NPASS Compound

Structure

NPC474289 OpenBabel07101719522D 28 29 0 0 1 0 0 0 0 0999 V2000 1.7321 -8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 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 2.5981 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 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 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -6.5000 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 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 17 1 0 0 0 0 5 18 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 16 2 0 0 0 0 8 17 2 0 0 0 0 9 10 2 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 11 15 2 0 0 0 0 11 21 1 0 0 0 0 12 16 1 0 0 0 0 12 21 1 0 0 0 0 13 19 1 0 0 0 0 13 22 2 0 0 0 0 14 20 2 0 0 0 0 14 23 1 0 0 0 0 17 18 1 0 0 0 0 18 22 1 0 0 0 0 19 23 2 0 0 0 0 20 25 1 0 0 0 0 21 26 2 0 0 0 0 22 24 1 0 0 0 0 23 28 1 0 0 0 0 24 27 2 0 0 0 0 24 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	380.2
Volume:	417.98
LogP:	4.194
LogD:	3.945
LogS:	-4.981
# Rotatable Bonds:	7
TPSA:	67.51
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.374
Synthetic Accessibility Score:	3.704
Fsp3:	0.333
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:	-4.793
MDCK Permeability:	1.9078124751104042e-05
Pgp-inhibitor:	0.926
Pgp-substrate:	0.661
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.074
30% Bioavailability (F30%):	0.077

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.02
Plasma Protein Binding (PPB):	99.07845306396484%
Volume Distribution (VD):	0.824
Pgp-substrate:	0.9808291792869568%

ADMET: Metabolism

CYP1A2-inhibitor:	0.9
CYP1A2-substrate:	0.959
CYP2C19-inhibitor:	0.957
CYP2C19-substrate:	0.72
CYP2C9-inhibitor:	0.943
CYP2C9-substrate:	0.93
CYP2D6-inhibitor:	0.904
CYP2D6-substrate:	0.872
CYP3A4-inhibitor:	0.826
CYP3A4-substrate:	0.531

ADMET: Excretion

Clearance (CL):	1.102
Half-life (T1/2):	0.644

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.644
Drug-inuced Liver Injury (DILI):	0.049
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.06
Maximum Recommended Daily Dose:	0.972
Skin Sensitization:	0.938
Carcinogencity:	0.138
Eye Corrosion:	0.005
Eye Irritation:	0.228
Respiratory Toxicity:	0.825

Download Data

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

Natural Product: NPC474289

Natural Product ID:	NPC474289
*Common Name:**	Fukanemarin A
IUPAC Name:	7-hydroxy-3-[(3E,6E)-3,7,11-trimethyl-9-oxododeca-3,6,10-trien-2-yl]chromen-2-one
Synonyms:
Standard InCHIKey:	NELRHPUZXIHWPT-GDWCLCACSA-N
Standard InCHI:	InChI=1S/C24H28O4/c1-15(2)11-21(26)12-16(3)7-6-8-17(4)18(5)22-13-19-9-10-20(25)14-23(19)28-24(22)27/h7-11,13-14,18,25H,6,12H2,1-5H3/b16-7+,17-8+
SMILES:	CC(C1=CC2=C(C=C(C=C2)O)OC1=O)C(=CCC=C(C)CC(=O)C=C(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464739
PubChem CID:	44566692
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene 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
NPO3780	Ferula fukanensis	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[15043424]
NPO3780	Ferula fukanensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043424]
NPO3780	Ferula fukanensis	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[15467238]
NPO3780	Ferula fukanensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15787437]
NPO3780	Ferula fukanensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16378364]
NPO3780	Ferula fukanensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3780	Ferula fukanensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]

☑ 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

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	19500.0	nM	PMID[502968]

☑ 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 NPC474289 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	365
0.1-0.2	1606
0.2-0.3	4065
0.3-0.4	9814
0.4-0.5	8669
0.5-0.6	3835
0.6-0.7	6221
0.7-0.8	5017
0.8-0.85	1954
0.85-0.9	907
0.9-0.95	218
0.95-1	26

