NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	426.28
Volume:	463.301
LogP:	5.126
LogD:	4.771
LogS:	-3.977
# Rotatable Bonds:	4
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.609
Synthetic Accessibility Score:	4.27
Fsp3:	0.704
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.106
MDCK Permeability:	2.12E-05
Pgp-inhibitor:	0.554
Pgp-substrate:	0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.669

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.078
Plasma Protein Binding (PPB):	99.20%
Volume Distribution (VD):	0.518
Pgp-substrate:	2.35%

ADMET: Metabolism

CYP1A2-inhibitor:	0.054
CYP1A2-substrate:	0.692
CYP2C19-inhibitor:	0.039
CYP2C19-substrate:	0.328
CYP2C9-inhibitor:	0.188
CYP2C9-substrate:	0.217
CYP2D6-inhibitor:	0.14
CYP2D6-substrate:	0.141
CYP3A4-inhibitor:	0.095
CYP3A4-substrate:	0.162

ADMET: Excretion

Clearance (CL):	4.346
Half-life (T1/2):	0.805

ADMET: Toxicity

hERG Blockers:	0.058
Human Hepatotoxicity (H-HT):	0.183
Drug-inuced Liver Injury (DILI):	0.42
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.125
Maximum Recommended Daily Dose:	0.111
Skin Sensitization:	0.498
Carcinogencity:	0.016
Eye Corrosion:	0.019
Eye Irritation:	0.601
Respiratory Toxicity:	0.96

Download Data

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

Natural Product: NPC477596

Natural Product ID:	NPC477596
*Common Name:**	Comnastin E
IUPAC Name:	3-[[(3R,3aR,5aS,6R,7R,9aS,9bR)-3-acetyl-3a,6,7,9a-tetramethyl-1,2,3,4,5,5a,7,8,9,9b-decahydrocyclopenta[a]naphthalen-6-yl]methyl]-4-hydroxybenzoic acid
Synonyms:	comnastin E
Standard InCHIKey:	PCLWWUDFTVTRTJ-PDWRVGQOSA-N
Standard InCHI:	InChI=1S/C27H38O4/c1-16-10-12-26(4)22-9-7-20(17(2)28)25(22,3)13-11-23(26)27(16,5)15-19-14-18(24(30)31)6-8-21(19)29/h6,8,14,16,20,22-23,29H,7,9-13,15H2,1-5H3,(H,30,31)/t16-,20+,22+,23-,25+,26-,27-/m1/s1
SMILES:	C[C@@H]1CC[C@@]2([C@H]3CC[C@H]([C@@]3(CC[C@H]2[C@]1(C)CC4=C(C=CC(=C4)C(=O)O)O)C)C(=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44583758
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO15743	0stoc commune	Species	0stocaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10096870]
NPO15743	0stoc commune	Species	0stocaceae	Bacteria	n.a.	Mellingen, Switzerland	1965	PMID[10757714]
NPO15743	0stoc commune	Species	0stocaceae	Bacteria	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
MIC	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	128	ppm	PMID[10757714]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	4	ppm	PMID[10757714]

