NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	236.04
Volume:	227.529
LogP:	2.059
LogD:	2.407
LogS:	-2.913
# Rotatable Bonds:	4
TPSA:	27.82
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.785
Synthetic Accessibility Score:	2.484
Fsp3:	0.182
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:	-4.857
MDCK Permeability:	1.9800630980171263e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.932
Plasma Protein Binding (PPB):	85.74559783935547%
Volume Distribution (VD):	1.19
Pgp-substrate:	12.032299995422363%

ADMET: Metabolism

CYP1A2-inhibitor:	0.992
CYP1A2-substrate:	0.707
CYP2C19-inhibitor:	0.973
CYP2C19-substrate:	0.35
CYP2C9-inhibitor:	0.878
CYP2C9-substrate:	0.948
CYP2D6-inhibitor:	0.886
CYP2D6-substrate:	0.903
CYP3A4-inhibitor:	0.91
CYP3A4-substrate:	0.155

ADMET: Excretion

Clearance (CL):	8.717
Half-life (T1/2):	0.906

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.467
Drug-inuced Liver Injury (DILI):	0.969
AMES Toxicity:	0.83
Rat Oral Acute Toxicity:	0.934
Maximum Recommended Daily Dose:	0.881
Skin Sensitization:	0.868
Carcinogencity:	0.124
Eye Corrosion:	0.01
Eye Irritation:	0.345
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC470823

Natural Product ID:	NPC470823
*Common Name:**	1H-Indol-3-Ylmethyl N-Methylcarbamodithioate
IUPAC Name:	1H-indol-3-ylmethyl N-methylcarbamodithioate
Synonyms:
Standard InCHIKey:	NIXSRAWVFMDSBC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H12N2S2/c1-12-11(14)15-7-8-6-13-10-5-3-2-4-9(8)10/h2-6,13H,7H2,1H3,(H,12,14)
SMILES:	CN=C(SCc1c[nH]c2c1cccc2)S
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2253036
PubChem CID:	76330012
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
NPO4482	Leptosphaeria maculans	Species	Leptosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18701303]
NPO4482	Leptosphaeria maculans	Species	Leptosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22672981]
NPO4482	Leptosphaeria maculans	Species	Leptosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4482	Leptosphaeria maculans	Species	Leptosphaeriaceae	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
Others	5

Activity Type	# Activity
Organism	3
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT35	Others	n.a.		T1/2	=	24.0	hr	PMID[543193]
NPT35	Others	n.a.		T1/2	=	20.0	hr	PMID[543193]
NPT4113	Organism	Leptosphaeria maculans	Leptosphaeria maculans	Inhibition	=	17.0	%	PMID[543193]
NPT4113	Organism	Leptosphaeria maculans	Leptosphaeria maculans	Inhibition	=	35.0	%	PMID[543193]
NPT4113	Organism	Leptosphaeria maculans	Leptosphaeria maculans	Inhibition	=	61.0	%	PMID[543193]

