NPASS Compound

Structure

CID204565 OpenBabel06191715592D 27 29 0 0 1 0 0 0 0 0999 V2000 -4.9939 -3.5427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5692 -2.5497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1044 -0.9024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7618 -4.4088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7618 -4.4088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -2.6361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1278 -3.0427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5298 -3.5427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6637 -3.0427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3275 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7322 -0.4601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6637 1.2157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3613 -1.5715 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7377 -0.5646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6637 0.2157 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3958 -3.0427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6637 -2.0427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5298 -1.5427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3958 -2.0427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4102 -1.2625 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4102 -0.5646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2618 -3.5427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1389 -1.3736 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 0.0000 -1.8271 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.2023 1.7157 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3613 -0.2556 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 2 0 0 0 0 2 13 1 0 0 0 0 3 13 1 0 0 0 0 4 22 1 0 0 0 0 5 22 1 0 0 0 0 6 25 1 0 0 0 0 7 22 1 0 0 0 0 8 9 2 0 0 0 0 8 16 1 0 0 0 0 9 17 1 0 0 0 0 10 14 1 0 0 0 0 10 15 1 0 0 0 0 11 14 2 0 0 0 0 11 23 1 0 0 0 0 12 26 1 0 0 0 0 14 18 1 0 0 0 0 15 12 1 1 0 0 0 15 24 1 0 0 0 0 16 19 2 0 0 0 0 16 22 1 0 0 0 0 17 18 2 0 0 0 0 17 25 1 0 0 0 0 18 19 1 0 0 0 0 19 23 1 0 0 0 0 20 13 1 6 0 0 0 20 21 1 0 0 0 0 20 25 1 0 0 0 0 21 24 2 3 0 0 0 21 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	369.24
Volume:	398.151
LogP:	3.981
LogD:	3.439
LogS:	-4.095
# Rotatable Bonds:	4
TPSA:	68.36
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.726
Synthetic Accessibility Score:	4.527
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.866
MDCK Permeability:	1.163977685791906e-05
Pgp-inhibitor:	0.024
Pgp-substrate:	0.783
Human Intestinal Absorption (HIA):	0.135
20% Bioavailability (F20%):	0.417
30% Bioavailability (F30%):	0.233

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.978
Plasma Protein Binding (PPB):	88.10250854492188%
Volume Distribution (VD):	1.207
Pgp-substrate:	11.955697059631348%

ADMET: Metabolism

CYP1A2-inhibitor:	0.535
CYP1A2-substrate:	0.428
CYP2C19-inhibitor:	0.896
CYP2C19-substrate:	0.49
CYP2C9-inhibitor:	0.772
CYP2C9-substrate:	0.594
CYP2D6-inhibitor:	0.856
CYP2D6-substrate:	0.801
CYP3A4-inhibitor:	0.934
CYP3A4-substrate:	0.626

ADMET: Excretion

Clearance (CL):	3.72
Half-life (T1/2):	0.386

ADMET: Toxicity

hERG Blockers:	0.085
Human Hepatotoxicity (H-HT):	0.318
Drug-inuced Liver Injury (DILI):	0.593
AMES Toxicity:	0.056
Rat Oral Acute Toxicity:	0.951
Maximum Recommended Daily Dose:	0.895
Skin Sensitization:	0.267
Carcinogencity:	0.529
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.856

Download Data

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

Natural Product: NPC204565

Natural Product ID:	NPC204565
*Common Name:**	Pendolmycin
IUPAC Name:	n.a.
Synonyms:	Pendolmycin
Standard InCHIKey:	JPJWIAYMFHOJRY-YWZLYKJASA-N
Standard InCHI:	InChI=1S/C22H31N3O2/c1-7-22(4,5)16-8-9-17-18-14(11-23-19(16)18)10-15(12-26)24-21(27)20(13(2)3)25(17)6/h7-9,11,13,15,20,23,26H,1,10,12H2,2-6H3,(H,24,27)/t15-,20-/m0/s1
SMILES:	C=CC(C)(C)c1ccc2c3c(C[C@@H](CO)N=C([C@H](C(C)C)N2C)O)c[nH]c13
Synthetic Gene Cluster:	BGC0000391;
ChEMBL Identifier:	CHEMBL519751
PubChem CID:	154206
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino acids and derivatives [CHEMONTID:0002309] Alpha amino acid amides

