NPASS Compound

Structure

CID250960 OpenBabel06191716052D 35 41 0 0 1 0 0 0 0 0999 V2000 -1.2301 -2.2063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6285 2.8853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7554 3.3219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4163 -2.2327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0701 -2.5842 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5362 -1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5638 1.2565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2893 1.9097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5022 -0.4881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4109 1.5752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9284 0.3017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1795 0.6269 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8454 -1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6192 0.3017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8454 0.4881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9284 -1.2778 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7668 0.3017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2177 1.6081 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6908 -0.9762 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6952 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4207 0.6532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7668 -1.2778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8454 -1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8138 2.3475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6192 -1.2778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6908 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1930 -0.4881 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.9762 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6952 -0.9762 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.6908 -0.9762 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 3.4651 -2.2063 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8454 -2.4405 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2938 0.2165 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8377 2.3621 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 24 1 0 0 0 0 3 24 1 0 0 0 0 4 25 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 17 1 0 0 0 0 8 18 1 0 0 0 0 9 11 1 0 0 0 0 9 16 1 0 0 0 0 10 12 2 0 0 0 0 10 24 1 0 0 0 0 11 31 1 0 0 0 0 12 34 1 0 0 0 0 13 19 1 0 0 0 0 13 28 1 0 0 0 0 14 26 1 0 0 0 0 15 26 1 0 0 0 0 15 31 1 0 0 0 0 16 28 1 1 0 0 0 17 20 2 0 0 0 0 17 27 1 0 0 0 0 18 21 2 0 0 0 0 18 35 1 0 0 0 0 19 25 1 0 0 0 0 19 26 1 6 0 0 0 20 21 1 0 0 0 0 20 29 1 0 0 0 0 21 34 1 0 0 0 0 22 27 1 0 0 0 0 22 29 2 0 0 0 0 22 32 1 0 0 0 0 23 28 1 0 0 0 0 23 30 1 0 0 0 0 23 33 2 0 0 0 0 24 35 1 0 0 0 0 25 27 1 0 0 0 0 26 30 1 1 0 0 0 27 14 1 1 0 0 0 28 31 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	477.26
Volume:	485.281
LogP:	4.9
LogD:	3.124
LogS:	-5.386
# Rotatable Bonds:	0
TPSA:	71.11
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	8
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.617
Synthetic Accessibility Score:	6.756
Fsp3:	0.643
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.058
MDCK Permeability:	2.294934165547602e-05
Pgp-inhibitor:	0.989
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.232
20% Bioavailability (F20%):	0.967
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.877
Plasma Protein Binding (PPB):	74.88636016845703%
Volume Distribution (VD):	2.199
Pgp-substrate:	34.00812530517578%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.468
CYP2C19-inhibitor:	0.304
CYP2C19-substrate:	0.945
CYP2C9-inhibitor:	0.713
CYP2C9-substrate:	0.389
CYP2D6-inhibitor:	0.511
CYP2D6-substrate:	0.234
CYP3A4-inhibitor:	0.954
CYP3A4-substrate:	0.943

ADMET: Excretion

Clearance (CL):	5.648
Half-life (T1/2):	0.302

ADMET: Toxicity

hERG Blockers:	0.388
Human Hepatotoxicity (H-HT):	0.832
Drug-inuced Liver Injury (DILI):	0.039
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.987
Maximum Recommended Daily Dose:	0.94
Skin Sensitization:	0.034
Carcinogencity:	0.983
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.934

Download Data

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

Natural Product: NPC250960

Natural Product ID:	NPC250960
*Common Name:**	Paraherquamide E
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XNXXZRQPTAQILV-PYGUQFFJSA-N
Standard InCHI:	InChI=1S/C28H35N3O4/c1-16-9-11-31-15-26-14-27(25(4,5)19(26)13-28(16,31)23(33)30(26)6)17-7-8-18-21(20(17)29-22(27)32)34-12-10-24(2,3)35-18/h7-8,10,12,16,19H,9,11,13-15H2,1-6H3,(H,29,32)/t16-,19-,26+,27+,28+/m0/s1
SMILES:	OC1=Nc2c([C@@]31C[C@]14[C@H](C3(C)C)C[C@]3(N(C1)CC[C@@H]3C)C(=O)N4C)ccc1c2OC=CC(O1)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2252929
PubChem CID:	9898611
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]
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]
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]

