NPASS Compound

Structure

CID269843 OpenBabel06191716072D 28 29 0 0 0 0 0 0 0 0999 V2000 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2583 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 2.0000 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 -7.7942 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 -6.0622 1.5000 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 -8.6603 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 -8.6603 2.0000 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 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 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 -9.5263 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 0.0000 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 -10.3923 2.0000 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 26 1 0 0 0 0 2 27 1 0 0 0 0 3 28 1 0 0 0 0 4 8 2 0 0 0 0 4 15 1 0 0 0 0 5 9 2 0 0 0 0 5 16 1 0 0 0 0 6 10 2 0 0 0 0 6 15 1 0 0 0 0 7 11 2 0 0 0 0 7 16 1 0 0 0 0 8 17 1 0 0 0 0 9 18 1 0 0 0 0 10 19 1 0 0 0 0 11 20 1 0 0 0 0 12 15 2 0 0 0 0 12 21 1 0 0 0 0 13 16 2 0 0 0 0 13 22 1 0 0 0 0 14 17 2 0 0 0 0 14 18 1 0 0 0 0 17 23 1 0 0 0 0 18 24 2 0 0 0 0 19 21 2 0 0 0 0 19 25 1 0 0 0 0 20 22 2 0 0 0 0 20 26 1 0 0 0 0 21 27 1 0 0 0 0 22 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	382.14
Volume:	398.332
LogP:	2.765
LogD:	2.823
LogS:	-4.708
# Rotatable Bonds:	9
TPSA:	82.06
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.526
Synthetic Accessibility Score:	2.339
Fsp3:	0.182
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.826
MDCK Permeability:	1.5946989151416346e-05
Pgp-inhibitor:	0.988
Pgp-substrate:	0.822
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.779

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.22
Plasma Protein Binding (PPB):	94.00357818603516%
Volume Distribution (VD):	0.377
Pgp-substrate:	2.390399217605591%

ADMET: Metabolism

CYP1A2-inhibitor:	0.43
CYP1A2-substrate:	0.776
CYP2C19-inhibitor:	0.336
CYP2C19-substrate:	0.302
CYP2C9-inhibitor:	0.561
CYP2C9-substrate:	0.947
CYP2D6-inhibitor:	0.031
CYP2D6-substrate:	0.901
CYP3A4-inhibitor:	0.706
CYP3A4-substrate:	0.697

ADMET: Excretion

Clearance (CL):	12.643
Half-life (T1/2):	0.939

ADMET: Toxicity

hERG Blockers:	0.403
Human Hepatotoxicity (H-HT):	0.318
Drug-inuced Liver Injury (DILI):	0.846
AMES Toxicity:	0.193
Rat Oral Acute Toxicity:	0.524
Maximum Recommended Daily Dose:	0.191
Skin Sensitization:	0.95
Carcinogencity:	0.831
Eye Corrosion:	0.01
Eye Irritation:	0.35
Respiratory Toxicity:	0.96

Download Data

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

Natural Product: NPC269843

Natural Product ID:	NPC269843
*Common Name:**	Methylcurcumin
IUPAC Name:	n.a.
Synonyms:	Methylcurcumin
Standard InCHIKey:	MXGYVBOZRLQICP-VUSYVUDMSA-N
Standard InCHI:	InChI=1S/C22H22O6/c1-26-20-11-7-16(13-22(20)28-3)5-9-18(24)14-17(23)8-4-15-6-10-19(25)21(12-15)27-2/h4-14,23,25H,1-3H3/b8-4+,9-5+,17-14-
SMILES:	COc1cc(/C=C/C(=O)/C=C(/C=C/c2ccc(c(c2)OC)O)O)ccc1OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL494826
PubChem CID:	NA
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids [CHEMONTID:0000356] Curcuminoids

*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
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	root	n.a.	PMID[18484537]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[18484537]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[19615910]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29323912]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[731398]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	root	n.a.	PMID[731398]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23911	Alpinia officinarum	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	6
Others	1