☑ 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 NPC477596 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	320
0.1-0.2	1347
0.2-0.3	2292
0.3-0.4	5185
0.4-0.5	11130
0.5-0.6	9613
0.6-0.7	10175
0.7-0.8	2540
0.8-0.85	80
0.85-0.9	7
0.9-0.95	4
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9922	High Similarity	NPC477594
0.9695	High Similarity	NPC477592
0.9621	High Similarity	NPC477593
0.9453	High Similarity	NPC229894
0.9407	High Similarity	NPC477595
0.9385	High Similarity	NPC18798
0.938	High Similarity	NPC117899
0.9302	High Similarity	NPC193203
0.8915	High Similarity	NPC174991
0.8788	High Similarity	NPC69424
0.8788	High Similarity	NPC84672
0.8788	High Similarity	NPC176130
0.8788	High Similarity	NPC78364
0.8681	High Similarity	NPC279442
0.8657	High Similarity	NPC276238
0.8647	High Similarity	NPC72667
0.8621	High Similarity	NPC142654
0.8594	High Similarity	NPC273282
0.8594	High Similarity	NPC474890
0.8594	High Similarity	NPC161943
0.8593	High Similarity	NPC108129
0.8571	High Similarity	NPC254492
0.8529	High Similarity	NPC471851
0.8521	High Similarity	NPC477209
0.8519	High Similarity	NPC303910
0.8519	High Similarity	NPC171460
0.8483	Intermediate Similarity	NPC5568
0.8478	Intermediate Similarity	NPC202225
0.8472	Intermediate Similarity	NPC75295
0.8451	Intermediate Similarity	NPC477275
0.8444	Intermediate Similarity	NPC96024
0.8438	Intermediate Similarity	NPC83718
0.8433	Intermediate Similarity	NPC473751
0.8421	Intermediate Similarity	NPC199273
0.8406	Intermediate Similarity	NPC477139
0.8406	Intermediate Similarity	NPC78307
0.8369	Intermediate Similarity	NPC234548
0.8369	Intermediate Similarity	NPC20210
0.8369	Intermediate Similarity	NPC248287
0.8358	Intermediate Similarity	NPC137416
0.8345	Intermediate Similarity	NPC475088
0.8345	Intermediate Similarity	NPC258856
0.8333	Intermediate Similarity	NPC271451
0.8333	Intermediate Similarity	NPC175738
0.8333	Intermediate Similarity	NPC249340
0.8333	Intermediate Similarity	NPC100242
0.8333	Intermediate Similarity	NPC162935
0.8333	Intermediate Similarity	NPC477207
0.8321	Intermediate Similarity	NPC190501
0.8321	Intermediate Similarity	NPC318552
0.8309	Intermediate Similarity	NPC3009
0.8298	Intermediate Similarity	NPC475957
0.8298	Intermediate Similarity	NPC36868
0.8298	Intermediate Similarity	NPC53001
0.8288	Intermediate Similarity	NPC477208
0.8273	Intermediate Similarity	NPC475457
0.8273	Intermediate Similarity	NPC111845
0.8273	Intermediate Similarity	NPC475627
0.8273	Intermediate Similarity	NPC18982
0.8273	Intermediate Similarity	NPC475346
0.8273	Intermediate Similarity	NPC49742
0.8271	Intermediate Similarity	NPC282577
0.8271	Intermediate Similarity	NPC475192
0.8264	Intermediate Similarity	NPC184935
0.8261	Intermediate Similarity	NPC476847
0.8258	Intermediate Similarity	NPC164852
0.8258	Intermediate Similarity	NPC190971
0.8258	Intermediate Similarity	NPC241001
0.8252	Intermediate Similarity	NPC169452
0.8252	Intermediate Similarity	NPC181560
0.8252	Intermediate Similarity	NPC471853
0.8252	Intermediate Similarity	NPC172311
0.8252	Intermediate Similarity	NPC315578
0.8248	Intermediate Similarity	NPC99731
0.8244	Intermediate Similarity	NPC473974
0.8244	Intermediate Similarity	NPC31296
0.8244	Intermediate Similarity	NPC79933
0.8244	Intermediate Similarity	NPC42657
0.8244	Intermediate Similarity	NPC258366
0.8239	Intermediate Similarity	NPC230811
0.8239	Intermediate Similarity	NPC4214
0.8239	Intermediate Similarity	NPC87723
0.8239	Intermediate Similarity	NPC473622
0.8231	Intermediate Similarity	NPC325032
0.8231	Intermediate Similarity	NPC477483
0.8227	Intermediate Similarity	NPC118919
0.8227	Intermediate Similarity	NPC191976
0.8227	Intermediate Similarity	NPC472308
0.8219	Intermediate Similarity	NPC208293
0.8217	Intermediate Similarity	NPC322197
0.8214	Intermediate Similarity	NPC293454
0.8209	Intermediate Similarity	NPC275145
0.8203	Intermediate Similarity	NPC242136
0.8195	Intermediate Similarity	NPC269923
0.8195	Intermediate Similarity	NPC167323
0.8195	Intermediate Similarity	NPC154696
0.8182	Intermediate Similarity	NPC242994
0.8182	Intermediate Similarity	NPC26924
0.8182	Intermediate Similarity	NPC138099
