NPASS Compound

Structure

CID41706 OpenBabel06191715372D 27 28 0 0 1 0 0 0 0 0999 V2000 -6.9282 1.0000 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 -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 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -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 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 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 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 26 1 0 0 0 0 3 4 2 0 0 0 0 3 9 1 0 0 0 0 4 13 1 0 0 0 0 5 8 2 0 0 0 0 5 13 1 0 0 0 0 6 7 2 0 0 0 0 6 14 1 0 0 0 0 7 15 1 0 0 0 0 8 16 1 0 0 0 0 9 21 1 0 0 0 0 10 13 2 0 0 0 0 10 18 1 0 0 0 0 11 14 2 0 0 0 0 11 17 1 0 0 0 0 12 22 1 0 0 0 0 14 20 1 0 0 0 0 15 17 2 0 0 0 0 15 23 1 0 0 0 0 16 18 2 0 0 0 0 16 27 1 0 0 0 0 17 25 1 0 0 0 0 18 26 1 0 0 0 0 19 12 1 6 0 0 0 19 20 1 0 0 0 0 19 27 1 0 0 0 0 20 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	376.15
Volume:	380.44
LogP:	0.899
LogD:	1.449
LogS:	-2.388
# Rotatable Bonds:	9
TPSA:	108.61
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.529
Synthetic Accessibility Score:	3.235
Fsp3:	0.3
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:	-5.037
MDCK Permeability:	6.41963561065495e-06
Pgp-inhibitor:	0.055
Pgp-substrate:	0.514
Human Intestinal Absorption (HIA):	0.1
20% Bioavailability (F20%):	0.017
30% Bioavailability (F30%):	0.171

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.589
Plasma Protein Binding (PPB):	89.08907318115234%
Volume Distribution (VD):	0.533
Pgp-substrate:	8.641013145446777%

ADMET: Metabolism

CYP1A2-inhibitor:	0.132
CYP1A2-substrate:	0.488
CYP2C19-inhibitor:	0.041
CYP2C19-substrate:	0.639
CYP2C9-inhibitor:	0.035
CYP2C9-substrate:	0.852
CYP2D6-inhibitor:	0.049
CYP2D6-substrate:	0.816
CYP3A4-inhibitor:	0.47
CYP3A4-substrate:	0.365

ADMET: Excretion

Clearance (CL):	9.065
Half-life (T1/2):	0.902

ADMET: Toxicity

hERG Blockers:	0.088
Human Hepatotoxicity (H-HT):	0.122
Drug-inuced Liver Injury (DILI):	0.368
AMES Toxicity:	0.204
Rat Oral Acute Toxicity:	0.031
Maximum Recommended Daily Dose:	0.018
Skin Sensitization:	0.342
Carcinogencity:	0.511
Eye Corrosion:	0.003
Eye Irritation:	0.084
Respiratory Toxicity:	0.013

Download Data

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

Natural Product: NPC41706

Natural Product ID:	NPC41706
*Common Name:**	Threo-Guaiacylglycerol-8-O-4'-Coniferyl Alcohol Ether
IUPAC Name:	(1R,2R)-1-(4-hydroxy-3-methoxyphenyl)-2-[4-[(E)-3-hydroxyprop-1-enyl]-2-methoxyphenoxy]propane-1,3-diol
Synonyms:
Standard InCHIKey:	FYEZJIXULOZDRT-FMEUAVTJSA-N
Standard InCHI:	InChI=1S/C20H24O7/c1-25-17-11-14(6-7-15(17)23)20(24)19(12-22)27-16-8-5-13(4-3-9-21)10-18(16)26-2/h3-8,10-11,19-24H,9,12H2,1-2H3/b4-3+/t19-,20-/m1/s1
SMILES:	OC/C=C/c1ccc(c(c1)OC)O[C@@H]([C@@H](c1ccc(c(c1)OC)O)O)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1689262
PubChem CID:	14274761
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds

