NPASS Compound

Structure

NPC35630 OpenBabel07101718192D 40 44 0 0 0 0 0 0 0 0999 V2000 -3.3871 -4.8889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3871 -1.9556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2339 -0.4889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5403 -0.4889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5403 0.4889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6936 -0.9778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6936 -1.9556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8468 -3.4222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8468 -3.4222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6936 -1.9556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2339 -2.4444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0807 -0.9778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3871 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5403 -1.4667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5403 -2.4444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6936 -3.9111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6936 -3.9111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5403 -2.4444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6936 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8468 1.4667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6936 1.9556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3871 -0.9778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6936 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8468 -2.4444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8468 -2.4444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8468 1.4667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0807 -1.9556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3871 -0.9778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5403 -3.4222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5403 -3.4222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8468 0.4889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8468 0.4889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9556 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 -1.6936 2.9333 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9275 -2.4444 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2339 -1.4667 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3871 -3.9111 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3871 -3.9111 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 40 1 0 0 0 0 2 12 1 0 0 0 0 2 23 2 0 0 0 0 3 13 2 0 0 0 0 3 23 1 0 0 0 0 4 20 3 0 0 0 0 4 23 1 0 0 0 0 5 14 1 0 0 0 0 5 24 2 0 0 0 0 6 15 2 0 0 0 0 6 24 1 0 0 0 0 7 16 2 0 0 0 0 7 25 1 0 0 0 0 8 17 2 0 0 0 0 8 25 1 0 0 0 0 9 18 1 0 0 0 0 9 26 2 0 0 0 0 10 19 2 0 0 0 0 10 26 1 0 0 0 0 11 21 2 0 0 0 0 11 27 1 0 0 0 0 12 28 2 0 0 0 0 13 28 1 0 0 0 0 14 29 2 0 0 0 0 15 29 1 0 0 0 0 16 30 1 0 0 0 0 17 30 1 0 0 0 0 18 31 2 0 0 0 0 19 31 1 0 0 0 0 20 33 1 0 0 0 0 21 32 1 0 0 0 0 22 27 1 0 0 0 0 22 36 1 0 0 0 0 24 32 1 0 0 0 0 25 34 2 3 0 0 0 26 34 1 0 0 0 0 27 33 2 0 0 0 0 28 37 1 0 0 0 0 29 38 1 0 0 0 0 30 39 2 0 0 0 0 31 40 1 0 0 0 0 32 35 2 0 0 0 0 33 35 1 0 0 0 0 34 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	526.18
Volume:	567.629
LogP:	5.494
LogD:	3.104
LogS:	-4.285
# Rotatable Bonds:	5
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.271
Synthetic Accessibility Score:	2.95
Fsp3:	0.057
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.159
MDCK Permeability:	1.0780100637930445e-05
Pgp-inhibitor:	0.922
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.018

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	101.1195297241211%
Volume Distribution (VD):	0.102
Pgp-substrate:	0.24183939397335052%

ADMET: Metabolism

CYP1A2-inhibitor:	0.503
CYP1A2-substrate:	0.636
CYP2C19-inhibitor:	0.841
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.717
CYP2C9-substrate:	0.958
CYP2D6-inhibitor:	0.369
CYP2D6-substrate:	0.919
CYP3A4-inhibitor:	0.41
CYP3A4-substrate:	0.524

ADMET: Excretion

Clearance (CL):	5.965
Half-life (T1/2):	0.277

ADMET: Toxicity

hERG Blockers:	0.077
Human Hepatotoxicity (H-HT):	0.031
Drug-inuced Liver Injury (DILI):	0.978
AMES Toxicity:	0.655
Rat Oral Acute Toxicity:	0.122
Maximum Recommended Daily Dose:	0.955
Skin Sensitization:	0.948
Carcinogencity:	0.785
Eye Corrosion:	0.003
Eye Irritation:	0.916
Respiratory Toxicity:	0.688

