NPASS Compound

Structure

NPC473275 OpenBabel07101719252D 50 53 0 0 1 0 0 0 0 0999 V2000 -6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5000 -2.8660 0.0000 C 0 0 0 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 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0000 -3.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 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 -2.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -3.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5000 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5000 -4.5981 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 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5000 -4.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 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 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5000 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0000 -5.4641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -5.4641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0000 -3.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -2.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -2.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 47 1 0 0 0 0 2 8 2 0 0 0 0 2 19 1 0 0 0 0 3 9 2 0 0 0 0 3 20 1 0 0 0 0 4 10 2 0 0 0 0 4 21 1 0 0 0 0 5 11 1 0 0 0 0 5 19 1 0 0 0 0 6 12 2 0 0 0 0 6 21 1 0 0 0 0 7 13 1 0 0 0 0 7 20 1 0 0 0 0 8 22 1 0 0 0 0 9 23 1 0 0 0 0 10 24 1 0 0 0 0 11 30 1 0 0 0 0 12 31 1 0 0 0 0 13 32 1 0 0 0 0 14 19 2 0 0 0 0 14 25 1 0 0 0 0 15 20 2 0 0 0 0 15 26 1 0 0 0 0 16 21 2 0 0 0 0 16 27 1 0 0 0 0 17 28 1 0 0 0 0 17 35 1 0 0 0 0 18 29 1 0 0 0 0 18 35 1 0 0 0 0 22 25 2 0 0 0 0 22 36 1 0 0 0 0 23 26 2 0 0 0 0 23 37 1 0 0 0 0 24 27 2 0 0 0 0 24 38 1 0 0 0 0 25 39 1 0 0 0 0 26 40 1 0 0 0 0 27 47 1 0 0 0 0 28 33 1 0 0 0 0 28 48 1 6 0 0 0 29 33 1 0 0 0 0 29 49 1 1 0 0 0 30 41 2 0 0 0 0 30 48 1 0 0 0 0 31 42 2 0 0 0 0 31 49 1 0 0 0 0 32 43 2 0 0 0 0 32 50 1 0 0 0 0 33 44 1 6 0 0 0 34 45 2 0 0 0 0 34 46 1 0 0 0 0 35 34 1 6 0 0 0 35 50 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	696.21
Volume:	674.633
LogP:	2.825
LogD:	1.064
LogS:	-2.95
# Rotatable Bonds:	16
TPSA:	246.81
# H-Bond Aceptor:	15
# H-Bond Donor:	7
# Rings:	4
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.059
Synthetic Accessibility Score:	4.372
Fsp3:	0.314
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.194
MDCK Permeability:	4.956887096341234e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.947
Human Intestinal Absorption (HIA):	0.945
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	98.09915161132812%
Volume Distribution (VD):	0.356
Pgp-substrate:	1.2974603176116943%

ADMET: Metabolism

CYP1A2-inhibitor:	0.481
CYP1A2-substrate:	0.033
CYP2C19-inhibitor:	0.187
CYP2C19-substrate:	0.04
CYP2C9-inhibitor:	0.872
CYP2C9-substrate:	0.772
CYP2D6-inhibitor:	0.197
CYP2D6-substrate:	0.19
CYP3A4-inhibitor:	0.412
CYP3A4-substrate:	0.11

ADMET: Excretion

Clearance (CL):	5.462
Half-life (T1/2):	0.968

ADMET: Toxicity

hERG Blockers:	0.096
Human Hepatotoxicity (H-HT):	0.325
Drug-inuced Liver Injury (DILI):	0.95
AMES Toxicity:	0.092
Rat Oral Acute Toxicity:	0.008
Maximum Recommended Daily Dose:	0.165
Skin Sensitization:	0.92
Carcinogencity:	0.18
Eye Corrosion:	0.003
Eye Irritation:	0.043
Respiratory Toxicity:	0.008

