NPASS Compound

Structure

NPC473051 OpenBabel07101718312D 26 27 0 0 1 0 0 0 0 0999 V2000 4.0996 -4.4168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6929 -3.5033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2916 -2.4852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0941 -4.5214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6819 -3.7123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2752 -2.7988 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 -1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8366 0.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5686 -0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 0.5055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8739 -1.7807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 -1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2807 -2.6943 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8794 -1.6762 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8366 -0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5686 0.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1045 -0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4781 -0.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4727 -0.7626 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 -1.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 0.2079 0.0000 C 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 -4.4347 0.5055 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0605 0.0464 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0169 -2.3794 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3849 1.1215 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 4 5 2 0 0 0 0 5 6 1 0 0 0 0 6 13 1 0 0 0 0 7 9 1 0 0 0 0 7 15 2 0 0 0 0 8 10 2 0 0 0 0 8 15 1 0 0 0 0 9 16 2 0 0 0 0 10 16 1 0 0 0 0 11 13 1 0 0 0 0 11 14 1 0 0 0 0 12 15 1 0 0 0 0 12 17 2 0 0 0 0 13 2 1 6 0 0 0 14 3 1 6 0 0 0 14 19 1 0 0 0 0 16 23 1 0 0 0 0 17 20 1 0 0 0 0 17 22 1 0 0 0 0 18 19 2 0 0 0 0 18 20 1 0 0 0 0 18 21 1 0 0 0 0 19 24 1 0 0 0 0 20 25 2 0 0 0 0 21 22 2 0 0 0 0 21 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	355.18
Volume:	379.725
LogP:	4.028
LogD:	2.579
LogS:	-3.656
# Rotatable Bonds:	7
TPSA:	93.55
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.436
Synthetic Accessibility Score:	3.835
Fsp3:	0.286
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:	-4.754
MDCK Permeability:	1.0718857993197162e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.964
30% Bioavailability (F30%):	0.961

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	100.65522003173828%
Volume Distribution (VD):	0.17
Pgp-substrate:	0.583113431930542%

ADMET: Metabolism

CYP1A2-inhibitor:	0.588
CYP1A2-substrate:	0.822
CYP2C19-inhibitor:	0.788
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.918
CYP2C9-substrate:	0.962
CYP2D6-inhibitor:	0.946
CYP2D6-substrate:	0.837
CYP3A4-inhibitor:	0.802
CYP3A4-substrate:	0.53

ADMET: Excretion

Clearance (CL):	4.568
Half-life (T1/2):	0.895

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.622
Drug-inuced Liver Injury (DILI):	0.972
AMES Toxicity:	0.031
Rat Oral Acute Toxicity:	0.31
Maximum Recommended Daily Dose:	0.019
Skin Sensitization:	0.233
Carcinogencity:	0.097
Eye Corrosion:	0.003
Eye Irritation:	0.045
Respiratory Toxicity:	0.86

Download Data

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

Natural Product: NPC473051

Natural Product ID:	NPC473051
*Common Name:**	OXQLEPRTPVNYJU-VANYGJKFSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	OXQLEPRTPVNYJU-VANYGJKFSA-N
Standard InCHI:	InChI=1S/C21H25NO4/c1-4-5-6-13(2)11-14(3)19(24)18-20(25)17(22-21(18)26)12-15-7-9-16(23)10-8-15/h4-5,7-10,12-14,23-24H,6,11H2,1-3H3,(H,22,26)/b5-4-,17-12-,19-18-/t13-,14-/m0/s1
SMILES:	C/C=CC[C@@H](C[C@@H](/C(=C1/C(=N/C(=Cc2ccc(cc2)O)/C1=O)O)/O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3608611
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0004646] 1-hydroxy-2-unsubstituted benzenoids

*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
NPO4374	Tolypocladium cylindrosporum	Species	Ophiocordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26356746]

☑ 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
IC50	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	40000.0	nM	PMID[567401]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[567401]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	40000.0	nM	PMID[567401]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	40000.0	nM	PMID[567401]