☑ 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 NPC470823 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	1664
0.1-0.2	15145
0.2-0.3	17212
0.3-0.4	3886
0.4-0.5	2108
0.5-0.6	1465
0.6-0.7	811
0.7-0.8	325
0.8-0.85	49
0.85-0.9	27
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9448	High Similarity	NPC216713
0.9241	High Similarity	NPC471957
0.9149	High Similarity	NPC84911
0.9078	High Similarity	NPC96102
0.9078	High Similarity	NPC261195
0.9078	High Similarity	NPC29886
0.9021	High Similarity	NPC110126
0.9021	High Similarity	NPC73767
0.9014	High Similarity	NPC105127
0.8958	High Similarity	NPC469768
0.8958	High Similarity	NPC469784
0.8958	High Similarity	NPC469761
0.8958	High Similarity	NPC469779
0.8958	High Similarity	NPC469780
0.8958	High Similarity	NPC469767
0.8958	High Similarity	NPC469783
0.8897	High Similarity	NPC469766
0.8867	High Similarity	NPC200214
0.8836	High Similarity	NPC190296
0.8828	High Similarity	NPC279081
0.8794	High Similarity	NPC82295
0.8716	High Similarity	NPC285731
0.8716	High Similarity	NPC314372
0.8699	High Similarity	NPC230002
0.8609	High Similarity	NPC148592
0.8591	High Similarity	NPC159856
0.8543	High Similarity	NPC321911
0.8533	High Similarity	NPC143872
0.8533	High Similarity	NPC288838
0.8487	Intermediate Similarity	NPC53947
0.8487	Intermediate Similarity	NPC105818
0.8487	Intermediate Similarity	NPC24678
0.8477	Intermediate Similarity	NPC179787
0.8477	Intermediate Similarity	NPC201380
0.8477	Intermediate Similarity	NPC469811
0.8457	Intermediate Similarity	NPC248454
0.8411	Intermediate Similarity	NPC63545
0.8377	Intermediate Similarity	NPC469763
0.8377	Intermediate Similarity	NPC141926
0.8377	Intermediate Similarity	NPC259644
0.8377	Intermediate Similarity	NPC25008
0.8377	Intermediate Similarity	NPC469760
0.8377	Intermediate Similarity	NPC469765
0.8377	Intermediate Similarity	NPC73952
0.8377	Intermediate Similarity	NPC469786
0.8354	Intermediate Similarity	NPC164228
0.8333	Intermediate Similarity	NPC22079
0.8323	Intermediate Similarity	NPC70922
0.8323	Intermediate Similarity	NPC75540
0.8323	Intermediate Similarity	NPC211572
0.8323	Intermediate Similarity	NPC34844
0.8323	Intermediate Similarity	NPC212376
0.8323	Intermediate Similarity	NPC80597
0.8299	Intermediate Similarity	NPC325252
0.8258	Intermediate Similarity	NPC325903
0.8253	Intermediate Similarity	NPC163055
0.8231	Intermediate Similarity	NPC198988
0.8217	Intermediate Similarity	NPC286427
0.8176	Intermediate Similarity	NPC218268
0.8165	Intermediate Similarity	NPC41257
0.8165	Intermediate Similarity	NPC56765
0.8165	Intermediate Similarity	NPC318065
0.8165	Intermediate Similarity	NPC206819
0.8156	Intermediate Similarity	NPC41174
0.8153	Intermediate Similarity	NPC469785
0.8121	Intermediate Similarity	NPC150259
0.8101	Intermediate Similarity	NPC216643
0.8101	Intermediate Similarity	NPC236711
0.8101	Intermediate Similarity	NPC469762
0.8077	Intermediate Similarity	NPC470233
0.8063	Intermediate Similarity	NPC282231
0.8056	Intermediate Similarity	NPC250361
0.8052	Intermediate Similarity	NPC316069
0.805	Intermediate Similarity	NPC92796
0.805	Intermediate Similarity	NPC135141
0.8014	Intermediate Similarity	NPC473587
0.8012	Intermediate Similarity	NPC90723
0.8012	Intermediate Similarity	NPC311276
0.8	Intermediate Similarity	NPC279918
0.8	Intermediate Similarity	NPC44773
0.8	Intermediate Similarity	NPC215584
0.8	Intermediate Similarity	NPC125746
0.8	Intermediate Similarity	NPC470204
0.8	Intermediate Similarity	NPC122141
0.8	Intermediate Similarity	NPC131718
0.7961	Intermediate Similarity	NPC2949
0.7961	Intermediate Similarity	NPC59084
0.7961	Intermediate Similarity	NPC115611
0.7959	Intermediate Similarity	NPC475428
0.795	Intermediate Similarity	NPC470203
0.7945	Intermediate Similarity	NPC473762
0.7937	Intermediate Similarity	NPC230869
0.7914	Intermediate Similarity	NPC49954
0.7914	Intermediate Similarity	NPC49217
0.7914	Intermediate Similarity	NPC160105
0.7914	Intermediate Similarity	NPC474561
0.7908	Intermediate Similarity	NPC63157
0.7908	Intermediate Similarity	NPC473868
0.7905	Intermediate Similarity	NPC179365
