NPASS Compound

Structure

CID179777 OpenBabel06191715552D 23 24 0 0 0 0 0 0 0 0999 V2000 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -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 10.3923 -0.0000 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 4.3301 0.5000 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 9.5263 0.5000 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 5.1962 -0.0000 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 6.9282 -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 8.6603 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 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 23 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 7 1 0 0 0 0 4 8 2 0 0 0 0 5 6 1 0 0 0 0 5 9 1 0 0 0 0 6 10 2 0 0 0 0 7 16 2 0 0 0 0 8 16 1 0 0 0 0 9 17 1 0 0 0 0 10 18 1 0 0 0 0 11 13 1 0 0 0 0 11 16 1 0 0 0 0 12 14 2 0 0 0 0 12 17 1 0 0 0 0 13 18 1 0 0 0 0 14 19 1 0 0 0 0 15 17 2 0 0 0 0 15 20 1 0 0 0 0 18 21 2 0 0 0 0 19 20 2 0 0 0 0 19 22 1 0 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	310.16
Volume:	342.642
LogP:	3.206
LogD:	3.287
LogS:	-3.567
# Rotatable Bonds:	8
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.747
Synthetic Accessibility Score:	2.241
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.699
MDCK Permeability:	2.2829262888990343e-05
Pgp-inhibitor:	0.598
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.288
Plasma Protein Binding (PPB):	97.98719787597656%
Volume Distribution (VD):	0.728
Pgp-substrate:	1.4826369285583496%

ADMET: Metabolism

CYP1A2-inhibitor:	0.965
CYP1A2-substrate:	0.766
CYP2C19-inhibitor:	0.963
CYP2C19-substrate:	0.115
CYP2C9-inhibitor:	0.896
CYP2C9-substrate:	0.916
CYP2D6-inhibitor:	0.848
CYP2D6-substrate:	0.91
CYP3A4-inhibitor:	0.822
CYP3A4-substrate:	0.29

ADMET: Excretion

Clearance (CL):	14.774
Half-life (T1/2):	0.936

ADMET: Toxicity

hERG Blockers:	0.047
Human Hepatotoxicity (H-HT):	0.165
Drug-inuced Liver Injury (DILI):	0.085
AMES Toxicity:	0.064
Rat Oral Acute Toxicity:	0.028
Maximum Recommended Daily Dose:	0.142
Skin Sensitization:	0.653
Carcinogencity:	0.803
Eye Corrosion:	0.007
Eye Irritation:	0.559
Respiratory Toxicity:	0.092

Download Data

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

Natural Product: NPC179777

Natural Product ID:	NPC179777
*Common Name:**	7-(4-Hydroxy-3-Methoxy-Phenyl)-1-Phenyl-Hept-4-En-3-One
IUPAC Name:	(E)-7-(4-hydroxy-3-methoxyphenyl)-1-phenylhept-4-en-3-one
Synonyms:
Standard InCHIKey:	NOHMOWQGVDSLNY-UXBLZVDNSA-N
Standard InCHI:	InChI=1S/C20H22O3/c1-23-20-15-17(12-14-19(20)22)9-5-6-10-18(21)13-11-16-7-3-2-4-8-16/h2-4,6-8,10,12,14-15,22H,5,9,11,13H2,1H3/b10-6+
SMILES:	COc1cc(CC/C=C/C(=O)CCc2ccccc2)ccc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL594765
PubChem CID:	5318278
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids

*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	3
Others	14

Activity Type	# Activity
Cell Line	1
Individual Protein	6
NON-MOLECULAR	6
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT319	Cell Line	B16	Mus musculus	IC50	=	10000.0	nM	PMID[552618]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	=	3.2	%	PMID[552618]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	=	3.0	%	PMID[552618]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	=	3.6	%	PMID[552618]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	=	5.3	%	PMID[552618]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	=	7.7	%	PMID[552618]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	IC50	>	100000.0	nM	PMID[552618]
NPT2	Others	Unspecified		Inhibition	=	11.6	%	PMID[552618]
NPT2	Others	Unspecified		Inhibition	=	22.5	%	PMID[552618]
NPT2	Others	Unspecified		Inhibition	=	49.3	%	PMID[552618]
NPT2	Others	Unspecified		Inhibition	=	80.1	%	PMID[552618]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	3.2	%	PMID[552618]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	3.8	%	PMID[552618]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	5.1	%	PMID[552618]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	2.6	%	PMID[552618]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	90.6	%	PMID[552618]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	60000.0	nM	PMID[552618]

