NPASS Compound

Structure

NPC474357 OpenBabel07101718222D 27 31 0 0 0 0 0 0 0 0999 V2000 -3.3305 -2.6303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9409 0.6460 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4644 -2.1303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9464 0.5415 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1965 -1.1303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1220 -1.0765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1280 0.4523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5886 -1.6810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1965 -2.1303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5287 -0.1630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4644 -1.1303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5396 -0.3720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7213 -0.4612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5886 -0.6810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3305 -0.6303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1274 -1.1810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 -0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0625 -2.6303 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 6.5232 -0.0584 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -3.1226 0.3478 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.5396 -1.9901 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 -1.4781 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 1.8841 0.9013 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 10 1 0 0 0 0 2 4 2 0 0 0 0 2 11 1 0 0 0 0 3 12 1 0 0 0 0 4 13 1 0 0 0 0 5 10 2 0 0 0 0 5 16 1 0 0 0 0 6 11 2 0 0 0 0 6 17 1 0 0 0 0 7 14 2 0 0 0 0 7 23 1 0 0 0 0 8 15 2 0 0 0 0 8 24 1 0 0 0 0 9 18 2 0 0 0 0 9 25 1 0 0 0 0 10 21 1 0 0 0 0 11 22 1 0 0 0 0 12 14 1 0 0 0 0 12 16 2 0 0 0 0 13 15 1 0 0 0 0 13 17 2 0 0 0 0 14 18 1 0 0 0 0 15 19 1 0 0 0 0 16 23 1 0 0 0 0 17 24 1 0 0 0 0 18 26 1 0 0 0 0 19 20 1 0 0 0 0 19 27 2 0 0 0 0 20 25 1 0 0 0 0 20 26 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	481.94
Volume:	374.037
LogP:	5.876
LogD:	4.009
LogS:	-5.077
# Rotatable Bonds:	3
TPSA:	77.33
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.284
Synthetic Accessibility Score:	2.975
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.253
MDCK Permeability:	8.259278729383368e-06
Pgp-inhibitor:	0.999
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.076
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.107

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.152
Plasma Protein Binding (PPB):	99.58890533447266%
Volume Distribution (VD):	1.432
Pgp-substrate:	0.7849515676498413%

ADMET: Metabolism

CYP1A2-inhibitor:	0.974
CYP1A2-substrate:	0.175
CYP2C19-inhibitor:	0.919
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.838
CYP2C9-substrate:	0.895
CYP2D6-inhibitor:	0.805
CYP2D6-substrate:	0.804
CYP3A4-inhibitor:	0.93
CYP3A4-substrate:	0.118

ADMET: Excretion

Clearance (CL):	2.412
Half-life (T1/2):	0.181

ADMET: Toxicity

hERG Blockers:	0.214
Human Hepatotoxicity (H-HT):	0.231
Drug-inuced Liver Injury (DILI):	0.948
AMES Toxicity:	0.031
Rat Oral Acute Toxicity:	0.75
Maximum Recommended Daily Dose:	0.99
Skin Sensitization:	0.086
Carcinogencity:	0.057
Eye Corrosion:	0.003
Eye Irritation:	0.349
Respiratory Toxicity:	0.47

Download Data

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

Natural Product: NPC474357

Natural Product ID:	NPC474357
*Common Name:**	Dibromodeoxytopsentin
IUPAC Name:	(6-bromo-1H-indol-3-yl)-[5-(6-bromo-1H-indol-3-yl)-1H-imidazol-2-yl]methanone
Synonyms:	Dibromodeoxytopsentin
Standard InCHIKey:	RSGZGJXKRHURTQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H12Br2N4O/c21-10-1-3-12-14(7-23-16(12)5-10)18-9-25-20(26-18)19(27)15-8-24-17-6-11(22)2-4-13(15)17/h1-9,23-24H,(H,25,26)
SMILES:	C1=CC2=C(C=C1Br)NC=C2C3=CN=C(N3)C(=O)C4=CNC5=C4C=CC(=C5)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465609
PubChem CID:	11363725
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0002013] Indolecarboxylic acids and derivatives

