NPASS Compound

Structure

NPC476266 OpenBabel07101719512D 24 26 0 0 1 0 0 0 0 0999 V2000 -4.0550 0.0582 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8739 1.7807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2916 2.4852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8366 0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2807 2.6943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6984 3.3988 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8366 2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7026 1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0169 2.3794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9781 -0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8794 1.6762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9706 1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6929 3.5033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7026 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 1.4013 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4781 0.6581 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4727 0.7626 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.1045 0.9945 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2738 3.0485 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0996 4.4168 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5686 2.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0605 -0.0464 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 23 1 0 0 0 0 2 6 1 0 0 0 0 2 12 2 0 0 0 0 3 7 2 0 0 0 0 3 12 1 0 0 0 0 4 8 1 0 0 0 0 4 13 2 0 0 0 0 5 9 2 0 0 0 0 5 13 1 0 0 0 0 6 14 2 0 0 0 0 7 14 1 0 0 0 0 8 15 2 0 0 0 0 9 15 1 0 0 0 0 10 20 1 0 0 0 0 11 17 1 0 0 0 0 11 24 1 0 0 0 0 12 18 1 0 0 0 0 14 21 1 0 0 0 0 15 22 1 0 0 0 0 16 10 1 1 0 0 0 16 17 1 0 0 0 0 16 19 1 0 0 0 0 17 18 1 6 0 0 0 18 23 1 0 0 0 0 19 13 1 6 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	330.15
Volume:	339.643
LogP:	2.037
LogD:	2.407
LogS:	-3.204
# Rotatable Bonds:	5
TPSA:	79.15
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.786
Synthetic Accessibility Score:	3.711
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:	-4.779
MDCK Permeability:	5.1229526434326544e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.64
Human Intestinal Absorption (HIA):	0.14
20% Bioavailability (F20%):	0.913
30% Bioavailability (F30%):	0.798

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.042
Plasma Protein Binding (PPB):	77.54485321044922%
Volume Distribution (VD):	1.226
Pgp-substrate:	16.952537536621094%

ADMET: Metabolism

CYP1A2-inhibitor:	0.048
CYP1A2-substrate:	0.135
CYP2C19-inhibitor:	0.071
CYP2C19-substrate:	0.329
CYP2C9-inhibitor:	0.126
CYP2C9-substrate:	0.705
CYP2D6-inhibitor:	0.175
CYP2D6-substrate:	0.625
CYP3A4-inhibitor:	0.273
CYP3A4-substrate:	0.288

ADMET: Excretion

Clearance (CL):	11.728
Half-life (T1/2):	0.637

ADMET: Toxicity

hERG Blockers:	0.204
Human Hepatotoxicity (H-HT):	0.144
Drug-inuced Liver Injury (DILI):	0.05
AMES Toxicity:	0.205
Rat Oral Acute Toxicity:	0.341
Maximum Recommended Daily Dose:	0.058
Skin Sensitization:	0.871
Carcinogencity:	0.279
Eye Corrosion:	0.003
Eye Irritation:	0.635
Respiratory Toxicity:	0.039

Download Data

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

Natural Product: NPC476266

Natural Product ID:	NPC476266
*Common Name:**	Chushizisin G
IUPAC Name:	4-[(2R,3S,4R)-3-(hydroxymethyl)-4-[(4-hydroxyphenyl)-methoxymethyl]oxolan-2-yl]phenol
Synonyms:	chushizisin G
Standard InCHIKey:	HPAZDJQKSZTHER-HFIAIYGTSA-N
Standard InCHI:	InChI=1S/C19H22O5/c1-23-18(12-2-6-14(21)7-3-12)17-11-24-19(16(17)10-20)13-4-8-15(22)9-5-13/h2-9,16-22H,10-11H2,1H3/t16-,17+,18?,19+/m1/s1
SMILES:	COC([C@H]1CO[C@H]([C@@H]1CO)c1ccc(cc1)O)c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL559774
PubChem CID:	42639502
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003686] Furanoid lignans [CHEMONTID:0001604] Tetrahydrofuran lignans [CHEMONTID:0003422] 7,9'-epoxylignans