0.8175	Intermediate Similarity	NPC473017
0.8169	Intermediate Similarity	NPC49911
0.8169	Intermediate Similarity	NPC277559
0.8162	Intermediate Similarity	NPC471935
0.8162	Intermediate Similarity	NPC471929
0.8162	Intermediate Similarity	NPC471930
0.8156	Intermediate Similarity	NPC290803
0.8156	Intermediate Similarity	NPC249272
0.8156	Intermediate Similarity	NPC283088
0.8156	Intermediate Similarity	NPC153088
0.8143	Intermediate Similarity	NPC180261
0.8143	Intermediate Similarity	NPC37299
0.8143	Intermediate Similarity	NPC115458
0.8143	Intermediate Similarity	NPC138472
0.8138	Intermediate Similarity	NPC193555
0.8138	Intermediate Similarity	NPC248068
0.8134	Intermediate Similarity	NPC67300
0.8134	Intermediate Similarity	NPC91478
0.8134	Intermediate Similarity	NPC121168
0.8134	Intermediate Similarity	NPC176208
0.8133	Intermediate Similarity	NPC124842
0.8129	Intermediate Similarity	NPC125153
0.8125	Intermediate Similarity	NPC470035
0.8125	Intermediate Similarity	NPC470986
0.8125	Intermediate Similarity	NPC96421
0.8121	Intermediate Similarity	NPC179128
0.8121	Intermediate Similarity	NPC162569
0.8121	Intermediate Similarity	NPC35160
0.8121	Intermediate Similarity	NPC267469
0.8121	Intermediate Similarity	NPC87630
0.8121	Intermediate Similarity	NPC327962
0.8121	Intermediate Similarity	NPC116292
0.812	Intermediate Similarity	NPC32322
0.812	Intermediate Similarity	NPC259703
0.8116	Intermediate Similarity	NPC474998
0.8116	Intermediate Similarity	NPC25736
0.8112	Intermediate Similarity	NPC471974
0.8112	Intermediate Similarity	NPC469680
0.8112	Intermediate Similarity	NPC469681
0.8112	Intermediate Similarity	NPC13715
0.8102	Intermediate Similarity	NPC23126
0.8102	Intermediate Similarity	NPC72158
0.8102	Intermediate Similarity	NPC266689
0.8102	Intermediate Similarity	NPC116513
0.8102	Intermediate Similarity	NPC19432
0.8102	Intermediate Similarity	NPC162612
0.8102	Intermediate Similarity	NPC30501
0.8102	Intermediate Similarity	NPC103356
0.8102	Intermediate Similarity	NPC169250
0.8102	Intermediate Similarity	NPC105157
0.8102	Intermediate Similarity	NPC100067
0.8102	Intermediate Similarity	NPC98254
0.8102	Intermediate Similarity	NPC190043
0.8099	Intermediate Similarity	NPC7464
0.8099	Intermediate Similarity	NPC193358
0.8095	Intermediate Similarity	NPC470038
0.8088	Intermediate Similarity	NPC137750
0.8088	Intermediate Similarity	NPC87985
0.8088	Intermediate Similarity	NPC123506
0.8085	Intermediate Similarity	NPC194970
0.8085	Intermediate Similarity	NPC166480
0.8085	Intermediate Similarity	NPC270899
0.8085	Intermediate Similarity	NPC288089
0.8085	Intermediate Similarity	NPC12070
0.8085	Intermediate Similarity	NPC282780
0.8077	Intermediate Similarity	NPC161151
0.8074	Intermediate Similarity	NPC85511
0.8069	Intermediate Similarity	NPC2681
0.8069	Intermediate Similarity	NPC272907
0.8069	Intermediate Similarity	NPC91019
0.8069	Intermediate Similarity	NPC106519
0.8067	Intermediate Similarity	NPC140133
0.806	Intermediate Similarity	NPC120545
0.8058	Intermediate Similarity	NPC247477
0.8058	Intermediate Similarity	NPC17840
0.8056	Intermediate Similarity	NPC112789
0.8056	Intermediate Similarity	NPC19622
0.8054	Intermediate Similarity	NPC477206
0.8054	Intermediate Similarity	NPC17600
0.8043	Intermediate Similarity	NPC21305
0.8043	Intermediate Similarity	NPC221777
0.8043	Intermediate Similarity	NPC48248
0.8043	Intermediate Similarity	NPC282923
0.8043	Intermediate Similarity	NPC473744
0.8042	Intermediate Similarity	NPC53414
0.8042	Intermediate Similarity	NPC53206
0.8042	Intermediate Similarity	NPC62272
0.8042	Intermediate Similarity	NPC170718
0.8042	Intermediate Similarity	NPC471905
0.8041	Intermediate Similarity	NPC25844
0.8029	Intermediate Similarity	NPC3224
0.8029	Intermediate Similarity	NPC71610
0.8029	Intermediate Similarity	NPC267846
0.8029	Intermediate Similarity	NPC269598
0.8029	Intermediate Similarity	NPC62952
0.8029	Intermediate Similarity	NPC15837
0.8029	Intermediate Similarity	NPC204579
0.8028	Intermediate Similarity	NPC475917
0.8028	Intermediate Similarity	NPC173569
0.8028	Intermediate Similarity	NPC279463
0.8028	Intermediate Similarity	NPC43353

