NPASS Compound

Structure

NPC474044 OpenBabel07101718192D 28 29 0 0 1 0 0 0 0 0999 V2000 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 4.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 5.5000 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 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 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 1.0000 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 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 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 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 2 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 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 0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 4.0000 0.0000 C 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 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 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 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 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 11 1 0 0 0 0 2 20 1 0 0 0 0 3 20 1 0 0 0 0 4 26 1 0 0 0 0 5 6 2 0 0 0 0 5 12 1 0 0 0 0 6 14 1 0 0 0 0 7 8 2 0 0 0 0 7 13 1 0 0 0 0 8 20 1 0 0 0 0 9 12 2 0 0 0 0 9 13 1 0 0 0 0 10 21 1 0 0 0 0 11 12 1 0 0 0 0 11 22 2 0 0 0 0 13 14 2 0 0 0 0 14 27 1 0 0 0 0 15 10 1 6 0 0 0 15 16 1 0 0 0 0 15 28 1 0 0 0 0 16 17 1 0 0 0 0 16 23 1 1 0 0 0 17 18 1 0 0 0 0 17 24 1 6 0 0 0 18 19 1 0 0 0 0 18 25 1 1 0 0 0 19 27 1 6 0 0 0 19 28 1 0 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	396.18
Volume:	394.503
LogP:	0.83
LogD:	0.947
LogS:	-2.935
# Rotatable Bonds:	7
TPSA:	125.68
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.491
Synthetic Accessibility Score:	4.036
Fsp3:	0.55
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.924
MDCK Permeability:	3.347202800796367e-05
Pgp-inhibitor:	0.17
Pgp-substrate:	0.196
Human Intestinal Absorption (HIA):	0.375
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.967

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.267
Plasma Protein Binding (PPB):	64.55335235595703%
Volume Distribution (VD):	0.508
Pgp-substrate:	30.58851432800293%

ADMET: Metabolism

CYP1A2-inhibitor:	0.124
CYP1A2-substrate:	0.127
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.711
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.564
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.497
CYP3A4-inhibitor:	0.011
CYP3A4-substrate:	0.198

ADMET: Excretion

Clearance (CL):	2.43
Half-life (T1/2):	0.743

ADMET: Toxicity

hERG Blockers:	0.096
Human Hepatotoxicity (H-HT):	0.044
Drug-inuced Liver Injury (DILI):	0.771
AMES Toxicity:	0.168
Rat Oral Acute Toxicity:	0.022
Maximum Recommended Daily Dose:	0.003
Skin Sensitization:	0.117
Carcinogencity:	0.247
Eye Corrosion:	0.003
Eye Irritation:	0.065
Respiratory Toxicity:	0.008

Download Data

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

Natural Product: NPC474044

Natural Product ID:	NPC474044
*Common Name:**	4-Beta-D-(Glucopyranosyloxy)-3-[3-Methoxy-Trans-Isopenten-1-Yl]Acetophenone
IUPAC Name:	1-[3-[(E)-3-methoxy-3-methylbut-1-enyl]-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]ethanone
Synonyms:
Standard InCHIKey:	VVFUESRNOVONAM-KOGRRYKMSA-N
Standard InCHI:	InChI=1S/C20H28O8/c1-11(22)12-5-6-14(13(9-12)7-8-20(2,3)26-4)27-19-18(25)17(24)16(23)15(10-21)28-19/h5-9,15-19,21,23-25H,10H2,1-4H3/b8-7+/t15-,16-,17+,18-,19-/m1/s1
SMILES:	OC[C@H]1O[C@@H](Oc2ccc(cc2/C=C/C(OC)(C)C)C(=O)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL459055
PubChem CID:	21607143
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0004165] Phenolic 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
NPO13981	Helianthella quinquenervis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8882437]
NPO13981	Helianthella quinquenervis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
ED50	3
IC50	2
Others	1

Activity Type	# Activity
Cell Line	3
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	44.0	ug ml-1	PMID[568516]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	61.0	ug ml-1	PMID[568516]
NPT81	Cell Line	A549	Homo sapiens	ED50	=	6.0	ug ml-1	PMID[568516]
NPT140	Organism	Artemia	Artemia	LC50	>	1000.0	ug.mL-1	PMID[568516]
NPT117	Organism	Echinochloa crus-galli	Echinochloa crus-galli	IC50	=	231.0	ug.mL-1	PMID[568516]
NPT965	Organism	Amaranthus hypochondriacus	Amaranthus hypochondriacus	IC50	=	148.0	ug.mL-1	PMID[568516]

