NPASS Compound

Structure

NPC310830 OpenBabel07101719132D 26 29 0 0 1 0 0 0 0 0999 V2000 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 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 -0.9706 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9487 -2.7024 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 -1.7796 -1.0933 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 4.3301 -1.5000 0.0000 C 0 0 0 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 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 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 6.0622 -1.5000 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 5.1962 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4487 -1.8364 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 3 24 1 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 5 14 2 0 0 0 0 6 17 1 0 0 0 0 7 9 1 0 0 0 0 7 15 1 0 0 0 0 8 10 2 0 0 0 0 8 13 1 0 0 0 0 9 20 1 0 0 0 0 10 25 1 0 0 0 0 11 16 1 0 0 0 0 11 21 1 0 0 0 0 12 13 2 0 0 0 0 12 25 1 0 0 0 0 14 18 1 0 0 0 0 14 20 1 0 0 0 0 15 19 1 0 0 0 0 15 21 1 1 0 0 0 16 13 1 1 0 0 0 16 26 1 0 0 0 0 17 20 1 1 0 0 0 17 21 1 0 0 0 0 18 22 2 0 0 0 0 18 24 1 0 0 0 0 19 23 2 0 0 0 0 19 26 1 0 0 0 0 20 1 1 6 0 0 0 21 2 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	358.18
Volume:	368.315
LogP:	4.178
LogD:	3.542
LogS:	-5.403
# Rotatable Bonds:	3
TPSA:	65.74
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.741
Synthetic Accessibility Score:	4.422
Fsp3:	0.619
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.733
MDCK Permeability:	2.547454641899094e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.972
30% Bioavailability (F30%):	0.974

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.118
Plasma Protein Binding (PPB):	92.5313949584961%
Volume Distribution (VD):	2.487
Pgp-substrate:	6.393166542053223%

ADMET: Metabolism

CYP1A2-inhibitor:	0.334
CYP1A2-substrate:	0.737
CYP2C19-inhibitor:	0.806
CYP2C19-substrate:	0.722
CYP2C9-inhibitor:	0.599
CYP2C9-substrate:	0.096
CYP2D6-inhibitor:	0.1
CYP2D6-substrate:	0.502
CYP3A4-inhibitor:	0.928
CYP3A4-substrate:	0.461

ADMET: Excretion

Clearance (CL):	13.127
Half-life (T1/2):	0.092

ADMET: Toxicity

hERG Blockers:	0.095
Human Hepatotoxicity (H-HT):	0.469
Drug-inuced Liver Injury (DILI):	0.24
AMES Toxicity:	0.03
Rat Oral Acute Toxicity:	0.966
Maximum Recommended Daily Dose:	0.89
Skin Sensitization:	0.137
Carcinogencity:	0.891
Eye Corrosion:	0.354
Eye Irritation:	0.12
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC310830

Natural Product ID:	NPC310830
*Common Name:**	Floribundic Ester
IUPAC Name:	methyl (2S,4aS,6aR,10aS,10bS)-2-(furan-3-yl)-6a,10b-dimethyl-4-oxo-1,2,4a,5,6,9,10,10a-octahydrobenzo[f]isochromene-7-carboxylate
Synonyms:	Floribundic Ester
Standard InCHIKey:	CCRPRTUMLVVFRR-BPERIUBUSA-N
Standard InCHI:	InChI=1S/C21H26O5/c1-20-9-7-15-19(23)26-16(13-8-10-25-12-13)11-21(15,2)17(20)6-4-5-14(20)18(22)24-3/h5,8,10,12,15-17H,4,6-7,9,11H2,1-3H3/t15-,16+,17-,20+,21-/m1/s1
SMILES:	C[C@]12CC[C@@H]3C(=O)O[C@@H](C[C@@]3(C)[C@@H]2CCC=C1C(=O)OC)c1ccoc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL483178
PubChem CID:	25110692
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO10715	Fibraurea tinctoria	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17994701]
NPO10715	Fibraurea tinctoria	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18829331]
NPO10715	Fibraurea tinctoria	Species	Menispermaceae	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	12

