NPASS Compound

Structure

CID314919 OpenBabel06191716132D 28 32 0 0 1 0 0 0 0 0999 V2000 1.8568 -1.6444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5108 2.1133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7071 0.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1939 -2.7159 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9428 -2.5310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3279 -3.2159 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9951 -1.5323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3279 -1.2159 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7869 -2.4403 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9230 -2.2159 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7895 0.3532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2507 0.8532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9877 0.1564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1939 -1.7159 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0518 -2.9849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4618 -1.7159 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5108 -1.4069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2018 -0.4558 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7346 -1.4417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2507 -0.1468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4618 -2.7159 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1564 -0.9877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4417 -0.7346 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.0599 -1.2159 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 0.0006 -3.9836 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 3.5108 -3.0249 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.2018 1.1622 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2 27 1 0 0 0 0 3 28 1 0 0 0 0 4 6 2 0 0 0 0 4 14 1 0 0 0 0 5 7 2 0 0 0 0 5 15 1 0 0 0 0 6 21 1 0 0 0 0 7 22 1 0 0 0 0 8 14 2 0 0 0 0 8 16 1 0 0 0 0 9 15 2 0 0 0 0 9 19 1 0 0 0 0 10 17 2 0 0 0 0 10 26 1 0 0 0 0 11 18 2 0 0 0 0 11 27 1 0 0 0 0 12 20 2 0 0 0 0 12 27 1 0 0 0 0 13 23 1 0 0 0 0 13 28 1 0 0 0 0 14 24 1 0 0 0 0 15 25 1 0 0 0 0 16 17 1 0 0 0 0 16 21 2 0 0 0 0 17 18 1 0 0 0 0 18 20 1 0 0 0 0 19 22 2 0 0 0 0 19 23 1 0 0 0 0 20 23 1 0 0 0 0 21 26 1 0 0 0 0 22 28 1 0 0 0 0 23 1 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	409.11
Volume:	403.266
LogP:	6.182
LogD:	4.63
LogS:	-6.871
# Rotatable Bonds:	2
TPSA:	23.96
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.416
Synthetic Accessibility Score:	3.456
Fsp3:	0.217
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.938
MDCK Permeability:	1.06E-05
Pgp-inhibitor:	0.99
Pgp-substrate:	0.994
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.274
30% Bioavailability (F30%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.217
Plasma Protein Binding (PPB):	97.18%
Volume Distribution (VD):	2.888
Pgp-substrate:	1.69%

ADMET: Metabolism

CYP1A2-inhibitor:	0.939
CYP1A2-substrate:	0.909
CYP2C19-inhibitor:	0.877
CYP2C19-substrate:	0.777
CYP2C9-inhibitor:	0.812
CYP2C9-substrate:	0.698
CYP2D6-inhibitor:	0.962
CYP2D6-substrate:	0.904
CYP3A4-inhibitor:	0.873
CYP3A4-substrate:	0.852

ADMET: Excretion

Clearance (CL):	9.55
Half-life (T1/2):	0.061

ADMET: Toxicity

hERG Blockers:	0.964
Human Hepatotoxicity (H-HT):	0.458
Drug-inuced Liver Injury (DILI):	0.848
AMES Toxicity:	0.423
Rat Oral Acute Toxicity:	0.382
Maximum Recommended Daily Dose:	0.937
Skin Sensitization:	0.064
Carcinogencity:	0.442
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.592

Download Data

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

Natural Product: NPC314919

Natural Product ID:	NPC314919
*Common Name:**	Indimicin E
IUPAC Name:	(3R)-5-chloro-3-[4-(5-chloro-1H-indol-3-yl)-1-methylpyrrol-3-yl]-1,3-dimethyl-2H-indole
Synonyms:
Standard InCHIKey:	CMOISPAWONHXEH-QHCPKHFHSA-N
Standard InCHI:	InChI=1S/C23H21Cl2N3/c1-23(13-28(3)22-7-5-15(25)9-19(22)23)20-12-27(2)11-18(20)17-10-26-21-6-4-14(24)8-16(17)21/h4-12,26H,13H2,1-3H3/t23-/m0/s1
SMILES:	Cn1cc(c(c1)[C@@]1(C)CN(c2c1cc(Cl)cc2)C)c1c[nH]c2c1cc(Cl)cc2
Synthetic Gene Cluster:	BGC0001782;
ChEMBL Identifier:	CHEMBL3326891
PubChem CID:	86342742
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0002497] Indoles

