NPASS Compound

Structure

CID188814 OpenBabel06191715572D 24 25 0 0 0 0 0 0 0 0999 V2000 -3.4641 -3.0000 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 -3.4641 -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 -6.9282 1.0000 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 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 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 1.7321 1.0000 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 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -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 0.8660 1.5000 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 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 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 1 2 1 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 6 1 0 0 0 0 4 9 1 0 0 0 0 5 7 2 0 0 0 0 5 8 1 0 0 0 0 6 11 1 0 0 0 0 7 12 1 0 0 0 0 8 13 2 0 0 0 0 9 14 1 0 0 0 0 10 15 2 0 0 0 0 10 16 1 0 0 0 0 11 17 1 0 0 0 0 12 17 2 0 0 0 0 13 17 1 0 0 0 0 14 18 1 0 0 0 0 15 19 1 0 0 0 0 16 20 2 0 0 0 0 18 21 1 0 0 0 0 18 22 2 0 0 0 0 19 21 2 0 0 0 0 19 23 1 0 0 0 0 20 21 1 0 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	326.19
Volume:	362.575
LogP:	6.413
LogD:	4.34
LogS:	-3.638
# Rotatable Bonds:	10
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.463
Synthetic Accessibility Score:	1.975
Fsp3:	0.381
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:	-4.877
MDCK Permeability:	1.4335696505440865e-05
Pgp-inhibitor:	0.964
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.237
Plasma Protein Binding (PPB):	99.12413787841797%
Volume Distribution (VD):	0.773
Pgp-substrate:	0.3685819208621979%

ADMET: Metabolism

CYP1A2-inhibitor:	0.959
CYP1A2-substrate:	0.199
CYP2C19-inhibitor:	0.941
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.724
CYP2C9-substrate:	0.948
CYP2D6-inhibitor:	0.895
CYP2D6-substrate:	0.239
CYP3A4-inhibitor:	0.608
CYP3A4-substrate:	0.163

ADMET: Excretion

Clearance (CL):	5.475
Half-life (T1/2):	0.361

ADMET: Toxicity

hERG Blockers:	0.05
Human Hepatotoxicity (H-HT):	0.024
Drug-inuced Liver Injury (DILI):	0.409
AMES Toxicity:	0.599
Rat Oral Acute Toxicity:	0.077
Maximum Recommended Daily Dose:	0.063
Skin Sensitization:	0.947
Carcinogencity:	0.208
Eye Corrosion:	0.09
Eye Irritation:	0.985
Respiratory Toxicity:	0.176

Download Data

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

Natural Product: NPC188814

Natural Product ID:	NPC188814
*Common Name:**	Malabaricone A
IUPAC Name:	1-(2,6-dihydroxyphenyl)-9-phenylnonan-1-one
Synonyms:	Malabaricone A
Standard InCHIKey:	IAXIHKJASWPASP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H26O3/c22-18(21-19(23)15-10-16-20(21)24)14-9-4-2-1-3-6-11-17-12-7-5-8-13-17/h5,7-8,10,12-13,15-16,23-24H,1-4,6,9,11,14H2
SMILES:	O=C(c1c(O)cccc1O)CCCCCCCCc1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1254269
PubChem CID:	324062
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0004296] Phenylketones [CHEMONTID:0004298] Alkyl-phenylketones

*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
NPO14474	Klasea sogdiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8263	Asclepias vestita	Species	Apocynaceae	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	9
MIC	1
Others	8