Activity Type	# Activity
Organism	12

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	13.07	%	PMID[518718]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	14.9	%	PMID[518718]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	13.95	%	PMID[518718]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	16.78	%	PMID[518718]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	15.46	%	PMID[518718]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	20.18	%	PMID[518718]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	21.85	%	PMID[518718]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	21.84	%	PMID[518718]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	21.51	%	PMID[518718]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	20.95	%	PMID[518718]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	16.27	%	PMID[518718]

☑ 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 NPC310830 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	325
0.1-0.2	1317
0.2-0.3	2753
0.3-0.4	6075
0.4-0.5	11473
0.5-0.6	10039
0.6-0.7	9242
0.7-0.8	1047
0.8-0.85	305
0.85-0.9	106
0.9-0.95	12
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9771	High Similarity	NPC220094
0.9771	High Similarity	NPC476943
0.9485	High Similarity	NPC142113
0.9394	High Similarity	NPC92941
0.9348	High Similarity	NPC346
0.9343	High Similarity	NPC476944
0.9281	High Similarity	NPC250228
0.9254	High Similarity	NPC470742
0.9209	High Similarity	NPC262198
0.9143	High Similarity	NPC470941
0.913	High Similarity	NPC223415
0.913	High Similarity	NPC470741
0.9085	High Similarity	NPC46551
0.9085	High Similarity	NPC159927
0.9085	High Similarity	NPC469335
0.9037	High Similarity	NPC146872
0.9015	High Similarity	NPC21460
0.9	High Similarity	NPC74612
0.8993	High Similarity	NPC267632
0.8971	High Similarity	NPC42400
0.8958	High Similarity	NPC469503
0.8951	High Similarity	NPC476122
0.8951	High Similarity	NPC477404
0.8951	High Similarity	NPC196864
0.8944	High Similarity	NPC476941
0.8944	High Similarity	NPC476942
0.8931	High Similarity	NPC95567
0.8931	High Similarity	NPC319140
0.8923	High Similarity	NPC179354
0.8897	High Similarity	NPC178932
0.8897	High Similarity	NPC57998
0.8873	High Similarity	NPC221809
0.8873	High Similarity	NPC10088
0.8873	High Similarity	NPC476938
0.8873	High Similarity	NPC476937
0.8849	High Similarity	NPC20500
0.8836	High Similarity	NPC214541
0.8836	High Similarity	NPC469850
0.8836	High Similarity	NPC44675
0.8836	High Similarity	NPC264943
0.8836	High Similarity	NPC281258
0.8836	High Similarity	NPC469336
0.8828	High Similarity	NPC476201
0.8828	High Similarity	NPC44577
0.8815	High Similarity	NPC470740
0.8806	High Similarity	NPC298190
0.8794	High Similarity	NPC86935
0.8777	High Similarity	NPC56197
0.8776	High Similarity	NPC209364
0.8776	High Similarity	NPC60973
