NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	234.08
Volume:	235.106
LogP:	2.607
LogD:	2.748
LogS:	-3.133
# Rotatable Bonds:	5
TPSA:	44.89
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.857
Synthetic Accessibility Score:	2.245
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.798
MDCK Permeability:	1.7055068383342586e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.761
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.263

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.621
Plasma Protein Binding (PPB):	88.52571868896484%
Volume Distribution (VD):	1.115
Pgp-substrate:	12.042521476745605%

ADMET: Metabolism

CYP1A2-inhibitor:	0.99
CYP1A2-substrate:	0.705
CYP2C19-inhibitor:	0.94
CYP2C19-substrate:	0.504
CYP2C9-inhibitor:	0.408
CYP2C9-substrate:	0.949
CYP2D6-inhibitor:	0.635
CYP2D6-substrate:	0.889
CYP3A4-inhibitor:	0.406
CYP3A4-substrate:	0.235

ADMET: Excretion

Clearance (CL):	8.847
Half-life (T1/2):	0.815

ADMET: Toxicity

hERG Blockers:	0.04
Human Hepatotoxicity (H-HT):	0.257
Drug-inuced Liver Injury (DILI):	0.836
AMES Toxicity:	0.264
Rat Oral Acute Toxicity:	0.661
Maximum Recommended Daily Dose:	0.852
Skin Sensitization:	0.928
Carcinogencity:	0.055
Eye Corrosion:	0.005
Eye Irritation:	0.306
Respiratory Toxicity:	0.363

Download Data

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

Natural Product: NPC471957

Natural Product ID:	NPC471957
*Common Name:**	UFBJIWZJGBIRMB-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	UFBJIWZJGBIRMB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H14N2OS/c1-16-12(15)13-7-6-9-8-14-11-5-3-2-4-10(9)11/h2-5,8,14H,6-7H2,1H3,(H,13,15)
SMILES:	CSC(=NCCc1c[nH]c2c1cccc2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3314413
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0002497] Indoles [CHEMONTID:0004196] 3-alkylindoles

*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
NPO13162	Glycosmis petelotii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24949913]
NPO13162	Glycosmis petelotii	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
IC50	4
Others	10

Activity Type	# Activity
Protein Family	14

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2685	Protein Family	Voltage-gated L-type calcium channel	Rattus norvegicus	IC50	=	79432.82	nM	PMID[544288]
NPT2685	Protein Family	Voltage-gated L-type calcium channel	Rattus norvegicus	Emax	=	77.8	%	PMID[544288]
NPT2685	Protein Family	Voltage-gated L-type calcium channel	Rattus norvegicus	IC50	=	125892.54	nM	PMID[544288]
NPT2685	Protein Family	Voltage-gated L-type calcium channel	Rattus norvegicus	Emax	=	76.1	%	PMID[544288]
NPT2685	Protein Family	Voltage-gated L-type calcium channel	Rattus norvegicus	IC50	=	50118.72	nM	PMID[544288]
NPT2685	Protein Family	Voltage-gated L-type calcium channel	Rattus norvegicus	Emax	=	70.0	%	PMID[544288]
NPT2685	Protein Family	Voltage-gated L-type calcium channel	Rattus norvegicus	IC50	=	63095.73	nM	PMID[544288]
NPT2685	Protein Family	Voltage-gated L-type calcium channel	Rattus norvegicus	Emax	=	67.8	%	PMID[544288]
NPT2685	Protein Family	Voltage-gated L-type calcium channel	Rattus norvegicus	AUC	=	57.6	n.a.	PMID[544288]
NPT2685	Protein Family	Voltage-gated L-type calcium channel	Rattus norvegicus	AUC	=	11.2	n.a.	PMID[544288]
NPT2685	Protein Family	Voltage-gated L-type calcium channel	Rattus norvegicus	Inhibition	=	98.8	%	PMID[544288]
NPT2685	Protein Family	Voltage-gated L-type calcium channel	Rattus norvegicus	Inhibition	=	73.9	%	PMID[544288]
NPT2685	Protein Family	Voltage-gated L-type calcium channel	Rattus norvegicus	Activity	=	75.9	%	PMID[544288]
NPT2685	Protein Family	Voltage-gated L-type calcium channel	Rattus norvegicus	Activity	=	53.4	%	PMID[544288]

