NPASS Compound

Structure

NPC470821 OpenBabel07101719252D 37 43 0 0 1 0 0 0 0 0999 V2000 7.6369 2.8885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7629 3.3256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4189 -2.2352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0746 -2.5871 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6557 -1.9332 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5390 -1.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5678 1.2579 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2940 1.9118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5039 -0.4886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4192 1.5770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9294 0.3020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1875 0.6276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8463 -1.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6221 0.3020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8463 0.4886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7710 0.3020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2235 1.6098 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6927 -0.9773 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7004 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4267 0.6539 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7710 -1.2793 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8463 -1.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8213 2.3501 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6221 -1.2793 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9294 -1.2793 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6927 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1966 -0.4886 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.9773 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.7004 -0.9773 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.6927 -0.9773 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 3.4690 -2.2087 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8463 -2.4432 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7263 -2.2352 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3975 0.8928 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3007 0.2168 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8442 2.3647 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 16 1 0 0 0 0 8 17 1 0 0 0 0 9 11 1 0 0 0 0 9 25 1 0 0 0 0 10 12 2 0 0 0 0 10 23 1 0 0 0 0 11 31 1 0 0 0 0 12 36 1 0 0 0 0 13 18 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 19 2 0 0 0 0 16 27 1 0 0 0 0 17 20 2 0 0 0 0 17 37 1 0 0 0 0 18 24 1 0 0 0 0 18 26 1 6 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 32 1 0 0 0 0 22 28 1 0 0 0 0 22 30 1 0 0 0 0 22 33 2 0 0 0 0 23 37 1 0 0 0 0 24 27 1 0 0 0 0 25 28 1 1 0 0 0 25 34 1 0 0 0 0 26 30 1 1 0 0 0 27 14 1 1 0 0 0 28 13 1 6 0 0 0 28 31 1 0 0 0 0 31 35 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	509.25
Volume:	502.862
LogP:	2.038
LogD:	1.965
LogS:	-2.235
# Rotatable Bonds:	0
TPSA:	111.16
# H-Bond Aceptor:	9
# H-Bond Donor:	2
# Rings:	8
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.411
Synthetic Accessibility Score:	7.168
Fsp3:	0.643
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:	-5.309
MDCK Permeability:	2.016936741711106e-05
Pgp-inhibitor:	0.214
Pgp-substrate:	0.851
Human Intestinal Absorption (HIA):	0.888
20% Bioavailability (F20%):	0.989
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.432
Plasma Protein Binding (PPB):	58.371219635009766%
