NPASS Compound

Structure

CID74216 OpenBabel06191715412D 37 43 0 0 1 0 0 0 0 0999 V2000 6.6298 -2.4295 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7124 -2.8713 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2593 -0.2598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2863 -0.5599 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5179 -0.8324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4100 3.0270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4161 -0.6674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1625 -1.3600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4234 -1.0598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1968 -0.0671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0617 0.1713 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0653 -1.2568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5348 1.8990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8055 0.6229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6426 0.3253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1354 -1.0598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6552 0.7257 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0761 -1.0154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6156 0.6254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3620 -0.0671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6673 1.9726 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0788 1.3951 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7885 -1.8559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5129 0.4327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6005 -0.3906 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6688 1.6319 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0565 1.1579 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9422 0.3861 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6308 1.6435 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.2734 2.0180 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.7006 -1.6738 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3671 2.9456 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0210 1.7813 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4418 0.1830 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2794 0.3746 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7703 -1.8559 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 24 1 0 0 0 0 5 25 1 0 0 0 0 6 30 1 0 0 0 0 7 8 2 0 0 0 0 7 15 1 0 0 0 0 8 16 1 0 0 0 0 9 10 2 0 0 0 0 9 23 1 0 0 0 0 10 36 1 0 0 0 0 11 17 1 0 0 0 0 12 18 1 0 0 0 0 12 25 1 0 0 0 0 14 26 1 0 0 0 0 14 31 1 0 0 0 0 15 19 2 0 0 0 0 15 27 1 0 0 0 0 16 20 2 0 0 0 0 16 37 1 0 0 0 0 17 24 1 0 0 0 0 17 26 1 6 0 0 0 18 31 1 0 0 0 0 18 32 2 0 0 0 0 19 20 1 0 0 0 0 19 29 1 0 0 0 0 20 36 1 0 0 0 0 21 27 1 0 0 0 0 21 29 2 0 0 0 0 21 33 1 0 0 0 0 22 28 1 0 0 0 0 22 30 1 0 0 0 0 22 34 2 0 0 0 0 23 37 1 0 0 0 0 24 27 1 0 0 0 0 25 28 1 6 0 0 0 25 35 1 0 0 0 0 26 13 1 1 0 0 0 26 30 1 0 0 0 0 27 13 1 6 0 0 0 28 11 1 1 0 0 0 28 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	507.24
Volume:	500.225
LogP:	3.356
LogD:	2.294
LogS:	-4.687
# Rotatable Bonds:	0
TPSA:	108.41
# H-Bond Aceptor:	9
# H-Bond Donor:	2
# Rings:	8
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.558
Synthetic Accessibility Score:	6.89
Fsp3:	0.607
Lipinski Rule-of-5:	Accepted
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:	-5.204
MDCK Permeability:	2.016872531385161e-05
Pgp-inhibitor:	0.899
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.838
20% Bioavailability (F20%):	0.963
30% Bioavailability (F30%):	0.981

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.719
Plasma Protein Binding (PPB):	71.35260772705078%
Volume Distribution (VD):	0.81
Pgp-substrate:	35.45790481567383%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.303
CYP2C19-inhibitor:	0.092
CYP2C19-substrate:	0.919
CYP2C9-inhibitor:	0.592
CYP2C9-substrate:	0.243
CYP2D6-inhibitor:	0.026
CYP2D6-substrate:	0.125
CYP3A4-inhibitor:	0.902
CYP3A4-substrate:	0.953

ADMET: Excretion

Clearance (CL):	4.292
Half-life (T1/2):	0.421

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.864
Drug-inuced Liver Injury (DILI):	0.203
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.979
Maximum Recommended Daily Dose:	0.944
Skin Sensitization:	0.027
Carcinogencity:	0.986
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.368

