NPASS Compound

Structure

NPC200331 OpenBabel07101719522D 27 29 0 0 1 0 0 0 0 0999 V2000 1.3660 3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1486 3.7892 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5249 -2.5814 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7689 -0.6394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2602 2.3023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1336 2.7893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5250 -2.5664 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 1.5388 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2453 1.3024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1037 0.7895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9921 2.2764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9771 1.2765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2379 -0.2014 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5469 -0.9242 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5509 -0.8346 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8655 2.7634 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -0.0121 -3.4249 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8356 0.7636 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1890 -0.5104 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8982 -1.8604 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0380 -1.6930 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 9 1 0 0 0 0 3 10 1 0 0 0 0 4 11 1 0 0 0 0 6 7 1 0 0 0 0 6 12 1 0 0 0 0 7 21 1 0 0 0 0 8 10 2 0 0 0 0 8 13 1 0 0 0 0 10 16 1 0 0 0 0 11 23 2 0 0 0 0 11 27 1 0 0 0 0 12 9 1 1 0 0 0 12 15 1 0 0 0 0 13 14 2 0 0 0 0 13 15 1 0 0 0 0 14 17 1 0 0 0 0 14 18 1 0 0 0 0 15 21 1 1 0 0 0 16 17 2 0 0 0 0 16 22 1 0 0 0 0 17 24 1 0 0 0 0 18 19 1 0 0 0 0 18 25 2 0 0 0 0 19 20 1 0 0 0 0 19 26 2 0 0 0 0 20 21 1 1 0 0 0 20 27 1 0 0 0 0 21 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	436.09
Volume:	393.519
LogP:	4.39
LogD:	3.059
LogS:	-4.733
# Rotatable Bonds:	3
TPSA:	80.67
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.551
Synthetic Accessibility Score:	4.372
Fsp3:	0.571
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.665
MDCK Permeability:	1.8252967493026517e-05
Pgp-inhibitor:	0.632
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.026
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.197
Plasma Protein Binding (PPB):	100.58631896972656%
Volume Distribution (VD):	0.557
Pgp-substrate:	1.6817102432250977%

ADMET: Metabolism

CYP1A2-inhibitor:	0.422
CYP1A2-substrate:	0.648
CYP2C19-inhibitor:	0.527
CYP2C19-substrate:	0.591
CYP2C9-inhibitor:	0.83
CYP2C9-substrate:	0.56
CYP2D6-inhibitor:	0.111
CYP2D6-substrate:	0.203
CYP3A4-inhibitor:	0.335
CYP3A4-substrate:	0.437

ADMET: Excretion

Clearance (CL):	1.157
Half-life (T1/2):	0.05

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.225
Drug-inuced Liver Injury (DILI):	0.731
AMES Toxicity:	0.074
Rat Oral Acute Toxicity:	0.491
Maximum Recommended Daily Dose:	0.425
Skin Sensitization:	0.141
Carcinogencity:	0.065
Eye Corrosion:	0.004
Eye Irritation:	0.078
Respiratory Toxicity:	0.638

Download Data

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

Natural Product: NPC200331

Natural Product ID:	NPC200331
*Common Name:**	Hamigeran C
IUPAC Name:	[(1R,3aR,4R,10bR)-8-bromo-7-hydroxy-3a,9-dimethyl-5,6-dioxo-1-propan-2-yl-2,3,4,10b-tetrahydro-1H-benzo[e]azulen-4-yl] acetate
Synonyms:	Hamigeran C
Standard InCHIKey:	RIFRKOGZXWRBEW-FSKQDFAOSA-N
Standard InCHI:	InChI=1S/C21H25BrO5/c1-9(2)12-6-7-21(5)15(12)13-8-10(3)16(22)17(24)14(13)18(25)19(26)20(21)27-11(4)23/h8-9,12,15,20,24H,6-7H2,1-5H3/t12-,15-,20+,21-/m1/s1
SMILES:	CC(C)[C@H]1CC[C@]2(C)[C@H]1c1cc(C)c(c(c1C(=O)C(=O)[C@@H]2OC(=O)C)O)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL480483
PubChem CID:	10320862
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones

*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
NPO2050	Hamigera tarangaensis	Species	Hymedesmiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10650083]
NPO2050	Hamigera tarangaensis	Species	Hymedesmiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[29373034]
NPO2050	Hamigera tarangaensis	Species	Hymedesmiidae	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
IC50	1
Others	3

Activity Type	# Activity
Cell Line	1
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	16000.0	nM	PMID[547491]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	3.0	mm	PMID[547491]

☑ 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 NPC200331 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	354
0.1-0.2	1616
0.2-0.3	3305
0.3-0.4	9209
0.4-0.5	12656
0.5-0.6	10235
0.6-0.7	5157
0.7-0.8	160
0.8-0.85	2
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8896	High Similarity	NPC293312
0.8766	High Similarity	NPC160839
0.8293	Intermediate Similarity	NPC474777
0.8176	Intermediate Similarity	NPC84426
0.7697	Intermediate Similarity	NPC5568
0.7576	Intermediate Similarity	NPC475923
0.7576	Intermediate Similarity	NPC474309
0.7557	Intermediate Similarity	NPC470566
0.7514	Intermediate Similarity	NPC470567
0.75	Intermediate Similarity	NPC474310
0.7485	Intermediate Similarity	NPC220496
0.7485	Intermediate Similarity	NPC241349
0.7485	Intermediate Similarity	NPC37992
0.7485	Intermediate Similarity	NPC32749
0.7485	Intermediate Similarity	NPC42262
0.7485	Intermediate Similarity	NPC327916
0.7485	Intermediate Similarity	NPC147542
0.7425	Intermediate Similarity	NPC120536
0.7423	Intermediate Similarity	NPC216312
0.7423	Intermediate Similarity	NPC476477
0.7423	Intermediate Similarity	NPC299405
0.7423	Intermediate Similarity	NPC256463
0.7423	Intermediate Similarity	NPC295339
0.7423	Intermediate Similarity	NPC29771
0.7423	Intermediate Similarity	NPC111422
0.7423	Intermediate Similarity	NPC471602
0.7423	Intermediate Similarity	NPC306835
0.7421	Intermediate Similarity	NPC309430
0.7416	Intermediate Similarity	NPC475976
0.7394	Intermediate Similarity	NPC308572
0.7386	Intermediate Similarity	NPC471687
0.7375	Intermediate Similarity	NPC254603
0.7374	Intermediate Similarity	NPC24435
0.7365	Intermediate Similarity	NPC474630
0.7362	Intermediate Similarity	NPC61590
0.7349	Intermediate Similarity	NPC21873
0.7337	Intermediate Similarity	NPC94781
0.7333	Intermediate Similarity	NPC257003
0.7333	Intermediate Similarity	NPC471444
0.7329	Intermediate Similarity	NPC474394
0.7329	Intermediate Similarity	NPC218854
0.7329	Intermediate Similarity	NPC52368
0.7326	Intermediate Similarity	NPC470102
0.7308	Intermediate Similarity	NPC287473
0.7305	Intermediate Similarity	NPC29932
0.7296	Intermediate Similarity	NPC475741
0.7294	Intermediate Similarity	NPC120171
0.7289	Intermediate Similarity	NPC474300
0.7273	Intermediate Similarity	NPC315578
0.7247	Intermediate Similarity	NPC90245
0.7246	Intermediate Similarity	NPC476473
0.7246	Intermediate Similarity	NPC471731
0.7246	Intermediate Similarity	NPC159721