☑ 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 NPC471957 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	815
0.1-0.2	12048
0.2-0.3	18691
0.3-0.4	5414
0.4-0.5	2328
0.5-0.6	1718
0.6-0.7	1035
0.7-0.8	498
0.8-0.85	96
0.85-0.9	16
0.9-0.95	35
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9648	High Similarity	NPC216713
0.9568	High Similarity	NPC190296
0.9433	High Similarity	NPC314372
0.9348	High Similarity	NPC84911
0.931	High Similarity	NPC200214
0.9296	High Similarity	NPC159856
0.9275	High Similarity	NPC29886
0.9275	High Similarity	NPC96102
0.9275	High Similarity	NPC261195
0.9241	High Similarity	NPC470823
0.9214	High Similarity	NPC110126
0.9214	High Similarity	NPC73767
0.9209	High Similarity	NPC105127
0.9172	High Similarity	NPC105818
0.9172	High Similarity	NPC24678
0.9149	High Similarity	NPC469780
0.9149	High Similarity	NPC469783
0.9149	High Similarity	NPC469767
0.9149	High Similarity	NPC469784
0.9149	High Similarity	NPC469761
0.9149	High Similarity	NPC469768
0.9149	High Similarity	NPC469779
0.9085	High Similarity	NPC469766
0.9048	High Similarity	NPC25008
0.9048	High Similarity	NPC469786
0.9048	High Similarity	NPC469765
0.9048	High Similarity	NPC259644
0.9048	High Similarity	NPC73952
0.9048	High Similarity	NPC469763
0.9048	High Similarity	NPC469760
0.9014	High Similarity	NPC279081
0.8986	High Similarity	NPC211572
0.8986	High Similarity	NPC82295
0.8986	High Similarity	NPC80597
0.8986	High Similarity	NPC70922
0.8986	High Similarity	NPC212376
0.8986	High Similarity	NPC75540
0.8881	High Similarity	NPC230002
0.88	High Similarity	NPC469785
0.8767	High Similarity	NPC285731
0.8742	High Similarity	NPC469762
0.8716	High Similarity	NPC321911
0.8707	High Similarity	NPC143872
0.8707	High Similarity	NPC288838
0.8693	High Similarity	NPC282231
0.8684	High Similarity	NPC135141
0.8684	High Similarity	NPC92796
0.8658	High Similarity	NPC53947
0.8649	High Similarity	NPC179787
0.8649	High Similarity	NPC201380
0.8649	High Similarity	NPC469811
0.8636	High Similarity	NPC311276
0.8627	High Similarity	NPC279918
0.8627	High Similarity	NPC131718
0.8616	High Similarity	NPC248454
0.8581	High Similarity	NPC63545
0.8562	High Similarity	NPC230869
0.8543	High Similarity	NPC141926
0.8526	High Similarity	NPC474561
0.8526	High Similarity	NPC49954
0.8526	High Similarity	NPC49217
0.8526	High Similarity	NPC160105
0.8516	High Similarity	NPC40779
0.8511	High Similarity	NPC22079
0.8487	Intermediate Similarity	NPC34844
0.8472	Intermediate Similarity	NPC325252
0.8421	Intermediate Similarity	NPC325903
0.8418	Intermediate Similarity	NPC194411
0.8408	Intermediate Similarity	NPC54988
0.8405	Intermediate Similarity	NPC163055
