NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	860.7
Volume:	935.639
LogP:	11.516
LogD:	4.983
LogS:	-2.849
# Rotatable Bonds:	39
TPSA:	178.53
# H-Bond Aceptor:	11
# H-Bond Donor:	7
# Rings:	2
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.029
Synthetic Accessibility Score:	4.932
Fsp3:	1.0
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.524
MDCK Permeability:	1.174966428152402e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.05
Human Intestinal Absorption (HIA):	0.033
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.905

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	101.8139877319336%
Volume Distribution (VD):	1.254
Pgp-substrate:	1.3651105165481567%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.102
CYP2C19-inhibitor:	0.072
CYP2C19-substrate:	0.04
CYP2C9-inhibitor:	0.021
CYP2C9-substrate:	0.976
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.003
CYP3A4-inhibitor:	0.054
CYP3A4-substrate:	0.002

ADMET: Excretion

Clearance (CL):	3.382
Half-life (T1/2):	0.027

ADMET: Toxicity

hERG Blockers:	0.642
Human Hepatotoxicity (H-HT):	0.009
Drug-inuced Liver Injury (DILI):	0.01
AMES Toxicity:	0.275
Rat Oral Acute Toxicity:	0.004
Maximum Recommended Daily Dose:	0.003
Skin Sensitization:	0.98
Carcinogencity:	0.011
Eye Corrosion:	0.004
Eye Irritation:	0.182
Respiratory Toxicity:	0.457

Download Data

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

Natural Product: NPC477754

Natural Product ID:	NPC477754
*Common Name:**	(2R,3S,4S,5S,6S)-2-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-(3-methylhexatriacontan-18-yloxy)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
IUPAC Name:	(2R,3S,4S,5S,6S)-2-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-(3-methylhexatriacontan-18-yloxy)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	JEOUIBBIISBGRA-ATAGJMRQSA-N
Standard InCHI:	InChI=1S/C49H96O11/c1-4-6-7-8-9-10-11-12-13-14-15-19-22-25-28-31-34-39(35-32-29-26-23-20-17-16-18-21-24-27-30-33-38(3)5-2)57-48-46(56)44(54)47(41(37-51)59-48)60-49-45(55)43(53)42(52)40(36-50)58-49/h38-56H,4-37H2,1-3H3/t38?,39?,40-,41-,42+,43-,44+,45-,46-,47-,48+,49+/m0/s1
SMILES:	CCCCCCCCCCCCCCCCCCC(CCCCCCCCCCCCCCC(C)CC)O[C@H]1[C@H]([C@H]([C@H]([C@@H](O1)CO)O[C@@H]2[C@H]([C@H]([C@@H]([C@@H](O2)CO)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	71716601
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001766] Fatty acyl glycosides [CHEMONTID:0002125] Alkyl glycosides [CHEMONTID:0001754] Simplexides

*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
NPO26409	Plakortis simplex	Species	Plakinidae	Eukaryota	n.a.	Caribbean	n.a.	PMID[10021943]
NPO26409	Plakortis simplex	Species	Plakinidae	Eukaryota	n.a.	Taiwan	n.a.	PMID[11277748]
NPO26409	Plakortis simplex	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921424]
NPO26409	Plakortis simplex	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23806071]
NPO26409	Plakortis simplex	Species	Plakinidae	Eukaryota	n.a.	China	n.a.	PMID[25115700]
NPO26409	Plakortis simplex	Species	Plakinidae	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
Others	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2246	Cell Line	T-cells		Inhibition	=	43	%	PMID[10021943]
NPT2246	Cell Line	T-cells		Inhibition	=	79	%	PMID[10021943]

