NPASS Compound

Structure

NPC475697 OpenBabel07101718182D 26 27 0 0 1 0 0 0 0 0999 V2000 7.7942 2.5000 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 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 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 4.3301 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 3.4641 1.0000 0.0000 C 0 0 3 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 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 0.0000 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 6.0622 2.5000 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 6.9282 1.0000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 Br 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 0.8660 -1.5000 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 -0.8660 -0.5000 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 6.9282 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 26 1 0 0 0 0 3 8 1 0 0 0 0 3 9 1 0 0 0 0 4 7 2 0 0 0 0 4 10 1 0 0 0 0 5 7 1 0 0 0 0 5 12 2 0 0 0 0 6 8 2 0 0 0 0 6 11 1 0 0 0 0 7 9 1 0 0 0 0 8 13 1 0 0 0 0 9 17 1 0 0 0 0 10 16 2 0 0 0 0 10 18 1 0 0 0 0 11 15 2 0 0 0 0 11 21 1 0 0 0 0 12 16 1 0 0 0 0 12 22 1 0 0 0 0 13 14 2 0 0 0 0 13 19 1 0 0 0 0 14 15 1 0 0 0 0 14 20 1 0 0 0 0 15 23 1 0 0 0 0 16 25 1 0 0 0 0 17 24 2 0 0 0 0 17 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	551.84
Volume:	377.612
LogP:	4.424
LogD:	3.398
LogS:	-3.995
# Rotatable Bonds:	6
TPSA:	96.22
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.369
Synthetic Accessibility Score:	3.394
Fsp3:	0.235
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.874
MDCK Permeability:	1.4045978787180502e-05
Pgp-inhibitor:	0.987
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.725
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.026
Plasma Protein Binding (PPB):	99.34590148925781%
Volume Distribution (VD):	0.367
Pgp-substrate:	2.118232011795044%

ADMET: Metabolism

CYP1A2-inhibitor:	0.812
CYP1A2-substrate:	0.927
CYP2C19-inhibitor:	0.642
CYP2C19-substrate:	0.156
CYP2C9-inhibitor:	0.879
CYP2C9-substrate:	0.828
CYP2D6-inhibitor:	0.455
CYP2D6-substrate:	0.282
CYP3A4-inhibitor:	0.524
CYP3A4-substrate:	0.324

ADMET: Excretion

Clearance (CL):	1.214
Half-life (T1/2):	0.612

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.193
Drug-inuced Liver Injury (DILI):	0.546
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.373
Maximum Recommended Daily Dose:	0.837
Skin Sensitization:	0.916
Carcinogencity:	0.039
Eye Corrosion:	0.003
Eye Irritation:	0.522
Respiratory Toxicity:	0.374

Download Data

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

Natural Product: NPC475697

Natural Product ID:	NPC475697
*Common Name:**	Methyl 2-(3-Bromo-5-Hydroxy-4-Methoxyphenyl)-3-(2,3-Dibromo-4,5-Dihydroxyphenyl)Propanoate
IUPAC Name:	methyl 2-(3-bromo-5-hydroxy-4-methoxyphenyl)-3-(2,3-dibromo-4,5-dihydroxyphenyl)propanoate
Synonyms:
Standard InCHIKey:	CGWFVWNCURPETC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H15Br3O6/c1-25-16-10(18)4-7(5-12(16)22)9(17(24)26-2)3-8-6-11(21)15(23)14(20)13(8)19/h4-6,9,21-23H,3H2,1-2H3
SMILES:	COC(=O)C(c1cc(O)c(c(c1)Br)OC)Cc1cc(O)c(c(c1Br)Br)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL511993
PubChem CID:	11444290
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes

*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
NPO14137	Rhodomela confervoides	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15217289]
NPO14137	Rhodomela confervoides	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921411]
NPO14137	Rhodomela confervoides	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499317]
NPO14137	Rhodomela confervoides	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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
IC50	5
MIC	3

Activity Type	# Activity
Cell Line	5
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[507071]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[507071]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[507071]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[507071]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[507071]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[507071]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[507071]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	100.0	ug.mL-1	PMID[507071]

