NPASS Compound

Structure

CID293641 OpenBabel06191716102D 21 21 0 0 1 0 0 0 0 0999 V2000 6.9282 7.0000 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 6.0622 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 7.0000 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 4.3301 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 4.0000 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 4.3301 4.5000 0.0000 C 0 0 1 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 -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 5.1962 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 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 14 1 0 0 0 0 7 9 1 0 0 0 0 7 13 1 0 0 0 0 8 10 2 0 0 0 0 8 13 1 0 0 0 0 9 15 1 0 0 0 0 10 17 1 0 0 0 0 11 13 2 0 0 0 0 11 16 1 0 0 0 0 12 14 1 0 0 0 0 12 15 1 0 0 0 0 14 18 1 6 0 0 0 15 19 2 0 0 0 0 16 17 2 0 0 0 0 16 20 1 0 0 0 0 17 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	294.18
Volume:	318.647
LogP:	2.812
LogD:	3.061
LogS:	-3.281
# Rotatable Bonds:	10
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.65
Synthetic Accessibility Score:	2.605
Fsp3:	0.588
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.602
MDCK Permeability:	2.8263861167943105e-05
Pgp-inhibitor:	0.068
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.979
30% Bioavailability (F30%):	0.06

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.492
Plasma Protein Binding (PPB):	88.78306579589844%
Volume Distribution (VD):	1.699
Pgp-substrate:	9.495307922363281%

ADMET: Metabolism

CYP1A2-inhibitor:	0.703
CYP1A2-substrate:	0.941
CYP2C19-inhibitor:	0.733
CYP2C19-substrate:	0.734
CYP2C9-inhibitor:	0.604
CYP2C9-substrate:	0.894
CYP2D6-inhibitor:	0.394
CYP2D6-substrate:	0.863
CYP3A4-inhibitor:	0.491
CYP3A4-substrate:	0.201

ADMET: Excretion

Clearance (CL):	14.181
Half-life (T1/2):	0.901

ADMET: Toxicity

hERG Blockers:	0.074
Human Hepatotoxicity (H-HT):	0.237
Drug-inuced Liver Injury (DILI):	0.041
AMES Toxicity:	0.159
Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.776
Skin Sensitization:	0.479
Carcinogencity:	0.054
Eye Corrosion:	0.065
Eye Irritation:	0.807
Respiratory Toxicity:	0.327

Download Data

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

Natural Product: NPC293641

Natural Product ID:	NPC293641
*Common Name:**	(S)-6-Gingerol
IUPAC Name:	(5S)-5-hydroxy-1-(3-hydroxy-4-methoxyphenyl)decan-3-one
Synonyms:	(S)-6-Gingerol
Standard InCHIKey:	LPRPIMHDDACJHT-AWEZNQCLSA-N
Standard InCHI:	InChI=1S/C17H26O4/c1-3-4-5-6-14(18)12-15(19)9-7-13-8-10-17(21-2)16(20)11-13/h8,10-11,14,18,20H,3-7,9,12H2,1-2H3/t14-/m0/s1
SMILES:	CCCCC[C@@H](CC(=O)CCc1ccc(c(c1)O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL471072
PubChem CID:	44559528
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0000190] Methoxyphenols

*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
NPO12458	Zingiber aromaticum	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	DOI[10.1080/10575639708043725]
NPO12458	Zingiber aromaticum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15270556]
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.	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	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.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12458	Zingiber aromaticum	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]
NPO12458	Zingiber aromaticum	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]
NPO12458	Zingiber aromaticum	Species	Zingiberaceae	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
IC50	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	IC50	=	36400.0	nM	PMID[568641]
NPT110	Individual Protein	Cytochrome P450 2D6	Homo sapiens	IC50	>	100000.0	nM	PMID[568641]

