NPASS Compound

Structure

CID211810 OpenBabel06191716002D 38 40 0 0 1 0 0 0 0 0999 V2000 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9601 0.0079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7177 -0.0794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4639 2.6854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9246 2.2938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4057 -0.8695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0230 -1.7934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6088 -0.7934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5178 -1.8449 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0849 -0.4759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8482 -1.0708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0812 1.7615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9332 2.4243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7071 -1.7071 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1310 -1.2969 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4142 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7071 -1.7071 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7071 0.7071 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7071 0.7071 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4142 -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 1 0 0 0 0 0 0 0 0 0 -5.7721 -1.4535 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6900 0.9682 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5505 3.3482 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 -0.3244 -2.6310 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0549 -1.6796 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0898 1.6310 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3244 1.6310 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 2 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 15 1 0 0 0 0 5 16 1 0 0 0 0 6 17 1 0 0 0 0 7 27 1 0 0 0 0 8 27 1 0 0 0 0 10 20 1 0 0 0 0 11 19 1 0 0 0 0 11 21 1 0 0 0 0 12 19 1 0 0 0 0 12 22 1 0 0 0 0 13 20 1 0 0 0 0 13 23 2 0 0 0 0 14 29 2 0 0 0 0 14 35 1 0 0 0 0 15 30 2 0 0 0 0 15 36 1 0 0 0 0 16 31 2 0 0 0 0 16 37 1 0 0 0 0 17 32 2 0 0 0 0 17 38 1 0 0 0 0 18 10 1 6 0 0 0 18 24 1 0 0 0 0 18 27 1 0 0 0 0 19 33 1 6 0 0 0 20 35 1 6 0 0 0 21 28 1 1 0 0 0 21 36 1 0 0 0 0 22 24 1 0 0 0 0 22 28 1 1 0 0 0 23 25 1 0 0 0 0 23 27 1 0 0 0 0 24 34 1 6 0 0 0 25 26 1 0 0 0 0 25 37 1 1 0 0 0 26 28 1 6 0 0 0 26 38 1 0 0 0 0 28 9 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	536.26
Volume:	539.258
LogP:	2.18
LogD:	2.211
LogS:	-3.957
# Rotatable Bonds:	8
TPSA:	145.66
# H-Bond Aceptor:	10
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.312
Synthetic Accessibility Score:	5.748
Fsp3:	0.714
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.355
MDCK Permeability:	0.00016103203233797103
Pgp-inhibitor:	0.993
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.902
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.967

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.051
Plasma Protein Binding (PPB):	68.65725708007812%
Volume Distribution (VD):	1.801
Pgp-substrate:	26.23651123046875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.016
CYP2C19-inhibitor:	0.007
CYP2C19-substrate:	0.087
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.035
CYP2D6-inhibitor:	0.277
CYP2D6-substrate:	0.059
CYP3A4-inhibitor:	0.197
CYP3A4-substrate:	0.309

ADMET: Excretion

Clearance (CL):	3.101
Half-life (T1/2):	0.266

ADMET: Toxicity

hERG Blockers:	0.099
Human Hepatotoxicity (H-HT):	0.952
Drug-inuced Liver Injury (DILI):	0.903
AMES Toxicity:	0.025
Rat Oral Acute Toxicity:	0.34
Maximum Recommended Daily Dose:	0.979
Skin Sensitization:	0.131
Carcinogencity:	0.045
Eye Corrosion:	0.01
Eye Irritation:	0.026
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC211810

Natural Product ID:	NPC211810
*Common Name:**	BACKFCRAHXFXCH-LNLYLEBQSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BACKFCRAHXFXCH-LNLYLEBQSA-N
Standard InCHI:	InChI=1S/C28H40O10/c1-12-19(33)11-21(36-15(4)30)28(9)22(12)24(34)18-10-20(35-14(3)29)13(2)23(27(18,7)8)25(37-16(5)31)26(28)38-17(6)32/h18-22,24-26,33-34H,1,10-11H2,2-9H3/t18-,19-,20-,21-,22-,24+,25+,26-,28+/m0/s1
SMILES:	CC(=O)O[C@H]1C[C@H]2[C@@H](O)[C@@H]3C(=C)[C@@H](O)C[C@@H]([C@]3([C@H]([C@@H](C(=C1C)C2(C)C)OC(=O)C)OC(=O)C)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL128080
PubChem CID:	44351600
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0000676] Taxanes and derivatives