Download Data

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

Natural Product: NPC35630

Natural Product ID:	NPC35630
*Common Name:**	Selaginellin M
IUPAC Name:	4-[[3-(hydroxymethyl)-6-(4-hydroxyphenyl)-2-[2-(4-hydroxyphenyl)ethynyl]phenyl]-(4-methoxyphenyl)methylidene]cyclohexa-2,5-dien-1-one
Synonyms:
Standard InCHIKey:	LPEPBNUNFHGLSZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C35H26O5/c1-40-31-18-9-26(10-19-31)34(25-7-16-30(39)17-8-25)35-32(24-5-14-29(38)15-6-24)21-11-27(22-36)33(35)20-4-23-2-12-28(37)13-3-23/h2-3,5-19,21,36-38H,22H2,1H3
SMILES:	COc1ccc(cc1)C(=C1C=CC(=O)C=C1)c1c(ccc(CO)c1C#Cc1ccc(cc1)O)c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3394770
PubChem CID:	71575995
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
NPO14158	Selaginella tamariscina	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25559759]
NPO14158	Selaginella tamariscina	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31244143]
NPO14158	Selaginella tamariscina	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14158	Selaginella tamariscina	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14158	Selaginella tamariscina	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14158	Selaginella tamariscina	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14158	Selaginella tamariscina	Species	Selaginellaceae	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
Ki	1
Others	1

Activity Type	# Activity
Individual Protein	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	11500.0	nM	PMID[548433]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Ki	=	8900.0	nM	PMID[548433]
NPT27	Others	Unspecified		Inhibition	=	50.0	%	PMID[548433]