Activity Type	# Activity
Cell Line	6
Protein Family	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	20900.0	nM	PMID[543768]
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	=	6800.0	nM	PMID[543768]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	15400.0	nM	PMID[543768]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	7200.0	nM	PMID[543768]
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	=	47000.0	nM	PMID[543769]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	33100.0	nM	PMID[543769]
NPT664	Protein Family	Histone deacetylase	Homo sapiens	Activity	=	13.0	%	PMID[543771]

☑ 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 NPC269843 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	275
0.1-0.2	1761
0.2-0.3	4822
0.3-0.4	13391
0.4-0.5	4356
0.5-0.6	4868
0.6-0.7	9030
0.7-0.8	3522
0.8-0.85	442
0.85-0.9	171
0.9-0.95	47
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC109083
1.0	High Similarity	NPC189844
1.0	High Similarity	NPC14007
1.0	High Similarity	NPC60962
1.0	High Similarity	NPC224814
0.9741	High Similarity	NPC229084
0.9741	High Similarity	NPC18984
0.9741	High Similarity	NPC160900
0.9741	High Similarity	NPC106659
0.9646	High Similarity	NPC280001
0.9496	High Similarity	NPC276014
0.9492	High Similarity	NPC246704
0.9487	High Similarity	NPC286573
0.9417	High Similarity	NPC123228
0.9417	High Similarity	NPC5018
0.9417	High Similarity	NPC123722
0.9417	High Similarity	NPC276466
0.9417	High Similarity	NPC151167
0.9412	High Similarity	NPC289459
0.9339	High Similarity	NPC110313
0.9333	High Similarity	NPC179777
0.9333	High Similarity	NPC84076
0.9333	High Similarity	NPC303680
0.9333	High Similarity	NPC120225
0.9333	High Similarity	NPC90128
0.9333	High Similarity	NPC213552
0.9316	High Similarity	NPC158949
0.9262	High Similarity	NPC304622
0.9224	High Similarity	NPC272471
0.9224	High Similarity	NPC137537
0.9224	High Similarity	NPC164706
0.9224	High Similarity	NPC70744
0.9224	High Similarity	NPC107588
0.9224	High Similarity	NPC470626
0.918	High Similarity	NPC478215
0.9153	High Similarity	NPC204466
0.9138	High Similarity	NPC39793
0.9138	High Similarity	NPC185738
0.9138	High Similarity	NPC293619
0.9106	High Similarity	NPC83062
0.9091	High Similarity	NPC53305
0.9091	High Similarity	NPC87113
0.9091	High Similarity	NPC257589
0.9083	High Similarity	NPC242372
0.9083	High Similarity	NPC164778
0.9083	High Similarity	NPC4181
0.9083	High Similarity	NPC257976
0.9076	High Similarity	NPC70752
0.9068	High Similarity	NPC2058
0.9068	High Similarity	NPC95614
0.9068	High Similarity	NPC232316
0.9068	High Similarity	NPC165133
0.9068	High Similarity	NPC117780
0.9068	High Similarity	NPC242885
0.9068	High Similarity	NPC56214
0.9068	High Similarity	NPC202474
0.9068	High Similarity	NPC227217
0.9032	High Similarity	NPC66905
0.9016	High Similarity	NPC92207
0.9016	High Similarity	NPC127937
0.9008	High Similarity	NPC60517
0.9008	High Similarity	NPC20443
0.9008	High Similarity	NPC312404
0.9008	High Similarity	NPC273686
0.9008	High Similarity	NPC146886
0.9	High Similarity	NPC114298
0.8992	High Similarity	NPC207613
0.8983	High Similarity	NPC310338
0.8983	High Similarity	NPC281298
0.8938	High Similarity	NPC7097
0.8938	High Similarity	NPC36108
0.8938	High Similarity	NPC233731
0.8938	High Similarity	NPC246358
0.8926	High Similarity	NPC238810
0.8917	High Similarity	NPC38996
0.8917	High Similarity	NPC160380
0.8917	High Similarity	NPC184651
0.8917	High Similarity	NPC470212
0.8917	High Similarity	NPC473853
0.8917	High Similarity	NPC113865
0.8917	High Similarity	NPC54872
0.8917	High Similarity	NPC343720
0.8917	High Similarity	NPC324571
0.8917	High Similarity	NPC312675
0.8917	High Similarity	NPC262156
0.8898	High Similarity	NPC277460
