NPASS Compound

Structure

NPC475054 OpenBabel07101718192D 37 40 0 0 1 0 0 0 0 0999 V2000 2.5981 -4.5000 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 1.7321 -1.0000 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 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 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 4.3301 -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 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 3 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 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 1 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 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 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 -1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 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 -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 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 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 0.8660 -0.5000 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 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 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 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 11 1 0 0 0 0 4 5 1 0 0 0 0 4 10 1 0 0 0 0 5 26 1 0 0 0 0 6 11 1 0 0 0 0 6 12 1 0 0 0 0 7 12 1 0 0 0 0 7 13 2 0 0 0 0 8 14 1 0 0 0 0 8 15 1 0 0 0 0 9 27 1 0 0 0 0 10 17 2 0 0 0 0 11 28 1 0 0 0 0 12 23 2 0 0 0 0 13 15 1 0 0 0 0 13 18 1 0 0 0 0 14 17 1 0 0 0 0 14 26 1 1 0 0 0 15 29 2 0 0 0 0 16 9 1 6 0 0 0 16 19 1 0 0 0 0 16 36 1 0 0 0 0 17 24 1 0 0 0 0 18 20 2 0 0 0 0 18 26 1 0 0 0 0 19 21 1 0 0 0 0 19 30 1 1 0 0 0 20 23 1 0 0 0 0 20 31 1 0 0 0 0 21 22 1 0 0 0 0 21 32 1 6 0 0 0 22 25 1 0 0 0 0 22 33 1 1 0 0 0 23 37 1 0 0 0 0 24 34 2 0 0 0 0 24 35 1 0 0 0 0 25 36 1 0 0 0 0 25 37 1 6 0 0 0 26 3 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	522.21
Volume:	504.9
LogP:	0.55
LogD:	0.006
LogS:	-2.672
# Rotatable Bonds:	6
TPSA:	194.21
# H-Bond Aceptor:	11
# H-Bond Donor:	7
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.269
Synthetic Accessibility Score:	4.943
Fsp3:	0.615
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.432
MDCK Permeability:	8.815446562948637e-06
Pgp-inhibitor:	0.129
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.881
20% Bioavailability (F20%):	0.064
30% Bioavailability (F30%):	0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.132
Plasma Protein Binding (PPB):	63.42784118652344%
Volume Distribution (VD):	0.301
Pgp-substrate:	24.389270782470703%

ADMET: Metabolism

CYP1A2-inhibitor:	0.04
CYP1A2-substrate:	0.064
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.076
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.116
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.134
CYP3A4-inhibitor:	0.011
CYP3A4-substrate:	0.062

ADMET: Excretion

Clearance (CL):	1.466
Half-life (T1/2):	0.713

ADMET: Toxicity

hERG Blockers:	0.068
Human Hepatotoxicity (H-HT):	0.333
Drug-inuced Liver Injury (DILI):	0.793
AMES Toxicity:	0.088
Rat Oral Acute Toxicity:	0.047
Maximum Recommended Daily Dose:	0.046
Skin Sensitization:	0.054
Carcinogencity:	0.036
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.203

Download Data

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

Natural Product: NPC475054

Natural Product ID:	NPC475054
*Common Name:**	(4As,10Ar)-5-Hydroxy-7-(2-Hydroxypropyl)-2,4A-Dimethyl-9-Oxo-6-[(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl]Oxy-3,4,10,10A-Tetrahydrophenanthrene-1-Carboxylic Acid
IUPAC Name:	(4aS,10aR)-5-hydroxy-7-(2-hydroxypropyl)-2,4a-dimethyl-9-oxo-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4,10,10a-tetrahydrophenanthrene-1-carboxylic acid
Synonyms:
Standard InCHIKey:	PURXKVQXMAJBLE-BOZADOMPSA-N
Standard InCHI:	InChI=1S/C26H34O11/c1-10-4-5-26(3)14(17(10)24(34)35)8-15(29)13-7-12(6-11(2)28)23(20(31)18(13)26)37-25-22(33)21(32)19(30)16(9-27)36-25/h7,11,14,16,19,21-22,25,27-28,30-33H,4-6,8-9H2,1-3H3,(H,34,35)/t11?,14-,16+,19+,21-,22+,25-,26-/m0/s1
SMILES:	OC[C@H]1O[C@@H](Oc2c(CC(O)C)cc3c(c2O)[C@@]2(C)CCC(=C([C@@H]2CC3=O)C(=O)O)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL494628
PubChem CID:	24879401
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001295] Hydroxysteroids [CHEMONTID:0004158] 1-hydroxysteroids

