NPASS Compound

Structure

NPC474839 OpenBabel07101719142D 24 25 0 0 0 0 0 0 0 0999 V2000 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -6.0000 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 -4.3301 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 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 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -3.0000 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 0.8660 -1.5000 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 -7.7942 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 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 1 2 1 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 9 1 0 0 0 0 7 10 1 0 0 0 0 8 11 2 0 0 0 0 8 12 1 0 0 0 0 9 17 1 0 0 0 0 10 19 1 0 0 0 0 11 20 1 0 0 0 0 12 21 2 0 0 0 0 13 15 1 0 0 0 0 13 17 2 0 0 0 0 14 16 2 0 0 0 0 14 17 1 0 0 0 0 15 18 2 0 0 0 0 16 18 1 0 0 0 0 18 22 1 0 0 0 0 19 20 2 0 0 0 0 19 21 1 0 0 0 0 20 23 1 0 0 0 0 21 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	328.2
Volume:	365.211
LogP:	6.181
LogD:	4.16
LogS:	-3.216
# Rotatable Bonds:	10
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.517
Synthetic Accessibility Score:	2.053
Fsp3:	0.429
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.992
MDCK Permeability:	1.4425664630834945e-05
Pgp-inhibitor:	0.073
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.038
Plasma Protein Binding (PPB):	99.18706512451172%
Volume Distribution (VD):	1.228
Pgp-substrate:	0.4306112825870514%

ADMET: Metabolism

CYP1A2-inhibitor:	0.913
CYP1A2-substrate:	0.213
CYP2C19-inhibitor:	0.915
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.397
CYP2C9-substrate:	0.978
CYP2D6-inhibitor:	0.926
CYP2D6-substrate:	0.894
CYP3A4-inhibitor:	0.333
CYP3A4-substrate:	0.206

ADMET: Excretion

Clearance (CL):	9.03
Half-life (T1/2):	0.765

ADMET: Toxicity

hERG Blockers:	0.062
Human Hepatotoxicity (H-HT):	0.019
Drug-inuced Liver Injury (DILI):	0.019
AMES Toxicity:	0.441
Rat Oral Acute Toxicity:	0.291
Maximum Recommended Daily Dose:	0.051
Skin Sensitization:	0.963
Carcinogencity:	0.07
Eye Corrosion:	0.819
Eye Irritation:	0.97
Respiratory Toxicity:	0.536

Download Data

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

Natural Product: NPC474839

Natural Product ID:	NPC474839
*Common Name:**	2-[9-(4-Hydroxyphenyl)Nonyl]Benzene-1,3-Diol
IUPAC Name:	2-[9-(4-hydroxyphenyl)nonyl]benzene-1,3-diol
Synonyms:
Standard InCHIKey:	GJRGOZGOAXXZFQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H28O3/c22-18-15-13-17(14-16-18)9-6-4-2-1-3-5-7-10-19-20(23)11-8-12-21(19)24/h8,11-16,22-24H,1-7,9-10H2
SMILES:	Oc1ccc(cc1)CCCCCCCCCc1c(O)cccc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL484655
PubChem CID:	44576027
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0001286] Benzenediols [CHEMONTID:0000137] Resorcinols

*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
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	seeds	n.a.	n.a.	PMID[17998162]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1955885]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	fruit	n.a.	PMID[20879744]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27419473]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Aril	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Leaf Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO5241	Myristica fragrans	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5241	Myristica fragrans	Species	Myristicaceae	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
MIC	12

Activity Type	# Activity
Organism	12

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	4.0	ug.mL-1	PMID[510306]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	4.0	ug.mL-1	PMID[510306]
NPT3730	Organism	Enterococcus durans	Enterococcus durans	MIC	=	4.0	ug.mL-1	PMID[510306]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	8.0	ug.mL-1	PMID[510306]
NPT3730	Organism	Enterococcus durans	Enterococcus durans	MIC	=	8.0	ug.mL-1	PMID[510306]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	16.0	ug.mL-1	PMID[510306]

