NPASS Compound

Structure

CID154072 OpenBabel06191715522D 32 35 0 0 1 0 0 0 0 0999 V2000 -0.2731 3.2269 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8252 5.6825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9269 4.7129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5355 0.5241 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0006 1.9867 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2251 -0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6902 0.9758 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6895 0.9749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2124 3.4302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6395 4.2191 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3803 0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8448 1.4636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6893 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3809 -1.9509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8456 -1.4637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8459 2.4380 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2254 -1.4627 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8456 1.4631 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6905 0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8454 -0.4877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5361 -1.4632 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8156 2.5397 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6910 -1.9514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0363 5.1097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5358 -0.4872 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0003 0.9754 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 5.0915 -1.9625 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3884 1.7508 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6913 -2.9514 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4635 5.8986 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 24 1 0 0 0 0 3 24 1 0 0 0 0 5 26 1 0 0 0 0 6 11 1 0 0 0 0 6 17 1 0 0 0 0 7 12 1 0 0 0 0 7 19 1 0 0 0 0 8 13 1 0 0 0 0 8 18 1 0 0 0 0 9 10 1 0 0 0 0 9 22 1 0 0 0 0 10 24 1 0 0 0 0 11 25 1 0 0 0 0 12 26 1 0 0 0 0 13 27 1 0 0 0 0 14 17 1 0 0 0 0 14 21 1 0 0 0 0 15 20 2 0 0 0 0 15 23 1 0 0 0 0 16 1 1 1 0 0 0 16 18 1 0 0 0 0 16 22 1 0 0 0 0 17 28 1 6 0 0 0 18 26 1 6 0 0 0 19 20 1 0 0 0 0 19 25 1 6 0 0 0 20 27 1 0 0 0 0 21 23 1 0 0 0 0 21 25 1 1 0 0 0 22 29 1 6 0 0 0 23 30 2 0 0 0 0 24 31 1 0 0 0 0 25 4 1 6 0 0 0 26 27 1 6 0 0 0 27 32 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	448.32
Volume:	480.0
LogP:	2.472
LogD:	2.241
LogS:	-3.955
# Rotatable Bonds:	5
TPSA:	97.99
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.478
Synthetic Accessibility Score:	5.109
Fsp3:	0.889
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.892
MDCK Permeability:	1.0191964065597858e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.987
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.187
30% Bioavailability (F30%):	0.041

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.396
Plasma Protein Binding (PPB):	80.1238021850586%
Volume Distribution (VD):	1.051
Pgp-substrate:	8.632550239562988%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.477
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.868
CYP2C9-inhibitor:	0.069
CYP2C9-substrate:	0.11
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.047
CYP3A4-inhibitor:	0.41
CYP3A4-substrate:	0.881

ADMET: Excretion

Clearance (CL):	6.806
Half-life (T1/2):	0.329

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.397
Drug-inuced Liver Injury (DILI):	0.066
AMES Toxicity:	0.035
Rat Oral Acute Toxicity:	0.087
Maximum Recommended Daily Dose:	0.906
Skin Sensitization:	0.302
Carcinogencity:	0.326
Eye Corrosion:	0.046
Eye Irritation:	0.067
Respiratory Toxicity:	0.87

Download Data

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

Natural Product: NPC154072

Natural Product ID:	NPC154072
*Common Name:**	2-Deoxyecdysone
IUPAC Name:	(3S,5R,9R,10R,13R,14S,17R)-17-[(2S,3R)-3,6-dihydroxy-6-methylheptan-2-yl]-3,14-dihydroxy-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
Synonyms:	2-Deoxyecdysone
Standard InCHIKey:	CRAPXAGGASWTPU-VQOIUDCISA-N
Standard InCHI:	InChI=1S/C27H44O5/c1-16(22(29)9-10-24(2,3)31)18-8-13-27(32)20-15-23(30)21-14-17(28)6-11-25(21,4)19(20)7-12-26(18,27)5/h15-19,21-22,28-29,31-32H,6-14H2,1-5H3/t16-,17-,18+,19-,21-,22+,25+,26+,27+/m0/s1
SMILES:	O[C@H]1CC[C@]2([C@@H](C1)C(=O)C=C1[C@@H]2CC[C@]2([C@@]1(O)CC[C@@H]2[C@@H]([C@@H](CCC(O)(C)C)O)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2087146
PubChem CID:	13939876
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:0001110] Tetrahydroxy 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
NPO10008	Tinospora capillipes	Species	Menispermaceae	Eukaryota	n.a.	root	n.a.	PMID[17340259]
NPO25734	Tinospora sagittata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28836430]
NPO10008	Tinospora capillipes	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10008	Tinospora capillipes	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25734	Tinospora sagittata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10008	Tinospora capillipes	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25734	Tinospora sagittata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10008	Tinospora capillipes	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25734	Tinospora sagittata	Species	Menispermaceae	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
Others	4