*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
NPO19548	Lepisorus contortus	Species	Polypodiaceae	Eukaryota	whole plant	Gongshan County, Yunnan, China	n.a.	PMID[21261296]
NPO19548	Lepisorus contortus	Species	Polypodiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21261296]
NPO19548	Lepisorus contortus	Species	Polypodiaceae	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
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT27	Others	Unspecified		Activity	=	116.8	%	PMID[569955]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	32560.0	nM	PMID[569955]

☑ 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 NPC41706 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	361
0.1-0.2	1407
0.2-0.3	4492
0.3-0.4	12093
0.4-0.5	6140
0.5-0.6	4368
0.6-0.7	7844
0.7-0.8	4333
0.8-0.85	941
0.85-0.9	489
0.9-0.95	187
0.95-1	42

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC118787
1.0	High Similarity	NPC292056
1.0	High Similarity	NPC147821
1.0	High Similarity	NPC319625
1.0	High Similarity	NPC183181
1.0	High Similarity	NPC163332
1.0	High Similarity	NPC111247
0.9917	High Similarity	NPC191037
0.9917	High Similarity	NPC58607
0.9917	High Similarity	NPC178284
0.9836	High Similarity	NPC5851
0.9836	High Similarity	NPC86030
0.9833	High Similarity	NPC194519
0.9754	High Similarity	NPC72529
0.975	High Similarity	NPC94276
0.975	High Similarity	NPC293701
0.975	High Similarity	NPC48990
0.975	High Similarity	NPC109822
0.975	High Similarity	NPC114901
0.9677	High Similarity	NPC472597
0.96	High Similarity	NPC35932
0.96	High Similarity	NPC184447
0.96	High Similarity	NPC7903
0.96	High Similarity	NPC16208
0.96	High Similarity	NPC160991
0.9597	High Similarity	NPC472338
0.9593	High Similarity	NPC474178
0.9593	High Similarity	NPC252307
0.9593	High Similarity	NPC245826
0.9583	High Similarity	NPC71090
0.9516	High Similarity	NPC273295
0.9516	High Similarity	NPC285339
0.9516	High Similarity	NPC470258
0.9516	High Similarity	NPC190629
0.9516	High Similarity	NPC222004
0.9516	High Similarity	NPC226788
0.9516	High Similarity	NPC218856
0.9516	High Similarity	NPC202582
0.9516	High Similarity	NPC210623
0.9516	High Similarity	NPC3439
0.9512	High Similarity	NPC165045
0.9512	High Similarity	NPC118533
0.9504	High Similarity	NPC471693
0.95	High Similarity	NPC470804
0.9449	High Similarity	NPC249791
0.9449	High Similarity	NPC476387
0.9449	High Similarity	NPC310854
0.9449	High Similarity	NPC119060
0.9449	High Similarity	NPC170694
0.9449	High Similarity	NPC237594
0.9444	High Similarity	NPC470752
0.944	High Similarity	NPC145305
0.944	High Similarity	NPC153739
0.944	High Similarity	NPC64201
0.944	High Similarity	NPC92164
0.944	High Similarity	NPC241522
0.944	High Similarity	NPC187998
0.944	High Similarity	NPC174495
0.944	High Similarity	NPC77040
0.944	High Similarity	NPC257582
0.944	High Similarity	NPC42300
0.944	High Similarity	NPC242807
0.9375	High Similarity	NPC472337
0.937	High Similarity	NPC475840
0.9365	High Similarity	NPC469625
0.9365	High Similarity	NPC469613
0.9365	High Similarity	NPC30043
0.9365	High Similarity	NPC277804
0.9365	High Similarity	NPC309787
0.9365	High Similarity	NPC470095
0.9365	High Similarity	NPC470096
0.936	High Similarity	NPC475875
0.936	High Similarity	NPC476968
0.936	High Similarity	NPC170844
0.9355	High Similarity	NPC474119
0.9355	High Similarity	NPC210355
0.9355	High Similarity	NPC5428
0.935	High Similarity	NPC148627
0.9339	High Similarity	NPC473853
0.9339	High Similarity	NPC54872
0.9339	High Similarity	NPC324571
0.9339	High Similarity	NPC290451
0.9339	High Similarity	NPC262156
0.9339	High Similarity	NPC343720
0.9339	High Similarity	NPC113865
0.9339	High Similarity	NPC312675
0.9339	High Similarity	NPC127389
