NPASS Compound

Structure

NPC471879 OpenBabel07101718292D 25 26 0 0 1 0 0 0 0 0999 V2000 4.9641 0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9641 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4641 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9641 1.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.9641 0.1340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 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 2 1 0 0 0 0 1 9 1 0 0 0 0 2 16 1 0 0 0 0 3 4 1 0 0 0 0 4 24 1 0 0 0 0 5 9 1 0 0 0 0 5 11 1 0 0 0 0 6 17 1 0 0 0 0 7 18 1 0 0 0 0 8 16 1 0 0 0 0 8 19 1 0 0 0 0 9 6 1 1 0 0 0 10 7 1 6 0 0 0 10 12 1 0 0 0 0 10 25 1 0 0 0 0 11 16 1 1 0 0 0 11 20 1 0 0 0 0 12 13 1 0 0 0 0 12 21 1 1 0 0 0 13 14 1 0 0 0 0 13 22 1 6 0 0 0 14 15 1 0 0 0 0 14 23 1 1 0 0 0 15 24 1 6 0 0 0 15 25 1 0 0 0 0 16 3 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	366.19
Volume:	347.291
LogP:	-1.72
LogD:	-1.829
LogS:	-0.406
# Rotatable Bonds:	7
TPSA:	160.07
# H-Bond Aceptor:	9
# H-Bond Donor:	7
# Rings:	2
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.255
Synthetic Accessibility Score:	4.613
Fsp3:	1.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.186
MDCK Permeability:	0.00014836122863925993
Pgp-inhibitor:	0.006
Pgp-substrate:	0.577
Human Intestinal Absorption (HIA):	0.954
20% Bioavailability (F20%):	0.973
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.192
Plasma Protein Binding (PPB):	17.60426902770996%
Volume Distribution (VD):	0.378
Pgp-substrate:	66.88726806640625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.051
CYP2C19-inhibitor:	0.005
CYP2C19-substrate:	0.104
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.027
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.074
CYP3A4-inhibitor:	0.013
CYP3A4-substrate:	0.019

ADMET: Excretion

Clearance (CL):	1.334
Half-life (T1/2):	0.869

ADMET: Toxicity

hERG Blockers:	0.137
Human Hepatotoxicity (H-HT):	0.401
Drug-inuced Liver Injury (DILI):	0.029
AMES Toxicity:	0.102
Rat Oral Acute Toxicity:	0.01
Maximum Recommended Daily Dose:	0.259
Skin Sensitization:	0.89
Carcinogencity:	0.443
Eye Corrosion:	0.003
Eye Irritation:	0.249
Respiratory Toxicity:	0.423

Download Data

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

Natural Product: NPC471879

Natural Product ID:	NPC471879
*Common Name:**	(2R,3R,4S,5S,6R)-2-[2-[(1R,2S,4S)-2-Hydroxy-1,4-Bis(Hydroxymethyl)Cyclohexyl]Ethoxy]-6-(Hydroxymethyl)Oxane-3,4,5-Triol
IUPAC Name:	(2R,3R,4S,5S,6R)-2-[2-[(1R,2S,4S)-2-hydroxy-1,4-bis(hydroxymethyl)cyclohexyl]ethoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	HFRGFNKHWRASCS-LZXKGRQDSA-N
Standard InCHI:	InChI=1S/C16H30O9/c17-6-9-1-2-16(8-19,11(20)5-9)3-4-24-15-14(23)13(22)12(21)10(7-18)25-15/h9-15,17-23H,1-8H2/t9-,10+,11-,12+,13-,14+,15+,16+/m0/s1
SMILES:	C1CC(C(CC1CO)O)(CCOC2C(C(C(C(O2)CO)O)O)O)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3262209
PubChem CID:	90676292
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001766] Fatty acyl glycosides [CHEMONTID:0003861] Fatty acyl glycosides of mono- and disaccharides

*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
NPO9348	Cananga odorata	Species	Annonaceae	Eukaryota	fruits	n.a.	n.a.	PMID[11374955]
NPO9348	Cananga odorata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21504145]
NPO9348	Cananga odorata	Species	Annonaceae	Eukaryota	flower buds	Thailand	n.a.	PMID[24601675]
NPO9348	Cananga odorata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9348	Cananga odorata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9348	Cananga odorata	Species	Annonaceae	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	6

