NPASS Compound

Structure

NPC473556 OpenBabel07101718312D 24 26 0 0 1 0 0 0 0 0999 V2000 2.5981 -0.5000 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 1.7321 -2.0000 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 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -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 0.8660 -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 2.5981 -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 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 0.0000 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 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 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 12 2 0 0 0 0 2 7 2 0 0 0 0 2 12 1 0 0 0 0 3 10 1 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 11 16 1 0 0 0 0 11 17 1 0 0 0 0 14 20 1 0 0 0 0 15 21 1 0 0 0 0 16 10 1 6 0 0 0 16 24 1 0 0 0 0 17 18 1 0 0 0 0 17 22 1 0 0 0 0 18 19 1 0 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:	2.215
LogD:	2.533
LogS:	-3.16
# Rotatable Bonds:	4
TPSA:	90.15
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.69
Synthetic Accessibility Score:	3.411
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:	-4.952
MDCK Permeability:	6.476904673036188e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.117
Human Intestinal Absorption (HIA):	0.317
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.056
Plasma Protein Binding (PPB):	90.92066192626953%
Volume Distribution (VD):	1.015
Pgp-substrate:	10.51115894317627%

ADMET: Metabolism

CYP1A2-inhibitor:	0.1
CYP1A2-substrate:	0.07
CYP2C19-inhibitor:	0.343
CYP2C19-substrate:	0.182
CYP2C9-inhibitor:	0.275
CYP2C9-substrate:	0.969
CYP2D6-inhibitor:	0.298
CYP2D6-substrate:	0.873
CYP3A4-inhibitor:	0.152
CYP3A4-substrate:	0.282

ADMET: Excretion

Clearance (CL):	13.789
Half-life (T1/2):	0.799

ADMET: Toxicity

hERG Blockers:	0.21
Human Hepatotoxicity (H-HT):	0.174
Drug-inuced Liver Injury (DILI):	0.023
AMES Toxicity:	0.316
Rat Oral Acute Toxicity:	0.27
Maximum Recommended Daily Dose:	0.884
Skin Sensitization:	0.923
Carcinogencity:	0.512
Eye Corrosion:	0.003
Eye Irritation:	0.121
Respiratory Toxicity:	0.126

Download Data

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

Natural Product: NPC473556

Natural Product ID:	NPC473556
*Common Name:**	(2R,6S)-2-(4-Hydroxyphenyl)-6-[2-(4-Hydroxyphenyl)Ethyl]Oxane-3,4-Diol
IUPAC Name:	(2R,6S)-2-(4-hydroxyphenyl)-6-[2-(4-hydroxyphenyl)ethyl]oxane-3,4-diol
Synonyms:
Standard InCHIKey:	RBJGEWFAPDFFEA-MKCYZYCBSA-N
Standard InCHI:	InChI=1S/C19H22O5/c20-14-6-1-12(2-7-14)3-10-16-11-17(22)18(23)19(24-16)13-4-8-15(21)9-5-13/h1-2,4-9,16-23H,3,10-11H2/t16-,17?,18?,19+/m0/s1
SMILES:	Oc1ccc(cc1)CC[C@H]1CC(O)C([C@H](O1)c1ccc(cc1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL445534
PubChem CID:	44584769
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
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	seeds	Mengha, Yunnan Province, China	1991-Aug	PMID[11277741]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11325233]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[11430002]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461664]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
ED50	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT453	Cell Line	HT-1080	Homo sapiens	ED50	=	83.7	uM	PMID[497134]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	49.4	uM	PMID[497134]

