NPASS Compound

Structure

NPC294365 OpenBabel07101718192D 26 28 0 0 1 0 0 0 0 0999 V2000 0.0000 3.0000 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 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 -0.3660 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 4.3301 1.5000 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 -0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 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 3.4641 2.0000 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 2.5981 0.5000 0.0000 C 0 0 0 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 1.5000 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 -1.7321 3.0000 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 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 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 -1.7321 2.0000 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 10 1 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 4 20 1 0 0 0 0 5 20 1 0 0 0 0 6 23 1 0 0 0 0 7 11 2 0 0 0 0 7 13 1 0 0 0 0 8 12 1 0 0 0 0 8 16 1 0 0 0 0 9 14 2 0 0 0 0 9 15 1 0 0 0 0 10 19 1 0 0 0 0 11 24 1 0 0 0 0 12 14 1 0 0 0 0 12 18 2 0 0 0 0 13 17 1 0 0 0 0 13 21 2 0 0 0 0 14 26 1 0 0 0 0 15 17 2 0 0 0 0 15 24 1 0 0 0 0 16 20 1 0 0 0 0 16 25 1 6 0 0 0 17 18 1 0 0 0 0 18 23 1 0 0 0 0 19 22 2 0 0 0 0 19 25 1 0 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	360.16
Volume:	365.729
LogP:	4.312
LogD:	2.983
LogS:	-3.487
# Rotatable Bonds:	4
TPSA:	74.97
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.781
Synthetic Accessibility Score:	3.513
Fsp3:	0.5
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:	-4.641
MDCK Permeability:	2.1854768419871107e-05
Pgp-inhibitor:	0.937
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.181

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.127
Plasma Protein Binding (PPB):	87.8138198852539%
Volume Distribution (VD):	0.987
Pgp-substrate:	11.387558937072754%

ADMET: Metabolism

CYP1A2-inhibitor:	0.422
CYP1A2-substrate:	0.942
CYP2C19-inhibitor:	0.688
CYP2C19-substrate:	0.857
CYP2C9-inhibitor:	0.777
CYP2C9-substrate:	0.866
CYP2D6-inhibitor:	0.039
CYP2D6-substrate:	0.522
CYP3A4-inhibitor:	0.373
CYP3A4-substrate:	0.787

ADMET: Excretion

Clearance (CL):	2.907
Half-life (T1/2):	0.152

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.943
Drug-inuced Liver Injury (DILI):	0.634
AMES Toxicity:	0.037
Rat Oral Acute Toxicity:	0.21
Maximum Recommended Daily Dose:	0.309
Skin Sensitization:	0.143
Carcinogencity:	0.401
Eye Corrosion:	0.003
Eye Irritation:	0.024
Respiratory Toxicity:	0.258

Download Data

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

Natural Product: NPC294365

Natural Product ID:	NPC294365
*Common Name:**	[(3R)-5-Methoxy-2,2,8-Trimethyl-6-Oxo-3,4-Dihydropyrano[3,2-G]Chromen-3-Yl] 2-Methylpropanoate
IUPAC Name:	[(3R)-5-methoxy-2,2,8-trimethyl-6-oxo-3,4-dihydropyrano[3,2-g]chromen-3-yl] 2-methylpropanoate
Synonyms:
Standard InCHIKey:	YLXXSWJDIFLXSG-MRXNPFEDSA-N
Standard InCHI:	InChI=1S/C20H24O6/c1-10(2)19(22)25-16-8-12-14(26-20(16,4)5)9-15-17(18(12)23-6)13(21)7-11(3)24-15/h7,9-10,16H,8H2,1-6H3/t16-/m1/s1
SMILES:	CC(C)C(=O)O[C@@H]1Cc2c(cc3c(c(=O)cc(C)o3)c2OC)OC1(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518222
PubChem CID:	11068391
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0003543] Pyranochromenes

*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
NPO32915	prionosciadium watsoni	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12088423]

☑ 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	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT965	Organism	Amaranthus hypochondriacus	Amaranthus hypochondriacus	IC50	=	74100.0	nM	PMID[475130]
NPT117	Organism	Echinochloa crus-galli	Echinochloa crus-galli	IC50	=	14800.0	nM	PMID[475130]

☑ 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 NPC294365 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	401
0.1-0.2	1603
0.2-0.3	3920
0.3-0.4	8979
0.4-0.5	9798
0.5-0.6	3999
0.6-0.7	6048
0.7-0.8	5271
0.8-0.85	2010
0.85-0.9	577
0.9-0.95	72
0.95-1	19

