NPASS Compound

Structure

CID318028 OpenBabel06191716142D 22 23 0 0 1 0 0 0 0 0999 V2000 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 I 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 I 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 2 0 0 0 0 1 8 1 0 0 0 0 2 3 2 0 0 0 0 2 9 1 0 0 0 0 3 13 1 0 0 0 0 4 14 1 0 0 0 0 5 8 2 0 0 0 0 5 11 1 0 0 0 0 6 8 1 0 0 0 0 6 12 1 0 0 0 0 7 9 2 0 0 0 0 7 10 1 0 0 0 0 9 22 1 0 0 0 0 10 13 2 0 0 0 0 10 16 1 0 0 0 0 11 14 2 0 0 0 0 11 17 1 0 0 0 0 12 15 1 0 0 0 0 12 18 1 0 0 0 0 13 19 1 0 0 0 0 14 22 1 0 0 0 0 15 20 2 0 0 0 0 15 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	524.89
Volume:	329.139
LogP:	2.702
LogD:	2.056
LogS:	-2.778
# Rotatable Bonds:	5
TPSA:	92.78
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.522
Synthetic Accessibility Score:	2.874
Fsp3:	0.133
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:	-4.828
MDCK Permeability:	1.6916985259740613e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.034
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.021
Plasma Protein Binding (PPB):	95.87047576904297%
Volume Distribution (VD):	0.26
Pgp-substrate:	2.6706788539886475%

ADMET: Metabolism

CYP1A2-inhibitor:	0.465
CYP1A2-substrate:	0.095
CYP2C19-inhibitor:	0.077
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.229
CYP2C9-substrate:	0.334
CYP2D6-inhibitor:	0.544
CYP2D6-substrate:	0.505
CYP3A4-inhibitor:	0.106
CYP3A4-substrate:	0.177

ADMET: Excretion

Clearance (CL):	6.292
Half-life (T1/2):	0.803

ADMET: Toxicity

hERG Blockers:	0.246
Human Hepatotoxicity (H-HT):	0.363
Drug-inuced Liver Injury (DILI):	0.016
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.638
Maximum Recommended Daily Dose:	0.748
Skin Sensitization:	0.67
Carcinogencity:	0.131
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.732

Download Data

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

Natural Product: NPC318028

Natural Product ID:	NPC318028
*Common Name:**	Diiodothyronine
IUPAC Name:	2-amino-3-[4-(4-hydroxy-3-iodophenoxy)-3-iodophenyl]propanoic acid
Synonyms:	Di-Iodothyronine
Standard InCHIKey:	CPCJBZABTUOGNM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H13I2NO4/c16-10-7-9(2-3-13(10)19)22-14-4-1-8(5-11(14)17)6-12(18)15(20)21/h1-5,7,12,19H,6,18H2,(H,20,21)
SMILES:	C1=CC(=C(C=C1CC(C(=O)O)N)I)OC2=CC(=C(C=C2)O)I
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1743303
PubChem CID:	65559 58185737
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino acids and derivatives [CHEMONTID:0004321] Phenylalanine and 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
NPO12323	Bos taurus	Species	Bovidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24211545]
NPO12323	Bos taurus	Species	Bovidae	Eukaryota	Urine	n.a.	n.a.	PMID[6330305]
NPO12323	Bos taurus	Species	Bovidae	Eukaryota	n.a.	n.a.	n.a.	PMID[932730]
NPO12323	Bos taurus	Species	Bovidae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO12323	Bos taurus	Species	Bovidae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO12323	Bos taurus	Species	Bovidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17393	Bubalus bubalis	Species	Bovidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17393	Bubalus bubalis	Species	Bovidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12323	Bos taurus	Species	Bovidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17393	Bubalus bubalis	Species	Bovidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12323	Bos taurus	Species	Bovidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12323	Bos taurus	Species	Bovidae	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
Others	6

Activity Type	# Activity
Organism	2
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		RBA	=	0.688	%	PMID[448210]
NPT2	Others	Unspecified		log(%)	=	-0.162	n.a.	PMID[448210]
NPT2	Others	Unspecified		log(%)	=	-0.301	n.a.	PMID[448210]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	0.056	%	PMID[448210]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	log(%)	=	-1.252	n.a.	PMID[448210]
NPT2	Others	Unspecified		RBA	=	0.5	%	PMID[448210]