*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
NPO20879	Clerodendrum bungei	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18348535]
NPO20879	Clerodendrum bungei	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20879	Clerodendrum bungei	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2511	Cell Line	HGC-27	Homo sapiens	IC50	>	10000.0	nM	PMID[557343]
NPT71	Cell Line	HEK293	Homo sapiens	IC50	>	10000.0	nM	PMID[557343]
NPT319	Cell Line	B16	Mus musculus	IC50	>	10000.0	nM	PMID[557343]

☑ 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 NPC475054 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	397
0.1-0.2	1564
0.2-0.3	3200
0.3-0.4	6735
0.4-0.5	9684
0.5-0.6	6463
0.6-0.7	6339
0.7-0.8	7488
0.8-0.85	753
0.85-0.9	72
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.8988	High Similarity	NPC263212
0.8982	High Similarity	NPC25889
0.8947	High Similarity	NPC316539
0.8947	High Similarity	NPC199357
0.8902	High Similarity	NPC47191
0.8869	High Similarity	NPC100420
0.8851	High Similarity	NPC212290
0.883	High Similarity	NPC52598
0.8793	High Similarity	NPC267549
0.8786	High Similarity	NPC193377
0.8786	High Similarity	NPC474345
0.8764	High Similarity	NPC205721
0.8736	High Similarity	NPC79736
0.8736	High Similarity	NPC67629
0.8735	High Similarity	NPC471405
0.8727	High Similarity	NPC62051
0.8713	High Similarity	NPC298847
0.8708	High Similarity	NPC105591
0.8698	High Similarity	NPC41009
0.8693	High Similarity	NPC188217
0.8693	High Similarity	NPC170203
0.8678	High Similarity	NPC469438
0.8678	High Similarity	NPC146803
0.8678	High Similarity	NPC68381
0.8675	High Similarity	NPC10205
0.8663	High Similarity	NPC191653
0.8629	High Similarity	NPC473713
0.8621	High Similarity	NPC166674
0.8621	High Similarity	NPC472054
0.8621	High Similarity	NPC219600
0.8621	High Similarity	NPC263119
0.8621	High Similarity	NPC46640
0.8621	High Similarity	NPC34436
0.8614	High Similarity	NPC191046
0.8614	High Similarity	NPC194095
0.8614	High Similarity	NPC327032
0.8613	High Similarity	NPC298778
0.8606	High Similarity	NPC124842
0.8598	High Similarity	NPC303989
0.8598	High Similarity	NPC183380
0.8596	High Similarity	NPC178281
0.8589	High Similarity	NPC474795
0.8589	High Similarity	NPC303013
0.8589	High Similarity	NPC130959
0.8589	High Similarity	NPC474940
0.8589	High Similarity	NPC159697
0.8588	High Similarity	NPC477860
0.8588	High Similarity	NPC475161
0.858	High Similarity	NPC21046
0.8571	High Similarity	NPC294149
0.8571	High Similarity	NPC133984
0.8571	High Similarity	NPC469354
0.8571	High Similarity	NPC476358
0.8563	High Similarity	NPC129930
0.8563	High Similarity	NPC474075
0.8563	High Similarity	NPC111536
0.8563	High Similarity	NPC471921
0.8563	High Similarity	NPC76128
0.8563	High Similarity	NPC312006
0.8563	High Similarity	NPC20114
