NPASS Compound

Structure

CID196137 OpenBabel06191715582D 30 32 0 0 0 0 0 0 0 0999 V2000 -0.0000 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -6.0000 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 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -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 -2.5981 -2.5000 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 -0.0000 -4.0000 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 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -5.5000 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 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 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 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 0.8660 -1.5000 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 -2.5000 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 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 -1.7321 -3.0000 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 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 15 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 2 0 0 0 0 8 16 2 0 0 0 0 9 16 1 0 0 0 0 10 11 1 0 0 0 0 10 14 2 0 0 0 0 11 17 1 0 0 0 0 12 15 1 0 0 0 0 12 19 1 0 0 0 0 13 18 2 0 0 0 0 13 20 1 0 0 0 0 16 18 1 0 0 0 0 17 23 2 0 0 0 0 17 24 1 0 0 0 0 18 21 1 0 0 0 0 19 22 1 0 0 0 0 19 26 2 0 0 0 0 20 27 2 0 0 0 0 20 30 1 0 0 0 0 21 23 1 0 0 0 0 21 25 2 0 0 0 0 22 24 2 0 0 0 0 22 25 1 0 0 0 0 23 28 1 0 0 0 0 24 29 1 0 0 0 0 25 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	406.18
Volume:	432.873
LogP:	6.247
LogD:	3.84
LogS:	-4.264
# Rotatable Bonds:	6
TPSA:	87.74
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.316
Synthetic Accessibility Score:	2.816
Fsp3:	0.28
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:	-4.772
MDCK Permeability:	1.7085825675167143e-05
Pgp-inhibitor:	0.708
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.037
30% Bioavailability (F30%):	0.825

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013
Plasma Protein Binding (PPB):	95.80303192138672%
Volume Distribution (VD):	0.604
Pgp-substrate:	3.1079282760620117%

ADMET: Metabolism

CYP1A2-inhibitor:	0.343
CYP1A2-substrate:	0.199
CYP2C19-inhibitor:	0.835
CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.846
CYP2C9-substrate:	0.921
CYP2D6-inhibitor:	0.03
CYP2D6-substrate:	0.176
CYP3A4-inhibitor:	0.119
CYP3A4-substrate:	0.098

ADMET: Excretion

Clearance (CL):	10.0
Half-life (T1/2):	0.141

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.835
Drug-inuced Liver Injury (DILI):	0.972
AMES Toxicity:	0.086
Rat Oral Acute Toxicity:	0.323
Maximum Recommended Daily Dose:	0.048
Skin Sensitization:	0.446
Carcinogencity:	0.261
Eye Corrosion:	0.003
Eye Irritation:	0.04
Respiratory Toxicity:	0.38

Download Data

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

Natural Product: NPC196137

Natural Product ID:	NPC196137
*Common Name:**	Isomammeisin
IUPAC Name:	5,7-dihydroxy-8-(3-methylbutanoyl)-6-(3-methylbut-2-enyl)-4-phenylchromen-2-one
Synonyms:	Isomammeisin
Standard InCHIKey:	SBHOAZQBEGVQLJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C25H26O5/c1-14(2)10-11-17-23(28)21-18(16-8-6-5-7-9-16)13-20(27)30-25(21)22(24(17)29)19(26)12-15(3)4/h5-10,13,15,28-29H,11-12H2,1-4H3
SMILES:	CC(=CCc1c(c2c(cc(=O)oc2c(C(=O)CC(C)C)c1O)c1ccccc1)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL511810
PubChem CID:	5748555
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001614] Neoflavonoids [CHEMONTID:0003650] Prenylated neoflavonoids

*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
NPO33501	marila pluricostata	Species	Calophyllaceae	Eukaryota	leaves	n.a.	n.a.	PMID[15787438]
NPO4756	Mesua elegans	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20943395]
NPO21645	Mammea americana	Species	Calophyllaceae	Eukaryota	n.a.	stem	n.a.	PMID[21214226]
NPO21645	Mammea americana	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21214226]
NPO21645	Mammea americana	Species	Calophyllaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO21645	Mammea americana	Species	Calophyllaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO21645	Mammea americana	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21645	Mammea americana	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13839	Mammea harmandii	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21645	Mammea americana	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4756	Mesua elegans	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21645	Mammea americana	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
GI50	3
IC50	5