☑ 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	=	0.089	ug	PMID[464365]

☑ 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 NPC250960 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	412
0.1-0.2	1723
0.2-0.3	5407
0.3-0.4	12838
0.4-0.5	14113
0.5-0.6	7059
0.6-0.7	1033
0.7-0.8	97
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
1.0	High Similarity	NPC71539
0.985	High Similarity	NPC266994
0.9752	High Similarity	NPC74216
0.9512	High Similarity	NPC470821
0.823	Intermediate Similarity	NPC205926
0.8186	Intermediate Similarity	NPC37957
0.8018	Intermediate Similarity	NPC153923
0.799	Intermediate Similarity	NPC204970
0.7923	Intermediate Similarity	NPC272706
0.7731	Intermediate Similarity	NPC476651
0.7718	Intermediate Similarity	NPC174629
0.7658	Intermediate Similarity	NPC10653
0.7658	Intermediate Similarity	NPC318525
0.7615	Intermediate Similarity	NPC82541
0.7581	Intermediate Similarity	NPC473422
0.7557	Intermediate Similarity	NPC470002
0.7557	Intermediate Similarity	NPC470001
0.7535	Intermediate Similarity	NPC473460
0.7511	Intermediate Similarity	NPC49583
0.7467	Intermediate Similarity	NPC46259
0.7421	Intermediate Similarity	NPC159815
0.7416	Intermediate Similarity	NPC217294
0.7378	Intermediate Similarity	NPC108826
0.7376	Intermediate Similarity	NPC471532
0.7364	Intermediate Similarity	NPC168250
0.7364	Intermediate Similarity	NPC471561
0.7343	Intermediate Similarity	NPC98197
0.7301	Intermediate Similarity	NPC219397
0.7256	Intermediate Similarity	NPC161804
0.719	Intermediate Similarity	NPC473007
0.7188	Intermediate Similarity	NPC470482
0.7188	Intermediate Similarity	NPC470481
0.7188	Intermediate Similarity	NPC10732
0.7186	Intermediate Similarity	NPC476436
0.7182	Intermediate Similarity	NPC14339
0.7168	Intermediate Similarity	NPC471531
0.7167	Intermediate Similarity	NPC477393
0.7163	Intermediate Similarity	NPC39822
0.7155	Intermediate Similarity	NPC248903
0.7155	Intermediate Similarity	NPC477395
0.7143	Intermediate Similarity	NPC231924
0.7136	Intermediate Similarity	NPC473008
0.713	Intermediate Similarity	NPC148124
0.713	Intermediate Similarity	NPC477160
0.7112	Intermediate Similarity	NPC26928
0.7107	Intermediate Similarity	NPC477396
0.7103	Intermediate Similarity	NPC28510
0.7094	Intermediate Similarity	NPC477397
0.7091	Intermediate Similarity	NPC474077
0.7087	Intermediate Similarity	NPC99724
0.7085	Intermediate Similarity	NPC317709
0.7085	Intermediate Similarity	NPC329329
0.7082	Intermediate Similarity	NPC470480
0.7078	Intermediate Similarity	NPC67904
0.7078	Intermediate Similarity	NPC127178