Volume Distribution (VD):	2.118
Pgp-substrate:	48.76722717285156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.12
CYP2C19-inhibitor:	0.039
CYP2C19-substrate:	0.908
CYP2C9-inhibitor:	0.234
CYP2C9-substrate:	0.331
CYP2D6-inhibitor:	0.023
CYP2D6-substrate:	0.127
CYP3A4-inhibitor:	0.597
CYP3A4-substrate:	0.958

ADMET: Excretion

Clearance (CL):	4.919
Half-life (T1/2):	0.896

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.618
Drug-inuced Liver Injury (DILI):	0.017
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.894
Maximum Recommended Daily Dose:	0.95
Skin Sensitization:	0.019
Carcinogencity:	0.975
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.579

Download Data

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

Natural Product: NPC470821

Natural Product ID:	NPC470821
*Common Name:**	N-Oxide Paraherquamide
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	IFVZXHLMGGKUOX-APYVQCPJSA-N
Standard InCHI:	InChI=1S/C28H35N3O6/c1-23(2)10-12-36-20-17(37-23)8-7-16-19(20)29-21(32)27(16)14-26-15-31(35)11-9-25(5,34)28(31,22(33)30(26)6)13-18(26)24(27,3)4/h7-8,10,12,18,34H,9,11,13-15H2,1-6H3,(H,29,32)/t18-,25+,26+,27+,28-,31?/m0/s1
SMILES:	CN1C(=O)[C@@]23C[C@@H]4[C@@]1(C[C@]1(C4(C)C)C(=Nc4c1ccc1c4OC=CC(O1)(C)C)O)CN3(=O)CC[C@@]2(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2252928
PubChem CID:	76315504
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
NPO23346	Penicillium cluniae	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16608209]
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	=	7.01	ug	PMID[449376]

☑ 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 NPC470821 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	417
0.1-0.2	1844
0.2-0.3	5919
0.3-0.4	12626
0.4-0.5	14722
0.5-0.6	6259
0.6-0.7	807
0.7-0.8	89
0.8-0.85	5
0.85-0.9	1
0.9-0.95	2
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9659	High Similarity	NPC266994
0.9565	High Similarity	NPC74216
0.9512	High Similarity	NPC250960
0.9512	High Similarity	NPC71539
0.8045	Intermediate Similarity	NPC37957
0.7917	Intermediate Similarity	NPC205926
0.7883	Intermediate Similarity	NPC153923
0.7844	Intermediate Similarity	NPC476651
0.7668	Intermediate Similarity	NPC470001
0.7668	Intermediate Similarity	NPC470002
0.7594	Intermediate Similarity	NPC204970
0.7535	Intermediate Similarity	NPC272706
0.7456	Intermediate Similarity	NPC318525
0.7456	Intermediate Similarity	NPC10653
0.7411	Intermediate Similarity	NPC471532
0.7399	Intermediate Similarity	NPC471561
0.7395	Intermediate Similarity	NPC49583
0.7336	Intermediate Similarity	NPC174629
0.7297	Intermediate Similarity	NPC473422
0.7277	Intermediate Similarity	NPC317709
0.7277	Intermediate Similarity	NPC329329
0.7257	Intermediate Similarity	NPC82541
0.7252	Intermediate Similarity	NPC473460
0.7225	Intermediate Similarity	NPC159815
0.7205	Intermediate Similarity	NPC471531
0.7198	Intermediate Similarity	NPC46259
0.7168	Intermediate Similarity	NPC477160
0.7143	Intermediate Similarity	NPC14339
0.7131	Intermediate Similarity	NPC477397
0.7097	Intermediate Similarity	NPC473008
0.7061	Intermediate Similarity	NPC477393
0.7051	Intermediate Similarity	NPC217294
0.7049	Intermediate Similarity	NPC477395
0.7039	Intermediate Similarity	NPC108826
0.7039	Intermediate Similarity	NPC219397
0.7032	Intermediate Similarity	NPC473004
0.7018	Intermediate Similarity	NPC168250
0.7004	Intermediate Similarity	NPC477396
0.7004	Intermediate Similarity	NPC476436
0.7	Intermediate Similarity	NPC10732
0.6991	Remote Similarity	NPC473007
0.6983	Remote Similarity	NPC291173