Activity Type	# Activity
Cell Line	5
Individual Protein	1
PROTEIN FAMILY	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	0.7	ug.mL-1	PMID[452899]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	=	0.8	ug.mL-1	PMID[452899]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	=	0.6	ug.mL-1	PMID[452899]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	IC50	>	20000.0	nM	PMID[452900]
NPT396	Cell Line	T47D	Homo sapiens	IC50	=	1570.0	nM	PMID[452901]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	2180.0	nM	PMID[452901]
NPT21802	PROTEIN FAMILY	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	Homo sapiens	IC50	=	3230.0	nM	PMID[452901]
NPT21802	PROTEIN FAMILY	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	Homo sapiens	IC50	=	3730.0	nM	PMID[452901]

☑ 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 NPC196137 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	380
0.1-0.2	1619
0.2-0.3	3863
0.3-0.4	9644
0.4-0.5	9034
0.5-0.6	3863
0.6-0.7	6000
0.7-0.8	4585
0.8-0.85	2155
0.85-0.9	1257
0.9-0.95	250
0.95-1	47

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC1886
0.9928	High Similarity	NPC196459
0.9928	High Similarity	NPC112791
0.9928	High Similarity	NPC181388
0.9928	High Similarity	NPC94794
0.9928	High Similarity	NPC154217
0.9928	High Similarity	NPC470322
0.9928	High Similarity	NPC188632
0.9928	High Similarity	NPC87609
0.9928	High Similarity	NPC470296
0.9856	High Similarity	NPC469935
0.9856	High Similarity	NPC178627
0.9855	High Similarity	NPC36181
0.9787	High Similarity	NPC208303
0.9787	High Similarity	NPC161864
0.9718	High Similarity	NPC469932
0.9716	High Similarity	NPC297886
0.9716	High Similarity	NPC140120
0.9716	High Similarity	NPC249942
0.965	High Similarity	NPC474735
0.9648	High Similarity	NPC469933
0.9645	High Similarity	NPC57470
0.9638	High Similarity	NPC473209
0.9583	High Similarity	NPC290671
0.958	High Similarity	NPC19238
0.9577	High Similarity	NPC180477
0.9574	High Similarity	NPC469953
0.9565	High Similarity	NPC199458
0.9565	High Similarity	NPC183639
0.95	High Similarity	NPC282300
0.95	High Similarity	NPC470555
0.9496	High Similarity	NPC301217
0.9496	High Similarity	NPC220062
0.9496	High Similarity	NPC96565
0.9496	High Similarity	NPC216978
0.9496	High Similarity	NPC241975
0.9496	High Similarity	NPC303633
0.9496	High Similarity	NPC217186
0.9496	High Similarity	NPC55018
0.9496	High Similarity	NPC53181
0.9496	High Similarity	NPC19476
0.9493	High Similarity	NPC138047
0.9493	High Similarity	NPC474624
0.9493	High Similarity	NPC131782
0.9448	High Similarity	NPC312549
0.9448	High Similarity	NPC209142
0.9444	High Similarity	NPC104236
0.9444	High Similarity	NPC164205
0.9437	High Similarity	NPC326500
0.9429	High Similarity	NPC261227
0.9429	High Similarity	NPC241100
0.9429	High Similarity	NPC270883
0.9429	High Similarity	NPC221173
0.9429	High Similarity	NPC172986
0.9429	High Similarity	NPC159275
0.9424	High Similarity	NPC201395
0.9424	High Similarity	NPC219584
0.9424	High Similarity	NPC470083
0.9388	High Similarity	NPC469934
0.9379	High Similarity	NPC151973
0.9366	High Similarity	NPC219915
0.9366	High Similarity	NPC293053
0.9366	High Similarity	NPC212932
0.9366	High Similarity	NPC11700
0.9366	High Similarity	NPC9117
0.9366	High Similarity	NPC24821
0.9366	High Similarity	NPC190637
0.9362	High Similarity	NPC118840
0.9362	High Similarity	NPC110969
0.9362	High Similarity	NPC64908
0.9362	High Similarity	NPC147688
0.9362	High Similarity	NPC156590
0.9362	High Similarity	NPC205006
0.9357	High Similarity	NPC472343
0.9357	High Similarity	NPC18260
0.9357	High Similarity	NPC78913
0.9357	High Similarity	NPC470986
0.9324	High Similarity	NPC474738
0.9324	High Similarity	NPC474609
0.9324	High Similarity	NPC129053
0.9324	High Similarity	NPC469936
0.9324	High Similarity	NPC475797
0.9324	High Similarity	NPC109967
0.9324	High Similarity	NPC321372
