NPASS Compound

Structure

NPC473209 OpenBabel07101718192D 36 38 0 0 0 0 0 0 0 0999 V2000 -3.3753 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 5.8462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 5.8462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3753 2.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 5.3590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2191 2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3753 2.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2191 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3753 0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 4.3846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 -0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 5.3590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 4.8718 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.8974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 -0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 1.4615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 5.3590 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 4.3846 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 -1.4615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 2.9231 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 2.9231 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 16 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 17 1 0 0 0 0 5 18 1 0 0 0 0 6 19 1 0 0 0 0 7 8 2 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 2 0 0 0 0 10 20 2 0 0 0 0 11 20 1 0 0 0 0 12 13 1 0 0 0 0 12 16 2 0 0 0 0 13 21 1 0 0 0 0 14 17 1 0 0 0 0 14 23 1 0 0 0 0 15 22 2 0 0 0 0 15 24 1 0 0 0 0 18 30 2 0 0 0 0 18 34 1 0 0 0 0 19 31 2 0 0 0 0 19 35 1 0 0 0 0 20 22 1 0 0 0 0 21 27 2 0 0 0 0 21 28 1 0 0 0 0 22 25 1 0 0 0 0 23 26 1 0 0 0 0 23 32 2 0 0 0 0 24 33 2 0 0 0 0 24 36 1 0 0 0 0 25 27 1 0 0 0 0 25 29 2 0 0 0 0 26 28 2 0 0 0 0 26 29 1 0 0 0 0 27 36 1 0 0 0 0 28 34 1 0 0 0 0 29 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	490.2
Volume:	514.365
LogP:	5.934
LogD:	3.615
LogS:	-4.703
# Rotatable Bonds:	10
TPSA:	99.88
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.125
Synthetic Accessibility Score:	3.007
Fsp3:	0.31
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:	-4.729
MDCK Permeability:	2.2846037609269843e-05
Pgp-inhibitor:	0.967
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.27
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.15
Plasma Protein Binding (PPB):	91.15003204345703%
Volume Distribution (VD):	1.255
Pgp-substrate:	7.423911094665527%

ADMET: Metabolism

CYP1A2-inhibitor:	0.206
CYP1A2-substrate:	0.073
CYP2C19-inhibitor:	0.725
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.85
CYP2C9-substrate:	0.784
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.091
CYP3A4-inhibitor:	0.13
CYP3A4-substrate:	0.12

ADMET: Excretion

Clearance (CL):	2.042
Half-life (T1/2):	0.199

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.109
Drug-inuced Liver Injury (DILI):	0.942
AMES Toxicity:	0.036
Rat Oral Acute Toxicity:	0.772
Maximum Recommended Daily Dose:	0.097
Skin Sensitization:	0.772
Carcinogencity:	0.368
Eye Corrosion:	0.003
Eye Irritation:	0.025
Respiratory Toxicity:	0.446

Download Data

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

Natural Product: NPC473209

Natural Product ID:	NPC473209
*Common Name:**	Mammeisin Diacetate
IUPAC Name:	[5-acetyloxy-6-(3-methylbutanoyl)-8-(3-methylbut-2-enyl)-2-oxo-4-phenylchromen-7-yl] acetate
Synonyms:	Mammeisin Diacetate
Standard InCHIKey:	OVAGITAYMDGGBZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C29H30O7/c1-16(2)12-13-21-27-25(22(15-24(33)36-27)20-10-8-7-9-11-20)29(35-19(6)31)26(23(32)14-17(3)4)28(21)34-18(5)30/h7-12,15,17H,13-14H2,1-6H3
SMILES:	CC(C)CC(=O)C1=C(C(=C2C(=C1OC(=O)C)C(=CC(=O)O2)C3=CC=CC=C3)CC=C(C)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL370146
PubChem CID:	6483319
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]

☑ 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
Others	3

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	Inhibition	=	50.4	%	PMID[570810]
NPT460	Cell Line	MT2	Homo sapiens	Cell death	=	15.7	%	PMID[570810]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	0.6	ug.mL-1	PMID[570811]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	=	0.6	ug.mL-1	PMID[570811]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	=	0.5	ug.mL-1	PMID[570811]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	81.1	%	PMID[570810]

☑ 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 NPC473209 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	453
0.1-0.2	1698
0.2-0.3	4212
0.3-0.4	10511
0.4-0.5	7968
0.5-0.6	4345
0.6-0.7	6086
0.7-0.8	4984
0.8-0.85	1613
0.85-0.9	648
0.9-0.95	157
0.95-1	22

