NPASS Compound

Structure

NPC471633 OpenBabel07101719252D 36 41 0 0 1 0 0 0 0 0999 V2000 6.9282 -1.0000 0.0000 C 0 0 0 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 0.4067 -1.9135 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 0.8660 1.5000 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 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2111 -2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6723 -3.0691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2601 -2.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 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 7.7942 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2111 -3.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.7942 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 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.6603 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0201 -4.1569 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 -3.8781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 28 1 0 0 0 0 4 5 1 0 0 0 0 4 18 1 0 0 0 0 5 22 1 0 0 0 0 6 9 1 0 0 0 0 6 19 1 0 0 0 0 7 10 1 0 0 0 0 7 21 1 0 0 0 0 8 11 1 0 0 0 0 8 20 1 0 0 0 0 9 27 1 0 0 0 0 10 28 1 0 0 0 0 11 29 1 0 0 0 0 12 17 2 0 0 0 0 12 24 1 0 0 0 0 13 18 1 0 0 0 0 13 19 1 0 0 0 0 14 23 1 0 0 0 0 14 25 1 0 0 0 0 15 17 1 0 0 0 0 15 34 1 0 0 0 0 16 1 1 6 0 0 0 16 26 1 0 0 0 0 16 35 1 0 0 0 0 17 20 1 0 0 0 0 18 27 1 1 0 0 0 19 36 1 1 0 0 0 20 28 1 1 0 0 0 21 22 1 0 0 0 0 21 27 1 1 0 0 0 22 29 1 6 0 0 0 23 26 1 0 0 0 0 23 30 1 6 0 0 0 24 31 2 0 0 0 0 24 34 1 0 0 0 0 25 35 1 0 0 0 0 25 36 1 1 0 0 0 26 32 1 6 0 0 0 27 2 1 1 0 0 0 28 29 1 1 0 0 0 29 33 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	504.31
Volume:	515.06
LogP:	3.96
LogD:	3.789
LogS:	-4.596
# Rotatable Bonds:	3
TPSA:	112.52
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.449
Synthetic Accessibility Score:	5.171
Fsp3:	0.862
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.987
MDCK Permeability:	2.416128700133413e-05
Pgp-inhibitor:	0.919
Pgp-substrate:	0.937
Human Intestinal Absorption (HIA):	0.04
20% Bioavailability (F20%):	0.455
30% Bioavailability (F30%):	0.044

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.168
Plasma Protein Binding (PPB):	96.5017318725586%
Volume Distribution (VD):	1.358
Pgp-substrate:	2.9178683757781982%

ADMET: Metabolism

CYP1A2-inhibitor:	0.021
CYP1A2-substrate:	0.846
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.542
CYP2C9-inhibitor:	0.179
CYP2C9-substrate:	0.223
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.539
CYP3A4-inhibitor:	0.388
CYP3A4-substrate:	0.279

ADMET: Excretion

Clearance (CL):	11.363
Half-life (T1/2):	0.111

ADMET: Toxicity

hERG Blockers:	0.553
Human Hepatotoxicity (H-HT):	0.332
Drug-inuced Liver Injury (DILI):	0.071
AMES Toxicity:	0.113
Rat Oral Acute Toxicity:	0.84
Maximum Recommended Daily Dose:	0.976
Skin Sensitization:	0.941
Carcinogencity:	0.784
Eye Corrosion:	0.003
Eye Irritation:	0.02
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC471633