Similarity Score	Similarity Level	Natural Product ID
0.9308	High Similarity	NPC317045
0.9308	High Similarity	NPC246177
0.9262	High Similarity	NPC302107
0.9206	High Similarity	NPC121740
0.9206	High Similarity	NPC243688
0.9206	High Similarity	NPC224774
0.9206	High Similarity	NPC258567
0.9187	High Similarity	NPC187868
0.9187	High Similarity	NPC52247
0.918	High Similarity	NPC247553
0.9167	High Similarity	NPC148738
0.9167	High Similarity	NPC319870
0.9167	High Similarity	NPC327612
0.9167	High Similarity	NPC73078
0.9134	High Similarity	NPC469453
0.9048	High Similarity	NPC93219
0.9048	High Similarity	NPC244495
0.9016	High Similarity	NPC152306
0.8992	High Similarity	NPC32463
0.8968	High Similarity	NPC27671
0.8952	High Similarity	NPC180006
0.8952	High Similarity	NPC235190
0.8952	High Similarity	NPC163200
0.8943	High Similarity	NPC298796
0.8898	High Similarity	NPC168259
0.8889	High Similarity	NPC183642
0.8889	High Similarity	NPC310370
0.8889	High Similarity	NPC109675
0.8889	High Similarity	NPC273772
0.8881	High Similarity	NPC221046
0.8881	High Similarity	NPC332594
0.8872	High Similarity	NPC223616
0.8862	High Similarity	NPC265547
0.8855	High Similarity	NPC307289
0.8852	High Similarity	NPC33717
0.8846	High Similarity	NPC113098
0.8837	High Similarity	NPC185066
0.8819	High Similarity	NPC201667
0.8819	High Similarity	NPC73413
0.8806	High Similarity	NPC471069
0.8806	High Similarity	NPC471068
0.8797	High Similarity	NPC61499
0.879	High Similarity	NPC281356
0.8788	High Similarity	NPC55147
0.8788	High Similarity	NPC31849
0.8788	High Similarity	NPC54503
0.8779	High Similarity	NPC267336
0.8779	High Similarity	NPC272650
0.8779	High Similarity	NPC29734
0.8759	High Similarity	NPC229916
0.875	High Similarity	NPC471828
0.875	High Similarity	NPC170812
0.875	High Similarity	NPC155552
0.875	High Similarity	NPC471827
0.8741	High Similarity	NPC471071
0.8741	High Similarity	NPC471070
0.8741	High Similarity	NPC471072
0.874	High Similarity	NPC472518
0.873	High Similarity	NPC144418
0.8722	High Similarity	NPC131950
0.872	High Similarity	NPC31314
0.872	High Similarity	NPC474874
0.872	High Similarity	NPC193193
0.8712	High Similarity	NPC194277
0.8712	High Similarity	NPC281558
0.871	High Similarity	NPC96705
0.8699	High Similarity	NPC128633
0.8692	High Similarity	NPC157212
0.8692	High Similarity	NPC472519
0.8676	High Similarity	NPC71903
0.8661	High Similarity	NPC96286
0.8661	High Similarity	NPC248429
0.8651	High Similarity	NPC319378
0.8647	High Similarity	NPC10971
0.8647	High Similarity	NPC163557
0.8647	High Similarity	NPC83535
0.8647	High Similarity	NPC469449
0.8647	High Similarity	NPC2363
0.8643	High Similarity	NPC154217
0.8633	High Similarity	NPC188632
0.8633	High Similarity	NPC470296
0.8633	High Similarity	NPC196459
0.8633	High Similarity	NPC112791
0.8633	High Similarity	NPC94794
0.8633	High Similarity	NPC295696
0.8633	High Similarity	NPC71739
0.8633	High Similarity	NPC87609
0.8626	High Similarity	NPC187907
0.8605	High Similarity	NPC202594
0.8605	High Similarity	NPC232692
0.8603	High Similarity	NPC474624
0.8603	High Similarity	NPC151946
0.8603	High Similarity	NPC138047
0.8603	High Similarity	NPC131782
0.8594	High Similarity	NPC315807
0.8593	High Similarity	NPC38099
0.8593	High Similarity	NPC266245
0.8593	High Similarity	NPC26954
0.8582	High Similarity	NPC50896
0.8582	High Similarity	NPC204353
0.8582	High Similarity	NPC326600
0.8582	High Similarity	NPC92830
0.8571	High Similarity	NPC178627
0.8571	High Similarity	NPC196137
0.8571	High Similarity	NPC1886
0.8571	High Similarity	NPC469935
0.8561	High Similarity	NPC36181
0.854	High Similarity	NPC199458
