NPASS Compound

Structure

NPC207400 OpenBabel07101718272D 27 30 0 0 1 0 0 0 0 0999 V2000 -6.7218 -0.4351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4347 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2577 -0.4351 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 -4.1237 -0.9351 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 -4.1237 1.0649 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 -0.9781 -0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3090 2.2673 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2577 0.5649 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 -1.4781 0.6581 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9898 0.5649 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 -4.9898 -0.4351 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 -2.3917 1.0649 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1045 0.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8090 1.4013 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8558 1.0649 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5686 0.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1399 2.1444 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8558 -0.9351 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 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2872 2.0594 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 25 1 0 0 0 0 3 5 2 0 0 0 0 3 11 1 0 0 0 0 4 6 2 0 0 0 0 4 12 1 0 0 0 0 5 16 1 0 0 0 0 6 17 1 0 0 0 0 7 11 2 0 0 0 0 7 14 1 0 0 0 0 8 12 2 0 0 0 0 8 15 1 0 0 0 0 9 13 1 0 0 0 0 9 26 1 0 0 0 0 10 20 1 0 0 0 0 10 27 1 0 0 0 0 12 19 1 0 0 0 0 13 18 1 0 0 0 0 13 20 1 6 0 0 0 14 16 2 0 0 0 0 14 21 1 0 0 0 0 15 17 2 0 0 0 0 15 22 1 0 0 0 0 16 24 1 0 0 0 0 17 25 1 0 0 0 0 18 11 1 1 0 0 0 18 27 1 0 0 0 0 19 20 1 1 0 0 0 19 26 1 0 0 0 0 20 23 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	374.14
Volume:	365.963
LogP:	1.87
LogD:	2.106
LogS:	-4.04
# Rotatable Bonds:	4
TPSA:	97.61
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.755
Synthetic Accessibility Score:	3.917
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.166
MDCK Permeability:	7.66343146096915e-06
Pgp-inhibitor:	0.006
Pgp-substrate:	0.724
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.056

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.08
Plasma Protein Binding (PPB):	91.51876068115234%
Volume Distribution (VD):	1.077
Pgp-substrate:	13.37601089477539%

ADMET: Metabolism

CYP1A2-inhibitor:	0.097
CYP1A2-substrate:	0.855
CYP2C19-inhibitor:	0.048
CYP2C19-substrate:	0.393
CYP2C9-inhibitor:	0.162
CYP2C9-substrate:	0.637
CYP2D6-inhibitor:	0.34
CYP2D6-substrate:	0.831
CYP3A4-inhibitor:	0.785
CYP3A4-substrate:	0.499

ADMET: Excretion

Clearance (CL):	12.443
Half-life (T1/2):	0.637

ADMET: Toxicity

hERG Blockers:	0.282
Human Hepatotoxicity (H-HT):	0.65
Drug-inuced Liver Injury (DILI):	0.701
AMES Toxicity:	0.635
Rat Oral Acute Toxicity:	0.119
Maximum Recommended Daily Dose:	0.181
Skin Sensitization:	0.907
Carcinogencity:	0.066
Eye Corrosion:	0.004
Eye Irritation:	0.541
Respiratory Toxicity:	0.862

Download Data

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

Natural Product: NPC207400

Natural Product ID:	NPC207400
*Common Name:**	5,5'-((1S,3As,4R,6Ar)-3A-Hydroxyhexahydrofuro[3,4-C]Furan-1,4-Diyl)Bis(2-Methoxyphenol)
IUPAC Name:	(3R,3aS,6S,6aR)-3,6-bis(3-hydroxy-4-methoxyphenyl)-3,4,6,6a-tetrahydro-1H-furo[3,4-c]furan-3a-ol
Synonyms:
Standard InCHIKey:	JNNJGAAXLBQGKG-WNISUXOKSA-N
Standard InCHI:	InChI=1S/C20H22O7/c1-24-16-5-3-11(7-14(16)21)18-13-9-26-19(20(13,23)10-27-18)12-4-6-17(25-2)15(22)8-12/h3-8,13,18-19,21-23H,9-10H2,1-2H3/t13-,18-,19-,20-/m1/s1
SMILES:	COc1ccc(cc1O)[C@@H]1[C@H]2CO[C@H](c3ccc(c(c3)O)OC)[C@]2(CO1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2313552
PubChem CID:	71719761
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003686] Furanoid lignans

