NPASS Compound

Structure

NPC475373 OpenBabel07101718302D 45 50 0 0 1 0 0 0 0 0999 V2000 7.4527 1.8478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9886 -4.1522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4527 -1.1522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9527 -0.2862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5348 -0.4612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8546 1.3478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8546 -1.6522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1847 0.8478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3187 0.3478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0508 0.3478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3187 -0.6522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0508 -0.6522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7861 1.9305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7807 1.8259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9886 -1.1522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1226 -0.6522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5867 0.3478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5867 -2.6522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 -0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5867 2.3478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8546 -3.6522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1847 -1.1522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 0.8090 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.3794 1.0169 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9886 0.8478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8546 -0.6522 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.5867 -0.6522 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.4527 -2.1522 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.7206 0.8478 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.7206 -2.1522 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2079 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1847 -2.1522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4527 -1.1522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1226 0.3478 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8546 0.3478 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.7206 -1.1522 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.5867 3.3478 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7206 -4.1522 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1215 1.3849 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.0508 -2.6522 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 5.7206 1.8478 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8546 -2.6522 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3187 -2.6522 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 22 1 0 0 0 0 3 34 1 0 0 0 0 4 34 1 0 0 0 0 8 9 2 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 2 0 0 0 0 11 23 2 0 0 0 0 12 23 1 0 0 0 0 13 14 1 0 0 0 0 13 25 1 0 0 0 0 14 26 2 0 0 0 0 15 16 1 0 0 0 0 15 27 1 0 0 0 0 16 35 1 0 0 0 0 17 24 1 0 0 0 0 17 32 1 0 0 0 0 18 28 1 0 0 0 0 18 30 1 0 0 0 0 19 29 1 0 0 0 0 19 31 1 0 0 0 0 20 24 1 0 0 0 0 20 42 1 0 0 0 0 21 38 2 0 0 0 0 21 43 1 0 0 0 0 22 39 2 0 0 0 0 22 44 1 0 0 0 0 23 33 1 0 0 0 0 24 25 1 0 0 0 0 25 35 1 6 0 0 0 26 35 1 0 0 0 0 26 36 1 0 0 0 0 27 36 1 1 0 0 0 27 37 1 0 0 0 0 28 34 1 0 0 0 0 28 37 1 1 0 0 0 29 34 1 0 0 0 0 29 45 1 6 0 0 0 30 36 1 6 0 0 0 30 43 1 0 0 0 0 31 37 1 6 0 0 0 31 44 1 0 0 0 0 32 40 2 0 0 0 0 32 42 1 0 0 0 0 33 41 2 0 0 0 0 33 45 1 0 0 0 0 35 5 1 6 0 0 0 36 6 1 1 0 0 0 37 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	620.33
Volume:	646.399
LogP:	5.69
LogD:	3.913
LogS:	-5.42
# Rotatable Bonds:	8
TPSA:	105.2
# H-Bond Aceptor:	8
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.21
Synthetic Accessibility Score:	5.1
Fsp3:	0.676
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:	-4.81
MDCK Permeability:	6.281078094616532e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.818
30% Bioavailability (F30%):	0.658

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.108
Plasma Protein Binding (PPB):	93.61839294433594%
Volume Distribution (VD):	1.469
Pgp-substrate:	8.485655784606934%

ADMET: Metabolism

CYP1A2-inhibitor:	0.036
CYP1A2-substrate:	0.043
CYP2C19-inhibitor:	0.123
CYP2C19-substrate:	0.113
CYP2C9-inhibitor:	0.395
CYP2C9-substrate:	0.05
CYP2D6-inhibitor:	0.04
CYP2D6-substrate:	0.049
CYP3A4-inhibitor:	0.582
CYP3A4-substrate:	0.442

ADMET: Excretion

Clearance (CL):	4.876
Half-life (T1/2):	0.235

ADMET: Toxicity

hERG Blockers:	0.118
Human Hepatotoxicity (H-HT):	0.179
Drug-inuced Liver Injury (DILI):	0.655
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.097
Maximum Recommended Daily Dose:	0.964
Skin Sensitization:	0.889
Carcinogencity:	0.102
Eye Corrosion:	0.006
Eye Irritation:	0.317
Respiratory Toxicity:	0.952

