NPASS Compound

Structure

NPC469384 OpenBabel07101719512D 44 48 0 0 1 0 0 0 0 0999 V2000 4.6140 -3.7556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3340 -2.2630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4800 0.7444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8385 1.3084 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6476 0.7206 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8080 1.7226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8135 1.8271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8205 -0.0929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8819 -0.7556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0159 -4.2556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7480 -4.2556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9250 0.9016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0159 0.7444 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2024 1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8819 0.2444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5430 -0.2739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6295 -0.6807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1499 -3.7556 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1499 0.2444 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1160 1.4894 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2839 -4.2556 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5822 -3.7556 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5822 -2.7556 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7480 0.7444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1499 -0.7556 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2839 -2.2556 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7480 -5.2556 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3520 -0.8617 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2205 2.4839 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2839 -5.2556 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4482 -4.2556 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4482 -2.2556 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7480 1.7444 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6637 -0.6386 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5250 -1.6752 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6140 0.2444 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8819 -3.7556 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0159 -1.2556 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1499 -2.7556 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2839 -1.2556 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 38 1 0 0 0 0 3 39 1 0 0 0 0 4 5 2 0 0 0 0 4 13 1 0 0 0 0 5 17 1 0 0 0 0 6 7 2 0 0 0 0 8 13 2 0 0 0 0 8 18 1 0 0 0 0 9 15 2 0 0 0 0 9 29 1 0 0 0 0 10 16 2 0 0 0 0 10 41 1 0 0 0 0 11 40 1 0 0 0 0 12 30 2 0 0 0 0 12 40 1 0 0 0 0 13 21 1 0 0 0 0 14 6 1 6 0 0 0 14 16 1 0 0 0 0 14 20 1 0 0 0 0 15 21 1 0 0 0 0 15 26 1 0 0 0 0 16 25 1 0 0 0 0 17 18 2 0 0 0 0 17 31 1 0 0 0 0 18 38 1 0 0 0 0 19 11 1 6 0 0 0 19 22 1 0 0 0 0 19 42 1 0 0 0 0 20 27 1 0 0 0 0 20 29 1 6 0 0 0 21 32 1 1 0 0 0 22 23 1 0 0 0 0 22 33 1 1 0 0 0 23 24 1 0 0 0 0 23 34 1 6 0 0 0 24 28 1 0 0 0 0 24 35 1 1 0 0 0 25 36 2 0 0 0 0 25 39 1 0 0 0 0 26 37 2 0 0 0 0 26 44 1 0 0 0 0 27 41 1 0 0 0 0 27 43 1 1 0 0 0 28 42 1 0 0 0 0 28 43 1 6 0 0 0 29 7 1 1 0 0 0 29 44 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	262.12
Volume:	272.862
LogP:	2.038
LogD:	2.13
LogS:	-2.492
# Rotatable Bonds:	2
TPSA:	73.83
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.754
Synthetic Accessibility Score:	4.187
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.06
MDCK Permeability:	1.028093265631469e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.718
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.012

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.054
Plasma Protein Binding (PPB):	87.91133880615234%
Volume Distribution (VD):	1.473
Pgp-substrate:	18.220060348510742%

ADMET: Metabolism

CYP1A2-inhibitor:	0.963
CYP1A2-substrate:	0.721
CYP2C19-inhibitor:	0.051
CYP2C19-substrate:	0.789
CYP2C9-inhibitor:	0.05
CYP2C9-substrate:	0.554
CYP2D6-inhibitor:	0.027
CYP2D6-substrate:	0.255
CYP3A4-inhibitor:	0.023
CYP3A4-substrate:	0.44

ADMET: Excretion

Clearance (CL):	9.404
Half-life (T1/2):	0.949

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.921
Drug-inuced Liver Injury (DILI):	0.982
AMES Toxicity:	0.557
Rat Oral Acute Toxicity:	0.562
Maximum Recommended Daily Dose:	0.686
Skin Sensitization:	0.694
Carcinogencity:	0.814
Eye Corrosion:	0.003
Eye Irritation:	0.02
Respiratory Toxicity:	0.59