Activity Type	# Activity
Individual Protein	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ratio	=	0.94	n.a.	PMID[528782]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	FICI	=	2.05	n.a.	PMID[528782]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	FICI	=	1.27	n.a.	PMID[528782]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	FICI	=	0.81	n.a.	PMID[528782]

☑ 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 NPC154072 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	190
0.1-0.2	1203
0.2-0.3	4405
0.3-0.4	9869
0.4-0.5	11705
0.5-0.6	6219
0.6-0.7	5716
0.7-0.8	2960
0.8-0.85	294
0.85-0.9	94
0.9-0.95	41
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9565	High Similarity	NPC271195
0.9485	High Similarity	NPC296945
0.9485	High Similarity	NPC319077
0.9485	High Similarity	NPC97202
0.9485	High Similarity	NPC48733
0.9485	High Similarity	NPC150531
0.9485	High Similarity	NPC50692
0.9485	High Similarity	NPC49958
0.9485	High Similarity	NPC152695
0.9485	High Similarity	NPC476027
0.9485	High Similarity	NPC214264
0.9485	High Similarity	NPC302607
0.9485	High Similarity	NPC202167
0.9485	High Similarity	NPC85829
0.9485	High Similarity	NPC260268
0.9485	High Similarity	NPC171137
0.9457	High Similarity	NPC111015
0.9388	High Similarity	NPC475060
0.9388	High Similarity	NPC83744
0.9388	High Similarity	NPC220229
0.9381	High Similarity	NPC209502
0.9381	High Similarity	NPC204833
0.9293	High Similarity	NPC217201
0.9293	High Similarity	NPC329417
0.9286	High Similarity	NPC257353
0.9286	High Similarity	NPC149047
0.92	High Similarity	NPC11710
0.9192	High Similarity	NPC477916
0.9175	High Similarity	NPC477915
0.9082	High Similarity	NPC249187
0.9082	High Similarity	NPC247957
0.9062	High Similarity	NPC103051
0.9043	High Similarity	NPC8993
0.9032	High Similarity	NPC473998
0.9032	High Similarity	NPC233116
0.9032	High Similarity	NPC475806
0.9022	High Similarity	NPC473999
0.9022	High Similarity	NPC309603
0.899	High Similarity	NPC72255
0.8947	High Similarity	NPC472485
0.8932	High Similarity	NPC207251
0.8925	High Similarity	NPC48010
0.8922	High Similarity	NPC76084
0.8911	High Similarity	NPC65941
0.8854	High Similarity	NPC249954
0.8846	High Similarity	NPC73300
0.8846	High Similarity	NPC250109
0.8846	High Similarity	NPC962
0.8846	High Similarity	NPC108721
0.8846	High Similarity	NPC317210
0.8842	High Similarity	NPC245972
0.8842	High Similarity	NPC196485
0.8817	High Similarity	NPC477943
0.8817	High Similarity	NPC2983
0.8788	High Similarity	NPC22388
0.8788	High Similarity	NPC473424
0.8788	High Similarity	NPC234892
0.8788	High Similarity	NPC293753
0.8763	High Similarity	NPC320306
0.8763	High Similarity	NPC107243
0.8763	High Similarity	NPC18509
0.8763	High Similarity	NPC190554
0.8762	High Similarity	NPC326542
0.875	High Similarity	NPC259286
0.875	High Similarity	NPC297199
0.8737	High Similarity	NPC69454
0.8737	High Similarity	NPC470376
0.8737	High Similarity	NPC475255
0.8737	High Similarity	NPC470375
0.8723	High Similarity	NPC320026
0.8713	High Similarity	NPC166607
0.871	High Similarity	NPC193360
0.87	High Similarity	NPC311612
0.87	High Similarity	NPC55872
0.8696	High Similarity	NPC472986
0.8696	High Similarity	NPC472985
0.8696	High Similarity	NPC469994
0.8679	High Similarity	NPC266728
0.8679	High Similarity	NPC49492
0.8673	High Similarity	NPC186810
0.8673	High Similarity	NPC48647
0.866	High Similarity	NPC49371
0.8646	High Similarity	NPC299100
0.8646	High Similarity	NPC292793
0.8641	High Similarity	NPC214644
0.8632	High Similarity	NPC63748
0.8627	High Similarity	NPC185
0.8617	High Similarity	NPC31985
0.8617	High Similarity	NPC1015
0.8617	High Similarity	NPC472971
0.8617	High Similarity	NPC472970
0.8617	High Similarity	NPC186688
0.8614	High Similarity	NPC160843
0.8614	High Similarity	NPC28656
0.8602	High Similarity	NPC475740
0.8602	High Similarity	NPC317590
0.86	High Similarity	NPC195290
0.86	High Similarity	NPC204450
0.86	High Similarity	NPC87351
