NPASS Compound

Structure

NPC121866 OpenBabel07101718322D 29 31 0 0 0 0 0 0 0 0999 V2000 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 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 0.8660 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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -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 1.7321 -0.0000 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 7.7942 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 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 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 29 1 0 0 0 0 2 3 1 0 0 0 0 2 17 2 0 0 0 0 3 18 2 0 0 0 0 4 12 1 0 0 0 0 4 13 1 0 0 0 0 5 14 1 0 0 0 0 5 15 1 0 0 0 0 6 12 2 0 0 0 0 6 17 1 0 0 0 0 7 13 2 0 0 0 0 7 20 1 0 0 0 0 8 14 1 0 0 0 0 8 19 2 0 0 0 0 9 15 2 0 0 0 0 9 22 1 0 0 0 0 10 16 1 0 0 0 0 10 21 2 0 0 0 0 11 16 1 0 0 0 0 11 29 1 0 0 0 0 12 18 1 0 0 0 0 13 19 1 0 0 0 0 14 20 2 0 0 0 0 15 21 1 0 0 0 0 16 22 2 0 0 0 0 17 23 1 0 0 0 0 18 24 1 0 0 0 0 19 25 1 0 0 0 0 20 26 1 0 0 0 0 21 27 1 0 0 0 0 22 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	398.14
Volume:	401.202
LogP:	2.536
LogD:	2.769
LogS:	-2.031
# Rotatable Bonds:	6
TPSA:	130.61
# H-Bond Aceptor:	7
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.351
Synthetic Accessibility Score:	2.814
Fsp3:	0.182
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.747
MDCK Permeability:	4.615309080691077e-06
Pgp-inhibitor:	0.115
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.815
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.017
Plasma Protein Binding (PPB):	92.4093246459961%
Volume Distribution (VD):	0.611
Pgp-substrate:	4.047421932220459%

ADMET: Metabolism

CYP1A2-inhibitor:	0.219
CYP1A2-substrate:	0.786
CYP2C19-inhibitor:	0.112
CYP2C19-substrate:	0.045
CYP2C9-inhibitor:	0.566
CYP2C9-substrate:	0.436
CYP2D6-inhibitor:	0.111
CYP2D6-substrate:	0.726
CYP3A4-inhibitor:	0.121
CYP3A4-substrate:	0.243

ADMET: Excretion

Clearance (CL):	13.24
Half-life (T1/2):	0.952

ADMET: Toxicity

hERG Blockers:	0.342
Human Hepatotoxicity (H-HT):	0.099
Drug-inuced Liver Injury (DILI):	0.784
AMES Toxicity:	0.302
Rat Oral Acute Toxicity:	0.053
Maximum Recommended Daily Dose:	0.468
Skin Sensitization:	0.97
Carcinogencity:	0.053
Eye Corrosion:	0.003
Eye Irritation:	0.949
Respiratory Toxicity:	0.026

Download Data

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

Natural Product: NPC121866

Natural Product ID:	NPC121866
*Common Name:**	2-[2,5-Dihydroxy-4-(Methoxymethyl)Benzyl]-5-(2,5-Dihydroxybenzyl)Benzene-1,4-Diol
IUPAC Name:	2-[[2,5-dihydroxy-4-(methoxymethyl)phenyl]methyl]-5-[(2,5-dihydroxyphenyl)methyl]benzene-1,4-diol
Synonyms:
Standard InCHIKey:	WMFZCOHRHOJWON-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C22H22O7/c1-29-11-16-10-21(27)15(9-22(16)28)5-14-8-19(25)13(7-20(14)26)4-12-6-17(23)2-3-18(12)24/h2-3,6-10,23-28H,4-5,11H2,1H3
SMILES:	COCc1cc(c(Cc2cc(c(Cc3cc(ccc3O)O)cc2O)O)cc1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL256568
PubChem CID:	24770577
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000369] Diphenylmethanes

*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
NPO28718	Penicillium terrestre	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18163588]
NPO28718	Penicillium terrestre	Species	Aspergillaceae	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	5