0.9324	High Similarity	NPC78554
0.9301	High Similarity	NPC311741
0.9301	High Similarity	NPC234629
0.9301	High Similarity	NPC273538
0.9301	High Similarity	NPC216538
0.9301	High Similarity	NPC271288
0.9296	High Similarity	NPC473042
0.9296	High Similarity	NPC266725
0.9296	High Similarity	NPC217083
0.9296	High Similarity	NPC299080
0.9296	High Similarity	NPC470556
0.9296	High Similarity	NPC226636
0.9296	High Similarity	NPC214236
0.9296	High Similarity	NPC62840
0.9296	High Similarity	NPC59739
0.9296	High Similarity	NPC293852
0.9296	High Similarity	NPC200694
0.9296	High Similarity	NPC78803
0.9296	High Similarity	NPC144499
0.9296	High Similarity	NPC11561
0.9291	High Similarity	NPC475680
0.9291	High Similarity	NPC235239
0.9291	High Similarity	NPC69769
0.9291	High Similarity	NPC150522
0.9291	High Similarity	NPC305355
0.9286	High Similarity	NPC470669
0.9286	High Similarity	NPC470668
0.9281	High Similarity	NPC13408
0.9257	High Similarity	NPC108937
0.9257	High Similarity	NPC279218
0.9236	High Similarity	NPC124729
0.9236	High Similarity	NPC178343
0.9236	High Similarity	NPC153758
0.9236	High Similarity	NPC474161
0.9236	High Similarity	NPC477955
0.9236	High Similarity	NPC220418
0.9236	High Similarity	NPC5820
0.9236	High Similarity	NPC306488
0.9236	High Similarity	NPC476088
0.9236	High Similarity	NPC25844
0.9231	High Similarity	NPC125894
0.9231	High Similarity	NPC307895
0.9231	High Similarity	NPC106985
0.9231	High Similarity	NPC474939
0.9231	High Similarity	NPC166138
0.9231	High Similarity	NPC107177
0.9231	High Similarity	NPC77794
0.9231	High Similarity	NPC85162
0.9231	High Similarity	NPC18585
0.9231	High Similarity	NPC96216
0.9231	High Similarity	NPC223812
0.9231	High Similarity	NPC81697
0.9231	High Similarity	NPC470909
0.9231	High Similarity	NPC278249
0.9231	High Similarity	NPC470553
0.9231	High Similarity	NPC38219
0.9225	High Similarity	NPC110038
0.9225	High Similarity	NPC14871
0.9225	High Similarity	NPC248372
0.9225	High Similarity	NPC103362
0.922	High Similarity	NPC283429
0.922	High Similarity	NPC240305
0.9214	High Similarity	NPC103001
0.9214	High Similarity	NPC228661
0.9214	High Similarity	NPC332594
0.9184	High Similarity	NPC78835
0.9184	High Similarity	NPC204561
0.9184	High Similarity	NPC316960
0.9184	High Similarity	NPC309512
0.9184	High Similarity	NPC317715
0.9184	High Similarity	NPC148945
0.9178	High Similarity	NPC470461
0.9172	High Similarity	NPC104406
0.9172	High Similarity	NPC14001
0.9172	High Similarity	NPC97716
0.9172	High Similarity	NPC296998
0.9172	High Similarity	NPC474108
0.9172	High Similarity	NPC237635
0.9172	High Similarity	NPC285748
0.9172	High Similarity	NPC24673
0.9172	High Similarity	NPC177995
0.9172	High Similarity	NPC308200
0.9172	High Similarity	NPC201731
0.9172	High Similarity	NPC79469
0.9172	High Similarity	NPC166757
0.9172	High Similarity	NPC473077
0.9167	High Similarity	NPC133060
0.9167	High Similarity	NPC257236
0.9167	High Similarity	NPC118059
0.9167	High Similarity	NPC288910
0.9167	High Similarity	NPC278175
0.9167	High Similarity	NPC235217
0.9167	High Similarity	NPC473014
0.9167	High Similarity	NPC206212
0.9167	High Similarity	NPC224714
0.9167	High Similarity	NPC131568
0.9167	High Similarity	NPC473015
0.9167	High Similarity	NPC71184
0.9167	High Similarity	NPC473013
0.9167	High Similarity	NPC131579
0.9167	High Similarity	NPC470554
0.9167	High Similarity	NPC319752
0.9161	High Similarity	NPC220998
0.9161	High Similarity	NPC112829
0.9161	High Similarity	NPC32739
0.9161	High Similarity	NPC265040
0.9161	High Similarity	NPC10937
0.9161	High Similarity	NPC228504
0.9161	High Similarity	NPC227579
0.9161	High Similarity	NPC76338
0.9161	High Similarity	NPC294432
0.9161	High Similarity	NPC324436
0.9161	High Similarity	NPC223500
0.9161	High Similarity	NPC125855
0.9161	High Similarity	NPC64915
0.9161	High Similarity	NPC66515