Download Data

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

Natural Product: NPC74216

Natural Product ID:	NPC74216
*Common Name:**	HHMKOJPJOSZYET-MGUBYGHDSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	HHMKOJPJOSZYET-MGUBYGHDSA-N
Standard InCHI:	InChI=1S/C28H33N3O6/c1-23(2)9-10-36-20-16(37-23)8-7-15-19(20)29-21(33)27(15)13-26-14-31-18(32)12-25(5,35)28(31,22(34)30(26)6)11-17(26)24(27,3)4/h7-10,17,35H,11-14H2,1-6H3,(H,29,33)/t17-,25+,26+,27+,28-/m0/s1
SMILES:	O=C1C[C@@]([C@]23N1C[C@@]1(C[C@]4(C([C@@H]1C2)(C)C)C(=Nc1c4ccc2c1OC=CC(O2)(C)C)O)N(C3=O)C)(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2252927
PubChem CID:	14337025
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000130] Azaspirodecane 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
NPO23507	Fissistigma balansae	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10978218]
NPO23039	Turbo stenogyrus	Species	Turbinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16038534]
NPO23346	Penicillium cluniae	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16608209]
NPO21925	Senecio serra	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17526	Entada abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23346	Penicillium cluniae	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23713	Helina dubia	Species	Muscidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21989	Uvaria tanzaniae	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23507	Fissistigma balansae	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23039	Turbo stenogyrus	Species	Turbinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22861	Amansia glomerata	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12670	Lactobacillus plantarum	Species	Lactobacillaceae	Bacteria	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
LD50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2212	Organism	Oncopeltus fasciatus	Oncopeltus fasciatus	LD50	=	0.91	ug	PMID[451675]