0.8563	High Similarity	NPC30432
0.8563	High Similarity	NPC471920
0.8563	High Similarity	NPC114550
0.8563	High Similarity	NPC471922
0.8563	High Similarity	NPC292712
0.8563	High Similarity	NPC5029
0.8563	High Similarity	NPC271385
0.8554	High Similarity	NPC137813
0.8554	High Similarity	NPC157898
0.8538	High Similarity	NPC147596
0.8537	High Similarity	NPC474893
0.8537	High Similarity	NPC181452
0.8537	High Similarity	NPC475940
0.8537	High Similarity	NPC220006
0.8523	High Similarity	NPC469397
0.8523	High Similarity	NPC46958
0.8523	High Similarity	NPC297574
0.8514	High Similarity	NPC473550
0.8512	High Similarity	NPC228357
0.8508	High Similarity	NPC314672
0.8506	High Similarity	NPC181778
0.8497	Intermediate Similarity	NPC63470
0.8497	Intermediate Similarity	NPC116745
0.8497	Intermediate Similarity	NPC477502
0.8494	Intermediate Similarity	NPC36130
0.8494	Intermediate Similarity	NPC134905
0.8485	Intermediate Similarity	NPC205054
0.8483	Intermediate Similarity	NPC53680
0.8483	Intermediate Similarity	NPC208797
0.848	Intermediate Similarity	NPC212099
0.848	Intermediate Similarity	NPC278329
0.848	Intermediate Similarity	NPC56735
0.848	Intermediate Similarity	NPC146837
0.848	Intermediate Similarity	NPC148273
0.848	Intermediate Similarity	NPC61594
0.848	Intermediate Similarity	NPC101116
0.8476	Intermediate Similarity	NPC290902
0.8476	Intermediate Similarity	NPC470757
0.8476	Intermediate Similarity	NPC474834
0.8476	Intermediate Similarity	NPC474856
0.8476	Intermediate Similarity	NPC117788
0.8476	Intermediate Similarity	NPC127046
0.8476	Intermediate Similarity	NPC52692
0.8476	Intermediate Similarity	NPC291326
0.8475	Intermediate Similarity	NPC35266
0.8471	Intermediate Similarity	NPC24627
0.8471	Intermediate Similarity	NPC203020
0.8471	Intermediate Similarity	NPC239966
0.847	Intermediate Similarity	NPC314020
0.8466	Intermediate Similarity	NPC199533
0.8466	Intermediate Similarity	NPC470454
0.8466	Intermediate Similarity	NPC63105
0.8462	Intermediate Similarity	NPC226759
0.8462	Intermediate Similarity	NPC167098
0.8462	Intermediate Similarity	NPC321046
0.8462	Intermediate Similarity	NPC264302
0.8462	Intermediate Similarity	NPC1913
0.8462	Intermediate Similarity	NPC296044
0.8457	Intermediate Similarity	NPC469778
0.8457	Intermediate Similarity	NPC32723
0.8457	Intermediate Similarity	NPC469777
0.8457	Intermediate Similarity	NPC472620
0.8457	Intermediate Similarity	NPC135334
0.8457	Intermediate Similarity	NPC469772
0.8457	Intermediate Similarity	NPC469773
0.8457	Intermediate Similarity	NPC469775
0.8457	Intermediate Similarity	NPC469774
0.8457	Intermediate Similarity	NPC469776
0.8457	Intermediate Similarity	NPC100925
0.8457	Intermediate Similarity	NPC295941
0.8453	Intermediate Similarity	NPC142291
0.8453	Intermediate Similarity	NPC7839