*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
NPO40641	Streptomyces sp. SCSIO 03032	Strain	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24547685]
NPO40641	Streptomyces sp. SCSIO 03032	Strain	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25069084]

☑ 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
MIC	5

Activity Type	# Activity
Cell Line	1
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[557334]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	128.0	ug.mL-1	PMID[557334]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	128.0	ug.mL-1	PMID[557334]
NPT1261	Organism	Bacillus thuringiensis	Bacillus thuringiensis	MIC	>	128.0	ug.mL-1	PMID[557334]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	128.0	ug.mL-1	PMID[557334]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	128.0	ug.mL-1	PMID[557334]

☑ 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 NPC314919 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	1205
0.1-0.2	14872
0.2-0.3	18002
0.3-0.4	4009
0.4-0.5	1937
0.5-0.6	1555
0.6-0.7	832
0.7-0.8	248
0.8-0.85	29
0.85-0.9	3
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9298	High Similarity	NPC315617
0.9298	High Similarity	NPC316359
0.9298	High Similarity	NPC316018
0.9298	High Similarity	NPC314058
0.8941	High Similarity	NPC83381
0.8634	High Similarity	NPC53947
0.8598	High Similarity	NPC216643
0.8562	High Similarity	NPC288838
0.8323	Intermediate Similarity	NPC477591
0.8214	Intermediate Similarity	NPC92796
0.8214	Intermediate Similarity	NPC135141
0.8187	Intermediate Similarity	NPC73767
0.8137	Intermediate Similarity	NPC469768
0.8137	Intermediate Similarity	NPC469784
0.8137	Intermediate Similarity	NPC469780
0.8137	Intermediate Similarity	NPC469767
0.8137	Intermediate Similarity	NPC469779
0.8137	Intermediate Similarity	NPC469761
0.8137	Intermediate Similarity	NPC469783
0.8086	Intermediate Similarity	NPC469766
0.8075	Intermediate Similarity	NPC110126
0.8063	Intermediate Similarity	NPC84911
0.8	Intermediate Similarity	NPC261195
0.8	Intermediate Similarity	NPC96102
0.8	Intermediate Similarity	NPC29886
0.7976	Intermediate Similarity	NPC325903
0.7965	Intermediate Similarity	NPC317105
0.795	Intermediate Similarity	NPC105127
0.7941	Intermediate Similarity	NPC286427
0.7904	Intermediate Similarity	NPC321911
0.7895	Intermediate Similarity	NPC41257
0.7882	Intermediate Similarity	NPC476464
0.7844	Intermediate Similarity	NPC469811
0.7844	Intermediate Similarity	NPC201380
0.7844	Intermediate Similarity	NPC179787
0.7831	Intermediate Similarity	NPC314372
0.7818	Intermediate Similarity	NPC190296
0.7811	Intermediate Similarity	NPC470233
0.7809	Intermediate Similarity	NPC280852
0.7805	Intermediate Similarity	NPC279081
0.7797	Intermediate Similarity	NPC477611
0.7791	Intermediate Similarity	NPC318065
0.7791	Intermediate Similarity	NPC56765
0.7791	Intermediate Similarity	NPC206819
0.7784	Intermediate Similarity	NPC63545
0.7758	Intermediate Similarity	NPC476454
0.7751	Intermediate Similarity	NPC24678
0.7751	Intermediate Similarity	NPC105818
0.775	Intermediate Similarity	NPC82295