☑ 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 NPC74216 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	409
0.1-0.2	1835
0.2-0.3	5745
0.3-0.4	12628
0.4-0.5	14477
0.5-0.6	6595
0.6-0.7	900
0.7-0.8	93
0.8-0.85	4
0.85-0.9	3
0.9-0.95	2
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9901	High Similarity	NPC266994
0.9752	High Similarity	NPC71539
0.9752	High Similarity	NPC250960
0.9565	High Similarity	NPC470821
0.8249	Intermediate Similarity	NPC37957
0.8122	Intermediate Similarity	NPC205926
0.8082	Intermediate Similarity	NPC153923
0.7799	Intermediate Similarity	NPC204970
0.7736	Intermediate Similarity	NPC272706
0.7644	Intermediate Similarity	NPC318525
0.7644	Intermediate Similarity	NPC10653
0.7636	Intermediate Similarity	NPC476651
0.7574	Intermediate Similarity	NPC49583
0.7545	Intermediate Similarity	NPC470001
0.7545	Intermediate Similarity	NPC470002
0.7536	Intermediate Similarity	NPC174629
0.7523	Intermediate Similarity	NPC82541
0.7489	Intermediate Similarity	NPC473422
0.7456	Intermediate Similarity	NPC46259
0.7443	Intermediate Similarity	NPC473460
0.7411	Intermediate Similarity	NPC159815
0.7289	Intermediate Similarity	NPC471532
0.7277	Intermediate Similarity	NPC471561
0.7277	Intermediate Similarity	NPC477160
0.7264	Intermediate Similarity	NPC473007
0.7257	Intermediate Similarity	NPC10732
0.7252	Intermediate Similarity	NPC14339
0.7243	Intermediate Similarity	NPC217294
0.7231	Intermediate Similarity	NPC477393
0.7222	Intermediate Similarity	NPC470480
0.722	Intermediate Similarity	NPC477395
0.7217	Intermediate Similarity	NPC219397
0.7217	Intermediate Similarity	NPC108826
0.7209	Intermediate Similarity	NPC473008
0.72	Intermediate Similarity	NPC168250
0.7181	Intermediate Similarity	NPC470482
0.7181	Intermediate Similarity	NPC470481
0.7179	Intermediate Similarity	NPC476436
0.7172	Intermediate Similarity	NPC477396
0.717	Intermediate Similarity	NPC98197
0.7169	Intermediate Similarity	NPC161804
0.7161	Intermediate Similarity	NPC477397
0.7143	Intermediate Similarity	NPC473004
0.7137	Intermediate Similarity	NPC231924
0.7087	Intermediate Similarity	NPC471531
0.7085	Intermediate Similarity	NPC473005
0.7083	Intermediate Similarity	NPC291173
0.7076	Intermediate Similarity	NPC471513
0.7076	Intermediate Similarity	NPC248903
0.7075	Intermediate Similarity	NPC39822
0.7072	Intermediate Similarity	NPC67904
0.7051	Intermediate Similarity	NPC148124
0.7034	Intermediate Similarity	NPC26928
0.7029	Intermediate Similarity	NPC476429
0.7025	Intermediate Similarity	NPC470785
0.7016	Intermediate Similarity	NPC133609
0.7013	Intermediate Similarity	NPC234772
0.7009	Intermediate Similarity	NPC99724
0.6983	Remote Similarity	NPC184680
0.6972	Remote Similarity	NPC473569
0.6966	Remote Similarity	NPC476069
0.6957	Remote Similarity	NPC127996
0.6955	Remote Similarity	NPC470485
0.6955	Remote Similarity	NPC474183
0.6944	Remote Similarity	NPC102760
0.6941	Remote Similarity	NPC28510
0.6933	Remote Similarity	NPC474077
0.693	Remote Similarity	NPC317709
0.693	Remote Similarity	NPC329329
0.6923	Remote Similarity	NPC230313
0.6923	Remote Similarity	NPC222046
0.692	Remote Similarity	NPC189079
0.692	Remote Similarity	NPC138830
0.692	Remote Similarity	NPC127178
0.692	Remote Similarity	NPC19175
0.6912	Remote Similarity	NPC276120
0.691	Remote Similarity	NPC195636
0.6901	Remote Similarity	NPC160113
0.6901	Remote Similarity	NPC476220
0.6887	Remote Similarity	NPC164608
0.6885	Remote Similarity	NPC470784
0.6878	Remote Similarity	NPC203972
0.6875	Remote Similarity	NPC123859
0.6872	Remote Similarity	NPC470484
0.6872	Remote Similarity	NPC163829
0.6872	Remote Similarity	NPC154922
0.6864	Remote Similarity	NPC470483
0.6864	Remote Similarity	NPC128476
0.6862	Remote Similarity	NPC473458
0.6855	Remote Similarity	NPC58209
0.6851	Remote Similarity	NPC288110
