NPASS Compound

Structure

CID98276 OpenBabel06191715442D 24 26 0 0 1 0 0 0 0 0999 V2000 3.4641 1.9563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6665 1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0733 0.1691 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 3.4641 0.0000 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 -2.0000 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 2.5981 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6720 0.9781 0.0000 C 0 0 1 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 6.0514 -0.0388 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 -0.0000 -3.0000 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 2.7210 1.2872 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 3 2 0 0 0 0 3 22 1 0 0 0 0 4 7 1 0 0 0 0 4 15 1 0 0 0 0 5 16 1 0 0 0 0 6 2 1 1 0 0 0 6 7 1 0 0 0 0 6 9 1 0 0 0 0 7 17 1 6 0 0 0 8 5 1 1 0 0 0 8 10 1 0 0 0 0 8 23 1 0 0 0 0 9 13 1 0 0 0 0 9 15 1 1 0 0 0 10 11 1 0 0 0 0 10 18 1 6 0 0 0 11 12 1 0 0 0 0 11 19 1 1 0 0 0 12 14 1 0 0 0 0 12 20 1 6 0 0 0 13 22 1 0 0 0 0 13 24 1 6 0 0 0 14 23 1 0 0 0 0 14 24 1 1 0 0 0 15 1 1 1 0 0 0 15 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	348.14
Volume:	318.802
LogP:	-1.355
LogD:	-0.217
LogS:	-1.106
# Rotatable Bonds:	3
TPSA:	149.07
# H-Bond Aceptor:	9
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.323
Synthetic Accessibility Score:	4.938
Fsp3:	0.867
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.077
MDCK Permeability:	0.000131018809042871
Pgp-inhibitor:	0.001
Pgp-substrate:	0.865
Human Intestinal Absorption (HIA):	0.948
20% Bioavailability (F20%):	0.058
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.247
Plasma Protein Binding (PPB):	21.06551170349121%
Volume Distribution (VD):	0.346
Pgp-substrate:	57.548736572265625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.063
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.436
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.067
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.078
CYP3A4-inhibitor:	0.015
CYP3A4-substrate:	0.041

ADMET: Excretion

Clearance (CL):	1.274
Half-life (T1/2):	0.835

ADMET: Toxicity

hERG Blockers:	0.081
Human Hepatotoxicity (H-HT):	0.198
Drug-inuced Liver Injury (DILI):	0.032
AMES Toxicity:	0.078
Rat Oral Acute Toxicity:	0.114
Maximum Recommended Daily Dose:	0.016
Skin Sensitization:	0.178
Carcinogencity:	0.91
Eye Corrosion:	0.004
Eye Irritation:	0.053
Respiratory Toxicity:	0.872

Download Data

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

Natural Product: NPC98276

Natural Product ID:	NPC98276
*Common Name:**	(2S,3R,4S,5S,6R)-2-[[(1R,4As,5S,7R,7Ar)-5,7-Dihydroxy-7-Methyl-4A,5,6,7A-Tetrahydro-1H-Cyclopenta[C]Pyran-1-Yl]Oxy]-6-(Hydroxymethyl)Oxane-3,4,5-Triol
IUPAC Name:	(2S,3R,4S,5S,6R)-2-[[(1R,4aS,5S,7R,7aR)-5,7-dihydroxy-7-methyl-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	VELYAQRXBJLJAK-NAYRNRKNSA-N
Standard InCHI:	InChI=1S/C15H24O9/c1-15(21)4-7(17)6-2-3-22-13(9(6)15)24-14-12(20)11(19)10(18)8(5-16)23-14/h2-3,6-14,16-21H,4-5H2,1H3/t6-,7+,8-,9+,10-,11+,12-,13-,14+,15-/m1/s1
SMILES:	C[C@]1(C[C@@H]([C@H]2C=CO[C@@H]([C@@H]12)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL595516
PubChem CID:	46227138
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0004081] Iridoid O-glycosides

*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
NPO33377	teucrium chamaedris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19674906]

☑ 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	4
Others	3

Activity Type	# Activity
NON-MOLECULAR	6
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	0.5	n.a.	PMID[475410]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	0.7	n.a.	PMID[475410]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	1.7	n.a.	PMID[475410]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	36800.0	nM	PMID[475410]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	41100.0	nM	PMID[475410]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	44100.0	nM	PMID[475410]
NPT1	Others	Radical scavenging activity		IC50	>	300000.0	nM	PMID[475410]