Download Data

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

Natural Product: NPC473275

Natural Product ID:	NPC473275
*Common Name:**	Feruloylpodospermic Acid A
IUPAC Name:	(1R,3R,4R,5R)-1,3-bis[3-(3,4-dihydroxyphenyl)propanoyloxy]-4-hydroxy-5-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxycyclohexane-1-carboxylic acid
Synonyms:
Standard InCHIKey:	XDEMNTIHYAATHM-XFSWUUJNSA-N
Standard InCHI:	InChI=1S/C35H36O15/c1-47-27-16-21(4-10-24(27)38)6-12-31(42)49-29-18-35(34(45)46,50-32(43)13-7-20-3-9-23(37)26(40)15-20)17-28(33(29)44)48-30(41)11-5-19-2-8-22(36)25(39)14-19/h2-4,6,8-10,12,14-16,28-29,33,36-40,44H,5,7,11,13,17-18H2,1H3,(H,45,46)/b12-6+/t28-,29-,33-,35-/m1/s1
SMILES:	COc1cc(/C=C/C(=O)O[C@@H]2C[C@](OC(=O)CCc3ccc(c(c3)O)O)(C[C@H]([C@H]2O)OC(=O)CCc2ccc(c(c2)O)O)C(=O)O)ccc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL390314
PubChem CID:	44424296
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000129] Alcohols and polyols [CHEMONTID:0001292] Cyclic alcohols and derivatives [CHEMONTID:0002509] Cyclitols and derivatives [CHEMONTID:0002512] Quinic acids 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
NPO13478	Scorzonera pseudodivaricata	Species	Asteraceae	Eukaryota	n.a.	Mongolian	n.a.	PMID[17542634]
NPO26200	Scorzonera divaricata	Species	Asteraceae	Eukaryota	n.a.	Mongolian	n.a.	PMID[17542634]
NPO13478	Scorzonera pseudodivaricata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26200	Scorzonera divaricata	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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC50	=	36360000.0	nM	PMID[487589]

