NPASS Compound

Structure

NPC33653 OpenBabel07101719152D 32 33 0 0 1 0 0 0 0 0999 V2000 1.7321 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 7.7942 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 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 5.1962 -5.0000 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 6.0622 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 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 3.4641 -2.0000 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 6.9282 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -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 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 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 0.8660 -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 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 -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 0.8660 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 7 1 0 0 0 0 3 15 1 0 0 0 0 4 15 1 0 0 0 0 5 16 1 0 0 0 0 6 9 1 0 0 0 0 7 19 1 0 0 0 0 8 10 1 0 0 0 0 8 11 1 0 0 0 0 9 20 1 0 0 0 0 10 15 2 0 0 0 0 11 16 1 0 0 0 0 12 13 1 0 0 0 0 12 16 2 0 0 0 0 13 17 1 0 0 0 0 14 18 2 0 0 0 0 14 21 1 0 0 0 0 17 24 2 0 0 0 0 17 25 1 0 0 0 0 18 19 1 0 0 0 0 18 22 1 0 0 0 0 19 27 1 1 0 0 0 20 23 1 0 0 0 0 20 28 2 0 0 0 0 21 29 2 0 0 0 0 21 32 1 0 0 0 0 22 24 1 0 0 0 0 22 26 2 0 0 0 0 23 25 2 0 0 0 0 23 26 1 0 0 0 0 24 30 1 0 0 0 0 25 31 1 0 0 0 0 26 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	442.24
Volume:	472.789
LogP:	6.477
LogD:	3.649
LogS:	-3.489
# Rotatable Bonds:	10
TPSA:	107.97
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.241
Synthetic Accessibility Score:	3.72
Fsp3:	0.462
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.839
MDCK Permeability:	1.252595211553853e-05
Pgp-inhibitor:	0.853
Pgp-substrate:	0.954
Human Intestinal Absorption (HIA):	0.575
20% Bioavailability (F20%):	0.966
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013
Plasma Protein Binding (PPB):	90.10293579101562%
Volume Distribution (VD):	1.532
Pgp-substrate:	7.341561317443848%

ADMET: Metabolism

CYP1A2-inhibitor:	0.441
CYP1A2-substrate:	0.472
CYP2C19-inhibitor:	0.715
CYP2C19-substrate:	0.104
CYP2C9-inhibitor:	0.86
CYP2C9-substrate:	0.931
CYP2D6-inhibitor:	0.482
CYP2D6-substrate:	0.211
CYP3A4-inhibitor:	0.156
CYP3A4-substrate:	0.101

ADMET: Excretion

Clearance (CL):	10.323
Half-life (T1/2):	0.261

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.918
Drug-inuced Liver Injury (DILI):	0.788
AMES Toxicity:	0.043
Rat Oral Acute Toxicity:	0.363
Maximum Recommended Daily Dose:	0.763
Skin Sensitization:	0.355
Carcinogencity:	0.548
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.313

Download Data

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

Natural Product: NPC33653

Natural Product ID:	NPC33653
*Common Name:**	Kayeassamin A
IUPAC Name:	8-butanoyl-6-[(2E)-3,7-dimethylocta-2,6-dienyl]-5,7-dihydroxy-4-[(1S)-1-hydroxypropyl]chromen-2-one
Synonyms:
Standard InCHIKey:	LVPCBEMZVHIBKU-BAILOTOSSA-N
Standard InCHI:	InChI=1S/C26H34O6/c1-6-9-20(28)23-25(31)17(13-12-16(5)11-8-10-15(3)4)24(30)22-18(19(27)7-2)14-21(29)32-26(22)23/h10,12,14,19,27,30-31H,6-9,11,13H2,1-5H3/b16-12+/t19-/m0/s1
SMILES:	CCCC(=O)c1c(c(C/C=C(C)/CCC=C(C)C)c(c2c(cc(=O)oc12)[C@H](CC)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL453869
PubChem CID:	25070689
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
NPO4557	Kayea assamica	Species	Calophyllaceae	Eukaryota	flower	Myanmar	n.a.	PMID[18640837]
NPO4557	Kayea assamica	Species	Calophyllaceae	Eukaryota	flowers	Myanmar	n.a.	PMID[18725180]
NPO32974	mammea siamensis	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22831798]
NPO32974	mammea siamensis	Species	Calophyllaceae	Eukaryota	flower	n.a.	n.a.	PMID[23206866]
NPO4557	Kayea assamica	Species	Calophyllaceae	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	10
Others	8

