NPASS Compound

Structure

NPC296712 OpenBabel07101718292D 29 29 0 0 1 0 0 0 0 0999 V2000 -6.9282 -12.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -9.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -12.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -12.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -11.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -10.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -9.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -6.5000 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 -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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -9.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 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 -0.8660 -3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -5.0000 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 -0.8660 -4.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 3 19 1 0 0 0 0 4 29 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 18 1 0 0 0 0 10 15 2 0 0 0 0 10 19 1 0 0 0 0 11 13 1 0 0 0 0 11 20 2 0 0 0 0 12 14 2 0 0 0 0 12 20 1 0 0 0 0 13 21 2 0 0 0 0 14 21 1 0 0 0 0 15 23 1 0 0 0 0 16 18 1 0 0 0 0 16 19 2 0 0 0 0 17 20 1 0 0 0 0 18 2 1 6 0 0 0 21 26 1 0 0 0 0 22 17 1 6 0 0 0 22 24 1 0 0 0 0 22 25 1 0 0 0 0 23 25 2 3 0 0 0 23 27 1 0 0 0 0 24 28 2 0 0 0 0 24 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	401.26
Volume:	442.806
LogP:	5.468
LogD:	4.688
LogS:	-4.555
# Rotatable Bonds:	14
TPSA:	75.96
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.22
Synthetic Accessibility Score:	3.357
Fsp3:	0.542
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:	-4.723
MDCK Permeability:	1.9076009266427718e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.996
30% Bioavailability (F30%):	0.565

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.051
Plasma Protein Binding (PPB):	99.28121185302734%
Volume Distribution (VD):	0.271
Pgp-substrate:	0.7622659802436829%

ADMET: Metabolism

CYP1A2-inhibitor:	0.316
CYP1A2-substrate:	0.789
CYP2C19-inhibitor:	0.884
CYP2C19-substrate:	0.662
CYP2C9-inhibitor:	0.928
CYP2C9-substrate:	0.969
CYP2D6-inhibitor:	0.368
CYP2D6-substrate:	0.322
CYP3A4-inhibitor:	0.888
CYP3A4-substrate:	0.537

ADMET: Excretion

Clearance (CL):	6.527
Half-life (T1/2):	0.616

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.805
Drug-inuced Liver Injury (DILI):	0.813
AMES Toxicity:	0.056
Rat Oral Acute Toxicity:	0.129
Maximum Recommended Daily Dose:	0.026
Skin Sensitization:	0.486
Carcinogencity:	0.1
Eye Corrosion:	0.003
Eye Irritation:	0.019
Respiratory Toxicity:	0.103

Download Data

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

Natural Product: NPC296712

Natural Product ID:	NPC296712
*Common Name:**	Gymnastatin H
IUPAC Name:	methyl (2S)-2-[[(2E,4E,6R)-4,6-dimethyldodeca-2,4-dienoyl]amino]-3-(4-hydroxyphenyl)propanoate
Synonyms:	Gymnastatin H
Standard InCHIKey:	GGAGAVWBROLYIO-UHGNHMIBSA-N
Standard InCHI:	InChI=1S/C24H35NO4/c1-5-6-7-8-9-18(2)16-19(3)10-15-23(27)25-22(24(28)29-4)17-20-11-13-21(26)14-12-20/h10-16,18,22,26H,5-9,17H2,1-4H3,(H,25,27)/b15-10+,19-16+/t18-,22+/m1/s1
SMILES:	CCCCCC[C@H](/C=C(/C=C/C(=N[C@H](C(=O)OC)Cc1ccc(cc1)O)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463204
PubChem CID:	16091098
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
NPO33119	gymnascella dankaliensis	Species	Gymnoascaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17067147]
NPO33119	gymnascella dankaliensis	Species	Gymnoascaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17988094]
NPO33119	gymnascella dankaliensis	Species	Gymnoascaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18284207]
NPO33119	gymnascella dankaliensis	Species	Gymnoascaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25600409]

☑ 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
ED50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	>	10.0	ug ml-1	PMID[566547]

