NPASS Compound

Structure

NPC470703 OpenBabel07101719522D 27 31 0 0 1 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 3 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 1 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:	483.95
Volume:	376.674
LogP:	5.16
LogD:	3.948
LogS:	-4.074
# Rotatable Bonds:	3
TPSA:	80.49
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.266
Synthetic Accessibility Score:	3.478
Fsp3:	0.05
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.215
MDCK Permeability:	6.646072506555356e-06
Pgp-inhibitor:	0.065
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.662
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.033

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.071
Plasma Protein Binding (PPB):	98.49653625488281%
Volume Distribution (VD):	1.027
Pgp-substrate:	1.3056309223175049%

ADMET: Metabolism

CYP1A2-inhibitor:	0.923
CYP1A2-substrate:	0.174
CYP2C19-inhibitor:	0.947
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.902
CYP2C9-substrate:	0.886
CYP2D6-inhibitor:	0.954
CYP2D6-substrate:	0.716
CYP3A4-inhibitor:	0.938
CYP3A4-substrate:	0.226

ADMET: Excretion

Clearance (CL):	2.222
Half-life (T1/2):	0.309

ADMET: Toxicity

hERG Blockers:	0.785
Human Hepatotoxicity (H-HT):	0.124
Drug-inuced Liver Injury (DILI):	0.719
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.93
Maximum Recommended Daily Dose:	0.992
Skin Sensitization:	0.245
Carcinogencity:	0.028
Eye Corrosion:	0.003
Eye Irritation:	0.019
Respiratory Toxicity:	0.738

Download Data

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

Natural Product: NPC470703

Natural Product ID:	NPC470703
*Common Name:**	Spongotine C
IUPAC Name:	(6-bromo-1H-indol-3-yl)-[5-(6-bromo-1H-indol-3-yl)-4,5-dihydro-1H-imidazol-2-yl]methanone
Synonyms:	spongotine C
Standard InCHIKey:	YFOAHBJMHACINK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H14Br2N4O/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/h1-8,18,23-24H,9H2,(H,25,26)
SMILES:	c1cc2c(c[nH]c2cc1Br)C1CNC(=N1)C(=O)c1c[nH]c2cc(ccc12)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL219505
PubChem CID:	16104846
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0002497] Indoles [CHEMONTID:0004196] 3-alkylindoles

*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]
NPO40773	Topsentia sp.	Species		Eukaryota	n.a.	n.a.	n.a.	PMID[28837335]
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	3
MIC	2

Activity Type	# Activity
Cell Line	7
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	5.22	ug ml-1	PMID[534562]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	=	4.81	ug ml-1	PMID[534562]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	4.82	ug ml-1	PMID[534562]
NPT574	Cell Line	XF498	Homo sapiens	ED50	=	5.16	ug ml-1	PMID[534562]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	4.88	ug ml-1	PMID[534562]
NPT4754	Cell Line	BSC-1	Chlorocebus aethiops	IC50	=	120000.0	nM	PMID[534563]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	180000.0	nM	PMID[534563]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[534563]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	11.0	ug.mL-1	PMID[534563]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	57000.0	nM	PMID[534563]