0.7905	Intermediate Similarity	NPC475450
0.7901	Intermediate Similarity	NPC40779
0.7901	Intermediate Similarity	NPC149265
0.7901	Intermediate Similarity	NPC317105
0.7895	Intermediate Similarity	NPC88097
0.7853	Intermediate Similarity	NPC17751
0.7853	Intermediate Similarity	NPC280864
0.7847	Intermediate Similarity	NPC46358
0.7818	Intermediate Similarity	NPC194411
0.7805	Intermediate Similarity	NPC54988
0.7793	Intermediate Similarity	NPC27740
0.7791	Intermediate Similarity	NPC102423
0.7784	Intermediate Similarity	NPC294693
0.7771	Intermediate Similarity	NPC470498
0.7763	Intermediate Similarity	NPC251722
0.7763	Intermediate Similarity	NPC314102
0.7758	Intermediate Similarity	NPC201700
0.7758	Intermediate Similarity	NPC63751
0.7756	Intermediate Similarity	NPC470440
0.7756	Intermediate Similarity	NPC204141
0.7744	Intermediate Similarity	NPC274229
0.7733	Intermediate Similarity	NPC473930
0.7725	Intermediate Similarity	NPC314603
0.7722	Intermediate Similarity	NPC2272
0.7711	Intermediate Similarity	NPC91895
0.7683	Intermediate Similarity	NPC194640
0.7679	Intermediate Similarity	NPC37423
0.7679	Intermediate Similarity	NPC275305
0.7665	Intermediate Similarity	NPC82331
0.7658	Intermediate Similarity	NPC470111
0.7658	Intermediate Similarity	NPC21605
0.7651	Intermediate Similarity	NPC78020
0.7636	Intermediate Similarity	NPC42372
0.7633	Intermediate Similarity	NPC474958
0.7633	Intermediate Similarity	NPC267885
0.7619	Intermediate Similarity	NPC313791
0.7619	Intermediate Similarity	NPC477611
0.7607	Intermediate Similarity	NPC474791
0.7605	Intermediate Similarity	NPC97343
0.76	Intermediate Similarity	NPC282398
0.7598	Intermediate Similarity	NPC272483
0.7588	Intermediate Similarity	NPC14113
0.7588	Intermediate Similarity	NPC68354
0.7588	Intermediate Similarity	NPC473380
0.7588	Intermediate Similarity	NPC84827
0.7588	Intermediate Similarity	NPC145885
0.7588	Intermediate Similarity	NPC240088
0.7574	Intermediate Similarity	NPC149155
0.7574	Intermediate Similarity	NPC203468
0.7574	Intermediate Similarity	NPC110500
0.7574	Intermediate Similarity	NPC293216
0.7562	Intermediate Similarity	NPC40070
0.7562	Intermediate Similarity	NPC33421
0.7544	Intermediate Similarity	NPC126709
0.7544	Intermediate Similarity	NPC11126
0.7544	Intermediate Similarity	NPC215795
0.7544	Intermediate Similarity	NPC265710
0.7544	Intermediate Similarity	NPC248041
0.7544	Intermediate Similarity	NPC176199
0.7529	Intermediate Similarity	NPC280852
0.7515	Intermediate Similarity	NPC225018
0.75	Intermediate Similarity	NPC91958
0.75	Intermediate Similarity	NPC245244
0.75	Intermediate Similarity	NPC16659
0.75	Intermediate Similarity	NPC146373
0.75	Intermediate Similarity	NPC37548
0.75	Intermediate Similarity	NPC314919
0.75	Intermediate Similarity	NPC166424
0.7485	Intermediate Similarity	NPC59269
0.7485	Intermediate Similarity	NPC284775
0.7485	Intermediate Similarity	NPC151939
0.7484	Intermediate Similarity	NPC169433
0.7471	Intermediate Similarity	NPC280297
0.7468	Intermediate Similarity	NPC242556
0.7466	Intermediate Similarity	NPC48564
0.7466	Intermediate Similarity	NPC182570
0.7466	Intermediate Similarity	NPC265605
0.7457	Intermediate Similarity	NPC233936
0.745	Intermediate Similarity	NPC476140
0.7442	Intermediate Similarity	NPC233050
0.7442	Intermediate Similarity	NPC283219
0.7442	Intermediate Similarity	NPC276540
0.7442	Intermediate Similarity	NPC213468
0.7436	Intermediate Similarity	NPC312092
0.7399	Intermediate Similarity	NPC300688
0.7394	Intermediate Similarity	NPC475990
0.7394	Intermediate Similarity	NPC221786
0.7394	Intermediate Similarity	NPC474880
0.7389	Intermediate Similarity	NPC284635
0.7384	Intermediate Similarity	NPC111275
0.7378	Intermediate Similarity	NPC51054
0.7378	Intermediate Similarity	NPC476464
0.7371	Intermediate Similarity	NPC228835
0.7371	Intermediate Similarity	NPC204717
0.7362	Intermediate Similarity	NPC232798
0.7361	Intermediate Similarity	NPC148140
0.7356	Intermediate Similarity	NPC243381
0.7356	Intermediate Similarity	NPC307191
0.7356	Intermediate Similarity	NPC275292
0.7356	Intermediate Similarity	NPC191415
0.7356	Intermediate Similarity	NPC470677

