NPASS Compound

Structure

CID211625 OpenBabel06191716002D 24 26 0 0 1 0 0 0 0 0999 V2000 3.3358 3.8519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8340 4.3333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1789 3.0922 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8340 2.4074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5019 4.3333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6679 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6679 0.9630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8340 -0.4815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8340 -0.4815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1497 0.4815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6679 3.8519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5837 1.2605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8340 1.4444 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6679 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6679 0.9630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8340 1.4444 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6679 2.8889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9630 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5019 2.4074 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9630 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5837 -0.2976 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8340 2.4074 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 12 1 0 0 0 0 3 13 1 0 0 0 0 4 14 1 0 0 0 0 5 19 1 0 0 0 0 6 12 2 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 14 1 0 0 0 0 9 20 1 0 0 0 0 10 15 1 0 0 0 0 10 20 1 0 0 0 0 11 13 2 0 0 0 0 11 23 1 0 0 0 0 12 18 1 0 0 0 0 13 16 1 0 0 0 0 14 19 1 6 0 0 0 15 16 2 0 0 0 0 15 23 1 0 0 0 0 16 17 1 0 0 0 0 17 19 1 6 0 0 0 17 24 1 0 0 0 0 18 21 2 0 0 0 0 18 24 1 0 0 0 0 19 20 1 6 0 0 0 20 22 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	332.2
Volume:	353.422
LogP:	3.827
LogD:	3.662
LogS:	-4.185
# Rotatable Bonds:	3
TPSA:	59.67
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.649
Synthetic Accessibility Score:	4.666
Fsp3:	0.65
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.554
MDCK Permeability:	2.4973369363578968e-05
Pgp-inhibitor:	0.898
Pgp-substrate:	0.012
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.071

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.609
Plasma Protein Binding (PPB):	90.7735595703125%
Volume Distribution (VD):	2.213
Pgp-substrate:	13.022269248962402%

ADMET: Metabolism

CYP1A2-inhibitor:	0.763
CYP1A2-substrate:	0.655
CYP2C19-inhibitor:	0.931
CYP2C19-substrate:	0.763
CYP2C9-inhibitor:	0.831
CYP2C9-substrate:	0.073
CYP2D6-inhibitor:	0.481
CYP2D6-substrate:	0.127
CYP3A4-inhibitor:	0.935
CYP3A4-substrate:	0.506

ADMET: Excretion

Clearance (CL):	14.491
Half-life (T1/2):	0.142

ADMET: Toxicity

hERG Blockers:	0.159
Human Hepatotoxicity (H-HT):	0.62
Drug-inuced Liver Injury (DILI):	0.351
AMES Toxicity:	0.038
Rat Oral Acute Toxicity:	0.925
Maximum Recommended Daily Dose:	0.922
Skin Sensitization:	0.542
Carcinogencity:	0.922
Eye Corrosion:	0.145
Eye Irritation:	0.072
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC211625

Natural Product ID:	NPC211625
*Common Name:**	((4S,4As,5S,8As)-8A-Hydroxy-3,4A,5-Trimethyl-4,4A,5,6,7,8,8A,9-Octahydronaphtho[2,3-B]Furan-4-Yl)2-Methylbut-2-Enoate
IUPAC Name:	[(4S,4aS,5S,8aS)-8a-hydroxy-3,4a,5-trimethyl-4,5,6,7,8,9-hexahydrobenzo[f][1]benzofuran-4-yl] (Z)-2-methylbut-2-enoate
Synonyms:
Standard InCHIKey:	WPNXICJHRZQRMC-HUVTZIOQSA-N
Standard InCHI:	InChI=1S/C20H28O4/c1-6-12(2)18(21)24-17-16-13(3)11-23-15(16)10-20(22)9-7-8-14(4)19(17,20)5/h6,11,14,17,22H,7-10H2,1-5H3/b12-6-/t14-,17+,19-,20-/m0/s1
SMILES:	C/C=C(/C)C(=O)O[C@@H]1c2c(C)coc2C[C@]2(CCC[C@H](C)[C@@]12C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2252624
PubChem CID:	76319166
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0003655] Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids

*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
NPO1183	Ligularia macrophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17672504]
NPO1183	Ligularia macrophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18044832]
NPO20047	Aconitum tuberosum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7008	Coniogramme intermedia	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26311	Panicum virgatum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1183	Ligularia macrophylla	Species	Asteraceae	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
IC50	1
Others	5

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT489	Organism	Coptotermes formosanus	Coptotermes formosanus	Activity	=	16.5	mg	PMID[537005]
NPT489	Organism	Coptotermes formosanus	Coptotermes formosanus	mortality	=	18.8	%	PMID[537005]
NPT489	Organism	Coptotermes formosanus	Coptotermes formosanus	mortality	=	16.3	%	PMID[537005]
NPT489	Organism	Coptotermes formosanus	Coptotermes formosanus	mortality	=	3.8	%	PMID[537005]
NPT489	Organism	Coptotermes formosanus	Coptotermes formosanus	mortality	=	1.3	%	PMID[537005]
NPT854	Organism	Lemna paucicostata	Lemna paucicostata	IC50	=	2940.0	nM	PMID[537005]

☑ 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 NPC211625 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	301
0.1-0.2	1281
0.2-0.3	2639
0.3-0.4	5571
0.4-0.5	10913
0.5-0.6	8586
0.6-0.7	7180
0.7-0.8	5819
0.8-0.85	330
0.85-0.9	60
0.9-0.95	15
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9724	High Similarity	NPC114880
0.965	High Similarity	NPC19747
0.9648	High Similarity	NPC62799
0.9524	High Similarity	NPC75310
0.9388	High Similarity	NPC475777
0.9333	High Similarity	NPC474611
0.9301	High Similarity	NPC64568
0.9301	High Similarity	NPC205071
0.9252	High Similarity	NPC212257
0.9241	High Similarity	NPC97904
0.9236	High Similarity	NPC84479
0.9211	High Similarity	NPC188649
0.92	High Similarity	NPC104736
0.92	High Similarity	NPC41880
0.915	High Similarity	NPC288602
0.915	High Similarity	NPC88841
0.9139	High Similarity	NPC81405
0.9139	High Similarity	NPC304692
0.9085	High Similarity	NPC18986
0.9079	High Similarity	NPC140952
0.9038	High Similarity	NPC296558
0.9032	High Similarity	NPC121995
0.902	High Similarity	NPC287559
0.9013	High Similarity	NPC194499
0.9013	High Similarity	NPC195954
0.9013	High Similarity	NPC88007
0.8968	High Similarity	NPC56358
0.8961	High Similarity	NPC68848
0.894	High Similarity	NPC282445
0.8926	High Similarity	NPC195325
0.8912	High Similarity	NPC41182
0.8903	High Similarity	NPC285567
0.8903	High Similarity	NPC283209
0.8889	High Similarity	NPC249021
0.8889	High Similarity	NPC472772
0.8874	High Similarity	NPC469503
0.8874	High Similarity	NPC75906
0.8867	High Similarity	NPC228842
0.8854	High Similarity	NPC270312
0.8844	High Similarity	NPC251865
0.8836	High Similarity	NPC263337