0.9339	High Similarity	NPC470212
0.9339	High Similarity	NPC184651
0.9333	High Similarity	NPC148615
0.9333	High Similarity	NPC35071
0.9333	High Similarity	NPC177475
0.9302	High Similarity	NPC263367
0.9302	High Similarity	NPC477939
0.9302	High Similarity	NPC472336
0.9302	High Similarity	NPC29799
0.9302	High Similarity	NPC472334
0.9302	High Similarity	NPC54743
0.9302	High Similarity	NPC156502
0.9302	High Similarity	NPC306441
0.9302	High Similarity	NPC177160
0.9302	High Similarity	NPC16435
0.9302	High Similarity	NPC10737
0.9302	High Similarity	NPC209985
0.9297	High Similarity	NPC478085
0.9291	High Similarity	NPC201587
0.9291	High Similarity	NPC253105
0.9286	High Similarity	NPC469612
0.9286	High Similarity	NPC469614
0.928	High Similarity	NPC282703
0.928	High Similarity	NPC11258
0.928	High Similarity	NPC45774
0.928	High Similarity	NPC184733
0.928	High Similarity	NPC470084
0.928	High Similarity	NPC129570
0.928	High Similarity	NPC206615
0.928	High Similarity	NPC186843
0.928	High Similarity	NPC128208
0.928	High Similarity	NPC21867
0.928	High Similarity	NPC470213
0.928	High Similarity	NPC98631
0.9262	High Similarity	NPC209567
0.9256	High Similarity	NPC207613
0.925	High Similarity	NPC320987
0.925	High Similarity	NPC135961
0.925	High Similarity	NPC181969
0.9231	High Similarity	NPC138738
0.9231	High Similarity	NPC126206
0.9231	High Similarity	NPC470413
0.9225	High Similarity	NPC112246
0.9225	High Similarity	NPC214729
0.9225	High Similarity	NPC121812
0.9225	High Similarity	NPC112939
0.9225	High Similarity	NPC470356
0.9225	High Similarity	NPC234333
0.9225	High Similarity	NPC94750
0.9225	High Similarity	NPC260898
0.9225	High Similarity	NPC474206
0.9225	High Similarity	NPC61946
0.9225	High Similarity	NPC47398
0.9219	High Similarity	NPC229442
0.9219	High Similarity	NPC168059
0.9213	High Similarity	NPC161557
0.9213	High Similarity	NPC7171
0.9213	High Similarity	NPC27843
0.9213	High Similarity	NPC115207
0.9213	High Similarity	NPC158079
0.9213	High Similarity	NPC228346
0.9213	High Similarity	NPC474017
0.9213	High Similarity	NPC40432
0.9187	High Similarity	NPC280704
0.918	High Similarity	NPC476343
0.9167	High Similarity	NPC255675
0.916	High Similarity	NPC22517
0.9154	High Similarity	NPC227503
0.9154	High Similarity	NPC471664
0.9154	High Similarity	NPC230734
0.9154	High Similarity	NPC474639
0.9154	High Similarity	NPC302701
0.9154	High Similarity	NPC269091
0.9154	High Similarity	NPC471665
0.9154	High Similarity	NPC77861
0.9147	High Similarity	NPC193026
0.9147	High Similarity	NPC187616
0.9147	High Similarity	NPC49603
0.9147	High Similarity	NPC135127
0.9147	High Similarity	NPC287745
0.9141	High Similarity	NPC4940
0.9141	High Similarity	NPC181049
0.9141	High Similarity	NPC207400
0.9134	High Similarity	NPC143483
0.912	High Similarity	NPC206882
0.9113	High Similarity	NPC228972
0.9113	High Similarity	NPC122792
0.9106	High Similarity	NPC85488
0.9091	High Similarity	NPC311595
0.9091	High Similarity	NPC266197
0.9091	High Similarity	NPC24474
0.9091	High Similarity	NPC267291
0.9091	High Similarity	NPC291101
0.9084	High Similarity	NPC102904
0.9084	High Similarity	NPC176051
0.9084	High Similarity	NPC211549
0.9084	High Similarity	NPC103976
0.9084	High Similarity	NPC107551
0.9084	High Similarity	NPC474390
0.9084	High Similarity	NPC326797
0.9084	High Similarity	NPC474282
0.9083	High Similarity	NPC86947
0.9077	High Similarity	NPC164787
0.9077	High Similarity	NPC151224
0.907	High Similarity	NPC263064
0.907	High Similarity	NPC11060
0.907	High Similarity	NPC26394
0.907	High Similarity	NPC158331
0.9062	High Similarity	NPC248307
0.9062	High Similarity	NPC65942
0.9055	High Similarity	NPC270849
0.9055	High Similarity	NPC26653
0.9055	High Similarity	NPC212015

