NPASS Compound

Structure

NPC473052 OpenBabel07101718312D 27 28 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 -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 -1.4781 -0.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1045 -0.9945 0.0000 C 0 0 2 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 0.9706 -1.4945 0.0000 C 0 0 2 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 0.9706 -2.4945 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 12 1 0 0 0 0 7 9 1 0 0 0 0 7 14 2 0 0 0 0 8 10 2 0 0 0 0 8 14 1 0 0 0 0 9 15 2 0 0 0 0 10 15 1 0 0 0 0 11 12 1 0 0 0 0 11 13 1 0 0 0 0 12 2 1 1 0 0 0 13 3 1 1 0 0 0 13 18 1 0 0 0 0 14 19 1 0 0 0 0 15 23 1 0 0 0 0 16 18 2 0 0 0 0 16 20 1 0 0 0 0 16 21 1 0 0 0 0 17 19 1 6 0 0 0 17 20 1 0 0 0 0 17 22 1 0 0 0 0 18 24 1 0 0 0 0 19 25 1 1 0 0 0 20 26 2 0 0 0 0 21 22 2 0 0 0 0 21 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	373.19
Volume:	391.152
LogP:	3.111
LogD:	2.035
LogS:	-4.06
# Rotatable Bonds:	8
TPSA:	113.78
# H-Bond Aceptor:	6
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.354
Synthetic Accessibility Score:	4.148
Fsp3:	0.381
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.88
MDCK Permeability:	4.416067895363085e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.026
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.939
30% Bioavailability (F30%):	0.847

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.021
Plasma Protein Binding (PPB):	99.71397399902344%
Volume Distribution (VD):	0.259
Pgp-substrate:	0.7541162371635437%

ADMET: Metabolism

CYP1A2-inhibitor:	0.398
CYP1A2-substrate:	0.832
CYP2C19-inhibitor:	0.361
CYP2C19-substrate:	0.096
CYP2C9-inhibitor:	0.881
CYP2C9-substrate:	0.962
CYP2D6-inhibitor:	0.939
CYP2D6-substrate:	0.676
CYP3A4-inhibitor:	0.528
CYP3A4-substrate:	0.521

ADMET: Excretion

Clearance (CL):	2.812
Half-life (T1/2):	0.836

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.308
Drug-inuced Liver Injury (DILI):	0.809
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.34
Maximum Recommended Daily Dose:	0.927
Skin Sensitization:	0.135
Carcinogencity:	0.054
Eye Corrosion:	0.003
Eye Irritation:	0.065
Respiratory Toxicity:	0.9

Download Data

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

Natural Product: NPC473052

Natural Product ID:	NPC473052
*Common Name:**	IWIISBMWNKBQQH-OMBQEDPYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	IWIISBMWNKBQQH-OMBQEDPYSA-N
Standard InCHI:	InChI=1S/C21H27NO5/c1-4-5-6-12(2)11-13(3)18(24)16-20(26)17(22-21(16)27)19(25)14-7-9-15(23)10-8-14/h4-5,7-10,12-13,17,19,23-25H,6,11H2,1-3H3,(H,22,27)/b5-4-,18-16-/t12-,13-,17+,19+/m0/s1
SMILES:	CC=CCC(C)CC(C)C(=C1C(=O)C(NC1=O)C(C2=CC=C(C=C2)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3608612
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[538468]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[538468]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	40000.0	nM	PMID[538468]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	40000.0	nM	PMID[538468]