☑ 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 NPC296712 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	129
0.1-0.2	761
0.2-0.3	3360
0.3-0.4	11137
0.4-0.5	9301
0.5-0.6	13980
0.6-0.7	3519
0.7-0.8	445
0.8-0.85	44
0.85-0.9	14
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.925	High Similarity	NPC319950
0.918	High Similarity	NPC474862
0.912	High Similarity	NPC476353
0.9024	High Similarity	NPC142577
0.8984	High Similarity	NPC45191
0.8976	High Similarity	NPC478147
0.8871	High Similarity	NPC27581
0.8855	High Similarity	NPC6570
0.8769	High Similarity	NPC244866
0.8731	High Similarity	NPC91953
0.8692	High Similarity	NPC326966
0.8682	High Similarity	NPC325651
0.8657	High Similarity	NPC197921
0.8626	High Similarity	NPC470392
0.8485	Intermediate Similarity	NPC328070
0.8456	Intermediate Similarity	NPC469360
0.8455	Intermediate Similarity	NPC317254
0.8444	Intermediate Similarity	NPC322526
0.8433	Intermediate Similarity	NPC6913
0.8413	Intermediate Similarity	NPC190663
0.8387	Intermediate Similarity	NPC188867
0.8387	Intermediate Similarity	NPC281686
0.8387	Intermediate Similarity	NPC106551
0.837	Intermediate Similarity	NPC473052
0.837	Intermediate Similarity	NPC473055
0.8347	Intermediate Similarity	NPC474149
0.8309	Intermediate Similarity	NPC471201
0.8281	Intermediate Similarity	NPC160493
0.8273	Intermediate Similarity	NPC81026
0.8268	Intermediate Similarity	NPC80150
0.825	Intermediate Similarity	NPC142297
0.8201	Intermediate Similarity	NPC266741
0.8189	Intermediate Similarity	NPC283760
0.8189	Intermediate Similarity	NPC239697
0.8125	Intermediate Similarity	NPC39431
0.8115	Intermediate Similarity	NPC258056
0.8092	Intermediate Similarity	NPC4974
0.808	Intermediate Similarity	NPC118202
0.8074	Intermediate Similarity	NPC88667
0.8062	Intermediate Similarity	NPC56634
0.8033	Intermediate Similarity	NPC31274
0.8017	Intermediate Similarity	NPC231705
0.8	Intermediate Similarity	NPC309808
0.7972	Intermediate Similarity	NPC132771
0.7969	Intermediate Similarity	NPC310467
0.7969	Intermediate Similarity	NPC317784
0.7969	Intermediate Similarity	NPC142638
0.7959	Intermediate Similarity	NPC56635
0.7923	Intermediate Similarity	NPC326079
0.7917	Intermediate Similarity	NPC178902
0.7891	Intermediate Similarity	NPC38458
0.7891	Intermediate Similarity	NPC169328
0.7891	Intermediate Similarity	NPC311737
0.7886	Intermediate Similarity	NPC96224
0.7886	Intermediate Similarity	NPC24101
0.7832	Intermediate Similarity	NPC16188
0.7812	Intermediate Similarity	NPC82963
0.7786	Intermediate Similarity	NPC48202
0.7778	Intermediate Similarity	NPC145888
0.7778	Intermediate Similarity	NPC16031
0.7778	Intermediate Similarity	NPC161593
0.7718	Intermediate Similarity	NPC212699
0.7718	Intermediate Similarity	NPC207675
0.7704	Intermediate Similarity	NPC321561
0.7704	Intermediate Similarity	NPC210950
0.7704	Intermediate Similarity	NPC199738
0.7703	Intermediate Similarity	NPC473580
0.7698	Intermediate Similarity	NPC163674
0.7698	Intermediate Similarity	NPC227553
0.7671	Intermediate Similarity	NPC324081
0.7667	Intermediate Similarity	NPC12730
0.7667	Intermediate Similarity	NPC245561
0.7638	Intermediate Similarity	NPC474584
0.7619	Intermediate Similarity	NPC233702
0.7616	Intermediate Similarity	NPC476194
0.7616	Intermediate Similarity	NPC469243
0.7609	Intermediate Similarity	NPC257390
0.7603	Intermediate Similarity	NPC52472
0.76	Intermediate Similarity	NPC153690
0.7597	Intermediate Similarity	NPC473502
0.7589	Intermediate Similarity	NPC313694
0.7589	Intermediate Similarity	NPC242159
0.758	Intermediate Similarity	NPC26108
0.758	Intermediate Similarity	NPC279871
0.7576	Intermediate Similarity	NPC476183
0.7568	Intermediate Similarity	NPC202198
0.7559	Intermediate Similarity	NPC166837
0.7557	Intermediate Similarity	NPC237420
0.7519	Intermediate Similarity	NPC476281
0.7519	Intermediate Similarity	NPC476184
0.7516	Intermediate Similarity	NPC306804
0.7516	Intermediate Similarity	NPC137627
0.75	Intermediate Similarity	NPC48525
0.75	Intermediate Similarity	NPC124776
0.75	Intermediate Similarity	NPC13495
0.75	Intermediate Similarity	NPC66518
0.75	Intermediate Similarity	NPC17693
0.75	Intermediate Similarity	NPC475544