Natural Product ID:	NPC471633
*Common Name:**	4-[3-(4,5-Dihydroxy-6-Methyl-Tetrahydro-Pyran-2-Yloxy)-14-Hydroxy-10,13-Dimethyl-Hexadecahydro-Cyclopenta[A]Phenanthren-17-Yl]-5H-Furan-2-One
IUPAC Name:	3-[(3S,5S,8R,9S,10S,13R,14R,17R)-3-[(2R,4S,5S,6S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-14-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
Synonyms:
Standard InCHIKey:	NQOMDNMTNVQXRR-SVWWHTAMSA-N
Standard InCHI:	InChI=1S/C29H44O7/c1-16-26(32)23(30)14-25(35-16)36-19-6-9-27(2)18(13-19)4-5-22-21(27)7-10-28(3)20(8-11-29(22,28)33)17-12-24(31)34-15-17/h12,16,18-23,25-26,30,32-33H,4-11,13-15H2,1-3H3/t16-,18-,19-,20+,21-,22+,23-,25-,26+,27-,28+,29+/m0/s1
SMILES:	CC1C(C(CC(O1)OC2CCC3(C(C2)CCC4C3CCC5(C4(CCC5C6=CC(=O)OC6)O)C)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3085490
PubChem CID:	76335204
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001555] Cardenolides and derivatives [CHEMONTID:0001559] Cardenolide glycosides 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
NPO32604	asclepias fructicosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3981544]

☑ 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
NPT2	Others	Unspecified		IC50	=	7.04	nM	PMID[470840]
NPT938	Organism	Cavia porcellus	Cavia porcellus	Relative ionotropic activity	=	15.0	n.a.	PMID[470841]

☑ 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 NPC471633 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	241
0.1-0.2	1654
0.2-0.3	5030
0.3-0.4	10955
0.4-0.5	10240
0.5-0.6	6368
0.6-0.7	4726
0.7-0.8	2781
0.8-0.85	417
0.85-0.9	144
0.9-0.95	86
0.95-1	55

