NPASS Compound

Structure

NPC475490 OpenBabel07101718312D 36 43 0 0 1 0 0 0 0 0999 V2000 1.2504 -2.9149 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4093 -2.6458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7481 1.2268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4286 -2.3555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0638 -1.5591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7828 -1.1610 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7374 -1.0314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6618 0.3327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7336 -2.0394 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7259 -1.9157 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1868 -0.8040 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6366 -1.2284 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1980 -0.1092 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4910 -1.2284 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4648 -0.4932 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9076 -0.6706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3901 -0.8234 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6366 -0.5669 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3093 -1.5119 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3093 -1.1339 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -4.0655 0.0754 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3273 -0.9449 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.9149 -0.9337 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8052 0.2284 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3273 -1.7008 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9820 0.1890 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4013 -0.1286 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1037 -1.2654 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3898 1.0214 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8204 -0.5094 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5163 -2.6828 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0093 0.7913 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0474 -1.0487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0394 -0.4505 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3273 -0.3780 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 24 1 0 0 0 0 6 17 1 0 0 0 0 7 16 1 0 0 0 0 8 13 1 0 0 0 0 9 1 1 1 0 0 0 9 10 1 0 0 0 0 9 20 1 0 0 0 0 10 2 1 6 0 0 0 10 23 1 0 0 0 0 11 6 1 6 0 0 0 11 12 1 0 0 0 0 11 13 1 0 0 0 0 12 5 1 1 0 0 0 12 18 1 0 0 0 0 13 24 1 1 0 0 0 14 5 1 6 0 0 0 14 19 1 0 0 0 0 14 35 1 0 0 0 0 15 7 1 1 0 0 0 15 21 1 0 0 0 0 15 33 1 0 0 0 0 16 24 1 0 0 0 0 16 28 2 0 0 0 0 17 27 1 1 0 0 0 17 33 1 0 0 0 0 18 19 1 0 0 0 0 18 26 1 1 0 0 0 19 25 1 6 0 0 0 20 22 1 0 0 0 0 20 34 1 0 0 0 0 21 27 1 0 0 0 0 21 29 2 0 0 0 0 22 25 1 0 0 0 0 22 36 1 0 0 0 0 23 30 2 0 0 0 0 23 34 1 0 0 0 0 24 27 1 1 0 0 0 25 4 1 1 0 0 0 25 31 1 0 0 0 0 26 8 1 1 0 0 0 26 35 1 0 0 0 0 26 36 1 0 0 0 0 27 32 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	502.22
Volume:	478.299
LogP:	2.588
LogD:	2.226
LogS:	-4.134
# Rotatable Bonds:	1
TPSA:	128.59
# H-Bond Aceptor:	9
# H-Bond Donor:	2
# Rings:	8
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.5
Synthetic Accessibility Score:	7.165
Fsp3:	0.889
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.332
MDCK Permeability:	9.725099516799673e-05
Pgp-inhibitor:	0.808
Pgp-substrate:	0.491
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.401
30% Bioavailability (F30%):	0.792

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.449
Plasma Protein Binding (PPB):	39.94659423828125%
Volume Distribution (VD):	0.869
Pgp-substrate:	44.756778717041016%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.794
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.825
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.009
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.073
CYP3A4-inhibitor:	0.6
CYP3A4-substrate:	0.707

ADMET: Excretion

Clearance (CL):	12.931
Half-life (T1/2):	0.56

ADMET: Toxicity

hERG Blockers:	0.205
Human Hepatotoxicity (H-HT):	0.771
Drug-inuced Liver Injury (DILI):	0.847
AMES Toxicity:	0.113
Rat Oral Acute Toxicity:	0.882
Maximum Recommended Daily Dose:	0.473
Skin Sensitization:	0.226
Carcinogencity:	0.266
Eye Corrosion:	0.006
Eye Irritation:	0.01
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC475490

Natural Product ID:	NPC475490
*Common Name:**	Subtrifloralactone K
IUPAC Name:	n.a.
Synonyms:	Subtrifloralactone K
Standard InCHIKey:	WGNSSHTUPLHGIN-AEMODRNGSA-N
Standard InCHI:	InChI=1S/C27H34O9/c1-9-10(2)23(30)34-20(9)22-25(4,31)19-14-5-12-11-6-17-27(32)21(29)15(33-17)7-16(28)24(27,3)13(11)8-26(35-14,36-22)18(12)19/h9-15,17-20,22,31-32H,5-8H2,1-4H3/t9-,10-,11+,12+,13+,14-,15+,17-,18-,19+,20?,22?,24+,25-,26+,27+/m1/s1
SMILES:	CC1C(C(=O)OC1C2C(C3C4CC5C3C(O4)(O2)CC6C5CC7C8(C6(C(=O)CC(C8=O)O7)C)O)(C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL506612
PubChem CID:	44559646
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides