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 NPC477596 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	276
0.1-0.2	813
0.2-0.3	1257
0.3-0.4	2536
0.4-0.5	2449
0.5-0.6	1328
0.6-0.7	435
0.7-0.8	54
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8321	Intermediate Similarity	NPD3019	Approved
0.8182	Intermediate Similarity	NPD2932	Approved
0.8106	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.8042	Intermediate Similarity	NPD5404	Approved
0.8042	Intermediate Similarity	NPD5408	Approved
0.8042	Intermediate Similarity	NPD5405	Approved
0.8042	Intermediate Similarity	NPD5406	Approved
0.8	Intermediate Similarity	NPD6663	Approved
0.8	Intermediate Similarity	NPD7458	Discontinued
0.7972	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7971	Intermediate Similarity	NPD5736	Approved
0.7956	Intermediate Similarity	NPD1470	Approved
0.7945	Intermediate Similarity	NPD7003	Approved
0.7929	Intermediate Similarity	NPD3764	Approved
0.7926	Intermediate Similarity	NPD1201	Approved
0.7877	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7863	Intermediate Similarity	NPD5951	Approved
0.7852	Intermediate Similarity	NPD3026	Approved
0.7852	Intermediate Similarity	NPD3023	Approved
0.7836	Intermediate Similarity	NPD3024	Approved
0.7836	Intermediate Similarity	NPD3025	Approved
0.7742	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.7734	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD8166	Discontinued
0.7698	Intermediate Similarity	NPD1164	Approved
0.7674	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD7390	Discontinued
0.7603	Intermediate Similarity	NPD2799	Discontinued
0.76	Intermediate Similarity	NPD7236	Approved
0.7584	Intermediate Similarity	NPD4628	Phase 3
0.7566	Intermediate Similarity	NPD6273	Approved
0.7518	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8032	Phase 2
0.75	Intermediate Similarity	NPD9545	Approved
0.7467	Intermediate Similarity	NPD3750	Approved
0.7452	Intermediate Similarity	NPD7819	Suspended
0.7432	Intermediate Similarity	NPD2935	Discontinued
0.7426	Intermediate Similarity	NPD7610	Discontinued
0.7423	Intermediate Similarity	NPD7473	Discontinued
0.7419	Intermediate Similarity	NPD3226	Approved
0.7391	Intermediate Similarity	NPD4059	Approved
0.7376	Intermediate Similarity	NPD1876	Approved
0.7372	Intermediate Similarity	NPD3091	Approved
0.7361	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD3972	Approved
0.7355	Intermediate Similarity	NPD7239	Suspended
0.7351	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD943	Approved
0.7325	Intermediate Similarity	NPD7411	Suspended
0.7312	Intermediate Similarity	NPD7075	Discontinued
0.7296	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD1930	Approved
0.7287	Intermediate Similarity	NPD1929	Approved
0.7286	Intermediate Similarity	NPD3092	Approved
0.7284	Intermediate Similarity	NPD8127	Discontinued
0.7273	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2798	Approved
0.7273	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2346	Discontinued
0.725	Intermediate Similarity	NPD7768	Phase 2
0.7248	Intermediate Similarity	NPD1510	Phase 2
0.7239	Intermediate Similarity	NPD6232	Discontinued
0.7233	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD1607	Approved
0.7226	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD1240	Approved
0.7205	Intermediate Similarity	NPD3749	Approved
0.7203	Intermediate Similarity	NPD3094	Phase 2
0.72	Intermediate Similarity	NPD6100	Approved
0.72	Intermediate Similarity	NPD6099	Approved
0.7192	Intermediate Similarity	NPD3268	Approved
0.7192	Intermediate Similarity	NPD2313	Discontinued
0.7161	Intermediate Similarity	NPD2532	Approved
0.7161	Intermediate Similarity	NPD2533	Approved
0.7161	Intermediate Similarity	NPD2534	Approved
0.7152	Intermediate Similarity	NPD2344	Approved
0.7152	Intermediate Similarity	NPD6599	Discontinued
0.7152	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD9266	Approved
0.7143	Intermediate Similarity	NPD74	Approved
0.7143	Intermediate Similarity	NPD3095	Discontinued
0.7143	Intermediate Similarity	NPD7961	Discontinued
0.7143	Intermediate Similarity	NPD3300	Phase 2
0.7133	Intermediate Similarity	NPD1283	Approved
0.7133	Intermediate Similarity	NPD3748	Approved
0.7133	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD7008	Discontinued
0.7114	Intermediate Similarity	NPD6651	Approved
