NPASS Compound

Structure

NPC153795 OpenBabel07101719512D 23 25 0 0 1 0 0 0 0 0999 V2000 0.8660 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 1.7321 -1.0000 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 -0.0000 2.0000 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 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 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 -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 1.7321 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 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 1 13 2 0 0 0 0 2 7 2 0 0 0 0 2 13 1 0 0 0 0 3 10 1 0 0 0 0 3 13 1 0 0 0 0 4 8 1 0 0 0 0 4 14 2 0 0 0 0 5 9 2 0 0 0 0 5 14 1 0 0 0 0 6 15 2 0 0 0 0 7 15 1 0 0 0 0 8 16 2 0 0 0 0 9 16 1 0 0 0 0 11 17 1 0 0 0 0 11 18 1 0 0 0 0 12 17 1 0 0 0 0 12 19 1 0 0 0 0 15 20 1 0 0 0 0 16 21 1 0 0 0 0 17 22 1 6 0 0 0 18 10 1 1 0 0 0 18 23 1 0 0 0 0 19 14 1 1 0 0 0 19 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	314.15
Volume:	330.853
LogP:	2.867
LogD:	3.011
LogS:	-3.175
# Rotatable Bonds:	4
TPSA:	69.92
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.81
Synthetic Accessibility Score:	3.187
Fsp3:	0.368
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:	-4.679
MDCK Permeability:	1.417483053955948e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.979
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.054
Plasma Protein Binding (PPB):	87.93822479248047%
Volume Distribution (VD):	1.006
Pgp-substrate:	9.577905654907227%

ADMET: Metabolism

CYP1A2-inhibitor:	0.575
CYP1A2-substrate:	0.2
CYP2C19-inhibitor:	0.895
CYP2C19-substrate:	0.324
CYP2C9-inhibitor:	0.822
CYP2C9-substrate:	0.96
CYP2D6-inhibitor:	0.666
CYP2D6-substrate:	0.883
CYP3A4-inhibitor:	0.515
CYP3A4-substrate:	0.373

ADMET: Excretion

Clearance (CL):	15.252
Half-life (T1/2):	0.849

ADMET: Toxicity

hERG Blockers:	0.335
Human Hepatotoxicity (H-HT):	0.39
Drug-inuced Liver Injury (DILI):	0.019
AMES Toxicity:	0.17
Rat Oral Acute Toxicity:	0.474
Maximum Recommended Daily Dose:	0.985
Skin Sensitization:	0.956
Carcinogencity:	0.764
Eye Corrosion:	0.341
Eye Irritation:	0.955
Respiratory Toxicity:	0.925

Download Data

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

Natural Product: NPC153795

Natural Product ID:	NPC153795
*Common Name:**	(1S,3S,5S)-1,7-Bis(4-Hydroxyphenyl)-1,5-Epoxy-3-Hydroxyheptane
IUPAC Name:	(2S,4S,6S)-2-(4-hydroxyphenyl)-6-[2-(4-hydroxyphenyl)ethyl]oxan-4-ol
Synonyms:
Standard InCHIKey:	MRIKNBIACKXKEJ-FHWLQOOXSA-N
Standard InCHI:	InChI=1S/C19H22O4/c20-15-6-1-13(2-7-15)3-10-18-11-17(22)12-19(23-18)14-4-8-16(21)9-5-14/h1-2,4-9,17-22H,3,10-12H2/t17-,18-,19-/m0/s1
SMILES:	Oc1ccc(cc1)CC[C@H]1C[C@H](O)C[C@H](O1)c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2398583
PubChem CID:	71546305
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
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	=	95.6	%	PMID[529626]
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	38110.0	nM	PMID[529626]