☑ 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 NPC179777 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	287
0.1-0.2	1494
0.2-0.3	4015
0.3-0.4	11014
0.4-0.5	7092
0.5-0.6	4084
0.6-0.7	8617
0.7-0.8	5441
0.8-0.85	433
0.85-0.9	155
0.9-0.95	45
0.95-1	20

Similarity Score	Similarity Level	Natural Product ID
0.9917	High Similarity	NPC151167
0.9917	High Similarity	NPC5018
0.9917	High Similarity	NPC123228
0.9917	High Similarity	NPC123722
0.9917	High Similarity	NPC276466
0.9833	High Similarity	NPC84076
0.9833	High Similarity	NPC303680
0.9833	High Similarity	NPC90128
0.9754	High Similarity	NPC304622
0.9748	High Similarity	NPC257976
0.9748	High Similarity	NPC242372
0.9748	High Similarity	NPC4181
0.9748	High Similarity	NPC164778
0.9667	High Similarity	NPC273686
0.9667	High Similarity	NPC312404
0.9664	High Similarity	NPC114298
0.9587	High Similarity	NPC257589
0.9587	High Similarity	NPC53305
0.9508	High Similarity	NPC276014
0.9508	High Similarity	NPC92207
0.9508	High Similarity	NPC127937
0.9421	High Similarity	NPC160900
0.9421	High Similarity	NPC229084
0.9421	High Similarity	NPC106659
0.9421	High Similarity	NPC18984
0.9417	High Similarity	NPC201777
0.936	High Similarity	NPC172673
0.936	High Similarity	NPC66905
0.9355	High Similarity	NPC226661
0.9333	High Similarity	NPC269843
0.9333	High Similarity	NPC60962
0.9333	High Similarity	NPC224814
0.9333	High Similarity	NPC14007
0.9333	High Similarity	NPC109083
0.9333	High Similarity	NPC158949
0.9333	High Similarity	NPC189844
0.9328	High Similarity	NPC299406
0.9268	High Similarity	NPC3221
0.9262	High Similarity	NPC163083
0.9213	High Similarity	NPC239302
0.9206	High Similarity	NPC275724
0.9206	High Similarity	NPC319282
0.9206	High Similarity	NPC65935
0.9206	High Similarity	NPC137427
0.9206	High Similarity	NPC244246
0.9206	High Similarity	NPC311419
0.9206	High Similarity	NPC123196
0.9206	High Similarity	NPC215941
0.918	High Similarity	NPC286573
0.9141	High Similarity	NPC327410
0.912	High Similarity	NPC16651
0.912	High Similarity	NPC32163
0.9084	High Similarity	NPC284409
0.9077	High Similarity	NPC90431
0.9076	High Similarity	NPC19290
0.904	High Similarity	NPC120225
0.904	High Similarity	NPC213552
0.9015	High Similarity	NPC474784
0.9	High Similarity	NPC204592
0.9	High Similarity	NPC280001
0.8976	High Similarity	NPC241354
0.8968	High Similarity	NPC20287
0.8968	High Similarity	NPC293641
0.8968	High Similarity	NPC12022
0.8968	High Similarity	NPC20404
0.896	High Similarity	NPC87113
0.896	High Similarity	NPC280767
0.896	High Similarity	NPC289459
0.8943	High Similarity	NPC194416
0.8943	High Similarity	NPC177291
0.8926	High Similarity	NPC470626
0.8923	High Similarity	NPC471110
0.8917	High Similarity	NPC61062
0.8917	High Similarity	NPC299252
0.8917	High Similarity	NPC277394
0.8898	High Similarity	NPC278308
0.8881	High Similarity	NPC472410
0.888	High Similarity	NPC246704
0.8872	High Similarity	NPC289690
0.8872	High Similarity	NPC288452
0.8855	High Similarity	NPC152209
0.8852	High Similarity	NPC310338
0.8852	High Similarity	NPC281298
0.8846	High Similarity	NPC475468
0.8843	High Similarity	NPC293619
0.8843	High Similarity	NPC185738
0.8828	High Similarity	NPC83062
0.8815	High Similarity	NPC229218
0.8815	High Similarity	NPC141817
0.8815	High Similarity	NPC192597
0.8815	High Similarity	NPC169214
0.8815	High Similarity	NPC176030
0.8806	High Similarity	NPC82336
0.8806	High Similarity	NPC78987
0.878	High Similarity	NPC95614
0.878	High Similarity	NPC56214
0.878	High Similarity	NPC242885
