NPASS Compound

Structure

CID325176 OpenBabel06191716182D 51 54 0 0 1 0 0 0 0 0999 V2000 -1.7321 -3.0000 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 7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8301 3.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0981 5.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1244 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.9904 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5752 4.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9874 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 4.0000 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 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2583 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2583 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 12.9904 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 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 -1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.3923 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 13.8564 6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 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 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 5.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5752 5.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 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 12.1244 6.0000 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 5.1962 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 35 1 0 0 0 0 5 35 1 0 0 0 0 6 36 1 0 0 0 0 7 9 1 0 0 0 0 7 20 1 0 0 0 0 8 10 2 0 0 0 0 8 21 1 0 0 0 0 10 27 1 0 0 0 0 11 13 1 0 0 0 0 11 20 2 0 0 0 0 12 14 2 0 0 0 0 12 22 1 0 0 0 0 13 46 1 0 0 0 0 14 45 1 0 0 0 0 15 23 2 0 0 0 0 15 24 1 0 0 0 0 16 28 1 0 0 0 0 16 36 1 0 0 0 0 17 29 1 0 0 0 0 17 36 1 0 0 0 0 18 47 1 0 0 0 0 19 48 1 0 0 0 0 21 24 2 0 0 0 0 21 33 1 0 0 0 0 22 23 1 0 0 0 0 22 33 2 0 0 0 0 23 45 1 0 0 0 0 24 49 1 0 0 0 0 25 18 1 1 0 0 0 25 30 1 0 0 0 0 25 50 1 0 0 0 0 26 9 1 6 0 0 0 26 35 1 0 0 0 0 26 51 1 0 0 0 0 27 37 2 0 0 0 0 27 49 1 0 0 0 0 28 38 2 0 0 0 0 28 47 1 0 0 0 0 29 39 2 0 0 0 0 29 51 1 0 0 0 0 30 31 1 0 0 0 0 30 40 1 6 0 0 0 31 32 1 0 0 0 0 31 41 1 1 0 0 0 32 34 1 0 0 0 0 32 42 1 6 0 0 0 33 46 1 0 0 0 0 34 48 1 1 0 0 0 34 50 1 0 0 0 0 35 43 1 0 0 0 0 36 44 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	720.3
Volume:	705.111
LogP:	3.107
LogD:	2.444
LogS:	-4.054
# Rotatable Bonds:	18
TPSA:	224.79
# H-Bond Aceptor:	15
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.081
Synthetic Accessibility Score:	5.117
Fsp3:	0.583
Lipinski Rule-of-5:	Rejected
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:	-5.446
MDCK Permeability:	6.749302701791748e-05
Pgp-inhibitor:	0.047
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.196
20% Bioavailability (F20%):	0.178
30% Bioavailability (F30%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.049
Plasma Protein Binding (PPB):	79.62005615234375%
Volume Distribution (VD):	0.688
Pgp-substrate:	10.454898834228516%

ADMET: Metabolism

CYP1A2-inhibitor:	0.03
CYP1A2-substrate:	0.099
CYP2C19-inhibitor:	0.047
CYP2C19-substrate:	0.079
CYP2C9-inhibitor:	0.597
CYP2C9-substrate:	0.136
CYP2D6-inhibitor:	0.101
CYP2D6-substrate:	0.088
CYP3A4-inhibitor:	0.301
CYP3A4-substrate:	0.26

ADMET: Excretion

Clearance (CL):	6.248
Half-life (T1/2):	0.791

ADMET: Toxicity

hERG Blockers:	0.109
Human Hepatotoxicity (H-HT):	0.448
Drug-inuced Liver Injury (DILI):	0.739
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.108
Maximum Recommended Daily Dose:	0.2
Skin Sensitization:	0.044
Carcinogencity:	0.19
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.006