Activity Type	# Activity
Cell Line	15
NON-MOLECULAR	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT461	Cell Line	PANC-1	Homo sapiens	Ratio	=	256.0	n.a.	PMID[507993]
NPT461	Cell Line	PANC-1	Homo sapiens	Cytotoxicity	=	1.0	uM	PMID[507993]
NPT461	Cell Line	PANC-1	Homo sapiens	Cytotoxicity	=	1.0	uM	PMID[507994]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	5.0	%	PMID[507995]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	15.0	%	PMID[507995]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	29.7	%	PMID[507995]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	56.6	%	PMID[507995]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	82.4	%	PMID[507995]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	26600.0	nM	PMID[507995]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	50000.0	nM	PMID[507996]
NPT148	Cell Line	HCT-15	Homo sapiens	IC50	>	50000.0	nM	PMID[507996]
NPT466	Cell Line	U-937	Homo sapiens	IC50	=	19950.0	nM	PMID[507996]
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	=	19790.0	nM	PMID[507996]
NPT1970	Cell Line	THP-1	Homo sapiens	IC50	=	16690.0	nM	PMID[507996]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	11860.0	nM	PMID[507996]
NPT27	Others	Unspecified		IC50	>	50000.0	nM	PMID[507996]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	11950.0	nM	PMID[507996]

☑ 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 NPC33653 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	351
0.1-0.2	1459
0.2-0.3	3597
0.3-0.4	7965
0.4-0.5	10938
0.5-0.6	3970
0.6-0.7	5913
0.7-0.8	4813
0.8-0.85	2510
0.85-0.9	976
0.9-0.95	185
0.95-1	20