*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
NPO33401	schisandra sphenathera	Species	Schisandraceae	Eukaryota	stems	n.a.	n.a.	PMID[23237974]

☑ 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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT176	Organism	Artemia salina	Artemia salina	LC50	>	100.0	ug.mL-1	PMID[501564]

☑ 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 NPC207400 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	392
0.1-0.2	1286
0.2-0.3	3631
0.3-0.4	10105
0.4-0.5	9034
0.5-0.6	5446
0.6-0.7	9221
0.7-0.8	2665
0.8-0.85	634
0.85-0.9	197
0.9-0.95	74
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC181049
0.992	High Similarity	NPC158079
0.992	High Similarity	NPC161557
0.992	High Similarity	NPC115207
0.992	High Similarity	NPC40432
0.992	High Similarity	NPC27843
0.992	High Similarity	NPC228346
0.992	High Similarity	NPC7171
0.9841	High Similarity	NPC4940
0.9762	High Similarity	NPC277804
0.9683	High Similarity	NPC42300
0.9683	High Similarity	NPC187998
0.9683	High Similarity	NPC64201
0.9683	High Similarity	NPC145305
0.9683	High Similarity	NPC174495
0.9683	High Similarity	NPC257582
0.9683	High Similarity	NPC153739
0.9683	High Similarity	NPC92164
0.9683	High Similarity	NPC241522
0.9683	High Similarity	NPC77040
0.9683	High Similarity	NPC242807
0.968	High Similarity	NPC282703
0.968	High Similarity	NPC11258
0.968	High Similarity	NPC184733
0.968	High Similarity	NPC45774
0.968	High Similarity	NPC129570
0.968	High Similarity	NPC128208
0.968	High Similarity	NPC21867
0.9612	High Similarity	NPC126409
0.9612	High Similarity	NPC99572
0.9603	High Similarity	NPC475875
0.9524	High Similarity	NPC470084
0.9462	High Similarity	NPC24490
0.9462	High Similarity	NPC34103
0.9462	High Similarity	NPC165155
0.9462	High Similarity	NPC141765
0.9462	High Similarity	NPC135777
0.9462	High Similarity	NPC142547
0.9457	High Similarity	NPC158331
0.9444	High Similarity	NPC5428
0.9444	High Similarity	NPC118533
0.9444	High Similarity	NPC165045
0.9394	High Similarity	NPC193666
0.9394	High Similarity	NPC123526
0.9394	High Similarity	NPC88640
0.9389	High Similarity	NPC471988
0.9385	High Similarity	NPC287745
0.9385	High Similarity	NPC67247
0.938	High Similarity	NPC175067
0.938	High Similarity	NPC204215
0.9365	High Similarity	NPC206882
0.936	High Similarity	NPC257682
0.936	High Similarity	NPC18449
0.936	High Similarity	NPC34902
0.936	High Similarity	NPC146355
0.936	High Similarity	NPC121783
0.936	High Similarity	NPC131747
0.9286	High Similarity	NPC148627
0.928	High Similarity	NPC317769
0.928	High Similarity	NPC31344
0.9242	High Similarity	NPC29799
0.9242	High Similarity	NPC263367
0.9242	High Similarity	NPC477939
0.9242	High Similarity	NPC177160
0.9242	High Similarity	NPC54743
0.9242	High Similarity	NPC209985
0.9242	High Similarity	NPC10737
0.9242	High Similarity	NPC156502
0.9237	High Similarity	NPC49603
0.9237	High Similarity	NPC471942
0.9237	High Similarity	NPC244983
0.9237	High Similarity	NPC193026
0.9237	High Similarity	NPC187616
0.9237	High Similarity	NPC326095
0.9231	High Similarity	NPC471505
0.9219	High Similarity	NPC252307
0.9219	High Similarity	NPC245826
0.9219	High Similarity	NPC474178
0.9191	High Similarity	NPC84181
0.9179	High Similarity	NPC55793
0.9179	High Similarity	NPC177868
0.9173	High Similarity	NPC281780
0.9167	High Similarity	NPC101624
0.9167	High Similarity	NPC184938
0.9154	High Similarity	NPC474017
0.9141	High Similarity	NPC147821
0.9141	High Similarity	NPC319625
0.9141	High Similarity	NPC118787
0.9141	High Similarity	NPC183181
0.9141	High Similarity	NPC163332
0.9141	High Similarity	NPC292056