☑ 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 NPC477754 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	481
0.1-0.2	4292
0.2-0.3	14059
0.3-0.4	11496
0.4-0.5	7658
0.5-0.6	3709
0.6-0.7	847
0.7-0.8	116
0.8-0.85	20
0.85-0.9	4
0.9-0.95	6
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477758
1.0	High Similarity	NPC477759
1.0	High Similarity	NPC477760
1.0	High Similarity	NPC477761
0.9839	High Similarity	NPC477752
0.9839	High Similarity	NPC477751
0.9839	High Similarity	NPC477764
0.9839	High Similarity	NPC477756
0.9032	High Similarity	NPC477755
0.9032	High Similarity	NPC477753
0.9032	High Similarity	NPC477762
0.9032	High Similarity	NPC477750
0.9032	High Similarity	NPC477757
0.9032	High Similarity	NPC477763
0.8571	High Similarity	NPC138273
0.8548	High Similarity	NPC472025
0.8485	Intermediate Similarity	NPC471761
0.8485	Intermediate Similarity	NPC190418
0.8485	Intermediate Similarity	NPC471760
0.8406	Intermediate Similarity	NPC471879
0.8387	Intermediate Similarity	NPC148424
0.8333	Intermediate Similarity	NPC279575
0.831	Intermediate Similarity	NPC166250
0.831	Intermediate Similarity	NPC308489
0.8154	Intermediate Similarity	NPC472026
0.8116	Intermediate Similarity	NPC67099
0.8108	Intermediate Similarity	NPC272841
0.8065	Intermediate Similarity	NPC303727
0.8	Intermediate Similarity	NPC170595
0.8	Intermediate Similarity	NPC211428
0.7971	Intermediate Similarity	NPC179823
0.7917	Intermediate Similarity	NPC470659
0.7917	Intermediate Similarity	NPC470660
0.7903	Intermediate Similarity	NPC67660
0.7903	Intermediate Similarity	NPC269166
0.7903	Intermediate Similarity	NPC107914
0.7903	Intermediate Similarity	NPC165198
0.7903	Intermediate Similarity	NPC89145
0.7903	Intermediate Similarity	NPC246558
0.7903	Intermediate Similarity	NPC145112
0.7903	Intermediate Similarity	NPC242073
0.7903	Intermediate Similarity	NPC58629
0.7903	Intermediate Similarity	NPC157514
0.7887	Intermediate Similarity	NPC53760
0.7887	Intermediate Similarity	NPC52268
0.7867	Intermediate Similarity	NPC177343
0.7857	Intermediate Similarity	NPC50228
0.7857	Intermediate Similarity	NPC97736
0.7846	Intermediate Similarity	NPC290179
0.7846	Intermediate Similarity	NPC34877
0.7846	Intermediate Similarity	NPC317023
0.7763	Intermediate Similarity	NPC294748
0.7763	Intermediate Similarity	NPC22742
0.7763	Intermediate Similarity	NPC158302
0.7763	Intermediate Similarity	NPC477346
0.7763	Intermediate Similarity	NPC477344
0.7763	Intermediate Similarity	NPC85759
0.7763	Intermediate Similarity	NPC146992
0.7746	Intermediate Similarity	NPC241265
0.7746	Intermediate Similarity	NPC285003
0.7733	Intermediate Similarity	NPC188793
0.7692	Intermediate Similarity	NPC219040
0.7671	Intermediate Similarity	NPC308096
0.7671	Intermediate Similarity	NPC206823