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC184738
0.9928	High Similarity	NPC133060
0.9928	High Similarity	NPC288910
0.9928	High Similarity	NPC118059
0.9928	High Similarity	NPC470554
0.9927	High Similarity	NPC112829
0.9927	High Similarity	NPC294432
0.9856	High Similarity	NPC470910
0.9855	High Similarity	NPC470553
0.9855	High Similarity	NPC470909
0.9855	High Similarity	NPC474939
0.9855	High Similarity	NPC307895
0.9855	High Similarity	NPC96216
0.9783	High Similarity	NPC470556
0.9645	High Similarity	NPC285748
0.9565	High Similarity	NPC19476
0.9565	High Similarity	NPC241975
0.95	High Similarity	NPC472344
0.9493	High Similarity	NPC219584
0.9493	High Similarity	NPC470083
0.9493	High Similarity	NPC199458
0.9493	High Similarity	NPC183639
0.9444	High Similarity	NPC470908
0.9444	High Similarity	NPC474735
0.942	High Similarity	NPC138047
0.942	High Similarity	NPC131782
0.942	High Similarity	NPC474624
0.9371	High Similarity	NPC474108
0.9371	High Similarity	NPC177995
0.931	High Similarity	NPC321387
0.931	High Similarity	NPC327059
0.9286	High Similarity	NPC139554
0.9247	High Similarity	NPC290671
0.9231	High Similarity	NPC224714
0.9225	High Similarity	NPC276565
0.922	High Similarity	NPC221173
0.9184	High Similarity	NPC256141
0.9178	High Similarity	NPC180351
0.9172	High Similarity	NPC472345
0.9167	High Similarity	NPC181388
0.9167	High Similarity	NPC470322
0.9161	High Similarity	NPC18886
0.9155	High Similarity	NPC470555
0.9137	High Similarity	NPC101752
0.911	High Similarity	NPC19238
0.9103	High Similarity	NPC91902
0.9097	High Similarity	NPC470890
0.9097	High Similarity	NPC196137
0.9097	High Similarity	NPC469935
0.9097	High Similarity	NPC178627
0.9097	High Similarity	NPC1886
0.9091	High Similarity	NPC36181
0.9085	High Similarity	NPC471587
0.9085	High Similarity	NPC307990
0.9085	High Similarity	NPC16455
0.9078	High Similarity	NPC131130
0.9071	High Similarity	NPC470982
0.9071	High Similarity	NPC470983
0.9071	High Similarity	NPC174999
0.906	High Similarity	NPC108937
0.906	High Similarity	NPC279218
0.9041	High Similarity	NPC10097
0.9034	High Similarity	NPC154217
0.9034	High Similarity	NPC472629
0.9028	High Similarity	NPC470296
0.9028	High Similarity	NPC188632
0.9028	High Similarity	NPC196459
0.9028	High Similarity	NPC112791
0.9028	High Similarity	NPC94794
0.9028	High Similarity	NPC87609
0.9021	High Similarity	NPC74397
0.9021	High Similarity	NPC476508
0.9014	High Similarity	NPC23257
0.9014	High Similarity	NPC472343
0.9	High Similarity	NPC475797
0.9	High Similarity	NPC78554
0.9	High Similarity	NPC469936
0.9	High Similarity	NPC109967
0.9	High Similarity	NPC60667
0.9	High Similarity	NPC84699
0.9	High Similarity	NPC321372
0.9	High Similarity	NPC474738
0.9	High Similarity	NPC474609
0.9	High Similarity	NPC129053
0.8993	High Similarity	NPC470984
0.8986	High Similarity	NPC185624
0.8986	High Similarity	NPC312549
0.8986	High Similarity	NPC209142
0.898	High Similarity	NPC307052
0.898	High Similarity	NPC139966
0.898	High Similarity	NPC469932
0.898	High Similarity	NPC164205
0.898	High Similarity	NPC104236
0.898	High Similarity	NPC5173
0.8978	High Similarity	NPC21378
0.8978	High Similarity	NPC470987
0.8973	High Similarity	NPC47388
0.8973	High Similarity	NPC140120
0.8973	High Similarity	NPC470670
0.8973	High Similarity	NPC202494