0.6982	Remote Similarity	NPC161804
0.6977	Remote Similarity	NPC98197
0.6975	Remote Similarity	NPC470480
0.6926	Remote Similarity	NPC470481
0.6926	Remote Similarity	NPC470482
0.6904	Remote Similarity	NPC248903
0.6904	Remote Similarity	NPC471513
0.6891	Remote Similarity	NPC231924
0.6889	Remote Similarity	NPC67904
0.6884	Remote Similarity	NPC39822
0.6878	Remote Similarity	NPC148124
0.6864	Remote Similarity	NPC476069
0.6862	Remote Similarity	NPC26928
0.686	Remote Similarity	NPC476429
0.6857	Remote Similarity	NPC470785
0.6853	Remote Similarity	NPC133609
0.6835	Remote Similarity	NPC99724
0.6828	Remote Similarity	NPC473005
0.682	Remote Similarity	NPC19175
0.6816	Remote Similarity	NPC230313
0.6816	Remote Similarity	NPC184680
0.6809	Remote Similarity	NPC195636
0.6789	Remote Similarity	NPC474183
0.6781	Remote Similarity	NPC127996
0.6771	Remote Similarity	NPC470485
0.6766	Remote Similarity	NPC234772
0.6765	Remote Similarity	NPC128476
0.6759	Remote Similarity	NPC189079
0.6758	Remote Similarity	NPC102760
0.6757	Remote Similarity	NPC28510
0.6754	Remote Similarity	NPC474077
0.6751	Remote Similarity	NPC222046
0.675	Remote Similarity	NPC477394
0.674	Remote Similarity	NPC127178
0.674	Remote Similarity	NPC138830
0.6739	Remote Similarity	NPC195787
0.6739	Remote Similarity	NPC246140
0.6727	Remote Similarity	NPC276120
0.6721	Remote Similarity	NPC470784
0.6712	Remote Similarity	NPC473569
0.6709	Remote Similarity	NPC77777
0.6698	Remote Similarity	NPC164608
0.6696	Remote Similarity	NPC163829
0.6696	Remote Similarity	NPC123859
0.6696	Remote Similarity	NPC470484
0.6696	Remote Similarity	NPC203972
0.6694	Remote Similarity	NPC473458
0.6682	Remote Similarity	NPC470483
0.6681	Remote Similarity	NPC288110
0.6681	Remote Similarity	NPC473006
0.6667	Remote Similarity	NPC126556
0.6667	Remote Similarity	NPC160113
0.6667	Remote Similarity	NPC476220
0.6667	Remote Similarity	NPC243626
0.6667	Remote Similarity	NPC158551
0.6651	Remote Similarity	NPC166169
0.664	Remote Similarity	NPC154922
0.6627	Remote Similarity	NPC469450
0.6627	Remote Similarity	NPC58209
0.6624	Remote Similarity	NPC269449
0.6581	Remote Similarity	NPC475133
0.6575	Remote Similarity	NPC32064
0.6574	Remote Similarity	NPC469451
0.6574	Remote Similarity	NPC469452
0.6564	Remote Similarity	NPC149962
0.6562	Remote Similarity	NPC29531
0.656	Remote Similarity	NPC476258
0.656	Remote Similarity	NPC304837
0.6543	Remote Similarity	NPC122886
0.6542	Remote Similarity	NPC475609
0.6535	Remote Similarity	NPC144314
0.6532	Remote Similarity	NPC138083
0.6532	Remote Similarity	NPC469460
0.653	Remote Similarity	NPC287152
0.6527	Remote Similarity	NPC313327
0.6524	Remote Similarity	NPC477161
0.6522	Remote Similarity	NPC329932
0.6522	Remote Similarity	NPC242728
0.652	Remote Similarity	NPC471563
0.6518	Remote Similarity	NPC230098
0.6508	Remote Similarity	NPC166712
0.6508	Remote Similarity	NPC113455
0.6507	Remote Similarity	NPC100863
0.6507	Remote Similarity	NPC50548
0.65	Remote Similarity	NPC474470
0.6498	Remote Similarity	NPC119722
0.6494	Remote Similarity	NPC469732
0.6489	Remote Similarity	NPC64140
0.6489	Remote Similarity	NPC174122
0.6483	Remote Similarity	NPC219664
0.6482	Remote Similarity	NPC160100
0.6481	Remote Similarity	NPC475147
0.6479	Remote Similarity	NPC59028
0.6479	Remote Similarity	NPC92191
0.6471	Remote Similarity	NPC270301
0.6466	Remote Similarity	NPC34770
0.6466	Remote Similarity	NPC311357
0.6463	Remote Similarity	NPC66909
0.6447	Remote Similarity	NPC59827
0.6447	Remote Similarity	NPC184933
0.6444	Remote Similarity	NPC314817
0.6444	Remote Similarity	NPC66191
0.6444	Remote Similarity	NPC316297
