NPASS Compound

Structure

NPC285350 OpenBabel07101719132D 23 24 0 0 1 0 0 0 0 0999 V2000 -8.6603 -0.0000 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 -1.7321 0.0000 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 -2.5981 -1.5000 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 -8.6603 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 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 -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 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 2 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 -6.0622 -2.5000 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 1 7 1 0 0 0 0 1 14 2 0 0 0 0 2 8 2 0 0 0 0 2 14 1 0 0 0 0 3 9 1 0 0 0 0 3 15 2 0 0 0 0 4 10 2 0 0 0 0 4 15 1 0 0 0 0 5 11 2 0 0 0 0 5 14 1 0 0 0 0 6 12 1 0 0 0 0 6 15 1 0 0 0 0 7 16 2 0 0 0 0 8 16 1 0 0 0 0 9 17 2 0 0 0 0 10 17 1 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 13 18 1 0 0 0 0 13 19 1 0 0 0 0 16 20 1 0 0 0 0 17 21 1 0 0 0 0 18 22 2 0 0 0 0 19 23 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	312.14
Volume:	334.136
LogP:	2.759
LogD:	2.791
LogS:	-3.542
# Rotatable Bonds:	7
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.687
Synthetic Accessibility Score:	2.664
Fsp3:	0.211
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.787
MDCK Permeability:	9.591539310349617e-06
Pgp-inhibitor:	0.014
Pgp-substrate:	0.99
Human Intestinal Absorption (HIA):	0.035
20% Bioavailability (F20%):	0.331
30% Bioavailability (F30%):	0.956

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.05
Plasma Protein Binding (PPB):	97.26376342773438%
Volume Distribution (VD):	0.515
Pgp-substrate:	1.4357718229293823%

ADMET: Metabolism

CYP1A2-inhibitor:	0.825
CYP1A2-substrate:	0.072
CYP2C19-inhibitor:	0.807
CYP2C19-substrate:	0.077
CYP2C9-inhibitor:	0.788
CYP2C9-substrate:	0.967
CYP2D6-inhibitor:	0.261
CYP2D6-substrate:	0.88
CYP3A4-inhibitor:	0.462
CYP3A4-substrate:	0.453

ADMET: Excretion

Clearance (CL):	16.664
Half-life (T1/2):	0.922

ADMET: Toxicity

hERG Blockers:	0.18
Human Hepatotoxicity (H-HT):	0.278
Drug-inuced Liver Injury (DILI):	0.052
AMES Toxicity:	0.344
Rat Oral Acute Toxicity:	0.348
Maximum Recommended Daily Dose:	0.932
Skin Sensitization:	0.956
Carcinogencity:	0.762
Eye Corrosion:	0.005
Eye Irritation:	0.897
Respiratory Toxicity:	0.705

Download Data

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

Natural Product: NPC285350

Natural Product ID:	NPC285350
*Common Name:**	(E,5R)-5-Hydroxy-1,7-Bis(4-Hydroxyphenyl)Hept-1-En-3-One
IUPAC Name:	(E,5R)-5-hydroxy-1,7-bis(4-hydroxyphenyl)hept-1-en-3-one
Synonyms:
Standard InCHIKey:	CWFOAVBXINFPCW-PHRJPNOBSA-N
Standard InCHI:	InChI=1S/C19H20O4/c20-16-7-1-14(2-8-16)5-11-18(22)13-19(23)12-6-15-3-9-17(21)10-4-15/h1-5,7-11,19-21,23H,6,12-13H2/b11-5+/t19-/m1/s1
SMILES:	c1cc(ccc1/C=C/C(=O)C[C@@H](CCc1ccc(cc1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2398588
PubChem CID:	73349024
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
NPO14409	Dioscorea nipponica	Species	Dioscoreaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[23707257]
NPO14409	Dioscorea nipponica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14409	Dioscorea nipponica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14409	Dioscorea nipponica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14409	Dioscorea nipponica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14409	Dioscorea nipponica	Species	Dioscoreaceae	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	1
Others	1

