NPASS Compound

Structure

NPC475935 OpenBabel07101719132D 27 31 0 0 1 0 0 0 0 0999 V2000 3.9049 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7709 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6230 -1.5903 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8799 -0.9211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0878 1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9049 -0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7820 -0.3031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0388 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7709 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5741 -1.2813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0388 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0388 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5000 0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6369 -0.1340 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -5.3172 -1.9504 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -4.0388 1.3660 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 1.7321 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.0878 0.0570 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 -1.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 10 1 0 0 0 0 2 11 1 0 0 0 0 3 4 2 0 0 0 0 3 12 1 0 0 0 0 4 13 1 0 0 0 0 5 10 1 0 0 0 0 5 17 2 0 0 0 0 6 11 2 0 0 0 0 6 15 1 0 0 0 0 7 12 2 0 0 0 0 7 16 1 0 0 0 0 8 14 2 0 0 0 0 8 23 1 0 0 0 0 9 18 1 0 0 0 0 9 24 1 0 0 0 0 10 15 2 0 0 0 0 11 21 1 0 0 0 0 12 22 1 0 0 0 0 13 14 1 0 0 0 0 13 16 2 0 0 0 0 15 25 1 0 0 0 0 16 23 1 0 0 0 0 17 25 1 0 0 0 0 18 17 1 6 0 0 0 18 26 1 0 0 0 0 19 14 1 1 0 0 0 19 20 1 0 0 0 0 19 24 1 0 0 0 0 20 26 2 0 0 0 0 20 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	485.97
Volume:	379.31
LogP:	5.29
LogD:	4.058
LogS:	-5.185
# Rotatable Bonds:	2
TPSA:	72.71
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.331
Synthetic Accessibility Score:	3.717
Fsp3:	0.15
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:	-5.565
MDCK Permeability:	9.448560376768e-06
Pgp-inhibitor:	0.998
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.139
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.571
Plasma Protein Binding (PPB):	95.86699676513672%
Volume Distribution (VD):	1.816
Pgp-substrate:	3.0699503421783447%

ADMET: Metabolism

CYP1A2-inhibitor:	0.797
CYP1A2-substrate:	0.617
CYP2C19-inhibitor:	0.863
CYP2C19-substrate:	0.131
CYP2C9-inhibitor:	0.649
CYP2C9-substrate:	0.682
CYP2D6-inhibitor:	0.796
CYP2D6-substrate:	0.871
CYP3A4-inhibitor:	0.934
CYP3A4-substrate:	0.386

ADMET: Excretion

Clearance (CL):	1.701
Half-life (T1/2):	0.179

ADMET: Toxicity

hERG Blockers:	0.772
Human Hepatotoxicity (H-HT):	0.62
Drug-inuced Liver Injury (DILI):	0.925
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.929
Maximum Recommended Daily Dose:	0.994
Skin Sensitization:	0.112
Carcinogencity:	0.078
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.838

Download Data

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

Natural Product: NPC475935

Natural Product ID:	NPC475935
*Common Name:**	Trans-3,4-Dihydrohamacnathin A
IUPAC Name:	(3R,6R)-6-(6-bromo-1H-indol-2-yl)-3-(6-bromo-1H-indol-3-yl)piperazin-2-one
Synonyms:
Standard InCHIKey:	BQZAYRKFIKQDOM-RTBURBONSA-N
Standard InCHI:	InChI=1S/C20H16Br2N4O/c21-11-2-1-10-5-17(25-15(10)6-11)18-9-24-19(20(27)26-18)14-8-23-16-7-12(22)3-4-13(14)16/h1-8,18-19,23-25H,9H2,(H,26,27)/t18-,19-/m1/s1
SMILES:	C1C(NC(=O)C(N1)C2=CNC3=C2C=CC(=C3)Br)C4=CC5=C(N4)C=C(C=C5)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518847
PubChem CID:	44584008
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
NPO32581	spongosorites sp.	Species	Halichondriidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921415]
NPO32581	spongosorites sp.	Species	Halichondriidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16154746]
NPO32581	spongosorites sp.	Species	Halichondriidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17253840]
NPO32581	spongosorites sp.	Species	Halichondriidae	Eukaryota	n.a.	southern australian	n.a.	PMID[9599272]