*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
NPO10122	Deprea subtriflora	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12932130]
NPO10122	Deprea subtriflora	Species	Solanaceae	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	2

Activity Type	# Activity
Individual Protein	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	CD	=	0.36	uM	PMID[546088]
NPT27	Others	Unspecified		IC50	=	4800.0	nM	PMID[546088]
NPT2	Others	Unspecified		Ratio	=	13.3	n.a.	PMID[546088]

☑ 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 NPC475490 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	655
0.1-0.2	4436
0.2-0.3	9690
0.3-0.4	13106
0.4-0.5	6891
0.5-0.6	4557
0.6-0.7	2781
0.7-0.8	554
0.8-0.85	18
0.85-0.9	8
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8972	High Similarity	NPC166079
0.8879	High Similarity	NPC100078
0.8796	High Similarity	NPC306776
0.8692	High Similarity	NPC213528
0.8692	High Similarity	NPC244969
0.8673	High Similarity	NPC470115
0.8673	High Similarity	NPC470116
0.8673	High Similarity	NPC79193
0.8598	High Similarity	NPC178853
0.8584	High Similarity	NPC97002
0.8571	High Similarity	NPC473062
0.8522	High Similarity	NPC179429
0.8519	High Similarity	NPC470172
0.844	Intermediate Similarity	NPC473406
0.844	Intermediate Similarity	NPC471253
0.8364	Intermediate Similarity	NPC88469
0.8349	Intermediate Similarity	NPC471254
0.8241	Intermediate Similarity	NPC253995
0.8224	Intermediate Similarity	NPC476728
0.8224	Intermediate Similarity	NPC116683
0.8214	Intermediate Similarity	NPC203974
0.8198	Intermediate Similarity	NPC470167
0.8174	Intermediate Similarity	NPC477489
0.8148	Intermediate Similarity	NPC471241
0.8131	Intermediate Similarity	NPC62407
0.8131	Intermediate Similarity	NPC287354
0.8131	Intermediate Similarity	NPC305808
0.8108	Intermediate Similarity	NPC107385
0.8087	Intermediate Similarity	NPC469824
0.807	Intermediate Similarity	NPC236753
0.807	Intermediate Similarity	NPC208333
0.807	Intermediate Similarity	NPC227879
0.807	Intermediate Similarity	NPC228190
0.7982	Intermediate Similarity	NPC472273
0.7982	Intermediate Similarity	NPC472079
0.7965	Intermediate Similarity	NPC215408
0.7953	Intermediate Similarity	NPC470117
0.7953	Intermediate Similarity	NPC475376
0.7946	Intermediate Similarity	NPC34562
0.7944	Intermediate Similarity	NPC182740
0.7944	Intermediate Similarity	NPC161035
0.7944	Intermediate Similarity	NPC256104
0.7944	Intermediate Similarity	NPC122083
0.7944	Intermediate Similarity	NPC211845
0.7928	Intermediate Similarity	NPC298266
0.7928	Intermediate Similarity	NPC259654
0.7913	Intermediate Similarity	NPC217041
0.7909	Intermediate Similarity	NPC472144
0.7909	Intermediate Similarity	NPC211087
0.7909	Intermediate Similarity	NPC292775
0.7895	Intermediate Similarity	NPC176756
0.7891	Intermediate Similarity	NPC256618
0.7891	Intermediate Similarity	NPC219058
0.789	Intermediate Similarity	NPC475765
0.789	Intermediate Similarity	NPC475785