0.7671	Intermediate Similarity	NPC169085
0.7671	Intermediate Similarity	NPC9763
0.7671	Intermediate Similarity	NPC39266
0.7671	Intermediate Similarity	NPC291228
0.7671	Intermediate Similarity	NPC225748
0.7654	Intermediate Similarity	NPC470282
0.7595	Intermediate Similarity	NPC241959
0.7581	Intermediate Similarity	NPC233726
0.7581	Intermediate Similarity	NPC23134
0.7581	Intermediate Similarity	NPC326533
0.7581	Intermediate Similarity	NPC124963
0.7564	Intermediate Similarity	NPC477317
0.7564	Intermediate Similarity	NPC472202
0.7564	Intermediate Similarity	NPC169345
0.7564	Intermediate Similarity	NPC472200
0.7564	Intermediate Similarity	NPC173328
0.7564	Intermediate Similarity	NPC477318
0.7564	Intermediate Similarity	NPC123204
0.7564	Intermediate Similarity	NPC184915
0.7564	Intermediate Similarity	NPC259294
0.7564	Intermediate Similarity	NPC290012
0.7564	Intermediate Similarity	NPC477331
0.7564	Intermediate Similarity	NPC27289
0.7564	Intermediate Similarity	NPC269318
0.7564	Intermediate Similarity	NPC477319
0.7564	Intermediate Similarity	NPC477347
0.7564	Intermediate Similarity	NPC44782
0.7564	Intermediate Similarity	NPC143421
0.7564	Intermediate Similarity	NPC472203
0.7564	Intermediate Similarity	NPC475327
0.7564	Intermediate Similarity	NPC475270
0.7564	Intermediate Similarity	NPC224953
0.7564	Intermediate Similarity	NPC475667
0.7564	Intermediate Similarity	NPC115013
0.7564	Intermediate Similarity	NPC472204
0.7564	Intermediate Similarity	NPC119583
0.7564	Intermediate Similarity	NPC307400
0.7564	Intermediate Similarity	NPC183888
0.7564	Intermediate Similarity	NPC238056
0.7564	Intermediate Similarity	NPC472201
0.7564	Intermediate Similarity	NPC472205
0.7564	Intermediate Similarity	NPC476087
0.7564	Intermediate Similarity	NPC126685
0.7564	Intermediate Similarity	NPC186992
0.7564	Intermediate Similarity	NPC297768
0.7564	Intermediate Similarity	NPC89843
0.7561	Intermediate Similarity	NPC470284
0.7536	Intermediate Similarity	NPC6848
0.7534	Intermediate Similarity	NPC184550
0.7534	Intermediate Similarity	NPC185419
0.747	Intermediate Similarity	NPC131466
0.7468	Intermediate Similarity	NPC20072
0.7465	Intermediate Similarity	NPC206601
0.7439	Intermediate Similarity	NPC140446
0.7439	Intermediate Similarity	NPC43912
0.7436	Intermediate Similarity	NPC267592
0.7436	Intermediate Similarity	NPC100697
0.7432	Intermediate Similarity	NPC163812
0.7432	Intermediate Similarity	NPC55652
0.7429	Intermediate Similarity	NPC12040
0.7429	Intermediate Similarity	NPC147292
0.7429	Intermediate Similarity	NPC76881
0.7424	Intermediate Similarity	NPC322148
0.7381	Intermediate Similarity	NPC65550
0.7375	Intermediate Similarity	NPC477332
0.7375	Intermediate Similarity	NPC60849
0.7375	Intermediate Similarity	NPC472352
0.7368	Intermediate Similarity	NPC477350