☑ 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 NPC35630 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	316
0.1-0.2	1671
0.2-0.3	3621
0.3-0.4	11142
0.4-0.5	7862
0.5-0.6	5613
0.6-0.7	10705
0.7-0.8	1732
0.8-0.85	22
0.85-0.9	7
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9771	High Similarity	NPC24635
0.9297	High Similarity	NPC283508
0.9297	High Similarity	NPC35341
0.9062	High Similarity	NPC12824
0.8828	High Similarity	NPC71870
0.8462	Intermediate Similarity	NPC103916
0.8333	Intermediate Similarity	NPC251259
0.8286	Intermediate Similarity	NPC472370
0.8258	Intermediate Similarity	NPC131868
0.8235	Intermediate Similarity	NPC428300
0.8169	Intermediate Similarity	NPC71465
0.8169	Intermediate Similarity	NPC472646
0.8156	Intermediate Similarity	NPC37410
0.8099	Intermediate Similarity	NPC472649
0.8099	Intermediate Similarity	NPC206525
0.8099	Intermediate Similarity	NPC170328
0.8099	Intermediate Similarity	NPC472648
0.8099	Intermediate Similarity	NPC133463
0.8099	Intermediate Similarity	NPC472647
0.8099	Intermediate Similarity	NPC191462
0.8058	Intermediate Similarity	NPC472369
0.8056	Intermediate Similarity	NPC273623
0.8028	Intermediate Similarity	NPC258780
0.8	Intermediate Similarity	NPC282508
0.7943	Intermediate Similarity	NPC189482
0.7929	Intermediate Similarity	NPC254000
0.7923	Intermediate Similarity	NPC35344
0.7923	Intermediate Similarity	NPC141003
0.7905	Intermediate Similarity	NPC91694
0.7905	Intermediate Similarity	NPC300603
0.7891	Intermediate Similarity	NPC69755
0.7868	Intermediate Similarity	NPC152946
0.7862	Intermediate Similarity	NPC475104
0.7857	Intermediate Similarity	NPC86257
0.7852	Intermediate Similarity	NPC129176
0.7832	Intermediate Similarity	NPC184269
0.7832	Intermediate Similarity	NPC141023
0.7829	Intermediate Similarity	NPC295977
0.7829	Intermediate Similarity	NPC58310
0.7826	Intermediate Similarity	NPC76119
0.7826	Intermediate Similarity	NPC133407
0.7826	Intermediate Similarity	NPC232387
0.7826	Intermediate Similarity	NPC4286
0.7826	Intermediate Similarity	NPC28476
0.782	Intermediate Similarity	NPC299180
0.782	Intermediate Similarity	NPC25648
0.7817	Intermediate Similarity	NPC303144
0.7808	Intermediate Similarity	NPC110699
0.7808	Intermediate Similarity	NPC470407
0.7808	Intermediate Similarity	NPC106055
0.78	Intermediate Similarity	NPC174251
0.78	Intermediate Similarity	NPC39361
0.78	Intermediate Similarity	NPC153182
0.7793	Intermediate Similarity	NPC186647
0.7786	Intermediate Similarity	NPC277458
0.7786	Intermediate Similarity	NPC321589
0.7786	Intermediate Similarity	NPC307050
0.7786	Intermediate Similarity	NPC215300
0.7786	Intermediate Similarity	NPC471064
0.7785	Intermediate Similarity	NPC101255
0.7785	Intermediate Similarity	NPC307205
0.7785	Intermediate Similarity	NPC475719
0.7785	Intermediate Similarity	NPC43716
0.7778	Intermediate Similarity	NPC306011
0.7778	Intermediate Similarity	NPC472838
0.777	Intermediate Similarity	NPC201297
0.7763	Intermediate Similarity	NPC118000
0.7763	Intermediate Similarity	NPC205501
0.7763	Intermediate Similarity	NPC162976
0.7762	Intermediate Similarity	NPC470406
0.7755	Intermediate Similarity	NPC78987
0.7755	Intermediate Similarity	NPC82336
0.7754	Intermediate Similarity	NPC164014
0.7754	Intermediate Similarity	NPC474532
0.7748	Intermediate Similarity	NPC478018
0.7748	Intermediate Similarity	NPC478163
0.7746	Intermediate Similarity	NPC471517
0.7746	Intermediate Similarity	NPC473309
0.7744	Intermediate Similarity	NPC19290
0.7737	Intermediate Similarity	NPC174977
0.7737	Intermediate Similarity	NPC30462
0.7733	Intermediate Similarity	NPC478019
0.7733	Intermediate Similarity	NPC471523
0.7733	Intermediate Similarity	NPC471524
0.7733	Intermediate Similarity	NPC215678
0.7733	Intermediate Similarity	NPC471473
0.7733	Intermediate Similarity	NPC274454
0.773	Intermediate Similarity	NPC471518
0.773	Intermediate Similarity	NPC471519
0.7724	Intermediate Similarity	NPC471522
0.7724	Intermediate Similarity	NPC475549
0.7724	Intermediate Similarity	NPC249817
0.7714	Intermediate Similarity	NPC53781
0.7712	Intermediate Similarity	NPC473579
0.7712	Intermediate Similarity	NPC475454
0.7712	Intermediate Similarity	NPC473680
0.7712	Intermediate Similarity	NPC475311