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT34	Cell Line	BV-2	Mus musculus	Activity	=	99.37	%	PMID[449520]
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	57050.0	nM	PMID[449520]

☑ 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 NPC285350 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	250
0.1-0.2	1184
0.2-0.3	3318
0.3-0.4	9318
0.4-0.5	10134
0.5-0.6	6399
0.6-0.7	9433
0.7-0.8	2448
0.8-0.85	161
0.85-0.9	34
0.9-0.95	13
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9722	High Similarity	NPC23402
0.9717	High Similarity	NPC177576
0.9623	High Similarity	NPC321252
0.9623	High Similarity	NPC252544
0.9459	High Similarity	NPC249435
0.9346	High Similarity	NPC88141
0.9252	High Similarity	NPC317305
0.9245	High Similarity	NPC29989
0.9245	High Similarity	NPC69332
0.9245	High Similarity	NPC95178
0.9245	High Similarity	NPC70843
0.9217	High Similarity	NPC86900
0.9065	High Similarity	NPC188677
0.9057	High Similarity	NPC8931
0.9057	High Similarity	NPC261573
0.9057	High Similarity	NPC120693
0.9035	High Similarity	NPC182240
0.8957	High Similarity	NPC265454
0.8957	High Similarity	NPC34634
0.8829	High Similarity	NPC114682
0.8785	High Similarity	NPC68269
0.8739	High Similarity	NPC21162
0.8739	High Similarity	NPC116842
0.8718	High Similarity	NPC98305
0.8692	High Similarity	NPC91461
0.8692	High Similarity	NPC7686
0.8692	High Similarity	NPC40258
0.8684	High Similarity	NPC322197
0.8679	High Similarity	NPC130193
0.8679	High Similarity	NPC132078
0.8679	High Similarity	NPC78119
0.8679	High Similarity	NPC216468
0.8679	High Similarity	NPC51333
0.8632	High Similarity	NPC473136
0.8621	High Similarity	NPC184527
0.8611	High Similarity	NPC135784
0.8609	High Similarity	NPC299252
0.8609	High Similarity	NPC19290
0.8609	High Similarity	NPC61062
0.8609	High Similarity	NPC277394
0.8598	High Similarity	NPC213730
0.8585	High Similarity	NPC201967
0.8583	High Similarity	NPC231767
0.8559	High Similarity	NPC17525
0.8548	High Similarity	NPC475042
0.8512	High Similarity	NPC127975
0.8496	Intermediate Similarity	NPC212718
0.8491	Intermediate Similarity	NPC289201
0.8487	Intermediate Similarity	NPC196976
0.8487	Intermediate Similarity	NPC31936
0.8482	Intermediate Similarity	NPC95172
0.8468	Intermediate Similarity	NPC141523
0.8455	Intermediate Similarity	NPC469930
0.8448	Intermediate Similarity	NPC325646
0.8448	Intermediate Similarity	NPC128249
0.8448	Intermediate Similarity	NPC28951
0.8421	Intermediate Similarity	NPC286222
0.8417	Intermediate Similarity	NPC68167
0.8413	Intermediate Similarity	NPC40524
0.8413	Intermediate Similarity	NPC213485
0.8413	Intermediate Similarity	NPC139074
0.8411	Intermediate Similarity	NPC260000
0.8407	Intermediate Similarity	NPC183700
0.8407	Intermediate Similarity	NPC63345
0.8407	Intermediate Similarity	NPC222905