☑ 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 NPC318028 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	241
0.1-0.2	1669
0.2-0.3	6389
0.3-0.4	11962
0.4-0.5	4790
0.5-0.6	12550
0.6-0.7	4988
0.7-0.8	89
0.8-0.85	8
0.85-0.9	2
0.9-0.95	0
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC317741
1.0	High Similarity	NPC328137
1.0	High Similarity	NPC259800
1.0	High Similarity	NPC282087
1.0	High Similarity	NPC318984
1.0	High Similarity	NPC241086
0.9847	High Similarity	NPC326860
0.9847	High Similarity	NPC197239
0.8692	High Similarity	NPC318357
0.8601	High Similarity	NPC17760
0.8538	High Similarity	NPC239697
0.8462	Intermediate Similarity	NPC317784
0.8462	Intermediate Similarity	NPC142638
0.8308	Intermediate Similarity	NPC188867
0.8308	Intermediate Similarity	NPC281686
0.8308	Intermediate Similarity	NPC106551
0.8143	Intermediate Similarity	NPC470392
0.8069	Intermediate Similarity	NPC66518
0.8058	Intermediate Similarity	NPC325651
0.7955	Intermediate Similarity	NPC51345
0.7941	Intermediate Similarity	NPC27581
0.7868	Intermediate Similarity	NPC326079
0.7842	Intermediate Similarity	NPC124776
0.7737	Intermediate Similarity	NPC56634
0.773	Intermediate Similarity	NPC145888
0.773	Intermediate Similarity	NPC161593
0.773	Intermediate Similarity	NPC16031
0.7721	Intermediate Similarity	NPC319950
0.7721	Intermediate Similarity	NPC264976
0.7692	Intermediate Similarity	NPC45191
0.7692	Intermediate Similarity	NPC326966
0.7681	Intermediate Similarity	NPC142577
0.7677	Intermediate Similarity	NPC56635
0.7639	Intermediate Similarity	NPC88667
0.7537	Intermediate Similarity	NPC26524
0.7448	Intermediate Similarity	NPC48909
0.7424	Intermediate Similarity	NPC97811
0.7413	Intermediate Similarity	NPC476353
0.7397	Intermediate Similarity	NPC244866
0.7394	Intermediate Similarity	NPC89630
0.7379	Intermediate Similarity	NPC241354
0.7368	Intermediate Similarity	NPC234639
0.7368	Intermediate Similarity	NPC259554
0.7361	Intermediate Similarity	NPC296712
0.7347	Intermediate Similarity	NPC307289
0.7338	Intermediate Similarity	NPC132771
0.7299	Intermediate Similarity	NPC296526
0.7297	Intermediate Similarity	NPC470441
0.7292	Intermediate Similarity	NPC321561
0.7266	Intermediate Similarity	NPC471033
0.7266	Intermediate Similarity	NPC311091
0.7248	Intermediate Similarity	NPC6913
0.7246	Intermediate Similarity	NPC19290
0.7246	Intermediate Similarity	NPC128249
0.7237	Intermediate Similarity	NPC204546
0.7222	Intermediate Similarity	NPC158900
0.7197	Intermediate Similarity	NPC42383
0.7192	Intermediate Similarity	NPC2596
0.7192	Intermediate Similarity	NPC478147
0.7178	Intermediate Similarity	NPC314725
0.7178	Intermediate Similarity	NPC313375
0.7163	Intermediate Similarity	NPC263835
0.7163	Intermediate Similarity	NPC474874
0.7153	Intermediate Similarity	NPC109241
0.7152	Intermediate Similarity	NPC223616
0.7143	Intermediate Similarity	NPC1065
0.7132	Intermediate Similarity	NPC266932
0.7132	Intermediate Similarity	NPC233238
0.7125	Intermediate Similarity	NPC207675
0.7125	Intermediate Similarity	NPC212699
0.7111	Intermediate Similarity	NPC79543
0.7105	Intermediate Similarity	NPC40321
0.7103	Intermediate Similarity	NPC3221
0.7103	Intermediate Similarity	NPC88403
0.7093	Intermediate Similarity	NPC235194
0.7092	Intermediate Similarity	NPC43275
0.7083	Intermediate Similarity	NPC140359
0.7083	Intermediate Similarity	NPC13020
0.708	Intermediate Similarity	NPC17693
0.7077	Intermediate Similarity	NPC245561
0.7077	Intermediate Similarity	NPC125732
0.7075	Intermediate Similarity	NPC226661
0.7063	Intermediate Similarity	NPC474862
0.7063	Intermediate Similarity	NPC177291
0.7063	Intermediate Similarity	NPC194416
0.7055	Intermediate Similarity	NPC474476
0.7055	Intermediate Similarity	NPC475236
0.7047	Intermediate Similarity	NPC141549
0.7039	Intermediate Similarity	NPC48202
0.7034	Intermediate Similarity	NPC474237
0.7029	Intermediate Similarity	NPC309808