*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
IC50	1
Others	4

Activity Type	# Activity
Cell Line	5
Individual Protein	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	>	30.0	ug ml-1	PMID[496147]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	>	30.0	ug ml-1	PMID[496147]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	>	30.0	ug ml-1	PMID[496147]
NPT574	Cell Line	XF498	Homo sapiens	ED50	>	30.0	ug ml-1	PMID[496147]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	>	30.0	ug ml-1	PMID[496147]
NPT6230	Individual Protein	Pyruvate kinase isozymes R/L	Homo sapiens	Inhibition	<	40.0	%	PMID[496148]
NPT52	Individual Protein	Pyruvate kinase isozymes M1/M2	Homo sapiens	Inhibition	=	0.0	%	PMID[496148]
NPT2	Others	Unspecified		IC50	=	2.1	nM	PMID[496148]

☑ 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 NPC474357 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	1267
0.1-0.2	14847
0.2-0.3	18788
0.3-0.4	3381
0.4-0.5	2048
0.5-0.6	1617
0.6-0.7	614
0.7-0.8	119
0.8-0.85	5
0.85-0.9	6
0.9-0.95	1
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9951	High Similarity	NPC267078
0.9951	High Similarity	NPC935
0.9807	High Similarity	NPC470323
0.932	High Similarity	NPC267811
0.89	High Similarity	NPC470703
0.8852	High Similarity	NPC470702
0.8852	High Similarity	NPC473218
0.875	High Similarity	NPC116555
0.8577	High Similarity	NPC77101
0.819	Intermediate Similarity	NPC237414
0.8038	Intermediate Similarity	NPC326422
0.8033	Intermediate Similarity	NPC63109
0.7974	Intermediate Similarity	NPC156003
0.785	Intermediate Similarity	NPC477004
0.7804	Intermediate Similarity	NPC474389
0.7783	Intermediate Similarity	NPC474180
0.7783	Intermediate Similarity	NPC188821
0.7783	Intermediate Similarity	NPC304203
0.7731	Intermediate Similarity	NPC269203
0.7731	Intermediate Similarity	NPC13456
0.7731	Intermediate Similarity	NPC77241
0.7731	Intermediate Similarity	NPC166209
0.7706	Intermediate Similarity	NPC317701
0.7685	Intermediate Similarity	NPC201266
0.7685	Intermediate Similarity	NPC153123
0.7685	Intermediate Similarity	NPC475914
0.7685	Intermediate Similarity	NPC220797
0.7685	Intermediate Similarity	NPC268744
0.7685	Intermediate Similarity	NPC474318
0.767	Intermediate Similarity	NPC284775
0.7571	Intermediate Similarity	NPC110158
0.756	Intermediate Similarity	NPC191415
0.756	Intermediate Similarity	NPC307191
0.7523	Intermediate Similarity	NPC476460
0.7401	Intermediate Similarity	NPC282247
0.7358	Intermediate Similarity	NPC102755
0.7356	Intermediate Similarity	NPC477611
0.7349	Intermediate Similarity	NPC74619
0.7324	Intermediate Similarity	NPC108011
0.7315	Intermediate Similarity	NPC231536
0.7303	Intermediate Similarity	NPC37152
0.7273	Intermediate Similarity	NPC475736
0.7273	Intermediate Similarity	NPC167710
0.7243	Intermediate Similarity	NPC477003