*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
NPO31006	Marinactinospora thermotolerans	Species	0cardiopsaceae	Bacteria	n.a.	spore	n.a.	PMID[21977916]
NPO31006	Marinactinospora thermotolerans	Species	0cardiopsaceae	Bacteria	n.a.	mycelium	n.a.	PMID[21977916]

☑ 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	9
MIC	8

Activity Type	# Activity
Cell Line	9
Organism	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT762	Cell Line	A-431	Homo sapiens	IC50	=	0.001	ug.mL-1	PMID[543527]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	50000.0	nM	PMID[543528]
NPT1312	Cell Line	SW1990	Homo sapiens	IC50	>	50000.0	nM	PMID[543528]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	50000.0	nM	PMID[543528]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	>	50000.0	nM	PMID[543528]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	50000.0	nM	PMID[543528]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	50000.0	nM	PMID[543528]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	>	50000.0	nM	PMID[543528]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	50000.0	nM	PMID[543528]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	25.0	ug.mL-1	PMID[543527]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	25.0	ug.mL-1	PMID[543527]
NPT1550	Organism	Bacillus anthracis	Bacillus anthracis	MIC	=	50.0	ug.mL-1	PMID[543527]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	50.0	ug.mL-1	PMID[543527]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	50.0	ug.mL-1	PMID[543527]
NPT5143	Organism	Corynebacterium bovis	Corynebacterium bovis	MIC	=	50.0	ug.mL-1	PMID[543527]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	=	50.0	ug.mL-1	PMID[543527]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	=	100.0	ug.mL-1	PMID[543527]