☑ 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 NPC473052 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	157
0.1-0.2	773
0.2-0.3	3438
0.3-0.4	11164
0.4-0.5	8230
0.5-0.6	14636
0.6-0.7	4078
0.7-0.8	199
0.8-0.85	14
0.85-0.9	1
0.9-0.95	2
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473055
0.9922	High Similarity	NPC322526
0.9688	High Similarity	NPC328070
0.9323	High Similarity	NPC471201
0.8514	High Similarity	NPC476194
0.837	Intermediate Similarity	NPC296712
0.8333	Intermediate Similarity	NPC474862
0.8309	Intermediate Similarity	NPC478147
0.8258	Intermediate Similarity	NPC473051
0.8258	Intermediate Similarity	NPC473050
0.8112	Intermediate Similarity	NPC91953
0.8106	Intermediate Similarity	NPC319950
0.8042	Intermediate Similarity	NPC197921
0.8029	Intermediate Similarity	NPC476353
0.7986	Intermediate Similarity	NPC469360
0.7929	Intermediate Similarity	NPC45191
0.7926	Intermediate Similarity	NPC142577
0.7832	Intermediate Similarity	NPC6570
0.7812	Intermediate Similarity	NPC317305
0.7803	Intermediate Similarity	NPC317254
0.7794	Intermediate Similarity	NPC27581
0.7786	Intermediate Similarity	NPC325651
0.7746	Intermediate Similarity	NPC244866
0.7727	Intermediate Similarity	NPC285350
0.7714	Intermediate Similarity	NPC116057
0.7692	Intermediate Similarity	NPC474149
0.7692	Intermediate Similarity	NPC169766
0.7677	Intermediate Similarity	NPC471203
0.7676	Intermediate Similarity	NPC326966
0.7669	Intermediate Similarity	NPC23402
0.7669	Intermediate Similarity	NPC188010
0.7647	Intermediate Similarity	NPC190663
0.7634	Intermediate Similarity	NPC177576
0.7622	Intermediate Similarity	NPC470392
0.7619	Intermediate Similarity	NPC251439
0.7594	Intermediate Similarity	NPC118202
0.7589	Intermediate Similarity	NPC472413
0.7586	Intermediate Similarity	NPC208725
0.7574	Intermediate Similarity	NPC283760
0.7557	Intermediate Similarity	NPC252544
0.7557	Intermediate Similarity	NPC321252
0.7554	Intermediate Similarity	NPC307020
0.7551	Intermediate Similarity	NPC150712
0.7536	Intermediate Similarity	NPC160493
0.7519	Intermediate Similarity	NPC231705
0.7518	Intermediate Similarity	NPC80150
0.7517	Intermediate Similarity	NPC473360
0.7484	Intermediate Similarity	NPC15506
0.7481	Intermediate Similarity	NPC106551
0.7481	Intermediate Similarity	NPC281686
0.7481	Intermediate Similarity	NPC258056
0.7481	Intermediate Similarity	NPC188867
0.7468	Intermediate Similarity	NPC39431
0.7467	Intermediate Similarity	NPC473804
0.7466	Intermediate Similarity	NPC64205
0.7466	Intermediate Similarity	NPC6913
0.7462	Intermediate Similarity	NPC142297
0.7447	Intermediate Similarity	NPC29477
0.7426	Intermediate Similarity	NPC311737
0.7426	Intermediate Similarity	NPC38458
0.7419	Intermediate Similarity	NPC244509
0.7417	Intermediate Similarity	NPC16188
0.7417	Intermediate Similarity	NPC119569