Activity Type	# Activity
Others	6

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	Inhibition	=	16.1	%	PMID[479196]
NPT2	Others	Unspecified	Inhibition	=	17.9	%	PMID[479196]
NPT2	Others	Unspecified	Inhibition	=	15.3	%	PMID[479196]
NPT2	Others	Unspecified	Inhibition	=	-2.5	%	PMID[479196]
NPT2	Others	Unspecified	Inhibition	=	-9.4	%	PMID[479196]
NPT27	Others	Unspecified	Activity	>	80.3	%	PMID[479196]

☑ 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 NPC471879 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	566
0.1-0.2	4512
0.2-0.3	12846
0.3-0.4	11959
0.4-0.5	6433
0.5-0.6	4667
0.6-0.7	1541
0.7-0.8	157
0.8-0.85	2
0.85-0.9	12
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9	High Similarity	NPC166250
0.8767	High Similarity	NPC272841
0.8767	High Similarity	NPC177343
0.8732	High Similarity	NPC308489
0.8442	Intermediate Similarity	NPC241959
0.8406	Intermediate Similarity	NPC179823
0.8406	Intermediate Similarity	NPC477758
0.8406	Intermediate Similarity	NPC477754
0.8406	Intermediate Similarity	NPC477761
0.8406	Intermediate Similarity	NPC477760
0.8406	Intermediate Similarity	NPC477759
0.8261	Intermediate Similarity	NPC477756
0.8261	Intermediate Similarity	NPC477752
0.8261	Intermediate Similarity	NPC477751
0.8261	Intermediate Similarity	NPC477764
0.8125	Intermediate Similarity	NPC268633
0.8025	Intermediate Similarity	NPC472396
0.8025	Intermediate Similarity	NPC43912
0.8025	Intermediate Similarity	NPC140446
0.8	Intermediate Similarity	NPC290612
0.7927	Intermediate Similarity	NPC281004
0.7901	Intermediate Similarity	NPC107603
0.7901	Intermediate Similarity	NPC471411
0.7901	Intermediate Similarity	NPC471410
0.7875	Intermediate Similarity	NPC474156
0.7831	Intermediate Similarity	NPC102725
0.7831	Intermediate Similarity	NPC131466
0.7831	Intermediate Similarity	NPC473472
0.7831	Intermediate Similarity	NPC82955
0.7821	Intermediate Similarity	NPC186588
0.7763	Intermediate Similarity	NPC279575
0.7763	Intermediate Similarity	NPC107963
0.7738	Intermediate Similarity	NPC65550
0.7738	Intermediate Similarity	NPC473542
0.7738	Intermediate Similarity	NPC223143
0.7738	Intermediate Similarity	NPC279329
0.7733	Intermediate Similarity	NPC200167
0.7733	Intermediate Similarity	NPC53868
0.7733	Intermediate Similarity	NPC209666
0.7733	Intermediate Similarity	NPC31046
0.7662	Intermediate Similarity	NPC188793
0.7654	Intermediate Similarity	NPC166279
0.7654	Intermediate Similarity	NPC18953
0.7647	Intermediate Similarity	NPC204881
0.7647	Intermediate Similarity	NPC473637
0.7647	Intermediate Similarity	NPC473830
0.7647	Intermediate Similarity	NPC36372
0.7647	Intermediate Similarity	NPC229801
0.7647	Intermediate Similarity	NPC293609
0.7647	Intermediate Similarity	NPC149966
0.7647	Intermediate Similarity	NPC476668
0.7647	Intermediate Similarity	NPC210759
0.7647	Intermediate Similarity	NPC5632
0.7647	Intermediate Similarity	NPC307167
0.7619	Intermediate Similarity	NPC20822
0.7558	Intermediate Similarity	NPC311246