0.8973	High Similarity	NPC473133
0.8973	High Similarity	NPC85773
0.8966	High Similarity	NPC87486
0.8966	High Similarity	NPC206212
0.8966	High Similarity	NPC124780
0.8966	High Similarity	NPC297788
0.8966	High Similarity	NPC469953
0.8966	High Similarity	NPC71184
0.894	High Similarity	NPC269495
0.8936	High Similarity	NPC268081
0.8936	High Similarity	NPC156910
0.8936	High Similarity	NPC470397
0.8929	High Similarity	NPC125920
0.8926	High Similarity	NPC273483
0.8921	High Similarity	NPC470988
0.8919	High Similarity	NPC38775
0.8919	High Similarity	NPC61258
0.8919	High Similarity	NPC37348
0.8912	High Similarity	NPC240622
0.8912	High Similarity	NPC470460
0.8912	High Similarity	NPC161864
0.8912	High Similarity	NPC469933
0.8912	High Similarity	NPC471642
0.8912	High Similarity	NPC471641
0.8912	High Similarity	NPC240253
0.8912	High Similarity	NPC168085
0.8912	High Similarity	NPC208303
0.8904	High Similarity	NPC474302
0.8904	High Similarity	NPC57470
0.8904	High Similarity	NPC290133
0.8904	High Similarity	NPC24136
0.8904	High Similarity	NPC187282
0.8904	High Similarity	NPC470458
0.8897	High Similarity	NPC51887
0.8897	High Similarity	NPC476178
0.8897	High Similarity	NPC185276
0.8897	High Similarity	NPC475705
0.8897	High Similarity	NPC117836
0.8889	High Similarity	NPC248372
0.8889	High Similarity	NPC470087
0.8889	High Similarity	NPC321980
0.8889	High Similarity	NPC156190
0.8889	High Similarity	NPC17170
0.8889	High Similarity	NPC166689
0.8889	High Similarity	NPC279650
0.8889	High Similarity	NPC96408
0.8889	High Similarity	NPC258630
0.8889	High Similarity	NPC201820
0.8889	High Similarity	NPC110038
0.8881	High Similarity	NPC217186
0.8881	High Similarity	NPC471697
0.8881	High Similarity	NPC53181
0.8881	High Similarity	NPC37206
0.8873	High Similarity	NPC332594
0.8873	High Similarity	NPC38153
0.8873	High Similarity	NPC253616
0.8867	High Similarity	NPC193200
0.8859	High Similarity	NPC471677
0.8857	High Similarity	NPC16197
0.8857	High Similarity	NPC93756
0.8857	High Similarity	NPC108113
0.8857	High Similarity	NPC223457
0.8851	High Similarity	NPC317492
0.8851	High Similarity	NPC470461
0.8844	High Similarity	NPC249942
0.8844	High Similarity	NPC283234
0.8844	High Similarity	NPC297886
0.8844	High Similarity	NPC180477
0.8844	High Similarity	NPC473077
0.8844	High Similarity	NPC8817
0.8844	High Similarity	NPC296998
0.8836	High Similarity	NPC235217
0.8836	High Similarity	NPC319752
0.8836	High Similarity	NPC236766
0.8836	High Similarity	NPC216538
0.8836	High Similarity	NPC197252
0.8836	High Similarity	NPC294365
0.8836	High Similarity	NPC171656
0.8836	High Similarity	NPC473014
0.8836	High Similarity	NPC273538
0.8828	High Similarity	NPC182852
0.8828	High Similarity	NPC324134
0.8828	High Similarity	NPC32739
0.8828	High Similarity	NPC76338
0.8828	High Similarity	NPC328164
0.8828	High Similarity	NPC78
0.8828	High Similarity	NPC148757
0.8828	High Similarity	NPC166482
0.8828	High Similarity	NPC194432
0.8828	High Similarity	NPC296917
0.8828	High Similarity	NPC66515
0.8828	High Similarity	NPC177354
0.8828	High Similarity	NPC40833
0.8828	High Similarity	NPC10937
0.8828	High Similarity	NPC76372
0.8828	High Similarity	NPC228504
0.8828	High Similarity	NPC306829
0.8828	High Similarity	NPC227579
0.8828	High Similarity	NPC324436
0.8828	High Similarity	NPC125855