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 NPC196137 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	347
0.1-0.2	964
0.2-0.3	1547
0.3-0.4	2564
0.4-0.5	2006
0.5-0.6	1169
0.6-0.7	364
0.7-0.8	122
0.8-0.85	39
0.85-0.9	19
0.9-0.95	9
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9301	High Similarity	NPD4378	Clinical (unspecified phase)
0.9167	High Similarity	NPD7410	Clinical (unspecified phase)
0.8926	High Similarity	NPD7411	Suspended
0.8882	High Similarity	NPD7075	Discontinued
0.8811	High Similarity	NPD1550	Clinical (unspecified phase)
0.8811	High Similarity	NPD1552	Clinical (unspecified phase)
0.8808	High Similarity	NPD7096	Clinical (unspecified phase)
0.8808	High Similarity	NPD7819	Suspended
0.8803	High Similarity	NPD1510	Phase 2
0.8759	High Similarity	NPD3750	Approved
0.875	High Similarity	NPD1549	Phase 2
0.875	High Similarity	NPD8443	Clinical (unspecified phase)
0.8742	High Similarity	NPD6801	Discontinued
0.8741	High Similarity	NPD2796	Approved
0.869	High Similarity	NPD1243	Approved
0.8684	High Similarity	NPD2393	Clinical (unspecified phase)
0.8652	High Similarity	NPD1240	Approved
0.8621	High Similarity	NPD970	Clinical (unspecified phase)
0.8609	High Similarity	NPD4380	Phase 2
0.8581	High Similarity	NPD1511	Approved
0.8581	High Similarity	NPD6799	Approved
0.8571	High Similarity	NPD7768	Phase 2
0.8562	High Similarity	NPD7421	Clinical (unspecified phase)
0.8544	High Similarity	NPD7852	Clinical (unspecified phase)
0.8542	High Similarity	NPD2799	Discontinued
0.8531	High Similarity	NPD1607	Approved
0.8516	High Similarity	NPD3749	Approved
0.8511	High Similarity	NPD2313	Discontinued
0.8467	Intermediate Similarity	NPD1512	Approved
0.8442	Intermediate Similarity	NPD2801	Approved
0.8435	Intermediate Similarity	NPD2800	Approved
0.8414	Intermediate Similarity	NPD3748	Approved
0.8411	Intermediate Similarity	NPD920	Approved
0.8397	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8389	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD3817	Phase 2
0.838	Intermediate Similarity	NPD3268	Approved
0.838	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8377	Intermediate Similarity	NPD1934	Approved
0.8366	Intermediate Similarity	NPD6599	Discontinued
0.8356	Intermediate Similarity	NPD1551	Phase 2
0.8356	Intermediate Similarity	NPD2935	Discontinued
0.8286	Intermediate Similarity	NPD2797	Approved
0.8286	Intermediate Similarity	NPD1203	Approved
0.8278	Intermediate Similarity	NPD2532	Approved
0.8278	Intermediate Similarity	NPD2534	Approved
0.8278	Intermediate Similarity	NPD2533	Approved
0.8278	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD6651	Approved
0.8272	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD7473	Discontinued
0.8187	Intermediate Similarity	NPD6232	Discontinued
0.8182	Intermediate Similarity	NPD3226	Approved
0.8171	Intermediate Similarity	NPD5953	Discontinued
0.817	Intermediate Similarity	NPD5403	Approved
0.8133	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD422	Phase 1
0.8125	Intermediate Similarity	NPD6959	Discontinued