0.707	Intermediate Similarity	NPC473004
0.7056	Intermediate Similarity	NPC473569
0.7043	Intermediate Similarity	NPC476069
0.7037	Intermediate Similarity	NPC470485
0.7037	Intermediate Similarity	NPC203972
0.7034	Intermediate Similarity	NPC476429
0.7028	Intermediate Similarity	NPC102760
0.7027	Intermediate Similarity	NPC163829
0.7017	Intermediate Similarity	NPC291173
0.7014	Intermediate Similarity	NPC473005
0.7013	Intermediate Similarity	NPC128476
0.7009	Intermediate Similarity	NPC471513
0.6996	Remote Similarity	NPC158551
0.6996	Remote Similarity	NPC19175
0.6987	Remote Similarity	NPC195636
0.6971	Remote Similarity	NPC164608
0.6958	Remote Similarity	NPC470785
0.6951	Remote Similarity	NPC133609
0.6951	Remote Similarity	NPC470484
0.6944	Remote Similarity	NPC470483
0.6923	Remote Similarity	NPC138830
0.692	Remote Similarity	NPC195787
0.692	Remote Similarity	NPC246140
0.6917	Remote Similarity	NPC184680
0.6913	Remote Similarity	NPC126556
0.6888	Remote Similarity	NPC474183
0.6886	Remote Similarity	NPC127996
0.6872	Remote Similarity	NPC269449
0.687	Remote Similarity	NPC234772
0.6855	Remote Similarity	NPC189079
0.6853	Remote Similarity	NPC222046
0.6849	Remote Similarity	NPC230313
0.684	Remote Similarity	NPC32064
0.684	Remote Similarity	NPC313327
0.6837	Remote Similarity	NPC276120
0.6833	Remote Similarity	NPC100863
0.6828	Remote Similarity	NPC475133
0.682	Remote Similarity	NPC29531
0.6818	Remote Similarity	NPC470784
0.6818	Remote Similarity	NPC149962
0.6802	Remote Similarity	NPC123859
0.6793	Remote Similarity	NPC473458
0.6792	Remote Similarity	NPC287152
0.6791	Remote Similarity	NPC138083
0.679	Remote Similarity	NPC469450
0.6787	Remote Similarity	NPC144314
0.6781	Remote Similarity	NPC288110
0.6774	Remote Similarity	NPC230098
0.6773	Remote Similarity	NPC471563
0.6771	Remote Similarity	NPC242728
0.6763	Remote Similarity	NPC476220
0.6763	Remote Similarity	NPC160113
0.6762	Remote Similarity	NPC276993
0.6762	Remote Similarity	NPC293255
0.6762	Remote Similarity	NPC181138
0.6762	Remote Similarity	NPC21752
0.6762	Remote Similarity	NPC210415
0.6762	Remote Similarity	NPC298851
0.6761	Remote Similarity	NPC166169
0.6757	Remote Similarity	NPC50548
0.6743	Remote Similarity	NPC64140
0.6743	Remote Similarity	NPC174122
0.6739	Remote Similarity	NPC119722
0.6738	Remote Similarity	NPC77777
0.6736	Remote Similarity	NPC154922
0.6735	Remote Similarity	NPC469451
0.6735	Remote Similarity	NPC469452
0.6729	Remote Similarity	NPC270301
0.6726	Remote Similarity	NPC268077
0.6726	Remote Similarity	NPC475147
0.6725	Remote Similarity	NPC219664