0.878	High Similarity	NPC227217
0.878	High Similarity	NPC117780
0.878	High Similarity	NPC232316
0.878	High Similarity	NPC165133
0.8779	High Similarity	NPC144662
0.8779	High Similarity	NPC176814
0.8779	High Similarity	NPC5310
0.8779	High Similarity	NPC300776
0.8779	High Similarity	NPC4982
0.8779	High Similarity	NPC68779
0.8769	High Similarity	NPC50763
0.875	High Similarity	NPC478215
0.875	High Similarity	NPC110313
0.875	High Similarity	NPC239608
0.875	High Similarity	NPC46161
0.875	High Similarity	NPC16353
0.875	High Similarity	NPC46880
0.8741	High Similarity	NPC110419
0.8731	High Similarity	NPC322021
0.873	High Similarity	NPC60517
0.873	High Similarity	NPC146886
0.873	High Similarity	NPC20443
0.8712	High Similarity	NPC113295
0.871	High Similarity	NPC207613
0.8689	High Similarity	NPC86947
0.8689	High Similarity	NPC39793
0.8686	High Similarity	NPC207732
0.8676	High Similarity	NPC312256
0.8672	High Similarity	NPC203719
0.8672	High Similarity	NPC117237
0.8667	High Similarity	NPC28398
0.8655	High Similarity	NPC8547
0.8655	High Similarity	NPC173746
0.8655	High Similarity	NPC257124
0.8655	High Similarity	NPC156840
0.8651	High Similarity	NPC244876
0.864	High Similarity	NPC38996
0.864	High Similarity	NPC473853
0.864	High Similarity	NPC262156
0.864	High Similarity	NPC160380
0.864	High Similarity	NPC184651
0.864	High Similarity	NPC343720
0.864	High Similarity	NPC324571
0.864	High Similarity	NPC312675
0.864	High Similarity	NPC54872
0.864	High Similarity	NPC113865
0.864	High Similarity	NPC470212
0.8623	High Similarity	NPC157133
0.8618	High Similarity	NPC137537
0.8618	High Similarity	NPC205502
0.8618	High Similarity	NPC272471
0.8618	High Similarity	NPC164706
0.8618	High Similarity	NPC107588
0.8618	High Similarity	NPC70744
0.8615	High Similarity	NPC142985
0.8615	High Similarity	NPC195292
0.8613	High Similarity	NPC254659
0.8613	High Similarity	NPC50954
0.8607	High Similarity	NPC268317
0.8571	High Similarity	NPC86900
0.8571	High Similarity	NPC85488
0.8571	High Similarity	NPC252343
0.8571	High Similarity	NPC139519
0.8561	High Similarity	NPC165389
0.856	High Similarity	NPC204466
0.856	High Similarity	NPC225245
0.856	High Similarity	NPC98305
0.8551	High Similarity	NPC300603
0.8551	High Similarity	NPC142165
0.8551	High Similarity	NPC53884
0.8551	High Similarity	NPC258671
0.8551	High Similarity	NPC91694
0.855	High Similarity	NPC469480
0.8537	High Similarity	NPC164386
0.8529	High Similarity	NPC326065
0.8529	High Similarity	NPC19158
0.8527	High Similarity	NPC281020
0.8507	High Similarity	NPC324929
0.8504	High Similarity	NPC471693
0.8504	High Similarity	NPC31344
0.8504	High Similarity	NPC317769
0.8504	High Similarity	NPC280704
0.8504	High Similarity	NPC474691
0.85	High Similarity	NPC297657
0.8496	Intermediate Similarity	NPC237594
0.8496	Intermediate Similarity	NPC476387
0.8496	Intermediate Similarity	NPC119060
0.8496	Intermediate Similarity	NPC249791
0.8496	Intermediate Similarity	NPC135127
0.8492	Intermediate Similarity	NPC70752
0.8492	Intermediate Similarity	NPC290451
0.8492	Intermediate Similarity	NPC127389
0.8489	Intermediate Similarity	NPC9370
0.8489	Intermediate Similarity	NPC287495
0.8487	Intermediate Similarity	NPC36108
0.8487	Intermediate Similarity	NPC233731
0.8487	Intermediate Similarity	NPC246358
0.8487	Intermediate Similarity	NPC7097
0.8485	Intermediate Similarity	NPC111888
0.848	Intermediate Similarity	NPC202474
0.848	Intermediate Similarity	NPC2058
0.8478	Intermediate Similarity	NPC304956
0.8478	Intermediate Similarity	NPC160378

