NPASS Compound

Structure

NPC184465 OpenBabel07101718222D 21 21 0 0 0 0 0 0 0 0999 V2000 1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -0.0000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 3 2 0 0 0 0 2 8 1 0 0 0 0 3 11 1 0 0 0 0 4 5 1 0 0 0 0 4 14 1 0 0 0 0 5 21 1 0 0 0 0 6 8 2 0 0 0 0 6 9 1 0 0 0 0 7 8 1 0 0 0 0 7 10 1 0 0 0 0 9 11 2 0 0 0 0 9 13 1 0 0 0 0 10 12 1 0 0 0 0 10 15 2 0 0 0 0 11 16 1 0 0 0 0 12 14 2 3 0 0 0 12 17 1 0 0 0 0 15 18 1 0 0 0 0 19 21 2 0 0 0 0 20 21 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	377.99
Volume:	298.107
LogP:	0.282
LogD:	0.143
LogS:	-2.717
# Rotatable Bonds:	7
TPSA:	116.06
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.382
Synthetic Accessibility Score:	2.674
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.123
MDCK Permeability:	1.4172340343066026e-05
Pgp-inhibitor:	0.018
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.12
20% Bioavailability (F20%):	0.019
30% Bioavailability (F30%):	0.046

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.257
Plasma Protein Binding (PPB):	56.22896194458008%
Volume Distribution (VD):	0.437
Pgp-substrate:	50.19834518432617%

ADMET: Metabolism

CYP1A2-inhibitor:	0.102
CYP1A2-substrate:	0.059
CYP2C19-inhibitor:	0.072
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.078
CYP2C9-substrate:	0.845
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.132
CYP3A4-inhibitor:	0.045
CYP3A4-substrate:	0.23

ADMET: Excretion

Clearance (CL):	1.318
Half-life (T1/2):	0.831

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.324
Drug-inuced Liver Injury (DILI):	0.958
AMES Toxicity:	0.196
Rat Oral Acute Toxicity:	0.072
Maximum Recommended Daily Dose:	0.014
Skin Sensitization:	0.052
Carcinogencity:	0.06
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.019

Download Data

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

Natural Product: NPC184465

Natural Product ID:	NPC184465
*Common Name:**	Psammaplin I
IUPAC Name:	(2E)-3-(3-bromo-4-hydroxyphenyl)-2-hydroxyimino-N-(2-methylsulfonylethyl)propanamide
Synonyms:	Psammaplin I
Standard InCHIKey:	KPZACOXJRSCTBD-XNTDXEJSSA-N
Standard InCHI:	InChI=1S/C12H15BrN2O5S/c1-21(19,20)5-4-14-12(17)10(15-18)7-8-2-3-11(16)9(13)6-8/h2-3,6,16,18H,4-5,7H2,1H3,(H,14,17)/b15-10+
SMILES:	CS(=O)(=O)CCN=C(/C(=N/O)/Cc1ccc(c(c1)Br)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL481500
PubChem CID:	10872570
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0002320] Halophenols [CHEMONTID:0002764] Bromophenols [CHEMONTID:0002768] O-bromophenols

*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
NPO33335	Jaspis sp.	Species	Ancorinidae	Eukaryota	n.a.	Vanuatu islands	n.a.	PMID[10924170]
NPO33335	Jaspis sp.	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11277766]
NPO33362	Poecillastra sp.	Species	Vulcanellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17378533]
NPO33335	Jaspis sp.	Species	Ancorinidae	Eukaryota	n.a.	depth of 25 m off the shore of Keomun Island, Korea	2004-AUG	PMID[18407691]
NPO33335	Jaspis sp.	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18990572]
NPO33362	Poecillastra sp.	Species	Vulcanellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18990572]
NPO33335	Jaspis sp.	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8326327]

☑ 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
EC50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	EC50	=	4.15	ug.mL-1	PMID[488399]
NPT146	Cell Line	SK-OV-3	Homo sapiens	EC50	=	1.76	ug.mL-1	PMID[488399]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	EC50	=	2.84	ug.mL-1	PMID[488399]
NPT574	Cell Line	XF498	Homo sapiens	EC50	=	2.96	ug.mL-1	PMID[488399]
NPT148	Cell Line	HCT-15	Homo sapiens	EC50	=	6.51	ug.mL-1	PMID[488399]

