NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	434.17
Volume:	444.483
LogP:	5.544
LogD:	3.899
LogS:	-2.326
# Rotatable Bonds:	2
TPSA:	78.13
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.628
Synthetic Accessibility Score:	3.675
Fsp3:	0.346
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:	-4.981
MDCK Permeability:	2.060519727820065e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.033
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.054

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.054
Plasma Protein Binding (PPB):	98.5063247680664%
Volume Distribution (VD):	0.348
Pgp-substrate:	2.346346139907837%

ADMET: Metabolism

CYP1A2-inhibitor:	0.325
CYP1A2-substrate:	0.821
CYP2C19-inhibitor:	0.662
CYP2C19-substrate:	0.134
CYP2C9-inhibitor:	0.825
CYP2C9-substrate:	0.875
CYP2D6-inhibitor:	0.862
CYP2D6-substrate:	0.724
CYP3A4-inhibitor:	0.787
CYP3A4-substrate:	0.663

ADMET: Excretion

Clearance (CL):	3.056
Half-life (T1/2):	0.062

ADMET: Toxicity

hERG Blockers:	0.315
Human Hepatotoxicity (H-HT):	0.92
Drug-inuced Liver Injury (DILI):	0.264
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.776
Maximum Recommended Daily Dose:	0.891
Skin Sensitization:	0.064
Carcinogencity:	0.854
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.903

Download Data

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

Natural Product: NPC477530

Natural Product ID:	NPC477530
*Common Name:**	Mundulone
IUPAC Name:	3-hydroxy-7-(5-methoxy-2,2-dimethylchromen-6-yl)-2,2-dimethyl-3,4-dihydropyrano[3,2-g]chromen-6-one
Synonyms:	Mundulone
Standard InCHIKey:	KJTDZAHLWHEULN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C26H26O6/c1-25(2)9-8-16-19(31-25)7-6-15(24(16)29-5)18-13-30-21-12-20-14(10-17(21)23(18)28)11-22(27)26(3,4)32-20/h6-10,12-13,22,27H,11H2,1-5H3
SMILES:	CC1(C=CC2=C(O1)C=CC(=C2OC)C3=COC4=C(C3=O)C=C5CC(C(OC5=C4)(C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	4587968
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0001612] Isoflavans [CHEMONTID:0001827] Isoflavanones [CHEMONTID:0003526] 6-prenylated isoflavanones

*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
NPO10386	Mundulea chapelieri	Species	Fabaceae	Eukaryota	bark	an elevation of 850 m (171725? S; 484030? E), Toamasina, Madagascar	2002-JAN	PMID[15043430]
NPO10386	Mundulea chapelieri	Species	Fabaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15043430]
NPO10386	Mundulea chapelieri	Species	Fabaceae	Eukaryota	n.a.	flower	n.a.	PMID[15043430]
NPO10386	Mundulea chapelieri	Species	Fabaceae	Eukaryota	n.a.	bark	n.a.	PMID[15043430]
NPO10386	Mundulea chapelieri	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	1
Others	2
Potency	26

