NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	262.12
Volume:	272.862
LogP:	2.134
LogD:	1.913
LogS:	-2.665
# Rotatable Bonds:	4
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.666
Synthetic Accessibility Score:	3.417
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.558
MDCK Permeability:	1.3323403436515946e-05
Pgp-inhibitor:	0.451
Pgp-substrate:	0.026
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.968
Plasma Protein Binding (PPB):	72.56584930419922%
Volume Distribution (VD):	1.104
Pgp-substrate:	21.351524353027344%

ADMET: Metabolism

CYP1A2-inhibitor:	0.841
CYP1A2-substrate:	0.474
CYP2C19-inhibitor:	0.067
CYP2C19-substrate:	0.715
CYP2C9-inhibitor:	0.033
CYP2C9-substrate:	0.851
CYP2D6-inhibitor:	0.085
CYP2D6-substrate:	0.771
CYP3A4-inhibitor:	0.031
CYP3A4-substrate:	0.268

ADMET: Excretion

Clearance (CL):	7.094
Half-life (T1/2):	0.45

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.144
Drug-inuced Liver Injury (DILI):	0.076
AMES Toxicity:	0.089
Rat Oral Acute Toxicity:	0.182
Maximum Recommended Daily Dose:	0.793
Skin Sensitization:	0.717
Carcinogencity:	0.881
Eye Corrosion:	0.022
Eye Irritation:	0.133
Respiratory Toxicity:	0.919

Download Data

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

Natural Product: NPC2190

Natural Product ID:	NPC2190
*Common Name:**	Wutaiensal
IUPAC Name:	(E)-3-[(2S)-2-(2-hydroxypropan-2-yl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]prop-2-enal
Synonyms:	Wutaiensal
Standard InCHIKey:	IUYQXZUODYUOIG-IHVVCDCBSA-N
Standard InCHI:	InChI=1S/C15H18O4/c1-15(2,17)13-9-11-7-10(5-4-6-16)8-12(18-3)14(11)19-13/h4-8,13,17H,9H2,1-3H3/b5-4+/t13-/m0/s1
SMILES:	CC(C)([C@@H]1Cc2cc(/C=C/C=O)cc(c2O1)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL506514
PubChem CID:	25015068
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000029] Cinnamaldehydes

*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
NPO26601	Zanthoxylum wutaiense	Species	Rutaceae	Eukaryota	root wood	n.a.	n.a.	PMID[18564877]
NPO26601	Zanthoxylum wutaiense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22472691]
NPO26601	Zanthoxylum wutaiense	Species	Rutaceae	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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	30.0	ug.mL-1	PMID[468677]