0.7349	Intermediate Similarity	NPC281004
0.7344	Intermediate Similarity	NPC130683
0.7344	Intermediate Similarity	NPC323361
0.7342	Intermediate Similarity	NPC216941
0.7342	Intermediate Similarity	NPC16090
0.7333	Intermediate Similarity	NPC31046
0.7333	Intermediate Similarity	NPC209666
0.7333	Intermediate Similarity	NPC53868
0.7333	Intermediate Similarity	NPC200167
0.7317	Intermediate Similarity	NPC470657
0.7317	Intermediate Similarity	NPC107603
0.7297	Intermediate Similarity	NPC470173
0.7294	Intermediate Similarity	NPC210759
0.7294	Intermediate Similarity	NPC229801
0.7294	Intermediate Similarity	NPC473830
0.7294	Intermediate Similarity	NPC307167
0.7294	Intermediate Similarity	NPC204881
0.7284	Intermediate Similarity	NPC476523
0.7284	Intermediate Similarity	NPC166279
0.7284	Intermediate Similarity	NPC474156
0.7273	Intermediate Similarity	NPC476782
0.7273	Intermediate Similarity	NPC216883
0.7273	Intermediate Similarity	NPC476783
0.7273	Intermediate Similarity	NPC476781
0.7262	Intermediate Similarity	NPC102725
0.7262	Intermediate Similarity	NPC82955
0.7262	Intermediate Similarity	NPC473472
0.7258	Intermediate Similarity	NPC42503
0.7258	Intermediate Similarity	NPC299781
0.7258	Intermediate Similarity	NPC282143
0.7258	Intermediate Similarity	NPC157193
0.725	Intermediate Similarity	NPC475849
0.7229	Intermediate Similarity	NPC472396
0.7229	Intermediate Similarity	NPC314364
0.7229	Intermediate Similarity	NPC31349
0.7229	Intermediate Similarity	NPC51662
0.7209	Intermediate Similarity	NPC48339
0.7209	Intermediate Similarity	NPC172838
0.7209	Intermediate Similarity	NPC144790
0.7209	Intermediate Similarity	NPC88962
0.7209	Intermediate Similarity	NPC141769
0.7209	Intermediate Similarity	NPC323231
0.7209	Intermediate Similarity	NPC250393
0.7209	Intermediate Similarity	NPC477451
0.7209	Intermediate Similarity	NPC477547
0.7209	Intermediate Similarity	NPC473726
0.7209	Intermediate Similarity	NPC234352
0.7209	Intermediate Similarity	NPC470623
0.7209	Intermediate Similarity	NPC171741
0.7209	Intermediate Similarity	NPC18724
0.7209	Intermediate Similarity	NPC149400
0.7209	Intermediate Similarity	NPC224003
0.7209	Intermediate Similarity	NPC249204
0.7209	Intermediate Similarity	NPC325828
0.7209	Intermediate Similarity	NPC137004
0.7209	Intermediate Similarity	NPC177834
0.7209	Intermediate Similarity	NPC297348
0.72	Intermediate Similarity	NPC248427
0.7195	Intermediate Similarity	NPC290612
0.7179	Intermediate Similarity	NPC477330
0.7179	Intermediate Similarity	NPC146380
0.7179	Intermediate Similarity	NPC477325
0.7179	Intermediate Similarity	NPC109887
0.7179	Intermediate Similarity	NPC477328
0.7179	Intermediate Similarity	NPC475425
0.7179	Intermediate Similarity	NPC477326
0.7179	Intermediate Similarity	NPC477329
0.7179	Intermediate Similarity	NPC477320