0.7708	Intermediate Similarity	NPC11266
0.7708	Intermediate Similarity	NPC71372
0.7707	Intermediate Similarity	NPC324736
0.7703	Intermediate Similarity	NPC183709
0.7703	Intermediate Similarity	NPC186033
0.7698	Intermediate Similarity	NPC266705
0.7698	Intermediate Similarity	NPC29008
0.7698	Intermediate Similarity	NPC228771
0.7698	Intermediate Similarity	NPC9067
0.7697	Intermediate Similarity	NPC472841
0.7692	Intermediate Similarity	NPC73656
0.7692	Intermediate Similarity	NPC228843
0.7692	Intermediate Similarity	NPC183103
0.7676	Intermediate Similarity	NPC245395
0.7676	Intermediate Similarity	NPC315769
0.7674	Intermediate Similarity	NPC201959
0.7671	Intermediate Similarity	NPC475482
0.7671	Intermediate Similarity	NPC470308
0.7671	Intermediate Similarity	NPC198621
0.7671	Intermediate Similarity	NPC470307
0.7671	Intermediate Similarity	NPC22676
0.7671	Intermediate Similarity	NPC216940
0.7662	Intermediate Similarity	NPC476552
0.7662	Intermediate Similarity	NPC476553
0.7662	Intermediate Similarity	NPC476551
0.766	Intermediate Similarity	NPC38017
0.766	Intermediate Similarity	NPC181675
0.7658	Intermediate Similarity	NPC470342
0.7658	Intermediate Similarity	NPC472060
0.7658	Intermediate Similarity	NPC472052
0.7656	Intermediate Similarity	NPC113457
0.7655	Intermediate Similarity	NPC173569
0.7655	Intermediate Similarity	NPC477874
0.7652	Intermediate Similarity	NPC322239
0.7647	Intermediate Similarity	NPC470619
0.7647	Intermediate Similarity	NPC208785
0.7647	Intermediate Similarity	NPC145527
0.7647	Intermediate Similarity	NPC261322
0.7647	Intermediate Similarity	NPC470618
0.7643	Intermediate Similarity	NPC170485
0.7639	Intermediate Similarity	NPC475457
0.7639	Intermediate Similarity	NPC475346
0.7639	Intermediate Similarity	NPC475627
0.7639	Intermediate Similarity	NPC18982
0.7635	Intermediate Similarity	NPC473499
0.763	Intermediate Similarity	NPC63010
0.7628	Intermediate Similarity	NPC226656
0.7628	Intermediate Similarity	NPC66508
0.7626	Intermediate Similarity	NPC265413
0.7626	Intermediate Similarity	NPC10154
0.7622	Intermediate Similarity	NPC191395
0.7619	Intermediate Similarity	NPC116742
0.7619	Intermediate Similarity	NPC139243
0.7619	Intermediate Similarity	NPC182249
0.7616	Intermediate Similarity	NPC126291
0.7615	Intermediate Similarity	NPC474272
0.7613	Intermediate Similarity	NPC43345
0.761	Intermediate Similarity	NPC472261
0.7609	Intermediate Similarity	NPC255026
0.7609	Intermediate Similarity	NPC71094
0.7603	Intermediate Similarity	NPC120852
0.76	Intermediate Similarity	NPC53016
0.7597	Intermediate Similarity	NPC118033
0.7595	Intermediate Similarity	NPC90497
0.7595	Intermediate Similarity	NPC105584
0.7593	Intermediate Similarity	NPC470341
0.7593	Intermediate Similarity	NPC105414
0.7593	Intermediate Similarity	NPC234497
0.7593	Intermediate Similarity	NPC324522
0.7593	Intermediate Similarity	NPC472058
0.7589	Intermediate Similarity	NPC186889
0.7586	Intermediate Similarity	NPC476615
0.7586	Intermediate Similarity	NPC476616
0.7586	Intermediate Similarity	NPC476617
0.7584	Intermediate Similarity	NPC472410
0.7582	Intermediate Similarity	NPC152233
0.758	Intermediate Similarity	NPC279605
0.758	Intermediate Similarity	NPC469507
0.758	Intermediate Similarity	NPC288353
0.7578	Intermediate Similarity	NPC469664
0.7576	Intermediate Similarity	NPC228988
0.7576	Intermediate Similarity	NPC46940
0.7571	Intermediate Similarity	NPC105031
0.7571	Intermediate Similarity	NPC113495
0.7569	Intermediate Similarity	NPC85595
0.7568	Intermediate Similarity	NPC221134
0.7568	Intermediate Similarity	NPC271494
0.7568	Intermediate Similarity	NPC470617
0.7568	Intermediate Similarity	NPC473591
0.7568	Intermediate Similarity	NPC155192
0.7568	Intermediate Similarity	NPC470616
0.7568	Intermediate Similarity	NPC1268
0.7566	Intermediate Similarity	NPC262297
0.7564	Intermediate Similarity	NPC324447
0.7552	Intermediate Similarity	NPC249425
0.7552	Intermediate Similarity	NPC27659
0.7551	Intermediate Similarity	NPC266006
0.755	Intermediate Similarity	NPC19862
0.755	Intermediate Similarity	NPC477913
0.755	Intermediate Similarity	NPC280717
0.755	Intermediate Similarity	NPC235195
0.755	Intermediate Similarity	NPC472836
0.755	Intermediate Similarity	NPC271607

