NPASS Compound

Structure

NPC266994 OpenBabel07101719132D 36 42 0 0 1 0 0 0 0 0999 V2000 7.6328 2.8869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7592 3.3238 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4176 -2.2340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0724 -2.5857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6548 -1.9321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5377 -1.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5659 1.2572 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2917 1.9108 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5031 -0.4884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4151 1.5761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9289 0.3018 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1836 0.6272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8459 -1.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6207 0.3018 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8459 0.4884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7689 0.3018 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2207 1.6090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6918 -0.9767 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.6979 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4237 0.6536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7689 -1.2786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8459 -1.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8176 2.3488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6207 -1.2786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9289 -1.2786 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6918 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1948 -0.4884 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.9767 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.6979 -0.9767 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.6918 -0.9767 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 3.4671 -2.2075 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8459 -2.4419 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7259 -2.2340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2973 0.2167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8410 2.3634 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 35 1 0 0 0 0 13 18 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 19 2 0 0 0 0 16 27 1 0 0 0 0 17 20 2 0 0 0 0 17 36 1 0 0 0 0 18 24 1 0 0 0 0 18 26 1 1 0 0 0 19 20 1 0 0 0 0 19 29 1 0 0 0 0 20 35 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 36 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 31 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	493.26
Volume:	494.071
LogP:	3.79
LogD:	2.623
LogS:	-4.67
# Rotatable Bonds:	0
TPSA:	91.34
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	8
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.578
Synthetic Accessibility Score:	6.819
Fsp3:	0.643
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.165
MDCK Permeability:	1.6542975572519936e-05
Pgp-inhibitor:	0.965
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.819
20% Bioavailability (F20%):	0.934
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.442
Plasma Protein Binding (PPB):	73.47588348388672%
Volume Distribution (VD):	1.896
Pgp-substrate:	37.39611053466797%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.437
CYP2C19-inhibitor:	0.195
CYP2C19-substrate:	0.933
CYP2C9-inhibitor:	0.665
CYP2C9-substrate:	0.454
CYP2D6-inhibitor:	0.271
CYP2D6-substrate:	0.173
CYP3A4-inhibitor:	0.938
CYP3A4-substrate:	0.956

ADMET: Excretion

Clearance (CL):	4.827
Half-life (T1/2):	0.439

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.836
Drug-inuced Liver Injury (DILI):	0.036
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.904
Maximum Recommended Daily Dose:	0.943
Skin Sensitization:	0.014
Carcinogencity:	0.978
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.59

Download Data

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

Natural Product: NPC266994

Natural Product ID:	NPC266994
*Common Name:**	Paraherquamide A
IUPAC Name:	n.a.
Synonyms:	Paraherquamide A
Standard InCHIKey:	UVZZDDLIOJPDKX-ZFXPIMNVSA-N
Standard InCHI:	InChI=1S/C28H35N3O5/c1-23(2)10-12-35-20-17(36-23)8-7-16-19(20)29-21(32)27(16)14-26-15-31-11-9-25(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+/m1/s1
SMILES:	CN1C(=O)[C@]23C[C@H]4[C@]1(CN2CC[C@@]3(C)O)C[C@]1(C4(C)C)C(=Nc2c1ccc1c2OC=CC(O1)(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2367904
PubChem CID:	26193229
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	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	LD50	<	15.0	mg.kg-1	PMID[451862]
NPT1016	Organism	Canis familiaris	Canis lupus familiaris	LD50	=	0.5	mg.kg-1	PMID[451862]
NPT2212	Organism	Oncopeltus fasciatus	Oncopeltus fasciatus	LD50	=	0.32	ug	PMID[451863]