☑ 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 NPC474839 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	309
0.1-0.2	1750
0.2-0.3	5463
0.3-0.4	13990
0.4-0.5	4581
0.5-0.6	7436
0.6-0.7	6796
0.7-0.8	1989
0.8-0.85	242
0.85-0.9	101
0.9-0.95	36
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9897	High Similarity	NPC119860
0.97	High Similarity	NPC61885
0.97	High Similarity	NPC63698
0.951	High Similarity	NPC475018
0.95	High Similarity	NPC248904
0.9417	High Similarity	NPC225679
0.9417	High Similarity	NPC165770
0.9417	High Similarity	NPC476632
0.9417	High Similarity	NPC4493
0.9327	High Similarity	NPC43525
0.9327	High Similarity	NPC166995
0.93	High Similarity	NPC30506
0.93	High Similarity	NPC241891
0.93	High Similarity	NPC102216
0.9286	High Similarity	NPC80027
0.9238	High Similarity	NPC117846
0.9223	High Similarity	NPC33728
0.9223	High Similarity	NPC19808
0.9208	High Similarity	NPC134829
0.9208	High Similarity	NPC292452
0.9151	High Similarity	NPC107240
0.9126	High Similarity	NPC174981
0.9118	High Similarity	NPC470700
0.9118	High Similarity	NPC39097
0.9118	High Similarity	NPC118286
0.9118	High Similarity	NPC109691
0.9118	High Similarity	NPC39664
0.9118	High Similarity	NPC302681
0.91	High Similarity	NPC100340
0.91	High Similarity	NPC143659
0.9072	High Similarity	NPC128062
0.9072	High Similarity	NPC151715
0.9048	High Similarity	NPC224527
0.9038	High Similarity	NPC202647
0.9029	High Similarity	NPC54844
0.902	High Similarity	NPC246056
0.9	High Similarity	NPC275053
0.9	High Similarity	NPC10588
0.9	High Similarity	NPC248573
0.9	High Similarity	NPC161571
0.8981	High Similarity	NPC229147
0.8981	High Similarity	NPC85292
0.8981	High Similarity	NPC54507
0.898	High Similarity	NPC26244
0.8911	High Similarity	NPC72947
0.8911	High Similarity	NPC284011
0.8899	High Similarity	NPC470760
0.8889	High Similarity	NPC464
0.8889	High Similarity	NPC185541
0.8889	High Similarity	NPC473388
0.8879	High Similarity	NPC261343
0.8866	High Similarity	NPC45040
0.8846	High Similarity	NPC204901
0.8846	High Similarity	NPC232523
0.8846	High Similarity	NPC158253
0.8835	High Similarity	NPC37802
0.8824	High Similarity	NPC313030
0.8824	High Similarity	NPC53051
0.8824	High Similarity	NPC249828
0.8824	High Similarity	NPC168303
0.8824	High Similarity	NPC146798
0.8824	High Similarity	NPC71002
0.8824	High Similarity	NPC85479
0.8824	High Similarity	NPC106396
0.8824	High Similarity	NPC302219
0.8824	High Similarity	NPC242342
0.8824	High Similarity	NPC168829
0.8824	High Similarity	NPC94351
0.8824	High Similarity	NPC24404
0.8824	High Similarity	NPC222522
0.8818	High Similarity	NPC144343
0.8818	High Similarity	NPC131118
0.8812	High Similarity	NPC166761
0.8812	High Similarity	NPC213730
0.8807	High Similarity	NPC115808
0.88	High Similarity	NPC291789
0.875	High Similarity	NPC201662
0.875	High Similarity	NPC12640
0.875	High Similarity	NPC99836
0.8738	High Similarity	NPC288411
0.8738	High Similarity	NPC244513
0.8738	High Similarity	NPC227458
0.8738	High Similarity	NPC218879
0.8727	High Similarity	NPC277588
0.8725	High Similarity	NPC147310
0.8725	High Similarity	NPC24407
0.8725	High Similarity	NPC7686
0.8725	High Similarity	NPC192032
0.8725	High Similarity	NPC91461
0.8725	High Similarity	NPC166313
0.8725	High Similarity	NPC294186
0.8725	High Similarity	NPC40258
0.8725	High Similarity	NPC11280
0.8725	High Similarity	NPC137415
0.8716	High Similarity	NPC84999
0.8716	High Similarity	NPC246760
0.8713	High Similarity	NPC216468
0.8713	High Similarity	NPC132078
0.8713	High Similarity	NPC51333
0.8713	High Similarity	NPC78119
0.8704	High Similarity	NPC23804
0.87	High Similarity	NPC132271
0.87	High Similarity	NPC292730
0.87	High Similarity	NPC216520