0.9141	High Similarity	NPC41706
0.9141	High Similarity	NPC111247
0.9127	High Similarity	NPC280704
0.9127	High Similarity	NPC473451
0.9127	High Similarity	NPC471693
0.912	High Similarity	NPC126935
0.912	High Similarity	NPC312713
0.912	High Similarity	NPC57268
0.912	High Similarity	NPC216929
0.912	High Similarity	NPC65933
0.912	High Similarity	NPC172676
0.9118	High Similarity	NPC298317
0.9118	High Similarity	NPC255566
0.9118	High Similarity	NPC265154
0.9118	High Similarity	NPC477898
0.9098	High Similarity	NPC77861
0.9084	High Similarity	NPC147616
0.9084	High Similarity	NPC106739
0.9084	High Similarity	NPC104077
0.9084	High Similarity	NPC259742
0.9084	High Similarity	NPC219671
0.907	High Similarity	NPC82862
0.907	High Similarity	NPC222127
0.9062	High Similarity	NPC178284
0.9062	High Similarity	NPC191037
0.9062	High Similarity	NPC58607
0.9058	High Similarity	NPC112861
0.9051	High Similarity	NPC471415
0.9051	High Similarity	NPC470097
0.9051	High Similarity	NPC114119
0.9048	High Similarity	NPC85488
0.9037	High Similarity	NPC254759
0.9037	High Similarity	NPC309124
0.9037	High Similarity	NPC184797
0.9037	High Similarity	NPC160283
0.903	High Similarity	NPC101807
0.9023	High Similarity	NPC174191
0.9023	High Similarity	NPC18576
0.9015	High Similarity	NPC169973
0.9015	High Similarity	NPC26394
0.9	High Similarity	NPC5851
0.9	High Similarity	NPC476968
0.9	High Similarity	NPC86030
0.9	High Similarity	NPC170844
0.8992	High Similarity	NPC473093
0.8992	High Similarity	NPC8050
0.8992	High Similarity	NPC127587
0.8992	High Similarity	NPC473092
0.8986	High Similarity	NPC38041
0.8986	High Similarity	NPC22150
0.8986	High Similarity	NPC223185
0.8986	High Similarity	NPC279298
0.8986	High Similarity	NPC18979
0.8984	High Similarity	NPC194519
0.8978	High Similarity	NPC12728
0.8978	High Similarity	NPC185071
0.8971	High Similarity	NPC263261
0.8971	High Similarity	NPC87725
0.8971	High Similarity	NPC471414
0.8971	High Similarity	NPC472711
0.8968	High Similarity	NPC470212
0.8968	High Similarity	NPC324571
0.8968	High Similarity	NPC262156
0.8968	High Similarity	NPC343720
0.8968	High Similarity	NPC312675
0.8968	High Similarity	NPC470804
0.8968	High Similarity	NPC476343
0.8968	High Similarity	NPC473853
0.8968	High Similarity	NPC184651
0.8968	High Similarity	NPC113865
0.8968	High Similarity	NPC54872
0.8963	High Similarity	NPC473739
0.8963	High Similarity	NPC292882
0.8963	High Similarity	NPC232164
0.8963	High Similarity	NPC236306
0.896	High Similarity	NPC117780
0.896	High Similarity	NPC242885
0.896	High Similarity	NPC232316
0.896	High Similarity	NPC56214
0.896	High Similarity	NPC227217
0.896	High Similarity	NPC95614
0.896	High Similarity	NPC165133
0.8947	High Similarity	NPC478085
0.8947	High Similarity	NPC311256
0.8947	High Similarity	NPC47181
0.8939	High Similarity	NPC253105
0.8939	High Similarity	NPC230219
0.8939	High Similarity	NPC201587
0.8931	High Similarity	NPC143483
0.8931	High Similarity	NPC173308
0.8931	High Similarity	NPC181079
0.8931	High Similarity	NPC275950
0.8923	High Similarity	NPC57119
0.8923	High Similarity	NPC158471
0.8923	High Similarity	NPC226862
0.8923	High Similarity	NPC470213
0.8923	High Similarity	NPC281864
0.8923	High Similarity	NPC72529
0.8923	High Similarity	NPC165128
0.8923	High Similarity	NPC54321
0.8923	High Similarity	NPC98631
0.8923	High Similarity	NPC206615
0.8923	High Similarity	NPC186843
0.8923	High Similarity	NPC328682
0.8921	High Similarity	NPC317053
0.8921	High Similarity	NPC324492
0.8915	High Similarity	NPC285725
0.8915	High Similarity	NPC76451
0.8915	High Similarity	NPC50683