0.741	Intermediate Similarity	NPC268348
0.7405	Intermediate Similarity	NPC156348
0.7394	Intermediate Similarity	NPC305717
0.7386	Intermediate Similarity	NPC473491
0.7376	Intermediate Similarity	NPC95733
0.7376	Intermediate Similarity	NPC62101
0.7375	Intermediate Similarity	NPC71205
0.7372	Intermediate Similarity	NPC249435
0.7355	Intermediate Similarity	NPC68967
0.7353	Intermediate Similarity	NPC82963
0.7351	Intermediate Similarity	NPC81026
0.7348	Intermediate Similarity	NPC290566
0.7348	Intermediate Similarity	NPC145638
0.7319	Intermediate Similarity	NPC239697
0.7301	Intermediate Similarity	NPC328494
0.7297	Intermediate Similarity	NPC242159
0.7297	Intermediate Similarity	NPC313694
0.729	Intermediate Similarity	NPC262166
0.7287	Intermediate Similarity	NPC178902
0.7285	Intermediate Similarity	NPC266741
0.7284	Intermediate Similarity	NPC101207
0.7279	Intermediate Similarity	NPC10286
0.7279	Intermediate Similarity	NPC213
0.7278	Intermediate Similarity	NPC244336
0.7273	Intermediate Similarity	NPC24101
0.7273	Intermediate Similarity	NPC153690
0.7273	Intermediate Similarity	NPC96224
0.7266	Intermediate Similarity	NPC478015
0.7266	Intermediate Similarity	NPC478016
0.7266	Intermediate Similarity	NPC478014
0.7254	Intermediate Similarity	NPC472414
0.7254	Intermediate Similarity	NPC474803
0.7252	Intermediate Similarity	NPC70843
0.7241	Intermediate Similarity	NPC183722
0.7241	Intermediate Similarity	NPC120251
0.7239	Intermediate Similarity	NPC114682
0.7234	Intermediate Similarity	NPC86900
0.7234	Intermediate Similarity	NPC472415
0.723	Intermediate Similarity	NPC109580
0.7226	Intermediate Similarity	NPC233702
0.7218	Intermediate Similarity	NPC88141
0.7214	Intermediate Similarity	NPC56634
0.7211	Intermediate Similarity	NPC477680
0.7208	Intermediate Similarity	NPC132771
0.7208	Intermediate Similarity	NPC476444
0.7197	Intermediate Similarity	NPC476268
0.7194	Intermediate Similarity	NPC182240
0.7192	Intermediate Similarity	NPC257390
0.7183	Intermediate Similarity	NPC211218
0.7181	Intermediate Similarity	NPC236795
0.7179	Intermediate Similarity	NPC202198
0.7172	Intermediate Similarity	NPC469930
0.7161	Intermediate Similarity	NPC324081
0.7152	Intermediate Similarity	NPC33011
0.7143	Intermediate Similarity	NPC475042
0.7143	Intermediate Similarity	NPC67080
0.7143	Intermediate Similarity	NPC265454
0.7143	Intermediate Similarity	NPC34634
0.7134	Intermediate Similarity	NPC314693
0.7133	Intermediate Similarity	NPC471316
0.7133	Intermediate Similarity	NPC4974
0.7133	Intermediate Similarity	NPC171372
0.7132	Intermediate Similarity	NPC309808
0.7122	Intermediate Similarity	NPC5932
0.7122	Intermediate Similarity	NPC142638
0.7122	Intermediate Similarity	NPC317784
0.7121	Intermediate Similarity	NPC69332
0.7121	Intermediate Similarity	NPC29989
