NPASS Compound

Structure

NPC474753 OpenBabel07101718232D 21 21 0 0 0 0 0 0 0 0999 V2000 -5.1962 -6.0000 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 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 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 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 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 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 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 0.8660 -1.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 N 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 -5.1962 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -5.5000 0.0000 O 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 12 1 0 0 0 0 5 15 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 14 1 0 0 0 0 10 13 1 0 0 0 0 10 16 2 0 0 0 0 11 17 1 0 0 0 0 12 18 2 0 0 0 0 12 21 1 0 0 0 0 13 15 2 3 0 0 0 13 19 1 0 0 0 0 16 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	358.02
Volume:	294.257
LogP:	1.54
LogD:	1.13
LogS:	-2.571
# Rotatable Bonds:	8
TPSA:	108.22
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.306
Synthetic Accessibility Score:	2.531
Fsp3:	0.308
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:	-4.642
MDCK Permeability:	1.4952050150895957e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.472
20% Bioavailability (F20%):	0.023
30% Bioavailability (F30%):	0.864

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.601
Plasma Protein Binding (PPB):	72.09941101074219%
Volume Distribution (VD):	0.566
Pgp-substrate:	33.335391998291016%

ADMET: Metabolism

CYP1A2-inhibitor:	0.587
CYP1A2-substrate:	0.078
CYP2C19-inhibitor:	0.752
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.541
CYP2C9-substrate:	0.89
CYP2D6-inhibitor:	0.044
CYP2D6-substrate:	0.236
CYP3A4-inhibitor:	0.183
CYP3A4-substrate:	0.178

ADMET: Excretion

Clearance (CL):	3.341
Half-life (T1/2):	0.935

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.207
Drug-inuced Liver Injury (DILI):	0.817
AMES Toxicity:	0.309
Rat Oral Acute Toxicity:	0.068
Maximum Recommended Daily Dose:	0.036
Skin Sensitization:	0.171
Carcinogencity:	0.154
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.029

Download Data

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

Natural Product: NPC474753

Natural Product ID:	NPC474753
*Common Name:**	Psammaplin M
IUPAC Name:	methyl 3-[[(2E)-3-(3-bromo-4-hydroxyphenyl)-2-hydroxyiminopropanoyl]amino]propanoate
Synonyms:	Psammaplin M
Standard InCHIKey:	MHONVVZOONJZBU-MHWRWJLKSA-N
Standard InCHI:	InChI=1S/C13H15BrN2O5/c1-21-12(18)4-5-15-13(19)10(16-20)7-8-2-3-11(17)9(14)6-8/h2-3,6,17,20H,4-5,7H2,1H3,(H,15,19)/b16-10+
SMILES:	O/N=C(/C(=NCCC(=O)OC)O)Cc1ccc(c(c1)Br)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL481499
PubChem CID:	44571895
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:0001878] Beta amino 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
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]
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[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	>	30.0	ug.mL-1	PMID[531620]
NPT146	Cell Line	SK-OV-3	Homo sapiens	EC50	>	30.0	ug.mL-1	PMID[531620]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	EC50	>	30.0	ug.mL-1	PMID[531620]
NPT574	Cell Line	XF498	Homo sapiens	EC50	>	30.0	ug.mL-1	PMID[531620]
NPT148	Cell Line	HCT-15	Homo sapiens	EC50	>	30.0	ug.mL-1	PMID[531620]

