NPASS Compound

Structure

NPC45191 OpenBabel07101719142D 25 26 0 0 1 0 0 0 0 0999 V2000 6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -2.5000 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 0.8660 -1.5000 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 -0.0000 -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 6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -3.0000 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 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 4.3301 -1.5000 0.0000 N 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 5.1962 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 2 0 0 0 0 5 13 2 0 0 0 0 6 13 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 14 1 0 0 0 0 12 13 1 0 0 0 0 12 17 2 0 0 0 0 15 21 1 0 0 0 0 16 11 1 1 0 0 0 16 19 1 0 0 0 0 16 20 1 0 0 0 0 17 18 1 0 0 0 0 17 25 1 0 0 0 0 18 20 2 3 0 0 0 18 22 1 0 0 0 0 19 23 2 0 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	341.13
Volume:	351.287
LogP:	1.883
LogD:	1.497
LogS:	-2.183
# Rotatable Bonds:	8
TPSA:	96.19
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.753
Synthetic Accessibility Score:	2.971
Fsp3:	0.211
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:	-5.419
MDCK Permeability:	1.97932622540975e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.104
20% Bioavailability (F20%):	0.102
30% Bioavailability (F30%):	0.041

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.078
Plasma Protein Binding (PPB):	94.79425048828125%
Volume Distribution (VD):	0.134
Pgp-substrate:	5.345660209655762%

ADMET: Metabolism

CYP1A2-inhibitor:	0.063
CYP1A2-substrate:	0.068
CYP2C19-inhibitor:	0.07
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.213
CYP2C9-substrate:	0.117
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.374
CYP3A4-inhibitor:	0.011
CYP3A4-substrate:	0.33

ADMET: Excretion

Clearance (CL):	3.653
Half-life (T1/2):	0.897

ADMET: Toxicity

hERG Blockers:	0.043
Human Hepatotoxicity (H-HT):	0.431
Drug-inuced Liver Injury (DILI):	0.97
AMES Toxicity:	0.156
Rat Oral Acute Toxicity:	0.349
Maximum Recommended Daily Dose:	0.012
Skin Sensitization:	0.094
Carcinogencity:	0.27
Eye Corrosion:	0.003
Eye Irritation:	0.029
Respiratory Toxicity:	0.073

Download Data

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

Natural Product: NPC45191

Natural Product ID:	NPC45191
*Common Name:**	Iotrochamides A
IUPAC Name:	(2S)-3-(4-hydroxyphenyl)-2-[[(Z)-2-methoxy-3-phenylprop-2-enoyl]amino]propanoic acid
Synonyms:	Iotrochamides A
Standard InCHIKey:	OSFOPIPOGIRMHL-BQGMYUGNSA-N
Standard InCHI:	InChI=1S/C19H19NO5/c1-25-17(12-13-5-3-2-4-6-13)18(22)20-16(19(23)24)11-14-7-9-15(21)10-8-14/h2-10,12,16,21H,11H2,1H3,(H,20,22)(H,23,24)/b17-12-/t16-/m0/s1
SMILES:	CO/C(=Cc1ccccc1)/C(=N[C@H](C(=O)O)Cc1ccc(cc1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2048802
PubChem CID:	70690448
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:0004319] Tyrosine 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
NPO32866	iotrochota sp.	Species	Iotrochotidae	Eukaryota	n.a.	Australian	n.a.	PMID[22677313]

☑ 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	1
Others	1

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT71	Cell Line	HEK293	Homo sapiens	GI	=	85.0	%	PMID[528817]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	=	4700.0	nM	PMID[528817]