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 NPC207400 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	313
0.1-0.2	769
0.2-0.3	1759
0.3-0.4	2765
0.4-0.5	1855
0.5-0.6	1057
0.6-0.7	549
0.7-0.8	79
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
0.9	High Similarity	NPD3027	Phase 3
0.84	Intermediate Similarity	NPD5283	Phase 1
0.8382	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8382	Intermediate Similarity	NPD1613	Approved
0.824	Intermediate Similarity	NPD228	Approved
0.8222	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD2861	Phase 2
0.8148	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8116	Intermediate Similarity	NPD3620	Phase 2
0.8116	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.8106	Intermediate Similarity	NPD3705	Approved
0.8092	Intermediate Similarity	NPD6234	Discontinued
0.808	Intermediate Similarity	NPD3022	Approved
0.808	Intermediate Similarity	NPD3021	Approved
0.7985	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD4965	Approved
0.7843	Intermediate Similarity	NPD4966	Approved
0.7843	Intermediate Similarity	NPD4967	Phase 2
0.7826	Intermediate Similarity	NPD4908	Phase 1
0.7744	Intermediate Similarity	NPD1357	Approved
0.7736	Intermediate Similarity	NPD7228	Approved
0.773	Intermediate Similarity	NPD1558	Phase 1
0.773	Intermediate Similarity	NPD4060	Phase 1
0.7721	Intermediate Similarity	NPD2982	Phase 2
0.7721	Intermediate Similarity	NPD2983	Phase 2
0.7714	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7704	Intermediate Similarity	NPD1610	Phase 2
0.7703	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD4237	Approved
0.7671	Intermediate Similarity	NPD4236	Phase 3
0.7655	Intermediate Similarity	NPD7266	Discontinued
0.7647	Intermediate Similarity	NPD1934	Approved
0.7647	Intermediate Similarity	NPD37	Approved
0.7647	Intermediate Similarity	NPD2981	Phase 2
0.7626	Intermediate Similarity	NPD3018	Phase 2
0.7591	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD2684	Approved
0.7576	Intermediate Similarity	NPD7157	Approved
0.7552	Intermediate Similarity	NPD5735	Approved
0.7551	Intermediate Similarity	NPD6674	Discontinued
0.7551	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD3060	Approved
0.7534	Intermediate Similarity	NPD1375	Discontinued
0.7534	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD5588	Approved
0.7517	Intermediate Similarity	NPD5058	Phase 3
0.75	Intermediate Similarity	NPD6331	Phase 2
0.75	Intermediate Similarity	NPD4110	Phase 3
0.75	Intermediate Similarity	NPD3882	Suspended
0.75	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD2978	Approved
0.7484	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD2977	Approved
0.7483	Intermediate Similarity	NPD2238	Phase 2
0.7481	Intermediate Similarity	NPD7843	Approved
0.747	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD2161	Phase 2
0.7464	Intermediate Similarity	NPD4749	Approved
0.7463	Intermediate Similarity	NPD5536	Phase 2
0.745	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD4538	Approved
0.7448	Intermediate Similarity	NPD4536	Approved