☑ 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 NPC474044 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	327
0.1-0.2	1334
0.2-0.3	3009
0.3-0.4	7553
0.4-0.5	10710
0.5-0.6	4726
0.6-0.7	6200
0.7-0.8	7756
0.8-0.85	967
0.85-0.9	108
0.9-0.95	4
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.958	High Similarity	NPC104172
0.958	High Similarity	NPC88886
0.9357	High Similarity	NPC79908
0.9348	High Similarity	NPC294470
0.9184	High Similarity	NPC23253
0.9172	High Similarity	NPC218685
0.9155	High Similarity	NPC184053
0.9133	High Similarity	NPC23817
0.9116	High Similarity	NPC213723
0.9085	High Similarity	NPC80098
0.9067	High Similarity	NPC17521
0.906	High Similarity	NPC211158
0.906	High Similarity	NPC78021
0.906	High Similarity	NPC87304
0.906	High Similarity	NPC268950
0.906	High Similarity	NPC108706
0.9034	High Similarity	NPC291153
0.9	High Similarity	NPC470603
0.9	High Similarity	NPC99233
0.9	High Similarity	NPC212729
0.9	High Similarity	NPC470605
0.9	High Similarity	NPC470604
0.8986	High Similarity	NPC106025
0.8986	High Similarity	NPC214454
0.8986	High Similarity	NPC477240
0.898	High Similarity	NPC199335
0.8947	High Similarity	NPC470607
0.894	High Similarity	NPC45165
0.8933	High Similarity	NPC106625
0.8929	High Similarity	NPC34456
0.8926	High Similarity	NPC190217
0.8912	High Similarity	NPC472339
0.8912	High Similarity	NPC23084
0.8889	High Similarity	NPC472320
0.8882	High Similarity	NPC43638
0.8882	High Similarity	NPC470606
0.8867	High Similarity	NPC121001
0.8867	High Similarity	NPC259182
0.8867	High Similarity	NPC88484
0.8867	High Similarity	NPC259767
0.8859	High Similarity	NPC38775
0.8859	High Similarity	NPC191154
0.8844	High Similarity	NPC469700
0.8839	High Similarity	NPC183672
0.8824	High Similarity	NPC43761
0.8824	High Similarity	NPC73511
0.8816	High Similarity	NPC149368
0.8816	High Similarity	NPC265480
0.8816	High Similarity	NPC170475
0.8816	High Similarity	NPC206378
0.8816	High Similarity	NPC127406
0.88	High Similarity	NPC134819
0.8792	High Similarity	NPC107197
0.8792	High Similarity	NPC205054
0.8786	High Similarity	NPC269421
0.8774	High Similarity	NPC44947
0.8774	High Similarity	NPC131745
0.8774	High Similarity	NPC259834
0.8774	High Similarity	NPC190450
0.8767	High Similarity	NPC471028
0.8766	High Similarity	NPC200708
0.8759	High Similarity	NPC31081
0.8759	High Similarity	NPC245219
0.8758	High Similarity	NPC258035
0.8758	High Similarity	NPC6985
0.8758	High Similarity	NPC156457
0.8758	High Similarity	NPC313163
0.8758	High Similarity	NPC197896
0.8758	High Similarity	NPC161749
0.875	High Similarity	NPC169248
0.875	High Similarity	NPC27408
0.875	High Similarity	NPC72649
0.875	High Similarity	NPC95090
0.875	High Similarity	NPC26195
0.875	High Similarity	NPC39351
0.875	High Similarity	NPC97052
0.8742	High Similarity	NPC137813
0.8718	High Similarity	NPC124155
0.8718	High Similarity	NPC278419
0.8718	High Similarity	NPC257566
0.8718	High Similarity	NPC179198
0.8718	High Similarity	NPC66087
0.8718	High Similarity	NPC471286
0.8716	High Similarity	NPC474302
0.871	High Similarity	NPC47923
0.871	High Similarity	NPC303913
0.8699	High Similarity	NPC242756
0.8693	High Similarity	NPC473657
0.8693	High Similarity	NPC295613
0.8684	High Similarity	NPC83283
0.8684	High Similarity	NPC210003
0.8684	High Similarity	NPC29763
0.8684	High Similarity	NPC39360
0.8684	High Similarity	NPC143851
0.8675	High Similarity	NPC472422
0.8675	High Similarity	NPC471676
0.8675	High Similarity	NPC263384
0.8675	High Similarity	NPC250488