0.87	High Similarity	NPC82664
0.8692	High Similarity	NPC268032
0.8679	High Similarity	NPC299568
0.8679	High Similarity	NPC186385
0.8661	High Similarity	NPC69006
0.8661	High Similarity	NPC223451
0.8654	High Similarity	NPC219286
0.8654	High Similarity	NPC138942
0.8654	High Similarity	NPC99557
0.86	High Similarity	NPC274678
0.8586	High Similarity	NPC271440
0.8584	High Similarity	NPC24125
0.8571	High Similarity	NPC191866
0.8571	High Similarity	NPC217174
0.8559	High Similarity	NPC33270
0.8559	High Similarity	NPC474933
0.8559	High Similarity	NPC69261
0.8545	High Similarity	NPC808
0.8532	High Similarity	NPC263753
0.8529	High Similarity	NPC92730
0.8509	High Similarity	NPC237667
0.8509	High Similarity	NPC476633
0.8509	High Similarity	NPC54972
0.8509	High Similarity	NPC196976
0.85	High Similarity	NPC76938
0.8491	Intermediate Similarity	NPC176527
0.8491	Intermediate Similarity	NPC305603
0.8491	Intermediate Similarity	NPC61033
0.8482	Intermediate Similarity	NPC190514
0.8476	Intermediate Similarity	NPC233396
0.8476	Intermediate Similarity	NPC154899
0.8469	Intermediate Similarity	NPC123273
0.8469	Intermediate Similarity	NPC318325
0.8469	Intermediate Similarity	NPC177420
0.8469	Intermediate Similarity	NPC242240
0.8469	Intermediate Similarity	NPC280347
0.8468	Intermediate Similarity	NPC150624
0.8468	Intermediate Similarity	NPC141090
0.8462	Intermediate Similarity	NPC168393
0.8455	Intermediate Similarity	NPC473137
0.844	Intermediate Similarity	NPC473521
0.8435	Intermediate Similarity	NPC120172
0.8435	Intermediate Similarity	NPC36016
0.8435	Intermediate Similarity	NPC100099
0.8431	Intermediate Similarity	NPC225464
0.8426	Intermediate Similarity	NPC224870
0.8421	Intermediate Similarity	NPC102639
0.8416	Intermediate Similarity	NPC32714
0.8411	Intermediate Similarity	NPC34864
0.8411	Intermediate Similarity	NPC262365
0.8411	Intermediate Similarity	NPC105727
0.8411	Intermediate Similarity	NPC95344
0.8411	Intermediate Similarity	NPC58427
0.8411	Intermediate Similarity	NPC114392
0.8407	Intermediate Similarity	NPC195262
0.8407	Intermediate Similarity	NPC184302
0.8407	Intermediate Similarity	NPC295259
0.8407	Intermediate Similarity	NPC188814
0.8396	Intermediate Similarity	NPC271274
0.8396	Intermediate Similarity	NPC92623
0.8396	Intermediate Similarity	NPC135464
0.8384	Intermediate Similarity	NPC55561
0.8381	Intermediate Similarity	NPC8931
0.8381	Intermediate Similarity	NPC261573
0.8381	Intermediate Similarity	NPC120693
0.8378	Intermediate Similarity	NPC53906
0.8367	Intermediate Similarity	NPC113460
0.8367	Intermediate Similarity	NPC25493
0.8364	Intermediate Similarity	NPC319803
0.8362	Intermediate Similarity	NPC53567
0.8362	Intermediate Similarity	NPC38761
0.8362	Intermediate Similarity	NPC474160
0.8362	Intermediate Similarity	NPC76465
0.8351	Intermediate Similarity	NPC155393
0.835	Intermediate Similarity	NPC128723
0.8348	Intermediate Similarity	NPC39029
0.8333	Intermediate Similarity	NPC472071
0.8333	Intermediate Similarity	NPC258979
0.8333	Intermediate Similarity	NPC265211
0.8333	Intermediate Similarity	NPC306045
0.8333	Intermediate Similarity	NPC93398
0.8333	Intermediate Similarity	NPC8283
0.8333	Intermediate Similarity	NPC159525
0.8319	Intermediate Similarity	NPC74821
0.8319	Intermediate Similarity	NPC206
0.8319	Intermediate Similarity	NPC9592
0.8319	Intermediate Similarity	NPC48781
0.8304	Intermediate Similarity	NPC203113
0.83	Intermediate Similarity	NPC204210
0.8291	Intermediate Similarity	NPC134195
0.8291	Intermediate Similarity	NPC197351
0.8291	Intermediate Similarity	NPC86502
0.8291	Intermediate Similarity	NPC246648
0.8291	Intermediate Similarity	NPC106914
0.8291	Intermediate Similarity	NPC97578
0.8288	Intermediate Similarity	NPC12656

