NPASS Compound

Structure

CID149846 OpenBabel06191715522D 44 50 0 0 0 0 0 0 0 0999 V2000 5.9541 -0.1427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3338 2.5491 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3043 -1.7896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7029 -1.2694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4504 1.0194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5673 2.5494 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3691 -4.8611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5254 -1.4585 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5262 -0.4852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6046 -0.8651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0032 -0.3449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3337 1.5292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4507 3.0592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3534 -1.9918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5672 1.5295 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5271 -4.3752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2114 -4.3745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5255 -0.4864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6835 -1.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6842 0.0006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5266 -1.4578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5267 -3.4027 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6843 -1.9443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2112 -3.4024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8419 -0.4859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6837 -0.0002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8417 -1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3690 -2.9162 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8421 -1.4580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8418 -0.4862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5555 -0.6629 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3527 0.3775 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2169 1.0192 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4508 4.0791 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6551 -4.8789 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0835 -4.8779 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4089 0.0234 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6833 -2.9643 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6840 1.0076 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0531 -2.9163 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6839 1.0197 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3686 -1.9436 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -1.9442 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 10 2 0 0 0 0 1 11 1 0 0 0 0 2 12 2 0 0 0 0 2 13 1 0 0 0 0 3 10 1 0 0 0 0 3 14 2 0 0 0 0 4 11 2 0 0 0 0 4 14 1 0 0 0 0 5 12 1 0 0 0 0 5 15 2 0 0 0 0 6 13 2 0 0 0 0 6 15 1 0 0 0 0 7 16 2 0 0 0 0 7 17 1 0 0 0 0 8 18 2 0 0 0 0 8 19 1 0 0 0 0 9 20 2 0 0 0 0 9 21 1 0 0 0 0 10 31 1 0 0 0 0 11 32 1 0 0 0 0 12 33 1 0 0 0 0 13 34 1 0 0 0 0 14 40 1 0 0 0 0 15 41 1 0 0 0 0 16 22 1 0 0 0 0 16 35 1 0 0 0 0 17 24 2 0 0 0 0 17 36 1 0 0 0 0 18 26 1 0 0 0 0 18 37 1 0 0 0 0 19 27 2 0 0 0 0 19 38 1 0 0 0 0 20 25 1 0 0 0 0 20 39 1 0 0 0 0 21 23 2 0 0 0 0 21 42 1 0 0 0 0 22 23 1 0 0 0 0 22 28 2 0 0 0 0 23 29 1 0 0 0 0 24 28 1 0 0 0 0 24 40 1 0 0 0 0 25 29 2 0 0 0 0 25 44 1 0 0 0 0 26 30 2 0 0 0 0 26 41 1 0 0 0 0 27 30 1 0 0 0 0 27 43 1 0 0 0 0 28 42 1 0 0 0 0 29 43 1 0 0 0 0 30 44 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	602.07
Volume:	551.057
LogP:	5.282
LogD:	2.774
LogS:	-9.109
# Rotatable Bonds:	4
TPSA:	232.13
# H-Bond Aceptor:	14
# H-Bond Donor:	9
# Rings:	7
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.106
Synthetic Accessibility Score:	3.695
Fsp3:	0.0
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.273
MDCK Permeability:	1.1323056241963059e-05
Pgp-inhibitor:	0.017
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.349
20% Bioavailability (F20%):	0.507
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	88.64530181884766%
Volume Distribution (VD):	0.391
Pgp-substrate:	14.74657917022705%

ADMET: Metabolism

CYP1A2-inhibitor:	0.852
CYP1A2-substrate:	0.106
CYP2C19-inhibitor:	0.13
CYP2C19-substrate:	0.03
CYP2C9-inhibitor:	0.539
CYP2C9-substrate:	0.85
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.225
CYP3A4-inhibitor:	0.069
CYP3A4-substrate:	0.053

ADMET: Excretion

Clearance (CL):	10.022
Half-life (T1/2):	0.843

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.035
Drug-inuced Liver Injury (DILI):	0.94
AMES Toxicity:	0.196
Rat Oral Acute Toxicity:	0.999
Maximum Recommended Daily Dose:	0.995
Skin Sensitization:	0.979
Carcinogencity:	0.094
Eye Corrosion:	0.003
Eye Irritation:	0.947
Respiratory Toxicity:	0.091