☑ 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 NPC2190 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	304
0.1-0.2	1476
0.2-0.3	4166
0.3-0.4	10797
0.4-0.5	7728
0.5-0.6	3658
0.6-0.7	9313
0.7-0.8	4980
0.8-0.85	242
0.85-0.9	28
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9051	High Similarity	NPC264706
0.9051	High Similarity	NPC284881
0.9051	High Similarity	NPC474444
0.9051	High Similarity	NPC93433
0.8794	High Similarity	NPC473408
0.8794	High Similarity	NPC236166
0.8714	High Similarity	NPC163898
0.8714	High Similarity	NPC213900
0.8667	High Similarity	NPC187616
0.8667	High Similarity	NPC16485
0.8667	High Similarity	NPC193026
0.8667	High Similarity	NPC237594
0.8667	High Similarity	NPC476387
0.8667	High Similarity	NPC49603
0.8667	High Similarity	NPC249791
0.8667	High Similarity	NPC119060
0.8657	High Similarity	NPC230219
0.8657	High Similarity	NPC18842
0.8593	High Similarity	NPC26394
0.8561	High Similarity	NPC98745
0.854	High Similarity	NPC54743
0.854	High Similarity	NPC156502
0.854	High Similarity	NPC263367
0.854	High Similarity	NPC177160
0.854	High Similarity	NPC477939
0.854	High Similarity	NPC29799
0.854	High Similarity	NPC209985
0.854	High Similarity	NPC10737
0.8529	High Similarity	NPC253574
0.8529	High Similarity	NPC98179
0.8511	High Similarity	NPC471763
0.85	High Similarity	NPC131971
0.8493	Intermediate Similarity	NPC131121
0.8493	Intermediate Similarity	NPC470769
0.8467	Intermediate Similarity	NPC214729
0.8467	Intermediate Similarity	NPC33986
0.8462	Intermediate Similarity	NPC71090
0.8409	Intermediate Similarity	NPC87113
0.8397	Intermediate Similarity	NPC108545
0.8378	Intermediate Similarity	NPC180901
0.8378	Intermediate Similarity	NPC300757
0.837	Intermediate Similarity	NPC233961
0.837	Intermediate Similarity	NPC280399
0.837	Intermediate Similarity	NPC339621
0.8359	Intermediate Similarity	NPC212743
0.8357	Intermediate Similarity	NPC267291
0.8345	Intermediate Similarity	NPC477938
0.8333	Intermediate Similarity	NPC94276
0.8333	Intermediate Similarity	NPC109822
0.8333	Intermediate Similarity	NPC55040
0.8321	Intermediate Similarity	NPC36490
0.8308	Intermediate Similarity	NPC475529
0.8308	Intermediate Similarity	NPC267064
0.8299	Intermediate Similarity	NPC470264
0.8298	Intermediate Similarity	NPC300611
0.8298	Intermediate Similarity	NPC472520
0.8298	Intermediate Similarity	NPC279851
0.8298	Intermediate Similarity	NPC87725
0.8298	Intermediate Similarity	NPC83375
0.8298	Intermediate Similarity	NPC471414
0.8298	Intermediate Similarity	NPC263261
0.8298	Intermediate Similarity	NPC224876
0.8295	Intermediate Similarity	NPC37858
0.8295	Intermediate Similarity	NPC135961
0.8284	Intermediate Similarity	NPC473993
0.8284	Intermediate Similarity	NPC469386
0.8281	Intermediate Similarity	NPC39793
0.8271	Intermediate Similarity	NPC194519
0.8271	Intermediate Similarity	NPC271985
0.8267	Intermediate Similarity	NPC470827
0.8264	Intermediate Similarity	NPC205361
0.8261	Intermediate Similarity	NPC62366
0.8248	Intermediate Similarity	NPC14248
0.8244	Intermediate Similarity	NPC470804
0.8243	Intermediate Similarity	NPC115203
0.8239	Intermediate Similarity	NPC193722
0.8239	Intermediate Similarity	NPC253878
0.8239	Intermediate Similarity	NPC278469
0.8235	Intermediate Similarity	NPC143483
0.8235	Intermediate Similarity	NPC11089
0.8222	Intermediate Similarity	NPC11258
0.8222	Intermediate Similarity	NPC128208
0.8222	Intermediate Similarity	NPC184733
0.8222	Intermediate Similarity	NPC470084
0.8222	Intermediate Similarity	NPC478215
0.8222	Intermediate Similarity	NPC21867
0.8222	Intermediate Similarity	NPC129570
0.8222	Intermediate Similarity	NPC45774
0.8222	Intermediate Similarity	NPC282703
0.8217	Intermediate Similarity	NPC255675
0.8214	Intermediate Similarity	NPC232246
0.8214	Intermediate Similarity	NPC153818
0.8214	Intermediate Similarity	NPC126206
0.8214	Intermediate Similarity	NPC155963
0.8212	Intermediate Similarity	NPC470828
0.8209	Intermediate Similarity	NPC191037
0.8209	Intermediate Similarity	NPC58607
0.8209	Intermediate Similarity	NPC206882
0.8209	Intermediate Similarity	NPC178284
0.8201	Intermediate Similarity	NPC472525
