NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	230.09
Volume:	244.139
LogP:	3.774
LogD:	3.553
LogS:	-2.759
# Rotatable Bonds:	2
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.83
Synthetic Accessibility Score:	2.162
Fsp3:	0.143
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.919
MDCK Permeability:	1.555394737806637e-05
Pgp-inhibitor:	0.093
Pgp-substrate:	0.016
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.968
30% Bioavailability (F30%):	0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.039
Plasma Protein Binding (PPB):	96.11409759521484%
Volume Distribution (VD):	0.584
Pgp-substrate:	2.47057843208313%

ADMET: Metabolism

CYP1A2-inhibitor:	0.96
CYP1A2-substrate:	0.761
CYP2C19-inhibitor:	0.874
CYP2C19-substrate:	0.098
CYP2C9-inhibitor:	0.581
CYP2C9-substrate:	0.961
CYP2D6-inhibitor:	0.954
CYP2D6-substrate:	0.889
CYP3A4-inhibitor:	0.568
CYP3A4-substrate:	0.187

ADMET: Excretion

Clearance (CL):	13.269
Half-life (T1/2):	0.889

ADMET: Toxicity

hERG Blockers:	0.071
Human Hepatotoxicity (H-HT):	0.076
Drug-inuced Liver Injury (DILI):	0.041
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.059
Maximum Recommended Daily Dose:	0.957
Skin Sensitization:	0.947
Carcinogencity:	0.264
Eye Corrosion:	0.661
Eye Irritation:	0.987
Respiratory Toxicity:	0.825

Download Data

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

Natural Product: NPC255068

Natural Product ID:	NPC255068
*Common Name:**	Diorcinol
IUPAC Name:	3-(3-hydroxy-5-methylphenoxy)-5-methylphenol
Synonyms:	Diorcinol
Standard InCHIKey:	SPCJQQBYWVGMQG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H14O3/c1-9-3-11(15)7-13(5-9)17-14-6-10(2)4-12(16)8-14/h3-8,15-16H,1-2H3
SMILES:	Cc1cc(cc(c1)Oc1cc(C)cc(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2332161
PubChem CID:	23396613
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0004155] Diphenylethers

*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
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	rhizosphere	Sonoran desert	n.a.	PMID[15620238]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17542490]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17564467]
NPO31451	Aspergillus sydowii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18505285]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19053517]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21366228]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21718031]
NPO31451	Aspergillus sydowii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21718031]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21854017]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	healthy leaf of Ginkgo biloba	campus of Nanjing University, Nanjing, China	2008-OCT	PMID[22196792]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	isolated from the sponge Xestospongia testudinaria	n.a.	n.a.	PMID[22225637]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	Isolated from a sandy-loam soil sample	50 m inland from Waikiki Beach, Honolulu, Hawaii	2010-JUL	PMID[22400916]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22703109]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23527875]
NPO31451	Aspergillus sydowii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23647825]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24050204]
NPO31451	Aspergillus sydowii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24057165]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25001296]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25581396]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26273902]
NPO40032	Aspergillus austroafricanus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27070198]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31012585]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33305943]

☑ 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	6
MIC	6
Others	6

Activity Type	# Activity
Cell Line	6
NON-MOLECULAR	4
Organism	6
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	10000.0	nM	PMID[463275]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	10000.0	nM	PMID[463275]
NPT1668	Cell Line	NCI-H157	Homo sapiens	IC50	=	20200.0	nM	PMID[463279]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	31600.0	nM	PMID[463279]
NPT81	Cell Line	A549	Homo sapiens	Activity	<	50.0	%	PMID[463279]
NPT1668	Cell Line	NCI-H157	Homo sapiens	Activity	<	50.0	%	PMID[463279]
NPT2911	Organism	Pseudomonas putida	Pseudomonas putida	MIC	=	100000.0	nM	PMID[463275]
NPT565	Organism	Vibrio parahaemolyticus	Vibrio parahaemolyticus	MIC	=	100000.0	nM	PMID[463275]
NPT1311	Organism	Listonella anguillarum	Listonella anguillarum	MIC	=	100000.0	nM	PMID[463275]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	54300.0	nM	PMID[463275]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	27200.0	nM	PMID[463275]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	39.78	%	PMID[463276]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10.0	ug.mL-1	PMID[463276]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	91.99	%	PMID[463276]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	12210.0	nM	PMID[463276]
NPT35	Others	n.a.		Activity	<	50.0	%	PMID[463277]
NPT2	Others	Unspecified		Inhibition	=	10.0	%	PMID[463277]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	34800.0	nM	PMID[463278]