☑ 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 NPC153795 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	297
0.1-0.2	1315
0.2-0.3	3335
0.3-0.4	10770
0.4-0.5	8660
0.5-0.6	6283
0.6-0.7	9056
0.7-0.8	2802
0.8-0.85	145
0.85-0.9	26
0.9-0.95	3
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC42911
1.0	High Similarity	NPC290353
0.963	High Similarity	NPC473556
0.963	High Similarity	NPC301651
0.9524	High Similarity	NPC306045
0.9524	High Similarity	NPC265211
0.9238	High Similarity	NPC135464
0.9238	High Similarity	NPC92623
0.9189	High Similarity	NPC476266
0.9143	High Similarity	NPC154899
0.9143	High Similarity	NPC233396
0.9043	High Similarity	NPC174977
0.9038	High Similarity	NPC91461
0.9038	High Similarity	NPC7686
0.9038	High Similarity	NPC40258
0.9	High Similarity	NPC176730
0.9	High Similarity	NPC123175
0.8942	High Similarity	NPC213730
0.8879	High Similarity	NPC255026
0.8846	High Similarity	NPC216468
0.8846	High Similarity	NPC78119
0.8846	High Similarity	NPC132078
0.8846	High Similarity	NPC51333
0.8807	High Similarity	NPC474272
0.8803	High Similarity	NPC38761
0.8803	High Similarity	NPC76465
0.8739	High Similarity	NPC276212
0.8727	High Similarity	NPC475018
0.8727	High Similarity	NPC63345
0.8718	High Similarity	NPC36016
0.8718	High Similarity	NPC100099
0.8707	High Similarity	NPC201402
0.8707	High Similarity	NPC160854
0.8707	High Similarity	NPC469704
0.8707	High Similarity	NPC469703
0.8655	High Similarity	NPC17809
0.8655	High Similarity	NPC188022
0.8655	High Similarity	NPC102540
0.8655	High Similarity	NPC285040
0.8655	High Similarity	NPC103420
0.8644	High Similarity	NPC473451
0.8632	High Similarity	NPC469686
0.8632	High Similarity	NPC54972
0.8621	High Similarity	NPC8283
0.8621	High Similarity	NPC258979
0.8621	High Similarity	NPC93398
0.8596	High Similarity	NPC175771
0.8595	High Similarity	NPC245826
0.8595	High Similarity	NPC274717
0.8595	High Similarity	NPC252307
0.8595	High Similarity	NPC148366
0.8595	High Similarity	NPC311293
0.8595	High Similarity	NPC474178
0.8571	High Similarity	NPC134195
0.8571	High Similarity	NPC86502
0.8571	High Similarity	NPC197351
0.8571	High Similarity	NPC246648
0.8571	High Similarity	NPC106914
0.8559	High Similarity	NPC471067
0.8547	High Similarity	NPC470414
0.8532	High Similarity	NPC113457
0.85	High Similarity	NPC207179
0.85	High Similarity	NPC278552
0.85	High Similarity	NPC167571
0.8487	Intermediate Similarity	NPC178449
0.8487	Intermediate Similarity	NPC470907
0.8487	Intermediate Similarity	NPC232454
0.8462	Intermediate Similarity	NPC151715
0.8443	Intermediate Similarity	NPC222572
0.8443	Intermediate Similarity	NPC87224