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 NPC470823 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	452
0.1-0.2	1009
0.2-0.3	993
0.3-0.4	2235
0.4-0.5	2324
0.5-0.6	1523
0.6-0.7	484
0.7-0.8	111
0.8-0.85	14
0.85-0.9	4
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9078	High Similarity	NPD198	Clinical (unspecified phase)
0.9021	High Similarity	NPD786	Approved
0.8767	High Similarity	NPD1722	Approved
0.8701	High Similarity	NPD1403	Approved
0.8701	High Similarity	NPD1404	Approved
0.8671	High Similarity	NPD3609	Approved
0.8671	High Similarity	NPD3610	Approved
0.8543	High Similarity	NPD3100	Discontinued
0.8487	Intermediate Similarity	NPD2172	Phase 1
0.8481	Intermediate Similarity	NPD2642	Approved
0.8481	Intermediate Similarity	NPD2639	Approved
0.8428	Intermediate Similarity	NPD2640	Approved
0.8428	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.8428	Intermediate Similarity	NPD2641	Approved
0.8421	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD5106	Approved
0.8253	Intermediate Similarity	NPD5105	Approved
0.8141	Intermediate Similarity	NPD2837	Discontinued
0.8063	Intermediate Similarity	NPD5315	Discontinued
0.8059	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD9583	Approved
0.8052	Intermediate Similarity	NPD1528	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD3323	Discontinued
0.7961	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD9357	Approved
0.7877	Intermediate Similarity	NPD991	Phase 2
0.7877	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD792	Discontinued
0.7806	Intermediate Similarity	NPD5254	Discontinued
0.777	Intermediate Similarity	NPD3654	Approved
0.7758	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD4510	Discontinued
0.7718	Intermediate Similarity	NPD3475	Approved
0.7718	Intermediate Similarity	NPD3476	Approved
0.7692	Intermediate Similarity	NPD3401	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD3015	Discontinued
0.7679	Intermediate Similarity	NPD4128	Approved
0.7673	Intermediate Similarity	NPD4462	Approved
0.7673	Intermediate Similarity	NPD4463	Approved
0.7658	Intermediate Similarity	NPD1661	Suspended
0.7658	Intermediate Similarity	NPD4547	Phase 3
0.7647	Intermediate Similarity	NPD1262	Discovery
0.7635	Intermediate Similarity	NPD2119	Approved
0.7635	Intermediate Similarity	NPD2118	Approved
0.7633	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD4075	Phase 2
0.7628	Intermediate Similarity	NPD2006	Phase 2
0.7622	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD2430	Phase 2
0.7595	Intermediate Similarity	NPD1683	Approved
0.7593	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD2580	Discontinued
0.759	Intermediate Similarity	NPD1248	Discontinued
0.7588	Intermediate Similarity	NPD2144	Approved
0.7588	Intermediate Similarity	NPD3505	Approved
0.7588	Intermediate Similarity	NPD4181	Approved
0.7588	Intermediate Similarity	NPD3506	Approved
0.758	Intermediate Similarity	NPD4509	Discontinued
0.7574	Intermediate Similarity	NPD482	Approved
0.7574	Intermediate Similarity	NPD5065	Approved
0.7566	Intermediate Similarity	NPD3385	Approved
0.7546	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD4079	Approved
0.7544	Intermediate Similarity	NPD4076	Approved
0.7516	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6595	Phase 3
0.75	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD8073	Approved
0.7485	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD649	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD268	Approved
0.7466	Intermediate Similarity	NPD271	Approved
0.7457	Intermediate Similarity	NPD1708	Approved
0.7457	Intermediate Similarity	NPD3038	Discontinued
0.7457	Intermediate Similarity	NPD1707	Approved
0.7451	Intermediate Similarity	NPD4028	Approved
0.7451	Intermediate Similarity	NPD4030	Approved
0.7451	Intermediate Similarity	NPD4029	Approved
0.7446	Intermediate Similarity	NPD8072	Approved
0.7443	Intermediate Similarity	NPD2310	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD9392	Approved
0.7431	Intermediate Similarity	NPD9396	Approved
0.7423	Intermediate Similarity	NPD2165	Phase 1
0.7414	Intermediate Similarity	NPD1332	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD269	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD8272	Phase 2
0.7378	Intermediate Similarity	NPD3113	Approved
0.7378	Intermediate Similarity	NPD3114	Approved
0.7378	Intermediate Similarity	NPD3115	Approved
0.7378	Intermediate Similarity	NPD3112	Approved
0.7371	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD715	Phase 3
0.7356	Intermediate Similarity	NPD1895	Discontinued
0.7338	Intermediate Similarity	NPD3944	Approved
0.7338	Intermediate Similarity	NPD3942	Approved