0.8889	High Similarity	NPC268317
0.888	High Similarity	NPC172673
0.8879	High Similarity	NPC294941
0.8871	High Similarity	NPC226661
0.8843	High Similarity	NPC262253
0.8843	High Similarity	NPC473411
0.8843	High Similarity	NPC71579
0.8843	High Similarity	NPC85488
0.8814	High Similarity	NPC86947
0.8783	High Similarity	NPC156840
0.8783	High Similarity	NPC8547
0.8783	High Similarity	NPC257124
0.8783	High Similarity	NPC297657
0.8783	High Similarity	NPC78918
0.8783	High Similarity	NPC173746
0.8783	High Similarity	NPC139617
0.877	High Similarity	NPC163083
0.877	High Similarity	NPC31344
0.877	High Similarity	NPC471693
0.877	High Similarity	NPC317769
0.877	High Similarity	NPC280704
0.876	High Similarity	NPC201777
0.875	High Similarity	NPC61516
0.875	High Similarity	NPC135127
0.875	High Similarity	NPC232084
0.875	High Similarity	NPC247364
0.875	High Similarity	NPC111635
0.875	High Similarity	NPC119060
0.875	High Similarity	NPC10932
0.875	High Similarity	NPC237594
0.875	High Similarity	NPC476387
0.875	High Similarity	NPC249791
0.875	High Similarity	NPC474565
0.874	High Similarity	NPC239302
0.8739	High Similarity	NPC275519
0.8739	High Similarity	NPC212743
0.873	High Similarity	NPC244246
0.873	High Similarity	NPC311419
0.873	High Similarity	NPC123196
0.873	High Similarity	NPC65935
0.873	High Similarity	NPC215941
0.873	High Similarity	NPC319282
0.873	High Similarity	NPC137427
0.873	High Similarity	NPC275724
0.8707	High Similarity	NPC51698
0.8699	High Similarity	NPC74478
0.8678	High Similarity	NPC471877
0.8678	High Similarity	NPC166759
0.8678	High Similarity	NPC470848
0.8678	High Similarity	NPC470849
0.8672	High Similarity	NPC36490
0.8672	High Similarity	NPC327410
0.8667	High Similarity	NPC24474
0.8667	High Similarity	NPC311595
0.8667	High Similarity	NPC299406
0.8667	High Similarity	NPC37858
0.8667	High Similarity	NPC141791
0.8667	High Similarity	NPC263386
0.8655	High Similarity	NPC164386
0.8629	High Similarity	NPC299584
0.8629	High Similarity	NPC271985
0.8629	High Similarity	NPC208950
0.8629	High Similarity	NPC82483
0.8629	High Similarity	NPC472093
0.8629	High Similarity	NPC228771
0.8629	High Similarity	NPC17943
0.8629	High Similarity	NPC251855
0.8629	High Similarity	NPC148627
0.8629	High Similarity	NPC265483
0.8629	High Similarity	NPC233410
0.8629	High Similarity	NPC58279
0.8629	High Similarity	NPC116907
0.8629	High Similarity	NPC300326
0.8629	High Similarity	NPC29008
0.8629	High Similarity	NPC194519
0.8629	High Similarity	NPC266705
0.8629	High Similarity	NPC9067
0.8629	High Similarity	NPC3221
0.8629	High Similarity	NPC298757
0.8629	High Similarity	NPC221077
0.8629	High Similarity	NPC57490
0.8629	High Similarity	NPC193544
0.8629	High Similarity	NPC117214
0.8629	High Similarity	NPC203133
0.8629	High Similarity	NPC475169
0.8626	High Similarity	NPC284409
0.8621	High Similarity	NPC226250
0.8618	High Similarity	NPC197757
0.8618	High Similarity	NPC228922
0.8615	High Similarity	NPC120852
0.8615	High Similarity	NPC90431
0.8607	High Similarity	NPC127389
0.8607	High Similarity	NPC290451
0.8594	High Similarity	NPC245120
0.8583	High Similarity	NPC124916
0.8583	High Similarity	NPC474214
0.8583	High Similarity	NPC474040
0.8571	High Similarity	NPC281277
0.8571	High Similarity	NPC109275
0.8561	High Similarity	NPC474784
0.856	High Similarity	NPC28730
0.856	High Similarity	NPC17837
0.856	High Similarity	NPC214406
0.856	High Similarity	NPC18924
0.856	High Similarity	NPC58607
0.856	High Similarity	NPC274356
0.856	High Similarity	NPC44748
0.856	High Similarity	NPC103823
0.856	High Similarity	NPC223136
0.856	High Similarity	NPC304630
0.856	High Similarity	NPC178284
0.856	High Similarity	NPC78974
0.856	High Similarity	NPC191037
0.8559	High Similarity	NPC33749