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 NPC41706 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	843
0.2-0.3	1870
0.3-0.4	2652
0.4-0.5	1642
0.5-0.6	924
0.6-0.7	701
0.7-0.8	195
0.8-0.85	6
0.85-0.9	1
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.936	High Similarity	NPD3027	Phase 3
0.8992	High Similarity	NPD1612	Clinical (unspecified phase)
0.8992	High Similarity	NPD1613	Approved
0.8682	High Similarity	NPD1529	Clinical (unspecified phase)
0.8605	High Similarity	NPD1530	Clinical (unspecified phase)
0.8583	High Similarity	NPD228	Approved
0.8295	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD5283	Phase 1
0.8284	Intermediate Similarity	NPD1558	Phase 1
0.8182	Intermediate Similarity	NPD2684	Approved
0.8182	Intermediate Similarity	NPD2861	Phase 2
0.8065	Intermediate Similarity	NPD7843	Approved
0.8058	Intermediate Similarity	NPD7266	Discontinued
0.8027	Intermediate Similarity	NPD1934	Approved
0.8016	Intermediate Similarity	NPD7157	Approved
0.8015	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.8015	Intermediate Similarity	NPD2982	Phase 2
0.8015	Intermediate Similarity	NPD2983	Phase 2
0.8015	Intermediate Similarity	NPD3620	Phase 2
0.8	Intermediate Similarity	NPD3705	Approved
0.8	Intermediate Similarity	NPD1091	Approved
0.7985	Intermediate Similarity	NPD4908	Phase 1
0.7971	Intermediate Similarity	NPD4538	Approved
0.7971	Intermediate Similarity	NPD4536	Approved
0.7971	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7969	Intermediate Similarity	NPD1548	Phase 1
0.7967	Intermediate Similarity	NPD3022	Approved
0.7967	Intermediate Similarity	NPD3021	Approved
0.7951	Intermediate Similarity	NPD290	Approved
0.7943	Intermediate Similarity	NPD3060	Approved
0.7943	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD2981	Phase 2
0.791	Intermediate Similarity	NPD3018	Phase 2
0.7907	Intermediate Similarity	NPD1357	Approved
0.7883	Intermediate Similarity	NPD4060	Phase 1
0.7877	Intermediate Similarity	NPD1653	Approved
0.7869	Intermediate Similarity	NPD968	Approved
0.7868	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7863	Intermediate Similarity	NPD1610	Phase 2
0.7852	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD2801	Approved
0.7833	Intermediate Similarity	NPD291	Approved
0.7817	Intermediate Similarity	NPD4236	Phase 3
0.7817	Intermediate Similarity	NPD4162	Approved
0.7817	Intermediate Similarity	NPD4237	Approved
0.7817	Intermediate Similarity	NPD6674	Discontinued
0.7793	Intermediate Similarity	NPD4123	Phase 3
0.7786	Intermediate Similarity	NPD5588	Approved
0.7786	Intermediate Similarity	NPD5960	Phase 3
0.7752	Intermediate Similarity	NPD5536	Phase 2
0.7748	Intermediate Similarity	NPD3882	Suspended
0.7742	Intermediate Similarity	NPD6166	Phase 2
0.7742	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7734	Intermediate Similarity	NPD6671	Approved
0.7721	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.771	Intermediate Similarity	NPD6516	Phase 2
0.771	Intermediate Similarity	NPD5846	Approved
0.7708	Intermediate Similarity	NPD2677	Approved
0.7704	Intermediate Similarity	NPD6584	Phase 3
0.7687	Intermediate Similarity	NPD8651	Approved