Activity Type	# Activity
Cell Line	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	33300.0	nM	PMID[536434]
NPT112	Cell Line	MOLT-4	Homo sapiens	IC50	=	5500.0	nM	PMID[536434]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	23500.0	nM	PMID[536434]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	=	57000.0	nM	PMID[536434]
NPT35	Others	n.a.		IC50	=	2600.0	nM	PMID[536434]

☑ 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 NPC121866 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	306
0.1-0.2	1548
0.2-0.3	4133
0.3-0.4	12818
0.4-0.5	6051
0.5-0.6	6031
0.6-0.7	9119
0.7-0.8	2399
0.8-0.85	276
0.85-0.9	14
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.964	High Similarity	NPC232165
0.8839	High Similarity	NPC169450
0.8833	High Similarity	NPC77789
0.8833	High Similarity	NPC18128
0.8783	High Similarity	NPC261343
0.8729	High Similarity	NPC190514
0.8696	High Similarity	NPC228452
0.8655	High Similarity	NPC184302
0.8651	High Similarity	NPC472590
0.8649	High Similarity	NPC130817
0.8618	High Similarity	NPC33654
0.8596	High Similarity	NPC33728
0.8596	High Similarity	NPC19808
0.8583	High Similarity	NPC218884
0.8527	High Similarity	NPC283009
0.8527	High Similarity	NPC261873
0.8527	High Similarity	NPC111655
0.8509	High Similarity	NPC174981
0.8487	Intermediate Similarity	NPC69261
0.8487	Intermediate Similarity	NPC320864
0.8487	Intermediate Similarity	NPC33270
0.8475	Intermediate Similarity	NPC808
0.8475	Intermediate Similarity	NPC246760
0.8475	Intermediate Similarity	NPC84999
0.8468	Intermediate Similarity	NPC113495
0.8462	Intermediate Similarity	NPC114155
0.8462	Intermediate Similarity	NPC300846
0.8462	Intermediate Similarity	NPC476639
0.8455	Intermediate Similarity	NPC261992
0.845	Intermediate Similarity	NPC103967
0.8448	Intermediate Similarity	NPC54373
0.8448	Intermediate Similarity	NPC224527
0.8417	Intermediate Similarity	NPC9592
0.8417	Intermediate Similarity	NPC48781
0.8403	Intermediate Similarity	NPC150624
0.8397	Intermediate Similarity	NPC6262
0.8397	Intermediate Similarity	NPC73535
0.8397	Intermediate Similarity	NPC90615
0.8397	Intermediate Similarity	NPC25111
0.8397	Intermediate Similarity	NPC272157
0.8397	Intermediate Similarity	NPC201145
0.839	Intermediate Similarity	NPC249270
0.8376	Intermediate Similarity	NPC302371
0.8376	Intermediate Similarity	NPC166995
0.8374	Intermediate Similarity	NPC188997
0.8361	Intermediate Similarity	NPC100108
0.8361	Intermediate Similarity	NPC277798
0.8361	Intermediate Similarity	NPC129176
0.8359	Intermediate Similarity	NPC471517
0.8333	Intermediate Similarity	NPC257947
0.8333	Intermediate Similarity	NPC127894
0.8333	Intermediate Similarity	NPC473221
0.8333	Intermediate Similarity	NPC219070
0.8333	Intermediate Similarity	NPC470759
0.8333	Intermediate Similarity	NPC66331
0.8333	Intermediate Similarity	NPC15860
0.8319	Intermediate Similarity	NPC301321
0.8319	Intermediate Similarity	NPC53906