0.7746	Intermediate Similarity	NPC44773
0.7746	Intermediate Similarity	NPC215584
0.7697	Intermediate Similarity	NPC2949
0.7697	Intermediate Similarity	NPC230002
0.7679	Intermediate Similarity	NPC143872
0.767	Intermediate Similarity	NPC315062
0.7667	Intermediate Similarity	NPC59269
0.7661	Intermediate Similarity	NPC73952
0.7661	Intermediate Similarity	NPC200214
0.7661	Intermediate Similarity	NPC25008
0.7661	Intermediate Similarity	NPC469760
0.7661	Intermediate Similarity	NPC469763
0.7661	Intermediate Similarity	NPC259644
0.7661	Intermediate Similarity	NPC469765
0.7661	Intermediate Similarity	NPC469786
0.7636	Intermediate Similarity	NPC315348
0.7636	Intermediate Similarity	NPC32002
0.7633	Intermediate Similarity	NPC471957
0.7622	Intermediate Similarity	NPC150259
0.7619	Intermediate Similarity	NPC159856
0.7616	Intermediate Similarity	NPC212376
0.7616	Intermediate Similarity	NPC70922
0.7616	Intermediate Similarity	NPC75540
0.7616	Intermediate Similarity	NPC80597
0.7616	Intermediate Similarity	NPC211572
0.76	Intermediate Similarity	NPC470203
0.7572	Intermediate Similarity	NPC115049
0.756	Intermediate Similarity	NPC316411
0.7557	Intermediate Similarity	NPC90723
0.7543	Intermediate Similarity	NPC229173
0.7543	Intermediate Similarity	NPC470204
0.7531	Intermediate Similarity	NPC475450
0.7529	Intermediate Similarity	NPC236711
0.7528	Intermediate Similarity	NPC201700
0.7524	Intermediate Similarity	NPC192712
0.7515	Intermediate Similarity	NPC314102
0.7515	Intermediate Similarity	NPC251722
0.7514	Intermediate Similarity	NPC34844
0.75	Intermediate Similarity	NPC198988
0.75	Intermediate Similarity	NPC470823
0.7486	Intermediate Similarity	NPC474880
0.7486	Intermediate Similarity	NPC221786
0.7486	Intermediate Similarity	NPC475990
0.7486	Intermediate Similarity	NPC194411
0.7485	Intermediate Similarity	NPC59084
0.7471	Intermediate Similarity	NPC469785
0.7469	Intermediate Similarity	NPC22079
0.7464	Intermediate Similarity	NPC244897
0.7457	Intermediate Similarity	NPC141926
0.7455	Intermediate Similarity	NPC325252
0.7443	Intermediate Similarity	NPC122141
0.7442	Intermediate Similarity	NPC33421
0.7442	Intermediate Similarity	NPC40070
0.744	Intermediate Similarity	NPC473868
0.744	Intermediate Similarity	NPC63157
0.7438	Intermediate Similarity	NPC250361
0.743	Intermediate Similarity	NPC63751
0.7429	Intermediate Similarity	NPC469762
0.7421	Intermediate Similarity	NPC304203
0.7419	Intermediate Similarity	NPC99939
0.7419	Intermediate Similarity	NPC308931
0.7419	Intermediate Similarity	NPC15102
0.7416	Intermediate Similarity	NPC267853
0.7407	Intermediate Similarity	NPC473587
0.7399	Intermediate Similarity	NPC216713
0.7389	Intermediate Similarity	NPC474897
0.7381	Intermediate Similarity	NPC115611
0.7378	Intermediate Similarity	NPC473930
0.7377	Intermediate Similarity	NPC284775
0.7374	Intermediate Similarity	NPC49954
0.7374	Intermediate Similarity	NPC474561
0.7363	Intermediate Similarity	NPC275305
0.7363	Intermediate Similarity	NPC37423
0.7362	Intermediate Similarity	NPC475428
0.736	Intermediate Similarity	NPC311276
0.7354	Intermediate Similarity	NPC231536