0.8675	High Similarity	NPC472420
0.8675	High Similarity	NPC244577
0.8667	High Similarity	NPC182350
0.8667	High Similarity	NPC227980
0.8658	High Similarity	NPC91902
0.8658	High Similarity	NPC473133
0.8658	High Similarity	NPC47388
0.8658	High Similarity	NPC14875
0.8658	High Similarity	NPC470670
0.8654	High Similarity	NPC93215
0.8645	High Similarity	NPC271270
0.8645	High Similarity	NPC153342
0.8645	High Similarity	NPC142860
0.8645	High Similarity	NPC271479
0.8645	High Similarity	NPC97285
0.8645	High Similarity	NPC246469
0.8636	High Similarity	NPC473512
0.8636	High Similarity	NPC44931
0.8636	High Similarity	NPC108831
0.8636	High Similarity	NPC129827
0.8636	High Similarity	NPC182634
0.8636	High Similarity	NPC60966
0.8636	High Similarity	NPC122809
0.8636	High Similarity	NPC65003
0.8627	High Similarity	NPC10205
0.8618	High Similarity	NPC157898
0.8618	High Similarity	NPC256141
0.8609	High Similarity	NPC473966
0.86	High Similarity	NPC10097
0.8592	High Similarity	NPC114116
0.8591	High Similarity	NPC473149
0.8581	High Similarity	NPC472459
0.8581	High Similarity	NPC111929
0.8581	High Similarity	NPC320283
0.8581	High Similarity	NPC85624
0.8581	High Similarity	NPC308265
0.8581	High Similarity	NPC138811
0.8581	High Similarity	NPC22062
0.8581	High Similarity	NPC41121
0.8581	High Similarity	NPC473634
0.8571	High Similarity	NPC203500
0.8571	High Similarity	NPC323593
0.8571	High Similarity	NPC307938
0.8571	High Similarity	NPC471405
0.8562	High Similarity	NPC135370
0.8562	High Similarity	NPC223701
0.8562	High Similarity	NPC472583
0.8562	High Similarity	NPC76047
0.8562	High Similarity	NPC7989
0.8553	High Similarity	NPC474744
0.8553	High Similarity	NPC471677
0.8553	High Similarity	NPC36130
0.8553	High Similarity	NPC318424
0.8553	High Similarity	NPC474772
0.8553	High Similarity	NPC472423
0.8553	High Similarity	NPC134905
0.8544	High Similarity	NPC294722
0.8544	High Similarity	NPC475979
0.8543	High Similarity	NPC472628
0.8543	High Similarity	NPC139966
0.8543	High Similarity	NPC307052
0.8543	High Similarity	NPC89442
0.8535	High Similarity	NPC127782
0.8535	High Similarity	NPC150164
0.8535	High Similarity	NPC300537
0.8535	High Similarity	NPC472876
0.8535	High Similarity	NPC216752
0.8533	High Similarity	NPC472627
0.8533	High Similarity	NPC85773
0.8531	High Similarity	NPC471029
0.8526	High Similarity	NPC187379
0.8526	High Similarity	NPC473623
0.8526	High Similarity	NPC306978
0.8516	High Similarity	NPC135391
0.8516	High Similarity	NPC54802
0.8516	High Similarity	NPC78263
0.8516	High Similarity	NPC197304
0.8516	High Similarity	NPC133671
0.8516	High Similarity	NPC77672
0.8516	High Similarity	NPC177742
0.8506	High Similarity	NPC477958
0.8506	High Similarity	NPC470681
0.8506	High Similarity	NPC477530
0.8503	High Similarity	NPC65833
0.85	High Similarity	NPC473202
0.85	High Similarity	NPC5319
0.8497	Intermediate Similarity	NPC56232
0.8497	Intermediate Similarity	NPC475790
0.8497	Intermediate Similarity	NPC244583
0.8497	Intermediate Similarity	NPC473996
0.8497	Intermediate Similarity	NPC150123
0.8497	Intermediate Similarity	NPC10807
0.8497	Intermediate Similarity	NPC171651
0.8497	Intermediate Similarity	NPC243171
0.8497	Intermediate Similarity	NPC35567
0.8497	Intermediate Similarity	NPC161881
0.8491	Intermediate Similarity	NPC178851
0.8487	Intermediate Similarity	NPC131874
0.8487	Intermediate Similarity	NPC180351
0.8487	Intermediate Similarity	NPC472421
0.8481	Intermediate Similarity	NPC91288
0.8481	Intermediate Similarity	NPC121703