☑ 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 NPC473556 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	325
0.1-0.2	1289
0.2-0.3	3273
0.3-0.4	9650
0.4-0.5	9665
0.5-0.6	5635
0.6-0.7	9441
0.7-0.8	3087
0.8-0.85	290
0.85-0.9	33
0.9-0.95	4
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC301651
0.963	High Similarity	NPC153795
0.963	High Similarity	NPC290353
0.963	High Similarity	NPC42911
0.9174	High Similarity	NPC306045
0.9174	High Similarity	NPC265211
0.9052	High Similarity	NPC160854
0.9052	High Similarity	NPC469703
0.9052	High Similarity	NPC201402
0.9052	High Similarity	NPC469704
0.9035	High Similarity	NPC476266
0.8974	High Similarity	NPC469686
0.8947	High Similarity	NPC175771
0.8926	High Similarity	NPC252307
0.8926	High Similarity	NPC245826
0.8926	High Similarity	NPC311293
0.8926	High Similarity	NPC474178
0.8926	High Similarity	NPC148366
0.8899	High Similarity	NPC92623
0.8899	High Similarity	NPC135464
0.8898	High Similarity	NPC471067
0.8833	High Similarity	NPC167571
0.8833	High Similarity	NPC278552
0.8833	High Similarity	NPC207179
0.8824	High Similarity	NPC232454
0.8824	High Similarity	NPC473451
0.8824	High Similarity	NPC178449
0.8824	High Similarity	NPC470907
0.8807	High Similarity	NPC154899
0.8807	High Similarity	NPC233396
0.8783	High Similarity	NPC148055
0.8772	High Similarity	NPC157338
0.8772	High Similarity	NPC313193
0.877	High Similarity	NPC222572
0.877	High Similarity	NPC72529
0.877	High Similarity	NPC87224
0.8739	High Similarity	NPC174977
0.8729	High Similarity	NPC470414
0.871	High Similarity	NPC103799
0.8704	High Similarity	NPC7686
0.8704	High Similarity	NPC91461
0.8704	High Similarity	NPC40258
0.8699	High Similarity	NPC86030
0.8699	High Similarity	NPC5851
0.8689	High Similarity	NPC288416
0.8684	High Similarity	NPC176730
0.8684	High Similarity	NPC123175
0.864	High Similarity	NPC254275
0.864	High Similarity	NPC201587
0.864	High Similarity	NPC253105
0.8611	High Similarity	NPC213730
0.8609	High Similarity	NPC473137
0.8595	High Similarity	NPC146355
0.8595	High Similarity	NPC257682
0.8595	High Similarity	NPC131747
0.8583	High Similarity	NPC476142
0.8583	High Similarity	NPC255026
0.8537	High Similarity	NPC108659
0.8537	High Similarity	NPC111247
0.8537	High Similarity	NPC41706
0.8537	High Similarity	NPC165045
0.8537	High Similarity	NPC163332
0.8537	High Similarity	NPC147821
0.8537	High Similarity	NPC231607
0.8537	High Similarity	NPC469687
0.8537	High Similarity	NPC292056
0.8537	High Similarity	NPC118787
0.8537	High Similarity	NPC264900
0.8537	High Similarity	NPC183181
0.8537	High Similarity	NPC319625
0.8537	High Similarity	NPC118533
0.8537	High Similarity	NPC79715
0.8519	High Similarity	NPC51333
0.8519	High Similarity	NPC78119
0.8519	High Similarity	NPC216468
0.8519	High Similarity	NPC132078
0.8512	High Similarity	NPC212176
0.8512	High Similarity	NPC76465
0.8512	High Similarity	NPC38761
0.8512	High Similarity	NPC471693
0.8512	High Similarity	NPC474160
0.85	High Similarity	NPC55608
0.85	High Similarity	NPC97432
0.85	High Similarity	NPC190454
0.8496	Intermediate Similarity	NPC474272
0.8487	Intermediate Similarity	NPC469702
0.8487	Intermediate Similarity	NPC282409
0.848	Intermediate Similarity	NPC187998
0.848	Intermediate Similarity	NPC64201
0.848	Intermediate Similarity	NPC77040
0.848	Intermediate Similarity	NPC145305
0.848	Intermediate Similarity	NPC174495
0.848	Intermediate Similarity	NPC241522
0.848	Intermediate Similarity	NPC92164
0.848	Intermediate Similarity	NPC42300
0.848	Intermediate Similarity	NPC257582
0.848	Intermediate Similarity	NPC242807
0.848	Intermediate Similarity	NPC153739
0.8468	Intermediate Similarity	NPC470084
0.8468	Intermediate Similarity	NPC471064
0.8468	Intermediate Similarity	NPC274717
0.8455	Intermediate Similarity	NPC58607
0.8455	Intermediate Similarity	NPC276212
0.8455	Intermediate Similarity	NPC94179
0.8455	Intermediate Similarity	NPC191037