☑ 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 NPC473275 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	349
0.1-0.2	1351
0.2-0.3	3225
0.3-0.4	7367
0.4-0.5	10198
0.5-0.6	5297
0.6-0.7	6589
0.7-0.8	7335
0.8-0.85	823
0.85-0.9	129
0.9-0.95	32
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470896
0.9404	High Similarity	NPC146277
0.9404	High Similarity	NPC19380
0.9338	High Similarity	NPC93498
0.9338	High Similarity	NPC163883
0.9324	High Similarity	NPC98356
0.9257	High Similarity	NPC477333
0.92	High Similarity	NPC471076
0.92	High Similarity	NPC192568
0.9156	High Similarity	NPC145425
0.9145	High Similarity	NPC477334
0.9122	High Similarity	NPC472016
0.9122	High Similarity	NPC303090
0.9122	High Similarity	NPC319628
0.9122	High Similarity	NPC277315
0.9122	High Similarity	NPC37331
0.9122	High Similarity	NPC284948
0.9122	High Similarity	NPC258469
0.9122	High Similarity	NPC43158
0.9122	High Similarity	NPC220664
0.9122	High Similarity	NPC192831
0.9114	High Similarity	NPC227297
0.9091	High Similarity	NPC469888
0.9054	High Similarity	NPC471027
0.9054	High Similarity	NPC477335
0.9054	High Similarity	NPC224389
0.9054	High Similarity	NPC297517
0.9054	High Similarity	NPC13818
0.9054	High Similarity	NPC35702
0.9054	High Similarity	NPC206095
0.9045	High Similarity	NPC476373
0.9026	High Similarity	NPC44730
0.902	High Similarity	NPC300329
0.9	High Similarity	NPC471823
0.8957	High Similarity	NPC476374
0.8954	High Similarity	NPC221091
0.8954	High Similarity	NPC259576
0.8944	High Similarity	NPC128403
0.8933	High Similarity	NPC160378
0.8931	High Similarity	NPC476372
0.8931	High Similarity	NPC476371
0.8919	High Similarity	NPC205751
0.8919	High Similarity	NPC295492
0.8919	High Similarity	NPC274891
0.8919	High Similarity	NPC474875
0.8919	High Similarity	NPC288452
0.8919	High Similarity	NPC476819
0.8919	High Similarity	NPC476820
0.8919	High Similarity	NPC26241
0.8919	High Similarity	NPC289690
0.8919	High Similarity	NPC303683
0.8896	High Similarity	NPC476370
0.8882	High Similarity	NPC322660
0.8882	High Similarity	NPC143892
0.8882	High Similarity	NPC299090
0.8882	High Similarity	NPC221383
0.8882	High Similarity	NPC283081
0.8874	High Similarity	NPC143120
0.8874	High Similarity	NPC473909
0.8874	High Similarity	NPC274960
0.8851	High Similarity	NPC152942
0.8851	High Similarity	NPC302857
0.8851	High Similarity	NPC37250
0.8851	High Similarity	NPC219428
0.8851	High Similarity	NPC142703
0.8851	High Similarity	NPC278068
0.8851	High Similarity	NPC24295
0.8851	High Similarity	NPC283560
0.8839	High Similarity	NPC246566
0.8839	High Similarity	NPC95498
0.8831	High Similarity	NPC306343
0.8824	High Similarity	NPC472969
0.8774	High Similarity	NPC252979
0.8774	High Similarity	NPC243891
0.8766	High Similarity	NPC98809
0.8766	High Similarity	NPC476394
0.8766	High Similarity	NPC42464
0.8766	High Similarity	NPC475250
0.875	High Similarity	NPC53884
0.875	High Similarity	NPC258671
0.8734	High Similarity	NPC134925
0.8718	High Similarity	NPC267091
0.8718	High Similarity	NPC75695
0.8718	High Similarity	NPC476434
0.8701	High Similarity	NPC43123
0.8701	High Similarity	NPC98009
0.8688	High Similarity	NPC53889
0.8684	High Similarity	NPC304956
0.8679	High Similarity	NPC133984
0.8679	High Similarity	NPC226759
0.8671	High Similarity	NPC131532
0.8659	High Similarity	NPC216403
0.8659	High Similarity	NPC41494
0.8659	High Similarity	NPC186100
0.8649	High Similarity	NPC70680
0.8649	High Similarity	NPC233350
0.8649	High Similarity	NPC182217
0.8645	High Similarity	NPC478242
0.8642	High Similarity	NPC173729
0.8642	High Similarity	NPC134047
0.8642	High Similarity	NPC272750
0.8642	High Similarity	NPC223006