Download Data

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

Natural Product: NPC325176

Natural Product ID:	NPC325176
*Common Name:**	Citrusoside B
IUPAC Name:	1-O-[(E,3R)-2-hydroxy-2,6-dimethyl-8-(7-oxofuro[3,2-g]chromen-4-yl)oxyoct-6-en-3-yl] 5-O-[[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-propan-2-yloxyoxan-2-yl]methyl] 3-hydroxy-3-methylpentanedioate
Synonyms:	Citrusoside B
Standard InCHIKey:	UBQMQNATXUCNPX-RCRVUDQWSA-N
Standard InCHI:	InChI=1S/C36H48O15/c1-19(2)48-34-32(42)31(41)30(40)25(50-34)18-47-28(38)16-36(6,44)17-29(39)51-26(35(4,5)43)9-7-20(3)11-13-46-33-21-8-10-27(37)49-24(21)15-23-22(33)12-14-45-23/h8,10-12,14-15,19,25-26,30-32,34,40-44H,7,9,13,16-18H2,1-6H3/b20-11+/t25-,26-,30-,31+,32-,34-,36?/m1/s1
SMILES:	C/C(=CCOc1c2ccoc2cc2c1ccc(=O)o2)/CC[C@H](C(O)(C)C)OC(=O)CC(CC(=O)OC[C@H]1O[C@@H](OC(C)C)[C@@H]([C@H]([C@@H]1O)O)O)(O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1651085
PubChem CID:	50901241
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003918] Saccharolipids

*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
NPO30686	Citrus hystrix	Species	Rutaceae	Eukaryota	n.a.	exocarp	n.a.	PMID[20964319]

☑ 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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT67	Individual Protein	Cholinesterase	Equus caballus	IC50	=	339000.0	nM	PMID[575422]