☑ 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 NPC45191 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	154
0.1-0.2	769
0.2-0.3	4113
0.3-0.4	12675
0.4-0.5	6208
0.5-0.6	13601
0.6-0.7	4715
0.7-0.8	424
0.8-0.85	24
0.85-0.9	12
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8984	High Similarity	NPC296712
0.8871	High Similarity	NPC319950
0.881	High Similarity	NPC142577
0.8797	High Similarity	NPC6913
0.8769	High Similarity	NPC325651
0.876	High Similarity	NPC476353
0.8712	High Similarity	NPC244866
0.8661	High Similarity	NPC474862
0.8657	High Similarity	NPC6570
0.8516	High Similarity	NPC27581
0.8496	Intermediate Similarity	NPC326966
0.8485	Intermediate Similarity	NPC478147
0.8433	Intermediate Similarity	NPC470392
0.8414	Intermediate Similarity	NPC56635
0.8254	Intermediate Similarity	NPC37302
0.8189	Intermediate Similarity	NPC281686
0.8189	Intermediate Similarity	NPC106551
0.8189	Intermediate Similarity	NPC188867
0.8182	Intermediate Similarity	NPC132771
0.8088	Intermediate Similarity	NPC275538
0.8045	Intermediate Similarity	NPC4974
0.8029	Intermediate Similarity	NPC328070
0.8029	Intermediate Similarity	NPC88667
0.8	Intermediate Similarity	NPC239697
0.8	Intermediate Similarity	NPC471201
0.7984	Intermediate Similarity	NPC38458
0.7984	Intermediate Similarity	NPC311737
0.7984	Intermediate Similarity	NPC24101
0.7984	Intermediate Similarity	NPC96224
0.7929	Intermediate Similarity	NPC473052
0.7929	Intermediate Similarity	NPC473055
0.7907	Intermediate Similarity	NPC82963
0.7887	Intermediate Similarity	NPC91953
0.7879	Intermediate Similarity	NPC83279
0.7879	Intermediate Similarity	NPC56634
0.7872	Intermediate Similarity	NPC322526
0.7868	Intermediate Similarity	NPC16031
0.7868	Intermediate Similarity	NPC161593
0.7868	Intermediate Similarity	NPC145888
0.7863	Intermediate Similarity	NPC43275
0.784	Intermediate Similarity	NPC153690
0.7832	Intermediate Similarity	NPC66518
0.7829	Intermediate Similarity	NPC317254
0.7826	Intermediate Similarity	NPC257390
0.7823	Intermediate Similarity	NPC153644
0.7817	Intermediate Similarity	NPC197921
0.7812	Intermediate Similarity	NPC309808
0.78	Intermediate Similarity	NPC207675
0.78	Intermediate Similarity	NPC212699
0.7794	Intermediate Similarity	NPC199738
0.7794	Intermediate Similarity	NPC210950
0.7786	Intermediate Similarity	NPC317784
0.7786	Intermediate Similarity	NPC122009
0.7786	Intermediate Similarity	NPC311091
0.7786	Intermediate Similarity	NPC471033
0.7786	Intermediate Similarity	NPC142638
0.777	Intermediate Similarity	NPC214869
0.7762	Intermediate Similarity	NPC469360
0.776	Intermediate Similarity	NPC142297
0.7754	Intermediate Similarity	NPC35961
0.7754	Intermediate Similarity	NPC195749
0.7754	Intermediate Similarity	NPC52029
0.7752	Intermediate Similarity	NPC118202
0.7744	Intermediate Similarity	NPC326079
0.7737	Intermediate Similarity	NPC251571
0.7734	Intermediate Similarity	NPC48525
0.7727	Intermediate Similarity	NPC268572
0.771	Intermediate Similarity	NPC283468
0.7704	Intermediate Similarity	NPC14141
0.7698	Intermediate Similarity	NPC114102
0.7698	Intermediate Similarity	NPC31274
0.7692	Intermediate Similarity	NPC318028
0.7692	Intermediate Similarity	NPC282087
0.7692	Intermediate Similarity	NPC259800
0.7692	Intermediate Similarity	NPC317741
0.7692	Intermediate Similarity	NPC241086
0.7692	Intermediate Similarity	NPC318984
0.7692	Intermediate Similarity	NPC328137
0.7681	Intermediate Similarity	NPC155838
0.768	Intermediate Similarity	NPC231705
0.7671	Intermediate Similarity	NPC16188
0.7669	Intermediate Similarity	NPC190663
0.7664	Intermediate Similarity	NPC321561
0.7662	Intermediate Similarity	NPC63931
0.7658	Intermediate Similarity	NPC26108
0.7647	Intermediate Similarity	NPC95733
0.7647	Intermediate Similarity	NPC62101
0.7643	Intermediate Similarity	NPC89831
0.7638	Intermediate Similarity	NPC258056
0.7622	Intermediate Similarity	NPC14600
0.7622	Intermediate Similarity	NPC160607
0.7622	Intermediate Similarity	NPC204848
0.7622	Intermediate Similarity	NPC41473
0.7622	Intermediate Similarity	NPC312770
0.7619	Intermediate Similarity	NPC9373
0.7619	Intermediate Similarity	NPC313414
0.7603	Intermediate Similarity	NPC81026
0.7594	Intermediate Similarity	NPC283760
