NPASS Compound

Structure

NPC88009 OpenBabel07101718332D 37 40 0 0 1 0 0 0 0 0999 V2000 -5.7633 -5.8212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1161 -6.3564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1890 -3.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1913 -2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4762 -4.6622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1453 -3.9190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 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 0.8660 -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 -4.7852 -5.6132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8581 -2.7601 0.0000 C 0 0 1 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 3.0000 0.0000 C 0 0 0 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 -3.5491 -1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8363 -2.9680 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 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 0.8660 1.5000 0.0000 C 0 0 1 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 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5054 -2.2248 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 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 4 19 1 0 0 0 0 5 20 1 0 0 0 0 8 11 1 0 0 0 0 8 17 1 0 0 0 0 9 10 1 0 0 0 0 9 22 1 0 0 0 0 10 23 1 0 0 0 0 11 25 1 0 0 0 0 12 14 1 0 0 0 0 12 24 1 0 0 0 0 13 15 1 0 0 0 0 13 26 1 0 0 0 0 14 30 1 0 0 0 0 15 31 1 0 0 0 0 16 21 2 0 0 0 0 16 27 1 0 0 0 0 18 3 1 6 0 0 0 18 22 1 0 0 0 0 18 25 1 0 0 0 0 19 32 2 0 0 0 0 19 36 1 0 0 0 0 20 33 2 0 0 0 0 20 37 1 0 0 0 0 21 23 1 0 0 0 0 21 24 1 0 0 0 0 22 30 1 1 0 0 0 23 30 1 1 0 0 0 24 31 1 1 0 0 0 25 34 1 1 0 0 0 26 29 1 0 0 0 0 26 35 1 1 0 0 0 27 28 1 0 0 0 0 27 36 1 6 0 0 0 28 29 1 0 0 0 0 28 31 1 1 0 0 0 29 37 1 1 0 0 0 30 6 1 1 0 0 0 31 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	518.36
Volume:	555.338
LogP:	5.002
LogD:	4.793
LogS:	-4.655
# Rotatable Bonds:	9
TPSA:	93.06
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.344
Synthetic Accessibility Score:	5.083
Fsp3:	0.871
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.706
MDCK Permeability:	6.184941594256088e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.986
Human Intestinal Absorption (HIA):	0.217
20% Bioavailability (F20%):	0.047
30% Bioavailability (F30%):	0.857

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	91.2330093383789%
Volume Distribution (VD):	1.666
Pgp-substrate:	2.23038387298584%

ADMET: Metabolism

CYP1A2-inhibitor:	0.068
CYP1A2-substrate:	0.106
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.44
CYP2C9-inhibitor:	0.325
CYP2C9-substrate:	0.1
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.071
CYP3A4-inhibitor:	0.482
CYP3A4-substrate:	0.347

ADMET: Excretion

Clearance (CL):	2.999
Half-life (T1/2):	0.299

ADMET: Toxicity

hERG Blockers:	0.102
Human Hepatotoxicity (H-HT):	0.885
Drug-inuced Liver Injury (DILI):	0.659
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.173
Maximum Recommended Daily Dose:	0.01
Skin Sensitization:	0.191
Carcinogencity:	0.014
Eye Corrosion:	0.044
Eye Irritation:	0.064
Respiratory Toxicity:	0.953

Download Data

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

Natural Product: NPC88009

Natural Product ID:	NPC88009
*Common Name:**	Agosterol C
IUPAC Name:	[(3S,4R,5S,6S,9R,10R,13R,14R,17R)-4-acetyloxy-3-hydroxy-17-[(2S,3R)-3-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,5,6,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-6-yl] acetate
Synonyms:	Agosterol C
Standard InCHIKey:	TYLRRLLZCVWGTR-PHIAUZCSSA-N
Standard InCHI:	InChI=1S/C31H50O6/c1-17(2)8-11-25(34)18(3)22-9-10-23-21-16-27(36-19(4)32)28-29(37-20(5)33)26(35)13-15-31(28,7)24(21)12-14-30(22,23)6/h16-18,22-29,34-35H,8-15H2,1-7H3/t18-,22+,23-,24-,25+,26-,27-,28-,29-,30+,31+/m0/s1
SMILES:	CC(CC[C@H]([C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1C2=C[C@@H]([C@@H]2[C@]1(C)CC[C@@H]([C@@H]2OC(=O)C)O)OC(=O)C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL457946
PubChem CID:	10414285
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001445] Bile acids, alcohols and derivatives [CHEMONTID:0002194] Hydroxy bile acids, alcohols and derivatives [CHEMONTID:0000516] Dihydroxy bile acids, alcohols 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
NPO32957	Acanthodendrilla sp.	Species	Dictyodendrillidae	Eukaryota	n.a.	n.a.	n.a.	PMID[14510593]
NPO32957	Acanthodendrilla sp.	Species	Dictyodendrillidae	Eukaryota	n.a.	Indonesia	n.a.	PMID[15568767]
NPO32957	Acanthodendrilla sp.	Species	Dictyodendrillidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18257533]
NPO32957	Acanthodendrilla sp.	Species	Dictyodendrillidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9834155]