☑ 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 NPC184465 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	232
0.1-0.2	3282
0.2-0.3	13827
0.3-0.4	8612
0.4-0.5	13239
0.5-0.6	3129
0.6-0.7	331
0.7-0.8	31
0.8-0.85	4
0.85-0.9	6
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9606	High Similarity	NPC166624
0.9444	High Similarity	NPC202776
0.9084	High Similarity	NPC163810
0.8872	High Similarity	NPC71888
0.8872	High Similarity	NPC120114
0.8741	High Similarity	NPC309667
0.8603	High Similarity	NPC475132
0.8603	High Similarity	NPC474587
0.854	High Similarity	NPC475293
0.8444	Intermediate Similarity	NPC474753
0.8433	Intermediate Similarity	NPC474091
0.837	Intermediate Similarity	NPC475735
0.8138	Intermediate Similarity	NPC20755
0.7972	Intermediate Similarity	NPC474128
0.7887	Intermediate Similarity	NPC197045
0.7714	Intermediate Similarity	NPC473724
0.7662	Intermediate Similarity	NPC123848
0.7424	Intermediate Similarity	NPC59387
0.7419	Intermediate Similarity	NPC473738
0.7394	Intermediate Similarity	NPC99280
0.7386	Intermediate Similarity	NPC475432
0.732	Intermediate Similarity	NPC258222
0.7308	Intermediate Similarity	NPC471495
0.7197	Intermediate Similarity	NPC473358
0.7192	Intermediate Similarity	NPC303993
0.7188	Intermediate Similarity	NPC178902
0.7185	Intermediate Similarity	NPC317254
0.7154	Intermediate Similarity	NPC231705
0.7153	Intermediate Similarity	NPC474536
0.7134	Intermediate Similarity	NPC156311
0.7122	Intermediate Similarity	NPC324702
0.7121	Intermediate Similarity	NPC258056
0.7111	Intermediate Similarity	NPC115803
0.7111	Intermediate Similarity	NPC118202
0.7097	Intermediate Similarity	NPC109968
0.7068	Intermediate Similarity	NPC474149
0.7047	Intermediate Similarity	NPC213471
0.7037	Intermediate Similarity	NPC309808
0.7008	Intermediate Similarity	NPC107619
0.7	Intermediate Similarity	NPC86966
0.6992	Remote Similarity	NPC54543
0.6982	Remote Similarity	NPC152205
0.6982	Remote Similarity	NPC475283
0.6978	Remote Similarity	NPC283760
0.697	Remote Similarity	NPC142297
0.6957	Remote Similarity	NPC311737
0.6957	Remote Similarity	NPC38458
0.6929	Remote Similarity	NPC112823
0.6918	Remote Similarity	NPC474087
0.6917	Remote Similarity	NPC153690
0.6884	Remote Similarity	NPC82963
0.6831	Remote Similarity	NPC136543
0.68	Remote Similarity	NPC470471
0.6791	Remote Similarity	NPC24101
0.6791	Remote Similarity	NPC96224
0.6779	Remote Similarity	NPC243404
0.6741	Remote Similarity	NPC473372
0.6739	Remote Similarity	NPC142599
0.6738	Remote Similarity	NPC38483
0.6738	Remote Similarity	NPC319950
0.673	Remote Similarity	NPC47672
0.6713	Remote Similarity	NPC7830
0.6711	Remote Similarity	NPC470470
0.671	Remote Similarity	NPC78530
0.6692	Remote Similarity	NPC275104
0.6691	Remote Similarity	NPC471487
0.6686	Remote Similarity	NPC225130
0.6667	Remote Similarity	NPC296202
0.6647	Remote Similarity	NPC469979
0.6641	Remote Similarity	NPC289381
0.6641	Remote Similarity	NPC155847
0.6622	Remote Similarity	NPC55113
0.662	Remote Similarity	NPC268572
0.662	Remote Similarity	NPC117759
0.6619	Remote Similarity	NPC94217
0.6608	Remote Similarity	NPC473462
0.6608	Remote Similarity	NPC126128
0.6608	Remote Similarity	NPC207819
0.6608	Remote Similarity	NPC298981
0.6608	Remote Similarity	NPC110454
0.6605	Remote Similarity	NPC233926
0.6603	Remote Similarity	NPC135349
0.6603	Remote Similarity	NPC470472
0.6597	Remote Similarity	NPC474862
0.6597	Remote Similarity	NPC27581
0.6575	Remote Similarity	NPC213414
0.6573	Remote Similarity	NPC180207
0.6571	Remote Similarity	NPC37302
0.657	Remote Similarity	NPC290534
0.656	Remote Similarity	NPC23167
0.6554	Remote Similarity	NPC78061
0.6554	Remote Similarity	NPC159987
0.6554	Remote Similarity	NPC122359