0.75	Intermediate Similarity	NPC43275
0.7484	Intermediate Similarity	NPC294516
0.7484	Intermediate Similarity	NPC107938
0.7483	Intermediate Similarity	NPC476989
0.7482	Intermediate Similarity	NPC275538
0.7482	Intermediate Similarity	NPC48909
0.7481	Intermediate Similarity	NPC211218
0.7468	Intermediate Similarity	NPC223207
0.7468	Intermediate Similarity	NPC155506
0.7468	Intermediate Similarity	NPC476227
0.7468	Intermediate Similarity	NPC63931
0.7468	Intermediate Similarity	NPC159767
0.7462	Intermediate Similarity	NPC197470
0.746	Intermediate Similarity	NPC317305
0.7452	Intermediate Similarity	NPC89831
0.745	Intermediate Similarity	NPC262166
0.7445	Intermediate Similarity	NPC305717
0.7444	Intermediate Similarity	NPC478016
0.7444	Intermediate Similarity	NPC478014
0.7444	Intermediate Similarity	NPC478015
0.7442	Intermediate Similarity	NPC148969
0.744	Intermediate Similarity	NPC188677
0.7438	Intermediate Similarity	NPC260000
0.7438	Intermediate Similarity	NPC194671
0.7438	Intermediate Similarity	NPC269750
0.7434	Intermediate Similarity	NPC287757
0.7434	Intermediate Similarity	NPC319320
0.7426	Intermediate Similarity	NPC62101
0.7426	Intermediate Similarity	NPC95733
0.7426	Intermediate Similarity	NPC47667
0.7424	Intermediate Similarity	NPC122009
0.7419	Intermediate Similarity	NPC8931
0.7419	Intermediate Similarity	NPC261573
0.7419	Intermediate Similarity	NPC471771
0.7419	Intermediate Similarity	NPC290755
0.7419	Intermediate Similarity	NPC120693
0.7419	Intermediate Similarity	NPC304074
0.7407	Intermediate Similarity	NPC469927
0.7407	Intermediate Similarity	NPC476278
0.7402	Intermediate Similarity	NPC326187
0.7394	Intermediate Similarity	NPC109580
0.7389	Intermediate Similarity	NPC196091
0.7389	Intermediate Similarity	NPC40234
0.7389	Intermediate Similarity	NPC475123
0.7389	Intermediate Similarity	NPC46009
0.7389	Intermediate Similarity	NPC475204
0.7388	Intermediate Similarity	NPC473051
0.7388	Intermediate Similarity	NPC473050
0.7385	Intermediate Similarity	NPC142599
0.7381	Intermediate Similarity	NPC228737
0.7377	Intermediate Similarity	NPC280869
0.7376	Intermediate Similarity	NPC169766
0.7376	Intermediate Similarity	NPC243404
0.7372	Intermediate Similarity	NPC209463
0.7372	Intermediate Similarity	NPC137416
0.7368	Intermediate Similarity	NPC268572
0.7364	Intermediate Similarity	NPC273814
0.7361	Intermediate Similarity	NPC328137
0.7361	Intermediate Similarity	NPC317741
0.7361	Intermediate Similarity	NPC318028
0.7361	Intermediate Similarity	NPC241086
0.7361	Intermediate Similarity	NPC318984
0.7361	Intermediate Similarity	NPC259800
0.7361	Intermediate Similarity	NPC150712
0.7361	Intermediate Similarity	NPC282087
0.7357	Intermediate Similarity	NPC246913
0.7355	Intermediate Similarity	NPC472923
0.7353	Intermediate Similarity	NPC307020
0.7353	Intermediate Similarity	NPC476260
0.7353	Intermediate Similarity	NPC476241
0.7353	Intermediate Similarity	NPC236981
0.7348	Intermediate Similarity	NPC283468
0.7348	Intermediate Similarity	NPC471926
0.7348	Intermediate Similarity	NPC325295
0.7348	Intermediate Similarity	NPC76308
0.7344	Intermediate Similarity	NPC63345
0.7342	Intermediate Similarity	NPC230611
0.7339	Intermediate Similarity	NPC164859
0.7333	Intermediate Similarity	NPC5194
0.7333	Intermediate Similarity	NPC261934
0.7333	Intermediate Similarity	NPC56685
0.7328	Intermediate Similarity	NPC23402
0.7328	Intermediate Similarity	NPC37302
0.7317	Intermediate Similarity	NPC289381
0.7317	Intermediate Similarity	NPC155847
0.7315	Intermediate Similarity	NPC473491
0.7313	Intermediate Similarity	NPC263835
0.7313	Intermediate Similarity	NPC478121
0.731	Intermediate Similarity	NPC251439
0.7308	Intermediate Similarity	NPC109241
0.7305	Intermediate Similarity	NPC471953
0.7305	Intermediate Similarity	NPC474753
0.7302	Intermediate Similarity	NPC274089
0.7302	Intermediate Similarity	NPC191215
0.7302	Intermediate Similarity	NPC70843
0.7302	Intermediate Similarity	NPC327481
0.7299	Intermediate Similarity	NPC476179
0.7299	Intermediate Similarity	NPC476125
0.7297	Intermediate Similarity	NPC9373
0.7296	Intermediate Similarity	NPC273755
0.7296	Intermediate Similarity	NPC248670
0.7287	Intermediate Similarity	NPC177576