0.6849	Remote Similarity	NPC122886
0.6842	Remote Similarity	NPC246140
0.6842	Remote Similarity	NPC158551
0.6842	Remote Similarity	NPC195787
0.6837	Remote Similarity	NPC166169
0.6818	Remote Similarity	NPC64140
0.6818	Remote Similarity	NPC174122
0.6809	Remote Similarity	NPC77777
0.6789	Remote Similarity	NPC304837
0.6789	Remote Similarity	NPC476258
0.6781	Remote Similarity	NPC473006
0.678	Remote Similarity	NPC475609
0.6778	Remote Similarity	NPC477394
0.6773	Remote Similarity	NPC234069
0.6771	Remote Similarity	NPC243626
0.6766	Remote Similarity	NPC126556
0.6759	Remote Similarity	NPC32064
0.6756	Remote Similarity	NPC100863
0.6742	Remote Similarity	NPC29531
0.6741	Remote Similarity	NPC149962
0.6734	Remote Similarity	NPC166712
0.6734	Remote Similarity	NPC113455
0.6734	Remote Similarity	NPC469451
0.6724	Remote Similarity	NPC269449
0.6721	Remote Similarity	NPC469450
0.6713	Remote Similarity	NPC287152
0.6712	Remote Similarity	NPC138083
0.6711	Remote Similarity	NPC475747
0.6711	Remote Similarity	NPC144314
0.6707	Remote Similarity	NPC160100
0.6696	Remote Similarity	NPC471563
0.6696	Remote Similarity	NPC242728
0.6695	Remote Similarity	NPC313327
0.6694	Remote Similarity	NPC34770
0.6681	Remote Similarity	NPC50548
0.6681	Remote Similarity	NPC475133
0.6681	Remote Similarity	NPC293624
0.668	Remote Similarity	NPC329932
0.6667	Remote Similarity	NPC469452
0.6653	Remote Similarity	NPC120239
0.6652	Remote Similarity	NPC219664
0.6651	Remote Similarity	NPC270301
0.664	Remote Similarity	NPC188400
0.6638	Remote Similarity	NPC311357
0.6637	Remote Similarity	NPC66909
0.6625	Remote Similarity	NPC470846
0.6623	Remote Similarity	NPC477161
0.6622	Remote Similarity	NPC230098
0.6622	Remote Similarity	NPC59827
0.6622	Remote Similarity	NPC184933
0.6609	Remote Similarity	NPC207971
0.6606	Remote Similarity	NPC262725
0.6606	Remote Similarity	NPC474470
0.6605	Remote Similarity	NPC293255
0.6605	Remote Similarity	NPC298851
0.6605	Remote Similarity	NPC21752
0.6605	Remote Similarity	NPC210415
0.6605	Remote Similarity	NPC181138
0.6605	Remote Similarity	NPC276993
0.6596	Remote Similarity	NPC119722
0.6596	Remote Similarity	NPC203168
0.6592	Remote Similarity	NPC22689
0.6592	Remote Similarity	NPC105055
0.6591	Remote Similarity	NPC302235
0.6588	Remote Similarity	NPC59028
0.6588	Remote Similarity	NPC92191
0.6584	Remote Similarity	NPC13249
0.658	Remote Similarity	NPC268077
0.658	Remote Similarity	NPC475147
0.6577	Remote Similarity	NPC329731
0.6577	Remote Similarity	NPC4910
0.6577	Remote Similarity	NPC21425
0.6574	Remote Similarity	NPC208364
0.6564	Remote Similarity	NPC475713
0.6564	Remote Similarity	NPC474432
0.6561	Remote Similarity	NPC315542
0.6555	Remote Similarity	NPC305984
0.655	Remote Similarity	NPC474427
0.6546	Remote Similarity	NPC131486
0.6546	Remote Similarity	NPC301501
0.654	Remote Similarity	NPC66191
0.654	Remote Similarity	NPC316297
0.654	Remote Similarity	NPC148391
0.654	Remote Similarity	NPC314817
0.6535	Remote Similarity	NPC71124
0.6535	Remote Similarity	NPC477527
0.6533	Remote Similarity	NPC196231
0.6532	Remote Similarity	NPC474746
0.6532	Remote Similarity	NPC475981
0.653	Remote Similarity	NPC222524
0.6529	Remote Similarity	NPC475292
0.6529	Remote Similarity	NPC475349
0.6529	Remote Similarity	NPC475565
0.6528	Remote Similarity	NPC82533
0.6528	Remote Similarity	NPC290759
0.6528	Remote Similarity	NPC266176
0.6528	Remote Similarity	NPC158148
0.6527	Remote Similarity	NPC87560
0.6526	Remote Similarity	NPC470069
0.6526	Remote Similarity	NPC52059
0.6526	Remote Similarity	NPC254700
0.6522	Remote Similarity	NPC64576
0.6522	Remote Similarity	NPC201055
0.6522	Remote Similarity	NPC151470
0.6522	Remote Similarity	NPC254045
0.652	Remote Similarity	NPC477258
0.6518	Remote Similarity	NPC283207
0.6518	Remote Similarity	NPC208890
0.6515	Remote Similarity	NPC76478

