NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	180.06
Volume:	156.517
LogP:	-2.198
LogD:	-1.709
LogS:	-0.067
# Rotatable Bonds:	1
TPSA:	110.38
# H-Bond Aceptor:	6
# H-Bond Donor:	5
# Rings:	1
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.29
Synthetic Accessibility Score:	4.138
Fsp3:	1.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.379
MDCK Permeability:	0.002639307174831629
Pgp-inhibitor:	0.001
Pgp-substrate:	0.08
Human Intestinal Absorption (HIA):	0.845
20% Bioavailability (F20%):	0.459
30% Bioavailability (F30%):	0.207

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.63
Plasma Protein Binding (PPB):	10.789892196655273%
Volume Distribution (VD):	0.562
Pgp-substrate:	81.19158935546875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.059
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.106
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.144
CYP3A4-inhibitor:	0.005
CYP3A4-substrate:	0.019

ADMET: Excretion

Clearance (CL):	2.133
Half-life (T1/2):	0.684

ADMET: Toxicity

hERG Blockers:	0.062
Human Hepatotoxicity (H-HT):	0.043
Drug-inuced Liver Injury (DILI):	0.056
AMES Toxicity:	0.08
Rat Oral Acute Toxicity:	0.015
Maximum Recommended Daily Dose:	0.002
Skin Sensitization:	0.051
Carcinogencity:	0.016
Eye Corrosion:	0.003
Eye Irritation:	0.026
Respiratory Toxicity:	0.011

Download Data

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

Natural Product: NPC320240

Natural Product ID:	NPC320240
*Common Name:**	2-(Hydroxymethyl)Oxane-2,3,4,5-Tetrol
IUPAC Name:	2-(hydroxymethyl)oxane-2,3,4,5-tetrol
Synonyms:
Standard InCHIKey:	LKDRXBCSQODPBY-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C6H12O6/c7-2-6(11)5(10)4(9)3(8)1-12-6/h3-5,7-11H,1-2H2
SMILES:	C1C(C(C(C(O1)(CO)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL23954
PubChem CID:	3426
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0001540] Monosaccharides

*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
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18409045]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[19926279]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	root	n.a.	PMID[2092947]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	berry	n.a.	n.a.	PMID[21216145]
NPO12582	Camptotheca acuminata	Species	Nyssaceae	Eukaryota	n.a.	xylem	n.a.	PMID[21348469]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	leaves	n.a.	n.a.	PMID[24290061]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24968750]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25152999]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	stems-leaves	n.a.	n.a.	PMID[26420067]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	stem	n.a.	PMID[27914541]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	Flower Buds	n.a.	n.a.	PMID[28345906]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32129622]
NPO12582	Camptotheca acuminata	Species	Nyssaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3735324]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12582	Camptotheca acuminata	Species	Nyssaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12582	Camptotheca acuminata	Species	Nyssaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12582	Camptotheca acuminata	Species	Nyssaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12582	Camptotheca acuminata	Species	Nyssaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26622	Taraxacum officinale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29141	Panax ginseng	Species	Araliaceae	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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1727	Individual Protein	Acrosin	Homo sapiens	Inhibition	=	58.0	%	PMID[467796]