☑ 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 NPC475697 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	382
0.1-0.2	1932
0.2-0.3	5354
0.3-0.4	13633
0.4-0.5	4386
0.5-0.6	7612
0.6-0.7	8744
0.7-0.8	643
0.8-0.85	7
0.85-0.9	1
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9932	High Similarity	NPC474535
0.9054	High Similarity	NPC184632
0.8516	High Similarity	NPC178097
0.8366	Intermediate Similarity	NPC89341
0.8355	Intermediate Similarity	NPC160932
0.8344	Intermediate Similarity	NPC473608
0.8267	Intermediate Similarity	NPC471328
0.825	Intermediate Similarity	NPC135103
0.8092	Intermediate Similarity	NPC245386
0.8089	Intermediate Similarity	NPC109346
0.8	Intermediate Similarity	NPC85049
0.7987	Intermediate Similarity	NPC281020
0.7947	Intermediate Similarity	NPC160081
0.7947	Intermediate Similarity	NPC226493
0.7908	Intermediate Similarity	NPC163560
0.7898	Intermediate Similarity	NPC250597
0.7852	Intermediate Similarity	NPC220311
0.7821	Intermediate Similarity	NPC156356
0.7821	Intermediate Similarity	NPC271942
0.7756	Intermediate Similarity	NPC224663
0.7742	Intermediate Similarity	NPC4982
0.7742	Intermediate Similarity	NPC300776
0.7742	Intermediate Similarity	NPC5310
0.7742	Intermediate Similarity	NPC176814
0.7742	Intermediate Similarity	NPC68779
0.7736	Intermediate Similarity	NPC253481
0.7736	Intermediate Similarity	NPC253722
0.7736	Intermediate Similarity	NPC31751
0.773	Intermediate Similarity	NPC152947
0.7722	Intermediate Similarity	NPC203351
0.7707	Intermediate Similarity	NPC168680
0.7692	Intermediate Similarity	NPC113295
0.7688	Intermediate Similarity	NPC477696
0.7688	Intermediate Similarity	NPC106920
0.7688	Intermediate Similarity	NPC477697
0.7688	Intermediate Similarity	NPC273657
0.7688	Intermediate Similarity	NPC470811
0.7677	Intermediate Similarity	NPC244890
0.7677	Intermediate Similarity	NPC129889
0.7677	Intermediate Similarity	NPC307006
0.7673	Intermediate Similarity	NPC326065
0.7673	Intermediate Similarity	NPC100675
0.7667	Intermediate Similarity	NPC137117
0.7647	Intermediate Similarity	NPC105702
0.7647	Intermediate Similarity	NPC474614
0.764	Intermediate Similarity	NPC239608
0.764	Intermediate Similarity	NPC46161
0.7619	Intermediate Similarity	NPC305490
0.7616	Intermediate Similarity	NPC53305
0.7616	Intermediate Similarity	NPC257589
0.7607	Intermediate Similarity	NPC58752
0.7595	Intermediate Similarity	NPC281780
0.7593	Intermediate Similarity	NPC223185
0.759	Intermediate Similarity	NPC267091
0.7584	Intermediate Similarity	NPC177291
0.7584	Intermediate Similarity	NPC194416
0.7582	Intermediate Similarity	NPC150929
0.758	Intermediate Similarity	NPC199089
0.758	Intermediate Similarity	NPC152209
0.7574	Intermediate Similarity	NPC38980
0.7566	Intermediate Similarity	NPC43706
0.7566	Intermediate Similarity	NPC92207