☑ 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 NPC266994 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	403
0.1-0.2	1807
0.2-0.3	5542
0.3-0.4	12725
0.4-0.5	13925
0.5-0.6	7200
0.6-0.7	975
0.7-0.8	105
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	NPC74216
0.985	High Similarity	NPC71539
0.985	High Similarity	NPC250960
0.9659	High Similarity	NPC470821
0.8326	Intermediate Similarity	NPC37957
0.8199	Intermediate Similarity	NPC205926
0.8157	Intermediate Similarity	NPC153923
0.7874	Intermediate Similarity	NPC204970
0.781	Intermediate Similarity	NPC272706
0.7713	Intermediate Similarity	NPC318525
0.7713	Intermediate Similarity	NPC10653
0.7706	Intermediate Similarity	NPC476651
0.7639	Intermediate Similarity	NPC49583
0.7613	Intermediate Similarity	NPC470001
0.7613	Intermediate Similarity	NPC470002
0.7608	Intermediate Similarity	NPC174629
0.7558	Intermediate Similarity	NPC473422
0.7512	Intermediate Similarity	NPC473460
0.7511	Intermediate Similarity	NPC82541
0.7477	Intermediate Similarity	NPC159815
0.7445	Intermediate Similarity	NPC46259
0.7354	Intermediate Similarity	NPC471532
0.7342	Intermediate Similarity	NPC471561
0.7311	Intermediate Similarity	NPC217294
0.7292	Intermediate Similarity	NPC477393
0.7281	Intermediate Similarity	NPC108826
0.7281	Intermediate Similarity	NPC219397
0.728	Intermediate Similarity	NPC477395
0.7265	Intermediate Similarity	NPC168250
0.7265	Intermediate Similarity	NPC477160
0.7251	Intermediate Similarity	NPC473007
0.7244	Intermediate Similarity	NPC10732
0.7241	Intermediate Similarity	NPC476436
0.724	Intermediate Similarity	NPC14339
0.7238	Intermediate Similarity	NPC98197
0.7235	Intermediate Similarity	NPC161804
0.7231	Intermediate Similarity	NPC477396
0.7222	Intermediate Similarity	NPC477397
0.721	Intermediate Similarity	NPC470480
0.7196	Intermediate Similarity	NPC473008
0.7168	Intermediate Similarity	NPC470481
0.7168	Intermediate Similarity	NPC470482
0.7149	Intermediate Similarity	NPC471531
0.7143	Intermediate Similarity	NPC39822
0.7143	Intermediate Similarity	NPC291173
0.7137	Intermediate Similarity	NPC471513
0.7137	Intermediate Similarity	NPC248903
0.7136	Intermediate Similarity	NPC67904
0.713	Intermediate Similarity	NPC473004
0.7124	Intermediate Similarity	NPC231924
0.7112	Intermediate Similarity	NPC148124
0.7094	Intermediate Similarity	NPC26928
0.7089	Intermediate Similarity	NPC476429
0.7083	Intermediate Similarity	NPC470785
0.7073	Intermediate Similarity	NPC133609
0.7072	Intermediate Similarity	NPC473005
0.7069	Intermediate Similarity	NPC99724
0.7042	Intermediate Similarity	NPC184680
0.7026	Intermediate Similarity	NPC476069
0.7018	Intermediate Similarity	NPC127996
0.7018	Intermediate Similarity	NPC470485
0.7012	Intermediate Similarity	NPC474183
0.7005	Intermediate Similarity	NPC28510
0.7	Intermediate Similarity	NPC234772
0.6996	Remote Similarity	NPC474077
0.6991	Remote Similarity	NPC329329
0.6991	Remote Similarity	NPC317709
0.6983	Remote Similarity	NPC222046
0.6982	Remote Similarity	NPC138830
0.6982	Remote Similarity	NPC127178
0.6979	Remote Similarity	NPC19175
0.6977	Remote Similarity	NPC276120
0.6976	Remote Similarity	NPC189079
0.697	Remote Similarity	NPC195636
0.6959	Remote Similarity	NPC473569
0.6952	Remote Similarity	NPC164608
0.6942	Remote Similarity	NPC470784
0.6941	Remote Similarity	NPC203972
0.6937	Remote Similarity	NPC123859
0.6933	Remote Similarity	NPC163829
0.6933	Remote Similarity	NPC470484
0.693	Remote Similarity	NPC102760
0.6927	Remote Similarity	NPC470483
0.6923	Remote Similarity	NPC128476
0.692	Remote Similarity	NPC473458
0.691	Remote Similarity	NPC288110
0.6909	Remote Similarity	NPC230313
0.6903	Remote Similarity	NPC195787
0.6903	Remote Similarity	NPC246140
0.6903	Remote Similarity	NPC158551
0.6901	Remote Similarity	NPC166169