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 NPC33653 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	312
0.1-0.2	937
0.2-0.3	1794
0.3-0.4	2526
0.4-0.5	1968
0.5-0.6	1071
0.6-0.7	363
0.7-0.8	126
0.8-0.85	38
0.85-0.9	12
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8836	High Similarity	NPD4378	Clinical (unspecified phase)
0.8707	High Similarity	NPD2533	Approved
0.8707	High Similarity	NPD2534	Approved
0.8707	High Similarity	NPD2532	Approved
0.8693	High Similarity	NPD7075	Discontinued
0.8621	High Similarity	NPD2800	Approved
0.8618	High Similarity	NPD7096	Clinical (unspecified phase)
0.8553	High Similarity	NPD6801	Discontinued
0.8543	High Similarity	NPD4380	Phase 2
0.8497	Intermediate Similarity	NPD7819	Suspended
0.8497	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8487	Intermediate Similarity	NPD7411	Suspended
0.8483	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8483	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD6651	Approved
0.8456	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8442	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8425	Intermediate Similarity	NPD1549	Phase 2
0.8425	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8414	Intermediate Similarity	NPD2796	Approved
0.8367	Intermediate Similarity	NPD1243	Approved
0.8345	Intermediate Similarity	NPD1510	Phase 2
0.8344	Intermediate Similarity	NPD920	Approved
0.8333	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD7768	Phase 2
0.8267	Intermediate Similarity	NPD6799	Approved
0.8264	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8264	Intermediate Similarity	NPD5124	Phase 1
0.8212	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.82	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD1240	Approved
0.8194	Intermediate Similarity	NPD1934	Approved
0.8188	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD3817	Phase 2
0.8082	Intermediate Similarity	NPD1607	Approved
0.8067	Intermediate Similarity	NPD3750	Approved
0.8065	Intermediate Similarity	NPD6599	Discontinued
0.8063	Intermediate Similarity	NPD6959	Discontinued
0.8041	Intermediate Similarity	NPD1551	Phase 2
0.8041	Intermediate Similarity	NPD2935	Discontinued
0.8026	Intermediate Similarity	NPD1511	Approved
0.8025	Intermediate Similarity	NPD2801	Approved
0.8012	Intermediate Similarity	NPD5710	Approved
0.8012	Intermediate Similarity	NPD5711	Approved
0.7988	Intermediate Similarity	NPD7286	Phase 2
0.7988	Intermediate Similarity	NPD7054	Approved
0.7987	Intermediate Similarity	NPD5403	Approved
0.7939	Intermediate Similarity	NPD7074	Phase 3
0.7939	Intermediate Similarity	NPD7472	Approved
0.7931	Intermediate Similarity	NPD2313	Discontinued
0.7927	Intermediate Similarity	NPD3818	Discontinued
0.7925	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD1512	Approved
0.7914	Intermediate Similarity	NPD6166	Phase 2
0.7914	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD5953	Discontinued
0.7879	Intermediate Similarity	NPD5844	Phase 1
0.7875	Intermediate Similarity	NPD3749	Approved
0.7866	Intermediate Similarity	NPD7473	Discontinued
0.7862	Intermediate Similarity	NPD5402	Approved
0.7857	Intermediate Similarity	NPD5401	Approved
0.7852	Intermediate Similarity	NPD2799	Discontinued
0.7844	Intermediate Similarity	NPD7251	Discontinued
0.7844	Intermediate Similarity	NPD6559	Discontinued
0.7829	Intermediate Similarity	NPD4628	Phase 3
0.7826	Intermediate Similarity	NPD919	Approved
0.7812	Intermediate Similarity	NPD3882	Suspended
0.7801	Intermediate Similarity	NPD422	Phase 1
0.7798	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD7808	Phase 3
0.7793	Intermediate Similarity	NPD6832	Phase 2
0.7791	Intermediate Similarity	NPD6232	Discontinued
0.7784	Intermediate Similarity	NPD6797	Phase 2
0.7746	Intermediate Similarity	NPD9717	Approved
0.7733	Intermediate Similarity	NPD3748	Approved
0.7733	Intermediate Similarity	NPD7033	Discontinued
0.7712	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD1203	Approved
0.7692	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD5494	Approved
0.7658	Intermediate Similarity	NPD3226	Approved
0.7574	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD3268	Approved
0.7562	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD230	Phase 1
0.7516	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2346	Discontinued
0.7516	Intermediate Similarity	NPD6004	Phase 3
0.7516	Intermediate Similarity	NPD6005	Phase 3
0.7516	Intermediate Similarity	NPD6002	Phase 3