☑ 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 NPC470703 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	792
0.1-0.2	11637
0.2-0.3	18982
0.3-0.4	6211
0.4-0.5	2033
0.5-0.6	1831
0.6-0.7	1004
0.7-0.8	174
0.8-0.85	25
0.85-0.9	4
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9947	High Similarity	NPC473218
0.9947	High Similarity	NPC470702
0.89	High Similarity	NPC474357
0.8852	High Similarity	NPC935
0.8852	High Similarity	NPC267078
0.8714	High Similarity	NPC470323
0.8528	High Similarity	NPC477004
0.8528	High Similarity	NPC237414
0.8485	Intermediate Similarity	NPC269203
0.8485	Intermediate Similarity	NPC77241
0.8485	Intermediate Similarity	NPC13456
0.8485	Intermediate Similarity	NPC166209
0.8434	Intermediate Similarity	NPC268744
0.8434	Intermediate Similarity	NPC153123
0.8434	Intermediate Similarity	NPC474318
0.8434	Intermediate Similarity	NPC475914
0.8434	Intermediate Similarity	NPC220797
0.8434	Intermediate Similarity	NPC201266
0.836	Intermediate Similarity	NPC284775
0.8274	Intermediate Similarity	NPC304203
0.8274	Intermediate Similarity	NPC326422
0.8238	Intermediate Similarity	NPC110158
0.823	Intermediate Similarity	NPC267811
0.82	Intermediate Similarity	NPC474389
0.8173	Intermediate Similarity	NPC476460
0.8107	Intermediate Similarity	NPC116555
0.809	Intermediate Similarity	NPC188821
0.809	Intermediate Similarity	NPC474180
0.801	Intermediate Similarity	NPC477611
0.7913	Intermediate Similarity	NPC317701
0.7868	Intermediate Similarity	NPC477003
0.7857	Intermediate Similarity	NPC191415
0.7739	Intermediate Similarity	NPC308931
0.7739	Intermediate Similarity	NPC99939
0.77	Intermediate Similarity	NPC471193
0.77	Intermediate Similarity	NPC471194
0.7692	Intermediate Similarity	NPC156003
0.7677	Intermediate Similarity	NPC307191
0.7645	Intermediate Similarity	NPC77101
0.7644	Intermediate Similarity	NPC94211
0.7644	Intermediate Similarity	NPC475935
0.7644	Intermediate Similarity	NPC52909
0.7638	Intermediate Similarity	NPC102755
0.7638	Intermediate Similarity	NPC117027
0.7621	Intermediate Similarity	NPC167710
0.76	Intermediate Similarity	NPC21429
0.7596	Intermediate Similarity	NPC106771
0.7596	Intermediate Similarity	NPC303820
0.7596	Intermediate Similarity	NPC23420
0.7596	Intermediate Similarity	NPC205254
0.7586	Intermediate Similarity	NPC231536
0.7583	Intermediate Similarity	NPC82053
0.757	Intermediate Similarity	NPC72956
0.7565	Intermediate Similarity	NPC42372
0.7565	Intermediate Similarity	NPC17751
0.7563	Intermediate Similarity	NPC474958
0.7548	Intermediate Similarity	NPC136957
0.7548	Intermediate Similarity	NPC19696
0.7544	Intermediate Similarity	NPC37152
0.7538	Intermediate Similarity	NPC16659
0.7538	Intermediate Similarity	NPC88110
0.7536	Intermediate Similarity	NPC174281
0.7536	Intermediate Similarity	NPC475286
0.7535	Intermediate Similarity	NPC153980
0.7535	Intermediate Similarity	NPC6865
0.7523	Intermediate Similarity	NPC475736
0.7487	Intermediate Similarity	NPC265710
0.7474	Intermediate Similarity	NPC274229
0.7455	Intermediate Similarity	NPC474195
0.7451	Intermediate Similarity	NPC473666
0.7447	Intermediate Similarity	NPC471536
0.7437	Intermediate Similarity	NPC240088
0.7437	Intermediate Similarity	NPC473380
0.7431	Intermediate Similarity	NPC471192
0.7426	Intermediate Similarity	NPC108011
0.7424	Intermediate Similarity	NPC293216
0.7421	Intermediate Similarity	NPC141926
0.7415	Intermediate Similarity	NPC324091
0.7411	Intermediate Similarity	NPC82331
0.7404	Intermediate Similarity	NPC329765
0.7404	Intermediate Similarity	NPC48117
0.7404	Intermediate Similarity	NPC476526
0.74	Intermediate Similarity	NPC233050
0.74	Intermediate Similarity	NPC276540
0.7399	Intermediate Similarity	NPC474196
0.7368	Intermediate Similarity	NPC174489
0.736	Intermediate Similarity	NPC471943
0.7357	Intermediate Similarity	NPC279189
0.7357	Intermediate Similarity	NPC200553
0.7343	Intermediate Similarity	NPC477166
0.7343	Intermediate Similarity	NPC477167
0.7343	Intermediate Similarity	NPC473342
0.7343	Intermediate Similarity	NPC304187
0.7337	Intermediate Similarity	NPC280297
0.7336	Intermediate Similarity	NPC162002
0.7333	Intermediate Similarity	NPC131887