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 NPC269843 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	245
0.1-0.2	1035
0.2-0.3	1437
0.3-0.4	2834
0.4-0.5	1801
0.5-0.6	1060
0.6-0.7	638
0.7-0.8	94
0.8-0.85	3
0.85-0.9	1
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9741	High Similarity	NPD4379	Clinical (unspecified phase)
0.9138	High Similarity	NPD5536	Phase 2
0.8783	High Similarity	NPD228	Approved
0.8475	Intermediate Similarity	NPD5283	Phase 1
0.8359	Intermediate Similarity	NPD3027	Phase 3
0.8346	Intermediate Similarity	NPD9494	Approved
0.8136	Intermediate Similarity	NPD3022	Approved
0.8136	Intermediate Similarity	NPD3021	Approved
0.7966	Intermediate Similarity	NPD1358	Approved
0.792	Intermediate Similarity	NPD1357	Approved
0.7891	Intermediate Similarity	NPD2983	Phase 2
0.7891	Intermediate Similarity	NPD2982	Phase 2
0.7812	Intermediate Similarity	NPD2981	Phase 2
0.7788	Intermediate Similarity	NPD9296	Approved
0.7761	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7761	Intermediate Similarity	NPD4060	Phase 1
0.7761	Intermediate Similarity	NPD3620	Phase 2
0.7744	Intermediate Similarity	NPD3145	Approved
0.7744	Intermediate Similarity	NPD3144	Approved
0.7731	Intermediate Similarity	NPD3134	Approved
0.773	Intermediate Similarity	NPD4357	Discontinued
0.7727	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD2674	Phase 3
0.7681	Intermediate Similarity	NPD7266	Discontinued
0.7652	Intermediate Similarity	NPD3018	Phase 2
0.7652	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD3882	Suspended
0.763	Intermediate Similarity	NPD1613	Approved
0.763	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD1558	Phase 1
0.7619	Intermediate Similarity	NPD2801	Approved
0.7615	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD2684	Approved
0.7578	Intermediate Similarity	NPD4626	Approved
0.7551	Intermediate Similarity	NPD1934	Approved
0.7537	Intermediate Similarity	NPD7095	Approved
0.75	Intermediate Similarity	NPD7843	Approved
0.7482	Intermediate Similarity	NPD2935	Discontinued
0.7478	Intermediate Similarity	NPD2934	Approved
0.7478	Intermediate Similarity	NPD2933	Approved
0.746	Intermediate Similarity	NPD7157	Approved
0.7447	Intermediate Similarity	NPD3060	Approved
0.7438	Intermediate Similarity	NPD968	Approved
0.7424	Intermediate Similarity	NPD2922	Phase 1
0.7414	Intermediate Similarity	NPD2860	Approved
0.7414	Intermediate Similarity	NPD2859	Approved
0.7397	Intermediate Similarity	NPD1653	Approved
0.7394	Intermediate Similarity	NPD8166	Discontinued
0.7385	Intermediate Similarity	NPD3847	Discontinued
0.7385	Intermediate Similarity	NPD3496	Discontinued
0.7383	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD3020	Approved
0.7364	Intermediate Similarity	NPD1651	Approved
0.7361	Intermediate Similarity	NPD1511	Approved
0.736	Intermediate Similarity	NPD5535	Approved
0.7353	Intermediate Similarity	NPD5111	Phase 2
0.7353	Intermediate Similarity	NPD5110	Phase 2
0.7353	Intermediate Similarity	NPD5109	Approved
0.7343	Intermediate Similarity	NPD6190	Approved