0.7349	Intermediate Similarity	NPC218268
0.7348	Intermediate Similarity	NPC82331
0.7346	Intermediate Similarity	NPC473762
0.7322	Intermediate Similarity	NPC474958
0.7321	Intermediate Similarity	NPC88097
0.7317	Intermediate Similarity	NPC179365
0.7303	Intermediate Similarity	NPC282231
0.7302	Intermediate Similarity	NPC321708
0.7297	Intermediate Similarity	NPC16659
0.7283	Intermediate Similarity	NPC2272
0.7283	Intermediate Similarity	NPC68354
0.7283	Intermediate Similarity	NPC151939
0.7278	Intermediate Similarity	NPC49217
0.7278	Intermediate Similarity	NPC160105
0.7263	Intermediate Similarity	NPC162799
0.7263	Intermediate Similarity	NPC40779
0.7247	Intermediate Similarity	NPC279918
0.7243	Intermediate Similarity	NPC215795
0.7243	Intermediate Similarity	NPC213468
0.7243	Intermediate Similarity	NPC176199
0.7243	Intermediate Similarity	NPC265710
0.7243	Intermediate Similarity	NPC104712
0.7225	Intermediate Similarity	NPC21605
0.7225	Intermediate Similarity	NPC476460
0.7225	Intermediate Similarity	NPC470111
0.7222	Intermediate Similarity	NPC274229
0.7219	Intermediate Similarity	NPC104483
0.7216	Intermediate Similarity	NPC476219
0.7216	Intermediate Similarity	NPC476297
0.7216	Intermediate Similarity	NPC477815
0.7204	Intermediate Similarity	NPC300688
0.7202	Intermediate Similarity	NPC125746
0.7198	Intermediate Similarity	NPC97343
0.7194	Intermediate Similarity	NPC252338
0.7193	Intermediate Similarity	NPC20144
0.7189	Intermediate Similarity	NPC473380
0.7189	Intermediate Similarity	NPC240088
0.7188	Intermediate Similarity	NPC41174
0.7184	Intermediate Similarity	NPC37548
0.7168	Intermediate Similarity	NPC316069
0.7167	Intermediate Similarity	NPC194640
0.7167	Intermediate Similarity	NPC149265
0.7151	Intermediate Similarity	NPC242556
0.7151	Intermediate Similarity	NPC131718
0.7135	Intermediate Similarity	NPC129721
0.7128	Intermediate Similarity	NPC227582
0.7127	Intermediate Similarity	NPC280864
0.7127	Intermediate Similarity	NPC17751
0.7126	Intermediate Similarity	NPC477134
0.7121	Intermediate Similarity	NPC260900
0.712	Intermediate Similarity	NPC314603
0.7118	Intermediate Similarity	NPC312092
0.7112	Intermediate Similarity	NPC164228
0.711	Intermediate Similarity	NPC204141
0.711	Intermediate Similarity	NPC470440
0.7105	Intermediate Similarity	NPC94752
0.7097	Intermediate Similarity	NPC248454
0.7095	Intermediate Similarity	NPC230869
0.709	Intermediate Similarity	NPC472294
0.7088	Intermediate Similarity	NPC54988
0.7079	Intermediate Similarity	NPC51054
0.7076	Intermediate Similarity	NPC284635
0.7074	Intermediate Similarity	NPC307191
0.7072	Intermediate Similarity	NPC478182
0.7068	Intermediate Similarity	NPC17059
0.7065	Intermediate Similarity	NPC470498
0.7062	Intermediate Similarity	NPC326422
0.7059	Intermediate Similarity	NPC11126
0.7056	Intermediate Similarity	NPC74413
0.7037	Intermediate Similarity	NPC46358
0.7031	Intermediate Similarity	NPC213629
0.7022	Intermediate Similarity	NPC470507
0.7022	Intermediate Similarity	NPC38736
0.7017	Intermediate Similarity	NPC225018
0.7005	Intermediate Similarity	NPC145885