0.7246	Intermediate Similarity	NPC354984
0.7239	Intermediate Similarity	NPC472308
0.7235	Intermediate Similarity	NPC470479
0.7235	Intermediate Similarity	NPC17600
0.7229	Intermediate Similarity	NPC149533
0.7219	Intermediate Similarity	NPC63918
0.7215	Intermediate Similarity	NPC19432
0.7212	Intermediate Similarity	NPC103337
0.7212	Intermediate Similarity	NPC26924
0.7212	Intermediate Similarity	NPC114620
0.7209	Intermediate Similarity	NPC205918
0.7202	Intermediate Similarity	NPC151607
0.7202	Intermediate Similarity	NPC469385
0.7202	Intermediate Similarity	NPC274085
0.7202	Intermediate Similarity	NPC42540
0.7202	Intermediate Similarity	NPC103910
0.7202	Intermediate Similarity	NPC89664
0.7195	Intermediate Similarity	NPC474771
0.7195	Intermediate Similarity	NPC474849
0.7195	Intermediate Similarity	NPC471452
0.7195	Intermediate Similarity	NPC149372
0.7195	Intermediate Similarity	NPC178467
0.7195	Intermediate Similarity	NPC65837
0.7193	Intermediate Similarity	NPC44378
0.7193	Intermediate Similarity	NPC52931
0.7193	Intermediate Similarity	NPC280753
0.7188	Intermediate Similarity	NPC198305
0.7186	Intermediate Similarity	NPC471733
0.7184	Intermediate Similarity	NPC471456
0.7178	Intermediate Similarity	NPC27407
0.7169	Intermediate Similarity	NPC168471
0.716	Intermediate Similarity	NPC97188
0.7152	Intermediate Similarity	NPC191835
0.7152	Intermediate Similarity	NPC475974
0.7152	Intermediate Similarity	NPC472403
0.7151	Intermediate Similarity	NPC203426
0.7143	Intermediate Similarity	NPC478164
0.7143	Intermediate Similarity	NPC271451
0.7143	Intermediate Similarity	NPC17083
0.7143	Intermediate Similarity	NPC7012
0.7135	Intermediate Similarity	NPC477206
0.7135	Intermediate Similarity	NPC106524
0.7135	Intermediate Similarity	NPC290695
0.7134	Intermediate Similarity	NPC38158
0.7134	Intermediate Similarity	NPC86524
0.7134	Intermediate Similarity	NPC68756
0.7134	Intermediate Similarity	NPC12818
0.7134	Intermediate Similarity	NPC152525
0.7126	Intermediate Similarity	NPC472603
0.7126	Intermediate Similarity	NPC244923
0.7126	Intermediate Similarity	NPC2681
0.7126	Intermediate Similarity	NPC272907
0.7125	Intermediate Similarity	NPC131684
0.7125	Intermediate Similarity	NPC278928
0.7119	Intermediate Similarity	NPC313368
0.7118	Intermediate Similarity	NPC469498
0.7118	Intermediate Similarity	NPC136878
0.711	Intermediate Similarity	NPC475093
0.711	Intermediate Similarity	NPC11892
0.7101	Intermediate Similarity	NPC477409
0.7099	Intermediate Similarity	NPC246693
0.7099	Intermediate Similarity	NPC165612
0.7099	Intermediate Similarity	NPC110609
0.7099	Intermediate Similarity	NPC88864
0.7099	Intermediate Similarity	NPC58685
0.7099	Intermediate Similarity	NPC242358
0.7091	Intermediate Similarity	NPC477592
0.7091	Intermediate Similarity	NPC475957
0.7091	Intermediate Similarity	NPC70380
0.7091	Intermediate Similarity	NPC119542
0.7089	Intermediate Similarity	NPC131799
0.7089	Intermediate Similarity	NPC167055
0.7089	Intermediate Similarity	NPC240744
