876
0.8788	High Similarity	NPC284409
0.8779	High Similarity	NPC90431
0.876	High Similarity	NPC164706
0.876	High Similarity	NPC107588
0.876	High Similarity	NPC137537
0.876	High Similarity	NPC70744
0.876	High Similarity	NPC272471
0.876	High Similarity	NPC205502
0.875	High Similarity	NPC195292
0.875	High Similarity	NPC19290
0.875	High Similarity	NPC142985
0.8731	High Similarity	NPC472410
0.873	High Similarity	NPC120225
0.873	High Similarity	NPC213552
0.8722	High Similarity	NPC474784
0.8722	High Similarity	NPC322021
0.8702	High Similarity	NPC139519
0.8699	High Similarity	NPC204466
0.8699	High Similarity	NPC225245
0.8682	High Similarity	NPC469480
0.8678	High Similarity	NPC164386
0.8678	High Similarity	NPC280001
0.8672	High Similarity	NPC83062
0.8672	High Similarity	NPC241354
0.8661	High Similarity	NPC281020
0.8651	High Similarity	NPC289459
0.8651	High Similarity	NPC87113
0.864	High Similarity	NPC474691
0.8632	High Similarity	NPC36108
0.8632	High Similarity	NPC246358
0.8632	High Similarity	NPC7097
0.8632	High Similarity	NPC233731
0.8629	High Similarity	NPC70752
0.8618	High Similarity	NPC202474
0.8615	High Similarity	NPC111888
0.8607	High Similarity	NPC212743
0.8607	High Similarity	NPC470626
0.8605	High Similarity	NPC298268
0.8595	High Similarity	NPC277394
0.8595	High Similarity	NPC61062
0.8595	High Similarity	NPC299252
0.8595	High Similarity	NPC268317
0.8582	High Similarity	NPC289690
0.8582	High Similarity	NPC288452
0.8571	High Similarity	NPC246704
0.8561	High Similarity	NPC152209
0.8561	High Similarity	NPC208760
0.855	High Similarity	NPC283823
0.855	High Similarity	NPC159418
0.8538	High Similarity	NPC477706
0.8537	High Similarity	NPC311595
0.8537	High Similarity	NPC281298
0.8537	High Similarity	NPC310338
0.8537	High Similarity	NPC24474
0.8529	High Similarity	NPC141817
0.8529	High Similarity	NPC176030
0.8529	High Similarity	NPC229218
0.8529	High Similarity	NPC169214
0.8529	High Similarity	NPC192597
0.8527	High Similarity	NPC261759
0.8525	High Similarity	NPC185738
0.8525	High Similarity	NPC293619
0.8519	High Similarity	NPC78987
0.8519	High Similarity	NPC138438
0.8519	High Similarity	NPC908
0.8519	High Similarity	NPC82336
0.8507	High Similarity	NPC325625
0.8492	Intermediate Similarity	NPC238810
0.8487	Intermediate Similarity	NPC139617
0.8487	Intermediate Similarity	NPC195873
0.8487	Intermediate Similarity	NPC78918
0.8485	Intermediate Similarity	NPC68779
0.8485	Intermediate Similarity	NPC144662
0.8485	Intermediate Similarity	NPC4982
0.8485	Intermediate Similarity	NPC5310
0.8485	Intermediate Similarity	NPC300776
0.8485	Intermediate Similarity	NPC176814
0.8468	Intermediate Similarity	NPC227217
0.8468	Intermediate Similarity	NPC232316
0.8468	Intermediate Similarity	NPC165133
0.8468	Intermediate Similarity	NPC56214
0.8468	Intermediate Similarity	NPC117780
0.8468	Intermediate Similarity	NPC2058
0.8468	Intermediate Similarity	NPC95614
0.8468	Intermediate Similarity	NPC242885
0.8467	Intermediate Similarity	NPC16353
0.8467	Intermediate Similarity	NPC239608
0.8467	Intermediate Similarity	NPC46161
0.8467	Intermediate Similarity	NPC469615
0.8467	Intermediate Similarity	NPC46880
0.8462	Intermediate Similarity	NPC477705
0.8462	Intermediate Similarity	NPC477694
0.8456	Intermediate Similarity	NPC110419
0.8455	Intermediate Similarity	NPC203124
0.845	Intermediate Similarity	NPC478215
0.845	Intermediate Similarity	NPC110313