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC31354
1.0	High Similarity	NPC69576
1.0	High Similarity	NPC84949
0.9906	High Similarity	NPC99620
0.9906	High Similarity	NPC193382
0.9906	High Similarity	NPC199428
0.9906	High Similarity	NPC5311
0.9906	High Similarity	NPC310341
0.9813	High Similarity	NPC471353
0.9813	High Similarity	NPC50305
0.9813	High Similarity	NPC471354
0.9813	High Similarity	NPC244402
0.9813	High Similarity	NPC142066
0.9813	High Similarity	NPC93883
0.9813	High Similarity	NPC27507
0.9813	High Similarity	NPC34390
0.9813	High Similarity	NPC290693
0.9813	High Similarity	NPC309034
0.9813	High Similarity	NPC474418
0.9813	High Similarity	NPC157376
0.9813	High Similarity	NPC473852
0.9813	High Similarity	NPC87250
0.9813	High Similarity	NPC471351
0.9813	High Similarity	NPC243196
0.9813	High Similarity	NPC152615
0.9813	High Similarity	NPC196429
0.9813	High Similarity	NPC77319
0.9813	High Similarity	NPC158344
0.9813	High Similarity	NPC471355
0.9813	High Similarity	NPC84987
0.9813	High Similarity	NPC99728
0.9722	High Similarity	NPC83287
0.9633	High Similarity	NPC44899
0.9633	High Similarity	NPC329905
0.9633	High Similarity	NPC292467
0.9633	High Similarity	NPC304260
0.9633	High Similarity	NPC5883
0.9633	High Similarity	NPC30483
0.9633	High Similarity	NPC469756
0.9633	High Similarity	NPC29639
0.9633	High Similarity	NPC55532
0.9633	High Similarity	NPC32177
0.9633	High Similarity	NPC236973
0.9633	High Similarity	NPC470897
0.963	High Similarity	NPC203862
0.9545	High Similarity	NPC72260
0.9545	High Similarity	NPC475136
0.9545	High Similarity	NPC474466
0.9545	High Similarity	NPC475629
0.9545	High Similarity	NPC475556
0.9459	High Similarity	NPC314535
0.9459	High Similarity	NPC40749
0.9459	High Similarity	NPC173555
0.9459	High Similarity	NPC475590
0.9459	High Similarity	NPC231518
0.9459	High Similarity	NPC120390
0.9459	High Similarity	NPC475219
0.9459	High Similarity	NPC475419
0.9459	High Similarity	NPC474908
0.9375	High Similarity	NPC264336
0.9375	High Similarity	NPC474423
0.9375	High Similarity	NPC74259
0.9375	High Similarity	NPC193893
0.9375	High Similarity	NPC115349
0.9364	High Similarity	NPC218093
0.934	High Similarity	NPC475030
0.9292	High Similarity	NPC117445
0.9292	High Similarity	NPC208193
0.9292	High Similarity	NPC308262
0.9292	High Similarity	NPC27363
0.9279	High Similarity	NPC268326
0.9279	High Similarity	NPC81222
0.9279	High Similarity	NPC153085
0.9279	High Similarity	NPC291820
0.9196	High Similarity	NPC107607
0.913	High Similarity	NPC250556
0.913	High Similarity	NPC469750
0.9052	High Similarity	NPC179412
0.9052	High Similarity	NPC240070
0.9052	High Similarity	NPC117702
0.9052	High Similarity	NPC146456
0.9052	High Similarity	NPC469757
0.9052	High Similarity	NPC329784
0.9052	High Similarity	NPC471357
0.9052	High Similarity	NPC471356
0.9048	High Similarity	NPC472821
0.9027	High Similarity	NPC470312
0.8972	High Similarity	NPC472820
0.8898	High Similarity	NPC284406
0.8898	High Similarity	NPC188234
0.8898	High Similarity	NPC469754
0.8898	High Similarity	NPC10823
0.8898	High Similarity	NPC471352
0.8898	High Similarity	NPC469753
0.8898	High Similarity	NPC232785
0.8898	High Similarity	NPC219085
0.8898	High Similarity	NPC276838
0.8898	High Similarity	NPC89514
0.8898	High Similarity	NPC197707
0.8898	High Similarity	NPC140092