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 NPC314919 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	465
0.1-0.2	965
0.2-0.3	1113
0.3-0.4	2261
0.4-0.5	2167
0.5-0.6	1571
0.6-0.7	509
0.7-0.8	92
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8293	Intermediate Similarity	NPD2172	Phase 1
0.8258	Intermediate Similarity	NPD6217	Discontinued
0.8081	Intermediate Similarity	NPD1248	Discontinued
0.8075	Intermediate Similarity	NPD786	Approved
0.8012	Intermediate Similarity	NPD3100	Discontinued
0.8012	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD1722	Approved
0.7941	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD2165	Phase 1
0.7882	Intermediate Similarity	NPD3115	Approved
0.7882	Intermediate Similarity	NPD3113	Approved
0.7882	Intermediate Similarity	NPD3112	Approved
0.7882	Intermediate Similarity	NPD3114	Approved
0.7882	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD2837	Discontinued
0.7759	Intermediate Similarity	NPD3323	Discontinued
0.7747	Intermediate Similarity	NPD5892	Approved
0.7713	Intermediate Similarity	NPD2316	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD5538	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD6595	Phase 3
0.767	Intermediate Similarity	NPD2639	Approved
0.767	Intermediate Similarity	NPD2642	Approved
0.7667	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD3339	Approved
0.7636	Intermediate Similarity	NPD2072	Approved
0.7636	Intermediate Similarity	NPD2074	Approved
0.7636	Intermediate Similarity	NPD2075	Approved
0.7636	Intermediate Similarity	NPD2073	Approved
0.7627	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD5254	Discontinued
0.753	Intermediate Similarity	NPD768	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD4547	Phase 3
0.7528	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5106	Approved
0.75	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5105	Approved
0.7486	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD2580	Discontinued
0.7447	Intermediate Similarity	NPD6133	Discontinued
0.7446	Intermediate Similarity	NPD1895	Discontinued
0.7444	Intermediate Similarity	NPD3609	Approved
0.7444	Intermediate Similarity	NPD3117	Approved
0.7444	Intermediate Similarity	NPD3116	Approved
0.7444	Intermediate Similarity	NPD3610	Approved
0.7443	Intermediate Similarity	NPD1403	Approved
0.7443	Intermediate Similarity	NPD1404	Approved
0.7439	Intermediate Similarity	NPD3385	Approved
0.743	Intermediate Similarity	NPD2641	Approved
0.743	Intermediate Similarity	NPD2640	Approved
0.7429	Intermediate Similarity	NPD6497	Approved
0.7405	Intermediate Similarity	NPD1332	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD4128	Approved
0.7363	Intermediate Similarity	NPD5065	Approved
0.7351	Intermediate Similarity	NPD1708	Approved
0.7351	Intermediate Similarity	NPD1707	Approved
0.7341	Intermediate Similarity	NPD4463	Approved
0.7341	Intermediate Similarity	NPD4462	Approved
0.7326	Intermediate Similarity	NPD1227	Phase 2
0.7322	Intermediate Similarity	NPD4075	Phase 2
0.7308	Intermediate Similarity	NPD7217	Approved
0.7308	Intermediate Similarity	NPD7216	Approved
0.7302	Intermediate Similarity	NPD2729	Approved
0.7302	Intermediate Similarity	NPD2730	Approved
0.7302	Intermediate Similarity	NPD2728	Approved
0.7301	Intermediate Similarity	NPD3654	Approved
0.7294	Intermediate Similarity	NPD2006	Phase 2
0.7283	Intermediate Similarity	NPD3505	Approved
0.7283	Intermediate Similarity	NPD2430	Phase 2
0.7283	Intermediate Similarity	NPD4181	Approved
0.7283	Intermediate Similarity	NPD3506	Approved
0.7268	Intermediate Similarity	NPD3230	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1683	Approved
0.7256	Intermediate Similarity	NPD3476	Approved
0.7256	Intermediate Similarity	NPD3475	Approved
0.7254	Intermediate Similarity	NPD6278	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD4848	Phase 1
0.7243	Intermediate Similarity	NPD4076	Approved
0.7243	Intermediate Similarity	NPD4079	Approved
0.7238	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD2868	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD45	Approved
0.7202	Intermediate Similarity	NPD6554	Approved
0.7198	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD1554	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD2144	Approved
0.7178	Intermediate Similarity	NPD2118	Approved
0.7178	Intermediate Similarity	NPD2119	Approved
0.7165	Intermediate Similarity	NPD2960	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3771	Phase 3