☑ 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 NPC474753 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	160
0.1-0.2	1598
0.2-0.3	8540
0.3-0.4	10637
0.4-0.5	13300
0.5-0.6	7482
0.6-0.7	878
0.7-0.8	91
0.8-0.85	8
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8864	High Similarity	NPC163810
0.8496	Intermediate Similarity	NPC474091
0.8485	Intermediate Similarity	NPC202776
0.8444	Intermediate Similarity	NPC184465
0.8433	Intermediate Similarity	NPC475735
0.837	Intermediate Similarity	NPC166624
0.8286	Intermediate Similarity	NPC474128
0.8248	Intermediate Similarity	NPC120114
0.8248	Intermediate Similarity	NPC71888
0.8129	Intermediate Similarity	NPC309667
0.7943	Intermediate Similarity	NPC197045
0.7899	Intermediate Similarity	NPC473724
0.7891	Intermediate Similarity	NPC309808
0.7872	Intermediate Similarity	NPC475132
0.7872	Intermediate Similarity	NPC474587
0.7823	Intermediate Similarity	NPC20755
0.7817	Intermediate Similarity	NPC475293
0.7718	Intermediate Similarity	NPC258222
0.7698	Intermediate Similarity	NPC99280
0.7612	Intermediate Similarity	NPC180207
0.7537	Intermediate Similarity	NPC319950
0.7535	Intermediate Similarity	NPC243404
0.7516	Intermediate Similarity	NPC156311
0.75	Intermediate Similarity	NPC474862
0.75	Intermediate Similarity	NPC7830
0.7483	Intermediate Similarity	NPC109968
0.7483	Intermediate Similarity	NPC303993
0.7481	Intermediate Similarity	NPC59387
0.7445	Intermediate Similarity	NPC296202
0.7434	Intermediate Similarity	NPC475432
0.7429	Intermediate Similarity	NPC159987
0.7429	Intermediate Similarity	NPC122359
0.7429	Intermediate Similarity	NPC78061
0.7372	Intermediate Similarity	NPC27581
0.7364	Intermediate Similarity	NPC471495
0.7338	Intermediate Similarity	NPC213414
0.7329	Intermediate Similarity	NPC213471
0.731	Intermediate Similarity	NPC6570
0.7305	Intermediate Similarity	NPC296712
0.7273	Intermediate Similarity	NPC275538
0.7273	Intermediate Similarity	NPC11449
0.7252	Intermediate Similarity	NPC473358
0.7246	Intermediate Similarity	NPC142577
0.7244	Intermediate Similarity	NPC178902
0.7244	Intermediate Similarity	NPC473738
0.7239	Intermediate Similarity	NPC317254
0.7209	Intermediate Similarity	NPC231705
0.7203	Intermediate Similarity	NPC474087
0.7197	Intermediate Similarity	NPC227553
0.7197	Intermediate Similarity	NPC163674
0.7194	Intermediate Similarity	NPC116562
0.7176	Intermediate Similarity	NPC258056
0.7164	Intermediate Similarity	NPC118202
0.7164	Intermediate Similarity	NPC115803
0.7153	Intermediate Similarity	NPC326966
0.7153	Intermediate Similarity	NPC45191
0.7152	Intermediate Similarity	NPC123848
0.7143	Intermediate Similarity	NPC105999
0.7133	Intermediate Similarity	NPC478147
0.7133	Intermediate Similarity	NPC325651
0.7121	Intermediate Similarity	NPC474149
0.7113	Intermediate Similarity	NPC476353
0.7103	Intermediate Similarity	NPC244866
0.7103	Intermediate Similarity	NPC259017
0.7097	Intermediate Similarity	NPC47672
0.7086	Intermediate Similarity	NPC78530
0.7083	Intermediate Similarity	NPC478071
0.7075	Intermediate Similarity	NPC470471
0.7063	Intermediate Similarity	NPC107619
0.7047	Intermediate Similarity	NPC471236
0.7047	Intermediate Similarity	NPC197766
0.7047	Intermediate Similarity	NPC197921
0.7045	Intermediate Similarity	NPC54543
0.7029	Intermediate Similarity	NPC283760
0.7023	Intermediate Similarity	NPC142297
0.7007	Intermediate Similarity	NPC38458
0.7007	Intermediate Similarity	NPC311737
0.7	Intermediate Similarity	NPC91953
0.7	Intermediate Similarity	NPC469360
0.698	Remote Similarity	NPC470470
0.6974	Remote Similarity	NPC135349
0.697	Remote Similarity	NPC153690
0.6962	Remote Similarity	NPC233926
0.6934	Remote Similarity	NPC82963
0.6933	Remote Similarity	NPC40321
0.6908	Remote Similarity	NPC266741
0.6906	Remote Similarity	NPC117759
0.6875	Remote Similarity	NPC245561
0.6875	Remote Similarity	NPC171843