☑ 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 NPC255068 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	397
0.1-0.2	2277
0.2-0.3	7850
0.3-0.4	11826
0.4-0.5	3701
0.5-0.6	5769
0.6-0.7	7938
0.7-0.8	2487
0.8-0.85	349
0.85-0.9	77
0.9-0.95	21
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9524	High Similarity	NPC94045
0.9346	High Similarity	NPC280606
0.9327	High Similarity	NPC164576
0.9252	High Similarity	NPC90520
0.9252	High Similarity	NPC296920
0.9174	High Similarity	NPC22610
0.9174	High Similarity	NPC180508
0.9174	High Similarity	NPC276737
0.9174	High Similarity	NPC228287
0.9091	High Similarity	NPC53906
0.9091	High Similarity	NPC167934
0.9035	High Similarity	NPC145780
0.9009	High Similarity	NPC141090
0.9009	High Similarity	NPC203113
0.9009	High Similarity	NPC150624
0.9009	High Similarity	NPC114064
0.8981	High Similarity	NPC168657
0.8938	High Similarity	NPC85895
0.8938	High Similarity	NPC137294
0.8929	High Similarity	NPC33270
0.8929	High Similarity	NPC470759
0.8929	High Similarity	NPC127894
0.8929	High Similarity	NPC15860
0.8929	High Similarity	NPC244816
0.8929	High Similarity	NPC474933
0.8929	High Similarity	NPC69261
0.8929	High Similarity	NPC219070
0.8929	High Similarity	NPC195466
0.8929	High Similarity	NPC221549
0.8929	High Similarity	NPC50521
0.8919	High Similarity	NPC808
0.8879	High Similarity	NPC35543
0.8803	High Similarity	NPC140521
0.8803	High Similarity	NPC78446
0.8803	High Similarity	NPC270030
0.8796	High Similarity	NPC245115
0.8783	High Similarity	NPC218753
0.8772	High Similarity	NPC226629
0.8772	High Similarity	NPC184302
0.8729	High Similarity	NPC249836
0.8716	High Similarity	NPC82016
0.8707	High Similarity	NPC212965
0.8684	High Similarity	NPC190514
0.8684	High Similarity	NPC74821
0.8654	High Similarity	NPC291789
0.8644	High Similarity	NPC122792
0.8644	High Similarity	NPC228972
0.8636	High Similarity	NPC2682
0.8636	High Similarity	NPC303521
0.8632	High Similarity	NPC120638
0.8632	High Similarity	NPC74137
0.8621	High Similarity	NPC102639
0.8621	High Similarity	NPC166759
0.8609	High Similarity	NPC295259
0.8598	High Similarity	NPC12987
0.8598	High Similarity	NPC474603
0.8584	High Similarity	NPC464
0.8584	High Similarity	NPC185541
0.8583	High Similarity	NPC210355
0.8583	High Similarity	NPC46978
0.8583	High Similarity	NPC216836
0.8559	High Similarity	NPC96940
0.8547	High Similarity	NPC193364
0.8547	High Similarity	NPC476633
0.8547	High Similarity	NPC75713
0.8534	High Similarity	NPC8283
0.8534	High Similarity	NPC474565
0.8534	High Similarity	NPC232084
0.8534	High Similarity	NPC10932
0.8534	High Similarity	NPC61516
0.8534	High Similarity	NPC258979
0.8534	High Similarity	NPC247364
0.8534	High Similarity	NPC93398
0.8512	High Similarity	NPC63179
0.8509	High Similarity	NPC85292
0.8509	High Similarity	NPC193067
0.8509	High Similarity	NPC229147
0.8509	High Similarity	NPC54507
0.85	High Similarity	NPC181361
0.8491	Intermediate Similarity	NPC161571
0.8491	Intermediate Similarity	NPC275053
0.8491	Intermediate Similarity	NPC248573
0.8475	Intermediate Similarity	NPC71579
0.8475	Intermediate Similarity	NPC18128
0.8475	Intermediate Similarity	NPC473411
0.8475	Intermediate Similarity	NPC262253
0.8475	Intermediate Similarity	NPC36016
0.8475	Intermediate Similarity	NPC100099
0.8475	Intermediate Similarity	NPC77789
0.8447	Intermediate Similarity	NPC295295
0.8443	Intermediate Similarity	NPC45824
0.8443	Intermediate Similarity	NPC96719
0.8443	Intermediate Similarity	NPC16577
0.8443	Intermediate Similarity	NPC222108
0.8435	Intermediate Similarity	NPC259638
0.843	Intermediate Similarity	NPC470699
0.843	Intermediate Similarity	NPC250432
0.843	Intermediate Similarity	NPC5447
0.8421	Intermediate Similarity	NPC301321
0.8417	Intermediate Similarity	NPC12308
0.8417	Intermediate Similarity	NPC476254
0.8417	Intermediate Similarity	NPC131397
0.8411	Intermediate Similarity	NPC100340
0.8411	Intermediate Similarity	NPC143659