Activity Type	# Activity
Cell Line	1
Individual Protein	19
Others	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	13	ug/ml	PMID[15043430]
NPT442	Individual Protein	Ferritin light chain	Equus caballus	Potency	=	10000	nM	PubChem BioAssay data set
NPT282	Individual Protein	MAP kinase ERK2	Homo sapiens	Potency	=	3162.3	nM	PubChem BioAssay data set
NPT45	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 2	Homo sapiens	Potency	=	10000	nM	PubChem BioAssay data set
NPT282	Individual Protein	MAP kinase ERK2	Homo sapiens	Potency	=	12589.3	nM	PubChem BioAssay data set
NPT151	Individual Protein	15-hydroxyprostaglandin dehydrogenase [NAD+]	Homo sapiens	Potency	=	15848.9	nM	PubChem BioAssay data set
NPT539	Individual Protein	Cellular tumor antigen p53	Homo sapiens	Potency	=	25118.9	nM	PubChem BioAssay data set
NPT539	Individual Protein	Cellular tumor antigen p53	Homo sapiens	Potency	=	19952.6	nM	PubChem BioAssay data set
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	1122	nM	PubChem BioAssay data set
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	2511.9	nM	PubChem BioAssay data set
NPT61	Individual Protein	Beta-glucocerebrosidase	Homo sapiens	Potency	n.a.	5011.9	nM	PubChem BioAssay data set
NPT1139	Individual Protein	Arachidonate 15-lipoxygenase, type II	Homo sapiens	Potency	n.a.	3981.1	nM	PubChem BioAssay data set
NPT444	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency	n.a.	35481.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	=	3162.3	nM	PubChem BioAssay data set
NPT93	Individual Protein	Survival motor neuron protein	Homo sapiens	Potency	=	316.2	nM	PubChem BioAssay data set
NPT791	Individual Protein	Cruzipain	Trypanosoma cruzi	Potency	=	10000	nM	PubChem BioAssay data set
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	12589.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	=	70.8	nM	PubChem BioAssay data set
NPT888	Individual Protein	78 kDa glucose-regulated protein	Homo sapiens	Potency	n.a.	39810.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	20.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	46.1	nM	PubChem BioAssay data set
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	31.23	%	PMID[23571415]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	45.15	%	PMID[23571415]
NPT2	Others	Unspecified		Potency	n.a.	11220.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	17782.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	10000	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	2238.7	nM	PubChem BioAssay data set