0.8898	High Similarity	NPC125077
0.8898	High Similarity	NPC17896
0.8898	High Similarity	NPC251866
0.8898	High Similarity	NPC469755
0.8898	High Similarity	NPC469751
0.8898	High Similarity	NPC180079
0.8898	High Similarity	NPC469752
0.8898	High Similarity	NPC329986
0.8898	High Similarity	NPC471358
0.8898	High Similarity	NPC70542
0.8898	High Similarity	NPC86159
0.8898	High Similarity	NPC471361
0.8898	High Similarity	NPC471359
0.8898	High Similarity	NPC471360
0.8898	High Similarity	NPC9499
0.8898	High Similarity	NPC6108
0.8879	High Similarity	NPC186668
0.8879	High Similarity	NPC473199
0.8879	High Similarity	NPC220217
0.8879	High Similarity	NPC472818
0.8879	High Similarity	NPC119855
0.8868	High Similarity	NPC187302
0.8868	High Similarity	NPC160583
0.8868	High Similarity	NPC10232
0.8868	High Similarity	NPC189588
0.8868	High Similarity	NPC196471
0.8868	High Similarity	NPC97487
0.886	High Similarity	NPC135369
0.8857	High Similarity	NPC268829
0.8857	High Similarity	NPC222875
0.8857	High Similarity	NPC25177
0.8857	High Similarity	NPC295110
0.8857	High Similarity	NPC247701
0.8824	High Similarity	NPC253456
0.8824	High Similarity	NPC16569
0.8824	High Similarity	NPC159338
0.8814	High Similarity	NPC311534
0.8807	High Similarity	NPC206618
0.8785	High Similarity	NPC472819
0.875	High Similarity	NPC19124
0.875	High Similarity	NPC93416
0.875	High Similarity	NPC42670
0.875	High Similarity	NPC477580
0.8739	High Similarity	NPC91
0.8716	High Similarity	NPC38948
0.8716	High Similarity	NPC38217
0.8716	High Similarity	NPC472988
0.8692	High Similarity	NPC281378
0.8678	High Similarity	NPC32793
0.8678	High Similarity	NPC146857
0.8678	High Similarity	NPC116075
0.8678	High Similarity	NPC477709
0.8678	High Similarity	NPC476221
0.8678	High Similarity	NPC247190
0.8678	High Similarity	NPC225385
0.8678	High Similarity	NPC298783
0.8678	High Similarity	NPC104585
0.8678	High Similarity	NPC469749
0.8678	High Similarity	NPC157817
0.8673	High Similarity	NPC232564
0.8673	High Similarity	NPC207637
0.8673	High Similarity	NPC113425
0.8661	High Similarity	NPC144068
0.8649	High Similarity	NPC114188
0.8636	High Similarity	NPC473570
0.8636	High Similarity	NPC43976
0.8636	High Similarity	NPC51925
0.8636	High Similarity	NPC154085
0.8636	High Similarity	NPC125361
0.8636	High Similarity	NPC472901
0.8636	High Similarity	NPC296761
0.8624	High Similarity	NPC234160
0.8611	High Similarity	NPC31430
0.8611	High Similarity	NPC85593
0.8607	High Similarity	NPC329636
0.8598	High Similarity	NPC472815
0.8598	High Similarity	NPC121423
0.8596	High Similarity	NPC20979
0.8596	High Similarity	NPC476690
0.8596	High Similarity	NPC100048
0.8585	High Similarity	NPC472826
0.8585	High Similarity	NPC477721
0.8585	High Similarity	NPC477716
0.8571	High Similarity	NPC216595
0.8571	High Similarity	NPC473567
0.8571	High Similarity	NPC231751
0.8571	High Similarity	NPC475354
0.8559	High Similarity	NPC191439
0.8559	High Similarity	NPC177047
0.8559	High Similarity	NPC103627
0.8559	High Similarity	NPC170974
0.8547	High Similarity	NPC471082
0.8537	High Similarity	NPC194716
0.8534	High Similarity	NPC257610
0.8532	High Similarity	NPC472899
0.8532	High Similarity	NPC51719
0.8532	High Similarity	NPC239961
0.8532	High Similarity	NPC472900
0.8532	High Similarity	NPC472898
0.8532	High Similarity	NPC85670