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 NPC179777 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	290
0.1-0.2	935
0.2-0.3	1377
0.3-0.4	2573
0.4-0.5	1973
0.5-0.6	1129
0.6-0.7	714
0.7-0.8	152
0.8-0.85	3
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9421	High Similarity	NPD4379	Clinical (unspecified phase)
0.8843	High Similarity	NPD5536	Phase 2
0.8672	High Similarity	NPD9494	Approved
0.8655	High Similarity	NPD228	Approved
0.8211	Intermediate Similarity	NPD5283	Phase 1
0.812	Intermediate Similarity	NPD3027	Phase 3
0.8041	Intermediate Similarity	NPD3882	Suspended
0.8028	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8027	Intermediate Similarity	NPD2801	Approved
0.7969	Intermediate Similarity	NPD1651	Approved
0.7959	Intermediate Similarity	NPD1934	Approved
0.792	Intermediate Similarity	NPD1241	Discontinued
0.7914	Intermediate Similarity	NPD2935	Discontinued
0.7886	Intermediate Similarity	NPD3021	Approved
0.7886	Intermediate Similarity	NPD3022	Approved
0.7863	Intermediate Similarity	NPD3972	Approved
0.7817	Intermediate Similarity	NPD8166	Discontinued
0.7785	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1511	Approved
0.7744	Intermediate Similarity	NPD1283	Approved
0.7744	Intermediate Similarity	NPD1876	Approved
0.7692	Intermediate Similarity	NPD4628	Phase 3
0.7692	Intermediate Similarity	NPD4110	Phase 3
0.7692	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7681	Intermediate Similarity	NPD1240	Approved
0.7681	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7681	Intermediate Similarity	NPD3620	Phase 2
0.7671	Intermediate Similarity	NPD1512	Approved
0.7664	Intermediate Similarity	NPD6798	Discontinued
0.7639	Intermediate Similarity	NPD6190	Approved
0.7635	Intermediate Similarity	NPD3455	Phase 2
0.763	Intermediate Similarity	NPD2798	Approved
0.7626	Intermediate Similarity	NPD447	Suspended
0.7626	Intermediate Similarity	NPD6355	Discontinued
0.7619	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD1894	Discontinued
0.7609	Intermediate Similarity	NPD6233	Phase 2
0.7609	Intermediate Similarity	NPD4062	Phase 3
0.7609	Intermediate Similarity	NPD2674	Phase 3
0.7591	Intermediate Similarity	NPD7095	Approved
0.7584	Intermediate Similarity	NPD7028	Phase 2
0.7576	Intermediate Similarity	NPD3847	Discontinued
0.7571	Intermediate Similarity	NPD1607	Approved
0.7566	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD6166	Phase 2
0.7557	Intermediate Similarity	NPD1357	Approved
0.7556	Intermediate Similarity	NPD2797	Approved
0.7554	Intermediate Similarity	NPD4060	Phase 1
0.7554	Intermediate Similarity	NPD1558	Phase 1
0.7554	Intermediate Similarity	NPD943	Approved
0.7534	Intermediate Similarity	NPD4357	Discontinued
0.752	Intermediate Similarity	NPD2684	Approved
0.7519	Intermediate Similarity	NPD1535	Discovery
0.7519	Intermediate Similarity	NPD1281	Approved
0.7518	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD824	Approved
0.75	Intermediate Similarity	NPD3817	Phase 2
0.75	Intermediate Similarity	NPD4626	Approved
0.75	Intermediate Similarity	NPD230	Phase 1
0.7483	Intermediate Similarity	NPD2344	Approved