Download Data

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

Natural Product: NPC149846

Natural Product ID:	NPC149846
*Common Name:**	Phlorofucofuroeckol A
IUPAC Name:	4,9-bis(3,5-dihydroxyphenoxy)-[1]benzofuro[3,2-a]oxanthrene-1,3,6,10,12-pentol
Synonyms:
Standard InCHIKey:	SLWPBUMYPRVYIJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C30H18O14/c31-10-1-11(32)4-14(3-10)40-24-17(36)7-16(35)22-23-21(42-28(22)24)9-20(39)25-29(23)43-27-19(38)8-18(37)26(30(27)44-25)41-15-5-12(33)2-13(34)6-15/h1-9,31-39H
SMILES:	Oc1cc(O)cc(c1)Oc1c(O)cc(c2c1Oc1c(O)cc3c(c1O2)c1c(O)cc(c(c1o3)Oc1cc(O)cc(c1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL510508
PubChem CID:	130976
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable tannins

*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
NPO14337	Ecklonia stolonifera	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12913249]
NPO27567	Eisenia bicyclis	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14575430]
NPO27567	Eisenia bicyclis	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14738398]
NPO22789	Ecklonia cava	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18693022]
NPO22789	Ecklonia cava	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19201199]
NPO27567	Eisenia bicyclis	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20462757]
NPO22789	Ecklonia cava	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23647823]
NPO20824	Ecklonia kurome	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14337	Ecklonia stolonifera	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20824	Ecklonia kurome	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14337	Ecklonia stolonifera	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20824	Ecklonia kurome	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22789	Ecklonia cava	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14337	Ecklonia stolonifera	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27567	Eisenia bicyclis	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20824	Ecklonia kurome	Species	Lessoniaceae	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	8
Ki	2
Others	3

Activity Type	# Activity
Cell Line	1
Individual Protein	5
NON-MOLECULAR	3
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	CC50	>	200000.0	nM	PMID[532781]
NPT1595	Individual Protein	Replicase polyprotein 1ab	SARS coronavirus	IC50	=	174600.0	nM	PMID[532781]
NPT1595	Individual Protein	Replicase polyprotein 1ab	SARS coronavirus	IC50	=	16700.0	nM	PMID[532781]
NPT1595	Individual Protein	Replicase polyprotein 1ab	SARS coronavirus	Ki	=	10600.0	nM	PMID[532781]
NPT1	Others	Radical scavenging activity		IC50	=	17660.0	nM	PMID[532778]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	39200.0	nM	PMID[532778]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	21600.0	nM	PMID[532778]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	21400.0	nM	PMID[532778]
NPT27	Others	Unspecified		Activity	=	1.0	uM	PMID[532779]
NPT740	Individual Protein	Beta-secretase 1	Homo sapiens	Ki	=	1300.0	nM	PMID[532780]
NPT740	Individual Protein	Beta-secretase 1	Homo sapiens	IC50	=	2130.0	nM	PMID[532780]
NPT2	Others	Unspecified		Ratio CC50/IC50	>	1.1	n.a.	PMID[532781]
NPT2	Others	Unspecified		IC50	=	16700.0	nM	PMID[532782]