Similarity Score	Similarity Level	Natural Product ID
0.9638	High Similarity	NPC196137
0.9638	High Similarity	NPC1886
0.9568	High Similarity	NPC470322
0.9568	High Similarity	NPC181388
0.9568	High Similarity	NPC154217
0.9565	High Similarity	NPC87609
0.9565	High Similarity	NPC470296
0.9565	High Similarity	NPC188632
0.9565	High Similarity	NPC112791
0.9565	High Similarity	NPC196459
0.9565	High Similarity	NPC94794
0.9556	High Similarity	NPC103001
0.9496	High Similarity	NPC469935
0.9496	High Similarity	NPC178627
0.9493	High Similarity	NPC36181
0.9485	High Similarity	NPC36414
0.9433	High Similarity	NPC161864
0.9433	High Similarity	NPC208303
0.9416	High Similarity	NPC472515
0.9416	High Similarity	NPC136095
0.9412	High Similarity	NPC253616
0.9366	High Similarity	NPC469932
0.9362	High Similarity	NPC297886
0.9362	High Similarity	NPC140120
0.9362	High Similarity	NPC249942
0.9362	High Similarity	NPC218300
0.9362	High Similarity	NPC282335
0.9338	High Similarity	NPC161196
0.9338	High Similarity	NPC268081
0.9301	High Similarity	NPC474735
0.9296	High Similarity	NPC469933
0.9291	High Similarity	NPC57470
0.9281	High Similarity	NPC24075
0.927	High Similarity	NPC38153
0.9236	High Similarity	NPC290671
0.9231	High Similarity	NPC19238
0.9225	High Similarity	NPC180477
0.922	High Similarity	NPC469953
0.9209	High Similarity	NPC474037
0.9203	High Similarity	NPC17848
0.9203	High Similarity	NPC183639
0.9203	High Similarity	NPC199458
0.9197	High Similarity	NPC472516
0.9197	High Similarity	NPC254741
0.9185	High Similarity	NPC473655
0.9185	High Similarity	NPC101294
0.9143	High Similarity	NPC470555
0.9143	High Similarity	NPC254010
0.9143	High Similarity	NPC282300
0.9143	High Similarity	NPC201820
0.9137	High Similarity	NPC19476
0.9137	High Similarity	NPC241975
0.9137	High Similarity	NPC220062
0.9137	High Similarity	NPC217186
0.9137	High Similarity	NPC55018
0.9137	High Similarity	NPC301217
0.9137	High Similarity	NPC303633
0.9137	High Similarity	NPC53181
0.9137	High Similarity	NPC96565
0.9137	High Similarity	NPC216978
0.913	High Similarity	NPC131782
0.913	High Similarity	NPC157855
0.913	High Similarity	NPC259685
0.913	High Similarity	NPC474624
0.913	High Similarity	NPC138047
0.9124	High Similarity	NPC46869
0.9118	High Similarity	NPC292998
0.9111	High Similarity	NPC278556
0.9103	High Similarity	NPC312549
0.9103	High Similarity	NPC209142
0.9097	High Similarity	NPC164205
0.9097	High Similarity	NPC164299
0.9097	High Similarity	NPC104236
0.9085	High Similarity	NPC326500
0.9085	High Similarity	NPC294365
0.9071	High Similarity	NPC150522
0.9071	High Similarity	NPC261227
0.9071	High Similarity	NPC221173
0.9071	High Similarity	NPC241100
0.9071	High Similarity	NPC159275
0.9071	High Similarity	NPC172986
0.9071	High Similarity	NPC270883
0.9065	High Similarity	NPC201395
0.9065	High Similarity	NPC219584
0.9065	High Similarity	NPC470083
0.9051	High Similarity	NPC66705
0.9048	High Similarity	NPC469934
0.9034	High Similarity	NPC151973
0.9021	High Similarity	NPC473927
0.9014	High Similarity	NPC9117
0.9014	High Similarity	NPC293053
0.9014	High Similarity	NPC24821
0.9014	High Similarity	NPC219915
0.9014	High Similarity	NPC212932
0.9014	High Similarity	NPC190637
0.9014	High Similarity	NPC11700
0.9007	High Similarity	NPC205006
0.9007	High Similarity	NPC52576
0.9007	High Similarity	NPC110969