0.7466	Intermediate Similarity	NPD2797	Approved
0.7458	Intermediate Similarity	NPD4360	Phase 2
0.7458	Intermediate Similarity	NPD4363	Phase 3
0.7451	Intermediate Similarity	NPD6099	Approved
0.7451	Intermediate Similarity	NPD6100	Approved
0.745	Intermediate Similarity	NPD1296	Phase 2
0.7419	Intermediate Similarity	NPD1652	Phase 2
0.7417	Intermediate Similarity	NPD447	Suspended
0.7417	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD1019	Discontinued
0.741	Intermediate Similarity	NPD1247	Approved
0.7403	Intermediate Similarity	NPD2344	Approved
0.7394	Intermediate Similarity	NPD9545	Approved
0.7386	Intermediate Similarity	NPD4308	Phase 3
0.7362	Intermediate Similarity	NPD1465	Phase 2
0.7345	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD411	Approved
0.7333	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD2654	Approved
0.7296	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD3225	Approved
0.7273	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD7229	Phase 3
0.7254	Intermediate Similarity	NPD9493	Approved
0.7241	Intermediate Similarity	NPD8313	Approved
0.7241	Intermediate Similarity	NPD8312	Approved
0.7233	Intermediate Similarity	NPD7390	Discontinued
0.723	Intermediate Similarity	NPD3266	Approved
0.723	Intermediate Similarity	NPD3267	Approved
0.7222	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4361	Phase 2
0.7222	Intermediate Similarity	NPD7458	Discontinued
0.7222	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD2309	Approved
0.7204	Intermediate Similarity	NPD7584	Approved
0.72	Intermediate Similarity	NPD4908	Phase 1
0.7193	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD6355	Discontinued
0.7181	Intermediate Similarity	NPD2798	Approved
0.716	Intermediate Similarity	NPD1653	Approved
0.7153	Intermediate Similarity	NPD1548	Phase 1
0.7152	Intermediate Similarity	NPD8455	Phase 2
0.7143	Intermediate Similarity	NPD1608	Approved
0.7135	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2424	Discontinued
0.7134	Intermediate Similarity	NPD5890	Approved
0.7134	Intermediate Similarity	NPD5889	Approved
0.7124	Intermediate Similarity	NPD4307	Phase 2
0.7124	Intermediate Similarity	NPD943	Approved
0.7119	Intermediate Similarity	NPD8434	Phase 2
0.711	Intermediate Similarity	NPD1729	Discontinued
0.7108	Intermediate Similarity	NPD4288	Approved
0.7105	Intermediate Similarity	NPD6798	Discontinued
0.7105	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD37	Approved
0.7086	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD1610	Phase 2
0.7074	Intermediate Similarity	NPD7585	Approved
0.7066	Intermediate Similarity	NPD4965	Approved
0.7066	Intermediate Similarity	NPD4966	Approved
0.7066	Intermediate Similarity	NPD4967	Phase 2
0.7039	Intermediate Similarity	NPD4287	Approved
0.7037	Intermediate Similarity	NPD8151	Discontinued
0.7037	Intermediate Similarity	NPD6273	Approved
0.7029	Intermediate Similarity	NPD6104	Discontinued
0.7021	Intermediate Similarity	NPD7583	Approved
0.7018	Intermediate Similarity	NPD3926	Phase 2
0.7013	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD1613	Approved
0.7006	Intermediate Similarity	NPD5408	Approved
0.7006	Intermediate Similarity	NPD4476	Approved
0.7006	Intermediate Similarity	NPD4477	Approved
0.7006	Intermediate Similarity	NPD5404	Approved
0.7006	Intermediate Similarity	NPD5406	Approved
0.7006	Intermediate Similarity	NPD5405	Approved
0.7006	Intermediate Similarity	NPD5353	Approved
0.7	Intermediate Similarity	NPD7199	Phase 2
0.7	Intermediate Similarity	NPD1164	Approved
0.6988	Remote Similarity	NPD6844	Discontinued
0.6982	Remote Similarity	NPD6234	Discontinued
0.6977	Remote Similarity	NPD2403	Approved
0.697	Remote Similarity	NPD6585	Discontinued
0.6968	Remote Similarity	NPD1933	Approved
0.6963	Remote Similarity	NPD7783	Phase 2
0.6963	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6667	Approved
0.6957	Remote Similarity	NPD6666	Approved
0.6952	Remote Similarity	NPD7435	Discontinued
0.6948	Remote Similarity	NPD6233	Phase 2
0.6946	Remote Similarity	NPD5761	Phase 2
0.6946	Remote Similarity	NPD5760	Phase 2
0.6939	Remote Similarity	NPD1778	Approved
0.6939	Remote Similarity	NPD17	Approved
0.6937	Remote Similarity	NPD7003	Approved
0.6933	Remote Similarity	NPD5049	Phase 3
0.6928	Remote Similarity	NPD3027	Phase 3
0.6927	Remote Similarity	NPD8150	Discontinued
0.6923	Remote Similarity	NPD1241	Discontinued

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