☑ 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 NPC149846 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	628
0.1-0.2	2411
0.2-0.3	5884
0.3-0.4	11629
0.4-0.5	5103
0.5-0.6	4549
0.6-0.7	5450
0.7-0.8	4743
0.8-0.85	1597
0.85-0.9	643
0.9-0.95	59
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9412	High Similarity	NPC226725
0.9353	High Similarity	NPC154527
0.9349	High Similarity	NPC47883
0.9281	High Similarity	NPC82217
0.9281	High Similarity	NPC216842
0.9281	High Similarity	NPC476640
0.9273	High Similarity	NPC470704
0.9226	High Similarity	NPC287243
0.9222	High Similarity	NPC174700
0.9222	High Similarity	NPC230619
0.9222	High Similarity	NPC54098
0.9212	High Similarity	NPC272560
0.9172	High Similarity	NPC49667
0.9172	High Similarity	NPC8127
0.9162	High Similarity	NPC476641
0.9152	High Similarity	NPC45449
0.9152	High Similarity	NPC36320
0.9133	High Similarity	NPC248315
0.9118	High Similarity	NPC98546
0.9118	High Similarity	NPC297807
0.9102	High Similarity	NPC247136
0.9091	High Similarity	NPC39305
0.9091	High Similarity	NPC1706
0.9091	High Similarity	NPC59295
0.9091	High Similarity	NPC263092
0.9091	High Similarity	NPC1755
0.9085	High Similarity	NPC34089
0.9085	High Similarity	NPC196179
0.9064	High Similarity	NPC476273
0.9059	High Similarity	NPC471841
0.9053	High Similarity	NPC473834
0.9053	High Similarity	NPC65885
0.9036	High Similarity	NPC259757
0.903	High Similarity	NPC238995
0.903	High Similarity	NPC312056
0.903	High Similarity	NPC84515
0.903	High Similarity	NPC272722
0.9018	High Similarity	NPC185526
0.9017	High Similarity	NPC476170
0.9	High Similarity	NPC99591
0.8976	High Similarity	NPC272064
0.8976	High Similarity	NPC133065
0.897	High Similarity	NPC231758
0.897	High Similarity	NPC188486
0.8963	High Similarity	NPC196879
0.8957	High Similarity	NPC472461
0.8941	High Similarity	NPC117450
0.8941	High Similarity	NPC310794
0.8929	High Similarity	NPC295082
0.8929	High Similarity	NPC50394
0.8922	High Similarity	NPC39306
0.8922	High Similarity	NPC37183
0.8916	High Similarity	NPC477841
0.8916	High Similarity	NPC219927
0.8902	High Similarity	NPC7973
0.8902	High Similarity	NPC78302
0.8902	High Similarity	NPC29841
0.8902	High Similarity	NPC235215
0.8902	High Similarity	NPC472438
0.8902	High Similarity	NPC112954
0.8895	High Similarity	NPC265380
0.8895	High Similarity	NPC475783
0.8889	High Similarity	NPC125300
0.8882	High Similarity	NPC257667
0.8882	High Similarity	NPC28589
0.8882	High Similarity	NPC186847
0.8882	High Similarity	NPC248593
0.8882	High Similarity	NPC472454
0.8876	High Similarity	NPC107627
0.8876	High Similarity	NPC202470
0.8869	High Similarity	NPC277480
0.8862	High Similarity	NPC41301
0.8857	High Similarity	NPC304322
0.8851	High Similarity	NPC150977
0.8851	High Similarity	NPC471842
0.8848	High Similarity	NPC176300
0.8848	High Similarity	NPC22472
0.8848	High Similarity	NPC288669
0.8848	High Similarity	NPC115798
0.8848	High Similarity	NPC105242
0.8848	High Similarity	NPC4481
0.8848	High Similarity	NPC19687
0.8848	High Similarity	NPC16935
0.8848	High Similarity	NPC300943
0.8848	High Similarity	NPC18772
0.8848	High Similarity	NPC195832
0.8848	High Similarity	NPC152166
0.8848	High Similarity	NPC204854
0.8848	High Similarity	NPC7846
0.8848	High Similarity	NPC25495
0.8848	High Similarity	NPC9609
0.8848	High Similarity	NPC253634
0.8848	High Similarity	NPC18607
0.8848	High Similarity	NPC154304
0.8848	High Similarity	NPC130894