0.8836	High Similarity	NPC121158
0.8816	High Similarity	NPC30222
0.8816	High Similarity	NPC178932
0.88	High Similarity	NPC472654
0.8792	High Similarity	NPC221809
0.8792	High Similarity	NPC255414
0.8776	High Similarity	NPC243577
0.8774	High Similarity	NPC8389
0.8766	High Similarity	NPC299038
0.8758	High Similarity	NPC469336
0.8758	High Similarity	NPC35000
0.875	High Similarity	NPC121615
0.875	High Similarity	NPC294511
0.8742	High Similarity	NPC196864
0.8742	High Similarity	NPC476122
0.8742	High Similarity	NPC477404
0.8732	High Similarity	NPC293253
0.8726	High Similarity	NPC472664
0.8718	High Similarity	NPC82851
0.8718	High Similarity	NPC79571
0.8718	High Similarity	NPC472771
0.8716	High Similarity	NPC476944
0.871	High Similarity	NPC475967
0.8693	High Similarity	NPC57998
0.8681	High Similarity	NPC46896
0.8675	High Similarity	NPC69647
0.8675	High Similarity	NPC125182
0.8667	High Similarity	NPC71821
0.8667	High Similarity	NPC286038
0.8662	High Similarity	NPC472773
0.8645	High Similarity	NPC261597
0.8645	High Similarity	NPC7059
0.8636	High Similarity	NPC472785
0.8636	High Similarity	NPC214541
0.8636	High Similarity	NPC44675
0.8636	High Similarity	NPC264943
0.863	High Similarity	NPC202260
0.8627	High Similarity	NPC268905
0.8627	High Similarity	NPC246164
0.8627	High Similarity	NPC476201
0.8618	High Similarity	NPC469335
0.8618	High Similarity	NPC159927
0.8618	High Similarity	NPC156189
0.8616	High Similarity	NPC473753
0.8616	High Similarity	NPC473766
0.8609	High Similarity	NPC66991
0.8608	High Similarity	NPC261184
0.86	High Similarity	NPC346
0.8599	High Similarity	NPC5079
0.8599	High Similarity	NPC200782
0.8599	High Similarity	NPC329938
0.859	High Similarity	NPC123153
0.8581	High Similarity	NPC20578
0.8581	High Similarity	NPC62103
0.8571	High Similarity	NPC148374
0.8571	High Similarity	NPC67003
0.8571	High Similarity	NPC475641
0.8571	High Similarity	NPC294512
0.8571	High Similarity	NPC475237
0.8562	High Similarity	NPC18135
0.8562	High Similarity	NPC476943
0.8553	High Similarity	NPC277618
0.8553	High Similarity	NPC475779
0.8544	High Similarity	NPC302369
0.8544	High Similarity	NPC165218
0.8544	High Similarity	NPC134254
0.8544	High Similarity	NPC472780
0.8544	High Similarity	NPC472783
0.8544	High Similarity	NPC477405
0.8544	High Similarity	NPC419
0.8544	High Similarity	NPC39986
0.8544	High Similarity	NPC234660
0.8544	High Similarity	NPC663
0.8544	High Similarity	NPC292389
0.8544	High Similarity	NPC224394
0.8544	High Similarity	NPC51568
0.8544	High Similarity	NPC469338
0.8543	High Similarity	NPC470941
0.8543	High Similarity	NPC250228
0.8542	High Similarity	NPC471998
0.8535	High Similarity	NPC335761
0.8535	High Similarity	NPC472299
0.8535	High Similarity	NPC25255
0.8535	High Similarity	NPC472653
0.8533	High Similarity	NPC5676
0.8526	High Similarity	NPC477674
0.8526	High Similarity	NPC187149
