NPASS Compound

Structure

NPC469633 OpenBabel07101718282D 47 52 0 0 1 0 0 0 0 0999 V2000 1.3315 -4.2602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8433 3.1036 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4601 2.5783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1976 -3.6714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2500 -0.4907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4892 -0.5620 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2273 -2.3783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0824 3.8509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3554 -4.3628 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5500 -1.4722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9966 0.3992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4000 -0.9815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6533 -0.3302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5500 1.4722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3300 0.6061 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2025 -0.9761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9334 -1.2848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5001 2.3743 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2215 -3.5688 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0999 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7000 -0.9815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5500 0.4907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0468 -0.3001 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8628 2.1651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4000 1.9630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8500 0.4907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2500 0.4907 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1968 1.4408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1777 -2.6722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9334 0.3033 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5103 -0.4907 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8500 -1.4722 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.9815 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 1.8361 2.0383 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4000 2.9445 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8500 1.4722 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8535 0.7114 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1538 -2.5696 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3992 0.8966 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4860 3.0714 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1626 -1.1802 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2500 1.4722 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2367 1.2367 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3992 -1.8781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 18 1 0 0 0 0 3 18 1 0 0 0 0 7 34 1 0 0 0 0 8 43 1 0 0 0 0 9 19 1 0 0 0 0 10 12 1 0 0 0 0 10 21 1 0 0 0 0 11 13 2 0 0 0 0 11 20 1 0 0 0 0 12 32 1 0 0 0 0 13 44 1 0 0 0 0 14 22 2 0 0 0 0 14 25 1 0 0 0 0 15 23 1 0 0 0 0 15 24 1 0 0 0 0 16 20 2 0 0 0 0 16 44 1 0 0 0 0 17 33 1 0 0 0 0 17 35 1 0 0 0 0 18 29 1 0 0 0 0 19 4 1 6 0 0 0 19 30 1 0 0 0 0 20 28 1 0 0 0 0 21 26 2 0 0 0 0 21 34 1 0 0 0 0 22 26 1 0 0 0 0 22 32 1 0 0 0 0 23 33 1 1 0 0 0 23 34 1 0 0 0 0 24 37 2 0 0 0 0 24 43 1 0 0 0 0 25 38 2 0 0 0 0 25 45 1 0 0 0 0 26 27 1 0 0 0 0 27 36 1 0 0 0 0 27 39 2 0 0 0 0 28 32 1 6 0 0 0 28 45 1 0 0 0 0 29 40 2 0 0 0 0 29 46 1 0 0 0 0 30 41 2 0 0 0 0 30 47 1 0 0 0 0 31 33 1 1 0 0 0 31 36 1 0 0 0 0 31 46 1 0 0 0 0 32 5 1 6 0 0 0 33 6 1 6 0 0 0 34 35 1 6 0 0 0 35 36 1 6 0 0 0 35 47 1 0 0 0 0 36 42 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	652.29
Volume:	652.838
LogP:	4.345
LogD:	2.062
LogS:	-5.351
# Rotatable Bonds:	11
TPSA:	155.64
# H-Bond Aceptor:	11
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.306
Synthetic Accessibility Score:	6.367
Fsp3:	0.639
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:	-5.252
MDCK Permeability:	1.3945771570433863e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.036
Human Intestinal Absorption (HIA):	0.061
20% Bioavailability (F20%):	0.997
30% Bioavailability (F30%):	0.958

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.395
Plasma Protein Binding (PPB):	88.89136505126953%
Volume Distribution (VD):	2.246
Pgp-substrate:	6.776479721069336%

ADMET: Metabolism

CYP1A2-inhibitor:	0.068
CYP1A2-substrate:	0.495
CYP2C19-inhibitor:	0.91
CYP2C19-substrate:	0.366
CYP2C9-inhibitor:	0.953
CYP2C9-substrate:	0.012
CYP2D6-inhibitor:	0.13
CYP2D6-substrate:	0.022
CYP3A4-inhibitor:	0.966
CYP3A4-substrate:	0.773