☑ 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 NPC98276 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	162
0.1-0.2	2080
0.2-0.3	8212
0.3-0.4	15558
0.4-0.5	9684
0.5-0.6	5639
0.6-0.7	1266
0.7-0.8	73
0.8-0.85	7
0.85-0.9	6
0.9-0.95	6
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC259296
0.9512	High Similarity	NPC148534
0.9506	High Similarity	NPC149018
0.9506	High Similarity	NPC171484
0.9398	High Similarity	NPC22918
0.9398	High Similarity	NPC50464
0.939	High Similarity	NPC258501
0.8953	High Similarity	NPC294643
0.8953	High Similarity	NPC274274
0.8953	High Similarity	NPC473150
0.8953	High Similarity	NPC276298
0.8941	High Similarity	NPC93190
0.8667	High Similarity	NPC470683
0.8667	High Similarity	NPC470684
0.814	Intermediate Similarity	NPC136699
0.814	Intermediate Similarity	NPC220167
0.7826	Intermediate Similarity	NPC280390
0.7677	Intermediate Similarity	NPC127235
0.766	Intermediate Similarity	NPC6765
0.766	Intermediate Similarity	NPC93869
0.7619	Intermediate Similarity	NPC279575
0.76	Intermediate Similarity	NPC148270
0.76	Intermediate Similarity	NPC197813
0.76	Intermediate Similarity	NPC80338
0.7558	Intermediate Similarity	NPC170595
0.7553	Intermediate Similarity	NPC274588
0.7553	Intermediate Similarity	NPC63897
0.7551	Intermediate Similarity	NPC304163
0.7527	Intermediate Similarity	NPC235051
0.75	Intermediate Similarity	NPC299527
0.7475	Intermediate Similarity	NPC475928
0.7475	Intermediate Similarity	NPC37240
0.747	Intermediate Similarity	NPC470659
0.747	Intermediate Similarity	NPC470660
0.7449	Intermediate Similarity	NPC287539
0.7449	Intermediate Similarity	NPC216911
0.7449	Intermediate Similarity	NPC3488
0.7444	Intermediate Similarity	NPC470658
0.7423	Intermediate Similarity	NPC37866
0.7396	Intermediate Similarity	NPC161293
0.7396	Intermediate Similarity	NPC170527
0.7396	Intermediate Similarity	NPC284063
0.7379	Intermediate Similarity	NPC193741
0.7374	Intermediate Similarity	NPC35185
0.7374	Intermediate Similarity	NPC474730
0.7374	Intermediate Similarity	NPC4899
0.7374	Intermediate Similarity	NPC177013
0.7347	Intermediate Similarity	NPC244878
0.7347	Intermediate Similarity	NPC476211
0.7347	Intermediate Similarity	NPC476320
0.7327	Intermediate Similarity	NPC170432
0.732	Intermediate Similarity	NPC76486
0.732	Intermediate Similarity	NPC86843
0.7312	Intermediate Similarity	NPC104129
0.7312	Intermediate Similarity	NPC249408
0.7303	Intermediate Similarity	NPC20072
0.73	Intermediate Similarity	NPC329834
0.7273	Intermediate Similarity	NPC27474
0.7273	Intermediate Similarity	NPC100697
0.7273	Intermediate Similarity	NPC20673
0.7273	Intermediate Similarity	NPC476230
0.7262	Intermediate Similarity	NPC248427
0.7245	Intermediate Similarity	NPC151093
0.7238	Intermediate Similarity	NPC475851
0.7238	Intermediate Similarity	NPC475924
0.7234	Intermediate Similarity	NPC117596
0.7184	Intermediate Similarity	NPC110701
0.7172	Intermediate Similarity	NPC91497
0.7158	Intermediate Similarity	NPC472125
0.7158	Intermediate Similarity	NPC472124
0.7158	Intermediate Similarity	NPC48463
0.7158	Intermediate Similarity	NPC472126
0.7157	Intermediate Similarity	NPC474569
0.7156	Intermediate Similarity	NPC219656
0.7143	Intermediate Similarity	NPC58267
0.7143	Intermediate Similarity	NPC263674
0.7143	Intermediate Similarity	NPC261372
0.7143	Intermediate Similarity	NPC472290
0.7129	Intermediate Similarity	NPC329704
0.71	Intermediate Similarity	NPC4637
0.71	Intermediate Similarity	NPC476228
0.71	Intermediate Similarity	NPC219038
0.71	Intermediate Similarity	NPC98859
0.7087	Intermediate Similarity	NPC226642
0.7083	Intermediate Similarity	NPC61201
0.7071	Intermediate Similarity	NPC157739
0.7071	Intermediate Similarity	NPC158088
0.7059	Intermediate Similarity	NPC312774
0.7059	Intermediate Similarity	NPC475521
0.7059	Intermediate Similarity	NPC475365
0.7053	Intermediate Similarity	NPC307699