☑ 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 NPC477530 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	410
0.1-0.2	1591
0.2-0.3	3623
0.3-0.4	9317
0.4-0.5	9614
0.5-0.6	3967
0.6-0.7	5905
0.7-0.8	4546
0.8-0.85	2661
0.85-0.9	962
0.9-0.95	99
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9664	High Similarity	NPC223701
0.9664	High Similarity	NPC88983
0.9664	High Similarity	NPC472583
0.9664	High Similarity	NPC469405
0.9664	High Similarity	NPC7989
0.96	High Similarity	NPC470681
0.953	High Similarity	NPC472420
0.953	High Similarity	NPC263384
0.953	High Similarity	NPC471676
0.953	High Similarity	NPC244577
0.953	High Similarity	NPC472422
0.947	High Similarity	NPC259710
0.947	High Similarity	NPC48579
0.947	High Similarity	NPC304207
0.947	High Similarity	NPC477958
0.947	High Similarity	NPC207809
0.947	High Similarity	NPC217706
0.9467	High Similarity	NPC150123
0.9467	High Similarity	NPC10807
0.9467	High Similarity	NPC161881
0.9467	High Similarity	NPC244583
0.9467	High Similarity	NPC475790
0.9467	High Similarity	NPC56232
0.9456	High Similarity	NPC474302
0.9404	High Similarity	NPC248793
0.9404	High Similarity	NPC112701
0.9404	High Similarity	NPC326592
0.9404	High Similarity	NPC180301
0.9404	High Similarity	NPC109594
0.94	High Similarity	NPC477897
0.94	High Similarity	NPC328740
0.94	High Similarity	NPC474021
0.94	High Similarity	NPC289774
0.94	High Similarity	NPC209846
0.94	High Similarity	NPC471677
0.94	High Similarity	NPC474023
0.9396	High Similarity	NPC5173
0.9351	High Similarity	NPC471976
0.9346	High Similarity	NPC78071
0.9342	High Similarity	NPC111341
0.9342	High Similarity	NPC476169
0.9342	High Similarity	NPC304745
0.9338	High Similarity	NPC476238
0.9338	High Similarity	NPC31627
0.9338	High Similarity	NPC243171
0.9338	High Similarity	NPC473996
0.9338	High Similarity	NPC171651
0.9338	High Similarity	NPC327269
0.9338	High Similarity	NPC35567
0.9338	High Similarity	NPC285623
0.9333	High Similarity	NPC177308
0.9333	High Similarity	NPC124478
0.9329	High Similarity	NPC6511
0.9329	High Similarity	NPC161191
0.9329	High Similarity	NPC266572
0.932	High Similarity	NPC59522
0.929	High Similarity	NPC3629
0.9286	High Similarity	NPC187792
0.9281	High Similarity	NPC208152
0.9281	High Similarity	NPC78492
0.9276	High Similarity	NPC311579
0.9276	High Similarity	NPC268193
0.9276	High Similarity	NPC293286
0.9276	High Similarity	NPC236756
0.9272	High Similarity	NPC278476
0.9272	High Similarity	NPC472423
0.9272	High Similarity	NPC319910
0.9272	High Similarity	NPC474772
0.9272	High Similarity	NPC471675
0.9272	High Similarity	NPC262038
0.9272	High Similarity	NPC262039
0.9272	High Similarity	NPC472580
0.9272	High Similarity	NPC472636
0.9272	High Similarity	NPC474744
0.9272	High Similarity	NPC254412
0.9267	High Similarity	NPC89442
0.9267	High Similarity	NPC472628
0.9262	High Similarity	NPC201731
0.9262	High Similarity	NPC472627
0.9262	High Similarity	NPC23728
0.9262	High Similarity	NPC237635
0.9262	High Similarity	NPC79469
0.9262	High Similarity	NPC24673
0.9262	High Similarity	NPC110303
0.9262	High Similarity	NPC222298
0.9262	High Similarity	NPC51070
0.9262	High Similarity	NPC473077
0.9262	High Similarity	NPC97716
0.9262	High Similarity	NPC104406
0.9262	High Similarity	NPC296998
0.9262	High Similarity	NPC85773
0.9257	High Similarity	NPC87486
0.9257	High Similarity	NPC179970
0.9257	High Similarity	NPC124780
0.9226	High Similarity	NPC475784