☑ 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 NPC320240 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	1254
0.1-0.2	11166
0.2-0.3	17935
0.3-0.4	9931
0.4-0.5	1951
0.5-0.6	293
0.6-0.7	78
0.7-0.8	36
0.8-0.85	22
0.85-0.9	15
0.9-0.95	4
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC70756
0.9524	High Similarity	NPC255377
0.9524	High Similarity	NPC21209
0.9524	High Similarity	NPC199857
0.9524	High Similarity	NPC285364
0.9524	High Similarity	NPC69445
0.9524	High Similarity	NPC92246
0.9524	High Similarity	NPC289758
0.9524	High Similarity	NPC73906
0.9524	High Similarity	NPC165846
0.9524	High Similarity	NPC176017
0.9302	High Similarity	NPC321087
0.9302	High Similarity	NPC277475
0.925	High Similarity	NPC266553
0.9091	High Similarity	NPC14144
0.9048	High Similarity	NPC29721
0.8889	High Similarity	NPC42503
0.8889	High Similarity	NPC157193
0.8889	High Similarity	NPC299781
0.8889	High Similarity	NPC282143
0.881	High Similarity	NPC86191
0.881	High Similarity	NPC134252
0.881	High Similarity	NPC213159
0.881	High Similarity	NPC291502
0.881	High Similarity	NPC317182
0.881	High Similarity	NPC298699
0.8696	High Similarity	NPC323574
0.8511	High Similarity	NPC124963
0.8511	High Similarity	NPC23134
0.8511	High Similarity	NPC326533
0.8511	High Similarity	NPC233726
0.8444	Intermediate Similarity	NPC252918
0.8444	Intermediate Similarity	NPC230789
0.8163	Intermediate Similarity	NPC89145
0.8163	Intermediate Similarity	NPC323361
0.8163	Intermediate Similarity	NPC317501
0.8163	Intermediate Similarity	NPC58629
0.8163	Intermediate Similarity	NPC269166
0.8163	Intermediate Similarity	NPC246558
0.8163	Intermediate Similarity	NPC67660
0.8163	Intermediate Similarity	NPC242073
0.8163	Intermediate Similarity	NPC157514
0.8163	Intermediate Similarity	NPC317626
0.8163	Intermediate Similarity	NPC165198
0.8163	Intermediate Similarity	NPC145112
0.8163	Intermediate Similarity	NPC130683
0.8163	Intermediate Similarity	NPC314821
0.8163	Intermediate Similarity	NPC107914
0.8085	Intermediate Similarity	NPC82512
0.8	Intermediate Similarity	NPC303727
0.8	Intermediate Similarity	NPC66052
0.8	Intermediate Similarity	NPC192065
0.8	Intermediate Similarity	NPC86412
0.8	Intermediate Similarity	NPC325034
0.8	Intermediate Similarity	NPC293908
0.7955	Intermediate Similarity	NPC320189
0.7755	Intermediate Similarity	NPC329095
0.7692	Intermediate Similarity	NPC148424
0.766	Intermediate Similarity	NPC88638
0.7609	Intermediate Similarity	NPC107091
0.7609	Intermediate Similarity	NPC207656
0.76	Intermediate Similarity	NPC320043
0.76	Intermediate Similarity	NPC103672
0.7547	Intermediate Similarity	NPC219040
0.7547	Intermediate Similarity	NPC472025
0.75	Intermediate Similarity	NPC102981
0.75	Intermediate Similarity	NPC111882
0.75	Intermediate Similarity	NPC99573
0.75	Intermediate Similarity	NPC88278
0.75	Intermediate Similarity	NPC227707
0.7407	Intermediate Similarity	NPC317023
0.7407	Intermediate Similarity	NPC320032
0.7407	Intermediate Similarity	NPC322855
0.7407	Intermediate Similarity	NPC290179
0.7407	Intermediate Similarity	NPC34877
0.7273	Intermediate Similarity	NPC143326
0.725	Intermediate Similarity	NPC187058
0.725	Intermediate Similarity	NPC197207
0.725	Intermediate Similarity	NPC182541
0.725	Intermediate Similarity	NPC149070
0.725	Intermediate Similarity	NPC127074
0.7143	Intermediate Similarity	NPC477750
0.7143	Intermediate Similarity	NPC477762
0.7143	Intermediate Similarity	NPC477763
0.7143	Intermediate Similarity	NPC477753
0.7143	Intermediate Similarity	NPC472026
0.7143	Intermediate Similarity	NPC155457
0.7143	Intermediate Similarity	NPC112363
0.7143	Intermediate Similarity	NPC477755
0.7143	Intermediate Similarity	NPC477757
0.6909	Remote Similarity	NPC220922
0.6905	Remote Similarity	NPC227267