0.6888	Remote Similarity	NPC160113
0.6888	Remote Similarity	NPC476220
0.6867	Remote Similarity	NPC77777
0.686	Remote Similarity	NPC154922
0.6842	Remote Similarity	NPC58209
0.6835	Remote Similarity	NPC477394
0.6824	Remote Similarity	NPC126556
0.6822	Remote Similarity	NPC32064
0.6804	Remote Similarity	NPC29531
0.6802	Remote Similarity	NPC149962
0.6783	Remote Similarity	NPC269449
0.6776	Remote Similarity	NPC287152
0.6776	Remote Similarity	NPC304837
0.6776	Remote Similarity	NPC469450
0.6776	Remote Similarity	NPC476258
0.6774	Remote Similarity	NPC138083
0.6771	Remote Similarity	NPC144314
0.6767	Remote Similarity	NPC473006
0.6766	Remote Similarity	NPC475609
0.6765	Remote Similarity	NPC122886
0.6757	Remote Similarity	NPC471563
0.6757	Remote Similarity	NPC243626
0.6756	Remote Similarity	NPC242728
0.6752	Remote Similarity	NPC313327
0.6741	Remote Similarity	NPC100863
0.6741	Remote Similarity	NPC50548
0.6739	Remote Similarity	NPC475133
0.6727	Remote Similarity	NPC64140
0.6727	Remote Similarity	NPC174122
0.6721	Remote Similarity	NPC166712
0.6721	Remote Similarity	NPC113455
0.6721	Remote Similarity	NPC469451
0.6721	Remote Similarity	NPC469452
0.6713	Remote Similarity	NPC270301
0.671	Remote Similarity	NPC219664
0.6696	Remote Similarity	NPC66909
0.6696	Remote Similarity	NPC311357
0.6694	Remote Similarity	NPC160100
0.6682	Remote Similarity	NPC184933
0.6682	Remote Similarity	NPC230098
0.6682	Remote Similarity	NPC234069
0.6682	Remote Similarity	NPC59827
0.668	Remote Similarity	NPC34770
0.6667	Remote Similarity	NPC181138
0.6667	Remote Similarity	NPC329932
0.6667	Remote Similarity	NPC210415
0.6667	Remote Similarity	NPC21752
0.6667	Remote Similarity	NPC298851
0.6667	Remote Similarity	NPC262725
0.6667	Remote Similarity	NPC474470
0.6667	Remote Similarity	NPC276993
0.6667	Remote Similarity	NPC293255
0.6652	Remote Similarity	NPC203168
0.6652	Remote Similarity	NPC22689
0.6652	Remote Similarity	NPC105055
0.6652	Remote Similarity	NPC119722
0.6651	Remote Similarity	NPC302235
0.6651	Remote Similarity	NPC59028
0.6651	Remote Similarity	NPC92191
0.664	Remote Similarity	NPC120239
0.6639	Remote Similarity	NPC13249
0.6638	Remote Similarity	NPC268077
0.6638	Remote Similarity	NPC475147
0.6636	Remote Similarity	NPC329731
0.6636	Remote Similarity	NPC4910
0.6627	Remote Similarity	NPC188400
0.6623	Remote Similarity	NPC475747
0.6621	Remote Similarity	NPC315542
0.6611	Remote Similarity	NPC470846
0.661	Remote Similarity	NPC305984
0.6609	Remote Similarity	NPC477161
0.6599	Remote Similarity	NPC131486
0.6596	Remote Similarity	NPC314817
0.6596	Remote Similarity	NPC66191
0.6596	Remote Similarity	NPC316297
0.6596	Remote Similarity	NPC148391
0.6594	Remote Similarity	NPC207971
0.6593	Remote Similarity	NPC477527
0.6593	Remote Similarity	NPC293624
0.6593	Remote Similarity	NPC71124
0.6591	Remote Similarity	NPC475981
0.6591	Remote Similarity	NPC474746
0.659	Remote Similarity	NPC222524
0.6589	Remote Similarity	NPC158148
0.6589	Remote Similarity	NPC290759
0.6589	Remote Similarity	NPC82533
0.6589	Remote Similarity	NPC266176
0.6588	Remote Similarity	NPC52059
0.6588	Remote Similarity	NPC254700
0.6588	Remote Similarity	NPC470069
0.6583	Remote Similarity	NPC475349
0.6583	Remote Similarity	NPC475565
0.6583	Remote Similarity	NPC475292
0.6582	Remote Similarity	NPC87560
0.6579	Remote Similarity	NPC64576
0.6579	Remote Similarity	NPC254045
0.6579	Remote Similarity	NPC151470
0.6579	Remote Similarity	NPC201055
0.6578	Remote Similarity	NPC477258
0.6577	Remote Similarity	NPC208890
0.6577	Remote Similarity	NPC283207
0.6569	Remote Similarity	NPC76478
0.6564	Remote Similarity	NPC207239
0.6564	Remote Similarity	NPC267414
0.6561	Remote Similarity	NPC21425
0.656	Remote Similarity	NPC208364
0.6556	Remote Similarity	NPC475624
0.6555	Remote Similarity	NPC263709
0.6555	Remote Similarity	NPC310403