0.8403	Intermediate Similarity	NPC76465
0.8403	Intermediate Similarity	NPC84086
0.8403	Intermediate Similarity	NPC136319
0.8403	Intermediate Similarity	NPC282496
0.8403	Intermediate Similarity	NPC95168
0.8403	Intermediate Similarity	NPC38761
0.8403	Intermediate Similarity	NPC233526
0.839	Intermediate Similarity	NPC190454
0.839	Intermediate Similarity	NPC54972
0.839	Intermediate Similarity	NPC97432
0.8374	Intermediate Similarity	NPC214860
0.8374	Intermediate Similarity	NPC474481
0.8374	Intermediate Similarity	NPC229231
0.8374	Intermediate Similarity	NPC472338
0.8362	Intermediate Similarity	NPC131118
0.8361	Intermediate Similarity	NPC46274
0.8361	Intermediate Similarity	NPC226331
0.8347	Intermediate Similarity	NPC230479
0.8347	Intermediate Similarity	NPC283049
0.8347	Intermediate Similarity	NPC50315
0.8347	Intermediate Similarity	NPC476006
0.8347	Intermediate Similarity	NPC26879
0.8333	Intermediate Similarity	NPC197351
0.8333	Intermediate Similarity	NPC228503
0.8333	Intermediate Similarity	NPC134195
0.8333	Intermediate Similarity	NPC5796
0.8333	Intermediate Similarity	NPC206487
0.8333	Intermediate Similarity	NPC246648
0.8333	Intermediate Similarity	NPC86502
0.8333	Intermediate Similarity	NPC138248
0.8333	Intermediate Similarity	NPC106914
0.8333	Intermediate Similarity	NPC159132
0.8319	Intermediate Similarity	NPC41562
0.8306	Intermediate Similarity	NPC160623
0.8306	Intermediate Similarity	NPC472597
0.8306	Intermediate Similarity	NPC8899
0.8306	Intermediate Similarity	NPC472590
0.8305	Intermediate Similarity	NPC199023
0.8305	Intermediate Similarity	NPC472596
0.8304	Intermediate Similarity	NPC242178
0.8304	Intermediate Similarity	NPC106141
0.8293	Intermediate Similarity	NPC3439
0.8293	Intermediate Similarity	NPC218856
0.8293	Intermediate Similarity	NPC273295
0.8293	Intermediate Similarity	NPC472797
0.8293	Intermediate Similarity	NPC218003
0.8293	Intermediate Similarity	NPC202582
0.8293	Intermediate Similarity	NPC222004
0.8293	Intermediate Similarity	NPC470258
0.8293	Intermediate Similarity	NPC285339
0.8293	Intermediate Similarity	NPC190629
0.8293	Intermediate Similarity	NPC226788
0.8293	Intermediate Similarity	NPC210623
0.8291	Intermediate Similarity	NPC20674
0.8288	Intermediate Similarity	NPC75440
0.8279	Intermediate Similarity	NPC474119
0.8279	Intermediate Similarity	NPC50368
0.8273	Intermediate Similarity	NPC473653
0.8264	Intermediate Similarity	NPC472093
0.8264	Intermediate Similarity	NPC251855
0.8264	Intermediate Similarity	NPC117214
0.8264	Intermediate Similarity	NPC208950
0.8264	Intermediate Similarity	NPC278955
0.8264	Intermediate Similarity	NPC299584
0.8264	Intermediate Similarity	NPC113495
0.8264	Intermediate Similarity	NPC193544
0.8264	Intermediate Similarity	NPC188022
0.8264	Intermediate Similarity	NPC221077
0.8264	Intermediate Similarity	NPC57490
0.8264	Intermediate Similarity	NPC285040
0.8264	Intermediate Similarity	NPC17943
0.8264	Intermediate Similarity	NPC105925
0.8264	Intermediate Similarity	NPC103420
0.8264	Intermediate Similarity	NPC102540
0.8264	Intermediate Similarity	NPC203133
0.8264	Intermediate Similarity	NPC105718
0.8264	Intermediate Similarity	NPC475169
0.8264	Intermediate Similarity	NPC17809
0.8264	Intermediate Similarity	NPC82483
0.8264	Intermediate Similarity	NPC234400
0.8264	Intermediate Similarity	NPC298757
0.8264	Intermediate Similarity	NPC60885
0.8264	Intermediate Similarity	NPC265483
0.8264	Intermediate Similarity	NPC116907
0.8264	Intermediate Similarity	NPC105031
0.8264	Intermediate Similarity	NPC233410
0.8257	Intermediate Similarity	NPC241891
0.8257	Intermediate Similarity	NPC102216
0.8257	Intermediate Similarity	NPC30506
0.825	Intermediate Similarity	NPC121115
0.825	Intermediate Similarity	NPC228922
0.825	Intermediate Similarity	NPC197757
0.824	Intermediate Similarity	NPC160991
0.824	Intermediate Similarity	NPC245120
0.824	Intermediate Similarity	NPC161203
0.824	Intermediate Similarity	NPC16208