*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
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	needles	Himalayan	n.a.	PMID[16480866]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	Stem Bark	n.a.	n.a.	PMID[28240909]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	Roots	n.a.	n.a.	PMID[28581744]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7264680]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17476	Austrotaxus spicata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17476	Austrotaxus spicata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17476	Austrotaxus spicata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23720	Taxus wallichiana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17476	Austrotaxus spicata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23720	Taxus wallichiana	Species	Taxaceae	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	3
Others	2

Activity Type	# Activity
Cell Line	1
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT137	Cell Line	L1210	Mus musculus	IC50	=	10.0	ug.mL-1	PMID[545088]
NPT2	Others	Unspecified		Control	=	205.0	%	PMID[545088]
NPT2	Others	Unspecified		Control	=	439.0	%	PMID[545088]
NPT27	Others	Unspecified		IC50	=	7.4	ug.mL-1	PMID[545088]
NPT2	Others	Unspecified		IC50	=	193000.0	nM	PMID[545089]

☑ 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 NPC211810 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	211
0.1-0.2	1487
0.2-0.3	4522
0.3-0.4	8379
0.4-0.5	14589
0.5-0.6	7485
0.6-0.7	5205
0.7-0.8	757
0.8-0.85	26
0.85-0.9	16
0.9-0.95	14
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC221801
1.0	High Similarity	NPC471765
1.0	High Similarity	NPC284194
0.9775	High Similarity	NPC472360
0.9775	High Similarity	NPC472416
0.9556	High Similarity	NPC182826
0.9556	High Similarity	NPC105375
0.9457	High Similarity	NPC473244
0.9438	High Similarity	NPC220216
0.9348	High Similarity	NPC129569
0.9333	High Similarity	NPC124374
0.9326	High Similarity	NPC261320
0.9231	High Similarity	NPC99653
0.9175	High Similarity	NPC111952
0.9111	High Similarity	NPC246028
0.9101	High Similarity	NPC471779
0.9082	High Similarity	NPC143609
0.9082	High Similarity	NPC472390
0.9053	High Similarity	NPC79303
0.9053	High Similarity	NPC188968
0.9032	High Similarity	NPC471786
0.9032	High Similarity	NPC37603
0.9011	High Similarity	NPC48732
0.8989	High Similarity	NPC102996
0.89	High Similarity	NPC475586
0.8889	High Similarity	NPC102640
0.8854	High Similarity	NPC271295
0.8791	High Similarity	NPC69713
0.8776	High Similarity	NPC8196
0.8763	High Similarity	NPC472554
0.8687	High Similarity	NPC473543
0.8673	High Similarity	NPC472552
0.8673	High Similarity	NPC475344
0.8673	High Similarity	NPC476471
0.8673	High Similarity	NPC137430
0.8667	High Similarity	NPC35933
0.866	High Similarity	NPC38855
0.8586	High Similarity	NPC474124
0.8586	High Similarity	NPC473523
0.8586	High Similarity	NPC99266
0.8571	High Similarity	NPC475617
0.8454	Intermediate Similarity	NPC254121
0.8438	Intermediate Similarity	NPC276110
0.8431	Intermediate Similarity	NPC151393
0.8384	Intermediate Similarity	NPC96784
0.8384	Intermediate Similarity	NPC97435