Download Data

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

Natural Product: NPC469384

Natural Product ID:	NPC469384
*Common Name:**	Methyl (1S,4As,7R,7As)-1-[(2S,3R,4S,5S,6R)-6-(Acetyloxymethyl)-3,4,5-Trihydroxyoxan-2-Yl]Oxy-4'-[(R)-Hydroxy-(4-Hydroxy-3-Methoxyphenyl)Methyl]-5'-Oxospiro[4A,7A-Dihydro-1H-Cyclopenta[C]Pyran-7,2'-Furan]-4-Carboxylate
IUPAC Name:	methyl (1S,4aS,7R,7aS)-1-[(2S,3R,4S,5S,6R)-6-(acetyloxymethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-4'-[(R)-hydroxy-(4-hydroxy-3-methoxyphenyl)methyl]-5'-oxospiro[4a,7a-dihydro-1H-cyclopenta[c]pyran-7,2'-furan]-4-carboxylate
Synonyms:
Standard InCHIKey:	UJGUSKGCTXMCER-LPWQJEQNSA-N
Standard InCHI:	InChI=1S/C29H32O15/c1-12(30)40-11-19-22(33)23(34)24(35)28(42-19)43-27-20-14(16(10-41-27)25(36)39-3)6-7-29(20)9-15(26(37)44-29)21(32)13-4-5-17(31)18(8-13)38-2/h4-10,14,19-24,27-28,31-35H,11H2,1-3H3/t14-,19-,20-,21-,22-,23+,24-,27+,28+,29-/m1/s1
SMILES:	COC(=O)C1=CO[C@H]([C@H]2[C@@H]1C=C[C@@]12OC(=O)C(=C1)[C@@H](c1ccc(c(c1)OC)O)O)O[C@@H]1O[C@H](COC(=O)C)[C@H]([C@@H]([C@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1077223
PubChem CID:	46881624
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0004081] Iridoid O-glycosides

*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
NPO22304	Morinda morindoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12542353]
NPO22304	Morinda morindoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20149652]
NPO22304	Morinda morindoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7775983]
NPO22304	Morinda morindoides	Species	Rubiaceae	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	1
Others	1

Activity Type	# Activity
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	100.0	nM	PMID[469446]
NPT27	Others	Unspecified		GI	=	9.3	%	PMID[469446]