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 NPC74216 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	230
0.1-0.2	616
0.2-0.3	946
0.3-0.4	2373
0.4-0.5	3067
0.5-0.6	1670
0.6-0.7	247
0.7-0.8	1
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
0.7251	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD5312	Approved
0.6901	Remote Similarity	NPD5313	Approved
0.6898	Remote Similarity	NPD7281	Phase 3
0.6898	Remote Similarity	NPD7280	Phase 3
0.6866	Remote Similarity	NPD6851	Approved
0.6866	Remote Similarity	NPD6853	Approved
0.6844	Remote Similarity	NPD7048	Phase 3
0.6818	Remote Similarity	NPD2843	Phase 2
0.6818	Remote Similarity	NPD2845	Phase 2
0.6797	Remote Similarity	NPD5645	Phase 3
0.6789	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6787	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD3592	Approved
0.6753	Remote Similarity	NPD3591	Approved
0.6741	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD5562	Approved
0.6723	Remote Similarity	NPD5561	Approved
0.6721	Remote Similarity	NPD6625	Approved
0.6708	Remote Similarity	NPD3442	Approved
0.6708	Remote Similarity	NPD3441	Approved
0.6698	Remote Similarity	NPD4498	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD6997	Phase 2
0.6695	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD4206	Approved
0.6682	Remote Similarity	NPD6297	Approved
0.6681	Remote Similarity	NPD7559	Phase 2
0.6667	Remote Similarity	NPD7278	Phase 2
0.6667	Remote Similarity	NPD5582	Discontinued
0.6667	Remote Similarity	NPD7279	Phase 2
0.6652	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD5772	Approved
0.6651	Remote Similarity	NPD5773	Approved
0.665	Remote Similarity	NPD4210	Discontinued
0.664	Remote Similarity	NPD4846	Phase 2
0.6637	Remote Similarity	NPD2975	Approved
0.6637	Remote Similarity	NPD2974	Approved
0.6637	Remote Similarity	NPD2973	Approved
0.6637	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD4580	Approved
0.6623	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD4885	Approved
0.6598	Remote Similarity	NPD7820	Phase 3
0.6589	Remote Similarity	NPD4166	Phase 2
0.6587	Remote Similarity	NPD8359	Phase 2
0.6579	Remote Similarity	NPD7810	Phase 3
0.6579	Remote Similarity	NPD7811	Phase 3
0.6578	Remote Similarity	NPD7125	Discontinued
0.6576	Remote Similarity	NPD8255	Phase 2
0.6571	Remote Similarity	NPD5294	Clinical (unspecified phase)
0.657	Remote Similarity	NPD7821	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD2899	Discontinued
0.6565	Remote Similarity	NPD3106	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD4157	Discontinued
0.6547	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.654	Remote Similarity	NPD6063	Approved
0.654	Remote Similarity	NPD5967	Approved
0.6523	Remote Similarity	NPD7859	Phase 2
0.6522	Remote Similarity	NPD2493	Approved
0.6522	Remote Similarity	NPD2494	Approved
0.6522	Remote Similarity	NPD3450	Approved
0.6522	Remote Similarity	NPD6321	Discontinued
0.6522	Remote Similarity	NPD3452	Approved
0.6515	Remote Similarity	NPD7805	Phase 3
0.6513	Remote Similarity	NPD5025	Approved
0.6513	Remote Similarity	NPD7047	Phase 3
0.6512	Remote Similarity	NPD7315	Approved
0.6509	Remote Similarity	NPD4583	Approved
0.6509	Remote Similarity	NPD4040	Phase 1
0.6509	Remote Similarity	NPD6644	Discontinued
0.6509	Remote Similarity	NPD4582	Approved
0.6498	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD8161	Suspended
0.6473	Remote Similarity	NPD7291	Discontinued
0.6466	Remote Similarity	NPD4004	Approved
0.6466	Remote Similarity	NPD4002	Approved
0.6465	Remote Similarity	NPD6107	Approved
0.6463	Remote Similarity	NPD5071	Phase 2
0.6462	Remote Similarity	NPD7955	Approved
0.6462	Remote Similarity	NPD7956	Approved
0.6461	Remote Similarity	NPD3912	Discontinued
0.646	Remote Similarity	NPD7296	Approved
0.6444	Remote Similarity	NPD8149	Discontinued
0.6441	Remote Similarity	NPD2968	Approved
0.6441	Remote Similarity	NPD2971	Approved
0.6435	Remote Similarity	NPD6071	Discontinued
0.6425	Remote Similarity	NPD6104	Discontinued
0.6423	Remote Similarity	NPD8461	Discontinued
0.6419	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6416	Remote Similarity	NPD2490	Approved
0.6416	Remote Similarity	NPD2488	Approved
0.6415	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD6668	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD5676	Approved
0.6407	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD3437	Discontinued
0.6398	Remote Similarity	NPD4772	Phase 2
