NPASS Compound

Structure

NPC271942 OpenBabel07101719242D 24 25 0 0 0 0 0 0 0 0999 V2000 6.0622 -0.5000 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 1.7321 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 6.9282 0.0000 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 6.0622 1.5000 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 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 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 2.5000 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 7.7942 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 O 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 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 1 7 1 0 0 0 0 2 4 1 0 0 0 0 2 24 1 0 0 0 0 3 5 1 0 0 0 0 3 24 1 0 0 0 0 4 6 1 0 0 0 0 4 9 2 0 0 0 0 5 8 2 0 0 0 0 5 10 1 0 0 0 0 6 15 1 0 0 0 0 7 12 2 0 0 0 0 7 20 1 0 0 0 0 8 11 1 0 0 0 0 8 16 1 0 0 0 0 9 12 1 0 0 0 0 9 17 1 0 0 0 0 10 13 2 0 0 0 0 10 18 1 0 0 0 0 11 14 2 0 0 0 0 11 19 1 0 0 0 0 12 21 1 0 0 0 0 13 14 1 0 0 0 0 13 22 1 0 0 0 0 14 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	651.64
Volume:	358.138
LogP:	5.597
LogD:	2.84
LogS:	-3.729
# Rotatable Bonds:	4
TPSA:	90.15
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.238
Synthetic Accessibility Score:	3.351
Fsp3:	0.143
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.002
MDCK Permeability:	1.57689064508304e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.967
20% Bioavailability (F20%):	0.054
30% Bioavailability (F30%):	0.05

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.099
Plasma Protein Binding (PPB):	101.6979751586914%
Volume Distribution (VD):	1.816
Pgp-substrate:	2.0937209129333496%

ADMET: Metabolism

CYP1A2-inhibitor:	0.688
CYP1A2-substrate:	0.203
CYP2C19-inhibitor:	0.08
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.808
CYP2C9-substrate:	0.184
CYP2D6-inhibitor:	0.043
CYP2D6-substrate:	0.164
CYP3A4-inhibitor:	0.054
CYP3A4-substrate:	0.066

ADMET: Excretion

Clearance (CL):	0.705
Half-life (T1/2):	0.92

ADMET: Toxicity

hERG Blockers:	0.19
Human Hepatotoxicity (H-HT):	0.193
Drug-inuced Liver Injury (DILI):	0.933
AMES Toxicity:	0.033
Rat Oral Acute Toxicity:	0.409
Maximum Recommended Daily Dose:	0.025
Skin Sensitization:	0.959
Carcinogencity:	0.04
Eye Corrosion:	0.004
Eye Irritation:	0.917
Respiratory Toxicity:	0.15

Download Data

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

Natural Product: NPC271942

Natural Product ID:	NPC271942
*Common Name:**	2,2',3,6,6'-Pentabromo-3',4,4',5-Tetrahydroxydibenzyl Ether
IUPAC Name:	3,4,6-tribromo-5-[(2,6-dibromo-3,4-dihydroxyphenyl)methoxymethyl]benzene-1,2-diol
Synonyms:
Standard InCHIKey:	KJDXYXMXPUYTEM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H9Br5O5/c15-6-1-7(20)12(21)9(17)4(6)2-24-3-5-8(16)11(19)14(23)13(22)10(5)18/h1,20-23H,2-3H2
SMILES:	Oc1c(O)cc(c(c1Br)COCc1c(Br)c(O)c(c(c1Br)Br)O)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463334
PubChem CID:	21778114
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0002542] Benzylethers

*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
NPO6092	Symphyocladia latiuscula	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11141124]
NPO6092	Symphyocladia latiuscula	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15844965]
NPO6092	Symphyocladia latiuscula	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17602526]
NPO6092	Symphyocladia latiuscula	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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT41	Individual Protein	Aldose reductase	Homo sapiens	IC50	=	0.11	ug.mL-1	PMID[470193]