0.8769	High Similarity	NPC16922
0.8768	High Similarity	NPC236532
0.8767	High Similarity	NPC30222
0.8767	High Similarity	NPC282445
0.875	High Similarity	NPC195325
0.8722	High Similarity	NPC112706
0.8722	High Similarity	NPC207294
0.8716	High Similarity	NPC261597
0.8716	High Similarity	NPC472283
0.8716	High Similarity	NPC286722
0.8714	High Similarity	NPC205765
0.8707	High Similarity	NPC476262
0.8707	High Similarity	NPC35000
0.8705	High Similarity	NPC90953
0.8705	High Similarity	NPC474722
0.869	High Similarity	NPC476936
0.8671	High Similarity	NPC276676
0.8671	High Similarity	NPC471292
0.8662	High Similarity	NPC238843
0.8662	High Similarity	NPC199044
0.8658	High Similarity	NPC477403
0.8658	High Similarity	NPC473473
0.8658	High Similarity	NPC262872
0.8658	High Similarity	NPC475295
0.8652	High Similarity	NPC473152
0.8649	High Similarity	NPC263265
0.8649	High Similarity	NPC107646
0.8649	High Similarity	NPC126723
0.8647	High Similarity	NPC83178
0.863	High Similarity	NPC18135
0.8621	High Similarity	NPC472654
0.8621	High Similarity	NPC329180
0.8603	High Similarity	NPC471817
0.86	High Similarity	NPC477402
0.8591	High Similarity	NPC249021
0.8591	High Similarity	NPC187149
0.8591	High Similarity	NPC472772
0.8591	High Similarity	NPC167142
0.8591	High Similarity	NPC36655
0.8591	High Similarity	NPC299038
0.8591	High Similarity	NPC45101
0.8571	High Similarity	NPC75906
0.8571	High Similarity	NPC476940
0.8571	High Similarity	NPC46536
0.8571	High Similarity	NPC476939
0.8571	High Similarity	NPC138139
0.8562	High Similarity	NPC156189
0.8562	High Similarity	NPC470997
0.8551	High Similarity	NPC158525
0.8543	High Similarity	NPC149896
0.8543	High Similarity	NPC69028
0.8543	High Similarity	NPC211777
0.8543	High Similarity	NPC5079
0.8542	High Similarity	NPC62799
0.854	High Similarity	NPC471006
0.8533	High Similarity	NPC307383
0.8533	High Similarity	NPC237155
0.8533	High Similarity	NPC475967
0.8531	High Similarity	NPC137295
0.8531	High Similarity	NPC251865
0.8529	High Similarity	NPC61788
0.8523	High Similarity	NPC469485
0.8521	High Similarity	NPC121158
0.8519	High Similarity	NPC198904
0.8493	Intermediate Similarity	NPC470791
0.8493	Intermediate Similarity	NPC470790
0.8487	Intermediate Similarity	NPC292389
0.8487	Intermediate Similarity	NPC198047
0.8487	Intermediate Similarity	NPC234660
0.8487	Intermediate Similarity	NPC165218
0.8487	Intermediate Similarity	NPC51568
0.8487	Intermediate Similarity	NPC469338
0.8478	Intermediate Similarity	NPC471998
0.8477	Intermediate Similarity	NPC475381
0.8477	Intermediate Similarity	NPC25255
0.8477	Intermediate Similarity	NPC335761
0.8477	Intermediate Similarity	NPC472653
0.8477	Intermediate Similarity	NPC305016
0.8473	Intermediate Similarity	NPC1848
0.8472	Intermediate Similarity	NPC41182
0.8467	Intermediate Similarity	NPC173544