*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
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[11395279]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	whole plants	n.a.	n.a.	PMID[11678652]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	whole plants	Shawnee National Forest, Harrisburg, IL, US	n.a.	PMID[11678652]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12419367]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	leaves	Kaohsiung, Taiwan	2006-SEP	PMID[18986201]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	Fruits	n.a.	n.a.	PMID[19296617]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	formosan	n.a.	PMID[8864236]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9358644]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5495	Broussonetia papyrifera	Species	Moraceae	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

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC50	=	281100.0	nM	PMID[568896]

☑ 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 NPC476266 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	263
0.1-0.2	1144
0.2-0.3	2807
0.3-0.4	7983
0.4-0.5	11420
0.5-0.6	6516
0.6-0.7	9482
0.7-0.8	2794
0.8-0.85	236
0.85-0.9	48
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9633	High Similarity	NPC123175
0.9633	High Similarity	NPC176730
0.9231	High Similarity	NPC473451
0.9189	High Similarity	NPC290353
0.9189	High Similarity	NPC153795
0.9189	High Similarity	NPC42911
0.9076	High Similarity	NPC81641
0.9035	High Similarity	NPC473556
0.9035	High Similarity	NPC301651
0.8992	High Similarity	NPC257682
0.8992	High Similarity	NPC131747
0.8992	High Similarity	NPC146355
0.8991	High Similarity	NPC92623
0.8991	High Similarity	NPC135464
0.8919	High Similarity	NPC306045
0.8919	High Similarity	NPC265211
0.8899	High Similarity	NPC154899
0.8899	High Similarity	NPC233396
0.8862	High Similarity	NPC64201
0.8862	High Similarity	NPC153739
0.8862	High Similarity	NPC145305
0.8862	High Similarity	NPC242807
0.8862	High Similarity	NPC42300
0.8862	High Similarity	NPC92164
0.8862	High Similarity	NPC241522
0.8862	High Similarity	NPC257582
0.8862	High Similarity	NPC187998
0.8862	High Similarity	NPC77040
0.8862	High Similarity	NPC174495
0.8852	High Similarity	NPC470084
0.8843	High Similarity	NPC206882
0.8824	High Similarity	NPC174977
0.8824	High Similarity	NPC150026
0.879	High Similarity	NPC277804
0.878	High Similarity	NPC475875
0.8699	High Similarity	NPC11258
0.8699	High Similarity	NPC184733
0.8699	High Similarity	NPC47283
0.8699	High Similarity	NPC128208
0.8699	High Similarity	NPC39064
0.8699	High Similarity	NPC282703
0.8699	High Similarity	NPC45774
0.8699	High Similarity	NPC21867
0.8699	High Similarity	NPC129570
0.8667	High Similarity	NPC255026
0.864	High Similarity	NPC161557
0.864	High Similarity	NPC476166
0.864	High Similarity	NPC280653
0.864	High Similarity	NPC164574