0.7143	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD4384	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD2793	Discontinued
0.7104	Intermediate Similarity	NPD5436	Phase 1
0.7101	Intermediate Similarity	NPD1262	Discovery
0.709	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD7185	Discontinued
0.7074	Intermediate Similarity	NPD3038	Discontinued
0.7073	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD991	Phase 2
0.7068	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD8431	Approved
0.7068	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD5426	Phase 3
0.7045	Intermediate Similarity	NPD3833	Phase 3
0.7045	Intermediate Similarity	NPD3835	Phase 3
0.7039	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD6615	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD7619	Phase 3
0.7026	Intermediate Similarity	NPD7618	Phase 3
0.7024	Intermediate Similarity	NPD4029	Approved
0.7024	Intermediate Similarity	NPD4030	Approved
0.7024	Intermediate Similarity	NPD4028	Approved
0.7017	Intermediate Similarity	NPD5315	Discontinued
0.7017	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1860	Approved
0.6995	Remote Similarity	NPD5145	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD3929	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD2007	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD3852	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD4383	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD3961	Discontinued
0.6965	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5021	Discontinued
0.6943	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD1256	Approved
0.6941	Remote Similarity	NPD1253	Approved
0.6941	Remote Similarity	NPD1255	Approved
0.6941	Remote Similarity	NPD1254	Approved
0.6931	Remote Similarity	NPD3310	Approved
0.6923	Remote Similarity	NPD3944	Approved
0.6923	Remote Similarity	NPD3942	Approved
0.6919	Remote Similarity	NPD4973	Approved
0.6919	Remote Similarity	NPD945	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD803	Phase 1
0.6904	Remote Similarity	NPD1851	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD4649	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD8458	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD7164	Discontinued
0.6882	Remote Similarity	NPD5472	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD3015	Discontinued
0.6865	Remote Similarity	NPD4639	Approved
0.6865	Remote Similarity	NPD4640	Approved
0.6865	Remote Similarity	NPD4638	Approved
0.6862	Remote Similarity	NPD6471	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD2771	Approved
0.686	Remote Similarity	NPD8488	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD1534	Approved
0.6853	Remote Similarity	NPD3791	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD4326	Phase 2
0.6845	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD4703	Approved
0.6836	Remote Similarity	NPD4702	Approved
0.6829	Remote Similarity	NPD2938	Approved
0.6829	Remote Similarity	NPD2940	Approved
0.6825	Remote Similarity	NPD2315	Approved
0.6811	Remote Similarity	NPD3361	Phase 1
0.6809	Remote Similarity	NPD482	Approved
0.6806	Remote Similarity	NPD2301	Approved
0.6806	Remote Similarity	NPD4891	Phase 2
0.6806	Remote Similarity	NPD4011	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD2310	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD2150	Discontinued
0.6791	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD3341	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD1937	Approved
0.6784	Remote Similarity	NPD2880	Discontinued
0.6774	Remote Similarity	NPD2333	Discontinued
0.6772	Remote Similarity	NPD5471	Phase 3
0.6771	Remote Similarity	NPD2094	Phase 2
0.6771	Remote Similarity	NPD2092	Phase 2
0.6771	Remote Similarity	NPD2095	Phase 2
0.6765	Remote Similarity	NPD2008	Discontinued
0.6761	Remote Similarity	NPD1918	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD5541	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD409	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD750	Phase 2
0.6754	Remote Similarity	NPD3927	Phase 2
0.6751	Remote Similarity	NPD4615	Phase 2
0.6748	Remote Similarity	NPD5397	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD715	Phase 3
0.6737	Remote Similarity	NPD7111	Discontinued
0.6737	Remote Similarity	NPD2731	Phase 2
0.6736	Remote Similarity	NPD2091	Phase 2
0.6736	Remote Similarity	NPD2096	Phase 2
0.6736	Remote Similarity	NPD7564	Discontinued

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