0.8587	High Similarity	NPC474218
0.8587	High Similarity	NPC470574
0.8587	High Similarity	NPC471224
0.8586	High Similarity	NPC327431
0.8586	High Similarity	NPC15390
0.8586	High Similarity	NPC144956
0.8586	High Similarity	NPC218383
0.8586	High Similarity	NPC470074
0.8571	High Similarity	NPC122294
0.8571	High Similarity	NPC57416
0.8571	High Similarity	NPC108078
0.8557	High Similarity	NPC472932
0.8557	High Similarity	NPC180950
0.8542	High Similarity	NPC243866
0.8542	High Similarity	NPC472930
0.8529	High Similarity	NPC323834
0.8526	High Similarity	NPC171441
0.8526	High Similarity	NPC100313
0.8515	High Similarity	NPC191892
0.8515	High Similarity	NPC236390
0.8511	High Similarity	NPC471722
0.8511	High Similarity	NPC328539
0.8495	Intermediate Similarity	NPC31564
0.8495	Intermediate Similarity	NPC474732
0.8495	Intermediate Similarity	NPC474778
0.8495	Intermediate Similarity	NPC474733
0.8495	Intermediate Similarity	NPC145879
0.8495	Intermediate Similarity	NPC72133
0.8485	Intermediate Similarity	NPC16021
0.8478	Intermediate Similarity	NPC85774
0.8478	Intermediate Similarity	NPC214043
0.8478	Intermediate Similarity	NPC329043
0.8478	Intermediate Similarity	NPC321187
0.8478	Intermediate Similarity	NPC82902
0.8478	Intermediate Similarity	NPC227064
0.8478	Intermediate Similarity	NPC161423
0.8478	Intermediate Similarity	NPC58841
0.8469	Intermediate Similarity	NPC155676
0.8469	Intermediate Similarity	NPC117133
0.8469	Intermediate Similarity	NPC7124
0.8454	Intermediate Similarity	NPC196227
0.8454	Intermediate Similarity	NPC474690
0.8454	Intermediate Similarity	NPC119562
0.8454	Intermediate Similarity	NPC279410
0.8447	Intermediate Similarity	NPC64844
0.8447	Intermediate Similarity	NPC42847
0.844	Intermediate Similarity	NPC475041
0.8438	Intermediate Similarity	NPC168027
0.8438	Intermediate Similarity	NPC116726
0.8438	Intermediate Similarity	NPC272746
0.8438	Intermediate Similarity	NPC154101
0.8438	Intermediate Similarity	NPC472978
0.8438	Intermediate Similarity	NPC73457
0.8438	Intermediate Similarity	NPC23434
0.8438	Intermediate Similarity	NPC185936
0.8421	Intermediate Similarity	NPC310010
0.8421	Intermediate Similarity	NPC326627
0.8421	Intermediate Similarity	NPC76879
0.8421	Intermediate Similarity	NPC472983
0.8421	Intermediate Similarity	NPC119416
0.8421	Intermediate Similarity	NPC275740
0.8421	Intermediate Similarity	NPC472973
0.8421	Intermediate Similarity	NPC86319
0.8421	Intermediate Similarity	NPC32830
0.8421	Intermediate Similarity	NPC474245
0.8416	Intermediate Similarity	NPC136289
0.8404	Intermediate Similarity	NPC58063
0.84	Intermediate Similarity	NPC83709
0.84	Intermediate Similarity	NPC144660
0.84	Intermediate Similarity	NPC299971
0.84	Intermediate Similarity	NPC474720
0.84	Intermediate Similarity	NPC307954
0.84	Intermediate Similarity	NPC476274
0.8387	Intermediate Similarity	NPC197823
0.8387	Intermediate Similarity	NPC474083
0.8384	Intermediate Similarity	NPC126815
0.8384	Intermediate Similarity	NPC475894
0.8384	Intermediate Similarity	NPC474785
0.8384	Intermediate Similarity	NPC474938
0.8384	Intermediate Similarity	NPC253826
0.8367	Intermediate Similarity	NPC472824
0.8367	Intermediate Similarity	NPC162001
0.8367	Intermediate Similarity	NPC45324
0.8367	Intermediate Similarity	NPC222845
0.8364	Intermediate Similarity	NPC109973
0.8351	Intermediate Similarity	NPC472942
0.8351	Intermediate Similarity	NPC109305
0.8351	Intermediate Similarity	NPC233118
0.8351	Intermediate Similarity	NPC474807
0.8351	Intermediate Similarity	NPC474736
0.835	Intermediate Similarity	NPC60681
0.8333	Intermediate Similarity	NPC191684
0.8333	Intermediate Similarity	NPC69622
0.8333	Intermediate Similarity	NPC478057
0.8333	Intermediate Similarity	NPC111323
0.8333	Intermediate Similarity	NPC126993
0.8333	Intermediate Similarity	NPC117185
0.8333	Intermediate Similarity	NPC85173
0.8333	Intermediate Similarity	NPC134321
0.8333	Intermediate Similarity	NPC469400
0.8333	Intermediate Similarity	NPC140723

