NPASS Compound

Structure

NPC469402 OpenBabel07101718292D 29 32 0 0 1 0 0 0 0 0999 V2000 1.5827 -2.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2330 -1.3612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9898 4.2969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9898 4.2969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3558 1.9309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4898 1.4309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3558 2.9309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7577 1.4309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6237 2.9309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4487 -1.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4898 -2.0303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6237 1.9309 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.8917 1.9309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9781 1.5241 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4781 0.6581 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5827 -0.3364 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7872 2.9254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 2.2673 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6691 -0.7431 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.4898 3.4309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3147 -2.3364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6977 -3.0085 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5303 3.5945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4487 -0.8364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4612 -1.7213 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8090 3.1333 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3955 1.8605 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 11 1 0 0 0 0 3 21 1 0 0 0 0 4 21 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 12 1 0 0 0 0 7 21 1 0 0 0 0 8 12 1 0 0 0 0 8 13 2 0 0 0 0 9 12 1 0 0 0 0 9 21 1 0 0 0 0 10 22 2 0 0 0 0 10 25 1 0 0 0 0 11 23 2 0 0 0 0 11 26 1 0 0 0 0 13 17 1 0 0 0 0 14 13 1 1 0 0 0 14 15 1 0 0 0 0 14 18 1 0 0 0 0 15 16 1 0 0 0 0 15 19 1 0 0 0 0 16 20 1 0 0 0 0 16 25 1 0 0 0 0 17 24 2 0 0 0 0 17 27 1 0 0 0 0 18 27 1 0 0 0 0 18 28 1 0 0 0 0 19 28 1 0 0 0 0 19 29 1 0 0 0 0 20 26 1 0 0 0 0 20 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	406.24
Volume:	422.89
LogP:	3.468
LogD:	3.144
LogS:	-3.763
# Rotatable Bonds:	5
TPSA:	82.06
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.716
Synthetic Accessibility Score:	4.959
Fsp3:	0.739
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:	-4.768
MDCK Permeability:	1.971409801626578e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.786

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.14
Plasma Protein Binding (PPB):	83.5249252319336%
Volume Distribution (VD):	1.609
Pgp-substrate:	23.510921478271484%

ADMET: Metabolism

CYP1A2-inhibitor:	0.037
CYP1A2-substrate:	0.182
CYP2C19-inhibitor:	0.052
CYP2C19-substrate:	0.692
CYP2C9-inhibitor:	0.103
CYP2C9-substrate:	0.046
CYP2D6-inhibitor:	0.25
CYP2D6-substrate:	0.043
CYP3A4-inhibitor:	0.553
CYP3A4-substrate:	0.306

ADMET: Excretion

Clearance (CL):	2.879
Half-life (T1/2):	0.24

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.576
Drug-inuced Liver Injury (DILI):	0.157
AMES Toxicity:	0.893
Rat Oral Acute Toxicity:	0.862
Maximum Recommended Daily Dose:	0.335
Skin Sensitization:	0.245
Carcinogencity:	0.811
Eye Corrosion:	0.078
Eye Irritation:	0.024
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC469402

Natural Product ID:	NPC469402
*Common Name:**	Gracilin K
IUPAC Name:	[(2R,3S,3aS,3bR,4Z,6aS,7aR)-2-acetyloxy-4-[(3,3-dimethylcyclohexyl)methylidene]-5-oxo-2,3,3a,3b,6a,7a-hexahydrodifuro[5,3-a:5',4'-d]furan-3-yl] acetate
Synonyms:	Gracilin K
Standard InCHIKey:	GOSUIVNRFQNSRC-QBTHFRSLSA-N
Standard InCHI:	InChI=1S/C21H28O8/c1-10(22)25-16-15-14-13(8-12-6-5-7-21(3,4)9-12)17(24)27-18(14)28-19(15)29-20(16)26-11(2)23/h8,12,14-16,18-20H,5-7,9H2,1-4H3/b13-8-/t12?,14-,15-,16-,18+,19+,20-/m0/s1
SMILES:	CC(=O)O[C@@H]1[C@@H](OC(=O)C)O[C@@H]2[C@H]1[C@H]1[C@@H](O2)OC(=O)/C/1=CC1CCCC(C1)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1077771
PubChem CID:	44254082
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0001986] Tricarboxylic acids 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
NPO33347	spongionella sp.	Species	Dictyodendrillidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19601607]