0.8448	Intermediate Similarity	NPC476017
0.8448	Intermediate Similarity	NPC259905
0.8448	Intermediate Similarity	NPC229687
0.8443	Intermediate Similarity	NPC475227
0.8443	Intermediate Similarity	NPC200645
0.8443	Intermediate Similarity	NPC180388
0.8443	Intermediate Similarity	NPC106669
0.8439	Intermediate Similarity	NPC13481
0.8439	Intermediate Similarity	NPC178851
0.8439	Intermediate Similarity	NPC207575
0.8436	Intermediate Similarity	NPC293227
0.8436	Intermediate Similarity	NPC313452
0.8436	Intermediate Similarity	NPC473717
0.8436	Intermediate Similarity	NPC473631
0.8436	Intermediate Similarity	NPC475662
0.8427	Intermediate Similarity	NPC275690
0.8427	Intermediate Similarity	NPC245059
0.8427	Intermediate Similarity	NPC80956
0.8427	Intermediate Similarity	NPC161609
0.8427	Intermediate Similarity	NPC84494
0.8418	Intermediate Similarity	NPC475233
0.8418	Intermediate Similarity	NPC472723
0.8418	Intermediate Similarity	NPC475246
0.8415	Intermediate Similarity	NPC474991
0.8415	Intermediate Similarity	NPC475299
0.8415	Intermediate Similarity	NPC58752
0.8412	Intermediate Similarity	NPC160780
0.8412	Intermediate Similarity	NPC289811
0.8409	Intermediate Similarity	NPC203751
0.8409	Intermediate Similarity	NPC172033
0.8409	Intermediate Similarity	NPC471969
0.8409	Intermediate Similarity	NPC213052
0.8409	Intermediate Similarity	NPC175230
0.8409	Intermediate Similarity	NPC208668
0.8409	Intermediate Similarity	NPC88560
0.84	Intermediate Similarity	NPC472803
0.84	Intermediate Similarity	NPC224462
0.84	Intermediate Similarity	NPC475058
0.84	Intermediate Similarity	NPC149011
0.84	Intermediate Similarity	NPC204937
0.8398	Intermediate Similarity	NPC174486
0.8391	Intermediate Similarity	NPC45400
0.8391	Intermediate Similarity	NPC474024
0.8391	Intermediate Similarity	NPC229729
0.8382	Intermediate Similarity	NPC165720
0.8382	Intermediate Similarity	NPC475738
0.8382	Intermediate Similarity	NPC294722
0.8382	Intermediate Similarity	NPC475979
0.8382	Intermediate Similarity	NPC99216
0.8382	Intermediate Similarity	NPC478026
0.838	Intermediate Similarity	NPC470452
0.838	Intermediate Similarity	NPC265795
0.838	Intermediate Similarity	NPC315221
0.838	Intermediate Similarity	NPC164047
0.838	Intermediate Similarity	NPC470448
0.838	Intermediate Similarity	NPC470453
0.8373	Intermediate Similarity	NPC474305
0.8372	Intermediate Similarity	NPC22324
0.8372	Intermediate Similarity	NPC216752
0.8372	Intermediate Similarity	NPC285108
0.8372	Intermediate Similarity	NPC33298
0.8371	Intermediate Similarity	NPC469418
0.8371	Intermediate Similarity	NPC469600
0.8363	Intermediate Similarity	NPC119125
0.8363	Intermediate Similarity	NPC328093
0.8363	Intermediate Similarity	NPC166277
0.8362	Intermediate Similarity	NPC3718
0.8362	Intermediate Similarity	NPC108202

