NPASS Compound

Structure

NPC261873 OpenBabel07101718322D 23 25 0 0 0 0 0 0 0 0999 V2000 -0.8660 -1.5000 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 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 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 -3.4641 -1.0000 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 3.0000 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 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 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 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -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 0.8660 0.5000 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 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 7 1 0 0 0 0 4 8 2 0 0 0 0 5 6 2 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 7 12 2 0 0 0 0 8 12 1 0 0 0 0 9 13 2 0 0 0 0 10 15 2 0 0 0 0 11 14 2 0 0 0 0 11 16 1 0 0 0 0 12 14 1 0 0 0 0 13 15 1 0 0 0 0 13 17 1 0 0 0 0 14 18 1 0 0 0 0 15 20 1 0 0 0 0 16 17 2 0 0 0 0 16 21 1 0 0 0 0 17 19 1 0 0 0 0 18 19 2 0 0 0 0 18 22 1 0 0 0 0 19 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	308.1
Volume:	322.944
LogP:	4.422
LogD:	3.445
LogS:	-3.878
# Rotatable Bonds:	3
TPSA:	69.92
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.636
Synthetic Accessibility Score:	2.149
Fsp3:	0.053
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.002
MDCK Permeability:	1.6374879123759456e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.95
30% Bioavailability (F30%):	0.654

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.103
Plasma Protein Binding (PPB):	100.25896453857422%
Volume Distribution (VD):	0.622
Pgp-substrate:	0.8604351282119751%

ADMET: Metabolism

CYP1A2-inhibitor:	0.952
CYP1A2-substrate:	0.602
CYP2C19-inhibitor:	0.804
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.682
CYP2C9-substrate:	0.856
CYP2D6-inhibitor:	0.604
CYP2D6-substrate:	0.81
CYP3A4-inhibitor:	0.313
CYP3A4-substrate:	0.221

ADMET: Excretion

Clearance (CL):	6.108
Half-life (T1/2):	0.354

ADMET: Toxicity

hERG Blockers:	0.193
Human Hepatotoxicity (H-HT):	0.029
Drug-inuced Liver Injury (DILI):	0.927
AMES Toxicity:	0.621
Rat Oral Acute Toxicity:	0.274
Maximum Recommended Daily Dose:	0.047
Skin Sensitization:	0.886
Carcinogencity:	0.135
Eye Corrosion:	0.003
Eye Irritation:	0.929
Respiratory Toxicity:	0.202

Download Data

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

Natural Product: NPC261873

Natural Product ID:	NPC261873
*Common Name:**	3'-Methoxy-[1,1';4',1'']Terphenyl-2',5',2''-Triol
IUPAC Name:	2-(2-hydroxyphenyl)-3-methoxy-5-phenylbenzene-1,4-diol
Synonyms:
Standard InCHIKey:	RBPPUBAYVVZZFE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H16O4/c1-23-19-17(13-9-5-6-10-15(13)20)16(21)11-14(18(19)22)12-7-3-2-4-8-12/h2-11,20-22H,1H3
SMILES:	COc1c(c2ccccc2O)c(cc(c2ccccc2)c1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL496051
PubChem CID:	11558611
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0002042] Terphenyls [CHEMONTID:0002126] P-terphenyls

*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
NPO32661	Phoma sp.	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562839]
NPO32661	Phoma sp.	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16643061]
NPO32661	Phoma sp.	Species	Didymellaceae	Eukaryota	giant jellyfish Nemopilema nomurai	n.a.	n.a.	PMID[22483395]
NPO32661	Phoma sp.	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26651221]
NPO32661	Phoma sp.	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30785282]
NPO32661	Phoma sp.	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31120749]
NPO32661	Phoma sp.	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7561907]

☑ 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	2

Activity Type	# Activity
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	5200.0	nM	PMID[517986]
NPT486	Organism	Toxoplasma gondii	Toxoplasma gondii	IC50	=	10400.0	nM	PMID[517986]

☑ 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 NPC261873 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	629
0.1-0.2	1963
0.2-0.3	6183
0.3-0.4	13001
0.4-0.5	3859
0.5-0.6	4627
0.6-0.7	7713
0.7-0.8	3803
0.8-0.85	536
0.85-0.9	298
0.9-0.95	60
0.95-1	25