0.8467	Intermediate Similarity	NPC472777
0.8467	Intermediate Similarity	NPC472776
0.8467	Intermediate Similarity	NPC472778
0.8462	Intermediate Similarity	NPC476946
0.8446	Intermediate Similarity	NPC33938
0.8444	Intermediate Similarity	NPC476917
0.8444	Intermediate Similarity	NPC477966
0.8444	Intermediate Similarity	NPC327527
0.8444	Intermediate Similarity	NPC477123
0.8433	Intermediate Similarity	NPC23086
0.8431	Intermediate Similarity	NPC276551
0.8431	Intermediate Similarity	NPC469849
0.8431	Intermediate Similarity	NPC470940
0.8431	Intermediate Similarity	NPC470182
0.8429	Intermediate Similarity	NPC310043
0.8429	Intermediate Similarity	NPC186626
0.8425	Intermediate Similarity	NPC19747
0.8421	Intermediate Similarity	NPC263432
0.8421	Intermediate Similarity	NPC18347
0.8421	Intermediate Similarity	NPC472771
0.8421	Intermediate Similarity	NPC470939
0.8421	Intermediate Similarity	NPC193798
0.8421	Intermediate Similarity	NPC82851
0.8421	Intermediate Similarity	NPC207978
0.8421	Intermediate Similarity	NPC200782
0.8414	Intermediate Similarity	NPC233763
0.8411	Intermediate Similarity	NPC474932
0.8411	Intermediate Similarity	NPC474611
0.8409	Intermediate Similarity	NPC36255
0.8403	Intermediate Similarity	NPC84479
0.84	Intermediate Similarity	NPC204663
0.8394	Intermediate Similarity	NPC89133
0.8385	Intermediate Similarity	NPC243704
0.8382	Intermediate Similarity	NPC208389
0.8377	Intermediate Similarity	NPC470875
0.8377	Intermediate Similarity	NPC478178
0.8367	Intermediate Similarity	NPC234494
0.8367	Intermediate Similarity	NPC471001
0.8367	Intermediate Similarity	NPC211625
0.8366	Intermediate Similarity	NPC477405
0.8366	Intermediate Similarity	NPC663
0.8366	Intermediate Similarity	NPC419
0.8366	Intermediate Similarity	NPC39986
0.8366	Intermediate Similarity	NPC134254
0.8366	Intermediate Similarity	NPC472773
0.8366	Intermediate Similarity	NPC469846
0.8366	Intermediate Similarity	NPC476197
0.8366	Intermediate Similarity	NPC224394
0.8366	Intermediate Similarity	NPC302369
0.8358	Intermediate Similarity	NPC230979
0.8357	Intermediate Similarity	NPC214572
0.8357	Intermediate Similarity	NPC46896
0.8356	Intermediate Similarity	NPC471174
0.8356	Intermediate Similarity	NPC255414
0.8344	Intermediate Similarity	NPC195131
0.8323	Intermediate Similarity	NPC473766
0.8323	Intermediate Similarity	NPC173516
0.8323	Intermediate Similarity	NPC100333
0.8323	Intermediate Similarity	NPC473753
0.8321	Intermediate Similarity	NPC476925
0.8312	Intermediate Similarity	NPC271657
0.8312	Intermediate Similarity	NPC476860
0.8312	Intermediate Similarity	NPC476858
0.8312	Intermediate Similarity	NPC476856
0.8312	Intermediate Similarity	NPC476857
0.8312	Intermediate Similarity	NPC123088
0.8312	Intermediate Similarity	NPC146991
0.8309	Intermediate Similarity	NPC477040
0.8309	Intermediate Similarity	NPC477039