☑ 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 NPC293641 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	268
0.1-0.2	1241
0.2-0.3	3569
0.3-0.4	9975
0.4-0.5	8891
0.5-0.6	4154
0.6-0.7	8915
0.7-0.8	5208
0.8-0.85	322
0.85-0.9	94
0.9-0.95	38
0.95-1	22

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC20287
1.0	High Similarity	NPC12022
1.0	High Similarity	NPC20404
0.9917	High Similarity	NPC278308
0.9756	High Similarity	NPC123196
0.9756	High Similarity	NPC215941
0.9756	High Similarity	NPC137427
0.9756	High Similarity	NPC65935
0.9756	High Similarity	NPC319282
0.9756	High Similarity	NPC244246
0.9756	High Similarity	NPC275724
0.9756	High Similarity	NPC311419
0.9667	High Similarity	NPC244876
0.9597	High Similarity	NPC195292
0.9504	High Similarity	NPC163083
0.95	High Similarity	NPC201777
0.944	High Similarity	NPC142985
0.9365	High Similarity	NPC469480
0.935	High Similarity	NPC53305
0.935	High Similarity	NPC257589
0.9274	High Similarity	NPC92207
0.9274	High Similarity	NPC127937
0.925	High Similarity	NPC299406
0.9194	High Similarity	NPC280767
0.9187	High Similarity	NPC4181
0.9187	High Similarity	NPC164778
0.9187	High Similarity	NPC242372
0.9187	High Similarity	NPC257976
0.9127	High Similarity	NPC226661
0.912	High Similarity	NPC303680
0.912	High Similarity	NPC90128
0.912	High Similarity	NPC84076
0.9113	High Similarity	NPC273686
0.9113	High Similarity	NPC312404
0.9106	High Similarity	NPC114298
0.9098	High Similarity	NPC158949
0.9091	High Similarity	NPC311595
0.9091	High Similarity	NPC24474
0.9091	High Similarity	NPC474784
0.9083	High Similarity	NPC164386
0.9077	High Similarity	NPC470990
0.907	High Similarity	NPC327410
0.9055	High Similarity	NPC304622
0.9048	High Similarity	NPC123228
0.9048	High Similarity	NPC151167
0.9048	High Similarity	NPC276466
0.9048	High Similarity	NPC123722
0.9048	High Similarity	NPC5018
0.9024	High Similarity	NPC177291
0.9024	High Similarity	NPC194416
0.9	High Similarity	NPC471110
0.8992	High Similarity	NPC50763
0.8984	High Similarity	NPC172673
0.8968	High Similarity	NPC179777
0.8943	High Similarity	NPC98305
0.8943	High Similarity	NPC207613
0.8889	High Similarity	NPC3221
0.8871	High Similarity	NPC343720
0.8871	High Similarity	NPC312675
0.8871	High Similarity	NPC473853
0.8871	High Similarity	NPC262156
0.8871	High Similarity	NPC184651
0.8871	High Similarity	NPC113865
0.8871	High Similarity	NPC470212
0.8871	High Similarity	NPC324571
0.8871	High Similarity	NPC54872
0.8862	High Similarity	NPC34634
0.8862	High Similarity	NPC265454
0.8846	High Similarity	NPC239302
0.8806	High Similarity	NPC322021
0.8788	High Similarity	NPC113295
0.8779	High Similarity	NPC475468
0.876	High Similarity	NPC241354
0.8731	High Similarity	NPC325625
0.873	High Similarity	NPC471693
0.872	High Similarity	NPC476343
0.8712	High Similarity	NPC176814
0.8712	High Similarity	NPC4982
0.8712	High Similarity	NPC68779
0.8712	High Similarity	NPC300776
0.8712	High Similarity	NPC5310
0.8699	High Similarity	NPC255675
0.8699	High Similarity	NPC470626
0.8699	High Similarity	NPC205502
0.8686	High Similarity	NPC239608
0.8686	High Similarity	NPC46161
0.8672	High Similarity	NPC276014
0.8651	High Similarity	NPC286573
0.8651	High Similarity	NPC86900
0.8651	High Similarity	NPC85488
0.8647	High Similarity	NPC152209
0.8636	High Similarity	NPC307006
0.8636	High Similarity	NPC129889
0.8633	High Similarity	NPC472333
0.8633	High Similarity	NPC208507
0.8629	High Similarity	NPC181969
0.8629	High Similarity	NPC320987
0.8618	High Similarity	NPC293619
0.8605	High Similarity	NPC16651
0.8605	High Similarity	NPC281020
0.8605	High Similarity	NPC32163
0.8603	High Similarity	NPC470991
0.8603	High Similarity	NPC100675