☑ 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 NPC325176 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	388
0.1-0.2	1625
0.2-0.3	3436
0.3-0.4	8336
0.4-0.5	10551
0.5-0.6	5051
0.6-0.7	5742
0.7-0.8	5777
0.8-0.85	1432
0.85-0.9	344
0.9-0.95	14
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9325	High Similarity	NPC14822
0.9264	High Similarity	NPC303210
0.9264	High Similarity	NPC49009
0.9264	High Similarity	NPC239270
0.9264	High Similarity	NPC95472
0.9146	High Similarity	NPC169
0.908	High Similarity	NPC17521
0.9024	High Similarity	NPC269495
0.897	High Similarity	NPC470607
0.897	High Similarity	NPC43761
0.8941	High Similarity	NPC76047
0.892	High Similarity	NPC73703
0.8909	High Similarity	NPC470606
0.8848	High Similarity	NPC45165
0.8834	High Similarity	NPC23253
0.8807	High Similarity	NPC106700
0.8795	High Similarity	NPC43638
0.8795	High Similarity	NPC23817
0.8788	High Similarity	NPC295608
0.8788	High Similarity	NPC250769
0.8788	High Similarity	NPC470604
0.8788	High Similarity	NPC278010
0.8788	High Similarity	NPC470605
0.8788	High Similarity	NPC470603
0.8779	High Similarity	NPC472584
0.8773	High Similarity	NPC191104
0.8772	High Similarity	NPC473202
0.8757	High Similarity	NPC124155
0.8757	High Similarity	NPC183672
0.8757	High Similarity	NPC257566
0.8743	High Similarity	NPC73511
0.8735	High Similarity	NPC127406
0.8735	High Similarity	NPC265480
0.8735	High Similarity	NPC149368
0.8727	High Similarity	NPC87304
0.8727	High Similarity	NPC268950
0.8727	High Similarity	NPC108706
0.8727	High Similarity	NPC131725
0.8727	High Similarity	NPC211158
0.8727	High Similarity	NPC78021
0.8721	High Similarity	NPC51404
0.8721	High Similarity	NPC120220
0.8712	High Similarity	NPC88445
0.8708	High Similarity	NPC282636
0.8708	High Similarity	NPC294863
0.8706	High Similarity	NPC72016
0.8706	High Similarity	NPC294722
0.8698	High Similarity	NPC131745
0.8698	High Similarity	NPC93215
0.8698	High Similarity	NPC44947
0.869	High Similarity	NPC74749
0.869	High Similarity	NPC19554
0.869	High Similarity	NPC200708
0.869	High Similarity	NPC472320
0.869	High Similarity	NPC43971
0.8683	High Similarity	NPC156457
0.8683	High Similarity	NPC313163
0.8683	High Similarity	NPC161749
0.8683	High Similarity	NPC122809
0.8683	High Similarity	NPC258035
0.8683	High Similarity	NPC197896
0.8678	High Similarity	NPC53917
0.8678	High Similarity	NPC224165
0.8678	High Similarity	NPC469601
0.8675	High Similarity	NPC279218
0.8675	High Similarity	NPC99233
0.8675	High Similarity	NPC108937
0.8667	High Similarity	NPC256141
0.8663	High Similarity	NPC5319
0.8659	High Similarity	NPC213723
0.8647	High Similarity	NPC179198
0.8647	High Similarity	NPC66087
0.8647	High Similarity	NPC471286
0.8647	High Similarity	NPC121703
0.8647	High Similarity	NPC278419
0.8647	High Similarity	NPC91288
0.8647	High Similarity	NPC472581
0.8639	High Similarity	NPC303913
0.8639	High Similarity	NPC45124
0.8639	High Similarity	NPC30655
0.8639	High Similarity	NPC101636
0.8639	High Similarity	NPC74854
0.8639	High Similarity	NPC47923
0.8631	High Similarity	NPC50430
0.8629	High Similarity	NPC107244
0.8623	High Similarity	NPC129053
0.8623	High Similarity	NPC321372
0.8623	High Similarity	NPC295613
0.8623	High Similarity	NPC474609
0.8623	High Similarity	NPC473657
0.8623	High Similarity	NPC475797
0.8623	High Similarity	NPC78554
0.8623	High Similarity	NPC109967
0.8623	High Similarity	NPC469936
0.8623	High Similarity	NPC474738
0.8614	High Similarity	NPC106625
0.8613	High Similarity	NPC175429