0.7121	Intermediate Similarity	NPC95178
0.7121	Intermediate Similarity	NPC188677
0.7117	Intermediate Similarity	NPC209463
0.7113	Intermediate Similarity	NPC469927
0.7109	Intermediate Similarity	NPC260000
0.7108	Intermediate Similarity	NPC26108
0.7108	Intermediate Similarity	NPC136797
0.7107	Intermediate Similarity	NPC56635
0.7103	Intermediate Similarity	NPC71271
0.7101	Intermediate Similarity	NPC28951
0.7101	Intermediate Similarity	NPC325646
0.7099	Intermediate Similarity	NPC261573
0.7099	Intermediate Similarity	NPC8931
0.7099	Intermediate Similarity	NPC63931
0.7099	Intermediate Similarity	NPC120693
0.7097	Intermediate Similarity	NPC227905
0.7097	Intermediate Similarity	NPC339338
0.7097	Intermediate Similarity	NPC146097
0.7092	Intermediate Similarity	NPC98305
0.7092	Intermediate Similarity	NPC326079
0.7092	Intermediate Similarity	NPC86966
0.7092	Intermediate Similarity	NPC149246
0.709	Intermediate Similarity	NPC95172
0.7089	Intermediate Similarity	NPC256689
0.7089	Intermediate Similarity	NPC123011
0.7086	Intermediate Similarity	NPC476989
0.7083	Intermediate Similarity	NPC127975
0.7075	Intermediate Similarity	NPC42423
0.7071	Intermediate Similarity	NPC473767
0.7071	Intermediate Similarity	NPC43275
0.707	Intermediate Similarity	NPC56685
0.7068	Intermediate Similarity	NPC228737
0.7066	Intermediate Similarity	NPC211713
0.7066	Intermediate Similarity	NPC88378
0.7063	Intermediate Similarity	NPC65761
0.7063	Intermediate Similarity	NPC472029
0.7059	Intermediate Similarity	NPC17693
0.7054	Intermediate Similarity	NPC280869
0.705	Intermediate Similarity	NPC121259
0.7048	Intermediate Similarity	NPC306804
0.7048	Intermediate Similarity	NPC12890
0.7048	Intermediate Similarity	NPC137627
0.7048	Intermediate Similarity	NPC54661
0.7048	Intermediate Similarity	NPC163924
0.7047	Intermediate Similarity	NPC213485
0.7047	Intermediate Similarity	NPC279045
0.7047	Intermediate Similarity	NPC139074
0.7047	Intermediate Similarity	NPC113325
0.7047	Intermediate Similarity	NPC40524
0.7045	Intermediate Similarity	NPC211551
0.7042	Intermediate Similarity	NPC196976
0.7042	Intermediate Similarity	NPC31936
0.7039	Intermediate Similarity	NPC168861
0.7034	Intermediate Similarity	NPC110211
0.7032	Intermediate Similarity	NPC313414
0.7027	Intermediate Similarity	NPC88667
0.7021	Intermediate Similarity	NPC294037
0.7021	Intermediate Similarity	NPC112823
0.702	Intermediate Similarity	NPC41473
0.702	Intermediate Similarity	NPC160607
0.702	Intermediate Similarity	NPC204848
0.702	Intermediate Similarity	NPC312770
0.702	Intermediate Similarity	NPC14600
0.702	Intermediate Similarity	NPC471283
0.702	Intermediate Similarity	NPC48202
0.7015	Intermediate Similarity	NPC31274
0.7012	Intermediate Similarity	NPC294516
0.7012	Intermediate Similarity	NPC107938
0.7007	Intermediate Similarity	NPC214246