0.8443	Intermediate Similarity	NPC221049
0.843	Intermediate Similarity	NPC294941
0.8421	Intermediate Similarity	NPC113295
0.8421	Intermediate Similarity	NPC252343
0.8406	Intermediate Similarity	NPC207732
0.8406	Intermediate Similarity	NPC469683
0.8403	Intermediate Similarity	NPC137685
0.84	Intermediate Similarity	NPC207613
0.8394	Intermediate Similarity	NPC312256
0.8382	Intermediate Similarity	NPC28398
0.8374	Intermediate Similarity	NPC150919
0.8374	Intermediate Similarity	NPC86947
0.8347	Intermediate Similarity	NPC148969
0.8345	Intermediate Similarity	NPC157133
0.8333	Intermediate Similarity	NPC160380
0.8333	Intermediate Similarity	NPC470212
0.8333	Intermediate Similarity	NPC254659
0.8333	Intermediate Similarity	NPC54872
0.8333	Intermediate Similarity	NPC209085
0.8333	Intermediate Similarity	NPC50954
0.8333	Intermediate Similarity	NPC343720
0.8333	Intermediate Similarity	NPC184651
0.8333	Intermediate Similarity	NPC324571
0.8333	Intermediate Similarity	NPC473853
0.8333	Intermediate Similarity	NPC262156
0.8333	Intermediate Similarity	NPC113865
0.8333	Intermediate Similarity	NPC38996
0.8333	Intermediate Similarity	NPC224884
0.8333	Intermediate Similarity	NPC312675

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 NPC273686 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	280
0.1-0.2	945
0.2-0.3	1542
0.3-0.4	2645
0.4-0.5	1874
0.5-0.6	1115
0.6-0.7	645
0.7-0.8	99
0.8-0.85	2
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9098	High Similarity	NPD4379	Clinical (unspecified phase)
0.881	High Similarity	NPD9494	Approved
0.8803	High Similarity	NPD228	Approved
0.8525	High Similarity	NPD5536	Phase 2
0.7903	Intermediate Similarity	NPD5283	Phase 1
0.7903	Intermediate Similarity	NPD1241	Discontinued
0.7836	Intermediate Similarity	NPD3027	Phase 3
0.7801	Intermediate Similarity	NPD8166	Discontinued
0.7785	Intermediate Similarity	NPD3882	Suspended
0.777	Intermediate Similarity	NPD2801	Approved
0.7762	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7737	Intermediate Similarity	NPD447	Suspended
0.7721	Intermediate Similarity	NPD2674	Phase 3
0.7703	Intermediate Similarity	NPD1934	Approved
0.7674	Intermediate Similarity	NPD1651	Approved
0.7674	Intermediate Similarity	NPD1357	Approved
0.7643	Intermediate Similarity	NPD2935	Discontinued
0.7642	Intermediate Similarity	NPD2684	Approved
0.7619	Intermediate Similarity	NPD824	Approved
0.7615	Intermediate Similarity	NPD4626	Approved
0.7609	Intermediate Similarity	NPD230	Phase 1
0.7581	Intermediate Similarity	NPD3022	Approved
0.7581	Intermediate Similarity	NPD3021	Approved
0.7576	Intermediate Similarity	NPD3972	Approved
0.7561	Intermediate Similarity	NPD1358	Approved
0.7552	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD4110	Phase 3
0.754	Intermediate Similarity	NPD7843	Approved
0.7536	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD3620	Phase 2
0.7533	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD9296	Approved
0.7518	Intermediate Similarity	NPD3144	Approved
0.7518	Intermediate Similarity	NPD3145	Approved
0.7517	Intermediate Similarity	NPD1511	Approved
0.75	Intermediate Similarity	NPD7157	Approved
0.7482	Intermediate Similarity	NPD6355	Discontinued
0.748	Intermediate Similarity	NPD3134	Approved
0.7463	Intermediate Similarity	NPD1876	Approved
0.7463	Intermediate Similarity	NPD1283	Approved
0.7462	Intermediate Similarity	NPD9545	Approved
0.745	Intermediate Similarity	NPD7028	Phase 2