0.8195	Intermediate Similarity	NPC60517
0.8195	Intermediate Similarity	NPC114901
0.8195	Intermediate Similarity	NPC48990
0.8195	Intermediate Similarity	NPC146886
0.8195	Intermediate Similarity	NPC293701
0.8195	Intermediate Similarity	NPC20443
0.8194	Intermediate Similarity	NPC476450
0.8188	Intermediate Similarity	NPC7526
0.8188	Intermediate Similarity	NPC475840
0.8188	Intermediate Similarity	NPC222036
0.8188	Intermediate Similarity	NPC263064
0.8182	Intermediate Similarity	NPC258083
0.8182	Intermediate Similarity	NPC474104
0.8182	Intermediate Similarity	NPC27220
0.8175	Intermediate Similarity	NPC277804
0.8168	Intermediate Similarity	NPC204466
0.816	Intermediate Similarity	NPC179309
0.8156	Intermediate Similarity	NPC270256
0.8156	Intermediate Similarity	NPC151946
0.8154	Intermediate Similarity	NPC181969
0.8154	Intermediate Similarity	NPC320987
0.8148	Intermediate Similarity	NPC474119
0.8148	Intermediate Similarity	NPC41706
0.8148	Intermediate Similarity	NPC118787
0.8148	Intermediate Similarity	NPC163332
0.8148	Intermediate Similarity	NPC111247
0.8148	Intermediate Similarity	NPC319625
0.8148	Intermediate Similarity	NPC147821
0.8148	Intermediate Similarity	NPC292056
0.8148	Intermediate Similarity	NPC21563
0.8148	Intermediate Similarity	NPC183181
0.8143	Intermediate Similarity	NPC38099
0.8143	Intermediate Similarity	NPC230734
0.8143	Intermediate Similarity	NPC474639
0.8143	Intermediate Similarity	NPC471988
0.8143	Intermediate Similarity	NPC471664
0.8143	Intermediate Similarity	NPC224543
0.8143	Intermediate Similarity	NPC188380
0.8143	Intermediate Similarity	NPC471665
0.8143	Intermediate Similarity	NPC78746
0.8143	Intermediate Similarity	NPC26954
0.8143	Intermediate Similarity	NPC227503
0.8134	Intermediate Similarity	NPC27352
0.8129	Intermediate Similarity	NPC224475
0.8129	Intermediate Similarity	NPC55149
0.8129	Intermediate Similarity	NPC145769
0.8129	Intermediate Similarity	NPC478085
0.8129	Intermediate Similarity	NPC180716
0.8129	Intermediate Similarity	NPC92830
0.8129	Intermediate Similarity	NPC307412
0.8129	Intermediate Similarity	NPC170779
0.8129	Intermediate Similarity	NPC135127
0.8129	Intermediate Similarity	NPC204353
0.8129	Intermediate Similarity	NPC326600
0.8129	Intermediate Similarity	NPC67247
0.8129	Intermediate Similarity	NPC213173
0.8129	Intermediate Similarity	NPC90083
0.8129	Intermediate Similarity	NPC50896
0.8129	Intermediate Similarity	NPC264956
0.8125	Intermediate Similarity	NPC79429
0.8125	Intermediate Similarity	NPC12641
0.8125	Intermediate Similarity	NPC45257
0.8125	Intermediate Similarity	NPC280092
0.8125	Intermediate Similarity	NPC217635
0.8125	Intermediate Similarity	NPC471667
0.8125	Intermediate Similarity	NPC93323
0.812	Intermediate Similarity	NPC279379
0.812	Intermediate Similarity	NPC471693
0.8116	Intermediate Similarity	NPC4940
0.8116	Intermediate Similarity	NPC181049
0.8116	Intermediate Similarity	NPC207400
0.8116	Intermediate Similarity	NPC123954
0.8112	Intermediate Similarity	NPC476842
0.8112	Intermediate Similarity	NPC476840
0.8112	Intermediate Similarity	NPC67467
0.811	Intermediate Similarity	NPC90903
0.8106	Intermediate Similarity	NPC70752
0.8106	Intermediate Similarity	NPC65933
0.8106	Intermediate Similarity	NPC216929
0.8106	Intermediate Similarity	NPC476343
0.8106	Intermediate Similarity	NPC126935
0.8106	Intermediate Similarity	NPC312713
0.8106	Intermediate Similarity	NPC172676
0.8106	Intermediate Similarity	NPC57268
0.8105	Intermediate Similarity	NPC469889
0.8105	Intermediate Similarity	NPC478267
0.8102	Intermediate Similarity	NPC19242
0.8102	Intermediate Similarity	NPC153739
0.8102	Intermediate Similarity	NPC242807
0.8102	Intermediate Similarity	NPC64201
0.8102	Intermediate Similarity	NPC92164
0.8102	Intermediate Similarity	NPC257582
0.8102	Intermediate Similarity	NPC145305
0.8102	Intermediate Similarity	NPC241522
0.8102	Intermediate Similarity	NPC42300
0.8102	Intermediate Similarity	NPC187998
0.8102	Intermediate Similarity	NPC174495
0.8102	Intermediate Similarity	NPC77040
0.8099	Intermediate Similarity	NPC309124
0.8099	Intermediate Similarity	NPC312881