0.7483	Intermediate Similarity	NPD7266	Discontinued
0.7468	Intermediate Similarity	NPD3818	Discontinued
0.7465	Intermediate Similarity	NPD1510	Phase 2
0.7465	Intermediate Similarity	NPD2799	Discontinued
0.7463	Intermediate Similarity	NPD1608	Approved
0.7463	Intermediate Similarity	NPD1481	Phase 2
0.7445	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD1358	Approved
0.7429	Intermediate Similarity	NPD1613	Approved
0.7429	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD7054	Approved
0.741	Intermediate Similarity	NPD3145	Approved
0.741	Intermediate Similarity	NPD3144	Approved
0.741	Intermediate Similarity	NPD3268	Approved
0.7407	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD2983	Phase 2
0.7407	Intermediate Similarity	NPD2982	Phase 2
0.7395	Intermediate Similarity	NPD2933	Approved
0.7395	Intermediate Similarity	NPD9296	Approved
0.7395	Intermediate Similarity	NPD2934	Approved
0.7379	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD1933	Approved
0.7375	Intermediate Similarity	NPD7472	Approved
0.7375	Intermediate Similarity	NPD7074	Phase 3
0.7368	Intermediate Similarity	NPD2932	Approved
0.7368	Intermediate Similarity	NPD3019	Approved
0.736	Intermediate Similarity	NPD3134	Approved
0.7355	Intermediate Similarity	NPD6234	Discontinued
0.7351	Intermediate Similarity	NPD4380	Phase 2
0.7348	Intermediate Similarity	NPD9545	Approved
0.7333	Intermediate Similarity	NPD2859	Approved
0.7333	Intermediate Similarity	NPD2981	Phase 2
0.7333	Intermediate Similarity	NPD2860	Approved
0.7329	Intermediate Similarity	NPD7003	Approved
0.7325	Intermediate Similarity	NPD6232	Discontinued
0.7319	Intermediate Similarity	NPD3018	Phase 2
0.731	Intermediate Similarity	NPD4534	Discontinued
0.7303	Intermediate Similarity	NPD6386	Approved
0.7303	Intermediate Similarity	NPD6385	Approved
0.7303	Intermediate Similarity	NPD6873	Phase 2
0.7299	Intermediate Similarity	NPD1203	Approved
0.7297	Intermediate Similarity	NPD6799	Approved
0.7296	Intermediate Similarity	NPD7473	Discontinued
0.7295	Intermediate Similarity	NPD3020	Approved
0.7293	Intermediate Similarity	NPD5585	Approved
0.7287	Intermediate Similarity	NPD7843	Approved
0.7286	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD7458	Discontinued
0.7279	Intermediate Similarity	NPD2309	Approved
0.7279	Intermediate Similarity	NPD2354	Approved
0.7273	Intermediate Similarity	NPD5978	Approved
0.7273	Intermediate Similarity	NPD5977	Approved
0.7266	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD2821	Approved
0.726	Intermediate Similarity	NPD3060	Approved
0.7259	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD37	Approved
0.7252	Intermediate Similarity	NPD7157	Approved
0.7252	Intermediate Similarity	NPD6671	Approved
0.7248	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD6584	Phase 3
0.7239	Intermediate Similarity	NPD17	Approved
0.7222	Intermediate Similarity	NPD968	Approved
0.7222	Intermediate Similarity	NPD6797	Phase 2
0.7212	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD3750	Approved
0.7208	Intermediate Similarity	NPD1465	Phase 2
0.72	Intermediate Similarity	NPD6273	Approved
0.7197	Intermediate Similarity	NPD9493	Approved