0.7445	Intermediate Similarity	NPD7095	Approved
0.7431	Intermediate Similarity	NPD4628	Phase 3
0.7415	Intermediate Similarity	NPD1512	Approved
0.741	Intermediate Similarity	NPD1240	Approved
0.7391	Intermediate Similarity	NPD6798	Discontinued
0.7383	Intermediate Similarity	NPD3455	Phase 2
0.7379	Intermediate Similarity	NPD6190	Approved
0.7365	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD6671	Approved
0.7353	Intermediate Similarity	NPD2798	Approved
0.7343	Intermediate Similarity	NPD7266	Discontinued
0.7338	Intermediate Similarity	NPD4062	Phase 3
0.7338	Intermediate Similarity	NPD6233	Phase 2
0.7328	Intermediate Similarity	NPD1894	Discontinued
0.7325	Intermediate Similarity	NPD6166	Phase 2
0.7325	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD9493	Approved
0.7305	Intermediate Similarity	NPD1607	Approved
0.7305	Intermediate Similarity	NPD6653	Approved
0.7296	Intermediate Similarity	NPD7054	Approved
0.7293	Intermediate Similarity	NPD3847	Discontinued
0.7293	Intermediate Similarity	NPD3496	Discontinued
0.7286	Intermediate Similarity	NPD825	Approved
0.7286	Intermediate Similarity	NPD1558	Phase 1
0.7286	Intermediate Similarity	NPD826	Approved
0.7286	Intermediate Similarity	NPD943	Approved
0.7286	Intermediate Similarity	NPD4060	Phase 1
0.7279	Intermediate Similarity	NPD4357	Discontinued
0.7279	Intermediate Similarity	NPD2797	Approved
0.7273	Intermediate Similarity	NPD5691	Approved
0.7255	Intermediate Similarity	NPD3817	Phase 2
0.725	Intermediate Similarity	NPD7074	Phase 3
0.725	Intermediate Similarity	NPD7472	Approved
0.7246	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD1535	Discovery
0.7239	Intermediate Similarity	NPD3705	Approved
0.7239	Intermediate Similarity	NPD1281	Approved
0.7233	Intermediate Similarity	NPD3818	Discontinued
0.7226	Intermediate Similarity	NPD257	Approved
0.7226	Intermediate Similarity	NPD5647	Approved
0.7226	Intermediate Similarity	NPD258	Approved
0.7222	Intermediate Similarity	NPD2344	Approved
0.7218	Intermediate Similarity	NPD2932	Approved
0.7218	Intermediate Similarity	NPD3019	Approved
0.7218	Intermediate Similarity	NPD1778	Approved
0.7214	Intermediate Similarity	NPD259	Phase 1
0.7203	Intermediate Similarity	NPD1510	Phase 2
0.7203	Intermediate Similarity	NPD2799	Discontinued
0.7185	Intermediate Similarity	NPD1608	Approved
0.7185	Intermediate Similarity	NPD1481	Phase 2
0.7185	Intermediate Similarity	NPD9269	Phase 2
0.7185	Intermediate Similarity	NPD9717	Approved
0.7174	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD6385	Approved
0.7171	Intermediate Similarity	NPD6386	Approved
0.7171	Intermediate Similarity	NPD6873	Phase 2
0.717	Intermediate Similarity	NPD7473	Discontinued
0.7163	Intermediate Similarity	NPD1613	Approved
0.7163	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3866	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7458	Discontinued
0.7143	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD290	Approved
0.7143	Intermediate Similarity	NPD3268	Approved
0.7134	Intermediate Similarity	NPD8127	Discontinued
0.7132	Intermediate Similarity	NPD2982	Phase 2
0.7132	Intermediate Similarity	NPD2983	Phase 2
0.7132	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6234	Discontinued
0.7113	Intermediate Similarity	NPD1933	Approved
0.7113	Intermediate Similarity	NPD555	Phase 2
0.7105	Intermediate Similarity	NPD4380	Phase 2
0.7092	Intermediate Similarity	NPD8032	Phase 2