0.8443	Intermediate Similarity	NPC72529
0.8435	Intermediate Similarity	NPC229147
0.8435	Intermediate Similarity	NPC85292
0.8435	Intermediate Similarity	NPC54507
0.8435	Intermediate Similarity	NPC148055
0.843	Intermediate Similarity	NPC26879
0.843	Intermediate Similarity	NPC50315
0.843	Intermediate Similarity	NPC283049
0.843	Intermediate Similarity	NPC230479
0.8421	Intermediate Similarity	NPC473137
0.8421	Intermediate Similarity	NPC313193
0.8421	Intermediate Similarity	NPC157338
0.8417	Intermediate Similarity	NPC257682
0.8417	Intermediate Similarity	NPC146355
0.8417	Intermediate Similarity	NPC131747
0.8411	Intermediate Similarity	NPC294741
0.8393	Intermediate Similarity	NPC183700
0.8387	Intermediate Similarity	NPC103799
0.8381	Intermediate Similarity	NPC26244
0.8381	Intermediate Similarity	NPC313650
0.8376	Intermediate Similarity	NPC172253
0.8376	Intermediate Similarity	NPC295259
0.8376	Intermediate Similarity	NPC59561
0.8374	Intermediate Similarity	NPC86030
0.8374	Intermediate Similarity	NPC5851
0.8362	Intermediate Similarity	NPC474933
0.8361	Intermediate Similarity	NPC149796
0.8361	Intermediate Similarity	NPC288416
0.8348	Intermediate Similarity	NPC185541
0.8348	Intermediate Similarity	NPC464
0.8347	Intermediate Similarity	NPC81641
0.8333	Intermediate Similarity	NPC474160
0.8333	Intermediate Similarity	NPC471693
0.832	Intermediate Similarity	NPC201587
0.832	Intermediate Similarity	NPC253105
0.832	Intermediate Similarity	NPC254275
0.8319	Intermediate Similarity	NPC187583
0.8319	Intermediate Similarity	NPC193364
0.8319	Intermediate Similarity	NPC179002
0.8319	Intermediate Similarity	NPC257430
0.8302	Intermediate Similarity	NPC473388
0.8293	Intermediate Similarity	NPC39064
0.8293	Intermediate Similarity	NPC53986
0.8293	Intermediate Similarity	NPC38664
0.8293	Intermediate Similarity	NPC47283
0.8293	Intermediate Similarity	NPC471064
0.8291	Intermediate Similarity	NPC74821
0.8291	Intermediate Similarity	NPC131118
0.8288	Intermediate Similarity	NPC251306
0.8279	Intermediate Similarity	NPC471215
0.8279	Intermediate Similarity	NPC262573
0.8276	Intermediate Similarity	NPC141090
0.8273	Intermediate Similarity	NPC474839
0.8273	Intermediate Similarity	NPC8302
0.8269	Intermediate Similarity	NPC45040
0.8264	Intermediate Similarity	NPC114901
0.8264	Intermediate Similarity	NPC293701
0.8264	Intermediate Similarity	NPC48990
0.8261	Intermediate Similarity	NPC120280
0.8261	Intermediate Similarity	NPC12656
0.8257	Intermediate Similarity	NPC305205
0.825	Intermediate Similarity	NPC150026
0.825	Intermediate Similarity	NPC476142
0.824	Intermediate Similarity	NPC162801
0.824	Intermediate Similarity	NPC476166