0.6871	Remote Similarity	NPC470392
0.6867	Remote Similarity	NPC177967
0.6867	Remote Similarity	NPC471237
0.6863	Remote Similarity	NPC470472
0.6863	Remote Similarity	NPC81026
0.6861	Remote Similarity	NPC37302
0.6857	Remote Similarity	NPC65714
0.6842	Remote Similarity	NPC31274
0.6842	Remote Similarity	NPC96224
0.6842	Remote Similarity	NPC24101
0.6839	Remote Similarity	NPC132771
0.6826	Remote Similarity	NPC225130
0.6822	Remote Similarity	NPC52472
0.6822	Remote Similarity	NPC253746
0.6815	Remote Similarity	NPC166837
0.6812	Remote Similarity	NPC281686
0.6812	Remote Similarity	NPC106551
0.6812	Remote Similarity	NPC188867
0.6791	Remote Similarity	NPC473372
0.6788	Remote Similarity	NPC142599
0.6786	Remote Similarity	NPC469979
0.6786	Remote Similarity	NPC38483
0.6779	Remote Similarity	NPC471328
0.6776	Remote Similarity	NPC81137
0.6765	Remote Similarity	NPC48525
0.6761	Remote Similarity	NPC136543
0.6757	Remote Similarity	NPC158078
0.6755	Remote Similarity	NPC48202
0.6753	Remote Similarity	NPC184632
0.6752	Remote Similarity	NPC76412
0.6746	Remote Similarity	NPC473462
0.6746	Remote Similarity	NPC110454
0.6746	Remote Similarity	NPC126128
0.6746	Remote Similarity	NPC207819
0.6746	Remote Similarity	NPC298981
0.6742	Remote Similarity	NPC127676
0.6742	Remote Similarity	NPC471592
0.6742	Remote Similarity	NPC13495
0.6741	Remote Similarity	NPC471487
0.6741	Remote Similarity	NPC63345
0.6718	Remote Similarity	NPC304638
0.6715	Remote Similarity	NPC148969
0.6713	Remote Similarity	NPC229213
0.6706	Remote Similarity	NPC290534
0.6693	Remote Similarity	NPC81010
0.6693	Remote Similarity	NPC32977
0.6692	Remote Similarity	NPC155847
0.6692	Remote Similarity	NPC289381
0.669	Remote Similarity	NPC110131
0.6686	Remote Similarity	NPC226001
0.6667	Remote Similarity	NPC475396
0.6667	Remote Similarity	NPC239697
0.6667	Remote Similarity	NPC471954
0.6667	Remote Similarity	NPC268572
0.6667	Remote Similarity	NPC473572
0.6667	Remote Similarity	NPC94217
0.6667	Remote Similarity	NPC474169
0.6667	Remote Similarity	NPC326187
0.6667	Remote Similarity	NPC260000
0.6667	Remote Similarity	NPC75272
0.6667	Remote Similarity	NPC43275
0.6667	Remote Similarity	NPC96275
0.6647	Remote Similarity	NPC191557
0.6647	Remote Similarity	NPC477255
0.6645	Remote Similarity	NPC474673
0.6644	Remote Similarity	NPC328070
0.6642	Remote Similarity	NPC17693
0.6641	Remote Similarity	NPC3371
0.6641	Remote Similarity	NPC318154
0.6628	Remote Similarity	NPC152205
0.6628	Remote Similarity	NPC214188
0.6628	Remote Similarity	NPC475283
0.6628	Remote Similarity	NPC74618
0.6628	Remote Similarity	NPC301941
0.6623	Remote Similarity	NPC64205
0.6623	Remote Similarity	NPC6913
0.662	Remote Similarity	NPC476183
0.6618	Remote Similarity	NPC183700
0.6617	Remote Similarity	NPC303141
0.6615	Remote Similarity	NPC280869
0.6614	Remote Similarity	NPC325292
0.6614	Remote Similarity	NPC138117
0.6613	Remote Similarity	NPC23167
0.6609	Remote Similarity	NPC8093
0.6609	Remote Similarity	NPC121571
0.6609	Remote Similarity	NPC49172
0.6594	Remote Similarity	NPC76400
0.6594	Remote Similarity	NPC264558
0.6594	Remote Similarity	NPC471488
0.6593	Remote Similarity	NPC309982
0.6591	Remote Similarity	NPC470202
0.6587	Remote Similarity	NPC300017
0.6575	Remote Similarity	NPC142776
0.6573	Remote Similarity	NPC83279
0.6573	Remote Similarity	NPC56634
0.6573	Remote Similarity	NPC471338
0.6573	Remote Similarity	NPC476184
0.6573	Remote Similarity	NPC473051
0.6573	Remote Similarity	NPC471486
0.6573	Remote Similarity	NPC476281
0.6573	Remote Similarity	NPC473050
0.6573	Remote Similarity	NPC474678
0.6571	Remote Similarity	NPC475658
0.6571	Remote Similarity	NPC79844
0.6571	Remote Similarity	NPC473892
0.6568	Remote Similarity	NPC288747
0.6562	Remote Similarity	NPC39431
0.6561	Remote Similarity	NPC122599
0.6561	Remote Similarity	NPC270848
0.6561	Remote Similarity	NPC272868
0.656	Remote Similarity	NPC25493