0.7566	Intermediate Similarity	NPC127937
0.7564	Intermediate Similarity	NPC283823
0.7564	Intermediate Similarity	NPC159418
0.7561	Intermediate Similarity	NPC470757
0.7547	Intermediate Similarity	NPC284409
0.7546	Intermediate Similarity	NPC113862
0.7533	Intermediate Similarity	NPC116562
0.7533	Intermediate Similarity	NPC229213
0.7532	Intermediate Similarity	NPC90431
0.7532	Intermediate Similarity	NPC241354
0.7531	Intermediate Similarity	NPC50954
0.753	Intermediate Similarity	NPC243891
0.7516	Intermediate Similarity	NPC474147
0.7516	Intermediate Similarity	NPC13004
0.7516	Intermediate Similarity	NPC473708
0.7516	Intermediate Similarity	NPC67247
0.75	Intermediate Similarity	NPC303011
0.75	Intermediate Similarity	NPC288452
0.75	Intermediate Similarity	NPC111888
0.75	Intermediate Similarity	NPC289690
0.75	Intermediate Similarity	NPC280767
0.75	Intermediate Similarity	NPC38483
0.7485	Intermediate Similarity	NPC124842
0.7485	Intermediate Similarity	NPC275278
0.7484	Intermediate Similarity	NPC66905
0.7483	Intermediate Similarity	NPC473572
0.7483	Intermediate Similarity	NPC474169
0.7468	Intermediate Similarity	NPC226661
0.7468	Intermediate Similarity	NPC470990
0.7455	Intermediate Similarity	NPC472969
0.7453	Intermediate Similarity	NPC29599
0.7453	Intermediate Similarity	NPC118794
0.7453	Intermediate Similarity	NPC166137
0.7453	Intermediate Similarity	NPC282291
0.7451	Intermediate Similarity	NPC90128
0.7451	Intermediate Similarity	NPC84076
0.7451	Intermediate Similarity	NPC303680
0.744	Intermediate Similarity	NPC295646
0.7434	Intermediate Similarity	NPC85565
0.7423	Intermediate Similarity	NPC469615
0.7423	Intermediate Similarity	NPC473090
0.7423	Intermediate Similarity	NPC46880
0.7421	Intermediate Similarity	NPC471988
0.7419	Intermediate Similarity	NPC304622
0.7417	Intermediate Similarity	NPC47790
0.741	Intermediate Similarity	NPC174512
0.741	Intermediate Similarity	NPC474965
0.741	Intermediate Similarity	NPC477695
0.741	Intermediate Similarity	NPC476394
0.741	Intermediate Similarity	NPC98809
0.741	Intermediate Similarity	NPC293757
0.741	Intermediate Similarity	NPC474903
0.741	Intermediate Similarity	NPC125570
0.741	Intermediate Similarity	NPC668
0.741	Intermediate Similarity	NPC216223
0.741	Intermediate Similarity	NPC145569
0.7407	Intermediate Similarity	NPC52664
0.7407	Intermediate Similarity	NPC110419
0.7403	Intermediate Similarity	NPC123722
0.7403	Intermediate Similarity	NPC151167
0.7403	Intermediate Similarity	NPC123228
0.7403	Intermediate Similarity	NPC276466
0.7403	Intermediate Similarity	NPC159987
0.7403	Intermediate Similarity	NPC122359
0.7403	Intermediate Similarity	NPC5018
0.7403	Intermediate Similarity	NPC78061
0.7396	Intermediate Similarity	NPC62051
0.7394	Intermediate Similarity	NPC138978
0.7391	Intermediate Similarity	NPC147379