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 NPC474044 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	281
0.1-0.2	835
0.2-0.3	1586
0.3-0.4	2575
0.4-0.5	2062
0.5-0.6	1147
0.6-0.7	477
0.7-0.8	177
0.8-0.85	10
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8758	High Similarity	NPD4381	Clinical (unspecified phase)
0.85	High Similarity	NPD7804	Clinical (unspecified phase)
0.8366	Intermediate Similarity	NPD4380	Phase 2
0.8323	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8311	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.828	Intermediate Similarity	NPD7075	Discontinued
0.8258	Intermediate Similarity	NPD6801	Discontinued
0.8255	Intermediate Similarity	NPD4628	Phase 3
0.8232	Intermediate Similarity	NPD6559	Discontinued
0.8221	Intermediate Similarity	NPD7074	Phase 3
0.821	Intermediate Similarity	NPD3818	Discontinued
0.8205	Intermediate Similarity	NPD8455	Phase 2
0.816	Intermediate Similarity	NPD7054	Approved
0.811	Intermediate Similarity	NPD7472	Approved
0.8092	Intermediate Similarity	NPD6799	Approved
0.8089	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD7411	Suspended
0.8061	Intermediate Similarity	NPD6797	Phase 2
0.8012	Intermediate Similarity	NPD7251	Discontinued
0.8	Intermediate Similarity	NPD1549	Phase 2
0.8	Intermediate Similarity	NPD1091	Approved
0.7975	Intermediate Similarity	NPD7819	Suspended
0.7964	Intermediate Similarity	NPD7808	Phase 3
0.7933	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD1934	Approved
0.7898	Intermediate Similarity	NPD6599	Discontinued
0.7881	Intermediate Similarity	NPD2424	Discontinued
0.7875	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD2796	Approved
0.7857	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD7458	Discontinued
0.7812	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD8312	Approved
0.7811	Intermediate Similarity	NPD8313	Approved
0.7803	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD6166	Phase 2
0.7755	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD5844	Phase 1
0.7707	Intermediate Similarity	NPD5403	Approved
0.7702	Intermediate Similarity	NPD3817	Phase 2
0.7692	Intermediate Similarity	NPD5401	Approved
0.7682	Intermediate Similarity	NPD2799	Discontinued
0.7651	Intermediate Similarity	NPD1240	Approved
0.7635	Intermediate Similarity	NPD6798	Discontinued
0.7622	Intermediate Similarity	NPD5494	Approved
0.7616	Intermediate Similarity	NPD7097	Phase 1
0.7595	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD7685	Pre-registration
0.7566	Intermediate Similarity	NPD7033	Discontinued
0.7566	Intermediate Similarity	NPD1510	Phase 2
0.755	Intermediate Similarity	NPD1607	Approved
0.7548	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD1653	Approved
0.7546	Intermediate Similarity	NPD3882	Suspended
0.7545	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD7584	Approved
0.7532	Intermediate Similarity	NPD5049	Phase 3
0.7531	Intermediate Similarity	NPD2801	Approved
0.7529	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD2313	Discontinued
0.7516	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2935	Discontinued
0.75	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6779	Approved
0.75	Intermediate Similarity	NPD6781	Approved
0.75	Intermediate Similarity	NPD6777	Approved
0.75	Intermediate Similarity	NPD3887	Approved
0.75	Intermediate Similarity	NPD2354	Approved
0.75	Intermediate Similarity	NPD6776	Approved
0.75	Intermediate Similarity	NPD6780	Approved
0.75	Intermediate Similarity	NPD6778	Approved
0.75	Intermediate Similarity	NPD6832	Phase 2
0.75	Intermediate Similarity	NPD6782	Approved
0.7485	Intermediate Similarity	NPD5402	Approved
0.7484	Intermediate Similarity	NPD920	Approved
0.7483	Intermediate Similarity	NPD6355	Discontinued
0.7483	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1933	Approved
0.7483	Intermediate Similarity	NPD5124	Phase 1
0.7482	Intermediate Similarity	NPD1241	Discontinued
0.747	Intermediate Similarity	NPD6959	Discontinued
0.747	Intermediate Similarity	NPD7199	Phase 2
0.7467	Intermediate Similarity	NPD6233	Phase 2
0.7465	Intermediate Similarity	NPD9545	Approved
0.7456	Intermediate Similarity	NPD3751	Discontinued
0.7452	Intermediate Similarity	NPD5058	Phase 3
0.7446	Intermediate Similarity	NPD7583	Approved
0.7436	Intermediate Similarity	NPD3750	Approved
0.7427	Intermediate Similarity	NPD3823	Discontinued
0.7425	Intermediate Similarity	NPD3787	Discontinued
0.7414	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD1511	Approved
0.7405	Intermediate Similarity	NPD7585	Approved
