NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	399.89
Volume:	282.94
LogP:	4.071
LogD:	2.639
LogS:	-3.606
# Rotatable Bonds:	0
TPSA:	80.92
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.506
Synthetic Accessibility Score:	3.02
Fsp3:	0.143
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.136
MDCK Permeability:	1.5343266568379477e-05
Pgp-inhibitor:	0.33
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.227
20% Bioavailability (F20%):	0.02
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.042
Plasma Protein Binding (PPB):	100.08199310302734%
Volume Distribution (VD):	0.617
Pgp-substrate:	0.6049625873565674%

ADMET: Metabolism

CYP1A2-inhibitor:	0.838
CYP1A2-substrate:	0.154
CYP2C19-inhibitor:	0.059
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.461
CYP2C9-substrate:	0.342
CYP2D6-inhibitor:	0.198
CYP2D6-substrate:	0.301
CYP3A4-inhibitor:	0.09
CYP3A4-substrate:	0.079

ADMET: Excretion

Clearance (CL):	1.712
Half-life (T1/2):	0.666

ADMET: Toxicity

hERG Blockers:	0.146
Human Hepatotoxicity (H-HT):	0.206
Drug-inuced Liver Injury (DILI):	0.654
AMES Toxicity:	0.299
Rat Oral Acute Toxicity:	0.114
Maximum Recommended Daily Dose:	0.454
Skin Sensitization:	0.952
Carcinogencity:	0.076
Eye Corrosion:	0.004
Eye Irritation:	0.902
Respiratory Toxicity:	0.162

Download Data

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

Natural Product: NPC312155

Natural Product ID:	NPC312155
*Common Name:**	4,7-Dibromo-9,10-Dihydrophenanthrene-2,3,5,6-Tetrol
IUPAC Name:	4,7-dibromo-9,10-dihydrophenanthrene-2,3,5,6-tetrol
Synonyms:
Standard InCHIKey:	SSPNVSUGGPBPEK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H10Br2O4/c15-7-3-5-1-2-6-4-8(17)13(19)11(16)9(6)10(5)14(20)12(7)18/h3-4,17-20H,1-2H2
SMILES:	Oc1c(Br)cc2c(c1O)c1c(CC2)cc(c(c1Br)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL403304
PubChem CID:	24770034
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives [CHEMONTID:0000223] Hydrophenanthrenes

*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
NPO17587	Polysiphonia urceolata	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17765551]
NPO17587	Polysiphonia urceolata	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18088100]
NPO17587	Polysiphonia urceolata	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18324823]
NPO17587	Polysiphonia urceolata	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21875052]
NPO17587	Polysiphonia urceolata	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
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT35	Others	n.a.		IC50	=	6100.0	nM	PMID[503837]