☑ 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	2

Activity Type	# Activity
Cell Line	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	22.0	ug.mL-1	PMID[549951]
NPT2	Others	Unspecified		IC50	=	10.0	ug.mL-1	PMID[549951]

☑ 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 NPC88009 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	176
0.1-0.2	1190
0.2-0.3	4254
0.3-0.4	10725
0.4-0.5	11105
0.5-0.6	6032
0.6-0.7	5728
0.7-0.8	3191
0.8-0.85	254
0.85-0.9	32
0.9-0.95	5
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9889	High Similarity	NPC210337
0.9674	High Similarity	NPC473510
0.9674	High Similarity	NPC230546
0.957	High Similarity	NPC475617
0.9368	High Similarity	NPC474124
0.9263	High Similarity	NPC475344
0.9263	High Similarity	NPC476471
0.9167	High Similarity	NPC473523
0.9072	High Similarity	NPC473543
0.8842	High Similarity	NPC475032
0.8842	High Similarity	NPC475033
0.8778	High Similarity	NPC474970
0.8713	High Similarity	NPC173905
0.8713	High Similarity	NPC472216
0.8713	High Similarity	NPC5475
0.8713	High Similarity	NPC284828
0.871	High Similarity	NPC234335
0.8696	High Similarity	NPC473647
0.8673	High Similarity	NPC258547
0.8673	High Similarity	NPC283343
0.866	High Similarity	NPC474190
0.8632	High Similarity	NPC8774
0.8617	High Similarity	NPC53555
0.8571	High Similarity	NPC155974
0.8571	High Similarity	NPC473160
0.8557	High Similarity	NPC102426
0.8557	High Similarity	NPC300179
0.8542	High Similarity	NPC227583
0.8542	High Similarity	NPC12103
0.8542	High Similarity	NPC98457
0.8542	High Similarity	NPC471903
0.8542	High Similarity	NPC288970
0.8539	High Similarity	NPC470049
0.8526	High Similarity	NPC127718
0.8526	High Similarity	NPC65402
0.8515	High Similarity	NPC131665
0.8515	High Similarity	NPC255387
0.8511	High Similarity	NPC189520
0.8511	High Similarity	NPC177641
0.8485	Intermediate Similarity	NPC273668
0.8478	Intermediate Similarity	NPC470620
0.8478	Intermediate Similarity	NPC166857
0.8469	Intermediate Similarity	NPC38855
0.8469	Intermediate Similarity	NPC208358
0.8462	Intermediate Similarity	NPC35933
0.8462	Intermediate Similarity	NPC266511
0.8454	Intermediate Similarity	NPC231751
0.8454	Intermediate Similarity	NPC274793
0.8431	Intermediate Similarity	NPC88701
0.8421	Intermediate Similarity	NPC38232
0.8421	Intermediate Similarity	NPC27918
0.8421	Intermediate Similarity	NPC307776
0.8416	Intermediate Similarity	NPC88349
0.8416	Intermediate Similarity	NPC186668
0.8404	Intermediate Similarity	NPC473269
0.8404	Intermediate Similarity	NPC78973
0.84	Intermediate Similarity	NPC281378
0.84	Intermediate Similarity	NPC472821
0.8384	Intermediate Similarity	NPC96784
0.8384	Intermediate Similarity	NPC289670
0.8384	Intermediate Similarity	NPC11974
0.8384	Intermediate Similarity	NPC472554
0.8384	Intermediate Similarity	NPC235920
0.837	Intermediate Similarity	NPC125399
0.837	Intermediate Similarity	NPC131813
0.837	Intermediate Similarity	NPC286153
0.8365	Intermediate Similarity	NPC470076
0.8352	Intermediate Similarity	NPC470077
0.8352	Intermediate Similarity	NPC185568
0.8351	Intermediate Similarity	NPC276103
0.8351	Intermediate Similarity	NPC72204
0.8351	Intermediate Similarity	NPC54248
0.8333	Intermediate Similarity	NPC30166
0.8333	Intermediate Similarity	NPC474922
0.8333	Intermediate Similarity	NPC473586
0.8317	Intermediate Similarity	NPC31430
0.8317	Intermediate Similarity	NPC474550
0.8317	Intermediate Similarity	NPC473577
0.8317	Intermediate Similarity	NPC85593
0.8317	Intermediate Similarity	NPC475585
0.8317	Intermediate Similarity	NPC152966
0.8316	Intermediate Similarity	NPC219516
0.8316	Intermediate Similarity	NPC210268
0.8315	Intermediate Similarity	NPC236112
0.83	Intermediate Similarity	NPC472552
0.8298	Intermediate Similarity	NPC475921
0.8298	Intermediate Similarity	NPC20946
0.8298	Intermediate Similarity	NPC246028
0.8298	Intermediate Similarity	NPC474704
0.8298	Intermediate Similarity	NPC82876
0.8298	Intermediate Similarity	NPC472240
0.8298	Intermediate Similarity	NPC262858
0.828	Intermediate Similarity	NPC149224
0.8269	Intermediate Similarity	NPC472214
0.8269	Intermediate Similarity	NPC472215
0.8252	Intermediate Similarity	NPC472218
0.8252	Intermediate Similarity	NPC472219