0.7876	Intermediate Similarity	NPC473526
0.7876	Intermediate Similarity	NPC327093
0.7876	Intermediate Similarity	NPC473701
0.787	Intermediate Similarity	NPC206878
0.7863	Intermediate Similarity	NPC477492
0.785	Intermediate Similarity	NPC216137
0.7845	Intermediate Similarity	NPC182185
0.7826	Intermediate Similarity	NPC167044
0.7826	Intermediate Similarity	NPC202898
0.7826	Intermediate Similarity	NPC92890
0.7826	Intermediate Similarity	NPC469826
0.7826	Intermediate Similarity	NPC475319
0.7823	Intermediate Similarity	NPC273962
0.7818	Intermediate Similarity	NPC472145
0.7798	Intermediate Similarity	NPC215570
0.7798	Intermediate Similarity	NPC21897
0.7797	Intermediate Similarity	NPC102619
0.7778	Intermediate Similarity	NPC472238
0.7778	Intermediate Similarity	NPC472237
0.7778	Intermediate Similarity	NPC476189
0.7778	Intermediate Similarity	NPC474379
0.7768	Intermediate Similarity	NPC477172
0.776	Intermediate Similarity	NPC2757
0.7759	Intermediate Similarity	NPC233433
0.7759	Intermediate Similarity	NPC273002
0.7759	Intermediate Similarity	NPC94086
0.7759	Intermediate Similarity	NPC220836
0.7759	Intermediate Similarity	NPC321661
0.7759	Intermediate Similarity	NPC473817
0.7759	Intermediate Similarity	NPC320475
0.7759	Intermediate Similarity	NPC92297
0.7739	Intermediate Similarity	NPC290247
0.7739	Intermediate Similarity	NPC469788
0.7739	Intermediate Similarity	NPC469787
0.7731	Intermediate Similarity	NPC477465
0.7727	Intermediate Similarity	NPC193785
0.7712	Intermediate Similarity	NPC98870
0.7706	Intermediate Similarity	NPC477495
0.7706	Intermediate Similarity	NPC247877
0.7706	Intermediate Similarity	NPC470424
0.7706	Intermediate Similarity	NPC309127
0.7692	Intermediate Similarity	NPC470622
0.7679	Intermediate Similarity	NPC20028
0.7679	Intermediate Similarity	NPC41843
0.7672	Intermediate Similarity	NPC316930
0.7664	Intermediate Similarity	NPC61688
0.7661	Intermediate Similarity	NPC267822
0.7658	Intermediate Similarity	NPC278028
0.7658	Intermediate Similarity	NPC470632
0.7658	Intermediate Similarity	NPC266417
0.7658	Intermediate Similarity	NPC328180
0.7658	Intermediate Similarity	NPC74466
0.7656	Intermediate Similarity	NPC42206
0.7652	Intermediate Similarity	NPC168890
0.7647	Intermediate Similarity	NPC471252
0.7627	Intermediate Similarity	NPC272242
0.7615	Intermediate Similarity	NPC472231
0.7615	Intermediate Similarity	NPC472232
0.7615	Intermediate Similarity	NPC228700
0.7611	Intermediate Similarity	NPC475574
0.7611	Intermediate Similarity	NPC162024
0.7607	Intermediate Similarity	NPC469825
0.7607	Intermediate Similarity	NPC274827
0.7603	Intermediate Similarity	NPC470778
0.7603	Intermediate Similarity	NPC473304
0.7603	Intermediate Similarity	NPC146432
0.76	Intermediate Similarity	NPC169818
0.7593	Intermediate Similarity	NPC470114
0.7593	Intermediate Similarity	NPC477433
0.7593	Intermediate Similarity	NPC477442
0.7593	Intermediate Similarity	NPC477444
0.7589	Intermediate Similarity	NPC476294