0.8625	High Similarity	NPC87317
0.8625	High Similarity	NPC469654
0.8608	High Similarity	NPC477299
0.86	High Similarity	NPC284409
0.859	High Similarity	NPC473091
0.8589	High Similarity	NPC142614
0.8581	High Similarity	NPC135127
0.8581	High Similarity	NPC68517
0.858	High Similarity	NPC144557
0.858	High Similarity	NPC285108
0.858	High Similarity	NPC33298
0.8571	High Similarity	NPC24164
0.8571	High Similarity	NPC301089
0.8571	High Similarity	NPC44507
0.8562	High Similarity	NPC289322
0.8562	High Similarity	NPC156818
0.8562	High Similarity	NPC40920
0.8562	High Similarity	NPC472860
0.8562	High Similarity	NPC223335
0.8562	High Similarity	NPC68324
0.8562	High Similarity	NPC160512
0.8562	High Similarity	NPC38779
0.8562	High Similarity	NPC114179
0.8562	High Similarity	NPC473090
0.8554	High Similarity	NPC5786
0.8554	High Similarity	NPC102851
0.8553	High Similarity	NPC38699
0.8545	High Similarity	NPC280493
0.8545	High Similarity	NPC658
0.8545	High Similarity	NPC197708
0.8544	High Similarity	NPC327225
0.8528	High Similarity	NPC45943
0.8521	High Similarity	NPC108191
0.8521	High Similarity	NPC93685
0.8516	High Similarity	NPC229264
0.8514	High Similarity	NPC475468
0.8514	High Similarity	NPC155209
0.8514	High Similarity	NPC168799
0.8506	High Similarity	NPC469683
0.85	High Similarity	NPC88803
0.85	High Similarity	NPC104983
0.85	High Similarity	NPC471405
0.85	High Similarity	NPC291948
0.85	High Similarity	NPC250436
0.85	High Similarity	NPC300845
0.8494	Intermediate Similarity	NPC472803
0.8494	Intermediate Similarity	NPC180768
0.8494	Intermediate Similarity	NPC476365
0.8491	Intermediate Similarity	NPC194095
0.8491	Intermediate Similarity	NPC327032
0.8491	Intermediate Similarity	NPC191046
0.848	Intermediate Similarity	NPC470416
0.8476	Intermediate Similarity	NPC471788
0.8466	Intermediate Similarity	NPC90905
0.8466	Intermediate Similarity	NPC4013
0.8462	Intermediate Similarity	NPC142528
0.8462	Intermediate Similarity	NPC252402
0.8462	Intermediate Similarity	NPC102934
0.8462	Intermediate Similarity	NPC1580
0.8457	Intermediate Similarity	NPC289346
0.8457	Intermediate Similarity	NPC24627
0.8457	Intermediate Similarity	NPC203020
0.8457	Intermediate Similarity	NPC239966
0.8456	Intermediate Similarity	NPC471110
0.8452	Intermediate Similarity	NPC287495
0.8452	Intermediate Similarity	NPC473630
0.8452	Intermediate Similarity	NPC9370
0.8446	Intermediate Similarity	NPC61
0.8446	Intermediate Similarity	NPC25581
0.8446	Intermediate Similarity	NPC18074
0.8446	Intermediate Similarity	NPC5419
0.8442	Intermediate Similarity	NPC114242
0.8442	Intermediate Similarity	NPC50221
0.8442	Intermediate Similarity	NPC469615
0.8438	Intermediate Similarity	NPC203757
0.8438	Intermediate Similarity	NPC10205
0.8434	Intermediate Similarity	NPC266545
0.8434	Intermediate Similarity	NPC202428
0.8434	Intermediate Similarity	NPC95421
0.8434	Intermediate Similarity	NPC198125
0.8431	Intermediate Similarity	NPC31751
0.8431	Intermediate Similarity	NPC67467
0.8431	Intermediate Similarity	NPC253722
0.8431	Intermediate Similarity	NPC253481
0.843	Intermediate Similarity	NPC474093
0.843	Intermediate Similarity	NPC104910
0.8421	Intermediate Similarity	NPC110699
0.8421	Intermediate Similarity	NPC36138
0.8421	Intermediate Similarity	NPC179505
0.8421	Intermediate Similarity	NPC322021
0.8421	Intermediate Similarity	NPC106055
0.8421	Intermediate Similarity	NPC156709
0.8415	Intermediate Similarity	NPC291977
0.8411	Intermediate Similarity	NPC126206
0.8405	Intermediate Similarity	NPC311803
0.8405	Intermediate Similarity	NPC472859
0.8405	Intermediate Similarity	NPC25389
0.8405	Intermediate Similarity	NPC216916