☑ 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 NPC271942 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	621
0.1-0.2	2941
0.2-0.3	12181
0.3-0.4	8603
0.4-0.5	6987
0.5-0.6	9204
0.6-0.7	2042
0.7-0.8	82
0.8-0.85	10
0.85-0.9	16
0.9-0.95	7
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9618	High Similarity	NPC245386
0.9615	High Similarity	NPC303011
0.9167	High Similarity	NPC226493
0.9167	High Similarity	NPC160081
0.9118	High Similarity	NPC168680
0.9091	High Similarity	NPC85049
0.9058	High Similarity	NPC89341
0.9051	High Similarity	NPC160932
0.9008	High Similarity	NPC134219
0.8939	High Similarity	NPC474147
0.8939	High Similarity	NPC473708
0.8865	High Similarity	NPC109346
0.8864	High Similarity	NPC43706
0.8797	High Similarity	NPC13004
0.8705	High Similarity	NPC156356
0.8686	High Similarity	NPC163560
0.8647	High Similarity	NPC220311
0.8636	High Similarity	NPC473572
0.8636	High Similarity	NPC84606
0.8636	High Similarity	NPC474169
0.8571	High Similarity	NPC137117
0.8561	High Similarity	NPC47790
0.8561	High Similarity	NPC229213
0.8561	High Similarity	NPC219444
0.855	High Similarity	NPC227976
0.8456	Intermediate Similarity	NPC150929
0.8435	Intermediate Similarity	NPC152947
0.8394	Intermediate Similarity	NPC474614
0.8369	Intermediate Similarity	NPC224663
0.8333	Intermediate Similarity	NPC474146
0.8286	Intermediate Similarity	NPC244890
0.812	Intermediate Similarity	NPC38483
0.8092	Intermediate Similarity	NPC50782
0.803	Intermediate Similarity	NPC79844
0.8014	Intermediate Similarity	NPC118794
0.7958	Intermediate Similarity	NPC300678
0.7941	Intermediate Similarity	NPC136543
0.7872	Intermediate Similarity	NPC105702
0.7842	Intermediate Similarity	NPC142776
0.7829	Intermediate Similarity	NPC7398
0.7821	Intermediate Similarity	NPC475697
0.7756	Intermediate Similarity	NPC474535
0.7724	Intermediate Similarity	NPC312155
0.7632	Intermediate Similarity	NPC88896
0.7622	Intermediate Similarity	NPC474536
0.7571	Intermediate Similarity	NPC68350
0.7571	Intermediate Similarity	NPC197576
0.7571	Intermediate Similarity	NPC81149
0.7571	Intermediate Similarity	NPC131940
0.7571	Intermediate Similarity	NPC230013
0.7554	Intermediate Similarity	NPC474375
0.7554	Intermediate Similarity	NPC137922
0.7554	Intermediate Similarity	NPC40302
0.7552	Intermediate Similarity	NPC55113
0.7534	Intermediate Similarity	NPC471328
0.7517	Intermediate Similarity	NPC43613
0.75	Intermediate Similarity	NPC175520
0.75	Intermediate Similarity	NPC25134
0.75	Intermediate Similarity	NPC97157
0.75	Intermediate Similarity	NPC159866
0.75	Intermediate Similarity	NPC295879
0.75	Intermediate Similarity	NPC64130