0.8403	Intermediate Similarity	NPC198988
0.8397	Intermediate Similarity	NPC102423
0.8377	Intermediate Similarity	NPC236711
0.8377	Intermediate Similarity	NPC286427
0.8365	Intermediate Similarity	NPC470498
0.8354	Intermediate Similarity	NPC201700
0.8354	Intermediate Similarity	NPC63751
0.8345	Intermediate Similarity	NPC218268
0.8333	Intermediate Similarity	NPC41174
0.8323	Intermediate Similarity	NPC206819
0.8323	Intermediate Similarity	NPC41257
0.8323	Intermediate Similarity	NPC56765
0.8323	Intermediate Similarity	NPC318065
0.8313	Intermediate Similarity	NPC314603
0.8288	Intermediate Similarity	NPC150259
0.828	Intermediate Similarity	NPC194640
0.8261	Intermediate Similarity	NPC37423
0.8261	Intermediate Similarity	NPC275305
0.8258	Intermediate Similarity	NPC216643
0.8239	Intermediate Similarity	NPC78020
0.8235	Intermediate Similarity	NPC470233
0.8227	Intermediate Similarity	NPC250361
0.8212	Intermediate Similarity	NPC316069
0.821	Intermediate Similarity	NPC267885
0.8199	Intermediate Similarity	NPC313791
0.8182	Intermediate Similarity	NPC473587
0.817	Intermediate Similarity	NPC148592
0.8165	Intermediate Similarity	NPC90723
0.8163	Intermediate Similarity	NPC125746
0.816	Intermediate Similarity	NPC68354
0.8153	Intermediate Similarity	NPC470204
0.8153	Intermediate Similarity	NPC44773
0.8153	Intermediate Similarity	NPC215584
0.8153	Intermediate Similarity	NPC122141
0.8148	Intermediate Similarity	NPC203468
0.8148	Intermediate Similarity	NPC149155
0.8148	Intermediate Similarity	NPC110500
0.8146	Intermediate Similarity	NPC470440
0.8125	Intermediate Similarity	NPC475428
0.8121	Intermediate Similarity	NPC59084
0.8121	Intermediate Similarity	NPC2949
0.8121	Intermediate Similarity	NPC115611
0.8112	Intermediate Similarity	NPC473762
0.811	Intermediate Similarity	NPC126709
0.811	Intermediate Similarity	NPC11126
0.811	Intermediate Similarity	NPC215795
0.811	Intermediate Similarity	NPC248041
0.811	Intermediate Similarity	NPC176199
0.8105	Intermediate Similarity	NPC37548
0.8101	Intermediate Similarity	NPC470203
0.8079	Intermediate Similarity	NPC242556
0.8069	Intermediate Similarity	NPC475450
0.8069	Intermediate Similarity	NPC179365
0.8067	Intermediate Similarity	NPC473868
0.8067	Intermediate Similarity	NPC63157
0.8061	Intermediate Similarity	NPC164228
0.8054	Intermediate Similarity	NPC88097
0.805	Intermediate Similarity	NPC317105
0.805	Intermediate Similarity	NPC149265
0.8049	Intermediate Similarity	NPC151939
0.8049	Intermediate Similarity	NPC59269
0.8039	Intermediate Similarity	NPC470111
0.8014	Intermediate Similarity	NPC46358
0.8012	Intermediate Similarity	NPC233936
0.8	Intermediate Similarity	NPC42372