0.7333	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD3705	Approved
0.7323	Intermediate Similarity	NPD6671	Approved
0.7319	Intermediate Similarity	NPD447	Suspended
0.7313	Intermediate Similarity	NPD6584	Phase 3
0.7302	Intermediate Similarity	NPD1241	Discontinued
0.7273	Intermediate Similarity	NPD4110	Phase 3
0.7273	Intermediate Similarity	NPD4628	Phase 3
0.7273	Intermediate Similarity	NPD3972	Approved
0.7273	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD2492	Phase 1
0.726	Intermediate Similarity	NPD1512	Approved
0.7258	Intermediate Similarity	NPD5451	Approved
0.725	Intermediate Similarity	NPD291	Approved
0.7236	Intermediate Similarity	NPD290	Approved
0.7231	Intermediate Similarity	NPD5691	Approved
0.723	Intermediate Similarity	NPD3866	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD3455	Phase 2
0.723	Intermediate Similarity	NPD824	Approved
0.7226	Intermediate Similarity	NPD6798	Discontinued
0.7226	Intermediate Similarity	NPD5718	Phase 2
0.7211	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD4162	Approved
0.7194	Intermediate Similarity	NPD4340	Discontinued
0.7194	Intermediate Similarity	NPD6355	Discontinued
0.7194	Intermediate Similarity	NPD230	Phase 1
0.7181	Intermediate Similarity	NPD7028	Phase 2
0.7179	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6166	Phase 2
0.7176	Intermediate Similarity	NPD6516	Phase 2
0.7176	Intermediate Similarity	NPD5846	Approved
0.7174	Intermediate Similarity	NPD4062	Phase 3
0.7174	Intermediate Similarity	NPD6233	Phase 2
0.7171	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD1242	Phase 1
0.7164	Intermediate Similarity	NPD1283	Approved
0.7164	Intermediate Similarity	NPD1876	Approved
0.7132	Intermediate Similarity	NPD2861	Phase 2
0.7122	Intermediate Similarity	NPD943	Approved
0.7122	Intermediate Similarity	NPD1240	Approved
0.7105	Intermediate Similarity	NPD3817	Phase 2
0.7103	Intermediate Similarity	NPD5241	Discontinued
0.7099	Intermediate Similarity	NPD5585	Approved
0.7092	Intermediate Similarity	NPD6896	Approved
0.7092	Intermediate Similarity	NPD6895	Approved
0.709	Intermediate Similarity	NPD6582	Phase 2
0.709	Intermediate Similarity	NPD6583	Phase 3
0.7089	Intermediate Similarity	NPD3818	Discontinued
0.7083	Intermediate Similarity	NPD4237	Approved
0.7083	Intermediate Similarity	NPD4236	Phase 3
0.708	Intermediate Similarity	NPD4908	Phase 1
0.7075	Intermediate Similarity	NPD4123	Phase 3
0.7071	Intermediate Similarity	NPD1933	Approved
0.7068	Intermediate Similarity	NPD422	Phase 1
0.7068	Intermediate Similarity	NPD1535	Discovery
0.7063	Intermediate Similarity	NPD3540	Phase 1
0.7059	Intermediate Similarity	NPD2798	Approved
0.705	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD2423	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD2668	Approved
0.7045	Intermediate Similarity	NPD2667	Approved
0.7044	Intermediate Similarity	NPD7054	Approved
0.7042	Intermediate Similarity	NPD1510	Phase 2
0.7042	Intermediate Similarity	NPD2799	Discontinued
0.7039	Intermediate Similarity	NPD2977	Approved
0.7039	Intermediate Similarity	NPD2978	Approved