ADMET: Excretion

Clearance (CL):	3.132
Half-life (T1/2):	0.172

ADMET: Toxicity

hERG Blockers:	0.455
Human Hepatotoxicity (H-HT):	0.761
Drug-inuced Liver Injury (DILI):	0.378
AMES Toxicity:	0.326
Rat Oral Acute Toxicity:	0.985
Maximum Recommended Daily Dose:	0.708
Skin Sensitization:	0.158
Carcinogencity:	0.739
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC469633

Natural Product ID:	NPC469633
*Common Name:**	Moluccensins H
IUPAC Name:	n.a.
Synonyms:	Moluccensins H
Standard InCHIKey:	RTUULIKPFWFGBC-RKVWQHKYSA-N
Standard InCHI:	InChI=1S/C36H44O11/c1-9-19(4)30(41)47-35-17-33(6)23(15-24(37)43-8)34(35,7)21-10-12-32(5)22(14-25(38)45-28(32)20-11-13-44-16-20)26(21)27(39)36(35,42)31(33)46-29(40)18(2)3/h11,13-14,16,18-19,23,28,31,42H,9-10,12,15,17H2,1-8H3/t19-,23-,28-,31-,32+,33-,34+,35+,36+/m0/s1
SMILES:	CCC(C)C(=O)OC12CC3(C(C1(C4=C(C5=CC(=O)OC(C5(CC4)C)C6=COC=C6)C(=O)C2(C3OC(=O)C(C)C)O)C)CC(=O)OC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1094916
PubChem CID:	46211773
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
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20112995]
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	Eukaryota	seeds	n.a.	n.a.	PMID[20146503]
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	Eukaryota	seeds	Thai	n.a.	PMID[21733687]
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	Eukaryota	seeds	n.a.	n.a.	PMID[22724531]
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	Eukaryota	seeds	n.a.	n.a.	PMID[26114936]
NPO6445	Xylocarpus moluccensis	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
Others	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4696	Organism	Brontispa longissima	Brontispa longissima	Activity	=	20.7	%	PMID[468261]
NPT4696	Organism	Brontispa longissima	Brontispa longissima	Activity	=	27.6	%	PMID[468261]