0.7591	Intermediate Similarity	NPC29477
0.7582	Intermediate Similarity	NPC476194
0.7581	Intermediate Similarity	NPC178902
0.7578	Intermediate Similarity	NPC474149
0.7574	Intermediate Similarity	NPC211218
0.7569	Intermediate Similarity	NPC299583
0.7569	Intermediate Similarity	NPC197239
0.7569	Intermediate Similarity	NPC326860
0.7556	Intermediate Similarity	NPC472271
0.7556	Intermediate Similarity	NPC160493
0.754	Intermediate Similarity	NPC70843
0.754	Intermediate Similarity	NPC188677
0.7538	Intermediate Similarity	NPC148969
0.7537	Intermediate Similarity	NPC80150
0.7537	Intermediate Similarity	NPC263835
0.7536	Intermediate Similarity	NPC301713
0.7534	Intermediate Similarity	NPC266741
0.752	Intermediate Similarity	NPC261573
0.752	Intermediate Similarity	NPC120693
0.752	Intermediate Similarity	NPC8931
0.7519	Intermediate Similarity	NPC163674
0.7519	Intermediate Similarity	NPC227553
0.75	Intermediate Similarity	NPC48202
0.75	Intermediate Similarity	NPC128249
0.75	Intermediate Similarity	NPC17760
0.75	Intermediate Similarity	NPC35996
0.75	Intermediate Similarity	NPC326187
0.7482	Intermediate Similarity	NPC153990
0.7482	Intermediate Similarity	NPC186898
0.7481	Intermediate Similarity	NPC284078
0.748	Intermediate Similarity	NPC245561
0.7468	Intermediate Similarity	NPC469243
0.7467	Intermediate Similarity	NPC233702
0.7464	Intermediate Similarity	NPC124776
0.7442	Intermediate Similarity	NPC63345
0.7438	Intermediate Similarity	NPC473354
0.7431	Intermediate Similarity	NPC242159
0.7431	Intermediate Similarity	NPC313694
0.7429	Intermediate Similarity	NPC217431
0.7424	Intermediate Similarity	NPC51345
0.7424	Intermediate Similarity	NPC23402
0.7419	Intermediate Similarity	NPC52472
0.7417	Intermediate Similarity	NPC202198
0.7415	Intermediate Similarity	NPC106183
0.7407	Intermediate Similarity	NPC476183
0.7402	Intermediate Similarity	NPC29989
0.7402	Intermediate Similarity	NPC69332
0.7402	Intermediate Similarity	NPC95178
0.7397	Intermediate Similarity	NPC168861
0.7391	Intermediate Similarity	NPC85565
0.7388	Intermediate Similarity	NPC237420
0.7385	Intermediate Similarity	NPC177576
0.7376	Intermediate Similarity	NPC241354
0.7375	Intermediate Similarity	NPC273755
0.7375	Intermediate Similarity	NPC248670
0.7372	Intermediate Similarity	NPC469927
0.7368	Intermediate Similarity	NPC39431
0.7368	Intermediate Similarity	NPC478189
0.7368	Intermediate Similarity	NPC19290
0.7365	Intermediate Similarity	NPC63628
0.7365	Intermediate Similarity	NPC178466
0.7364	Intermediate Similarity	NPC88141
0.7358	Intermediate Similarity	NPC196091
0.7358	Intermediate Similarity	NPC269383
0.7358	Intermediate Similarity	NPC151030
0.7357	Intermediate Similarity	NPC477839
0.7355	Intermediate Similarity	NPC475544
0.7353	Intermediate Similarity	NPC98305
0.7353	Intermediate Similarity	NPC476184
0.7353	Intermediate Similarity	NPC476281
0.7348	Intermediate Similarity	NPC142599
0.7339	Intermediate Similarity	NPC12730
0.7338	Intermediate Similarity	NPC257589
0.7338	Intermediate Similarity	NPC280767
0.7338	Intermediate Similarity	NPC53305
0.7333	Intermediate Similarity	NPC471048
0.7333	Intermediate Similarity	NPC471049
0.7333	Intermediate Similarity	NPC294951
0.7333	Intermediate Similarity	NPC471050
0.7329	Intermediate Similarity	NPC476989
0.7329	Intermediate Similarity	NPC471165
0.7329	Intermediate Similarity	NPC296898
0.7329	Intermediate Similarity	NPC279871
0.7325	Intermediate Similarity	NPC223207
0.7324	Intermediate Similarity	NPC473724
0.7324	Intermediate Similarity	NPC48909
0.7323	Intermediate Similarity	NPC211551
0.7323	Intermediate Similarity	NPC13495
0.732	Intermediate Similarity	NPC476268
0.7319	Intermediate Similarity	NPC307020
0.7319	Intermediate Similarity	NPC236981
0.7313	Intermediate Similarity	NPC76308
0.7313	Intermediate Similarity	NPC175799
0.7313	Intermediate Similarity	NPC325295
0.7313	Intermediate Similarity	NPC145023
0.7313	Intermediate Similarity	NPC200988
0.7313	Intermediate Similarity	NPC610
0.7308	Intermediate Similarity	NPC183700
0.7308	Intermediate Similarity	NPC252544
0.7308	Intermediate Similarity	NPC222084
0.7308	Intermediate Similarity	NPC321252
0.7308	Intermediate Similarity	NPC319579