0.864	High Similarity	NPC300875
0.864	High Similarity	NPC27843
0.864	High Similarity	NPC206224
0.864	High Similarity	NPC228369
0.864	High Similarity	NPC236014
0.864	High Similarity	NPC268917
0.864	High Similarity	NPC150011
0.864	High Similarity	NPC118114
0.864	High Similarity	NPC129106
0.864	High Similarity	NPC228346
0.864	High Similarity	NPC40432
0.864	High Similarity	NPC12875
0.864	High Similarity	NPC129784
0.864	High Similarity	NPC196765
0.864	High Similarity	NPC158079
0.864	High Similarity	NPC207892
0.864	High Similarity	NPC115207
0.864	High Similarity	NPC7171
0.864	High Similarity	NPC17343
0.8624	High Similarity	NPC7686
0.8624	High Similarity	NPC91461
0.8624	High Similarity	NPC40258
0.8618	High Similarity	NPC118533
0.8618	High Similarity	NPC165045
0.8584	High Similarity	NPC474272
0.8583	High Similarity	NPC287745
0.8571	High Similarity	NPC181049
0.8571	High Similarity	NPC207400
0.8571	High Similarity	NPC13005
0.856	High Similarity	NPC470225
0.856	High Similarity	NPC27187
0.8537	High Similarity	NPC262573
0.8537	High Similarity	NPC50315
0.8537	High Similarity	NPC230479
0.8537	High Similarity	NPC283049
0.8537	High Similarity	NPC471215
0.8537	High Similarity	NPC26879
0.8534	High Similarity	NPC12656
0.8534	High Similarity	NPC473137
0.8532	High Similarity	NPC213730
0.8509	High Similarity	NPC63345
0.8504	High Similarity	NPC158331
0.8504	High Similarity	NPC26394
0.8496	Intermediate Similarity	NPC201959
0.8492	Intermediate Similarity	NPC162801
0.8492	Intermediate Similarity	NPC271945
0.8492	Intermediate Similarity	NPC181497
0.8468	Intermediate Similarity	NPC323810
0.8468	Intermediate Similarity	NPC5428
0.8455	Intermediate Similarity	NPC148627
0.845	Intermediate Similarity	NPC263367
0.845	Intermediate Similarity	NPC477939
0.845	Intermediate Similarity	NPC29799
0.845	Intermediate Similarity	NPC177160
0.845	Intermediate Similarity	NPC209985
0.845	Intermediate Similarity	NPC54743
0.845	Intermediate Similarity	NPC156502
0.845	Intermediate Similarity	NPC10737
0.8443	Intermediate Similarity	NPC474160
0.844	Intermediate Similarity	NPC132078
0.844	Intermediate Similarity	NPC78119
0.844	Intermediate Similarity	NPC216468
0.844	Intermediate Similarity	NPC51333
0.8438	Intermediate Similarity	NPC296915
0.8438	Intermediate Similarity	NPC223008
0.8438	Intermediate Similarity	NPC225696
0.8438	Intermediate Similarity	NPC97834
0.8438	Intermediate Similarity	NPC198154
0.8438	Intermediate Similarity	NPC115335
0.8438	Intermediate Similarity	NPC326095
0.8438	Intermediate Similarity	NPC244983
0.8438	Intermediate Similarity	NPC67247
0.843	Intermediate Similarity	NPC57268
0.843	Intermediate Similarity	NPC216929
0.843	Intermediate Similarity	NPC312713
0.843	Intermediate Similarity	NPC126935
0.843	Intermediate Similarity	NPC65933
0.843	Intermediate Similarity	NPC172676
0.8425	Intermediate Similarity	NPC175067
0.8425	Intermediate Similarity	NPC4940
