NPASS Compound

Structure

CID314058 OpenBabel06191716122D 28 33 0 0 1 0 0 0 0 0999 V2000 -1.5054 1.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4760 4.8324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6823 -0.7582 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4138 1.4363 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5055 -0.7859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5718 0.9503 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5386 -0.8878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5722 2.8955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3291 0.8888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0008 3.8472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3617 3.0608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4140 2.4092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9008 0.1024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7296 2.4095 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2028 2.8962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3622 0.7869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6393 2.4102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7294 1.4366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9670 -0.1014 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0452 2.4098 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0450 1.4370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2024 0.9510 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6395 1.4373 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.2802 2.9090 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -3.9152 0.2093 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 1.8873 0.9506 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.9661 3.9490 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 12 1 0 0 0 0 5 7 2 0 0 0 0 5 13 1 0 0 0 0 6 18 1 0 0 0 0 7 19 1 0 0 0 0 8 12 2 0 0 0 0 8 14 1 0 0 0 0 9 13 2 0 0 0 0 9 16 1 0 0 0 0 10 15 2 0 0 0 0 10 27 1 0 0 0 0 11 17 2 0 0 0 0 11 27 1 0 0 0 0 12 24 1 0 0 0 0 13 25 1 0 0 0 0 14 18 2 0 0 0 0 14 20 1 0 0 0 0 15 17 1 0 0 0 0 15 20 1 0 0 0 0 16 19 2 0 0 0 0 16 23 1 0 0 0 0 17 23 1 0 0 0 0 18 26 1 0 0 0 0 19 28 1 0 0 0 0 20 21 2 0 0 0 0 21 22 1 0 0 0 0 21 26 1 0 0 0 0 22 23 1 1 0 0 0 22 28 1 0 0 0 0 23 1 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	407.1
Volume:	394.71
LogP:	6.521
LogD:	4.64
LogS:	-8.052
# Rotatable Bonds:	0
TPSA:	23.96
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.363
Synthetic Accessibility Score:	3.901
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:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.027
MDCK Permeability:	1.3895745723857544e-05
Pgp-inhibitor:	0.991
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.446
30% Bioavailability (F30%):	0.958

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.021
Plasma Protein Binding (PPB):	97.37657165527344%
Volume Distribution (VD):	2.391
Pgp-substrate:	1.5001274347305298%

ADMET: Metabolism

CYP1A2-inhibitor:	0.93
CYP1A2-substrate:	0.914
CYP2C19-inhibitor:	0.872
CYP2C19-substrate:	0.472
CYP2C9-inhibitor:	0.827
CYP2C9-substrate:	0.305
CYP2D6-inhibitor:	0.873
CYP2D6-substrate:	0.857
CYP3A4-inhibitor:	0.599
CYP3A4-substrate:	0.855

ADMET: Excretion

Clearance (CL):	7.975
Half-life (T1/2):	0.026

ADMET: Toxicity

hERG Blockers:	0.919
Human Hepatotoxicity (H-HT):	0.155
Drug-inuced Liver Injury (DILI):	0.912
AMES Toxicity:	0.424
Rat Oral Acute Toxicity:	0.571
Maximum Recommended Daily Dose:	0.983
Skin Sensitization:	0.127
Carcinogencity:	0.864
Eye Corrosion:	0.003
Eye Irritation:	0.019
Respiratory Toxicity:	0.952

Download Data

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

Natural Product: NPC314058

Natural Product ID:	NPC314058
*Common Name:**	VOENECZXFQZIKA-PKTZIBPZSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	VOENECZXFQZIKA-PKTZIBPZSA-N
Standard InCHI:	InChI=1S/C23H19Cl2N3/c1-23-16-9-13(25)5-7-19(16)28(3)22(23)21-20(15-10-27(2)11-17(15)23)14-8-12(24)4-6-18(14)26-21/h4-11,22,26H,1-3H3/t22-,23+/m1/s1
SMILES:	Cn1cc2c(c1)[C@]1(C)c3cc(Cl)ccc3N([C@@H]1c1c2c2cc(Cl)ccc2[nH]1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3326887
PubChem CID:	86342557
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0000210] Carbazoles [CHEMONTID:0001865] Pyrrolocarbazoles [CHEMONTID:0001866] Indolocarbazoles