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 NPC474753 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	122
0.1-0.2	640
0.2-0.3	1335
0.3-0.4	2549
0.4-0.5	2987
0.5-0.6	1372
0.6-0.7	138
0.7-0.8	7
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
0.7465	Intermediate Similarity	NPD5729	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD9718	Approved
0.7324	Intermediate Similarity	NPD3136	Phase 2
0.708	Intermediate Similarity	NPD1759	Phase 1
0.705	Intermediate Similarity	NPD3421	Phase 3
0.7021	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD1758	Phase 1
0.7	Intermediate Similarity	NPD7978	Discontinued
0.6867	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD9568	Approved
0.6765	Remote Similarity	NPD821	Approved
0.6739	Remote Similarity	NPD256	Approved
0.6739	Remote Similarity	NPD255	Approved
0.6735	Remote Similarity	NPD1223	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD6346	Approved
0.6688	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9608	Approved
0.6667	Remote Similarity	NPD9610	Approved
0.6646	Remote Similarity	NPD2184	Approved
0.6646	Remote Similarity	NPD2183	Approved
0.6644	Remote Similarity	NPD7451	Discontinued
0.6623	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD1066	Discontinued
0.6604	Remote Similarity	NPD7523	Phase 3
0.6536	Remote Similarity	NPD1169	Approved
0.6533	Remote Similarity	NPD259	Phase 1
0.6516	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.651	Remote Similarity	NPD5163	Phase 2
0.6494	Remote Similarity	NPD7450	Phase 2
0.649	Remote Similarity	NPD468	Phase 1
0.6489	Remote Similarity	NPD9712	Approved
0.6475	Remote Similarity	NPD2229	Approved
0.6475	Remote Similarity	NPD2228	Approved
0.6475	Remote Similarity	NPD2234	Approved
0.6467	Remote Similarity	NPD1048	Approved
0.6463	Remote Similarity	NPD1770	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD3847	Discontinued
0.6447	Remote Similarity	NPD555	Phase 2
0.6438	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD6390	Discontinued
0.6434	Remote Similarity	NPD2933	Approved
0.6434	Remote Similarity	NPD2934	Approved
0.6433	Remote Similarity	NPD1662	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD9710	Approved
0.6412	Remote Similarity	NPD9711	Approved
0.6408	Remote Similarity	NPD318	Approved
0.6408	Remote Similarity	NPD317	Approved
0.6402	Remote Similarity	NPD8019	Approved
0.6395	Remote Similarity	NPD196	Phase 1
0.6385	Remote Similarity	NPD2859	Approved
0.6385	Remote Similarity	NPD2860	Approved
0.6377	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD9569	Approved
0.6371	Remote Similarity	NPD111	Approved
0.637	Remote Similarity	NPD1040	Phase 2
0.6329	Remote Similarity	NPD3400	Discontinued
0.6327	Remote Similarity	NPD3685	Discontinued
0.6324	Remote Similarity	NPD1445	Approved
0.6324	Remote Similarity	NPD1444	Approved
0.6316	Remote Similarity	NPD2674	Phase 3
0.6316	Remote Similarity	NPD5745	Approved
0.6316	Remote Similarity	NPD520	Approved