0.8425	Intermediate Similarity	NPC230219
0.8425	Intermediate Similarity	NPC204215
0.84	Intermediate Similarity	NPC53986
0.84	Intermediate Similarity	NPC274717
0.84	Intermediate Similarity	NPC474178
0.84	Intermediate Similarity	NPC245826
0.84	Intermediate Similarity	NPC38664
0.84	Intermediate Similarity	NPC148366
0.84	Intermediate Similarity	NPC252307
0.84	Intermediate Similarity	NPC311293
0.8376	Intermediate Similarity	NPC120280
0.8374	Intermediate Similarity	NPC294156
0.8374	Intermediate Similarity	NPC256015
0.8374	Intermediate Similarity	NPC121783
0.8374	Intermediate Similarity	NPC34902
0.8374	Intermediate Similarity	NPC18449
0.8372	Intermediate Similarity	NPC101624
0.8372	Intermediate Similarity	NPC126409
0.8372	Intermediate Similarity	NPC184938
0.8372	Intermediate Similarity	NPC99572
0.8361	Intermediate Similarity	NPC471067
0.8359	Intermediate Similarity	NPC85435
0.8348	Intermediate Similarity	NPC475018
0.8347	Intermediate Similarity	NPC470414
0.8346	Intermediate Similarity	NPC474017
0.8333	Intermediate Similarity	NPC262365
0.8333	Intermediate Similarity	NPC93962
0.8333	Intermediate Similarity	NPC214246
0.8321	Intermediate Similarity	NPC475836
0.832	Intermediate Similarity	NPC183181
0.832	Intermediate Similarity	NPC111247
0.832	Intermediate Similarity	NPC319625
0.832	Intermediate Similarity	NPC163332
0.832	Intermediate Similarity	NPC118787
0.832	Intermediate Similarity	NPC292056
0.832	Intermediate Similarity	NPC147821
0.832	Intermediate Similarity	NPC41706
0.8319	Intermediate Similarity	NPC474933
0.8319	Intermediate Similarity	NPC113457
0.8308	Intermediate Similarity	NPC471988
0.8308	Intermediate Similarity	NPC77861
0.8306	Intermediate Similarity	NPC124030
0.8305	Intermediate Similarity	NPC232165
0.8295	Intermediate Similarity	NPC187616
0.8295	Intermediate Similarity	NPC117048
0.8295	Intermediate Similarity	NPC193026
0.8295	Intermediate Similarity	NPC124085
0.8295	Intermediate Similarity	NPC49603
0.8295	Intermediate Similarity	NPC471942
0.8293	Intermediate Similarity	NPC31344
0.8293	Intermediate Similarity	NPC280704
0.8293	Intermediate Similarity	NPC178449
0.8293	Intermediate Similarity	NPC470907
0.8293	Intermediate Similarity	NPC76465
0.8293	Intermediate Similarity	NPC38761
0.8293	Intermediate Similarity	NPC232454
0.8293	Intermediate Similarity	NPC471693
0.8293	Intermediate Similarity	NPC317769
0.8281	Intermediate Similarity	NPC104077
0.8281	Intermediate Similarity	NPC471505
0.8281	Intermediate Similarity	NPC219671
0.8281	Intermediate Similarity	NPC259742
0.8281	Intermediate Similarity	NPC106739
0.8281	Intermediate Similarity	NPC147616
0.8279	Intermediate Similarity	NPC469686
0.8276	Intermediate Similarity	NPC308689
0.8264	Intermediate Similarity	NPC469702
0.8264	Intermediate Similarity	NPC282409
0.8257	Intermediate Similarity	NPC132271
0.8257	Intermediate Similarity	NPC292730
0.8257	Intermediate Similarity	NPC216520