*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[549640]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	128.0	ug.mL-1	PMID[549640]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	128.0	ug.mL-1	PMID[549640]
NPT1261	Organism	Bacillus thuringiensis	Bacillus thuringiensis	MIC	>	128.0	ug.mL-1	PMID[549640]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	128.0	ug.mL-1	PMID[549640]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	128.0	ug.mL-1	PMID[549640]

☑ 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 NPC314058 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	1271
0.1-0.2	13928
0.2-0.3	18932
0.3-0.4	3947
0.4-0.5	1995
0.5-0.6	1594
0.6-0.7	842
0.7-0.8	178
0.8-0.85	5
0.85-0.9	0
0.9-0.95	1
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC316018
0.9883	High Similarity	NPC316359
0.9883	High Similarity	NPC315617
0.9298	High Similarity	NPC314919
0.8343	Intermediate Similarity	NPC83381
0.8208	Intermediate Similarity	NPC216643
0.8057	Intermediate Similarity	NPC477591
0.8057	Intermediate Similarity	NPC41257
0.8023	Intermediate Similarity	NPC53947
0.7955	Intermediate Similarity	NPC206819
0.7955	Intermediate Similarity	NPC56765
0.7955	Intermediate Similarity	NPC318065
0.7953	Intermediate Similarity	NPC288838
0.791	Intermediate Similarity	NPC44773
0.791	Intermediate Similarity	NPC215584
0.7898	Intermediate Similarity	NPC286427
0.7772	Intermediate Similarity	NPC280852
0.7727	Intermediate Similarity	NPC325903
0.7722	Intermediate Similarity	NPC317105
0.7714	Intermediate Similarity	NPC33421
0.7654	Intermediate Similarity	NPC135141
0.7654	Intermediate Similarity	NPC92796
0.7602	Intermediate Similarity	NPC73767
0.76	Intermediate Similarity	NPC201380
0.76	Intermediate Similarity	NPC179787
0.7558	Intermediate Similarity	NPC469783
0.7558	Intermediate Similarity	NPC469784
0.7558	Intermediate Similarity	NPC469761
0.7558	Intermediate Similarity	NPC469768
0.7558	Intermediate Similarity	NPC469779
0.7558	Intermediate Similarity	NPC469767
0.7558	Intermediate Similarity	NPC469780
0.7557	Intermediate Similarity	NPC321911
0.7554	Intermediate Similarity	NPC194411
0.7543	Intermediate Similarity	NPC63545
0.7527	Intermediate Similarity	NPC90723
0.7514	Intermediate Similarity	NPC229173
0.7514	Intermediate Similarity	NPC469766
0.75	Intermediate Similarity	NPC110126
0.75	Intermediate Similarity	NPC469811
0.7485	Intermediate Similarity	NPC84911
0.7472	Intermediate Similarity	NPC470233
0.7444	Intermediate Similarity	NPC476464
0.7433	Intermediate Similarity	NPC37423
0.7433	Intermediate Similarity	NPC275305
0.7427	Intermediate Similarity	NPC96102
0.7427	Intermediate Similarity	NPC261195
0.7427	Intermediate Similarity	NPC29886
0.7416	Intermediate Similarity	NPC40070
0.7414	Intermediate Similarity	NPC476454
0.7407	Intermediate Similarity	NPC215795
0.7407	Intermediate Similarity	NPC176199