0.7448	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD6671	Approved
0.7431	Intermediate Similarity	NPD6355	Discontinued
0.7421	Intermediate Similarity	NPD7199	Phase 2
0.7407	Intermediate Similarity	NPD1548	Phase 1
0.7394	Intermediate Similarity	NPD4625	Phase 3
0.7394	Intermediate Similarity	NPD7095	Approved
0.7372	Intermediate Similarity	NPD2801	Approved
0.736	Intermediate Similarity	NPD3020	Approved
0.7357	Intermediate Similarity	NPD3094	Phase 2
0.7343	Intermediate Similarity	NPD5110	Phase 2
0.7343	Intermediate Similarity	NPD5111	Phase 2
0.7343	Intermediate Similarity	NPD5109	Approved
0.7343	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6190	Approved
0.7329	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD1091	Approved
0.7315	Intermediate Similarity	NPD5177	Phase 3
0.731	Intermediate Similarity	NPD3657	Discovery
0.7305	Intermediate Similarity	NPD6584	Phase 3
0.7303	Intermediate Similarity	NPD4123	Phase 3
0.7301	Intermediate Similarity	NPD3818	Discontinued
0.7297	Intermediate Similarity	NPD5763	Approved
0.7297	Intermediate Similarity	NPD5762	Approved
0.7292	Intermediate Similarity	NPD2674	Phase 3
0.7287	Intermediate Similarity	NPD968	Approved
0.7286	Intermediate Similarity	NPD8651	Approved
0.7286	Intermediate Similarity	NPD6696	Suspended
0.7284	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD6166	Phase 2
0.7279	Intermediate Similarity	NPD5960	Phase 3
0.7278	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1653	Approved
0.7273	Intermediate Similarity	NPD4210	Discontinued
0.7267	Intermediate Similarity	NPD4628	Phase 3
0.7266	Intermediate Similarity	NPD2233	Approved
0.7266	Intermediate Similarity	NPD2232	Approved
0.7266	Intermediate Similarity	NPD2230	Approved
0.726	Intermediate Similarity	NPD6653	Approved
0.726	Intermediate Similarity	NPD6353	Approved
0.7255	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD7312	Approved
0.7246	Intermediate Similarity	NPD7310	Approved
0.7246	Intermediate Similarity	NPD7313	Approved
0.7246	Intermediate Similarity	NPD7311	Approved
0.7233	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD290	Approved
0.7229	Intermediate Similarity	NPD7685	Pre-registration
0.7229	Intermediate Similarity	NPD7240	Approved
0.7226	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD3144	Approved
0.7222	Intermediate Similarity	NPD3145	Approved
0.7219	Intermediate Similarity	NPD2677	Approved
0.7215	Intermediate Similarity	NPD2563	Approved
0.7215	Intermediate Similarity	NPD2560	Approved
0.7215	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD5327	Phase 3
0.7203	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7309	Approved
0.7202	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD4162	Approved
0.7194	Intermediate Similarity	NPD3092	Approved
0.719	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD4624	Approved
0.7179	Intermediate Similarity	NPD4675	Approved
0.7179	Intermediate Similarity	NPD4678	Approved
0.7178	Intermediate Similarity	NPD2489	Approved
0.7178	Intermediate Similarity	NPD27	Approved