0.7452	Intermediate Similarity	NPC135103
0.7429	Intermediate Similarity	NPC88733
0.7429	Intermediate Similarity	NPC173511
0.741	Intermediate Similarity	NPC41232
0.741	Intermediate Similarity	NPC63317
0.7407	Intermediate Similarity	NPC471488
0.7368	Intermediate Similarity	NPC184632
0.7368	Intermediate Similarity	NPC54543
0.7357	Intermediate Similarity	NPC196371
0.7357	Intermediate Similarity	NPC226737
0.7357	Intermediate Similarity	NPC470414
0.7357	Intermediate Similarity	NPC170824
0.7357	Intermediate Similarity	NPC471486
0.7357	Intermediate Similarity	NPC153580
0.7357	Intermediate Similarity	NPC47769
0.7357	Intermediate Similarity	NPC299939
0.7338	Intermediate Similarity	NPC117759
0.7329	Intermediate Similarity	NPC38980
0.7329	Intermediate Similarity	NPC178301
0.7315	Intermediate Similarity	NPC199089
0.7313	Intermediate Similarity	NPC473358
0.7308	Intermediate Similarity	NPC473608
0.7279	Intermediate Similarity	NPC110800
0.7273	Intermediate Similarity	NPC236265
0.7266	Intermediate Similarity	NPC104124
0.726	Intermediate Similarity	NPC206183
0.726	Intermediate Similarity	NPC222684
0.7214	Intermediate Similarity	NPC44270
0.7214	Intermediate Similarity	NPC86007
0.7203	Intermediate Similarity	NPC105999
0.7203	Intermediate Similarity	NPC473451
0.7179	Intermediate Similarity	NPC113862
0.7164	Intermediate Similarity	NPC471495
0.7153	Intermediate Similarity	NPC257682
0.7153	Intermediate Similarity	NPC146355
0.7153	Intermediate Similarity	NPC213414
0.7153	Intermediate Similarity	NPC33244
0.7153	Intermediate Similarity	NPC131747
0.7143	Intermediate Similarity	NPC191194
0.7143	Intermediate Similarity	NPC71186
0.7134	Intermediate Similarity	NPC178097
0.7114	Intermediate Similarity	NPC474135
0.7101	Intermediate Similarity	NPC94217
0.7095	Intermediate Similarity	NPC11449
0.7063	Intermediate Similarity	NPC147654
0.7059	Intermediate Similarity	NPC471487
0.7055	Intermediate Similarity	NPC191037
0.7055	Intermediate Similarity	NPC58607
0.7055	Intermediate Similarity	NPC45728
0.7055	Intermediate Similarity	NPC305490
0.7055	Intermediate Similarity	NPC178284
0.7029	Intermediate Similarity	NPC471485
0.7021	Intermediate Similarity	NPC275519
0.7014	Intermediate Similarity	NPC296202
0.7007	Intermediate Similarity	NPC118787
0.7007	Intermediate Similarity	NPC292056
0.7007	Intermediate Similarity	NPC183181
0.7007	Intermediate Similarity	NPC111247
0.7007	Intermediate Similarity	NPC41706
0.7007	Intermediate Similarity	NPC319625
0.7007	Intermediate Similarity	NPC147821
0.7007	Intermediate Similarity	NPC163332
0.7	Intermediate Similarity	NPC264379