0.7558	Intermediate Similarity	NPC149400
0.7558	Intermediate Similarity	NPC476669
0.7558	Intermediate Similarity	NPC88962
0.7558	Intermediate Similarity	NPC277774
0.7558	Intermediate Similarity	NPC473726
0.7558	Intermediate Similarity	NPC323231
0.7558	Intermediate Similarity	NPC18724
0.7558	Intermediate Similarity	NPC470623
0.7558	Intermediate Similarity	NPC224003
0.7558	Intermediate Similarity	NPC172838
0.7558	Intermediate Similarity	NPC137004
0.7558	Intermediate Similarity	NPC171741
0.7558	Intermediate Similarity	NPC144790
0.7558	Intermediate Similarity	NPC167644
0.7536	Intermediate Similarity	NPC477757
0.7536	Intermediate Similarity	NPC477763
0.7536	Intermediate Similarity	NPC477755
0.7536	Intermediate Similarity	NPC477750
0.7536	Intermediate Similarity	NPC477762
0.7536	Intermediate Similarity	NPC477753
0.7529	Intermediate Similarity	NPC474249
0.7529	Intermediate Similarity	NPC261990
0.75	Intermediate Similarity	NPC470872
0.75	Intermediate Similarity	NPC16090
0.75	Intermediate Similarity	NPC138273
0.7471	Intermediate Similarity	NPC305418
0.7471	Intermediate Similarity	NPC151214
0.7471	Intermediate Similarity	NPC131693
0.7471	Intermediate Similarity	NPC113500
0.7471	Intermediate Similarity	NPC174024
0.7471	Intermediate Similarity	NPC179859
0.7471	Intermediate Similarity	NPC471373
0.7471	Intermediate Similarity	NPC473774
0.7471	Intermediate Similarity	NPC45959
0.7471	Intermediate Similarity	NPC252253
0.7471	Intermediate Similarity	NPC309866
0.7471	Intermediate Similarity	NPC175
0.7471	Intermediate Similarity	NPC267238
0.7471	Intermediate Similarity	NPC475325
0.7471	Intermediate Similarity	NPC3538
0.7471	Intermediate Similarity	NPC24960
0.7471	Intermediate Similarity	NPC291547
0.7471	Intermediate Similarity	NPC475436
0.7471	Intermediate Similarity	NPC473851
0.7471	Intermediate Similarity	NPC77717
0.7471	Intermediate Similarity	NPC473503
0.7471	Intermediate Similarity	NPC477224
0.7471	Intermediate Similarity	NPC312678
0.7471	Intermediate Similarity	NPC253611
0.7471	Intermediate Similarity	NPC253268
0.7471	Intermediate Similarity	NPC148593
0.7471	Intermediate Similarity	NPC191915
0.7468	Intermediate Similarity	NPC170595
0.7463	Intermediate Similarity	NPC148424
0.7403	Intermediate Similarity	NPC472950
0.7403	Intermediate Similarity	NPC472952
0.7386	Intermediate Similarity	NPC477494
0.7386	Intermediate Similarity	NPC94582
0.7386	Intermediate Similarity	NPC473067
0.7386	Intermediate Similarity	NPC57964
0.7386	Intermediate Similarity	NPC471429
0.7386	Intermediate Similarity	NPC473064
0.7386	Intermediate Similarity	NPC473065
0.7386	Intermediate Similarity	NPC471424
0.7386	Intermediate Similarity	NPC205129
0.7386	Intermediate Similarity	NPC92196
0.7386	Intermediate Similarity	NPC189575
0.7386	Intermediate Similarity	NPC469710
0.7386	Intermediate Similarity	NPC106701
0.7386	Intermediate Similarity	NPC471425
0.7381	Intermediate Similarity	NPC110365
0.7381	Intermediate Similarity	NPC62202