0.7384	Intermediate Similarity	NPC105127
0.7366	Intermediate Similarity	NPC474897
0.7363	Intermediate Similarity	NPC474880
0.7363	Intermediate Similarity	NPC221786
0.7363	Intermediate Similarity	NPC475990
0.7354	Intermediate Similarity	NPC68354
0.7354	Intermediate Similarity	NPC59269
0.7348	Intermediate Similarity	NPC51054
0.7337	Intermediate Similarity	NPC162799
0.7308	Intermediate Similarity	NPC236711
0.7306	Intermediate Similarity	NPC99939
0.7306	Intermediate Similarity	NPC15102
0.7306	Intermediate Similarity	NPC308931
0.7303	Intermediate Similarity	NPC477134
0.7299	Intermediate Similarity	NPC312092
0.7299	Intermediate Similarity	NPC88097
0.7288	Intermediate Similarity	NPC314372
0.7287	Intermediate Similarity	NPC477611
0.7283	Intermediate Similarity	NPC314102
0.7283	Intermediate Similarity	NPC251722
0.7283	Intermediate Similarity	NPC470203
0.7273	Intermediate Similarity	NPC190296
0.7267	Intermediate Similarity	NPC198988
0.7257	Intermediate Similarity	NPC279081
0.7257	Intermediate Similarity	NPC2949
0.7251	Intermediate Similarity	NPC473930
0.7245	Intermediate Similarity	NPC231536
0.7235	Intermediate Similarity	NPC315062
0.7228	Intermediate Similarity	NPC122141
0.7228	Intermediate Similarity	NPC470204
0.7225	Intermediate Similarity	NPC325252
0.7222	Intermediate Similarity	NPC105818
0.7222	Intermediate Similarity	NPC24678
0.7219	Intermediate Similarity	NPC201700
0.7207	Intermediate Similarity	NPC21605
0.72	Intermediate Similarity	NPC315348
0.72	Intermediate Similarity	NPC32002
0.7193	Intermediate Similarity	NPC82295
0.7193	Intermediate Similarity	NPC475450
0.7188	Intermediate Similarity	NPC300688
0.7184	Intermediate Similarity	NPC150259
0.7175	Intermediate Similarity	NPC20144
0.7173	Intermediate Similarity	NPC151939
0.7159	Intermediate Similarity	NPC230002
0.7151	Intermediate Similarity	NPC143872
0.7143	Intermediate Similarity	NPC73952
0.7143	Intermediate Similarity	NPC25008
0.7143	Intermediate Similarity	NPC469765
0.7143	Intermediate Similarity	NPC200214
0.7143	Intermediate Similarity	NPC259644
0.7143	Intermediate Similarity	NPC469786
0.7143	Intermediate Similarity	NPC469763
0.7143	Intermediate Similarity	NPC82331
0.7143	Intermediate Similarity	NPC469760
0.7136	Intermediate Similarity	NPC316411
0.7136	Intermediate Similarity	NPC304203
0.7128	Intermediate Similarity	NPC63751
0.7126	Intermediate Similarity	NPC218268
0.712	Intermediate Similarity	NPC474958
0.7119	Intermediate Similarity	NPC473868
0.7119	Intermediate Similarity	NPC63157
0.7111	Intermediate Similarity	NPC471957
0.7104	Intermediate Similarity	NPC70922
0.7104	Intermediate Similarity	NPC211572
0.7104	Intermediate Similarity	NPC212376
0.7104	Intermediate Similarity	NPC80597
0.7104	Intermediate Similarity	NPC75540
0.7097	Intermediate Similarity	NPC192712
0.7095	Intermediate Similarity	NPC159856
0.7093	Intermediate Similarity	NPC179365