0.6444	Remote Similarity	NPC234069
0.6435	Remote Similarity	NPC293624
0.6432	Remote Similarity	NPC475326
0.6431	Remote Similarity	NPC120239
0.6429	Remote Similarity	NPC474746
0.6429	Remote Similarity	NPC262725
0.6429	Remote Similarity	NPC203168
0.6429	Remote Similarity	NPC475981
0.6423	Remote Similarity	NPC13249
0.6422	Remote Similarity	NPC298851
0.6422	Remote Similarity	NPC210415
0.6422	Remote Similarity	NPC266176
0.6422	Remote Similarity	NPC181138
0.6422	Remote Similarity	NPC82533
0.6422	Remote Similarity	NPC276993
0.6422	Remote Similarity	NPC293255
0.6422	Remote Similarity	NPC21752
0.6422	Remote Similarity	NPC158148
0.6422	Remote Similarity	NPC290759
0.6417	Remote Similarity	NPC188400
0.6416	Remote Similarity	NPC105055
0.6416	Remote Similarity	NPC22689
0.6413	Remote Similarity	NPC302235
0.641	Remote Similarity	NPC268077
0.64	Remote Similarity	NPC329731
0.64	Remote Similarity	NPC4910
0.6395	Remote Similarity	NPC475747
0.6395	Remote Similarity	NPC1464
0.6393	Remote Similarity	NPC470846
0.6391	Remote Similarity	NPC475559
0.639	Remote Similarity	NPC305984
0.6389	Remote Similarity	NPC131486
0.6389	Remote Similarity	NPC301501
0.6384	Remote Similarity	NPC315542
0.6378	Remote Similarity	NPC469722
0.6376	Remote Similarity	NPC284842
0.6375	Remote Similarity	NPC148391
0.6371	Remote Similarity	NPC223242
0.6368	Remote Similarity	NPC474745
0.6368	Remote Similarity	NPC207971
0.6367	Remote Similarity	NPC475565
0.6367	Remote Similarity	NPC475292
0.6367	Remote Similarity	NPC475349
0.6364	Remote Similarity	NPC57272
0.6364	Remote Similarity	NPC477527
0.6364	Remote Similarity	NPC477640
0.6364	Remote Similarity	NPC470739
0.6364	Remote Similarity	NPC87560
0.6364	Remote Similarity	NPC225597
0.6364	Remote Similarity	NPC71124
0.636	Remote Similarity	NPC196231
0.6359	Remote Similarity	NPC231198
0.6353	Remote Similarity	NPC208364
0.6352	Remote Similarity	NPC151470
0.6352	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 NPC470821 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	621
0.2-0.3	958
0.3-0.4	2394
0.4-0.5	3075
0.5-0.6	1648
0.6-0.7	223
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
0.7056	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD7048	Phase 3
0.6713	Remote Similarity	NPD5312	Approved
0.6713	Remote Similarity	NPD5313	Approved
0.6682	Remote Similarity	NPD6853	Approved
0.6682	Remote Similarity	NPD6851	Approved
0.6637	Remote Similarity	NPD2843	Phase 2
0.6637	Remote Similarity	NPD2845	Phase 2
0.6636	Remote Similarity	NPD7281	Phase 3
0.6636	Remote Similarity	NPD7280	Phase 3
0.6627	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD5645	Phase 3
0.6598	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD3592	Approved
0.6581	Remote Similarity	NPD3591	Approved
0.6564	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD6625	Approved
0.6555	Remote Similarity	NPD5562	Approved
0.6555	Remote Similarity	NPD5561	Approved
0.6549	Remote Similarity	NPD7125	Discontinued
0.6533	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD4206	Approved
0.6514	Remote Similarity	NPD4498	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD7559	Phase 2
0.65	Remote Similarity	NPD6297	Approved
0.6491	Remote Similarity	NPD5582	Discontinued
0.6481	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD3441	Approved
0.6478	Remote Similarity	NPD3442	Approved
0.6463	Remote Similarity	NPD2974	Approved
0.6463	Remote Similarity	NPD2973	Approved
0.6463	Remote Similarity	NPD2975	Approved
0.6462	Remote Similarity	NPD5773	Approved
0.6462	Remote Similarity	NPD5772	Approved
0.6461	Remote Similarity	NPD6997	Phase 2