☑ 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	2
Others	1

Activity Type	# Activity
Cell Line	2
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	=	8500.0	nM	PMID[546451]
NPT927	Cell Line	PBMC	Homo sapiens	IC50	=	9000.0	nM	PMID[546451]
NPT285	Individual Protein	Epidermal growth factor receptor erbB1	Homo sapiens	Inhibition	=	19.0	%	PMID[546451]

☑ 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 NPC469402 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	248
0.1-0.2	1478
0.2-0.3	6050
0.3-0.4	12362
0.4-0.5	10917
0.5-0.6	7443
0.6-0.7	3904
0.7-0.8	292
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9485	High Similarity	NPC469401
0.8077	Intermediate Similarity	NPC305157
0.8077	Intermediate Similarity	NPC307846
0.8019	Intermediate Similarity	NPC475960
0.7959	Intermediate Similarity	NPC80875
0.7941	Intermediate Similarity	NPC279561
0.7876	Intermediate Similarity	NPC151616
0.7778	Intermediate Similarity	NPC112457
0.7745	Intermediate Similarity	NPC306041
0.7736	Intermediate Similarity	NPC474917
0.7727	Intermediate Similarity	NPC222834
0.7714	Intermediate Similarity	NPC310804
0.7714	Intermediate Similarity	NPC261117
0.77	Intermediate Similarity	NPC65513
0.7692	Intermediate Similarity	NPC473219
0.7692	Intermediate Similarity	NPC470761
0.7685	Intermediate Similarity	NPC219900
0.7685	Intermediate Similarity	NPC392
0.7685	Intermediate Similarity	NPC177524
0.7658	Intermediate Similarity	NPC470120
0.7652	Intermediate Similarity	NPC204731
0.7647	Intermediate Similarity	NPC473369
0.7636	Intermediate Similarity	NPC474750
0.7624	Intermediate Similarity	NPC475657
0.7619	Intermediate Similarity	NPC473384
0.7611	Intermediate Similarity	NPC23046
0.7607	Intermediate Similarity	NPC86346
0.7607	Intermediate Similarity	NPC469379
0.7607	Intermediate Similarity	NPC75856
0.76	Intermediate Similarity	NPC475748
0.7573	Intermediate Similarity	NPC311166
0.7573	Intermediate Similarity	NPC54731
0.7549	Intermediate Similarity	NPC473330
0.7549	Intermediate Similarity	NPC473316
0.7547	Intermediate Similarity	NPC250545
0.7545	Intermediate Similarity	NPC235014
0.7522	Intermediate Similarity	NPC277583
0.7521	Intermediate Similarity	NPC469382
0.75	Intermediate Similarity	NPC293658
0.75	Intermediate Similarity	NPC157441
0.75	Intermediate Similarity	NPC264153
0.75	Intermediate Similarity	NPC473535
0.75	Intermediate Similarity	NPC474410
0.75	Intermediate Similarity	NPC473250
0.7477	Intermediate Similarity	NPC471364
0.7477	Intermediate Similarity	NPC132395
0.7477	Intermediate Similarity	NPC471365
0.7476	Intermediate Similarity	NPC167893
0.7475	Intermediate Similarity	NPC231889
0.7453	Intermediate Similarity	NPC28304
0.7453	Intermediate Similarity	NPC298255
0.7451	Intermediate Similarity	NPC476300
0.7451	Intermediate Similarity	NPC179746
0.7451	Intermediate Similarity	NPC471571
0.7451	Intermediate Similarity	NPC81419
0.7449	Intermediate Similarity	NPC155873
0.7436	Intermediate Similarity	NPC473231