☑ 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
ED50	5
MIC	9

Activity Type	# Activity
Cell Line	5
Organism	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	8.28	ug ml-1	PMID[533160]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	=	8.03	ug ml-1	PMID[533160]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	9.14	ug ml-1	PMID[533160]
NPT574	Cell Line	XF498	Homo sapiens	ED50	=	6.88	ug ml-1	PMID[533160]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	5.35	ug ml-1	PMID[533160]
NPT1228	Organism	Streptococcus pyogenes	Streptococcus pyogenes	MIC	=	12.5	ug.mL-1	PMID[533160]
NPT1228	Organism	Streptococcus pyogenes	Streptococcus pyogenes	MIC	>	25.0	ug.mL-1	PMID[533160]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	>	25.0	ug.mL-1	PMID[533160]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	25.0	ug.mL-1	PMID[533160]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	25.0	ug.mL-1	PMID[533160]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	25.0	ug.mL-1	PMID[533160]
NPT4997	Organism	Klebsiella oxytoca	Klebsiella oxytoca	MIC	>	25.0	ug.mL-1	PMID[533160]

☑ 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 NPC475935 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	700
0.1-0.2	10117
0.2-0.3	19877
0.3-0.4	5661
0.4-0.5	2854
0.5-0.6	1894
0.6-0.7	1170
0.7-0.8	392
0.8-0.85	21
0.85-0.9	3
0.9-0.95	1
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC52909
1.0	High Similarity	NPC94211
0.9944	High Similarity	NPC106771
0.9944	High Similarity	NPC303820
0.9944	High Similarity	NPC23420
0.9944	High Similarity	NPC205254
0.9213	High Similarity	NPC15102
0.8667	High Similarity	NPC59269
0.861	High Similarity	NPC473342
0.861	High Similarity	NPC477167
0.8603	High Similarity	NPC477611
0.8535	High Similarity	NPC477610
0.8413	Intermediate Similarity	NPC304187
0.8413	Intermediate Similarity	NPC477166
0.8408	Intermediate Similarity	NPC477114
0.8394	Intermediate Similarity	NPC13456
0.8394	Intermediate Similarity	NPC166209
0.8394	Intermediate Similarity	NPC77241
0.8394	Intermediate Similarity	NPC269203
0.8342	Intermediate Similarity	NPC268744
0.8342	Intermediate Similarity	NPC153123
0.8342	Intermediate Similarity	NPC201266
0.8342	Intermediate Similarity	NPC220797
0.8342	Intermediate Similarity	NPC475914
0.8342	Intermediate Similarity	NPC474318
0.8333	Intermediate Similarity	NPC63751
0.8211	Intermediate Similarity	NPC231536
0.8186	Intermediate Similarity	NPC477609
0.8182	Intermediate Similarity	NPC477607
0.8182	Intermediate Similarity	NPC477608
0.8108	Intermediate Similarity	NPC474958
0.8077	Intermediate Similarity	NPC474561
0.8077	Intermediate Similarity	NPC49954
0.8066	Intermediate Similarity	NPC63031
0.8056	Intermediate Similarity	NPC279918
0.803	Intermediate Similarity	NPC473761
0.8011	Intermediate Similarity	NPC282231
0.801	Intermediate Similarity	NPC475736
0.7969	Intermediate Similarity	NPC321708
0.795	Intermediate Similarity	NPC470505
0.7946	Intermediate Similarity	NPC82331
0.7923	Intermediate Similarity	NPC274229
0.7923	Intermediate Similarity	NPC17751
0.7901	Intermediate Similarity	NPC92796
0.7901	Intermediate Similarity	NPC230869
0.7901	Intermediate Similarity	NPC135141