0.7041	Intermediate Similarity	NPC207617
0.7041	Intermediate Similarity	NPC241911
0.7041	Intermediate Similarity	NPC472989
0.7037	Intermediate Similarity	NPC147292
0.703	Intermediate Similarity	NPC471599
0.703	Intermediate Similarity	NPC136816
0.703	Intermediate Similarity	NPC272015
0.703	Intermediate Similarity	NPC106668
0.7027	Intermediate Similarity	NPC233500
0.7024	Intermediate Similarity	NPC474078
0.7021	Intermediate Similarity	NPC248312
0.7	Intermediate Similarity	NPC22149
0.7	Intermediate Similarity	NPC471247
0.7	Intermediate Similarity	NPC306344
0.7	Intermediate Similarity	NPC255677
0.699	Remote Similarity	NPC473923
0.699	Remote Similarity	NPC181845
0.699	Remote Similarity	NPC26798
0.699	Remote Similarity	NPC242748
0.699	Remote Similarity	NPC473476
0.6979	Remote Similarity	NPC66504
0.697	Remote Similarity	NPC471770
0.697	Remote Similarity	NPC278939
0.697	Remote Similarity	NPC473555
0.697	Remote Similarity	NPC243728
0.697	Remote Similarity	NPC473890
0.6964	Remote Similarity	NPC196130
0.6962	Remote Similarity	NPC155457
0.6961	Remote Similarity	NPC27687
0.6952	Remote Similarity	NPC42482
0.6952	Remote Similarity	NPC40440
0.6939	Remote Similarity	NPC101051
0.6931	Remote Similarity	NPC267510
0.6931	Remote Similarity	NPC4831
0.6931	Remote Similarity	NPC31346
0.6931	Remote Similarity	NPC309425
0.6931	Remote Similarity	NPC472023
0.6931	Remote Similarity	NPC88000
0.6931	Remote Similarity	NPC470168
0.6931	Remote Similarity	NPC47566
0.6931	Remote Similarity	NPC129372
0.6931	Remote Similarity	NPC298255
0.6931	Remote Similarity	NPC160734
0.6931	Remote Similarity	NPC28304
0.6923	Remote Similarity	NPC230507
0.6923	Remote Similarity	NPC305423
0.6923	Remote Similarity	NPC473469
0.6923	Remote Similarity	NPC470432
0.6923	Remote Similarity	NPC94272
0.6923	Remote Similarity	NPC14704
0.6923	Remote Similarity	NPC113044
0.6923	Remote Similarity	NPC283829
0.6923	Remote Similarity	NPC161676
0.6923	Remote Similarity	NPC33053
0.6916	Remote Similarity	NPC308140
0.6916	Remote Similarity	NPC19888
0.6914	Remote Similarity	NPC31496
0.6914	Remote Similarity	NPC13143
0.6914	Remote Similarity	NPC294813
0.6909	Remote Similarity	NPC472080
0.6903	Remote Similarity	NPC219804
0.69	Remote Similarity	NPC469918
0.69	Remote Similarity	NPC469919
0.69	Remote Similarity	NPC223700
0.69	Remote Similarity	NPC117066
0.69	Remote Similarity	NPC96399
0.6893	Remote Similarity	NPC470885
0.6893	Remote Similarity	NPC187400
0.6893	Remote Similarity	NPC221562
0.6893	Remote Similarity	NPC86095
0.6893	Remote Similarity	NPC474464
0.6882	Remote Similarity	NPC477746
0.6882	Remote Similarity	NPC477747
0.6875	Remote Similarity	NPC327253
0.6869	Remote Similarity	NPC474297
0.6863	Remote Similarity	NPC154452
0.6863	Remote Similarity	NPC261117
0.6863	Remote Similarity	NPC222062
0.6863	Remote Similarity	NPC310804
0.6863	Remote Similarity	NPC195510
0.6863	Remote Similarity	NPC13171
0.686	Remote Similarity	NPC55652
0.6857	Remote Similarity	NPC476541
0.6857	Remote Similarity	NPC476539
0.6857	Remote Similarity	NPC235824
0.6857	Remote Similarity	NPC472896
0.6857	Remote Similarity	NPC476538
0.6857	Remote Similarity	NPC7213
0.6857	Remote Similarity	NPC476540
0.6857	Remote Similarity	NPC472897
0.6857	Remote Similarity	NPC98696
0.6857	Remote Similarity	NPC475634
0.6857	Remote Similarity	NPC295980
0.6852	Remote Similarity	NPC476546
0.6832	Remote Similarity	NPC473200
0.6832	Remote Similarity	NPC317019
0.6832	Remote Similarity	NPC473146
0.6832	Remote Similarity	NPC469942
0.6832	Remote Similarity	NPC7341
0.6832	Remote Similarity	NPC282669
0.6827	Remote Similarity	NPC472899
0.6827	Remote Similarity	NPC309448
0.6827	Remote Similarity	NPC474015
0.6827	Remote Similarity	NPC472898
0.6827	Remote Similarity	NPC472900
0.6822	Remote Similarity	NPC477028
0.6822	Remote Similarity	NPC124677
0.6822	Remote Similarity	NPC197231
0.6822	Remote Similarity	NPC477032