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 NPC2190 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	269
0.1-0.2	928
0.2-0.3	1781
0.3-0.4	2772
0.4-0.5	1705
0.5-0.6	923
0.6-0.7	665
0.7-0.8	107
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7857	Intermediate Similarity	NPD1613	Approved
0.7857	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD228	Approved
0.777	Intermediate Similarity	NPD3027	Phase 3
0.773	Intermediate Similarity	NPD4060	Phase 1
0.7724	Intermediate Similarity	NPD2424	Discontinued
0.7721	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD2684	Approved
0.7704	Intermediate Similarity	NPD3705	Approved
0.7698	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD8651	Approved
0.7638	Intermediate Similarity	NPD290	Approved
0.7626	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD9494	Approved
0.7616	Intermediate Similarity	NPD1653	Approved
0.7615	Intermediate Similarity	NPD7843	Approved
0.7613	Intermediate Similarity	NPD3882	Suspended
0.7612	Intermediate Similarity	NPD1357	Approved
0.7612	Intermediate Similarity	NPD5691	Approved
0.7597	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD5536	Phase 2
0.7576	Intermediate Similarity	NPD7157	Approved
0.7557	Intermediate Similarity	NPD5283	Phase 1
0.7556	Intermediate Similarity	NPD4626	Approved
0.7534	Intermediate Similarity	NPD1375	Discontinued
0.7534	Intermediate Similarity	NPD5763	Approved
0.7534	Intermediate Similarity	NPD5762	Approved
0.7532	Intermediate Similarity	NPD1934	Approved
0.7516	Intermediate Similarity	NPD919	Approved
0.75	Intermediate Similarity	NPD3496	Discontinued
0.75	Intermediate Similarity	NPD1358	Approved
0.75	Intermediate Similarity	NPD2861	Phase 2
0.7468	Intermediate Similarity	NPD5494	Approved
0.7467	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD6674	Discontinued
0.7432	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD5124	Phase 1
0.7431	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD6355	Discontinued
0.7426	Intermediate Similarity	NPD1778	Approved
0.7421	Intermediate Similarity	NPD1247	Approved
0.7413	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD6696	Suspended
0.7383	Intermediate Similarity	NPD4110	Phase 3
0.7383	Intermediate Similarity	NPD4628	Phase 3
0.7383	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD6798	Discontinued
0.7319	Intermediate Similarity	NPD1091	Approved
0.7319	Intermediate Similarity	NPD422	Phase 1
0.7315	Intermediate Similarity	NPD4236	Phase 3
0.7315	Intermediate Similarity	NPD1652	Phase 2
0.7315	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD4237	Approved
0.7313	Intermediate Similarity	NPD6671	Approved
0.7312	Intermediate Similarity	NPD8127	Discontinued
0.731	Intermediate Similarity	NPD447	Suspended
0.7301	Intermediate Similarity	NPD3818	Discontinued
0.7285	Intermediate Similarity	NPD5058	Phase 3
0.7279	Intermediate Similarity	NPD5588	Approved
0.7278	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7095	Approved
0.7267	Intermediate Similarity	NPD6331	Phase 2
0.7261	Intermediate Similarity	NPD2801	Approved
0.7261	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD5844	Phase 1
0.7254	Intermediate Similarity	NPD3018	Phase 2
0.7244	Intermediate Similarity	NPD291	Approved
0.7241	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1558	Phase 1
0.7241	Intermediate Similarity	NPD3620	Phase 2
0.723	Intermediate Similarity	NPD2161	Phase 2
0.7229	Intermediate Similarity	NPD6559	Discontinued
0.7215	Intermediate Similarity	NPD3817	Phase 2
0.7211	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD4536	Approved
0.7211	Intermediate Similarity	NPD4538	Approved
0.7205	Intermediate Similarity	NPD7199	Phase 2
0.7203	Intermediate Similarity	NPD4908	Phase 1
0.7194	Intermediate Similarity	NPD1610	Phase 2
0.7192	Intermediate Similarity	NPD5735	Approved
0.7181	Intermediate Similarity	NPD6002	Phase 3
0.7181	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD7266	Discontinued
0.7181	Intermediate Similarity	NPD6005	Phase 3
0.7181	Intermediate Similarity	NPD6004	Phase 3
0.7181	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD6166	Phase 2
0.7164	Intermediate Similarity	NPD1241	Discontinued
0.7161	Intermediate Similarity	NPD3686	Approved
0.7161	Intermediate Similarity	NPD3687	Approved
0.7161	Intermediate Similarity	NPD4210	Discontinued
0.7154	Intermediate Similarity	NPD3134	Approved