☑ 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 NPC473051 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	163
0.1-0.2	1708
0.2-0.3	6337
0.3-0.4	11084
0.4-0.5	9819
0.5-0.6	11728
0.6-0.7	1771
0.7-0.8	75
0.8-0.85	9
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473050
0.8516	High Similarity	NPC328070
0.8258	Intermediate Similarity	NPC473055
0.8258	Intermediate Similarity	NPC473052
0.8195	Intermediate Similarity	NPC322526
0.7926	Intermediate Similarity	NPC471201
0.777	Intermediate Similarity	NPC473804
0.7731	Intermediate Similarity	NPC231705
0.7714	Intermediate Similarity	NPC119569
0.7699	Intermediate Similarity	NPC181709
0.7672	Intermediate Similarity	NPC130193
0.7667	Intermediate Similarity	NPC142297
0.7627	Intermediate Similarity	NPC68269
0.7623	Intermediate Similarity	NPC474149
0.7609	Intermediate Similarity	NPC106688
0.76	Intermediate Similarity	NPC317254
0.7597	Intermediate Similarity	NPC474862
0.7594	Intermediate Similarity	NPC478147
0.7586	Intermediate Similarity	NPC201967
0.7542	Intermediate Similarity	NPC472585
0.7541	Intermediate Similarity	NPC258056
0.7479	Intermediate Similarity	NPC178902
0.746	Intermediate Similarity	NPC37302
0.7459	Intermediate Similarity	NPC24101
0.7459	Intermediate Similarity	NPC96224
0.7402	Intermediate Similarity	NPC258992
0.7388	Intermediate Similarity	NPC296712
0.7381	Intermediate Similarity	NPC118202
0.7372	Intermediate Similarity	NPC169766
0.7368	Intermediate Similarity	NPC476249
0.7364	Intermediate Similarity	NPC283760
0.7364	Intermediate Similarity	NPC319950
0.7339	Intermediate Similarity	NPC222905
0.7328	Intermediate Similarity	NPC81010
0.7328	Intermediate Similarity	NPC268348
0.7328	Intermediate Similarity	NPC32977
0.7323	Intermediate Similarity	NPC23402
0.7317	Intermediate Similarity	NPC153690
0.7295	Intermediate Similarity	NPC95178
0.7295	Intermediate Similarity	NPC70843
0.7295	Intermediate Similarity	NPC69332
0.7295	Intermediate Similarity	NPC29989
0.7288	Intermediate Similarity	NPC107619
0.728	Intermediate Similarity	NPC227553
0.728	Intermediate Similarity	NPC163674
0.7265	Intermediate Similarity	NPC286006
0.7258	Intermediate Similarity	NPC88141
0.7244	Intermediate Similarity	NPC285350
0.7226	Intermediate Similarity	NPC326966
0.7209	Intermediate Similarity	NPC311737
0.7209	Intermediate Similarity	NPC38458
0.7197	Intermediate Similarity	NPC142577
0.7194	Intermediate Similarity	NPC470441
0.719	Intermediate Similarity	NPC135784
0.7177	Intermediate Similarity	NPC317305
0.7176	Intermediate Similarity	NPC41801
0.7167	Intermediate Similarity	NPC253746
0.7165	Intermediate Similarity	NPC309808