0.7091	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD6232	Discontinued
0.7086	Intermediate Similarity	NPD1653	Approved
0.7083	Intermediate Similarity	NPD2934	Approved
0.7083	Intermediate Similarity	NPD2933	Approved
0.7083	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD1006	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD7003	Approved
0.7075	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2981	Phase 2
0.7055	Intermediate Similarity	NPD4534	Discontinued
0.7055	Intermediate Similarity	NPD2424	Discontinued
0.7055	Intermediate Similarity	NPD7251	Discontinued
0.7055	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD7685	Pre-registration
0.7051	Intermediate Similarity	NPD7075	Discontinued
0.705	Intermediate Similarity	NPD3018	Phase 2
0.705	Intermediate Similarity	NPD9569	Approved
0.7047	Intermediate Similarity	NPD6799	Approved
0.7045	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD3142	Approved
0.7042	Intermediate Similarity	NPD3140	Approved
0.7034	Intermediate Similarity	NPD6099	Approved
0.7034	Intermediate Similarity	NPD6100	Approved
0.7032	Intermediate Similarity	NPD5978	Approved
0.7032	Intermediate Similarity	NPD5977	Approved
0.7029	Intermediate Similarity	NPD1203	Approved
0.7027	Intermediate Similarity	NPD2354	Approved
0.7027	Intermediate Similarity	NPD2309	Approved
0.7025	Intermediate Similarity	NPD2821	Approved
0.7025	Intermediate Similarity	NPD2859	Approved
0.7025	Intermediate Similarity	NPD2860	Approved
0.7023	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD411	Approved
0.7021	Intermediate Similarity	NPD5718	Phase 2
0.702	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD5585	Approved
0.7013	Intermediate Similarity	NPD37	Approved
0.7012	Intermediate Similarity	NPD7808	Phase 3
0.7008	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD3060	Approved
0.7	Intermediate Similarity	NPD3146	Approved
0.7	Intermediate Similarity	NPD821	Approved
0.7	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD9379	Approved
0.7	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD9377	Approved
0.7	Intermediate Similarity	NPD2614	Approved
0.7	Intermediate Similarity	NPD6832	Phase 2
0.6994	Remote Similarity	NPD6797	Phase 2
0.6992	Remote Similarity	NPD3020	Approved
0.6985	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD422	Phase 1
0.6978	Remote Similarity	NPD6584	Phase 3
0.6972	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD1465	Phase 2
0.6968	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD17	Approved
0.6959	Remote Similarity	NPD3750	Approved
0.6959	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD196	Phase 1
0.6954	Remote Similarity	NPD6273	Approved
0.6944	Remote Similarity	NPD2653	Approved
0.6944	Remote Similarity	NPD2492	Phase 1
0.6942	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD7153	Discontinued
0.6939	Remote Similarity	NPD1549	Phase 2
0.6939	Remote Similarity	NPD5958	Discontinued
0.6929	Remote Similarity	NPD968	Approved
0.6928	Remote Similarity	NPD2649	Approved
0.6928	Remote Similarity	NPD2651	Approved
0.6923	Remote Similarity	NPD2979	Phase 3
0.6918	Remote Similarity	NPD2240	Approved
0.6918	Remote Similarity	NPD2239	Approved
0.6918	Remote Similarity	NPD2438	Suspended
0.6918	Remote Similarity	NPD2796	Approved
0.6918	Remote Similarity	NPD2161	Phase 2
0.6914	Remote Similarity	NPD7228	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