0.8384	Intermediate Similarity	NPC235920
0.8352	Intermediate Similarity	NPC102048
0.8351	Intermediate Similarity	NPC165632
0.8351	Intermediate Similarity	NPC475304
0.8333	Intermediate Similarity	NPC471205
0.8333	Intermediate Similarity	NPC475781
0.8333	Intermediate Similarity	NPC112780
0.8333	Intermediate Similarity	NPC473586
0.8317	Intermediate Similarity	NPC470768
0.8316	Intermediate Similarity	NPC477574
0.83	Intermediate Similarity	NPC11956
0.8298	Intermediate Similarity	NPC20946
0.8298	Intermediate Similarity	NPC314727
0.8283	Intermediate Similarity	NPC272223
0.828	Intermediate Similarity	NPC131329
0.8252	Intermediate Similarity	NPC135015
0.8252	Intermediate Similarity	NPC472439
0.8252	Intermediate Similarity	NPC50124
0.8252	Intermediate Similarity	NPC48548
0.8252	Intermediate Similarity	NPC128795
0.8252	Intermediate Similarity	NPC217921
0.8252	Intermediate Similarity	NPC475263
0.8252	Intermediate Similarity	NPC469916
0.8252	Intermediate Similarity	NPC38948
0.8247	Intermediate Similarity	NPC476720
0.8247	Intermediate Similarity	NPC86893
0.8247	Intermediate Similarity	NPC292178
0.8229	Intermediate Similarity	NPC53555
0.8222	Intermediate Similarity	NPC25554
0.8218	Intermediate Similarity	NPC7613
0.8218	Intermediate Similarity	NPC127933
0.8218	Intermediate Similarity	NPC23584
0.8218	Intermediate Similarity	NPC475889
0.8218	Intermediate Similarity	NPC7644
0.8211	Intermediate Similarity	NPC209816
0.8211	Intermediate Similarity	NPC78973
0.82	Intermediate Similarity	NPC11974
0.819	Intermediate Similarity	NPC17791
0.8182	Intermediate Similarity	NPC275086
0.8182	Intermediate Similarity	NPC247233
0.8182	Intermediate Similarity	NPC325229
0.8173	Intermediate Similarity	NPC40728
0.8173	Intermediate Similarity	NPC206618
0.8173	Intermediate Similarity	NPC316974
0.8163	Intermediate Similarity	NPC472995
0.8163	Intermediate Similarity	NPC88009
0.8163	Intermediate Similarity	NPC57664
0.8155	Intermediate Similarity	NPC67321
0.8155	Intermediate Similarity	NPC88013
0.8155	Intermediate Similarity	NPC125423
0.8155	Intermediate Similarity	NPC187435
0.8152	Intermediate Similarity	NPC83702
0.8144	Intermediate Similarity	NPC105490
0.8144	Intermediate Similarity	NPC474922
0.8137	Intermediate Similarity	NPC264867
0.8137	Intermediate Similarity	NPC470321
0.8137	Intermediate Similarity	NPC475585
0.8137	Intermediate Similarity	NPC474550
0.8137	Intermediate Similarity	NPC473577
0.8137	Intermediate Similarity	NPC201880
0.8137	Intermediate Similarity	NPC81567
0.8137	Intermediate Similarity	NPC473207
0.8125	Intermediate Similarity	NPC249034
0.8125	Intermediate Similarity	NPC41239
0.8125	Intermediate Similarity	NPC234335
0.8119	Intermediate Similarity	NPC238397
0.8119	Intermediate Similarity	NPC471363
0.8119	Intermediate Similarity	NPC475038
0.8119	Intermediate Similarity	NPC109195
0.8119	Intermediate Similarity	NPC165578
0.8119	Intermediate Similarity	NPC295791
0.8113	Intermediate Similarity	NPC317460
0.8113	Intermediate Similarity	NPC470025
0.8113	Intermediate Similarity	NPC321272
0.8113	Intermediate Similarity	NPC328074
0.8105	Intermediate Similarity	NPC16265