0.7391	Intermediate Similarity	NPC474784
0.7386	Intermediate Similarity	NPC142776
0.7386	Intermediate Similarity	NPC148627
0.7378	Intermediate Similarity	NPC469683
0.7378	Intermediate Similarity	NPC207732
0.7375	Intermediate Similarity	NPC110899
0.7375	Intermediate Similarity	NPC112068
0.7375	Intermediate Similarity	NPC95679
0.7375	Intermediate Similarity	NPC25305
0.7375	Intermediate Similarity	NPC471236
0.7375	Intermediate Similarity	NPC197766
0.7375	Intermediate Similarity	NPC125417
0.7372	Intermediate Similarity	NPC311419
0.7372	Intermediate Similarity	NPC137427
0.7372	Intermediate Similarity	NPC65935
0.7372	Intermediate Similarity	NPC142985
0.7372	Intermediate Similarity	NPC285776
0.7372	Intermediate Similarity	NPC123196
0.7372	Intermediate Similarity	NPC215941
0.7372	Intermediate Similarity	NPC244246
0.7372	Intermediate Similarity	NPC275724
0.7372	Intermediate Similarity	NPC319282
0.7372	Intermediate Similarity	NPC11449
0.7368	Intermediate Similarity	NPC163083
0.7365	Intermediate Similarity	NPC235033
0.7365	Intermediate Similarity	NPC471235
0.7365	Intermediate Similarity	NPC73132
0.7365	Intermediate Similarity	NPC470710
0.7362	Intermediate Similarity	NPC312256
0.7362	Intermediate Similarity	NPC229218
0.7362	Intermediate Similarity	NPC141817
0.7362	Intermediate Similarity	NPC176030
0.7362	Intermediate Similarity	NPC192597
0.7362	Intermediate Similarity	NPC169214
0.7353	Intermediate Similarity	NPC38898
0.7351	Intermediate Similarity	NPC201777
0.7349	Intermediate Similarity	NPC1580
0.7349	Intermediate Similarity	NPC98009
0.7346	Intermediate Similarity	NPC470991
0.7346	Intermediate Similarity	NPC28398
0.7346	Intermediate Similarity	NPC19158
0.7338	Intermediate Similarity	NPC76451
0.7338	Intermediate Similarity	NPC179777
0.7338	Intermediate Similarity	NPC134219
0.7337	Intermediate Similarity	NPC294870
0.7333	Intermediate Similarity	NPC157133
0.7333	Intermediate Similarity	NPC242885
0.7333	Intermediate Similarity	NPC117780
0.7333	Intermediate Similarity	NPC227217
0.7333	Intermediate Similarity	NPC287275
0.7333	Intermediate Similarity	NPC56214
0.7333	Intermediate Similarity	NPC95614
0.7333	Intermediate Similarity	NPC165133
0.7333	Intermediate Similarity	NPC232316
0.7325	Intermediate Similarity	NPC469480
0.7321	Intermediate Similarity	NPC477700
0.7315	Intermediate Similarity	NPC205502
0.7312	Intermediate Similarity	NPC471237
0.7312	Intermediate Similarity	NPC177967
0.731	Intermediate Similarity	NPC227062
0.7305	Intermediate Similarity	NPC7398
0.7296	Intermediate Similarity	NPC312155
0.729	Intermediate Similarity	NPC223807
0.729	Intermediate Similarity	NPC5428
0.729	Intermediate Similarity	NPC165045
0.729	Intermediate Similarity	NPC118533
0.729	Intermediate Similarity	NPC127587
0.7284	Intermediate Similarity	NPC191280
0.7278	Intermediate Similarity	NPC476434