0.8613	High Similarity	NPC209550
0.8613	High Similarity	NPC212748
0.8613	High Similarity	NPC138990
0.8613	High Similarity	NPC277532
0.8606	High Similarity	NPC250488
0.8605	High Similarity	NPC320789
0.8598	High Similarity	NPC88886
0.8598	High Similarity	NPC104172
0.8596	High Similarity	NPC259007
0.8596	High Similarity	NPC204088
0.8596	High Similarity	NPC329215
0.8596	High Similarity	NPC7752
0.8596	High Similarity	NPC475979
0.8589	High Similarity	NPC74539
0.8589	High Similarity	NPC218685
0.8589	High Similarity	NPC304443
0.8588	High Similarity	NPC150164
0.8588	High Similarity	NPC298171
0.8588	High Similarity	NPC259834
0.8588	High Similarity	NPC219861
0.8588	High Similarity	NPC27942
0.8588	High Similarity	NPC190450
0.858	High Similarity	NPC469600
0.858	High Similarity	NPC306978
0.8571	High Similarity	NPC270044
0.8571	High Similarity	NPC6985
0.8563	High Similarity	NPC27408
0.8563	High Similarity	NPC95090
0.8563	High Similarity	NPC477530
0.8563	High Similarity	NPC235575
0.8554	High Similarity	NPC31627
0.8554	High Similarity	NPC259767
0.8554	High Similarity	NPC473996
0.8554	High Similarity	NPC476238
0.8554	High Similarity	NPC327269
0.8554	High Similarity	NPC259182
0.8554	High Similarity	NPC285623
0.8554	High Similarity	NPC121001
0.8554	High Similarity	NPC88484
0.8554	High Similarity	NPC477957
0.8547	High Similarity	NPC260504
0.8547	High Similarity	NPC298666
0.8547	High Similarity	NPC89809
0.8547	High Similarity	NPC473278
0.8547	High Similarity	NPC68592
0.8547	High Similarity	NPC323137
0.8547	High Similarity	NPC262222
0.8545	High Similarity	NPC155882
0.8545	High Similarity	NPC38775
0.8545	High Similarity	NPC191154
0.8545	High Similarity	NPC180351
0.8539	High Similarity	NPC473883
0.8539	High Similarity	NPC35924
0.8539	High Similarity	NPC199172
0.8529	High Similarity	NPC85707
0.8529	High Similarity	NPC472994
0.8529	High Similarity	NPC195685
0.8529	High Similarity	NPC159579
0.8529	High Similarity	NPC210961
0.8529	High Similarity	NPC216496
0.8529	High Similarity	NPC282169
0.8529	High Similarity	NPC477628
0.8529	High Similarity	NPC92589
0.8529	High Similarity	NPC259957
0.8529	High Similarity	NPC270675
0.8529	High Similarity	NPC48093
0.8529	High Similarity	NPC224530
0.8529	High Similarity	NPC129217
0.8529	High Similarity	NPC477629
0.8528	High Similarity	NPC296377
0.8528	High Similarity	NPC474302
0.8528	High Similarity	NPC469700
0.8523	High Similarity	NPC475233
0.8521	High Similarity	NPC279732
0.8521	High Similarity	NPC473634
0.8521	High Similarity	NPC22062
0.8521	High Similarity	NPC138811
0.8514	High Similarity	NPC98776
0.8514	High Similarity	NPC72455
0.8512	High Similarity	NPC170475
0.8512	High Similarity	NPC206378
0.8506	High Similarity	NPC188815
0.8503	High Similarity	NPC469405
0.8503	High Similarity	NPC122365
0.8503	High Similarity	NPC7989
0.8503	High Similarity	NPC83283
0.8503	High Similarity	NPC39360
0.8503	High Similarity	NPC29763
0.8503	High Similarity	NPC223701
0.8503	High Similarity	NPC472583
0.8503	High Similarity	NPC210003
0.8503	High Similarity	NPC143851
0.8497	Intermediate Similarity	NPC476459
0.8497	Intermediate Similarity	NPC116745
0.8497	Intermediate Similarity	NPC249977
0.8497	Intermediate Similarity	NPC135345
0.8494	Intermediate Similarity	NPC472422
0.8494	Intermediate Similarity	NPC474772
0.8494	Intermediate Similarity	NPC471677
0.8494	Intermediate Similarity	NPC472580
0.8494	Intermediate Similarity	NPC471676
0.8494	Intermediate Similarity	NPC190217
0.8494	Intermediate Similarity	NPC472420