0.7163	Intermediate Similarity	NPC471283
0.7155	Intermediate Similarity	NPC270547
0.7154	Intermediate Similarity	NPC6984
0.7143	Intermediate Similarity	NPC166837
0.7143	Intermediate Similarity	NPC470355
0.7143	Intermediate Similarity	NPC260000
0.7132	Intermediate Similarity	NPC82963
0.7131	Intermediate Similarity	NPC79672
0.7131	Intermediate Similarity	NPC52087
0.713	Intermediate Similarity	NPC177420
0.713	Intermediate Similarity	NPC280347
0.713	Intermediate Similarity	NPC98772
0.7121	Intermediate Similarity	NPC83279
0.712	Intermediate Similarity	NPC95172
0.7105	Intermediate Similarity	NPC184169
0.7101	Intermediate Similarity	NPC45191
0.7097	Intermediate Similarity	NPC226699
0.7092	Intermediate Similarity	NPC236795
0.7087	Intermediate Similarity	NPC51698
0.7087	Intermediate Similarity	NPC17693
0.7083	Intermediate Similarity	NPC280869
0.708	Intermediate Similarity	NPC325651
0.708	Intermediate Similarity	NPC248817
0.7073	Intermediate Similarity	NPC303141
0.7073	Intermediate Similarity	NPC243677
0.7069	Intermediate Similarity	NPC55561
0.7068	Intermediate Similarity	NPC27581
0.7063	Intermediate Similarity	NPC116842
0.7059	Intermediate Similarity	NPC473388
0.7059	Intermediate Similarity	NPC476353
0.7054	Intermediate Similarity	NPC303370
0.705	Intermediate Similarity	NPC244866
0.7049	Intermediate Similarity	NPC304638
0.7045	Intermediate Similarity	NPC252817
0.7043	Intermediate Similarity	NPC25493
0.7043	Intermediate Similarity	NPC113460
0.704	Intermediate Similarity	NPC224584
0.7039	Intermediate Similarity	NPC103250
0.7039	Intermediate Similarity	NPC476194
0.7025	Intermediate Similarity	NPC289381
0.7025	Intermediate Similarity	NPC155847
0.7023	Intermediate Similarity	NPC122009
0.7021	Intermediate Similarity	NPC6570
0.7018	Intermediate Similarity	NPC197783
0.7016	Intermediate Similarity	NPC188677
0.7008	Intermediate Similarity	NPC177576
0.7008	Intermediate Similarity	NPC297657
0.7008	Intermediate Similarity	NPC114682
0.7	Intermediate Similarity	NPC325646
0.7	Intermediate Similarity	NPC140619
0.7	Intermediate Similarity	NPC28951
0.6993	Remote Similarity	NPC197921
0.6992	Remote Similarity	NPC120693
0.6992	Remote Similarity	NPC8931
0.6992	Remote Similarity	NPC261573
0.6991	Remote Similarity	NPC265146
0.6991	Remote Similarity	NPC124436
0.6984	Remote Similarity	NPC79543
0.6983	Remote Similarity	NPC242240
0.6983	Remote Similarity	NPC318325
0.6983	Remote Similarity	NPC258219
0.6983	Remote Similarity	NPC123273
0.6975	Remote Similarity	NPC26244
0.6975	Remote Similarity	NPC257182
0.6975	Remote Similarity	NPC246679
0.697	Remote Similarity	NPC43275
0.697	Remote Similarity	NPC268572