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 NPC266994 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	226
0.1-0.2	612
0.2-0.3	923
0.3-0.4	2337
0.4-0.5	3020
0.5-0.6	1758
0.6-0.7	273
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
0.7321	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD5312	Approved
0.6967	Remote Similarity	NPD5313	Approved
0.693	Remote Similarity	NPD6851	Approved
0.693	Remote Similarity	NPD6853	Approved
0.6884	Remote Similarity	NPD7281	Phase 3
0.6884	Remote Similarity	NPD7280	Phase 3
0.6881	Remote Similarity	NPD2845	Phase 2
0.6881	Remote Similarity	NPD2843	Phase 2
0.6856	Remote Similarity	NPD5645	Phase 3
0.6844	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD7048	Phase 3
0.6812	Remote Similarity	NPD3591	Approved
0.6812	Remote Similarity	NPD3592	Approved
0.6802	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD5561	Approved
0.6781	Remote Similarity	NPD5562	Approved
0.6777	Remote Similarity	NPD6625	Approved
0.6773	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD4498	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD4206	Approved
0.6744	Remote Similarity	NPD6297	Approved
0.6738	Remote Similarity	NPD7559	Phase 2
0.6726	Remote Similarity	NPD5582	Discontinued
0.6716	Remote Similarity	NPD4210	Discontinued
0.6715	Remote Similarity	NPD5773	Approved
0.6715	Remote Similarity	NPD5772	Approved
0.6711	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD2973	Approved
0.6696	Remote Similarity	NPD2974	Approved
0.6696	Remote Similarity	NPD2975	Approved
0.6694	Remote Similarity	NPD3442	Approved
0.6694	Remote Similarity	NPD3441	Approved
0.6681	Remote Similarity	NPD6997	Phase 2
0.6681	Remote Similarity	NPD4580	Approved
0.6681	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4885	Approved
0.6653	Remote Similarity	NPD7278	Phase 2
0.6653	Remote Similarity	NPD7279	Phase 2
0.6637	Remote Similarity	NPD7811	Phase 3
0.6637	Remote Similarity	NPD7810	Phase 3
0.6637	Remote Similarity	NPD7125	Discontinued
0.6627	Remote Similarity	NPD8255	Phase 2
0.6626	Remote Similarity	NPD4846	Phase 2
0.6624	Remote Similarity	NPD2899	Discontinued
0.6623	Remote Similarity	NPD3106	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD4157	Discontinued
0.6606	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD6063	Approved
0.6603	Remote Similarity	NPD5967	Approved
0.6583	Remote Similarity	NPD7820	Phase 3
0.6579	Remote Similarity	NPD2494	Approved
0.6579	Remote Similarity	NPD3452	Approved
0.6579	Remote Similarity	NPD2493	Approved
0.6579	Remote Similarity	NPD6321	Discontinued
0.6579	Remote Similarity	NPD3450	Approved
0.6575	Remote Similarity	NPD7859	Phase 2
0.6574	Remote Similarity	NPD8359	Phase 2
0.6573	Remote Similarity	NPD7315	Approved
0.6573	Remote Similarity	NPD4166	Phase 2
0.6568	Remote Similarity	NPD7047	Phase 3
0.6565	Remote Similarity	NPD6644	Discontinued
0.6565	Remote Similarity	NPD4582	Approved
0.6565	Remote Similarity	NPD4583	Approved
0.6556	Remote Similarity	NPD7821	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD5294	Clinical (unspecified phase)
0.6537	Remote Similarity	NPD8161	Suspended
0.6532	Remote Similarity	NPD7291	Discontinued
0.6526	Remote Similarity	NPD6107	Approved
0.6522	Remote Similarity	NPD4004	Approved
0.6522	Remote Similarity	NPD4002	Approved
0.652	Remote Similarity	NPD5071	Phase 2
0.6518	Remote Similarity	NPD7296	Approved
0.6512	Remote Similarity	NPD7955	Approved
0.6512	Remote Similarity	NPD7956	Approved
0.65	Remote Similarity	NPD7805	Phase 3
0.65	Remote Similarity	NPD2968	Approved
0.65	Remote Similarity	NPD2971	Approved
0.6498	Remote Similarity	NPD8149	Discontinued
0.6498	Remote Similarity	NPD5025	Approved
0.6495	Remote Similarity	NPD6071	Discontinued
0.6494	Remote Similarity	NPD4040	Phase 1
0.6483	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD2490	Approved
0.6473	Remote Similarity	NPD2488	Approved
0.6459	Remote Similarity	NPD4773	Phase 2
0.6459	Remote Similarity	NPD4772	Phase 2
0.6447	Remote Similarity	NPD4420	Approved
0.6446	Remote Similarity	NPD3912	Discontinued
0.6438	Remote Similarity	NPD7263	Phase 2
0.6438	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD3640	Phase 3
0.6425	Remote Similarity	NPD7131	Phase 3