☑ 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 NPC469384 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	342
0.1-0.2	1291
0.2-0.3	3026
0.3-0.4	6390
0.4-0.5	10156
0.5-0.6	6695
0.6-0.7	7689
0.7-0.8	6444
0.8-0.85	592
0.85-0.9	60
0.9-0.95	8
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9933	High Similarity	NPC286919
0.9933	High Similarity	NPC475663
0.9551	High Similarity	NPC180586
0.9355	High Similarity	NPC76211
0.9231	High Similarity	NPC179914
0.9216	High Similarity	NPC203664
0.92	High Similarity	NPC119773
0.92	High Similarity	NPC474268
0.92	High Similarity	NPC143246
0.92	High Similarity	NPC475539
0.9133	High Similarity	NPC475528
0.9067	High Similarity	NPC63304
0.9045	High Similarity	NPC226759
0.902	High Similarity	NPC478242
0.8938	High Similarity	NPC476011
0.8903	High Similarity	NPC474620
0.8896	High Similarity	NPC21956
0.8861	High Similarity	NPC478055
0.8812	High Similarity	NPC474936
0.8808	High Similarity	NPC296643
0.8797	High Similarity	NPC475484
0.8797	High Similarity	NPC131532
0.8797	High Similarity	NPC38699
0.879	High Similarity	NPC115466
0.879	High Similarity	NPC61604
0.879	High Similarity	NPC245615
0.879	High Similarity	NPC44730
0.879	High Similarity	NPC299706
0.8782	High Similarity	NPC478249
0.8782	High Similarity	NPC269914
0.8773	High Similarity	NPC130730
0.8773	High Similarity	NPC301910
0.875	High Similarity	NPC469654
0.8742	High Similarity	NPC163635
0.8742	High Similarity	NPC471405
0.8734	High Similarity	NPC191046
0.8734	High Similarity	NPC194095
0.8734	High Similarity	NPC327032
0.8718	High Similarity	NPC69367
0.8712	High Similarity	NPC475738
0.8696	High Similarity	NPC44507
0.8693	High Similarity	NPC110063
0.8688	High Similarity	NPC472860
0.8688	High Similarity	NPC187205
0.8688	High Similarity	NPC223335
0.8688	High Similarity	NPC40920
0.8684	High Similarity	NPC140502
0.8679	High Similarity	NPC10205
0.8671	High Similarity	NPC157898
0.865	High Similarity	NPC109990
0.8645	High Similarity	NPC473149
0.8636	High Similarity	NPC252292
0.8636	High Similarity	NPC34587
0.8636	High Similarity	NPC100998
0.8636	High Similarity	NPC476382
0.8636	High Similarity	NPC34927
0.8627	High Similarity	NPC475213
0.8627	High Similarity	NPC152796
0.8609	High Similarity	NPC226005
0.8608	High Similarity	NPC134905
0.8608	High Similarity	NPC36130
0.8608	High Similarity	NPC478268
0.86	High Similarity	NPC157554
0.8599	High Similarity	NPC147224
0.8599	High Similarity	NPC470934
0.8599	High Similarity	NPC158635
0.8599	High Similarity	NPC188393
0.8599	High Similarity	NPC229882
0.8599	High Similarity	NPC205054
0.859	High Similarity	NPC308178
0.8589	High Similarity	NPC206815
0.8589	High Similarity	NPC145847
0.8589	High Similarity	NPC41009
0.8581	High Similarity	NPC473867
0.858	High Similarity	NPC239966
0.858	High Similarity	NPC203020
0.8571	High Similarity	NPC469438
0.8571	High Similarity	NPC133984
0.8571	High Similarity	NPC296659
0.8571	High Similarity	NPC202391
0.8562	High Similarity	NPC186316
0.8553	High Similarity	NPC89693
0.8553	High Similarity	NPC478241
0.8553	High Similarity	NPC137813
0.8553	High Similarity	NPC229548
0.8545	High Similarity	NPC282551
0.8544	High Similarity	NPC475379
0.8537	High Similarity	NPC100420
0.8535	High Similarity	NPC111785
0.8526	High Similarity	NPC232992
0.8519	High Similarity	NPC160780
0.8519	High Similarity	NPC289811
0.8516	High Similarity	NPC210330
0.8516	High Similarity	NPC262182
0.8516	High Similarity	NPC83743
0.8516	High Similarity	NPC216819
0.8516	High Similarity	NPC287615
0.8512	High Similarity	NPC316539
0.8509	High Similarity	NPC478248
0.8509	High Similarity	NPC475378
0.8509	High Similarity	NPC11411
0.8509	High Similarity	NPC228357
0.8506	High Similarity	NPC478239
0.85	High Similarity	NPC477299
0.85	High Similarity	NPC136757
0.85	High Similarity	NPC472128
0.85	High Similarity	NPC472127