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 NPC476266 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	235
0.1-0.2	767
0.2-0.3	1368
0.3-0.4	2604
0.4-0.5	2245
0.5-0.6	1194
0.6-0.7	633
0.7-0.8	100
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.844	Intermediate Similarity	NPD3020	Approved
0.832	Intermediate Similarity	NPD2861	Phase 2
0.8254	Intermediate Similarity	NPD4908	Phase 1
0.8189	Intermediate Similarity	NPD3027	Phase 3
0.8165	Intermediate Similarity	NPD2859	Approved
0.8165	Intermediate Similarity	NPD2860	Approved
0.813	Intermediate Similarity	NPD1610	Phase 2
0.8125	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8073	Intermediate Similarity	NPD2934	Approved
0.8073	Intermediate Similarity	NPD2933	Approved
0.7949	Intermediate Similarity	NPD3021	Approved
0.7949	Intermediate Similarity	NPD3022	Approved
0.7874	Intermediate Similarity	NPD3094	Phase 2
0.7823	Intermediate Similarity	NPD5125	Phase 3
0.7823	Intermediate Similarity	NPD5126	Approved
0.7805	Intermediate Similarity	NPD7741	Discontinued
0.7805	Intermediate Similarity	NPD3091	Approved
0.7805	Intermediate Similarity	NPD1548	Phase 1
0.7748	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD1613	Approved
0.7727	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD2684	Approved
0.7705	Intermediate Similarity	NPD7157	Approved
0.7698	Intermediate Similarity	NPD3092	Approved
0.7692	Intermediate Similarity	NPD968	Approved
0.7686	Intermediate Similarity	NPD5283	Phase 1
0.768	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD940	Approved
0.7652	Intermediate Similarity	NPD846	Approved
0.763	Intermediate Similarity	NPD5588	Approved
0.7603	Intermediate Similarity	NPD7843	Approved
0.7594	Intermediate Similarity	NPD2238	Phase 2
0.7576	Intermediate Similarity	NPD3764	Approved
0.7565	Intermediate Similarity	NPD1242	Phase 1
0.7556	Intermediate Similarity	NPD4538	Approved
0.7556	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD4536	Approved
0.754	Intermediate Similarity	NPD3095	Discontinued
0.7536	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD7266	Discontinued
0.75	Intermediate Similarity	NPD4750	Phase 3
0.75	Intermediate Similarity	NPD5058	Phase 3
0.7463	Intermediate Similarity	NPD4060	Phase 1
0.7444	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD6583	Phase 3
0.7442	Intermediate Similarity	NPD4749	Approved
0.7442	Intermediate Similarity	NPD4659	Approved
0.7442	Intermediate Similarity	NPD6582	Phase 2
0.7424	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7422	Intermediate Similarity	NPD1091	Approved
0.7422	Intermediate Similarity	NPD3705	Approved
0.7419	Intermediate Similarity	NPD6671	Approved
0.7407	Intermediate Similarity	NPD6355	Discontinued
0.7407	Intermediate Similarity	NPD5735	Approved
0.7405	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD6584	Phase 3
0.7402	Intermediate Similarity	NPD2667	Approved
0.7402	Intermediate Similarity	NPD2668	Approved
0.7398	Intermediate Similarity	NPD2234	Approved
0.7398	Intermediate Similarity	NPD2229	Approved
0.7398	Intermediate Similarity	NPD2228	Approved
0.7391	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6004	Phase 3
0.7391	Intermediate Similarity	NPD6002	Phase 3
0.7391	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6005	Phase 3
0.7388	Intermediate Similarity	NPD6407	Approved
0.7388	Intermediate Similarity	NPD6405	Approved
0.7385	Intermediate Similarity	NPD8651	Approved
0.7372	Intermediate Similarity	NPD5960	Phase 3
0.7372	Intermediate Similarity	NPD7033	Discontinued
0.7368	Intermediate Similarity	NPD4625	Phase 3
0.7364	Intermediate Similarity	NPD2235	Phase 2
0.7364	Intermediate Similarity	NPD2231	Phase 2
0.7357	Intermediate Similarity	NPD4628	Phase 3
0.7355	Intermediate Similarity	NPD5451	Approved
0.7348	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD5736	Approved
0.7345	Intermediate Similarity	NPD845	Approved
0.7333	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD290	Approved
0.7333	Intermediate Similarity	NPD4140	Approved
0.7333	Intermediate Similarity	NPD3620	Phase 2
0.7328	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD4103	Phase 2
0.7328	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD5535	Approved
0.7317	Intermediate Similarity	NPD7635	Approved
0.7313	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD3685	Discontinued
0.7308	Intermediate Similarity	NPD5327	Phase 3
0.7304	Intermediate Similarity	NPD288	Approved
0.7299	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD6516	Phase 2