0.7434	Intermediate Similarity	NPC90472
0.7429	Intermediate Similarity	NPC187268
0.7429	Intermediate Similarity	NPC472186
0.7429	Intermediate Similarity	NPC318917
0.7429	Intermediate Similarity	NPC476800
0.7429	Intermediate Similarity	NPC471366
0.7426	Intermediate Similarity	NPC473619
0.7423	Intermediate Similarity	NPC469
0.7423	Intermediate Similarity	NPC170286
0.7414	Intermediate Similarity	NPC163693
0.7414	Intermediate Similarity	NPC147635
0.7414	Intermediate Similarity	NPC48692
0.7411	Intermediate Similarity	NPC194951
0.7411	Intermediate Similarity	NPC12046
0.7407	Intermediate Similarity	NPC203659
0.7407	Intermediate Similarity	NPC86095
0.7404	Intermediate Similarity	NPC112654
0.7404	Intermediate Similarity	NPC256230
0.7387	Intermediate Similarity	NPC253906
0.7387	Intermediate Similarity	NPC5103
0.7387	Intermediate Similarity	NPC83005
0.7383	Intermediate Similarity	NPC13171
0.7383	Intermediate Similarity	NPC195510
0.7379	Intermediate Similarity	NPC2003
0.7379	Intermediate Similarity	NPC474338
0.7379	Intermediate Similarity	NPC88507
0.7379	Intermediate Similarity	NPC25701
0.7374	Intermediate Similarity	NPC284902
0.7368	Intermediate Similarity	NPC471816
0.7364	Intermediate Similarity	NPC10150
0.7358	Intermediate Similarity	NPC473204
0.7358	Intermediate Similarity	NPC306344
0.7358	Intermediate Similarity	NPC22149
0.7358	Intermediate Similarity	NPC255677
0.7358	Intermediate Similarity	NPC472187
0.7358	Intermediate Similarity	NPC473545
0.7355	Intermediate Similarity	NPC470851
0.7353	Intermediate Similarity	NPC9447
0.7353	Intermediate Similarity	NPC473321
0.7353	Intermediate Similarity	NPC208886
0.7353	Intermediate Similarity	NPC12172
0.7347	Intermediate Similarity	NPC38569
0.7347	Intermediate Similarity	NPC163615
0.7347	Intermediate Similarity	NPC41856
0.7339	Intermediate Similarity	NPC153095
0.7339	Intermediate Similarity	NPC239961
0.7333	Intermediate Similarity	NPC298841
0.7333	Intermediate Similarity	NPC204054
0.7333	Intermediate Similarity	NPC42399
0.7333	Intermediate Similarity	NPC257726
0.7333	Intermediate Similarity	NPC472188
0.7328	Intermediate Similarity	NPC475834
0.7328	Intermediate Similarity	NPC474179
0.7327	Intermediate Similarity	NPC151770
0.7327	Intermediate Similarity	NPC166919
0.7327	Intermediate Similarity	NPC78008
0.7321	Intermediate Similarity	NPC179798
0.7321	Intermediate Similarity	NPC304180
0.7315	Intermediate Similarity	NPC151516
0.7315	Intermediate Similarity	NPC254202
0.7315	Intermediate Similarity	NPC110989
0.7308	Intermediate Similarity	NPC471141
0.7308	Intermediate Similarity	NPC471142
0.7308	Intermediate Similarity	NPC36954
0.7304	Intermediate Similarity	NPC473968
0.7304	Intermediate Similarity	NPC13713
0.73	Intermediate Similarity	NPC475703
0.7297	Intermediate Similarity	NPC469370
0.7297	Intermediate Similarity	NPC187876
0.729	Intermediate Similarity	NPC198992
0.7288	Intermediate Similarity	NPC287236