0.788	Intermediate Similarity	NPC160105
0.788	Intermediate Similarity	NPC54988
0.7877	Intermediate Similarity	NPC141926
0.7869	Intermediate Similarity	NPC194640
0.7854	Intermediate Similarity	NPC128084
0.7842	Intermediate Similarity	NPC307191
0.7833	Intermediate Similarity	NPC314957
0.7824	Intermediate Similarity	NPC17059
0.7807	Intermediate Similarity	NPC64055
0.7806	Intermediate Similarity	NPC88315
0.7784	Intermediate Similarity	NPC109447
0.7784	Intermediate Similarity	NPC213629
0.7778	Intermediate Similarity	NPC259644
0.7778	Intermediate Similarity	NPC469763
0.7778	Intermediate Similarity	NPC469786
0.7778	Intermediate Similarity	NPC25008
0.7778	Intermediate Similarity	NPC73952
0.7778	Intermediate Similarity	NPC469760
0.7778	Intermediate Similarity	NPC469765
0.7773	Intermediate Similarity	NPC17487
0.7773	Intermediate Similarity	NPC201831
0.7767	Intermediate Similarity	NPC207020
0.7762	Intermediate Similarity	NPC474195
0.7761	Intermediate Similarity	NPC193761
0.7757	Intermediate Similarity	NPC156003
0.7738	Intermediate Similarity	NPC477108
0.7738	Intermediate Similarity	NPC477107
0.7738	Intermediate Similarity	NPC477109
0.7735	Intermediate Similarity	NPC70922
0.7735	Intermediate Similarity	NPC80597
0.7735	Intermediate Similarity	NPC212376
0.7735	Intermediate Similarity	NPC75540
0.7735	Intermediate Similarity	NPC211572
0.7725	Intermediate Similarity	NPC121903
0.772	Intermediate Similarity	NPC308931
0.772	Intermediate Similarity	NPC99939
0.7713	Intermediate Similarity	NPC314603
0.7703	Intermediate Similarity	NPC477715
0.77	Intermediate Similarity	NPC474196
0.7697	Intermediate Similarity	NPC288838
0.7696	Intermediate Similarity	NPC166492
0.7696	Intermediate Similarity	NPC473362
0.7692	Intermediate Similarity	NPC469785
0.7688	Intermediate Similarity	NPC262898
0.7684	Intermediate Similarity	NPC248454
0.768	Intermediate Similarity	NPC94752
0.7672	Intermediate Similarity	NPC280297
0.7668	Intermediate Similarity	NPC108011
0.7667	Intermediate Similarity	NPC53947
0.7667	Intermediate Similarity	NPC477714
0.7663	Intermediate Similarity	NPC131718
0.765	Intermediate Similarity	NPC131887
0.765	Intermediate Similarity	NPC469762
0.765	Intermediate Similarity	NPC470499
0.7647	Intermediate Similarity	NPC317430
0.7644	Intermediate Similarity	NPC470703
0.7638	Intermediate Similarity	NPC179701
0.7638	Intermediate Similarity	NPC222018
0.7619	Intermediate Similarity	NPC288074
0.7606	Intermediate Similarity	NPC194411
0.76	Intermediate Similarity	NPC227582
0.7598	Intermediate Similarity	NPC475070
0.7596	Intermediate Similarity	NPC285469
0.7596	Intermediate Similarity	NPC470702
0.7596	Intermediate Similarity	NPC473218
0.7581	Intermediate Similarity	NPC317105
0.7581	Intermediate Similarity	NPC311276
0.7581	Intermediate Similarity	NPC149265
0.7577	Intermediate Similarity	NPC165495
0.7577	Intermediate Similarity	NPC471536
0.7577	Intermediate Similarity	NPC472294
0.7574	Intermediate Similarity	NPC470497
0.7565	Intermediate Similarity	NPC233936
0.7563	Intermediate Similarity	NPC95783
0.7562	Intermediate Similarity	NPC265576
0.7554	Intermediate Similarity	NPC216643
0.7542	Intermediate Similarity	NPC314372
