NPASS Compound

Structure

CID261320 OpenBabel06191716062D 33 35 0 0 1 0 0 0 0 0999 V2000 -2.3958 0.9145 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4850 -1.6323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0592 -2.2700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9007 -1.9490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3167 2.2006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9545 -0.1683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2460 1.4850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2878 -0.4110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0592 0.3315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4850 0.6630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8216 -0.6630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4846 0.8394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6533 0.2915 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4850 -0.6630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8986 -1.7854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1582 -2.5721 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4059 2.5321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0592 -0.3315 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0791 -1.2860 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1683 0.9545 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7425 0.6230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9108 -0.3315 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1683 -0.9545 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4846 -0.8394 0.0000 C 0 0 1 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 0.9108 0.3315 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7380 -2.2700 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3265 -3.5266 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2376 3.4866 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9693 -1.6788 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8986 -0.8161 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2474 -2.2406 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3366 1.9091 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 14 2 0 0 0 0 3 15 1 0 0 0 0 4 16 1 0 0 0 0 5 17 1 0 0 0 0 6 25 1 0 0 0 0 7 25 1 0 0 0 0 9 10 1 0 0 0 0 9 18 1 0 0 0 0 10 26 1 0 0 0 0 11 13 1 0 0 0 0 11 19 1 0 0 0 0 12 20 1 0 0 0 0 12 26 1 0 0 0 0 13 21 2 0 0 0 0 14 18 1 0 0 0 0 14 22 1 0 0 0 0 15 27 2 0 0 0 0 15 31 1 0 0 0 0 16 28 2 0 0 0 0 16 32 1 0 0 0 0 17 29 2 0 0 0 0 17 33 1 0 0 0 0 18 31 1 6 0 0 0 19 23 1 0 0 0 0 19 32 1 1 0 0 0 20 21 1 0 0 0 0 20 33 1 1 0 0 0 21 25 1 0 0 0 0 22 24 1 0 0 0 0 22 26 1 1 0 0 0 23 24 1 0 0 0 0 23 25 1 6 0 0 0 24 30 1 6 0 0 0 26 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	462.26
Volume:	480.932
LogP:	3.799
LogD:	3.079
LogS:	-3.668
# Rotatable Bonds:	6
TPSA:	99.13
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.386
Synthetic Accessibility Score:	5.668
Fsp3:	0.731
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.043
MDCK Permeability:	6.994291470618919e-05
Pgp-inhibitor:	0.809
Pgp-substrate:	0.992
Human Intestinal Absorption (HIA):	0.025
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.96

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.142
Plasma Protein Binding (PPB):	66.02922821044922%
Volume Distribution (VD):	1.856
Pgp-substrate:	32.3650016784668%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.042
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.446
CYP2C9-inhibitor:	0.011
CYP2C9-substrate:	0.033
CYP2D6-inhibitor:	0.175
CYP2D6-substrate:	0.059
CYP3A4-inhibitor:	0.358
CYP3A4-substrate:	0.476

ADMET: Excretion

Clearance (CL):	4.662
Half-life (T1/2):	0.009

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.682
Drug-inuced Liver Injury (DILI):	0.902
AMES Toxicity:	0.032
Rat Oral Acute Toxicity:	0.892
Maximum Recommended Daily Dose:	0.838
Skin Sensitization:	0.171
Carcinogencity:	0.482
Eye Corrosion:	0.54
Eye Irritation:	0.036
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: NPC261320

Natural Product ID:	NPC261320
*Common Name:**	XRSWXKSZTUARNM-SFPMZPPXSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XRSWXKSZTUARNM-SFPMZPPXSA-N
Standard InCHI:	InChI=1S/C26H38O7/c1-13-11-19(32-16(4)28)23-24(30)22-14(2)18(31-15(3)27)9-10-26(22,8)12-20(33-17(5)29)21(13)25(23,6)7/h18-20,22-24,30H,2,9-12H2,1,3-8H3/t18-,19-,20-,22-,23-,24-,26-/m0/s1
SMILES:	CC(=O)O[C@H]1CC[C@@]2([C@@H](C1=C)[C@H](O)[C@@H]1[C@@H](OC(=O)C)CC(=C([C@H](C2)OC(=O)C)C1(C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL246989
PubChem CID:	6325381
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]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	wood	n.a.	n.a.	PMID[12444707]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	xylem	n.a.	PMID[21138310]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	wood	Yunnang Province, China	2000-OCT	PMID[21138310]
NPO23059	Ligularia intermedia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23059	Ligularia intermedia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29841	Taxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23059	Ligularia intermedia	Species	Asteraceae	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	9