0.646	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6459	Remote Similarity	NPD4210	Discontinued
0.6453	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD4885	Approved
0.645	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.645	Remote Similarity	NPD4580	Approved
0.6434	Remote Similarity	NPD7278	Phase 2
0.6434	Remote Similarity	NPD7279	Phase 2
0.6423	Remote Similarity	NPD8255	Phase 2
0.642	Remote Similarity	NPD7556	Discontinued
0.6414	Remote Similarity	NPD4846	Phase 2
0.6407	Remote Similarity	NPD7810	Phase 3
0.6407	Remote Similarity	NPD7811	Phase 3
0.6405	Remote Similarity	NPD2899	Discontinued
0.6395	Remote Similarity	NPD3106	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD5676	Approved
0.6383	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD4157	Discontinued
0.6372	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD7859	Phase 2
0.6367	Remote Similarity	NPD3912	Discontinued
0.6367	Remote Similarity	NPD7820	Phase 3
0.6367	Remote Similarity	NPD8359	Phase 2
0.6355	Remote Similarity	NPD5967	Approved
0.6355	Remote Similarity	NPD6063	Approved
0.6352	Remote Similarity	NPD6321	Discontinued
0.6352	Remote Similarity	NPD2493	Approved
0.6352	Remote Similarity	NPD2494	Approved
0.6352	Remote Similarity	NPD3450	Approved
0.6352	Remote Similarity	NPD3452	Approved
0.6349	Remote Similarity	NPD7047	Phase 3
0.6341	Remote Similarity	NPD7821	Clinical (unspecified phase)
0.634	Remote Similarity	NPD4583	Approved
0.634	Remote Similarity	NPD4582	Approved
0.634	Remote Similarity	NPD6644	Discontinued
0.633	Remote Similarity	NPD7315	Approved
0.633	Remote Similarity	NPD4166	Phase 2
0.633	Remote Similarity	NPD6071	Discontinued
0.6314	Remote Similarity	NPD8161	Suspended
0.6312	Remote Similarity	NPD7956	Approved
0.6312	Remote Similarity	NPD7955	Approved
0.6311	Remote Similarity	NPD3437	Discontinued
0.6308	Remote Similarity	NPD5294	Clinical (unspecified phase)
0.63	Remote Similarity	NPD7291	Discontinued
0.6298	Remote Similarity	NPD4004	Approved
0.6298	Remote Similarity	NPD4002	Approved
0.6296	Remote Similarity	NPD7684	Approved
0.6296	Remote Similarity	NPD7682	Approved
0.6293	Remote Similarity	NPD5071	Phase 2
0.6288	Remote Similarity	NPD7296	Approved
0.6286	Remote Similarity	NPD7805	Phase 3
0.6284	Remote Similarity	NPD6107	Approved
0.6281	Remote Similarity	NPD8149	Discontinued
0.6281	Remote Similarity	NPD5025	Approved
0.6276	Remote Similarity	NPD5726	Clinical (unspecified phase)
0.6274	Remote Similarity	NPD8461	Discontinued
0.6271	Remote Similarity	NPD4040	Phase 1
0.6267	Remote Similarity	NPD2971	Approved
0.6267	Remote Similarity	NPD2968	Approved
0.6266	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6245	Remote Similarity	NPD2490	Approved
0.6245	Remote Similarity	NPD2488	Approved
0.6233	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6223	Remote Similarity	NPD4420	Approved
0.622	Remote Similarity	NPD7907	Approved
0.6218	Remote Similarity	NPD7263	Phase 2
0.6215	Remote Similarity	NPD4773	Phase 2
0.6215	Remote Similarity	NPD4772	Phase 2
0.6208	Remote Similarity	NPD5914	Approved
0.6205	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD7891	Discontinued
0.6197	Remote Similarity	NPD6874	Approved
0.6194	Remote Similarity	NPD7803	Approved
0.6192	Remote Similarity	NPD2907	Approved
0.6192	Remote Similarity	NPD8027	Approved
0.6192	Remote Similarity	NPD2906	Approved
0.619	Remote Similarity	NPD3631	Phase 3
0.6189	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD5006	Approved
0.6186	Remote Similarity	NPD5005	Approved
0.618	Remote Similarity	NPD4605	Approved
0.618	Remote Similarity	NPD4604	Approved