0.854	High Similarity	NPC219584
0.854	High Similarity	NPC470083
0.854	High Similarity	NPC470668
0.854	High Similarity	NPC183639
0.854	High Similarity	NPC470669
0.8529	High Similarity	NPC131198
0.8529	High Similarity	NPC155963
0.8529	High Similarity	NPC13408
0.8529	High Similarity	NPC309452
0.8527	High Similarity	NPC291899
0.8527	High Similarity	NPC98509
0.8527	High Similarity	NPC229113
0.8519	High Similarity	NPC66705
0.8516	High Similarity	NPC13007
0.8516	High Similarity	NPC257188
0.8511	High Similarity	NPC153758
0.8511	High Similarity	NPC181388
0.8511	High Similarity	NPC470322
0.8507	High Similarity	NPC25937
0.8496	Intermediate Similarity	NPC37009
0.8496	Intermediate Similarity	NPC5515
0.8496	Intermediate Similarity	NPC73738
0.8496	Intermediate Similarity	NPC270369
0.8496	Intermediate Similarity	NPC250727
0.8496	Intermediate Similarity	NPC66430
0.8489	Intermediate Similarity	NPC470555
0.8485	Intermediate Similarity	NPC168710
0.8478	Intermediate Similarity	NPC195357
0.8478	Intermediate Similarity	NPC19476
0.8478	Intermediate Similarity	NPC230902
0.8478	Intermediate Similarity	NPC152771
0.8478	Intermediate Similarity	NPC241975
0.8478	Intermediate Similarity	NPC287286
0.8467	Intermediate Similarity	NPC211110
0.8467	Intermediate Similarity	NPC43500
0.8467	Intermediate Similarity	NPC250266
0.8467	Intermediate Similarity	NPC164148
0.8467	Intermediate Similarity	NPC266597
0.8467	Intermediate Similarity	NPC279573
0.8467	Intermediate Similarity	NPC188879
0.8467	Intermediate Similarity	NPC253616
0.8467	Intermediate Similarity	NPC307883
0.8456	Intermediate Similarity	NPC471630
0.8456	Intermediate Similarity	NPC283019
0.8456	Intermediate Similarity	NPC55615
0.8456	Intermediate Similarity	NPC160727
0.8456	Intermediate Similarity	NPC149320
0.8456	Intermediate Similarity	NPC128529
0.8456	Intermediate Similarity	NPC177281
0.8456	Intermediate Similarity	NPC476455
0.8451	Intermediate Similarity	NPC180477
0.8451	Intermediate Similarity	NPC297886
0.8451	Intermediate Similarity	NPC142863
0.8451	Intermediate Similarity	NPC249942
0.845	Intermediate Similarity	NPC290605
0.845	Intermediate Similarity	NPC154176
0.845	Intermediate Similarity	NPC50720
0.845	Intermediate Similarity	NPC173350
0.8444	Intermediate Similarity	NPC62366
0.8444	Intermediate Similarity	NPC224475
0.8444	Intermediate Similarity	NPC213173
0.8444	Intermediate Similarity	NPC180716
0.844	Intermediate Similarity	NPC469953
0.844	Intermediate Similarity	NPC287275
0.8433	Intermediate Similarity	NPC112192
0.8433	Intermediate Similarity	NPC164236
0.8433	Intermediate Similarity	NPC309717
0.8433	Intermediate Similarity	NPC66384
0.8433	Intermediate Similarity	NPC475589
0.8433	Intermediate Similarity	NPC189106
0.8433	Intermediate Similarity	NPC175159
0.8433	Intermediate Similarity	NPC113006
0.8433	Intermediate Similarity	NPC31872
0.8433	Intermediate Similarity	NPC128348
0.8433	Intermediate Similarity	NPC473584
0.8433	Intermediate Similarity	NPC137949
0.8433	Intermediate Similarity	NPC245120
0.8421	Intermediate Similarity	NPC2989
0.8421	Intermediate Similarity	NPC19242
0.8421	Intermediate Similarity	NPC469929
0.8421	Intermediate Similarity	NPC146615
0.8421	Intermediate Similarity	NPC247779
0.8421	Intermediate Similarity	NPC42292
0.8421	Intermediate Similarity	NPC307732
0.8417	Intermediate Similarity	NPC270883
0.8417	Intermediate Similarity	NPC172986
0.8417	Intermediate Similarity	NPC261227
0.8417	Intermediate Similarity	NPC221173
0.8409	Intermediate Similarity	NPC219923
0.8406	Intermediate Similarity	NPC36414
0.8406	Intermediate Similarity	NPC124269
0.8406	Intermediate Similarity	NPC312881