Activity Type	# Activity
Cell Line	4
Individual Protein	6
Organism	1
Others	3
SINGLE PROTEIN	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	12.0	%	PMID[496968]
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	IC50	=	1310.0	nM	PMID[496970]
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	Inhibition	=	97.42	%	PMID[496970]
NPT3809	Individual Protein	Pancreatic alpha-amylase	Sus scrofa	IC50	=	19070.0	nM	PMID[496971]
NPT589	Individual Protein	Serum albumin	Bos taurus	IC50	=	19280.0	nM	PMID[496971]
NPT839	Cell Line	L6	Rattus norvegicus	Activity	=	32.9	%	PMID[496971]
NPT839	Cell Line	L6	Rattus norvegicus	Activity	=	33.4	%	PMID[496971]
NPT839	Cell Line	L6	Rattus norvegicus	Activity	=	36.7	%	PMID[496971]
NPT115	Organism	Mycobacterium tuberculosis H37Ra	Mycobacterium tuberculosis H37Ra	MIC	=	25.0	ug.mL-1	PMID[496969]
NPT67	Individual Protein	Cholinesterase	Equus caballus	IC50	=	39210.0	nM	PMID[496970]
NPT67	Individual Protein	Cholinesterase	Equus caballus	Inhibition	=	69.55	%	PMID[496970]
NPT2	Others	Unspecified		Ratio IC50	=	32.95	n.a.	PMID[496970]
NPT2	Others	Unspecified		Ratio IC50	=	0.04	n.a.	PMID[496970]
NPT2	Others	Unspecified		IC50	=	91440.0	nM	PMID[496971]
NPT23158	SINGLE PROTEIN	Phosphatidylcholine:ceramide cholinephosphotransferase 1	Homo sapiens	IC50	=	4000.0	nM	PMID[496972]
NPT23159	SINGLE PROTEIN	Phosphatidylcholine:ceramide cholinephosphotransferase 2	Homo sapiens	IC50	=	4000.0	nM	PMID[496972]
NPT23158	SINGLE PROTEIN	Phosphatidylcholine:ceramide cholinephosphotransferase 1	Homo sapiens	IC50	=	2000.0	nM	PMID[496972]
NPT23159	SINGLE PROTEIN	Phosphatidylcholine:ceramide cholinephosphotransferase 2	Homo sapiens	IC50	=	1000.0	nM	PMID[496972]