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 NPC474839 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	310
0.1-0.2	1026
0.2-0.3	1324
0.3-0.4	2954
0.4-0.5	1863
0.5-0.6	1171
0.6-0.7	418
0.7-0.8	71
0.8-0.85	5
0.85-0.9	7
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.949	High Similarity	NPD940	Approved
0.949	High Similarity	NPD846	Approved
0.9	High Similarity	NPD1242	Phase 1
0.898	High Similarity	NPD2859	Approved
0.898	High Similarity	NPD2860	Approved
0.8878	High Similarity	NPD2933	Approved
0.8878	High Similarity	NPD2934	Approved
0.8713	High Similarity	NPD3020	Approved
0.8679	High Similarity	NPD4750	Phase 3
0.8319	Intermediate Similarity	NPD1548	Phase 1
0.819	Intermediate Similarity	NPD1610	Phase 2
0.8137	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.8058	Intermediate Similarity	NPD1809	Phase 2
0.8058	Intermediate Similarity	NPD844	Approved
0.8039	Intermediate Similarity	NPD845	Approved
0.8017	Intermediate Similarity	NPD4908	Phase 1
0.8	Intermediate Similarity	NPD3021	Approved
0.8	Intermediate Similarity	NPD3022	Approved
0.7959	Intermediate Similarity	NPD111	Approved
0.7886	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7835	Intermediate Similarity	NPD9089	Approved
0.781	Intermediate Similarity	NPD288	Approved
0.7757	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7757	Intermediate Similarity	NPD3028	Approved
0.7732	Intermediate Similarity	NPD9093	Approved
0.7731	Intermediate Similarity	NPD422	Phase 1
0.7724	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD3027	Phase 3
0.7661	Intermediate Similarity	NPD4625	Phase 3
0.7658	Intermediate Similarity	NPD2342	Discontinued
0.7652	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD7635	Approved
0.7603	Intermediate Similarity	NPD4749	Approved
0.757	Intermediate Similarity	NPD9273	Approved
0.7565	Intermediate Similarity	NPD2234	Approved
0.7565	Intermediate Similarity	NPD2229	Approved
0.7565	Intermediate Similarity	NPD2228	Approved
0.7563	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD5304	Approved
0.7542	Intermediate Similarity	NPD5303	Approved
0.748	Intermediate Similarity	NPD1240	Approved
0.748	Intermediate Similarity	NPD943	Approved
0.748	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD1613	Approved
0.746	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD4589	Approved
0.7402	Intermediate Similarity	NPD6407	Approved
0.7402	Intermediate Similarity	NPD6405	Approved
0.7391	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD9094	Approved
0.7368	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD1607	Approved
0.736	Intermediate Similarity	NPD2861	Phase 2
0.7344	Intermediate Similarity	NPD1555	Discontinued
0.7317	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD4659	Approved
0.7288	Intermediate Similarity	NPD6671	Approved
0.728	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD968	Approved
0.7252	Intermediate Similarity	NPD1510	Phase 2