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 NPC474289 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	335
0.1-0.2	965
0.2-0.3	1586
0.3-0.4	2599
0.4-0.5	1936
0.5-0.6	1166
0.6-0.7	367
0.7-0.8	131
0.8-0.85	39
0.85-0.9	19
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9187	High Similarity	NPD422	Phase 1
0.8561	High Similarity	NPD6859	Clinical (unspecified phase)
0.8551	High Similarity	NPD3750	Approved
0.8527	High Similarity	NPD3225	Approved
0.8462	Intermediate Similarity	NPD2797	Approved
0.8421	Intermediate Similarity	NPD3268	Approved
0.837	Intermediate Similarity	NPD5124	Phase 1
0.837	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8286	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8284	Intermediate Similarity	NPD1296	Phase 2
0.8271	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.8231	Intermediate Similarity	NPD9717	Approved
0.8188	Intermediate Similarity	NPD3748	Approved
0.8182	Intermediate Similarity	NPD1203	Approved
0.8143	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD1551	Phase 2
0.8125	Intermediate Similarity	NPD1548	Phase 1
0.8112	Intermediate Similarity	NPD6799	Approved
0.8056	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8045	Intermediate Similarity	NPD3267	Approved
0.8045	Intermediate Similarity	NPD3266	Approved
0.8029	Intermediate Similarity	NPD1240	Approved
0.8028	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD1549	Phase 2
0.8	Intermediate Similarity	NPD4908	Phase 1
0.7973	Intermediate Similarity	NPD7411	Suspended
0.7958	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7958	Intermediate Similarity	NPD1652	Phase 2
0.7951	Intermediate Similarity	NPD9697	Approved
0.7943	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD1510	Phase 2
0.7914	Intermediate Similarity	NPD1607	Approved
0.7883	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD1610	Phase 2
0.7872	Intermediate Similarity	NPD2796	Approved
0.7832	Intermediate Similarity	NPD1243	Approved
0.7829	Intermediate Similarity	NPD7075	Discontinued
0.7823	Intermediate Similarity	NPD5403	Approved
0.7801	Intermediate Similarity	NPD4308	Phase 3
0.7801	Intermediate Similarity	NPD2799	Discontinued
0.78	Intermediate Similarity	NPD6801	Discontinued
0.7785	Intermediate Similarity	NPD6599	Discontinued
0.777	Intermediate Similarity	NPD1653	Approved
0.7763	Intermediate Similarity	NPD7768	Phase 2
0.7761	Intermediate Similarity	NPD4749	Approved
0.7748	Intermediate Similarity	NPD7819	Suspended
0.7748	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD6099	Approved
0.7746	Intermediate Similarity	NPD6100	Approved
0.7742	Intermediate Similarity	NPD3134	Approved
0.774	Intermediate Similarity	NPD1511	Approved
0.7737	Intermediate Similarity	NPD6832	Phase 2
0.7727	Intermediate Similarity	NPD1778	Approved
0.7712	Intermediate Similarity	NPD3749	Approved
0.771	Intermediate Similarity	NPD9545	Approved
0.7687	Intermediate Similarity	NPD5401	Approved
0.7676	Intermediate Similarity	NPD7033	Discontinued
0.7656	Intermediate Similarity	NPD5535	Approved
0.7635	Intermediate Similarity	NPD1512	Approved
0.7632	Intermediate Similarity	NPD2801	Approved
0.7626	Intermediate Similarity	NPD411	Approved
0.7622	Intermediate Similarity	NPD2935	Discontinued
0.7616	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7612	Intermediate Similarity	NPD1535	Discovery
0.7597	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD1241	Discontinued
0.7589	Intermediate Similarity	NPD447	Suspended
0.7584	Intermediate Similarity	NPD920	Approved
0.7582	Intermediate Similarity	NPD3817	Phase 2
0.7582	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD9493	Approved
0.7556	Intermediate Similarity	NPD1608	Approved
0.7556	Intermediate Similarity	NPD1481	Phase 2
0.7551	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD4380	Phase 2
0.754	Intermediate Similarity	NPD1358	Approved
0.7537	Intermediate Similarity	NPD3496	Discontinued
0.7534	Intermediate Similarity	NPD4628	Phase 3
0.7532	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD3882	Suspended
0.7518	Intermediate Similarity	NPD4307	Phase 2
0.7516	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2313	Discontinued
0.75	Intermediate Similarity	NPD6798	Discontinued
0.7482	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD2614	Approved
0.7468	Intermediate Similarity	NPD5402	Approved
0.7468	Intermediate Similarity	NPD4288	Approved
0.7466	Intermediate Similarity	NPD2800	Approved
0.7465	Intermediate Similarity	NPD6355	Discontinued
0.7465	Intermediate Similarity	NPD230	Phase 1