0.655	Remote Similarity	NPC226001
0.6547	Remote Similarity	NPC76400
0.6547	Remote Similarity	NPC471488
0.6534	Remote Similarity	NPC144823
0.6528	Remote Similarity	NPC471486
0.6522	Remote Similarity	NPC227553
0.6522	Remote Similarity	NPC166837
0.6522	Remote Similarity	NPC163674
0.651	Remote Similarity	NPC150929
0.6508	Remote Similarity	NPC25493
0.6508	Remote Similarity	NPC113460
0.6494	Remote Similarity	NPC74618
0.6494	Remote Similarity	NPC301941
0.6494	Remote Similarity	NPC214188
0.649	Remote Similarity	NPC158078
0.648	Remote Similarity	NPC197783
0.6457	Remote Similarity	NPC318325
0.6457	Remote Similarity	NPC258219
0.6457	Remote Similarity	NPC177420
0.6457	Remote Similarity	NPC280347
0.6457	Remote Similarity	NPC242240
0.6457	Remote Similarity	NPC123273
0.6439	Remote Similarity	NPC125732
0.6438	Remote Similarity	NPC229213
0.6437	Remote Similarity	NPC475396
0.6434	Remote Similarity	NPC122009
0.6434	Remote Similarity	NPC325292
0.6434	Remote Similarity	NPC138117
0.6429	Remote Similarity	NPC33244
0.6424	Remote Similarity	NPC326966
0.6424	Remote Similarity	NPC11449
0.6419	Remote Similarity	NPC220311
0.6416	Remote Similarity	NPC475615
0.6414	Remote Similarity	NPC284078
0.6408	Remote Similarity	NPC79844
0.6406	Remote Similarity	NPC300017
0.6406	Remote Similarity	NPC55561
0.64	Remote Similarity	NPC175313
0.64	Remote Similarity	NPC478147
0.64	Remote Similarity	NPC248817
0.64	Remote Similarity	NPC325651
0.6398	Remote Similarity	NPC76412
0.6395	Remote Similarity	NPC473572
0.6395	Remote Similarity	NPC474169
0.6395	Remote Similarity	NPC105999
0.6389	Remote Similarity	NPC43275
0.6384	Remote Similarity	NPC49172
0.6382	Remote Similarity	NPC244866
0.637	Remote Similarity	NPC142577
0.6364	Remote Similarity	NPC6570
0.6364	Remote Similarity	NPC283468
0.6364	Remote Similarity	NPC64205
0.6358	Remote Similarity	NPC478071
0.6357	Remote Similarity	NPC304541
0.6357	Remote Similarity	NPC45040
0.6351	Remote Similarity	NPC137117
0.6348	Remote Similarity	NPC473892
0.6348	Remote Similarity	NPC475658
0.6336	Remote Similarity	NPC313650
0.6336	Remote Similarity	NPC26244
0.6333	Remote Similarity	NPC296712
0.632	Remote Similarity	NPC265146
0.632	Remote Similarity	NPC124436
0.6319	Remote Similarity	NPC469721
0.6316	Remote Similarity	NPC275538
0.6313	Remote Similarity	NPC82741
0.6313	Remote Similarity	NPC470951
0.6313	Remote Similarity	NPC473409
0.6313	Remote Similarity	NPC141405
0.6309	Remote Similarity	NPC476249
0.6309	Remote Similarity	NPC142776
0.6309	Remote Similarity	NPC110131
0.6304	Remote Similarity	NPC309982
0.6301	Remote Similarity	NPC83279
0.6299	Remote Similarity	NPC307235
0.6299	Remote Similarity	NPC407
0.6299	Remote Similarity	NPC184169
0.6291	Remote Similarity	NPC271808
0.6288	Remote Similarity	NPC473388
0.6282	Remote Similarity	NPC474673
0.626	Remote Similarity	NPC316301
0.626	Remote Similarity	NPC128062
0.626	Remote Similarity	NPC27323
0.626	Remote Similarity	NPC151715
0.6259	Remote Similarity	NPC145638
0.6259	Remote Similarity	NPC290566
0.6259	Remote Similarity	NPC316052
0.6257	Remote Similarity	NPC471591
0.625	Remote Similarity	NPC469731
0.625	Remote Similarity	NPC27974
0.625	Remote Similarity	NPC104216
0.625	Remote Similarity	NPC474614
0.6241	Remote Similarity	NPC260000
0.6241	Remote Similarity	NPC315921
0.6234	Remote Similarity	NPC300678
0.6234	Remote Similarity	NPC267237
0.6233	Remote Similarity	NPC41801
0.6231	Remote Similarity	NPC270547
0.6231	Remote Similarity	NPC155908
0.6231	Remote Similarity	NPC204210
0.6224	Remote Similarity	NPC213
0.6224	Remote Similarity	NPC10286
0.6224	Remote Similarity	NPC303370
0.622	Remote Similarity	NPC155393
0.622	Remote Similarity	NPC198747
0.6216	Remote Similarity	NPC116562
0.6212	Remote Similarity	NPC274678