0.7083	Intermediate Similarity	NPC248068
0.7081	Intermediate Similarity	NPC163169
0.7081	Intermediate Similarity	NPC123
0.7076	Intermediate Similarity	NPC476821
0.7076	Intermediate Similarity	NPC52161
0.7076	Intermediate Similarity	NPC471734
0.7076	Intermediate Similarity	NPC53362
0.7076	Intermediate Similarity	NPC8817
0.7076	Intermediate Similarity	NPC162751
0.7076	Intermediate Similarity	NPC166583
0.7073	Intermediate Similarity	NPC290803
0.7073	Intermediate Similarity	NPC477596
0.7073	Intermediate Similarity	NPC142027
0.707	Intermediate Similarity	NPC275145
0.7069	Intermediate Similarity	NPC471347
0.7069	Intermediate Similarity	NPC471349
0.7066	Intermediate Similarity	NPC472600
0.7066	Intermediate Similarity	NPC472601
0.7063	Intermediate Similarity	NPC476024
0.7063	Intermediate Similarity	NPC165257
0.7062	Intermediate Similarity	NPC314795
0.7059	Intermediate Similarity	NPC170055
0.7059	Intermediate Similarity	NPC75694
0.7059	Intermediate Similarity	NPC478160
0.7056	Intermediate Similarity	NPC316262
0.7056	Intermediate Similarity	NPC211592
0.7056	Intermediate Similarity	NPC314653
0.7055	Intermediate Similarity	NPC314048
0.7055	Intermediate Similarity	NPC37299
0.7055	Intermediate Similarity	NPC180261
0.7055	Intermediate Similarity	NPC78307
0.7055	Intermediate Similarity	NPC49742
0.7055	Intermediate Similarity	NPC114183
0.7055	Intermediate Similarity	NPC115458
0.7055	Intermediate Similarity	NPC193169
0.7052	Intermediate Similarity	NPC37642
0.7048	Intermediate Similarity	NPC9121
0.7048	Intermediate Similarity	NPC477593
0.7048	Intermediate Similarity	NPC212693
0.7048	Intermediate Similarity	NPC94248
0.7048	Intermediate Similarity	NPC177307
0.7048	Intermediate Similarity	NPC33144
0.7048	Intermediate Similarity	NPC478200
0.7044	Intermediate Similarity	NPC227741
0.7044	Intermediate Similarity	NPC231774
0.7044	Intermediate Similarity	NPC295202
0.7044	Intermediate Similarity	NPC136342
0.7044	Intermediate Similarity	NPC49647
0.7043	Intermediate Similarity	NPC471686
0.7041	Intermediate Similarity	NPC143898
0.7041	Intermediate Similarity	NPC472006
0.7041	Intermediate Similarity	NPC477207
0.7041	Intermediate Similarity	NPC100242
0.7032	Intermediate Similarity	NPC133302
0.703	Intermediate Similarity	NPC472599
0.703	Intermediate Similarity	NPC291454
0.703	Intermediate Similarity	NPC158481
0.703	Intermediate Similarity	NPC156967
0.7029	Intermediate Similarity	NPC218870
0.7029	Intermediate Similarity	NPC470408
0.7029	Intermediate Similarity	NPC312482
0.7029	Intermediate Similarity	NPC205172
0.7029	Intermediate Similarity	NPC209393
0.7029	Intermediate Similarity	NPC182921
0.7029	Intermediate Similarity	NPC474824
0.7025	Intermediate Similarity	NPC234890
0.7025	Intermediate Similarity	NPC74507
0.7024	Intermediate Similarity	NPC91019
0.7024	Intermediate Similarity	NPC283292
0.7024	Intermediate Similarity	NPC477595
0.7024	Intermediate Similarity	NPC472604
0.7024	Intermediate Similarity	NPC106519
0.7024	Intermediate Similarity	NPC472605
0.7024	Intermediate Similarity	NPC478217