☑ 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 NPC204565 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	378
0.1-0.2	2945
0.2-0.3	20223
0.3-0.4	12018
0.4-0.5	3103
0.5-0.6	2139
0.6-0.7	1383
0.7-0.8	433
0.8-0.85	48
0.85-0.9	17
0.9-0.95	2
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.994	High Similarity	NPC173028
0.994	High Similarity	NPC65215
0.988	High Similarity	NPC317030
0.982	High Similarity	NPC474707
0.9708	High Similarity	NPC474177
0.9651	High Similarity	NPC133366
0.9581	High Similarity	NPC233936
0.9429	High Similarity	NPC229332
0.8817	High Similarity	NPC314957
0.8647	High Similarity	NPC474561
0.8647	High Similarity	NPC49954
0.8647	High Similarity	NPC160105
0.8639	High Similarity	NPC194640
0.8596	High Similarity	NPC201700
0.8538	High Similarity	NPC54988
0.8512	High Similarity	NPC469762
0.8471	Intermediate Similarity	NPC282231
0.8452	Intermediate Similarity	NPC469785
0.8448	Intermediate Similarity	NPC314603
0.8412	Intermediate Similarity	NPC279918
0.8382	Intermediate Similarity	NPC63751
0.8372	Intermediate Similarity	NPC470508
0.8363	Intermediate Similarity	NPC16667
0.8333	Intermediate Similarity	NPC259644
0.8333	Intermediate Similarity	NPC73952
0.8333	Intermediate Similarity	NPC469786
0.8333	Intermediate Similarity	NPC469760
0.8333	Intermediate Similarity	NPC469763
0.8333	Intermediate Similarity	NPC25008
0.8333	Intermediate Similarity	NPC469765
0.8314	Intermediate Similarity	NPC311276
0.8305	Intermediate Similarity	NPC151939
0.8284	Intermediate Similarity	NPC80597
0.8284	Intermediate Similarity	NPC212376
0.8284	Intermediate Similarity	NPC75540
0.8284	Intermediate Similarity	NPC211572
0.8284	Intermediate Similarity	NPC70922
0.8251	Intermediate Similarity	NPC95783
0.8246	Intermediate Similarity	NPC230869
0.8246	Intermediate Similarity	NPC67056
0.8222	Intermediate Similarity	NPC163055
0.8212	Intermediate Similarity	NPC300688
0.8208	Intermediate Similarity	NPC40779
0.8202	Intermediate Similarity	NPC68354
0.8187	Intermediate Similarity	NPC129721
0.8176	Intermediate Similarity	NPC207726
0.8136	Intermediate Similarity	NPC34508
0.8129	Intermediate Similarity	NPC285469
0.8125	Intermediate Similarity	NPC280548
0.8101	Intermediate Similarity	NPC248454
0.8101	Intermediate Similarity	NPC59269
0.8098	Intermediate Similarity	NPC213629
0.809	Intermediate Similarity	NPC275305
0.809	Intermediate Similarity	NPC37423
0.8084	Intermediate Similarity	NPC314372
0.8077	Intermediate Similarity	NPC165495
0.8056	Intermediate Similarity	NPC213468
0.8056	Intermediate Similarity	NPC126709
0.8056	Intermediate Similarity	NPC248041
0.8045	Intermediate Similarity	NPC267885
0.8042	Intermediate Similarity	NPC473640
0.8	Intermediate Similarity	NPC84827
0.8	Intermediate Similarity	NPC14113
0.8	Intermediate Similarity	NPC145885
0.8	Intermediate Similarity	NPC100321
0.7989	Intermediate Similarity	NPC329688
0.7989	Intermediate Similarity	NPC189812
0.7989	Intermediate Similarity	NPC203468
0.7989	Intermediate Similarity	NPC110500
0.7989	Intermediate Similarity	NPC149155
0.7964	Intermediate Similarity	NPC190296
0.7956	Intermediate Similarity	NPC215795
0.7956	Intermediate Similarity	NPC283219
0.7956	Intermediate Similarity	NPC176199
0.7956	Intermediate Similarity	NPC270009
0.7923	Intermediate Similarity	NPC19679
0.7921	Intermediate Similarity	NPC194411
0.7917	Intermediate Similarity	NPC475506
0.7898	Intermediate Similarity	NPC102423
0.7895	Intermediate Similarity	NPC105818
0.7895	Intermediate Similarity	NPC24678
0.7892	Intermediate Similarity	NPC94752
0.7892	Intermediate Similarity	NPC235684
0.7889	Intermediate Similarity	NPC472586
0.7877	Intermediate Similarity	NPC158129
0.7876	Intermediate Similarity	NPC155143
0.7869	Intermediate Similarity	NPC192270
0.7865	Intermediate Similarity	NPC78020
0.7861	Intermediate Similarity	NPC38736
0.7857	Intermediate Similarity	NPC472443
0.7838	Intermediate Similarity	NPC15102
0.7838	Intermediate Similarity	NPC188387
0.7838	Intermediate Similarity	NPC163421
0.7833	Intermediate Similarity	NPC313791
0.7833	Intermediate Similarity	NPC472123
0.7784	Intermediate Similarity	NPC228835
0.7784	Intermediate Similarity	NPC73767
0.7784	Intermediate Similarity	NPC110126