Activity Type	# Activity
Cell Line	2
Individual Protein	9
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1475	Cell Line	WI-38 VA13	Homo sapiens	IC50	=	104000.0	nM	PMID[516273]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	122000.0	nM	PMID[516273]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Activity	=	99.0	%	PMID[516273]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Activity	=	111.0	%	PMID[516273]
NPT27	Others	Unspecified		IC50	=	130400.0	nM	PMID[516273]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Activity	=	101.0	%	PMID[516273]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Activity	=	144.0	%	PMID[516273]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Activity	=	259.0	%	PMID[516273]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Activity	=	89.0	%	PMID[516273]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Activity	=	84.0	%	PMID[516273]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Activity	=	74.0	%	PMID[516273]

☑ 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 NPC261320 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	197
0.1-0.2	1366
0.2-0.3	4508
0.3-0.4	10864
0.4-0.5	12655
0.5-0.6	7105
0.6-0.7	5206
0.7-0.8	743
0.8-0.85	23
0.85-0.9	12
0.9-0.95	12
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9881	High Similarity	NPC220216
0.9765	High Similarity	NPC124374
0.9759	High Similarity	NPC471779
0.9651	High Similarity	NPC99653
0.9432	High Similarity	NPC37603
0.9432	High Similarity	NPC471786
0.9419	High Similarity	NPC48732
0.9405	High Similarity	NPC102996
0.9326	High Similarity	NPC284194
0.9326	High Similarity	NPC211810
0.9326	High Similarity	NPC471765
0.9326	High Similarity	NPC221801
0.9318	High Similarity	NPC472416
0.9318	High Similarity	NPC472360
0.9294	High Similarity	NPC102640
0.9186	High Similarity	NPC69713
0.9101	High Similarity	NPC182826
0.9101	High Similarity	NPC105375
0.8901	High Similarity	NPC129569
0.8864	High Similarity	NPC246028
0.8804	High Similarity	NPC473244
0.8721	High Similarity	NPC102048
0.8667	High Similarity	NPC234335
0.8667	High Similarity	NPC477574
0.8632	High Similarity	NPC137430
0.8617	High Similarity	NPC79303
0.8617	High Similarity	NPC188968
0.8587	High Similarity	NPC276110
0.8557	High Similarity	NPC111952
0.8542	High Similarity	NPC99266
0.8542	High Similarity	NPC8196
0.8526	High Similarity	NPC475617
0.8478	Intermediate Similarity	NPC105490
0.8471	Intermediate Similarity	NPC469802
0.8469	Intermediate Similarity	NPC472390
0.8469	Intermediate Similarity	NPC143609
0.8438	Intermediate Similarity	NPC476471
0.8438	Intermediate Similarity	NPC475344
0.8438	Intermediate Similarity	NPC238397
0.8438	Intermediate Similarity	NPC471363
0.8421	Intermediate Similarity	NPC477971
0.8421	Intermediate Similarity	NPC219285
0.8421	Intermediate Similarity	NPC477972
0.8421	Intermediate Similarity	NPC477968
0.8421	Intermediate Similarity	NPC228251
0.8421	Intermediate Similarity	NPC20113
0.8421	Intermediate Similarity	NPC161527
0.8421	Intermediate Similarity	NPC271295
0.8409	Intermediate Similarity	NPC35933