0.839	Intermediate Similarity	NPC473767
0.8387	Intermediate Similarity	NPC102829
0.8387	Intermediate Similarity	NPC120488
0.8349	Intermediate Similarity	NPC472585
0.8333	Intermediate Similarity	NPC280869
0.8333	Intermediate Similarity	NPC268388
0.8319	Intermediate Similarity	NPC326187
0.8306	Intermediate Similarity	NPC158673
0.8304	Intermediate Similarity	NPC226699
0.8302	Intermediate Similarity	NPC151715
0.8302	Intermediate Similarity	NPC206764
0.8293	Intermediate Similarity	NPC71610
0.8288	Intermediate Similarity	NPC233396
0.8288	Intermediate Similarity	NPC154899
0.8281	Intermediate Similarity	NPC283590
0.8281	Intermediate Similarity	NPC70859
0.8281	Intermediate Similarity	NPC61153
0.8281	Intermediate Similarity	NPC130899
0.8279	Intermediate Similarity	NPC474803
0.8264	Intermediate Similarity	NPC133909
0.8264	Intermediate Similarity	NPC32032
0.8261	Intermediate Similarity	NPC228988
0.8257	Intermediate Similarity	NPC294741
0.8254	Intermediate Similarity	NPC108553
0.825	Intermediate Similarity	NPC216216
0.824	Intermediate Similarity	NPC214246
0.8235	Intermediate Similarity	NPC195262
0.8235	Intermediate Similarity	NPC188814
0.823	Intermediate Similarity	NPC31274
0.823	Intermediate Similarity	NPC224584
0.8226	Intermediate Similarity	NPC105157
0.8226	Intermediate Similarity	NPC72158
0.8226	Intermediate Similarity	NPC169250
0.8226	Intermediate Similarity	NPC190043
0.8226	Intermediate Similarity	NPC162612
0.8226	Intermediate Similarity	NPC98254
0.8226	Intermediate Similarity	NPC100067
0.8226	Intermediate Similarity	NPC103356
0.8226	Intermediate Similarity	NPC23126
0.8226	Intermediate Similarity	NPC266689
0.8226	Intermediate Similarity	NPC30501
0.8224	Intermediate Similarity	NPC26244
0.8214	Intermediate Similarity	NPC135464
0.8214	Intermediate Similarity	NPC6984
0.8214	Intermediate Similarity	NPC92623
0.8198	Intermediate Similarity	NPC249067
0.819	Intermediate Similarity	NPC242136
0.819	Intermediate Similarity	NPC11824
0.8182	Intermediate Similarity	NPC73532
0.8182	Intermediate Similarity	NPC295034
0.8182	Intermediate Similarity	NPC242895
0.8182	Intermediate Similarity	NPC143427
0.8182	Intermediate Similarity	NPC224273
0.8182	Intermediate Similarity	NPC45438
0.8182	Intermediate Similarity	NPC156139
0.8182	Intermediate Similarity	NPC115159
0.8182	Intermediate Similarity	NPC19174
0.8182	Intermediate Similarity	NPC267552
0.8175	Intermediate Similarity	NPC65935
0.8175	Intermediate Similarity	NPC137427
0.8175	Intermediate Similarity	NPC123196
0.8175	Intermediate Similarity	NPC215941
0.8175	Intermediate Similarity	NPC470122
0.8175	Intermediate Similarity	NPC319282
0.8175	Intermediate Similarity	NPC244246
0.8175	Intermediate Similarity	NPC275724
0.8175	Intermediate Similarity	NPC469705