0.81	Intermediate Similarity	NPC228251
0.81	Intermediate Similarity	NPC477971
0.81	Intermediate Similarity	NPC477972
0.81	Intermediate Similarity	NPC161527
0.81	Intermediate Similarity	NPC477968
0.81	Intermediate Similarity	NPC473510
0.81	Intermediate Similarity	NPC219285
0.81	Intermediate Similarity	NPC230546
0.81	Intermediate Similarity	NPC20113
0.8095	Intermediate Similarity	NPC177047
0.8085	Intermediate Similarity	NPC44538
0.8085	Intermediate Similarity	NPC166857
0.8085	Intermediate Similarity	NPC245004
0.8081	Intermediate Similarity	NPC210337
0.8081	Intermediate Similarity	NPC274793
0.8081	Intermediate Similarity	NPC51499
0.8077	Intermediate Similarity	NPC311223
0.8077	Intermediate Similarity	NPC470024
0.8061	Intermediate Similarity	NPC241047
0.8058	Intermediate Similarity	NPC470763
0.8058	Intermediate Similarity	NPC88349
0.8058	Intermediate Similarity	NPC51719
0.8058	Intermediate Similarity	NPC470767
0.8058	Intermediate Similarity	NPC475290
0.8058	Intermediate Similarity	NPC471206
0.8041	Intermediate Similarity	NPC472641
0.8041	Intermediate Similarity	NPC7349
0.8041	Intermediate Similarity	NPC472640
0.8039	Intermediate Similarity	NPC475623
0.8039	Intermediate Similarity	NPC473694
0.8039	Intermediate Similarity	NPC159533
0.8039	Intermediate Similarity	NPC134270
0.8039	Intermediate Similarity	NPC475334
0.8039	Intermediate Similarity	NPC281378
0.8037	Intermediate Similarity	NPC470027
0.802	Intermediate Similarity	NPC280991
0.802	Intermediate Similarity	NPC476132
0.8	Intermediate Similarity	NPC216478
0.8	Intermediate Similarity	NPC284828
0.8	Intermediate Similarity	NPC242767
0.8	Intermediate Similarity	NPC477876
0.8	Intermediate Similarity	NPC278673
0.8	Intermediate Similarity	NPC477875
0.8	Intermediate Similarity	NPC173905
0.8	Intermediate Similarity	NPC470260
0.8	Intermediate Similarity	NPC472216
0.8	Intermediate Similarity	NPC5475
0.8	Intermediate Similarity	NPC75443
0.8	Intermediate Similarity	NPC477928
0.7981	Intermediate Similarity	NPC122816
0.7981	Intermediate Similarity	NPC184512
0.7981	Intermediate Similarity	NPC109376
0.798	Intermediate Similarity	NPC171598
0.798	Intermediate Similarity	NPC54248
0.798	Intermediate Similarity	NPC111834
0.798	Intermediate Similarity	NPC292718
0.798	Intermediate Similarity	NPC202833
0.798	Intermediate Similarity	NPC169270
0.798	Intermediate Similarity	NPC306797
0.798	Intermediate Similarity	NPC288970
0.798	Intermediate Similarity	NPC276103
0.7979	Intermediate Similarity	NPC255143
0.7979	Intermediate Similarity	NPC475684
0.7961	Intermediate Similarity	NPC80809
0.7961	Intermediate Similarity	NPC201144
0.7961	Intermediate Similarity	NPC181104
0.7961	Intermediate Similarity	NPC152966
0.7961	Intermediate Similarity	NPC475331
0.7961	Intermediate Similarity	NPC288502
0.7961	Intermediate Similarity	NPC121518
0.7961	Intermediate Similarity	NPC103298
0.7961	Intermediate Similarity	NPC475335
0.7959	Intermediate Similarity	NPC469491
0.7959	Intermediate Similarity	NPC3359
0.7941	Intermediate Similarity	NPC476081
0.7938	Intermediate Similarity	NPC8729
0.7938	Intermediate Similarity	NPC91251
0.7938	Intermediate Similarity	NPC130840