☑ 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 NPC312155 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	680
0.1-0.2	2505
0.2-0.3	9223
0.3-0.4	11467
0.4-0.5	6322
0.5-0.6	9606
0.6-0.7	2730
0.7-0.8	138
0.8-0.85	12
0.85-0.9	10
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9764	High Similarity	NPC43613
0.9091	High Similarity	NPC300678
0.9008	High Similarity	NPC474614
0.8929	High Similarity	NPC88896
0.8741	High Similarity	NPC163560
0.874	High Similarity	NPC38483
0.8652	High Similarity	NPC109346
0.8623	High Similarity	NPC156356
0.8603	High Similarity	NPC244890
0.8571	High Similarity	NPC118794
0.8561	High Similarity	NPC220311
0.8551	High Similarity	NPC224663
0.8483	Intermediate Similarity	NPC7398
0.8429	Intermediate Similarity	NPC160932
0.831	Intermediate Similarity	NPC89341
0.8209	Intermediate Similarity	NPC137117
0.8162	Intermediate Similarity	NPC13004
0.812	Intermediate Similarity	NPC136543
0.8102	Intermediate Similarity	NPC150929
0.803	Intermediate Similarity	NPC176893
0.8014	Intermediate Similarity	NPC245386
0.797	Intermediate Similarity	NPC474146
0.7943	Intermediate Similarity	NPC471328
0.7939	Intermediate Similarity	NPC79844
0.7926	Intermediate Similarity	NPC47790
0.7868	Intermediate Similarity	NPC84606
0.7826	Intermediate Similarity	NPC43706
0.781	Intermediate Similarity	NPC224342
0.7806	Intermediate Similarity	NPC38980
0.7794	Intermediate Similarity	NPC229213
0.7794	Intermediate Similarity	NPC219444
0.7786	Intermediate Similarity	NPC85049
0.777	Intermediate Similarity	NPC474147
0.777	Intermediate Similarity	NPC473708
0.7737	Intermediate Similarity	NPC473572
0.7737	Intermediate Similarity	NPC474169
0.7734	Intermediate Similarity	NPC233835
0.7734	Intermediate Similarity	NPC471495
0.773	Intermediate Similarity	NPC160081
0.773	Intermediate Similarity	NPC226493
0.7724	Intermediate Similarity	NPC271942
0.7724	Intermediate Similarity	NPC168680
0.763	Intermediate Similarity	NPC117759
0.7626	Intermediate Similarity	NPC142776
0.7615	Intermediate Similarity	NPC473358
0.7615	Intermediate Similarity	NPC471487
0.7594	Intermediate Similarity	NPC472893
0.7591	Intermediate Similarity	NPC39029
0.7576	Intermediate Similarity	NPC471485
0.7576	Intermediate Similarity	NPC471488
0.7538	Intermediate Similarity	NPC473372
0.7538	Intermediate Similarity	NPC54543
0.7519	Intermediate Similarity	NPC94217
0.7518	Intermediate Similarity	NPC471486
0.75	Intermediate Similarity	NPC471179
0.7481	Intermediate Similarity	NPC16030
0.7464	Intermediate Similarity	NPC237667
0.7445	Intermediate Similarity	NPC472071
0.7445	Intermediate Similarity	NPC475245
0.7444	Intermediate Similarity	NPC33244
0.7444	Intermediate Similarity	NPC76400
0.7444	Intermediate Similarity	NPC317869
0.7424	Intermediate Similarity	NPC151537
0.7424	Intermediate Similarity	NPC95716
0.7422	Intermediate Similarity	NPC471511
0.7413	Intermediate Similarity	NPC474536
0.741	Intermediate Similarity	NPC471794
0.7405	Intermediate Similarity	NPC314187
0.7403	Intermediate Similarity	NPC152947
0.7379	Intermediate Similarity	NPC303011
0.7379	Intermediate Similarity	NPC228843
0.7372	Intermediate Similarity	NPC217174
0.7372	Intermediate Similarity	NPC191866
0.7368	Intermediate Similarity	NPC46940
0.7364	Intermediate Similarity	NPC239291
0.7357	Intermediate Similarity	NPC53567
0.7353	Intermediate Similarity	NPC277588
0.7342	Intermediate Similarity	NPC474535
0.7299	Intermediate Similarity	NPC144343
0.7296	Intermediate Similarity	NPC475697
0.7293	Intermediate Similarity	NPC268032
0.7292	Intermediate Similarity	NPC105702
0.7279	Intermediate Similarity	NPC125649
0.7279	Intermediate Similarity	NPC160697
0.7273	Intermediate Similarity	NPC228343
0.7273	Intermediate Similarity	NPC254833
0.7273	Intermediate Similarity	NPC476536
0.7266	Intermediate Similarity	NPC470414
0.7266	Intermediate Similarity	NPC24125
0.7266	Intermediate Similarity	NPC227976
0.7259	Intermediate Similarity	NPC249270
0.7259	Intermediate Similarity	NPC120280
0.723	Intermediate Similarity	NPC69029
0.723	Intermediate Similarity	NPC158142
0.723	Intermediate Similarity	NPC108198
0.723	Intermediate Similarity	NPC200557