0.8526	High Similarity	NPC36655
0.8526	High Similarity	NPC472776
0.8526	High Similarity	NPC472778
0.8526	High Similarity	NPC167142
0.8526	High Similarity	NPC472777
0.8523	High Similarity	NPC267632
0.8523	High Similarity	NPC223415
0.8516	High Similarity	NPC477669
0.8516	High Similarity	NPC476262
0.8516	High Similarity	NPC469850
0.8509	High Similarity	NPC302392
0.8509	High Similarity	NPC472660
0.85	High Similarity	NPC472784
0.85	High Similarity	NPC472775
0.85	High Similarity	NPC173516
0.85	High Similarity	NPC472774
0.8493	Intermediate Similarity	NPC310043
0.8493	Intermediate Similarity	NPC307401
0.8491	Intermediate Similarity	NPC476860
0.8491	Intermediate Similarity	NPC476858
0.8491	Intermediate Similarity	NPC469849
0.8491	Intermediate Similarity	NPC276735
0.8491	Intermediate Similarity	NPC476856
0.8491	Intermediate Similarity	NPC276551
0.8491	Intermediate Similarity	NPC476857
0.8491	Intermediate Similarity	NPC470182
0.8491	Intermediate Similarity	NPC470940
0.8487	Intermediate Similarity	NPC93666
0.8483	Intermediate Similarity	NPC158525
0.8481	Intermediate Similarity	NPC18347
0.8481	Intermediate Similarity	NPC472782
0.8481	Intermediate Similarity	NPC472781
0.8481	Intermediate Similarity	NPC149896
0.8481	Intermediate Similarity	NPC69028
0.8481	Intermediate Similarity	NPC193798
0.8481	Intermediate Similarity	NPC472767
0.8477	Intermediate Similarity	NPC233763
0.8476	Intermediate Similarity	NPC472665
0.8471	Intermediate Similarity	NPC307383
0.8471	Intermediate Similarity	NPC473368
0.8471	Intermediate Similarity	NPC475226
0.8471	Intermediate Similarity	NPC84349
0.8471	Intermediate Similarity	NPC477403
0.8462	Intermediate Similarity	NPC107646
0.8462	Intermediate Similarity	NPC209364
0.8447	Intermediate Similarity	NPC160651
0.8447	Intermediate Similarity	NPC471397
0.8446	Intermediate Similarity	NPC18904
0.8442	Intermediate Similarity	NPC472787
0.8438	Intermediate Similarity	NPC23387
0.8438	Intermediate Similarity	NPC86800
0.8438	Intermediate Similarity	NPC470875
0.8438	Intermediate Similarity	NPC308156
0.8438	Intermediate Similarity	NPC100849
0.8438	Intermediate Similarity	NPC472141
0.8435	Intermediate Similarity	NPC471996
0.8431	Intermediate Similarity	NPC470790
0.8431	Intermediate Similarity	NPC470791
0.8425	Intermediate Similarity	NPC214572
0.8424	Intermediate Similarity	NPC295914
0.8424	Intermediate Similarity	NPC472661
0.8421	Intermediate Similarity	NPC471174
0.8421	Intermediate Similarity	NPC216755
0.8418	Intermediate Similarity	NPC477402
0.8415	Intermediate Similarity	NPC56953
0.8415	Intermediate Similarity	NPC176413
0.8408	Intermediate Similarity	NPC45101
0.8408	Intermediate Similarity	NPC286722
0.84	Intermediate Similarity	NPC476946
0.84	Intermediate Similarity	NPC103134
0.84	Intermediate Similarity	NPC470741
0.8389	Intermediate Similarity	NPC20500