0.7023	Intermediate Similarity	NPC52472
0.7021	Intermediate Similarity	NPC205502
0.7021	Intermediate Similarity	NPC293424
0.7014	Intermediate Similarity	NPC291189
0.7014	Intermediate Similarity	NPC69403
0.7013	Intermediate Similarity	NPC13696
0.7013	Intermediate Similarity	NPC79372
0.7007	Intermediate Similarity	NPC95034
0.7007	Intermediate Similarity	NPC142087
0.7007	Intermediate Similarity	NPC21890
0.7007	Intermediate Similarity	NPC22783
0.7	Intermediate Similarity	NPC243404
0.7	Intermediate Similarity	NPC163398
0.6986	Remote Similarity	NPC168259
0.6986	Remote Similarity	NPC320242
0.6986	Remote Similarity	NPC4164
0.6986	Remote Similarity	NPC280767
0.6985	Remote Similarity	NPC145638
0.6985	Remote Similarity	NPC290566
0.698	Remote Similarity	NPC257390
0.698	Remote Similarity	NPC7569
0.698	Remote Similarity	NPC326599
0.698	Remote Similarity	NPC329595
0.698	Remote Similarity	NPC278787
0.698	Remote Similarity	NPC475102
0.698	Remote Similarity	NPC2989
0.6978	Remote Similarity	NPC235250
0.6975	Remote Similarity	NPC319320
0.6975	Remote Similarity	NPC287757
0.697	Remote Similarity	NPC307425
0.6968	Remote Similarity	NPC310370
0.6968	Remote Similarity	NPC183642
0.6966	Remote Similarity	NPC328267
0.6966	Remote Similarity	NPC473942
0.6963	Remote Similarity	NPC186469
0.6962	Remote Similarity	NPC324081
0.6959	Remote Similarity	NPC201419
0.6948	Remote Similarity	NPC91953
0.6943	Remote Similarity	NPC9373
0.6943	Remote Similarity	NPC313414
0.694	Remote Similarity	NPC473855
0.694	Remote Similarity	NPC13495
0.6939	Remote Similarity	NPC218323
0.6934	Remote Similarity	NPC183700
0.6929	Remote Similarity	NPC301321
0.6923	Remote Similarity	NPC10781
0.6923	Remote Similarity	NPC122493
0.6923	Remote Similarity	NPC14177
0.6923	Remote Similarity	NPC293628
0.6918	Remote Similarity	NPC95733
0.6918	Remote Similarity	NPC111088
0.6918	Remote Similarity	NPC62101
0.6918	Remote Similarity	NPC221798
0.6918	Remote Similarity	NPC193805
0.6918	Remote Similarity	NPC229113
0.6917	Remote Similarity	NPC298224
0.6913	Remote Similarity	NPC238309
0.6913	Remote Similarity	NPC473019
0.6912	Remote Similarity	NPC206341
0.6912	Remote Similarity	NPC31274
0.6908	Remote Similarity	NPC6570
0.6908	Remote Similarity	NPC176814
0.6908	Remote Similarity	NPC4982
0.6908	Remote Similarity	NPC5310
0.6908	Remote Similarity	NPC68779
0.6908	Remote Similarity	NPC300776
0.6897	Remote Similarity	NPC311219
0.6897	Remote Similarity	NPC302211
0.6894	Remote Similarity	NPC107101
0.6889	Remote Similarity	NPC188677
0.6889	Remote Similarity	NPC113457
0.6889	Remote Similarity	NPC70843
0.6887	Remote Similarity	NPC113006
0.6887	Remote Similarity	NPC169766
0.6883	Remote Similarity	NPC197921
0.6879	Remote Similarity	NPC470860
0.6879	Remote Similarity	NPC33717
0.6875	Remote Similarity	NPC139839
0.6871	Remote Similarity	NPC257589
0.6871	Remote Similarity	NPC53305
0.6871	Remote Similarity	NPC29477
0.6867	Remote Similarity	NPC109778
0.6867	Remote Similarity	NPC275538
0.6866	Remote Similarity	NPC38209
0.6866	Remote Similarity	NPC8931
0.6866	Remote Similarity	NPC261573
0.6866	Remote Similarity	NPC283546
0.6866	Remote Similarity	NPC120693
0.6863	Remote Similarity	NPC476018
0.6863	Remote Similarity	NPC113295
0.6863	Remote Similarity	NPC248872
0.6863	Remote Similarity	NPC475029
0.6863	Remote Similarity	NPC475011
0.6859	Remote Similarity	NPC170812
0.6859	Remote Similarity	NPC326065
0.6853	Remote Similarity	NPC61779
0.6853	Remote Similarity	NPC283760
0.6849	Remote Similarity	NPC93730
0.6849	Remote Similarity	NPC248786
0.6849	Remote Similarity	NPC211218
0.6849	Remote Similarity	NPC14141
0.6846	Remote Similarity	NPC2401
0.6842	Remote Similarity	NPC287533
0.6839	Remote Similarity	NPC319870
0.6839	Remote Similarity	NPC73078
0.6839	Remote Similarity	NPC265335
0.6839	Remote Similarity	NPC189724
0.6839	Remote Similarity	NPC469360
0.6839	Remote Similarity	NPC148738