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 NPC184465 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	142
0.1-0.2	920
0.2-0.3	1256
0.3-0.4	3152
0.4-0.5	2835
0.5-0.6	775
0.6-0.7	70
0.7-0.8	0
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
0.7	Intermediate Similarity	NPD3143	Discontinued
0.6985	Remote Similarity	NPD475	Phase 2
0.6933	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD1223	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD3421	Phase 3
0.6815	Remote Similarity	NPD7303	Discontinued
0.6736	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD9718	Approved
0.662	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD9610	Approved
0.6617	Remote Similarity	NPD9608	Approved
0.6599	Remote Similarity	NPD7451	Discontinued
0.6556	Remote Similarity	NPD468	Phase 1
0.6516	Remote Similarity	NPD1803	Phase 3
0.6494	Remote Similarity	NPD1169	Approved
0.6478	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD821	Approved
0.6467	Remote Similarity	NPD3136	Phase 2
0.6438	Remote Similarity	NPD3070	Discontinued
0.6398	Remote Similarity	NPD2183	Approved
0.6398	Remote Similarity	NPD2184	Approved
0.6385	Remote Similarity	NPD2933	Approved
0.6385	Remote Similarity	NPD2934	Approved
0.6382	Remote Similarity	NPD3058	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6336	Remote Similarity	NPD2860	Approved
0.6336	Remote Similarity	NPD2859	Approved
0.6335	Remote Similarity	NPD4739	Approved
0.6333	Remote Similarity	NPD767	Phase 1
0.6331	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.632	Remote Similarity	NPD111	Approved
0.6319	Remote Similarity	NPD1759	Phase 1
0.6312	Remote Similarity	NPD2234	Approved
0.6312	Remote Similarity	NPD2228	Approved
0.6312	Remote Similarity	NPD2229	Approved
0.6303	Remote Similarity	NPD7438	Suspended
0.6296	Remote Similarity	NPD6390	Discontinued
0.6291	Remote Similarity	NPD682	Discontinued
0.6277	Remote Similarity	NPD1444	Approved
0.6277	Remote Similarity	NPD1445	Approved
0.626	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6259	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6258	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.625	Remote Similarity	NPD318	Approved
0.625	Remote Similarity	NPD317	Approved
0.625	Remote Similarity	NPD1758	Phase 1
0.6241	Remote Similarity	NPD9273	Approved
0.6231	Remote Similarity	NPD159	Clinical (unspecified phase)
0.6194	Remote Similarity	NPD3020	Approved
0.619	Remote Similarity	NPD542	Phase 1
0.6149	Remote Similarity	NPD804	Clinical (unspecified phase)
0.6144	Remote Similarity	NPD2372	Approved
0.6143	Remote Similarity	NPD1792	Phase 2
0.6139	Remote Similarity	NPD7450	Phase 2
0.6138	Remote Similarity	NPD16	Approved
0.6138	Remote Similarity	NPD856	Approved
0.6131	Remote Similarity	NPD9244	Approved
0.6127	Remote Similarity	NPD9379	Approved
0.6127	Remote Similarity	NPD9377	Approved
0.6118	Remote Similarity	NPD2098	Approved
0.6118	Remote Similarity	NPD4212	Discontinued
0.6108	Remote Similarity	NPD3796	Clinical (unspecified phase)
0.6107	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6103	Remote Similarity	NPD940	Approved