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 NPC154072 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	156
0.1-0.2	1482
0.2-0.3	3956
0.3-0.4	2401
0.4-0.5	661
0.5-0.6	158
0.6-0.7	136
0.7-0.8	114
0.8-0.85	68
0.85-0.9	17
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8936	High Similarity	NPD4202	Approved
0.8788	High Similarity	NPD5211	Phase 2
0.8763	High Similarity	NPD4755	Approved
0.8696	High Similarity	NPD3618	Phase 1
0.8617	High Similarity	NPD5328	Approved
0.8614	High Similarity	NPD5141	Approved
0.8586	High Similarity	NPD5286	Approved
0.8586	High Similarity	NPD5285	Approved
0.8586	High Similarity	NPD4700	Approved
0.8586	High Similarity	NPD4696	Approved
0.85	High Similarity	NPD5223	Approved
0.8478	Intermediate Similarity	NPD3666	Approved
0.8478	Intermediate Similarity	NPD3133	Approved
0.8478	Intermediate Similarity	NPD3665	Phase 1
0.8438	Intermediate Similarity	NPD6079	Approved
0.8421	Intermediate Similarity	NPD4753	Phase 2
0.8416	Intermediate Similarity	NPD4633	Approved
0.8416	Intermediate Similarity	NPD5225	Approved
0.8416	Intermediate Similarity	NPD5226	Approved
0.8416	Intermediate Similarity	NPD5224	Approved
0.835	Intermediate Similarity	NPD6675	Approved
0.835	Intermediate Similarity	NPD5739	Approved
0.835	Intermediate Similarity	NPD7128	Approved
0.835	Intermediate Similarity	NPD6402	Approved
0.8333	Intermediate Similarity	NPD4754	Approved
0.8333	Intermediate Similarity	NPD5174	Approved
0.8333	Intermediate Similarity	NPD5175	Approved
0.8286	Intermediate Similarity	NPD6372	Approved
0.8286	Intermediate Similarity	NPD6373	Approved
0.8283	Intermediate Similarity	NPD4697	Phase 3
0.828	Intermediate Similarity	NPD4786	Approved
0.8261	Intermediate Similarity	NPD4221	Approved
0.8261	Intermediate Similarity	NPD4223	Phase 3
0.8218	Intermediate Similarity	NPD7640	Approved
0.8218	Intermediate Similarity	NPD7639	Approved
0.8208	Intermediate Similarity	NPD4634	Approved
0.8191	Intermediate Similarity	NPD5329	Approved
0.819	Intermediate Similarity	NPD7320	Approved
0.819	Intermediate Similarity	NPD6899	Approved
0.819	Intermediate Similarity	NPD6881	Approved
0.8182	Intermediate Similarity	NPD4629	Approved
0.8182	Intermediate Similarity	NPD5210	Approved
0.8173	Intermediate Similarity	NPD4768	Approved
0.8173	Intermediate Similarity	NPD4767	Approved
0.8131	Intermediate Similarity	NPD6649	Approved
0.8131	Intermediate Similarity	NPD6650	Approved
0.8119	Intermediate Similarity	NPD7638	Approved
0.8105	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.81	Intermediate Similarity	NPD5222	Approved
0.81	Intermediate Similarity	NPD5221	Approved
0.81	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD5701	Approved
0.8095	Intermediate Similarity	NPD5697	Approved
0.8085	Intermediate Similarity	NPD4197	Approved
0.8065	Intermediate Similarity	NPD3667	Approved
0.8037	Intermediate Similarity	NPD7290	Approved
0.8037	Intermediate Similarity	NPD7102	Approved
0.8037	Intermediate Similarity	NPD6883	Approved
0.802	Intermediate Similarity	NPD6083	Phase 2
0.802	Intermediate Similarity	NPD5173	Approved
0.802	Intermediate Similarity	NPD6084	Phase 2
0.8019	Intermediate Similarity	NPD4729	Approved
0.8019	Intermediate Similarity	NPD6011	Approved