0.8175	Intermediate Similarity	NPC17968
0.8175	Intermediate Similarity	NPC311419
0.8174	Intermediate Similarity	NPC297657
0.8174	Intermediate Similarity	NPC470355
0.8167	Intermediate Similarity	NPC473662
0.8167	Intermediate Similarity	NPC159525
0.8167	Intermediate Similarity	NPC7151
0.8167	Intermediate Similarity	NPC216297
0.8165	Intermediate Similarity	NPC245561
0.816	Intermediate Similarity	NPC221777
0.816	Intermediate Similarity	NPC21305
0.816	Intermediate Similarity	NPC473017
0.8151	Intermediate Similarity	NPC41567
0.8151	Intermediate Similarity	NPC104514
0.8148	Intermediate Similarity	NPC473388
0.8145	Intermediate Similarity	NPC471929
0.8145	Intermediate Similarity	NPC62952
0.8145	Intermediate Similarity	NPC471935
0.8145	Intermediate Similarity	NPC267846
0.8145	Intermediate Similarity	NPC471930
0.8142	Intermediate Similarity	NPC260952
0.8142	Intermediate Similarity	NPC228737
0.8125	Intermediate Similarity	NPC13495
0.8115	Intermediate Similarity	NPC469927
0.8115	Intermediate Similarity	NPC139171
0.8113	Intermediate Similarity	NPC45040
0.811	Intermediate Similarity	NPC476407
0.8103	Intermediate Similarity	NPC51698
0.8099	Intermediate Similarity	NPC248363
0.8099	Intermediate Similarity	NPC297186
0.8095	Intermediate Similarity	NPC476119
0.8095	Intermediate Similarity	NPC474998
0.8091	Intermediate Similarity	NPC52472
0.8087	Intermediate Similarity	NPC79793
0.8087	Intermediate Similarity	NPC120982
0.8087	Intermediate Similarity	NPC475018
0.8087	Intermediate Similarity	NPC147634
0.8087	Intermediate Similarity	NPC226401
0.8087	Intermediate Similarity	NPC44732
0.8087	Intermediate Similarity	NPC174096
0.8083	Intermediate Similarity	NPC158222
0.808	Intermediate Similarity	NPC116513
0.807	Intermediate Similarity	NPC262365
0.807	Intermediate Similarity	NPC206341
0.8067	Intermediate Similarity	NPC325295
0.8067	Intermediate Similarity	NPC76308
0.8065	Intermediate Similarity	NPC137416
0.8056	Intermediate Similarity	NPC286006
0.8049	Intermediate Similarity	NPC236981
0.8049	Intermediate Similarity	NPC14141
0.8049	Intermediate Similarity	NPC198014
0.8047	Intermediate Similarity	NPC471066
0.8047	Intermediate Similarity	NPC471095
0.8037	Intermediate Similarity	NPC138117
0.8037	Intermediate Similarity	NPC181709
0.8037	Intermediate Similarity	NPC325292
0.8036	Intermediate Similarity	NPC323810
0.803	Intermediate Similarity	NPC474784
0.8019	Intermediate Similarity	NPC187725
0.8019	Intermediate Similarity	NPC300017
0.8019	Intermediate Similarity	NPC141607
0.8017	Intermediate Similarity	NPC179002
0.8017	Intermediate Similarity	NPC257430
0.8017	Intermediate Similarity	NPC187583
0.8017	Intermediate Similarity	NPC308689
0.8	Intermediate Similarity	NPC470210
0.8	Intermediate Similarity	NPC8745
0.8	Intermediate Similarity	NPC311091