Download Data

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

Natural Product: NPC475373

Natural Product ID:	NPC475373
*Common Name:**	Melianin C
IUPAC Name:	[(1S,3R,5S,7R,8R,9R,10S,13S,17S)-1,7-diacetyloxy-4,4,8,10,13-pentamethyl-17-(5-oxooxolan-3-yl)-2,3,5,6,7,9,11,12,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl] benzoate
Synonyms:	Melianin C
Standard InCHIKey:	UMDZHCRPOCMGPU-RCRHGASGSA-N
Standard InCHI:	InChI=1S/C37H48O8/c1-21(38)43-30-18-28-34(3,4)29(45-33(41)23-11-9-8-10-12-23)19-31(44-22(2)39)37(28,7)27-15-16-35(5)25(24-17-32(40)42-20-24)13-14-26(35)36(27,30)6/h8-12,14,24-25,27-31H,13,15-20H2,1-7H3/t24?,25-,27-,28-,29+,30+,31-,35-,36-,37+/m0/s1
SMILES:	O=C1OCC(C1)[C@@H]1CC=C2[C@@]1(C)CC[C@H]1[C@@]2(C)[C@H](OC(=O)C)C[C@@H]2[C@]1(C)[C@@H](OC(=O)C)C[C@H](C2(C)C)OC(=O)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL504483
PubChem CID:	44566527
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids [CHEMONTID:0002380] Limonoids

*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
NPO4571	Melia volkensii	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10217705]
NPO4571	Melia volkensii	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461654]
NPO4571	Melia volkensii	Species	Meliaceae	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
ED50	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	21.85	ug ml-1	PMID[523070]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	14.47	ug ml-1	PMID[523070]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	18.05	ug ml-1	PMID[523070]
NPT376	Cell Line	A498	Homo sapiens	ED50	=	26.52	ug ml-1	PMID[523070]
NPT306	Cell Line	PC-3	Homo sapiens	ED50	=	4.73	10'-1 ug/ml	PMID[523070]
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	ED50	=	20.62	ug ml-1	PMID[523070]