0.7174	Intermediate Similarity	NPD2668	Approved
0.7174	Intermediate Similarity	NPD2667	Approved
0.7174	Intermediate Similarity	NPD6516	Phase 2
0.7174	Intermediate Similarity	NPD5846	Approved
0.7174	Intermediate Similarity	NPD5125	Phase 3
0.7174	Intermediate Similarity	NPD5126	Approved
0.7172	Intermediate Similarity	NPD6233	Phase 2
0.7172	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD7124	Phase 2
0.7162	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD5772	Approved
0.7152	Intermediate Similarity	NPD5773	Approved
0.7143	Intermediate Similarity	NPD2231	Phase 2
0.7143	Intermediate Similarity	NPD4578	Approved
0.7143	Intermediate Similarity	NPD4577	Approved
0.7143	Intermediate Similarity	NPD1608	Approved
0.7143	Intermediate Similarity	NPD2235	Phase 2
0.7143	Intermediate Similarity	NPD5494	Approved
0.7143	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7526	Approved
0.7143	Intermediate Similarity	NPD52	Approved
0.7133	Intermediate Similarity	NPD9494	Approved
0.7124	Intermediate Similarity	NPD4357	Discontinued
0.7124	Intermediate Similarity	NPD1511	Approved
0.7123	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD4140	Approved
0.712	Intermediate Similarity	NPD2859	Approved
0.712	Intermediate Similarity	NPD2860	Approved
0.7118	Intermediate Similarity	NPD4663	Approved
0.7117	Intermediate Similarity	NPD2969	Approved
0.7117	Intermediate Similarity	NPD2970	Approved
0.7115	Intermediate Similarity	NPD4005	Discontinued
0.7109	Intermediate Similarity	NPD291	Approved
0.7108	Intermediate Similarity	NPD7074	Phase 3
0.7105	Intermediate Similarity	NPD5241	Discontinued
0.7103	Intermediate Similarity	NPD6798	Discontinued
0.7095	Intermediate Similarity	NPD6895	Approved
0.7095	Intermediate Similarity	NPD6896	Approved
0.7092	Intermediate Similarity	NPD6583	Phase 3
0.7092	Intermediate Similarity	NPD6582	Phase 2
0.7076	Intermediate Similarity	NPD7906	Approved
0.707	Intermediate Similarity	NPD7028	Phase 2
0.7067	Intermediate Similarity	NPD6004	Phase 3
0.7067	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD3540	Phase 1
0.7067	Intermediate Similarity	NPD6002	Phase 3
0.7067	Intermediate Similarity	NPD6005	Phase 3
0.7055	Intermediate Similarity	NPD3051	Approved
0.7051	Intermediate Similarity	NPD3687	Approved
0.7051	Intermediate Similarity	NPD3686	Approved
0.7048	Intermediate Similarity	NPD7054	Approved
0.7047	Intermediate Similarity	NPD7033	Discontinued
0.7044	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD2934	Approved
0.704	Intermediate Similarity	NPD2933	Approved
0.704	Intermediate Similarity	NPD9296	Approved
0.7039	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD1512	Approved
0.7032	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD3091	Approved
0.7029	Intermediate Similarity	NPD1182	Approved
0.7021	Intermediate Similarity	NPD1840	Phase 2
0.702	Intermediate Similarity	NPD2424	Discontinued
0.702	Intermediate Similarity	NPD7037	Approved
0.7007	Intermediate Similarity	NPD3061	Approved
0.7007	Intermediate Similarity	NPD3062	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