0.8494	Intermediate Similarity	NPC298847
0.8494	Intermediate Similarity	NPC128403
0.8494	Intermediate Similarity	NPC116745
0.8491	Intermediate Similarity	NPC106818
0.8491	Intermediate Similarity	NPC267091
0.8491	Intermediate Similarity	NPC289438
0.8487	Intermediate Similarity	NPC220942
0.8487	Intermediate Similarity	NPC100389
0.8485	Intermediate Similarity	NPC472130
0.8485	Intermediate Similarity	NPC472131
0.8481	Intermediate Similarity	NPC240592
0.8481	Intermediate Similarity	NPC117346
0.8481	Intermediate Similarity	NPC12006
0.848	Intermediate Similarity	NPC188217
0.8471	Intermediate Similarity	NPC23677
0.8466	Intermediate Similarity	NPC138993
0.8466	Intermediate Similarity	NPC239818
0.8466	Intermediate Similarity	NPC218471
0.8462	Intermediate Similarity	NPC212808
0.8462	Intermediate Similarity	NPC98356
0.8462	Intermediate Similarity	NPC469354
0.8457	Intermediate Similarity	NPC1913
0.8457	Intermediate Similarity	NPC104275
0.8457	Intermediate Similarity	NPC4747
0.8452	Intermediate Similarity	NPC473281
0.8452	Intermediate Similarity	NPC77922
0.8452	Intermediate Similarity	NPC235575
0.8452	Intermediate Similarity	NPC84181
0.8452	Intermediate Similarity	NPC297342
0.8447	Intermediate Similarity	NPC172920
0.8447	Intermediate Similarity	NPC156624
0.8442	Intermediate Similarity	NPC157816
0.8442	Intermediate Similarity	NPC104956
0.8438	Intermediate Similarity	NPC310661
0.8438	Intermediate Similarity	NPC105827
0.8438	Intermediate Similarity	NPC87403
0.8431	Intermediate Similarity	NPC202700
0.843	Intermediate Similarity	NPC199172
0.843	Intermediate Similarity	NPC35924
0.8428	Intermediate Similarity	NPC243891
0.8428	Intermediate Similarity	NPC289021
0.8428	Intermediate Similarity	NPC158546
0.8424	Intermediate Similarity	NPC227297
0.8421	Intermediate Similarity	NPC304152
0.8418	Intermediate Similarity	NPC98809
0.8418	Intermediate Similarity	NPC476398
0.8418	Intermediate Similarity	NPC96599
0.8418	Intermediate Similarity	NPC106138
0.8418	Intermediate Similarity	NPC470933
0.8418	Intermediate Similarity	NPC476394
0.8418	Intermediate Similarity	NPC259347
0.8418	Intermediate Similarity	NPC306890
0.8418	Intermediate Similarity	NPC473427
0.8418	Intermediate Similarity	NPC471062
0.8418	Intermediate Similarity	NPC476386
0.8418	Intermediate Similarity	NPC94871
0.8415	Intermediate Similarity	NPC472859
0.8415	Intermediate Similarity	NPC25389
0.8415	Intermediate Similarity	NPC311803
0.8412	Intermediate Similarity	NPC469397
0.8402	Intermediate Similarity	NPC472993
0.8397	Intermediate Similarity	NPC223185
0.8393	Intermediate Similarity	NPC43434
0.8393	Intermediate Similarity	NPC212748
0.8393	Intermediate Similarity	NPC472129
0.8387	Intermediate Similarity	NPC477898
0.8383	Intermediate Similarity	NPC229729
0.8377	Intermediate Similarity	NPC472711
0.8377	Intermediate Similarity	NPC186406
0.8375	Intermediate Similarity	NPC477699
0.8375	Intermediate Similarity	NPC56184
0.8373	Intermediate Similarity	NPC311830
0.8373	Intermediate Similarity	NPC22832
0.8366	Intermediate Similarity	NPC328273
0.8366	Intermediate Similarity	NPC321184
0.8366	Intermediate Similarity	NPC220936
0.8366	Intermediate Similarity	NPC321638
0.8366	Intermediate Similarity	NPC171134
0.8366	Intermediate Similarity	NPC31745
0.8365	Intermediate Similarity	NPC227980
0.8365	Intermediate Similarity	NPC257970
0.8365	Intermediate Similarity	NPC470927
0.8364	Intermediate Similarity	NPC285108
0.8364	Intermediate Similarity	NPC33298
0.8364	Intermediate Similarity	NPC246024
0.8364	Intermediate Similarity	NPC22324
0.8364	Intermediate Similarity	NPC76687
0.8355	Intermediate Similarity	NPC186418
0.8355	Intermediate Similarity	NPC470572
0.8355	Intermediate Similarity	NPC472132
0.8355	Intermediate Similarity	NPC37468
0.8354	Intermediate Similarity	NPC473428
0.8354	Intermediate Similarity	NPC116229