0.8848	High Similarity	NPC190487
0.8848	High Similarity	NPC143828
0.8848	High Similarity	NPC191459
0.8848	High Similarity	NPC261004
0.8844	High Similarity	NPC324742
0.8844	High Similarity	NPC185275
0.8841	High Similarity	NPC200388
0.8841	High Similarity	NPC45131
0.8841	High Similarity	NPC100916
0.8841	High Similarity	NPC268161
0.8841	High Similarity	NPC274730
0.8841	High Similarity	NPC474520
0.8841	High Similarity	NPC55619
0.8824	High Similarity	NPC102277
0.8824	High Similarity	NPC279209
0.8817	High Similarity	NPC14662
0.8817	High Similarity	NPC247973
0.8817	High Similarity	NPC243877
0.881	High Similarity	NPC58223
0.881	High Similarity	NPC477840
0.881	High Similarity	NPC224280
0.881	High Similarity	NPC7688
0.881	High Similarity	NPC36
0.881	High Similarity	NPC7154
0.881	High Similarity	NPC72787
0.881	High Similarity	NPC125039
0.881	High Similarity	NPC36916
0.8807	High Similarity	NPC139683
0.8807	High Similarity	NPC73929
0.8807	High Similarity	NPC269625
0.8807	High Similarity	NPC47905
0.88	High Similarity	NPC71260
0.8795	High Similarity	NPC188967
0.8795	High Similarity	NPC246478
0.8795	High Similarity	NPC200746
0.8788	High Similarity	NPC287979
0.8788	High Similarity	NPC93376
0.8788	High Similarity	NPC110070
0.8788	High Similarity	NPC227192
0.8788	High Similarity	NPC189179
0.8788	High Similarity	NPC305663
0.8788	High Similarity	NPC203891
0.8788	High Similarity	NPC176665
0.8788	High Similarity	NPC224137
0.8788	High Similarity	NPC75215
0.8788	High Similarity	NPC101830
0.8788	High Similarity	NPC300727
0.8788	High Similarity	NPC241904
0.8788	High Similarity	NPC469584
0.8788	High Similarity	NPC163524
0.8773	High Similarity	NPC27208
0.8765	High Similarity	NPC280493
0.8765	High Similarity	NPC61620
0.8757	High Similarity	NPC171985
0.8757	High Similarity	NPC320741
0.8757	High Similarity	NPC224851
0.875	High Similarity	NPC475985
0.875	High Similarity	NPC470459
0.8735	High Similarity	NPC100123
0.8735	High Similarity	NPC193842
0.8735	High Similarity	NPC152904
0.8735	High Similarity	NPC476242
0.8728	High Similarity	NPC24258
0.8728	High Similarity	NPC216307
0.8727	High Similarity	NPC292107
0.8727	High Similarity	NPC138243
0.8727	High Similarity	NPC43243
0.8727	High Similarity	NPC245546
0.8727	High Similarity	NPC178854
0.8727	High Similarity	NPC49824
0.8727	High Similarity	NPC98661
0.8727	High Similarity	NPC191146
0.8727	High Similarity	NPC68093
0.8727	High Similarity	NPC266960
0.8727	High Similarity	NPC137100
0.8727	High Similarity	NPC247017
0.872	High Similarity	NPC162351
0.872	High Similarity	NPC246204
0.872	High Similarity	NPC276409
0.872	High Similarity	NPC58382
0.872	High Similarity	NPC89474
0.872	High Similarity	NPC250822
0.872	High Similarity	NPC75279
0.8713	High Similarity	NPC78830
0.8713	High Similarity	NPC218533
0.8713	High Similarity	NPC131866
0.8712	High Similarity	NPC251110
0.8712	High Similarity	NPC225731
0.8708	High Similarity	NPC295436
0.8706	High Similarity	NPC86477
0.8706	High Similarity	NPC260266
0.8706	High Similarity	NPC76482
0.8698	High Similarity	NPC29411
0.8698	High Similarity	NPC234052
0.8698	High Similarity	NPC470457
0.8698	High Similarity	NPC326520
0.8698	High Similarity	NPC291110
0.869	High Similarity	NPC25152
0.8683	High Similarity	NPC139036
0.8683	High Similarity	NPC228785
0.8683	High Similarity	NPC320359
0.8683	High Similarity	NPC101731
0.8683	High Similarity	NPC56085
0.8683	High Similarity	NPC204290
0.8683	High Similarity	NPC14353