0.6897	Remote Similarity	NPC317651
0.6897	Remote Similarity	NPC258690
0.6897	Remote Similarity	NPC268243
0.6897	Remote Similarity	NPC277570
0.6897	Remote Similarity	NPC325773
0.6863	Remote Similarity	NPC329128
0.6863	Remote Similarity	NPC322158
0.678	Remote Similarity	NPC294813
0.678	Remote Similarity	NPC31496
0.678	Remote Similarity	NPC13143
0.678	Remote Similarity	NPC6848
0.6667	Remote Similarity	NPC471761
0.6667	Remote Similarity	NPC190418
0.6667	Remote Similarity	NPC76881
0.6667	Remote Similarity	NPC12040
0.6667	Remote Similarity	NPC471760
0.6667	Remote Similarity	NPC147292
0.66	Remote Similarity	NPC314613
0.6591	Remote Similarity	NPC313405
0.6557	Remote Similarity	NPC477752
0.6557	Remote Similarity	NPC322801
0.6557	Remote Similarity	NPC477756
0.6557	Remote Similarity	NPC477764
0.6557	Remote Similarity	NPC129100
0.6557	Remote Similarity	NPC291650
0.6557	Remote Similarity	NPC477751
0.65	Remote Similarity	NPC301586
0.65	Remote Similarity	NPC33415
0.6452	Remote Similarity	NPC477759
0.6452	Remote Similarity	NPC179823
0.6452	Remote Similarity	NPC477761
0.6452	Remote Similarity	NPC206601
0.6452	Remote Similarity	NPC32148
0.6452	Remote Similarity	NPC477754
0.6452	Remote Similarity	NPC477758
0.6452	Remote Similarity	NPC477760
0.6349	Remote Similarity	NPC50228
0.6349	Remote Similarity	NPC97736
0.6349	Remote Similarity	NPC250619
0.6349	Remote Similarity	NPC67099
0.6346	Remote Similarity	NPC61270
0.6346	Remote Similarity	NPC325822
0.6316	Remote Similarity	NPC293692
0.625	Remote Similarity	NPC320326
0.625	Remote Similarity	NPC326557
0.625	Remote Similarity	NPC211428
0.625	Remote Similarity	NPC285003
0.625	Remote Similarity	NPC327486
0.625	Remote Similarity	NPC241265
0.625	Remote Similarity	NPC223174
0.625	Remote Similarity	NPC327753
0.6207	Remote Similarity	NPC182903
0.62	Remote Similarity	NPC62014
0.6154	Remote Similarity	NPC471879
0.6154	Remote Similarity	NPC247546
0.6154	Remote Similarity	NPC52268
0.6154	Remote Similarity	NPC53760
0.6154	Remote Similarity	NPC474078
0.6154	Remote Similarity	NPC172086
0.6102	Remote Similarity	NPC174485
0.6098	Remote Similarity	NPC325345
0.6071	Remote Similarity	NPC289979
0.6061	Remote Similarity	NPC184550
0.6061	Remote Similarity	NPC185419
0.6038	Remote Similarity	NPC46254
0.6	Remote Similarity	NPC321102
0.6	Remote Similarity	NPC322803
0.6	Remote Similarity	NPC277878
0.6	Remote Similarity	NPC325153
0.6	Remote Similarity	NPC278465
0.597	Remote Similarity	NPC308096
0.597	Remote Similarity	NPC169085
0.597	Remote Similarity	NPC248427
0.597	Remote Similarity	NPC9763
0.597	Remote Similarity	NPC291228
0.597	Remote Similarity	NPC206823
0.597	Remote Similarity	NPC132938
0.597	Remote Similarity	NPC163812
0.597	Remote Similarity	NPC225748
0.597	Remote Similarity	NPC39266
0.5962	Remote Similarity	NPC8597
0.5932	Remote Similarity	NPC476209
0.5893	Remote Similarity	NPC196612
0.5882	Remote Similarity	NPC85078
0.5882	Remote Similarity	NPC472174
0.5882	Remote Similarity	NPC308489
0.5882	Remote Similarity	NPC472173
0.5882	Remote Similarity	NPC166250
0.5882	Remote Similarity	NPC138273
0.5854	Remote Similarity	NPC272307
0.58	Remote Similarity	NPC228782
0.58	Remote Similarity	NPC313565
0.58	Remote Similarity	NPC259982
0.5789	Remote Similarity	NPC23155
0.5789	Remote Similarity	NPC320588
0.5789	Remote Similarity	NPC469937
0.5789	Remote Similarity	NPC53463
0.5763	Remote Similarity	NPC322148
0.575	Remote Similarity	NPC213764
0.5738	Remote Similarity	NPC475412
0.5735	Remote Similarity	NPC55652
0.5735	Remote Similarity	NPC470660
0.5735	Remote Similarity	NPC470659
0.5714	Remote Similarity	NPC300235
0.5714	Remote Similarity	NPC476149
0.5714	Remote Similarity	NPC229655
0.5714	Remote Similarity	NPC244869
0.5714	Remote Similarity	NPC152008