Similarity Score	Similarity Level	Natural Product ID
0.9856	High Similarity	NPC171656
0.958	High Similarity	NPC164299
0.9514	High Similarity	NPC180351
0.9384	High Similarity	NPC256141
0.9371	High Similarity	NPC474302
0.9225	High Similarity	NPC201820
0.9178	High Similarity	NPC307052
0.9178	High Similarity	NPC139966
0.9172	High Similarity	NPC470670
0.9172	High Similarity	NPC282335
0.9172	High Similarity	NPC85773
0.9172	High Similarity	NPC218300
0.9172	High Similarity	NPC473133
0.9172	High Similarity	NPC47388
0.9149	High Similarity	NPC36414
0.9143	High Similarity	NPC268081
0.911	High Similarity	NPC10097
0.9085	High Similarity	NPC472515
0.9085	High Similarity	NPC11566
0.9085	High Similarity	NPC473209
0.9078	High Similarity	NPC253616
0.9078	High Similarity	NPC259685
0.9073	High Similarity	NPC50430
0.9071	High Similarity	NPC46869
0.9067	High Similarity	NPC469936
0.9067	High Similarity	NPC109967
0.9067	High Similarity	NPC78554
0.9067	High Similarity	NPC475797
0.9067	High Similarity	NPC470625
0.9067	High Similarity	NPC474738
0.9067	High Similarity	NPC474609
0.9067	High Similarity	NPC129053
0.9067	High Similarity	NPC321372
0.9048	High Similarity	NPC164205
0.9048	High Similarity	NPC104236
0.9041	High Similarity	NPC91902
0.9028	High Similarity	NPC470556
0.9021	High Similarity	NPC470856
0.9021	High Similarity	NPC472409
0.9013	High Similarity	NPC43971
0.9013	High Similarity	NPC19554
0.9013	High Similarity	NPC74749
0.9007	High Similarity	NPC161196
0.9	High Similarity	NPC108937
0.9	High Similarity	NPC279218
0.8993	High Similarity	NPC40033
0.8986	High Similarity	NPC321387
0.8986	High Similarity	NPC327059
0.8986	High Similarity	NPC470908
0.8986	High Similarity	NPC474735
0.898	High Similarity	NPC472345
0.898	High Similarity	NPC476342
0.8966	High Similarity	NPC59522
0.8966	High Similarity	NPC96216
0.8966	High Similarity	NPC470909
0.8966	High Similarity	NPC18886
0.8966	High Similarity	NPC470553
0.8966	High Similarity	NPC307895
0.8966	High Similarity	NPC474939
0.8958	High Similarity	NPC52576
0.8951	High Similarity	NPC136095
0.8944	High Similarity	NPC38153
0.894	High Similarity	NPC17521
0.8936	High Similarity	NPC160727
0.8936	High Similarity	NPC55615
0.8936	High Similarity	NPC283019
0.8936	High Similarity	NPC177281
0.8936	High Similarity	NPC476455
0.8936	High Similarity	NPC99854
0.8936	High Similarity	NPC128529
0.8936	High Similarity	NPC149320
0.8936	High Similarity	NPC471630
0.8933	High Similarity	NPC7989
0.8933	High Similarity	NPC469405
0.8933	High Similarity	NPC236756
0.8933	High Similarity	NPC223701
0.8933	High Similarity	NPC311579
0.8933	High Similarity	NPC472583
0.8926	High Similarity	NPC472422
0.8926	High Similarity	NPC474021
0.8926	High Similarity	NPC472636
0.8926	High Similarity	NPC244577
0.8926	High Similarity	NPC471677
0.8926	High Similarity	NPC263384
0.8926	High Similarity	NPC474023
0.8926	High Similarity	NPC471675
0.8926	High Similarity	NPC471676
0.8926	High Similarity	NPC290671
0.8926	High Similarity	NPC295650
0.8926	High Similarity	NPC472420
0.8919	High Similarity	NPC19238
0.8912	High Similarity	NPC473077
0.8912	High Similarity	NPC177995
0.8912	High Similarity	NPC202494
0.8912	High Similarity	NPC296998
0.8912	High Similarity	NPC474108
0.8912	High Similarity	NPC285748
0.8904	High Similarity	NPC131568
0.8904	High Similarity	NPC131579
