NPASS Compound

Structure

CID18984 OpenBabel06191715342D 27 28 0 0 0 0 0 0 0 0999 V2000 10.3923 -3.0000 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 6.9282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 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 0.0000 -2.0000 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 0.8660 -1.5000 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 -0.8660 -0.5000 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 -1.7321 -0.0000 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 -0.0000 1.0000 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 7 2 3 0 0 0 3 14 1 0 0 0 0 4 8 2 3 0 0 0 4 15 1 0 0 0 0 5 9 2 0 0 0 0 5 14 1 0 0 0 0 6 10 2 0 0 0 0 6 15 1 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 14 2 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 1 0 0 0 0 13 17 1 0 0 0 0 16 22 2 0 0 0 0 17 23 2 0 0 0 0 18 20 2 0 0 0 0 18 24 1 0 0 0 0 19 21 2 0 0 0 0 19 25 1 0 0 0 0 20 26 1 0 0 0 0 21 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	368.13
Volume:	381.036
LogP:	2.742
LogD:	2.82
LogS:	-3.921
# Rotatable Bonds:	8
TPSA:	93.06
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.548
Synthetic Accessibility Score:	2.426
Fsp3:	0.143
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:	-4.834
MDCK Permeability:	1.632656858419068e-05
Pgp-inhibitor:	0.284
Pgp-substrate:	0.014
Human Intestinal Absorption (HIA):	0.06
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.171

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.103
Plasma Protein Binding (PPB):	99.79946899414062%
Volume Distribution (VD):	0.369
Pgp-substrate:	1.0492939949035645%

ADMET: Metabolism

CYP1A2-inhibitor:	0.593
CYP1A2-substrate:	0.758
CYP2C19-inhibitor:	0.287
CYP2C19-substrate:	0.12
CYP2C9-inhibitor:	0.661
CYP2C9-substrate:	0.906
CYP2D6-inhibitor:	0.037
CYP2D6-substrate:	0.895
CYP3A4-inhibitor:	0.674
CYP3A4-substrate:	0.517

ADMET: Excretion

Clearance (CL):	13.839
Half-life (T1/2):	0.948

ADMET: Toxicity

hERG Blockers:	0.214
Human Hepatotoxicity (H-HT):	0.475
Drug-inuced Liver Injury (DILI):	0.895
AMES Toxicity:	0.234
Rat Oral Acute Toxicity:	0.896
Maximum Recommended Daily Dose:	0.776
Skin Sensitization:	0.958
Carcinogencity:	0.706
Eye Corrosion:	0.007
Eye Irritation:	0.792
Respiratory Toxicity:	0.951

Download Data

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

Natural Product: NPC18984

Natural Product ID:	NPC18984
*Common Name:**	1,7-Bis(4-Hydroxy-3-Methoxyphenyl)Hepta-1,6-Diene-3,5-Dione
IUPAC Name:	1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-dione
Synonyms:
Standard InCHIKey:	VFLDPWHFBUODDF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H20O6/c1-26-20-11-14(5-9-18(20)24)3-7-16(22)13-17(23)8-4-15-6-10-19(25)21(12-15)27-2/h3-12,24-25H,13H2,1-2H3
SMILES:	COc1cc(C=CC(=O)CC(=O)C=Cc2ccc(c(c2)OC)O)ccc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3187799
PubChem CID:	2889
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
NPO9241	Adiantum capillus-veneris	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7308	Fraxinus quadrangulata	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3251	Jacobaea maritima	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7308	Fraxinus quadrangulata	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9241	Adiantum capillus-veneris	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9241	Adiantum capillus-veneris	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25160	Goniothalamus borneensis	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3532	Tridentata marginata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO9241	Adiantum capillus-veneris	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7308	Fraxinus quadrangulata	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3251	Jacobaea maritima	Species	Asteraceae	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
Potency	2

Activity Type	# Activity
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Potency	n.a.	5304.5	nM	PMID[498306]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Potency	n.a.	8407.1	nM	PMID[498306]