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 NPC310830 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	279
0.1-0.2	916
0.2-0.3	1840
0.3-0.4	2710
0.4-0.5	2028
0.5-0.6	1058
0.6-0.7	294
0.7-0.8	23
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8212	Intermediate Similarity	NPD5760	Phase 2
0.8212	Intermediate Similarity	NPD5761	Phase 2
0.7885	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD920	Approved
0.7568	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD8434	Phase 2
0.7451	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD6832	Phase 2
0.7333	Intermediate Similarity	NPD1471	Phase 3
0.7333	Intermediate Similarity	NPD2346	Discontinued
0.732	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD4628	Phase 3
0.729	Intermediate Similarity	NPD6273	Approved
0.7262	Intermediate Similarity	NPD6765	Approved
0.7262	Intermediate Similarity	NPD6764	Approved
0.72	Intermediate Similarity	NPD2799	Discontinued
0.7188	Intermediate Similarity	NPD7819	Suspended
0.7178	Intermediate Similarity	NPD5494	Approved
0.7152	Intermediate Similarity	NPD2796	Approved
0.7152	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2313	Discontinued
0.7124	Intermediate Similarity	NPD1243	Approved
0.7115	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6599	Discontinued
0.7103	Intermediate Similarity	NPD1019	Discontinued
0.7093	Intermediate Similarity	NPD6784	Approved
0.7093	Intermediate Similarity	NPD6785	Approved
0.7092	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD3972	Approved
0.7055	Intermediate Similarity	NPD3749	Approved
0.7047	Intermediate Similarity	NPD4307	Phase 2
0.7034	Intermediate Similarity	NPD3266	Approved
0.7034	Intermediate Similarity	NPD3267	Approved
0.7012	Intermediate Similarity	NPD919	Approved
0.7006	Intermediate Similarity	NPD2532	Approved
0.7006	Intermediate Similarity	NPD2533	Approved
0.7006	Intermediate Similarity	NPD2534	Approved
0.7	Intermediate Similarity	NPD1933	Approved
0.6993	Remote Similarity	NPD2344	Approved
0.6988	Remote Similarity	NPD6808	Phase 2
0.6985	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.698	Remote Similarity	NPD8032	Phase 2
0.6974	Remote Similarity	NPD3748	Approved
0.6959	Remote Similarity	NPD6559	Discontinued
0.6957	Remote Similarity	NPD7411	Suspended
0.6951	Remote Similarity	NPD7075	Discontinued
0.6944	Remote Similarity	NPD9717	Approved
0.6937	Remote Similarity	NPD3226	Approved
0.6928	Remote Similarity	NPD1551	Phase 2
0.6928	Remote Similarity	NPD2935	Discontinued
0.6923	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD2797	Approved
0.6913	Remote Similarity	NPD3268	Approved
0.6903	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD2800	Approved
0.6901	Remote Similarity	NPD5585	Approved
0.6871	Remote Similarity	NPD2798	Approved
0.6863	Remote Similarity	NPD4308	Phase 3
0.6859	Remote Similarity	NPD7003	Approved
0.6853	Remote Similarity	NPD17	Approved
0.6839	Remote Similarity	NPD1549	Phase 2
0.6835	Remote Similarity	NPD6799	Approved
0.6835	Remote Similarity	NPD1241	Discontinued
0.6832	Remote Similarity	NPD7458	Discontinued
0.6829	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD1247	Approved
0.6821	Remote Similarity	NPD2979	Phase 3
0.6815	Remote Similarity	NPD2309	Approved
0.681	Remote Similarity	NPD6801	Discontinued
0.6803	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD1203	Approved
0.6792	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD5844	Phase 1
0.6776	Remote Similarity	NPD4622	Approved
0.6776	Remote Similarity	NPD447	Suspended
0.6776	Remote Similarity	NPD4618	Approved
0.6774	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD7236	Approved
0.6768	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD7033	Discontinued
0.6752	Remote Similarity	NPD3750	Approved
0.6748	Remote Similarity	NPD5889	Approved
0.6748	Remote Similarity	NPD5890	Approved
0.6735	Remote Similarity	NPD1876	Approved
0.6733	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD2182	Approved
0.6712	Remote Similarity	NPD1608	Approved
0.6711	Remote Similarity	NPD4140	Approved
0.671	Remote Similarity	NPD2438	Suspended
0.6709	Remote Similarity	NPD3887	Approved
0.6707	Remote Similarity	NPD6279	Approved