0.8904	High Similarity	NPC224714
0.8904	High Similarity	NPC87486
0.8904	High Similarity	NPC470554
0.8904	High Similarity	NPC133060
0.8904	High Similarity	NPC470890
0.8904	High Similarity	NPC288910
0.8904	High Similarity	NPC124780
0.8904	High Similarity	NPC316535
0.8904	High Similarity	NPC118059
0.8897	High Similarity	NPC472344
0.8897	High Similarity	NPC147145
0.8897	High Similarity	NPC276565
0.8897	High Similarity	NPC471643
0.8897	High Similarity	NPC471639
0.8897	High Similarity	NPC294432
0.8897	High Similarity	NPC112829
0.8889	High Similarity	NPC477164
0.8881	High Similarity	NPC470671
0.8881	High Similarity	NPC470672
0.8881	High Similarity	NPC474487
0.8881	High Similarity	NPC474504
0.8881	High Similarity	NPC131130
0.8881	High Similarity	NPC17848
0.8874	High Similarity	NPC217706
0.8874	High Similarity	NPC470603
0.8874	High Similarity	NPC470604
0.8874	High Similarity	NPC259710
0.8874	High Similarity	NPC207809
0.8874	High Similarity	NPC304207
0.8874	High Similarity	NPC477530
0.8874	High Similarity	NPC470605
0.8874	High Similarity	NPC48579
0.8873	High Similarity	NPC254741
0.8873	High Similarity	NPC472516
0.8867	High Similarity	NPC216035
0.8867	High Similarity	NPC475790
0.8867	High Similarity	NPC327269
0.8867	High Similarity	NPC161881
0.8867	High Similarity	NPC150123
0.8867	High Similarity	NPC56232
0.8867	High Similarity	NPC10807
0.8867	High Similarity	NPC473996
0.8867	High Similarity	NPC244583
0.8867	High Similarity	NPC288534
0.8867	High Similarity	NPC31627
0.8867	High Similarity	NPC217149
0.8867	High Similarity	NPC476238
0.8865	High Similarity	NPC86892
0.8865	High Similarity	NPC471909
0.8865	High Similarity	NPC471625
0.8865	High Similarity	NPC472424
0.8865	High Similarity	NPC281241
0.8859	High Similarity	NPC471115
0.8859	High Similarity	NPC29777
0.8859	High Similarity	NPC472633
0.8857	High Similarity	NPC229646
0.8844	High Similarity	NPC214774
0.8844	High Similarity	NPC472629
0.8844	High Similarity	NPC54577
0.8844	High Similarity	NPC470322
0.8844	High Similarity	NPC470910
0.8844	High Similarity	NPC267375
0.8844	High Similarity	NPC470647
0.8844	High Similarity	NPC154217
0.8844	High Similarity	NPC301276
0.8844	High Similarity	NPC127059
0.8844	High Similarity	NPC67805
0.8844	High Similarity	NPC111786
0.8844	High Similarity	NPC142405
0.8844	High Similarity	NPC20488
0.8844	High Similarity	NPC176229
0.8844	High Similarity	NPC88964
0.8844	High Similarity	NPC24136
0.8844	High Similarity	NPC312973
0.8844	High Similarity	NPC187282
0.8844	High Similarity	NPC290133
0.8844	High Similarity	NPC285630
0.8844	High Similarity	NPC195621
0.8844	High Similarity	NPC246948
0.8844	High Similarity	NPC475052
0.8844	High Similarity	NPC83357
0.8841	High Similarity	NPC473894
0.8836	High Similarity	NPC214166
0.8836	High Similarity	NPC184738
0.8836	High Similarity	NPC478086
0.8836	High Similarity	NPC33653
0.8836	High Similarity	NPC85162
0.8836	High Similarity	NPC125894
0.8836	High Similarity	NPC223812
0.8836	High Similarity	NPC278249
0.8836	High Similarity	NPC316816
0.8836	High Similarity	NPC77794
0.8836	High Similarity	NPC81697
0.8836	High Similarity	NPC107177
0.8831	High Similarity	NPC92589
0.8831	High Similarity	NPC97812
0.8828	High Similarity	NPC471644
0.8828	High Similarity	NPC22467
0.8828	High Similarity	NPC17170
0.8828	High Similarity	NPC166689
0.8828	High Similarity	NPC156190