0.7581	Intermediate Similarity	NPC65858
0.757	Intermediate Similarity	NPC128475
0.757	Intermediate Similarity	NPC476435
0.7568	Intermediate Similarity	NPC145553
0.7568	Intermediate Similarity	NPC156377
0.7565	Intermediate Similarity	NPC154962
0.7565	Intermediate Similarity	NPC169089
0.7565	Intermediate Similarity	NPC18044
0.7565	Intermediate Similarity	NPC469827
0.7565	Intermediate Similarity	NPC18433
0.7565	Intermediate Similarity	NPC114365
0.7565	Intermediate Similarity	NPC132304
0.7565	Intermediate Similarity	NPC88890
0.7565	Intermediate Similarity	NPC177518
0.7565	Intermediate Similarity	NPC123070
0.7563	Intermediate Similarity	NPC474927
0.7559	Intermediate Similarity	NPC188291
0.7545	Intermediate Similarity	NPC477224
0.7545	Intermediate Similarity	NPC113500
0.7545	Intermediate Similarity	NPC3538
0.7544	Intermediate Similarity	NPC80191
0.7544	Intermediate Similarity	NPC310031
0.7544	Intermediate Similarity	NPC80640
0.7542	Intermediate Similarity	NPC137104
0.7542	Intermediate Similarity	NPC320383
0.7542	Intermediate Similarity	NPC85391
0.7542	Intermediate Similarity	NPC106760
0.7542	Intermediate Similarity	NPC474786
0.7542	Intermediate Similarity	NPC471093
0.754	Intermediate Similarity	NPC104427
0.754	Intermediate Similarity	NPC174367
0.754	Intermediate Similarity	NPC47113
0.7523	Intermediate Similarity	NPC474065
0.7523	Intermediate Similarity	NPC475878
0.7522	Intermediate Similarity	NPC80417
0.7521	Intermediate Similarity	NPC220773
0.7521	Intermediate Similarity	NPC88945
0.7521	Intermediate Similarity	NPC278693
0.7521	Intermediate Similarity	NPC63841
0.7521	Intermediate Similarity	NPC16081
0.7521	Intermediate Similarity	NPC173686
0.7521	Intermediate Similarity	NPC89929
0.752	Intermediate Similarity	NPC135038
0.752	Intermediate Similarity	NPC43252
0.75	Intermediate Similarity	NPC471459
0.75	Intermediate Similarity	NPC477440
0.75	Intermediate Similarity	NPC228311
0.75	Intermediate Similarity	NPC41674
0.75	Intermediate Similarity	NPC477443
0.75	Intermediate Similarity	NPC67653
0.75	Intermediate Similarity	NPC200580
0.75	Intermediate Similarity	NPC469441
0.75	Intermediate Similarity	NPC470478
0.75	Intermediate Similarity	NPC285086
0.7481	Intermediate Similarity	NPC171619
0.748	Intermediate Similarity	NPC258592
0.748	Intermediate Similarity	NPC178548
0.748	Intermediate Similarity	NPC292290
0.7479	Intermediate Similarity	NPC213320
0.7479	Intermediate Similarity	NPC29505
0.7477	Intermediate Similarity	NPC210658
0.7477	Intermediate Similarity	NPC263802
0.7477	Intermediate Similarity	NPC161928
0.7477	Intermediate Similarity	NPC470920
0.7477	Intermediate Similarity	NPC17336
0.7462	Intermediate Similarity	NPC88668
0.746	Intermediate Similarity	NPC473255
0.7458	Intermediate Similarity	NPC131903
0.7458	Intermediate Similarity	NPC87393
0.7456	Intermediate Similarity	NPC108227
0.7456	Intermediate Similarity	NPC477225
0.7456	Intermediate Similarity	NPC472081
0.7456	Intermediate Similarity	NPC476512