0.7101	Intermediate Similarity	NPD9493	Approved
0.7089	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD2797	Approved
0.7078	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD9267	Approved
0.7068	Intermediate Similarity	NPD9264	Approved
0.7068	Intermediate Similarity	NPD9263	Approved
0.7059	Intermediate Similarity	NPD2800	Approved
0.7054	Intermediate Similarity	NPD2066	Phase 3
0.7054	Intermediate Similarity	NPD3020	Approved
0.7047	Intermediate Similarity	NPD6355	Discontinued
0.7044	Intermediate Similarity	NPD4380	Phase 2
0.7039	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD5844	Phase 1
0.7021	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD4626	Approved
0.702	Intermediate Similarity	NPD4308	Phase 3
0.702	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD5760	Phase 2
0.7019	Intermediate Similarity	NPD5761	Phase 2
0.7	Intermediate Similarity	NPD7009	Phase 2
0.6993	Remote Similarity	NPD9269	Phase 2
0.6993	Remote Similarity	NPD1608	Approved
0.6993	Remote Similarity	NPD1549	Phase 2
0.6987	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.698	Remote Similarity	NPD4140	Approved
0.6968	Remote Similarity	NPD2309	Approved
0.6959	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6801	Discontinued
0.6953	Remote Similarity	NPD1809	Phase 2
0.695	Remote Similarity	NPD9268	Approved
0.6937	Remote Similarity	NPD7028	Phase 2
0.6936	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD7635	Approved
0.6934	Remote Similarity	NPD6858	Approved
0.6934	Remote Similarity	NPD7094	Approved
0.6933	Remote Similarity	NPD7057	Phase 3
0.6933	Remote Similarity	NPD7058	Phase 2
0.6928	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1281	Approved
0.6914	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD8150	Discontinued
0.6879	Remote Similarity	NPD6799	Approved
0.6875	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4878	Approved
0.6867	Remote Similarity	NPD6959	Discontinued
0.6864	Remote Similarity	NPD7799	Discontinued
0.6864	Remote Similarity	NPD7177	Discontinued
0.6863	Remote Similarity	NPD2796	Approved
0.6855	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD1203	Approved
0.6849	Remote Similarity	NPD3266	Approved
0.6849	Remote Similarity	NPD3267	Approved
0.6839	Remote Similarity	NPD1243	Approved
0.6835	Remote Similarity	NPD9281	Approved
0.6829	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD1755	Approved
0.6824	Remote Similarity	NPD6020	Phase 2
0.6822	Remote Similarity	NPD2859	Approved
0.6822	Remote Similarity	NPD2860	Approved
0.6821	Remote Similarity	NPD230	Phase 1
0.6818	Remote Similarity	NPD6005	Phase 3
0.6818	Remote Similarity	NPD6002	Phase 3
0.6818	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5762	Approved
0.6818	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6004	Phase 3
0.6818	Remote Similarity	NPD5763	Approved
0.6818	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD2342	Discontinued
0.6803	Remote Similarity	NPD4624	Approved
0.6802	Remote Similarity	NPD6765	Approved
0.6802	Remote Similarity	NPD6764	Approved
0.68	Remote Similarity	NPD8434	Phase 2
0.6797	Remote Similarity	NPD7305	Phase 1
0.6797	Remote Similarity	NPD845	Approved
0.6797	Remote Similarity	NPD7033	Discontinued
0.6795	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD3400	Discontinued
0.6783	Remote Similarity	NPD17	Approved
0.6779	Remote Similarity	NPD7095	Approved
0.6767	Remote Similarity	NPD9261	Approved
0.6766	Remote Similarity	NPD7199	Phase 2
0.6761	Remote Similarity	NPD7741	Discontinued
0.6759	Remote Similarity	NPD9717	Approved
0.6755	Remote Similarity	NPD2979	Phase 3
0.6755	Remote Similarity	NPD4307	Phase 2
0.6755	Remote Similarity	NPD4060	Phase 1
0.6753	Remote Similarity	NPD4476	Approved
0.6753	Remote Similarity	NPD4477	Approved
0.6753	Remote Similarity	NPD1551	Phase 2
0.6752	Remote Similarity	NPD6190	Approved
0.6744	Remote Similarity	NPD2934	Approved
0.6744	Remote Similarity	NPD1693	Approved
0.6744	Remote Similarity	NPD2933	Approved
0.6742	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD6798	Discontinued
0.6726	Remote Similarity	NPD7229	Phase 3
0.6724	Remote Similarity	NPD8312	Approved
0.6724	Remote Similarity	NPD8313	Approved
0.6715	Remote Similarity	NPD4750	Phase 3
0.6715	Remote Similarity	NPD3021	Approved
0.6715	Remote Similarity	NPD3022	Approved
0.6714	Remote Similarity	NPD2629	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