0.6103	Remote Similarity	NPD846	Approved
0.6101	Remote Similarity	NPD7978	Discontinued
0.6096	Remote Similarity	NPD5303	Approved
0.6096	Remote Similarity	NPD5304	Approved
0.6093	Remote Similarity	NPD1770	Clinical (unspecified phase)
0.6076	Remote Similarity	NPD3846	Clinical (unspecified phase)
0.6074	Remote Similarity	NPD1785	Approved
0.6074	Remote Similarity	NPD1787	Approved
0.6074	Remote Similarity	NPD1786	Approved
0.6069	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6069	Remote Similarity	NPD9568	Approved
0.6065	Remote Similarity	NPD2674	Phase 3
0.6061	Remote Similarity	NPD1409	Phase 3
0.6049	Remote Similarity	NPD2586	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD9614	Approved
0.6042	Remote Similarity	NPD9618	Approved
0.604	Remote Similarity	NPD4480	Approved
0.604	Remote Similarity	NPD3151	Clinical (unspecified phase)
0.6027	Remote Similarity	NPD6360	Discontinued
0.6026	Remote Similarity	NPD6346	Approved
0.6014	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6012	Remote Similarity	NPD2890	Approved
0.6012	Remote Similarity	NPD2888	Approved
0.6012	Remote Similarity	NPD2017	Approved
0.6012	Remote Similarity	NPD2889	Approved
0.6	Remote Similarity	NPD2561	Approved
0.6	Remote Similarity	NPD7737	Approved
0.6	Remote Similarity	NPD7738	Approved
0.6	Remote Similarity	NPD2562	Approved
0.6	Remote Similarity	NPD2097	Approved
0.6	Remote Similarity	NPD255	Approved
0.6	Remote Similarity	NPD256	Approved
0.6	Remote Similarity	NPD7494	Clinical (unspecified phase)
0.5987	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD4652	Approved
0.5975	Remote Similarity	NPD3152	Clinical (unspecified phase)
0.5973	Remote Similarity	NPD1671	Clinical (unspecified phase)
0.597	Remote Similarity	NPD1809	Phase 2
0.597	Remote Similarity	NPD844	Approved
0.5962	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD1423	Approved
0.596	Remote Similarity	NPD1669	Approved
0.596	Remote Similarity	NPD4659	Approved
0.596	Remote Similarity	NPD3685	Discontinued
0.5946	Remote Similarity	NPD4093	Discontinued
0.5943	Remote Similarity	NPD644	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.594	Remote Similarity	NPD845	Approved
0.5931	Remote Similarity	NPD1793	Approved
0.5931	Remote Similarity	NPD1791	Approved
0.5926	Remote Similarity	NPD288	Approved
0.5921	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD9615	Approved
0.5918	Remote Similarity	NPD9616	Approved
0.5918	Remote Similarity	NPD9613	Approved
0.5915	Remote Similarity	NPD3022	Approved
0.5915	Remote Similarity	NPD3021	Approved
0.5912	Remote Similarity	NPD3555	Approved
0.5912	Remote Similarity	NPD3552	Approved
0.5912	Remote Similarity	NPD3553	Approved
0.5912	Remote Similarity	NPD289	Clinical (unspecified phase)
0.5912	Remote Similarity	NPD9248	Phase 1
0.5912	Remote Similarity	NPD3554	Approved
0.5912	Remote Similarity	NPD4760	Clinical (unspecified phase)
0.5906	Remote Similarity	NPD1751	Approved
0.5903	Remote Similarity	NPD1105	Clinical (unspecified phase)
0.5901	Remote Similarity	NPD6809	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD3144	Approved