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 NPC200331 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	323
0.1-0.2	1011
0.2-0.3	2000
0.3-0.4	3021
0.4-0.5	1967
0.5-0.6	721
0.6-0.7	107
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7059	Intermediate Similarity	NPD2532	Approved
0.7059	Intermediate Similarity	NPD2534	Approved
0.7059	Intermediate Similarity	NPD2533	Approved
0.6786	Remote Similarity	NPD5406	Approved
0.6786	Remote Similarity	NPD5408	Approved
0.6786	Remote Similarity	NPD5404	Approved
0.6786	Remote Similarity	NPD5405	Approved
0.677	Remote Similarity	NPD1470	Approved
0.6746	Remote Similarity	NPD2346	Discontinued
0.673	Remote Similarity	NPD1201	Approved
0.6727	Remote Similarity	NPD6663	Approved
0.6705	Remote Similarity	NPD3226	Approved
0.6687	Remote Similarity	NPD5736	Approved
0.6667	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD8150	Discontinued
0.6529	Remote Similarity	NPD2799	Discontinued
0.6519	Remote Similarity	NPD4288	Approved
0.6519	Remote Similarity	NPD2296	Approved
0.65	Remote Similarity	NPD2932	Approved
0.65	Remote Similarity	NPD3019	Approved
0.6495	Remote Similarity	NPD4287	Approved
0.6486	Remote Similarity	NPD5710	Approved
0.6486	Remote Similarity	NPD5711	Approved
0.648	Remote Similarity	NPD6599	Discontinued
0.6471	Remote Similarity	NPD7473	Discontinued
0.6467	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6464	Remote Similarity	NPD7819	Suspended
0.6457	Remote Similarity	NPD7236	Approved
0.6456	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD5762	Approved
0.6453	Remote Similarity	NPD5763	Approved
0.6448	Remote Similarity	NPD7075	Discontinued
0.6441	Remote Similarity	NPD6273	Approved
0.6437	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.642	Remote Similarity	NPD7390	Discontinued
0.6406	Remote Similarity	NPD8312	Approved
0.6406	Remote Similarity	NPD8313	Approved
0.6398	Remote Similarity	NPD6232	Discontinued
0.6395	Remote Similarity	NPD2935	Discontinued
0.6384	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD3764	Approved
0.6369	Remote Similarity	NPD7239	Suspended
0.6364	Remote Similarity	NPD3300	Phase 2
0.6358	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD6005	Phase 3
0.6358	Remote Similarity	NPD6004	Phase 3
0.6358	Remote Similarity	NPD6002	Phase 3
0.6358	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD6959	Discontinued
0.6343	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD7003	Approved
0.6343	Remote Similarity	NPD4628	Phase 3
0.6337	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD7961	Discontinued
0.631	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD2800	Approved
0.6272	Remote Similarity	NPD2313	Discontinued
0.6263	Remote Similarity	NPD7799	Discontinued
0.625	Remote Similarity	NPD9493	Approved
0.625	Remote Similarity	NPD8166	Discontinued
0.625	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5402	Approved
0.6244	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.623	Remote Similarity	NPD6801	Discontinued
0.6226	Remote Similarity	NPD5951	Approved
0.6226	Remote Similarity	NPD2629	Approved
0.6216	Remote Similarity	NPD3882	Suspended
0.6207	Remote Similarity	NPD1551	Phase 2
0.62	Remote Similarity	NPD7539	Clinical (unspecified phase)
0.6199	Remote Similarity	NPD4060	Phase 1
0.6196	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD4626	Approved
0.6196	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6193	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD9545	Approved
0.6171	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD1164	Approved
0.6165	Remote Similarity	NPD8320	Phase 1
0.6165	Remote Similarity	NPD8319	Approved
0.6163	Remote Similarity	NPD6355	Discontinued
0.6162	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6159	Remote Similarity	NPD3023	Approved
0.6159	Remote Similarity	NPD3026	Approved
0.6154	Remote Similarity	NPD7458	Discontinued
0.6145	Remote Similarity	NPD6799	Approved
0.6142	Remote Similarity	NPD8434	Phase 2
0.6135	Remote Similarity	NPD3024	Approved
0.6135	Remote Similarity	NPD5691	Approved
0.6135	Remote Similarity	NPD3025	Approved
0.6134	Remote Similarity	NPD6559	Discontinued
0.6133	Remote Similarity	NPD5403	Approved
0.6129	Remote Similarity	NPD7768	Phase 2
0.6127	Remote Similarity	NPD6651	Approved
0.6119	Remote Similarity	NPD6535	Approved