☑ 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 NPC18984 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	281
0.1-0.2	1628
0.2-0.3	4623
0.3-0.4	12936
0.4-0.5	4942
0.5-0.6	4722
0.6-0.7	9240
0.7-0.8	3773
0.8-0.85	380
0.85-0.9	125
0.9-0.95	35
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC160900
1.0	High Similarity	NPC106659
1.0	High Similarity	NPC229084
0.9741	High Similarity	NPC14007
0.9741	High Similarity	NPC109083
0.9741	High Similarity	NPC224814
0.9741	High Similarity	NPC269843
0.9741	High Similarity	NPC189844
0.9741	High Similarity	NPC60962
0.9583	High Similarity	NPC276014
0.9576	High Similarity	NPC286573
0.9508	High Similarity	NPC304622
0.9504	High Similarity	NPC276466
0.9504	High Similarity	NPC123722
0.9504	High Similarity	NPC123228
0.9504	High Similarity	NPC5018
0.9504	High Similarity	NPC151167
0.9421	High Similarity	NPC84076
0.9421	High Similarity	NPC179777
0.9421	High Similarity	NPC90128
0.9421	High Similarity	NPC303680
0.9407	High Similarity	NPC158949
0.9397	High Similarity	NPC280001
0.9397	High Similarity	NPC185738
0.9262	High Similarity	NPC92207
0.9262	High Similarity	NPC127937
0.9256	High Similarity	NPC246704
0.918	High Similarity	NPC257589
0.918	High Similarity	NPC289459
0.918	High Similarity	NPC53305
0.9174	High Similarity	NPC164778
0.9174	High Similarity	NPC4181
0.9174	High Similarity	NPC257976
0.9174	High Similarity	NPC242372
0.912	High Similarity	NPC66905
0.9113	High Similarity	NPC110313
0.9106	High Similarity	NPC120225
0.9106	High Similarity	NPC213552
0.9098	High Similarity	NPC273686
0.9098	High Similarity	NPC312404
0.9091	High Similarity	NPC114298
0.9016	High Similarity	NPC163083
0.8992	High Similarity	NPC164706
0.8992	High Similarity	NPC137537
0.8992	High Similarity	NPC272471
0.8992	High Similarity	NPC107588
0.8992	High Similarity	NPC470626
0.8992	High Similarity	NPC70744
0.8983	High Similarity	NPC268317
0.8968	High Similarity	NPC172673
0.8966	High Similarity	NPC51698
0.896	High Similarity	NPC478215
0.896	High Similarity	NPC226661
0.8926	High Similarity	NPC204466
0.8908	High Similarity	NPC293619
0.8908	High Similarity	NPC39793
0.8889	High Similarity	NPC83062
0.8871	High Similarity	NPC87113
0.8852	High Similarity	NPC201777
0.8852	High Similarity	NPC70752
0.8843	High Similarity	NPC95614
0.8843	High Similarity	NPC227217
0.8843	High Similarity	NPC56214
0.8843	High Similarity	NPC232316
0.8843	High Similarity	NPC117780
0.8843	High Similarity	NPC165133
0.8843	High Similarity	NPC202474
0.8843	High Similarity	NPC242885
0.8843	High Similarity	NPC2058
0.8828	High Similarity	NPC239302
0.8819	High Similarity	NPC137427
0.8819	High Similarity	NPC244246
0.8819	High Similarity	NPC215941
0.8819	High Similarity	NPC311419
0.8819	High Similarity	NPC65935
0.8819	High Similarity	NPC123196
0.8819	High Similarity	NPC319282
0.8819	High Similarity	NPC275724
0.879	High Similarity	NPC60517
0.879	High Similarity	NPC146886
0.879	High Similarity	NPC20443
0.8788	High Similarity	NPC474784
0.877	High Similarity	NPC207613
0.877	High Similarity	NPC471877
0.876	High Similarity	NPC327410
0.876	High Similarity	NPC310338
0.876	High Similarity	NPC281298
0.876	High Similarity	NPC299406
0.872	High Similarity	NPC3221
0.8712	High Similarity	NPC284409
0.871	High Similarity	NPC238810
0.8707	High Similarity	NPC246358
0.8707	High Similarity	NPC36108
0.8707	High Similarity	NPC7097
0.8707	High Similarity	NPC233731
0.8702	High Similarity	NPC90431
0.8699	High Similarity	NPC113865
0.8699	High Similarity	NPC184651
0.8699	High Similarity	NPC54872
0.8699	High Similarity	NPC343720
0.8699	High Similarity	NPC160380