0.8594	High Similarity	NPC148627
0.8583	High Similarity	NPC78918
0.8583	High Similarity	NPC156840
0.8583	High Similarity	NPC160900
0.8583	High Similarity	NPC139617
0.8583	High Similarity	NPC18984
0.8583	High Similarity	NPC106659
0.8583	High Similarity	NPC280704
0.8583	High Similarity	NPC8547
0.8583	High Similarity	NPC229084
0.8583	High Similarity	NPC173746
0.8583	High Similarity	NPC257124
0.8582	High Similarity	NPC90431
0.8571	High Similarity	NPC470804
0.8571	High Similarity	NPC290451
0.8571	High Similarity	NPC127389
0.856	High Similarity	NPC95614
0.856	High Similarity	NPC56214
0.856	High Similarity	NPC227217
0.856	High Similarity	NPC242885
0.856	High Similarity	NPC177475
0.856	High Similarity	NPC35071
0.856	High Similarity	NPC165133
0.856	High Similarity	NPC117780
0.856	High Similarity	NPC232316
0.856	High Similarity	NPC148615
0.855	High Similarity	NPC66905
0.8548	High Similarity	NPC474214
0.8537	High Similarity	NPC221049
0.8529	High Similarity	NPC203351
0.8516	High Similarity	NPC146886
0.8516	High Similarity	NPC60517
0.8516	High Similarity	NPC20443
0.8507	High Similarity	NPC139519
0.8507	High Similarity	NPC204592
0.85	High Similarity	NPC137685
0.8492	Intermediate Similarity	NPC109083
0.8492	Intermediate Similarity	NPC60962
0.8492	Intermediate Similarity	NPC269843
0.8492	Intermediate Similarity	NPC189844
0.8492	Intermediate Similarity	NPC224814
0.8492	Intermediate Similarity	NPC14007
0.8489	Intermediate Similarity	NPC53884
0.8489	Intermediate Similarity	NPC223185
0.8489	Intermediate Similarity	NPC258671
0.848	Intermediate Similarity	NPC474320
0.848	Intermediate Similarity	NPC310338
0.848	Intermediate Similarity	NPC281298
0.848	Intermediate Similarity	NPC135961
0.8467	Intermediate Similarity	NPC78987
0.8467	Intermediate Similarity	NPC82336
0.8462	Intermediate Similarity	NPC118533
0.8462	Intermediate Similarity	NPC165045
0.8456	Intermediate Similarity	NPC284409
0.845	Intermediate Similarity	NPC194519
0.844	Intermediate Similarity	NPC1580
0.8438	Intermediate Similarity	NPC31344
0.8438	Intermediate Similarity	NPC317769
0.8429	Intermediate Similarity	NPC474799
0.8425	Intermediate Similarity	NPC160380
0.8425	Intermediate Similarity	NPC38996
0.8417	Intermediate Similarity	NPC7097
0.8417	Intermediate Similarity	NPC246358
0.8417	Intermediate Similarity	NPC304956
0.8417	Intermediate Similarity	NPC36108
0.8417	Intermediate Similarity	NPC233731
0.8406	Intermediate Similarity	NPC52664
0.8406	Intermediate Similarity	NPC104956
0.84	Intermediate Similarity	NPC474040
0.8397	Intermediate Similarity	NPC470213
0.8397	Intermediate Similarity	NPC252307
0.8397	Intermediate Similarity	NPC186843
0.8397	Intermediate Similarity	NPC245826
0.8397	Intermediate Similarity	NPC206615
0.8397	Intermediate Similarity	NPC474178
0.8397	Intermediate Similarity	NPC98631
0.8394	Intermediate Similarity	NPC289690
0.8394	Intermediate Similarity	NPC288452
0.8394	Intermediate Similarity	NPC4796
0.8394	Intermediate Similarity	NPC147379
0.8385	Intermediate Similarity	NPC213552
0.8385	Intermediate Similarity	NPC58607
0.8385	Intermediate Similarity	NPC120225
0.8385	Intermediate Similarity	NPC178284
0.8385	Intermediate Similarity	NPC191037
0.838	Intermediate Similarity	NPC474903
0.8372	Intermediate Similarity	NPC48990
0.8372	Intermediate Similarity	NPC114901
0.8372	Intermediate Similarity	NPC293701
0.837	Intermediate Similarity	NPC252343
0.8369	Intermediate Similarity	NPC299090
0.8369	Intermediate Similarity	NPC283081
0.8369	Intermediate Similarity	NPC143892
0.8369	Intermediate Similarity	NPC221383
0.8359	Intermediate Similarity	NPC209567
0.8357	Intermediate Similarity	NPC469683
0.8346	Intermediate Similarity	NPC204466