0.6721	Remote Similarity	NPC58209
0.6712	Remote Similarity	NPC66909
0.6711	Remote Similarity	NPC311357
0.671	Remote Similarity	NPC473006
0.6709	Remote Similarity	NPC477394
0.6697	Remote Similarity	NPC184933
0.6697	Remote Similarity	NPC243626
0.6697	Remote Similarity	NPC234069
0.6697	Remote Similarity	NPC59827
0.6695	Remote Similarity	NPC305984
0.6683	Remote Similarity	NPC52059
0.6683	Remote Similarity	NPC470069
0.6682	Remote Similarity	NPC474470
0.6682	Remote Similarity	NPC71124
0.6681	Remote Similarity	NPC207971
0.668	Remote Similarity	NPC329932
0.6667	Remote Similarity	NPC59028
0.6667	Remote Similarity	NPC92191
0.6667	Remote Similarity	NPC203168
0.6653	Remote Similarity	NPC476258
0.6653	Remote Similarity	NPC304837
0.6652	Remote Similarity	NPC267414
0.6651	Remote Similarity	NPC21425
0.6651	Remote Similarity	NPC4910
0.6651	Remote Similarity	NPC329731
0.665	Remote Similarity	NPC263709
0.665	Remote Similarity	NPC97380
0.665	Remote Similarity	NPC243673
0.665	Remote Similarity	NPC310403
0.665	Remote Similarity	NPC63210
0.665	Remote Similarity	NPC148468
0.6639	Remote Similarity	NPC122886
0.6638	Remote Similarity	NPC475609
0.6623	Remote Similarity	NPC476500
0.6621	Remote Similarity	NPC477186
0.662	Remote Similarity	NPC474745
0.6619	Remote Similarity	NPC231198
0.6612	Remote Similarity	NPC131486
0.6609	Remote Similarity	NPC314817
0.6609	Remote Similarity	NPC316297
0.6609	Remote Similarity	NPC66191
0.6607	Remote Similarity	NPC477527
0.6607	Remote Similarity	NPC293624
0.6604	Remote Similarity	NPC82533
0.6604	Remote Similarity	NPC158148
0.6604	Remote Similarity	NPC266176
0.6604	Remote Similarity	NPC290759
0.6603	Remote Similarity	NPC254700
0.6599	Remote Similarity	NPC113455
0.6599	Remote Similarity	NPC166712
0.6593	Remote Similarity	NPC64576
0.6593	Remote Similarity	NPC254045
0.6593	Remote Similarity	NPC151470
0.6593	Remote Similarity	NPC201055
0.6591	Remote Similarity	NPC22689
0.6591	Remote Similarity	NPC105055
0.659	Remote Similarity	NPC115906
0.658	Remote Similarity	NPC14390
0.6579	Remote Similarity	NPC87714
0.6574	Remote Similarity	NPC474325
0.6573	Remote Similarity	NPC474708
0.6573	Remote Similarity	NPC188400
0.6573	Remote Similarity	NPC160100
0.6564	Remote Similarity	NPC1464
0.6561	Remote Similarity	NPC477526
0.656	Remote Similarity	NPC229234
0.6558	Remote Similarity	NPC49353
0.6558	Remote Similarity	NPC304675
0.6557	Remote Similarity	NPC34770
0.6555	Remote Similarity	NPC470846
0.655	Remote Similarity	NPC477161
0.6545	Remote Similarity	NPC301501
0.6542	Remote Similarity	NPC225597
0.6542	Remote Similarity	NPC470739