0.6316	Remote Similarity	NPD1423	Approved
0.6316	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD475	Phase 2
0.6309	Remote Similarity	NPD257	Approved
0.6309	Remote Similarity	NPD258	Approved
0.6308	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD7495	Discontinued
0.6294	Remote Similarity	NPD16	Approved
0.6294	Remote Similarity	NPD856	Approved
0.6288	Remote Similarity	NPD9273	Approved
0.6279	Remote Similarity	NPD159	Clinical (unspecified phase)
0.6276	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD825	Approved
0.6275	Remote Similarity	NPD826	Approved
0.6268	Remote Similarity	NPD1348	Approved
0.625	Remote Similarity	NPD9545	Approved
0.625	Remote Similarity	NPD7554	Discontinued
0.625	Remote Similarity	NPD2802	Phase 3
0.6241	Remote Similarity	NPD3020	Approved
0.6241	Remote Similarity	NPD1067	Discontinued
0.6233	Remote Similarity	NPD3143	Discontinued
0.6216	Remote Similarity	NPD1669	Approved
0.6197	Remote Similarity	NPD9618	Approved
0.6197	Remote Similarity	NPD9614	Approved
0.6187	Remote Similarity	NPD1792	Phase 2
0.6184	Remote Similarity	NPD2372	Approved
0.6184	Remote Similarity	NPD9537	Phase 1
0.6184	Remote Similarity	NPD5746	Approved
0.6184	Remote Similarity	NPD9536	Phase 1
0.6178	Remote Similarity	NPD2240	Approved
0.6178	Remote Similarity	NPD1725	Approved
0.6178	Remote Similarity	NPD2239	Approved
0.6176	Remote Similarity	NPD9244	Approved
0.6173	Remote Similarity	NPD4739	Approved
0.617	Remote Similarity	NPD9377	Approved
0.617	Remote Similarity	NPD9379	Approved
0.6164	Remote Similarity	NPD2668	Approved
0.6164	Remote Similarity	NPD2667	Approved
0.6159	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD2098	Approved
0.6149	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6149	Remote Similarity	NPD2561	Approved
0.6149	Remote Similarity	NPD2562	Approved
0.6149	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD940	Approved
0.6148	Remote Similarity	NPD846	Approved
0.6145	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.6144	Remote Similarity	NPD3145	Approved
0.6144	Remote Similarity	NPD3144	Approved
0.6139	Remote Similarity	NPD3656	Approved
0.6138	Remote Similarity	NPD5303	Approved
0.6138	Remote Similarity	NPD5304	Approved
0.6138	Remote Similarity	NPD2218	Phase 2
0.6138	Remote Similarity	NPD2217	Approved
0.6133	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD4103	Phase 2
0.6129	Remote Similarity	NPD275	Approved
0.6129	Remote Similarity	NPD274	Approved
0.6118	Remote Similarity	NPD4207	Discontinued
0.6118	Remote Similarity	NPD2614	Approved
0.6111	Remote Similarity	NPD9493	Approved
0.6107	Remote Similarity	NPD6583	Phase 3
0.6107	Remote Similarity	NPD4659	Approved
0.6107	Remote Similarity	NPD6582	Phase 2
0.6105	Remote Similarity	NPD4652	Approved
0.6104	Remote Similarity	NPD839	Approved
0.6104	Remote Similarity	NPD840	Approved
0.6084	Remote Similarity	NPD6502	Phase 2
0.6081	Remote Similarity	NPD1535	Discovery
