NPASS Compound

Structure

NPC471786 OpenBabel07101719252D 40 42 0 0 1 0 0 0 0 0999 V2000 -2.4092 0.9197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7478 -1.0001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4933 -1.6414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5796 -1.6668 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6031 -0.8207 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3241 2.2129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4873 -2.5323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9599 -0.1693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2530 1.4933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2894 -0.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0707 0.3334 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4933 0.6667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8318 -0.6667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4873 0.8441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6626 0.2932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9170 -1.9600 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4933 -0.6667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8329 -2.2934 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.7590 -0.3334 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4082 2.5463 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4873 -2.5323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0707 -0.3334 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0852 -1.2933 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1693 0.9599 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7467 0.6265 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9159 -0.3334 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1693 -0.9599 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4873 -0.8441 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1703 -2.5865 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 0.9159 0.3334 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0022 -3.2532 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7590 0.6413 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2389 3.5062 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9747 -3.3765 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3396 -3.5464 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9148 -0.8207 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3385 1.9198 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9747 -1.6882 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2544 -2.2531 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 3 17 2 0 0 0 0 4 18 1 0 0 0 0 5 19 1 0 0 0 0 6 20 1 0 0 0 0 7 21 1 0 0 0 0 8 30 1 0 0 0 0 9 30 1 0 0 0 0 11 12 1 0 0 0 0 11 22 1 0 0 0 0 12 31 1 0 0 0 0 13 15 1 0 0 0 0 13 23 1 0 0 0 0 14 24 1 0 0 0 0 14 31 1 0 0 0 0 15 25 2 0 0 0 0 16 2 1 6 0 0 0 16 18 1 0 0 0 0 16 29 1 0 0 0 0 17 22 1 0 0 0 0 17 26 1 0 0 0 0 18 32 1 0 0 0 0 19 33 2 0 0 0 0 19 37 1 0 0 0 0 20 34 2 0 0 0 0 20 38 1 0 0 0 0 21 35 2 0 0 0 0 21 39 1 0 0 0 0 22 37 1 6 0 0 0 23 27 1 0 0 0 0 23 40 1 1 0 0 0 24 25 1 0 0 0 0 24 38 1 1 0 0 0 25 30 1 0 0 0 0 26 28 1 0 0 0 0 26 31 1 1 0 0 0 27 28 1 0 0 0 0 27 30 1 6 0 0 0 28 39 1 6 0 0 0 29 36 2 0 0 0 0 29 40 1 0 0 0 0 31 10 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	562.31
Volume:	582.356
LogP:	4.33
LogD:	2.944
LogS:	-3.229
# Rotatable Bonds:	10
TPSA:	125.43
# H-Bond Aceptor:	9
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.284
Synthetic Accessibility Score:	5.983
Fsp3:	0.742
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:	-5.174
MDCK Permeability:	0.00010047091927845031
Pgp-inhibitor:	0.985
Pgp-substrate:	0.985
Human Intestinal Absorption (HIA):	0.098
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.969