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 NPC325176 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	331
0.1-0.2	907
0.2-0.3	1827
0.3-0.4	2689
0.4-0.5	2051
0.5-0.6	946
0.6-0.7	244
0.7-0.8	128
0.8-0.85	22
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8947	High Similarity	NPD6559	Discontinued
0.8683	High Similarity	NPD4381	Clinical (unspecified phase)
0.8663	High Similarity	NPD7804	Clinical (unspecified phase)
0.8589	High Similarity	NPD920	Approved
0.8503	High Similarity	NPD7096	Clinical (unspecified phase)
0.8497	Intermediate Similarity	NPD3818	Discontinued
0.8466	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD7075	Discontinued
0.8344	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6801	Discontinued
0.8323	Intermediate Similarity	NPD4380	Phase 2
0.8284	Intermediate Similarity	NPD7819	Suspended
0.8239	Intermediate Similarity	NPD7054	Approved
0.8198	Intermediate Similarity	NPD919	Approved
0.8192	Intermediate Similarity	NPD7472	Approved
0.8192	Intermediate Similarity	NPD7074	Phase 3
0.8166	Intermediate Similarity	NPD7411	Suspended
0.816	Intermediate Similarity	NPD1243	Approved
0.8156	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8156	Intermediate Similarity	NPD7808	Phase 3
0.8101	Intermediate Similarity	NPD7251	Discontinued
0.8045	Intermediate Similarity	NPD6797	Phase 2
0.8035	Intermediate Similarity	NPD3749	Approved
0.8023	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1247	Approved
0.8	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7978	Intermediate Similarity	NPD8434	Phase 2
0.7966	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD6799	Approved
0.7919	Intermediate Similarity	NPD3817	Phase 2
0.7917	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD2796	Approved
0.7861	Intermediate Similarity	NPD8455	Phase 2
0.7841	Intermediate Similarity	NPD5494	Approved
0.7824	Intermediate Similarity	NPD5403	Approved
0.7816	Intermediate Similarity	NPD5402	Approved
0.7814	Intermediate Similarity	NPD8312	Approved
0.7814	Intermediate Similarity	NPD8313	Approved
0.7811	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD5401	Approved
0.7803	Intermediate Similarity	NPD1934	Approved
0.7791	Intermediate Similarity	NPD6599	Discontinued
0.7771	Intermediate Similarity	NPD7768	Phase 2
0.7771	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD1549	Phase 2
0.7735	Intermediate Similarity	NPD5844	Phase 1
0.7711	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD3882	Suspended
0.7667	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD6166	Phase 2
0.7667	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD2801	Approved
0.7653	Intermediate Similarity	NPD7584	Approved
0.7624	Intermediate Similarity	NPD7473	Discontinued
0.7619	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD1510	Phase 2
0.7588	Intermediate Similarity	NPD7783	Phase 2
0.7588	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD8151	Discontinued
0.7563	Intermediate Similarity	NPD7583	Approved
0.7556	Intermediate Similarity	NPD6232	Discontinued
0.7554	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD7585	Approved
0.7514	Intermediate Similarity	NPD7685	Pre-registration
0.7513	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2532	Approved
0.75	Intermediate Similarity	NPD7435	Discontinued
0.75	Intermediate Similarity	NPD2534	Approved
0.75	Intermediate Similarity	NPD6959	Discontinued
0.75	Intermediate Similarity	NPD2533	Approved
0.75	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7199	Phase 2
0.7486	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD4628	Phase 3
0.7471	Intermediate Similarity	NPD1653	Approved
0.7461	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD1511	Approved
0.744	Intermediate Similarity	NPD1551	Phase 2
0.7439	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD2313	Discontinued
0.7429	Intermediate Similarity	NPD3226	Approved
0.7418	Intermediate Similarity	NPD3926	Phase 2
0.7412	Intermediate Similarity	NPD2800	Approved
0.7401	Intermediate Similarity	NPD37	Approved
0.7391	Intermediate Similarity	NPD3751	Discontinued
0.7391	Intermediate Similarity	NPD7228	Approved
0.7381	Intermediate Similarity	NPD2799	Discontinued
0.7374	Intermediate Similarity	NPD4965	Approved
0.7374	Intermediate Similarity	NPD4966	Approved
0.7374	Intermediate Similarity	NPD4967	Phase 2
0.7368	Intermediate Similarity	NPD3750	Approved
0.7366	Intermediate Similarity	NPD5953	Discontinued
0.7363	Intermediate Similarity	NPD7874	Approved