0.8305	Intermediate Similarity	NPC23804
0.8305	Intermediate Similarity	NPC117846
0.8304	Intermediate Similarity	NPC477685
0.8293	Intermediate Similarity	NPC476633
0.8291	Intermediate Similarity	NPC77772
0.8279	Intermediate Similarity	NPC69006
0.8276	Intermediate Similarity	NPC473524
0.8271	Intermediate Similarity	NPC295719
0.8271	Intermediate Similarity	NPC165026
0.8271	Intermediate Similarity	NPC73505
0.8271	Intermediate Similarity	NPC34431
0.8268	Intermediate Similarity	NPC38017
0.8268	Intermediate Similarity	NPC215300
0.8268	Intermediate Similarity	NPC266691
0.8261	Intermediate Similarity	NPC204901
0.8261	Intermediate Similarity	NPC232523
0.8261	Intermediate Similarity	NPC158253
0.8261	Intermediate Similarity	NPC233320
0.8261	Intermediate Similarity	NPC66834
0.8261	Intermediate Similarity	NPC474352
0.8254	Intermediate Similarity	NPC82299
0.8254	Intermediate Similarity	NPC170485
0.825	Intermediate Similarity	NPC114064
0.825	Intermediate Similarity	NPC141001
0.8246	Intermediate Similarity	NPC37802
0.8246	Intermediate Similarity	NPC47284
0.8235	Intermediate Similarity	NPC276737
0.8235	Intermediate Similarity	NPC471534
0.8235	Intermediate Similarity	NPC22610
0.8231	Intermediate Similarity	NPC469610
0.8231	Intermediate Similarity	NPC269528
0.823	Intermediate Similarity	NPC235762
0.823	Intermediate Similarity	NPC471228
0.822	Intermediate Similarity	NPC290353
0.822	Intermediate Similarity	NPC43525
0.822	Intermediate Similarity	NPC153795
0.822	Intermediate Similarity	NPC42911
0.8217	Intermediate Similarity	NPC8899
0.8217	Intermediate Similarity	NPC237424
0.8217	Intermediate Similarity	NPC238168
0.8217	Intermediate Similarity	NPC282508
0.8214	Intermediate Similarity	NPC130103
0.8214	Intermediate Similarity	NPC174911
0.8214	Intermediate Similarity	NPC129373
0.8214	Intermediate Similarity	NPC248396
0.8214	Intermediate Similarity	NPC48730
0.8203	Intermediate Similarity	NPC471518
0.8203	Intermediate Similarity	NPC471519
0.8198	Intermediate Similarity	NPC152097
0.8197	Intermediate Similarity	NPC151197
0.819	Intermediate Similarity	NPC241549
0.8189	Intermediate Similarity	NPC53781
0.8189	Intermediate Similarity	NPC236760
0.8182	Intermediate Similarity	NPC472647
0.8182	Intermediate Similarity	NPC206525
0.8182	Intermediate Similarity	NPC133463
0.8182	Intermediate Similarity	NPC170328
0.8182	Intermediate Similarity	NPC472648
0.8182	Intermediate Similarity	NPC476698
0.8182	Intermediate Similarity	NPC470760
0.8182	Intermediate Similarity	NPC244816
0.8182	Intermediate Similarity	NPC141717
0.8182	Intermediate Similarity	NPC50521
0.8182	Intermediate Similarity	NPC474933
0.8182	Intermediate Similarity	NPC205442
0.8182	Intermediate Similarity	NPC221549
0.8182	Intermediate Similarity	NPC472649
0.8182	Intermediate Similarity	NPC476266
0.8182	Intermediate Similarity	NPC191462
0.8175	Intermediate Similarity	NPC476254
0.8175	Intermediate Similarity	NPC105718