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 NPC45191 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	119
0.1-0.2	441
0.2-0.3	965
0.3-0.4	1885
0.4-0.5	2646
0.5-0.6	2151
0.6-0.7	838
0.7-0.8	99
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8284	Intermediate Similarity	NPD3136	Phase 2
0.8189	Intermediate Similarity	NPD9568	Approved
0.8062	Intermediate Similarity	NPD1759	Phase 1
0.8029	Intermediate Similarity	NPD5729	Clinical (unspecified phase)
0.8029	Intermediate Similarity	NPD259	Phase 1
0.8	Intermediate Similarity	NPD6866	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6867	Clinical (unspecified phase)
0.7984	Intermediate Similarity	NPD1758	Phase 1
0.7972	Intermediate Similarity	NPD3400	Discontinued
0.7969	Intermediate Similarity	NPD255	Approved
0.7969	Intermediate Similarity	NPD256	Approved
0.7958	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD7450	Phase 2
0.7914	Intermediate Similarity	NPD555	Phase 2
0.7868	Intermediate Similarity	NPD9569	Approved
0.7785	Intermediate Similarity	NPD3455	Phase 2
0.7778	Intermediate Similarity	NPD196	Phase 1
0.7748	Intermediate Similarity	NPD8019	Approved
0.7714	Intermediate Similarity	NPD826	Approved
0.7714	Intermediate Similarity	NPD825	Approved
0.7692	Intermediate Similarity	NPD1519	Approved
0.7692	Intermediate Similarity	NPD1538	Phase 1
0.7692	Intermediate Similarity	NPD1537	Approved
0.7664	Intermediate Similarity	NPD258	Approved
0.7664	Intermediate Similarity	NPD257	Approved
0.7651	Intermediate Similarity	NPD7131	Phase 3
0.7639	Intermediate Similarity	NPD7978	Discontinued
0.7632	Intermediate Similarity	NPD7495	Discontinued
0.763	Intermediate Similarity	NPD5108	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD9537	Phase 1
0.7626	Intermediate Similarity	NPD9536	Phase 1
0.7584	Intermediate Similarity	NPD6390	Discontinued
0.758	Intermediate Similarity	NPD7608	Discontinued
0.7569	Intermediate Similarity	NPD1523	Approved
0.7569	Intermediate Similarity	NPD1522	Approved
0.7568	Intermediate Similarity	NPD6682	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD1536	Approved
0.7536	Intermediate Similarity	NPD7451	Discontinued
0.7534	Intermediate Similarity	NPD2976	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD3536	Discontinued
0.75	Intermediate Similarity	NPD6502	Phase 2
0.7481	Intermediate Similarity	NPD3847	Discontinued
0.7468	Intermediate Similarity	NPD7972	Discontinued
0.7448	Intermediate Similarity	NPD2239	Approved
0.7448	Intermediate Similarity	NPD9570	Approved
0.7448	Intermediate Similarity	NPD2240	Approved
0.7445	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD1521	Approved
0.7431	Intermediate Similarity	NPD1520	Approved
0.7429	Intermediate Similarity	NPD5202	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD2614	Approved
0.7417	Intermediate Similarity	NPD7523	Phase 3
0.7372	Intermediate Similarity	NPD2562	Approved
0.7372	Intermediate Similarity	NPD2561	Approved
0.7353	Intermediate Similarity	NPD4106	Approved
0.7353	Intermediate Similarity	NPD4136	Approved
0.7353	Intermediate Similarity	NPD4135	Approved
0.7343	Intermediate Similarity	NPD6346	Approved
0.7342	Intermediate Similarity	NPD6746	Phase 2
0.7333	Intermediate Similarity	NPD4102	Approved