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 NPC149846 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	505
0.1-0.2	1105
0.2-0.3	2117
0.3-0.4	2750
0.4-0.5	1542
0.5-0.6	779
0.6-0.7	244
0.7-0.8	78
0.8-0.85	21
0.85-0.9	8
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.881	High Similarity	NPD6168	Clinical (unspecified phase)
0.881	High Similarity	NPD6167	Clinical (unspecified phase)
0.881	High Similarity	NPD6166	Phase 2
0.8614	High Similarity	NPD3882	Suspended
0.8606	High Similarity	NPD2801	Approved
0.8457	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8448	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8434	Intermediate Similarity	NPD1934	Approved
0.8405	Intermediate Similarity	NPD1512	Approved
0.8393	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD1511	Approved
0.8276	Intermediate Similarity	NPD3818	Discontinued
0.8274	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8246	Intermediate Similarity	NPD5494	Approved
0.8239	Intermediate Similarity	NPD6797	Phase 2
0.8235	Intermediate Similarity	NPD3749	Approved
0.8225	Intermediate Similarity	NPD3817	Phase 2
0.8208	Intermediate Similarity	NPD3926	Phase 2
0.8198	Intermediate Similarity	NPD6959	Discontinued
0.8192	Intermediate Similarity	NPD7251	Discontinued
0.8182	Intermediate Similarity	NPD7074	Phase 3
0.8166	Intermediate Similarity	NPD1465	Phase 2
0.8146	Intermediate Similarity	NPD7808	Phase 3
0.8125	Intermediate Similarity	NPD7054	Approved
0.8092	Intermediate Similarity	NPD1247	Approved
0.8079	Intermediate Similarity	NPD7472	Approved
0.8046	Intermediate Similarity	NPD6232	Discontinued
0.8011	Intermediate Similarity	NPD7473	Discontinued
0.7921	Intermediate Similarity	NPD5844	Phase 1
0.7919	Intermediate Similarity	NPD7075	Discontinued
0.7907	Intermediate Similarity	NPD5402	Approved
0.7904	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD4380	Phase 2
0.788	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.779	Intermediate Similarity	NPD6559	Discontinued
0.7771	Intermediate Similarity	NPD919	Approved
0.7746	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD3787	Discontinued
0.7738	Intermediate Similarity	NPD7390	Discontinued
0.7697	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD3751	Discontinued
0.7651	Intermediate Similarity	NPD1549	Phase 2
0.7633	Intermediate Similarity	NPD6799	Approved
0.763	Intermediate Similarity	NPD7411	Suspended
0.7606	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD2344	Approved
0.7586	Intermediate Similarity	NPD6801	Discontinued
0.7572	Intermediate Similarity	NPD6599	Discontinued
0.7557	Intermediate Similarity	NPD7768	Phase 2
0.7546	Intermediate Similarity	NPD943	Approved
0.7543	Intermediate Similarity	NPD7819	Suspended
0.7527	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2800	Approved
0.75	Intermediate Similarity	NPD5403	Approved
0.75	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD1510	Phase 2
0.7453	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD8313	Approved
0.7419	Intermediate Similarity	NPD8312	Approved
0.7412	Intermediate Similarity	NPD2309	Approved
0.7407	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD7199	Phase 2
0.7384	Intermediate Similarity	NPD5401	Approved
0.7377	Intermediate Similarity	NPD7228	Approved
0.7374	Intermediate Similarity	NPD6234	Discontinued
0.7365	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD3750	Approved
0.7333	Intermediate Similarity	NPD1240	Approved
0.7321	Intermediate Similarity	NPD2796	Approved
0.7316	Intermediate Similarity	NPD4287	Approved
0.731	Intermediate Similarity	NPD6190	Approved
0.7294	Intermediate Similarity	NPD1243	Approved
0.7283	Intermediate Similarity	NPD2534	Approved
0.7283	Intermediate Similarity	NPD2532	Approved
0.7283	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD2533	Approved
0.7246	Intermediate Similarity	NPD1607	Approved
0.7245	Intermediate Similarity	NPD6776	Approved
0.7245	Intermediate Similarity	NPD6782	Approved
0.7245	Intermediate Similarity	NPD6778	Approved
0.7245	Intermediate Similarity	NPD6780	Approved
0.7245	Intermediate Similarity	NPD6777	Approved
0.7245	Intermediate Similarity	NPD6781	Approved
0.7245	Intermediate Similarity	NPD6779	Approved
0.7235	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD1613	Approved