☑ 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 NPC188814 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	313
0.1-0.2	1530
0.2-0.3	4239
0.3-0.4	12504
0.4-0.5	6491
0.5-0.6	5680
0.6-0.7	7444
0.7-0.8	3808
0.8-0.85	546
0.85-0.9	96
0.9-0.95	41
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC195262
0.9737	High Similarity	NPC196976
0.9643	High Similarity	NPC121259
0.9397	High Similarity	NPC156139
0.9397	High Similarity	NPC242895
0.9375	High Similarity	NPC276111
0.9375	High Similarity	NPC118288
0.9328	High Similarity	NPC267846
0.9328	High Similarity	NPC62952
0.9316	High Similarity	NPC133909
0.9316	High Similarity	NPC32032
0.931	High Similarity	NPC297186
0.925	High Similarity	NPC103356
0.925	High Similarity	NPC266689
0.925	High Similarity	NPC116513
0.925	High Similarity	NPC105157
0.925	High Similarity	NPC30501
0.925	High Similarity	NPC162612
0.925	High Similarity	NPC100067
0.925	High Similarity	NPC23126
0.925	High Similarity	NPC169250
0.925	High Similarity	NPC72158
0.925	High Similarity	NPC98254
0.925	High Similarity	NPC190043
0.9231	High Similarity	NPC45438
0.9231	High Similarity	NPC73532
0.9231	High Similarity	NPC143427
0.9231	High Similarity	NPC267552
0.9231	High Similarity	NPC224273
0.9231	High Similarity	NPC115159
0.9231	High Similarity	NPC19174
0.9174	High Similarity	NPC473017
0.9174	High Similarity	NPC21305
0.9174	High Similarity	NPC221777
0.9145	High Similarity	NPC149246
0.9098	High Similarity	NPC474998
0.9098	High Similarity	NPC92624
0.9098	High Similarity	NPC109123
0.906	High Similarity	NPC159525
0.9024	High Similarity	NPC244441
0.9024	High Similarity	NPC259942
0.9008	High Similarity	NPC8745
0.9	High Similarity	NPC13238
0.8992	High Similarity	NPC309765
0.8992	High Similarity	NPC91105
0.8974	High Similarity	NPC158222
0.8974	High Similarity	NPC161617
0.8952	High Similarity	NPC475042
0.8926	High Similarity	NPC10926
0.8917	High Similarity	NPC65761
0.8917	High Similarity	NPC472029
0.8908	High Similarity	NPC215392
0.8908	High Similarity	NPC303737
0.8898	High Similarity	NPC294037
0.8889	High Similarity	NPC209486
0.8889	High Similarity	NPC40649
0.888	High Similarity	NPC475009
0.888	High Similarity	NPC175738
0.888	High Similarity	NPC475008
0.888	High Similarity	NPC186097
0.8824	High Similarity	NPC146642
0.881	High Similarity	NPC213485
0.881	High Similarity	NPC40524
0.881	High Similarity	NPC139074
0.88	High Similarity	NPC275504
0.879	High Similarity	NPC476119
0.879	High Similarity	NPC102829
0.879	High Similarity	NPC120488
0.8783	High Similarity	NPC223004
0.877	High Similarity	NPC475733
0.877	High Similarity	NPC477454
0.875	High Similarity	NPC141523
0.874	High Similarity	NPC282780
0.874	High Similarity	NPC28753
0.874	High Similarity	NPC166480
0.874	High Similarity	NPC20560
0.874	High Similarity	NPC159623
0.874	High Similarity	NPC144051
0.874	High Similarity	NPC204960
0.874	High Similarity	NPC82225
0.874	High Similarity	NPC294593
0.874	High Similarity	NPC18877
0.872	High Similarity	NPC115998
0.872	High Similarity	NPC233056
0.872	High Similarity	NPC39753
0.8699	High Similarity	NPC473691
0.8678	High Similarity	NPC244351
0.8673	High Similarity	NPC224584
0.8672	High Similarity	NPC61153
0.8672	High Similarity	NPC283590
0.8672	High Similarity	NPC130899
0.8672	High Similarity	NPC470210
0.8672	High Similarity	NPC70859
0.8672	High Similarity	NPC286336
0.8667	High Similarity	NPC229649
0.8667	High Similarity	NPC248363
0.8651	High Similarity	NPC137264
0.864	High Similarity	NPC197425
0.864	High Similarity	NPC187907
0.8605	High Similarity	NPC13575
0.8605	High Similarity	NPC264112
0.8605	High Similarity	NPC65005
