NPASS Compound

Structure

NPC289244 OpenBabel07101719152D 41 43 0 0 0 0 0 0 0 0999 V2000 9.9899 7.0220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1472 -8.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9953 6.9175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1472 -7.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5886 6.0039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 -7.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5941 5.8994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 -6.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1873 4.9858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -5.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1928 4.8813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -4.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7861 3.9678 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -4.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7916 3.8632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3848 2.9497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3903 2.8452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9836 1.9316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9890 1.8271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 2.6361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5823 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 2.5316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8080 3.5497 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1701 0.1045 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1810 3.3406 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 1.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 5 1 0 0 0 0 3 40 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 13 15 1 0 0 0 0 14 16 1 0 0 0 0 15 17 1 0 0 0 0 16 18 1 0 0 0 0 17 19 1 0 0 0 0 18 20 1 0 0 0 0 19 21 1 0 0 0 0 20 22 1 0 0 0 0 21 23 1 0 0 0 0 22 25 1 0 0 0 0 23 26 1 0 0 0 0 24 27 1 0 0 0 0 24 28 2 0 0 0 0 25 31 2 0 0 0 0 25 32 1 0 0 0 0 26 30 2 0 0 0 0 26 34 1 0 0 0 0 27 29 1 0 0 0 0 27 34 2 0 0 0 0 28 30 1 0 0 0 0 28 40 1 0 0 0 0 29 33 1 0 0 0 0 29 35 2 0 0 0 0 30 36 1 0 0 0 0 31 33 1 0 0 0 0 31 37 1 0 0 0 0 32 35 1 0 0 0 0 32 38 2 0 0 0 0 33 39 2 0 0 0 0 34 41 1 0 0 0 0 35 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	568.38
Volume:	622.533
LogP:	10.963
LogD:	5.593
LogS:	-3.222
# Rotatable Bonds:	20
TPSA:	103.29
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.061
Synthetic Accessibility Score:	3.175
Fsp3:	0.6
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.418
MDCK Permeability:	1.1566548892005812e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.016
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.996
30% Bioavailability (F30%):	0.272

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.017
Plasma Protein Binding (PPB):	104.60321044921875%
Volume Distribution (VD):	6.387
Pgp-substrate:	2.121145725250244%

ADMET: Metabolism

CYP1A2-inhibitor:	0.145
CYP1A2-substrate:	0.188
CYP2C19-inhibitor:	0.546
CYP2C19-substrate:	0.069
CYP2C9-inhibitor:	0.11
CYP2C9-substrate:	0.967
CYP2D6-inhibitor:	0.068
CYP2D6-substrate:	0.769
CYP3A4-inhibitor:	0.062
CYP3A4-substrate:	0.012

ADMET: Excretion

Clearance (CL):	3.841
Half-life (T1/2):	0.131

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.144
Drug-inuced Liver Injury (DILI):	0.972
AMES Toxicity:	0.278
Rat Oral Acute Toxicity:	0.156
Maximum Recommended Daily Dose:	0.612
Skin Sensitization:	0.965
Carcinogencity:	0.035
Eye Corrosion:	0.003
Eye Irritation:	0.874
Respiratory Toxicity:	0.566

Download Data

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

Natural Product: NPC289244

Natural Product ID:	NPC289244
*Common Name:**	2,7-Dihydroxy-8-Methoxy-3,6-Diundecyldibenzofuran-1,4-Dione
IUPAC Name:	2,7-dihydroxy-8-methoxy-3,6-di(undecyl)dibenzofuran-1,4-dione
Synonyms:
Standard InCHIKey:	GMGRAGPXURLASU-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C35H52O6/c1-4-6-8-10-12-14-16-18-20-22-25-31(37)33(39)29-27-24-28(40-3)30(36)26(34(27)41-35(29)32(25)38)23-21-19-17-15-13-11-9-7-5-2/h24,36-37H,4-23H2,1-3H3
SMILES:	CCCCCCCCCCCC1=C(O)C(=O)c2c(C1=O)oc1c2cc(c(c1CCCCCCCCCCC)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL473660
PubChem CID:	11353603
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans

*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
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	twig	n.a.	DOI[10.1021/np50063a031]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1021/np50063a031]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15165134]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	stem	n.a.	PMID[16254827]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	twig	n.a.	PMID[16254827]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22316191]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2778454]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[514881]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[514881]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[514881]
NPT466	Cell Line	U-937	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[514881]