☑ 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 NPC475373 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	334
0.1-0.2	1263
0.2-0.3	2217
0.3-0.4	4770
0.4-0.5	9850
0.5-0.6	14438
0.6-0.7	8275
0.7-0.8	1237
0.8-0.85	142
0.85-0.9	134
0.9-0.95	36
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.916	High Similarity	NPC147561
0.9137	High Similarity	NPC475552
0.9118	High Similarity	NPC473081
0.9118	High Similarity	NPC43241
0.9118	High Similarity	NPC473758
0.9118	High Similarity	NPC473109
0.9118	High Similarity	NPC211137
0.9118	High Similarity	NPC184747
0.9118	High Similarity	NPC473085
0.9118	High Similarity	NPC476094
0.9118	High Similarity	NPC473060
0.9118	High Similarity	NPC4341
0.9118	High Similarity	NPC473112
0.9118	High Similarity	NPC48017
0.9118	High Similarity	NPC200592
0.9118	High Similarity	NPC473613
0.9118	High Similarity	NPC147880
0.9098	High Similarity	NPC472656
0.9091	High Similarity	NPC470278
0.9044	High Similarity	NPC475652
0.9044	High Similarity	NPC210591
0.9044	High Similarity	NPC214550
0.9007	High Similarity	NPC473403
0.9	High Similarity	NPC473602
0.8971	High Similarity	NPC283375
0.8971	High Similarity	NPC183122
0.8963	High Similarity	NPC291638
0.8963	High Similarity	NPC66761
0.8963	High Similarity	NPC195647
0.8963	High Similarity	NPC472577
0.8963	High Similarity	NPC17877
0.8921	High Similarity	NPC177340
0.8921	High Similarity	NPC147217
0.8921	High Similarity	NPC246480
0.8921	High Similarity	NPC139067
0.8921	High Similarity	NPC270498
0.8921	High Similarity	NPC191082
0.8921	High Similarity	NPC475429
0.8921	High Similarity	NPC473673
0.8889	High Similarity	NPC474608
0.8889	High Similarity	NPC48929
0.8857	High Similarity	NPC470231
0.8857	High Similarity	NPC57628
0.8857	High Similarity	NPC51314
0.8857	High Similarity	NPC188865
0.8857	High Similarity	NPC95265
0.8857	High Similarity	NPC163719
0.8857	High Similarity	NPC472570
0.8857	High Similarity	NPC11685
0.8857	High Similarity	NPC95810
0.8857	High Similarity	NPC70716
0.8857	High Similarity	NPC67777
0.8857	High Similarity	NPC472573
0.8857	High Similarity	NPC125106
0.8857	High Similarity	NPC472569
0.8857	High Similarity	NPC25768
0.8857	High Similarity	NPC476974
0.8841	High Similarity	NPC183270
0.8841	High Similarity	NPC477904
0.8824	High Similarity	NPC473399
0.8824	High Similarity	NPC473216
0.8794	High Similarity	NPC472575
0.8794	High Similarity	NPC469349
0.8794	High Similarity	NPC473088
0.8794	High Similarity	NPC171525
0.8794	High Similarity	NPC470159
0.8794	High Similarity	NPC471104
0.8794	High Similarity	NPC472572
0.8794	High Similarity	NPC200471
0.8794	High Similarity	NPC158663
0.8794	High Similarity	NPC29704
0.8794	High Similarity	NPC472568
0.8794	High Similarity	NPC184817
0.8794	High Similarity	NPC174982
0.8794	High Similarity	NPC472571
0.8794	High Similarity	NPC470157
0.8794	High Similarity	NPC96903
0.8794	High Similarity	NPC476973
0.8794	High Similarity	NPC177940
0.8794	High Similarity	NPC70403
0.8786	High Similarity	NPC163087
0.8777	High Similarity	NPC16912
0.875	High Similarity	NPC203486
0.8723	High Similarity	NPC475759
0.8723	High Similarity	NPC475122
0.8723	High Similarity	NPC470152
0.8723	High Similarity	NPC241951
0.8714	High Similarity	NPC475135
0.8705	High Similarity	NPC171207
0.8705	High Similarity	NPC97667
0.8705	High Similarity	NPC90614
0.8686	High Similarity	NPC471864
0.8681	High Similarity	NPC254558
0.8671	High Similarity	NPC281717
0.8662	High Similarity	NPC472556
0.8652	High Similarity	NPC191387
0.8652	High Similarity	NPC131966
0.8647	High Similarity	NPC470753
0.8647	High Similarity	NPC473220
0.8643	High Similarity	NPC472576
0.8643	High Similarity	NPC27377
0.8643	High Similarity	NPC118080
0.8643	High Similarity	NPC87448
0.8643	High Similarity	NPC41481