0.6398	Remote Similarity	NPD4773	Phase 2
0.6391	Remote Similarity	NPD4420	Approved
0.6383	Remote Similarity	NPD7263	Phase 2
0.638	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3639	Approved
0.6364	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6874	Approved
0.6364	Remote Similarity	NPD7131	Phase 3
0.6364	Remote Similarity	NPD3641	Approved
0.6364	Remote Similarity	NPD3640	Phase 3
0.636	Remote Similarity	NPD3631	Phase 3
0.6356	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD2907	Approved
0.6356	Remote Similarity	NPD8027	Approved
0.6356	Remote Similarity	NPD2906	Approved
0.6352	Remote Similarity	NPD5006	Approved
0.6352	Remote Similarity	NPD5005	Approved
0.6349	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD4605	Approved
0.6348	Remote Similarity	NPD4604	Approved
0.6344	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.634	Remote Similarity	NPD7803	Approved
0.6339	Remote Similarity	NPD6716	Phase 1
0.6336	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD4124	Clinical (unspecified phase)
0.633	Remote Similarity	NPD2216	Approved
0.633	Remote Similarity	NPD2215	Approved
0.6327	Remote Similarity	NPD7906	Approved
0.6314	Remote Similarity	NPD7043	Discontinued
0.6313	Remote Similarity	NPD7126	Discontinued
0.6311	Remote Similarity	NPD7907	Approved
0.6311	Remote Similarity	NPD7556	Discontinued
0.631	Remote Similarity	NPD6982	Phase 2
0.6305	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.6291	Remote Similarity	NPD1769	Discontinued
0.6286	Remote Similarity	NPD2122	Discontinued
0.6284	Remote Similarity	NPD8492	Approved
0.6284	Remote Similarity	NPD3051	Approved
0.6283	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6278	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD7426	Phase 1
0.6274	Remote Similarity	NPD5617	Suspended
0.6273	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6268	Remote Similarity	NPD4123	Phase 3
0.6267	Remote Similarity	NPD6618	Phase 2
0.6265	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD2970	Approved
0.6256	Remote Similarity	NPD2969	Approved
0.625	Remote Similarity	NPD7831	Phase 2
0.625	Remote Similarity	NPD7833	Phase 2
0.625	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7225	Discontinued
0.6244	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD7110	Phase 1
0.6244	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD6238	Discontinued
0.6233	Remote Similarity	NPD6878	Phase 2
0.6233	Remote Similarity	NPD6879	Phase 2
0.6233	Remote Similarity	NPD2563	Approved
0.6233	Remote Similarity	NPD2560	Approved
0.6233	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.623	Remote Similarity	NPD4665	Approved
0.623	Remote Similarity	NPD4111	Phase 1
0.6228	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6227	Remote Similarity	NPD2898	Approved
0.6227	Remote Similarity	NPD4481	Phase 3
0.6223	Remote Similarity	NPD5547	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD4577	Approved
0.6222	Remote Similarity	NPD4578	Approved
0.6218	Remote Similarity	NPD8459	Approved
0.6218	Remote Similarity	NPD8460	Approved
0.6213	Remote Similarity	NPD3057	Approved
0.6213	Remote Similarity	NPD956	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD4663	Approved
0.621	Remote Similarity	NPD7608	Discontinued
0.621	Remote Similarity	NPD3263	Phase 3
0.6208	Remote Similarity	NPD1945	Phase 1
0.6208	Remote Similarity	NPD683	Approved
0.6201	Remote Similarity	NPD6505	Approved
0.6201	Remote Similarity	NPD6504	Approved
0.6197	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.6197	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6197	Remote Similarity	NPD6519	Phase 2
0.6196	Remote Similarity	NPD8016	Phase 3
0.6196	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD2161	Phase 2
0.6194	Remote Similarity	NPD5566	Clinical (unspecified phase)
0.6193	Remote Similarity	NPD2904	Discontinued
0.6193	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6193	Remote Similarity	NPD5677	Discontinued
0.6193	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6192	Remote Similarity	NPD8367	Approved
0.619	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6189	Remote Similarity	NPD7708	Approved
0.6189	Remote Similarity	NPD6568	Discontinued
0.6188	Remote Similarity	NPD5557	Phase 1
0.6186	Remote Similarity	NPD7497	Discontinued
0.6184	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD4237	Approved
0.6184	Remote Similarity	NPD5620	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