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 NPC250960 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	224
0.1-0.2	609
0.2-0.3	891
0.3-0.4	2317
0.4-0.5	3058
0.5-0.6	1757
0.6-0.7	293
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
0.7343	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7280	Phase 3
0.6981	Remote Similarity	NPD7281	Phase 3
0.6948	Remote Similarity	NPD6851	Approved
0.6948	Remote Similarity	NPD6853	Approved
0.6905	Remote Similarity	NPD5312	Approved
0.6905	Remote Similarity	NPD5313	Approved
0.6898	Remote Similarity	NPD2845	Phase 2
0.6898	Remote Similarity	NPD2843	Phase 2
0.6872	Remote Similarity	NPD5645	Phase 3
0.6866	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4206	Approved
0.6828	Remote Similarity	NPD3591	Approved
0.6828	Remote Similarity	NPD3592	Approved
0.6826	Remote Similarity	NPD7559	Phase 2
0.6818	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD5772	Approved
0.6814	Remote Similarity	NPD5773	Approved
0.6792	Remote Similarity	NPD6625	Approved
0.679	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD4498	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD6297	Approved
0.675	Remote Similarity	NPD4885	Approved
0.6742	Remote Similarity	NPD5582	Discontinued
0.6733	Remote Similarity	NPD4210	Discontinued
0.6727	Remote Similarity	NPD7125	Discontinued
0.6726	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD2975	Approved
0.6712	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD2973	Approved
0.6712	Remote Similarity	NPD2974	Approved
0.6708	Remote Similarity	NPD3442	Approved
0.6708	Remote Similarity	NPD7048	Phase 3
0.6708	Remote Similarity	NPD3441	Approved
0.6699	Remote Similarity	NPD5967	Approved
0.6697	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD4580	Approved
0.6695	Remote Similarity	NPD6997	Phase 2
0.6695	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7278	Phase 2
0.6667	Remote Similarity	NPD4166	Phase 2
0.6667	Remote Similarity	NPD7279	Phase 2
0.6652	Remote Similarity	NPD5561	Approved
0.6652	Remote Similarity	NPD5562	Approved
0.664	Remote Similarity	NPD8255	Phase 2
0.6637	Remote Similarity	NPD3106	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD7291	Discontinued
0.6621	Remote Similarity	NPD4157	Discontinued
0.6619	Remote Similarity	NPD6107	Approved
0.6618	Remote Similarity	NPD6063	Approved
0.6607	Remote Similarity	NPD5071	Phase 2
0.6597	Remote Similarity	NPD7820	Phase 3
0.6593	Remote Similarity	NPD2494	Approved
0.6593	Remote Similarity	NPD6321	Discontinued
0.6593	Remote Similarity	NPD3452	Approved
0.6593	Remote Similarity	NPD3450	Approved
0.6593	Remote Similarity	NPD2493	Approved
0.659	Remote Similarity	NPD2971	Approved
0.659	Remote Similarity	NPD2968	Approved
0.6588	Remote Similarity	NPD6071	Discontinued
0.6586	Remote Similarity	NPD8359	Phase 2
0.6581	Remote Similarity	NPD5025	Approved
0.6581	Remote Similarity	NPD7047	Phase 3
0.6579	Remote Similarity	NPD4582	Approved
0.6579	Remote Similarity	NPD6644	Discontinued
0.6579	Remote Similarity	NPD4583	Approved
0.6579	Remote Similarity	NPD4040	Phase 1
0.657	Remote Similarity	NPD5294	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD7821	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD2490	Approved
0.6561	Remote Similarity	NPD2488	Approved
0.6553	Remote Similarity	NPD4772	Phase 2
0.6553	Remote Similarity	NPD4773	Phase 2
0.655	Remote Similarity	NPD8161	Suspended
0.6535	Remote Similarity	NPD4002	Approved
0.6535	Remote Similarity	NPD4004	Approved
0.652	Remote Similarity	NPD3641	Approved
0.652	Remote Similarity	NPD3639	Approved
0.652	Remote Similarity	NPD3640	Phase 3
0.6511	Remote Similarity	NPD8149	Discontinued
0.6509	Remote Similarity	NPD7315	Approved
0.6504	Remote Similarity	NPD7810	Phase 3
0.6504	Remote Similarity	NPD7811	Phase 3
0.6504	Remote Similarity	NPD4846	Phase 2
0.6502	Remote Similarity	NPD3631	Phase 3
0.6498	Remote Similarity	NPD2899	Discontinued
0.6494	Remote Similarity	NPD8027	Approved
0.649	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6459	Remote Similarity	NPD7956	Approved
0.6459	Remote Similarity	NPD7955	Approved
0.6458	Remote Similarity	NPD3912	Discontinued
0.6457	Remote Similarity	NPD7296	Approved
0.6457	Remote Similarity	NPD7859	Phase 2
0.6452	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.645	Remote Similarity	NPD7263	Phase 2
0.6439	Remote Similarity	NPD7131	Phase 3