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 NPC469384 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	280
0.1-0.2	828
0.2-0.3	1785
0.3-0.4	2623
0.4-0.5	1976
0.5-0.6	1083
0.6-0.7	477
0.7-0.8	91
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8623	High Similarity	NPD7685	Pre-registration
0.8333	Intermediate Similarity	NPD7054	Approved
0.8314	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8284	Intermediate Similarity	NPD7472	Approved
0.828	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8274	Intermediate Similarity	NPD3818	Discontinued
0.8247	Intermediate Similarity	NPD7266	Discontinued
0.8176	Intermediate Similarity	NPD7074	Phase 3
0.8166	Intermediate Similarity	NPD7228	Approved
0.814	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8081	Intermediate Similarity	NPD7251	Discontinued
0.8075	Intermediate Similarity	NPD1653	Approved
0.8072	Intermediate Similarity	NPD6234	Discontinued
0.8035	Intermediate Similarity	NPD7808	Phase 3
0.8023	Intermediate Similarity	NPD6797	Phase 2
0.7952	Intermediate Similarity	NPD4967	Phase 2
0.7952	Intermediate Similarity	NPD4966	Approved
0.7952	Intermediate Similarity	NPD4965	Approved
0.7925	Intermediate Similarity	NPD6190	Approved
0.7904	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD37	Approved
0.787	Intermediate Similarity	NPD7199	Phase 2
0.7771	Intermediate Similarity	NPD1934	Approved
0.7738	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD3817	Phase 2
0.7674	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD7240	Approved
0.763	Intermediate Similarity	NPD6166	Phase 2
0.763	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD2801	Approved
0.7619	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD6559	Discontinued
0.7569	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD4380	Phase 2
0.7531	Intermediate Similarity	NPD4628	Phase 3
0.7529	Intermediate Similarity	NPD3882	Suspended
0.7486	Intermediate Similarity	NPD8312	Approved
0.7486	Intermediate Similarity	NPD8313	Approved
0.7486	Intermediate Similarity	NPD7473	Discontinued
0.7485	Intermediate Similarity	NPD7075	Discontinued
0.7468	Intermediate Similarity	NPD230	Phase 1
0.7457	Intermediate Similarity	NPD8127	Discontinued
0.7414	Intermediate Similarity	NPD6232	Discontinued
0.7412	Intermediate Similarity	NPD8455	Phase 2
0.7407	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD5844	Phase 1
0.7394	Intermediate Similarity	NPD1511	Approved
0.7345	Intermediate Similarity	NPD3751	Discontinued
0.734	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD7033	Discontinued
0.7325	Intermediate Similarity	NPD3027	Phase 3
0.7318	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7819	Suspended
0.731	Intermediate Similarity	NPD1465	Phase 2
0.731	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD9494	Approved
0.7305	Intermediate Similarity	NPD1512	Approved
0.7299	Intermediate Similarity	NPD5494	Approved
0.7296	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD7680	Approved
0.7273	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD6674	Discontinued
0.7255	Intermediate Similarity	NPD3705	Approved
0.7253	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD6801	Discontinued
0.7235	Intermediate Similarity	NPD7028	Phase 2
0.7216	Intermediate Similarity	NPD3787	Discontinued
0.7212	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD4110	Phase 3
0.7212	Intermediate Similarity	NPD8166	Discontinued
0.7212	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD6653	Approved
0.7204	Intermediate Similarity	NPD7296	Approved
0.7188	Intermediate Similarity	NPD7435	Discontinued
0.7176	Intermediate Similarity	NPD7458	Discontinued
0.7174	Intermediate Similarity	NPD8434	Phase 2
0.7172	Intermediate Similarity	NPD7930	Approved
0.7168	Intermediate Similarity	NPD5402	Approved
0.7168	Intermediate Similarity	NPD5353	Approved
0.7143	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6355	Discontinued
0.7143	Intermediate Similarity	NPD447	Suspended
0.7143	Intermediate Similarity	NPD1933	Approved
0.7093	Intermediate Similarity	NPD6385	Approved
0.7093	Intermediate Similarity	NPD6386	Approved
0.7083	Intermediate Similarity	NPD6799	Approved
0.7081	Intermediate Similarity	NPD1613	Approved
0.7081	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD2935	Discontinued
0.7069	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5403	Approved