0.8455	Intermediate Similarity	NPC178284
0.8448	Intermediate Similarity	NPC12656
0.8443	Intermediate Similarity	NPC94276
0.8443	Intermediate Similarity	NPC293701
0.8443	Intermediate Similarity	NPC114901
0.8443	Intermediate Similarity	NPC109822
0.8443	Intermediate Similarity	NPC48990
0.8438	Intermediate Similarity	NPC164787
0.8438	Intermediate Similarity	NPC79957
0.8438	Intermediate Similarity	NPC61946
0.843	Intermediate Similarity	NPC100099
0.843	Intermediate Similarity	NPC36016
0.8421	Intermediate Similarity	NPC63345
0.8421	Intermediate Similarity	NPC475018
0.8417	Intermediate Similarity	NPC469412
0.8417	Intermediate Similarity	NPC198734
0.8417	Intermediate Similarity	NPC269242
0.8417	Intermediate Similarity	NPC476445
0.8417	Intermediate Similarity	NPC469548
0.8417	Intermediate Similarity	NPC476448
0.8413	Intermediate Similarity	NPC277804
0.8413	Intermediate Similarity	NPC46137
0.8413	Intermediate Similarity	NPC225384
0.8413	Intermediate Similarity	NPC478255
0.8413	Intermediate Similarity	NPC138777
0.8413	Intermediate Similarity	NPC235294
0.8413	Intermediate Similarity	NPC246869
0.8413	Intermediate Similarity	NPC162801
0.84	Intermediate Similarity	NPC184092
0.84	Intermediate Similarity	NPC475875
0.84	Intermediate Similarity	NPC170844
0.84	Intermediate Similarity	NPC476968
0.8387	Intermediate Similarity	NPC5428
0.8374	Intermediate Similarity	NPC103420
0.8374	Intermediate Similarity	NPC83218
0.8374	Intermediate Similarity	NPC194519
0.8374	Intermediate Similarity	NPC17809
0.8374	Intermediate Similarity	NPC285040
0.8374	Intermediate Similarity	NPC102540
0.8374	Intermediate Similarity	NPC148627
0.8374	Intermediate Similarity	NPC188022
0.8374	Intermediate Similarity	NPC126991
0.8372	Intermediate Similarity	NPC16435
0.8372	Intermediate Similarity	NPC52277
0.8372	Intermediate Similarity	NPC302701
0.8372	Intermediate Similarity	NPC269091
0.8372	Intermediate Similarity	NPC306441
0.8372	Intermediate Similarity	NPC177035
0.8372	Intermediate Similarity	NPC199459
0.8359	Intermediate Similarity	NPC117048
0.8359	Intermediate Similarity	NPC478085
0.8359	Intermediate Similarity	NPC124085
0.8359	Intermediate Similarity	NPC170694
0.8348	Intermediate Similarity	NPC308689
0.8348	Intermediate Similarity	NPC257430
0.8348	Intermediate Similarity	NPC179002
0.8348	Intermediate Similarity	NPC187583
0.8347	Intermediate Similarity	NPC470212
0.8347	Intermediate Similarity	NPC343720
0.8347	Intermediate Similarity	NPC113865
0.8347	Intermediate Similarity	NPC473853
0.8347	Intermediate Similarity	NPC262156
0.8347	Intermediate Similarity	NPC312675
0.8347	Intermediate Similarity	NPC54972
0.8347	Intermediate Similarity	NPC184651
0.8347	Intermediate Similarity	NPC324571
0.8347	Intermediate Similarity	NPC54872
0.8347	Intermediate Similarity	NPC470804
0.8346	Intermediate Similarity	NPC15658
0.8346	Intermediate Similarity	NPC126029
0.8346	Intermediate Similarity	NPC185604
0.8346	Intermediate Similarity	NPC219876
0.8346	Intermediate Similarity	NPC470752
0.8346	Intermediate Similarity	NPC61477
0.8346	Intermediate Similarity	NPC261619
0.8346	Intermediate Similarity	NPC78770
0.8333	Intermediate Similarity	NPC469705
0.8333	Intermediate Similarity	NPC17968
0.8333	Intermediate Similarity	NPC470122
0.8333	Intermediate Similarity	NPC60589
0.8333	Intermediate Similarity	NPC258979
0.8333	Intermediate Similarity	NPC469708
0.8333	Intermediate Similarity	NPC93398
0.8333	Intermediate Similarity	NPC8283
0.832	Intermediate Similarity	NPC129570
0.832	Intermediate Similarity	NPC98631
0.832	Intermediate Similarity	NPC225307
0.832	Intermediate Similarity	NPC148982
0.832	Intermediate Similarity	NPC206615
0.832	Intermediate Similarity	NPC21867
0.832	Intermediate Similarity	NPC11258
0.832	Intermediate Similarity	NPC128208
0.832	Intermediate Similarity	NPC470213
0.832	Intermediate Similarity	NPC282703
0.832	Intermediate Similarity	NPC158673