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 NPC211810 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	182
0.1-0.2	1884
0.2-0.3	3698
0.3-0.4	2196
0.4-0.5	823
0.5-0.6	286
0.6-0.7	77
0.7-0.8	4
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7843	Intermediate Similarity	NPD5344	Discontinued
0.7745	Intermediate Similarity	NPD7639	Approved
0.7745	Intermediate Similarity	NPD7640	Approved
0.7647	Intermediate Similarity	NPD4225	Approved
0.7647	Intermediate Similarity	NPD7638	Approved
0.7573	Intermediate Similarity	NPD6648	Approved
0.75	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD7327	Approved
0.7434	Intermediate Similarity	NPD7328	Approved
0.7431	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7516	Approved
0.7264	Intermediate Similarity	NPD7632	Discontinued
0.7248	Intermediate Similarity	NPD6686	Approved
0.7241	Intermediate Similarity	NPD8296	Approved
0.7241	Intermediate Similarity	NPD8380	Approved
0.7241	Intermediate Similarity	NPD8033	Approved
0.7241	Intermediate Similarity	NPD8378	Approved
0.7241	Intermediate Similarity	NPD8335	Approved
0.7241	Intermediate Similarity	NPD8379	Approved
0.7156	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD8294	Approved
0.7155	Intermediate Similarity	NPD8377	Approved
0.7129	Intermediate Similarity	NPD46	Approved
0.7129	Intermediate Similarity	NPD7838	Discovery
0.7129	Intermediate Similarity	NPD6698	Approved
0.7094	Intermediate Similarity	NPD7503	Approved
0.7059	Intermediate Similarity	NPD7637	Suspended
0.7043	Intermediate Similarity	NPD7115	Discovery
0.7041	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7524	Approved
0.699	Remote Similarity	NPD5778	Approved
0.699	Remote Similarity	NPD5779	Approved
0.6939	Remote Similarity	NPD6695	Phase 3
0.6937	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7645	Phase 2
0.6869	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7507	Approved
0.6829	Remote Similarity	NPD7319	Approved
0.6827	Remote Similarity	NPD6399	Phase 3
0.6822	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD8133	Approved
0.6762	Remote Similarity	NPD7748	Approved
0.6752	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD7983	Approved
0.6731	Remote Similarity	NPD7515	Phase 2
0.6729	Remote Similarity	NPD7902	Approved
0.6701	Remote Similarity	NPD6929	Approved
0.6699	Remote Similarity	NPD6051	Approved
0.6696	Remote Similarity	NPD8297	Approved
0.6667	Remote Similarity	NPD7750	Discontinued
0.6667	Remote Similarity	NPD8513	Phase 3
0.6667	Remote Similarity	NPD8516	Approved
0.6667	Remote Similarity	NPD8517	Approved
0.6667	Remote Similarity	NPD8515	Approved
0.6633	Remote Similarity	NPD6930	Phase 2
0.6633	Remote Similarity	NPD7525	Registered
0.6633	Remote Similarity	NPD6931	Approved
0.6632	Remote Similarity	NPD8264	Approved
0.6607	Remote Similarity	NPD5739	Approved
0.6607	Remote Similarity	NPD6402	Approved
0.6607	Remote Similarity	NPD7128	Approved
0.6607	Remote Similarity	NPD6675	Approved
0.6583	Remote Similarity	NPD6319	Approved
0.6579	Remote Similarity	NPD6372	Approved
0.6579	Remote Similarity	NPD6373	Approved
0.6571	Remote Similarity	NPD6411	Approved
0.6557	Remote Similarity	NPD8328	Phase 3
0.6552	Remote Similarity	NPD6053	Discontinued
0.6549	Remote Similarity	NPD6412	Phase 2
0.6545	Remote Similarity	NPD4159	Approved
0.6522	Remote Similarity	NPD6371	Approved
0.6505	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD4632	Approved
0.6495	Remote Similarity	NPD6925	Approved
0.6495	Remote Similarity	NPD5776	Phase 2
0.6491	Remote Similarity	NPD6899	Approved
0.6491	Remote Similarity	NPD7320	Approved
0.6491	Remote Similarity	NPD6881	Approved
0.6476	Remote Similarity	NPD3168	Discontinued
0.6466	Remote Similarity	NPD6650	Approved
0.6466	Remote Similarity	NPD6649	Approved
0.6466	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD7332	Phase 2
0.6465	Remote Similarity	NPD7514	Phase 3
0.6458	Remote Similarity	NPD7339	Approved
0.6458	Remote Similarity	NPD6942	Approved
0.6449	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD7900	Approved
0.6429	Remote Similarity	NPD7145	Approved
0.6415	Remote Similarity	NPD8034	Phase 2
0.6415	Remote Similarity	NPD7087	Discontinued
0.6415	Remote Similarity	NPD8035	Phase 2
0.641	Remote Similarity	NPD6882	Approved
0.6404	Remote Similarity	NPD5697	Approved
0.6404	Remote Similarity	NPD5701	Approved