0.6179	Remote Similarity	NPD3640	Phase 3
0.6179	Remote Similarity	NPD7131	Phase 3
0.6179	Remote Similarity	NPD3639	Approved
0.6179	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD3641	Approved
0.6178	Remote Similarity	NPD6104	Discontinued
0.617	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6157	Remote Similarity	NPD6982	Phase 2
0.6157	Remote Similarity	NPD7906	Approved
0.6157	Remote Similarity	NPD6668	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD2969	Approved
0.6154	Remote Similarity	NPD2216	Approved
0.6154	Remote Similarity	NPD2215	Approved
0.6154	Remote Similarity	NPD2970	Approved
0.6151	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.6151	Remote Similarity	NPD6296	Discontinued
0.6138	Remote Similarity	NPD4111	Phase 1
0.6138	Remote Similarity	NPD4665	Approved
0.6136	Remote Similarity	NPD8492	Approved
0.6129	Remote Similarity	NPD2560	Approved
0.6129	Remote Similarity	NPD2563	Approved
0.6126	Remote Similarity	NPD4481	Phase 3
0.6126	Remote Similarity	NPD2898	Approved
0.6125	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD6716	Phase 1
0.6123	Remote Similarity	NPD7311	Approved
0.6123	Remote Similarity	NPD7310	Approved
0.6123	Remote Similarity	NPD7313	Approved
0.6123	Remote Similarity	NPD7312	Approved
0.612	Remote Similarity	NPD7426	Phase 1
0.6118	Remote Similarity	NPD3057	Approved
0.6118	Remote Similarity	NPD3533	Approved
0.6118	Remote Similarity	NPD2972	Approved
0.6116	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD1769	Discontinued
0.6111	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6109	Remote Similarity	NPD3051	Approved
0.6106	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6104	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6103	Remote Similarity	NPD2122	Discontinued
0.6099	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6096	Remote Similarity	NPD6618	Phase 2
0.6096	Remote Similarity	NPD7309	Approved
0.6093	Remote Similarity	NPD5617	Suspended
0.6091	Remote Similarity	NPD7225	Discontinued
0.6087	Remote Similarity	NPD3398	Discontinued
0.6085	Remote Similarity	NPD4123	Phase 3
0.6083	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD7043	Discontinued
0.6079	Remote Similarity	NPD8460	Approved
0.6079	Remote Similarity	NPD8459	Approved
0.6076	Remote Similarity	NPD6238	Discontinued
0.6075	Remote Similarity	NPD4124	Clinical (unspecified phase)
0.6073	Remote Similarity	NPD5519	Discontinued
0.6073	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6073	Remote Similarity	NPD7831	Phase 2
0.6073	Remote Similarity	NPD7833	Phase 2
0.6065	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6065	Remote Similarity	NPD7110	Phase 1
0.6063	Remote Similarity	NPD7126	Discontinued
0.6062	Remote Similarity	NPD6878	Phase 2
0.6062	Remote Similarity	NPD6879	Phase 2
0.6062	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6059	Remote Similarity	NPD5547	Clinical (unspecified phase)
0.6056	Remote Similarity	NPD3263	Phase 3
0.6054	Remote Similarity	NPD2489	Approved
0.6054	Remote Similarity	NPD27	Approved
0.6053	Remote Similarity	NPD4577	Approved
0.6053	Remote Similarity	NPD4578	Approved
0.605	Remote Similarity	NPD2491	Approved
0.605	Remote Similarity	NPD956	Clinical (unspecified phase)
0.605	Remote Similarity	NPD3448	Approved
0.6049	Remote Similarity	NPD683	Approved
0.6049	Remote Similarity	NPD1945	Phase 1
0.6047	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD8016	Phase 3
0.6046	Remote Similarity	NPD8367	Approved
0.6045	Remote Similarity	NPD7708	Approved
0.6043	Remote Similarity	NPD4663	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