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 NPC211625 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	273
0.1-0.2	894
0.2-0.3	1755
0.3-0.4	2580
0.4-0.5	2120
0.5-0.6	1071
0.6-0.7	355
0.7-0.8	99
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8397	Intermediate Similarity	NPD5761	Phase 2
0.8397	Intermediate Similarity	NPD5760	Phase 2
0.8383	Intermediate Similarity	NPD8434	Phase 2
0.8302	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.8117	Intermediate Similarity	NPD2532	Approved
0.8117	Intermediate Similarity	NPD2534	Approved
0.8117	Intermediate Similarity	NPD2533	Approved
0.8013	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD920	Approved
0.7937	Intermediate Similarity	NPD7819	Suspended
0.7908	Intermediate Similarity	NPD2800	Approved
0.7885	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD6764	Approved
0.787	Intermediate Similarity	NPD6765	Approved
0.7862	Intermediate Similarity	NPD6599	Discontinued
0.7857	Intermediate Similarity	NPD4628	Phase 3
0.7791	Intermediate Similarity	NPD3749	Approved
0.7756	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD6785	Approved
0.7688	Intermediate Similarity	NPD6784	Approved
0.7677	Intermediate Similarity	NPD1243	Approved
0.7662	Intermediate Similarity	NPD2346	Discontinued
0.7661	Intermediate Similarity	NPD6559	Discontinued
0.7647	Intermediate Similarity	NPD2799	Discontinued
0.7628	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD1551	Phase 2
0.7597	Intermediate Similarity	NPD2796	Approved
0.7595	Intermediate Similarity	NPD6799	Approved
0.7593	Intermediate Similarity	NPD7411	Suspended
0.759	Intermediate Similarity	NPD5494	Approved
0.7578	Intermediate Similarity	NPD3226	Approved
0.7576	Intermediate Similarity	NPD7075	Discontinued
0.7564	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD1471	Phase 3
0.7547	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD919	Approved
0.75	Intermediate Similarity	NPD1549	Phase 2
0.75	Intermediate Similarity	NPD6273	Approved
0.75	Intermediate Similarity	NPD5710	Approved
0.75	Intermediate Similarity	NPD5711	Approved
0.75	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6100	Approved
0.7484	Intermediate Similarity	NPD6099	Approved
0.7483	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD2313	Discontinued
0.7455	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD6959	Discontinued
0.7439	Intermediate Similarity	NPD6801	Discontinued
0.7438	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD2344	Approved
0.741	Intermediate Similarity	NPD3882	Suspended
0.741	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD3750	Approved
0.7384	Intermediate Similarity	NPD5844	Phase 1
0.7372	Intermediate Similarity	NPD2935	Discontinued
0.7368	Intermediate Similarity	NPD7473	Discontinued
0.7368	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD3817	Phase 2
0.7337	Intermediate Similarity	NPD1247	Approved
0.7333	Intermediate Similarity	NPD1934	Approved
0.7326	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD3818	Discontinued
0.7317	Intermediate Similarity	NPD4380	Phase 2
0.7312	Intermediate Similarity	NPD7236	Approved
0.731	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7033	Discontinued
0.7308	Intermediate Similarity	NPD1510	Phase 2
0.7308	Intermediate Similarity	NPD3748	Approved
0.7305	Intermediate Similarity	NPD7768	Phase 2
0.7297	Intermediate Similarity	NPD1608	Approved
0.7294	Intermediate Similarity	NPD6232	Discontinued
0.729	Intermediate Similarity	NPD6651	Approved
0.729	Intermediate Similarity	NPD1607	Approved
0.7273	Intermediate Similarity	NPD1240	Approved
0.7262	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD8404	Phase 2
0.725	Intermediate Similarity	NPD2309	Approved
0.7246	Intermediate Similarity	NPD5402	Approved
0.7237	Intermediate Similarity	NPD6832	Phase 2
0.7229	Intermediate Similarity	NPD37	Approved
0.7215	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD6005	Phase 3
0.7215	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD6002	Phase 3
0.7215	Intermediate Similarity	NPD6004	Phase 3
0.7202	Intermediate Similarity	NPD4967	Phase 2
0.7202	Intermediate Similarity	NPD4965	Approved
0.7202	Intermediate Similarity	NPD4966	Approved
0.7193	Intermediate Similarity	NPD7229	Phase 3