0.725	Intermediate Similarity	NPD3091	Approved
0.7236	Intermediate Similarity	NPD2562	Approved
0.7236	Intermediate Similarity	NPD2561	Approved
0.7232	Intermediate Similarity	NPD9610	Approved
0.7232	Intermediate Similarity	NPD9608	Approved
0.7231	Intermediate Similarity	NPD2568	Approved
0.7222	Intermediate Similarity	NPD3018	Phase 2
0.7217	Intermediate Similarity	NPD1792	Phase 2
0.7217	Intermediate Similarity	NPD5451	Approved
0.72	Intermediate Similarity	NPD4103	Phase 2
0.72	Intermediate Similarity	NPD1129	Approved
0.72	Intermediate Similarity	NPD1133	Approved
0.72	Intermediate Similarity	NPD1164	Approved
0.72	Intermediate Similarity	NPD1135	Approved
0.72	Intermediate Similarity	NPD1131	Approved
0.72	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1134	Approved
0.719	Intermediate Similarity	NPD4093	Discontinued
0.7188	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD3553	Approved
0.7176	Intermediate Similarity	NPD3554	Approved
0.7176	Intermediate Similarity	NPD3555	Approved
0.7176	Intermediate Similarity	NPD3552	Approved
0.7154	Intermediate Similarity	NPD3092	Approved
0.7154	Intermediate Similarity	NPD1201	Approved
0.7143	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD2286	Discontinued
0.7131	Intermediate Similarity	NPD2932	Approved
0.7131	Intermediate Similarity	NPD4059	Approved
0.7131	Intermediate Similarity	NPD3019	Approved
0.713	Intermediate Similarity	NPD2684	Approved
0.7121	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD3750	Approved
0.7107	Intermediate Similarity	NPD7330	Discontinued
0.7105	Intermediate Similarity	NPD1445	Approved
0.7105	Intermediate Similarity	NPD1444	Approved
0.709	Intermediate Similarity	NPD1549	Phase 2
0.7083	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD7213	Phase 3
0.708	Intermediate Similarity	NPD7212	Phase 2
0.7063	Intermediate Similarity	NPD2797	Approved
0.7063	Intermediate Similarity	NPD3094	Phase 2
0.7043	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD6582	Phase 2
0.704	Intermediate Similarity	NPD2982	Phase 2
0.704	Intermediate Similarity	NPD6583	Phase 3
0.704	Intermediate Similarity	NPD2983	Phase 2
0.7034	Intermediate Similarity	NPD5535	Approved
0.7029	Intermediate Similarity	NPD7447	Phase 1
0.7029	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD856	Approved
0.7025	Intermediate Similarity	NPD16	Approved
0.701	Intermediate Similarity	NPD9087	Approved
0.6983	Remote Similarity	NPD74	Approved
0.6983	Remote Similarity	NPD9266	Approved
0.6975	Remote Similarity	NPD5283	Phase 1
0.6967	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD1759	Phase 1
0.696	Remote Similarity	NPD2981	Phase 2
0.6957	Remote Similarity	NPD7390	Discontinued
0.6949	Remote Similarity	NPD228	Approved
0.694	Remote Similarity	NPD6100	Approved
0.694	Remote Similarity	NPD5404	Approved
0.694	Remote Similarity	NPD5408	Approved
0.694	Remote Similarity	NPD5405	Approved