☑ 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 NPC469633 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	394
0.1-0.2	1575
0.2-0.3	3465
0.3-0.4	6684
0.4-0.5	11300
0.5-0.6	9199
0.6-0.7	8899
0.7-0.8	1024
0.8-0.85	116
0.85-0.9	34
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9938	High Similarity	NPC469576
0.9693	High Similarity	NPC94763
0.9573	High Similarity	NPC236004
0.9341	High Similarity	NPC478177
0.9329	High Similarity	NPC327922
0.9222	High Similarity	NPC471437
0.9202	High Similarity	NPC165218
0.9152	High Similarity	NPC478179
0.9091	High Similarity	NPC478178
0.9006	High Similarity	NPC470938
0.8929	High Similarity	NPC472659
0.8876	High Similarity	NPC159232
0.8876	High Similarity	NPC285227
0.8869	High Similarity	NPC472766
0.8869	High Similarity	NPC472765
0.8851	High Similarity	NPC242068
0.8851	High Similarity	NPC247563
0.8841	High Similarity	NPC472778
0.8841	High Similarity	NPC472777
0.8841	High Similarity	NPC472776
0.881	High Similarity	NPC472764
0.881	High Similarity	NPC476224
0.8802	High Similarity	NPC469849
0.8795	High Similarity	NPC329938
0.8772	High Similarity	NPC471632
0.875	High Similarity	NPC472141
0.875	High Similarity	NPC470875
0.875	High Similarity	NPC149945
0.8743	High Similarity	NPC105395
0.8743	High Similarity	NPC469338
0.8743	High Similarity	NPC292389
0.8727	High Similarity	NPC36655
0.8727	High Similarity	NPC261597
0.8727	High Similarity	NPC173544
0.872	High Similarity	NPC214541
0.872	High Similarity	NPC44675
0.8713	High Similarity	NPC469848
0.8698	High Similarity	NPC173516
0.869	High Similarity	NPC276551
0.869	High Similarity	NPC470940
0.8683	High Similarity	NPC82851
0.8675	High Similarity	NPC475226
0.8675	High Similarity	NPC475967
0.8675	High Similarity	NPC474932
0.8671	High Similarity	NPC470181
0.8667	High Similarity	NPC469485
0.8647	High Similarity	NPC471397
0.8647	High Similarity	NPC160651
0.8639	High Similarity	NPC214600
0.8631	High Similarity	NPC663
0.8631	High Similarity	NPC224394
0.8631	High Similarity	NPC472669
0.8623	High Similarity	NPC470789
0.8623	High Similarity	NPC472653
0.8623	High Similarity	NPC477402
0.8614	High Similarity	NPC187149
0.8614	High Similarity	NPC470118
0.8606	High Similarity	NPC264943
0.8596	High Similarity	NPC470995
0.8588	High Similarity	NPC472775
0.8588	High Similarity	NPC472774
0.8571	High Similarity	NPC472668
0.8571	High Similarity	NPC470792
0.8571	High Similarity	NPC472767
0.8571	High Similarity	NPC471166
0.8571	High Similarity	NPC471167
0.8571	High Similarity	NPC6326
0.8571	High Similarity	NPC188649
0.8571	High Similarity	NPC69028
0.8571	High Similarity	NPC149896
0.8563	High Similarity	NPC477403
0.8563	High Similarity	NPC472779
0.8555	High Similarity	NPC477824
0.8538	High Similarity	NPC472652
0.8538	High Similarity	NPC271235
0.8521	High Similarity	NPC288602
0.8521	High Similarity	NPC472773
0.8521	High Similarity	NPC472139
0.8521	High Similarity	NPC88841
0.8521	High Similarity	NPC471168
0.8521	High Similarity	NPC477405
0.8503	High Similarity	NPC197137
0.8503	High Similarity	NPC299038
0.8503	High Similarity	NPC45101
0.8503	High Similarity	NPC249021
0.8503	High Similarity	NPC195131
0.8494	Intermediate Similarity	NPC155939
0.8494	Intermediate Similarity	NPC296807
0.8494	Intermediate Similarity	NPC141538
0.8488	Intermediate Similarity	NPC472650
0.8485	Intermediate Similarity	NPC44577
0.848	Intermediate Similarity	NPC472282
0.848	Intermediate Similarity	NPC472651
0.8471	Intermediate Similarity	NPC470182
0.8471	Intermediate Similarity	NPC259943
0.8471	Intermediate Similarity	NPC271657
0.8462	Intermediate Similarity	NPC472771
0.8462	Intermediate Similarity	NPC18347
0.8462	Intermediate Similarity	NPC197596
0.8462	Intermediate Similarity	NPC200782
0.8462	Intermediate Similarity	NPC5079
0.8462	Intermediate Similarity	NPC5741
0.8452	Intermediate Similarity	NPC307383
0.8452	Intermediate Similarity	NPC472671
0.8443	Intermediate Similarity	NPC204663