0.7076	Intermediate Similarity	NPC473587
0.7071	Intermediate Similarity	NPC95783
0.7065	Intermediate Similarity	NPC115049
0.7062	Intermediate Similarity	NPC59084
0.7062	Intermediate Similarity	NPC115611
0.7045	Intermediate Similarity	NPC244897
0.7045	Intermediate Similarity	NPC169433
0.7035	Intermediate Similarity	NPC475428
0.7035	Intermediate Similarity	NPC22079
0.7021	Intermediate Similarity	NPC274229
0.7019	Intermediate Similarity	NPC87755
0.7018	Intermediate Similarity	NPC473762
0.7017	Intermediate Similarity	NPC470111
0.7014	Intermediate Similarity	NPC473757
0.7011	Intermediate Similarity	NPC34844
0.7011	Intermediate Similarity	NPC476219
0.701	Intermediate Similarity	NPC16659
0.7	Intermediate Similarity	NPC97343
0.7	Intermediate Similarity	NPC250361
0.7	Intermediate Similarity	NPC267853
0.6995	Remote Similarity	NPC265576
0.6995	Remote Similarity	NPC470823
0.699	Remote Similarity	NPC472294
0.6984	Remote Similarity	NPC474561
0.6984	Remote Similarity	NPC49954
0.6973	Remote Similarity	NPC469785
0.6971	Remote Similarity	NPC166492
0.6971	Remote Similarity	NPC473362
0.6968	Remote Similarity	NPC478182
0.6966	Remote Similarity	NPC284635
0.6963	Remote Similarity	NPC201634
0.6963	Remote Similarity	NPC477714
0.6959	Remote Similarity	NPC265710
0.6959	Remote Similarity	NPC213468
0.6957	Remote Similarity	NPC141926
0.6957	Remote Similarity	NPC200743
0.6952	Remote Similarity	NPC126066
0.6952	Remote Similarity	NPC475422
0.6948	Remote Similarity	NPC472027
0.6935	Remote Similarity	NPC321708
0.6935	Remote Similarity	NPC469762
0.6919	Remote Similarity	NPC38736
0.6919	Remote Similarity	NPC476297
0.6919	Remote Similarity	NPC94752
0.6916	Remote Similarity	NPC477715
0.6915	Remote Similarity	NPC282231
0.6907	Remote Similarity	NPC473380
0.6907	Remote Similarity	NPC240088
0.6907	Remote Similarity	NPC284775
0.6906	Remote Similarity	NPC204141
0.6906	Remote Similarity	NPC470440
0.6902	Remote Similarity	NPC216713
0.6895	Remote Similarity	NPC160105
0.6885	Remote Similarity	NPC37548
0.6884	Remote Similarity	NPC17059
0.6881	Remote Similarity	NPC326422
0.6878	Remote Similarity	NPC311276
0.6878	Remote Similarity	NPC478184
0.6878	Remote Similarity	NPC194640
0.6872	Remote Similarity	NPC11126
0.6862	Remote Similarity	NPC279918
0.6856	Remote Similarity	NPC288785
0.6853	Remote Similarity	NPC19679
0.685	Remote Similarity	NPC213629
0.6847	Remote Similarity	NPC195314
0.6845	Remote Similarity	NPC106771
0.6845	Remote Similarity	NPC205254
0.6845	Remote Similarity	NPC303820
0.6845	Remote Similarity	NPC252338
0.6845	Remote Similarity	NPC23420
0.6844	Remote Similarity	NPC104712
0.6839	Remote Similarity	NPC161861
0.6832	Remote Similarity	NPC47190
0.6829	Remote Similarity	NPC171317
0.6825	Remote Similarity	NPC225018
0.6818	Remote Similarity	NPC228835
0.6816	Remote Similarity	NPC104483
0.6812	Remote Similarity	NPC52909