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 NPC35630 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	279
0.1-0.2	1083
0.2-0.3	1193
0.3-0.4	2693
0.4-0.5	2061
0.5-0.6	1241
0.6-0.7	547
0.7-0.8	53
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
0.8069	Intermediate Similarity	NPD7003	Approved
0.7778	Intermediate Similarity	NPD4626	Approved
0.7704	Intermediate Similarity	NPD1651	Approved
0.7574	Intermediate Similarity	NPD5691	Approved
0.7554	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD7458	Discontinued
0.7518	Intermediate Similarity	NPD4624	Approved
0.75	Intermediate Similarity	NPD1283	Approved
0.7467	Intermediate Similarity	NPD8166	Discontinued
0.7448	Intermediate Similarity	NPD4060	Phase 1
0.7419	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD4908	Phase 1
0.7391	Intermediate Similarity	NPD6959	Discontinued
0.7388	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD7768	Phase 2
0.7338	Intermediate Similarity	NPD6273	Approved
0.7329	Intermediate Similarity	NPD4140	Approved
0.731	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD1281	Approved
0.7285	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4625	Phase 3
0.7234	Intermediate Similarity	NPD3972	Approved
0.723	Intermediate Similarity	NPD6353	Approved
0.7219	Intermediate Similarity	NPD7037	Approved
0.7218	Intermediate Similarity	NPD5451	Approved
0.7211	Intermediate Similarity	NPD3620	Phase 2
0.7211	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD2979	Phase 3
0.7209	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5404	Approved
0.72	Intermediate Similarity	NPD5408	Approved
0.72	Intermediate Similarity	NPD5406	Approved
0.72	Intermediate Similarity	NPD5405	Approved
0.7197	Intermediate Similarity	NPD2342	Discontinued
0.7185	Intermediate Similarity	NPD5535	Approved
0.7183	Intermediate Similarity	NPD6582	Phase 2
0.7183	Intermediate Similarity	NPD6583	Phase 3
0.7153	Intermediate Similarity	NPD6584	Phase 3
0.7133	Intermediate Similarity	NPD1876	Approved
0.7124	Intermediate Similarity	NPD3750	Approved
0.7124	Intermediate Similarity	NPD4628	Phase 3
0.7123	Intermediate Similarity	NPD7008	Discontinued
0.7122	Intermediate Similarity	NPD3091	Approved
0.7114	Intermediate Similarity	NPD4097	Suspended
0.7097	Intermediate Similarity	NPD7390	Discontinued
0.7097	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7041	Phase 2
0.7086	Intermediate Similarity	NPD2935	Discontinued
0.7081	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD3764	Approved
0.7063	Intermediate Similarity	NPD5327	Phase 3
0.7063	Intermediate Similarity	NPD1669	Approved
0.7059	Intermediate Similarity	NPD7843	Approved
0.7059	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD3020	Approved
0.705	Intermediate Similarity	NPD5536	Phase 2
0.7047	Intermediate Similarity	NPD5735	Approved
0.7044	Intermediate Similarity	NPD7028	Phase 2
0.7042	Intermediate Similarity	NPD1611	Approved
0.7039	Intermediate Similarity	NPD2346	Discontinued
0.7029	Intermediate Similarity	NPD7157	Approved
0.7024	Intermediate Similarity	NPD5844	Phase 1
0.7021	Intermediate Similarity	NPD2932	Approved
0.7021	Intermediate Similarity	NPD5846	Approved
0.7021	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD2286	Discontinued
0.7021	Intermediate Similarity	NPD6516	Phase 2
0.7021	Intermediate Similarity	NPD3019	Approved
0.7021	Intermediate Similarity	NPD4059	Approved
0.702	Intermediate Similarity	NPD2799	Discontinued
0.7019	Intermediate Similarity	NPD8455	Phase 2
0.7018	Intermediate Similarity	NPD8313	Approved
0.7018	Intermediate Similarity	NPD8312	Approved
0.7015	Intermediate Similarity	NPD2684	Approved
0.7014	Intermediate Similarity	NPD8651	Approved
0.7007	Intermediate Similarity	NPD1241	Discontinued
0.7007	Intermediate Similarity	NPD5283	Phase 1
0.7	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD3134	Approved
0.6974	Remote Similarity	NPD2438	Suspended
0.6974	Remote Similarity	NPD2531	Phase 2
0.6972	Remote Similarity	NPD3847	Discontinued
0.6964	Remote Similarity	NPD7177	Discontinued
0.6959	Remote Similarity	NPD6798	Discontinued
0.6959	Remote Similarity	NPD7294	Phase 1
0.6954	Remote Similarity	NPD7097	Phase 1
0.6953	Remote Similarity	NPD2859	Approved
0.6953	Remote Similarity	NPD2860	Approved