0.8	Intermediate Similarity	NPC213468
0.8	Intermediate Similarity	NPC283219
0.8	Intermediate Similarity	NPC280864
0.8	Intermediate Similarity	NPC17751
0.7958	Intermediate Similarity	NPC27740
0.7952	Intermediate Similarity	NPC300688
0.7939	Intermediate Similarity	NPC84827
0.7939	Intermediate Similarity	NPC240088
0.7939	Intermediate Similarity	NPC145885
0.7939	Intermediate Similarity	NPC111275
0.7939	Intermediate Similarity	NPC473380
0.7939	Intermediate Similarity	NPC14113
0.7927	Intermediate Similarity	NPC293216
0.7919	Intermediate Similarity	NPC314102
0.7919	Intermediate Similarity	NPC294693
0.7919	Intermediate Similarity	NPC251722
0.7917	Intermediate Similarity	NPC204717
0.7917	Intermediate Similarity	NPC228835
0.7908	Intermediate Similarity	NPC204141
0.7898	Intermediate Similarity	NPC38736
0.7898	Intermediate Similarity	NPC470507
0.7892	Intermediate Similarity	NPC55772
0.7892	Intermediate Similarity	NPC265710
0.7891	Intermediate Similarity	NPC473930
0.7888	Intermediate Similarity	NPC274229
0.7875	Intermediate Similarity	NPC225018
0.7871	Intermediate Similarity	NPC2272
0.7871	Intermediate Similarity	NPC124005
0.7871	Intermediate Similarity	NPC187951
0.787	Intermediate Similarity	NPC314002
0.787	Intermediate Similarity	NPC163421
0.787	Intermediate Similarity	NPC188387
0.787	Intermediate Similarity	NPC280290
0.7857	Intermediate Similarity	NPC469358
0.7857	Intermediate Similarity	NPC220765
0.7848	Intermediate Similarity	NPC285469
0.7844	Intermediate Similarity	NPC16659
0.7831	Intermediate Similarity	NPC284775
0.7824	Intermediate Similarity	NPC235684
0.7824	Intermediate Similarity	NPC94752
0.7824	Intermediate Similarity	NPC171171
0.7806	Intermediate Similarity	NPC21605
0.7805	Intermediate Similarity	NPC82331
0.7799	Intermediate Similarity	NPC129721
0.7798	Intermediate Similarity	NPC71037
0.7784	Intermediate Similarity	NPC233050
0.7784	Intermediate Similarity	NPC276540
0.7778	Intermediate Similarity	NPC317030
0.7771	Intermediate Similarity	NPC474958
0.7765	Intermediate Similarity	NPC15102
0.7758	Intermediate Similarity	NPC477611
0.7755	Intermediate Similarity	NPC282398
0.7751	Intermediate Similarity	NPC48938
0.7744	Intermediate Similarity	NPC91895
0.7744	Intermediate Similarity	NPC97343
0.7736	Intermediate Similarity	NPC51054
0.7736	Intermediate Similarity	NPC141353
0.7733	Intermediate Similarity	NPC213629
0.773	Intermediate Similarity	NPC109447
0.7727	Intermediate Similarity	NPC272483
0.7719	Intermediate Similarity	NPC474707
0.7707	Intermediate Similarity	NPC33421
0.7707	Intermediate Similarity	NPC40070
0.7703	Intermediate Similarity	NPC256893
0.7697	Intermediate Similarity	NPC104483