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 NPC314058 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	479
0.1-0.2	860
0.2-0.3	1266
0.3-0.4	2317
0.4-0.5	2138
0.5-0.6	1542
0.6-0.7	469
0.7-0.8	78
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8023	Intermediate Similarity	NPD3323	Discontinued
0.7956	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD2172	Phase 1
0.7914	Intermediate Similarity	NPD6217	Discontinued
0.7772	Intermediate Similarity	NPD2316	Clinical (unspecified phase)
0.7735	Intermediate Similarity	NPD1248	Discontinued
0.7657	Intermediate Similarity	NPD3100	Discontinued
0.764	Intermediate Similarity	NPD473	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD4181	Approved
0.7622	Intermediate Similarity	NPD4128	Approved
0.7619	Intermediate Similarity	NPD5892	Approved
0.7609	Intermediate Similarity	NPD3610	Approved
0.7609	Intermediate Similarity	NPD3609	Approved
0.7602	Intermediate Similarity	NPD786	Approved
0.7596	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD5538	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD1683	Approved
0.7542	Intermediate Similarity	NPD2580	Discontinued
0.7529	Intermediate Similarity	NPD5254	Discontinued
0.7528	Intermediate Similarity	NPD2837	Discontinued
0.7487	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD3115	Approved
0.7444	Intermediate Similarity	NPD3113	Approved
0.7444	Intermediate Similarity	NPD3114	Approved
0.7444	Intermediate Similarity	NPD3112	Approved
0.7427	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD1722	Approved
0.7405	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD4547	Phase 3
0.7394	Intermediate Similarity	NPD4075	Phase 2
0.7389	Intermediate Similarity	NPD2165	Phase 1
0.7377	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7354	Intermediate Similarity	NPD3506	Approved
0.7354	Intermediate Similarity	NPD3505	Approved
0.7351	Intermediate Similarity	NPD2639	Approved
0.7351	Intermediate Similarity	NPD2642	Approved
0.7333	Intermediate Similarity	NPD3339	Approved
0.733	Intermediate Similarity	NPD1895	Discontinued
0.7323	Intermediate Similarity	NPD2960	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD4076	Approved
0.7316	Intermediate Similarity	NPD4079	Approved
0.7292	Intermediate Similarity	NPD5106	Approved
0.7292	Intermediate Similarity	NPD5105	Approved
0.7283	Intermediate Similarity	NPD5315	Discontinued
0.7277	Intermediate Similarity	NPD6595	Phase 3
0.7268	Intermediate Similarity	NPD2793	Discontinued
0.7245	Intermediate Similarity	NPD6133	Discontinued
0.7231	Intermediate Similarity	NPD3961	Discontinued
0.7231	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD1227	Phase 2
0.7213	Intermediate Similarity	NPD6497	Approved
0.72	Intermediate Similarity	NPD2072	Approved
0.72	Intermediate Similarity	NPD2075	Approved
0.72	Intermediate Similarity	NPD2073	Approved
0.72	Intermediate Similarity	NPD2074	Approved
0.7196	Intermediate Similarity	NPD7217	Approved
0.7196	Intermediate Similarity	NPD7216	Approved
0.7189	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD6615	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD3230	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD6278	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8431	Approved
0.7135	Intermediate Similarity	NPD1404	Approved
0.7135	Intermediate Similarity	NPD1403	Approved
0.7128	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD2640	Approved
0.7128	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD2641	Approved
0.711	Intermediate Similarity	NPD3385	Approved
0.7107	Intermediate Similarity	NPD2729	Approved
0.7107	Intermediate Similarity	NPD2730	Approved
0.7107	Intermediate Similarity	NPD2728	Approved
0.7102	Intermediate Similarity	NPD768	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD7185	Discontinued
0.7074	Intermediate Similarity	NPD3929	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD5145	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD5065	Approved
0.7062	Intermediate Similarity	NPD1707	Approved
0.7062	Intermediate Similarity	NPD1708	Approved
0.7053	Intermediate Similarity	NPD3116	Approved
0.7053	Intermediate Similarity	NPD3117	Approved
0.7041	Intermediate Similarity	NPD2868	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4640	Approved
0.7037	Intermediate Similarity	NPD4638	Approved
0.7037	Intermediate Similarity	NPD4639	Approved
0.7037	Intermediate Similarity	NPD5021	Discontinued
0.7031	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD1332	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD2144	Approved