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 NPC318028 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	173
0.1-0.2	721
0.2-0.3	1206
0.3-0.4	2140
0.4-0.5	2432
0.5-0.6	1697
0.6-0.7	692
0.7-0.8	75
0.8-0.85	4
0.85-0.9	2
0.9-0.95	1
0.95-1	7

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD1537	Approved
1.0	High Similarity	NPD1538	Phase 1
1.0	High Similarity	NPD1519	Approved
0.9847	High Similarity	NPD1522	Approved
0.9847	High Similarity	NPD1523	Approved
0.9846	High Similarity	NPD1536	Approved
0.9695	High Similarity	NPD1521	Approved
0.9695	High Similarity	NPD1520	Approved
0.8769	High Similarity	NPD1535	Discovery
0.8702	High Similarity	NPD1481	Phase 2
0.8571	High Similarity	NPD196	Phase 1
0.8456	Intermediate Similarity	NPD2614	Approved
0.8308	Intermediate Similarity	NPD9568	Approved
0.8264	Intermediate Similarity	NPD2976	Clinical (unspecified phase)
0.8045	Intermediate Similarity	NPD1894	Discontinued
0.7823	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.782	Intermediate Similarity	NPD256	Approved
0.782	Intermediate Similarity	NPD255	Approved
0.7748	Intermediate Similarity	NPD3536	Discontinued
0.773	Intermediate Similarity	NPD9569	Approved
0.7687	Intermediate Similarity	NPD2239	Approved
0.7687	Intermediate Similarity	NPD2240	Approved
0.7655	Intermediate Similarity	NPD555	Phase 2
0.7639	Intermediate Similarity	NPD259	Phase 1
0.7628	Intermediate Similarity	NPD5355	Approved
0.7628	Intermediate Similarity	NPD5356	Approved
0.7622	Intermediate Similarity	NPD5163	Phase 2
0.7603	Intermediate Similarity	NPD3052	Approved
0.7603	Intermediate Similarity	NPD3054	Approved
0.7548	Intermediate Similarity	NPD3455	Phase 2
0.75	Intermediate Similarity	NPD9536	Phase 1
0.75	Intermediate Similarity	NPD9537	Phase 1
0.7448	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD6233	Phase 2
0.7397	Intermediate Similarity	NPD5745	Approved
0.7379	Intermediate Similarity	NPD3136	Phase 2
0.7376	Intermediate Similarity	NPD2231	Phase 2
0.7376	Intermediate Similarity	NPD2235	Phase 2
0.7357	Intermediate Similarity	NPD3847	Discontinued
0.7333	Intermediate Similarity	NPD9570	Approved
0.7308	Intermediate Similarity	NPD7131	Phase 3
0.7296	Intermediate Similarity	NPD4018	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD258	Approved
0.7292	Intermediate Similarity	NPD257	Approved
0.7273	Intermediate Similarity	NPD968	Approved
0.7267	Intermediate Similarity	NPD6867	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6866	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD5746	Approved
0.726	Intermediate Similarity	NPD9718	Approved
0.7256	Intermediate Similarity	NPD7608	Discontinued
0.7252	Intermediate Similarity	NPD9608	Approved
0.7252	Intermediate Similarity	NPD9610	Approved
0.725	Intermediate Similarity	NPD3465	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD2030	Discontinued
0.7233	Intermediate Similarity	NPD6677	Suspended
0.7233	Intermediate Similarity	NPD2541	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD826	Approved
0.723	Intermediate Similarity	NPD825	Approved
0.7222	Intermediate Similarity	NPD1203	Approved