0.7381	Intermediate Similarity	NPC213658
0.7381	Intermediate Similarity	NPC45833
0.7368	Intermediate Similarity	NPC470660
0.7368	Intermediate Similarity	NPC470659
0.7356	Intermediate Similarity	NPC477451
0.7356	Intermediate Similarity	NPC177834
0.7356	Intermediate Similarity	NPC325828
0.7356	Intermediate Similarity	NPC477547
0.7356	Intermediate Similarity	NPC141769
0.7356	Intermediate Similarity	NPC297348
0.7356	Intermediate Similarity	NPC48339
0.7356	Intermediate Similarity	NPC234352
0.7356	Intermediate Similarity	NPC250393
0.7356	Intermediate Similarity	NPC249204
0.7356	Intermediate Similarity	NPC475307
0.7353	Intermediate Similarity	NPC472025
0.7349	Intermediate Similarity	NPC235402
0.7342	Intermediate Similarity	NPC477577
0.7333	Intermediate Similarity	NPC5209
0.7333	Intermediate Similarity	NPC51956
0.7333	Intermediate Similarity	NPC29005
0.7317	Intermediate Similarity	NPC213737
0.7317	Intermediate Similarity	NPC475820
0.7317	Intermediate Similarity	NPC474346
0.7317	Intermediate Similarity	NPC474284
0.7317	Intermediate Similarity	NPC474253
0.7303	Intermediate Similarity	NPC203434
0.7303	Intermediate Similarity	NPC237071
0.7303	Intermediate Similarity	NPC90583
0.7303	Intermediate Similarity	NPC142264
0.7303	Intermediate Similarity	NPC121453
0.7303	Intermediate Similarity	NPC473287
0.7303	Intermediate Similarity	NPC304011
0.7303	Intermediate Similarity	NPC296936
0.7303	Intermediate Similarity	NPC238796
0.7303	Intermediate Similarity	NPC472989
0.7303	Intermediate Similarity	NPC476510
0.7303	Intermediate Similarity	NPC252056
0.7303	Intermediate Similarity	NPC139271
0.7286	Intermediate Similarity	NPC472026
0.7284	Intermediate Similarity	NPC470156
0.7284	Intermediate Similarity	NPC216941
0.7273	Intermediate Similarity	NPC89145
0.7273	Intermediate Similarity	NPC242073
0.7273	Intermediate Similarity	NPC305160
0.7273	Intermediate Similarity	NPC165198
0.7273	Intermediate Similarity	NPC72817
0.7273	Intermediate Similarity	NPC291203
0.7273	Intermediate Similarity	NPC269166
0.7273	Intermediate Similarity	NPC157514
0.7273	Intermediate Similarity	NPC67660
0.7273	Intermediate Similarity	NPC471464
0.7273	Intermediate Similarity	NPC222731
0.7273	Intermediate Similarity	NPC145112
0.7273	Intermediate Similarity	NPC30687
0.7273	Intermediate Similarity	NPC294686
0.7273	Intermediate Similarity	NPC217205
0.7273	Intermediate Similarity	NPC477927
0.7273	Intermediate Similarity	NPC264101
0.7273	Intermediate Similarity	NPC107914
0.7273	Intermediate Similarity	NPC58629
0.7273	Intermediate Similarity	NPC470151
0.7273	Intermediate Similarity	NPC246558
0.7262	Intermediate Similarity	NPC471240
0.7241	Intermediate Similarity	NPC289361
0.7241	Intermediate Similarity	NPC59006
0.7231	Intermediate Similarity	NPC307022
0.7231	Intermediate Similarity	NPC326533
0.7222	Intermediate Similarity	NPC233649
0.7222	Intermediate Similarity	NPC476112
0.7222	Intermediate Similarity	NPC475207
0.7222	Intermediate Similarity	NPC477222