0.6989	Remote Similarity	NPD45	Approved
0.6989	Remote Similarity	NPD6554	Approved
0.6974	Remote Similarity	NPD4649	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD7164	Discontinued
0.6954	Remote Similarity	NPD3771	Phase 3
0.694	Remote Similarity	NPD4463	Approved
0.694	Remote Similarity	NPD4462	Approved
0.6936	Remote Similarity	NPD3475	Approved
0.6936	Remote Similarity	NPD3476	Approved
0.6931	Remote Similarity	NPD7618	Phase 3
0.6931	Remote Similarity	NPD7619	Phase 3
0.6915	Remote Similarity	NPD4384	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD5436	Phase 1
0.6897	Remote Similarity	NPD4848	Phase 1
0.6893	Remote Similarity	NPD1262	Discovery
0.6889	Remote Similarity	NPD2006	Phase 2
0.6888	Remote Similarity	NPD3038	Discontinued
0.6887	Remote Similarity	NPD8458	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD2430	Phase 2
0.6884	Remote Similarity	NPD2310	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD7394	Phase 2
0.6879	Remote Similarity	NPD3654	Approved
0.6875	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5012	Phase 2
0.6875	Remote Similarity	NPD6714	Phase 3
0.6866	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD6664	Approved
0.6854	Remote Similarity	NPD8488	Clinical (unspecified phase)
0.6834	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD977	Approved
0.6828	Remote Similarity	NPD975	Approved
0.6828	Remote Similarity	NPD976	Approved
0.6823	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD7111	Discontinued
0.6818	Remote Similarity	NPD1860	Approved
0.6816	Remote Similarity	NPD945	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD1554	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD5426	Phase 3
0.6791	Remote Similarity	NPD6803	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.678	Remote Similarity	NPD4880	Discontinued
0.6763	Remote Similarity	NPD2119	Approved
0.6763	Remote Similarity	NPD2118	Approved
0.6751	Remote Similarity	NPD3310	Approved
0.6742	Remote Similarity	NPD1254	Approved
0.6742	Remote Similarity	NPD1253	Approved
0.6742	Remote Similarity	NPD1256	Approved
0.6742	Remote Similarity	NPD1255	Approved
0.6736	Remote Similarity	NPD4973	Approved
0.6734	Remote Similarity	NPD4957	Phase 2
0.6733	Remote Similarity	NPD6281	Approved
0.673	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD2411	Approved
0.6726	Remote Similarity	NPD7824	Approved
0.6723	Remote Similarity	NPD4029	Approved
0.6723	Remote Similarity	NPD3944	Approved
0.6723	Remote Similarity	NPD4028	Approved
0.6723	Remote Similarity	NPD4030	Approved
0.6723	Remote Similarity	NPD3942	Approved
0.6719	Remote Similarity	NPD3361	Phase 1
0.6717	Remote Similarity	NPD4011	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD5590	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD2007	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD4047	Discontinued
0.6702	Remote Similarity	NPD2150	Discontinued
0.6701	Remote Similarity	NPD6827	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD6828	Phase 2
0.6701	Remote Similarity	NPD3341	Clinical (unspecified phase)
0.67	Remote Similarity	NPD2774	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD7271	Approved
0.6696	Remote Similarity	NPD8316	Phase 2
0.6696	Remote Similarity	NPD8317	Phase 2
0.6684	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD6471	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD1534	Approved
0.6682	Remote Similarity	NPD7781	Approved
0.6682	Remote Similarity	NPD7780	Approved
0.6667	Remote Similarity	NPD5541	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3835	Phase 3
0.6667	Remote Similarity	NPD4902	Discontinued
0.6667	Remote Similarity	NPD991	Phase 2
0.6667	Remote Similarity	NPD992	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3833	Phase 3
0.6651	Remote Similarity	NPD8093	Discontinued
0.665	Remote Similarity	NPD2315	Approved
0.665	Remote Similarity	NPD1887	Clinical (unspecified phase)
0.665	Remote Similarity	NPD1851	Clinical (unspecified phase)
0.665	Remote Similarity	NPD7564	Discontinued
0.6637	Remote Similarity	NPD7731	Approved
0.6637	Remote Similarity	NPD7789	Approved
0.6637	Remote Similarity	NPD7790	Approved
0.6637	Remote Similarity	NPD7953	Approved
0.6637	Remote Similarity	NPD7730	Approved
0.6637	Remote Similarity	NPD7950	Approved
0.6637	Remote Similarity	NPD7951	Approved
0.6637	Remote Similarity	NPD7952	Approved
0.6637	Remote Similarity	NPD7791	Approved
0.6633	Remote Similarity	NPD2301	Approved
0.6633	Remote Similarity	NPD4383	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD3799	Suspended

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