0.723	Intermediate Similarity	NPC294884
0.723	Intermediate Similarity	NPC10314
0.7226	Intermediate Similarity	NPC278652
0.7226	Intermediate Similarity	NPC299180
0.7219	Intermediate Similarity	NPC474850
0.7219	Intermediate Similarity	NPC474851
0.7208	Intermediate Similarity	NPC113862
0.7206	Intermediate Similarity	NPC50782
0.7197	Intermediate Similarity	NPC11554
0.7197	Intermediate Similarity	NPC95344
0.7188	Intermediate Similarity	NPC223393
0.7185	Intermediate Similarity	NPC715
0.7185	Intermediate Similarity	NPC322239
0.7181	Intermediate Similarity	NPC202846
0.7181	Intermediate Similarity	NPC143139
0.7153	Intermediate Similarity	NPC115808
0.7153	Intermediate Similarity	NPC261973
0.7143	Intermediate Similarity	NPC58865
0.7143	Intermediate Similarity	NPC303144
0.7143	Intermediate Similarity	NPC202647
0.7133	Intermediate Similarity	NPC29008
0.7133	Intermediate Similarity	NPC151656
0.7133	Intermediate Similarity	NPC200935
0.7133	Intermediate Similarity	NPC266705
0.7133	Intermediate Similarity	NPC56329
0.7133	Intermediate Similarity	NPC230919
0.7133	Intermediate Similarity	NPC266453
0.7133	Intermediate Similarity	NPC228771
0.7133	Intermediate Similarity	NPC22902
0.7133	Intermediate Similarity	NPC242715
0.7132	Intermediate Similarity	NPC195922
0.7114	Intermediate Similarity	NPC313081
0.7114	Intermediate Similarity	NPC241241
0.7101	Intermediate Similarity	NPC172219
0.7101	Intermediate Similarity	NPC470760
0.7101	Intermediate Similarity	NPC304510
0.709	Intermediate Similarity	NPC226401
0.709	Intermediate Similarity	NPC120982
0.709	Intermediate Similarity	NPC79793
0.709	Intermediate Similarity	NPC147634
0.709	Intermediate Similarity	NPC174096
0.7086	Intermediate Similarity	NPC220344
0.7086	Intermediate Similarity	NPC29868
0.7086	Intermediate Similarity	NPC212942
0.7086	Intermediate Similarity	NPC243996
0.7086	Intermediate Similarity	NPC243759
0.7086	Intermediate Similarity	NPC79622
0.7086	Intermediate Similarity	NPC105847
0.7086	Intermediate Similarity	NPC275061
0.7086	Intermediate Similarity	NPC218131
0.7086	Intermediate Similarity	NPC132804
0.7083	Intermediate Similarity	NPC134219
0.7075	Intermediate Similarity	NPC312341
0.7068	Intermediate Similarity	NPC105727
0.7068	Intermediate Similarity	NPC34864
0.7068	Intermediate Similarity	NPC114392
0.7068	Intermediate Similarity	NPC58427
0.7067	Intermediate Similarity	NPC30632
0.7059	Intermediate Similarity	NPC184632
0.705	Intermediate Similarity	NPC471671
0.7047	Intermediate Similarity	NPC311256
0.7047	Intermediate Similarity	NPC209199
0.7045	Intermediate Similarity	NPC54765
0.7042	Intermediate Similarity	NPC321402
0.7039	Intermediate Similarity	NPC308768
0.7039	Intermediate Similarity	NPC12668
0.7037	Intermediate Similarity	NPC179002
0.7037	Intermediate Similarity	NPC187583
0.7037	Intermediate Similarity	NPC260323
0.7037	Intermediate Similarity	NPC257430
0.7037	Intermediate Similarity	NPC176279
0.7034	Intermediate Similarity	NPC21563
0.7031	Intermediate Similarity	NPC32674
0.7031	Intermediate Similarity	NPC109955
0.7031	Intermediate Similarity	NPC156313
0.7027	Intermediate Similarity	NPC73656
0.7027	Intermediate Similarity	NPC161958
0.7027	Intermediate Similarity	NPC14224
0.7024	Intermediate Similarity	NPC24435
0.7023	Intermediate Similarity	NPC238696
0.7023	Intermediate Similarity	NPC120719
0.7023	Intermediate Similarity	NPC12278
0.7015	Intermediate Similarity	NPC62258
0.7015	Intermediate Similarity	NPC55617
0.7014	Intermediate Similarity	NPC9067
0.7007	Intermediate Similarity	NPC107240
0.7007	Intermediate Similarity	NPC473137
0.7007	Intermediate Similarity	NPC12656
0.7	Intermediate Similarity	NPC469644
0.6992	Remote Similarity	NPC151477
0.6992	Remote Similarity	NPC176527
0.6986	Remote Similarity	NPC277458
0.6986	Remote Similarity	NPC307050
0.6986	Remote Similarity	NPC472968
0.6986	Remote Similarity	NPC23012
0.6986	Remote Similarity	NPC234175
0.698	Remote Similarity	NPC294226
0.6974	Remote Similarity	NPC6300
0.6974	Remote Similarity	NPC230124
0.6974	Remote Similarity	NPC114171
0.6974	Remote Similarity	NPC184613
0.6974	Remote Similarity	NPC61398
0.6974	Remote Similarity	NPC416
0.6972	Remote Similarity	NPC475166