0.7391	Intermediate Similarity	NPD3226	Approved
0.7377	Intermediate Similarity	NPD7435	Discontinued
0.7372	Intermediate Similarity	NPD1652	Phase 2
0.7372	Intermediate Similarity	NPD6674	Discontinued
0.7372	Intermediate Similarity	NPD1243	Approved
0.7372	Intermediate Similarity	NPD2800	Approved
0.7365	Intermediate Similarity	NPD2798	Approved
0.7358	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD7266	Discontinued
0.7355	Intermediate Similarity	NPD2346	Discontinued
0.7355	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD6005	Phase 3
0.7355	Intermediate Similarity	NPD6004	Phase 3
0.7355	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD6002	Phase 3
0.7342	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD3748	Approved
0.7333	Intermediate Similarity	NPD7768	Phase 2
0.7329	Intermediate Similarity	NPD9717	Approved
0.7329	Intermediate Similarity	NPD3972	Approved
0.732	Intermediate Similarity	NPD6651	Approved
0.7312	Intermediate Similarity	NPD1512	Approved
0.7303	Intermediate Similarity	NPD3142	Approved
0.7303	Intermediate Similarity	NPD3140	Approved
0.7288	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD7843	Approved
0.7285	Intermediate Similarity	NPD3268	Approved
0.7284	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7696	Phase 3
0.7283	Intermediate Similarity	NPD7697	Approved
0.7283	Intermediate Similarity	NPD7698	Approved
0.7278	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD8434	Phase 2
0.7256	Intermediate Similarity	NPD37	Approved
0.725	Intermediate Similarity	NPD4662	Approved
0.725	Intermediate Similarity	NPD2532	Approved
0.725	Intermediate Similarity	NPD4661	Approved
0.725	Intermediate Similarity	NPD2533	Approved
0.725	Intermediate Similarity	NPD2534	Approved
0.725	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD2684	Approved
0.7246	Intermediate Similarity	NPD919	Approved
0.7244	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD2353	Approved
0.7244	Intermediate Similarity	NPD2344	Approved
0.7243	Intermediate Similarity	NPD7870	Phase 2
0.7243	Intermediate Similarity	NPD7871	Phase 2
0.7237	Intermediate Similarity	NPD4062	Phase 3
0.723	Intermediate Similarity	NPD8651	Approved
0.7229	Intermediate Similarity	NPD4966	Approved
0.7229	Intermediate Similarity	NPD4967	Phase 2
0.7229	Intermediate Similarity	NPD4965	Approved
0.7228	Intermediate Similarity	NPD6823	Phase 2
0.7226	Intermediate Similarity	NPD4308	Phase 3
0.7225	Intermediate Similarity	NPD5953	Discontinued
0.7222	Intermediate Similarity	NPD6535	Approved
0.7222	Intermediate Similarity	NPD6534	Approved
0.7219	Intermediate Similarity	NPD6232	Discontinued
0.7219	Intermediate Similarity	NPD7701	Phase 2
0.7215	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD1465	Phase 2
0.7211	Intermediate Similarity	NPD1608	Approved
0.7209	Intermediate Similarity	NPD7286	Phase 2
0.7197	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD7783	Phase 2
0.7195	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD7473	Discontinued
0.7186	Intermediate Similarity	NPD3749	Approved
0.7181	Intermediate Similarity	NPD1203	Approved
0.7181	Intermediate Similarity	NPD2797	Approved
0.7179	Intermediate Similarity	NPD1551	Phase 2
0.7175	Intermediate Similarity	NPD3863	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD290	Approved
0.717	Intermediate Similarity	NPD6190	Approved
0.7161	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD4538	Approved
0.7161	Intermediate Similarity	NPD4536	Approved
0.716	Intermediate Similarity	NPD1247	Approved
0.7152	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7228	Approved
0.7143	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD447	Suspended
0.7143	Intermediate Similarity	NPD6234	Discontinued
0.7143	Intermediate Similarity	NPD7874	Approved
0.7143	Intermediate Similarity	NPD230	Phase 1
0.7133	Intermediate Similarity	NPD7157	Approved
0.7133	Intermediate Similarity	NPD1019	Discontinued
0.7105	Intermediate Similarity	NPD7801	Approved
0.7104	Intermediate Similarity	NPD7699	Phase 2
0.7104	Intermediate Similarity	NPD7700	Phase 2
0.7099	Intermediate Similarity	NPD6273	Approved
0.709	Intermediate Similarity	NPD8151	Discontinued
0.7086	Intermediate Similarity	NPD9494	Approved
0.7078	Intermediate Similarity	NPD1613	Approved
0.7078	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD4060	Phase 1
0.7078	Intermediate Similarity	NPD4307	Phase 2
0.707	Intermediate Similarity	NPD6099	Approved
0.707	Intermediate Similarity	NPD6100	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