0.696	Remote Similarity	NPC260952
0.696	Remote Similarity	NPC228737
0.6957	Remote Similarity	NPC23167
0.6947	Remote Similarity	NPC283468
0.6947	Remote Similarity	NPC323948
0.6944	Remote Similarity	NPC91953
0.6944	Remote Similarity	NPC469360
0.6935	Remote Similarity	NPC127676
0.6934	Remote Similarity	NPC305717
0.693	Remote Similarity	NPC175313
0.6929	Remote Similarity	NPC471535
0.6929	Remote Similarity	NPC321252
0.6929	Remote Similarity	NPC252544
0.6929	Remote Similarity	NPC21162
0.6929	Remote Similarity	NPC471953
0.6929	Remote Similarity	NPC183700
0.6923	Remote Similarity	NPC322197
0.6923	Remote Similarity	NPC249899
0.6918	Remote Similarity	NPC323798
0.6917	Remote Similarity	NPC283711
0.6917	Remote Similarity	NPC82664
0.6917	Remote Similarity	NPC216520
0.6917	Remote Similarity	NPC292730
0.6917	Remote Similarity	NPC132271
0.6911	Remote Similarity	NPC470202
0.6906	Remote Similarity	NPC120251
0.6905	Remote Similarity	NPC17525
0.6905	Remote Similarity	NPC470039
0.6899	Remote Similarity	NPC242136
0.6897	Remote Similarity	NPC104216
0.6894	Remote Similarity	NPC5932
0.6894	Remote Similarity	NPC249435
0.6892	Remote Similarity	NPC2672
0.6891	Remote Similarity	NPC151715
0.688	Remote Similarity	NPC1786
0.688	Remote Similarity	NPC294902
0.688	Remote Similarity	NPC1075
0.6875	Remote Similarity	NPC228609
0.6875	Remote Similarity	NPC139946
0.6875	Remote Similarity	NPC476989
0.687	Remote Similarity	NPC61062
0.687	Remote Similarity	NPC299252
0.687	Remote Similarity	NPC19290
0.687	Remote Similarity	NPC277394
0.6866	Remote Similarity	NPC86966
0.6864	Remote Similarity	NPC304541
0.686	Remote Similarity	NPC315921
0.6859	Remote Similarity	NPC71205
0.685	Remote Similarity	NPC98392
0.685	Remote Similarity	NPC75272
0.685	Remote Similarity	NPC471954
0.6846	Remote Similarity	NPC142599
0.6846	Remote Similarity	NPC473491
0.6842	Remote Similarity	NPC256369
0.6829	Remote Similarity	NPC94343
0.6825	Remote Similarity	NPC34715
0.6822	Remote Similarity	NPC231717
0.6818	Remote Similarity	NPC471203
0.6818	Remote Similarity	NPC269414
0.6807	Remote Similarity	NPC325292
0.6807	Remote Similarity	NPC138117
0.6803	Remote Similarity	NPC171843
0.6803	Remote Similarity	NPC245561
0.6803	Remote Similarity	NPC125732
0.68	Remote Similarity	NPC13495
0.6797	Remote Similarity	NPC208229
0.6794	Remote Similarity	NPC296526
0.6794	Remote Similarity	NPC474967
0.6791	Remote Similarity	NPC112823
0.6788	Remote Similarity	NPC171372
0.6783	Remote Similarity	NPC138365
0.6783	Remote Similarity	NPC6913
0.678	Remote Similarity	NPC300017
0.678	Remote Similarity	NPC151764
0.6776	Remote Similarity	NPC244509