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 NPC293641 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	259
0.1-0.2	851
0.2-0.3	1664
0.3-0.4	2623
0.4-0.5	1842
0.5-0.6	1087
0.6-0.7	704
0.7-0.8	115
0.8-0.85	3
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8583	High Similarity	NPD4379	Clinical (unspecified phase)
0.8583	High Similarity	NPD228	Approved
0.8333	Intermediate Similarity	NPD3027	Phase 3
0.8321	Intermediate Similarity	NPD9494	Approved
0.8031	Intermediate Similarity	NPD5536	Phase 2
0.8027	Intermediate Similarity	NPD1934	Approved
0.8	Intermediate Similarity	NPD5283	Phase 1
0.7907	Intermediate Similarity	NPD1357	Approved
0.7887	Intermediate Similarity	NPD4110	Phase 3
0.7887	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD2684	Approved
0.7883	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7883	Intermediate Similarity	NPD3620	Phase 2
0.7852	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD5647	Approved
0.7778	Intermediate Similarity	NPD7843	Approved
0.7748	Intermediate Similarity	NPD3882	Suspended
0.7742	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD6166	Phase 2
0.7737	Intermediate Similarity	NPD6798	Discontinued
0.7734	Intermediate Similarity	NPD7157	Approved
0.7733	Intermediate Similarity	NPD2801	Approved
0.7698	Intermediate Similarity	NPD6355	Discontinued
0.768	Intermediate Similarity	NPD3022	Approved
0.768	Intermediate Similarity	NPD3021	Approved
0.7634	Intermediate Similarity	NPD1651	Approved
0.7626	Intermediate Similarity	NPD1613	Approved
0.7626	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD2935	Discontinued
0.7603	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD447	Suspended
0.7554	Intermediate Similarity	NPD4062	Phase 3
0.7554	Intermediate Similarity	NPD6233	Phase 2
0.7554	Intermediate Similarity	NPD2674	Phase 3
0.7547	Intermediate Similarity	NPD7074	Phase 3
0.7532	Intermediate Similarity	NPD3818	Discontinued
0.7518	Intermediate Similarity	NPD6653	Approved
0.7517	Intermediate Similarity	NPD8166	Discontinued
0.7517	Intermediate Similarity	NPD4628	Phase 3
0.75	Intermediate Similarity	NPD825	Approved
0.75	Intermediate Similarity	NPD4060	Phase 1
0.75	Intermediate Similarity	NPD826	Approved
0.7484	Intermediate Similarity	NPD7054	Approved
0.7483	Intermediate Similarity	NPD1511	Approved
0.7442	Intermediate Similarity	NPD1241	Discontinued
0.7438	Intermediate Similarity	NPD7472	Approved
0.7434	Intermediate Similarity	NPD37	Approved
0.7426	Intermediate Similarity	NPD1283	Approved
0.7419	Intermediate Similarity	NPD6234	Discontinued
0.7417	Intermediate Similarity	NPD4380	Phase 2
0.741	Intermediate Similarity	NPD7095	Approved
0.7388	Intermediate Similarity	NPD3847	Discontinued
0.7383	Intermediate Similarity	NPD1512	Approved
0.7381	Intermediate Similarity	NPD290	Approved
0.7357	Intermediate Similarity	NPD3145	Approved
0.7357	Intermediate Similarity	NPD3144	Approved
0.7347	Intermediate Similarity	NPD6190	Approved
0.7338	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD3817	Phase 2
0.7333	Intermediate Similarity	NPD9296	Approved
0.7333	Intermediate Similarity	NPD3705	Approved