☑ 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 NPC289244 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	460
0.1-0.2	1906
0.2-0.3	4872
0.3-0.4	11142
0.4-0.5	6842
0.5-0.6	4083
0.6-0.7	5311
0.7-0.8	5433
0.8-0.85	1637
0.85-0.9	912
0.9-0.95	96
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9695	High Similarity	NPC30550
0.9693	High Similarity	NPC28042
0.9217	High Similarity	NPC95715
0.9212	High Similarity	NPC45449
0.9176	High Similarity	NPC221820
0.9176	High Similarity	NPC77179
0.9176	High Similarity	NPC23553
0.9162	High Similarity	NPC202470
0.9128	High Similarity	NPC8927
0.9128	High Similarity	NPC228209
0.9118	High Similarity	NPC49667
0.9118	High Similarity	NPC8127
0.9096	High Similarity	NPC36320
0.9091	High Similarity	NPC238995
0.9036	High Similarity	NPC39305
0.9036	High Similarity	NPC1706
0.9036	High Similarity	NPC59295
0.9036	High Similarity	NPC263092
0.9036	High Similarity	NPC1755
0.9017	High Similarity	NPC246153
0.9017	High Similarity	NPC471842
0.9006	High Similarity	NPC471841
0.9	High Similarity	NPC82217
0.9	High Similarity	NPC65885
0.9	High Similarity	NPC277510
0.9	High Similarity	NPC216842
0.9	High Similarity	NPC476640
0.8988	High Similarity	NPC247973
0.8982	High Similarity	NPC39306
0.8977	High Similarity	NPC295436
0.8976	High Similarity	NPC84515
0.8976	High Similarity	NPC312056
0.8976	High Similarity	NPC272722
0.8971	High Similarity	NPC240808
0.8947	High Similarity	NPC287243
0.8947	High Similarity	NPC245975
0.8941	High Similarity	NPC230619
0.8941	High Similarity	NPC54098
0.8935	High Similarity	NPC247136
0.8922	High Similarity	NPC133065
0.8916	High Similarity	NPC188486
0.8909	High Similarity	NPC195832
0.8909	High Similarity	NPC196879
0.8908	High Similarity	NPC240508
0.8902	High Similarity	NPC476273
0.8895	High Similarity	NPC24258
0.8889	High Similarity	NPC473834
0.8889	High Similarity	NPC117450
0.8882	High Similarity	NPC476641
0.8876	High Similarity	NPC50394
0.8869	High Similarity	NPC291110
0.8869	High Similarity	NPC37183
0.8855	High Similarity	NPC246478
0.8841	High Similarity	NPC234485
0.8837	High Similarity	NPC227906
0.8817	High Similarity	NPC277480
0.8802	High Similarity	NPC258331
0.8795	High Similarity	NPC16935
0.8788	High Similarity	NPC45131
0.878	High Similarity	NPC127172
0.8779	High Similarity	NPC37606
0.8779	High Similarity	NPC261471
0.8779	High Similarity	NPC233956
0.8779	High Similarity	NPC310794
0.8772	High Similarity	NPC78830
0.8772	High Similarity	NPC218533
0.8772	High Similarity	NPC281835
0.8765	High Similarity	NPC470704
0.8765	High Similarity	NPC186392
0.875	High Similarity	NPC71260
0.875	High Similarity	NPC81679
0.8736	High Similarity	NPC246877
0.8735	High Similarity	NPC262286
0.8735	High Similarity	NPC36852
0.8721	High Similarity	NPC174700
0.8721	High Similarity	NPC307286
0.8715	High Similarity	NPC60848
0.8706	High Similarity	NPC470462
0.8706	High Similarity	NPC62444
0.8698	High Similarity	NPC476822
0.8698	High Similarity	NPC236132
0.8698	High Similarity	NPC470459
0.8698	High Similarity	NPC41301
0.8698	High Similarity	NPC270837
0.869	High Similarity	NPC264293
0.869	High Similarity	NPC278052
0.869	High Similarity	NPC40491
0.8683	High Similarity	NPC193842
0.8678	High Similarity	NPC164384
0.8678	High Similarity	NPC107244
0.8675	High Similarity	NPC138243
0.8675	High Similarity	NPC472461
0.8675	High Similarity	NPC268161
0.8667	High Similarity	NPC189130
0.8663	High Similarity	NPC131866
0.8655	High Similarity	NPC126204