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 NPC475490 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	697
0.1-0.2	4144
0.2-0.3	2909
0.3-0.4	827
0.4-0.5	296
0.5-0.6	200
0.6-0.7	70
0.7-0.8	7
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8091	Intermediate Similarity	NPD1700	Approved
0.7876	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7565	Intermediate Similarity	NPD4056	Clinical (unspecified phase)
0.7565	Intermediate Similarity	NPD4057	Clinical (unspecified phase)
0.7422	Intermediate Similarity	NPD7736	Approved
0.7344	Intermediate Similarity	NPD7078	Approved
0.7323	Intermediate Similarity	NPD7492	Approved
0.728	Intermediate Similarity	NPD6059	Approved
0.728	Intermediate Similarity	NPD6054	Approved
0.7266	Intermediate Similarity	NPD6616	Approved
0.7231	Intermediate Similarity	NPD7319	Approved
0.7227	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD8293	Discontinued
0.7177	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD6370	Approved
0.7087	Intermediate Similarity	NPD6016	Approved
0.7087	Intermediate Similarity	NPD6015	Approved
0.7031	Intermediate Similarity	NPD5988	Approved
0.7008	Intermediate Similarity	NPD6319	Approved
0.7	Intermediate Similarity	NPD7507	Approved
0.6991	Remote Similarity	NPD8171	Discontinued
0.6977	Remote Similarity	NPD8328	Phase 3
0.6885	Remote Similarity	NPD6373	Approved
0.6885	Remote Similarity	NPD6372	Approved
0.6885	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD6882	Approved
0.6822	Remote Similarity	NPD6928	Phase 2
0.68	Remote Similarity	NPD8133	Approved
0.6774	Remote Similarity	NPD6649	Approved
0.6774	Remote Similarity	NPD6650	Approved
0.6772	Remote Similarity	NPD6009	Approved
0.6767	Remote Similarity	NPD6033	Approved
0.672	Remote Similarity	NPD8297	Approved
0.6692	Remote Similarity	NPD6921	Approved
0.6667	Remote Similarity	NPD7516	Approved
0.6667	Remote Similarity	NPD7320	Approved
0.6639	Remote Similarity	NPD6402	Approved
0.6639	Remote Similarity	NPD5739	Approved
0.6639	Remote Similarity	NPD7128	Approved
0.6639	Remote Similarity	NPD6675	Approved
0.6636	Remote Similarity	NPD6697	Approved
0.6636	Remote Similarity	NPD6115	Approved
0.6636	Remote Similarity	NPD6118	Approved
0.6636	Remote Similarity	NPD6114	Approved
0.6589	Remote Similarity	NPD7327	Approved
0.6589	Remote Similarity	NPD7328	Approved
0.6542	Remote Similarity	NPD6116	Phase 1
0.6535	Remote Similarity	NPD4632	Approved
0.6532	Remote Similarity	NPD6881	Approved
0.6532	Remote Similarity	NPD6899	Approved
0.6509	Remote Similarity	NPD3702	Approved
0.6466	Remote Similarity	NPD8034	Phase 2
0.6466	Remote Similarity	NPD8035	Phase 2
0.6452	Remote Similarity	NPD6412	Phase 2
0.6452	Remote Similarity	NPD5697	Approved
0.6452	Remote Similarity	NPD5701	Approved
0.6449	Remote Similarity	NPD6117	Approved
0.6439	Remote Similarity	NPD8378	Approved
0.6439	Remote Similarity	NPD8335	Approved
0.6439	Remote Similarity	NPD8296	Approved
0.6439	Remote Similarity	NPD8380	Approved
0.6439	Remote Similarity	NPD8379	Approved
0.6434	Remote Similarity	NPD6940	Discontinued
0.6429	Remote Similarity	NPD6883	Approved
0.6429	Remote Similarity	NPD7290	Approved
0.6429	Remote Similarity	NPD7102	Approved
0.6378	Remote Similarity	NPD6869	Approved
0.6378	Remote Similarity	NPD6847	Approved
0.6378	Remote Similarity	NPD6617	Approved
0.6378	Remote Similarity	NPD8130	Phase 1
0.6371	Remote Similarity	NPD6008	Approved
0.6364	Remote Similarity	NPD8294	Approved
0.6364	Remote Similarity	NPD8377	Approved
0.6355	Remote Similarity	NPD3703	Phase 2
0.6349	Remote Similarity	NPD6013	Approved
0.6349	Remote Similarity	NPD6014	Approved
0.6349	Remote Similarity	NPD6012	Approved
0.6343	Remote Similarity	NPD7604	Phase 2
0.6339	Remote Similarity	NPD3669	Approved
0.6339	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5983	Phase 2
0.6316	Remote Similarity	NPD8033	Approved
0.6299	Remote Similarity	NPD4634	Approved
0.627	Remote Similarity	NPD6011	Approved
0.6262	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6336	Discontinued
0.625	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD5777	Approved
0.6182	Remote Similarity	NPD4238	Approved
0.6182	Remote Similarity	NPD4802	Phase 2
0.6172	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD1780	Approved
0.6161	Remote Similarity	NPD1779	Approved
0.6075	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD5956	Approved