0.6986	Remote Similarity	NPC194519
0.6985	Remote Similarity	NPC473372
0.6975	Remote Similarity	NPC294870
0.6972	Remote Similarity	NPC181969
0.6972	Remote Similarity	NPC226629
0.6972	Remote Similarity	NPC477803
0.6972	Remote Similarity	NPC320987
0.6966	Remote Similarity	NPC212541
0.6966	Remote Similarity	NPC471693
0.6959	Remote Similarity	NPC252307
0.6959	Remote Similarity	NPC474178
0.6959	Remote Similarity	NPC11258
0.6959	Remote Similarity	NPC282703
0.6959	Remote Similarity	NPC184733
0.6959	Remote Similarity	NPC129570
0.6959	Remote Similarity	NPC72529
0.6959	Remote Similarity	NPC128208
0.6959	Remote Similarity	NPC45774
0.6959	Remote Similarity	NPC21867
0.6959	Remote Similarity	NPC245826
0.6944	Remote Similarity	NPC470804
0.6944	Remote Similarity	NPC7830
0.6933	Remote Similarity	NPC158078
0.6923	Remote Similarity	NPC35071
0.6923	Remote Similarity	NPC148615
0.6923	Remote Similarity	NPC177475
0.6918	Remote Similarity	NPC94276
0.6918	Remote Similarity	NPC109822
0.6914	Remote Similarity	NPC471591
0.6913	Remote Similarity	NPC478071
0.6913	Remote Similarity	NPC86030
0.6913	Remote Similarity	NPC5851
0.6906	Remote Similarity	NPC264558
0.6901	Remote Similarity	NPC255675
0.6897	Remote Similarity	NPC209567
0.6894	Remote Similarity	NPC223393
0.6892	Remote Similarity	NPC165045
0.6892	Remote Similarity	NPC118533
0.6892	Remote Similarity	NPC78061
0.6892	Remote Similarity	NPC159987
0.6892	Remote Similarity	NPC5428
0.6892	Remote Similarity	NPC122359
0.6879	Remote Similarity	NPC221049
0.6875	Remote Similarity	NPC141405
0.6875	Remote Similarity	NPC473409
0.6875	Remote Similarity	NPC82741
0.6871	Remote Similarity	NPC148627
0.6867	Remote Similarity	NPC242807
0.6867	Remote Similarity	NPC77040
0.6867	Remote Similarity	NPC153739
0.6867	Remote Similarity	NPC145305
0.6867	Remote Similarity	NPC257582
0.6867	Remote Similarity	NPC92164
0.6867	Remote Similarity	NPC42300
0.6867	Remote Similarity	NPC187998
0.6867	Remote Similarity	NPC241522
0.6867	Remote Similarity	NPC174495
0.6867	Remote Similarity	NPC64201
0.6866	Remote Similarity	NPC12278
0.6866	Remote Similarity	NPC471511
0.6859	Remote Similarity	NPC250597
0.6859	Remote Similarity	NPC8577
0.6857	Remote Similarity	NPC120280
0.6857	Remote Similarity	NPC221301
0.6853	Remote Similarity	NPC141791
0.6853	Remote Similarity	NPC263386
0.6849	Remote Similarity	NPC136319
0.6849	Remote Similarity	NPC84086
0.6846	Remote Similarity	NPC214553
0.6846	Remote Similarity	NPC472968
0.6831	Remote Similarity	NPC293619
0.6828	Remote Similarity	NPC472271
0.6828	Remote Similarity	NPC145780
0.6824	Remote Similarity	NPC288747
0.6821	Remote Similarity	NPC27843