0.7329	Intermediate Similarity	NPD3060	Approved
0.7324	Intermediate Similarity	NPD230	Phase 1
0.7319	Intermediate Similarity	NPD257	Approved
0.7319	Intermediate Similarity	NPD258	Approved
0.7313	Intermediate Similarity	NPD4626	Approved
0.7303	Intermediate Similarity	NPD7028	Phase 2
0.7293	Intermediate Similarity	NPD1894	Discontinued
0.7292	Intermediate Similarity	NPD1510	Phase 2
0.729	Intermediate Similarity	NPD4967	Phase 2
0.729	Intermediate Similarity	NPD4966	Approved
0.729	Intermediate Similarity	NPD4965	Approved
0.729	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD6797	Phase 2
0.7266	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD2424	Discontinued
0.726	Intermediate Similarity	NPD4534	Discontinued
0.7258	Intermediate Similarity	NPD291	Approved
0.7254	Intermediate Similarity	NPD943	Approved
0.7254	Intermediate Similarity	NPD1240	Approved
0.7244	Intermediate Similarity	NPD1358	Approved
0.7241	Intermediate Similarity	NPD2240	Approved
0.7241	Intermediate Similarity	NPD9570	Approved
0.7241	Intermediate Similarity	NPD2438	Suspended
0.7241	Intermediate Similarity	NPD2239	Approved
0.7241	Intermediate Similarity	NPD5712	Approved
0.7239	Intermediate Similarity	NPD7251	Discontinued
0.7237	Intermediate Similarity	NPD3455	Phase 2
0.7226	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD1535	Discovery
0.7206	Intermediate Similarity	NPD1281	Approved
0.7205	Intermediate Similarity	NPD7228	Approved
0.7203	Intermediate Similarity	NPD555	Phase 2
0.7197	Intermediate Similarity	NPD6671	Approved
0.7195	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD7808	Phase 3
0.7194	Intermediate Similarity	NPD2798	Approved
0.7192	Intermediate Similarity	NPD7266	Discontinued
0.7192	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD3019	Approved
0.7185	Intermediate Similarity	NPD2932	Approved
0.7185	Intermediate Similarity	NPD1778	Approved
0.7183	Intermediate Similarity	NPD259	Phase 1
0.7183	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD2799	Discontinued
0.7172	Intermediate Similarity	NPD7033	Discontinued
0.7171	Intermediate Similarity	NPD3687	Approved
0.7171	Intermediate Similarity	NPD3686	Approved
0.717	Intermediate Similarity	NPD6232	Discontinued
0.7153	Intermediate Similarity	NPD1481	Phase 2
0.7153	Intermediate Similarity	NPD1607	Approved
0.7153	Intermediate Similarity	NPD1608	Approved
0.7153	Intermediate Similarity	NPD3972	Approved
0.7143	Intermediate Similarity	NPD7473	Discontinued
0.7143	Intermediate Similarity	NPD5958	Discontinued
0.7143	Intermediate Similarity	NPD1549	Phase 2
0.7134	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7075	Discontinued
0.7133	Intermediate Similarity	NPD1558	Phase 1
0.7133	Intermediate Similarity	NPD2979	Phase 3
0.7132	Intermediate Similarity	NPD3496	Discontinued
0.7124	Intermediate Similarity	NPD824	Approved
0.7123	Intermediate Similarity	NPD2161	Phase 2
0.7113	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD5691	Approved
0.7107	Intermediate Similarity	NPD7199	Phase 2
0.7107	Intermediate Similarity	NPD8127	Discontinued