0.7219	Intermediate Similarity	NPD4477	Approved
0.7219	Intermediate Similarity	NPD4476	Approved
0.7219	Intermediate Similarity	NPD7450	Phase 2
0.72	Intermediate Similarity	NPD5688	Approved
0.72	Intermediate Similarity	NPD5689	Approved
0.7192	Intermediate Similarity	NPD600	Approved
0.7192	Intermediate Similarity	NPD596	Approved
0.7179	Intermediate Similarity	NPD5348	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD5709	Phase 3
0.7172	Intermediate Similarity	NPD558	Phase 2
0.717	Intermediate Similarity	NPD6502	Phase 2
0.7169	Intermediate Similarity	NPD3451	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3686	Approved
0.7152	Intermediate Similarity	NPD3687	Approved
0.7143	Intermediate Similarity	NPD7972	Discontinued
0.7134	Intermediate Similarity	NPD4666	Phase 3
0.7134	Intermediate Similarity	NPD6390	Discontinued
0.7134	Intermediate Similarity	NPD4186	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1608	Approved
0.7133	Intermediate Similarity	NPD2653	Approved
0.7118	Intermediate Similarity	NPD7039	Approved
0.7118	Intermediate Similarity	NPD7038	Approved
0.7107	Intermediate Similarity	NPD3769	Discontinued
0.7103	Intermediate Similarity	NPD2797	Approved
0.7095	Intermediate Similarity	NPD3374	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD6798	Discontinued
0.7083	Intermediate Similarity	NPD6583	Phase 3
0.7083	Intermediate Similarity	NPD6582	Phase 2
0.708	Intermediate Similarity	NPD5535	Approved
0.7073	Intermediate Similarity	NPD6315	Phase 2
0.7067	Intermediate Similarity	NPD4618	Approved
0.7067	Intermediate Similarity	NPD4622	Approved
0.7051	Intermediate Similarity	NPD6667	Approved
0.7051	Intermediate Similarity	NPD6666	Approved
0.7047	Intermediate Similarity	NPD4062	Phase 3
0.7032	Intermediate Similarity	NPD3400	Discontinued
0.7025	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2203	Discontinued
0.6993	Remote Similarity	NPD6032	Approved
0.6993	Remote Similarity	NPD2935	Discontinued
0.6986	Remote Similarity	NPD1817	Approved
0.6986	Remote Similarity	NPD1818	Approved
0.6986	Remote Similarity	NPD1820	Approved
0.6986	Remote Similarity	NPD1819	Approved
0.6985	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD3909	Discontinued
0.6981	Remote Similarity	NPD7427	Discontinued
0.698	Remote Similarity	NPD3268	Approved
0.6975	Remote Similarity	NPD8019	Approved
0.6968	Remote Similarity	NPD2459	Approved
0.6968	Remote Similarity	NPD2460	Phase 3
0.6968	Remote Similarity	NPD2458	Approved
0.6966	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD2428	Approved
0.6966	Remote Similarity	NPD2429	Approved
0.6954	Remote Similarity	NPD274	Approved
0.6954	Remote Similarity	NPD6355	Discontinued
0.6954	Remote Similarity	NPD275	Approved
0.6948	Remote Similarity	NPD7978	Discontinued
0.6948	Remote Similarity	NPD5865	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD6584	Phase 3
0.6928	Remote Similarity	NPD6746	Phase 2
0.6923	Remote Similarity	NPD17	Approved
0.6923	Remote Similarity	NPD9566	Approved
0.6923	Remote Similarity	NPD2556	Approved
0.6923	Remote Similarity	NPD2554	Approved