0.837	Intermediate Similarity	NPC7349
0.8353	Intermediate Similarity	NPC242767
0.8352	Intermediate Similarity	NPC78973
0.8351	Intermediate Similarity	NPC7613
0.8351	Intermediate Similarity	NPC134270
0.8351	Intermediate Similarity	NPC475889
0.8351	Intermediate Similarity	NPC474124
0.8351	Intermediate Similarity	NPC127933
0.8351	Intermediate Similarity	NPC7644
0.8333	Intermediate Similarity	NPC472554
0.8333	Intermediate Similarity	NPC97435
0.8315	Intermediate Similarity	NPC471219
0.83	Intermediate Similarity	NPC475586
0.8298	Intermediate Similarity	NPC165632
0.828	Intermediate Similarity	NPC474922
0.8265	Intermediate Similarity	NPC470321
0.8265	Intermediate Similarity	NPC264867
0.8265	Intermediate Similarity	NPC473207
0.8265	Intermediate Similarity	NPC473543
0.8265	Intermediate Similarity	NPC81567
0.8265	Intermediate Similarity	NPC201880
0.8261	Intermediate Similarity	NPC41239
0.8247	Intermediate Similarity	NPC472552
0.8242	Intermediate Similarity	NPC314727
0.8242	Intermediate Similarity	NPC16265
0.8229	Intermediate Similarity	NPC38855
0.8222	Intermediate Similarity	NPC166857
0.8211	Intermediate Similarity	NPC51499
0.8211	Intermediate Similarity	NPC98112
0.82	Intermediate Similarity	NPC151393
0.8191	Intermediate Similarity	NPC471372
0.8191	Intermediate Similarity	NPC472189
0.8191	Intermediate Similarity	NPC471362
0.8182	Intermediate Similarity	NPC23748
0.8182	Intermediate Similarity	NPC252296
0.8163	Intermediate Similarity	NPC473523
0.8161	Intermediate Similarity	NPC25554
0.8152	Intermediate Similarity	NPC209816
0.8144	Intermediate Similarity	NPC11974
0.8132	Intermediate Similarity	NPC291665
0.8125	Intermediate Similarity	NPC278673
0.8125	Intermediate Similarity	NPC275086
0.8125	Intermediate Similarity	NPC216478
0.8125	Intermediate Similarity	NPC325229
0.8111	Intermediate Similarity	NPC131813
0.8105	Intermediate Similarity	NPC57664
0.8105	Intermediate Similarity	NPC276103
0.8105	Intermediate Similarity	NPC171598
0.8105	Intermediate Similarity	NPC54248
0.8105	Intermediate Similarity	NPC88009
0.81	Intermediate Similarity	NPC88013
0.81	Intermediate Similarity	NPC473586
0.81	Intermediate Similarity	NPC184512
0.81	Intermediate Similarity	NPC475781
0.81	Intermediate Similarity	NPC109376
0.81	Intermediate Similarity	NPC125423
0.809	Intermediate Similarity	NPC83702
0.8085	Intermediate Similarity	NPC250075
0.8085	Intermediate Similarity	NPC3359
0.8085	Intermediate Similarity	NPC469491
0.8068	Intermediate Similarity	NPC256112
0.8068	Intermediate Similarity	NPC471218
0.8065	Intermediate Similarity	NPC249034
0.8065	Intermediate Similarity	NPC130840
0.8061	Intermediate Similarity	NPC31058
0.8061	Intermediate Similarity	NPC273005
0.8061	Intermediate Similarity	NPC476081
0.8061	Intermediate Similarity	NPC469606
0.8061	Intermediate Similarity	NPC475038
0.8061	Intermediate Similarity	NPC165250
0.8061	Intermediate Similarity	NPC109195
0.8061	Intermediate Similarity	NPC11956
0.8043	Intermediate Similarity	NPC470819
0.8043	Intermediate Similarity	NPC473647
0.8043	Intermediate Similarity	NPC20946