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 NPC296712 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	109
0.1-0.2	460
0.2-0.3	863
0.3-0.4	1938
0.4-0.5	2686
0.5-0.6	2159
0.6-0.7	846
0.7-0.8	80
0.8-0.85	7
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.876	High Similarity	NPD3136	Phase 2
0.8626	High Similarity	NPD5729	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD9568	Approved
0.8306	Intermediate Similarity	NPD255	Approved
0.8306	Intermediate Similarity	NPD256	Approved
0.8254	Intermediate Similarity	NPD1759	Phase 1
0.8175	Intermediate Similarity	NPD1758	Phase 1
0.8112	Intermediate Similarity	NPD6390	Discontinued
0.8074	Intermediate Similarity	NPD259	Phase 1
0.8058	Intermediate Similarity	NPD7978	Discontinued
0.8043	Intermediate Similarity	NPD6866	Clinical (unspecified phase)
0.8043	Intermediate Similarity	NPD6867	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD7450	Phase 2
0.7972	Intermediate Similarity	NPD6682	Clinical (unspecified phase)
0.7956	Intermediate Similarity	NPD555	Phase 2
0.7931	Intermediate Similarity	NPD7523	Phase 3
0.7905	Intermediate Similarity	NPD8019	Approved
0.7887	Intermediate Similarity	NPD3400	Discontinued
0.7883	Intermediate Similarity	NPD825	Approved
0.7883	Intermediate Similarity	NPD826	Approved
0.782	Intermediate Similarity	NPD196	Phase 1
0.7785	Intermediate Similarity	NPD7495	Discontinued
0.7778	Intermediate Similarity	NPD9569	Approved
0.7744	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7704	Intermediate Similarity	NPD258	Approved
0.7704	Intermediate Similarity	NPD257	Approved
0.7669	Intermediate Similarity	NPD5108	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD6346	Approved
0.7619	Intermediate Similarity	NPD3643	Approved
0.7619	Intermediate Similarity	NPD3642	Approved
0.7619	Intermediate Similarity	NPD3644	Approved
0.7616	Intermediate Similarity	NPD7972	Discontinued
0.7574	Intermediate Similarity	NPD7451	Discontinued
0.7568	Intermediate Similarity	NPD7131	Phase 3
0.7536	Intermediate Similarity	NPD9537	Phase 1
0.7536	Intermediate Similarity	NPD9536	Phase 1
0.7462	Intermediate Similarity	NPD1348	Approved
0.7442	Intermediate Similarity	NPD2228	Approved
0.7442	Intermediate Similarity	NPD2234	Approved
0.7442	Intermediate Similarity	NPD2229	Approved
0.7432	Intermediate Similarity	NPD5348	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD9608	Approved
0.7419	Intermediate Similarity	NPD9610	Approved
0.7417	Intermediate Similarity	NPD6502	Phase 2
0.7383	Intermediate Similarity	NPD4186	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD1538	Phase 1
0.7361	Intermediate Similarity	NPD9570	Approved
0.7361	Intermediate Similarity	NPD1519	Approved
0.7361	Intermediate Similarity	NPD1537	Approved
0.7353	Intermediate Similarity	NPD4659	Approved
0.7351	Intermediate Similarity	NPD3455	Phase 2
0.7338	Intermediate Similarity	NPD2614	Approved
0.7329	Intermediate Similarity	NPD2976	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD275	Approved
0.7324	Intermediate Similarity	NPD274	Approved
0.7305	Intermediate Similarity	NPD5745	Approved
0.7286	Intermediate Similarity	NPD9718	Approved
0.7286	Intermediate Similarity	NPD4738	Phase 2