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC283009
0.9922	High Similarity	NPC103967
0.9846	High Similarity	NPC90615
0.9846	High Similarity	NPC25111
0.9846	High Similarity	NPC201145
0.9846	High Similarity	NPC272157
0.9846	High Similarity	NPC6262
0.9846	High Similarity	NPC73535
0.9769	High Similarity	NPC114155
0.9769	High Similarity	NPC300846
0.9769	High Similarity	NPC476639
0.9766	High Similarity	NPC218884
0.9697	High Similarity	NPC34431
0.9697	High Similarity	NPC73505
0.9697	High Similarity	NPC165026
0.9697	High Similarity	NPC295719
0.9692	High Similarity	NPC111655
0.9552	High Similarity	NPC175838
0.9474	High Similarity	NPC79622
0.9474	High Similarity	NPC212942
0.9474	High Similarity	NPC29868
0.9453	High Similarity	NPC266691
0.9403	High Similarity	NPC308768
0.9403	High Similarity	NPC12668
0.9375	High Similarity	NPC236760
0.9328	High Similarity	NPC243996
0.9328	High Similarity	NPC132804
0.9328	High Similarity	NPC275061
0.9328	High Similarity	NPC243759
0.9328	High Similarity	NPC105847
0.9328	High Similarity	NPC218131
0.9328	High Similarity	NPC220344
0.9323	High Similarity	NPC143139
0.9323	High Similarity	NPC205442
0.9323	High Similarity	NPC202846
0.9313	High Similarity	NPC6451
0.9308	High Similarity	NPC234488
0.9308	High Similarity	NPC299221
0.9308	High Similarity	NPC311680
0.9308	High Similarity	NPC51840
0.9254	High Similarity	NPC242715
0.9254	High Similarity	NPC200935
0.9254	High Similarity	NPC266453
0.9254	High Similarity	NPC56329
0.9254	High Similarity	NPC151656
0.9254	High Similarity	NPC22902
0.9254	High Similarity	NPC230919
0.9254	High Similarity	NPC266006
0.9248	High Similarity	NPC255147
0.9248	High Similarity	NPC10314
0.9248	High Similarity	NPC294884
0.9248	High Similarity	NPC281521
0.9248	High Similarity	NPC158142
0.9248	High Similarity	NPC108198
0.9248	High Similarity	NPC201357
0.9248	High Similarity	NPC69029
0.9248	High Similarity	NPC200557
0.9237	High Similarity	NPC474356
0.9237	High Similarity	NPC232275
0.9237	High Similarity	NPC45715
0.9237	High Similarity	NPC12275
0.9231	High Similarity	NPC58164
0.9231	High Similarity	NPC10225
0.9179	High Similarity	NPC30632
0.9173	High Similarity	NPC125649
0.9173	High Similarity	NPC160697
0.916	High Similarity	NPC224157
0.916	High Similarity	NPC192687
0.9154	High Similarity	NPC154866
0.9147	High Similarity	NPC245060
0.9147	High Similarity	NPC112596
0.9124	High Similarity	NPC183709
0.9104	High Similarity	NPC313081
0.9104	High Similarity	NPC241241
0.9098	High Similarity	NPC269528
0.9098	High Similarity	NPC94236
0.9098	High Similarity	NPC37196
0.9084	High Similarity	NPC190144
0.9077	High Similarity	NPC159968
0.9077	High Similarity	NPC324112
0.9077	High Similarity	NPC82679
0.9077	High Similarity	NPC236791
0.9077	High Similarity	NPC74817
0.9077	High Similarity	NPC266555
0.9077	High Similarity	NPC293054
0.9077	High Similarity	NPC169474
0.9077	High Similarity	NPC246620
0.9077	High Similarity	NPC282000
0.9077	High Similarity	NPC124452
0.9071	High Similarity	NPC170239
0.9071	High Similarity	NPC97937
0.9071	High Similarity	NPC275125
0.9062	High Similarity	NPC95168
0.9062	High Similarity	NPC121115
0.9051	High Similarity	NPC472089
0.9044	High Similarity	NPC127218
0.9044	High Similarity	NPC184613
0.9044	High Similarity	NPC245207
0.9044	High Similarity	NPC25966