0.721	Intermediate Similarity	NPC474195
0.7207	Intermediate Similarity	NPC19696
0.7207	Intermediate Similarity	NPC136957
0.7195	Intermediate Similarity	NPC475286
0.7195	Intermediate Similarity	NPC174281
0.7183	Intermediate Similarity	NPC16659
0.717	Intermediate Similarity	NPC473380
0.717	Intermediate Similarity	NPC240088
0.7161	Intermediate Similarity	NPC474196
0.7156	Intermediate Similarity	NPC324091
0.7137	Intermediate Similarity	NPC174489
0.7136	Intermediate Similarity	NPC265710
0.7125	Intermediate Similarity	NPC279189
0.7125	Intermediate Similarity	NPC200553
0.7123	Intermediate Similarity	NPC474958
0.7119	Intermediate Similarity	NPC229893
0.7115	Intermediate Similarity	NPC274229
0.7115	Intermediate Similarity	NPC17751
0.7109	Intermediate Similarity	NPC252572
0.7107	Intermediate Similarity	NPC162002
0.7102	Intermediate Similarity	NPC17487
0.7102	Intermediate Similarity	NPC201831
0.708	Intermediate Similarity	NPC471536
0.7078	Intermediate Similarity	NPC26641
0.7073	Intermediate Similarity	NPC477108
0.7073	Intermediate Similarity	NPC477107
0.7073	Intermediate Similarity	NPC477109
0.7072	Intermediate Similarity	NPC128244
0.7072	Intermediate Similarity	NPC329765
0.7072	Intermediate Similarity	NPC48117
0.7072	Intermediate Similarity	NPC476526
0.7062	Intermediate Similarity	NPC82331
0.7056	Intermediate Similarity	NPC471193
0.7056	Intermediate Similarity	NPC471194
0.7051	Intermediate Similarity	NPC99939
0.7051	Intermediate Similarity	NPC308931
0.7042	Intermediate Similarity	NPC69843
0.7018	Intermediate Similarity	NPC82053
0.7005	Intermediate Similarity	NPC21429
0.6991	Remote Similarity	NPC94211
0.6991	Remote Similarity	NPC475935
0.6991	Remote Similarity	NPC52909
0.6986	Remote Similarity	NPC317105
0.6963	Remote Similarity	NPC151635
0.6952	Remote Similarity	NPC42372
0.6947	Remote Similarity	NPC205254
0.6947	Remote Similarity	NPC106771
0.6947	Remote Similarity	NPC23420
0.6947	Remote Similarity	NPC303820
0.6944	Remote Similarity	NPC88110
0.694	Remote Similarity	NPC72956
0.694	Remote Similarity	NPC54981
0.6938	Remote Similarity	NPC253687
0.6938	Remote Similarity	NPC470203
0.6937	Remote Similarity	NPC477166
0.6937	Remote Similarity	NPC477167
0.6937	Remote Similarity	NPC473342
0.6937	Remote Similarity	NPC304187
0.6936	Remote Similarity	NPC477114
0.692	Remote Similarity	NPC102592
0.692	Remote Similarity	NPC79356
0.6916	Remote Similarity	NPC280297
0.6914	Remote Similarity	NPC207686
0.691	Remote Similarity	NPC6865
0.691	Remote Similarity	NPC153980
0.6906	Remote Similarity	NPC19342
0.6905	Remote Similarity	NPC247987
0.689	Remote Similarity	NPC470204
0.6883	Remote Similarity	NPC476524
0.6883	Remote Similarity	NPC476525
0.6881	Remote Similarity	NPC117027
0.6864	Remote Similarity	NPC17273
0.6864	Remote Similarity	NPC135601
0.6864	Remote Similarity	NPC27041
0.6864	Remote Similarity	NPC141612