0.6439	Remote Similarity	NPD2122	Discontinued
0.6432	Remote Similarity	NPD3051	Approved
0.6425	Remote Similarity	NPD5617	Suspended
0.6419	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6416	Remote Similarity	NPD4604	Approved
0.6416	Remote Similarity	NPD4605	Approved
0.6411	Remote Similarity	NPD6668	Clinical (unspecified phase)
0.641	Remote Similarity	NPD5676	Approved
0.6409	Remote Similarity	NPD6618	Phase 2
0.6402	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD3437	Discontinued
0.6402	Remote Similarity	NPD2970	Approved
0.6402	Remote Similarity	NPD2969	Approved
0.6402	Remote Similarity	NPD2216	Approved
0.6402	Remote Similarity	NPD2215	Approved
0.6398	Remote Similarity	NPD7833	Phase 2
0.6398	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD7831	Phase 2
0.6396	Remote Similarity	NPD7906	Approved
0.6394	Remote Similarity	NPD7110	Phase 1
0.6394	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD7225	Discontinued
0.6381	Remote Similarity	NPD2563	Approved
0.6381	Remote Similarity	NPD2560	Approved
0.6375	Remote Similarity	NPD7556	Discontinued
0.6375	Remote Similarity	NPD7805	Phase 3
0.6372	Remote Similarity	NPD4481	Phase 3
0.6372	Remote Similarity	NPD2898	Approved
0.6368	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6367	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD1769	Discontinued
0.636	Remote Similarity	NPD6874	Approved
0.6359	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD8461	Discontinued
0.6355	Remote Similarity	NPD7608	Discontinued
0.6351	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.635	Remote Similarity	NPD2161	Phase 2
0.6347	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6347	Remote Similarity	NPD6104	Discontinued
0.6346	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD4123	Phase 3
0.6339	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD7426	Phase 1
0.6336	Remote Similarity	NPD7803	Approved
0.6335	Remote Similarity	NPD6716	Phase 1
0.6333	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.633	Remote Similarity	NPD5557	Phase 1
0.6329	Remote Similarity	NPD4124	Clinical (unspecified phase)
0.6323	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.632	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.632	Remote Similarity	NPD7497	Discontinued
0.632	Remote Similarity	NPD8016	Phase 3
0.6316	Remote Similarity	NPD4420	Approved
0.6316	Remote Similarity	NPD6877	Discontinued
0.6311	Remote Similarity	NPD3633	Approved
0.6311	Remote Similarity	NPD3634	Approved
0.6308	Remote Similarity	NPD7126	Discontinued
0.6308	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD6238	Discontinued
0.6301	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD5811	Approved
0.6298	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD27	Approved
0.6296	Remote Similarity	NPD2489	Approved
0.629	Remote Similarity	NPD7311	Approved
0.629	Remote Similarity	NPD7310	Approved
0.629	Remote Similarity	NPD7313	Approved
0.629	Remote Similarity	NPD4578	Approved
0.629	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.629	Remote Similarity	NPD7312	Approved
0.629	Remote Similarity	NPD4577	Approved
0.6288	Remote Similarity	NPD5547	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD8156	Discontinued
0.6282	Remote Similarity	NPD2906	Approved
0.6282	Remote Similarity	NPD5658	Approved
0.6282	Remote Similarity	NPD2907	Approved
0.6279	Remote Similarity	NPD8492	Approved
0.6278	Remote Similarity	NPD4663	Approved
0.6277	Remote Similarity	NPD5005	Approved
0.6277	Remote Similarity	NPD5006	Approved
0.6277	Remote Similarity	NPD3057	Approved
0.6276	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD5677	Discontinued
0.6262	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD2904	Discontinued
0.6261	Remote Similarity	NPD6519	Phase 2
0.6261	Remote Similarity	NPD6612	Phase 2
0.6261	Remote Similarity	NPD7309	Approved
0.6261	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD8053	Approved
0.6261	Remote Similarity	NPD8054	Approved
0.626	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD4237	Approved
0.6256	Remote Similarity	NPD4236	Phase 3
0.6255	Remote Similarity	NPD5566	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6568	Discontinued
0.625	Remote Similarity	NPD6494	Phase 2
0.625	Remote Similarity	NPD3349	Phase 2
0.625	Remote Similarity	NPD7243	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