0.8439	Intermediate Similarity	NPC475237
0.8439	Intermediate Similarity	NPC475641
0.8439	Intermediate Similarity	NPC160818
0.8439	Intermediate Similarity	NPC169299
0.8434	Intermediate Similarity	NPC253201
0.8434	Intermediate Similarity	NPC302054
0.843	Intermediate Similarity	NPC472673
0.8412	Intermediate Similarity	NPC469846
0.8412	Intermediate Similarity	NPC51568
0.8412	Intermediate Similarity	NPC302369
0.8412	Intermediate Similarity	NPC134254
0.8412	Intermediate Similarity	NPC39986
0.8412	Intermediate Similarity	NPC234660
0.8402	Intermediate Similarity	NPC191828
0.8402	Intermediate Similarity	NPC25255
0.8393	Intermediate Similarity	NPC214495
0.8393	Intermediate Similarity	NPC472283
0.8393	Intermediate Similarity	NPC475066
0.8393	Intermediate Similarity	NPC470119
0.8393	Intermediate Similarity	NPC286722
0.8393	Intermediate Similarity	NPC167142
0.8393	Intermediate Similarity	NPC88007
0.8383	Intermediate Similarity	NPC476262
0.8383	Intermediate Similarity	NPC92979
0.8382	Intermediate Similarity	NPC82602
0.8373	Intermediate Similarity	NPC33938
0.8373	Intermediate Similarity	NPC472672
0.8373	Intermediate Similarity	NPC476201
0.8373	Intermediate Similarity	NPC469503
0.8373	Intermediate Similarity	NPC246164
0.8372	Intermediate Similarity	NPC476850
0.8372	Intermediate Similarity	NPC476861
0.8364	Intermediate Similarity	NPC470997
0.8363	Intermediate Similarity	NPC476856
0.8363	Intermediate Similarity	NPC476858
0.8363	Intermediate Similarity	NPC476857
0.8363	Intermediate Similarity	NPC123088
0.8353	Intermediate Similarity	NPC68848
0.8353	Intermediate Similarity	NPC193798
0.8353	Intermediate Similarity	NPC263432
0.8343	Intermediate Similarity	NPC473473
0.8343	Intermediate Similarity	NPC475295
0.8333	Intermediate Similarity	NPC209364
0.8333	Intermediate Similarity	NPC175964
0.8333	Intermediate Similarity	NPC471169
0.8324	Intermediate Similarity	NPC296558
0.8323	Intermediate Similarity	NPC237259
0.8323	Intermediate Similarity	NPC282445
0.8323	Intermediate Similarity	NPC30222
0.8323	Intermediate Similarity	NPC98206
0.8323	Intermediate Similarity	NPC34421
0.8314	Intermediate Similarity	NPC121995
0.8313	Intermediate Similarity	NPC116717
0.8313	Intermediate Similarity	NPC18135
0.8304	Intermediate Similarity	NPC285567
0.8303	Intermediate Similarity	NPC471001
0.8303	Intermediate Similarity	NPC69647
0.8303	Intermediate Similarity	NPC472654
0.8303	Intermediate Similarity	NPC125182
0.8303	Intermediate Similarity	NPC234494
0.8294	Intermediate Similarity	NPC335761
0.8293	Intermediate Similarity	NPC255414
0.8284	Intermediate Similarity	NPC472772
0.8284	Intermediate Similarity	NPC195954
0.8284	Intermediate Similarity	NPC194499
0.8284	Intermediate Similarity	NPC469847
0.8274	Intermediate Similarity	NPC471175
0.8274	Intermediate Similarity	NPC35000
0.8274	Intermediate Similarity	NPC469336
0.8266	Intermediate Similarity	NPC476853
0.8266	Intermediate Similarity	NPC100333
0.8263	Intermediate Similarity	NPC182427
0.8263	Intermediate Similarity	NPC268905
0.8263	Intermediate Similarity	NPC470996
0.8263	Intermediate Similarity	NPC29695
0.8263	Intermediate Similarity	NPC308205
0.8263	Intermediate Similarity	NPC322546
0.8256	Intermediate Similarity	NPC261184
0.8256	Intermediate Similarity	NPC476860
0.8253	Intermediate Similarity	NPC196846
0.8253	Intermediate Similarity	NPC156189
0.8246	Intermediate Similarity	NPC117986
0.8246	Intermediate Similarity	NPC470939
0.8246	Intermediate Similarity	NPC211777
0.8246	Intermediate Similarity	NPC290400
0.8246	Intermediate Similarity	NPC18986
0.8246	Intermediate Similarity	NPC96443
0.8229	Intermediate Similarity	NPC294512
0.8225	Intermediate Similarity	NPC107646
0.8225	Intermediate Similarity	NPC126723
0.8214	Intermediate Similarity	NPC57998
0.8214	Intermediate Similarity	NPC178932
0.8208	Intermediate Similarity	NPC472670
0.8208	Intermediate Similarity	NPC23387
0.8208	Intermediate Similarity	NPC475779