0.8041	Intermediate Similarity	NPC474190
0.8041	Intermediate Similarity	NPC324841
0.8041	Intermediate Similarity	NPC473510
0.8022	Intermediate Similarity	NPC471796
0.8022	Intermediate Similarity	NPC131329
0.8021	Intermediate Similarity	NPC155319
0.8021	Intermediate Similarity	NPC96597
0.8021	Intermediate Similarity	NPC125551
0.8021	Intermediate Similarity	NPC239547
0.8021	Intermediate Similarity	NPC472188
0.8021	Intermediate Similarity	NPC210337
0.8021	Intermediate Similarity	NPC91197
0.8021	Intermediate Similarity	NPC309503
0.802	Intermediate Similarity	NPC470024
0.802	Intermediate Similarity	NPC48548
0.802	Intermediate Similarity	NPC128795
0.802	Intermediate Similarity	NPC311223
0.802	Intermediate Similarity	NPC475263
0.802	Intermediate Similarity	NPC135015
0.802	Intermediate Similarity	NPC224660
0.802	Intermediate Similarity	NPC217921
0.802	Intermediate Similarity	NPC469916
0.802	Intermediate Similarity	NPC472439
0.8	Intermediate Similarity	NPC220217
0.8	Intermediate Similarity	NPC135224
0.8	Intermediate Similarity	NPC172867
0.8	Intermediate Similarity	NPC476720
0.8	Intermediate Similarity	NPC119855
0.8	Intermediate Similarity	NPC477969
0.8	Intermediate Similarity	NPC88349
0.798	Intermediate Similarity	NPC23584
0.798	Intermediate Similarity	NPC45897
0.798	Intermediate Similarity	NPC120009
0.7979	Intermediate Similarity	NPC472640
0.7979	Intermediate Similarity	NPC53555
0.7979	Intermediate Similarity	NPC472641
0.7978	Intermediate Similarity	NPC49208
0.7959	Intermediate Similarity	NPC235920
0.7959	Intermediate Similarity	NPC96784
0.7957	Intermediate Similarity	NPC232202
0.7957	Intermediate Similarity	NPC470817
0.7955	Intermediate Similarity	NPC142163
0.7941	Intermediate Similarity	NPC40728
0.7941	Intermediate Similarity	NPC316974
0.7938	Intermediate Similarity	NPC476800
0.7938	Intermediate Similarity	NPC318917
0.7938	Intermediate Similarity	NPC472186
0.7938	Intermediate Similarity	NPC247233
0.7938	Intermediate Similarity	NPC471366
0.7931	Intermediate Similarity	NPC100906
0.7921	Intermediate Similarity	NPC112780
0.7917	Intermediate Similarity	NPC304899
0.7917	Intermediate Similarity	NPC475304
0.7917	Intermediate Similarity	NPC94905
0.7917	Intermediate Similarity	NPC202833
0.7917	Intermediate Similarity	NPC253115
0.7917	Intermediate Similarity	NPC8954
0.7912	Intermediate Similarity	NPC473226
0.7912	Intermediate Similarity	NPC474970
0.7912	Intermediate Similarity	NPC329692
0.7907	Intermediate Similarity	NPC283619
0.79	Intermediate Similarity	NPC473577
0.79	Intermediate Similarity	NPC470768
0.79	Intermediate Similarity	NPC475585
0.79	Intermediate Similarity	NPC474550
0.7895	Intermediate Similarity	NPC189513
0.7895	Intermediate Similarity	NPC104925
0.7895	Intermediate Similarity	NPC298973
0.7895	Intermediate Similarity	NPC57117
0.7895	Intermediate Similarity	NPC140277
0.7889	Intermediate Similarity	NPC46320
0.7889	Intermediate Similarity	NPC299963
0.7879	Intermediate Similarity	NPC273668
0.7879	Intermediate Similarity	NPC295791
0.7872	Intermediate Similarity	NPC72845
0.7864	Intermediate Similarity	NPC316708