0.8101	Intermediate Similarity	NPD3882	Suspended
0.8082	Intermediate Similarity	NPD5124	Phase 1
0.8082	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8071	Intermediate Similarity	NPD9717	Approved
0.8054	Intermediate Similarity	NPD2346	Discontinued
0.8049	Intermediate Similarity	NPD7286	Phase 2
0.8041	Intermediate Similarity	NPD4308	Phase 3
0.8039	Intermediate Similarity	NPD5401	Approved
0.8028	Intermediate Similarity	NPD3266	Approved
0.8028	Intermediate Similarity	NPD3267	Approved
0.8013	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD919	Approved
0.7988	Intermediate Similarity	NPD3818	Discontinued
0.7987	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD6832	Phase 2
0.7975	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD6166	Phase 2
0.7975	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7972	Intermediate Similarity	NPD2798	Approved
0.7958	Intermediate Similarity	NPD3225	Approved
0.795	Intermediate Similarity	NPD5494	Approved
0.7939	Intermediate Similarity	NPD5844	Phase 1
0.7939	Intermediate Similarity	NPD7054	Approved
0.7933	Intermediate Similarity	NPD2344	Approved
0.7925	Intermediate Similarity	NPD5402	Approved
0.7919	Intermediate Similarity	NPD7033	Discontinued
0.7904	Intermediate Similarity	NPD6559	Discontinued
0.7895	Intermediate Similarity	NPD4628	Phase 3
0.7892	Intermediate Similarity	NPD7472	Approved
0.7892	Intermediate Similarity	NPD7074	Phase 3
0.7877	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD6099	Approved
0.7867	Intermediate Similarity	NPD6100	Approved
0.7857	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD6797	Phase 2
0.7817	Intermediate Similarity	NPD1608	Approved
0.78	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD7251	Discontinued
0.777	Intermediate Similarity	NPD4307	Phase 2
0.7755	Intermediate Similarity	NPD1296	Phase 2
0.7751	Intermediate Similarity	NPD7808	Phase 3
0.775	Intermediate Similarity	NPD1465	Phase 2
0.774	Intermediate Similarity	NPD4908	Phase 1
0.7736	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD2309	Approved
0.7702	Intermediate Similarity	NPD4288	Approved
0.7651	Intermediate Similarity	NPD943	Approved
0.7636	Intermediate Similarity	NPD5711	Approved
0.7636	Intermediate Similarity	NPD5710	Approved
0.7635	Intermediate Similarity	NPD411	Approved
0.7632	Intermediate Similarity	NPD5405	Approved
0.7632	Intermediate Similarity	NPD5406	Approved
0.7632	Intermediate Similarity	NPD5404	Approved
0.7632	Intermediate Similarity	NPD5408	Approved
0.7628	Intermediate Similarity	NPD7390	Discontinued
0.7627	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD1610	Phase 2
0.7614	Intermediate Similarity	NPD4363	Phase 3
0.7614	Intermediate Similarity	NPD4360	Phase 2
0.761	Intermediate Similarity	NPD7458	Discontinued
0.7606	Intermediate Similarity	NPD17	Approved
0.76	Intermediate Similarity	NPD447	Suspended
0.76	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD1548	Phase 1
0.7586	Intermediate Similarity	NPD4287	Approved
0.7582	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD4361	Phase 2
0.7571	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD6585	Discontinued