0.6861	Remote Similarity	NPC216550
0.6857	Remote Similarity	NPC97902
0.6844	Remote Similarity	NPC63031
0.6837	Remote Similarity	NPC293216
0.6827	Remote Similarity	NPC295452
0.6827	Remote Similarity	NPC171393
0.6822	Remote Similarity	NPC471192
0.682	Remote Similarity	NPC276540
0.682	Remote Similarity	NPC233050
0.6818	Remote Similarity	NPC133003
0.6812	Remote Similarity	NPC141926
0.681	Remote Similarity	NPC71238
0.6802	Remote Similarity	NPC235685
0.6795	Remote Similarity	NPC82370
0.6794	Remote Similarity	NPC117980
0.6792	Remote Similarity	NPC280864
0.6787	Remote Similarity	NPC63571
0.6776	Remote Similarity	NPC97343
0.6776	Remote Similarity	NPC471943
0.6774	Remote Similarity	NPC101350
0.6773	Remote Similarity	NPC467063
0.6759	Remote Similarity	NPC317054
0.6758	Remote Similarity	NPC275292
0.6758	Remote Similarity	NPC243381
0.6757	Remote Similarity	NPC310633
0.6756	Remote Similarity	NPC88315
0.6744	Remote Similarity	NPC54214
0.6742	Remote Similarity	NPC476341
0.674	Remote Similarity	NPC227582
0.6739	Remote Similarity	NPC473761
0.673	Remote Similarity	NPC122141
0.6726	Remote Similarity	NPC473666
0.6714	Remote Similarity	NPC216643
0.6712	Remote Similarity	NPC111566
0.6712	Remote Similarity	NPC476527
0.6711	Remote Similarity	NPC272458
0.6695	Remote Similarity	NPC477413
0.6695	Remote Similarity	NPC469717
0.6694	Remote Similarity	NPC130570
0.6682	Remote Similarity	NPC470677
0.6681	Remote Similarity	NPC74413
0.6681	Remote Similarity	NPC36405
0.6667	Remote Similarity	NPC274981
0.6667	Remote Similarity	NPC266249
0.6652	Remote Similarity	NPC321708
0.6652	Remote Similarity	NPC470205
0.6652	Remote Similarity	NPC252338
0.6652	Remote Similarity	NPC103119
0.6651	Remote Similarity	NPC325903
0.665	Remote Similarity	NPC288838
0.6638	Remote Similarity	NPC131887
0.6638	Remote Similarity	NPC67288
0.6636	Remote Similarity	NPC115232
0.6624	Remote Similarity	NPC207020
0.6622	Remote Similarity	NPC154339
0.6621	Remote Similarity	NPC237188
0.6621	Remote Similarity	NPC157583
0.6611	Remote Similarity	NPC470731
0.6611	Remote Similarity	NPC470732
0.661	Remote Similarity	NPC123839
0.6609	Remote Similarity	NPC88115
0.6609	Remote Similarity	NPC81535
0.6604	Remote Similarity	NPC135141
0.6604	Remote Similarity	NPC474492
0.6604	Remote Similarity	NPC92796
0.6595	Remote Similarity	NPC260900
0.6595	Remote Similarity	NPC106757
0.6593	Remote Similarity	NPC210123
0.659	Remote Similarity	NPC227489
0.659	Remote Similarity	NPC28096
0.659	Remote Similarity	NPC476421
0.6589	Remote Similarity	NPC206148
0.6589	Remote Similarity	NPC149265
0.6577	Remote Similarity	NPC270834
0.657	Remote Similarity	NPC276657
0.6564	Remote Similarity	NPC47190
0.6561	Remote Similarity	NPC40530
0.6561	Remote Similarity	NPC73994
0.6561	Remote Similarity	NPC314281
0.6555	Remote Similarity	NPC53947
0.6552	Remote Similarity	NPC469308