0.8699	High Similarity	NPC262156
0.8699	High Similarity	NPC38996
0.8699	High Similarity	NPC312675
0.8699	High Similarity	NPC473853
0.8699	High Similarity	NPC470212
0.8699	High Similarity	NPC324571
0.8678	High Similarity	NPC277460
0.8657	High Similarity	NPC472410
0.8655	High Similarity	NPC294941
0.8629	High Similarity	NPC262253
0.8629	High Similarity	NPC71579
0.8629	High Similarity	NPC473411
0.8629	High Similarity	NPC85488
0.8626	High Similarity	NPC477301
0.8595	High Similarity	NPC86947
0.8594	High Similarity	NPC241354
0.8583	High Similarity	NPC20404
0.8583	High Similarity	NPC16651
0.8583	High Similarity	NPC293641
0.8583	High Similarity	NPC32163
0.8583	High Similarity	NPC20287
0.8583	High Similarity	NPC12022
0.8571	High Similarity	NPC280767
0.8571	High Similarity	NPC67951
0.8571	High Similarity	NPC197832
0.856	High Similarity	NPC317769
0.856	High Similarity	NPC31344
0.856	High Similarity	NPC306100
0.856	High Similarity	NPC280704
0.856	High Similarity	NPC471693
0.8559	High Similarity	NPC78918
0.8559	High Similarity	NPC173746
0.8559	High Similarity	NPC8547
0.8559	High Similarity	NPC297657
0.8559	High Similarity	NPC156840
0.8559	High Similarity	NPC139617
0.8559	High Similarity	NPC257124
0.855	High Similarity	NPC119060
0.855	High Similarity	NPC111635
0.855	High Similarity	NPC135127
0.855	High Similarity	NPC237594
0.855	High Similarity	NPC471110
0.855	High Similarity	NPC249791
0.855	High Similarity	NPC476387
0.8548	High Similarity	NPC194416
0.8548	High Similarity	NPC177291
0.8537	High Similarity	NPC474565
0.8537	High Similarity	NPC247364
0.8537	High Similarity	NPC232084
0.8537	High Similarity	NPC61516
0.8537	High Similarity	NPC10932
0.8525	High Similarity	NPC212743
0.8525	High Similarity	NPC275519
0.8516	High Similarity	NPC278308
0.8512	High Similarity	NPC19290
0.8512	High Similarity	NPC61062
0.8512	High Similarity	NPC299252
0.8512	High Similarity	NPC277394
0.8507	High Similarity	NPC288452
0.8507	High Similarity	NPC289690
0.8504	High Similarity	NPC118584
0.8492	Intermediate Similarity	NPC74478
0.8485	Intermediate Similarity	NPC152209
0.8485	Intermediate Similarity	NPC204592
0.848	Intermediate Similarity	NPC256167
0.8473	Intermediate Similarity	NPC36490
0.8473	Intermediate Similarity	NPC475468
0.8468	Intermediate Similarity	NPC470849
0.8468	Intermediate Similarity	NPC470848
0.8468	Intermediate Similarity	NPC166759
0.8456	Intermediate Similarity	NPC169214
0.8456	Intermediate Similarity	NPC229218
0.8456	Intermediate Similarity	NPC192597
0.8456	Intermediate Similarity	NPC141817
0.8456	Intermediate Similarity	NPC176030
0.8455	Intermediate Similarity	NPC24474
0.8455	Intermediate Similarity	NPC141791
0.8455	Intermediate Similarity	NPC311595
0.8455	Intermediate Similarity	NPC37858
0.8455	Intermediate Similarity	NPC263386
0.8444	Intermediate Similarity	NPC78987
0.8444	Intermediate Similarity	NPC82336
0.8443	Intermediate Similarity	NPC164386
0.8438	Intermediate Similarity	NPC117237
0.8438	Intermediate Similarity	NPC203719
0.8425	Intermediate Similarity	NPC271985
0.8425	Intermediate Similarity	NPC116907
0.8425	Intermediate Similarity	NPC228771
0.8425	Intermediate Similarity	NPC58279
0.8425	Intermediate Similarity	NPC193544
0.8425	Intermediate Similarity	NPC221077
0.8425	Intermediate Similarity	NPC298757
0.8425	Intermediate Similarity	NPC265483
0.8425	Intermediate Similarity	NPC17943
0.8425	Intermediate Similarity	NPC472093
0.8425	Intermediate Similarity	NPC266705
0.8425	Intermediate Similarity	NPC57490
0.8425	Intermediate Similarity	NPC148627
0.8425	Intermediate Similarity	NPC194519