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.075
Plasma Protein Binding (PPB):	63.36272430419922%
Volume Distribution (VD):	1.786
Pgp-substrate:	27.507966995239258%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.033
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.366
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.027
CYP2D6-inhibitor:	0.204
CYP2D6-substrate:	0.042
CYP3A4-inhibitor:	0.468
CYP3A4-substrate:	0.516

ADMET: Excretion

Clearance (CL):	6.253
Half-life (T1/2):	0.002

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.956
Drug-inuced Liver Injury (DILI):	0.914
AMES Toxicity:	0.027
Rat Oral Acute Toxicity:	0.927
Maximum Recommended Daily Dose:	0.461
Skin Sensitization:	0.122
Carcinogencity:	0.334
Eye Corrosion:	0.009
Eye Irritation:	0.015
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC471786

Natural Product ID:	NPC471786
*Common Name:**	FMPIEMVVEJGMCY-UJMFWCJWSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	FMPIEMVVEJGMCY-UJMFWCJWSA-N
Standard InCHI:	InChI=1S/C31H46O9/c1-15-13-23(40-29(36)16(2)18(4)32)27-28(39-21(7)35)26-17(3)22(37-19(5)33)11-12-31(26,10)14-24(38-20(6)34)25(15)30(27,8)9/h16,18,22-24,26-28,32H,3,11-14H2,1-2,4-10H3/t16-,18?,22-,23-,24-,26-,27-,28-,31-/m0/s1
SMILES:	CC1=C2C(CC3(CCC(C(=C)C3C(C(C2(C)C)C(C1)OC(=O)C(C)C(C)O)OC(=O)C)OC(=O)C)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL323283
PubChem CID:	44326761
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
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12217376]
NPO31343	Taxus chinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12217376]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	wood	n.a.	n.a.	PMID[12444707]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	wood	Yunnang Province, China	2000-OCT	PMID[21138310]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	xylem	n.a.	PMID[21138310]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31343	Taxus chinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO31343	Taxus chinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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
ED50	3

Activity Type	# Activity
Cell Line	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1178	Cell Line	KB 3-1	Homo sapiens	ED50	=	8.6	ug ml-1	PMID[551405]
NPT1178	Cell Line	KB 3-1	Homo sapiens	ED50	=	4.3	ug ml-1	PMID[551405]
NPT27	Others	Unspecified		ED50	=	9.8	ug ml-1	PMID[551405]

☑ 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 NPC471786 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	207
0.1-0.2	1326
0.2-0.3	4345
0.3-0.4	8679
0.4-0.5	14411
0.5-0.6	7041
0.6-0.7	5898
0.7-0.8	746
0.8-0.85	13
0.85-0.9	11
0.9-0.95	17
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC37603
0.9551	High Similarity	NPC99653
0.9438	High Similarity	NPC124374
0.9432	High Similarity	NPC261320
0.9326	High Similarity	NPC48732
0.9326	High Similarity	NPC220216
0.9318	High Similarity	NPC69713
0.9205	High Similarity	NPC471779
0.9205	High Similarity	NPC102640
0.9091	High Similarity	NPC102996
0.9032	High Similarity	NPC211810
0.9032	High Similarity	NPC221801
0.9032	High Similarity	NPC284194
0.9032	High Similarity	NPC471765
0.9022	High Similarity	NPC472360
0.9022	High Similarity	NPC472416
0.8817	High Similarity	NPC182826
0.8817	High Similarity	NPC105375
0.87	High Similarity	NPC151393
0.8687	High Similarity	NPC111952
0.8673	High Similarity	NPC8196
0.8632	High Similarity	NPC129569
0.8602	High Similarity	NPC477574
0.86	High Similarity	NPC143609
0.8571	High Similarity	NPC137430
0.8542	High Similarity	NPC473244
0.8485	Intermediate Similarity	NPC127933
0.8485	Intermediate Similarity	NPC475889
0.8485	Intermediate Similarity	NPC7644
0.8485	Intermediate Similarity	NPC7613
0.8485	Intermediate Similarity	NPC99266
0.8416	Intermediate Similarity	NPC112780