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 NPC294365 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	337
0.1-0.2	950
0.2-0.3	1771
0.3-0.4	2603
0.4-0.5	1899
0.5-0.6	1062
0.6-0.7	366
0.7-0.8	125
0.8-0.85	32
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8933	High Similarity	NPD7096	Clinical (unspecified phase)
0.8873	High Similarity	NPD2796	Approved
0.8758	High Similarity	NPD7075	Discontinued
0.8742	High Similarity	NPD6801	Discontinued
0.8649	High Similarity	NPD4378	Clinical (unspecified phase)
0.8609	High Similarity	NPD4380	Phase 2
0.8581	High Similarity	NPD6799	Approved
0.8562	High Similarity	NPD1243	Approved
0.8562	High Similarity	NPD2393	Clinical (unspecified phase)
0.8562	High Similarity	NPD7819	Suspended
0.8553	High Similarity	NPD7411	Suspended
0.8533	High Similarity	NPD920	Approved
0.8526	High Similarity	NPD5494	Approved
0.8506	High Similarity	NPD3817	Phase 2
0.8425	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8425	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8397	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8389	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8377	Intermediate Similarity	NPD1934	Approved
0.8367	Intermediate Similarity	NPD1549	Phase 2
0.8366	Intermediate Similarity	NPD6599	Discontinued
0.8278	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8272	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8243	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD919	Approved
0.817	Intermediate Similarity	NPD5403	Approved
0.8163	Intermediate Similarity	NPD1510	Phase 2
0.8163	Intermediate Similarity	NPD3748	Approved
0.8158	Intermediate Similarity	NPD5401	Approved
0.8101	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD2801	Approved
0.8086	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD2534	Approved
0.8039	Intermediate Similarity	NPD2533	Approved
0.8039	Intermediate Similarity	NPD2532	Approved
0.8038	Intermediate Similarity	NPD5402	Approved
0.8012	Intermediate Similarity	NPD6959	Discontinued
0.8	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD7768	Phase 2
0.7975	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD6166	Phase 2
0.7974	Intermediate Similarity	NPD1511	Approved
0.7959	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD5124	Phase 1
0.7947	Intermediate Similarity	NPD2800	Approved
0.7939	Intermediate Similarity	NPD7054	Approved
0.7939	Intermediate Similarity	NPD5844	Phase 1
0.7927	Intermediate Similarity	NPD7473	Discontinued
0.7919	Intermediate Similarity	NPD2799	Discontinued
0.7904	Intermediate Similarity	NPD6559	Discontinued
0.7901	Intermediate Similarity	NPD1247	Approved
0.7895	Intermediate Similarity	NPD3750	Approved
0.7892	Intermediate Similarity	NPD7472	Approved
0.7892	Intermediate Similarity	NPD7074	Phase 3
0.7891	Intermediate Similarity	NPD1240	Approved
0.7879	Intermediate Similarity	NPD3818	Discontinued
0.7877	Intermediate Similarity	NPD2313	Discontinued
0.7871	Intermediate Similarity	NPD1512	Approved
0.7862	Intermediate Similarity	NPD6832	Phase 2
0.7857	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD6232	Discontinued
0.7844	Intermediate Similarity	NPD6797	Phase 2
0.7826	Intermediate Similarity	NPD3749	Approved
0.7798	Intermediate Similarity	NPD7251	Discontinued
0.7785	Intermediate Similarity	NPD6651	Approved
0.7785	Intermediate Similarity	NPD1607	Approved
0.7778	Intermediate Similarity	NPD4628	Phase 3
0.7778	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD3882	Suspended
0.7751	Intermediate Similarity	NPD7808	Phase 3
0.7748	Intermediate Similarity	NPD1551	Phase 2
0.7748	Intermediate Similarity	NPD2935	Discontinued
0.7746	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD1933	Approved
0.7707	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD7033	Discontinued
0.7655	Intermediate Similarity	NPD3267	Approved
0.7655	Intermediate Similarity	NPD3266	Approved
0.7651	Intermediate Similarity	NPD2403	Approved
0.7635	Intermediate Similarity	NPD1296	Phase 2
0.7633	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD5953	Discontinued
0.7625	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD7286	Phase 2
0.7603	Intermediate Similarity	NPD1019	Discontinued
0.76	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD1652	Phase 2
0.7597	Intermediate Similarity	NPD2654	Approved
0.7593	Intermediate Similarity	NPD5353	Approved
0.7582	Intermediate Similarity	NPD2346	Discontinued
0.7545	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD4307	Phase 2