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 NPC255068 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	379
0.1-0.2	1086
0.2-0.3	1884
0.3-0.4	2648
0.4-0.5	1592
0.5-0.6	982
0.6-0.7	498
0.7-0.8	69
0.8-0.85	8
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8684	High Similarity	NPD1548	Phase 1
0.8559	High Similarity	NPD4749	Approved
0.8547	High Similarity	NPD1610	Phase 2
0.8491	Intermediate Similarity	NPD1242	Phase 1
0.8443	Intermediate Similarity	NPD4625	Phase 3
0.843	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8361	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8273	Intermediate Similarity	NPD968	Approved
0.8235	Intermediate Similarity	NPD422	Phase 1
0.8211	Intermediate Similarity	NPD4908	Phase 1
0.8095	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD1613	Approved
0.808	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.808	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3027	Phase 3
0.7949	Intermediate Similarity	NPD6671	Approved
0.7869	Intermediate Similarity	NPD1608	Approved
0.7805	Intermediate Similarity	NPD2983	Phase 2
0.7805	Intermediate Similarity	NPD2982	Phase 2
0.7786	Intermediate Similarity	NPD6099	Approved
0.7786	Intermediate Similarity	NPD6100	Approved
0.776	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7739	Intermediate Similarity	NPD4750	Phase 3
0.7724	Intermediate Similarity	NPD2981	Phase 2
0.7719	Intermediate Similarity	NPD290	Approved
0.7698	Intermediate Similarity	NPD2861	Phase 2
0.7656	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7623	Intermediate Similarity	NPD17	Approved
0.7607	Intermediate Similarity	NPD228	Approved
0.7589	Intermediate Similarity	NPD846	Approved
0.7589	Intermediate Similarity	NPD940	Approved
0.7559	Intermediate Similarity	NPD3018	Phase 2
0.7538	Intermediate Similarity	NPD1558	Phase 1
0.7519	Intermediate Similarity	NPD1551	Phase 2
0.75	Intermediate Similarity	NPD1091	Approved
0.748	Intermediate Similarity	NPD1778	Approved
0.748	Intermediate Similarity	NPD6584	Phase 3
0.746	Intermediate Similarity	NPD6696	Suspended
0.746	Intermediate Similarity	NPD3225	Approved
0.7426	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD1240	Approved
0.7391	Intermediate Similarity	NPD1511	Approved
0.7364	Intermediate Similarity	NPD2934	Approved
0.7364	Intermediate Similarity	NPD2933	Approved
0.7355	Intermediate Similarity	NPD709	Approved
0.735	Intermediate Similarity	NPD2684	Approved
0.7339	Intermediate Similarity	NPD2423	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD1182	Approved
0.7302	Intermediate Similarity	NPD2231	Phase 2
0.7302	Intermediate Similarity	NPD2235	Phase 2
0.7299	Intermediate Similarity	NPD3750	Approved
0.7299	Intermediate Similarity	NPD3892	Phase 2
0.7297	Intermediate Similarity	NPD2859	Approved
0.7297	Intermediate Similarity	NPD2860	Approved
0.7293	Intermediate Similarity	NPD1607	Approved
0.7286	Intermediate Similarity	NPD1512	Approved
0.7282	Intermediate Similarity	NPD9093	Approved
0.7279	Intermediate Similarity	NPD1549	Phase 2