0.7333	Intermediate Similarity	NPC247987
0.7327	Intermediate Similarity	NPC275292
0.7327	Intermediate Similarity	NPC243381
0.7308	Intermediate Similarity	NPC88315
0.7304	Intermediate Similarity	NPC26641
0.7304	Intermediate Similarity	NPC133003
0.7291	Intermediate Similarity	NPC470205
0.7286	Intermediate Similarity	NPC252572
0.7286	Intermediate Similarity	NPC227582
0.7282	Intermediate Similarity	NPC321708
0.7277	Intermediate Similarity	NPC229893
0.7273	Intermediate Similarity	NPC97343
0.7253	Intermediate Similarity	NPC17487
0.7253	Intermediate Similarity	NPC201831
0.7251	Intermediate Similarity	NPC67288
0.7249	Intermediate Similarity	NPC288838
0.7241	Intermediate Similarity	NPC470677
0.724	Intermediate Similarity	NPC477114
0.7225	Intermediate Similarity	NPC19342
0.7222	Intermediate Similarity	NPC477107
0.7222	Intermediate Similarity	NPC477108
0.7222	Intermediate Similarity	NPC477109
0.7217	Intermediate Similarity	NPC74413
0.7215	Intermediate Similarity	NPC207020
0.7214	Intermediate Similarity	NPC151635
0.7208	Intermediate Similarity	NPC280864
0.7205	Intermediate Similarity	NPC63031
0.7189	Intermediate Similarity	NPC476525
0.7189	Intermediate Similarity	NPC476524
0.7183	Intermediate Similarity	NPC252338
0.7179	Intermediate Similarity	NPC92796
0.7179	Intermediate Similarity	NPC135141
0.7177	Intermediate Similarity	NPC216550
0.7171	Intermediate Similarity	NPC467063
0.7163	Intermediate Similarity	NPC154339
0.7157	Intermediate Similarity	NPC149265
0.7157	Intermediate Similarity	NPC274981
0.7156	Intermediate Similarity	NPC79356
0.7156	Intermediate Similarity	NPC102592
0.7135	Intermediate Similarity	NPC53947
0.7121	Intermediate Similarity	NPC115232
0.7116	Intermediate Similarity	NPC260900
0.7109	Intermediate Similarity	NPC195239
0.7109	Intermediate Similarity	NPC157828
0.7107	Intermediate Similarity	NPC63109
0.7104	Intermediate Similarity	NPC282247
0.7101	Intermediate Similarity	NPC17273
0.7101	Intermediate Similarity	NPC135601
0.7101	Intermediate Similarity	NPC141612
0.7101	Intermediate Similarity	NPC63571
0.7097	Intermediate Similarity	NPC471191
0.7095	Intermediate Similarity	NPC272458
0.7095	Intermediate Similarity	NPC47190
0.7092	Intermediate Similarity	NPC474492
0.7085	Intermediate Similarity	NPC27041
0.7079	Intermediate Similarity	NPC469529
0.7075	Intermediate Similarity	NPC11445
0.7075	Intermediate Similarity	NPC128244
0.7075	Intermediate Similarity	NPC179701
0.7071	Intermediate Similarity	NPC317105
0.7069	Intermediate Similarity	NPC97902
0.7067	Intermediate Similarity	NPC17059
0.7067	Intermediate Similarity	NPC310633
0.7067	Intermediate Similarity	NPC276657
0.7065	Intermediate Similarity	NPC54214
0.7062	Intermediate Similarity	NPC267343
0.7059	Intermediate Similarity	NPC477413
0.7056	Intermediate Similarity	NPC207686
0.7042	Intermediate Similarity	NPC262898
0.7041	Intermediate Similarity	NPC216643
0.7037	Intermediate Similarity	NPC476073
0.7037	Intermediate Similarity	NPC473761
0.7027	Intermediate Similarity	NPC477610
0.7026	Intermediate Similarity	NPC34844
0.702	Intermediate Similarity	NPC470203
0.702	Intermediate Similarity	NPC242116
0.7019	Intermediate Similarity	NPC111566
0.7019	Intermediate Similarity	NPC476527
0.7019	Intermediate Similarity	NPC94752
0.7014	Intermediate Similarity	NPC82370
0.7	Intermediate Similarity	NPC49217
0.6995	Remote Similarity	NPC2272
0.6986	Remote Similarity	NPC278434
0.6978	Remote Similarity	NPC469717
0.6976	Remote Similarity	NPC11126
0.6974	Remote Similarity	NPC325903
0.6971	Remote Similarity	NPC15102
0.697	Remote Similarity	NPC100104
0.697	Remote Similarity	NPC470204
0.697	Remote Similarity	NPC470680
0.6967	Remote Similarity	NPC138370
0.6952	Remote Similarity	NPC103119
0.695	Remote Similarity	NPC233380
0.6948	Remote Similarity	NPC202812
0.6942	Remote Similarity	NPC79777
0.6942	Remote Similarity	NPC477042
0.6942	Remote Similarity	NPC73994
0.6942	Remote Similarity	NPC234403
0.6936	Remote Similarity	NPC235685
0.6935	Remote Similarity	NPC214106
0.6927	Remote Similarity	NPC237188
0.6927	Remote Similarity	NPC59269
0.6927	Remote Similarity	NPC157583
0.6923	Remote Similarity	NPC228835