0.8655	High Similarity	NPC470456
0.8655	High Similarity	NPC478059
0.8655	High Similarity	NPC158761
0.8655	High Similarity	NPC470377
0.8655	High Similarity	NPC241820
0.8655	High Similarity	NPC478060
0.8655	High Similarity	NPC471975
0.8655	High Similarity	NPC470374
0.8655	High Similarity	NPC86477
0.8647	High Similarity	NPC326520
0.8647	High Similarity	NPC470457
0.8644	High Similarity	NPC476170
0.8639	High Similarity	NPC294965
0.8636	High Similarity	NPC47883
0.8636	High Similarity	NPC475996
0.8631	High Similarity	NPC14353
0.8631	High Similarity	NPC56085
0.8631	High Similarity	NPC320359
0.8631	High Similarity	NPC228785
0.8631	High Similarity	NPC476980
0.8629	High Similarity	NPC98546
0.8629	High Similarity	NPC297807
0.8629	High Similarity	NPC5671
0.8623	High Similarity	NPC78225
0.8623	High Similarity	NPC7973
0.8623	High Similarity	NPC203891
0.8623	High Similarity	NPC101830
0.8623	High Similarity	NPC472438
0.8623	High Similarity	NPC78302
0.8623	High Similarity	NPC29841
0.8623	High Similarity	NPC110070
0.8623	High Similarity	NPC235215
0.8621	High Similarity	NPC224165
0.8621	High Similarity	NPC53917
0.8614	High Similarity	NPC268008
0.8614	High Similarity	NPC113906
0.8614	High Similarity	NPC472048
0.8613	High Similarity	NPC28589
0.8613	High Similarity	NPC248593
0.8606	High Similarity	NPC125300
0.8606	High Similarity	NPC304954
0.8605	High Similarity	NPC211309
0.8605	High Similarity	NPC242395
0.8605	High Similarity	NPC152477
0.8598	High Similarity	NPC103509
0.8596	High Similarity	NPC304322
0.8596	High Similarity	NPC170245
0.8596	High Similarity	NPC476255
0.8588	High Similarity	NPC7483
0.8588	High Similarity	NPC473313
0.8588	High Similarity	NPC472278
0.8588	High Similarity	NPC472281
0.8588	High Similarity	NPC18100
0.8588	High Similarity	NPC472582
0.8588	High Similarity	NPC205265
0.8588	High Similarity	NPC329669
0.858	High Similarity	NPC183843
0.858	High Similarity	NPC475883
0.858	High Similarity	NPC66288
0.858	High Similarity	NPC61010
0.858	High Similarity	NPC474351
0.8571	High Similarity	NPC130894
0.8571	High Similarity	NPC250076
0.8571	High Similarity	NPC300943
0.8571	High Similarity	NPC191459
0.8571	High Similarity	NPC176300
0.8571	High Similarity	NPC253634
0.8571	High Similarity	NPC22472
0.8571	High Similarity	NPC105242
0.8571	High Similarity	NPC115798
0.8571	High Similarity	NPC152166
0.8571	High Similarity	NPC477410
0.8571	High Similarity	NPC204854
0.8571	High Similarity	NPC19687
0.8571	High Similarity	NPC9609
0.8571	High Similarity	NPC7846
0.8571	High Similarity	NPC288669
0.8571	High Similarity	NPC4481
0.8571	High Similarity	NPC18607
0.8571	High Similarity	NPC18772
0.8571	High Similarity	NPC143828
0.8571	High Similarity	NPC25495
0.8571	High Similarity	NPC100123
0.8571	High Similarity	NPC261004
0.8563	High Similarity	NPC474520
0.8563	High Similarity	NPC43243
0.8563	High Similarity	NPC149846
0.8563	High Similarity	NPC474167
0.8563	High Similarity	NPC100916
0.8563	High Similarity	NPC292107
0.8563	High Similarity	NPC200388
0.8563	High Similarity	NPC55619
0.8563	High Similarity	NPC471969
0.8563	High Similarity	NPC265511
0.8563	High Similarity	NPC470762
0.8563	High Similarity	NPC245546
0.8563	High Similarity	NPC49824
0.8563	High Similarity	NPC191146
0.8563	High Similarity	NPC266960
0.8563	High Similarity	NPC68093
0.8555	High Similarity	NPC472276
0.8554	High Similarity	NPC476631
0.8547	High Similarity	NPC73929
0.8547	High Similarity	NPC174486