0.9007	High Similarity	NPC103362
0.9007	High Similarity	NPC147688
0.9007	High Similarity	NPC64908
0.9007	High Similarity	NPC156590
0.9007	High Similarity	NPC118840
0.9	High Similarity	NPC78913
0.9	High Similarity	NPC11566
0.9	High Similarity	NPC262635
0.9	High Similarity	NPC470986
0.9	High Similarity	NPC472343
0.9	High Similarity	NPC18260
0.8986	High Similarity	NPC321372
0.8986	High Similarity	NPC129053
0.8986	High Similarity	NPC469936
0.8986	High Similarity	NPC109967
0.8986	High Similarity	NPC474609
0.8986	High Similarity	NPC475797
0.8986	High Similarity	NPC474738
0.8986	High Similarity	NPC99854
0.8986	High Similarity	NPC78554
0.8978	High Similarity	NPC223354
0.8971	High Similarity	NPC284424
0.8951	High Similarity	NPC216538
0.8951	High Similarity	NPC171656
0.8951	High Similarity	NPC234629
0.8951	High Similarity	NPC271288
0.8951	High Similarity	NPC273538
0.8951	High Similarity	NPC311741
0.8951	High Similarity	NPC179970
0.8944	High Similarity	NPC226636
0.8944	High Similarity	NPC62840
0.8944	High Similarity	NPC144499
0.8944	High Similarity	NPC473042
0.8944	High Similarity	NPC59739
0.8944	High Similarity	NPC299080
0.8944	High Similarity	NPC200694
0.8944	High Similarity	NPC11561
0.8944	High Similarity	NPC470556
0.8944	High Similarity	NPC214236
0.8944	High Similarity	NPC266725
0.8944	High Similarity	NPC217083
0.8944	High Similarity	NPC313036
0.8944	High Similarity	NPC293852
0.8944	High Similarity	NPC78803
0.8936	High Similarity	NPC470856
0.8936	High Similarity	NPC305355
0.8936	High Similarity	NPC472409
0.8936	High Similarity	NPC475680
0.8936	High Similarity	NPC235239
0.8936	High Similarity	NPC69769
0.8929	High Similarity	NPC470669
0.8929	High Similarity	NPC470668
0.8921	High Similarity	NPC13408
0.8921	High Similarity	NPC72452
0.8921	High Similarity	NPC61546
0.8919	High Similarity	NPC108937
0.8919	High Similarity	NPC279218
0.8913	High Similarity	NPC125269
0.8905	High Similarity	NPC55147
0.8905	High Similarity	NPC54503
0.8905	High Similarity	NPC229646
0.8905	High Similarity	NPC182428
0.8904	High Similarity	NPC474660
0.8904	High Similarity	NPC191104
0.8904	High Similarity	NPC473466
0.8889	High Similarity	NPC477955
0.8889	High Similarity	NPC306488
0.8889	High Similarity	NPC5820
0.8889	High Similarity	NPC124729
0.8889	High Similarity	NPC153758
0.8889	High Similarity	NPC220418
0.8889	High Similarity	NPC178343
0.8889	High Similarity	NPC474161
0.8889	High Similarity	NPC476088
0.8889	High Similarity	NPC25844
0.8889	High Similarity	NPC473894
0.8881	High Similarity	NPC77794
0.8881	High Similarity	NPC85162
0.8881	High Similarity	NPC17262
0.8881	High Similarity	NPC125894
0.8881	High Similarity	NPC223812
0.8881	High Similarity	NPC278249
0.8881	High Similarity	NPC107177
0.8881	High Similarity	NPC470553
0.8881	High Similarity	NPC96216
0.8881	High Similarity	NPC38219
0.8881	High Similarity	NPC18585
0.8881	High Similarity	NPC81697
0.8881	High Similarity	NPC189650
0.8881	High Similarity	NPC307895
0.8881	High Similarity	NPC166138
0.8881	High Similarity	NPC59522
0.8881	High Similarity	NPC474939
0.8881	High Similarity	NPC470909
0.8881	High Similarity	NPC106985
0.8873	High Similarity	NPC110038
0.8873	High Similarity	NPC248372
0.8873	High Similarity	NPC14871
0.8873	High Similarity	NPC22467
0.8865	High Similarity	NPC283429
0.8865	High Similarity	NPC240305