0.7784	Intermediate Similarity	NPC131718
0.7772	Intermediate Similarity	NPC71037
0.7765	Intermediate Similarity	NPC317430
0.7765	Intermediate Similarity	NPC159856
0.776	Intermediate Similarity	NPC265576
0.776	Intermediate Similarity	NPC171317
0.7759	Intermediate Similarity	NPC470507
0.7738	Intermediate Similarity	NPC469780
0.7738	Intermediate Similarity	NPC469784
0.7738	Intermediate Similarity	NPC469768
0.7738	Intermediate Similarity	NPC469783
0.7738	Intermediate Similarity	NPC469761
0.7738	Intermediate Similarity	NPC469779
0.7738	Intermediate Similarity	NPC469767
0.7733	Intermediate Similarity	NPC187951
0.7732	Intermediate Similarity	NPC300183
0.773	Intermediate Similarity	NPC472444
0.772	Intermediate Similarity	NPC293917
0.7713	Intermediate Similarity	NPC321708
0.7705	Intermediate Similarity	NPC293472
0.7705	Intermediate Similarity	NPC64436
0.7692	Intermediate Similarity	NPC469766
0.768	Intermediate Similarity	NPC470498
0.768	Intermediate Similarity	NPC470497
0.7674	Intermediate Similarity	NPC471957
0.7665	Intermediate Similarity	NPC105127
0.7665	Intermediate Similarity	NPC84911
0.7663	Intermediate Similarity	NPC248462
0.766	Intermediate Similarity	NPC17059
0.7656	Intermediate Similarity	NPC11445
0.765	Intermediate Similarity	NPC134586
0.765	Intermediate Similarity	NPC288785
0.7638	Intermediate Similarity	NPC223791
0.7638	Intermediate Similarity	NPC107077
0.7634	Intermediate Similarity	NPC469358
0.7634	Intermediate Similarity	NPC472108
0.7634	Intermediate Similarity	NPC139291
0.7634	Intermediate Similarity	NPC48938
0.763	Intermediate Similarity	NPC37548
0.763	Intermediate Similarity	NPC124005
0.7627	Intermediate Similarity	NPC206819
0.7627	Intermediate Similarity	NPC56765
0.7627	Intermediate Similarity	NPC41257
0.7627	Intermediate Similarity	NPC318065
0.7626	Intermediate Similarity	NPC54420
0.7617	Intermediate Similarity	NPC262898
0.7609	Intermediate Similarity	NPC211997
0.7606	Intermediate Similarity	NPC315555
0.7606	Intermediate Similarity	NPC171171
0.7605	Intermediate Similarity	NPC261195
0.7605	Intermediate Similarity	NPC96102
0.7605	Intermediate Similarity	NPC29886
0.7604	Intermediate Similarity	NPC157828
0.7604	Intermediate Similarity	NPC195239
0.7602	Intermediate Similarity	NPC476874
0.7598	Intermediate Similarity	NPC90723
0.7592	Intermediate Similarity	NPC477167
0.7592	Intermediate Similarity	NPC473342
0.7577	Intermediate Similarity	NPC470499
0.7576	Intermediate Similarity	NPC475288
0.7574	Intermediate Similarity	NPC475602
0.7571	Intermediate Similarity	NPC286427
0.7569	Intermediate Similarity	NPC154293
0.7568	Intermediate Similarity	NPC133261
0.7568	Intermediate Similarity	NPC55772
0.7568	Intermediate Similarity	NPC11126
0.7565	Intermediate Similarity	NPC179701
0.7563	Intermediate Similarity	NPC98715
0.7562	Intermediate Similarity	NPC320968
0.7553	Intermediate Similarity	NPC62510
0.7553	Intermediate Similarity	NPC314002
0.755	Intermediate Similarity	NPC271862
0.755	Intermediate Similarity	NPC162860
0.754	Intermediate Similarity	NPC472109
0.754	Intermediate Similarity	NPC472110
0.7539	Intermediate Similarity	NPC243716
0.7538	Intermediate Similarity	NPC166492
0.7538	Intermediate Similarity	NPC473362
0.7528	Intermediate Similarity	NPC135141
0.7528	Intermediate Similarity	NPC92796
0.7526	Intermediate Similarity	NPC46413
0.7525	Intermediate Similarity	NPC75634
0.7525	Intermediate Similarity	NPC473376
0.7514	Intermediate Similarity	NPC129042
0.7514	Intermediate Similarity	NPC49217
0.7514	Intermediate Similarity	NPC111275
0.7513	Intermediate Similarity	NPC193761
0.7512	Intermediate Similarity	NPC477714
0.75	Intermediate Similarity	NPC127677
0.75	Intermediate Similarity	NPC204717
0.75	Intermediate Similarity	NPC200214
0.75	Intermediate Similarity	NPC258062
0.75	Intermediate Similarity	NPC472587
0.7486	Intermediate Similarity	NPC473320
0.7486	Intermediate Similarity	NPC6982
0.7486	Intermediate Similarity	NPC53947
0.7463	Intermediate Similarity	NPC478158
0.7461	Intermediate Similarity	NPC267343
0.746	Intermediate Similarity	NPC280290
0.7459	Intermediate Similarity	NPC203754
0.7459	Intermediate Similarity	NPC150048
0.745	Intermediate Similarity	NPC46225