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 NPC477754 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	474
0.1-0.2	4321
0.2-0.3	3039
0.3-0.4	751
0.4-0.5	359
0.5-0.6	150
0.6-0.7	45
0.7-0.8	6
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7903	Intermediate Similarity	NPD888	Phase 3
0.7903	Intermediate Similarity	NPD892	Phase 3
0.7903	Intermediate Similarity	NPD890	Clinical (unspecified phase)
0.7903	Intermediate Similarity	NPD893	Approved
0.7903	Intermediate Similarity	NPD891	Phase 3
0.7742	Intermediate Similarity	NPD2269	Approved
0.7639	Intermediate Similarity	NPD7532	Clinical (unspecified phase)
0.7612	Intermediate Similarity	NPD6123	Approved
0.7581	Intermediate Similarity	NPD905	Approved
0.7581	Intermediate Similarity	NPD904	Phase 3
0.7344	Intermediate Similarity	NPD894	Approved
0.7344	Intermediate Similarity	NPD889	Approved
0.7344	Intermediate Similarity	NPD895	Approved
0.7344	Intermediate Similarity	NPD887	Approved
0.7333	Intermediate Similarity	NPD1811	Approved
0.7333	Intermediate Similarity	NPD1810	Approved
0.7273	Intermediate Similarity	NPD2267	Suspended
0.7231	Intermediate Similarity	NPD7346	Approved
0.7209	Intermediate Similarity	NPD8171	Discontinued
0.6933	Remote Similarity	NPD2686	Approved
0.6933	Remote Similarity	NPD2687	Approved
0.6933	Remote Similarity	NPD2254	Approved
0.6806	Remote Similarity	NPD371	Approved
0.6774	Remote Similarity	NPD9000	Phase 3
0.6774	Remote Similarity	NPD8998	Phase 2
0.6774	Remote Similarity	NPD8993	Phase 1
0.6774	Remote Similarity	NPD8997	Approved
0.6774	Remote Similarity	NPD8999	Phase 3
0.6747	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD3669	Approved
0.6667	Remote Similarity	NPD369	Approved
0.6596	Remote Similarity	NPD8139	Approved
0.6596	Remote Similarity	NPD8084	Approved
0.6596	Remote Similarity	NPD8085	Approved
0.6596	Remote Similarity	NPD8086	Approved
0.6596	Remote Similarity	NPD8138	Approved
0.6596	Remote Similarity	NPD8082	Approved
0.6596	Remote Similarity	NPD8083	Approved
0.6562	Remote Similarity	NPD8966	Approved
0.6562	Remote Similarity	NPD8965	Approved
0.6538	Remote Similarity	NPD3181	Approved
0.6526	Remote Similarity	NPD8276	Approved
0.6526	Remote Similarity	NPD8275	Approved
0.6458	Remote Similarity	NPD8081	Approved
0.6458	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD847	Phase 1
0.6392	Remote Similarity	NPD8393	Approved
0.6327	Remote Similarity	NPD8307	Discontinued
0.6327	Remote Similarity	NPD8140	Approved
0.6324	Remote Similarity	NPD9036	Phase 3
0.6324	Remote Similarity	NPD9035	Clinical (unspecified phase)
0.629	Remote Similarity	NPD8788	Approved
0.6265	Remote Similarity	NPD7329	Approved
0.62	Remote Similarity	NPD8306	Approved
0.62	Remote Similarity	NPD8305	Approved
0.619	Remote Similarity	NPD6928	Phase 2
0.6139	Remote Similarity	NPD8087	Discontinued
0.6133	Remote Similarity	NPD7909	Approved
0.6105	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6104	Remote Similarity	NPD896	Approved
0.6104	Remote Similarity	NPD898	Approved
0.6104	Remote Similarity	NPD897	Approved
0.604	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5968	Remote Similarity	NPD7536	Approved
0.5962	Remote Similarity	NPD8133	Approved
0.5941	Remote Similarity	NPD6686	Approved
0.5938	Remote Similarity	NPD9006	Approved
0.593	Remote Similarity	NPD1779	Approved
0.593	Remote Similarity	NPD1780	Approved
0.5921	Remote Similarity	NPD1457	Discontinued
0.587	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.587	Remote Similarity	NPD46	Approved
0.587	Remote Similarity	NPD6698	Approved
0.5842	Remote Similarity	NPD6412	Phase 2
0.5794	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5784	Remote Similarity	NPD8174	Phase 2
0.5775	Remote Similarity	NPD3728	Approved
0.5775	Remote Similarity	NPD3730	Approved
0.5769	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD8301	Approved
0.5758	Remote Similarity	NPD8300	Approved
0.5714	Remote Similarity	NPD4835	Approved
0.5714	Remote Similarity	NPD4837	Approved
0.5714	Remote Similarity	NPD4836	Approved
0.5714	Remote Similarity	NPD4838	Approved
0.5699	Remote Similarity	NPD7838	Discovery
0.5694	Remote Similarity	NPD885	Approved
0.5694	Remote Similarity	NPD884	Clinical (unspecified phase)
0.5638	Remote Similarity	NPD7983	Approved
0.5636	Remote Similarity	NPD8347	Approved
0.5636	Remote Similarity	NPD8377	Approved
0.5636	Remote Similarity	NPD8294	Approved
0.5636	Remote Similarity	NPD8346	Approved
0.5636	Remote Similarity	NPD8345	Approved
0.5606	Remote Similarity	NPD9219	Approved
0.5606	Remote Similarity	NPD9218	Clinical (unspecified phase)
0.5604	Remote Similarity	NPD3200	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