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 NPC473052 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	117
0.1-0.2	471
0.2-0.3	948
0.3-0.4	1979
0.4-0.5	2864
0.5-0.6	2190
0.6-0.7	545
0.7-0.8	35
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8116	Intermediate Similarity	NPD3136	Phase 2
0.7945	Intermediate Similarity	NPD3400	Discontinued
0.7746	Intermediate Similarity	NPD5729	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD7978	Discontinued
0.7554	Intermediate Similarity	NPD4659	Approved
0.75	Intermediate Similarity	NPD1759	Phase 1
0.7481	Intermediate Similarity	NPD9568	Approved
0.7432	Intermediate Similarity	NPD7450	Phase 2
0.7432	Intermediate Similarity	NPD9570	Approved
0.7426	Intermediate Similarity	NPD318	Approved
0.7426	Intermediate Similarity	NPD317	Approved
0.7426	Intermediate Similarity	NPD1758	Phase 1
0.7407	Intermediate Similarity	NPD256	Approved
0.7407	Intermediate Similarity	NPD255	Approved
0.7357	Intermediate Similarity	NPD2561	Approved
0.7357	Intermediate Similarity	NPD2562	Approved
0.7348	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD4103	Phase 2
0.732	Intermediate Similarity	NPD6682	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD16	Approved
0.7299	Intermediate Similarity	NPD856	Approved
0.7297	Intermediate Similarity	NPD3553	Approved
0.7297	Intermediate Similarity	NPD3554	Approved
0.7297	Intermediate Similarity	NPD3555	Approved
0.7297	Intermediate Similarity	NPD3552	Approved
0.7266	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD7972	Discontinued
0.7226	Intermediate Similarity	NPD6390	Discontinued
0.7219	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD6325	Discontinued
0.7133	Intermediate Similarity	NPD6867	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD6866	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD5035	Approved
0.7113	Intermediate Similarity	NPD5108	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD3123	Discovery
0.7083	Intermediate Similarity	NPD1135	Approved
0.7083	Intermediate Similarity	NPD1131	Approved
0.7083	Intermediate Similarity	NPD1133	Approved
0.7083	Intermediate Similarity	NPD1134	Approved
0.7083	Intermediate Similarity	NPD1129	Approved
0.707	Intermediate Similarity	NPD7523	Phase 3
0.707	Intermediate Similarity	NPD7131	Phase 3
0.7063	Intermediate Similarity	NPD7495	Discontinued
0.7047	Intermediate Similarity	NPD555	Phase 2
0.7034	Intermediate Similarity	NPD7451	Discontinued
0.7027	Intermediate Similarity	NPD259	Phase 1
0.7007	Intermediate Similarity	NPD2234	Approved
0.7007	Intermediate Similarity	NPD2228	Approved
0.7007	Intermediate Similarity	NPD2229	Approved
0.6986	Remote Similarity	NPD9569	Approved
0.698	Remote Similarity	NPD825	Approved
0.698	Remote Similarity	NPD826	Approved
0.697	Remote Similarity	NPD9610	Approved
0.697	Remote Similarity	NPD9608	Approved
0.6959	Remote Similarity	NPD4954	Approved
0.6959	Remote Similarity	NPD5026	Approved
0.6959	Remote Similarity	NPD5028	Approved
0.6959	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD4955	Approved
0.6959	Remote Similarity	NPD5034	Approved
0.6959	Remote Similarity	NPD36	Approved
0.6957	Remote Similarity	NPD9618	Approved
0.6957	Remote Similarity	NPD9614	Approved
0.6944	Remote Similarity	NPD5157	Phase 1
0.6944	Remote Similarity	NPD5159	Phase 2
0.6944	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD9622	Approved
0.6918	Remote Similarity	NPD258	Approved
0.6918	Remote Similarity	NPD257	Approved
0.6901	Remote Similarity	NPD5030	Phase 2
0.6897	Remote Similarity	NPD196	Phase 1
0.6897	Remote Similarity	NPD5037	Approved
0.6897	Remote Similarity	NPD5038	Approved
0.6887	Remote Similarity	NPD2568	Approved
0.6875	Remote Similarity	NPD3455	Phase 2
0.6867	Remote Similarity	NPD468	Phase 1
0.6863	Remote Similarity	NPD2161	Phase 2
0.6859	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD3421	Phase 3
0.6852	Remote Similarity	NPD8019	Approved
0.6846	Remote Similarity	NPD601	Approved
0.6846	Remote Similarity	NPD597	Approved
0.6846	Remote Similarity	NPD598	Approved
0.6842	Remote Similarity	NPD3823	Discontinued
0.6839	Remote Similarity	NPD5036	Approved
0.6828	Remote Similarity	NPD1755	Approved
0.6828	Remote Similarity	NPD3685	Discontinued
0.6807	Remote Similarity	NPD6746	Phase 2
0.68	Remote Similarity	NPD1130	Approved
0.68	Remote Similarity	NPD6407	Approved
0.68	Remote Similarity	NPD6405	Approved
0.68	Remote Similarity	NPD1132	Approved