0.8643	High Similarity	NPC97947
0.8643	High Similarity	NPC224491
0.8643	High Similarity	NPC266374
0.8643	High Similarity	NPC291599
0.8633	High Similarity	NPC472371
0.8633	High Similarity	NPC472395
0.863	High Similarity	NPC472658
0.863	High Similarity	NPC472657
0.8613	High Similarity	NPC329913
0.8611	High Similarity	NPC92293
0.8611	High Similarity	NPC476975
0.8611	High Similarity	NPC266265
0.8611	High Similarity	NPC270590
0.8611	High Similarity	NPC471101
0.8611	High Similarity	NPC301556
0.8603	High Similarity	NPC472394
0.8601	High Similarity	NPC474935
0.8571	High Similarity	NPC475400
0.8571	High Similarity	NPC275592
0.8571	High Similarity	NPC100913
0.8571	High Similarity	NPC470765
0.8562	High Similarity	NPC477905
0.8552	High Similarity	NPC31829
0.8552	High Similarity	NPC470245
0.8552	High Similarity	NPC473214
0.8531	High Similarity	NPC471107
0.8531	High Similarity	NPC471100
0.8529	High Similarity	NPC72915
0.8521	High Similarity	NPC91703
0.8493	Intermediate Similarity	NPC470153
0.8489	Intermediate Similarity	NPC472545
0.8489	Intermediate Similarity	NPC472551
0.8483	Intermediate Similarity	NPC473215
0.8478	Intermediate Similarity	NPC126516
0.8472	Intermediate Similarity	NPC209592
0.8472	Intermediate Similarity	NPC240115
0.8472	Intermediate Similarity	NPC48599
0.8467	Intermediate Similarity	NPC238370
0.8451	Intermediate Similarity	NPC472546
0.8451	Intermediate Similarity	NPC192658
0.8446	Intermediate Similarity	NPC282239
0.8446	Intermediate Similarity	NPC473611
0.844	Intermediate Similarity	NPC87934
0.844	Intermediate Similarity	NPC472547
0.844	Intermediate Similarity	NPC162613
0.8435	Intermediate Similarity	NPC472548
0.8429	Intermediate Similarity	NPC39549
0.8429	Intermediate Similarity	NPC262324
0.8425	Intermediate Similarity	NPC7095
0.8425	Intermediate Similarity	NPC112216
0.8414	Intermediate Similarity	NPC473760
0.8392	Intermediate Similarity	NPC477894
0.8392	Intermediate Similarity	NPC95449
0.8389	Intermediate Similarity	NPC217091
0.8389	Intermediate Similarity	NPC106895
0.837	Intermediate Similarity	NPC169913
0.8369	Intermediate Similarity	NPC9905
0.8367	Intermediate Similarity	NPC51602
0.8357	Intermediate Similarity	NPC472374
0.8357	Intermediate Similarity	NPC472372
0.8356	Intermediate Similarity	NPC60509
0.8356	Intermediate Similarity	NPC81698
0.8356	Intermediate Similarity	NPC250046
0.8333	Intermediate Similarity	NPC472393
0.8333	Intermediate Similarity	NPC34943
0.8322	Intermediate Similarity	NPC34012
0.8322	Intermediate Similarity	NPC473632
0.8322	Intermediate Similarity	NPC469730
0.8322	Intermediate Similarity	NPC182869
0.8322	Intermediate Similarity	NPC472549
0.8322	Intermediate Similarity	NPC132599
0.8321	Intermediate Similarity	NPC475508
0.831	Intermediate Similarity	NPC79921
0.8309	Intermediate Similarity	NPC195224
0.8299	Intermediate Similarity	NPC161239
0.8299	Intermediate Similarity	NPC165260
0.8299	Intermediate Similarity	NPC198455
0.8298	Intermediate Similarity	NPC327511
0.8298	Intermediate Similarity	NPC205305
0.8298	Intermediate Similarity	NPC243893
0.8296	Intermediate Similarity	NPC275576
0.8296	Intermediate Similarity	NPC473082
0.8289	Intermediate Similarity	NPC476077
0.8286	Intermediate Similarity	NPC477893
0.8278	Intermediate Similarity	NPC471102
0.8276	Intermediate Similarity	NPC125882
0.8276	Intermediate Similarity	NPC127857
0.8267	Intermediate Similarity	NPC323001
0.8267	Intermediate Similarity	NPC326235
0.8255	Intermediate Similarity	NPC237549
0.8255	Intermediate Similarity	NPC265395
0.8255	Intermediate Similarity	NPC77719
0.8255	Intermediate Similarity	NPC249471
0.8255	Intermediate Similarity	NPC473414
0.8255	Intermediate Similarity	NPC256142
0.8255	Intermediate Similarity	NPC472030