0.8605	High Similarity	NPC131039
0.8605	High Similarity	NPC194764
0.8595	High Similarity	NPC226275
0.8594	High Similarity	NPC337373
0.8594	High Similarity	NPC475088
0.8594	High Similarity	NPC56031
0.8594	High Similarity	NPC139813
0.8594	High Similarity	NPC312318
0.8594	High Similarity	NPC263670
0.8594	High Similarity	NPC192304
0.8594	High Similarity	NPC175098
0.8594	High Similarity	NPC188646
0.8594	High Similarity	NPC472365
0.8594	High Similarity	NPC242294
0.8583	High Similarity	NPC64359
0.8583	High Similarity	NPC135801
0.8583	High Similarity	NPC262359
0.8583	High Similarity	NPC313618
0.8583	High Similarity	NPC308037
0.8571	High Similarity	NPC26697
0.8559	High Similarity	NPC477453
0.8538	High Similarity	NPC477244
0.8538	High Similarity	NPC66349
0.8538	High Similarity	NPC477243
0.8538	High Similarity	NPC213603
0.8538	High Similarity	NPC98115
0.8538	High Similarity	NPC249606
0.8538	High Similarity	NPC41461
0.8538	High Similarity	NPC25287
0.8538	High Similarity	NPC474110
0.8538	High Similarity	NPC12165
0.8538	High Similarity	NPC477242
0.8538	High Similarity	NPC290030
0.8538	High Similarity	NPC1486
0.8538	High Similarity	NPC186838
0.8538	High Similarity	NPC44960
0.8538	High Similarity	NPC274109
0.8538	High Similarity	NPC168105
0.8538	High Similarity	NPC150399
0.8527	High Similarity	NPC103842
0.8525	High Similarity	NPC232708
0.8516	High Similarity	NPC129132
0.8516	High Similarity	NPC257756
0.8516	High Similarity	NPC205468
0.8516	High Similarity	NPC87231
0.8516	High Similarity	NPC212631
0.8504	High Similarity	NPC469526
0.8504	High Similarity	NPC34070
0.85	High Similarity	NPC184579
0.85	High Similarity	NPC233165
0.8473	Intermediate Similarity	NPC472419
0.8473	Intermediate Similarity	NPC153979
0.8473	Intermediate Similarity	NPC317119
0.8462	Intermediate Similarity	NPC118919
0.8462	Intermediate Similarity	NPC156092
0.8462	Intermediate Similarity	NPC191976
0.845	Intermediate Similarity	NPC44437
0.8438	Intermediate Similarity	NPC112192
0.8438	Intermediate Similarity	NPC164236
0.8438	Intermediate Similarity	NPC309717
0.8438	Intermediate Similarity	NPC128348
0.8438	Intermediate Similarity	NPC189106
0.8438	Intermediate Similarity	NPC113006
0.8438	Intermediate Similarity	NPC66384
0.843	Intermediate Similarity	NPC294964
0.8425	Intermediate Similarity	NPC17840
0.8425	Intermediate Similarity	NPC247477
0.8417	Intermediate Similarity	NPC283844
0.8417	Intermediate Similarity	NPC184527
0.8417	Intermediate Similarity	NPC249435
0.8417	Intermediate Similarity	NPC241089
0.8413	Intermediate Similarity	NPC475017
0.8409	Intermediate Similarity	NPC243528
0.8409	Intermediate Similarity	NPC242994
0.8409	Intermediate Similarity	NPC124269
0.8409	Intermediate Similarity	NPC472368
0.8409	Intermediate Similarity	NPC251681
0.8409	Intermediate Similarity	NPC138099
0.8409	Intermediate Similarity	NPC472903
0.8409	Intermediate Similarity	NPC112789
0.8409	Intermediate Similarity	NPC21350
0.8409	Intermediate Similarity	NPC19622
0.8407	Intermediate Similarity	NPC474839
0.84	Intermediate Similarity	NPC160499
0.84	Intermediate Similarity	NPC328983
0.8397	Intermediate Similarity	NPC240593
0.8397	Intermediate Similarity	NPC473391
0.8397	Intermediate Similarity	NPC13408
0.8397	Intermediate Similarity	NPC472367
0.8397	Intermediate Similarity	NPC472364
0.8397	Intermediate Similarity	NPC476333
0.8387	Intermediate Similarity	NPC173978
0.8385	Intermediate Similarity	NPC161632
0.8374	Intermediate Similarity	NPC283514
0.8372	Intermediate Similarity	NPC128216
0.8372	Intermediate Similarity	NPC267205
0.8362	Intermediate Similarity	NPC116842
0.8361	Intermediate Similarity	NPC292665