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 NPC475054 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	349
0.1-0.2	956
0.2-0.3	1890
0.3-0.4	2577
0.4-0.5	1922
0.5-0.6	920
0.6-0.7	400
0.7-0.8	127
0.8-0.85	9
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8315	Intermediate Similarity	NPD8312	Approved
0.8315	Intermediate Similarity	NPD8313	Approved
0.8295	Intermediate Similarity	NPD7074	Phase 3
0.8287	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD7054	Approved
0.8239	Intermediate Similarity	NPD5844	Phase 1
0.8192	Intermediate Similarity	NPD7472	Approved
0.8187	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD7228	Approved
0.8182	Intermediate Similarity	NPD3818	Discontinued
0.8156	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8122	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD7685	Pre-registration
0.8098	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD6674	Discontinued
0.8023	Intermediate Similarity	NPD7473	Discontinued
0.8	Intermediate Similarity	NPD7251	Discontinued
0.7989	Intermediate Similarity	NPD6234	Discontinued
0.7965	Intermediate Similarity	NPD1465	Phase 2
0.7956	Intermediate Similarity	NPD7808	Phase 3
0.7944	Intermediate Similarity	NPD6797	Phase 2
0.7941	Intermediate Similarity	NPD7458	Discontinued
0.7931	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD37	Approved
0.7901	Intermediate Similarity	NPD6559	Discontinued
0.7892	Intermediate Similarity	NPD4628	Phase 3
0.7874	Intermediate Similarity	NPD4967	Phase 2
0.7874	Intermediate Similarity	NPD4966	Approved
0.7874	Intermediate Similarity	NPD4965	Approved
0.7861	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD6232	Discontinued
0.7845	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7833	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD1934	Approved
0.7765	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD6166	Phase 2
0.7765	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD7819	Suspended
0.7733	Intermediate Similarity	NPD3226	Approved
0.7727	Intermediate Similarity	NPD7075	Discontinued
0.7705	Intermediate Similarity	NPD7240	Approved
0.7697	Intermediate Similarity	NPD8127	Discontinued
0.7697	Intermediate Similarity	NPD7199	Phase 2
0.7688	Intermediate Similarity	NPD8434	Phase 2
0.768	Intermediate Similarity	NPD7435	Discontinued
0.7665	Intermediate Similarity	NPD8151	Discontinued
0.7657	Intermediate Similarity	NPD8455	Phase 2
0.764	Intermediate Similarity	NPD5494	Approved
0.7619	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD7266	Discontinued
0.7598	Intermediate Similarity	NPD6959	Discontinued
0.7594	Intermediate Similarity	NPD8150	Discontinued
0.7586	Intermediate Similarity	NPD4380	Phase 2
0.7574	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD1653	Approved
0.7557	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD2801	Approved
0.7543	Intermediate Similarity	NPD7411	Suspended
0.7529	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD6782	Approved
0.7526	Intermediate Similarity	NPD6778	Approved
0.7526	Intermediate Similarity	NPD6776	Approved
0.7526	Intermediate Similarity	NPD6779	Approved
0.7526	Intermediate Similarity	NPD6781	Approved
0.7526	Intermediate Similarity	NPD6780	Approved
0.7526	Intermediate Similarity	NPD6777	Approved
0.7524	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD3817	Phase 2
0.75	Intermediate Similarity	NPD2532	Approved
0.75	Intermediate Similarity	NPD2534	Approved
0.75	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2533	Approved
0.75	Intermediate Similarity	NPD7783	Phase 2
0.75	Intermediate Similarity	NPD2346	Discontinued
0.75	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD3882	Suspended
0.7471	Intermediate Similarity	NPD8166	Discontinued
0.745	Intermediate Similarity	NPD7874	Approved
0.745	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD7698	Approved
0.7411	Intermediate Similarity	NPD7697	Approved
0.7411	Intermediate Similarity	NPD7696	Phase 3
0.7401	Intermediate Similarity	NPD6801	Discontinued
0.7391	Intermediate Similarity	NPD3751	Discontinued
0.7386	Intermediate Similarity	NPD6599	Discontinued
0.7385	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7871	Phase 2
0.7374	Intermediate Similarity	NPD8320	Phase 1
0.7374	Intermediate Similarity	NPD7870	Phase 2
0.7374	Intermediate Similarity	NPD8319	Approved
0.7368	Intermediate Similarity	NPD3750	Approved