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 NPC473275 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	293
0.1-0.2	833
0.2-0.3	1712
0.3-0.4	2613
0.4-0.5	1984
0.5-0.6	1036
0.6-0.7	539
0.7-0.8	128
0.8-0.85	11
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9122	High Similarity	NPD6190	Approved
0.8521	High Similarity	NPD8055	Clinical (unspecified phase)
0.85	High Similarity	NPD4868	Clinical (unspecified phase)
0.8443	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD6166	Phase 2
0.8235	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD7685	Pre-registration
0.8098	Intermediate Similarity	NPD3817	Phase 2
0.8049	Intermediate Similarity	NPD3882	Suspended
0.8038	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD7808	Phase 3
0.8013	Intermediate Similarity	NPD6233	Phase 2
0.8	Intermediate Similarity	NPD5844	Phase 1
0.8	Intermediate Similarity	NPD7266	Discontinued
0.7966	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD7251	Discontinued
0.7955	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD2801	Approved
0.7907	Intermediate Similarity	NPD6797	Phase 2
0.7895	Intermediate Similarity	NPD7054	Approved
0.7892	Intermediate Similarity	NPD7075	Discontinued
0.7879	Intermediate Similarity	NPD5402	Approved
0.7866	Intermediate Similarity	NPD1934	Approved
0.7849	Intermediate Similarity	NPD7074	Phase 3
0.7849	Intermediate Similarity	NPD7472	Approved
0.7844	Intermediate Similarity	NPD6234	Discontinued
0.7836	Intermediate Similarity	NPD7228	Approved
0.7836	Intermediate Similarity	NPD3818	Discontinued
0.7811	Intermediate Similarity	NPD6232	Discontinued
0.7792	Intermediate Similarity	NPD230	Phase 1
0.7778	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7473	Discontinued
0.7765	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD3027	Phase 3
0.7758	Intermediate Similarity	NPD37	Approved
0.7751	Intermediate Similarity	NPD8127	Discontinued
0.7736	Intermediate Similarity	NPD4628	Phase 3
0.7733	Intermediate Similarity	NPD3751	Discontinued
0.7725	Intermediate Similarity	NPD4965	Approved
0.7725	Intermediate Similarity	NPD4967	Phase 2
0.7725	Intermediate Similarity	NPD4966	Approved
0.7712	Intermediate Similarity	NPD6798	Discontinued
0.7711	Intermediate Similarity	NPD1465	Phase 2
0.7711	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD3787	Discontinued
0.7651	Intermediate Similarity	NPD6801	Discontinued
0.7647	Intermediate Similarity	NPD7199	Phase 2
0.7636	Intermediate Similarity	NPD4380	Phase 2
0.7625	Intermediate Similarity	NPD8166	Discontinued
0.7622	Intermediate Similarity	NPD1653	Approved
0.7607	Intermediate Similarity	NPD1512	Approved
0.76	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD6799	Approved
0.7586	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD5403	Approved
0.7542	Intermediate Similarity	NPD8434	Phase 2
0.7532	Intermediate Similarity	NPD7095	Approved
0.7516	Intermediate Similarity	NPD9494	Approved
0.75	Intermediate Similarity	NPD8455	Phase 2
0.7485	Intermediate Similarity	NPD1511	Approved
0.7485	Intermediate Similarity	NPD6386	Approved
0.7485	Intermediate Similarity	NPD6385	Approved
0.7484	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD6355	Discontinued
0.7447	Intermediate Similarity	NPD7435	Discontinued
0.7444	Intermediate Similarity	NPD8150	Discontinued
0.7439	Intermediate Similarity	NPD5401	Approved
0.7412	Intermediate Similarity	NPD7768	Phase 2
0.7396	Intermediate Similarity	NPD7819	Suspended
0.7389	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD1613	Approved
0.7384	Intermediate Similarity	NPD5494	Approved
0.7381	Intermediate Similarity	NPD7411	Suspended
0.7374	Intermediate Similarity	NPD8313	Approved
0.7374	Intermediate Similarity	NPD8312	Approved
0.736	Intermediate Similarity	NPD7240	Approved
0.7353	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD4062	Phase 3
0.7321	Intermediate Similarity	NPD6599	Discontinued
0.7314	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD7874	Approved
0.7306	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2935	Discontinued
0.7263	Intermediate Similarity	NPD7039	Approved
0.7263	Intermediate Similarity	NPD7038	Approved
0.7261	Intermediate Similarity	NPD3764	Approved
0.7251	Intermediate Similarity	NPD5353	Approved
0.725	Intermediate Similarity	NPD7097	Phase 1
0.7229	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7870	Phase 2