0.6066	Remote Similarity	NPD4755	Approved
0.6066	Remote Similarity	NPD6083	Phase 2
0.6066	Remote Similarity	NPD6084	Phase 2
0.6061	Remote Similarity	NPD6274	Approved
0.6045	Remote Similarity	NPD7101	Approved
0.6045	Remote Similarity	NPD7100	Approved
0.6033	Remote Similarity	NPD7991	Discontinued
0.6016	Remote Similarity	NPD5696	Approved
0.6015	Remote Similarity	NPD7115	Discovery
0.6	Remote Similarity	NPD6399	Phase 3
0.5981	Remote Similarity	NPD4789	Approved
0.5981	Remote Similarity	NPD4245	Approved
0.5981	Remote Similarity	NPD4244	Approved
0.597	Remote Similarity	NPD6335	Approved
0.5969	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5968	Remote Similarity	NPD5286	Approved
0.5968	Remote Similarity	NPD4696	Approved
0.5968	Remote Similarity	NPD5285	Approved
0.5968	Remote Similarity	NPD4700	Approved
0.5956	Remote Similarity	NPD8515	Approved
0.5956	Remote Similarity	NPD8513	Phase 3
0.5956	Remote Similarity	NPD6908	Approved
0.5956	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5956	Remote Similarity	NPD8516	Approved
0.5956	Remote Similarity	NPD7503	Approved
0.5956	Remote Similarity	NPD6909	Approved
0.5956	Remote Similarity	NPD8517	Approved
0.5948	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD229	Approved
0.5943	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD5360	Phase 3
0.5938	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD6081	Approved
0.5902	Remote Similarity	NPD5695	Phase 3
0.5896	Remote Similarity	NPD6317	Approved
0.5891	Remote Similarity	NPD6686	Approved
0.5888	Remote Similarity	NPD3698	Phase 2
0.5888	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.5873	Remote Similarity	NPD5225	Approved
0.5873	Remote Similarity	NPD8138	Approved
0.5873	Remote Similarity	NPD4633	Approved
0.5873	Remote Similarity	NPD8086	Approved
0.5873	Remote Similarity	NPD5211	Phase 2
0.5873	Remote Similarity	NPD8083	Approved
0.5873	Remote Similarity	NPD8082	Approved
0.5873	Remote Similarity	NPD8139	Approved
0.5873	Remote Similarity	NPD5226	Approved
0.5873	Remote Similarity	NPD8085	Approved
0.5873	Remote Similarity	NPD5224	Approved
0.5873	Remote Similarity	NPD8084	Approved
0.587	Remote Similarity	NPD6067	Discontinued
0.5859	Remote Similarity	NPD8393	Approved
0.5859	Remote Similarity	NPD4767	Approved
0.5859	Remote Similarity	NPD4768	Approved
0.5852	Remote Similarity	NPD6314	Approved
0.5852	Remote Similarity	NPD6313	Approved
0.5841	Remote Similarity	NPD7329	Approved
0.5833	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5827	Remote Similarity	NPD8276	Approved
0.5827	Remote Similarity	NPD5174	Approved
0.5827	Remote Similarity	NPD8275	Approved
0.5827	Remote Similarity	NPD5175	Approved
0.5806	Remote Similarity	NPD7902	Approved
0.5794	Remote Similarity	NPD5223	Approved
0.5781	Remote Similarity	NPD5141	Approved
0.5781	Remote Similarity	NPD8081	Approved
0.5772	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD4730	Approved
0.5769	Remote Similarity	NPD4729	Approved
0.576	Remote Similarity	NPD7638	Approved
0.5755	Remote Similarity	NPD4224	Phase 2
0.5749	Remote Similarity	NPD7799	Discontinued
0.5726	Remote Similarity	NPD4697	Phase 3
0.5714	Remote Similarity	NPD7639	Approved
0.5714	Remote Similarity	NPD7640	Approved
0.5703	Remote Similarity	NPD4754	Approved
0.5692	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5682	Remote Similarity	NPD5251	Approved
0.5682	Remote Similarity	NPD5247	Approved
0.5682	Remote Similarity	NPD5250	Approved
0.5682	Remote Similarity	NPD5249	Phase 3
0.5682	Remote Similarity	NPD5248	Approved
0.5676	Remote Similarity	NPD6334	Approved
0.5676	Remote Similarity	NPD6333	Approved
0.566	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.5649	Remote Similarity	NPD5128	Approved
0.5639	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD4758	Discontinued
0.5634	Remote Similarity	NPD8074	Phase 3
0.563	Remote Similarity	NPD6098	Approved
0.5625	Remote Similarity	NPD7632	Discontinued
0.5625	Remote Similarity	NPD8301	Approved
0.5625	Remote Similarity	NPD8300	Approved
0.562	Remote Similarity	NPD6080	Approved
0.562	Remote Similarity	NPD6673	Approved
0.562	Remote Similarity	NPD6904	Approved
0.5614	Remote Similarity	NPD5364	Discontinued
0.5612	Remote Similarity	NPD8267	Approved
0.5612	Remote Similarity	NPD8266	Approved
0.5612	Remote Similarity	NPD8268	Approved
0.5612	Remote Similarity	NPD8269	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