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 NPC473556 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	286
0.1-0.2	754
0.2-0.3	1430
0.3-0.4	2782
0.4-0.5	2016
0.5-0.6	1139
0.6-0.7	658
0.7-0.8	81
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.84	Intermediate Similarity	NPD3027	Phase 3
0.8346	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8346	Intermediate Similarity	NPD1613	Approved
0.8095	Intermediate Similarity	NPD2861	Phase 2
0.8087	Intermediate Similarity	NPD2684	Approved
0.8073	Intermediate Similarity	NPD2859	Approved
0.8073	Intermediate Similarity	NPD2860	Approved
0.8049	Intermediate Similarity	NPD1091	Approved
0.8049	Intermediate Similarity	NPD1610	Phase 2
0.8031	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8031	Intermediate Similarity	NPD4908	Phase 1
0.8017	Intermediate Similarity	NPD1548	Phase 1
0.8015	Intermediate Similarity	NPD4536	Approved
0.8015	Intermediate Similarity	NPD4538	Approved
0.8015	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7982	Intermediate Similarity	NPD2934	Approved
0.7982	Intermediate Similarity	NPD2933	Approved
0.797	Intermediate Similarity	NPD7266	Discontinued
0.7966	Intermediate Similarity	NPD7843	Approved
0.7955	Intermediate Similarity	NPD5588	Approved
0.7955	Intermediate Similarity	NPD5960	Phase 3
0.7953	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD5846	Approved
0.7886	Intermediate Similarity	NPD5125	Phase 3
0.7886	Intermediate Similarity	NPD5126	Approved
0.7886	Intermediate Similarity	NPD6516	Phase 2
0.7857	Intermediate Similarity	NPD3020	Approved
0.7769	Intermediate Similarity	NPD7157	Approved
0.7759	Intermediate Similarity	NPD968	Approved
0.7742	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7721	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD3021	Approved
0.7712	Intermediate Similarity	NPD3022	Approved
0.7704	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD290	Approved
0.7681	Intermediate Similarity	NPD5058	Phase 3
0.7656	Intermediate Similarity	NPD3094	Phase 2
0.7578	Intermediate Similarity	NPD8651	Approved
0.7576	Intermediate Similarity	NPD6233	Phase 2
0.7565	Intermediate Similarity	NPD940	Approved
0.7565	Intermediate Similarity	NPD846	Approved
0.7552	Intermediate Similarity	NPD4380	Phase 2
0.75	Intermediate Similarity	NPD6798	Discontinued
0.75	Intermediate Similarity	NPD6582	Phase 2
0.75	Intermediate Similarity	NPD4659	Approved
0.75	Intermediate Similarity	NPD6583	Phase 3
0.7482	Intermediate Similarity	NPD6190	Approved
0.7481	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD3092	Approved
0.7478	Intermediate Similarity	NPD1242	Phase 1
0.7463	Intermediate Similarity	NPD4340	Discontinued
0.7459	Intermediate Similarity	NPD5283	Phase 1
0.7438	Intermediate Similarity	NPD228	Approved
0.7417	Intermediate Similarity	NPD5451	Approved
0.741	Intermediate Similarity	NPD4628	Phase 3
0.741	Intermediate Similarity	NPD4535	Phase 3
0.7388	Intermediate Similarity	NPD4060	Phase 1
0.7385	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD4103	Phase 2
0.7377	Intermediate Similarity	NPD5535	Approved
0.7345	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD6671	Approved
0.7338	Intermediate Similarity	NPD1652	Phase 2
0.7328	Intermediate Similarity	NPD6584	Phase 3
0.7319	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD6407	Approved
0.7313	Intermediate Similarity	NPD6405	Approved
0.7302	Intermediate Similarity	NPD3091	Approved
0.7302	Intermediate Similarity	NPD7741	Discontinued
0.7299	Intermediate Similarity	NPD7033	Discontinued
0.7293	Intermediate Similarity	NPD4625	Phase 3
0.7273	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD1549	Phase 2
0.7259	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD3620	Phase 2
0.7254	Intermediate Similarity	NPD7213	Phase 3
0.7254	Intermediate Similarity	NPD7212	Phase 2
0.7248	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD3764	Approved
0.7239	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD4749	Approved
0.7226	Intermediate Similarity	NPD7097	Phase 1
0.7211	Intermediate Similarity	NPD1934	Approved
0.7206	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD5124	Phase 1
0.7206	Intermediate Similarity	NPD5735	Approved
0.7206	Intermediate Similarity	NPD6355	Discontinued
0.7203	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD4062	Phase 3
0.7179	Intermediate Similarity	NPD3028	Approved