0.7191	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD2801	Approved
0.7182	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7458	Discontinued
0.7151	Intermediate Similarity	NPD3926	Phase 2
0.7143	Intermediate Similarity	NPD3764	Approved
0.7143	Intermediate Similarity	NPD3268	Approved
0.7135	Intermediate Similarity	NPD8127	Discontinued
0.7134	Intermediate Similarity	NPD5403	Approved
0.7118	Intermediate Similarity	NPD6234	Discontinued
0.7117	Intermediate Similarity	NPD5401	Approved
0.7115	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD5953	Discontinued
0.7095	Intermediate Similarity	NPD17	Approved
0.7093	Intermediate Similarity	NPD6808	Phase 2
0.7091	Intermediate Similarity	NPD7239	Suspended
0.7089	Intermediate Similarity	NPD4308	Phase 3
0.7086	Intermediate Similarity	NPD7286	Phase 2
0.7081	Intermediate Similarity	NPD7003	Approved
0.7079	Intermediate Similarity	NPD8312	Approved
0.7079	Intermediate Similarity	NPD8313	Approved
0.7067	Intermediate Similarity	NPD3972	Approved
0.7067	Intermediate Similarity	NPD9717	Approved
0.7055	Intermediate Similarity	NPD1511	Approved
0.7039	Intermediate Similarity	NPD2797	Approved
0.7039	Intermediate Similarity	NPD1203	Approved
0.703	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD7799	Discontinued
0.7011	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD6166	Phase 2
0.7006	Intermediate Similarity	NPD447	Suspended
0.7006	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD230	Phase 1
0.7006	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD5124	Phase 1
0.7006	Intermediate Similarity	NPD6355	Discontinued
0.6993	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD2798	Approved
0.6989	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD8032	Phase 2
0.6982	Remote Similarity	NPD1465	Phase 2
0.698	Remote Similarity	NPD1778	Approved
0.6978	Remote Similarity	NPD4287	Approved
0.6975	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD4110	Phase 3
0.697	Remote Similarity	NPD1512	Approved
0.6949	Remote Similarity	NPD7074	Phase 3
0.6944	Remote Similarity	NPD8407	Phase 2
0.6943	Remote Similarity	NPD4307	Phase 2
0.6943	Remote Similarity	NPD4140	Approved
0.6936	Remote Similarity	NPD7199	Phase 2
0.6932	Remote Similarity	NPD3751	Discontinued
0.6928	Remote Similarity	NPD3266	Approved
0.6928	Remote Similarity	NPD3267	Approved
0.6927	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD411	Approved
0.6897	Remote Similarity	NPD3787	Discontinued
0.6893	Remote Similarity	NPD7054	Approved
0.6887	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD1019	Discontinued
0.6875	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD8368	Discontinued
0.6868	Remote Similarity	NPD8150	Discontinued
0.6867	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD1283	Approved
0.6859	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD7472	Approved
0.6848	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD9545	Approved
0.6842	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD7228	Approved
0.6836	Remote Similarity	NPD7177	Discontinued
0.6835	Remote Similarity	NPD2979	Phase 3
0.6829	Remote Similarity	NPD3887	Approved
0.6824	Remote Similarity	NPD6279	Approved
0.6824	Remote Similarity	NPD6280	Approved
0.6818	Remote Similarity	NPD2403	Approved
0.6816	Remote Similarity	NPD6797	Phase 2
0.6815	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD7435	Discontinued
0.6802	Remote Similarity	NPD7057	Phase 3
0.6802	Remote Similarity	NPD7058	Phase 2
0.68	Remote Similarity	NPD5585	Approved
0.6793	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.679	Remote Similarity	NPD5763	Approved
0.679	Remote Similarity	NPD5762	Approved
0.6778	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD7251	Discontinued
0.6774	Remote Similarity	NPD5647	Approved
0.6766	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD1876	Approved
0.6748	Remote Similarity	NPD2424	Discontinued
0.6744	Remote Similarity	NPD2296	Approved
0.6744	Remote Similarity	NPD5353	Approved
0.674	Remote Similarity	NPD7808	Phase 3
0.6737	Remote Similarity	NPD6782	Approved
0.6737	Remote Similarity	NPD6777	Approved
0.6737	Remote Similarity	NPD6778	Approved
0.6737	Remote Similarity	NPD6776	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