0.7464	Intermediate Similarity	NPD1019	Discontinued
0.7451	Intermediate Similarity	NPD1934	Approved
0.745	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD1894	Discontinued
0.7429	Intermediate Similarity	NPD4625	Phase 3
0.7419	Intermediate Similarity	NPD940	Approved
0.7419	Intermediate Similarity	NPD846	Approved
0.7413	Intermediate Similarity	NPD6651	Approved
0.741	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD3847	Discontinued
0.7394	Intermediate Similarity	NPD4060	Phase 1
0.7376	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD1091	Approved
0.7343	Intermediate Similarity	NPD4340	Discontinued
0.7343	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD2798	Approved
0.7333	Intermediate Similarity	NPD2532	Approved
0.7333	Intermediate Similarity	NPD2534	Approved
0.7333	Intermediate Similarity	NPD4626	Approved
0.7333	Intermediate Similarity	NPD17	Approved
0.7333	Intermediate Similarity	NPD2533	Approved
0.7329	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6004	Phase 3
0.7329	Intermediate Similarity	NPD6002	Phase 3
0.7329	Intermediate Similarity	NPD6005	Phase 3
0.7329	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD6233	Phase 2
0.7301	Intermediate Similarity	NPD5953	Discontinued
0.729	Intermediate Similarity	NPD1465	Phase 2
0.7284	Intermediate Similarity	NPD5844	Phase 1
0.7284	Intermediate Similarity	NPD7286	Phase 2
0.7273	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1613	Approved
0.7267	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD6971	Discontinued
0.7259	Intermediate Similarity	NPD5585	Approved
0.7255	Intermediate Similarity	NPD3226	Approved
0.7254	Intermediate Similarity	NPD3764	Approved
0.7222	Intermediate Similarity	NPD1933	Approved
0.7222	Intermediate Similarity	NPD3818	Discontinued
0.7219	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD6671	Approved
0.7215	Intermediate Similarity	NPD919	Approved
0.7211	Intermediate Similarity	NPD2344	Approved
0.7203	Intermediate Similarity	NPD4062	Phase 3
0.72	Intermediate Similarity	NPD6666	Approved
0.72	Intermediate Similarity	NPD6667	Approved
0.7183	Intermediate Similarity	NPD3027	Phase 3
0.7183	Intermediate Similarity	NPD7095	Approved
0.7178	Intermediate Similarity	NPD7054	Approved
0.7178	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD2861	Phase 2
0.7162	Intermediate Similarity	NPD2424	Discontinued
0.716	Intermediate Similarity	NPD7473	Discontinued
0.7152	Intermediate Similarity	NPD6559	Discontinued
0.7152	Intermediate Similarity	NPD7213	Phase 3
0.7152	Intermediate Similarity	NPD7212	Phase 2
0.7143	Intermediate Similarity	NPD6362	Approved
0.7143	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7472	Approved
0.7132	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD5691	Approved
0.7132	Intermediate Similarity	NPD290	Approved
0.7125	Intermediate Similarity	NPD7199	Phase 2
0.7124	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD7097	Phase 1
0.7111	Intermediate Similarity	NPD5536	Phase 2
0.7108	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD7447	Phase 1
0.7099	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD6166	Phase 2
0.7095	Intermediate Similarity	NPD2346	Discontinued
0.7095	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD5647	Approved
0.7091	Intermediate Similarity	NPD6797	Phase 2
0.7091	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD8032	Phase 2
0.7081	Intermediate Similarity	NPD6232	Discontinued
0.7081	Intermediate Similarity	NPD7229	Phase 3
0.7077	Intermediate Similarity	NPD2684	Approved
0.7077	Intermediate Similarity	NPD74	Approved
0.7077	Intermediate Similarity	NPD9266	Approved
0.7067	Intermediate Similarity	NPD7003	Approved
0.7059	Intermediate Similarity	NPD5049	Phase 3
0.7055	Intermediate Similarity	NPD6653	Approved
0.7054	Intermediate Similarity	NPD968	Approved
0.7048	Intermediate Similarity	NPD7251	Discontinued
0.7042	Intermediate Similarity	NPD3018	Phase 2
0.7039	Intermediate Similarity	NPD4357	Discontinued
0.7039	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD7074	Phase 3
0.7027	Intermediate Similarity	NPD4476	Approved
0.7027	Intermediate Similarity	NPD4477	Approved
0.7023	Intermediate Similarity	NPD4750	Phase 3
0.702	Intermediate Similarity	NPD2354	Approved
0.702	Intermediate Similarity	NPD2309	Approved
0.7019	Intermediate Similarity	NPD6959	Discontinued
0.7014	Intermediate Similarity	NPD1048	Approved
0.7007	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7549	Discontinued
0.7006	Intermediate Similarity	NPD7808	Phase 3

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