0.84	Intermediate Similarity	NPC470321
0.84	Intermediate Similarity	NPC473207
0.84	Intermediate Similarity	NPC264867
0.84	Intermediate Similarity	NPC201880
0.84	Intermediate Similarity	NPC81567
0.8387	Intermediate Similarity	NPC246028
0.8384	Intermediate Similarity	NPC471363
0.8384	Intermediate Similarity	NPC238397
0.8367	Intermediate Similarity	NPC188968
0.8367	Intermediate Similarity	NPC79303
0.83	Intermediate Similarity	NPC134270
0.8283	Intermediate Similarity	NPC97435
0.8252	Intermediate Similarity	NPC475586
0.8242	Intermediate Similarity	NPC102048
0.8235	Intermediate Similarity	NPC125423
0.8235	Intermediate Similarity	NPC184512
0.8235	Intermediate Similarity	NPC88013
0.8235	Intermediate Similarity	NPC472390
0.8211	Intermediate Similarity	NPC234335
0.82	Intermediate Similarity	NPC475344
0.82	Intermediate Similarity	NPC472552
0.82	Intermediate Similarity	NPC474709
0.82	Intermediate Similarity	NPC476471
0.8182	Intermediate Similarity	NPC474718
0.8182	Intermediate Similarity	NPC271295
0.8163	Intermediate Similarity	NPC287668
0.8155	Intermediate Similarity	NPC217921
0.8155	Intermediate Similarity	NPC311223
0.8155	Intermediate Similarity	NPC322903
0.8155	Intermediate Similarity	NPC472439
0.8155	Intermediate Similarity	NPC135015
0.8155	Intermediate Similarity	NPC469916
0.8155	Intermediate Similarity	NPC48548
0.8155	Intermediate Similarity	NPC128795
0.8144	Intermediate Similarity	NPC276110
0.8137	Intermediate Similarity	NPC284365
0.8137	Intermediate Similarity	NPC252296
0.8137	Intermediate Similarity	NPC123726
0.8125	Intermediate Similarity	NPC199543
0.8119	Intermediate Similarity	NPC474124
0.8119	Intermediate Similarity	NPC69171
0.8119	Intermediate Similarity	NPC159533
0.8119	Intermediate Similarity	NPC474165
0.81	Intermediate Similarity	NPC475617
0.81	Intermediate Similarity	NPC472554
0.8081	Intermediate Similarity	NPC471366
0.8081	Intermediate Similarity	NPC476800
0.8081	Intermediate Similarity	NPC472186
0.8081	Intermediate Similarity	NPC216478
0.8081	Intermediate Similarity	NPC318917
0.8077	Intermediate Similarity	NPC316974
0.8077	Intermediate Similarity	NPC40728
0.8061	Intermediate Similarity	NPC165632
0.8058	Intermediate Similarity	NPC473586
0.8041	Intermediate Similarity	NPC105490
0.8041	Intermediate Similarity	NPC250075
0.8039	Intermediate Similarity	NPC475585
0.8039	Intermediate Similarity	NPC474550
0.8039	Intermediate Similarity	NPC473577
0.8039	Intermediate Similarity	NPC473543
0.802	Intermediate Similarity	NPC475038
0.802	Intermediate Similarity	NPC273005
0.802	Intermediate Similarity	NPC476081
0.802	Intermediate Similarity	NPC31058
0.802	Intermediate Similarity	NPC183571
0.802	Intermediate Similarity	NPC469606
0.802	Intermediate Similarity	NPC165250
0.802	Intermediate Similarity	NPC109195
0.8019	Intermediate Similarity	NPC317687
0.8019	Intermediate Similarity	NPC277769
0.8	Intermediate Similarity	NPC469802
0.8	Intermediate Similarity	NPC219285
0.8	Intermediate Similarity	NPC228251
0.8	Intermediate Similarity	NPC474012
0.8	Intermediate Similarity	NPC477971
0.8	Intermediate Similarity	NPC119550
0.8	Intermediate Similarity	NPC473545
0.8	Intermediate Similarity	NPC20113
0.8	Intermediate Similarity	NPC476299
0.8	Intermediate Similarity	NPC472187
0.8	Intermediate Similarity	NPC314727
0.8	Intermediate Similarity	NPC477972
0.8	Intermediate Similarity	NPC473204
0.8	Intermediate Similarity	NPC477968
0.8	Intermediate Similarity	NPC161527
0.7981	Intermediate Similarity	NPC476802
0.7981	Intermediate Similarity	NPC476479
0.7981	Intermediate Similarity	NPC89171
0.7981	Intermediate Similarity	NPC475263
0.798	Intermediate Similarity	NPC472188
0.798	Intermediate Similarity	NPC285513
0.798	Intermediate Similarity	NPC73911
0.798	Intermediate Similarity	NPC474395
0.7961	Intermediate Similarity	NPC475290
0.7957	Intermediate Similarity	NPC35933