0.754	Intermediate Similarity	NPC280864
0.7538	Intermediate Similarity	NPC474180
0.7538	Intermediate Similarity	NPC188821
0.7535	Intermediate Similarity	NPC245348
0.7526	Intermediate Similarity	NPC48938
0.7526	Intermediate Similarity	NPC163055
0.7525	Intermediate Similarity	NPC293917
0.7525	Intermediate Similarity	NPC100321
0.7524	Intermediate Similarity	NPC478157
0.7514	Intermediate Similarity	NPC2272
0.7513	Intermediate Similarity	NPC97343
0.75	Intermediate Similarity	NPC476073
0.75	Intermediate Similarity	NPC60006
0.75	Intermediate Similarity	NPC141353
0.75	Intermediate Similarity	NPC68354
0.7488	Intermediate Similarity	NPC252338
0.7487	Intermediate Similarity	NPC324149
0.7487	Intermediate Similarity	NPC37423
0.7487	Intermediate Similarity	NPC102423
0.7487	Intermediate Similarity	NPC228835
0.7487	Intermediate Similarity	NPC247987
0.7487	Intermediate Similarity	NPC275305
0.7486	Intermediate Similarity	NPC325903
0.7477	Intermediate Similarity	NPC470502
0.7475	Intermediate Similarity	NPC171317
0.7475	Intermediate Similarity	NPC474389
0.7475	Intermediate Similarity	NPC473640
0.746	Intermediate Similarity	NPC201700
0.7453	Intermediate Similarity	NPC476041
0.7453	Intermediate Similarity	NPC304926
0.7446	Intermediate Similarity	NPC475746
0.7446	Intermediate Similarity	NPC34844
0.7442	Intermediate Similarity	NPC470501
0.7441	Intermediate Similarity	NPC250835
0.744	Intermediate Similarity	NPC54420
0.7437	Intermediate Similarity	NPC243716
0.7433	Intermediate Similarity	NPC16667
0.743	Intermediate Similarity	NPC190296
0.7429	Intermediate Similarity	NPC75726
0.7429	Intermediate Similarity	NPC75634
0.7429	Intermediate Similarity	NPC110602
0.7429	Intermediate Similarity	NPC31385
0.7416	Intermediate Similarity	NPC5145
0.7411	Intermediate Similarity	NPC62749
0.7409	Intermediate Similarity	NPC151939
0.7409	Intermediate Similarity	NPC111275
0.7407	Intermediate Similarity	NPC167908
0.7407	Intermediate Similarity	NPC470503
0.74	Intermediate Similarity	NPC99666
0.7396	Intermediate Similarity	NPC110500
0.7396	Intermediate Similarity	NPC149155
0.7396	Intermediate Similarity	NPC203468
0.7391	Intermediate Similarity	NPC476121
0.7389	Intermediate Similarity	NPC67288
0.7385	Intermediate Similarity	NPC71037
0.7381	Intermediate Similarity	NPC72956
0.7377	Intermediate Similarity	NPC105818
0.7377	Intermediate Similarity	NPC24678
0.7374	Intermediate Similarity	NPC317030
0.7371	Intermediate Similarity	NPC11126
0.7371	Intermediate Similarity	NPC126709
0.7371	Intermediate Similarity	NPC248041
0.7371	Intermediate Similarity	NPC233050
0.7371	Intermediate Similarity	NPC283219
0.7371	Intermediate Similarity	NPC276540
0.7368	Intermediate Similarity	NPC162860
0.7368	Intermediate Similarity	NPC478158
0.7368	Intermediate Similarity	NPC80596
0.7366	Intermediate Similarity	NPC475506
0.736	Intermediate Similarity	NPC188387
0.736	Intermediate Similarity	NPC163421
0.7358	Intermediate Similarity	NPC280852
0.7358	Intermediate Similarity	NPC267885
0.7351	Intermediate Similarity	NPC207726
0.7348	Intermediate Similarity	NPC159856
0.7346	Intermediate Similarity	NPC153980
0.7346	Intermediate Similarity	NPC6865