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 NPC474357 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	527
0.1-0.2	946
0.2-0.3	1639
0.3-0.4	2361
0.4-0.5	1843
0.5-0.6	1414
0.6-0.7	394
0.7-0.8	24
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8302	Intermediate Similarity	NPD2008	Discontinued
0.8241	Intermediate Similarity	NPD2411	Approved
0.7972	Intermediate Similarity	NPD2442	Approved
0.7972	Intermediate Similarity	NPD2443	Approved
0.7907	Intermediate Similarity	NPD2881	Approved
0.7907	Intermediate Similarity	NPD2879	Approved
0.7854	Intermediate Similarity	NPD1600	Suspended
0.7844	Intermediate Similarity	NPD1506	Discontinued
0.7773	Intermediate Similarity	NPD2408	Discontinued
0.7763	Intermediate Similarity	NPD3905	Phase 3
0.7617	Intermediate Similarity	NPD460	Discontinued
0.7545	Intermediate Similarity	NPD4863	Approved
0.75	Intermediate Similarity	NPD6470	Phase 3
0.7477	Intermediate Similarity	NPD1982	Phase 1
0.7476	Intermediate Similarity	NPD1895	Discontinued
0.7431	Intermediate Similarity	NPD2880	Discontinued
0.7301	Intermediate Similarity	NPD2295	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD7657	Approved
0.7281	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD7656	Approved
0.7273	Intermediate Similarity	NPD5446	Phase 2
0.7249	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD8256	Approved
0.7229	Intermediate Similarity	NPD8258	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD8257	Approved
0.721	Intermediate Similarity	NPD6579	Phase 2
0.7202	Intermediate Similarity	NPD1658	Discontinued
0.7195	Intermediate Similarity	NPD1952	Discontinued
0.7149	Intermediate Similarity	NPD7023	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3347	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD6715	Discontinued
0.7124	Intermediate Similarity	NPD6229	Phase 2
0.7107	Intermediate Similarity	NPD6986	Phase 1
0.7101	Intermediate Similarity	NPD6165	Phase 2
0.7101	Intermediate Similarity	NPD6164	Phase 2
0.7097	Intermediate Similarity	NPD2793	Discontinued
0.7095	Intermediate Similarity	NPD8047	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD5198	Approved
0.7094	Intermediate Similarity	NPD5199	Approved
0.7091	Intermediate Similarity	NPD3431	Approved
0.7091	Intermediate Similarity	NPD3430	Approved
0.7082	Intermediate Similarity	NPD5643	Phase 2
0.708	Intermediate Similarity	NPD2364	Suspended
0.707	Intermediate Similarity	NPD4649	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD2009	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD6210	Phase 3
0.7062	Intermediate Similarity	NPD1567	Clinical (unspecified phase)
0.7061	Intermediate Similarity	NPD3839	Phase 2
0.7061	Intermediate Similarity	NPD3840	Phase 2
0.7051	Intermediate Similarity	NPD4541	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7207	Approved
0.7048	Intermediate Similarity	NPD4299	Phase 1
0.7048	Intermediate Similarity	NPD7209	Approved
0.7048	Intermediate Similarity	NPD7208	Approved
0.7026	Intermediate Similarity	NPD2363	Discontinued
0.7	Intermediate Similarity	NPD7704	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD6837	Clinical (unspecified phase)
0.698	Remote Similarity	NPD3360	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD2930	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD5831	Discontinued
0.6962	Remote Similarity	NPD4854	Phase 3
0.6953	Remote Similarity	NPD4341	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD5962	Phase 2
0.6937	Remote Similarity	NPD1896	Approved
0.6933	Remote Similarity	NPD5001	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD5415	Approved
0.6923	Remote Similarity	NPD4395	Phase 1
0.6913	Remote Similarity	NPD7445	Phase 1
0.6894	Remote Similarity	NPD2412	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD4924	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD8316	Phase 2
0.6872	Remote Similarity	NPD8317	Phase 2
0.687	Remote Similarity	NPD6271	Approved
0.6851	Remote Similarity	NPD6481	Clinical (unspecified phase)
0.6844	Remote Similarity	NPD1871	Approved
0.684	Remote Similarity	NPD6328	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD5854	Approved
0.6816	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6459	Phase 2
0.6808	Remote Similarity	NPD2333	Discontinued
0.6802	Remote Similarity	NPD5016	Approved
0.6797	Remote Similarity	NPD6458	Discontinued
0.6797	Remote Similarity	NPD4023	Clinical (unspecified phase)
0.679	Remote Similarity	NPD7887	Approved
0.679	Remote Similarity	NPD7888	Approved
0.6789	Remote Similarity	NPD6465	Phase 2
0.6787	Remote Similarity	NPD4940	Approved
0.6787	Remote Similarity	NPD3378	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD7459	Phase 2
0.6777	Remote Similarity	NPD5887	Clinical (unspecified phase)
0.6773	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.677	Remote Similarity	NPD6278	Clinical (unspecified phase)
0.677	Remote Similarity	NPD2316	Clinical (unspecified phase)