0.8019	Intermediate Similarity	NPD4730	Approved
0.8019	Intermediate Similarity	NPD5128	Approved
0.8	Intermediate Similarity	NPD6008	Approved
0.7982	Intermediate Similarity	NPD4632	Approved
0.798	Intermediate Similarity	NPD6399	Phase 3
0.7963	Intermediate Similarity	NPD8130	Phase 1
0.7963	Intermediate Similarity	NPD6617	Approved
0.7963	Intermediate Similarity	NPD6869	Approved
0.7963	Intermediate Similarity	NPD6847	Approved
0.7963	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7944	Intermediate Similarity	NPD6012	Approved
0.7944	Intermediate Similarity	NPD6014	Approved
0.7944	Intermediate Similarity	NPD6013	Approved
0.7917	Intermediate Similarity	NPD5205	Approved
0.7917	Intermediate Similarity	NPD4688	Approved
0.7917	Intermediate Similarity	NPD4689	Approved
0.7917	Intermediate Similarity	NPD4693	Phase 3
0.7917	Intermediate Similarity	NPD4138	Approved
0.7917	Intermediate Similarity	NPD4690	Approved
0.789	Intermediate Similarity	NPD6882	Approved
0.789	Intermediate Similarity	NPD8297	Approved
0.7879	Intermediate Similarity	NPD5281	Approved
0.7879	Intermediate Similarity	NPD5284	Approved
0.7879	Intermediate Similarity	NPD7515	Phase 2
0.787	Intermediate Similarity	NPD5249	Phase 3
0.787	Intermediate Similarity	NPD5247	Approved
0.787	Intermediate Similarity	NPD5250	Approved
0.787	Intermediate Similarity	NPD5135	Approved
0.787	Intermediate Similarity	NPD5169	Approved
0.787	Intermediate Similarity	NPD5248	Approved
0.787	Intermediate Similarity	NPD5251	Approved
0.787	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD7525	Registered
0.7835	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7822	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD5215	Approved
0.7798	Intermediate Similarity	NPD5216	Approved
0.7798	Intermediate Similarity	NPD5127	Approved
0.7798	Intermediate Similarity	NPD5217	Approved
0.7789	Intermediate Similarity	NPD4788	Approved
0.7768	Intermediate Similarity	NPD6009	Approved
0.7768	Intermediate Similarity	NPD7115	Discovery
0.7767	Intermediate Similarity	NPD5696	Approved
0.7757	Intermediate Similarity	NPD6412	Phase 2
0.7732	Intermediate Similarity	NPD4694	Approved
0.7732	Intermediate Similarity	NPD6409	Approved
0.7732	Intermediate Similarity	NPD6684	Approved
0.7732	Intermediate Similarity	NPD5330	Approved
0.7732	Intermediate Similarity	NPD5690	Phase 2
0.7732	Intermediate Similarity	NPD7521	Approved
0.7732	Intermediate Similarity	NPD7334	Approved
0.7732	Intermediate Similarity	NPD7146	Approved
0.7732	Intermediate Similarity	NPD5280	Approved
0.7732	Intermediate Similarity	NPD5279	Phase 3
0.7719	Intermediate Similarity	NPD6054	Approved
0.7719	Intermediate Similarity	NPD6059	Approved
0.767	Intermediate Similarity	NPD7902	Approved
0.7647	Intermediate Similarity	NPD5695	Phase 3
0.7589	Intermediate Similarity	NPD5167	Approved
0.7586	Intermediate Similarity	NPD6370	Approved
0.7576	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD6903	Approved
0.7565	Intermediate Similarity	NPD6319	Approved
0.7553	Intermediate Similarity	NPD4195	Approved
0.7551	Intermediate Similarity	NPD4623	Approved
0.7551	Intermediate Similarity	NPD4519	Discontinued
0.7549	Intermediate Similarity	NPD7748	Approved
0.7547	Intermediate Similarity	NPD7632	Discontinued