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 NPC471957 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	311
0.1-0.2	845
0.2-0.3	975
0.3-0.4	1856
0.4-0.5	2392
0.5-0.6	1791
0.6-0.7	772
0.7-0.8	177
0.8-0.85	25
0.85-0.9	4
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9275	High Similarity	NPD198	Clinical (unspecified phase)
0.9214	High Similarity	NPD786	Approved
0.8951	High Similarity	NPD1722	Approved
0.875	High Similarity	NPD1404	Approved
0.875	High Similarity	NPD1403	Approved
0.8716	High Similarity	NPD3100	Discontinued
0.8658	High Similarity	NPD2172	Phase 1
0.8591	High Similarity	NPD4374	Clinical (unspecified phase)
0.8526	High Similarity	NPD2639	Approved
0.8526	High Similarity	NPD2642	Approved
0.8471	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD2641	Approved
0.8471	Intermediate Similarity	NPD2640	Approved
0.8418	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.8365	Intermediate Similarity	NPD3610	Approved
0.8365	Intermediate Similarity	NPD3609	Approved
0.8354	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.8301	Intermediate Similarity	NPD2837	Discontinued
0.8289	Intermediate Similarity	NPD4462	Approved
0.8289	Intermediate Similarity	NPD4463	Approved
0.8261	Intermediate Similarity	NPD4128	Approved
0.821	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD3323	Discontinued
0.816	Intermediate Similarity	NPD4181	Approved
0.816	Intermediate Similarity	NPD3505	Approved
0.816	Intermediate Similarity	NPD3506	Approved
0.816	Intermediate Similarity	NPD2144	Approved
0.8155	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD482	Approved
0.8148	Intermediate Similarity	NPD5065	Approved
0.8121	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD4079	Approved
0.811	Intermediate Similarity	NPD4076	Approved
0.8072	Intermediate Similarity	NPD5106	Approved
0.8072	Intermediate Similarity	NPD5105	Approved
0.8061	Intermediate Similarity	NPD6595	Phase 3
0.8049	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.8042	Intermediate Similarity	NPD991	Phase 2
0.8042	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD3038	Discontinued
0.7988	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD4075	Phase 2
0.7987	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7972	Intermediate Similarity	NPD9583	Approved
0.7961	Intermediate Similarity	NPD5254	Discontinued
0.7931	Intermediate Similarity	NPD3654	Approved
0.7922	Intermediate Similarity	NPD1661	Suspended
0.7895	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD3476	Approved
0.7877	Intermediate Similarity	NPD3475	Approved
0.787	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD750	Phase 2
0.7857	Intermediate Similarity	NPD2095	Phase 2
0.7857	Intermediate Similarity	NPD2092	Phase 2
0.7857	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD2094	Phase 2
0.7832	Intermediate Similarity	NPD9357	Approved
0.7811	Intermediate Similarity	NPD2091	Phase 2
0.7811	Intermediate Similarity	NPD2096	Phase 2
0.7806	Intermediate Similarity	NPD4547	Phase 3
0.78	Intermediate Similarity	NPD1262	Discovery
0.7793	Intermediate Similarity	NPD2118	Approved
0.7793	Intermediate Similarity	NPD2119	Approved
0.7791	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3961	Discontinued
0.7778	Intermediate Similarity	NPD8431	Approved
0.7778	Intermediate Similarity	NPD2006	Phase 2
0.7764	Intermediate Similarity	NPD5315	Discontinued
0.7764	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD2430	Phase 2
0.7742	Intermediate Similarity	NPD1528	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD1683	Approved
0.7738	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD2580	Discontinued
0.7736	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD1248	Discontinued
0.7718	Intermediate Similarity	NPD3385	Approved
0.7712	Intermediate Similarity	NPD1592	Phase 3
0.7706	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD2720	Phase 1
0.7662	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD1326	Approved
0.7636	Intermediate Similarity	NPD1325	Approved
0.7622	Intermediate Similarity	NPD268	Approved
0.7622	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD271	Approved
0.7616	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD6217	Discontinued
0.7611	Intermediate Similarity	NPD8073	Approved
0.76	Intermediate Similarity	NPD4029	Approved
0.76	Intermediate Similarity	NPD4028	Approved
0.76	Intermediate Similarity	NPD4030	Approved
0.7589	Intermediate Similarity	NPD9396	Approved
0.7589	Intermediate Similarity	NPD9392	Approved
0.7588	Intermediate Similarity	NPD1707	Approved
0.7588	Intermediate Similarity	NPD1708	Approved
0.758	Intermediate Similarity	NPD4702	Approved