0.8252	Intermediate Similarity	NPC472217
0.8252	Intermediate Similarity	NPC475263
0.8247	Intermediate Similarity	NPC276110
0.8242	Intermediate Similarity	NPC207013
0.8242	Intermediate Similarity	NPC317458
0.8235	Intermediate Similarity	NPC475414
0.8235	Intermediate Similarity	NPC475290
0.8235	Intermediate Similarity	NPC220217
0.8235	Intermediate Similarity	NPC173172
0.8235	Intermediate Similarity	NPC471206
0.8235	Intermediate Similarity	NPC119855
0.8222	Intermediate Similarity	NPC474759
0.8222	Intermediate Similarity	NPC474531
0.8222	Intermediate Similarity	NPC82986
0.8222	Intermediate Similarity	NPC474683
0.8222	Intermediate Similarity	NPC25554
0.8222	Intermediate Similarity	NPC474752
0.8222	Intermediate Similarity	NPC7505
0.8222	Intermediate Similarity	NPC474731
0.8218	Intermediate Similarity	NPC297617
0.8218	Intermediate Similarity	NPC10232
0.8218	Intermediate Similarity	NPC112009
0.8218	Intermediate Similarity	NPC196471
0.8218	Intermediate Similarity	NPC187302
0.8218	Intermediate Similarity	NPC189588
0.8218	Intermediate Similarity	NPC97487
0.8218	Intermediate Similarity	NPC160583
0.8211	Intermediate Similarity	NPC471896
0.82	Intermediate Similarity	NPC222875
0.82	Intermediate Similarity	NPC21064
0.82	Intermediate Similarity	NPC121072
0.82	Intermediate Similarity	NPC25177
0.82	Intermediate Similarity	NPC295110
0.82	Intermediate Similarity	NPC268829
0.82	Intermediate Similarity	NPC49532
0.82	Intermediate Similarity	NPC247701
0.8191	Intermediate Similarity	NPC471952
0.8191	Intermediate Similarity	NPC133588
0.8191	Intermediate Similarity	NPC67872
0.8191	Intermediate Similarity	NPC474668
0.8182	Intermediate Similarity	NPC477875
0.8182	Intermediate Similarity	NPC470066
0.8182	Intermediate Similarity	NPC470067
0.8182	Intermediate Similarity	NPC477876
0.8182	Intermediate Similarity	NPC247233
0.8182	Intermediate Similarity	NPC470068
0.8182	Intermediate Similarity	NPC476895
0.8182	Intermediate Similarity	NPC92275
0.8172	Intermediate Similarity	NPC175145
0.8172	Intermediate Similarity	NPC475069
0.8163	Intermediate Similarity	NPC190713
0.8163	Intermediate Similarity	NPC169270
0.8163	Intermediate Similarity	NPC306797
0.8163	Intermediate Similarity	NPC111834
0.8163	Intermediate Similarity	NPC253115
0.8163	Intermediate Similarity	NPC284194
0.8163	Intermediate Similarity	NPC292718
0.8163	Intermediate Similarity	NPC304899
0.8163	Intermediate Similarity	NPC471765
0.8163	Intermediate Similarity	NPC221801
0.8163	Intermediate Similarity	NPC211810
0.8155	Intermediate Similarity	NPC472820
0.8155	Intermediate Similarity	NPC475176
0.8155	Intermediate Similarity	NPC475781
0.8155	Intermediate Similarity	NPC471205
0.8155	Intermediate Similarity	NPC144459
0.8148	Intermediate Similarity	NPC203862
0.8148	Intermediate Similarity	NPC152615
0.8144	Intermediate Similarity	NPC105490
0.8144	Intermediate Similarity	NPC472360
0.8144	Intermediate Similarity	NPC211238
0.8144	Intermediate Similarity	NPC201725
0.8144	Intermediate Similarity	NPC215700
0.8144	Intermediate Similarity	NPC472416
0.8137	Intermediate Similarity	NPC471293
0.8137	Intermediate Similarity	NPC93352
0.8132	Intermediate Similarity	NPC101462
0.8131	Intermediate Similarity	NPC471633
0.8131	Intermediate Similarity	NPC147912
0.8131	Intermediate Similarity	NPC84949
0.8131	Intermediate Similarity	NPC69576
0.8131	Intermediate Similarity	NPC31354
0.8131	Intermediate Similarity	NPC67259
0.8125	Intermediate Similarity	NPC329842
0.8125	Intermediate Similarity	NPC41554
0.8125	Intermediate Similarity	NPC97404
0.8125	Intermediate Similarity	NPC130840
0.8125	Intermediate Similarity	NPC471453
0.8119	Intermediate Similarity	NPC154452
0.8119	Intermediate Similarity	NPC11956
0.8119	Intermediate Similarity	NPC177701
0.8119	Intermediate Similarity	NPC470972
0.8105	Intermediate Similarity	NPC470361
0.8105	Intermediate Similarity	NPC146554
0.8105	Intermediate Similarity	NPC261320
0.8105	Intermediate Similarity	NPC16265
0.81	Intermediate Similarity	NPC161527
0.81	Intermediate Similarity	NPC228251
0.81	Intermediate Similarity	NPC477971
0.81	Intermediate Similarity	NPC472826
0.81	Intermediate Similarity	NPC201406
0.81	Intermediate Similarity	NPC477972
0.81	Intermediate Similarity	NPC167974