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 NPC469633 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	341
0.1-0.2	1130
0.2-0.3	2425
0.3-0.4	2706
0.4-0.5	1659
0.5-0.6	677
0.6-0.7	200
0.7-0.8	12
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
0.8494	Intermediate Similarity	NPD5761	Phase 2
0.8494	Intermediate Similarity	NPD5760	Phase 2
0.8268	Intermediate Similarity	NPD8434	Phase 2
0.8081	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7889	Intermediate Similarity	NPD6764	Approved
0.7889	Intermediate Similarity	NPD6765	Approved
0.7717	Intermediate Similarity	NPD6785	Approved
0.7717	Intermediate Similarity	NPD6784	Approved
0.7377	Intermediate Similarity	NPD7799	Discontinued
0.734	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7075	Discontinued
0.722	Intermediate Similarity	NPD8404	Phase 2
0.7175	Intermediate Similarity	NPD6599	Discontinued
0.7151	Intermediate Similarity	NPD7819	Suspended
0.7128	Intermediate Similarity	NPD7685	Pre-registration
0.7111	Intermediate Similarity	NPD3817	Phase 2
0.7095	Intermediate Similarity	NPD6801	Discontinued
0.7088	Intermediate Similarity	NPD919	Approved
0.7069	Intermediate Similarity	NPD7236	Approved
0.7037	Intermediate Similarity	NPD6559	Discontinued
0.7011	Intermediate Similarity	NPD8127	Discontinued
0.7006	Intermediate Similarity	NPD920	Approved
0.6974	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD7239	Suspended
0.6965	Remote Similarity	NPD7497	Discontinued
0.6954	Remote Similarity	NPD4628	Phase 3
0.6943	Remote Similarity	NPD8150	Discontinued
0.6935	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD6799	Approved
0.6923	Remote Similarity	NPD5402	Approved
0.6919	Remote Similarity	NPD1247	Approved
0.6915	Remote Similarity	NPD3818	Discontinued
0.6893	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD3882	Suspended
0.6878	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD5494	Approved
0.6862	Remote Similarity	NPD7473	Discontinued
0.6854	Remote Similarity	NPD6273	Approved
0.6839	Remote Similarity	NPD8407	Phase 2
0.6828	Remote Similarity	NPD7199	Phase 2
0.6816	Remote Similarity	NPD5403	Approved
0.6798	Remote Similarity	NPD5401	Approved
0.6798	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD4380	Phase 2
0.6793	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD5763	Approved
0.6782	Remote Similarity	NPD5762	Approved
0.678	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD8368	Discontinued
0.6761	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD7907	Approved
0.6757	Remote Similarity	NPD3749	Approved
0.6757	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD7808	Phase 3
0.6721	Remote Similarity	NPD1934	Approved
0.672	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.672	Remote Similarity	NPD6166	Phase 2
0.672	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD2534	Approved
0.6704	Remote Similarity	NPD2532	Approved
0.6704	Remote Similarity	NPD2533	Approved
0.6703	Remote Similarity	NPD7028	Phase 2
0.6702	Remote Similarity	NPD6232	Discontinued
0.6702	Remote Similarity	NPD5844	Phase 1
0.6701	Remote Similarity	NPD8313	Approved
0.6701	Remote Similarity	NPD8312	Approved
0.6701	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD6002	Phase 3
0.6686	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD6004	Phase 3
0.6686	Remote Similarity	NPD6005	Phase 3
0.6685	Remote Similarity	NPD2801	Approved
0.6684	Remote Similarity	NPD7251	Discontinued
0.6667	Remote Similarity	NPD3926	Phase 2
0.6667	Remote Similarity	NPD7411	Suspended
0.6649	Remote Similarity	NPD3751	Discontinued
0.6648	Remote Similarity	NPD3226	Approved
0.6632	Remote Similarity	NPD6797	Phase 2
0.6631	Remote Similarity	NPD6234	Discontinued
0.6629	Remote Similarity	NPD2796	Approved
0.662	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD7054	Approved
0.6613	Remote Similarity	NPD7057	Phase 3
0.6613	Remote Similarity	NPD4966	Approved
0.6613	Remote Similarity	NPD7058	Phase 2
0.6613	Remote Similarity	NPD4965	Approved
0.6613	Remote Similarity	NPD4967	Phase 2
0.6611	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.661	Remote Similarity	NPD1243	Approved
0.661	Remote Similarity	NPD2800	Approved
0.6591	Remote Similarity	NPD1471	Phase 3