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 NPC475697 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	363
0.1-0.2	1071
0.2-0.3	2041
0.3-0.4	2894
0.4-0.5	1610
0.5-0.6	951
0.6-0.7	212
0.7-0.8	8
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
0.7378	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD4288	Approved
0.7303	Intermediate Similarity	NPD1608	Approved
0.7105	Intermediate Similarity	NPD17	Approved
0.7091	Intermediate Similarity	NPD4628	Phase 3
0.7035	Intermediate Similarity	NPD1934	Approved
0.7032	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD6234	Discontinued
0.7011	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD4010	Discontinued
0.6987	Remote Similarity	NPD1283	Approved
0.6981	Remote Similarity	NPD3027	Phase 3
0.6962	Remote Similarity	NPD9494	Approved
0.6954	Remote Similarity	NPD2296	Approved
0.6936	Remote Similarity	NPD37	Approved
0.6914	Remote Similarity	NPD230	Phase 1
0.691	Remote Similarity	NPD6232	Discontinued
0.6897	Remote Similarity	NPD2801	Approved
0.6897	Remote Similarity	NPD1465	Phase 2
0.6889	Remote Similarity	NPD7473	Discontinued
0.6886	Remote Similarity	NPD4110	Phase 3
0.6886	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD5283	Phase 1
0.6854	Remote Similarity	NPD7199	Phase 2
0.6846	Remote Similarity	NPD228	Approved
0.6842	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4966	Approved
0.6818	Remote Similarity	NPD3882	Suspended
0.6818	Remote Similarity	NPD4965	Approved
0.6818	Remote Similarity	NPD4967	Phase 2
0.681	Remote Similarity	NPD6355	Discontinued
0.6809	Remote Similarity	NPD4287	Approved
0.68	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD1281	Approved
0.6778	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD1511	Approved
0.6761	Remote Similarity	NPD3817	Phase 2
0.6758	Remote Similarity	NPD7228	Approved
0.6748	Remote Similarity	NPD4060	Phase 1
0.6746	Remote Similarity	NPD6190	Approved
0.6738	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD7685	Pre-registration
0.6686	Remote Similarity	NPD1512	Approved
0.6667	Remote Similarity	NPD7095	Approved
0.6648	Remote Similarity	NPD6166	Phase 2
0.6648	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD2935	Discontinued
0.6646	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.663	Remote Similarity	NPD5844	Phase 1
0.6628	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD6798	Discontinued
0.6605	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.66	Remote Similarity	NPD3021	Approved
0.66	Remote Similarity	NPD3022	Approved
0.6595	Remote Similarity	NPD7074	Phase 3
0.6591	Remote Similarity	NPD6386	Approved
0.6591	Remote Similarity	NPD6385	Approved
0.6588	Remote Similarity	NPD8166	Discontinued
0.6581	Remote Similarity	NPD5536	Phase 2
0.6576	Remote Similarity	NPD3818	Discontinued
0.6559	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD2438	Suspended
0.6545	Remote Similarity	NPD2979	Phase 3
0.6545	Remote Similarity	NPD3620	Phase 2
0.6545	Remote Similarity	NPD1613	Approved
0.6545	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD1240	Approved
0.6545	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD1481	Phase 2
0.6541	Remote Similarity	NPD7054	Approved
0.6538	Remote Similarity	NPD9545	Approved
0.6532	Remote Similarity	NPD3146	Approved
0.6532	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD3764	Approved
0.6519	Remote Similarity	NPD3847	Discontinued
0.6508	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD7472	Approved
0.65	Remote Similarity	NPD7075	Discontinued
0.6491	Remote Similarity	NPD3750	Approved
0.6489	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD1510	Phase 2
0.6485	Remote Similarity	NPD6233	Phase 2
0.6485	Remote Similarity	NPD4062	Phase 3
0.6478	Remote Similarity	NPD1535	Discovery
0.6477	Remote Similarity	NPD7458	Discontinued
0.6474	Remote Similarity	NPD6799	Approved
0.6467	Remote Similarity	NPD1607	Approved
0.6458	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.645	Remote Similarity	NPD6100	Approved
0.645	Remote Similarity	NPD6099	Approved
0.6446	Remote Similarity	NPD1558	Phase 1
0.6446	Remote Similarity	NPD943	Approved
0.6441	Remote Similarity	NPD6599	Discontinued
0.6438	Remote Similarity	NPD9269	Phase 2
0.6433	Remote Similarity	NPD1894	Discontinued
0.6425	Remote Similarity	NPD7819	Suspended