0.7944	Intermediate Similarity	NPC159333
0.7941	Intermediate Similarity	NPC95899
0.7941	Intermediate Similarity	NPC473523
0.7938	Intermediate Similarity	NPC7349
0.7925	Intermediate Similarity	NPC317107
0.7921	Intermediate Similarity	NPC111292
0.7921	Intermediate Similarity	NPC476132
0.7921	Intermediate Similarity	NPC11974
0.7917	Intermediate Similarity	NPC232202
0.7917	Intermediate Similarity	NPC78973
0.7905	Intermediate Similarity	NPC42662
0.7905	Intermediate Similarity	NPC31522
0.789	Intermediate Similarity	NPC134430
0.7889	Intermediate Similarity	NPC242767
0.7885	Intermediate Similarity	NPC109376
0.7885	Intermediate Similarity	NPC475781
0.7879	Intermediate Similarity	NPC202833
0.7879	Intermediate Similarity	NPC171598
0.7872	Intermediate Similarity	NPC329692
0.7872	Intermediate Similarity	NPC473226
0.7872	Intermediate Similarity	NPC471219
0.7864	Intermediate Similarity	NPC475036
0.7864	Intermediate Similarity	NPC239162
0.7857	Intermediate Similarity	NPC474922
0.7857	Intermediate Similarity	NPC57117
0.785	Intermediate Similarity	NPC4573
0.785	Intermediate Similarity	NPC90952
0.7843	Intermediate Similarity	NPC471914
0.7843	Intermediate Similarity	NPC473788
0.7843	Intermediate Similarity	NPC478156
0.7843	Intermediate Similarity	NPC295791
0.7843	Intermediate Similarity	NPC475558
0.7835	Intermediate Similarity	NPC41239
0.7835	Intermediate Similarity	NPC72845
0.7822	Intermediate Similarity	NPC47024
0.7822	Intermediate Similarity	NPC38855
0.7822	Intermediate Similarity	NPC272223
0.7822	Intermediate Similarity	NPC476195
0.7822	Intermediate Similarity	NPC476933
0.7822	Intermediate Similarity	NPC251680
0.7822	Intermediate Similarity	NPC54705
0.7812	Intermediate Similarity	NPC16265
0.781	Intermediate Similarity	NPC300614
0.781	Intermediate Similarity	NPC470024
0.781	Intermediate Similarity	NPC275539
0.781	Intermediate Similarity	NPC189075
0.781	Intermediate Similarity	NPC90946
0.781	Intermediate Similarity	NPC94377
0.781	Intermediate Similarity	NPC224660
0.78	Intermediate Similarity	NPC254496
0.78	Intermediate Similarity	NPC98112
0.78	Intermediate Similarity	NPC100912
0.78	Intermediate Similarity	NPC51499
0.7789	Intermediate Similarity	NPC166857
0.7788	Intermediate Similarity	NPC172867
0.7788	Intermediate Similarity	NPC472389
0.7788	Intermediate Similarity	NPC218158
0.7788	Intermediate Similarity	NPC469607
0.7788	Intermediate Similarity	NPC88349
0.7778	Intermediate Similarity	NPC264153
0.7778	Intermediate Similarity	NPC471362
0.7778	Intermediate Similarity	NPC111273
0.7778	Intermediate Similarity	NPC471372
0.7778	Intermediate Similarity	NPC157686
0.7778	Intermediate Similarity	NPC472189
0.7778	Intermediate Similarity	NPC259042
0.7767	Intermediate Similarity	NPC23584
0.7767	Intermediate Similarity	NPC36688
0.7767	Intermediate Similarity	NPC475623
0.7767	Intermediate Similarity	NPC120321
0.7767	Intermediate Similarity	NPC471938
0.7767	Intermediate Similarity	NPC475334
0.7767	Intermediate Similarity	NPC473694

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 NPC471786 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	176
0.1-0.2	1763
0.2-0.3	3690
0.3-0.4	2318
0.4-0.5	790
0.5-0.6	320
0.6-0.7	82
0.7-0.8	11
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
0.79	Intermediate Similarity	NPD7638	Approved
0.7822	Intermediate Similarity	NPD7640	Approved
0.7822	Intermediate Similarity	NPD7639	Approved
0.7723	Intermediate Similarity	NPD4225	Approved
0.7576	Intermediate Similarity	NPD5779	Approved
0.7576	Intermediate Similarity	NPD5778	Approved
0.7475	Intermediate Similarity	NPD7637	Suspended
0.7333	Intermediate Similarity	NPD7632	Discontinued
0.7315	Intermediate Similarity	NPD6686	Approved
0.73	Intermediate Similarity	NPD6411	Approved
0.7248	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD6399	Phase 3
0.72	Intermediate Similarity	NPD6698	Approved