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 NPC204565 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	198
0.1-0.2	562
0.2-0.3	1083
0.3-0.4	1605
0.4-0.5	2723
0.5-0.6	2059
0.6-0.7	787
0.7-0.8	122
0.8-0.85	9
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8547	High Similarity	NPD4184	Clinical (unspecified phase)
0.8514	High Similarity	NPD2144	Approved
0.8475	Intermediate Similarity	NPD3038	Discontinued
0.8436	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.8315	Intermediate Similarity	NPD6595	Phase 3
0.8258	Intermediate Similarity	NPD4076	Approved
0.8258	Intermediate Similarity	NPD4079	Approved
0.8202	Intermediate Similarity	NPD3505	Approved
0.8202	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.8202	Intermediate Similarity	NPD3506	Approved
0.8043	Intermediate Similarity	NPD8431	Approved
0.8	Intermediate Similarity	NPD2172	Phase 1
0.7989	Intermediate Similarity	NPD482	Approved
0.7966	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7944	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD3100	Discontinued
0.7923	Intermediate Similarity	NPD2094	Phase 2
0.7923	Intermediate Similarity	NPD2092	Phase 2
0.7923	Intermediate Similarity	NPD2095	Phase 2
0.7903	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7889	Intermediate Similarity	NPD5065	Approved
0.788	Intermediate Similarity	NPD2091	Phase 2
0.788	Intermediate Similarity	NPD2096	Phase 2
0.7865	Intermediate Similarity	NPD4638	Approved
0.7865	Intermediate Similarity	NPD4640	Approved
0.7865	Intermediate Similarity	NPD4639	Approved
0.7857	Intermediate Similarity	NPD8386	Phase 2
0.7833	Intermediate Similarity	NPD750	Phase 2
0.7826	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD1325	Approved
0.7821	Intermediate Similarity	NPD1326	Approved
0.7795	Intermediate Similarity	NPD8272	Phase 2
0.7784	Intermediate Similarity	NPD786	Approved
0.7747	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.772	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD3404	Approved
0.7684	Intermediate Similarity	NPD1404	Approved
0.7684	Intermediate Similarity	NPD1403	Approved
0.7667	Intermediate Similarity	NPD2641	Approved
0.7667	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD2640	Approved
0.7667	Intermediate Similarity	NPD5021	Discontinued
0.766	Intermediate Similarity	NPD3961	Discontinued
0.766	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD2639	Approved
0.7611	Intermediate Similarity	NPD2642	Approved
0.7605	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD1722	Approved
0.7576	Intermediate Similarity	NPD7957	Phase 1
0.7576	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD4703	Approved
0.7572	Intermediate Similarity	NPD4702	Approved
0.7563	Intermediate Similarity	NPD8072	Approved
0.7556	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD4075	Phase 2
0.7525	Intermediate Similarity	NPD3330	Phase 1
0.7514	Intermediate Similarity	NPD4181	Approved
0.75	Intermediate Similarity	NPD3323	Discontinued
0.75	Intermediate Similarity	NPD4128	Approved
0.75	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD3117	Approved
0.7486	Intermediate Similarity	NPD3116	Approved
0.7475	Intermediate Similarity	NPD7470	Discontinued
0.745	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7437	Intermediate Similarity	NPD5901	Discontinued
0.7436	Intermediate Similarity	NPD7948	Phase 1
0.7426	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD1038	Approved
0.7371	Intermediate Similarity	NPD4547	Phase 3
0.7371	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD5426	Phase 3
0.7341	Intermediate Similarity	NPD3717	Discontinued
0.734	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD8073	Approved
0.7333	Intermediate Similarity	NPD7619	Phase 3
0.7333	Intermediate Similarity	NPD7618	Phase 3
0.7333	Intermediate Similarity	NPD7944	Discontinued
0.733	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD8122	Approved
0.7326	Intermediate Similarity	NPD8123	Approved
0.7316	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD6281	Approved
0.7306	Intermediate Similarity	NPD4499	Approved
0.7304	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD2837	Discontinued
0.7297	Intermediate Similarity	NPD3610	Approved
0.7297	Intermediate Similarity	NPD3609	Approved
0.7291	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD4463	Approved
0.7288	Intermediate Similarity	NPD4462	Approved
0.7283	Intermediate Similarity	NPD5862	Discovery