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 NPC320240 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	1516
0.1-0.2	5232
0.2-0.3	1706
0.3-0.4	446
0.4-0.5	144
0.5-0.6	47
0.6-0.7	28
0.7-0.8	6
0.8-0.85	15
0.85-0.9	3
0.9-0.95	2
0.95-1	5

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9524	High Similarity	NPD9000	Phase 3
0.9524	High Similarity	NPD8999	Phase 3
0.9524	High Similarity	NPD8993	Phase 1
0.9524	High Similarity	NPD8998	Phase 2
0.9524	High Similarity	NPD8997	Approved
0.9091	High Similarity	NPD8966	Approved
0.9091	High Similarity	NPD8965	Approved
0.9048	High Similarity	NPD9006	Approved
0.881	High Similarity	NPD8788	Approved
0.8511	High Similarity	NPD905	Approved
0.8511	High Similarity	NPD904	Phase 3
0.8222	Intermediate Similarity	NPD8994	Approved
0.8163	Intermediate Similarity	NPD893	Approved
0.8163	Intermediate Similarity	NPD890	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD892	Phase 3
0.8163	Intermediate Similarity	NPD891	Phase 3
0.8163	Intermediate Similarity	NPD9036	Phase 3
0.8163	Intermediate Similarity	NPD889	Approved
0.8163	Intermediate Similarity	NPD894	Approved
0.8163	Intermediate Similarity	NPD895	Approved
0.8163	Intermediate Similarity	NPD888	Phase 3
0.8163	Intermediate Similarity	NPD887	Approved
0.8163	Intermediate Similarity	NPD9035	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD9052	Approved
0.8	Intermediate Similarity	NPD9051	Approved
0.8	Intermediate Similarity	NPD9053	Approved
0.7959	Intermediate Similarity	NPD2269	Approved
0.7955	Intermediate Similarity	NPD8957	Approved
0.7609	Intermediate Similarity	NPD9219	Approved
0.7609	Intermediate Similarity	NPD9218	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD9050	Approved
0.76	Intermediate Similarity	NPD9049	Discontinued
0.7556	Intermediate Similarity	NPD8958	Phase 2
0.75	Intermediate Similarity	NPD8995	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8996	Phase 3
0.725	Intermediate Similarity	NPD8814	Phase 3
0.7143	Intermediate Similarity	NPD6123	Approved
0.7143	Intermediate Similarity	NPD9139	Approved
0.7037	Intermediate Similarity	NPD2267	Suspended
0.6909	Remote Similarity	NPD8959	Approved
0.6897	Remote Similarity	NPD847	Phase 1
0.6897	Remote Similarity	NPD8961	Approved
0.6607	Remote Similarity	NPD369	Approved
0.6557	Remote Similarity	NPD9031	Approved
0.6557	Remote Similarity	NPD9032	Approved
0.6557	Remote Similarity	NPD9033	Approved
0.6557	Remote Similarity	NPD9030	Approved
0.65	Remote Similarity	NPD8549	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD896	Approved
0.6452	Remote Similarity	NPD898	Approved
0.6452	Remote Similarity	NPD897	Approved
0.6364	Remote Similarity	NPD7346	Approved
0.6346	Remote Similarity	NPD9061	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD8977	Phase 3
0.6304	Remote Similarity	NPD8976	Approved
0.625	Remote Similarity	NPD884	Clinical (unspecified phase)
0.625	Remote Similarity	NPD9445	Approved
0.625	Remote Similarity	NPD885	Approved
0.623	Remote Similarity	NPD1457	Discontinued
0.6154	Remote Similarity	NPD9003	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD9004	Approved
0.6154	Remote Similarity	NPD9005	Phase 3
0.6111	Remote Similarity	NPD1400	Approved
0.6111	Remote Similarity	NPD1399	Approved
0.6098	Remote Similarity	NPD8988	Clinical (unspecified phase)
0.6	Remote Similarity	NPD64	Approved
0.6	Remote Similarity	NPD8960	Approved
0.6	Remote Similarity	NPD9009	Approved
0.6	Remote Similarity	NPD72	Approved
0.6	Remote Similarity	NPD66	Approved
0.6	Remote Similarity	NPD9007	Approved
0.6	Remote Similarity	NPD9008	Approved
0.6	Remote Similarity	NPD9010	Approved
0.6	Remote Similarity	NPD65	Approved
0.6	Remote Similarity	NPD9011	Approved
0.597	Remote Similarity	NPD67	Phase 2
0.597	Remote Similarity	NPD3181	Approved
0.597	Remote Similarity	NPD389	Phase 3
0.597	Remote Similarity	NPD9034	Approved
0.5918	Remote Similarity	NPD8967	Approved
0.5909	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD9110	Approved
0.5818	Remote Similarity	NPD9002	Approved
0.5818	Remote Similarity	NPD9001	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD3730	Approved
0.5789	Remote Similarity	NPD3728	Approved
0.5714	Remote Similarity	NPD371	Approved
0.5714	Remote Similarity	NPD7536	Approved
0.5714	Remote Similarity	NPD372	Clinical (unspecified phase)
0.5634	Remote Similarity	NPD9435	Approved
0.5634	Remote Similarity	NPD9434	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data