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 NPC98276 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	147
0.1-0.2	2631
0.2-0.3	4194
0.3-0.4	1494
0.4-0.5	442
0.5-0.6	224
0.6-0.7	18
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
0.6726	Remote Similarity	NPD7503	Approved
0.6632	Remote Similarity	NPD4249	Approved
0.6562	Remote Similarity	NPD4250	Approved
0.6562	Remote Similarity	NPD4251	Approved
0.6449	Remote Similarity	NPD6412	Phase 2
0.6435	Remote Similarity	NPD8033	Approved
0.6316	Remote Similarity	NPD7328	Approved
0.6316	Remote Similarity	NPD7327	Approved
0.6261	Remote Similarity	NPD7516	Approved
0.6238	Remote Similarity	NPD8171	Discontinued
0.6224	Remote Similarity	NPD7524	Approved
0.6207	Remote Similarity	NPD8377	Approved
0.6207	Remote Similarity	NPD8294	Approved
0.617	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD8380	Approved
0.6154	Remote Similarity	NPD8335	Approved
0.6154	Remote Similarity	NPD8379	Approved
0.6154	Remote Similarity	NPD8296	Approved
0.6154	Remote Similarity	NPD8378	Approved
0.6106	Remote Similarity	NPD8133	Approved
0.6082	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6076	Remote Similarity	NPD889	Approved
0.6076	Remote Similarity	NPD895	Approved
0.6076	Remote Similarity	NPD893	Approved
0.6076	Remote Similarity	NPD888	Phase 3
0.6076	Remote Similarity	NPD892	Phase 3
0.6076	Remote Similarity	NPD887	Approved
0.6076	Remote Similarity	NPD894	Approved
0.6076	Remote Similarity	NPD891	Phase 3
0.6076	Remote Similarity	NPD890	Clinical (unspecified phase)
0.6026	Remote Similarity	NPD905	Approved
0.6026	Remote Similarity	NPD904	Phase 3
0.6	Remote Similarity	NPD4820	Approved
0.6	Remote Similarity	NPD4821	Approved
0.6	Remote Similarity	NPD4822	Approved
0.6	Remote Similarity	NPD4819	Approved
0.5979	Remote Similarity	NPD6695	Phase 3
0.5957	Remote Similarity	NPD4268	Approved
0.5957	Remote Similarity	NPD4271	Approved
0.595	Remote Similarity	NPD7507	Approved
0.5946	Remote Similarity	NPD6686	Approved
0.5943	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD8513	Phase 3
0.5877	Remote Similarity	NPD6053	Discontinued
0.5876	Remote Similarity	NPD6435	Approved
0.587	Remote Similarity	NPD1811	Approved
0.587	Remote Similarity	NPD1810	Approved
0.5854	Remote Similarity	NPD2267	Suspended
0.5851	Remote Similarity	NPD6932	Approved
0.5833	Remote Similarity	NPD6370	Approved
0.5806	Remote Similarity	NPD7319	Approved
0.575	Remote Similarity	NPD2269	Approved
0.575	Remote Similarity	NPD8517	Approved
0.575	Remote Similarity	NPD8515	Approved
0.575	Remote Similarity	NPD8516	Approved
0.5745	Remote Similarity	NPD6933	Approved
0.5743	Remote Similarity	NPD7750	Discontinued
0.5728	Remote Similarity	NPD46	Approved
0.5728	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD6698	Approved
0.5714	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.567	Remote Similarity	NPD7514	Phase 3
0.567	Remote Similarity	NPD6928	Phase 2
0.567	Remote Similarity	NPD5368	Approved
0.567	Remote Similarity	NPD6930	Phase 2
0.567	Remote Similarity	NPD6931	Approved
0.5669	Remote Similarity	NPD8449	Approved
0.5667	Remote Similarity	NPD6054	Approved
0.5657	Remote Similarity	NPD7154	Phase 3
0.5625	Remote Similarity	NPD7145	Approved
0.5625	Remote Similarity	NPD8450	Suspended
0.562	Remote Similarity	NPD6015	Approved
0.562	Remote Similarity	NPD6016	Approved
0.5612	Remote Similarity	NPD5369	Approved
0.56	Remote Similarity	NPD7736	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