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 NPC18984 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	266
0.1-0.2	958
0.2-0.3	1464
0.3-0.4	2795
0.4-0.5	1866
0.5-0.6	1087
0.6-0.7	613
0.7-0.8	95
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
1.0	High Similarity	NPD4379	Clinical (unspecified phase)
0.9397	High Similarity	NPD5536	Phase 2
0.8559	High Similarity	NPD228	Approved
0.8438	Intermediate Similarity	NPD9494	Approved
0.8264	Intermediate Similarity	NPD5283	Phase 1
0.8168	Intermediate Similarity	NPD3027	Phase 3
0.7934	Intermediate Similarity	NPD3022	Approved
0.7934	Intermediate Similarity	NPD3021	Approved
0.7817	Intermediate Similarity	NPD4357	Discontinued
0.7769	Intermediate Similarity	NPD1358	Approved
0.7734	Intermediate Similarity	NPD1357	Approved
0.7718	Intermediate Similarity	NPD3882	Suspended
0.771	Intermediate Similarity	NPD2983	Phase 2
0.771	Intermediate Similarity	NPD2982	Phase 2
0.7703	Intermediate Similarity	NPD2801	Approved
0.7692	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD1934	Approved
0.7634	Intermediate Similarity	NPD2981	Phase 2
0.763	Intermediate Similarity	NPD7095	Approved
0.7591	Intermediate Similarity	NPD4060	Phase 1
0.7591	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7591	Intermediate Similarity	NPD3620	Phase 2
0.7586	Intermediate Similarity	NPD9296	Approved
0.7574	Intermediate Similarity	NPD3145	Approved
0.7574	Intermediate Similarity	NPD3144	Approved
0.7571	Intermediate Similarity	NPD2935	Discontinued
0.7556	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD3134	Approved
0.7518	Intermediate Similarity	NPD2674	Phase 3
0.7518	Intermediate Similarity	NPD7266	Discontinued
0.75	Intermediate Similarity	NPD3972	Approved
0.7483	Intermediate Similarity	NPD8166	Discontinued
0.7481	Intermediate Similarity	NPD3018	Phase 2
0.7481	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD3847	Discontinued
0.7467	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD1613	Approved
0.7464	Intermediate Similarity	NPD1558	Phase 1
0.7464	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD1651	Approved
0.7448	Intermediate Similarity	NPD1511	Approved
0.7444	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD6190	Approved
0.7419	Intermediate Similarity	NPD2684	Approved
0.741	Intermediate Similarity	NPD447	Suspended
0.7405	Intermediate Similarity	NPD4626	Approved
0.7402	Intermediate Similarity	NPD1241	Discontinued
0.7388	Intermediate Similarity	NPD1876	Approved
0.7361	Intermediate Similarity	NPD4628	Phase 3
0.7361	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD4110	Phase 3
0.7347	Intermediate Similarity	NPD1512	Approved
0.7323	Intermediate Similarity	NPD7843	Approved
0.7319	Intermediate Similarity	NPD6798	Discontinued
0.7315	Intermediate Similarity	NPD3455	Phase 2
0.7315	Intermediate Similarity	NPD824	Approved
0.7297	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD3060	Approved
0.7288	Intermediate Similarity	NPD2934	Approved
0.7288	Intermediate Similarity	NPD2933	Approved
0.7287	Intermediate Similarity	NPD7157	Approved