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 NPC188814 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	324
0.1-0.2	936
0.2-0.3	1282
0.3-0.4	2816
0.4-0.5	2143
0.5-0.6	1171
0.6-0.7	372
0.7-0.8	89
0.8-0.85	14
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8595	High Similarity	NPD1201	Approved
0.8583	High Similarity	NPD943	Approved
0.8583	High Similarity	NPD1240	Approved
0.845	Intermediate Similarity	NPD1607	Approved
0.8348	Intermediate Similarity	NPD9266	Approved
0.8348	Intermediate Similarity	NPD74	Approved
0.8321	Intermediate Similarity	NPD1510	Phase 2
0.832	Intermediate Similarity	NPD1470	Approved
0.8261	Intermediate Similarity	NPD9264	Approved
0.8261	Intermediate Similarity	NPD9263	Approved
0.8261	Intermediate Similarity	NPD9267	Approved
0.8195	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8195	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8175	Intermediate Similarity	NPD1164	Approved
0.8134	Intermediate Similarity	NPD1549	Phase 2
0.8099	Intermediate Similarity	NPD9493	Approved
0.8099	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8043	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7982	Intermediate Similarity	NPD940	Approved
0.7982	Intermediate Similarity	NPD846	Approved
0.7971	Intermediate Similarity	NPD7390	Discontinued
0.7914	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7913	Intermediate Similarity	NPD9261	Approved
0.7891	Intermediate Similarity	NPD1203	Approved
0.7852	Intermediate Similarity	NPD5408	Approved
0.7852	Intermediate Similarity	NPD1551	Phase 2
0.7852	Intermediate Similarity	NPD5405	Approved
0.7852	Intermediate Similarity	NPD2796	Approved
0.7852	Intermediate Similarity	NPD5404	Approved
0.7852	Intermediate Similarity	NPD5406	Approved
0.7829	Intermediate Similarity	NPD2798	Approved
0.7787	Intermediate Similarity	NPD9281	Approved
0.7778	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7762	Intermediate Similarity	NPD4380	Phase 2
0.7754	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7754	Intermediate Similarity	NPD3750	Approved
0.7721	Intermediate Similarity	NPD2935	Discontinued
0.7714	Intermediate Similarity	NPD1511	Approved
0.7667	Intermediate Similarity	NPD4750	Phase 3
0.7647	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD1512	Approved
0.7603	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD6799	Approved
0.7586	Intermediate Similarity	NPD7411	Suspended
0.7586	Intermediate Similarity	NPD1242	Phase 1
0.7578	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD5403	Approved
0.7551	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD2859	Approved
0.7544	Intermediate Similarity	NPD2860	Approved
0.7542	Intermediate Similarity	NPD1237	Approved
0.7534	Intermediate Similarity	NPD1934	Approved
0.7519	Intermediate Similarity	NPD9717	Approved
0.75	Intermediate Similarity	NPD6651	Approved
0.7483	Intermediate Similarity	NPD2801	Approved
0.7482	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD2797	Approved
0.7463	Intermediate Similarity	NPD2313	Discontinued
0.7456	Intermediate Similarity	NPD2934	Approved
0.7456	Intermediate Similarity	NPD2933	Approved
0.745	Intermediate Similarity	NPD7075	Discontinued
0.745	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD6832	Phase 2
0.7413	Intermediate Similarity	NPD5401	Approved
0.741	Intermediate Similarity	NPD2344	Approved
0.7397	Intermediate Similarity	NPD6599	Discontinued
0.7391	Intermediate Similarity	NPD2799	Discontinued
0.7391	Intermediate Similarity	NPD3748	Approved
0.7383	Intermediate Similarity	NPD3882	Suspended
0.7383	Intermediate Similarity	NPD7768	Phase 2
0.7365	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD7819	Suspended
0.735	Intermediate Similarity	NPD3020	Approved
0.7333	Intermediate Similarity	NPD3268	Approved
0.7333	Intermediate Similarity	NPD3749	Approved
0.7333	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD3764	Approved
0.7305	Intermediate Similarity	NPD2800	Approved
0.7297	Intermediate Similarity	NPD6801	Discontinued
0.7279	Intermediate Similarity	NPD520	Approved
0.7273	Intermediate Similarity	NPD3300	Phase 2
0.7266	Intermediate Similarity	NPD9545	Approved
0.7252	Intermediate Similarity	NPD9269	Phase 2
0.7214	Intermediate Similarity	NPD6099	Approved
0.7214	Intermediate Similarity	NPD6100	Approved
0.7209	Intermediate Similarity	NPD9268	Approved
0.7203	Intermediate Similarity	NPD2309	Approved
0.72	Intermediate Similarity	NPD5402	Approved