0.9211	High Similarity	NPC477957
0.9211	High Similarity	NPC210597
0.9211	High Similarity	NPC256141
0.9211	High Similarity	NPC217149
0.9211	High Similarity	NPC216035
0.9211	High Similarity	NPC138288
0.9205	High Similarity	NPC105136
0.9205	High Similarity	NPC472633
0.9205	High Similarity	NPC472421
0.9205	High Similarity	NPC29777
0.9205	High Similarity	NPC61258
0.9205	High Similarity	NPC471115
0.92	High Similarity	NPC160821
0.92	High Similarity	NPC10097
0.92	High Similarity	NPC132592
0.92	High Similarity	NPC189087
0.92	High Similarity	NPC321623
0.9195	High Similarity	NPC472629
0.9195	High Similarity	NPC67805
0.9195	High Similarity	NPC176229
0.9195	High Similarity	NPC142405
0.9195	High Similarity	NPC316769
0.9195	High Similarity	NPC246948
0.9195	High Similarity	NPC214774
0.9195	High Similarity	NPC111786
0.9195	High Similarity	NPC312973
0.9195	High Similarity	NPC20488
0.9195	High Similarity	NPC88964
0.9195	High Similarity	NPC301276
0.9195	High Similarity	NPC195621
0.9195	High Similarity	NPC267375
0.9195	High Similarity	NPC54577
0.9195	High Similarity	NPC475052
0.9195	High Similarity	NPC83357
0.9195	High Similarity	NPC470647
0.9184	High Similarity	NPC52576
0.9167	High Similarity	NPC97812
0.9167	High Similarity	NPC474038
0.9156	High Similarity	NPC10754
0.9156	High Similarity	NPC20530
0.9156	High Similarity	NPC45165
0.9156	High Similarity	NPC146636
0.9156	High Similarity	NPC215917
0.915	High Similarity	NPC203080
0.915	High Similarity	NPC100134
0.915	High Similarity	NPC20907
0.915	High Similarity	NPC244250
0.915	High Similarity	NPC209760
0.9145	High Similarity	NPC471229
0.9139	High Similarity	NPC164299
0.9139	High Similarity	NPC317492
0.9139	High Similarity	NPC139966
0.9139	High Similarity	NPC307052
0.9133	High Similarity	NPC470670
0.9133	High Similarity	NPC91902
0.9133	High Similarity	NPC473133
0.9133	High Similarity	NPC283234
0.9133	High Similarity	NPC47388
0.9128	High Similarity	NPC319752
0.9128	High Similarity	NPC209040
0.9128	High Similarity	NPC234629
0.9128	High Similarity	NPC224714
0.9128	High Similarity	NPC470890
0.9128	High Similarity	NPC311741
0.9122	High Similarity	NPC147145
0.9116	High Similarity	NPC472409
0.9108	High Similarity	NPC44947
0.9108	High Similarity	NPC474034
0.9108	High Similarity	NPC474033
0.9103	High Similarity	NPC192686
0.9103	High Similarity	NPC119209
0.9103	High Similarity	NPC118256
0.9097	High Similarity	NPC473272
0.9097	High Similarity	NPC284820
0.9091	High Similarity	NPC92395
0.9091	High Similarity	NPC471116
0.9091	High Similarity	NPC87404
0.9085	High Similarity	NPC40033
0.9079	High Similarity	NPC188403
0.9079	High Similarity	NPC180351
0.9079	High Similarity	NPC267117
0.9073	High Similarity	NPC168085
0.9073	High Similarity	NPC39195
0.9073	High Similarity	NPC296869
0.9073	High Similarity	NPC244407
0.9067	High Similarity	NPC474161
0.9067	High Similarity	NPC476088
0.906	High Similarity	NPC38219
0.906	High Similarity	NPC310130
0.906	High Similarity	NPC221432
0.906	High Similarity	NPC475705
0.906	High Similarity	NPC175504
0.906	High Similarity	NPC117836
0.906	High Similarity	NPC91560
0.906	High Similarity	NPC166138
0.906	High Similarity	NPC18585
0.906	High Similarity	NPC106985
0.906	High Similarity	NPC316816
0.906	High Similarity	NPC255133
0.906	High Similarity	NPC214166
0.906	High Similarity	NPC257097
0.906	High Similarity	NPC39329
0.906	High Similarity	NPC478086
0.906	High Similarity	NPC143896
0.906	High Similarity	NPC68104