0.7286	Intermediate Similarity	NPD230	Phase 1
0.7286	Intermediate Similarity	NPD6355	Discontinued
0.7267	Intermediate Similarity	NPD7028	Phase 2
0.7266	Intermediate Similarity	NPD6233	Phase 2
0.7266	Intermediate Similarity	NPD4062	Phase 3
0.7261	Intermediate Similarity	NPD6166	Phase 2
0.7261	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD1283	Approved
0.7259	Intermediate Similarity	NPD2922	Phase 1
0.7258	Intermediate Similarity	NPD968	Approved
0.7255	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD1653	Approved
0.7227	Intermediate Similarity	NPD2860	Approved
0.7227	Intermediate Similarity	NPD2859	Approved
0.7218	Intermediate Similarity	NPD3496	Discontinued
0.7214	Intermediate Similarity	NPD943	Approved
0.7214	Intermediate Similarity	NPD1240	Approved
0.72	Intermediate Similarity	NPD3866	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD5585	Approved
0.7194	Intermediate Similarity	NPD5111	Phase 2
0.7194	Intermediate Similarity	NPD5110	Phase 2
0.7194	Intermediate Similarity	NPD5109	Approved
0.719	Intermediate Similarity	NPD3020	Approved
0.719	Intermediate Similarity	NPD3817	Phase 2
0.7188	Intermediate Similarity	NPD5535	Approved
0.7174	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD3818	Discontinued
0.7164	Intermediate Similarity	NPD3705	Approved
0.7164	Intermediate Similarity	NPD1535	Discovery
0.7163	Intermediate Similarity	NPD1933	Approved
0.7154	Intermediate Similarity	NPD6671	Approved
0.7153	Intermediate Similarity	NPD2344	Approved
0.7153	Intermediate Similarity	NPD6584	Phase 3
0.7153	Intermediate Similarity	NPD2798	Approved
0.7133	Intermediate Similarity	NPD2799	Discontinued
0.7133	Intermediate Similarity	NPD1510	Phase 2
0.7125	Intermediate Similarity	NPD7054	Approved
0.7121	Intermediate Similarity	NPD1894	Discontinued
0.7113	Intermediate Similarity	NPD1607	Approved
0.7113	Intermediate Similarity	NPD2492	Phase 1
0.7111	Intermediate Similarity	NPD1481	Phase 2
0.7103	Intermediate Similarity	NPD2424	Discontinued
0.7087	Intermediate Similarity	NPD5451	Approved
0.7081	Intermediate Similarity	NPD7074	Phase 3
0.7081	Intermediate Similarity	NPD7472	Approved
0.708	Intermediate Similarity	NPD2797	Approved
0.708	Intermediate Similarity	NPD1203	Approved
0.7073	Intermediate Similarity	NPD291	Approved
0.7071	Intermediate Similarity	NPD3268	Approved
0.7071	Intermediate Similarity	NPD5718	Phase 2
0.707	Intermediate Similarity	NPD2821	Approved
0.7068	Intermediate Similarity	NPD5691	Approved
0.7063	Intermediate Similarity	NPD290	Approved
0.7055	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD4162	Approved
0.7051	Intermediate Similarity	NPD6234	Discontinued
0.7042	Intermediate Similarity	NPD4340	Discontinued
0.7039	Intermediate Similarity	NPD4380	Phase 2
0.7037	Intermediate Similarity	NPD1281	Approved
0.7025	Intermediate Similarity	NPD6232	Discontinued
0.7015	Intermediate Similarity	NPD5846	Approved
0.7015	Intermediate Similarity	NPD1778	Approved
0.7015	Intermediate Similarity	NPD6516	Phase 2
0.7007	Intermediate Similarity	NPD3225	Approved
0.7	Intermediate Similarity	NPD7473	Discontinued