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 NPC289244 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	391
0.1-0.2	1049
0.2-0.3	2118
0.3-0.4	2740
0.4-0.5	1590
0.5-0.6	839
0.6-0.7	297
0.7-0.8	99
0.8-0.85	20
0.85-0.9	7
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.869	High Similarity	NPD1247	Approved
0.8675	High Similarity	NPD3882	Suspended
0.8443	Intermediate Similarity	NPD2801	Approved
0.8266	Intermediate Similarity	NPD3926	Phase 2
0.8225	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8198	Intermediate Similarity	NPD5494	Approved
0.8166	Intermediate Similarity	NPD1934	Approved
0.814	Intermediate Similarity	NPD919	Approved
0.8068	Intermediate Similarity	NPD7473	Discontinued
0.8024	Intermediate Similarity	NPD1512	Approved
0.8023	Intermediate Similarity	NPD3818	Discontinued
0.8011	Intermediate Similarity	NPD6166	Phase 2
0.8011	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8011	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6232	Discontinued
0.7988	Intermediate Similarity	NPD2800	Approved
0.7977	Intermediate Similarity	NPD7075	Discontinued
0.7965	Intermediate Similarity	NPD3817	Phase 2
0.7964	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD1511	Approved
0.7901	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7802	Intermediate Similarity	NPD7808	Phase 3
0.7778	Intermediate Similarity	NPD5844	Phase 1
0.7759	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7747	Intermediate Similarity	NPD7251	Discontinued
0.7747	Intermediate Similarity	NPD6559	Discontinued
0.7746	Intermediate Similarity	NPD6801	Discontinued
0.7735	Intermediate Similarity	NPD7074	Phase 3
0.7733	Intermediate Similarity	NPD6599	Discontinued
0.773	Intermediate Similarity	NPD8434	Phase 2
0.7714	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD1465	Phase 2
0.7701	Intermediate Similarity	NPD7819	Suspended
0.7692	Intermediate Similarity	NPD6797	Phase 2
0.7692	Intermediate Similarity	NPD6799	Approved
0.768	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD7054	Approved
0.7661	Intermediate Similarity	NPD920	Approved
0.7651	Intermediate Similarity	NPD2344	Approved
0.7647	Intermediate Similarity	NPD2534	Approved
0.7647	Intermediate Similarity	NPD2533	Approved
0.7647	Intermediate Similarity	NPD2532	Approved
0.7647	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD6959	Discontinued
0.7637	Intermediate Similarity	NPD7472	Approved
0.763	Intermediate Similarity	NPD4380	Phase 2
0.7596	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD1243	Approved
0.7557	Intermediate Similarity	NPD5402	Approved
0.7545	Intermediate Similarity	NPD1471	Phase 3
0.7514	Intermediate Similarity	NPD2403	Approved
0.7514	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD7411	Suspended
0.7472	Intermediate Similarity	NPD3749	Approved
0.7471	Intermediate Similarity	NPD2309	Approved
0.7442	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD7768	Phase 2
0.741	Intermediate Similarity	NPD6651	Approved
0.741	Intermediate Similarity	NPD1607	Approved
0.7396	Intermediate Similarity	NPD1549	Phase 2
0.7394	Intermediate Similarity	NPD943	Approved
0.7394	Intermediate Similarity	NPD1240	Approved
0.7381	Intermediate Similarity	NPD2935	Discontinued
0.7374	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD3226	Approved
0.7337	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD3751	Discontinued
0.7333	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD1510	Phase 2
0.7321	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD2796	Approved
0.7246	Intermediate Similarity	NPD230	Phase 1
0.7238	Intermediate Similarity	NPD6234	Discontinued
0.7219	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7907	Approved
0.7174	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD5403	Approved
0.7151	Intermediate Similarity	NPD2163	Approved
0.7151	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD447	Suspended
0.712	Intermediate Similarity	NPD5710	Approved
0.712	Intermediate Similarity	NPD5711	Approved
0.7112	Intermediate Similarity	NPD7286	Phase 2
0.711	Intermediate Similarity	NPD3750	Approved
0.711	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD7435	Discontinued
0.7083	Intermediate Similarity	NPD8150	Discontinued
0.7059	Intermediate Similarity	NPD7228	Approved
0.7056	Intermediate Similarity	NPD37	Approved