0.7279	Intermediate Similarity	NPD6624	Discontinued
0.7278	Intermediate Similarity	NPD7608	Discontinued
0.7259	Intermediate Similarity	NPD3847	Discontinued
0.7241	Intermediate Similarity	NPD1523	Approved
0.7241	Intermediate Similarity	NPD1522	Approved
0.7239	Intermediate Similarity	NPD5981	Approved
0.7226	Intermediate Similarity	NPD3685	Discontinued
0.7222	Intermediate Similarity	NPD1536	Approved
0.7218	Intermediate Similarity	NPD318	Approved
0.7218	Intermediate Similarity	NPD317	Approved
0.7208	Intermediate Similarity	NPD5355	Approved
0.7208	Intermediate Similarity	NPD5356	Approved
0.7206	Intermediate Similarity	NPD4806	Approved
0.7206	Intermediate Similarity	NPD4807	Approved
0.7197	Intermediate Similarity	NPD8303	Discontinued
0.7165	Intermediate Similarity	NPD1445	Approved
0.7165	Intermediate Similarity	NPD1444	Approved
0.7164	Intermediate Similarity	NPD2218	Phase 2
0.7164	Intermediate Similarity	NPD5304	Approved
0.7164	Intermediate Similarity	NPD2217	Approved
0.7164	Intermediate Similarity	NPD5303	Approved
0.7163	Intermediate Similarity	NPD5746	Approved
0.7153	Intermediate Similarity	NPD2561	Approved
0.7153	Intermediate Similarity	NPD2562	Approved
0.7152	Intermediate Similarity	NPD6746	Phase 2
0.7143	Intermediate Similarity	NPD3123	Discovery
0.7132	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD3421	Phase 3
0.7123	Intermediate Similarity	NPD2239	Approved
0.7123	Intermediate Similarity	NPD2240	Approved
0.7122	Intermediate Similarity	NPD4103	Phase 2
0.7122	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD1521	Approved
0.7103	Intermediate Similarity	NPD1520	Approved
0.7101	Intermediate Similarity	NPD1755	Approved
0.7092	Intermediate Similarity	NPD5202	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD16	Approved
0.709	Intermediate Similarity	NPD856	Approved
0.7087	Intermediate Similarity	NPD1040	Phase 2
0.7059	Intermediate Similarity	NPD2667	Approved
0.7059	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2668	Approved
0.7037	Intermediate Similarity	NPD4479	Discontinued
0.7032	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD2541	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD3655	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD2203	Discontinued
0.7012	Intermediate Similarity	NPD5557	Phase 1
0.7007	Intermediate Similarity	NPD4135	Approved
0.7007	Intermediate Similarity	NPD4136	Approved
0.7007	Intermediate Similarity	NPD4106	Approved
0.7	Intermediate Similarity	NPD1792	Phase 2
0.6994	Remote Similarity	NPD3909	Discontinued
0.6993	Remote Similarity	NPD4619	Approved
0.6993	Remote Similarity	NPD4621	Approved
0.6993	Remote Similarity	NPD1048	Approved
0.6992	Remote Similarity	NPD2860	Approved
0.6992	Remote Similarity	NPD2859	Approved
0.6992	Remote Similarity	NPD9614	Approved
0.6992	Remote Similarity	NPD9618	Approved
0.6986	Remote Similarity	NPD3554	Approved
0.6986	Remote Similarity	NPD3552	Approved
0.6986	Remote Similarity	NPD5688	Approved
0.6986	Remote Similarity	NPD3555	Approved
0.6986	Remote Similarity	NPD3553	Approved
0.6986	Remote Similarity	NPD5689	Approved
0.6985	Remote Similarity	NPD4105	Approved
0.6985	Remote Similarity	NPD4102	Approved
0.6985	Remote Similarity	NPD4093	Discontinued