0.8175	Intermediate Similarity	NPC105031
0.8175	Intermediate Similarity	NPC131397
0.8175	Intermediate Similarity	NPC278955
0.8174	Intermediate Similarity	NPC470700
0.8174	Intermediate Similarity	NPC109691
0.8174	Intermediate Similarity	NPC302681
0.8174	Intermediate Similarity	NPC99836
0.8174	Intermediate Similarity	NPC53740
0.8174	Intermediate Similarity	NPC201662
0.8174	Intermediate Similarity	NPC12640
0.8174	Intermediate Similarity	NPC39664
0.8174	Intermediate Similarity	NPC39097
0.8174	Intermediate Similarity	NPC118286
0.816	Intermediate Similarity	NPC474160
0.8158	Intermediate Similarity	NPC475225
0.8158	Intermediate Similarity	NPC227458
0.8158	Intermediate Similarity	NPC323810
0.8158	Intermediate Similarity	NPC241891
0.8158	Intermediate Similarity	NPC244513
0.8158	Intermediate Similarity	NPC102216
0.8158	Intermediate Similarity	NPC218879
0.8154	Intermediate Similarity	NPC469611
0.8151	Intermediate Similarity	NPC319803
0.8148	Intermediate Similarity	NPC175838
0.8142	Intermediate Similarity	NPC80800
0.8142	Intermediate Similarity	NPC12221
0.814	Intermediate Similarity	NPC299221
0.814	Intermediate Similarity	NPC234488
0.814	Intermediate Similarity	NPC311680
0.814	Intermediate Similarity	NPC254000
0.814	Intermediate Similarity	NPC224157
0.814	Intermediate Similarity	NPC51840
0.814	Intermediate Similarity	NPC192687
0.8136	Intermediate Similarity	NPC275627
0.8136	Intermediate Similarity	NPC4493
0.8136	Intermediate Similarity	NPC266937
0.8136	Intermediate Similarity	NPC165770
0.8136	Intermediate Similarity	NPC225679
0.8136	Intermediate Similarity	NPC476632
0.8136	Intermediate Similarity	NPC470770
0.813	Intermediate Similarity	NPC223451
0.813	Intermediate Similarity	NPC260832
0.813	Intermediate Similarity	NPC103916
0.813	Intermediate Similarity	NPC328485
0.813	Intermediate Similarity	NPC135467
0.8125	Intermediate Similarity	NPC148366
0.8125	Intermediate Similarity	NPC260775
0.8125	Intermediate Similarity	NPC311293
0.812	Intermediate Similarity	NPC71465
0.812	Intermediate Similarity	NPC472646
0.812	Intermediate Similarity	NPC186385
0.812	Intermediate Similarity	NPC306045
0.812	Intermediate Similarity	NPC299568
0.812	Intermediate Similarity	NPC266006
0.812	Intermediate Similarity	NPC265211
0.8115	Intermediate Similarity	NPC283616
0.8115	Intermediate Similarity	NPC63010
0.8115	Intermediate Similarity	NPC144343
0.811	Intermediate Similarity	NPC50315
0.811	Intermediate Similarity	NPC283049
0.811	Intermediate Similarity	NPC230479
0.811	Intermediate Similarity	NPC26879
0.8106	Intermediate Similarity	NPC258780
0.8106	Intermediate Similarity	NPC201357
0.8106	Intermediate Similarity	NPC37410
0.8106	Intermediate Similarity	NPC195022
0.8106	Intermediate Similarity	NPC281521
0.8106	Intermediate Similarity	NPC255147
0.8103	Intermediate Similarity	NPC54844
0.8103	Intermediate Similarity	NPC320439
0.8099	Intermediate Similarity	NPC473556