0.7548	Intermediate Similarity	NPD7003	Approved
0.7534	Intermediate Similarity	NPD1164	Approved
0.753	Intermediate Similarity	NPD7229	Phase 3
0.7529	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD3764	Approved
0.7516	Intermediate Similarity	NPD5890	Approved
0.7516	Intermediate Similarity	NPD5889	Approved
0.75	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1933	Approved
0.747	Intermediate Similarity	NPD1247	Approved
0.7465	Intermediate Similarity	NPD9545	Approved
0.745	Intermediate Similarity	NPD4625	Phase 3
0.7447	Intermediate Similarity	NPD9493	Approved
0.7421	Intermediate Similarity	NPD5049	Phase 3
0.7405	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD6798	Discontinued
0.7383	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD3926	Phase 2
0.7372	Intermediate Similarity	NPD2654	Approved
0.7368	Intermediate Similarity	NPD230	Phase 1
0.7368	Intermediate Similarity	NPD6355	Discontinued
0.7365	Intermediate Similarity	NPD1019	Discontinued
0.7365	Intermediate Similarity	NPD7199	Phase 2
0.7355	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD6004	Phase 3
0.7355	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD6005	Phase 3
0.7355	Intermediate Similarity	NPD6002	Phase 3
0.7329	Intermediate Similarity	NPD1481	Phase 2
0.7312	Intermediate Similarity	NPD6273	Approved
0.7303	Intermediate Similarity	NPD4060	Phase 1
0.7303	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD8312	Approved
0.7299	Intermediate Similarity	NPD8313	Approved
0.729	Intermediate Similarity	NPD4476	Approved
0.729	Intermediate Similarity	NPD4477	Approved
0.7286	Intermediate Similarity	NPD5535	Approved
0.7279	Intermediate Similarity	NPD4749	Approved
0.7278	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD2354	Approved
0.7267	Intermediate Similarity	NPD1729	Discontinued
0.7267	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD1652	Phase 2
0.726	Intermediate Similarity	NPD1535	Discovery
0.726	Intermediate Similarity	NPD1201	Approved
0.7251	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD1283	Approved
0.7222	Intermediate Similarity	NPD1894	Discontinued
0.7211	Intermediate Similarity	NPD3972	Approved
0.72	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD6971	Discontinued
0.7181	Intermediate Similarity	NPD1470	Approved
0.7175	Intermediate Similarity	NPD8434	Phase 2
0.7169	Intermediate Similarity	NPD2296	Approved
0.7166	Intermediate Similarity	NPD7584	Approved
0.7152	Intermediate Similarity	NPD2614	Approved
0.7152	Intermediate Similarity	NPD37	Approved
0.7151	Intermediate Similarity	NPD7177	Discontinued
0.7143	Intermediate Similarity	NPD6234	Discontinued
0.7134	Intermediate Similarity	NPD1471	Phase 3
0.7134	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2353	Approved
0.7134	Intermediate Similarity	NPD6502	Phase 2
0.7126	Intermediate Similarity	NPD4967	Phase 2
0.7126	Intermediate Similarity	NPD4965	Approved
0.7126	Intermediate Similarity	NPD4966	Approved
0.7125	Intermediate Similarity	NPD6667	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