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 NPC473209 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	381
0.1-0.2	961
0.2-0.3	1547
0.3-0.4	2662
0.4-0.5	1965
0.5-0.6	1094
0.6-0.7	361
0.7-0.8	129
0.8-0.85	28
0.85-0.9	17
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9058	High Similarity	NPD2796	Approved
0.9	High Similarity	NPD1243	Approved
0.8951	High Similarity	NPD4378	Clinical (unspecified phase)
0.8819	High Similarity	NPD7410	Clinical (unspecified phase)
0.8725	High Similarity	NPD7819	Suspended
0.8725	High Similarity	NPD7096	Clinical (unspecified phase)
0.8716	High Similarity	NPD7411	Suspended
0.8714	High Similarity	NPD3748	Approved
0.8699	High Similarity	NPD920	Approved
0.8681	High Similarity	NPD643	Clinical (unspecified phase)
0.8658	High Similarity	NPD6801	Discontinued
0.8621	High Similarity	NPD6799	Approved
0.8562	High Similarity	NPD642	Clinical (unspecified phase)
0.8553	High Similarity	NPD7075	Discontinued
0.8462	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8451	Intermediate Similarity	NPD2799	Discontinued
0.8451	Intermediate Similarity	NPD1510	Phase 2
0.8421	Intermediate Similarity	NPD3817	Phase 2
0.8421	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8417	Intermediate Similarity	NPD2313	Discontinued
0.8414	Intermediate Similarity	NPD3750	Approved
0.8403	Intermediate Similarity	NPD1549	Phase 2
0.84	Intermediate Similarity	NPD6599	Discontinued
0.8355	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8345	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8321	Intermediate Similarity	NPD3267	Approved
0.8321	Intermediate Similarity	NPD3266	Approved
0.8298	Intermediate Similarity	NPD1240	Approved
0.8286	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8278	Intermediate Similarity	NPD4380	Phase 2
0.8276	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8273	Intermediate Similarity	NPD6832	Phase 2
0.8258	Intermediate Similarity	NPD919	Approved
0.8247	Intermediate Similarity	NPD7768	Phase 2
0.8243	Intermediate Similarity	NPD1511	Approved
0.8228	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD5494	Approved
0.8194	Intermediate Similarity	NPD3749	Approved
0.8182	Intermediate Similarity	NPD1607	Approved
0.8156	Intermediate Similarity	NPD3268	Approved
0.8133	Intermediate Similarity	NPD1512	Approved
0.8117	Intermediate Similarity	NPD2801	Approved
0.8095	Intermediate Similarity	NPD2800	Approved
0.8079	Intermediate Similarity	NPD5403	Approved
0.8077	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD5401	Approved
0.8058	Intermediate Similarity	NPD2797	Approved
0.8052	Intermediate Similarity	NPD1934	Approved
0.8042	Intermediate Similarity	NPD4307	Phase 2
0.8028	Intermediate Similarity	NPD1296	Phase 2
0.8014	Intermediate Similarity	NPD1551	Phase 2
0.8014	Intermediate Similarity	NPD2935	Discontinued
0.8	Intermediate Similarity	NPD2798	Approved
0.7974	Intermediate Similarity	NPD3226	Approved
0.7963	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD2346	Discontinued
0.795	Intermediate Similarity	NPD7473	Discontinued
0.7947	Intermediate Similarity	NPD2534	Approved
0.7947	Intermediate Similarity	NPD2532	Approved
0.7947	Intermediate Similarity	NPD2533	Approved
0.7931	Intermediate Similarity	NPD6651	Approved
0.7929	Intermediate Similarity	NPD1203	Approved
0.7883	Intermediate Similarity	NPD17	Approved
0.7875	Intermediate Similarity	NPD6232	Discontinued
0.7866	Intermediate Similarity	NPD5953	Discontinued
0.7862	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD5124	Phase 1
0.7843	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7842	Intermediate Similarity	NPD9717	Approved
0.7834	Intermediate Similarity	NPD5402	Approved
0.7823	Intermediate Similarity	NPD4308	Phase 3
0.7812	Intermediate Similarity	NPD6959	Discontinued
0.7806	Intermediate Similarity	NPD6585	Discontinued
0.78	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD3882	Suspended
0.7771	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD422	Phase 1
0.777	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD5889	Approved
0.7756	Intermediate Similarity	NPD5890	Approved
0.7744	Intermediate Similarity	NPD7286	Phase 2
0.7744	Intermediate Similarity	NPD5844	Phase 1
0.774	Intermediate Similarity	NPD1933	Approved
0.773	Intermediate Similarity	NPD3225	Approved
0.7714	Intermediate Similarity	NPD1608	Approved
0.7703	Intermediate Similarity	NPD7033	Discontinued
0.7702	Intermediate Similarity	NPD1247	Approved
0.7683	Intermediate Similarity	NPD3818	Discontinued
0.7682	Intermediate Similarity	NPD4628	Phase 3
0.7682	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD6166	Phase 2