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 NPC470703 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	370
0.1-0.2	836
0.2-0.3	1197
0.3-0.4	2451
0.4-0.5	2100
0.5-0.6	1697
0.6-0.7	480
0.7-0.8	19
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7837	Intermediate Similarity	NPD2008	Discontinued
0.7783	Intermediate Similarity	NPD2411	Approved
0.7512	Intermediate Similarity	NPD2443	Approved
0.7512	Intermediate Similarity	NPD2442	Approved
0.7441	Intermediate Similarity	NPD2881	Approved
0.7441	Intermediate Similarity	NPD2879	Approved
0.7426	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD2408	Discontinued
0.7315	Intermediate Similarity	NPD1600	Suspended
0.7302	Intermediate Similarity	NPD3905	Phase 3
0.726	Intermediate Similarity	NPD4922	Phase 2
0.7184	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD4848	Phase 1
0.7143	Intermediate Similarity	NPD1506	Discontinued
0.711	Intermediate Similarity	NPD2510	Approved
0.711	Intermediate Similarity	NPD2509	Approved
0.7108	Intermediate Similarity	NPD5473	Discontinued
0.7108	Intermediate Similarity	NPD2479	Phase 3
0.7108	Intermediate Similarity	NPD2481	Approved
0.7089	Intermediate Similarity	NPD1982	Phase 1
0.7067	Intermediate Similarity	NPD4988	Discontinued
0.7062	Intermediate Similarity	NPD460	Discontinued
0.7045	Intermediate Similarity	NPD4051	Discontinued
0.7042	Intermediate Similarity	NPD6664	Approved
0.7032	Intermediate Similarity	NPD6459	Phase 2
0.7028	Intermediate Similarity	NPD7619	Phase 3
0.7028	Intermediate Similarity	NPD7618	Phase 3
0.7024	Intermediate Similarity	NPD1291	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD5199	Approved
0.7022	Intermediate Similarity	NPD5198	Approved
0.7014	Intermediate Similarity	NPD4614	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7564	Discontinued
0.6995	Remote Similarity	NPD4128	Approved
0.699	Remote Similarity	NPD1895	Discontinued
0.6972	Remote Similarity	NPD5426	Phase 3
0.6968	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD2880	Discontinued
0.6957	Remote Similarity	NPD6164	Phase 2
0.6957	Remote Similarity	NPD6165	Phase 2
0.6942	Remote Similarity	NPD6595	Phase 3
0.6937	Remote Similarity	NPD4863	Approved
0.6927	Remote Similarity	NPD4181	Approved
0.6916	Remote Similarity	NPD2289	Phase 3
0.6916	Remote Similarity	NPD2290	Phase 3
0.6909	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6470	Phase 3
0.6889	Remote Similarity	NPD3394	Approved
0.6889	Remote Similarity	NPD3393	Approved
0.6889	Remote Similarity	NPD3389	Approved
0.6884	Remote Similarity	NPD5446	Phase 2
0.688	Remote Similarity	NPD8047	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6858	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6844	Remote Similarity	NPD6481	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1996	Discontinued
0.6829	Remote Similarity	NPD482	Approved
0.6827	Remote Similarity	NPD4011	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD4374	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4299	Phase 1
0.6818	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD4851	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD7666	Phase 3
0.6802	Remote Similarity	NPD7665	Phase 2
0.6796	Remote Similarity	NPD4075	Phase 2
0.6794	Remote Similarity	NPD3320	Approved
0.6794	Remote Similarity	NPD3319	Phase 1
0.6794	Remote Similarity	NPD3318	Approved
0.6791	Remote Similarity	NPD5853	Phase 3
0.6791	Remote Similarity	NPD5855	Phase 3
0.6772	Remote Similarity	NPD198	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD2295	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD2096	Phase 2
0.6762	Remote Similarity	NPD2091	Phase 2
0.6759	Remote Similarity	NPD7027	Phase 3
0.6754	Remote Similarity	NPD786	Approved
0.6745	Remote Similarity	NPD3961	Discontinued
0.6743	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD6999	Discontinued
0.6743	Remote Similarity	NPD5854	Approved
0.6742	Remote Similarity	NPD7208	Approved
0.6742	Remote Similarity	NPD7207	Approved
0.6742	Remote Similarity	NPD7209	Approved
0.6741	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD2007	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD3347	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD1952	Discontinued
0.6726	Remote Similarity	NPD6787	Phase 2
0.6716	Remote Similarity	NPD1343	Approved
0.6715	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD2095	Phase 2
0.6714	Remote Similarity	NPD2092	Phase 2
0.6714	Remote Similarity	NPD7175	Phase 1
0.6714	Remote Similarity	NPD2094	Phase 2