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 NPC312155 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	553
0.1-0.2	1074
0.2-0.3	2326
0.3-0.4	3046
0.4-0.5	1434
0.5-0.6	624
0.6-0.7	91
0.7-0.8	2
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
0.7273	Intermediate Similarity	NPD3021	Approved
0.7273	Intermediate Similarity	NPD3022	Approved
0.7121	Intermediate Similarity	NPD2342	Discontinued
0.6894	Remote Similarity	NPD9244	Approved
0.6803	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD7635	Approved
0.6736	Remote Similarity	NPD3092	Approved
0.6736	Remote Similarity	NPD1201	Approved
0.6713	Remote Similarity	NPD2286	Discontinued
0.6667	Remote Similarity	NPD4010	Discontinued
0.6667	Remote Similarity	NPD3094	Phase 2
0.6667	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1470	Approved
0.6591	Remote Similarity	NPD3020	Approved
0.6579	Remote Similarity	NPD1613	Approved
0.6579	Remote Similarity	NPD3620	Phase 2
0.6579	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD3091	Approved
0.6565	Remote Similarity	NPD288	Approved
0.6541	Remote Similarity	NPD1242	Phase 1
0.6538	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD4750	Phase 3
0.65	Remote Similarity	NPD2420	Approved
0.65	Remote Similarity	NPD2421	Approved
0.6489	Remote Similarity	NPD2860	Approved
0.6489	Remote Similarity	NPD2859	Approved
0.6489	Remote Similarity	NPD844	Approved
0.6483	Remote Similarity	NPD3019	Approved
0.6483	Remote Similarity	NPD4059	Approved
0.6475	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD943	Approved
0.6454	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD228	Approved
0.6419	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD4093	Discontinued
0.6412	Remote Similarity	NPD2934	Approved
0.6412	Remote Similarity	NPD2933	Approved
0.641	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD497	Approved
0.6407	Remote Similarity	NPD4288	Approved
0.6383	Remote Similarity	NPD9379	Approved
0.6383	Remote Similarity	NPD9377	Approved
0.6382	Remote Similarity	NPD4625	Phase 3
0.6382	Remote Similarity	NPD3027	Phase 3
0.637	Remote Similarity	NPD940	Approved
0.637	Remote Similarity	NPD2932	Approved
0.637	Remote Similarity	NPD846	Approved
0.637	Remote Similarity	NPD3095	Discontinued
0.6369	Remote Similarity	NPD5408	Approved
0.6369	Remote Similarity	NPD5404	Approved
0.6369	Remote Similarity	NPD5405	Approved
0.6369	Remote Similarity	NPD5406	Approved
0.6364	Remote Similarity	NPD1809	Phase 2
0.6358	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.634	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6338	Remote Similarity	NPD498	Approved
0.6338	Remote Similarity	NPD496	Approved
0.6338	Remote Similarity	NPD495	Approved
0.6288	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD1223	Clinical (unspecified phase)
0.6259	Remote Similarity	NPD9381	Approved
0.6259	Remote Similarity	NPD9384	Approved
0.6258	Remote Similarity	NPD4060	Phase 1
0.6235	Remote Similarity	NPD3845	Phase 1
0.6224	Remote Similarity	NPD5283	Phase 1
0.6212	Remote Similarity	NPD845	Approved
0.6211	Remote Similarity	NPD8166	Discontinued
0.6203	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD7390	Discontinued
0.6174	Remote Similarity	NPD1610	Phase 2
0.6159	Remote Similarity	NPD5310	Approved
0.6159	Remote Similarity	NPD5311	Approved
0.6154	Remote Similarity	NPD3062	Approved
0.6154	Remote Similarity	NPD3059	Approved
0.6154	Remote Similarity	NPD3061	Approved
0.6149	Remote Similarity	NPD1751	Approved
0.6149	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6144	Remote Similarity	NPD2861	Phase 2
0.6144	Remote Similarity	NPD5736	Approved
0.6135	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD3055	Approved
0.6118	Remote Similarity	NPD3053	Approved
0.6118	Remote Similarity	NPD2296	Approved
0.6107	Remote Similarity	NPD3026	Approved
0.6107	Remote Similarity	NPD3023	Approved
0.6105	Remote Similarity	NPD6234	Discontinued
0.6104	Remote Similarity	NPD4908	Phase 1
0.6096	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6093	Remote Similarity	NPD9622	Approved
0.6093	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6081	Remote Similarity	NPD3024	Approved
0.6081	Remote Similarity	NPD3025	Approved
0.6076	Remote Similarity	NPD5314	Approved
0.6069	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6065	Remote Similarity	NPD9718	Approved
0.6065	Remote Similarity	NPD5155	Approved