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 NPC471879 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	602
0.1-0.2	4386
0.2-0.3	2829
0.3-0.4	759
0.4-0.5	378
0.5-0.6	150
0.6-0.7	37
0.7-0.8	9
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
0.7808	Intermediate Similarity	NPD7532	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD1811	Approved
0.7733	Intermediate Similarity	NPD1810	Approved
0.7465	Intermediate Similarity	NPD371	Approved
0.7356	Intermediate Similarity	NPD8171	Discontinued
0.7333	Intermediate Similarity	NPD2686	Approved
0.7333	Intermediate Similarity	NPD2687	Approved
0.7333	Intermediate Similarity	NPD2254	Approved
0.7273	Intermediate Similarity	NPD893	Approved
0.7273	Intermediate Similarity	NPD891	Phase 3
0.7273	Intermediate Similarity	NPD892	Phase 3
0.7273	Intermediate Similarity	NPD888	Phase 3
0.7273	Intermediate Similarity	NPD890	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD904	Phase 3
0.7231	Intermediate Similarity	NPD905	Approved
0.7121	Intermediate Similarity	NPD2269	Approved
0.7108	Intermediate Similarity	NPD3670	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD3669	Approved
0.7015	Intermediate Similarity	NPD887	Approved
0.7015	Intermediate Similarity	NPD889	Approved
0.7015	Intermediate Similarity	NPD895	Approved
0.7015	Intermediate Similarity	NPD894	Approved
0.6806	Remote Similarity	NPD6123	Approved
0.6747	Remote Similarity	NPD6928	Phase 2
0.6714	Remote Similarity	NPD2267	Suspended
0.6598	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.65	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD9000	Phase 3
0.6462	Remote Similarity	NPD8998	Phase 2
0.6462	Remote Similarity	NPD8997	Approved
0.6462	Remote Similarity	NPD8993	Phase 1
0.6462	Remote Similarity	NPD8999	Phase 3
0.6329	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD1779	Approved
0.6279	Remote Similarity	NPD1780	Approved
0.6269	Remote Similarity	NPD8965	Approved
0.6269	Remote Similarity	NPD8966	Approved
0.6197	Remote Similarity	NPD7346	Approved
0.6184	Remote Similarity	NPD847	Phase 1
0.6164	Remote Similarity	NPD369	Approved
0.6139	Remote Similarity	NPD6412	Phase 2
0.6119	Remote Similarity	NPD384	Approved
0.6119	Remote Similarity	NPD385	Approved
0.6095	Remote Similarity	NPD8133	Approved
0.6078	Remote Similarity	NPD6686	Approved
0.6075	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6056	Remote Similarity	NPD9036	Phase 3
0.6056	Remote Similarity	NPD9035	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD7328	Approved
0.6019	Remote Similarity	NPD7327	Approved
0.6	Remote Similarity	NPD8788	Approved
0.5963	Remote Similarity	NPD7516	Approved
0.5909	Remote Similarity	NPD8377	Approved
0.5909	Remote Similarity	NPD8294	Approved
0.5904	Remote Similarity	NPD3181	Approved
0.59	Remote Similarity	NPD8086	Approved
0.59	Remote Similarity	NPD8082	Approved
0.59	Remote Similarity	NPD8083	Approved
0.59	Remote Similarity	NPD8084	Approved
0.59	Remote Similarity	NPD8085	Approved
0.59	Remote Similarity	NPD8139	Approved
0.59	Remote Similarity	NPD8138	Approved
0.5875	Remote Similarity	NPD897	Approved
0.5875	Remote Similarity	NPD896	Approved
0.5875	Remote Similarity	NPD898	Approved
0.5856	Remote Similarity	NPD7503	Approved
0.5856	Remote Similarity	NPD8380	Approved
0.5856	Remote Similarity	NPD8378	Approved
0.5856	Remote Similarity	NPD8296	Approved
0.5856	Remote Similarity	NPD8379	Approved
0.5856	Remote Similarity	NPD8033	Approved
0.5856	Remote Similarity	NPD8335	Approved
0.5842	Remote Similarity	NPD8275	Approved
0.5842	Remote Similarity	NPD8276	Approved
0.5833	Remote Similarity	NPD6940	Discontinued
0.5784	Remote Similarity	NPD8081	Approved
0.5773	Remote Similarity	NPD7991	Discontinued
0.5769	Remote Similarity	NPD8174	Phase 2
0.5752	Remote Similarity	NPD8328	Phase 3
0.5747	Remote Similarity	NPD6115	Approved
0.5747	Remote Similarity	NPD6118	Approved
0.5747	Remote Similarity	NPD6114	Approved
0.5747	Remote Similarity	NPD6697	Approved
0.5728	Remote Similarity	NPD8393	Approved
0.5673	Remote Similarity	NPD8307	Discontinued
0.5673	Remote Similarity	NPD8140	Approved
0.5672	Remote Similarity	NPD9006	Approved
0.5652	Remote Similarity	NPD7507	Approved
0.5632	Remote Similarity	NPD6116	Phase 1
0.5631	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5631	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5619	Remote Similarity	NPD5345	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