0.5897	Remote Similarity	NPD3145	Approved
0.589	Remote Similarity	NPD7066	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD1133	Approved
0.5882	Remote Similarity	NPD1134	Approved
0.5882	Remote Similarity	NPD3055	Approved
0.5882	Remote Similarity	NPD1129	Approved
0.5882	Remote Similarity	NPD3053	Approved
0.5882	Remote Similarity	NPD1131	Approved
0.5882	Remote Similarity	NPD4103	Phase 2
0.5882	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD1135	Approved
0.5878	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.5878	Remote Similarity	NPD316	Approved
0.586	Remote Similarity	NPD840	Approved
0.586	Remote Similarity	NPD839	Approved
0.5855	Remote Similarity	NPD6583	Phase 3
0.5855	Remote Similarity	NPD9622	Approved
0.5855	Remote Similarity	NPD6582	Phase 2
0.5848	Remote Similarity	NPD7089	Clinical (unspecified phase)
0.5848	Remote Similarity	NPD5929	Approved
0.5846	Remote Similarity	NPD9538	Approved
0.5839	Remote Similarity	NPD1261	Approved
0.5839	Remote Similarity	NPD9712	Approved
0.5839	Remote Similarity	NPD1067	Discontinued
0.5828	Remote Similarity	NPD4127	Clinical (unspecified phase)
0.5823	Remote Similarity	NPD1555	Discontinued
0.5823	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.5817	Remote Similarity	NPD5310	Approved
0.5817	Remote Similarity	NPD5311	Approved
0.5806	Remote Similarity	NPD1712	Approved
0.5806	Remote Similarity	NPD7828	Discontinued
0.5806	Remote Similarity	NPD4993	Discontinued
0.5802	Remote Similarity	NPD1101	Approved
0.58	Remote Similarity	NPD9381	Approved
0.58	Remote Similarity	NPD9384	Approved
0.58	Remote Similarity	NPD2667	Approved
0.58	Remote Similarity	NPD2668	Approved
0.5797	Remote Similarity	NPD3028	Approved
0.5797	Remote Similarity	NPD1242	Phase 1
0.5789	Remote Similarity	NPD5356	Approved
0.5789	Remote Similarity	NPD530	Approved
0.5789	Remote Similarity	NPD5355	Approved
0.5789	Remote Similarity	NPD5702	Clinical (unspecified phase)
0.5786	Remote Similarity	NPD179	Clinical (unspecified phase)
0.5776	Remote Similarity	NPD3693	Clinical (unspecified phase)
0.5776	Remote Similarity	NPD7742	Approved
0.5776	Remote Similarity	NPD7743	Approved
0.5775	Remote Similarity	NPD6406	Approved
0.5775	Remote Similarity	NPD3269	Clinical (unspecified phase)
0.5774	Remote Similarity	NPD7523	Phase 3
0.5772	Remote Similarity	NPD6093	Discontinued
0.5767	Remote Similarity	NPD6119	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD9710	Approved
0.5766	Remote Similarity	NPD9711	Approved
0.5759	Remote Similarity	NPD7477	Discontinued
0.575	Remote Similarity	NPD2157	Approved
0.575	Remote Similarity	NPD5212	Clinical (unspecified phase)
0.5746	Remote Similarity	NPD752	Approved
0.5742	Remote Similarity	NPD6584	Phase 3
0.5742	Remote Similarity	NPD9621	Approved
0.5742	Remote Similarity	NPD9619	Approved
0.5742	Remote Similarity	NPD9620	Approved
0.5741	Remote Similarity	NPD1725	Approved
0.5732	Remote Similarity	NPD3599	Approved
0.5724	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.5724	Remote Similarity	NPD228	Approved
0.5724	Remote Similarity	NPD5350	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