0.7282	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5100	Phase 3
0.7268	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD5106	Approved
0.7263	Intermediate Similarity	NPD5105	Approved
0.7255	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD4957	Phase 2
0.7222	Intermediate Similarity	NPD2580	Discontinued
0.7214	Intermediate Similarity	NPD4886	Phase 2
0.7208	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD802	Phase 2
0.7189	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD5555	Phase 1
0.7184	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD2381	Approved
0.7181	Intermediate Similarity	NPD2382	Approved
0.7181	Intermediate Similarity	NPD2380	Approved
0.7173	Intermediate Similarity	NPD2391	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD6664	Approved
0.7166	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD4999	Phase 3
0.7157	Intermediate Similarity	NPD4998	Phase 3
0.715	Intermediate Similarity	NPD484	Approved
0.715	Intermediate Similarity	NPD4600	Approved
0.715	Intermediate Similarity	NPD4601	Approved
0.7119	Intermediate Similarity	NPD1683	Approved
0.7114	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD1392	Approved
0.7107	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD5254	Discontinued
0.7101	Intermediate Similarity	NPD8093	Discontinued
0.7101	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD3082	Discontinued
0.7095	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5596	Phase 2
0.7083	Intermediate Similarity	NPD7824	Approved
0.7067	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD706	Phase 1
0.7056	Intermediate Similarity	NPD4615	Phase 2
0.7056	Intermediate Similarity	NPD7271	Approved
0.7049	Intermediate Similarity	NPD5255	Approved
0.7048	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD2006	Phase 2
0.7041	Intermediate Similarity	NPD3654	Approved
0.7039	Intermediate Similarity	NPD2430	Phase 2
0.7033	Intermediate Similarity	NPD6026	Approved
0.7029	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD8129	Discovery
0.7027	Intermediate Similarity	NPD5140	Approved
0.7027	Intermediate Similarity	NPD5138	Approved
0.7024	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD8410	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD8036	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD8037	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5612	Discontinued
0.6991	Remote Similarity	NPD7731	Approved
0.6991	Remote Similarity	NPD7730	Approved
0.6989	Remote Similarity	NPD1592	Phase 3
0.6986	Remote Similarity	NPD8094	Discontinued
0.6974	Remote Similarity	NPD6217	Discontinued
0.6973	Remote Similarity	NPD972	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD8026	Phase 1
0.6971	Remote Similarity	NPD5067	Phase 2
0.6971	Remote Similarity	NPD5066	Phase 2
0.6967	Remote Similarity	NPD7423	Phase 2
0.6966	Remote Similarity	NPD5995	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD5145	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD2928	Phase 2
0.6946	Remote Similarity	NPD4511	Phase 1
0.6943	Remote Similarity	NPD1708	Approved
0.6943	Remote Similarity	NPD1707	Approved
0.694	Remote Similarity	NPD3115	Approved
0.694	Remote Similarity	NPD3113	Approved
0.694	Remote Similarity	NPD3112	Approved
0.694	Remote Similarity	NPD3114	Approved
0.6939	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD8020	Approved
0.6939	Remote Similarity	NPD3002	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD2383	Phase 1
0.6939	Remote Similarity	NPD5590	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD8021	Approved
0.6927	Remote Similarity	NPD6987	Phase 1
0.6923	Remote Similarity	NPD2119	Approved
0.6923	Remote Similarity	NPD3014	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3013	Phase 3
0.6923	Remote Similarity	NPD2118	Approved
0.6919	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD5082	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD5913	Phase 3
0.6919	Remote Similarity	NPD5081	Phase 1
0.6902	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD2865	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD2581	Approved
0.6902	Remote Similarity	NPD2582	Approved
0.6901	Remote Similarity	NPD3475	Approved
0.6901	Remote Similarity	NPD3476	Approved
0.6898	Remote Similarity	NPD4550	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD2719	Clinical (unspecified phase)

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