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 NPC475935 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	324
0.1-0.2	718
0.2-0.3	1105
0.3-0.4	2071
0.4-0.5	2420
0.5-0.6	1908
0.6-0.7	545
0.7-0.8	56
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8289	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.827	Intermediate Similarity	NPD6595	Phase 3
0.8261	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7957	Intermediate Similarity	NPD5065	Approved
0.7796	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7789	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7732	Intermediate Similarity	NPD8431	Approved
0.7644	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD7948	Phase 1
0.7598	Intermediate Similarity	NPD5426	Phase 3
0.7596	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD4076	Approved
0.7552	Intermediate Similarity	NPD4079	Approved
0.7525	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3505	Approved
0.75	Intermediate Similarity	NPD3506	Approved
0.7487	Intermediate Similarity	NPD4128	Approved
0.7474	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD3961	Discontinued
0.7436	Intermediate Similarity	NPD2094	Phase 2
0.7436	Intermediate Similarity	NPD2092	Phase 2
0.7436	Intermediate Similarity	NPD2095	Phase 2
0.7398	Intermediate Similarity	NPD2096	Phase 2
0.7398	Intermediate Similarity	NPD2091	Phase 2
0.7396	Intermediate Similarity	NPD482	Approved
0.7368	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD1325	Approved
0.733	Intermediate Similarity	NPD1326	Approved
0.732	Intermediate Similarity	NPD2144	Approved
0.7313	Intermediate Similarity	NPD3404	Approved
0.7299	Intermediate Similarity	NPD7470	Discontinued
0.7295	Intermediate Similarity	NPD4886	Phase 2
0.7291	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD786	Approved
0.726	Intermediate Similarity	NPD5901	Discontinued
0.7251	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD7666	Phase 3
0.7238	Intermediate Similarity	NPD7665	Phase 2
0.7236	Intermediate Similarity	NPD706	Phase 1
0.7231	Intermediate Similarity	NPD4181	Approved
0.7228	Intermediate Similarity	NPD3100	Discontinued
0.7217	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD3038	Discontinued
0.7204	Intermediate Similarity	NPD2837	Discontinued
0.72	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD2172	Phase 1
0.7184	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD6999	Discontinued
0.7183	Intermediate Similarity	NPD8093	Discontinued
0.7182	Intermediate Similarity	NPD1722	Approved
0.7179	Intermediate Similarity	NPD4075	Phase 2
0.7176	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD7618	Phase 3
0.7157	Intermediate Similarity	NPD7619	Phase 3
0.7157	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD6217	Discontinued
0.7143	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7957	Phase 1
0.713	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD8386	Phase 2
0.7103	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD4640	Approved
0.7098	Intermediate Similarity	NPD4638	Approved
0.7098	Intermediate Similarity	NPD4639	Approved
0.7092	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD4703	Approved
0.7081	Intermediate Similarity	NPD4702	Approved
0.7081	Intermediate Similarity	NPD8073	Approved
0.7077	Intermediate Similarity	NPD750	Phase 2
0.7075	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD6165	Phase 2
0.7072	Intermediate Similarity	NPD6164	Phase 2
0.7062	Intermediate Similarity	NPD7001	Phase 3
0.7059	Intermediate Similarity	NPD4890	Phase 2
0.7053	Intermediate Similarity	NPD3230	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD5409	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD8072	Approved
0.7031	Intermediate Similarity	NPD3323	Discontinued
0.7031	Intermediate Similarity	NPD5140	Approved
0.7031	Intermediate Similarity	NPD5138	Approved
0.7027	Intermediate Similarity	NPD7711	Discontinued
0.7024	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD8272	Phase 2
0.7014	Intermediate Similarity	NPD7717	Approved
0.7014	Intermediate Similarity	NPD7716	Approved
0.7009	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD4462	Approved
0.7005	Intermediate Similarity	NPD4463	Approved
0.6995	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.699	Remote Similarity	NPD7944	Discontinued