0.6918	Remote Similarity	NPD3225	Approved
0.6918	Remote Similarity	NPD1283	Approved
0.6913	Remote Similarity	NPD6179	Discontinued
0.6906	Remote Similarity	NPD1241	Discontinued
0.6901	Remote Similarity	NPD1759	Phase 1
0.6901	Remote Similarity	NPD5557	Phase 1
0.6899	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD9717	Approved
0.6897	Remote Similarity	NPD2562	Approved
0.6897	Remote Similarity	NPD2561	Approved
0.6875	Remote Similarity	NPD7523	Phase 3
0.6871	Remote Similarity	NPD7495	Discontinued
0.6871	Remote Similarity	NPD4433	Discontinued
0.6867	Remote Similarity	NPD2313	Discontinued
0.686	Remote Similarity	NPD6297	Approved
0.6859	Remote Similarity	NPD3060	Approved
0.6859	Remote Similarity	NPD4162	Approved
0.6857	Remote Similarity	NPD595	Approved
0.6857	Remote Similarity	NPD9618	Approved
0.6857	Remote Similarity	NPD9614	Approved
0.6857	Remote Similarity	NPD593	Approved
0.6855	Remote Similarity	NPD2874	Phase 2
0.6853	Remote Similarity	NPD3049	Approved
0.6853	Remote Similarity	NPD6382	Discontinued
0.6839	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD2370	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD317	Approved
0.6831	Remote Similarity	NPD1758	Phase 1
0.6831	Remote Similarity	NPD318	Approved
0.6828	Remote Similarity	NPD422	Phase 1
0.6824	Remote Similarity	NPD3690	Phase 2
0.6824	Remote Similarity	NPD3691	Phase 2
0.6824	Remote Similarity	NPD3366	Approved
0.6824	Remote Similarity	NPD7451	Discontinued
0.6821	Remote Similarity	NPD839	Approved
0.6821	Remote Similarity	NPD1423	Approved
0.6821	Remote Similarity	NPD840	Approved
0.6821	Remote Similarity	NPD7477	Discontinued
0.6818	Remote Similarity	NPD2799	Discontinued
0.6815	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD3750	Approved
0.6815	Remote Similarity	NPD4110	Phase 3
0.6813	Remote Similarity	NPD2186	Approved
0.681	Remote Similarity	NPD6385	Approved
0.681	Remote Similarity	NPD6386	Approved
0.681	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD955	Approved
0.6807	Remote Similarity	NPD8031	Discontinued
0.6806	Remote Similarity	NPD2668	Approved
0.6806	Remote Similarity	NPD2667	Approved
0.68	Remote Similarity	NPD6853	Approved
0.68	Remote Similarity	NPD3167	Approved
0.68	Remote Similarity	NPD3179	Approved
0.68	Remote Similarity	NPD3166	Approved
0.68	Remote Similarity	NPD3180	Approved
0.68	Remote Similarity	NPD6851	Approved
0.68	Remote Similarity	NPD3164	Approved
0.68	Remote Similarity	NPD7095	Approved
0.68	Remote Similarity	NPD3165	Approved
0.6797	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD594	Approved
0.6786	Remote Similarity	NPD592	Approved
0.6786	Remote Similarity	NPD7484	Phase 3
0.6786	Remote Similarity	NPD7485	Phase 3
0.6784	Remote Similarity	NPD6620	Discovery
0.6779	Remote Similarity	NPD454	Approved
0.6776	Remote Similarity	NPD3142	Approved
0.6776	Remote Similarity	NPD3140	Approved
0.6772	Remote Similarity	NPD2309	Approved
0.6765	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD3596	Phase 2
0.6759	Remote Similarity	NPD3496	Discontinued
0.6757	Remote Similarity	NPD3266	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