0.736	Intermediate Similarity	NPD6823	Phase 2
0.7358	Intermediate Similarity	NPD6535	Approved
0.7358	Intermediate Similarity	NPD6534	Approved
0.7356	Intermediate Similarity	NPD6273	Approved
0.735	Intermediate Similarity	NPD7701	Phase 2
0.7337	Intermediate Similarity	NPD6100	Approved
0.7337	Intermediate Similarity	NPD6099	Approved
0.7333	Intermediate Similarity	NPD7699	Phase 2
0.7333	Intermediate Similarity	NPD7700	Phase 2
0.7327	Intermediate Similarity	NPD7801	Approved
0.7299	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7003	Approved
0.7241	Intermediate Similarity	NPD1511	Approved
0.7236	Intermediate Similarity	NPD7680	Approved
0.7225	Intermediate Similarity	NPD6190	Approved
0.7222	Intermediate Similarity	NPD5402	Approved
0.7216	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD6212	Phase 3
0.7216	Intermediate Similarity	NPD6213	Phase 3
0.7204	Intermediate Similarity	NPD7799	Discontinued
0.7202	Intermediate Similarity	NPD230	Phase 1
0.7198	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD7028	Phase 2
0.7174	Intermediate Similarity	NPD3787	Discontinued
0.7172	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD1512	Approved
0.7151	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD2800	Approved
0.7102	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD7768	Phase 2
0.7081	Intermediate Similarity	NPD5710	Approved
0.7081	Intermediate Similarity	NPD5711	Approved
0.7076	Intermediate Similarity	NPD3748	Approved
0.7076	Intermediate Similarity	NPD2799	Discontinued
0.7074	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD4110	Phase 3
0.7069	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD1549	Phase 2
0.7049	Intermediate Similarity	NPD3749	Approved
0.7045	Intermediate Similarity	NPD6799	Approved
0.7041	Intermediate Similarity	NPD4060	Phase 1
0.7035	Intermediate Similarity	NPD2935	Discontinued
0.7035	Intermediate Similarity	NPD8285	Discontinued
0.7022	Intermediate Similarity	NPD5403	Approved
0.7021	Intermediate Similarity	NPD7177	Discontinued
0.7018	Intermediate Similarity	NPD7097	Phase 1
0.7015	Intermediate Similarity	NPD3057	Approved
0.7015	Intermediate Similarity	NPD2491	Approved
0.701	Intermediate Similarity	NPD7585	Approved
0.7	Intermediate Similarity	NPD447	Suspended
0.7	Intermediate Similarity	NPD1933	Approved
0.6995	Remote Similarity	NPD7999	Approved
0.6994	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD7930	Approved
0.6965	Remote Similarity	NPD2494	Approved
0.6965	Remote Similarity	NPD2493	Approved
0.6964	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD8368	Discontinued
0.6963	Remote Similarity	NPD6764	Approved
0.6963	Remote Similarity	NPD6765	Approved
0.6961	Remote Similarity	NPD7584	Approved
0.6961	Remote Similarity	NPD7583	Approved
0.6959	Remote Similarity	NPD6651	Approved
0.6946	Remote Similarity	NPD9494	Approved
0.6946	Remote Similarity	NPD4582	Approved
0.6946	Remote Similarity	NPD4583	Approved
0.6941	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD3620	Phase 2
0.6941	Remote Similarity	NPD1613	Approved
0.6941	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.694	Remote Similarity	NPD5353	Approved
0.6939	Remote Similarity	NPD2488	Approved
0.6939	Remote Similarity	NPD2490	Approved
0.6936	Remote Similarity	NPD2438	Suspended
0.6935	Remote Similarity	NPD1247	Approved
0.6934	Remote Similarity	NPD7907	Approved
0.6931	Remote Similarity	NPD3533	Approved
0.6931	Remote Similarity	NPD2972	Approved
0.6931	Remote Similarity	NPD3448	Approved
0.6923	Remote Similarity	NPD2313	Discontinued
0.6923	Remote Similarity	NPD7985	Registered
0.6923	Remote Similarity	NPD3268	Approved
0.6923	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD4111	Phase 1
0.6919	Remote Similarity	NPD4665	Approved
0.6919	Remote Similarity	NPD919	Approved
0.6915	Remote Similarity	NPD4107	Approved
0.6914	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.691	Remote Similarity	NPD5401	Approved
0.6901	Remote Similarity	NPD6355	Discontinued
0.6898	Remote Similarity	NPD7229	Phase 3
0.6897	Remote Similarity	NPD5763	Approved
0.6897	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5762	Approved
0.6897	Remote Similarity	NPD4002	Approved
0.6897	Remote Similarity	NPD4004	Approved
0.6893	Remote Similarity	NPD7236	Approved
0.6889	Remote Similarity	NPD7239	Suspended
0.6885	Remote Similarity	NPD5761	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