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 NPC285350 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	230
0.1-0.2	869
0.2-0.3	1228
0.3-0.4	2485
0.4-0.5	2362
0.5-0.6	1324
0.6-0.7	571
0.7-0.8	75
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8224	Intermediate Similarity	NPD2860	Approved
0.8224	Intermediate Similarity	NPD2859	Approved
0.8198	Intermediate Similarity	NPD1237	Approved
0.8131	Intermediate Similarity	NPD2934	Approved
0.8131	Intermediate Similarity	NPD2933	Approved
0.8	Intermediate Similarity	NPD3020	Approved
0.7778	Intermediate Similarity	NPD1470	Approved
0.7778	Intermediate Similarity	NPD1164	Approved
0.7742	Intermediate Similarity	NPD1201	Approved
0.7724	Intermediate Similarity	NPD3019	Approved
0.7724	Intermediate Similarity	NPD2932	Approved
0.7686	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7672	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD1510	Phase 2
0.7642	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD1240	Approved
0.7634	Intermediate Similarity	NPD943	Approved
0.763	Intermediate Similarity	NPD1549	Phase 2
0.7612	Intermediate Similarity	NPD2935	Discontinued
0.7607	Intermediate Similarity	NPD9266	Approved
0.7607	Intermediate Similarity	NPD74	Approved
0.76	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7583	Intermediate Similarity	NPD1241	Discontinued
0.7561	Intermediate Similarity	NPD9545	Approved
0.7556	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD3022	Approved
0.7542	Intermediate Similarity	NPD3021	Approved
0.7541	Intermediate Similarity	NPD9493	Approved
0.754	Intermediate Similarity	NPD3972	Approved
0.7521	Intermediate Similarity	NPD9267	Approved
0.7521	Intermediate Similarity	NPD9263	Approved
0.7521	Intermediate Similarity	NPD9264	Approved
0.7519	Intermediate Similarity	NPD1607	Approved
0.7481	Intermediate Similarity	NPD3764	Approved
0.748	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD2798	Approved
0.7419	Intermediate Similarity	NPD1894	Discontinued
0.7413	Intermediate Similarity	NPD4380	Phase 2
0.7407	Intermediate Similarity	NPD2799	Discontinued
0.7391	Intermediate Similarity	NPD3400	Discontinued
0.7391	Intermediate Similarity	NPD4628	Phase 3
0.7381	Intermediate Similarity	NPD3847	Discontinued
0.7364	Intermediate Similarity	NPD1203	Approved
0.7353	Intermediate Similarity	NPD5408	Approved
0.7353	Intermediate Similarity	NPD5404	Approved
0.7353	Intermediate Similarity	NPD5406	Approved
0.7353	Intermediate Similarity	NPD5405	Approved
0.735	Intermediate Similarity	NPD5048	Discontinued
0.7348	Intermediate Similarity	NPD6798	Discontinued
0.7323	Intermediate Similarity	NPD1535	Discovery
0.7319	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD256	Approved
0.7317	Intermediate Similarity	NPD255	Approved
0.7304	Intermediate Similarity	NPD3028	Approved
0.7302	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD2344	Approved
0.7293	Intermediate Similarity	NPD6663	Approved
0.729	Intermediate Similarity	NPD111	Approved
0.7287	Intermediate Similarity	NPD1876	Approved
0.7281	Intermediate Similarity	NPD9495	Approved
0.728	Intermediate Similarity	NPD3091	Approved
0.7279	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD1481	Phase 2
0.7266	Intermediate Similarity	NPD8166	Discontinued
0.7252	Intermediate Similarity	NPD5736	Approved
0.7244	Intermediate Similarity	NPD3023	Approved
0.7244	Intermediate Similarity	NPD3026	Approved
0.7241	Intermediate Similarity	NPD940	Approved
0.7241	Intermediate Similarity	NPD846	Approved
0.7236	Intermediate Similarity	NPD9281	Approved
0.7231	Intermediate Similarity	NPD2797	Approved
0.7226	Intermediate Similarity	NPD2796	Approved
0.7222	Intermediate Similarity	NPD1651	Approved
0.7222	Intermediate Similarity	NPD3025	Approved
0.7222	Intermediate Similarity	NPD3024	Approved
0.7218	Intermediate Similarity	NPD2313	Discontinued
0.7218	Intermediate Similarity	NPD3268	Approved
0.7217	Intermediate Similarity	NPD2066	Phase 3
0.7214	Intermediate Similarity	NPD6190	Approved
0.7209	Intermediate Similarity	NPD5157	Phase 1
0.7209	Intermediate Similarity	NPD5159	Phase 2
0.7209	Intermediate Similarity	NPD5158	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5536	Phase 2
0.7197	Intermediate Similarity	NPD6832	Phase 2
0.7185	Intermediate Similarity	NPD6355	Discontinued
0.7183	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD9261	Approved
0.7179	Intermediate Similarity	NPD6647	Phase 2
0.7167	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD4062	Phase 3