0.7282	Intermediate Similarity	NPC61201
0.7282	Intermediate Similarity	NPC472196
0.7282	Intermediate Similarity	NPC472195
0.7282	Intermediate Similarity	NPC238090
0.7282	Intermediate Similarity	NPC475912
0.7282	Intermediate Similarity	NPC156553
0.7273	Intermediate Similarity	NPC474285
0.7273	Intermediate Similarity	NPC133422
0.7273	Intermediate Similarity	NPC254538
0.7273	Intermediate Similarity	NPC184512
0.7273	Intermediate Similarity	NPC180744
0.7265	Intermediate Similarity	NPC4548
0.7264	Intermediate Similarity	NPC23364
0.7264	Intermediate Similarity	NPC208233
0.7264	Intermediate Similarity	NPC81483
0.7264	Intermediate Similarity	NPC169468
0.7264	Intermediate Similarity	NPC61630
0.7264	Intermediate Similarity	NPC198422
0.7264	Intermediate Similarity	NPC40182
0.7264	Intermediate Similarity	NPC472015
0.7264	Intermediate Similarity	NPC473307
0.7264	Intermediate Similarity	NPC307517
0.7264	Intermediate Similarity	NPC473154
0.7257	Intermediate Similarity	NPC471570
0.7255	Intermediate Similarity	NPC312042
0.7255	Intermediate Similarity	NPC51004
0.7248	Intermediate Similarity	NPC472748
0.7248	Intermediate Similarity	NPC146731
0.7241	Intermediate Similarity	NPC475913
0.7238	Intermediate Similarity	NPC17585
0.7238	Intermediate Similarity	NPC476315
0.7238	Intermediate Similarity	NPC171598
0.7232	Intermediate Similarity	NPC46407
0.7232	Intermediate Similarity	NPC119550
0.7228	Intermediate Similarity	NPC226863
0.7227	Intermediate Similarity	NPC42747
0.7222	Intermediate Similarity	NPC80144
0.7222	Intermediate Similarity	NPC225353
0.7222	Intermediate Similarity	NPC58329
0.7222	Intermediate Similarity	NPC86077
0.7222	Intermediate Similarity	NPC222062
0.7217	Intermediate Similarity	NPC138372
0.7217	Intermediate Similarity	NPC106228
0.7217	Intermediate Similarity	NPC243981
0.7212	Intermediate Similarity	NPC140543
0.7212	Intermediate Similarity	NPC159698
0.7212	Intermediate Similarity	NPC471147
0.7212	Intermediate Similarity	NPC476267
0.7207	Intermediate Similarity	NPC135015
0.7207	Intermediate Similarity	NPC48548
0.7207	Intermediate Similarity	NPC128795
0.7207	Intermediate Similarity	NPC217921
0.7203	Intermediate Similarity	NPC470829
0.7203	Intermediate Similarity	NPC473228
0.7193	Intermediate Similarity	NPC469454
0.7193	Intermediate Similarity	NPC311592
0.7193	Intermediate Similarity	NPC469463
0.7193	Intermediate Similarity	NPC469496
0.7193	Intermediate Similarity	NPC75167
0.7193	Intermediate Similarity	NPC56448
0.719	Intermediate Similarity	NPC11732
0.7184	Intermediate Similarity	NPC233437
0.7184	Intermediate Similarity	NPC184463
0.7184	Intermediate Similarity	NPC207641
0.7184	Intermediate Similarity	NPC290651
0.7184	Intermediate Similarity	NPC472197
0.7184	Intermediate Similarity	NPC30515
0.7184	Intermediate Similarity	NPC70595
0.7184	Intermediate Similarity	NPC477749
0.7184	Intermediate Similarity	NPC150978
0.7184	Intermediate Similarity	NPC123177
0.7184	Intermediate Similarity	NPC470379