0.7279	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD1203	Approved
0.7266	Intermediate Similarity	NPD2797	Approved
0.7258	Intermediate Similarity	NPD5585	Approved
0.7257	Intermediate Similarity	NPD3020	Approved
0.725	Intermediate Similarity	NPD5535	Approved
0.725	Intermediate Similarity	NPD821	Approved
0.7244	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD6582	Phase 2
0.7244	Intermediate Similarity	NPD6583	Phase 3
0.7222	Intermediate Similarity	NPD1535	Discovery
0.7222	Intermediate Similarity	NPD9295	Approved
0.7214	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD7447	Phase 1
0.7212	Intermediate Similarity	NPD9089	Approved
0.719	Intermediate Similarity	NPD1398	Phase 1
0.719	Intermediate Similarity	NPD5283	Phase 1
0.7185	Intermediate Similarity	NPD1510	Phase 2
0.717	Intermediate Similarity	NPD111	Approved
0.7165	Intermediate Similarity	NPD1481	Phase 2
0.7143	Intermediate Similarity	NPD7212	Phase 2
0.7143	Intermediate Similarity	NPD844	Approved
0.7143	Intermediate Similarity	NPD7213	Phase 3
0.7143	Intermediate Similarity	NPD3496	Discontinued
0.7143	Intermediate Similarity	NPD4060	Phase 1
0.7107	Intermediate Similarity	NPD7843	Approved
0.7103	Intermediate Similarity	NPD1934	Approved
0.7099	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD9697	Approved
0.7091	Intermediate Similarity	NPD9365	Approved
0.7087	Intermediate Similarity	NPD1611	Approved
0.7083	Intermediate Similarity	NPD4675	Approved
0.7083	Intermediate Similarity	NPD4678	Approved
0.708	Intermediate Similarity	NPD288	Approved
0.7073	Intermediate Similarity	NPD7157	Approved
0.7063	Intermediate Similarity	NPD2107	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD2801	Approved
0.7045	Intermediate Similarity	NPD7095	Approved
0.7043	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD1894	Discontinued
0.7031	Intermediate Similarity	NPD2230	Approved
0.7031	Intermediate Similarity	NPD2233	Approved
0.7031	Intermediate Similarity	NPD1840	Phase 2
0.7031	Intermediate Similarity	NPD2232	Approved
0.7031	Intermediate Similarity	NPD9717	Approved
0.7031	Intermediate Similarity	NPD1244	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD2407	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD4357	Discontinued
0.7016	Intermediate Similarity	NPD7340	Approved
0.7015	Intermediate Similarity	NPD2238	Phase 2
0.7007	Intermediate Similarity	NPD2796	Approved
0.7	Intermediate Similarity	NPD3021	Approved
0.7	Intermediate Similarity	NPD3022	Approved
0.7	Intermediate Similarity	NPD5451	Approved
0.6992	Remote Similarity	NPD3268	Approved
0.6984	Remote Similarity	NPD1357	Approved
0.6983	Remote Similarity	NPD291	Approved
0.6978	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD4359	Approved
0.6972	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD5124	Phase 1
0.6963	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD230	Phase 1
0.696	Remote Similarity	NPD5536	Phase 2
0.6959	Remote Similarity	NPD3882	Suspended
0.6957	Remote Similarity	NPD3540	Phase 1
0.6953	Remote Similarity	NPD776	Approved