0.9044	High Similarity	NPC319647
0.9023	High Similarity	NPC161203
0.9015	High Similarity	NPC126836
0.9	High Similarity	NPC103823
0.9	High Similarity	NPC214406
0.9	High Similarity	NPC223953
0.9	High Similarity	NPC44748
0.9	High Similarity	NPC18924
0.9	High Similarity	NPC223136
0.9	High Similarity	NPC28730
0.9	High Similarity	NPC78974
0.8986	High Similarity	NPC472088
0.8986	High Similarity	NPC472087
0.8984	High Similarity	NPC135414
0.8971	High Similarity	NPC107551
0.8971	High Similarity	NPC326797
0.8971	High Similarity	NPC176051
0.8971	High Similarity	NPC103976
0.8971	High Similarity	NPC102904
0.8971	High Similarity	NPC276490
0.8971	High Similarity	NPC474282
0.8963	High Similarity	NPC256262
0.8963	High Similarity	NPC134968
0.8955	High Similarity	NPC32778
0.8944	High Similarity	NPC113790
0.8931	High Similarity	NPC216836
0.8931	High Similarity	NPC127587
0.8929	High Similarity	NPC125617
0.8923	High Similarity	NPC298757
0.8923	High Similarity	NPC116907
0.8923	High Similarity	NPC233410
0.8923	High Similarity	NPC117214
0.8923	High Similarity	NPC57490
0.8923	High Similarity	NPC193544
0.8923	High Similarity	NPC251855
0.8923	High Similarity	NPC203133
0.8923	High Similarity	NPC472093
0.8923	High Similarity	NPC221077
0.8923	High Similarity	NPC17943
0.8923	High Similarity	NPC265483
0.8923	High Similarity	NPC208950
0.8923	High Similarity	NPC299584
0.8923	High Similarity	NPC475169
0.8923	High Similarity	NPC82483
0.8923	High Similarity	NPC105925
0.8923	High Similarity	NPC234400
0.8923	High Similarity	NPC60885
0.8921	High Similarity	NPC477616
0.8921	High Similarity	NPC469630
0.8913	High Similarity	NPC471389
0.8906	High Similarity	NPC75713
0.8905	High Similarity	NPC230124
0.8905	High Similarity	NPC6300
0.8905	High Similarity	NPC22517
0.8905	High Similarity	NPC114171
0.8897	High Similarity	NPC270456
0.8897	High Similarity	NPC248727
0.8897	High Similarity	NPC472336
0.8897	High Similarity	NPC173660
0.8897	High Similarity	NPC162659
0.8897	High Similarity	NPC265433
0.8897	High Similarity	NPC472334
0.8897	High Similarity	NPC476698
0.8889	High Similarity	NPC289258
0.8889	High Similarity	NPC106215
0.8889	High Similarity	NPC188378
0.8889	High Similarity	NPC276026
0.8889	High Similarity	NPC209199
0.8889	High Similarity	NPC469659
0.8889	High Similarity	NPC56764
0.8889	High Similarity	NPC555
0.8889	High Similarity	NPC7515
0.8889	High Similarity	NPC206737
0.8881	High Similarity	NPC161958
0.8881	High Similarity	NPC14224
0.8881	High Similarity	NPC127624
0.8881	High Similarity	NPC86655
0.8881	High Similarity	NPC228843
0.8881	High Similarity	NPC202762
0.8872	High Similarity	NPC229231
0.8872	High Similarity	NPC214860
0.8872	High Similarity	NPC220935
0.8865	High Similarity	NPC126291
0.8864	High Similarity	NPC28765
0.8855	High Similarity	NPC76451
0.8849	High Similarity	NPC107161
0.8846	High Similarity	NPC183446
0.8846	High Similarity	NPC206487
0.8846	High Similarity	NPC5796
0.8841	High Similarity	NPC472090
0.8841	High Similarity	NPC472092
0.8841	High Similarity	NPC22317
0.8841	High Similarity	NPC160283
0.8841	High Similarity	NPC61783
0.8841	High Similarity	NPC259519
0.8841	High Similarity	NPC254759
0.8841	High Similarity	NPC284464
0.8841	High Similarity	NPC472091
0.8841	High Similarity	NPC20520
0.8837	High Similarity	NPC246967
0.8837	High Similarity	NPC474864