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 NPC271942 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	509
0.1-0.2	1175
0.2-0.3	2933
0.3-0.4	2654
0.4-0.5	1311
0.5-0.6	538
0.6-0.7	30
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
0.6992	Remote Similarity	NPD9244	Approved
0.68	Remote Similarity	NPD3027	Phase 3
0.6779	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD1613	Approved
0.6776	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD228	Approved
0.6619	Remote Similarity	NPD3022	Approved
0.6619	Remote Similarity	NPD3021	Approved
0.655	Remote Similarity	NPD4010	Discontinued
0.6415	Remote Similarity	NPD7266	Discontinued
0.6415	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.641	Remote Similarity	NPD230	Phase 1
0.64	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD1558	Phase 1
0.6338	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD968	Approved
0.6277	Remote Similarity	NPD1242	Phase 1
0.6258	Remote Similarity	NPD6190	Approved
0.6242	Remote Similarity	NPD9384	Approved
0.6242	Remote Similarity	NPD9381	Approved
0.6234	Remote Similarity	NPD2861	Phase 2
0.6216	Remote Similarity	NPD1548	Phase 1
0.6207	Remote Similarity	NPD5283	Phase 1
0.6199	Remote Similarity	NPD4288	Approved
0.6159	Remote Similarity	NPD1610	Phase 2
0.6159	Remote Similarity	NPD3705	Approved
0.6139	Remote Similarity	NPD3059	Approved
0.6139	Remote Similarity	NPD3061	Approved
0.6139	Remote Similarity	NPD3062	Approved
0.6084	Remote Similarity	NPD1511	Approved
0.6078	Remote Similarity	NPD2982	Phase 2
0.6078	Remote Similarity	NPD2983	Phase 2
0.6078	Remote Similarity	NPD9622	Approved
0.6062	Remote Similarity	NPD5314	Approved
0.6048	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD3620	Phase 2
0.6029	Remote Similarity	NPD2934	Approved
0.6029	Remote Similarity	NPD2933	Approved
0.6027	Remote Similarity	NPD9379	Approved
0.6027	Remote Similarity	NPD9377	Approved
0.6026	Remote Similarity	NPD3018	Phase 2
0.6013	Remote Similarity	NPD2981	Phase 2
0.6012	Remote Similarity	NPD1512	Approved
0.6012	Remote Similarity	NPD2296	Approved
0.5988	Remote Similarity	NPD1934	Approved
0.5988	Remote Similarity	NPD1169	Approved
0.5987	Remote Similarity	NPD4908	Phase 1
0.5985	Remote Similarity	NPD2859	Approved
0.5985	Remote Similarity	NPD2860	Approved
0.5971	Remote Similarity	NPD3020	Approved
0.5962	Remote Similarity	NPD9620	Approved
0.5962	Remote Similarity	NPD9621	Approved
0.5962	Remote Similarity	NPD9619	Approved
0.596	Remote Similarity	NPD1357	Approved
0.5955	Remote Similarity	NPD6688	Approved
0.5955	Remote Similarity	NPD6687	Approved
0.5954	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD4123	Phase 3
0.5949	Remote Similarity	NPD9718	Approved
0.5948	Remote Similarity	NPD1091	Approved
0.5941	Remote Similarity	NPD1653	Approved
0.5939	Remote Similarity	NPD3060	Approved
0.5938	Remote Similarity	NPD4060	Phase 1
0.5933	Remote Similarity	NPD5536	Phase 2
0.5924	Remote Similarity	NPD9494	Approved
0.5912	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.5894	Remote Similarity	NPD9545	Approved
0.5894	Remote Similarity	NPD1182	Approved
0.5886	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.5871	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD2684	Approved
0.5862	Remote Similarity	NPD2801	Approved
0.586	Remote Similarity	NPD6584	Phase 3
0.5855	Remote Similarity	NPD8095	Phase 1
0.5851	Remote Similarity	NPD4287	Approved
0.5849	Remote Similarity	NPD1223	Clinical (unspecified phase)
0.5843	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.5843	Remote Similarity	NPD4236	Phase 3
0.5843	Remote Similarity	NPD4237	Approved
0.5839	Remote Similarity	NPD943	Approved
0.5833	Remote Similarity	NPD5311	Approved
0.5833	Remote Similarity	NPD5310	Approved
0.5824	Remote Similarity	NPD2183	Approved
0.5824	Remote Similarity	NPD2184	Approved
0.5819	Remote Similarity	NPD6234	Discontinued
0.5813	Remote Similarity	NPD601	Approved
0.5813	Remote Similarity	NPD597	Approved
0.5813	Remote Similarity	NPD598	Approved
0.5811	Remote Similarity	NPD7843	Approved