0.7164	Intermediate Similarity	NPD6233	Phase 2
0.7155	Intermediate Similarity	NPD1242	Phase 1
0.7153	Intermediate Similarity	NPD7033	Discontinued
0.712	Intermediate Similarity	NPD9568	Approved
0.7114	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1809	Phase 2
0.7105	Intermediate Similarity	NPD844	Approved
0.7097	Intermediate Similarity	NPD2629	Approved
0.7092	Intermediate Similarity	NPD2309	Approved
0.709	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD845	Approved
0.708	Intermediate Similarity	NPD1202	Approved
0.7077	Intermediate Similarity	NPD4659	Approved
0.7063	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD3092	Approved
0.7045	Intermediate Similarity	NPD5647	Approved
0.7045	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD520	Approved
0.7034	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD1929	Approved
0.7034	Intermediate Similarity	NPD1930	Approved
0.7031	Intermediate Similarity	NPD3095	Discontinued
0.7029	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD2684	Approved
0.7023	Intermediate Similarity	NPD1283	Approved
0.7021	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD3750	Approved
0.7016	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD2234	Approved
0.7016	Intermediate Similarity	NPD2228	Approved
0.7016	Intermediate Similarity	NPD2229	Approved
0.7008	Intermediate Similarity	NPD1759	Phase 1
0.7007	Intermediate Similarity	NPD7411	Suspended
0.7	Intermediate Similarity	NPD9717	Approved
0.7	Intermediate Similarity	NPD968	Approved
0.7	Intermediate Similarity	NPD3134	Approved
0.7	Intermediate Similarity	NPD7075	Discontinued
0.7	Intermediate Similarity	NPD2561	Approved
0.7	Intermediate Similarity	NPD2562	Approved
0.6993	Remote Similarity	NPD7390	Discontinued
0.6993	Remote Similarity	NPD6799	Approved
0.6992	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD4208	Discontinued
0.698	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD1551	Phase 2
0.6975	Remote Similarity	NPD5909	Discontinued
0.697	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.697	Remote Similarity	NPD3094	Phase 2
0.697	Remote Similarity	NPD4103	Phase 2
0.6966	Remote Similarity	NPD5403	Approved
0.6964	Remote Similarity	NPD9258	Approved
0.6964	Remote Similarity	NPD9256	Approved
0.696	Remote Similarity	NPD5951	Approved
0.6959	Remote Similarity	NPD1934	Approved
0.6959	Remote Similarity	NPD6801	Discontinued
0.695	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD1755	Approved
0.6944	Remote Similarity	NPD4662	Approved
0.6944	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD4661	Approved
0.6942	Remote Similarity	NPD1358	Approved
0.6935	Remote Similarity	NPD5535	Approved
0.6935	Remote Similarity	NPD7843	Approved
0.6929	Remote Similarity	NPD7266	Discontinued
0.6929	Remote Similarity	NPD1758	Phase 1
0.6923	Remote Similarity	NPD7440	Discontinued
0.6923	Remote Similarity	NPD1238	Approved
0.6913	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD7003	Approved
0.6897	Remote Similarity	NPD6273	Approved
0.6897	Remote Similarity	NPD288	Approved
0.6889	Remote Similarity	NPD3136	Phase 2
0.6889	Remote Similarity	NPD3027	Phase 3
0.6871	Remote Similarity	NPD7458	Discontinued
0.6871	Remote Similarity	NPD3455	Phase 2
0.687	Remote Similarity	NPD4878	Approved
0.6866	Remote Similarity	NPD9494	Approved
0.6864	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD825	Approved
0.6861	Remote Similarity	NPD826	Approved
0.6857	Remote Similarity	NPD9570	Approved
0.6853	Remote Similarity	NPD3887	Approved
0.6853	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3267	Approved
0.6842	Remote Similarity	NPD3266	Approved
0.6829	Remote Similarity	NPD5451	Approved
0.6828	Remote Similarity	NPD5401	Approved
0.6824	Remote Similarity	NPD6599	Discontinued
0.6821	Remote Similarity	NPD7768	Phase 2
0.6821	Remote Similarity	NPD3882	Suspended
0.6818	Remote Similarity	NPD6583	Phase 3
0.6818	Remote Similarity	NPD6582	Phase 2
0.6818	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD2614	Approved
0.6809	Remote Similarity	NPD2346	Discontinued
0.6807	Remote Similarity	NPD1932	Approved
0.6806	Remote Similarity	NPD3300	Phase 2
0.6803	Remote Similarity	NPD2342	Discontinued
0.68	Remote Similarity	NPD7635	Approved
0.68	Remote Similarity	NPD7819	Suspended
0.6797	Remote Similarity	NPD16	Approved
0.6797	Remote Similarity	NPD856	Approved
0.6794	Remote Similarity	NPD1281	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