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 NPC261873 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	523
0.1-0.2	943
0.2-0.3	1878
0.3-0.4	2800
0.4-0.5	1527
0.5-0.6	937
0.6-0.7	469
0.7-0.8	68
0.8-0.85	2
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8797	High Similarity	NPD3027	Phase 3
0.8582	High Similarity	NPD1529	Clinical (unspecified phase)
0.8507	High Similarity	NPD1530	Clinical (unspecified phase)
0.8467	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8467	Intermediate Similarity	NPD1613	Approved
0.8248	Intermediate Similarity	NPD4625	Phase 3
0.8175	Intermediate Similarity	NPD4908	Phase 1
0.8074	Intermediate Similarity	NPD4749	Approved
0.8058	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7971	Intermediate Similarity	NPD3018	Phase 2
0.7908	Intermediate Similarity	NPD2801	Approved
0.7898	Intermediate Similarity	NPD6232	Discontinued
0.781	Intermediate Similarity	NPD2983	Phase 2
0.781	Intermediate Similarity	NPD2982	Phase 2
0.7801	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7794	Intermediate Similarity	NPD1610	Phase 2
0.7786	Intermediate Similarity	NPD5283	Phase 1
0.777	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7769	Intermediate Similarity	NPD228	Approved
0.7764	Intermediate Similarity	NPD5844	Phase 1
0.775	Intermediate Similarity	NPD7473	Discontinued
0.7737	Intermediate Similarity	NPD2981	Phase 2
0.7727	Intermediate Similarity	NPD1934	Approved
0.7714	Intermediate Similarity	NPD2861	Phase 2
0.7707	Intermediate Similarity	NPD6234	Discontinued
0.763	Intermediate Similarity	NPD1548	Phase 1
0.7615	Intermediate Similarity	NPD4750	Phase 3
0.7613	Intermediate Similarity	NPD37	Approved
0.7582	Intermediate Similarity	NPD1653	Approved
0.758	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD6166	Phase 2
0.7578	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD3620	Phase 2
0.7564	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7537	Intermediate Similarity	NPD6671	Approved
0.7481	Intermediate Similarity	NPD3022	Approved
0.7481	Intermediate Similarity	NPD3021	Approved
0.7468	Intermediate Similarity	NPD4965	Approved
0.7468	Intermediate Similarity	NPD4967	Phase 2
0.7468	Intermediate Similarity	NPD4966	Approved
0.7434	Intermediate Similarity	NPD1511	Approved
0.7432	Intermediate Similarity	NPD6100	Approved
0.7432	Intermediate Similarity	NPD6099	Approved
0.74	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD6674	Discontinued
0.7391	Intermediate Similarity	NPD7199	Phase 2
0.7383	Intermediate Similarity	NPD3540	Phase 1
0.7378	Intermediate Similarity	NPD7228	Approved
0.7376	Intermediate Similarity	NPD6696	Suspended
0.7358	Intermediate Similarity	NPD3882	Suspended
0.7338	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD1512	Approved
0.7315	Intermediate Similarity	NPD3539	Phase 1
0.7313	Intermediate Similarity	NPD7635	Approved
0.7305	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD5177	Phase 3
0.7273	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD7549	Discontinued
0.7237	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD1465	Phase 2
0.7222	Intermediate Similarity	NPD6746	Phase 2
0.7211	Intermediate Similarity	NPD4060	Phase 1
0.7211	Intermediate Similarity	NPD1558	Phase 1
0.7208	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD4005	Discontinued
0.7197	Intermediate Similarity	NPD2342	Discontinued
0.7188	Intermediate Similarity	NPD3817	Phase 2
0.7186	Intermediate Similarity	NPD7074	Phase 3
0.7179	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD8054	Approved
0.7176	Intermediate Similarity	NPD8053	Approved
0.7169	Intermediate Similarity	NPD3818	Discontinued
0.7163	Intermediate Similarity	NPD1091	Approved
0.7163	Intermediate Similarity	NPD3705	Approved
0.7163	Intermediate Similarity	NPD1611	Approved
0.7161	Intermediate Similarity	NPD7447	Phase 1
0.7152	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7124	Phase 2
0.7126	Intermediate Similarity	NPD7054	Approved
0.7121	Intermediate Similarity	NPD968	Approved
0.7117	Intermediate Similarity	NPD5494	Approved
0.7114	Intermediate Similarity	NPD1607	Approved
0.7114	Intermediate Similarity	NPD4097	Suspended
0.711	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD4055	Discovery
0.7099	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7212	Phase 2