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 NPC88009 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	145
0.1-0.2	1360
0.2-0.3	3910
0.3-0.4	2490
0.4-0.5	732
0.5-0.6	221
0.6-0.7	183
0.7-0.8	108
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8182	Intermediate Similarity	NPD7638	Approved
0.81	Intermediate Similarity	NPD7639	Approved
0.81	Intermediate Similarity	NPD7640	Approved
0.8	Intermediate Similarity	NPD7516	Approved
0.8	Intermediate Similarity	NPD4225	Approved
0.7982	Intermediate Similarity	NPD7115	Discovery
0.7917	Intermediate Similarity	NPD6051	Approved
0.7912	Intermediate Similarity	NPD7525	Registered
0.7909	Intermediate Similarity	NPD7328	Approved
0.7909	Intermediate Similarity	NPD7327	Approved
0.7857	Intermediate Similarity	NPD6399	Phase 3
0.7768	Intermediate Similarity	NPD8377	Approved
0.7768	Intermediate Similarity	NPD8294	Approved
0.7714	Intermediate Similarity	NPD5739	Approved
0.7714	Intermediate Similarity	NPD7128	Approved
0.7714	Intermediate Similarity	NPD6675	Approved
0.7714	Intermediate Similarity	NPD6402	Approved
0.7699	Intermediate Similarity	NPD8033	Approved
0.7699	Intermediate Similarity	NPD8379	Approved
0.7699	Intermediate Similarity	NPD8378	Approved
0.7699	Intermediate Similarity	NPD8296	Approved
0.7699	Intermediate Similarity	NPD8335	Approved
0.7699	Intermediate Similarity	NPD7503	Approved
0.7699	Intermediate Similarity	NPD8380	Approved
0.7664	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD8297	Approved
0.757	Intermediate Similarity	NPD6881	Approved
0.757	Intermediate Similarity	NPD6899	Approved
0.757	Intermediate Similarity	NPD7320	Approved
0.7556	Intermediate Similarity	NPD6942	Approved
0.7556	Intermediate Similarity	NPD7339	Approved
0.7526	Intermediate Similarity	NPD7524	Approved
0.75	Intermediate Similarity	NPD6373	Approved
0.75	Intermediate Similarity	NPD6372	Approved
0.7477	Intermediate Similarity	NPD5701	Approved
0.7477	Intermediate Similarity	NPD5697	Approved
0.7436	Intermediate Similarity	NPD7507	Approved
0.7431	Intermediate Similarity	NPD6883	Approved
0.7431	Intermediate Similarity	NPD7290	Approved
0.7431	Intermediate Similarity	NPD7102	Approved
0.7429	Intermediate Similarity	NPD7632	Discontinued
0.7419	Intermediate Similarity	NPD7645	Phase 2
0.7407	Intermediate Similarity	NPD6686	Approved
0.74	Intermediate Similarity	NPD8035	Phase 2
0.74	Intermediate Similarity	NPD8034	Phase 2
0.7396	Intermediate Similarity	NPD4786	Approved
0.7379	Intermediate Similarity	NPD6084	Phase 2
0.7379	Intermediate Similarity	NPD6083	Phase 2
0.7374	Intermediate Similarity	NPD5328	Approved
0.7364	Intermediate Similarity	NPD6847	Approved
0.7364	Intermediate Similarity	NPD8130	Phase 1
0.7364	Intermediate Similarity	NPD6617	Approved
0.7364	Intermediate Similarity	NPD6649	Approved
0.7364	Intermediate Similarity	NPD6650	Approved
0.7364	Intermediate Similarity	NPD6869	Approved
0.7339	Intermediate Similarity	NPD6014	Approved
0.7339	Intermediate Similarity	NPD6013	Approved