0.7229	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7435	Discontinued
0.7214	Intermediate Similarity	NPD8151	Discontinued
0.7211	Intermediate Similarity	NPD8434	Phase 2
0.72	Intermediate Similarity	NPD920	Approved
0.7191	Intermediate Similarity	NPD37	Approved
0.7186	Intermediate Similarity	NPD7871	Phase 2
0.7186	Intermediate Similarity	NPD7870	Phase 2
0.7184	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD4966	Approved
0.7167	Intermediate Similarity	NPD4965	Approved
0.7167	Intermediate Similarity	NPD4967	Phase 2
0.7119	Intermediate Similarity	NPD3226	Approved
0.7118	Intermediate Similarity	NPD2935	Discontinued
0.7118	Intermediate Similarity	NPD6099	Approved
0.7118	Intermediate Similarity	NPD6100	Approved
0.7086	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD230	Phase 1
0.7083	Intermediate Similarity	NPD447	Suspended
0.7081	Intermediate Similarity	NPD2403	Approved
0.7071	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD1653	Approved
0.7059	Intermediate Similarity	NPD3748	Approved
0.7059	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD8455	Phase 2
0.705	Intermediate Similarity	NPD7696	Phase 3
0.705	Intermediate Similarity	NPD7698	Approved
0.705	Intermediate Similarity	NPD7697	Approved
0.7031	Intermediate Similarity	NPD8150	Discontinued
0.701	Intermediate Similarity	NPD7874	Approved
0.701	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7907	Approved
0.6995	Remote Similarity	NPD7701	Phase 2
0.6994	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.699	Remote Similarity	NPD6534	Approved
0.699	Remote Similarity	NPD6535	Approved
0.6988	Remote Similarity	NPD4908	Phase 1
0.6977	Remote Similarity	NPD1471	Phase 3
0.6976	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD7783	Phase 2
0.6947	Remote Similarity	NPD7240	Approved
0.6947	Remote Similarity	NPD7685	Pre-registration
0.6946	Remote Similarity	NPD3027	Phase 3
0.6923	Remote Similarity	NPD2296	Approved
0.6919	Remote Similarity	NPD5406	Approved
0.6919	Remote Similarity	NPD1551	Phase 2
0.6919	Remote Similarity	NPD5408	Approved
0.6919	Remote Similarity	NPD5404	Approved
0.6919	Remote Similarity	NPD5405	Approved
0.6911	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD4665	Approved
0.6905	Remote Similarity	NPD4111	Phase 1
0.6893	Remote Similarity	NPD7801	Approved
0.6884	Remote Similarity	NPD7699	Phase 2
0.6884	Remote Similarity	NPD7700	Phase 2
0.6882	Remote Similarity	NPD7229	Phase 3
0.6882	Remote Similarity	NPD5710	Approved
0.6882	Remote Similarity	NPD5711	Approved
0.6879	Remote Similarity	NPD2346	Discontinued
0.6866	Remote Similarity	NPD3452	Approved
0.6866	Remote Similarity	NPD3450	Approved
0.6866	Remote Similarity	NPD2494	Approved
0.6866	Remote Similarity	NPD2493	Approved
0.6864	Remote Similarity	NPD6233	Phase 2
0.686	Remote Similarity	NPD2799	Discontinued
0.6857	Remote Similarity	NPD4628	Phase 3
0.6857	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6651	Approved
0.684	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD6823	Phase 2
0.6825	Remote Similarity	NPD2163	Approved
0.6823	Remote Similarity	NPD7549	Discontinued
0.6806	Remote Similarity	NPD5953	Discontinued
0.6805	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD2313	Discontinued
0.6805	Remote Similarity	NPD3764	Approved
0.6805	Remote Similarity	NPD6798	Discontinued
0.6798	Remote Similarity	NPD4004	Approved
0.6798	Remote Similarity	NPD4002	Approved
0.6784	Remote Similarity	NPD1933	Approved
0.6765	Remote Similarity	NPD4583	Approved
0.6765	Remote Similarity	NPD4582	Approved
0.674	Remote Similarity	NPD7458	Discontinued
0.674	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD9269	Phase 2
0.6726	Remote Similarity	NPD2861	Phase 2
0.6726	Remote Similarity	NPD9494	Approved
0.672	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.672	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD7680	Approved
0.6707	Remote Similarity	NPD1203	Approved
0.6702	Remote Similarity	NPD7286	Phase 2
0.6698	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD6355	Discontinued
0.6686	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD8319	Approved
0.6683	Remote Similarity	NPD8320	Phase 1
0.6667	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7003	Approved
0.6667	Remote Similarity	NPD2975	Approved
0.6667	Remote Similarity	NPD2973	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