0.7225	Intermediate Similarity	NPD7871	Phase 2
0.7219	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD7033	Discontinued
0.7196	Intermediate Similarity	NPD6778	Approved
0.7196	Intermediate Similarity	NPD6776	Approved
0.7196	Intermediate Similarity	NPD6777	Approved
0.7196	Intermediate Similarity	NPD6782	Approved
0.7196	Intermediate Similarity	NPD6779	Approved
0.7196	Intermediate Similarity	NPD6780	Approved
0.7196	Intermediate Similarity	NPD6781	Approved
0.7173	Intermediate Similarity	NPD7697	Approved
0.7173	Intermediate Similarity	NPD7698	Approved
0.7173	Intermediate Similarity	NPD7696	Phase 3
0.7173	Intermediate Similarity	NPD7680	Approved
0.717	Intermediate Similarity	NPD4060	Phase 1
0.7167	Intermediate Similarity	NPD6559	Discontinued
0.716	Intermediate Similarity	NPD7458	Discontinued
0.7159	Intermediate Similarity	NPD5242	Approved
0.7143	Intermediate Similarity	NPD6959	Discontinued
0.7134	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD5536	Phase 2
0.7126	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD919	Approved
0.7126	Intermediate Similarity	NPD3146	Approved
0.7125	Intermediate Similarity	NPD4340	Discontinued
0.7125	Intermediate Similarity	NPD447	Suspended
0.7113	Intermediate Similarity	NPD7701	Phase 2
0.7099	Intermediate Similarity	NPD1510	Phase 2
0.7091	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD4110	Phase 3
0.7091	Intermediate Similarity	NPD3750	Approved
0.7086	Intermediate Similarity	NPD9545	Approved
0.7083	Intermediate Similarity	NPD6273	Approved
0.7078	Intermediate Similarity	NPD9269	Phase 2
0.7078	Intermediate Similarity	NPD1608	Approved
0.7077	Intermediate Similarity	NPD8151	Discontinued
0.7073	Intermediate Similarity	NPD1549	Phase 2
0.7073	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD3749	Approved
0.7062	Intermediate Similarity	NPD3926	Phase 2
0.7059	Intermediate Similarity	NPD3455	Phase 2
0.7053	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD3887	Approved
0.7048	Intermediate Similarity	NPD2354	Approved
0.7047	Intermediate Similarity	NPD8319	Approved
0.7047	Intermediate Similarity	NPD8320	Phase 1
0.7045	Intermediate Similarity	NPD1247	Approved
0.7033	Intermediate Similarity	NPD7549	Discontinued
0.703	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7229	Phase 3
0.7005	Intermediate Similarity	NPD7801	Approved
0.7	Intermediate Similarity	NPD7699	Phase 2
0.7	Intermediate Similarity	NPD7700	Phase 2
0.6979	Remote Similarity	NPD2494	Approved
0.6979	Remote Similarity	NPD2493	Approved
0.6975	Remote Similarity	NPD6653	Approved
0.697	Remote Similarity	NPD4534	Discontinued
0.6964	Remote Similarity	NPD4357	Discontinued
0.6959	Remote Similarity	NPD228	Approved
0.6959	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD3226	Approved
0.6957	Remote Similarity	NPD1240	Approved
0.6957	Remote Similarity	NPD943	Approved
0.6957	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD2796	Approved
0.6931	Remote Similarity	NPD6534	Approved
0.6931	Remote Similarity	NPD6535	Approved
0.6923	Remote Similarity	NPD2534	Approved
0.6923	Remote Similarity	NPD2533	Approved
0.6923	Remote Similarity	NPD2532	Approved
0.6923	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7783	Phase 2
0.6919	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD4908	Phase 1
0.6909	Remote Similarity	NPD5762	Approved
0.6909	Remote Similarity	NPD5763	Approved
0.6905	Remote Similarity	NPD7440	Discontinued
0.6903	Remote Similarity	NPD1535	Discovery
0.6891	Remote Similarity	NPD3452	Approved
0.6891	Remote Similarity	NPD3450	Approved
0.6886	Remote Similarity	NPD7003	Approved
0.6886	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD17	Approved
0.6882	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD3225	Approved
0.6879	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6971	Discontinued
0.6872	Remote Similarity	NPD4582	Approved
0.6872	Remote Similarity	NPD4583	Approved
0.6871	Remote Similarity	NPD1607	Approved
0.6867	Remote Similarity	NPD5958	Discontinued
0.6859	Remote Similarity	NPD1481	Phase 2
0.6856	Remote Similarity	NPD6823	Phase 2
0.6852	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD3620	Phase 2
0.6848	Remote Similarity	NPD6100	Approved
0.6848	Remote Similarity	NPD6099	Approved
0.6848	Remote Similarity	NPD1551	Phase 2

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