0.6425	Remote Similarity	NPD3639	Approved
0.6425	Remote Similarity	NPD3641	Approved
0.6419	Remote Similarity	NPD6874	Approved
0.6416	Remote Similarity	NPD3631	Phase 3
0.641	Remote Similarity	NPD8027	Approved
0.641	Remote Similarity	NPD2906	Approved
0.641	Remote Similarity	NPD2907	Approved
0.6409	Remote Similarity	NPD8461	Discontinued
0.6409	Remote Similarity	NPD6104	Discontinued
0.6407	Remote Similarity	NPD5006	Approved
0.6407	Remote Similarity	NPD5005	Approved
0.6404	Remote Similarity	NPD4605	Approved
0.6404	Remote Similarity	NPD4604	Approved
0.6402	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD5676	Approved
0.6398	Remote Similarity	NPD6668	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.639	Remote Similarity	NPD3437	Discontinued
0.639	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD2215	Approved
0.6389	Remote Similarity	NPD2216	Approved
0.6388	Remote Similarity	NPD7803	Approved
0.6384	Remote Similarity	NPD7906	Approved
0.6364	Remote Similarity	NPD7556	Discontinued
0.636	Remote Similarity	NPD6982	Phase 2
0.6356	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD1769	Discontinued
0.6347	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD2122	Discontinued
0.6343	Remote Similarity	NPD3051	Approved
0.634	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD5617	Suspended
0.6332	Remote Similarity	NPD8492	Approved
0.633	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD4123	Phase 3
0.6327	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD7426	Phase 1
0.6324	Remote Similarity	NPD6716	Phase 1
0.6323	Remote Similarity	NPD6618	Phase 2
0.6321	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD4124	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD2969	Approved
0.6313	Remote Similarity	NPD2970	Approved
0.6308	Remote Similarity	NPD7831	Phase 2
0.6308	Remote Similarity	NPD7833	Phase 2
0.6308	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD7225	Discontinued
0.6303	Remote Similarity	NPD7110	Phase 1
0.6303	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD7043	Discontinued
0.6296	Remote Similarity	NPD7907	Approved
0.6296	Remote Similarity	NPD7126	Discontinued
0.6293	Remote Similarity	NPD6238	Discontinued
0.6291	Remote Similarity	NPD2563	Approved
0.6291	Remote Similarity	NPD2560	Approved
0.629	Remote Similarity	NPD6879	Phase 2
0.629	Remote Similarity	NPD6878	Phase 2
0.629	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD4481	Phase 3
0.6284	Remote Similarity	NPD2898	Approved
0.6283	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6278	Remote Similarity	NPD4577	Approved
0.6278	Remote Similarity	NPD4578	Approved
0.6277	Remote Similarity	NPD5547	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD4663	Approved
0.6267	Remote Similarity	NPD7608	Discontinued
0.6266	Remote Similarity	NPD956	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD8460	Approved
0.6264	Remote Similarity	NPD8459	Approved
0.6261	Remote Similarity	NPD683	Approved
0.6261	Remote Similarity	NPD1945	Phase 1
0.626	Remote Similarity	NPD3263	Phase 3
0.6256	Remote Similarity	NPD6505	Approved
0.6256	Remote Similarity	NPD2161	Phase 2
0.6256	Remote Similarity	NPD6504	Approved
0.6256	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5677	Discontinued
0.625	Remote Similarity	NPD2904	Discontinued
0.625	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6519	Phase 2
0.6245	Remote Similarity	NPD5566	Clinical (unspecified phase)
0.6245	Remote Similarity	NPD8016	Phase 3
0.6245	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD5557	Phase 1
0.6244	Remote Similarity	NPD4237	Approved
0.6244	Remote Similarity	NPD4236	Phase 3
0.624	Remote Similarity	NPD6568	Discontinued
0.624	Remote Similarity	NPD8367	Approved
0.6239	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD7497	Discontinued
0.6236	Remote Similarity	NPD7708	Approved
0.6234	Remote Similarity	NPD7178	Clinical (unspecified phase)
0.6234	Remote Similarity	NPD6877	Discontinued
0.6228	Remote Similarity	NPD3633	Approved
0.6228	Remote Similarity	NPD3634	Approved
0.6227	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6223	Remote Similarity	NPD7566	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