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 NPC473051 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	132
0.1-0.2	640
0.2-0.3	944
0.3-0.4	2216
0.4-0.5	3260
0.5-0.6	1762
0.6-0.7	192
0.7-0.8	4
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
0.7279	Intermediate Similarity	NPD3136	Phase 2
0.7174	Intermediate Similarity	NPD5729	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD1759	Phase 1
0.7122	Intermediate Similarity	NPD468	Phase 1
0.7077	Intermediate Similarity	NPD1758	Phase 1
0.7034	Intermediate Similarity	NPD2934	Approved
0.7034	Intermediate Similarity	NPD2933	Approved
0.7007	Intermediate Similarity	NPD4357	Discontinued
0.6991	Remote Similarity	NPD111	Approved
0.6975	Remote Similarity	NPD2859	Approved
0.6975	Remote Similarity	NPD2860	Approved
0.6944	Remote Similarity	NPD7978	Discontinued
0.6942	Remote Similarity	NPD3020	Approved
0.6923	Remote Similarity	NPD256	Approved
0.6923	Remote Similarity	NPD255	Approved
0.6918	Remote Similarity	NPD5481	Discontinued
0.6899	Remote Similarity	NPD2234	Approved
0.6899	Remote Similarity	NPD2229	Approved
0.6899	Remote Similarity	NPD2228	Approved
0.6866	Remote Similarity	NPD3421	Phase 3
0.6866	Remote Similarity	NPD3143	Discontinued
0.686	Remote Similarity	NPD9273	Approved
0.6855	Remote Similarity	NPD9610	Approved
0.6855	Remote Similarity	NPD9608	Approved
0.6838	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD7451	Discontinued
0.6806	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD3070	Discontinued
0.6759	Remote Similarity	NPD7450	Phase 2
0.675	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD1445	Approved
0.6746	Remote Similarity	NPD1444	Approved
0.6742	Remote Similarity	NPD9568	Approved
0.6693	Remote Similarity	NPD9507	Approved
0.6667	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD6346	Approved
0.6643	Remote Similarity	NPD4208	Discontinued
0.6643	Remote Similarity	NPD4993	Discontinued
0.6642	Remote Similarity	NPD5303	Approved
0.6642	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD5304	Approved
0.662	Remote Similarity	NPD3145	Approved
0.662	Remote Similarity	NPD3144	Approved
0.6614	Remote Similarity	NPD3134	Approved
0.66	Remote Similarity	NPD3281	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD4207	Discontinued
0.6594	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD475	Phase 2
0.6589	Remote Similarity	NPD3021	Approved
0.6589	Remote Similarity	NPD1792	Phase 2
0.6589	Remote Similarity	NPD3022	Approved
0.6565	Remote Similarity	NPD821	Approved
0.6562	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.656	Remote Similarity	NPD940	Approved
0.656	Remote Similarity	NPD846	Approved
0.6558	Remote Similarity	NPD5811	Approved
0.6547	Remote Similarity	NPD6325	Discontinued
0.6544	Remote Similarity	NPD3019	Approved
0.6544	Remote Similarity	NPD2932	Approved
0.6544	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD9712	Approved
0.6529	Remote Similarity	NPD845	Approved
0.6512	Remote Similarity	NPD9266	Approved
0.6512	Remote Similarity	NPD74	Approved
0.6493	Remote Similarity	NPD9493	Approved
0.6475	Remote Similarity	NPD4659	Approved
0.6471	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4093	Discontinued
0.6467	Remote Similarity	NPD3400	Discontinued
0.6462	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD2674	Phase 3
0.6458	Remote Similarity	NPD3058	Clinical (unspecified phase)
0.6454	Remote Similarity	NPD258	Approved
0.6454	Remote Similarity	NPD257	Approved
0.6452	Remote Similarity	NPD9711	Approved
0.6452	Remote Similarity	NPD9710	Approved
0.6444	Remote Similarity	NPD16	Approved
0.6444	Remote Similarity	NPD856	Approved
0.6444	Remote Similarity	NPD318	Approved
0.6444	Remote Similarity	NPD317	Approved
0.6434	Remote Similarity	NPD2372	Approved
0.6434	Remote Similarity	NPD9267	Approved
0.6434	Remote Similarity	NPD9263	Approved
0.6434	Remote Similarity	NPD1358	Approved
0.6434	Remote Similarity	NPD9264	Approved
0.6433	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7523	Phase 3
0.6423	Remote Similarity	NPD844	Approved
0.6423	Remote Similarity	NPD1809	Phase 2
0.6419	Remote Similarity	NPD2161	Phase 2
0.641	Remote Similarity	NPD5617	Suspended
0.6408	Remote Similarity	NPD4212	Discontinued
0.6403	Remote Similarity	NPD2562	Approved
0.6403	Remote Similarity	NPD6624	Discontinued
0.6403	Remote Similarity	NPD2561	Approved
0.6397	Remote Similarity	NPD9545	Approved
0.6397	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD6636	Phase 3