0.6065	Remote Similarity	NPD5156	Approved
0.6061	Remote Similarity	NPD3645	Discontinued
0.6056	Remote Similarity	NPD1792	Phase 2
0.6053	Remote Similarity	NPD1283	Approved
0.6051	Remote Similarity	NPD1558	Phase 1
0.6049	Remote Similarity	NPD6674	Discontinued
0.604	Remote Similarity	NPD4626	Approved
0.6032	Remote Similarity	NPD8095	Phase 1
0.6027	Remote Similarity	NPD709	Approved
0.6026	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6026	Remote Similarity	NPD3764	Approved
0.6025	Remote Similarity	NPD7266	Discontinued
0.6025	Remote Similarity	NPD4721	Approved
0.6025	Remote Similarity	NPD4726	Approved
0.6025	Remote Similarity	NPD4725	Approved
0.6014	Remote Similarity	NPD1548	Phase 1
0.6013	Remote Similarity	NPD5735	Approved
0.6	Remote Similarity	NPD37	Approved
0.6	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6	Remote Similarity	NPD2606	Approved
0.6	Remote Similarity	NPD2605	Approved
0.6	Remote Similarity	NPD6232	Discontinued
0.6	Remote Similarity	NPD1169	Approved
0.6	Remote Similarity	NPD3595	Approved
0.6	Remote Similarity	NPD1511	Approved
0.6	Remote Similarity	NPD3594	Approved
0.5987	Remote Similarity	NPD4749	Approved
0.5987	Remote Similarity	NPD6663	Approved
0.5975	Remote Similarity	NPD4097	Suspended
0.5974	Remote Similarity	NPD9620	Approved
0.5974	Remote Similarity	NPD4624	Approved
0.5974	Remote Similarity	NPD258	Approved
0.5974	Remote Similarity	NPD9621	Approved
0.5974	Remote Similarity	NPD9619	Approved
0.5974	Remote Similarity	NPD257	Approved
0.5973	Remote Similarity	NPD1651	Approved
0.5972	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.5969	Remote Similarity	NPD111	Approved
0.5966	Remote Similarity	NPD6687	Approved
0.5966	Remote Similarity	NPD6688	Approved
0.5965	Remote Similarity	NPD1465	Phase 2
0.596	Remote Similarity	NPD1611	Approved
0.5948	Remote Similarity	NPD6696	Suspended
0.5948	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD4287	Approved
0.5939	Remote Similarity	NPD3300	Phase 2
0.5935	Remote Similarity	NPD3636	Approved
0.5935	Remote Similarity	NPD3635	Approved
0.5935	Remote Similarity	NPD3637	Approved
0.5933	Remote Similarity	NPD4589	Approved
0.5928	Remote Similarity	NPD1512	Approved
0.5921	Remote Similarity	NPD9269	Phase 2
0.5912	Remote Similarity	NPD3657	Discovery
0.5909	Remote Similarity	NPD1164	Approved
0.5906	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.5906	Remote Similarity	NPD5303	Approved
0.5906	Remote Similarity	NPD5304	Approved
0.5899	Remote Similarity	NPD7473	Discontinued
0.5896	Remote Similarity	NPD4966	Approved
0.5896	Remote Similarity	NPD4967	Phase 2
0.5896	Remote Similarity	NPD4965	Approved
0.589	Remote Similarity	NPD2234	Approved
0.589	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.589	Remote Similarity	NPD2229	Approved
0.589	Remote Similarity	NPD2228	Approved
0.5882	Remote Similarity	NPD1669	Approved
0.5879	Remote Similarity	NPD6190	Approved
0.5878	Remote Similarity	NPD405	Clinical (unspecified phase)
0.5875	Remote Similarity	NPD817	Approved
0.5875	Remote Similarity	NPD823	Approved
0.5872	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.5871	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.5871	Remote Similarity	NPD2195	Approved
0.5871	Remote Similarity	NPD2194	Approved
0.5866	Remote Similarity	NPD7228	Approved
0.586	Remote Similarity	NPD7095	Approved
0.5855	Remote Similarity	NPD3705	Approved
0.5855	Remote Similarity	NPD1281	Approved
0.5845	Remote Similarity	NPD1444	Approved
0.5845	Remote Similarity	NPD1445	Approved
0.5833	Remote Similarity	NPD3018	Phase 2
0.5833	Remote Similarity	NPD9569	Approved
0.5828	Remote Similarity	NPD5762	Approved
0.5828	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.5828	Remote Similarity	NPD5763	Approved
0.5827	Remote Similarity	NPD3028	Approved
0.5823	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.5823	Remote Similarity	NPD597	Approved
0.5823	Remote Similarity	NPD601	Approved
0.5823	Remote Similarity	NPD598	Approved
0.582	Remote Similarity	NPD7539	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD1934	Approved
0.5811	Remote Similarity	NPD6671	Approved
0.5808	Remote Similarity	NPD7041	Phase 2
0.5808	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.5805	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.5802	Remote Similarity	NPD7742	Approved
0.5802	Remote Similarity	NPD7743	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