0.6994	Remote Similarity	NPD7685	Pre-registration
0.6993	Remote Similarity	NPD6873	Phase 2
0.6993	Remote Similarity	NPD6653	Approved
0.6993	Remote Similarity	NPD6386	Approved
0.6993	Remote Similarity	NPD6385	Approved
0.6992	Remote Similarity	NPD9545	Approved
0.6992	Remote Similarity	NPD1242	Phase 1
0.6985	Remote Similarity	NPD1608	Approved
0.698	Remote Similarity	NPD6799	Approved
0.6978	Remote Similarity	NPD2861	Phase 2
0.6974	Remote Similarity	NPD7458	Discontinued
0.6966	Remote Similarity	NPD6032	Approved
0.6959	Remote Similarity	NPD2309	Approved
0.6959	Remote Similarity	NPD2354	Approved
0.6959	Remote Similarity	NPD5241	Discontinued
0.695	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD37	Approved
0.6944	Remote Similarity	NPD6895	Approved
0.6944	Remote Similarity	NPD6896	Approved
0.6939	Remote Similarity	NPD4236	Phase 3
0.6939	Remote Similarity	NPD4237	Approved
0.6934	Remote Similarity	NPD4359	Approved
0.6934	Remote Similarity	NPD6582	Phase 2
0.6934	Remote Similarity	NPD6583	Phase 3
0.6933	Remote Similarity	NPD4123	Phase 3
0.6933	Remote Similarity	NPD6797	Phase 2
0.6933	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD4908	Phase 1
0.6928	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD3540	Phase 1
0.6912	Remote Similarity	NPD422	Phase 1
0.6909	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD5647	Approved
0.6903	Remote Similarity	NPD1465	Phase 2
0.6903	Remote Similarity	NPD2978	Approved
0.6903	Remote Similarity	NPD2977	Approved
0.6901	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD6331	Phase 2
0.6892	Remote Similarity	NPD3750	Approved
0.6892	Remote Similarity	NPD7003	Approved
0.689	Remote Similarity	NPD7251	Discontinued
0.6889	Remote Similarity	NPD2668	Approved
0.6889	Remote Similarity	NPD2667	Approved
0.6889	Remote Similarity	NPD3019	Approved
0.6889	Remote Similarity	NPD2932	Approved
0.6889	Remote Similarity	NPD2423	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7075	Discontinued
0.6875	Remote Similarity	NPD2653	Approved
0.6871	Remote Similarity	NPD1549	Phase 2
0.6871	Remote Similarity	NPD4534	Discontinued
0.6867	Remote Similarity	NPD5297	Approved
0.6866	Remote Similarity	NPD1548	Phase 1
0.6863	Remote Similarity	NPD3111	Phase 1
0.6861	Remote Similarity	NPD2232	Approved
0.6861	Remote Similarity	NPD9269	Phase 2
0.6861	Remote Similarity	NPD2230	Approved
0.6861	Remote Similarity	NPD9717	Approved
0.6861	Remote Similarity	NPD2233	Approved
0.6859	Remote Similarity	NPD5977	Approved
0.6859	Remote Similarity	NPD5978	Approved
0.6855	Remote Similarity	NPD8127	Discontinued
0.6853	Remote Similarity	NPD2979	Phase 3
0.6853	Remote Similarity	NPD825	Approved
0.6853	Remote Similarity	NPD826	Approved
0.6849	Remote Similarity	NPD2438	Suspended
0.6849	Remote Similarity	NPD3539	Phase 1
0.6848	Remote Similarity	NPD7808	Phase 3
0.6848	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD2219	Phase 1
0.6842	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD9493	Approved
0.6835	Remote Similarity	NPD3053	Approved
0.6835	Remote Similarity	NPD3055	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