0.6978	Remote Similarity	NPD1669	Approved
0.6975	Remote Similarity	NPD5822	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7959	Clinical (unspecified phase)
0.696	Remote Similarity	NPD9712	Approved
0.696	Remote Similarity	NPD3020	Approved
0.6957	Remote Similarity	NPD4480	Approved
0.6957	Remote Similarity	NPD7315	Approved
0.6954	Remote Similarity	NPD6667	Approved
0.6954	Remote Similarity	NPD6666	Approved
0.6944	Remote Similarity	NPD520	Approved
0.6944	Remote Similarity	NPD7477	Discontinued
0.6944	Remote Similarity	NPD6663	Approved
0.6944	Remote Similarity	NPD2674	Phase 3
0.6943	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD9566	Approved
0.6934	Remote Similarity	NPD5306	Approved
0.6934	Remote Similarity	NPD5305	Approved
0.6933	Remote Similarity	NPD7066	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD3098	Discontinued
0.6929	Remote Similarity	NPD6325	Discontinued
0.6929	Remote Similarity	NPD3125	Approved
0.6928	Remote Similarity	NPD8014	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD7303	Discontinued
0.6918	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD2098	Approved
0.6917	Remote Similarity	NPD2650	Approved
0.6917	Remote Similarity	NPD2652	Approved
0.6912	Remote Similarity	NPD9545	Approved
0.6911	Remote Similarity	NPD2934	Approved
0.6911	Remote Similarity	NPD2933	Approved
0.6906	Remote Similarity	NPD2584	Suspended
0.6901	Remote Similarity	NPD3664	Approved
0.6901	Remote Similarity	NPD3663	Approved
0.6901	Remote Similarity	NPD3661	Approved
0.6901	Remote Similarity	NPD3662	Phase 3
0.6901	Remote Similarity	NPD5736	Approved
0.6899	Remote Similarity	NPD2379	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD7318	Phase 3
0.6897	Remote Similarity	NPD468	Phase 1
0.6892	Remote Similarity	NPD4476	Approved
0.6892	Remote Similarity	NPD4477	Approved
0.6887	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.688	Remote Similarity	NPD9710	Approved
0.688	Remote Similarity	NPD9711	Approved
0.6879	Remote Similarity	NPD1135	Approved
0.6879	Remote Similarity	NPD2626	Approved
0.6879	Remote Similarity	NPD2159	Approved
0.6879	Remote Similarity	NPD1134	Approved
0.6879	Remote Similarity	NPD2160	Approved
0.6879	Remote Similarity	NPD2625	Approved
0.6879	Remote Similarity	NPD1133	Approved
0.6879	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD1129	Approved
0.6879	Remote Similarity	NPD2628	Approved
0.6879	Remote Similarity	NPD1131	Approved
0.6879	Remote Similarity	NPD2627	Approved
0.6875	Remote Similarity	NPD3144	Approved
0.6875	Remote Similarity	NPD3145	Approved
0.6863	Remote Similarity	NPD4739	Approved
0.6863	Remote Similarity	NPD3536	Discontinued
0.6861	Remote Similarity	NPD4209	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD4504	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD6583	Phase 3
0.6857	Remote Similarity	NPD6582	Phase 2
0.6857	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD5201	Approved
0.6853	Remote Similarity	NPD4620	Approved
0.6853	Remote Similarity	NPD4617	Approved
0.6853	Remote Similarity	NPD5203	Approved
0.6849	Remote Similarity	NPD4622	Approved
0.6849	Remote Similarity	NPD4618	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