0.824	Intermediate Similarity	NPC196765
0.824	Intermediate Similarity	NPC300875
0.824	Intermediate Similarity	NPC280653
0.824	Intermediate Similarity	NPC164574
0.824	Intermediate Similarity	NPC228369
0.824	Intermediate Similarity	NPC206224
0.824	Intermediate Similarity	NPC268917
0.824	Intermediate Similarity	NPC150011
0.824	Intermediate Similarity	NPC129106
0.824	Intermediate Similarity	NPC118114
0.824	Intermediate Similarity	NPC207892
0.824	Intermediate Similarity	NPC12875
0.824	Intermediate Similarity	NPC129784
0.824	Intermediate Similarity	NPC17343
0.824	Intermediate Similarity	NPC236014
0.823	Intermediate Similarity	NPC174096
0.823	Intermediate Similarity	NPC226401
0.823	Intermediate Similarity	NPC147634
0.823	Intermediate Similarity	NPC120982
0.823	Intermediate Similarity	NPC79793
0.823	Intermediate Similarity	NPC44732
0.8226	Intermediate Similarity	NPC93962
0.822	Intermediate Similarity	NPC121866
0.8214	Intermediate Similarity	NPC201959
0.8214	Intermediate Similarity	NPC262365
0.8214	Intermediate Similarity	NPC206341
0.8214	Intermediate Similarity	NPC75440
0.8211	Intermediate Similarity	NPC231607
0.8211	Intermediate Similarity	NPC183181
0.8211	Intermediate Similarity	NPC292056
0.8211	Intermediate Similarity	NPC319625
0.8211	Intermediate Similarity	NPC118787
0.8211	Intermediate Similarity	NPC163332
0.8211	Intermediate Similarity	NPC108659
0.8211	Intermediate Similarity	NPC111247
0.8211	Intermediate Similarity	NPC147821
0.8211	Intermediate Similarity	NPC469687
0.8211	Intermediate Similarity	NPC118533
0.8211	Intermediate Similarity	NPC41706
0.8211	Intermediate Similarity	NPC264900
0.8211	Intermediate Similarity	NPC79715
0.8211	Intermediate Similarity	NPC165045
0.8205	Intermediate Similarity	NPC219070
0.8205	Intermediate Similarity	NPC127894
0.8205	Intermediate Similarity	NPC15860
0.8205	Intermediate Similarity	NPC470759
0.8205	Intermediate Similarity	NPC122117
0.8197	Intermediate Similarity	NPC148627
0.8197	Intermediate Similarity	NPC194519
0.819	Intermediate Similarity	NPC232165
0.819	Intermediate Similarity	NPC53906
0.819	Intermediate Similarity	NPC138117
0.819	Intermediate Similarity	NPC325292
0.8189	Intermediate Similarity	NPC478085
0.8182	Intermediate Similarity	NPC212176
0.8182	Intermediate Similarity	NPC119860
0.8182	Intermediate Similarity	NPC323810
0.8175	Intermediate Similarity	NPC13005
0.8173	Intermediate Similarity	NPC300478
0.8173	Intermediate Similarity	NPC300017
0.8167	Intermediate Similarity	NPC312675
0.8167	Intermediate Similarity	NPC184651
0.8167	Intermediate Similarity	NPC476633
0.8167	Intermediate Similarity	NPC97432
0.8167	Intermediate Similarity	NPC54872