0.6944	Remote Similarity	NPD1653	Approved
0.6935	Remote Similarity	NPD2557	Approved
0.6934	Remote Similarity	NPD7033	Discontinued
0.6934	Remote Similarity	NPD3748	Approved
0.6929	Remote Similarity	NPD5846	Approved
0.6929	Remote Similarity	NPD6516	Phase 2
0.6923	Remote Similarity	NPD1283	Approved
0.6912	Remote Similarity	NPD3052	Approved
0.6912	Remote Similarity	NPD3054	Approved
0.6911	Remote Similarity	NPD1241	Discontinued
0.6903	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD9296	Approved
0.6891	Remote Similarity	NPD3134	Approved
0.6884	Remote Similarity	NPD3539	Phase 1
0.688	Remote Similarity	NPD3596	Phase 2
0.6866	Remote Similarity	NPD411	Approved
0.6866	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD1296	Phase 2
0.6861	Remote Similarity	NPD4538	Approved
0.6861	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD4536	Approved
0.6857	Remote Similarity	NPD1652	Phase 2
0.6853	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.685	Remote Similarity	NPD3444	Approved
0.685	Remote Similarity	NPD3445	Approved
0.685	Remote Similarity	NPD1651	Approved
0.685	Remote Similarity	NPD3443	Approved
0.6846	Remote Similarity	NPD5327	Phase 3
0.6846	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD1669	Approved
0.6838	Remote Similarity	NPD5735	Approved
0.6838	Remote Similarity	NPD447	Suspended
0.6833	Remote Similarity	NPD1358	Approved
0.6825	Remote Similarity	NPD1408	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD7046	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD7819	Suspended
0.6822	Remote Similarity	NPD3705	Approved
0.6818	Remote Similarity	NPD558	Phase 2
0.6818	Remote Similarity	NPD9094	Approved
0.6812	Remote Similarity	NPD4308	Phase 3
0.6809	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD7466	Approved
0.6797	Remote Similarity	NPD2667	Approved
0.6797	Remote Similarity	NPD2668	Approved
0.6797	Remote Similarity	NPD4626	Approved
0.6794	Remote Similarity	NPD8651	Approved
0.6783	Remote Similarity	NPD6799	Approved
0.678	Remote Similarity	NPD9500	Approved
0.6779	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD9545	Approved
0.6772	Remote Similarity	NPD2486	Discontinued
0.6772	Remote Similarity	NPD6581	Approved
0.6772	Remote Similarity	NPD6580	Approved
0.6767	Remote Similarity	NPD1712	Approved
0.6767	Remote Similarity	NPD4993	Discontinued
0.6765	Remote Similarity	NPD4140	Approved
0.6763	Remote Similarity	NPD2935	Discontinued
0.6761	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD2219	Phase 1
0.6744	Remote Similarity	NPD3847	Discontinued
0.6742	Remote Similarity	NPD3267	Approved
0.6742	Remote Similarity	NPD3266	Approved
0.6739	Remote Similarity	NPD2200	Suspended
0.6738	Remote Similarity	NPD1243	Approved
0.6738	Remote Similarity	NPD2800	Approved
0.6736	Remote Similarity	NPD4123	Phase 3
0.6733	Remote Similarity	NPD7768	Phase 2
0.6721	Remote Similarity	NPD1792	Phase 2
0.6719	Remote Similarity	NPD6382	Discontinued
0.6719	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD2595	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