0.7339	Intermediate Similarity	NPD6012	Approved
0.7333	Intermediate Similarity	NPD4159	Approved
0.7333	Intermediate Similarity	NPD5344	Discontinued
0.732	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6882	Approved
0.7283	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD7748	Approved
0.725	Intermediate Similarity	NPD7319	Approved
0.7248	Intermediate Similarity	NPD6011	Approved
0.7245	Intermediate Similarity	NPD3618	Phase 1
0.7232	Intermediate Similarity	NPD4632	Approved
0.7228	Intermediate Similarity	NPD7515	Phase 2
0.7228	Intermediate Similarity	NPD6079	Approved
0.7228	Intermediate Similarity	NPD7637	Suspended
0.7216	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD4755	Approved
0.7212	Intermediate Similarity	NPD7902	Approved
0.7207	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD3667	Approved
0.7157	Intermediate Similarity	NPD4202	Approved
0.7156	Intermediate Similarity	NPD6412	Phase 2
0.7155	Intermediate Similarity	NPD6319	Approved
0.7113	Intermediate Similarity	NPD6695	Phase 3
0.7103	Intermediate Similarity	NPD5211	Phase 2
0.71	Intermediate Similarity	NPD6672	Approved
0.71	Intermediate Similarity	NPD5737	Approved
0.7097	Intermediate Similarity	NPD6933	Approved
0.7091	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD8133	Approved
0.7075	Intermediate Similarity	NPD4700	Approved
0.7075	Intermediate Similarity	NPD5286	Approved
0.7075	Intermediate Similarity	NPD4696	Approved
0.7075	Intermediate Similarity	NPD5285	Approved
0.7071	Intermediate Similarity	NPD7146	Approved
0.7071	Intermediate Similarity	NPD6409	Approved
0.7071	Intermediate Similarity	NPD6684	Approved
0.7071	Intermediate Similarity	NPD5330	Approved
0.7071	Intermediate Similarity	NPD7521	Approved
0.7071	Intermediate Similarity	NPD7334	Approved
0.7027	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD5695	Phase 3
0.7	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD5696	Approved
0.6972	Remote Similarity	NPD5141	Approved
0.697	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6274	Approved
0.6952	Remote Similarity	NPD5221	Approved
0.6952	Remote Similarity	NPD4697	Phase 3
0.6952	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD5222	Approved
0.6944	Remote Similarity	NPD5226	Approved
0.6944	Remote Similarity	NPD5225	Approved
0.6944	Remote Similarity	NPD4633	Approved
0.6944	Remote Similarity	NPD5224	Approved
0.6931	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD6903	Approved
0.6923	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7900	Approved
0.6923	Remote Similarity	NPD7101	Approved
0.6923	Remote Similarity	NPD7100	Approved
0.6917	Remote Similarity	NPD7492	Approved
0.6916	Remote Similarity	NPD6648	Approved
0.6897	Remote Similarity	NPD6009	Approved
0.6893	Remote Similarity	NPD5693	Phase 1
0.6887	Remote Similarity	NPD5173	Approved
0.6882	Remote Similarity	NPD6926	Approved
0.6882	Remote Similarity	NPD6924	Approved
0.6881	Remote Similarity	NPD5175	Approved
0.6881	Remote Similarity	NPD5174	Approved
0.6875	Remote Similarity	NPD6929	Approved