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 NPC153795 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	268
0.1-0.2	809
0.2-0.3	1325
0.3-0.4	2737
0.4-0.5	2054
0.5-0.6	1193
0.6-0.7	661
0.7-0.8	95
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8381	Intermediate Similarity	NPD2860	Approved
0.8381	Intermediate Similarity	NPD2859	Approved
0.8319	Intermediate Similarity	NPD1610	Phase 2
0.8293	Intermediate Similarity	NPD4908	Phase 1
0.8291	Intermediate Similarity	NPD1548	Phase 1
0.8286	Intermediate Similarity	NPD2933	Approved
0.8286	Intermediate Similarity	NPD2934	Approved
0.8211	Intermediate Similarity	NPD2861	Phase 2
0.816	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD3020	Approved
0.808	Intermediate Similarity	NPD3027	Phase 3
0.8031	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8031	Intermediate Similarity	NPD1613	Approved
0.8	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD2684	Approved
0.7876	Intermediate Similarity	NPD968	Approved
0.7838	Intermediate Similarity	NPD940	Approved
0.7838	Intermediate Similarity	NPD846	Approved
0.7778	Intermediate Similarity	NPD7843	Approved
0.7748	Intermediate Similarity	NPD1242	Phase 1
0.7742	Intermediate Similarity	NPD6582	Phase 2
0.7742	Intermediate Similarity	NPD4659	Approved
0.7742	Intermediate Similarity	NPD6583	Phase 3
0.7724	Intermediate Similarity	NPD1091	Approved
0.7717	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.771	Intermediate Similarity	NPD4536	Approved
0.771	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.771	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.771	Intermediate Similarity	NPD4538	Approved
0.7705	Intermediate Similarity	NPD5846	Approved
0.7705	Intermediate Similarity	NPD6516	Phase 2
0.7672	Intermediate Similarity	NPD3021	Approved
0.7672	Intermediate Similarity	NPD3022	Approved
0.7672	Intermediate Similarity	NPD5451	Approved
0.7669	Intermediate Similarity	NPD7266	Discontinued
0.7652	Intermediate Similarity	NPD5960	Phase 3
0.7652	Intermediate Similarity	NPD5588	Approved
0.7638	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD5535	Approved
0.7619	Intermediate Similarity	NPD4103	Phase 2
0.7619	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7583	Intermediate Similarity	NPD7157	Approved
0.7561	Intermediate Similarity	NPD5125	Phase 3
0.7561	Intermediate Similarity	NPD5126	Approved
0.7559	Intermediate Similarity	NPD6584	Phase 3
0.7556	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD7741	Discontinued
0.7541	Intermediate Similarity	NPD3091	Approved
0.7538	Intermediate Similarity	NPD6407	Approved
0.7538	Intermediate Similarity	NPD6405	Approved
0.7537	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7537	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7537	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD7033	Discontinued
0.7519	Intermediate Similarity	NPD4625	Phase 3
0.75	Intermediate Similarity	NPD290	Approved
0.7481	Intermediate Similarity	NPD1549	Phase 2
0.748	Intermediate Similarity	NPD3094	Phase 2
0.7464	Intermediate Similarity	NPD7212	Phase 2
0.7464	Intermediate Similarity	NPD7213	Phase 3
0.7462	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD3764	Approved
0.746	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD4749	Approved
0.744	Intermediate Similarity	NPD3092	Approved
0.7438	Intermediate Similarity	NPD6671	Approved
0.7434	Intermediate Similarity	NPD3028	Approved
0.7429	Intermediate Similarity	NPD111	Approved
0.7424	Intermediate Similarity	NPD5124	Phase 1
0.7424	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD5283	Phase 1
0.7402	Intermediate Similarity	NPD8651	Approved
0.7398	Intermediate Similarity	NPD9545	Approved
0.7391	Intermediate Similarity	NPD5058	Phase 3
0.7381	Intermediate Similarity	NPD2561	Approved
0.7381	Intermediate Similarity	NPD2562	Approved
0.7368	Intermediate Similarity	NPD3052	Approved
0.7368	Intermediate Similarity	NPD3054	Approved
0.736	Intermediate Similarity	NPD3847	Discontinued
0.7333	Intermediate Similarity	NPD821	Approved
0.7328	Intermediate Similarity	NPD6798	Discontinued
0.7323	Intermediate Similarity	NPD3685	Discontinued
0.7302	Intermediate Similarity	NPD422	Phase 1
0.7293	Intermediate Similarity	NPD4340	Discontinued
0.7286	Intermediate Similarity	NPD7447	Phase 1
0.728	Intermediate Similarity	NPD3095	Discontinued
0.7273	Intermediate Similarity	NPD6233	Phase 2
0.7273	Intermediate Similarity	NPD4380	Phase 2
0.7266	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD1510	Phase 2