0.6982	Remote Similarity	NPD7271	Approved
0.6981	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD1853	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD7781	Approved
0.6964	Remote Similarity	NPD7780	Approved
0.6963	Remote Similarity	NPD6545	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD4520	Approved
0.6954	Remote Similarity	NPD2928	Phase 2
0.6952	Remote Similarity	NPD1183	Approved
0.695	Remote Similarity	NPD1895	Discontinued
0.6948	Remote Similarity	NPD8410	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD3330	Phase 1
0.6942	Remote Similarity	NPD802	Phase 2
0.6942	Remote Similarity	NPD1038	Approved
0.6938	Remote Similarity	NPD3814	Phase 1
0.693	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD5612	Discontinued
0.6927	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2185	Clinical (unspecified phase)
0.692	Remote Similarity	NPD7731	Approved
0.692	Remote Similarity	NPD7730	Approved
0.6912	Remote Similarity	NPD8094	Discontinued
0.6905	Remote Similarity	NPD484	Approved
0.6902	Remote Similarity	NPD1592	Phase 3
0.69	Remote Similarity	NPD6452	Discontinued
0.6891	Remote Similarity	NPD8026	Phase 1
0.6885	Remote Similarity	NPD2070	Approved
0.6885	Remote Similarity	NPD2068	Approved
0.6885	Remote Similarity	NPD2069	Approved
0.6885	Remote Similarity	NPD2071	Approved
0.6884	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD7970	Approved
0.6881	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD6158	Phase 2
0.6878	Remote Similarity	NPD5117	Phase 2
0.6878	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7603	Discontinued
0.6875	Remote Similarity	NPD5255	Approved
0.6872	Remote Similarity	NPD2639	Approved
0.6872	Remote Similarity	NPD2642	Approved
0.6869	Remote Similarity	NPD8322	Phase 2
0.6858	Remote Similarity	NPD7824	Approved
0.6842	Remote Similarity	NPD7953	Approved
0.6842	Remote Similarity	NPD7950	Approved
0.6842	Remote Similarity	NPD7789	Approved
0.6842	Remote Similarity	NPD7791	Approved
0.6842	Remote Similarity	NPD7952	Approved
0.6842	Remote Similarity	NPD7951	Approved
0.6842	Remote Similarity	NPD7790	Approved
0.6837	Remote Similarity	NPD2390	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD5862	Discovery
0.6837	Remote Similarity	NPD4779	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD5021	Discontinued
0.6832	Remote Similarity	NPD5105	Approved
0.6832	Remote Similarity	NPD5106	Approved
0.683	Remote Similarity	NPD6976	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD3813	Approved
0.6822	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD6178	Phase 3
0.6794	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD6278	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD4511	Phase 1
0.6789	Remote Similarity	NPD4852	Phase 2
0.6789	Remote Similarity	NPD2882	Phase 1
0.6777	Remote Similarity	NPD8395	Approved
0.6777	Remote Similarity	NPD8396	Approved
0.6773	Remote Similarity	NPD6803	Clinical (unspecified phase)
0.677	Remote Similarity	NPD6978	Phase 2
0.677	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD7558	Phase 2
0.6768	Remote Similarity	NPD3609	Approved
0.6768	Remote Similarity	NPD3610	Approved
0.6765	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7424	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD5913	Phase 3
0.6763	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD3943	Clinical (unspecified phase)
0.675	Remote Similarity	NPD2380	Approved
0.675	Remote Similarity	NPD2381	Approved
0.675	Remote Similarity	NPD2382	Approved
0.6749	Remote Similarity	NPD5596	Phase 2
0.6746	Remote Similarity	NPD4998	Phase 3
0.6746	Remote Similarity	NPD4999	Phase 3
0.6734	Remote Similarity	NPD4112	Clinical (unspecified phase)
0.672	Remote Similarity	NPD4547	Phase 3
0.672	Remote Similarity	NPD1661	Suspended
0.6718	Remote Similarity	NPD972	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD8122	Approved
0.6716	Remote Similarity	NPD8123	Approved
0.6715	Remote Similarity	NPD4499	Approved
0.6715	Remote Similarity	NPD6281	Approved
0.6714	Remote Similarity	NPD5017	Discontinued
0.6714	Remote Similarity	NPD2960	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD4865	Approved
0.6713	Remote Similarity	NPD1392	Approved
0.6712	Remote Similarity	NPD6749	Phase 1
0.67	Remote Similarity	NPD6492	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