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 NPC469402 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	209
0.1-0.2	1921
0.2-0.3	4258
0.3-0.4	1924
0.4-0.5	538
0.5-0.6	239
0.6-0.7	60
0.7-0.8	1
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
0.7685	Intermediate Similarity	NPD6686	Approved
0.71	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD7507	Approved
0.6923	Remote Similarity	NPD6698	Approved
0.6923	Remote Similarity	NPD46	Approved
0.6822	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.68	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7319	Approved
0.6789	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD4225	Approved
0.6667	Remote Similarity	NPD1695	Approved
0.6639	Remote Similarity	NPD8516	Approved
0.6639	Remote Similarity	NPD8517	Approved
0.6639	Remote Similarity	NPD8515	Approved
0.6639	Remote Similarity	NPD8513	Phase 3
0.6602	Remote Similarity	NPD1694	Approved
0.6579	Remote Similarity	NPD6008	Approved
0.6529	Remote Similarity	NPD7327	Approved
0.6529	Remote Similarity	NPD7328	Approved
0.6522	Remote Similarity	NPD6412	Phase 2
0.6522	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD8033	Approved
0.6496	Remote Similarity	NPD6371	Approved
0.6475	Remote Similarity	NPD7516	Approved
0.6457	Remote Similarity	NPD7736	Approved
0.6452	Remote Similarity	NPD6370	Approved
0.6449	Remote Similarity	NPD7838	Discovery
0.6441	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD8294	Approved
0.6423	Remote Similarity	NPD8377	Approved
0.64	Remote Similarity	NPD8328	Phase 3
0.6389	Remote Similarity	NPD7983	Approved
0.6378	Remote Similarity	NPD8293	Discontinued
0.6378	Remote Similarity	NPD7078	Approved
0.6371	Remote Similarity	NPD8296	Approved
0.6371	Remote Similarity	NPD8380	Approved
0.6371	Remote Similarity	NPD8335	Approved
0.6371	Remote Similarity	NPD8379	Approved
0.6371	Remote Similarity	NPD8378	Approved
0.6371	Remote Similarity	NPD7503	Approved
0.6356	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD7492	Approved
0.6346	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD7638	Approved
0.6311	Remote Similarity	NPD5209	Approved
0.6299	Remote Similarity	NPD6616	Approved
0.629	Remote Similarity	NPD6054	Approved
0.6283	Remote Similarity	NPD7639	Approved
0.6283	Remote Similarity	NPD7640	Approved
0.6273	Remote Similarity	NPD5282	Discontinued
0.627	Remote Similarity	NPD7829	Approved
0.627	Remote Similarity	NPD7642	Approved
0.627	Remote Similarity	NPD7830	Approved
0.626	Remote Similarity	NPD7641	Discontinued
0.625	Remote Similarity	NPD6053	Discontinued
0.624	Remote Similarity	NPD6016	Approved
0.624	Remote Similarity	NPD6015	Approved
0.6198	Remote Similarity	NPD8133	Approved
0.619	Remote Similarity	NPD5988	Approved
0.6179	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD6009	Approved
0.616	Remote Similarity	NPD6059	Approved
0.6147	Remote Similarity	NPD5785	Approved
0.614	Remote Similarity	NPD6648	Approved
0.6134	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD8074	Phase 3
0.6116	Remote Similarity	NPD6882	Approved
0.6087	Remote Similarity	NPD5344	Discontinued
0.6075	Remote Similarity	NPD4249	Approved
0.6074	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD7260	Phase 2
0.6048	Remote Similarity	NPD7115	Discovery
0.6032	Remote Similarity	NPD6319	Approved
0.6019	Remote Similarity	NPD4250	Approved
0.6019	Remote Similarity	NPD4251	Approved
0.6018	Remote Similarity	NPD7839	Suspended
0.6015	Remote Similarity	NPD6845	Suspended
0.5984	Remote Similarity	NPD8297	Approved
0.5984	Remote Similarity	NPD8444	Approved
0.5963	Remote Similarity	NPD6903	Approved
0.5954	Remote Similarity	NPD8337	Approved
0.5954	Remote Similarity	NPD8336	Approved