0.6081	Remote Similarity	NPD4480	Approved
0.6078	Remote Similarity	NPD4738	Phase 2
0.6076	Remote Similarity	NPD9570	Approved
0.6076	Remote Similarity	NPD1538	Phase 1
0.6076	Remote Similarity	NPD1537	Approved
0.6076	Remote Similarity	NPD1519	Approved
0.6071	Remote Similarity	NPD7972	Discontinued
0.6071	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6069	Remote Similarity	NPD9613	Approved
0.6069	Remote Similarity	NPD9616	Approved
0.6069	Remote Similarity	NPD9615	Approved
0.6067	Remote Similarity	NPD3098	Discontinued
0.6065	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD4993	Discontinued
0.6053	Remote Similarity	NPD4208	Discontinued
0.6053	Remote Similarity	NPD1712	Approved
0.6051	Remote Similarity	NPD3552	Approved
0.6051	Remote Similarity	NPD3554	Approved
0.6051	Remote Similarity	NPD3555	Approved
0.6051	Remote Similarity	NPD3553	Approved
0.6047	Remote Similarity	NPD2017	Approved
0.6047	Remote Similarity	NPD2890	Approved
0.6047	Remote Similarity	NPD2889	Approved
0.6047	Remote Similarity	NPD2888	Approved
0.6043	Remote Similarity	NPD1358	Approved
0.604	Remote Similarity	NPD6624	Discontinued
0.604	Remote Similarity	NPD1481	Phase 2
0.6037	Remote Similarity	NPD7303	Discontinued
0.6036	Remote Similarity	NPD2097	Approved
0.6027	Remote Similarity	NPD316	Approved
0.6026	Remote Similarity	NPD1135	Approved
0.6026	Remote Similarity	NPD1134	Approved
0.6026	Remote Similarity	NPD1131	Approved
0.6026	Remote Similarity	NPD1129	Approved
0.6026	Remote Similarity	NPD1133	Approved
0.6023	Remote Similarity	NPD8303	Discontinued
0.6015	Remote Similarity	NPD844	Approved
0.6015	Remote Similarity	NPD1809	Phase 2
0.6012	Remote Similarity	NPD7608	Discontinued
0.6	Remote Similarity	NPD1755	Approved
0.6	Remote Similarity	NPD3123	Discovery
0.6	Remote Similarity	NPD7131	Phase 3
0.6	Remote Similarity	NPD3058	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7477	Discontinued
0.6	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6	Remote Similarity	NPD9622	Approved
0.5988	Remote Similarity	NPD1411	Approved
0.5987	Remote Similarity	NPD6584	Phase 3
0.5987	Remote Similarity	NPD2157	Approved
0.5986	Remote Similarity	NPD228	Approved
0.5986	Remote Similarity	NPD4093	Discontinued
0.5985	Remote Similarity	NPD845	Approved
0.5976	Remote Similarity	NPD3536	Discontinued
0.5976	Remote Similarity	NPD3985	Discontinued
0.5975	Remote Similarity	NPD4476	Approved
0.5975	Remote Similarity	NPD6032	Approved
0.5975	Remote Similarity	NPD4477	Approved
0.5975	Remote Similarity	NPD1523	Approved
0.5975	Remote Similarity	NPD1522	Approved
0.5973	Remote Similarity	NPD422	Phase 1
0.5973	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.5973	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.5972	Remote Similarity	NPD1793	Approved
0.5972	Remote Similarity	NPD1791	Approved
0.5971	Remote Similarity	NPD3134	Approved
0.5971	Remote Similarity	NPD467	Phase 1

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