0.6943	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.694	Remote Similarity	NPD1358	Approved
0.6937	Remote Similarity	NPD4380	Phase 2
0.6934	Remote Similarity	NPD7635	Approved
0.6928	Remote Similarity	NPD6232	Discontinued
0.6928	Remote Similarity	NPD2344	Approved
0.6923	Remote Similarity	NPD1610	Phase 2
0.6923	Remote Similarity	NPD3092	Approved
0.6918	Remote Similarity	NPD2798	Approved
0.6918	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7819	Suspended
0.6913	Remote Similarity	NPD8032	Phase 2
0.6908	Remote Similarity	NPD1510	Phase 2
0.6908	Remote Similarity	NPD4108	Discontinued
0.6905	Remote Similarity	NPD7473	Discontinued
0.6901	Remote Similarity	NPD3095	Discontinued
0.6899	Remote Similarity	NPD4319	Phase 2
0.6894	Remote Similarity	NPD7411	Suspended
0.6892	Remote Similarity	NPD3027	Phase 3
0.6892	Remote Similarity	NPD7095	Approved
0.6887	Remote Similarity	NPD1607	Approved
0.6875	Remote Similarity	NPD3226	Approved
0.6875	Remote Similarity	NPD2934	Approved
0.6875	Remote Similarity	NPD2933	Approved
0.6871	Remote Similarity	NPD5736	Approved
0.6871	Remote Similarity	NPD2861	Phase 2
0.6867	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD968	Approved
0.6863	Remote Similarity	NPD4477	Approved
0.6863	Remote Similarity	NPD4476	Approved
0.6849	Remote Similarity	NPD2797	Approved
0.6849	Remote Similarity	NPD3094	Phase 2
0.6846	Remote Similarity	NPD3268	Approved
0.6846	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD7773	Phase 2
0.6821	Remote Similarity	NPD5124	Phase 1
0.6821	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6233	Phase 2
0.68	Remote Similarity	NPD7265	Discontinued
0.6797	Remote Similarity	NPD3748	Approved
0.6788	Remote Similarity	NPD3749	Approved
0.6783	Remote Similarity	NPD2667	Approved
0.6783	Remote Similarity	NPD2668	Approved
0.6779	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD2424	Discontinued
0.6767	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD8127	Discontinued
0.6761	Remote Similarity	NPD6580	Approved
0.6761	Remote Similarity	NPD6581	Approved
0.6761	Remote Similarity	NPD1548	Phase 1
0.6755	Remote Similarity	NPD1240	Approved
0.6752	Remote Similarity	NPD2309	Approved
0.675	Remote Similarity	NPD7427	Discontinued
0.6742	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD228	Approved
0.6736	Remote Similarity	NPD3496	Discontinued
0.6735	Remote Similarity	NPD1470	Approved
0.6733	Remote Similarity	NPD2313	Discontinued
0.6732	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD4538	Approved
0.6732	Remote Similarity	NPD4536	Approved
0.6731	Remote Similarity	NPD6674	Discontinued
0.6715	Remote Similarity	NPD3021	Approved
0.6715	Remote Similarity	NPD3022	Approved
0.6713	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD4749	Approved
0.6711	Remote Similarity	NPD6355	Discontinued
0.671	Remote Similarity	NPD5763	Approved
0.671	Remote Similarity	NPD5865	Clinical (unspecified phase)
0.671	Remote Similarity	NPD5762	Approved
0.6707	Remote Similarity	NPD5929	Approved
0.669	Remote Similarity	NPD1201	Approved
0.6689	Remote Similarity	NPD6663	Approved
0.6688	Remote Similarity	NPD4308	Phase 3
0.6688	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD7438	Suspended
0.6687	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1549	Phase 2
0.6667	Remote Similarity	NPD6696	Suspended
0.6667	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD709	Approved
0.6667	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6671	Approved
0.6647	Remote Similarity	NPD5709	Phase 3
0.6646	Remote Similarity	NPD37	Approved
0.6646	Remote Similarity	NPD7577	Discontinued
0.6644	Remote Similarity	NPD2232	Approved
0.6644	Remote Similarity	NPD2233	Approved
0.6644	Remote Similarity	NPD2230	Approved
0.6643	Remote Similarity	NPD1398	Phase 1
0.6643	Remote Similarity	NPD1894	Discontinued
0.6627	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD7447	Phase 1
0.6621	Remote Similarity	NPD3026	Approved
0.6621	Remote Similarity	NPD3023	Approved
0.662	Remote Similarity	NPD7340	Approved
0.6615	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD6559	Discontinued
0.6607	Remote Similarity	NPD4666	Phase 3
0.6606	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD6667	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