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 NPC477530 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	358
0.1-0.2	906
0.2-0.3	1683
0.3-0.4	2678
0.4-0.5	1977
0.5-0.6	1027
0.6-0.7	346
0.7-0.8	124
0.8-0.85	42
0.85-0.9	8
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9333	High Similarity	NPD4380	Phase 2
0.9026	High Similarity	NPD7096	Clinical (unspecified phase)
0.8974	High Similarity	NPD4381	Clinical (unspecified phase)
0.8903	High Similarity	NPD2393	Clinical (unspecified phase)
0.8874	High Similarity	NPD4378	Clinical (unspecified phase)
0.8854	High Similarity	NPD7075	Discontinued
0.8844	High Similarity	NPD2796	Approved
0.8839	High Similarity	NPD6801	Discontinued
0.8827	High Similarity	NPD7804	Clinical (unspecified phase)
0.875	High Similarity	NPD7410	Clinical (unspecified phase)
0.8725	High Similarity	NPD1549	Phase 2
0.8718	High Similarity	NPD1934	Approved
0.8658	High Similarity	NPD1550	Clinical (unspecified phase)
0.8658	High Similarity	NPD1552	Clinical (unspecified phase)
0.8654	High Similarity	NPD7411	Suspended
0.8642	High Similarity	NPD6166	Phase 2
0.8642	High Similarity	NPD6167	Clinical (unspecified phase)
0.8642	High Similarity	NPD6168	Clinical (unspecified phase)
0.8625	High Similarity	NPD5494	Approved
0.8608	High Similarity	NPD8443	Clinical (unspecified phase)
0.8562	High Similarity	NPD6799	Approved
0.8544	High Similarity	NPD2801	Approved
0.8544	High Similarity	NPD7819	Suspended
0.8523	High Similarity	NPD1510	Phase 2
0.8516	High Similarity	NPD5403	Approved
0.8506	High Similarity	NPD5401	Approved
0.8491	Intermediate Similarity	NPD5402	Approved
0.8485	Intermediate Similarity	NPD7054	Approved
0.8434	Intermediate Similarity	NPD7074	Phase 3
0.8434	Intermediate Similarity	NPD7472	Approved
0.8424	Intermediate Similarity	NPD3818	Discontinued
0.8383	Intermediate Similarity	NPD6797	Phase 2
0.8375	Intermediate Similarity	NPD3817	Phase 2
0.8354	Intermediate Similarity	NPD6599	Discontinued
0.8344	Intermediate Similarity	NPD6959	Discontinued
0.8333	Intermediate Similarity	NPD7251	Discontinued
0.8323	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD1511	Approved
0.8323	Intermediate Similarity	NPD3882	Suspended
0.8303	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8284	Intermediate Similarity	NPD7808	Phase 3
0.8255	Intermediate Similarity	NPD1240	Approved
0.8225	Intermediate Similarity	NPD6559	Discontinued
0.8217	Intermediate Similarity	NPD1512	Approved
0.8176	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD920	Approved
0.8155	Intermediate Similarity	NPD5844	Phase 1
0.8146	Intermediate Similarity	NPD1607	Approved
0.8098	Intermediate Similarity	NPD7768	Phase 2
0.8065	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD3749	Approved
0.8038	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD3750	Approved
0.8013	Intermediate Similarity	NPD4628	Phase 3
0.8	Intermediate Similarity	NPD2313	Discontinued
0.7949	Intermediate Similarity	NPD2800	Approved
0.7949	Intermediate Similarity	NPD1243	Approved
0.7922	Intermediate Similarity	NPD3748	Approved
0.7922	Intermediate Similarity	NPD2799	Discontinued
0.7911	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD1247	Approved
0.7882	Intermediate Similarity	NPD3751	Discontinued
0.7881	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD6232	Discontinued
0.7857	Intermediate Similarity	NPD3787	Discontinued
0.7843	Intermediate Similarity	NPD5124	Phase 1
0.7843	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD7473	Discontinued
0.7785	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD919	Approved
0.7771	Intermediate Similarity	NPD2424	Discontinued
0.7759	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD1551	Phase 2
0.7756	Intermediate Similarity	NPD2935	Discontinued
0.7755	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD5953	Discontinued
0.7742	Intermediate Similarity	NPD7584	Approved
0.7735	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD7286	Phase 2
0.7722	Intermediate Similarity	NPD4360	Phase 2
0.7722	Intermediate Similarity	NPD4363	Phase 3
0.7714	Intermediate Similarity	NPD8312	Approved
0.7714	Intermediate Similarity	NPD8313	Approved
0.7707	Intermediate Similarity	NPD2346	Discontinued
0.7702	Intermediate Similarity	NPD2533	Approved
0.7702	Intermediate Similarity	NPD2534	Approved
0.7702	Intermediate Similarity	NPD2532	Approved
0.7692	Intermediate Similarity	NPD7033	Discontinued
0.7658	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD1465	Phase 2
0.7651	Intermediate Similarity	NPD8455	Phase 2
0.7647	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD3226	Approved
0.7609	Intermediate Similarity	NPD6777	Approved