0.7681	Intermediate Similarity	NPD6233	Phase 2
0.7669	Intermediate Similarity	NPD2235	Phase 2
0.7669	Intermediate Similarity	NPD2231	Phase 2
0.7655	Intermediate Similarity	NPD5058	Phase 3
0.7651	Intermediate Similarity	NPD4678	Approved
0.7651	Intermediate Similarity	NPD4675	Approved
0.7639	Intermediate Similarity	NPD4628	Phase 3
0.7635	Intermediate Similarity	NPD3687	Approved
0.7635	Intermediate Similarity	NPD3686	Approved
0.7632	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD2977	Approved
0.7616	Intermediate Similarity	NPD2978	Approved
0.7603	Intermediate Similarity	NPD1511	Approved
0.7595	Intermediate Similarity	NPD7054	Approved
0.7586	Intermediate Similarity	NPD6190	Approved
0.7571	Intermediate Similarity	NPD5735	Approved
0.7554	Intermediate Similarity	NPD2674	Phase 3
0.7554	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD1375	Discontinued
0.7547	Intermediate Similarity	NPD7472	Approved
0.7547	Intermediate Similarity	NPD7074	Phase 3
0.7536	Intermediate Similarity	NPD7095	Approved
0.7536	Intermediate Similarity	NPD4625	Phase 3
0.7532	Intermediate Similarity	NPD3818	Discontinued
0.7532	Intermediate Similarity	NPD6234	Discontinued
0.7518	Intermediate Similarity	NPD6653	Approved
0.7517	Intermediate Similarity	NPD4110	Phase 3
0.7517	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD6331	Phase 2
0.75	Intermediate Similarity	NPD1512	Approved
0.75	Intermediate Similarity	NPD5772	Approved
0.75	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5773	Approved
0.7483	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1774	Approved
0.7482	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD6798	Discontinued
0.7482	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD4749	Approved
0.7481	Intermediate Similarity	NPD6583	Phase 3
0.7481	Intermediate Similarity	NPD6582	Phase 2
0.7466	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD3817	Phase 2
0.7451	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD5177	Phase 3
0.7447	Intermediate Similarity	NPD4340	Discontinued
0.7447	Intermediate Similarity	NPD6355	Discontinued
0.7434	Intermediate Similarity	NPD37	Approved
0.7431	Intermediate Similarity	NPD5763	Approved
0.7431	Intermediate Similarity	NPD5762	Approved
0.7429	Intermediate Similarity	NPD4062	Phase 3
0.741	Intermediate Similarity	NPD3179	Approved
0.741	Intermediate Similarity	NPD3180	Approved
0.7403	Intermediate Similarity	NPD4966	Approved
0.7403	Intermediate Similarity	NPD4965	Approved
0.7403	Intermediate Similarity	NPD4967	Phase 2
0.7397	Intermediate Similarity	NPD4535	Phase 3
0.7394	Intermediate Similarity	NPD3052	Approved
0.7394	Intermediate Similarity	NPD3054	Approved
0.7391	Intermediate Similarity	NPD6797	Phase 2
0.7391	Intermediate Similarity	NPD9494	Approved
0.7388	Intermediate Similarity	NPD3496	Discontinued
0.7383	Intermediate Similarity	NPD7526	Approved
0.7383	Intermediate Similarity	NPD52	Approved
0.7383	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD3061	Approved
0.7376	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD3062	Approved
0.7376	Intermediate Similarity	NPD3059	Approved