0.7544	Intermediate Similarity	NPD6335	Approved
0.7526	Intermediate Similarity	NPD3668	Phase 3
0.7522	Intermediate Similarity	NPD6274	Approved
0.7521	Intermediate Similarity	NPD7604	Phase 2
0.75	Intermediate Similarity	NPD6673	Approved
0.75	Intermediate Similarity	NPD6904	Approved
0.75	Intermediate Similarity	NPD5983	Phase 2
0.75	Intermediate Similarity	NPD6016	Approved
0.75	Intermediate Similarity	NPD6080	Approved
0.75	Intermediate Similarity	NPD6015	Approved
0.7478	Intermediate Similarity	NPD7101	Approved
0.7478	Intermediate Similarity	NPD7100	Approved
0.7458	Intermediate Similarity	NPD7492	Approved
0.7456	Intermediate Similarity	NPD6317	Approved
0.7449	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD5988	Approved
0.7419	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD6672	Approved
0.74	Intermediate Similarity	NPD5737	Approved
0.7395	Intermediate Similarity	NPD6616	Approved
0.7395	Intermediate Similarity	NPD7507	Approved
0.7395	Intermediate Similarity	NPD6336	Discontinued
0.7391	Intermediate Similarity	NPD6313	Approved
0.7391	Intermediate Similarity	NPD6314	Approved
0.7379	Intermediate Similarity	NPD6001	Approved
0.7379	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD7900	Approved
0.7364	Intermediate Similarity	NPD5168	Approved
0.7353	Intermediate Similarity	NPD8035	Phase 2
0.7353	Intermediate Similarity	NPD8034	Phase 2
0.7353	Intermediate Similarity	NPD5693	Phase 1
0.735	Intermediate Similarity	NPD6908	Approved
0.735	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD6909	Approved
0.7333	Intermediate Similarity	NPD8293	Discontinued
0.7333	Intermediate Similarity	NPD7078	Approved
0.7312	Intermediate Similarity	NPD6942	Approved
0.7312	Intermediate Similarity	NPD7339	Approved
0.7273	Intermediate Similarity	NPD7736	Approved
0.7273	Intermediate Similarity	NPD6033	Approved
0.7263	Intermediate Similarity	NPD3617	Approved
0.7257	Intermediate Similarity	NPD6053	Discontinued
0.7255	Intermediate Similarity	NPD4096	Approved
0.7228	Intermediate Similarity	NPD5208	Approved
0.7227	Intermediate Similarity	NPD6067	Discontinued
0.7222	Intermediate Similarity	NPD5091	Approved
0.7216	Intermediate Similarity	NPD4139	Approved
0.7216	Intermediate Similarity	NPD4692	Approved
0.7213	Intermediate Similarity	NPD7319	Approved
0.72	Intermediate Similarity	NPD6098	Approved
0.7184	Intermediate Similarity	NPD6050	Approved
0.7179	Intermediate Similarity	NPD4522	Approved
0.7174	Intermediate Similarity	NPD4243	Approved
0.7172	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD5133	Approved
0.7113	Intermediate Similarity	NPD6931	Approved
0.7113	Intermediate Similarity	NPD4695	Discontinued
0.7113	Intermediate Similarity	NPD6930	Phase 2
0.71	Intermediate Similarity	NPD5363	Approved
0.7094	Intermediate Similarity	NPD7327	Approved
0.7094	Intermediate Similarity	NPD7328	Approved
0.7087	Intermediate Similarity	NPD5207	Approved
0.7087	Intermediate Similarity	NPD5692	Phase 3
0.7087	Intermediate Similarity	NPD5785	Approved
0.7083	Intermediate Similarity	NPD6118	Approved
0.7083	Intermediate Similarity	NPD6114	Approved
0.7083	Intermediate Similarity	NPD6697	Approved
0.7083	Intermediate Similarity	NPD5784	Clinical (unspecified phase)

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