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 NPC475373 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	265
0.1-0.2	796
0.2-0.3	1324
0.3-0.4	2863
0.4-0.5	2394
0.5-0.6	1237
0.6-0.7	246
0.7-0.8	25
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8027	Intermediate Similarity	NPD7236	Approved
0.7881	Intermediate Similarity	NPD7239	Suspended
0.7769	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD7799	Discontinued
0.7676	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD7961	Discontinued
0.7552	Intermediate Similarity	NPD7008	Discontinued
0.7465	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD7741	Discontinued
0.7421	Intermediate Similarity	NPD7057	Phase 3
0.7421	Intermediate Similarity	NPD7058	Phase 2
0.7403	Intermediate Similarity	NPD6273	Approved
0.7388	Intermediate Similarity	NPD6858	Approved
0.7388	Intermediate Similarity	NPD7094	Approved
0.7348	Intermediate Similarity	NPD2182	Approved
0.7346	Intermediate Similarity	NPD8127	Discontinued
0.726	Intermediate Similarity	NPD3764	Approved
0.7193	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD8166	Discontinued
0.7186	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD5951	Approved
0.7135	Intermediate Similarity	NPD8407	Phase 2
0.7122	Intermediate Similarity	NPD7610	Discontinued
0.7113	Intermediate Similarity	NPD6287	Discontinued
0.7105	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD6663	Approved
0.7095	Intermediate Similarity	NPD8032	Phase 2
0.7081	Intermediate Similarity	NPD7819	Suspended
0.7081	Intermediate Similarity	NPD5761	Phase 2
0.7081	Intermediate Similarity	NPD5760	Phase 2
0.7078	Intermediate Similarity	NPD7003	Approved
0.7059	Intermediate Similarity	NPD8368	Discontinued
0.7052	Intermediate Similarity	NPD8434	Phase 2
0.7045	Intermediate Similarity	NPD164	Approved
0.7044	Intermediate Similarity	NPD6591	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1238	Approved
0.6994	Remote Similarity	NPD7768	Phase 2
0.698	Remote Similarity	NPD7713	Phase 3
0.6974	Remote Similarity	NPD3748	Approved
0.6972	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD8360	Approved
0.6971	Remote Similarity	NPD8435	Approved
0.6971	Remote Similarity	NPD8361	Approved
0.6968	Remote Similarity	NPD4628	Phase 3
0.6963	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD5736	Approved
0.6937	Remote Similarity	NPD7458	Discontinued
0.6909	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD2629	Approved
0.6899	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.689	Remote Similarity	NPD4965	Approved
0.689	Remote Similarity	NPD4967	Phase 2
0.689	Remote Similarity	NPD4966	Approved
0.6859	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD4198	Discontinued
0.6833	Remote Similarity	NPD8485	Approved
0.6832	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5408	Approved
0.6818	Remote Similarity	NPD5405	Approved
0.6818	Remote Similarity	NPD5404	Approved
0.6818	Remote Similarity	NPD5406	Approved
0.6813	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.681	Remote Similarity	NPD37	Approved
0.6807	Remote Similarity	NPD6234	Discontinued
0.6795	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD2534	Approved
0.6792	Remote Similarity	NPD2532	Approved
0.6792	Remote Similarity	NPD2533	Approved
0.6782	Remote Similarity	NPD8313	Approved
0.6782	Remote Similarity	NPD8312	Approved
0.6779	Remote Similarity	NPD6832	Phase 2
0.6766	Remote Similarity	NPD5494	Approved
0.6752	Remote Similarity	NPD3750	Approved
0.6748	Remote Similarity	NPD7411	Suspended
0.6735	Remote Similarity	NPD1876	Approved
0.6728	Remote Similarity	NPD3226	Approved
0.6725	Remote Similarity	NPD7228	Approved
0.6721	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.671	Remote Similarity	NPD2438	Suspended
0.671	Remote Similarity	NPD2796	Approved
0.6706	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD7997	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD7497	Discontinued
0.6687	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD6599	Discontinued
0.6686	Remote Similarity	NPD5844	Phase 1
0.6667	Remote Similarity	NPD3025	Approved
0.6667	Remote Similarity	NPD7055	Discontinued
0.6667	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6002	Phase 3
0.6667	Remote Similarity	NPD2067	Discontinued