0.7609	Intermediate Similarity	NPD6778	Approved
0.7609	Intermediate Similarity	NPD6779	Approved
0.7609	Intermediate Similarity	NPD6780	Approved
0.7609	Intermediate Similarity	NPD6781	Approved
0.7609	Intermediate Similarity	NPD6776	Approved
0.7609	Intermediate Similarity	NPD6782	Approved
0.7602	Intermediate Similarity	NPD3926	Phase 2
0.7595	Intermediate Similarity	NPD2344	Approved
0.759	Intermediate Similarity	NPD6844	Discontinued
0.7564	Intermediate Similarity	NPD6651	Approved
0.7548	Intermediate Similarity	NPD943	Approved
0.7548	Intermediate Similarity	NPD1613	Approved
0.7548	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6832	Phase 2
0.7516	Intermediate Similarity	NPD4908	Phase 1
0.7515	Intermediate Similarity	NPD7458	Discontinued
0.75	Intermediate Similarity	NPD2798	Approved
0.75	Intermediate Similarity	NPD1652	Phase 2
0.7487	Intermediate Similarity	NPD7435	Discontinued
0.7486	Intermediate Similarity	NPD8150	Discontinued
0.7486	Intermediate Similarity	NPD8434	Phase 2
0.7468	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD3823	Discontinued
0.7423	Intermediate Similarity	NPD7390	Discontinued
0.7421	Intermediate Similarity	NPD6099	Approved
0.7421	Intermediate Similarity	NPD6100	Approved
0.7419	Intermediate Similarity	NPD6798	Discontinued
0.741	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD2309	Approved
0.7403	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD7698	Approved
0.7394	Intermediate Similarity	NPD7696	Phase 3
0.7394	Intermediate Similarity	NPD7697	Approved
0.7394	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD1933	Approved
0.7382	Intermediate Similarity	NPD8151	Discontinued
0.7378	Intermediate Similarity	NPD4662	Approved
0.7378	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD4661	Approved
0.7368	Intermediate Similarity	NPD7583	Approved
0.7358	Intermediate Similarity	NPD4308	Phase 3
0.7354	Intermediate Similarity	NPD7870	Phase 2
0.7354	Intermediate Similarity	NPD7871	Phase 2
0.7346	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD6823	Phase 2
0.7337	Intermediate Similarity	NPD6534	Approved
0.7337	Intermediate Similarity	NPD6535	Approved
0.733	Intermediate Similarity	NPD7585	Approved
0.733	Intermediate Similarity	NPD7701	Phase 2
0.7326	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD5889	Approved
0.7321	Intermediate Similarity	NPD5890	Approved
0.732	Intermediate Similarity	NPD1203	Approved
0.7308	Intermediate Similarity	NPD3268	Approved
0.7306	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD7783	Phase 2
0.7297	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD4361	Phase 2
0.7296	Intermediate Similarity	NPD7097	Phase 1
0.729	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD1610	Phase 2
0.7283	Intermediate Similarity	NPD7199	Phase 2
0.7278	Intermediate Similarity	NPD230	Phase 1
0.7278	Intermediate Similarity	NPD6355	Discontinued
0.7278	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD447	Suspended
0.7267	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD6585	Discontinued
0.7261	Intermediate Similarity	NPD6233	Phase 2
0.7257	Intermediate Similarity	NPD2403	Approved
0.7255	Intermediate Similarity	NPD3225	Approved
0.7254	Intermediate Similarity	NPD7874	Approved
0.7254	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD1548	Phase 1
0.7244	Intermediate Similarity	NPD3027	Phase 3
0.7241	Intermediate Similarity	NPD7229	Phase 3
0.7241	Intermediate Similarity	NPD5710	Approved
0.7241	Intermediate Similarity	NPD5711	Approved
0.7238	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD9717	Approved
0.7235	Intermediate Similarity	NPD5761	Phase 2
0.7235	Intermediate Similarity	NPD5760	Phase 2
0.7229	Intermediate Similarity	NPD5049	Phase 3
0.7226	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7700	Phase 2
0.7219	Intermediate Similarity	NPD7699	Phase 2
0.7216	Intermediate Similarity	NPD7801	Approved
0.7215	Intermediate Similarity	NPD4307	Phase 2
0.7208	Intermediate Similarity	NPD2797	Approved
0.7207	Intermediate Similarity	NPD7685	Pre-registration
0.7198	Intermediate Similarity	NPD3863	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD3887	Approved
0.7195	Intermediate Similarity	NPD6190	Approved
0.7195	Intermediate Similarity	NPD2354	Approved
0.7193	Intermediate Similarity	NPD4288	Approved
0.7188	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4536	Approved
0.7188	Intermediate Similarity	NPD4538	Approved
0.7181	Intermediate Similarity	NPD8285	Discontinued
0.7178	Intermediate Similarity	NPD2654	Approved
0.7178	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD37	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