0.733	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD1227	Phase 2
0.7326	Intermediate Similarity	NPD6044	Discontinued
0.7325	Intermediate Similarity	NPD768	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD2720	Phase 1
0.7317	Intermediate Similarity	NPD1597	Phase 1
0.7317	Intermediate Similarity	NPD977	Approved
0.7317	Intermediate Similarity	NPD976	Approved
0.7317	Intermediate Similarity	NPD975	Approved
0.7314	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD2094	Phase 2
0.7314	Intermediate Similarity	NPD2095	Phase 2
0.7314	Intermediate Similarity	NPD2092	Phase 2
0.731	Intermediate Similarity	NPD750	Phase 2
0.7301	Intermediate Similarity	NPD4641	Discontinued
0.7294	Intermediate Similarity	NPD5436	Phase 1
0.7288	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD6217	Discontinued
0.7273	Intermediate Similarity	NPD2091	Phase 2
0.7273	Intermediate Similarity	NPD2096	Phase 2
0.7249	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD8431	Approved
0.7247	Intermediate Similarity	NPD3961	Discontinued
0.7244	Intermediate Similarity	NPD1254	Approved
0.7244	Intermediate Similarity	NPD1256	Approved
0.7244	Intermediate Similarity	NPD1255	Approved
0.7244	Intermediate Similarity	NPD1253	Approved
0.7225	Intermediate Similarity	NPD3348	Phase 2
0.7211	Intermediate Similarity	NPD3843	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD803	Phase 1
0.7171	Intermediate Similarity	NPD1598	Discontinued
0.7143	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD206	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD1592	Phase 3
0.7118	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD2068	Approved
0.7107	Intermediate Similarity	NPD2070	Approved
0.7107	Intermediate Similarity	NPD2072	Approved
0.7107	Intermediate Similarity	NPD2074	Approved
0.7107	Intermediate Similarity	NPD2069	Approved
0.7107	Intermediate Similarity	NPD2071	Approved
0.7107	Intermediate Similarity	NPD2073	Approved
0.7107	Intermediate Similarity	NPD2075	Approved
0.7102	Intermediate Similarity	NPD1873	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD1326	Approved
0.7093	Intermediate Similarity	NPD1325	Approved
0.7089	Intermediate Similarity	NPD6554	Approved
0.7089	Intermediate Similarity	NPD45	Approved
0.7083	Intermediate Similarity	NPD704	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD947	Approved
0.7072	Intermediate Similarity	NPD5145	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD748	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD2150	Discontinued
0.7052	Intermediate Similarity	NPD1567	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD1038	Approved
0.7049	Intermediate Similarity	NPD802	Phase 2
0.7048	Intermediate Similarity	NPD3339	Approved
0.7045	Intermediate Similarity	NPD1327	Discontinued
0.7035	Intermediate Similarity	NPD4639	Approved
0.7035	Intermediate Similarity	NPD4638	Approved
0.7035	Intermediate Similarity	NPD4640	Approved
0.7033	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD3833	Phase 3
0.703	Intermediate Similarity	NPD3835	Phase 3
0.7029	Intermediate Similarity	NPD2771	Approved
0.7022	Intermediate Similarity	NPD3512	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD4702	Approved
0.7012	Intermediate Similarity	NPD4703	Approved
0.7011	Intermediate Similarity	NPD7619	Phase 3
0.7011	Intermediate Similarity	NPD7618	Phase 3
0.7	Intermediate Similarity	NPD9598	Discontinued
0.7	Intermediate Similarity	NPD680	Discontinued
0.6995	Remote Similarity	NPD7127	Clinical (unspecified phase)
0.699	Remote Similarity	NPD5818	Discontinued
0.6975	Remote Similarity	NPD4047	Discontinued
0.6973	Remote Similarity	NPD2960	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD4318	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4649	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD2748	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD4880	Discontinued
0.6957	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD3117	Approved
0.6954	Remote Similarity	NPD3116	Approved
0.6936	Remote Similarity	NPD2390	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD5021	Discontinued
0.6935	Remote Similarity	NPD6664	Approved
0.6914	Remote Similarity	NPD4112	Clinical (unspecified phase)
0.691	Remote Similarity	NPD4050	Phase 1
0.6905	Remote Similarity	NPD1328	Approved
0.6882	Remote Similarity	NPD1042	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD6278	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD1251	Discontinued
0.6875	Remote Similarity	NPD3859	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD1183	Approved
0.6865	Remote Similarity	NPD2717	Phase 2

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