0.694	Remote Similarity	NPD5406	Approved
0.694	Remote Similarity	NPD6099	Approved
0.6935	Remote Similarity	NPD3847	Discontinued
0.6935	Remote Similarity	NPD3421	Phase 3
0.6929	Remote Similarity	NPD1470	Approved
0.6917	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.69	Remote Similarity	NPD9088	Approved
0.6897	Remote Similarity	NPD9264	Approved
0.6897	Remote Similarity	NPD9267	Approved
0.6897	Remote Similarity	NPD9263	Approved
0.6897	Remote Similarity	NPD290	Approved
0.6894	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD5124	Phase 1
0.6891	Remote Similarity	NPD9377	Approved
0.6891	Remote Similarity	NPD9379	Approved
0.6891	Remote Similarity	NPD7843	Approved
0.6885	Remote Similarity	NPD318	Approved
0.6885	Remote Similarity	NPD317	Approved
0.6885	Remote Similarity	NPD1758	Phase 1
0.688	Remote Similarity	NPD1091	Approved
0.6875	Remote Similarity	NPD6584	Phase 3
0.6864	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.686	Remote Similarity	NPD255	Approved
0.686	Remote Similarity	NPD256	Approved
0.6855	Remote Similarity	NPD4626	Approved
0.6855	Remote Similarity	NPD2668	Approved
0.6855	Remote Similarity	NPD5846	Approved
0.6855	Remote Similarity	NPD6516	Phase 2
0.6855	Remote Similarity	NPD3095	Discontinued
0.6855	Remote Similarity	NPD1751	Approved
0.6855	Remote Similarity	NPD2667	Approved
0.685	Remote Similarity	NPD3225	Approved
0.685	Remote Similarity	NPD5310	Approved
0.685	Remote Similarity	NPD5311	Approved
0.6818	Remote Similarity	NPD2238	Phase 2
0.6818	Remote Similarity	NPD468	Phase 1
0.6818	Remote Similarity	NPD4060	Phase 1
0.6815	Remote Similarity	NPD2935	Discontinued
0.6815	Remote Similarity	NPD2796	Approved
0.6803	Remote Similarity	NPD9493	Approved
0.68	Remote Similarity	NPD1983	Approved
0.68	Remote Similarity	NPD1981	Approved
0.68	Remote Similarity	NPD3143	Discontinued
0.68	Remote Similarity	NPD1980	Approved
0.68	Remote Similarity	NPD9294	Approved
0.6797	Remote Similarity	NPD3053	Approved
0.6797	Remote Similarity	NPD3055	Approved
0.6794	Remote Similarity	NPD3268	Approved
0.6794	Remote Similarity	NPD3764	Approved
0.6783	Remote Similarity	NPD4380	Phase 2
0.6777	Remote Similarity	NPD497	Approved
0.6765	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.675	Remote Similarity	NPD821	Approved
0.6746	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD1535	Discovery
0.6746	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD599	Approved
0.6744	Remote Similarity	NPD7451	Discontinued
0.6744	Remote Similarity	NPD859	Approved
0.6744	Remote Similarity	NPD602	Approved
0.6744	Remote Similarity	NPD858	Approved
0.6741	Remote Similarity	NPD3748	Approved
0.6741	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD3400	Discontinued
0.6739	Remote Similarity	NPD3892	Phase 2
0.6721	Remote Similarity	NPD6387	Discontinued
0.6721	Remote Similarity	NPD7157	Approved
0.6721	Remote Similarity	NPD709	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