0.7059	Intermediate Similarity	NPD1357	Approved
0.7055	Intermediate Similarity	NPD7097	Phase 1
0.7041	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD2532	Approved
0.7041	Intermediate Similarity	NPD2534	Approved
0.7041	Intermediate Similarity	NPD2533	Approved
0.7032	Intermediate Similarity	NPD1091	Approved
0.7031	Intermediate Similarity	NPD6780	Approved
0.7031	Intermediate Similarity	NPD6776	Approved
0.7031	Intermediate Similarity	NPD6779	Approved
0.7031	Intermediate Similarity	NPD6781	Approved
0.7031	Intermediate Similarity	NPD6777	Approved
0.7031	Intermediate Similarity	NPD6778	Approved
0.7031	Intermediate Similarity	NPD6782	Approved
0.7026	Intermediate Similarity	NPD7999	Approved
0.7025	Intermediate Similarity	NPD5647	Approved
0.7019	Intermediate Similarity	NPD6233	Phase 2
0.7012	Intermediate Similarity	NPD1510	Phase 2
0.7005	Intermediate Similarity	NPD8151	Discontinued
0.6994	Remote Similarity	NPD7411	Suspended
0.6993	Remote Similarity	NPD9545	Approved
0.6989	Remote Similarity	NPD8150	Discontinued
0.6988	Remote Similarity	NPD1549	Phase 2
0.6987	Remote Similarity	NPD1608	Approved
0.697	Remote Similarity	NPD7874	Approved
0.697	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD919	Approved
0.6946	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD5401	Approved
0.6941	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD6599	Discontinued
0.6935	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD7783	Phase 2
0.6928	Remote Similarity	NPD6005	Phase 3
0.6928	Remote Similarity	NPD6002	Phase 3
0.6928	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD6004	Phase 3
0.6923	Remote Similarity	NPD7698	Approved
0.6923	Remote Similarity	NPD7696	Phase 3
0.6923	Remote Similarity	NPD7697	Approved
0.6894	Remote Similarity	NPD7095	Approved
0.6893	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD8320	Phase 1
0.6888	Remote Similarity	NPD8319	Approved
0.6888	Remote Similarity	NPD7871	Phase 2
0.6888	Remote Similarity	NPD7870	Phase 2
0.6872	Remote Similarity	NPD6823	Phase 2
0.6871	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD3620	Phase 2
0.6869	Remote Similarity	NPD7701	Phase 2
0.6868	Remote Similarity	NPD7799	Discontinued
0.6867	Remote Similarity	NPD2796	Approved
0.6867	Remote Similarity	NPD228	Approved
0.6867	Remote Similarity	NPD6099	Approved
0.6867	Remote Similarity	NPD6100	Approved
0.6855	Remote Similarity	NPD2797	Approved
0.6852	Remote Similarity	NPD6798	Discontinued
0.6852	Remote Similarity	NPD3268	Approved
0.6852	Remote Similarity	NPD3764	Approved
0.6851	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.685	Remote Similarity	NPD7801	Approved
0.6845	Remote Similarity	NPD1652	Phase 2
0.6842	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD7768	Phase 2
0.6832	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD5124	Phase 1
0.6829	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7584	Approved
0.6818	Remote Similarity	NPD5536	Phase 2
0.6813	Remote Similarity	NPD2798	Approved
0.6811	Remote Similarity	NPD7038	Approved
0.6811	Remote Similarity	NPD7039	Approved
0.6805	Remote Similarity	NPD3750	Approved
0.6802	Remote Similarity	NPD6273	Approved
0.6798	Remote Similarity	NPD3749	Approved
0.6796	Remote Similarity	NPD5242	Approved
0.6795	Remote Similarity	NPD17	Approved
0.6786	Remote Similarity	NPD2424	Discontinued
0.6784	Remote Similarity	NPD7585	Approved
0.6782	Remote Similarity	NPD3455	Phase 2
0.6782	Remote Similarity	NPD3226	Approved
0.6778	Remote Similarity	NPD6959	Discontinued
0.6772	Remote Similarity	NPD9269	Phase 2
0.6771	Remote Similarity	NPD6535	Approved
0.6771	Remote Similarity	NPD6534	Approved
0.677	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.677	Remote Similarity	NPD2861	Phase 2
0.6768	Remote Similarity	NPD4060	Phase 1
0.6768	Remote Similarity	NPD1240	Approved
0.6766	Remote Similarity	NPD2438	Suspended
0.6753	Remote Similarity	NPD7700	Phase 2
0.6753	Remote Similarity	NPD7699	Phase 2
0.6753	Remote Similarity	NPD4420	Approved
0.6744	Remote Similarity	NPD3146	Approved
0.6744	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.674	Remote Similarity	NPD7315	Approved
0.6737	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD7583	Approved
0.6728	Remote Similarity	NPD6832	Phase 2
0.6726	Remote Similarity	NPD1375	Discontinued

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