0.7105	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD2982	Phase 2
0.7101	Intermediate Similarity	NPD2983	Phase 2
0.7095	Intermediate Similarity	NPD4162	Approved
0.7095	Intermediate Similarity	NPD4236	Phase 3
0.7095	Intermediate Similarity	NPD4237	Approved
0.7086	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD3146	Approved
0.7086	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD2344	Approved
0.7071	Intermediate Similarity	NPD6584	Phase 3
0.7059	Intermediate Similarity	NPD5846	Approved
0.7059	Intermediate Similarity	NPD1653	Approved
0.7059	Intermediate Similarity	NPD6516	Phase 2
0.7051	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD1876	Approved
0.7047	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD5494	Approved
0.7041	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD9545	Approved
0.7031	Intermediate Similarity	NPD3134	Approved
0.7029	Intermediate Similarity	NPD9717	Approved
0.7029	Intermediate Similarity	NPD2981	Phase 2
0.7027	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD9569	Approved
0.7021	Intermediate Similarity	NPD3018	Phase 2
0.7021	Intermediate Similarity	NPD2861	Phase 2
0.702	Intermediate Similarity	NPD6799	Approved
0.7015	Intermediate Similarity	NPD9493	Approved
0.7014	Intermediate Similarity	NPD4140	Approved
0.7013	Intermediate Similarity	NPD3866	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD6032	Approved
0.7007	Intermediate Similarity	NPD2796	Approved
0.7	Intermediate Similarity	NPD5241	Discontinued
0.7	Intermediate Similarity	NPD2797	Approved
0.6993	Remote Similarity	NPD3268	Approved
0.6993	Remote Similarity	NPD5109	Approved
0.6993	Remote Similarity	NPD5110	Phase 2
0.6993	Remote Similarity	NPD5111	Phase 2
0.6992	Remote Similarity	NPD2860	Approved
0.6992	Remote Similarity	NPD2629	Approved
0.6992	Remote Similarity	NPD2859	Approved
0.6987	Remote Similarity	NPD6801	Discontinued
0.6986	Remote Similarity	NPD7097	Phase 1
0.6985	Remote Similarity	NPD5585	Approved
0.698	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.698	Remote Similarity	NPD5177	Phase 3
0.6978	Remote Similarity	NPD3685	Discontinued
0.6974	Remote Similarity	NPD4662	Approved
0.6974	Remote Similarity	NPD4661	Approved
0.6972	Remote Similarity	NPD2614	Approved
0.6972	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.697	Remote Similarity	NPD821	Approved
0.697	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.697	Remote Similarity	NPD5535	Approved
0.6966	Remote Similarity	NPD275	Approved
0.6966	Remote Similarity	NPD1933	Approved
0.6966	Remote Similarity	NPD3657	Discovery
0.6966	Remote Similarity	NPD274	Approved
0.6966	Remote Similarity	NPD5735	Approved
0.6964	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.696	Remote Similarity	NPD3020	Approved
0.6959	Remote Similarity	NPD6002	Phase 3
0.6959	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD5762	Approved
0.6959	Remote Similarity	NPD6005	Phase 3
0.6959	Remote Similarity	NPD5763	Approved
0.6959	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6004	Phase 3
0.6951	Remote Similarity	NPD5844	Phase 1

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