0.64	Remote Similarity	NPD6902	Approved
0.64	Remote Similarity	NPD8074	Phase 3
0.6393	Remote Similarity	NPD6921	Approved
0.6392	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD6101	Approved
0.6381	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD7290	Approved
0.6379	Remote Similarity	NPD6883	Approved
0.6379	Remote Similarity	NPD7102	Approved
0.6373	Remote Similarity	NPD4786	Approved
0.6371	Remote Similarity	NPD7492	Approved
0.6346	Remote Similarity	NPD4251	Approved
0.6346	Remote Similarity	NPD4250	Approved
0.6337	Remote Similarity	NPD3667	Approved
0.6337	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD6009	Approved
0.6325	Remote Similarity	NPD6869	Approved
0.6325	Remote Similarity	NPD6617	Approved
0.6325	Remote Similarity	NPD8130	Phase 1
0.6325	Remote Similarity	NPD6847	Approved
0.632	Remote Similarity	NPD6616	Approved
0.6316	Remote Similarity	NPD6008	Approved
0.6316	Remote Similarity	NPD6640	Phase 3
0.6311	Remote Similarity	NPD6054	Approved
0.6311	Remote Similarity	NPD1694	Approved
0.6311	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD6893	Approved
0.6311	Remote Similarity	NPD6059	Approved
0.63	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD6013	Approved
0.6293	Remote Similarity	NPD6014	Approved
0.6293	Remote Similarity	NPD6012	Approved
0.629	Remote Similarity	NPD7604	Phase 2
0.6273	Remote Similarity	NPD6084	Phase 2
0.6273	Remote Similarity	NPD6083	Phase 2
0.627	Remote Similarity	NPD7078	Approved
0.627	Remote Similarity	NPD8293	Discontinued
0.6261	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.626	Remote Similarity	NPD5983	Phase 2
0.625	Remote Similarity	NPD4249	Approved
0.625	Remote Similarity	NPD3618	Phase 1
0.6238	Remote Similarity	NPD6898	Phase 1
0.6226	Remote Similarity	NPD5328	Approved
0.622	Remote Similarity	NPD7736	Approved
0.6211	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.621	Remote Similarity	NPD6370	Approved
0.6207	Remote Similarity	NPD6011	Approved
0.6202	Remote Similarity	NPD7260	Phase 2
0.6195	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD5211	Phase 2
0.619	Remote Similarity	NPD6336	Discontinued
0.6186	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD6932	Approved
0.6154	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD4822	Approved
0.6139	Remote Similarity	NPD4820	Approved
0.6139	Remote Similarity	NPD4819	Approved
0.6139	Remote Similarity	NPD4821	Approved
0.6129	Remote Similarity	NPD6015	Approved
0.6129	Remote Similarity	NPD6016	Approved
0.6126	Remote Similarity	NPD4755	Approved
0.6117	Remote Similarity	NPD7154	Phase 3
0.6111	Remote Similarity	NPD6079	Approved
0.61	Remote Similarity	NPD4268	Approved
0.61	Remote Similarity	NPD4271	Approved
0.6095	Remote Similarity	NPD7146	Approved
0.6095	Remote Similarity	NPD7521	Approved
0.6095	Remote Similarity	NPD6409	Approved
0.6095	Remote Similarity	NPD7334	Approved
0.6095	Remote Similarity	NPD5330	Approved
0.6095	Remote Similarity	NPD6684	Approved
0.6091	Remote Similarity	NPD5695	Phase 3
0.6087	Remote Similarity	NPD5141	Approved
0.608	Remote Similarity	NPD5988	Approved
0.6061	Remote Similarity	NPD6933	Approved
0.6055	Remote Similarity	NPD4202	Approved
0.6044	Remote Similarity	NPD368	Approved
0.604	Remote Similarity	NPD6683	Phase 2
0.6036	Remote Similarity	NPD7839	Suspended
0.6034	Remote Similarity	NPD5357	Phase 1
0.6032	Remote Similarity	NPD6067	Discontinued
0.6031	Remote Similarity	NPD6845	Suspended
0.602	Remote Similarity	NPD6926	Approved
0.602	Remote Similarity	NPD6924	Approved
0.6019	Remote Similarity	NPD5785	Approved
0.6018	Remote Similarity	NPD4700	Approved
0.6018	Remote Similarity	NPD5285	Approved
0.6018	Remote Similarity	NPD5286	Approved
0.6018	Remote Similarity	NPD4696	Approved
0.5984	Remote Similarity	NPD6274	Approved
0.5981	Remote Similarity	NPD6672	Approved
0.5981	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD6903	Approved
0.5981	Remote Similarity	NPD5737	Approved
0.598	Remote Similarity	NPD7509	Discontinued
0.598	Remote Similarity	NPD4748	Discontinued
0.5968	Remote Similarity	NPD7101	Approved
0.5968	Remote Similarity	NPD7100	Approved
0.5966	Remote Similarity	NPD4634	Approved
0.5962	Remote Similarity	NPD5362	Discontinued
0.596	Remote Similarity	NPD8039	Approved
0.5946	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD6114	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