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 NPC471633 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	207
0.1-0.2	1768
0.2-0.3	4069
0.3-0.4	2075
0.4-0.5	547
0.5-0.6	264
0.6-0.7	171
0.7-0.8	31
0.8-0.85	5
0.85-0.9	1
0.9-0.95	9
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9722	High Similarity	NPD7328	Approved
0.9722	High Similarity	NPD7327	Approved
0.9633	High Similarity	NPD7516	Approved
0.9545	High Similarity	NPD8294	Approved
0.9545	High Similarity	NPD8377	Approved
0.9459	High Similarity	NPD8380	Approved
0.9459	High Similarity	NPD8033	Approved
0.9459	High Similarity	NPD8296	Approved
0.9459	High Similarity	NPD8379	Approved
0.9459	High Similarity	NPD8378	Approved
0.9459	High Similarity	NPD8335	Approved
0.913	High Similarity	NPD7507	Approved
0.8898	High Similarity	NPD7319	Approved
0.8783	High Similarity	NPD7503	Approved
0.8214	Intermediate Similarity	NPD6686	Approved
0.8148	Intermediate Similarity	NPD7638	Approved
0.8125	Intermediate Similarity	NPD6412	Phase 2
0.8073	Intermediate Similarity	NPD7640	Approved
0.8073	Intermediate Similarity	NPD7639	Approved
0.8017	Intermediate Similarity	NPD8133	Approved
0.7903	Intermediate Similarity	NPD7736	Approved
0.7704	Intermediate Similarity	NPD7625	Phase 1
0.768	Intermediate Similarity	NPD8293	Discontinued
0.7642	Intermediate Similarity	NPD6370	Approved
0.752	Intermediate Similarity	NPD7492	Approved
0.748	Intermediate Similarity	NPD6054	Approved
0.748	Intermediate Similarity	NPD6059	Approved
0.746	Intermediate Similarity	NPD6616	Approved
0.7456	Intermediate Similarity	NPD7632	Discontinued
0.7402	Intermediate Similarity	NPD7078	Approved
0.7377	Intermediate Similarity	NPD7115	Discovery
0.7377	Intermediate Similarity	NPD6009	Approved
0.7373	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6882	Approved
0.7302	Intermediate Similarity	NPD8328	Phase 3
0.7288	Intermediate Similarity	NPD7320	Approved
0.728	Intermediate Similarity	NPD6015	Approved
0.728	Intermediate Similarity	NPD6016	Approved
0.7273	Intermediate Similarity	NPD4632	Approved
0.7265	Intermediate Similarity	NPD7128	Approved
0.7265	Intermediate Similarity	NPD6675	Approved
0.7265	Intermediate Similarity	NPD6402	Approved
0.7265	Intermediate Similarity	NPD5739	Approved
0.7227	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5988	Approved
0.7207	Intermediate Similarity	NPD8171	Discontinued
0.72	Intermediate Similarity	NPD6319	Approved
0.7193	Intermediate Similarity	NPD4225	Approved
0.719	Intermediate Similarity	NPD8297	Approved
0.7165	Intermediate Similarity	NPD6067	Discontinued
0.7143	Intermediate Similarity	NPD6881	Approved
0.7143	Intermediate Similarity	NPD6899	Approved
0.7091	Intermediate Similarity	NPD6051	Approved
0.7083	Intermediate Similarity	NPD6372	Approved
0.7083	Intermediate Similarity	NPD6373	Approved
0.7069	Intermediate Similarity	NPD5344	Discontinued
0.7059	Intermediate Similarity	NPD5701	Approved
0.7059	Intermediate Similarity	NPD5697	Approved
0.7049	Intermediate Similarity	NPD6053	Discontinued
0.7048	Intermediate Similarity	NPD7525	Registered
0.7025	Intermediate Similarity	NPD7102	Approved
0.7025	Intermediate Similarity	NPD7290	Approved
0.7025	Intermediate Similarity	NPD6883	Approved
0.7025	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6008	Approved
0.6967	Remote Similarity	NPD6869	Approved
0.6967	Remote Similarity	NPD6847	Approved
0.6967	Remote Similarity	NPD6649	Approved
0.6967	Remote Similarity	NPD8130	Phase 1
0.6967	Remote Similarity	NPD6617	Approved
0.6967	Remote Similarity	NPD6650	Approved
0.696	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6083	Phase 2
0.6957	Remote Similarity	NPD6084	Phase 2
0.6947	Remote Similarity	NPD6033	Approved
0.6942	Remote Similarity	NPD6012	Approved
0.6942	Remote Similarity	NPD6013	Approved
0.6942	Remote Similarity	NPD6014	Approved
0.6899	Remote Similarity	NPD7604	Phase 2
0.6891	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6928	Phase 2
0.6875	Remote Similarity	NPD8513	Phase 3
0.6875	Remote Similarity	NPD8516	Approved
0.6875	Remote Similarity	NPD8517	Approved
0.6875	Remote Similarity	NPD8515	Approved
0.6875	Remote Similarity	NPD5983	Phase 2
0.686	Remote Similarity	NPD6011	Approved
0.6829	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.681	Remote Similarity	NPD4755	Approved
0.6794	Remote Similarity	NPD6336	Discontinued
0.6789	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD7524	Approved