0.7669	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD7054	Approved
0.7622	Intermediate Similarity	NPD1019	Discontinued
0.7616	Intermediate Similarity	NPD2654	Approved
0.761	Intermediate Similarity	NPD4288	Approved
0.7607	Intermediate Similarity	NPD3926	Phase 2
0.7605	Intermediate Similarity	NPD6559	Discontinued
0.76	Intermediate Similarity	NPD2344	Approved
0.759	Intermediate Similarity	NPD7074	Phase 3
0.759	Intermediate Similarity	NPD7472	Approved
0.756	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD5535	Approved
0.7545	Intermediate Similarity	NPD6797	Phase 2
0.7534	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD6100	Approved
0.7533	Intermediate Similarity	NPD6099	Approved
0.7532	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7251	Discontinued
0.7483	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD3972	Approved
0.7456	Intermediate Similarity	NPD7808	Phase 3
0.7455	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD7229	Phase 3
0.7438	Intermediate Similarity	NPD1465	Phase 2
0.7415	Intermediate Similarity	NPD411	Approved
0.7405	Intermediate Similarity	NPD7458	Discontinued
0.7403	Intermediate Similarity	NPD2309	Approved
0.7397	Intermediate Similarity	NPD4908	Phase 1
0.7383	Intermediate Similarity	NPD447	Suspended
0.7372	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD2353	Approved
0.7368	Intermediate Similarity	NPD1471	Phase 3
0.7365	Intermediate Similarity	NPD8032	Phase 2
0.7345	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD7003	Approved
0.7333	Intermediate Similarity	NPD5710	Approved
0.7333	Intermediate Similarity	NPD5711	Approved
0.733	Intermediate Similarity	NPD4360	Phase 2
0.733	Intermediate Similarity	NPD4363	Phase 3
0.7325	Intermediate Similarity	NPD5049	Phase 3
0.7315	Intermediate Similarity	NPD943	Approved
0.7308	Intermediate Similarity	NPD7390	Discontinued
0.7303	Intermediate Similarity	NPD5405	Approved
0.7303	Intermediate Similarity	NPD5404	Approved
0.7303	Intermediate Similarity	NPD5406	Approved
0.7303	Intermediate Similarity	NPD5408	Approved
0.7299	Intermediate Similarity	NPD4287	Approved
0.7297	Intermediate Similarity	NPD6798	Discontinued
0.7296	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD3887	Approved
0.7288	Intermediate Similarity	NPD4361	Phase 2
0.7288	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1610	Phase 2
0.7273	Intermediate Similarity	NPD7199	Phase 2
0.7273	Intermediate Similarity	NPD1281	Approved
0.7267	Intermediate Similarity	NPD6355	Discontinued
0.7246	Intermediate Similarity	NPD2403	Approved
0.7246	Intermediate Similarity	NPD1241	Discontinued
0.7241	Intermediate Similarity	NPD1876	Approved
0.7235	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD1548	Phase 1
0.7229	Intermediate Similarity	NPD6808	Phase 2
0.7215	Intermediate Similarity	NPD6273	Approved
0.72	Intermediate Similarity	NPD2979	Phase 3
0.7197	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD1164	Approved
0.719	Intermediate Similarity	NPD4476	Approved
0.719	Intermediate Similarity	NPD4477	Approved
0.7186	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD3764	Approved
0.7179	Intermediate Similarity	NPD2354	Approved
0.7161	Intermediate Similarity	NPD1652	Phase 2
0.7143	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6004	Phase 3
0.7143	Intermediate Similarity	NPD6002	Phase 3
0.7143	Intermediate Similarity	NPD6005	Phase 3
0.7143	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD1283	Approved
0.7114	Intermediate Similarity	NPD4625	Phase 3
0.7113	Intermediate Similarity	NPD9545	Approved
0.7113	Intermediate Similarity	NPD1894	Discontinued
0.7092	Intermediate Similarity	NPD9493	Approved
0.7091	Intermediate Similarity	NPD6971	Discontinued
0.7089	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5242	Approved
0.7081	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD2438	Suspended
0.707	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5691	Approved
0.7063	Intermediate Similarity	NPD1651	Approved
0.7055	Intermediate Similarity	NPD6280	Approved
0.7055	Intermediate Similarity	NPD6279	Approved
0.7047	Intermediate Similarity	NPD2614	Approved
0.7039	Intermediate Similarity	NPD4622	Approved
0.7039	Intermediate Similarity	NPD230	Phase 1
0.7039	Intermediate Similarity	NPD4618	Approved
0.7037	Intermediate Similarity	NPD9697	Approved
0.7034	Intermediate Similarity	NPD1611	Approved
0.7022	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD6233	Phase 2
0.7012	Intermediate Similarity	NPD8455	Phase 2

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