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 NPC261320 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	169
0.1-0.2	1805
0.2-0.3	3721
0.3-0.4	2328
0.4-0.5	732
0.5-0.6	290
0.6-0.7	100
0.7-0.8	5
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
0.7938	Intermediate Similarity	NPD7638	Approved
0.7857	Intermediate Similarity	NPD7640	Approved
0.7857	Intermediate Similarity	NPD7639	Approved
0.7426	Intermediate Similarity	NPD5344	Discontinued
0.74	Intermediate Similarity	NPD4225	Approved
0.7353	Intermediate Similarity	NPD7632	Discontinued
0.7264	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD5778	Approved
0.7245	Intermediate Similarity	NPD6399	Phase 3
0.7245	Intermediate Similarity	NPD5779	Approved
0.717	Intermediate Similarity	NPD6686	Approved
0.7157	Intermediate Similarity	NPD6648	Approved
0.7143	Intermediate Similarity	NPD7637	Suspended
0.7143	Intermediate Similarity	NPD7645	Phase 2
0.7128	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD6051	Approved
0.7054	Intermediate Similarity	NPD7328	Approved
0.7054	Intermediate Similarity	NPD7327	Approved
0.7041	Intermediate Similarity	NPD6698	Approved
0.7041	Intermediate Similarity	NPD7838	Discovery
0.7041	Intermediate Similarity	NPD46	Approved
0.7037	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD6695	Phase 3
0.7018	Intermediate Similarity	NPD8033	Approved
0.7	Intermediate Similarity	NPD7748	Approved
0.6991	Remote Similarity	NPD7516	Approved
0.697	Remote Similarity	NPD6411	Approved
0.697	Remote Similarity	NPD7515	Phase 2
0.6961	Remote Similarity	NPD7902	Approved
0.693	Remote Similarity	NPD8294	Approved
0.693	Remote Similarity	NPD8377	Approved
0.6909	Remote Similarity	NPD6053	Discontinued
0.6889	Remote Similarity	NPD6942	Approved
0.6889	Remote Similarity	NPD8264	Approved
0.6889	Remote Similarity	NPD7339	Approved
0.6882	Remote Similarity	NPD7525	Registered
0.687	Remote Similarity	NPD8380	Approved
0.687	Remote Similarity	NPD8335	Approved
0.687	Remote Similarity	NPD8379	Approved
0.687	Remote Similarity	NPD8378	Approved
0.687	Remote Similarity	NPD8296	Approved
0.687	Remote Similarity	NPD7503	Approved
0.6822	Remote Similarity	NPD6675	Approved
0.6822	Remote Similarity	NPD7128	Approved
0.6822	Remote Similarity	NPD5739	Approved
0.6822	Remote Similarity	NPD6402	Approved
0.6814	Remote Similarity	NPD7115	Discovery
0.6813	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6929	Approved
0.6771	Remote Similarity	NPD4786	Approved
0.6768	Remote Similarity	NPD6101	Approved
0.6768	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD3667	Approved
0.6735	Remote Similarity	NPD7524	Approved
0.6735	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD7750	Discontinued
0.6702	Remote Similarity	NPD6931	Approved
0.6702	Remote Similarity	NPD6930	Phase 2
0.6697	Remote Similarity	NPD7320	Approved
0.6697	Remote Similarity	NPD6881	Approved
0.6697	Remote Similarity	NPD6899	Approved
0.6697	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD8133	Approved
0.6667	Remote Similarity	NPD7900	Approved
0.6667	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD7507	Approved
0.6636	Remote Similarity	NPD6372	Approved
0.6636	Remote Similarity	NPD6373	Approved
0.6635	Remote Similarity	NPD6083	Phase 2
0.6635	Remote Similarity	NPD6084	Phase 2
0.6634	Remote Similarity	NPD8035	Phase 2
0.6634	Remote Similarity	NPD8034	Phase 2
0.6606	Remote Similarity	NPD5701	Approved
0.6606	Remote Similarity	NPD6412	Phase 2
0.6606	Remote Similarity	NPD5697	Approved
0.6577	Remote Similarity	NPD7290	Approved
0.6577	Remote Similarity	NPD7102	Approved
0.6577	Remote Similarity	NPD6883	Approved
0.6571	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD4251	Approved
0.6566	Remote Similarity	NPD4250	Approved
0.6559	Remote Similarity	NPD5776	Phase 2
0.6559	Remote Similarity	NPD6925	Approved
0.6531	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD1694	Approved
0.6531	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD7332	Phase 2
0.6526	Remote Similarity	NPD7514	Phase 3
0.6526	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD6847	Approved
0.6518	Remote Similarity	NPD6869	Approved
0.6518	Remote Similarity	NPD6617	Approved
0.6518	Remote Similarity	NPD8130	Phase 1
0.6518	Remote Similarity	NPD6649	Approved
0.6518	Remote Similarity	NPD6650	Approved