0.6754	Remote Similarity	NPD4202	Approved
0.6748	Remote Similarity	NPD4634	Approved
0.6723	Remote Similarity	NPD5211	Phase 2
0.6721	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD7748	Approved
0.6696	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD5286	Approved
0.6695	Remote Similarity	NPD6648	Approved
0.6695	Remote Similarity	NPD5285	Approved
0.6695	Remote Similarity	NPD4700	Approved
0.6695	Remote Similarity	NPD4696	Approved
0.6667	Remote Similarity	NPD8035	Phase 2
0.6667	Remote Similarity	NPD7515	Phase 2
0.6667	Remote Similarity	NPD8034	Phase 2
0.6667	Remote Similarity	NPD7902	Approved
0.6638	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD5695	Phase 3
0.6636	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD8449	Approved
0.6614	Remote Similarity	NPD6274	Approved
0.6613	Remote Similarity	NPD6371	Approved
0.6612	Remote Similarity	NPD5141	Approved
0.661	Remote Similarity	NPD5696	Approved
0.661	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD6399	Phase 3
0.6607	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD7100	Approved
0.6589	Remote Similarity	NPD7101	Approved
0.6583	Remote Similarity	NPD5224	Approved
0.6583	Remote Similarity	NPD5226	Approved
0.6583	Remote Similarity	NPD4633	Approved
0.6583	Remote Similarity	NPD5225	Approved
0.6579	Remote Similarity	NPD46	Approved
0.6579	Remote Similarity	NPD6698	Approved
0.6577	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD8450	Suspended
0.656	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD6903	Approved
0.6545	Remote Similarity	NPD6695	Phase 3
0.6529	Remote Similarity	NPD5174	Approved
0.6529	Remote Similarity	NPD5175	Approved
0.6522	Remote Similarity	NPD7637	Suspended
0.6522	Remote Similarity	NPD5693	Phase 1
0.6518	Remote Similarity	NPD6409	Approved
0.6518	Remote Similarity	NPD7146	Approved
0.6518	Remote Similarity	NPD6684	Approved
0.6518	Remote Similarity	NPD7521	Approved
0.6518	Remote Similarity	NPD5330	Approved
0.6518	Remote Similarity	NPD7334	Approved
0.6512	Remote Similarity	NPD6335	Approved
0.6504	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4159	Approved
0.65	Remote Similarity	NPD5223	Approved
0.6491	Remote Similarity	NPD4753	Phase 2
0.6491	Remote Similarity	NPD5328	Approved
0.6489	Remote Similarity	NPD6909	Approved
0.6489	Remote Similarity	NPD6908	Approved
0.6481	Remote Similarity	NPD7645	Phase 2
0.6471	Remote Similarity	NPD5956	Approved
0.6435	Remote Similarity	NPD7838	Discovery
0.6434	Remote Similarity	NPD6317	Approved
0.6429	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD4767	Approved
0.6423	Remote Similarity	NPD4768	Approved
0.641	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.641	Remote Similarity	NPD7900	Approved
0.6393	Remote Similarity	NPD4754	Approved
0.6385	Remote Similarity	NPD6313	Approved
0.6385	Remote Similarity	NPD6314	Approved
0.6379	Remote Similarity	NPD6079	Approved
0.6375	Remote Similarity	NPD7799	Discontinued
0.6372	Remote Similarity	NPD3618	Phase 1
0.6364	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD6904	Approved
0.6348	Remote Similarity	NPD6080	Approved
0.6348	Remote Similarity	NPD6673	Approved
0.6339	Remote Similarity	NPD3666	Approved
0.6339	Remote Similarity	NPD3665	Phase 1
0.6339	Remote Similarity	NPD3133	Approved
0.633	Remote Similarity	NPD4195	Approved
0.632	Remote Similarity	NPD5128	Approved
0.632	Remote Similarity	NPD4730	Approved
0.632	Remote Similarity	NPD4729	Approved
0.6316	Remote Similarity	NPD7750	Discontinued
0.6306	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD6930	Phase 2
0.6273	Remote Similarity	NPD6931	Approved
0.6271	Remote Similarity	NPD6001	Approved
0.6262	Remote Similarity	NPD6942	Approved
0.6262	Remote Similarity	NPD7339	Approved
0.6261	Remote Similarity	NPD6672	Approved
0.6261	Remote Similarity	NPD5737	Approved
0.625	Remote Similarity	NPD8074	Phase 3
0.6239	Remote Similarity	NPD5284	Approved
0.6239	Remote Similarity	NPD5281	Approved
0.6231	Remote Similarity	NPD6940	Discontinued
0.622	Remote Similarity	NPD5251	Approved
0.622	Remote Similarity	NPD5250	Approved
0.622	Remote Similarity	NPD5247	Approved
0.622	Remote Similarity	NPD5249	Phase 3
0.622	Remote Similarity	NPD5248	Approved
0.6218	Remote Similarity	NPD5210	Approved
0.6218	Remote Similarity	NPD4629	Approved
0.6204	Remote Similarity	NPD6933	Approved
0.6195	Remote Similarity	NPD4786	Approved
0.6182	Remote Similarity	NPD6929	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