0.7333	Intermediate Similarity	NPD4105	Approved
0.7324	Intermediate Similarity	NPD4621	Approved
0.7324	Intermediate Similarity	NPD4619	Approved
0.7319	Intermediate Similarity	NPD4659	Approved
0.7308	Intermediate Similarity	NPD3642	Approved
0.7308	Intermediate Similarity	NPD3643	Approved
0.7308	Intermediate Similarity	NPD3644	Approved
0.7292	Intermediate Similarity	NPD275	Approved
0.7292	Intermediate Similarity	NPD274	Approved
0.7273	Intermediate Similarity	NPD2228	Approved
0.7273	Intermediate Similarity	NPD2229	Approved
0.7273	Intermediate Similarity	NPD5745	Approved
0.7273	Intermediate Similarity	NPD2234	Approved
0.7246	Intermediate Similarity	NPD6624	Discontinued
0.7244	Intermediate Similarity	NPD9608	Approved
0.7244	Intermediate Similarity	NPD9610	Approved
0.7226	Intermediate Similarity	NPD3421	Phase 3
0.7214	Intermediate Similarity	NPD3055	Approved
0.7214	Intermediate Similarity	NPD2625	Approved
0.7214	Intermediate Similarity	NPD2628	Approved
0.7214	Intermediate Similarity	NPD3053	Approved
0.7214	Intermediate Similarity	NPD2627	Approved
0.7214	Intermediate Similarity	NPD4103	Phase 2
0.7214	Intermediate Similarity	NPD2159	Approved
0.7214	Intermediate Similarity	NPD2160	Approved
0.7214	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD2626	Approved
0.7203	Intermediate Similarity	NPD6798	Discontinued
0.7183	Intermediate Similarity	NPD5203	Approved
0.7183	Intermediate Similarity	NPD4620	Approved
0.7183	Intermediate Similarity	NPD4617	Approved
0.7183	Intermediate Similarity	NPD5201	Approved
0.7174	Intermediate Similarity	NPD4807	Approved
0.7174	Intermediate Similarity	NPD4806	Approved
0.7171	Intermediate Similarity	NPD5348	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD5822	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD2933	Approved
0.7154	Intermediate Similarity	NPD2934	Approved
0.7153	Intermediate Similarity	NPD4062	Phase 3
0.7153	Intermediate Similarity	NPD2674	Phase 3
0.7153	Intermediate Similarity	NPD5305	Approved
0.7153	Intermediate Similarity	NPD5306	Approved
0.7153	Intermediate Similarity	NPD6233	Phase 2
0.7133	Intermediate Similarity	NPD9718	Approved
0.7133	Intermediate Similarity	NPD4738	Phase 2
0.7133	Intermediate Similarity	NPD5746	Approved
0.7132	Intermediate Similarity	NPD5304	Approved
0.7132	Intermediate Similarity	NPD5303	Approved
0.7132	Intermediate Similarity	NPD2217	Approved
0.7132	Intermediate Similarity	NPD2218	Phase 2
0.7124	Intermediate Similarity	NPD4186	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD5204	Approved
0.7097	Intermediate Similarity	NPD2859	Approved
0.7097	Intermediate Similarity	NPD2860	Approved
0.7095	Intermediate Similarity	NPD4477	Approved
0.7095	Intermediate Similarity	NPD4476	Approved
0.7089	Intermediate Similarity	NPD2379	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1048	Approved
0.7081	Intermediate Similarity	NPD2821	Approved
0.708	Intermediate Similarity	NPD5981	Approved
0.7075	Intermediate Similarity	NPD3555	Approved
0.7075	Intermediate Similarity	NPD3552	Approved
0.7075	Intermediate Similarity	NPD3553	Approved
0.7075	Intermediate Similarity	NPD3554	Approved
0.7071	Intermediate Similarity	NPD1669	Approved
0.707	Intermediate Similarity	NPD5356	Approved
0.707	Intermediate Similarity	NPD5355	Approved