0.7195	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD1549	Phase 2
0.7192	Intermediate Similarity	NPD5958	Discontinued
0.7188	Intermediate Similarity	NPD5451	Approved
0.7185	Intermediate Similarity	NPD3496	Discontinued
0.7183	Intermediate Similarity	NPD2979	Phase 3
0.7183	Intermediate Similarity	NPD826	Approved
0.7183	Intermediate Similarity	NPD825	Approved
0.7179	Intermediate Similarity	NPD7075	Discontinued
0.7178	Intermediate Similarity	NPD7685	Pre-registration
0.7178	Intermediate Similarity	NPD7251	Discontinued
0.7172	Intermediate Similarity	NPD2796	Approved
0.7172	Intermediate Similarity	NPD2438	Suspended
0.7171	Intermediate Similarity	NPD3866	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD5691	Approved
0.7163	Intermediate Similarity	NPD2313	Discontinued
0.7163	Intermediate Similarity	NPD5111	Phase 2
0.7163	Intermediate Similarity	NPD5110	Phase 2
0.7163	Intermediate Similarity	NPD5718	Phase 2
0.7163	Intermediate Similarity	NPD3764	Approved
0.7163	Intermediate Similarity	NPD5109	Approved
0.7154	Intermediate Similarity	NPD5535	Approved
0.7152	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD8127	Discontinued
0.7143	Intermediate Similarity	NPD6832	Phase 2
0.7143	Intermediate Similarity	NPD2614	Approved
0.7134	Intermediate Similarity	NPD7808	Phase 3
0.7134	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD3705	Approved
0.7123	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD2346	Discontinued
0.7122	Intermediate Similarity	NPD257	Approved
0.7122	Intermediate Similarity	NPD5647	Approved
0.7122	Intermediate Similarity	NPD258	Approved
0.7117	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD4965	Approved
0.7115	Intermediate Similarity	NPD4967	Phase 2
0.7115	Intermediate Similarity	NPD4966	Approved
0.7113	Intermediate Similarity	NPD8032	Phase 2
0.7113	Intermediate Similarity	NPD259	Phase 1
0.7111	Intermediate Similarity	NPD6516	Phase 2
0.7111	Intermediate Similarity	NPD1778	Approved
0.7111	Intermediate Similarity	NPD5846	Approved
0.7105	Intermediate Similarity	NPD1653	Approved
0.7103	Intermediate Similarity	NPD4308	Phase 3
0.7101	Intermediate Similarity	NPD2922	Phase 1
0.7099	Intermediate Similarity	NPD5844	Phase 1
0.7097	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1006	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD5494	Approved
0.7086	Intermediate Similarity	NPD5049	Phase 3
0.7083	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6653	Approved
0.708	Intermediate Similarity	NPD9717	Approved
0.708	Intermediate Similarity	NPD9269	Phase 2
0.7075	Intermediate Similarity	NPD2424	Discontinued
0.7075	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD2861	Phase 2
0.707	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD3142	Approved
0.7063	Intermediate Similarity	NPD3140	Approved
0.7059	Intermediate Similarity	NPD2651	Approved
0.7059	Intermediate Similarity	NPD2649	Approved
0.7055	Intermediate Similarity	NPD6099	Approved
0.7055	Intermediate Similarity	NPD1501	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD4476	Approved
0.7055	Intermediate Similarity	NPD4477	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