0.6667	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2346	Discontinued
0.6667	Remote Similarity	NPD8150	Discontinued
0.6667	Remote Similarity	NPD6764	Approved
0.6667	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7473	Discontinued
0.6667	Remote Similarity	NPD3024	Approved
0.6667	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6005	Phase 3
0.6667	Remote Similarity	NPD6004	Phase 3
0.6667	Remote Similarity	NPD6765	Approved
0.6647	Remote Similarity	NPD7075	Discontinued
0.6645	Remote Similarity	NPD2799	Discontinued
0.6627	Remote Similarity	NPD7199	Phase 2
0.6621	Remote Similarity	NPD5125	Phase 3
0.6621	Remote Similarity	NPD5126	Approved
0.6617	Remote Similarity	NPD7798	Approved
0.6601	Remote Similarity	NPD2979	Phase 3
0.6601	Remote Similarity	NPD4140	Approved
0.6599	Remote Similarity	NPD3972	Approved
0.6597	Remote Similarity	NPD9545	Approved
0.6593	Remote Similarity	NPD6647	Phase 2
0.6593	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD1930	Approved
0.6593	Remote Similarity	NPD1929	Approved
0.6592	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD6232	Discontinued
0.6581	Remote Similarity	NPD2567	Approved
0.6581	Remote Similarity	NPD2569	Approved
0.6575	Remote Similarity	NPD3023	Approved
0.6575	Remote Similarity	NPD3026	Approved
0.6571	Remote Similarity	NPD7240	Approved
0.6571	Remote Similarity	NPD7685	Pre-registration
0.6566	Remote Similarity	NPD8455	Phase 2
0.6554	Remote Similarity	NPD5327	Phase 3
0.655	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD4766	Approved
0.6548	Remote Similarity	NPD3749	Approved
0.6544	Remote Similarity	NPD5909	Discontinued
0.6538	Remote Similarity	NPD7305	Phase 1
0.6536	Remote Similarity	NPD7714	Approved
0.6536	Remote Similarity	NPD7715	Approved
0.6533	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD6085	Phase 2
0.6532	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD1281	Approved
0.6529	Remote Similarity	NPD6959	Discontinued
0.6527	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD5402	Approved
0.6522	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD6784	Approved
0.6517	Remote Similarity	NPD6785	Approved
0.6515	Remote Similarity	NPD1989	Approved
0.6507	Remote Similarity	NPD17	Approved
0.6507	Remote Similarity	NPD3019	Approved
0.6506	Remote Similarity	NPD6801	Discontinued
0.6503	Remote Similarity	NPD920	Approved
0.6503	Remote Similarity	NPD5403	Approved
0.65	Remote Similarity	NPD6190	Approved
0.6497	Remote Similarity	NPD2935	Discontinued
0.6494	Remote Similarity	NPD4307	Phase 2
0.6493	Remote Similarity	NPD2066	Phase 3
0.6491	Remote Similarity	NPD7229	Phase 3
0.6489	Remote Similarity	NPD1202	Approved
0.6486	Remote Similarity	NPD6637	Approved
0.6485	Remote Similarity	NPD4380	Phase 2
0.6485	Remote Similarity	NPD7028	Phase 2
0.6483	Remote Similarity	NPD7009	Phase 2
0.6481	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD5401	Approved
0.6481	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD7097	Phase 1
0.6471	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD2313	Discontinued
0.6467	Remote Similarity	NPD1470	Approved
0.6456	Remote Similarity	NPD1471	Phase 3
0.6456	Remote Similarity	NPD5762	Approved
0.6456	Remote Similarity	NPD5763	Approved
0.6452	Remote Similarity	NPD6355	Discontinued
0.6452	Remote Similarity	NPD230	Phase 1
0.6449	Remote Similarity	NPD6685	Approved
0.6438	Remote Similarity	NPD5691	Approved
0.6437	Remote Similarity	NPD7177	Discontinued
0.6434	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD2798	Approved
0.642	Remote Similarity	NPD6799	Approved
0.642	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD6039	Approved
0.6402	Remote Similarity	NPD8320	Phase 1
0.6402	Remote Similarity	NPD8319	Approved
0.64	Remote Similarity	NPD2198	Approved
0.64	Remote Similarity	NPD2199	Approved
0.64	Remote Similarity	NPD1283	Approved
0.6398	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD2932	Approved
0.6392	Remote Similarity	NPD2531	Phase 2
0.6392	Remote Similarity	NPD6100	Approved
0.6392	Remote Similarity	NPD6099	Approved
0.6392	Remote Similarity	NPD1551	Phase 2
0.6384	Remote Similarity	NPD6559	Discontinued
0.6383	Remote Similarity	NPD4141	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