0.7363	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD3787	Discontinued
0.736	Intermediate Similarity	NPD1465	Phase 2
0.7356	Intermediate Similarity	NPD1512	Approved
0.7351	Intermediate Similarity	NPD7286	Phase 2
0.7349	Intermediate Similarity	NPD1240	Approved
0.7347	Intermediate Similarity	NPD6781	Approved
0.7347	Intermediate Similarity	NPD6779	Approved
0.7347	Intermediate Similarity	NPD6782	Approved
0.7347	Intermediate Similarity	NPD6780	Approved
0.7347	Intermediate Similarity	NPD6777	Approved
0.7347	Intermediate Similarity	NPD6778	Approved
0.7347	Intermediate Similarity	NPD6776	Approved
0.733	Intermediate Similarity	NPD7458	Discontinued
0.7323	Intermediate Similarity	NPD7696	Phase 3
0.7323	Intermediate Similarity	NPD7698	Approved
0.7323	Intermediate Similarity	NPD7697	Approved
0.7322	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD6832	Phase 2
0.7305	Intermediate Similarity	NPD5124	Phase 1
0.7305	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD2344	Approved
0.7293	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD6234	Discontinued
0.7286	Intermediate Similarity	NPD7870	Phase 2
0.7286	Intermediate Similarity	NPD7871	Phase 2
0.7278	Intermediate Similarity	NPD7033	Discontinued
0.7278	Intermediate Similarity	NPD3748	Approved
0.7264	Intermediate Similarity	NPD7701	Phase 2
0.7262	Intermediate Similarity	NPD1607	Approved
0.7251	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD2935	Discontinued
0.7234	Intermediate Similarity	NPD7240	Approved
0.722	Intermediate Similarity	NPD7930	Approved
0.7209	Intermediate Similarity	NPD1652	Phase 2
0.7202	Intermediate Similarity	NPD1933	Approved
0.72	Intermediate Similarity	NPD8320	Phase 1
0.72	Intermediate Similarity	NPD8319	Approved
0.7196	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD2346	Discontinued
0.7186	Intermediate Similarity	NPD6823	Phase 2
0.7174	Intermediate Similarity	NPD7229	Phase 3
0.7167	Intermediate Similarity	NPD5761	Phase 2
0.7167	Intermediate Similarity	NPD5760	Phase 2
0.7157	Intermediate Similarity	NPD7699	Phase 2
0.7157	Intermediate Similarity	NPD7700	Phase 2
0.7157	Intermediate Similarity	NPD7801	Approved
0.7151	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD2424	Discontinued
0.715	Intermediate Similarity	NPD4287	Approved
0.7143	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD8150	Discontinued
0.7126	Intermediate Similarity	NPD2309	Approved
0.7097	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD6534	Approved
0.7092	Intermediate Similarity	NPD6535	Approved
0.7081	Intermediate Similarity	NPD6808	Phase 2
0.7081	Intermediate Similarity	NPD5710	Approved
0.7081	Intermediate Similarity	NPD5711	Approved
0.7069	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD8404	Phase 2
0.7059	Intermediate Similarity	NPD6651	Approved
0.7041	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD8285	Discontinued
0.7024	Intermediate Similarity	NPD3268	Approved
0.7018	Intermediate Similarity	NPD7097	Phase 1
0.7014	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD447	Suspended
0.7	Intermediate Similarity	NPD6355	Discontinued
0.6995	Remote Similarity	NPD7999	Approved
0.6988	Remote Similarity	NPD2798	Approved
0.6977	Remote Similarity	NPD4308	Phase 3
0.6963	Remote Similarity	NPD6764	Approved
0.6963	Remote Similarity	NPD6765	Approved
0.6951	Remote Similarity	NPD9717	Approved
0.6944	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD1203	Approved
0.6923	Remote Similarity	NPD6798	Discontinued
0.6919	Remote Similarity	NPD4360	Phase 2
0.6919	Remote Similarity	NPD4363	Phase 3
0.6915	Remote Similarity	NPD2403	Approved
0.6915	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD230	Phase 1
0.6901	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7266	Discontinued
0.6893	Remote Similarity	NPD5058	Phase 3
0.689	Remote Similarity	NPD1091	Approved
0.689	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD5889	Approved
0.6868	Remote Similarity	NPD5890	Approved
0.6845	Remote Similarity	NPD8127	Discontinued
0.6842	Remote Similarity	NPD7799	Discontinued
0.6842	Remote Similarity	NPD4307	Phase 2
0.6836	Remote Similarity	NPD6190	Approved
0.6831	Remote Similarity	NPD6844	Discontinued
0.6826	Remote Similarity	NPD3267	Approved
0.6826	Remote Similarity	NPD2797	Approved
0.6826	Remote Similarity	NPD3266	Approved
0.6821	Remote Similarity	NPD6784	Approved
0.6821	Remote Similarity	NPD6785	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