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 NPC121866 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	278
0.1-0.2	955
0.2-0.3	1377
0.3-0.4	2811
0.4-0.5	1936
0.5-0.6	1128
0.6-0.7	594
0.7-0.8	68
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8125	Intermediate Similarity	NPD4908	Phase 1
0.812	Intermediate Similarity	NPD4750	Phase 3
0.8067	Intermediate Similarity	NPD7635	Approved
0.8047	Intermediate Similarity	NPD2861	Phase 2
0.8018	Intermediate Similarity	NPD844	Approved
0.8017	Intermediate Similarity	NPD6671	Approved
0.8	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD2342	Discontinued
0.7923	Intermediate Similarity	NPD4625	Phase 3
0.7895	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD4749	Approved
0.7788	Intermediate Similarity	NPD288	Approved
0.7786	Intermediate Similarity	NPD3027	Phase 3
0.7727	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD1610	Phase 2
0.7712	Intermediate Similarity	NPD968	Approved
0.7699	Intermediate Similarity	NPD2859	Approved
0.7699	Intermediate Similarity	NPD2860	Approved
0.7692	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD1548	Phase 1
0.7672	Intermediate Similarity	NPD940	Approved
0.7672	Intermediate Similarity	NPD846	Approved
0.7652	Intermediate Similarity	NPD3020	Approved
0.7612	Intermediate Similarity	NPD1613	Approved
0.7612	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD2934	Approved
0.7611	Intermediate Similarity	NPD2933	Approved
0.7597	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD1242	Phase 1
0.7576	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD6584	Phase 3
0.7538	Intermediate Similarity	NPD6696	Suspended
0.7521	Intermediate Similarity	NPD3022	Approved
0.7521	Intermediate Similarity	NPD3021	Approved
0.75	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3496	Discontinued
0.7481	Intermediate Similarity	NPD3094	Phase 2
0.7464	Intermediate Similarity	NPD2935	Discontinued
0.7429	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7402	Intermediate Similarity	NPD3091	Approved
0.7377	Intermediate Similarity	NPD5451	Approved
0.7372	Intermediate Similarity	NPD4097	Suspended
0.736	Intermediate Similarity	NPD497	Approved
0.7328	Intermediate Similarity	NPD6583	Phase 3
0.7328	Intermediate Similarity	NPD6582	Phase 2
0.7308	Intermediate Similarity	NPD3092	Approved
0.7308	Intermediate Similarity	NPD1611	Approved
0.7287	Intermediate Similarity	NPD4626	Approved
0.728	Intermediate Similarity	NPD1398	Phase 1
0.728	Intermediate Similarity	NPD5283	Phase 1
0.728	Intermediate Similarity	NPD496	Approved
0.728	Intermediate Similarity	NPD498	Approved
0.728	Intermediate Similarity	NPD495	Approved
0.7252	Intermediate Similarity	NPD2233	Approved
0.7252	Intermediate Similarity	NPD2230	Approved
0.7252	Intermediate Similarity	NPD2232	Approved
0.7244	Intermediate Similarity	NPD7340	Approved
0.7226	Intermediate Similarity	NPD2238	Phase 2
0.7226	Intermediate Similarity	NPD4060	Phase 1
0.7218	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD845	Approved
0.7214	Intermediate Similarity	NPD6099	Approved
0.7214	Intermediate Similarity	NPD6100	Approved
0.7194	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD596	Approved
0.7185	Intermediate Similarity	NPD600	Approved
0.7176	Intermediate Similarity	NPD1091	Approved
0.7176	Intermediate Similarity	NPD1201	Approved
0.7172	Intermediate Similarity	NPD7447	Phase 1
0.7163	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD5125	Phase 3
0.7154	Intermediate Similarity	NPD1778	Approved
0.7154	Intermediate Similarity	NPD2286	Discontinued
0.7154	Intermediate Similarity	NPD3095	Discontinued
0.7154	Intermediate Similarity	NPD5126	Approved
0.7153	Intermediate Similarity	NPD840	Approved
0.7153	Intermediate Similarity	NPD839	Approved
0.7153	Intermediate Similarity	NPD6233	Phase 2
0.712	Intermediate Similarity	NPD228	Approved
0.7111	Intermediate Similarity	NPD3018	Phase 2
0.7103	Intermediate Similarity	NPD7041	Phase 2
0.7103	Intermediate Similarity	NPD7213	Phase 3
0.7103	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD7212	Phase 2
0.7092	Intermediate Similarity	NPD5405	Approved
0.7092	Intermediate Similarity	NPD5404	Approved
0.7092	Intermediate Similarity	NPD5408	Approved
0.7092	Intermediate Similarity	NPD5406	Approved
0.709	Intermediate Similarity	NPD1470	Approved
0.709	Intermediate Similarity	NPD2797	Approved
0.708	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD6798	Discontinued