0.6382	Remote Similarity	NPD3300	Phase 2
0.6377	Remote Similarity	NPD3847	Discontinued
0.6377	Remote Similarity	NPD1980	Approved
0.6377	Remote Similarity	NPD1983	Approved
0.6377	Remote Similarity	NPD1981	Approved
0.6371	Remote Similarity	NPD288	Approved
0.637	Remote Similarity	NPD3123	Discovery
0.637	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.637	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6390	Discontinued
0.6364	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD1196	Approved
0.6357	Remote Similarity	NPD3685	Discontinued
0.6357	Remote Similarity	NPD1755	Approved
0.6349	Remote Similarity	NPD3028	Approved
0.6349	Remote Similarity	NPD1242	Phase 1
0.6346	Remote Similarity	NPD3866	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD3111	Phase 1
0.6333	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD5536	Phase 2
0.6316	Remote Similarity	NPD9379	Approved
0.6316	Remote Similarity	NPD9377	Approved
0.6312	Remote Similarity	NPD3125	Approved
0.6311	Remote Similarity	NPD159	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD1751	Approved
0.6304	Remote Similarity	NPD2667	Approved
0.6304	Remote Similarity	NPD2668	Approved
0.6301	Remote Similarity	NPD825	Approved
0.6301	Remote Similarity	NPD826	Approved
0.6299	Remote Similarity	NPD5556	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD9342	Approved
0.6294	Remote Similarity	NPD9569	Approved
0.6291	Remote Similarity	NPD1195	Approved
0.6289	Remote Similarity	NPD7972	Discontinued
0.6284	Remote Similarity	NPD9279	Approved
0.6284	Remote Similarity	NPD3552	Approved
0.6284	Remote Similarity	NPD3554	Approved
0.6284	Remote Similarity	NPD3555	Approved
0.6284	Remote Similarity	NPD3553	Approved
0.6282	Remote Similarity	NPD4003	Phase 3
0.6276	Remote Similarity	NPD1048	Approved
0.6268	Remote Similarity	NPD4103	Phase 2
0.6268	Remote Similarity	NPD3053	Approved
0.6268	Remote Similarity	NPD3055	Approved
0.6268	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD7083	Clinical (unspecified phase)
0.6266	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.6266	Remote Similarity	NPD2366	Approved
0.6258	Remote Similarity	NPD2888	Approved
0.6258	Remote Similarity	NPD2017	Approved
0.6258	Remote Similarity	NPD2821	Approved
0.6258	Remote Similarity	NPD2889	Approved
0.6258	Remote Similarity	NPD7303	Discontinued
0.6258	Remote Similarity	NPD3286	Discontinued
0.6258	Remote Similarity	NPD2890	Approved
0.625	Remote Similarity	NPD682	Discontinued
0.6242	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6234	Remote Similarity	NPD1543	Discontinued
0.6233	Remote Similarity	NPD259	Phase 1
0.6233	Remote Similarity	NPD520	Approved
0.6232	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD7495	Discontinued
0.6222	Remote Similarity	NPD1793	Approved
0.6222	Remote Similarity	NPD1791	Approved
0.6222	Remote Similarity	NPD9614	Approved
0.6222	Remote Similarity	NPD9281	Approved
0.6222	Remote Similarity	NPD9618	Approved
0.622	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD7131	Phase 3
0.6216	Remote Similarity	NPD2157	Approved
0.6216	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.62	Remote Similarity	NPD5712	Approved
0.6197	Remote Similarity	NPD3098	Discontinued
0.6187	Remote Similarity	NPD1362	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD6406	Approved
0.6181	Remote Similarity	NPD3637	Approved
0.6181	Remote Similarity	NPD3636	Approved
0.6181	Remote Similarity	NPD1712	Approved
0.6181	Remote Similarity	NPD3635	Approved
0.617	Remote Similarity	NPD9717	Approved
0.617	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6164	Remote Similarity	NPD2789	Approved
0.6159	Remote Similarity	NPD6809	Clinical (unspecified phase)
0.6159	Remote Similarity	NPD3091	Approved
0.6154	Remote Similarity	NPD1131	Approved
0.6154	Remote Similarity	NPD1134	Approved
0.6154	Remote Similarity	NPD5445	Approved
0.6154	Remote Similarity	NPD9509	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD1129	Approved
0.6154	Remote Similarity	NPD1164	Approved
0.6154	Remote Similarity	NPD1040	Phase 2
0.6154	Remote Similarity	NPD1133	Approved
0.6154	Remote Similarity	NPD1470	Approved
0.6154	Remote Similarity	NPD1135	Approved
0.6149	Remote Similarity	NPD275	Approved
0.6149	Remote Similarity	NPD555	Phase 2
0.6149	Remote Similarity	NPD274	Approved
0.6148	Remote Similarity	NPD1241	Discontinued

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