0.7153	Intermediate Similarity	NPD4625	Phase 3
0.7153	Intermediate Similarity	NPD1548	Phase 1
0.7143	Intermediate Similarity	NPD2157	Approved
0.7143	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD7075	Discontinued
0.7124	Intermediate Similarity	NPD1511	Approved
0.7124	Intermediate Similarity	NPD1774	Approved
0.7123	Intermediate Similarity	NPD4140	Approved
0.7117	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD2560	Approved
0.7107	Intermediate Similarity	NPD2563	Approved
0.7105	Intermediate Similarity	NPD2677	Approved
0.7103	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD5976	Discontinued
0.7095	Intermediate Similarity	NPD7097	Phase 1
0.7092	Intermediate Similarity	NPD2982	Phase 2
0.7092	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD4749	Approved
0.7092	Intermediate Similarity	NPD2983	Phase 2
0.709	Intermediate Similarity	NPD821	Approved
0.7089	Intermediate Similarity	NPD37	Approved
0.7081	Intermediate Similarity	NPD6234	Discontinued
0.7075	Intermediate Similarity	NPD4340	Discontinued
0.707	Intermediate Similarity	NPD4380	Phase 2
0.7067	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD4967	Phase 2
0.7063	Intermediate Similarity	NPD4966	Approved
0.7063	Intermediate Similarity	NPD3690	Phase 2
0.7063	Intermediate Similarity	NPD4965	Approved
0.7063	Intermediate Similarity	NPD3691	Phase 2
0.7055	Intermediate Similarity	NPD3051	Approved
0.7047	Intermediate Similarity	NPD7033	Discontinued
0.7047	Intermediate Similarity	NPD2799	Discontinued
0.7047	Intermediate Similarity	NPD5960	Phase 3
0.7044	Intermediate Similarity	NPD7819	Suspended
0.7039	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD1512	Approved
0.7027	Intermediate Similarity	NPD6653	Approved
0.7021	Intermediate Similarity	NPD1608	Approved
0.7021	Intermediate Similarity	NPD2981	Phase 2
0.702	Intermediate Similarity	NPD1549	Phase 2
0.702	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD1712	Approved
0.7013	Intermediate Similarity	NPD6799	Approved
0.7013	Intermediate Similarity	NPD4357	Discontinued
0.7012	Intermediate Similarity	NPD2970	Approved
0.7012	Intermediate Similarity	NPD2969	Approved
0.7006	Intermediate Similarity	NPD7074	Phase 3
0.7006	Intermediate Similarity	NPD3866	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6032	Approved
0.7	Intermediate Similarity	NPD2935	Discontinued
0.7	Intermediate Similarity	NPD2796	Approved
0.7	Intermediate Similarity	NPD2415	Discontinued
0.6993	Remote Similarity	NPD987	Approved
0.6988	Remote Similarity	NPD2163	Approved
0.6987	Remote Similarity	NPD920	Approved
0.6987	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6801	Discontinued
0.6974	Remote Similarity	NPD4162	Approved
0.6972	Remote Similarity	NPD5327	Phase 3
0.6968	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD5535	Approved
0.6962	Remote Similarity	NPD7028	Phase 2
0.6959	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD230	Phase 1
0.6954	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.695	Remote Similarity	NPD776	Approved
0.695	Remote Similarity	NPD1611	Approved
0.6948	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD9697	Approved
0.6946	Remote Similarity	NPD7054	Approved
0.6939	Remote Similarity	NPD6233	Phase 2
0.6939	Remote Similarity	NPD4062	Phase 3
0.6937	Remote Similarity	NPD5772	Approved
0.6937	Remote Similarity	NPD5773	Approved
0.6933	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD6516	Phase 2
0.6929	Remote Similarity	NPD5846	Approved
0.6918	Remote Similarity	NPD3179	Approved
0.6918	Remote Similarity	NPD3180	Approved
0.6918	Remote Similarity	NPD5090	Approved
0.6918	Remote Similarity	NPD5089	Approved
0.6913	Remote Similarity	NPD6353	Approved
0.6909	Remote Similarity	NPD3926	Phase 2
0.6905	Remote Similarity	NPD7472	Approved
0.6887	Remote Similarity	NPD1551	Phase 2
0.6883	Remote Similarity	NPD6190	Approved
0.6882	Remote Similarity	NPD7549	Discontinued
0.6867	Remote Similarity	NPD27	Approved
0.6867	Remote Similarity	NPD2489	Approved
0.6867	Remote Similarity	NPD4481	Phase 3
0.6866	Remote Similarity	NPD3022	Approved
0.6866	Remote Similarity	NPD3021	Approved
0.6863	Remote Similarity	NPD3060	Approved
0.6859	Remote Similarity	NPD2533	Approved
0.6859	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD3146	Approved
0.6859	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD7410	Clinical (unspecified phase)

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