0.7077	Intermediate Similarity	NPD5691	Approved
0.7073	Intermediate Similarity	NPD290	Approved
0.7063	Intermediate Similarity	NPD5177	Phase 3
0.7063	Intermediate Similarity	NPD5535	Approved
0.7042	Intermediate Similarity	NPD6800	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD7266	Discontinued
0.7037	Intermediate Similarity	NPD4624	Approved
0.7031	Intermediate Similarity	NPD709	Approved
0.7029	Intermediate Similarity	NPD6407	Approved
0.7029	Intermediate Similarity	NPD7477	Discontinued
0.7029	Intermediate Similarity	NPD6405	Approved
0.7023	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD6516	Phase 2
0.7023	Intermediate Similarity	NPD5846	Approved
0.7023	Intermediate Similarity	NPD3019	Approved
0.7023	Intermediate Similarity	NPD4059	Approved
0.7021	Intermediate Similarity	NPD7033	Discontinued
0.7021	Intermediate Similarity	NPD1510	Phase 2
0.7016	Intermediate Similarity	NPD2684	Approved
0.7014	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD6746	Phase 2
0.7008	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD6090	Discontinued
0.7	Intermediate Similarity	NPD7741	Discontinued
0.7	Intermediate Similarity	NPD1607	Approved
0.6992	Remote Similarity	NPD2231	Phase 2
0.6992	Remote Similarity	NPD2235	Phase 2
0.6986	Remote Similarity	NPD7390	Discontinued
0.6985	Remote Similarity	NPD5736	Approved
0.698	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD3620	Phase 2
0.6978	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.696	Remote Similarity	NPD1792	Phase 2
0.6957	Remote Similarity	NPD3764	Approved
0.6957	Remote Similarity	NPD3268	Approved
0.695	Remote Similarity	NPD4536	Approved
0.695	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.695	Remote Similarity	NPD4538	Approved
0.6949	Remote Similarity	NPD1809	Phase 2
0.6947	Remote Similarity	NPD1651	Approved
0.6947	Remote Similarity	NPD4093	Discontinued
0.6944	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.694	Remote Similarity	NPD2983	Phase 2
0.694	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.694	Remote Similarity	NPD2982	Phase 2
0.694	Remote Similarity	NPD5327	Phase 3
0.6939	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD5735	Approved
0.6929	Remote Similarity	NPD7843	Approved
0.6923	Remote Similarity	NPD6232	Discontinued
0.6923	Remote Similarity	NPD5762	Approved
0.6923	Remote Similarity	NPD5763	Approved
0.6918	Remote Similarity	NPD5844	Phase 1
0.6917	Remote Similarity	NPD422	Phase 1
0.6917	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD5929	Approved
0.6908	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD2801	Approved
0.6901	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD4308	Phase 3
0.6899	Remote Similarity	NPD2557	Approved
0.6899	Remote Similarity	NPD7157	Approved
0.6899	Remote Similarity	NPD4198	Discontinued
0.6897	Remote Similarity	NPD3892	Phase 2
0.6894	Remote Similarity	NPD2932	Approved
0.6889	Remote Similarity	NPD1283	Approved
0.6889	Remote Similarity	NPD3225	Approved
0.6889	Remote Similarity	NPD8651	Approved
0.6884	Remote Similarity	NPD7095	Approved
0.6879	Remote Similarity	NPD2568	Approved
0.6875	Remote Similarity	NPD7037	Approved
0.687	Remote Similarity	NPD9295	Approved
0.687	Remote Similarity	NPD6580	Approved
0.687	Remote Similarity	NPD6581	Approved
0.6866	Remote Similarity	NPD1608	Approved
0.6866	Remote Similarity	NPD2981	Phase 2
0.6861	Remote Similarity	NPD2237	Approved
0.686	Remote Similarity	NPD3028	Approved
0.6859	Remote Similarity	NPD6959	Discontinued
0.6857	Remote Similarity	NPD4140	Approved
0.6857	Remote Similarity	NPD1240	Approved
0.6855	Remote Similarity	NPD1444	Approved
0.6855	Remote Similarity	NPD1445	Approved
0.6853	Remote Similarity	NPD6032	Approved
0.6853	Remote Similarity	NPD1551	Phase 2
0.685	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD6190	Approved
0.6846	Remote Similarity	NPD9493	Approved
0.6842	Remote Similarity	NPD3847	Discontinued
0.6842	Remote Similarity	NPD1934	Approved
0.6842	Remote Similarity	NPD37	Approved
0.6835	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD6674	Discontinued
0.6824	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5585	Approved
0.6818	Remote Similarity	NPD3444	Approved
0.6818	Remote Similarity	NPD3445	Approved
0.6818	Remote Similarity	NPD3443	Approved
0.6818	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD4659	Approved
0.6814	Remote Similarity	NPD111	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