0.5808	Remote Similarity	NPD8166	Discontinued
0.5806	Remote Similarity	NPD9269	Phase 2
0.5806	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.58	Remote Similarity	NPD6671	Approved
0.58	Remote Similarity	NPD7157	Approved
0.5799	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.5796	Remote Similarity	NPD3055	Approved
0.5796	Remote Similarity	NPD3053	Approved
0.5796	Remote Similarity	NPD3094	Phase 2
0.5795	Remote Similarity	NPD3882	Suspended
0.5793	Remote Similarity	NPD290	Approved
0.578	Remote Similarity	NPD4678	Approved
0.578	Remote Similarity	NPD4675	Approved
0.5776	Remote Similarity	NPD1136	Approved
0.5776	Remote Similarity	NPD1132	Approved
0.5776	Remote Similarity	NPD1130	Approved
0.5776	Remote Similarity	NPD2674	Phase 3
0.5771	Remote Similarity	NPD2978	Approved
0.5771	Remote Similarity	NPD2977	Approved
0.5767	Remote Similarity	NPD823	Approved
0.5767	Remote Similarity	NPD817	Approved
0.5742	Remote Similarity	NPD1535	Discovery
0.5742	Remote Similarity	NPD3092	Approved
0.5741	Remote Similarity	NPD825	Approved
0.5741	Remote Similarity	NPD826	Approved
0.5732	Remote Similarity	NPD4538	Approved
0.5732	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.5732	Remote Similarity	NPD4536	Approved
0.5723	Remote Similarity	NPD3455	Phase 2
0.5723	Remote Similarity	NPD1375	Discontinued
0.5714	Remote Similarity	NPD3145	Approved
0.5714	Remote Similarity	NPD3144	Approved
0.5714	Remote Similarity	NPD3764	Approved
0.5714	Remote Similarity	NPD111	Approved
0.5714	Remote Similarity	NPD6516	Phase 2
0.5714	Remote Similarity	NPD5846	Approved
0.5706	Remote Similarity	NPD4340	Discontinued
0.5706	Remote Similarity	NPD555	Phase 2
0.5705	Remote Similarity	NPD1481	Phase 2
0.5705	Remote Similarity	NPD2231	Phase 2
0.5705	Remote Similarity	NPD1608	Approved
0.5705	Remote Similarity	NPD1840	Phase 2
0.5705	Remote Similarity	NPD2235	Phase 2
0.5704	Remote Similarity	NPD289	Clinical (unspecified phase)
0.5697	Remote Similarity	NPD5588	Approved
0.5697	Remote Similarity	NPD5960	Phase 3
0.5687	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.5683	Remote Similarity	NPD9296	Approved
0.5683	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.5682	Remote Similarity	NPD1465	Phase 2
0.568	Remote Similarity	NPD2677	Approved
0.568	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.5669	Remote Similarity	NPD6582	Phase 2
0.5669	Remote Similarity	NPD4749	Approved
0.5669	Remote Similarity	NPD6583	Phase 3
0.5664	Remote Similarity	NPD846	Approved
0.5664	Remote Similarity	NPD940	Approved
0.5663	Remote Similarity	NPD9570	Approved
0.5659	Remote Similarity	NPD6166	Phase 2
0.5659	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.5659	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.5655	Remote Similarity	NPD6674	Discontinued
0.5655	Remote Similarity	NPD4162	Approved
0.5652	Remote Similarity	NPD7095	Approved
0.5652	Remote Similarity	NPD4625	Phase 3
0.5643	Remote Similarity	NPD844	Approved
0.5641	Remote Similarity	NPD422	Phase 1
0.564	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.5633	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.5633	Remote Similarity	NPD8651	Approved
0.5633	Remote Similarity	NPD6696	Suspended
0.5629	Remote Similarity	NPD3540	Phase 1
0.5625	Remote Similarity	NPD37	Approved
0.5621	Remote Similarity	NPD4628	Phase 3
0.5618	Remote Similarity	NPD4965	Approved
0.5618	Remote Similarity	NPD4967	Phase 2
0.5618	Remote Similarity	NPD4966	Approved
0.5617	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.5617	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.5617	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.5614	Remote Similarity	NPD4357	Discontinued
0.5613	Remote Similarity	NPD1778	Approved
0.561	Remote Similarity	NPD5735	Approved
0.5608	Remote Similarity	NPD4750	Phase 3
0.5608	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.5607	Remote Similarity	NPD2122	Discontinued
0.5603	Remote Similarity	NPD288	Approved
0.5602	Remote Similarity	NPD1510	Phase 2
0.56	Remote Similarity	NPD821	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