0.6119	Remote Similarity	NPD6534	Approved
0.6118	Remote Similarity	NPD7008	Discontinued
0.6117	Remote Similarity	NPD7435	Discontinued
0.6114	Remote Similarity	NPD6099	Approved
0.6114	Remote Similarity	NPD6100	Approved
0.6108	Remote Similarity	NPD1283	Approved
0.6098	Remote Similarity	NPD1778	Approved
0.6091	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD7411	Suspended
0.6085	Remote Similarity	NPD8127	Discontinued
0.6082	Remote Similarity	NPD411	Approved
0.6076	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD3817	Phase 2
0.6074	Remote Similarity	NPD3091	Approved
0.6069	Remote Similarity	NPD230	Phase 1
0.6067	Remote Similarity	NPD3750	Approved
0.6062	Remote Similarity	NPD5844	Phase 1
0.6057	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6051	Remote Similarity	NPD74	Approved
0.6051	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6051	Remote Similarity	NPD6765	Approved
0.6051	Remote Similarity	NPD9266	Approved
0.6051	Remote Similarity	NPD6764	Approved
0.6047	Remote Similarity	NPD8032	Phase 2
0.6043	Remote Similarity	NPD7058	Phase 2
0.6043	Remote Similarity	NPD7057	Phase 3
0.6036	Remote Similarity	NPD2798	Approved
0.6036	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD6085	Phase 2
0.6036	Remote Similarity	NPD5647	Approved
0.6034	Remote Similarity	NPD1607	Approved
0.6033	Remote Similarity	NPD4380	Phase 2
0.6029	Remote Similarity	NPD7699	Phase 2
0.6029	Remote Similarity	NPD7700	Phase 2
0.6024	Remote Similarity	NPD3092	Approved
0.6022	Remote Similarity	NPD5761	Phase 2
0.6022	Remote Similarity	NPD5760	Phase 2
0.6022	Remote Similarity	NPD5401	Approved
0.6012	Remote Similarity	NPD6696	Suspended
0.6012	Remote Similarity	NPD943	Approved
0.6012	Remote Similarity	NPD2979	Phase 3
0.6012	Remote Similarity	NPD4140	Approved
0.6011	Remote Similarity	NPD3749	Approved
0.601	Remote Similarity	NPD7177	Discontinued
0.6	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.599	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.5989	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.5989	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.5989	Remote Similarity	NPD1471	Phase 3
0.5988	Remote Similarity	NPD9717	Approved
0.5987	Remote Similarity	NPD9264	Approved
0.5987	Remote Similarity	NPD9263	Approved
0.5987	Remote Similarity	NPD9267	Approved
0.5979	Remote Similarity	NPD6234	Discontinued
0.5979	Remote Similarity	NPD919	Approved
0.5979	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD447	Suspended
0.5976	Remote Similarity	NPD3094	Phase 2
0.5971	Remote Similarity	NPD6779	Approved
0.5971	Remote Similarity	NPD6781	Approved
0.5971	Remote Similarity	NPD6777	Approved
0.5971	Remote Similarity	NPD6776	Approved
0.5971	Remote Similarity	NPD6780	Approved
0.5971	Remote Similarity	NPD6778	Approved
0.5971	Remote Similarity	NPD6782	Approved
0.5968	Remote Similarity	NPD37	Approved
0.5968	Remote Similarity	NPD1934	Approved
0.5966	Remote Similarity	NPD7033	Discontinued
0.5966	Remote Similarity	NPD1510	Phase 2
0.5957	Remote Similarity	NPD4967	Phase 2
0.5957	Remote Similarity	NPD4965	Approved
0.5957	Remote Similarity	NPD4966	Approved
0.5955	Remote Similarity	NPD1549	Phase 2
0.5954	Remote Similarity	NPD4248	Discontinued
0.5947	Remote Similarity	NPD5494	Approved
0.5944	Remote Similarity	NPD6190	Approved
0.5943	Remote Similarity	NPD7874	Approved
0.5943	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD3269	Clinical (unspecified phase)
0.5939	Remote Similarity	NPD5034	Approved
0.5939	Remote Similarity	NPD5026	Approved
0.5939	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.5939	Remote Similarity	NPD4955	Approved
0.5939	Remote Similarity	NPD5028	Approved
0.5939	Remote Similarity	NPD36	Approved
0.5939	Remote Similarity	NPD4954	Approved
0.5938	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.5934	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD2438	Suspended
0.593	Remote Similarity	NPD6785	Approved
0.593	Remote Similarity	NPD6784	Approved
0.5928	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.5928	Remote Similarity	NPD1281	Approved
0.592	Remote Similarity	NPD1240	Approved
0.5917	Remote Similarity	NPD1876	Approved
0.5911	Remote Similarity	NPD6213	Phase 3
0.5911	Remote Similarity	NPD6212	Phase 3

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