0.5946	Remote Similarity	NPD7637	Suspended
0.5935	Remote Similarity	NPD4632	Approved
0.5926	Remote Similarity	NPD7521	Approved
0.5926	Remote Similarity	NPD7146	Approved
0.5926	Remote Similarity	NPD6409	Approved
0.5926	Remote Similarity	NPD5330	Approved
0.5926	Remote Similarity	NPD6684	Approved
0.5926	Remote Similarity	NPD7334	Approved
0.5923	Remote Similarity	NPD8451	Approved
0.5902	Remote Similarity	NPD6650	Approved
0.5902	Remote Similarity	NPD6649	Approved
0.5893	Remote Similarity	NPD6399	Phase 3
0.5893	Remote Similarity	NPD5779	Approved
0.5893	Remote Similarity	NPD5778	Approved
0.5891	Remote Similarity	NPD6067	Discontinued
0.5878	Remote Similarity	NPD8448	Approved
0.5868	Remote Similarity	NPD6373	Approved
0.5868	Remote Similarity	NPD6372	Approved
0.5859	Remote Similarity	NPD8268	Approved
0.5859	Remote Similarity	NPD8269	Approved
0.5859	Remote Similarity	NPD8266	Approved
0.5859	Remote Similarity	NPD8267	Approved
0.5841	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD7900	Approved
0.5833	Remote Similarity	NPD5697	Approved
0.5833	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD5737	Approved
0.5818	Remote Similarity	NPD6672	Approved
0.5818	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD5693	Phase 1
0.5798	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5798	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD6110	Phase 1
0.5789	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5785	Remote Similarity	NPD7320	Approved
0.5785	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5785	Remote Similarity	NPD6899	Approved
0.5785	Remote Similarity	NPD6881	Approved
0.5784	Remote Similarity	NPD8039	Approved
0.5778	Remote Similarity	NPD8338	Approved
0.5763	Remote Similarity	NPD7632	Discontinued
0.575	Remote Similarity	NPD6675	Approved
0.575	Remote Similarity	NPD7128	Approved
0.575	Remote Similarity	NPD6402	Approved
0.575	Remote Similarity	NPD5739	Approved
0.5746	Remote Similarity	NPD8391	Approved
0.5746	Remote Similarity	NPD8392	Approved
0.5746	Remote Similarity	NPD8390	Approved
0.5738	Remote Similarity	NPD6014	Approved
0.5738	Remote Similarity	NPD6013	Approved
0.5738	Remote Similarity	NPD6012	Approved
0.5736	Remote Similarity	NPD5983	Phase 2
0.5727	Remote Similarity	NPD3573	Approved
0.5725	Remote Similarity	NPD8341	Approved
0.5725	Remote Similarity	NPD8299	Approved
0.5725	Remote Similarity	NPD8340	Approved
0.5725	Remote Similarity	NPD8342	Approved
0.5714	Remote Similarity	NPD5207	Approved
0.5714	Remote Similarity	NPD6033	Approved
0.5702	Remote Similarity	NPD5701	Approved
0.5701	Remote Similarity	NPD6435	Approved
0.5691	Remote Similarity	NPD7102	Approved
0.5691	Remote Similarity	NPD6883	Approved
0.5691	Remote Similarity	NPD7290	Approved
0.569	Remote Similarity	NPD7902	Approved
0.5688	Remote Similarity	NPD5363	Approved
0.5664	Remote Similarity	NPD6411	Approved
0.566	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5656	Remote Similarity	NPD6011	Approved
0.5652	Remote Similarity	NPD5695	Phase 3
0.5649	Remote Similarity	NPD7122	Discontinued
0.5649	Remote Similarity	NPD7604	Phase 2
0.5648	Remote Similarity	NPD5362	Discontinued
0.5648	Remote Similarity	NPD7154	Phase 3
0.5645	Remote Similarity	NPD2204	Approved
0.5645	Remote Similarity	NPD6847	Approved
0.5645	Remote Similarity	NPD8130	Phase 1
0.5645	Remote Similarity	NPD6617	Approved
0.5645	Remote Similarity	NPD6869	Approved
0.5641	Remote Similarity	NPD5696	Approved
0.5636	Remote Similarity	NPD5786	Approved
0.563	Remote Similarity	NPD5956	Approved
0.5625	Remote Similarity	NPD6051	Approved
0.5619	Remote Similarity	NPD5784	Clinical (unspecified phase)

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