0.68	Remote Similarity	NPD1136	Approved
0.6788	Remote Similarity	NPD3643	Approved
0.6788	Remote Similarity	NPD3642	Approved
0.6788	Remote Similarity	NPD3644	Approved
0.6786	Remote Similarity	NPD5137	Approved
0.6784	Remote Similarity	NPD5557	Phase 1
0.6783	Remote Similarity	NPD9384	Approved
0.6783	Remote Similarity	NPD9381	Approved
0.6779	Remote Similarity	NPD4738	Phase 2
0.6779	Remote Similarity	NPD9537	Phase 1
0.6779	Remote Similarity	NPD9536	Phase 1
0.6776	Remote Similarity	NPD3052	Approved
0.6776	Remote Similarity	NPD3054	Approved
0.6765	Remote Similarity	NPD3909	Discontinued
0.6763	Remote Similarity	NPD5032	Approved
0.6761	Remote Similarity	NPD2218	Phase 2
0.6761	Remote Similarity	NPD5304	Approved
0.6761	Remote Similarity	NPD2217	Approved
0.6761	Remote Similarity	NPD5303	Approved
0.6755	Remote Similarity	NPD6346	Approved
0.6741	Remote Similarity	NPD1445	Approved
0.6741	Remote Similarity	NPD1444	Approved
0.6731	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD6502	Phase 2
0.6726	Remote Similarity	NPD7315	Approved
0.6711	Remote Similarity	NPD2613	Approved
0.6705	Remote Similarity	NPD5029	Approved
0.6705	Remote Similarity	NPD5027	Approved
0.6705	Remote Similarity	NPD5031	Approved
0.6692	Remote Similarity	NPD854	Approved
0.6692	Remote Similarity	NPD855	Approved
0.669	Remote Similarity	NPD9616	Approved
0.669	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.669	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.669	Remote Similarity	NPD9615	Approved
0.669	Remote Similarity	NPD9613	Approved
0.6689	Remote Similarity	NPD9619	Approved
0.6689	Remote Similarity	NPD829	Discontinued
0.6689	Remote Similarity	NPD9621	Approved
0.6689	Remote Similarity	NPD602	Approved
0.6689	Remote Similarity	NPD9620	Approved
0.6689	Remote Similarity	NPD599	Approved
0.6687	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3286	Discontinued
0.6667	Remote Similarity	NPD8172	Phase 2
0.6667	Remote Similarity	NPD4357	Discontinued
0.6667	Remote Similarity	NPD8173	Phase 2
0.6667	Remote Similarity	NPD817	Approved
0.6667	Remote Similarity	NPD3019	Approved
0.6667	Remote Similarity	NPD823	Approved
0.6667	Remote Similarity	NPD2932	Approved
0.6648	Remote Similarity	NPD5968	Phase 3
0.6646	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD3059	Approved
0.6645	Remote Similarity	NPD2240	Approved
0.6645	Remote Similarity	NPD3061	Approved
0.6645	Remote Similarity	NPD3062	Approved
0.6645	Remote Similarity	NPD2239	Approved
0.6644	Remote Similarity	NPD4208	Discontinued
0.6643	Remote Similarity	NPD316	Approved
0.6643	Remote Similarity	NPD9545	Approved
0.6629	Remote Similarity	NPD6836	Approved
0.6627	Remote Similarity	NPD7608	Discontinued
0.6625	Remote Similarity	NPD3536	Discontinued
0.6624	Remote Similarity	NPD2654	Approved
0.6621	Remote Similarity	NPD3143	Discontinued
0.6612	Remote Similarity	NPD7811	Phase 3
0.6612	Remote Similarity	NPD7810	Phase 3
0.6604	Remote Similarity	NPD3300	Phase 2
0.6604	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD274	Approved
0.6601	Remote Similarity	NPD275	Approved
0.66	Remote Similarity	NPD4207	Discontinued
0.6597	Remote Similarity	NPD5981	Approved
0.6597	Remote Similarity	NPD4093	Discontinued
0.6594	Remote Similarity	NPD1792	Phase 2
0.6591	Remote Similarity	NPD9611	Approved
0.6591	Remote Similarity	NPD9609	Approved
0.6591	Remote Similarity	NPD9612	Approved
0.659	Remote Similarity	NPD4956	Approved
0.6582	Remote Similarity	NPD2575	Approved
0.6579	Remote Similarity	NPD5745	Approved
0.6579	Remote Similarity	NPD3615	Approved
0.6579	Remote Similarity	NPD4746	Phase 3
0.6579	Remote Similarity	NPD3614	Approved
0.6579	Remote Similarity	NPD840	Approved
0.6579	Remote Similarity	NPD520	Approved
0.6579	Remote Similarity	NPD3616	Approved
0.6579	Remote Similarity	NPD3088	Approved
0.6579	Remote Similarity	NPD3087	Approved
0.6579	Remote Similarity	NPD3090	Approved
0.6579	Remote Similarity	NPD2573	Approved
0.6579	Remote Similarity	NPD2570	Approved
0.6579	Remote Similarity	NPD2566	Approved
0.6579	Remote Similarity	NPD4745	Approved
0.6579	Remote Similarity	NPD2574	Discontinued
0.6579	Remote Similarity	NPD839	Approved
0.6579	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD2674	Phase 3
0.6579	Remote Similarity	NPD3089	Approved
0.6579	Remote Similarity	NPD2571	Approved
0.6577	Remote Similarity	NPD858	Approved
0.6577	Remote Similarity	NPD859	Approved
0.6575	Remote Similarity	NPD4215	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