0.7097	Intermediate Similarity	NPD4357	Discontinued
0.7097	Intermediate Similarity	NPD7213	Phase 3
0.7086	Intermediate Similarity	NPD2935	Discontinued
0.7083	Intermediate Similarity	NPD7472	Approved
0.7077	Intermediate Similarity	NPD846	Approved
0.7077	Intermediate Similarity	NPD940	Approved
0.7075	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6959	Discontinued
0.7059	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD5536	Phase 2
0.7044	Intermediate Similarity	NPD4678	Approved
0.7044	Intermediate Similarity	NPD4675	Approved
0.7044	Intermediate Similarity	NPD4380	Phase 2
0.7042	Intermediate Similarity	NPD422	Phase 1
0.7041	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7266	Discontinued
0.7034	Intermediate Similarity	NPD6584	Phase 3
0.7027	Intermediate Similarity	NPD6233	Phase 2
0.7021	Intermediate Similarity	NPD4626	Approved
0.702	Intermediate Similarity	NPD1510	Phase 2
0.7014	Intermediate Similarity	NPD2922	Phase 1
0.7014	Intermediate Similarity	NPD8651	Approved
0.7013	Intermediate Similarity	NPD3892	Phase 2
0.7007	Intermediate Similarity	NPD7095	Approved
0.7007	Intermediate Similarity	NPD1398	Phase 1
0.7	Intermediate Similarity	NPD6559	Discontinued
0.7	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1242	Phase 1
0.6993	Remote Similarity	NPD2233	Approved
0.6993	Remote Similarity	NPD2232	Approved
0.6993	Remote Similarity	NPD2230	Approved
0.6981	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.698	Remote Similarity	NPD1240	Approved
0.698	Remote Similarity	NPD2238	Phase 2
0.6978	Remote Similarity	NPD7340	Approved
0.6975	Remote Similarity	NPD5402	Approved
0.6972	Remote Similarity	NPD3496	Discontinued
0.6968	Remote Similarity	NPD6190	Approved
0.6968	Remote Similarity	NPD2219	Phase 1
0.6963	Remote Similarity	NPD5451	Approved
0.6959	Remote Similarity	NPD6798	Discontinued
0.6954	Remote Similarity	NPD6111	Discontinued
0.6953	Remote Similarity	NPD844	Approved
0.6948	Remote Similarity	NPD3060	Approved
0.6941	Remote Similarity	NPD6797	Phase 2
0.694	Remote Similarity	NPD290	Approved
0.6936	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6788	Approved
0.6933	Remote Similarity	NPD7768	Phase 2
0.6928	Remote Similarity	NPD3787	Discontinued
0.6928	Remote Similarity	NPD5762	Approved
0.6928	Remote Similarity	NPD5763	Approved
0.6913	Remote Similarity	NPD2674	Phase 3
0.6906	Remote Similarity	NPD709	Approved
0.6906	Remote Similarity	NPD7157	Approved
0.6903	Remote Similarity	NPD3750	Approved
0.6901	Remote Similarity	NPD6516	Phase 2
0.6901	Remote Similarity	NPD7240	Approved
0.6901	Remote Similarity	NPD7251	Discontinued
0.6901	Remote Similarity	NPD5846	Approved
0.6899	Remote Similarity	NPD288	Approved
0.6899	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD2684	Approved
0.6879	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD9296	Approved
0.6871	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD943	Approved
0.6863	Remote Similarity	NPD1551	Phase 2
0.686	Remote Similarity	NPD7808	Phase 3
0.6859	Remote Similarity	NPD2677	Approved
0.6857	Remote Similarity	NPD7906	Approved
0.6849	Remote Similarity	NPD2797	Approved
0.6849	Remote Similarity	NPD3094	Phase 2
0.6846	Remote Similarity	NPD5110	Phase 2
0.6846	Remote Similarity	NPD5111	Phase 2
0.6846	Remote Similarity	NPD5109	Approved
0.6842	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4536	Approved
0.6842	Remote Similarity	NPD4538	Approved
0.6839	Remote Similarity	NPD1652	Phase 2
0.6835	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD6599	Discontinued
0.6831	Remote Similarity	NPD1651	Approved
0.6831	Remote Similarity	NPD1357	Approved
0.6828	Remote Similarity	NPD6582	Phase 2
0.6828	Remote Similarity	NPD6583	Phase 3
0.6826	Remote Similarity	NPD7229	Phase 3
0.6821	Remote Similarity	NPD3657	Discovery
0.6821	Remote Similarity	NPD230	Phase 1
0.6821	Remote Similarity	NPD5735	Approved
0.6818	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD7843	Approved
0.681	Remote Similarity	NPD5929	Approved
0.681	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD4624	Approved
0.68	Remote Similarity	NPD4663	Approved
0.6797	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD4628	Phase 3
0.6795	Remote Similarity	NPD7466	Approved
0.6794	Remote Similarity	NPD3020	Approved
0.679	Remote Similarity	NPD5089	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