0.7034	Intermediate Similarity	NPD6331	Phase 2
0.7023	Intermediate Similarity	NPD1548	Phase 1
0.7023	Intermediate Similarity	NPD1894	Discontinued
0.7021	Intermediate Similarity	NPD1607	Approved
0.7015	Intermediate Similarity	NPD2233	Approved
0.7015	Intermediate Similarity	NPD2232	Approved
0.7015	Intermediate Similarity	NPD1481	Phase 2
0.7015	Intermediate Similarity	NPD2230	Approved
0.7014	Intermediate Similarity	NPD2424	Discontinued
0.7007	Intermediate Similarity	NPD5297	Approved
0.7	Intermediate Similarity	NPD7074	Phase 3
0.7	Intermediate Similarity	NPD7472	Approved
0.6993	Remote Similarity	NPD3539	Phase 1
0.6991	Remote Similarity	NPD111	Approved
0.6987	Remote Similarity	NPD2821	Approved
0.6986	Remote Similarity	NPD2219	Phase 1
0.6985	Remote Similarity	NPD2797	Approved
0.6985	Remote Similarity	NPD3053	Approved
0.6985	Remote Similarity	NPD1203	Approved
0.6985	Remote Similarity	NPD3055	Approved
0.6978	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD3268	Approved
0.6968	Remote Similarity	NPD6234	Discontinued
0.6966	Remote Similarity	NPD5177	Phase 3
0.6966	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD1669	Approved
0.6962	Remote Similarity	NPD2898	Approved
0.6954	Remote Similarity	NPD4380	Phase 2
0.6953	Remote Similarity	NPD821	Approved
0.6953	Remote Similarity	NPD9379	Approved
0.6953	Remote Similarity	NPD9377	Approved
0.695	Remote Similarity	NPD3657	Discovery
0.6944	Remote Similarity	NPD2344	Approved
0.6943	Remote Similarity	NPD6232	Discontinued
0.694	Remote Similarity	NPD1281	Approved
0.694	Remote Similarity	NPD1610	Phase 2
0.6935	Remote Similarity	NPD9697	Approved
0.6934	Remote Similarity	NPD4624	Approved
0.6929	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD709	Approved
0.6918	Remote Similarity	NPD7473	Discontinued
0.6917	Remote Similarity	NPD1778	Approved
0.6914	Remote Similarity	NPD7685	Pre-registration
0.6912	Remote Similarity	NPD5311	Approved
0.6912	Remote Similarity	NPD5310	Approved
0.6912	Remote Similarity	NPD3225	Approved
0.6908	Remote Similarity	NPD6873	Phase 2
0.6908	Remote Similarity	NPD6386	Approved
0.6908	Remote Similarity	NPD6385	Approved
0.6901	Remote Similarity	NPD6653	Approved
0.6901	Remote Similarity	NPD2653	Approved
0.6897	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD9295	Approved
0.6894	Remote Similarity	NPD9545	Approved
0.6894	Remote Similarity	NPD1182	Approved
0.6892	Remote Similarity	NPD6799	Approved
0.6891	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD1608	Approved
0.6889	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD2235	Phase 2
0.6889	Remote Similarity	NPD2231	Phase 2
0.6887	Remote Similarity	NPD7458	Discontinued
0.6887	Remote Similarity	NPD3111	Phase 1
0.6879	Remote Similarity	NPD4140	Approved
0.6879	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6032	Approved
0.6875	Remote Similarity	NPD2161	Phase 2
0.6871	Remote Similarity	NPD2354	Approved
0.6863	Remote Similarity	NPD37	Approved
0.6857	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD4536	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