0.753	Intermediate Similarity	NPD5711	Approved
0.753	Intermediate Similarity	NPD5710	Approved
0.7517	Intermediate Similarity	NPD3268	Approved
0.7516	Intermediate Similarity	NPD6099	Approved
0.7516	Intermediate Similarity	NPD5890	Approved
0.7516	Intermediate Similarity	NPD6100	Approved
0.7516	Intermediate Similarity	NPD5889	Approved
0.75	Intermediate Similarity	NPD3887	Approved
0.75	Intermediate Similarity	NPD3226	Approved
0.7485	Intermediate Similarity	NPD3926	Phase 2
0.7483	Intermediate Similarity	NPD2798	Approved
0.7455	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD6585	Discontinued
0.7448	Intermediate Similarity	NPD9717	Approved
0.743	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD1465	Phase 2
0.7419	Intermediate Similarity	NPD2424	Discontinued
0.7416	Intermediate Similarity	NPD4360	Phase 2
0.7416	Intermediate Similarity	NPD4363	Phase 3
0.7415	Intermediate Similarity	NPD2797	Approved
0.7401	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD6798	Discontinued
0.7391	Intermediate Similarity	NPD7458	Discontinued
0.7379	Intermediate Similarity	NPD422	Phase 1
0.7368	Intermediate Similarity	NPD447	Suspended
0.7368	Intermediate Similarity	NPD230	Phase 1
0.7368	Intermediate Similarity	NPD6355	Discontinued
0.7361	Intermediate Similarity	NPD17	Approved
0.7358	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD4308	Phase 3
0.7321	Intermediate Similarity	NPD7229	Phase 3
0.7317	Intermediate Similarity	NPD8455	Phase 2
0.7299	Intermediate Similarity	NPD8312	Approved
0.7299	Intermediate Similarity	NPD8313	Approved
0.7297	Intermediate Similarity	NPD1203	Approved
0.7284	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD8434	Phase 2
0.7273	Intermediate Similarity	NPD7097	Phase 1
0.7267	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4908	Phase 1
0.7262	Intermediate Similarity	NPD7199	Phase 2
0.7258	Intermediate Similarity	NPD7584	Approved
0.7256	Intermediate Similarity	NPD37	Approved
0.7244	Intermediate Similarity	NPD2353	Approved
0.7244	Intermediate Similarity	NPD6005	Phase 3
0.7244	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD6004	Phase 3
0.7244	Intermediate Similarity	NPD6002	Phase 3
0.7244	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD6233	Phase 2
0.7234	Intermediate Similarity	NPD1241	Discontinued
0.7229	Intermediate Similarity	NPD4966	Approved
0.7229	Intermediate Similarity	NPD4965	Approved
0.7229	Intermediate Similarity	NPD4967	Phase 2
0.7219	Intermediate Similarity	NPD3787	Discontinued
0.7211	Intermediate Similarity	NPD1608	Approved
0.7179	Intermediate Similarity	NPD2438	Suspended
0.7176	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD5242	Approved
0.7169	Intermediate Similarity	NPD4288	Approved
0.7158	Intermediate Similarity	NPD8285	Discontinued
0.7151	Intermediate Similarity	NPD3751	Discontinued
0.7143	Intermediate Similarity	NPD6234	Discontinued
0.7143	Intermediate Similarity	NPD1610	Phase 2
0.7134	Intermediate Similarity	NPD2344	Approved
0.7125	Intermediate Similarity	NPD6652	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD6808	Phase 2
0.7117	Intermediate Similarity	NPD1653	Approved
0.7115	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD3225	Approved
0.7103	Intermediate Similarity	NPD9545	Approved
0.7099	Intermediate Similarity	NPD5049	Phase 3
0.7099	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD3972	Approved
0.7088	Intermediate Similarity	NPD4361	Phase 2
0.7088	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7390	Discontinued
0.7079	Intermediate Similarity	NPD8150	Discontinued
0.7078	Intermediate Similarity	NPD2979	Phase 3
0.7078	Intermediate Similarity	NPD1613	Approved
0.7078	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD3142	Approved
0.7078	Intermediate Similarity	NPD3140	Approved
0.7074	Intermediate Similarity	NPD7583	Approved
0.7063	Intermediate Similarity	NPD2354	Approved
0.7059	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD411	Approved
0.7055	Intermediate Similarity	NPD5691	Approved
0.7047	Intermediate Similarity	NPD4749	Approved
0.7037	Intermediate Similarity	NPD7585	Approved
0.7032	Intermediate Similarity	NPD4622	Approved
0.7032	Intermediate Similarity	NPD4618	Approved
0.7022	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7435	Discontinued
0.7	Intermediate Similarity	NPD7003	Approved
0.7	Intermediate Similarity	NPD8397	Clinical (unspecified phase)

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