0.6869	Remote Similarity	NPD3665	Phase 1
0.6869	Remote Similarity	NPD3133	Approved
0.6869	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD3666	Approved
0.6864	Remote Similarity	NPD6054	Approved
0.6864	Remote Similarity	NPD6059	Approved
0.6863	Remote Similarity	NPD4753	Phase 2
0.686	Remote Similarity	NPD6616	Approved
0.6857	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD5223	Approved
0.6848	Remote Similarity	NPD4243	Approved
0.6842	Remote Similarity	NPD6053	Discontinued
0.6842	Remote Similarity	NPD6116	Phase 1
0.6838	Remote Similarity	NPD6335	Approved
0.6837	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD7604	Phase 2
0.6832	Remote Similarity	NPD7750	Discontinued
0.6814	Remote Similarity	NPD4634	Approved
0.6813	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6868	Approved
0.6807	Remote Similarity	NPD5983	Phase 2
0.6807	Remote Similarity	NPD6908	Approved
0.6807	Remote Similarity	NPD6909	Approved
0.6804	Remote Similarity	NPD6930	Phase 2
0.6804	Remote Similarity	NPD6931	Approved
0.6803	Remote Similarity	NPD8293	Discontinued
0.6803	Remote Similarity	NPD7078	Approved
0.6757	Remote Similarity	NPD4768	Approved
0.6757	Remote Similarity	NPD4767	Approved
0.6757	Remote Similarity	NPD6008	Approved
0.6752	Remote Similarity	NPD6317	Approved
0.675	Remote Similarity	NPD6370	Approved
0.6748	Remote Similarity	NPD7736	Approved
0.6737	Remote Similarity	NPD6117	Approved
0.6733	Remote Similarity	NPD6098	Approved
0.6731	Remote Similarity	NPD6411	Approved
0.6727	Remote Similarity	NPD4754	Approved
0.6721	Remote Similarity	NPD6336	Discontinued
0.6702	Remote Similarity	NPD4784	Approved
0.6702	Remote Similarity	NPD4785	Approved
0.6701	Remote Similarity	NPD4195	Approved
0.67	Remote Similarity	NPD3668	Phase 3
0.6699	Remote Similarity	NPD6080	Approved
0.6699	Remote Similarity	NPD6673	Approved
0.6699	Remote Similarity	NPD6904	Approved
0.6695	Remote Similarity	NPD6313	Approved
0.6695	Remote Similarity	NPD6314	Approved
0.6667	Remote Similarity	NPD7152	Approved
0.6667	Remote Similarity	NPD6925	Approved
0.6667	Remote Similarity	NPD7151	Approved
0.6667	Remote Similarity	NPD5776	Phase 2
0.6667	Remote Similarity	NPD6016	Approved
0.6667	Remote Similarity	NPD7150	Approved
0.6667	Remote Similarity	NPD6015	Approved
0.6637	Remote Similarity	NPD5128	Approved
0.6637	Remote Similarity	NPD4730	Approved
0.6637	Remote Similarity	NPD4729	Approved
0.6636	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD6698	Approved
0.6635	Remote Similarity	NPD7838	Discovery
0.6635	Remote Similarity	NPD46	Approved
0.6634	Remote Similarity	NPD1694	Approved
0.6633	Remote Similarity	NPD4748	Discontinued
0.6633	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD7509	Discontinued
0.6633	Remote Similarity	NPD7514	Phase 3
0.663	Remote Similarity	NPD6923	Approved
0.663	Remote Similarity	NPD6922	Approved
0.6612	Remote Similarity	NPD5988	Approved
0.6598	Remote Similarity	NPD6118	Approved
0.6598	Remote Similarity	NPD6697	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