0.659	Remote Similarity	NPD6355	Discontinued
0.6589	Remote Similarity	NPD4665	Approved
0.6589	Remote Similarity	NPD4111	Phase 1
0.658	Remote Similarity	NPD7472	Approved
0.658	Remote Similarity	NPD7074	Phase 3
0.6575	Remote Similarity	NPD1512	Approved
0.6573	Remote Similarity	NPD3750	Approved
0.6554	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6553	Remote Similarity	NPD7435	Discontinued
0.6545	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD37	Approved
0.6533	Remote Similarity	NPD8361	Approved
0.6533	Remote Similarity	NPD8435	Approved
0.6533	Remote Similarity	NPD8360	Approved
0.6526	Remote Similarity	NPD3787	Discontinued
0.6524	Remote Similarity	NPD7768	Phase 2
0.6519	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD2346	Discontinued
0.6494	Remote Similarity	NPD5735	Approved
0.6488	Remote Similarity	NPD4107	Approved
0.6477	Remote Similarity	NPD7033	Discontinued
0.6477	Remote Similarity	NPD2799	Discontinued
0.6477	Remote Similarity	NPD3748	Approved
0.6477	Remote Similarity	NPD7228	Approved
0.6477	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD6959	Discontinued
0.6471	Remote Similarity	NPD5647	Approved
0.6467	Remote Similarity	NPD7458	Discontinued
0.6464	Remote Similarity	NPD1511	Approved
0.6461	Remote Similarity	NPD1549	Phase 2
0.6457	Remote Similarity	NPD6653	Approved
0.6456	Remote Similarity	NPD4482	Phase 3
0.6448	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6445	Remote Similarity	NPD7874	Approved
0.6445	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD6099	Approved
0.6441	Remote Similarity	NPD1551	Phase 2
0.6441	Remote Similarity	NPD6100	Approved
0.6425	Remote Similarity	NPD3057	Approved
0.6425	Remote Similarity	NPD3533	Approved
0.6425	Remote Similarity	NPD2972	Approved
0.6422	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD1465	Phase 2
0.6416	Remote Similarity	NPD2313	Discontinued
0.6408	Remote Similarity	NPD6780	Approved
0.6408	Remote Similarity	NPD6781	Approved
0.6408	Remote Similarity	NPD6776	Approved
0.6408	Remote Similarity	NPD6779	Approved
0.6408	Remote Similarity	NPD6782	Approved
0.6408	Remote Similarity	NPD6777	Approved
0.6408	Remote Similarity	NPD6778	Approved
0.6404	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6394	Remote Similarity	NPD7696	Phase 3
0.6394	Remote Similarity	NPD7698	Approved
0.6394	Remote Similarity	NPD7697	Approved
0.6384	Remote Similarity	NPD1510	Phase 2
0.6379	Remote Similarity	NPD8032	Phase 2
0.6374	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD2403	Approved
0.6372	Remote Similarity	NPD7048	Phase 3
0.6364	Remote Similarity	NPD8320	Phase 1
0.6364	Remote Similarity	NPD8319	Approved
0.6364	Remote Similarity	NPD7871	Phase 2
0.6364	Remote Similarity	NPD7870	Phase 2
0.6359	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD7315	Approved
0.6354	Remote Similarity	NPD6190	Approved
0.6354	Remote Similarity	NPD7229	Phase 3
0.6351	Remote Similarity	NPD7701	Phase 2
0.635	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD2491	Approved
0.6345	Remote Similarity	NPD7240	Approved
0.6343	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD4140	Approved
0.6341	Remote Similarity	NPD8485	Approved
0.6338	Remote Similarity	NPD7801	Approved
0.6322	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD2344	Approved
0.6308	Remote Similarity	NPD8462	Phase 1
0.6307	Remote Similarity	NPD447	Suspended
0.6301	Remote Similarity	NPD6832	Phase 2
0.6298	Remote Similarity	NPD4110	Phase 3
0.6298	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD8166	Discontinued
0.6298	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD7078	Approved
0.629	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD6663	Approved
0.6284	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.628	Remote Similarity	NPD8285	Discontinued
0.6271	Remote Similarity	NPD6651	Approved
0.6271	Remote Similarity	NPD6353	Approved
0.6269	Remote Similarity	NPD5711	Approved
0.6269	Remote Similarity	NPD5710	Approved
0.6268	Remote Similarity	NPD3448	Approved
0.6264	Remote Similarity	NPD7095	Approved
0.6262	Remote Similarity	NPD5676	Approved
0.6257	Remote Similarity	NPD2935	Discontinued
0.625	Remote Similarity	NPD7930	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