0.6425	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD3268	Approved
0.642	Remote Similarity	NPD2797	Approved
0.6413	Remote Similarity	NPD5242	Approved
0.6412	Remote Similarity	NPD7266	Discontinued
0.6407	Remote Similarity	NPD447	Suspended
0.6404	Remote Similarity	NPD6873	Phase 2
0.6395	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD8127	Discontinued
0.6392	Remote Similarity	NPD1651	Approved
0.6391	Remote Similarity	NPD7033	Discontinued
0.6391	Remote Similarity	NPD2799	Discontinued
0.6384	Remote Similarity	NPD3455	Phase 2
0.6383	Remote Similarity	NPD6797	Phase 2
0.6375	Remote Similarity	NPD3705	Approved
0.6374	Remote Similarity	NPD5958	Discontinued
0.6374	Remote Similarity	NPD4534	Discontinued
0.6358	Remote Similarity	NPD2354	Approved
0.6353	Remote Similarity	NPD2531	Phase 2
0.6349	Remote Similarity	NPD7240	Approved
0.6349	Remote Similarity	NPD7251	Discontinued
0.6348	Remote Similarity	NPD7028	Phase 2
0.6348	Remote Similarity	NPD6876	Approved
0.6348	Remote Similarity	NPD4380	Phase 2
0.6348	Remote Similarity	NPD6875	Approved
0.6343	Remote Similarity	NPD2534	Approved
0.6343	Remote Similarity	NPD2533	Approved
0.6343	Remote Similarity	NPD2532	Approved
0.6343	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD5494	Approved
0.6335	Remote Similarity	NPD3972	Approved
0.6328	Remote Similarity	NPD2370	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD6688	Approved
0.6324	Remote Similarity	NPD6687	Approved
0.6316	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7808	Phase 3
0.6316	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD7003	Approved
0.6298	Remote Similarity	NPD5353	Approved
0.6296	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD2983	Phase 2
0.6296	Remote Similarity	NPD2982	Phase 2
0.6292	Remote Similarity	NPD3226	Approved
0.6289	Remote Similarity	NPD5585	Approved
0.6287	Remote Similarity	NPD4870	Approved
0.6284	Remote Similarity	NPD919	Approved
0.628	Remote Similarity	NPD258	Approved
0.628	Remote Similarity	NPD257	Approved
0.6279	Remote Similarity	NPD1549	Phase 2
0.6278	Remote Similarity	NPD6801	Discontinued
0.6272	Remote Similarity	NPD6653	Approved
0.6271	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD9718	Approved
0.6263	Remote Similarity	NPD1298	Discontinued
0.6258	Remote Similarity	NPD1876	Approved
0.6257	Remote Similarity	NPD4477	Approved
0.6257	Remote Similarity	NPD4476	Approved
0.625	Remote Similarity	NPD4626	Approved
0.625	Remote Similarity	NPD1778	Approved
0.625	Remote Similarity	NPD825	Approved
0.625	Remote Similarity	NPD826	Approved
0.6243	Remote Similarity	NPD8455	Phase 2
0.6242	Remote Similarity	NPD2861	Phase 2
0.6242	Remote Similarity	NPD3018	Phase 2
0.6235	Remote Similarity	NPD2981	Phase 2
0.623	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD3269	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD7110	Phase 1
0.6222	Remote Similarity	NPD7411	Suspended
0.6222	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6221	Remote Similarity	NPD5762	Approved
0.6221	Remote Similarity	NPD2344	Approved
0.6221	Remote Similarity	NPD5763	Approved
0.622	Remote Similarity	NPD3267	Approved
0.622	Remote Similarity	NPD3266	Approved
0.6215	Remote Similarity	NPD6273	Approved
0.6213	Remote Similarity	NPD1933	Approved
0.6209	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6205	Remote Similarity	NPD2614	Approved
0.6205	Remote Similarity	NPD4908	Phase 1
0.62	Remote Similarity	NPD8095	Phase 1
0.6199	Remote Similarity	NPD3748	Approved
0.6193	Remote Similarity	NPD4357	Discontinued
0.619	Remote Similarity	NPD259	Phase 1
0.619	Remote Similarity	NPD8032	Phase 2
0.6188	Remote Similarity	NPD9268	Approved
0.6183	Remote Similarity	NPD7229	Phase 3
0.6182	Remote Similarity	NPD2798	Approved
0.6182	Remote Similarity	NPD5647	Approved
0.618	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6178	Remote Similarity	NPD7039	Approved
0.6178	Remote Similarity	NPD7038	Approved
0.6175	Remote Similarity	NPD7768	Phase 2
0.6173	Remote Similarity	NPD1610	Phase 2
0.6163	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD1551	Phase 2
0.6159	Remote Similarity	NPD3225	Approved
0.6158	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5535	Approved
0.6154	Remote Similarity	NPD1006	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