0.676	Remote Similarity	NPD3914	Clinical (unspecified phase)
0.676	Remote Similarity	NPD7857	Phase 3
0.676	Remote Similarity	NPD7856	Phase 2
0.6743	Remote Similarity	NPD3341	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD4872	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD5853	Phase 3
0.6726	Remote Similarity	NPD7406	Phase 2
0.6726	Remote Similarity	NPD8641	Approved
0.6726	Remote Similarity	NPD5855	Phase 3
0.6724	Remote Similarity	NPD5489	Phase 1
0.6724	Remote Similarity	NPD5491	Phase 3
0.6714	Remote Similarity	NPD1313	Approved
0.6711	Remote Similarity	NPD4922	Phase 2
0.6708	Remote Similarity	NPD5827	Discontinued
0.6708	Remote Similarity	NPD1996	Discontinued
0.6706	Remote Similarity	NPD3959	Phase 2
0.6706	Remote Similarity	NPD3962	Phase 2
0.6694	Remote Similarity	NPD2400	Phase 2
0.6694	Remote Similarity	NPD7661	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD2392	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD1708	Approved
0.6682	Remote Similarity	NPD1707	Approved
0.6682	Remote Similarity	NPD4988	Discontinued
0.6681	Remote Similarity	NPD2446	Approved
0.6681	Remote Similarity	NPD4051	Discontinued
0.6681	Remote Similarity	NPD2445	Approved
0.6681	Remote Similarity	NPD3485	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD4446	Approved
0.668	Remote Similarity	NPD3811	Discontinued
0.6667	Remote Similarity	NPD8484	Phase 2
0.6667	Remote Similarity	NPD5462	Discontinued
0.6667	Remote Similarity	NPD3419	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6268	Phase 1
0.6667	Remote Similarity	NPD6269	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5985	Phase 2
0.6653	Remote Similarity	NPD8159	Discontinued
0.6653	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.6653	Remote Similarity	NPD6970	Phase 2
0.6653	Remote Similarity	NPD5465	Phase 2
0.6652	Remote Similarity	NPD1332	Clinical (unspecified phase)
0.664	Remote Similarity	NPD3786	Phase 3
0.664	Remote Similarity	NPD7172	Approved
0.664	Remote Similarity	NPD7173	Approved
0.6638	Remote Similarity	NPD6469	Phase 3
0.6638	Remote Similarity	NPD2819	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD6468	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD4615	Phase 2
0.6636	Remote Similarity	NPD5508	Phase 1
0.6636	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD2960	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD4848	Phase 1
0.6622	Remote Similarity	NPD5686	Approved
0.6622	Remote Similarity	NPD2456	Phase 2
0.6622	Remote Similarity	NPD5145	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD2457	Phase 2
0.6622	Remote Similarity	NPD5685	Approved
0.661	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD6520	Phase 3
0.6596	Remote Similarity	NPD6521	Phase 3
0.6583	Remote Similarity	NPD2812	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD2813	Phase 3
0.6582	Remote Similarity	NPD3265	Phase 1
0.658	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD3960	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD3860	Discontinued
0.6565	Remote Similarity	NPD465	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD2591	Phase 2
0.6562	Remote Similarity	NPD6721	Phase 1
0.6562	Remote Similarity	NPD4902	Discontinued
0.6561	Remote Similarity	NPD2481	Approved
0.6561	Remote Similarity	NPD2479	Phase 3
0.6558	Remote Similarity	NPD1333	Phase 3
0.6553	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD4318	Clinical (unspecified phase)
0.6546	Remote Similarity	NPD7415	Suspended
0.6545	Remote Similarity	NPD7694	Discontinued
0.6542	Remote Similarity	NPD1015	Phase 2
0.6542	Remote Similarity	NPD1016	Phase 2
0.6542	Remote Similarity	NPD4851	Clinical (unspecified phase)
0.654	Remote Similarity	NPD5072	Discontinued
0.6538	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD6265	Discontinued
0.6533	Remote Similarity	NPD3246	Discontinued
0.6528	Remote Similarity	NPD2478	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD2510	Approved
0.6525	Remote Similarity	NPD2509	Approved
0.6525	Remote Similarity	NPD2311	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD3830	Phase 1
0.652	Remote Similarity	NPD7709	Discontinued
0.6518	Remote Similarity	NPD7767	Approved
0.6518	Remote Similarity	NPD4298	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD3432	Approved
0.6509	Remote Similarity	NPD6816	Phase 3
0.6498	Remote Similarity	NPD8523	Approved
0.6498	Remote Similarity	NPD4558	Phase 2
0.6496	Remote Similarity	NPD5821	Approved
0.649	Remote Similarity	NPD6850	Phase 2
0.649	Remote Similarity	NPD6849	Phase 2
0.6489	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD2872	Phase 2
0.6488	Remote Similarity	NPD5533	Discontinued
0.6486	Remote Similarity	NPD5473	Discontinued
0.6485	Remote Similarity	NPD4352	Phase 1
0.6485	Remote Similarity	NPD6954	Phase 2
0.6483	Remote Similarity	NPD8410	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD4142	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