0.6707	Remote Similarity	NPD6280	Approved
0.6706	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD411	Approved
0.6688	Remote Similarity	NPD5689	Approved
0.6688	Remote Similarity	NPD5688	Approved
0.6687	Remote Similarity	NPD4380	Phase 2
0.6687	Remote Similarity	NPD7768	Phase 2
0.6687	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6355	Discontinued
0.6667	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6002	Phase 3
0.6667	Remote Similarity	NPD4359	Approved
0.6667	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6005	Phase 3
0.6667	Remote Similarity	NPD6004	Phase 3
0.6647	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD4110	Phase 3
0.6644	Remote Similarity	NPD1281	Approved
0.6644	Remote Similarity	NPD5647	Approved
0.6627	Remote Similarity	NPD6959	Discontinued
0.6627	Remote Similarity	NPD5402	Approved
0.6627	Remote Similarity	NPD3817	Phase 2
0.6627	Remote Similarity	NPD8127	Discontinued
0.6606	Remote Similarity	NPD1934	Approved
0.6605	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD5403	Approved
0.6603	Remote Similarity	NPD6100	Approved
0.6603	Remote Similarity	NPD6099	Approved
0.6601	Remote Similarity	NPD3142	Approved
0.6601	Remote Similarity	NPD3140	Approved
0.6591	Remote Similarity	NPD8313	Approved
0.6591	Remote Similarity	NPD8312	Approved
0.6588	Remote Similarity	NPD6232	Discontinued
0.6588	Remote Similarity	NPD5711	Approved
0.6588	Remote Similarity	NPD5710	Approved
0.6585	Remote Similarity	NPD6585	Discontinued
0.6584	Remote Similarity	NPD5401	Approved
0.6579	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD3764	Approved
0.6579	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.657	Remote Similarity	NPD7473	Discontinued
0.6564	Remote Similarity	NPD7239	Suspended
0.6554	Remote Similarity	NPD5327	Phase 3
0.6552	Remote Similarity	NPD5691	Approved
0.655	Remote Similarity	NPD3926	Phase 2
0.6546	Remote Similarity	NPD8404	Phase 2
0.6541	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD4107	Approved
0.6538	Remote Similarity	NPD1510	Phase 2
0.6536	Remote Similarity	NPD4870	Approved
0.6536	Remote Similarity	NPD6233	Phase 2
0.6532	Remote Similarity	NPD3818	Discontinued
0.6519	Remote Similarity	NPD2897	Discontinued
0.651	Remote Similarity	NPD1283	Approved
0.6507	Remote Similarity	NPD1778	Approved
0.6497	Remote Similarity	NPD2531	Phase 2
0.6491	Remote Similarity	NPD7229	Phase 3
0.6488	Remote Similarity	NPD3882	Suspended
0.6481	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD7097	Phase 1
0.6471	Remote Similarity	NPD6798	Discontinued
0.6467	Remote Similarity	NPD6362	Approved
0.6463	Remote Similarity	NPD3496	Discontinued
0.6458	Remote Similarity	NPD9493	Approved
0.6456	Remote Similarity	NPD2353	Approved
0.6456	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD3134	Approved
0.6438	Remote Similarity	NPD8166	Discontinued
0.6429	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5353	Approved
0.6425	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD164	Approved
0.6417	Remote Similarity	NPD4482	Phase 3
0.6415	Remote Similarity	NPD2424	Discontinued
0.641	Remote Similarity	NPD6653	Approved
0.641	Remote Similarity	NPD1607	Approved
0.6408	Remote Similarity	NPD5535	Approved
0.6407	Remote Similarity	NPD6844	Discontinued
0.6407	Remote Similarity	NPD37	Approved
0.6405	Remote Similarity	NPD7008	Discontinued
0.64	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD4476	Approved
0.6392	Remote Similarity	NPD4477	Approved
0.6391	Remote Similarity	NPD4965	Approved
0.6391	Remote Similarity	NPD4967	Phase 2
0.6391	Remote Similarity	NPD4966	Approved
0.6389	Remote Similarity	NPD8150	Discontinued
0.6387	Remote Similarity	NPD1240	Approved
0.637	Remote Similarity	NPD9545	Approved
0.6369	Remote Similarity	NPD2801	Approved
0.6364	Remote Similarity	NPD6010	Discontinued
0.6358	Remote Similarity	NPD7440	Discontinued
0.6351	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6347	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD7177	Discontinued
0.6331	Remote Similarity	NPD2296	Approved
0.6328	Remote Similarity	NPD5953	Discontinued
0.6327	Remote Similarity	NPD1651	Approved
0.6323	Remote Similarity	NPD6663	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