0.7045	Intermediate Similarity	NPD5401	Approved
0.7037	Intermediate Similarity	NPD5953	Discontinued
0.7035	Intermediate Similarity	NPD6780	Approved
0.7035	Intermediate Similarity	NPD6776	Approved
0.7035	Intermediate Similarity	NPD6777	Approved
0.7035	Intermediate Similarity	NPD6779	Approved
0.7035	Intermediate Similarity	NPD6781	Approved
0.7035	Intermediate Similarity	NPD6778	Approved
0.7035	Intermediate Similarity	NPD6782	Approved
0.7033	Intermediate Similarity	NPD4965	Approved
0.7033	Intermediate Similarity	NPD4966	Approved
0.7033	Intermediate Similarity	NPD4967	Phase 2
0.7027	Intermediate Similarity	NPD3787	Discontinued
0.7018	Intermediate Similarity	NPD2799	Discontinued
0.7015	Intermediate Similarity	NPD7697	Approved
0.7015	Intermediate Similarity	NPD7696	Phase 3
0.7015	Intermediate Similarity	NPD7698	Approved
0.7011	Intermediate Similarity	NPD4628	Phase 3
0.701	Intermediate Similarity	NPD8151	Discontinued
0.6989	Remote Similarity	NPD7390	Discontinued
0.6988	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.698	Remote Similarity	NPD7871	Phase 2
0.698	Remote Similarity	NPD7870	Phase 2
0.6978	Remote Similarity	NPD2296	Approved
0.6977	Remote Similarity	NPD1551	Phase 2
0.6977	Remote Similarity	NPD6100	Approved
0.6977	Remote Similarity	NPD6099	Approved
0.6976	Remote Similarity	NPD7874	Approved
0.6976	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD7199	Phase 2
0.6971	Remote Similarity	NPD6190	Approved
0.697	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD7701	Phase 2
0.6952	Remote Similarity	NPD4111	Phase 1
0.6952	Remote Similarity	NPD4665	Approved
0.6946	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD2346	Discontinued
0.6936	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD8312	Approved
0.6927	Remote Similarity	NPD8313	Approved
0.6914	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD3027	Phase 3
0.6893	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD9494	Approved
0.6882	Remote Similarity	NPD1613	Approved
0.6882	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7801	Approved
0.6854	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.685	Remote Similarity	NPD7700	Phase 2
0.685	Remote Similarity	NPD7699	Phase 2
0.6848	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD6808	Phase 2
0.6845	Remote Similarity	NPD7229	Phase 3
0.6833	Remote Similarity	NPD1653	Approved
0.6823	Remote Similarity	NPD7685	Pre-registration
0.6821	Remote Similarity	NPD3748	Approved
0.6806	Remote Similarity	NPD1729	Discontinued
0.6784	Remote Similarity	NPD6535	Approved
0.6784	Remote Similarity	NPD6534	Approved
0.6779	Remote Similarity	NPD7783	Phase 2
0.6779	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD6279	Approved
0.6776	Remote Similarity	NPD6280	Approved
0.6765	Remote Similarity	NPD2313	Discontinued
0.6744	Remote Similarity	NPD6355	Discontinued
0.6739	Remote Similarity	NPD5761	Phase 2
0.6739	Remote Similarity	NPD5760	Phase 2
0.672	Remote Similarity	NPD5242	Approved
0.6716	Remote Similarity	NPD3057	Approved
0.6703	Remote Similarity	NPD5353	Approved
0.6698	Remote Similarity	NPD8404	Phase 2
0.6687	Remote Similarity	NPD9269	Phase 2
0.6686	Remote Similarity	NPD4060	Phase 1
0.6684	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2654	Approved
0.6667	Remote Similarity	NPD2493	Approved
0.6667	Remote Similarity	NPD2494	Approved
0.6667	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4287	Approved
0.6651	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.665	Remote Similarity	NPD8319	Approved
0.665	Remote Similarity	NPD8320	Phase 1
0.6649	Remote Similarity	NPD7240	Approved
0.6649	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD1933	Approved
0.6636	Remote Similarity	NPD8067	Phase 3
0.6634	Remote Similarity	NPD2491	Approved
0.6634	Remote Similarity	NPD6823	Phase 2
0.6634	Remote Similarity	NPD3533	Approved
0.6634	Remote Similarity	NPD2972	Approved
0.6633	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD8127	Discontinued
0.6612	Remote Similarity	NPD7458	Discontinued
0.6608	Remote Similarity	NPD4625	Phase 3
0.6607	Remote Similarity	NPD6696	Suspended
0.6585	Remote Similarity	NPD3450	Approved
0.6585	Remote Similarity	NPD3452	Approved
0.6584	Remote Similarity	NPD4361	Phase 2

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