0.758	Intermediate Similarity	NPD4703	Approved
0.7578	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD4640	Approved
0.7576	Intermediate Similarity	NPD4639	Approved
0.7576	Intermediate Similarity	NPD4638	Approved
0.7572	Intermediate Similarity	NPD2310	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD269	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD8072	Approved
0.7562	Intermediate Similarity	NPD2165	Phase 1
0.7557	Intermediate Similarity	NPD1038	Approved
0.7544	Intermediate Similarity	NPD1332	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD8272	Phase 2
0.7517	Intermediate Similarity	NPD715	Phase 3
0.7516	Intermediate Similarity	NPD3112	Approved
0.7516	Intermediate Similarity	NPD3115	Approved
0.7516	Intermediate Similarity	NPD3113	Approved
0.7516	Intermediate Similarity	NPD3114	Approved
0.7516	Intermediate Similarity	NPD2748	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7619	Phase 3
0.7514	Intermediate Similarity	NPD7618	Phase 3
0.7485	Intermediate Similarity	NPD3117	Approved
0.7485	Intermediate Similarity	NPD3116	Approved
0.7485	Intermediate Similarity	NPD1895	Discontinued
0.7483	Intermediate Similarity	NPD3942	Approved
0.7483	Intermediate Similarity	NPD3944	Approved
0.747	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD5021	Discontinued
0.7468	Intermediate Similarity	NPD768	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD802	Phase 2
0.7453	Intermediate Similarity	NPD975	Approved
0.7453	Intermediate Similarity	NPD977	Approved
0.7453	Intermediate Similarity	NPD976	Approved
0.744	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD6664	Approved
0.7425	Intermediate Similarity	NPD5436	Phase 1
0.7421	Intermediate Similarity	NPD1183	Approved
0.7418	Intermediate Similarity	NPD3015	Discontinued
0.7391	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD3401	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD1256	Approved
0.7386	Intermediate Similarity	NPD1255	Approved
0.7386	Intermediate Similarity	NPD792	Discontinued
0.7386	Intermediate Similarity	NPD1254	Approved
0.7386	Intermediate Similarity	NPD1253	Approved
0.7381	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD3835	Phase 3
0.7375	Intermediate Similarity	NPD3833	Phase 3
0.736	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD1227	Phase 2
0.7353	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD803	Phase 1
0.7348	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7948	Phase 1
0.7333	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD3843	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD1598	Discontinued
0.7303	Intermediate Similarity	NPD4615	Phase 2
0.7296	Intermediate Similarity	NPD7469	Discontinued
0.7289	Intermediate Similarity	NPD5138	Approved
0.7289	Intermediate Similarity	NPD5140	Approved
0.7278	Intermediate Similarity	NPD4509	Discontinued
0.7278	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1327	Discontinued
0.7256	Intermediate Similarity	NPD4326	Phase 2
0.7251	Intermediate Similarity	NPD6044	Discontinued
0.7244	Intermediate Similarity	NPD2074	Approved
0.7244	Intermediate Similarity	NPD2073	Approved
0.7244	Intermediate Similarity	NPD2072	Approved
0.7244	Intermediate Similarity	NPD2075	Approved
0.7244	Intermediate Similarity	NPD2070	Approved
0.7244	Intermediate Similarity	NPD2068	Approved
0.7244	Intermediate Similarity	NPD2071	Approved
0.7244	Intermediate Similarity	NPD2069	Approved
0.7234	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD5995	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD45	Approved
0.7226	Intermediate Similarity	NPD6554	Approved
0.7225	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4641	Discontinued
0.7219	Intermediate Similarity	NPD947	Approved
0.7215	Intermediate Similarity	NPD3717	Discontinued
0.7215	Intermediate Similarity	NPD4510	Discontinued
0.7213	Intermediate Similarity	NPD484	Approved
0.7212	Intermediate Similarity	NPD704	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD748	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD3404	Approved
0.7195	Intermediate Similarity	NPD2150	Discontinued
0.7191	Intermediate Similarity	NPD5145	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD3339	Approved
0.7176	Intermediate Similarity	NPD1567	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD649	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD8386	Phase 2
0.7151	Intermediate Similarity	NPD3348	Phase 2
0.7143	Intermediate Similarity	NPD9598	Discontinued
0.7143	Intermediate Similarity	NPD2089	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD509	Phase 3

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