0.72	Intermediate Similarity	NPD46	Approved
0.7182	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD7115	Discovery
0.71	Intermediate Similarity	NPD6101	Approved
0.71	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD5344	Discontinued
0.703	Intermediate Similarity	NPD7838	Discovery
0.7	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.699	Remote Similarity	NPD7748	Approved
0.6961	Remote Similarity	NPD7515	Phase 2
0.6961	Remote Similarity	NPD7983	Approved
0.6957	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD7902	Approved
0.6937	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6053	Discontinued
0.6897	Remote Similarity	NPD7327	Approved
0.6897	Remote Similarity	NPD7328	Approved
0.6885	Remote Similarity	NPD7319	Approved
0.6864	Remote Similarity	NPD8033	Approved
0.6842	Remote Similarity	NPD8133	Approved
0.6838	Remote Similarity	NPD7516	Approved
0.6822	Remote Similarity	NPD6648	Approved
0.6818	Remote Similarity	NPD6402	Approved
0.6818	Remote Similarity	NPD5739	Approved
0.6818	Remote Similarity	NPD7128	Approved
0.6818	Remote Similarity	NPD6675	Approved
0.6786	Remote Similarity	NPD6372	Approved
0.6786	Remote Similarity	NPD6373	Approved
0.678	Remote Similarity	NPD6319	Approved
0.678	Remote Similarity	NPD8294	Approved
0.678	Remote Similarity	NPD8377	Approved
0.6777	Remote Similarity	NPD7507	Approved
0.6771	Remote Similarity	NPD7645	Phase 2
0.6768	Remote Similarity	NPD4786	Approved
0.6768	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD6051	Approved
0.675	Remote Similarity	NPD8328	Phase 3
0.6735	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD3667	Approved
0.6729	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD6371	Approved
0.6723	Remote Similarity	NPD8379	Approved
0.6723	Remote Similarity	NPD8517	Approved
0.6723	Remote Similarity	NPD8515	Approved
0.6723	Remote Similarity	NPD8296	Approved
0.6723	Remote Similarity	NPD8378	Approved
0.6723	Remote Similarity	NPD8516	Approved
0.6723	Remote Similarity	NPD8380	Approved
0.6723	Remote Similarity	NPD8335	Approved
0.6723	Remote Similarity	NPD7503	Approved
0.6723	Remote Similarity	NPD8513	Phase 3
0.6696	Remote Similarity	NPD7320	Approved
0.6696	Remote Similarity	NPD6899	Approved
0.6696	Remote Similarity	NPD6881	Approved
0.6667	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6649	Approved
0.6667	Remote Similarity	NPD7900	Approved
0.6667	Remote Similarity	NPD6650	Approved
0.6667	Remote Similarity	NPD6695	Phase 3
0.6636	Remote Similarity	NPD6083	Phase 2
0.6636	Remote Similarity	NPD6084	Phase 2
0.6635	Remote Similarity	NPD8035	Phase 2
0.6635	Remote Similarity	NPD8034	Phase 2
0.6609	Remote Similarity	NPD6882	Approved
0.6609	Remote Similarity	NPD8297	Approved
0.6607	Remote Similarity	NPD6412	Phase 2
0.6607	Remote Similarity	NPD5701	Approved
0.6607	Remote Similarity	NPD5697	Approved
0.6607	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD7290	Approved
0.6579	Remote Similarity	NPD7102	Approved
0.6579	Remote Similarity	NPD6883	Approved
0.6569	Remote Similarity	NPD4250	Approved
0.6569	Remote Similarity	NPD4251	Approved
0.6557	Remote Similarity	NPD7492	Approved
0.6542	Remote Similarity	NPD7839	Suspended
0.6538	Remote Similarity	NPD5785	Approved
0.6535	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD1694	Approved
0.6535	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD7525	Registered
0.6531	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD7339	Approved
0.6526	Remote Similarity	NPD6942	Approved
0.6526	Remote Similarity	NPD8264	Approved
0.6522	Remote Similarity	NPD8130	Phase 1
0.6522	Remote Similarity	NPD6869	Approved
0.6522	Remote Similarity	NPD6617	Approved
0.6522	Remote Similarity	NPD6847	Approved
0.6518	Remote Similarity	NPD6008	Approved
0.6504	Remote Similarity	NPD6616	Approved
0.65	Remote Similarity	NPD6059	Approved