0.7376	Intermediate Similarity	NPD2238	Phase 2
0.7364	Intermediate Similarity	NPD821	Approved
0.7364	Intermediate Similarity	NPD5535	Approved
0.7361	Intermediate Similarity	NPD2161	Phase 2
0.7357	Intermediate Similarity	NPD3144	Approved
0.7357	Intermediate Similarity	NPD3145	Approved
0.7351	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD5241	Discontinued
0.7346	Intermediate Similarity	NPD7251	Discontinued
0.7338	Intermediate Similarity	NPD2563	Approved
0.7338	Intermediate Similarity	NPD2560	Approved
0.7333	Intermediate Similarity	NPD2933	Approved
0.7333	Intermediate Similarity	NPD2934	Approved
0.7333	Intermediate Similarity	NPD9296	Approved
0.7333	Intermediate Similarity	NPD422	Phase 1
0.7329	Intermediate Similarity	NPD1652	Phase 2
0.7325	Intermediate Similarity	NPD7199	Phase 2
0.7315	Intermediate Similarity	NPD3536	Discontinued
0.7313	Intermediate Similarity	NPD9381	Approved
0.7313	Intermediate Similarity	NPD9384	Approved
0.7312	Intermediate Similarity	NPD7228	Approved
0.731	Intermediate Similarity	NPD3540	Phase 1
0.7301	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD7808	Phase 3
0.7293	Intermediate Similarity	NPD1182	Approved
0.7292	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD7033	Discontinued
0.7292	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD1608	Approved
0.7279	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2860	Approved
0.7273	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5314	Approved
0.7273	Intermediate Similarity	NPD2859	Approved
0.7267	Intermediate Similarity	NPD5844	Phase 1
0.7266	Intermediate Similarity	NPD556	Approved
0.726	Intermediate Similarity	NPD2424	Discontinued
0.7254	Intermediate Similarity	NPD4140	Approved
0.7248	Intermediate Similarity	NPD4357	Discontinued
0.7246	Intermediate Similarity	NPD3094	Phase 2
0.7244	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6032	Approved
0.7241	Intermediate Similarity	NPD3539	Phase 1
0.7239	Intermediate Similarity	NPD5585	Approved
0.7237	Intermediate Similarity	NPD4005	Discontinued
0.7236	Intermediate Similarity	NPD3020	Approved
0.7234	Intermediate Similarity	NPD5111	Phase 2
0.7234	Intermediate Similarity	NPD5109	Approved
0.7234	Intermediate Similarity	NPD5110	Phase 2
0.7226	Intermediate Similarity	NPD9622	Approved
0.7226	Intermediate Similarity	NPD3685	Discontinued
0.7226	Intermediate Similarity	NPD5327	Phase 3
0.7219	Intermediate Similarity	NPD2122	Discontinued
0.7206	Intermediate Similarity	NPD1535	Discovery
0.7203	Intermediate Similarity	NPD230	Phase 1
0.7194	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD558	Phase 2
0.719	Intermediate Similarity	NPD4380	Phase 2
0.7188	Intermediate Similarity	NPD2489	Approved
0.7188	Intermediate Similarity	NPD27	Approved
0.7185	Intermediate Similarity	NPD1778	Approved
0.7178	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD1242	Phase 1
0.7174	Intermediate Similarity	NPD6696	Suspended
0.7174	Intermediate Similarity	NPD2922	Phase 1
0.7172	Intermediate Similarity	NPD2156	Approved
0.7172	Intermediate Similarity	NPD2154	Approved
0.7172	Intermediate Similarity	NPD2155	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