0.7183	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD1243	Approved
0.7176	Intermediate Similarity	NPD422	Phase 1
0.7161	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD6166	Phase 2
0.7154	Intermediate Similarity	NPD3019	Approved
0.7154	Intermediate Similarity	NPD2932	Approved
0.7143	Intermediate Similarity	NPD4308	Phase 3
0.7143	Intermediate Similarity	NPD6232	Discontinued
0.7132	Intermediate Similarity	NPD1759	Phase 1
0.7132	Intermediate Similarity	NPD1548	Phase 1
0.7121	Intermediate Similarity	NPD3972	Approved
0.7115	Intermediate Similarity	NPD7473	Discontinued
0.7094	Intermediate Similarity	NPD844	Approved
0.7086	Intermediate Similarity	NPD3817	Phase 2
0.7078	Intermediate Similarity	NPD6959	Discontinued
0.707	Intermediate Similarity	NPD3818	Discontinued
0.7069	Intermediate Similarity	NPD845	Approved
0.7063	Intermediate Similarity	NPD2654	Approved
0.7055	Intermediate Similarity	NPD2532	Approved
0.7055	Intermediate Similarity	NPD2534	Approved
0.7055	Intermediate Similarity	NPD2533	Approved
0.7055	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD1758	Phase 1
0.7045	Intermediate Similarity	NPD1610	Phase 2
0.7042	Intermediate Similarity	NPD2346	Discontinued
0.7034	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD1930	Approved
0.7025	Intermediate Similarity	NPD1929	Approved
0.7025	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD3225	Approved
0.7014	Intermediate Similarity	NPD1196	Approved
0.7014	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD1543	Discontinued
0.6981	Remote Similarity	NPD7074	Phase 3
0.698	Remote Similarity	NPD3226	Approved
0.6963	Remote Similarity	NPD3267	Approved
0.6963	Remote Similarity	NPD3266	Approved
0.6957	Remote Similarity	NPD9256	Approved
0.6957	Remote Similarity	NPD411	Approved
0.6957	Remote Similarity	NPD9258	Approved
0.6953	Remote Similarity	NPD5951	Approved
0.6944	Remote Similarity	NPD1195	Approved
0.6939	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD5953	Discontinued
0.6934	Remote Similarity	NPD4908	Phase 1
0.6929	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD447	Suspended
0.6929	Remote Similarity	NPD230	Phase 1
0.6929	Remote Similarity	NPD1933	Approved
0.6928	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1202	Approved
0.6918	Remote Similarity	NPD6020	Phase 2
0.6918	Remote Similarity	NPD7286	Phase 2
0.6918	Remote Similarity	NPD7054	Approved
0.6917	Remote Similarity	NPD2066	Phase 3
0.6901	Remote Similarity	NPD7033	Discontinued
0.6897	Remote Similarity	NPD3400	Discontinued
0.6894	Remote Similarity	NPD6559	Discontinued
0.6891	Remote Similarity	NPD288	Approved
0.6889	Remote Similarity	NPD1876	Approved
0.6884	Remote Similarity	NPD4625	Phase 3
0.6875	Remote Similarity	NPD7472	Approved
0.6866	Remote Similarity	NPD1608	Approved
0.6866	Remote Similarity	NPD4878	Approved
0.6864	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.686	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD4307	Phase 2
0.6852	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD9089	Approved
0.6846	Remote Similarity	NPD920	Approved
0.6835	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD1296	Phase 2
0.6832	Remote Similarity	NPD6797	Phase 2
0.6825	Remote Similarity	NPD3022	Approved
0.6825	Remote Similarity	NPD3021	Approved
0.6824	Remote Similarity	NPD4662	Approved
0.6824	Remote Similarity	NPD4661	Approved
0.6822	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD4749	Approved
0.6815	Remote Similarity	NPD1755	Approved
0.6807	Remote Similarity	NPD1809	Phase 2
0.6803	Remote Similarity	NPD1932	Approved
0.68	Remote Similarity	NPD2342	Discontinued
0.6797	Remote Similarity	NPD7635	Approved
0.6795	Remote Similarity	NPD5494	Approved
0.679	Remote Similarity	NPD7251	Discontinued
0.6788	Remote Similarity	NPD1019	Discontinued
0.6788	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD4628	Phase 3
0.6781	Remote Similarity	NPD7003	Approved
0.6774	Remote Similarity	NPD5048	Discontinued
0.6769	Remote Similarity	NPD255	Approved
0.6769	Remote Similarity	NPD256	Approved
0.6757	Remote Similarity	NPD9093	Approved
0.6753	Remote Similarity	NPD4288	Approved
0.6748	Remote Similarity	NPD7808	Phase 3
0.6748	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD1241	Discontinued
0.6741	Remote Similarity	NPD1481	Phase 2
0.6733	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD9279	Approved
0.6694	Remote Similarity	NPD5909	Discontinued
0.6694	Remote Similarity	NPD9273	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