0.7258	Intermediate Similarity	NPD1894	Discontinued
0.7258	Intermediate Similarity	NPD6581	Approved
0.7258	Intermediate Similarity	NPD6580	Approved
0.725	Intermediate Similarity	NPD228	Approved
0.7246	Intermediate Similarity	NPD4628	Phase 3
0.7244	Intermediate Similarity	NPD2235	Phase 2
0.7244	Intermediate Similarity	NPD2231	Phase 2
0.7236	Intermediate Similarity	NPD3596	Phase 2
0.7232	Intermediate Similarity	NPD844	Approved
0.7232	Intermediate Similarity	NPD1809	Phase 2
0.7227	Intermediate Similarity	NPD4750	Phase 3
0.7218	Intermediate Similarity	NPD4060	Phase 1
0.7218	Intermediate Similarity	NPD2238	Phase 2
0.7207	Intermediate Similarity	NPD845	Approved
0.72	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD6190	Approved
0.7177	Intermediate Similarity	NPD856	Approved
0.7177	Intermediate Similarity	NPD16	Approved
0.7174	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD1535	Discovery
0.7165	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD5735	Approved
0.7163	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2668	Approved
0.7143	Intermediate Similarity	NPD2667	Approved
0.7132	Intermediate Similarity	NPD3225	Approved
0.7131	Intermediate Similarity	NPD2229	Approved
0.7131	Intermediate Similarity	NPD2228	Approved
0.7131	Intermediate Similarity	NPD2234	Approved
0.7131	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD4535	Phase 3
0.7121	Intermediate Similarity	NPD6179	Discontinued
0.7119	Intermediate Similarity	NPD3134	Approved
0.7109	Intermediate Similarity	NPD1481	Phase 2
0.7107	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD5736	Approved
0.709	Intermediate Similarity	NPD4140	Approved
0.709	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD3620	Phase 2
0.709	Intermediate Similarity	NPD1240	Approved
0.7077	Intermediate Similarity	NPD2797	Approved
0.7077	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1358	Approved
0.7059	Intermediate Similarity	NPD2342	Discontinued
0.7059	Intermediate Similarity	NPD7097	Phase 1
0.7054	Intermediate Similarity	NPD2982	Phase 2
0.7054	Intermediate Similarity	NPD2983	Phase 2
0.7054	Intermediate Similarity	NPD5327	Phase 3
0.7054	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD1652	Phase 2
0.705	Intermediate Similarity	NPD3060	Approved
0.7042	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD317	Approved
0.704	Intermediate Similarity	NPD318	Approved
0.7037	Intermediate Similarity	NPD6355	Discontinued
0.7034	Intermediate Similarity	NPD5048	Discontinued
0.7023	Intermediate Similarity	NPD3690	Phase 2
0.7023	Intermediate Similarity	NPD3691	Phase 2
0.7018	Intermediate Similarity	NPD288	Approved
0.7016	Intermediate Similarity	NPD2557	Approved
0.7015	Intermediate Similarity	NPD4062	Phase 3
0.7007	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD4108	Discontinued
0.7007	Intermediate Similarity	NPD3846	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3750	Approved
0.6992	Remote Similarity	NPD3180	Approved
0.6992	Remote Similarity	NPD7095	Approved
0.6992	Remote Similarity	NPD3179	Approved
0.6986	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD2568	Approved
0.6985	Remote Similarity	NPD1607	Approved
0.6983	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD2549	Approved
0.6983	Remote Similarity	NPD2550	Approved
0.6983	Remote Similarity	NPD2553	Approved
0.6983	Remote Similarity	NPD2552	Approved
0.6983	Remote Similarity	NPD2555	Approved
0.6983	Remote Similarity	NPD2558	Approved
0.698	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD1608	Approved
0.6977	Remote Similarity	NPD2981	Phase 2
0.6975	Remote Similarity	NPD3526	Approved
0.6975	Remote Similarity	NPD3524	Approved
0.6972	Remote Similarity	NPD7041	Phase 2
0.6972	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.697	Remote Similarity	NPD3018	Phase 2
0.6966	Remote Similarity	NPD6057	Approved
0.6966	Remote Similarity	NPD6056	Approved
0.6963	Remote Similarity	NPD3059	Approved
0.6963	Remote Similarity	NPD3062	Approved
0.6963	Remote Similarity	NPD3061	Approved
0.6959	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD2796	Approved
0.6947	Remote Similarity	NPD1131	Approved
0.6947	Remote Similarity	NPD1133	Approved
0.6947	Remote Similarity	NPD1129	Approved
0.6947	Remote Similarity	NPD1135	Approved
0.6947	Remote Similarity	NPD1134	Approved
0.694	Remote Similarity	NPD3268	Approved
0.6939	Remote Similarity	NPD1934	Approved
0.6935	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD3553	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