0.6514	Remote Similarity	NPD6008	Approved
0.6489	Remote Similarity	NPD7145	Approved
0.6486	Remote Similarity	NPD6013	Approved
0.6486	Remote Similarity	NPD6014	Approved
0.6486	Remote Similarity	NPD6012	Approved
0.6475	Remote Similarity	NPD7319	Approved
0.6471	Remote Similarity	NPD7983	Approved
0.6471	Remote Similarity	NPD7087	Discontinued
0.6465	Remote Similarity	NPD4249	Approved
0.6465	Remote Similarity	NPD7146	Approved
0.6465	Remote Similarity	NPD5330	Approved
0.6465	Remote Similarity	NPD3618	Phase 1
0.6465	Remote Similarity	NPD7521	Approved
0.6465	Remote Similarity	NPD6684	Approved
0.6465	Remote Similarity	NPD7334	Approved
0.6465	Remote Similarity	NPD6409	Approved
0.646	Remote Similarity	NPD6882	Approved
0.646	Remote Similarity	NPD8297	Approved
0.6458	Remote Similarity	NPD6902	Approved
0.6442	Remote Similarity	NPD5695	Phase 3
0.6436	Remote Similarity	NPD5328	Approved
0.6429	Remote Similarity	NPD6371	Approved
0.6413	Remote Similarity	NPD6926	Approved
0.6413	Remote Similarity	NPD6924	Approved
0.6404	Remote Similarity	NPD4632	Approved
0.6396	Remote Similarity	NPD6011	Approved
0.6383	Remote Similarity	NPD6932	Approved
0.6372	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6893	Approved
0.6356	Remote Similarity	NPD6319	Approved
0.6354	Remote Similarity	NPD4820	Approved
0.6354	Remote Similarity	NPD4822	Approved
0.6354	Remote Similarity	NPD4748	Discontinued
0.6354	Remote Similarity	NPD4819	Approved
0.6354	Remote Similarity	NPD4821	Approved
0.6354	Remote Similarity	NPD7509	Discontinued
0.6344	Remote Similarity	NPD8039	Approved
0.6337	Remote Similarity	NPD6903	Approved
0.6337	Remote Similarity	NPD6672	Approved
0.6337	Remote Similarity	NPD5737	Approved
0.6337	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD8328	Phase 3
0.6327	Remote Similarity	NPD7154	Phase 3
0.6322	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD4755	Approved
0.6316	Remote Similarity	NPD4271	Approved
0.6316	Remote Similarity	NPD4268	Approved
0.6311	Remote Similarity	NPD6079	Approved
0.6303	Remote Similarity	NPD8517	Approved
0.6303	Remote Similarity	NPD8513	Phase 3
0.6303	Remote Similarity	NPD8515	Approved
0.6303	Remote Similarity	NPD8516	Approved
0.6296	Remote Similarity	NPD4159	Approved
0.6289	Remote Similarity	NPD6898	Phase 1
0.6286	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD7492	Approved
0.6277	Remote Similarity	NPD6933	Approved
0.6263	Remote Similarity	NPD3133	Approved
0.6263	Remote Similarity	NPD3668	Phase 3
0.6263	Remote Similarity	NPD3666	Approved
0.6263	Remote Similarity	NPD3665	Phase 1
0.6262	Remote Similarity	NPD5696	Approved
0.625	Remote Similarity	NPD6683	Phase 2
0.625	Remote Similarity	NPD4202	Approved
0.6239	Remote Similarity	NPD6009	Approved
0.6239	Remote Similarity	NPD5211	Phase 2
0.623	Remote Similarity	NPD6616	Approved
0.6228	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD6059	Approved
0.6218	Remote Similarity	NPD6054	Approved
0.6214	Remote Similarity	NPD3168	Discontinued
0.6214	Remote Similarity	NPD5785	Approved
0.6204	Remote Similarity	NPD5286	Approved
0.6204	Remote Similarity	NPD4700	Approved
0.6204	Remote Similarity	NPD4696	Approved
0.6204	Remote Similarity	NPD5285	Approved
0.6198	Remote Similarity	NPD7604	Phase 2
0.6196	Remote Similarity	NPD7150	Approved
0.6196	Remote Similarity	NPD7152	Approved
0.6196	Remote Similarity	NPD7151	Approved
0.6179	Remote Similarity	NPD7078	Approved
0.6179	Remote Similarity	NPD8293	Discontinued
0.6167	Remote Similarity	NPD5983	Phase 2
0.6162	Remote Similarity	NPD5362	Discontinued
0.6161	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5693	Phase 1
0.6154	Remote Similarity	NPD6923	Approved
0.6154	Remote Similarity	NPD6274	Approved
0.6154	Remote Similarity	NPD6922	Approved
0.6146	Remote Similarity	NPD6115	Approved
0.6146	Remote Similarity	NPD6697	Approved
0.6146	Remote Similarity	NPD6118	Approved
0.6146	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD6114	Approved
0.6146	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD7100	Approved
0.6134	Remote Similarity	NPD7101	Approved
0.6129	Remote Similarity	NPD7736	Approved
0.6126	Remote Similarity	NPD5141	Approved
0.6117	Remote Similarity	NPD7285	Clinical (unspecified phase)

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