0.6713	Remote Similarity	NPD7024	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD2172	Phase 1
0.6698	Remote Similarity	NPD7026	Phase 2
0.6696	Remote Similarity	NPD7970	Approved
0.6696	Remote Similarity	NPD6579	Phase 2
0.6696	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD1722	Approved
0.6682	Remote Similarity	NPD1851	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD6278	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD5017	Discontinued
0.6681	Remote Similarity	NPD7661	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD8458	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5901	Discontinued
0.6667	Remote Similarity	NPD3246	Discontinued
0.6652	Remote Similarity	NPD8488	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD2590	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD8257	Approved
0.6638	Remote Similarity	NPD8256	Approved
0.6638	Remote Similarity	NPD5415	Approved
0.6638	Remote Similarity	NPD8258	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD7001	Phase 3
0.6634	Remote Similarity	NPD2390	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD2837	Discontinued
0.6625	Remote Similarity	NPD3360	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.662	Remote Similarity	NPD7098	Clinical (unspecified phase)
0.662	Remote Similarity	NPD2793	Discontinued
0.662	Remote Similarity	NPD3431	Approved
0.662	Remote Similarity	NPD3430	Approved
0.662	Remote Similarity	NPD6217	Discontinued
0.6619	Remote Similarity	NPD6277	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD3914	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD6986	Phase 1
0.6608	Remote Similarity	NPD7656	Approved
0.6608	Remote Similarity	NPD7657	Approved
0.6607	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD2960	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD7817	Phase 1
0.6605	Remote Similarity	NPD5685	Approved
0.6605	Remote Similarity	NPD5686	Approved
0.6599	Remote Similarity	NPD1270	Approved
0.6592	Remote Similarity	NPD6229	Phase 2
0.6589	Remote Similarity	NPD2009	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD1708	Approved
0.6588	Remote Similarity	NPD1707	Approved
0.6588	Remote Similarity	NPD4649	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD5065	Approved
0.6579	Remote Similarity	NPD4341	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD4924	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD1658	Discontinued
0.6574	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD3583	Phase 2
0.6566	Remote Similarity	NPD3100	Discontinued
0.6565	Remote Similarity	NPD5643	Phase 2
0.6564	Remote Similarity	NPD6152	Phase 1
0.6562	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD1284	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD1332	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD2367	Phase 2
0.6553	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6210	Phase 3
0.6538	Remote Similarity	NPD750	Phase 2
0.6535	Remote Similarity	NPD7454	Approved
0.6535	Remote Similarity	NPD6954	Phase 2
0.6535	Remote Similarity	NPD7455	Approved
0.6533	Remote Similarity	NPD3839	Phase 2
0.6533	Remote Similarity	NPD3840	Phase 2
0.6532	Remote Similarity	NPD6837	Clinical (unspecified phase)
0.653	Remote Similarity	NPD7023	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD3871	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD3870	Clinical (unspecified phase)
0.652	Remote Similarity	NPD1853	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD6987	Phase 1
0.6516	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD1248	Discontinued
0.6496	Remote Similarity	NPD5001	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD7470	Discontinued
0.6489	Remote Similarity	NPD4023	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD3323	Discontinued
0.6481	Remote Similarity	NPD5016	Approved
0.6481	Remote Similarity	NPD6242	Discontinued
0.648	Remote Similarity	NPD4637	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD2185	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7459	Phase 2
0.6468	Remote Similarity	NPD1896	Approved
0.6466	Remote Similarity	NPD4541	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD4852	Phase 2
0.6454	Remote Similarity	NPD6458	Discontinued
0.6452	Remote Similarity	NPD5145	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD1905	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD6204	Clinical (unspecified phase)
0.6445	Remote Similarity	NPD2144	Approved

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