0.707	Intermediate Similarity	NPD3812	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD317	Approved
0.7059	Intermediate Similarity	NPD318	Approved
0.7055	Intermediate Similarity	NPD6355	Discontinued
0.705	Intermediate Similarity	NPD1535	Discovery
0.7048	Intermediate Similarity	NPD7959	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD3823	Discontinued
0.7037	Intermediate Similarity	NPD1348	Approved
0.7037	Intermediate Similarity	NPD7315	Approved
0.7032	Intermediate Similarity	NPD4003	Phase 3
0.7029	Intermediate Similarity	NPD2668	Approved
0.7029	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD2667	Approved
0.7025	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD3465	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD5163	Phase 2
0.7007	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD3054	Approved
0.7007	Intermediate Similarity	NPD1894	Discontinued
0.7007	Intermediate Similarity	NPD3052	Approved
0.7007	Intermediate Similarity	NPD4479	Discontinued
0.7006	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6386	Approved
0.7006	Intermediate Similarity	NPD8014	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6677	Suspended
0.7006	Intermediate Similarity	NPD6385	Approved
0.7	Intermediate Similarity	NPD1481	Phase 2
0.6986	Remote Similarity	NPD6310	Approved
0.6986	Remote Similarity	NPD5121	Approved
0.6986	Remote Similarity	NPD6309	Approved
0.6986	Remote Similarity	NPD6311	Approved
0.6986	Remote Similarity	NPD5120	Approved
0.6986	Remote Similarity	NPD5119	Approved
0.6982	Remote Similarity	NPD5946	Clinical (unspecified phase)
0.698	Remote Similarity	NPD6032	Approved
0.697	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD3374	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD3145	Approved
0.6966	Remote Similarity	NPD3144	Approved
0.6962	Remote Similarity	NPD4018	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD5688	Approved
0.6959	Remote Similarity	NPD5689	Approved
0.6957	Remote Similarity	NPD4093	Discontinued
0.6957	Remote Similarity	NPD4504	Clinical (unspecified phase)
0.695	Remote Similarity	NPD6583	Phase 3
0.695	Remote Similarity	NPD1755	Approved
0.695	Remote Similarity	NPD6582	Phase 2
0.6948	Remote Similarity	NPD4739	Approved
0.6934	Remote Similarity	NPD856	Approved
0.6934	Remote Similarity	NPD16	Approved
0.6933	Remote Similarity	NPD3656	Approved
0.6929	Remote Similarity	NPD3020	Approved
0.6928	Remote Similarity	NPD6666	Approved
0.6928	Remote Similarity	NPD6667	Approved
0.6918	Remote Similarity	NPD7477	Discontinued
0.6914	Remote Similarity	NPD4666	Phase 3
0.6903	Remote Similarity	NPD7303	Discontinued
0.6901	Remote Similarity	NPD5311	Approved
0.6901	Remote Similarity	NPD5310	Approved
0.6899	Remote Similarity	NPD6072	Discontinued
0.6899	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD3274	Phase 2
0.6892	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD2568	Approved
0.6887	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD5557	Phase 1
0.6884	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4993	Discontinued
0.6871	Remote Similarity	NPD3059	Approved
0.6871	Remote Similarity	NPD3061	Approved
0.6871	Remote Similarity	NPD3062	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