0.65	Remote Similarity	NPD6054	Approved
0.6491	Remote Similarity	NPD6012	Approved
0.6491	Remote Similarity	NPD6013	Approved
0.6491	Remote Similarity	NPD6014	Approved
0.6471	Remote Similarity	NPD6409	Approved
0.6471	Remote Similarity	NPD4249	Approved
0.6471	Remote Similarity	NPD7521	Approved
0.6471	Remote Similarity	NPD7146	Approved
0.6471	Remote Similarity	NPD3618	Phase 1
0.6471	Remote Similarity	NPD5330	Approved
0.6471	Remote Similarity	NPD6684	Approved
0.6471	Remote Similarity	NPD7334	Approved
0.6458	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD8293	Discontinued
0.6452	Remote Similarity	NPD7078	Approved
0.6452	Remote Similarity	NPD8074	Phase 3
0.6449	Remote Similarity	NPD5695	Phase 3
0.6446	Remote Similarity	NPD6921	Approved
0.6442	Remote Similarity	NPD5328	Approved
0.6429	Remote Similarity	NPD6929	Approved
0.641	Remote Similarity	NPD4632	Approved
0.6408	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD7524	Approved
0.6408	Remote Similarity	NPD7750	Discontinued
0.6404	Remote Similarity	NPD6011	Approved
0.64	Remote Similarity	NPD7736	Approved
0.6393	Remote Similarity	NPD6370	Approved
0.6379	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4821	Approved
0.6364	Remote Similarity	NPD4822	Approved
0.6364	Remote Similarity	NPD4820	Approved
0.6364	Remote Similarity	NPD4819	Approved
0.6364	Remote Similarity	NPD6930	Phase 2
0.6364	Remote Similarity	NPD6931	Approved
0.6355	Remote Similarity	NPD5282	Discontinued
0.6354	Remote Similarity	NPD8039	Approved
0.6346	Remote Similarity	NPD6672	Approved
0.6346	Remote Similarity	NPD5737	Approved
0.6346	Remote Similarity	NPD6903	Approved
0.6346	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD7154	Phase 3
0.633	Remote Similarity	NPD4755	Approved
0.6327	Remote Similarity	NPD4268	Approved
0.6327	Remote Similarity	NPD4271	Approved
0.6321	Remote Similarity	NPD6079	Approved
0.6311	Remote Similarity	NPD6016	Approved
0.6311	Remote Similarity	NPD6015	Approved
0.6293	Remote Similarity	NPD4634	Approved
0.6275	Remote Similarity	NPD3666	Approved
0.6275	Remote Similarity	NPD3133	Approved
0.6275	Remote Similarity	NPD3668	Phase 3
0.6275	Remote Similarity	NPD3665	Phase 1
0.6273	Remote Similarity	NPD5696	Approved
0.6262	Remote Similarity	NPD4202	Approved
0.626	Remote Similarity	NPD5988	Approved
0.625	Remote Similarity	NPD6009	Approved
0.625	Remote Similarity	NPD5211	Phase 2
0.6238	Remote Similarity	NPD4269	Approved
0.6238	Remote Similarity	NPD4270	Approved
0.6224	Remote Similarity	NPD6925	Approved
0.6224	Remote Similarity	NPD5776	Phase 2
0.6216	Remote Similarity	NPD5286	Approved
0.6216	Remote Similarity	NPD4700	Approved
0.6216	Remote Similarity	NPD4696	Approved
0.6216	Remote Similarity	NPD5285	Approved
0.621	Remote Similarity	NPD7604	Phase 2
0.62	Remote Similarity	NPD7332	Phase 2
0.62	Remote Similarity	NPD7514	Phase 3
0.6179	Remote Similarity	NPD5983	Phase 2
0.6176	Remote Similarity	NPD5362	Discontinued
0.6168	Remote Similarity	NPD7087	Discontinued
0.6168	Remote Similarity	NPD5693	Phase 1
0.6167	Remote Similarity	NPD6274	Approved
0.6162	Remote Similarity	NPD7145	Approved
0.6162	Remote Similarity	NPD6115	Approved
0.6162	Remote Similarity	NPD6114	Approved
0.6162	Remote Similarity	NPD6697	Approved
0.6162	Remote Similarity	NPD6118	Approved
0.6162	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5786	Approved
0.6148	Remote Similarity	NPD7101	Approved
0.6148	Remote Similarity	NPD7100	Approved
0.614	Remote Similarity	NPD5141	Approved
0.6139	Remote Similarity	NPD5369	Approved
0.6139	Remote Similarity	NPD6902	Approved
0.6132	Remote Similarity	NPD4753	Phase 2
0.6132	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD7260	Phase 2
0.6111	Remote Similarity	NPD6336	Discontinued
0.6106	Remote Similarity	NPD5224	Approved
0.6106	Remote Similarity	NPD5226	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