0.7266	Intermediate Similarity	NPD5846	Approved
0.7265	Intermediate Similarity	NPD3028	Approved
0.7265	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD6696	Suspended
0.7248	Intermediate Similarity	NPD111	Approved
0.7244	Intermediate Similarity	NPD9545	Approved
0.7236	Intermediate Similarity	NPD228	Approved
0.7231	Intermediate Similarity	NPD2233	Approved
0.7231	Intermediate Similarity	NPD2230	Approved
0.7231	Intermediate Similarity	NPD1608	Approved
0.7231	Intermediate Similarity	NPD2562	Approved
0.7231	Intermediate Similarity	NPD2232	Approved
0.7231	Intermediate Similarity	NPD2561	Approved
0.7226	Intermediate Similarity	NPD3052	Approved
0.7226	Intermediate Similarity	NPD3054	Approved
0.7217	Intermediate Similarity	NPD1809	Phase 2
0.7217	Intermediate Similarity	NPD844	Approved
0.7213	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD3847	Discontinued
0.7188	Intermediate Similarity	NPD1357	Approved
0.7177	Intermediate Similarity	NPD821	Approved
0.7163	Intermediate Similarity	NPD4236	Phase 3
0.7163	Intermediate Similarity	NPD4237	Approved
0.7162	Intermediate Similarity	NPD37	Approved
0.7154	Intermediate Similarity	NPD422	Phase 1
0.7154	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD5124	Phase 1
0.7143	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5762	Approved
0.7143	Intermediate Similarity	NPD5763	Approved
0.7143	Intermediate Similarity	NPD4624	Approved
0.7133	Intermediate Similarity	NPD4965	Approved
0.7133	Intermediate Similarity	NPD6666	Approved
0.7133	Intermediate Similarity	NPD6667	Approved
0.7133	Intermediate Similarity	NPD4967	Phase 2
0.7133	Intermediate Similarity	NPD4966	Approved
0.7132	Intermediate Similarity	NPD4059	Approved
0.7132	Intermediate Similarity	NPD6233	Phase 2
0.7132	Intermediate Similarity	NPD2932	Approved
0.7132	Intermediate Similarity	NPD3019	Approved
0.7132	Intermediate Similarity	NPD6663	Approved
0.712	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD3892	Phase 2
0.7109	Intermediate Similarity	NPD1182	Approved
0.7107	Intermediate Similarity	NPD3134	Approved
0.7101	Intermediate Similarity	NPD2568	Approved
0.7101	Intermediate Similarity	NPD6353	Approved
0.7101	Intermediate Similarity	NPD6653	Approved
0.7099	Intermediate Similarity	NPD1840	Phase 2
0.7097	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD7037	Approved
0.7087	Intermediate Similarity	NPD3596	Phase 2
0.7083	Intermediate Similarity	NPD7212	Phase 2
0.7083	Intermediate Similarity	NPD7213	Phase 3
0.708	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD1792	Phase 2
0.7068	Intermediate Similarity	NPD6362	Approved
0.7068	Intermediate Similarity	NPD2797	Approved
0.7063	Intermediate Similarity	NPD6190	Approved
0.7059	Intermediate Similarity	NPD6798	Discontinued
0.7054	Intermediate Similarity	NPD4093	Discontinued
0.7054	Intermediate Similarity	NPD5585	Approved
0.7045	Intermediate Similarity	NPD2983	Phase 2
0.7045	Intermediate Similarity	NPD2982	Phase 2
0.7045	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD3060	Approved
0.7039	Intermediate Similarity	NPD6234	Discontinued
0.7034	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD7447	Phase 1
0.7031	Intermediate Similarity	NPD16	Approved
0.7031	Intermediate Similarity	NPD856	Approved
0.7027	Intermediate Similarity	NPD4380	Phase 2
0.7023	Intermediate Similarity	NPD1535	Discovery
0.7021	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD3690	Phase 2
0.7015	Intermediate Similarity	NPD558	Phase 2
0.7015	Intermediate Similarity	NPD3691	Phase 2
0.7015	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1510	Phase 2
0.7	Intermediate Similarity	NPD4626	Approved
0.7	Intermediate Similarity	NPD17	Approved
0.7	Intermediate Similarity	NPD4108	Discontinued
0.6993	Remote Similarity	NPD4535	Phase 3
0.6993	Remote Similarity	NPD7466	Approved
0.6992	Remote Similarity	NPD1283	Approved
0.6992	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD7095	Approved
0.6978	Remote Similarity	NPD4097	Suspended
0.6977	Remote Similarity	NPD6581	Approved
0.6977	Remote Similarity	NPD5304	Approved
0.6977	Remote Similarity	NPD6580	Approved
0.6977	Remote Similarity	NPD1894	Discontinued
0.6977	Remote Similarity	NPD5303	Approved
0.6972	Remote Similarity	NPD2424	Discontinued
0.6972	Remote Similarity	NPD1549	Phase 2
0.697	Remote Similarity	NPD2981	Phase 2
0.697	Remote Similarity	NPD1481	Phase 2
0.6967	Remote Similarity	NPD1444	Approved
0.6967	Remote Similarity	NPD1445	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