0.7165	Intermediate Similarity	NPD9545	Approved
0.7164	Intermediate Similarity	NPD7095	Approved
0.7164	Intermediate Similarity	NPD3180	Approved
0.7164	Intermediate Similarity	NPD3179	Approved
0.7162	Intermediate Similarity	NPD8455	Phase 2
0.7162	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD111	Approved
0.7154	Intermediate Similarity	NPD2231	Phase 2
0.7154	Intermediate Similarity	NPD2561	Approved
0.7154	Intermediate Similarity	NPD2562	Approved
0.7154	Intermediate Similarity	NPD2235	Phase 2
0.7153	Intermediate Similarity	NPD3054	Approved
0.7153	Intermediate Similarity	NPD3052	Approved
0.7143	Intermediate Similarity	NPD2424	Discontinued
0.7132	Intermediate Similarity	NPD3059	Approved
0.7132	Intermediate Similarity	NPD2238	Phase 2
0.7132	Intermediate Similarity	NPD3847	Discontinued
0.7132	Intermediate Similarity	NPD3061	Approved
0.7132	Intermediate Similarity	NPD3062	Approved
0.7107	Intermediate Similarity	NPD1358	Approved
0.7099	Intermediate Similarity	NPD2983	Phase 2
0.7099	Intermediate Similarity	NPD3685	Discontinued
0.7099	Intermediate Similarity	NPD7876	Discontinued
0.7099	Intermediate Similarity	NPD2982	Phase 2
0.7097	Intermediate Similarity	NPD821	Approved
0.7092	Intermediate Similarity	NPD3060	Approved
0.7092	Intermediate Similarity	NPD6674	Discontinued
0.7083	Intermediate Similarity	NPD3536	Discontinued
0.7083	Intermediate Similarity	NPD7447	Phase 1
0.7077	Intermediate Similarity	NPD422	Phase 1
0.7077	Intermediate Similarity	NPD1535	Discovery
0.7077	Intermediate Similarity	NPD3705	Approved
0.7067	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD4198	Discontinued
0.7059	Intermediate Similarity	NPD4404	Approved
0.7055	Intermediate Similarity	NPD1653	Approved
0.7054	Intermediate Similarity	NPD9384	Approved
0.7054	Intermediate Similarity	NPD9381	Approved
0.7054	Intermediate Similarity	NPD3095	Discontinued
0.705	Intermediate Similarity	NPD1510	Phase 2
0.7045	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD6580	Approved
0.7031	Intermediate Similarity	NPD1894	Discontinued
0.7031	Intermediate Similarity	NPD6581	Approved
0.7029	Intermediate Similarity	NPD5314	Approved
0.7023	Intermediate Similarity	NPD1481	Phase 2
0.7023	Intermediate Similarity	NPD2981	Phase 2
0.702	Intermediate Similarity	NPD7075	Discontinued
0.7015	Intermediate Similarity	NPD3018	Phase 2
0.7008	Intermediate Similarity	NPD3596	Phase 2
0.7007	Intermediate Similarity	NPD6057	Approved
0.7007	Intermediate Similarity	NPD6056	Approved
0.7007	Intermediate Similarity	NPD1558	Phase 1
0.6993	Remote Similarity	NPD2677	Approved
0.6992	Remote Similarity	NPD4750	Phase 3
0.6983	Remote Similarity	NPD844	Approved
0.6983	Remote Similarity	NPD1809	Phase 2
0.6977	Remote Similarity	NPD1357	Approved
0.6977	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD291	Approved
0.6972	Remote Similarity	NPD5177	Phase 3
0.6972	Remote Similarity	NPD4236	Phase 3
0.6972	Remote Similarity	NPD4237	Approved
0.6972	Remote Similarity	NPD5061	Approved
0.6972	Remote Similarity	NPD5062	Approved
0.6972	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD6166	Phase 2
0.6966	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD845	Approved
0.6953	Remote Similarity	NPD856	Approved
0.6953	Remote Similarity	NPD16	Approved
0.695	Remote Similarity	NPD5763	Approved
0.695	Remote Similarity	NPD5762	Approved
0.6947	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD3122	Phase 3
0.694	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.693	Remote Similarity	NPD9365	Approved
0.6923	Remote Similarity	NPD2667	Approved
0.6923	Remote Similarity	NPD2668	Approved
0.6917	Remote Similarity	NPD3225	Approved
0.6913	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD6179	Discontinued
0.6906	Remote Similarity	NPD2568	Approved
0.6906	Remote Similarity	NPD6653	Approved
0.6905	Remote Similarity	NPD2229	Approved
0.6905	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD2228	Approved
0.6905	Remote Similarity	NPD2234	Approved
0.6905	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD5736	Approved
0.6885	Remote Similarity	NPD3134	Approved
0.6884	Remote Similarity	NPD1240	Approved
0.6884	Remote Similarity	NPD3597	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD4140	Approved
0.688	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD5403	Approved
0.6867	Remote Similarity	NPD37	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