NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	244.07
Volume:	244.373
LogP:	3.374
LogD:	2.57
LogS:	-3.277
# Rotatable Bonds:	0
TPSA:	59.67
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.774
Synthetic Accessibility Score:	3.054
Fsp3:	0.214
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.663
MDCK Permeability:	2.8643242330872454e-05
Pgp-inhibitor:	0.024
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.013

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.065
Plasma Protein Binding (PPB):	94.92514038085938%
Volume Distribution (VD):	0.728
Pgp-substrate:	7.219175338745117%

ADMET: Metabolism

CYP1A2-inhibitor:	0.956
CYP1A2-substrate:	0.69
CYP2C19-inhibitor:	0.569
CYP2C19-substrate:	0.291
CYP2C9-inhibitor:	0.701
CYP2C9-substrate:	0.89
CYP2D6-inhibitor:	0.852
CYP2D6-substrate:	0.445
CYP3A4-inhibitor:	0.604
CYP3A4-substrate:	0.198

ADMET: Excretion

Clearance (CL):	2.123
Half-life (T1/2):	0.445

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.478
Drug-inuced Liver Injury (DILI):	0.694
AMES Toxicity:	0.106
Rat Oral Acute Toxicity:	0.697
Maximum Recommended Daily Dose:	0.333
Skin Sensitization:	0.738
Carcinogencity:	0.871
Eye Corrosion:	0.004
Eye Irritation:	0.511
Respiratory Toxicity:	0.907

Download Data

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

Natural Product: NPC473076

Natural Product ID:	NPC473076
*Common Name:**	5-Hydroxy-2,2-Dimethyl-2H,6H-Benzodipyran-6-One
IUPAC Name:	5-hydroxy-2,2-dimethylpyrano[3,2-g]chromen-6-one
Synonyms:
Standard InCHIKey:	MMGLCBWVIVENBV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H12O4/c1-14(2)5-3-8-10(18-14)7-11-12(13(8)16)9(15)4-6-17-11/h3-7,16H,1-2H3
SMILES:	O=c1ccoc2c1c(O)c1c(c2)OC(C=C1)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3609149
PubChem CID:	13545810
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0003543] Pyranochromenes

*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
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[15787460]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15787460]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16203143]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16919944]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	root bark	n.a.	n.a.	PMID[17608532]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17950599]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	fruits	n.a.	n.a.	PMID[19113968]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	Roots	n.a.	n.a.	PMID[19191562]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[19280148]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19285413]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19660948]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[21319773]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	Roots	n.a.	n.a.	PMID[25322455]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	root barks	purchased from the local herbal market, Chungbuk, Korea	2012-JUL	PMID[26227773]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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	1

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1120	Individual Protein	Pancreatic triacylglycerol lipase	Sus scrofa	Inhibition	=	27.5	%	PMID[564899]
NPT1120	Individual Protein	Pancreatic triacylglycerol lipase	Sus scrofa	IC50	>	100000.0	nM	PMID[564899]

☑ 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 NPC473076 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	377
0.1-0.2	1829
0.2-0.3	4861
0.3-0.4	12208
0.4-0.5	5753
0.5-0.6	4630
0.6-0.7	5773
0.7-0.8	4192
0.8-0.85	1861
0.85-0.9	929
0.9-0.95	281
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9565	High Similarity	NPC255133
0.9565	High Similarity	NPC242100
0.9559	High Similarity	NPC23257
0.9552	High Similarity	NPC60667
0.9552	High Similarity	NPC151113
0.95	High Similarity	NPC79469
0.95	High Similarity	NPC237635
0.95	High Similarity	NPC24673
0.95	High Similarity	NPC104406
0.95	High Similarity	NPC97716
0.95	High Similarity	NPC201731
0.9493	High Similarity	NPC11561
0.9493	High Similarity	NPC226636
0.9493	High Similarity	NPC162476
0.9489	High Similarity	NPC471587
0.9478	High Similarity	NPC125920
0.9433	High Similarity	NPC6511
0.9433	High Similarity	NPC266572
0.942	High Similarity	NPC118840
0.942	High Similarity	NPC205006
0.942	High Similarity	NPC147688
0.942	High Similarity	NPC110969
0.942	High Similarity	NPC103362
0.942	High Similarity	NPC156590
0.942	High Similarity	NPC64908
0.942	High Similarity	NPC3188
0.9416	High Similarity	NPC18260
0.9416	High Similarity	NPC78913
0.9403	High Similarity	NPC108113
0.9403	High Similarity	NPC93756
0.9362	High Similarity	NPC110303
0.9362	High Similarity	NPC23728
0.9357	High Similarity	NPC209040
0.9357	High Similarity	NPC319752
0.9357	High Similarity	NPC234629
0.9357	High Similarity	NPC311741
0.9353	High Similarity	NPC214236
0.9353	High Similarity	NPC299080
0.9353	High Similarity	NPC59739
0.9353	High Similarity	NPC217083
0.9353	High Similarity	NPC78803
0.9353	High Similarity	NPC62840
0.9353	High Similarity	NPC293852
0.9348	High Similarity	NPC475680
0.9348	High Similarity	NPC270883
0.9348	High Similarity	NPC305355
0.9348	High Similarity	NPC235239
0.9348	High Similarity	NPC172986
0.9348	High Similarity	NPC241100
0.9348	High Similarity	NPC261227
0.9348	High Similarity	NPC150522
0.9348	High Similarity	NPC159275
0.9343	High Similarity	NPC470668
0.9343	High Similarity	NPC131130
0.9343	High Similarity	NPC470669
0.9343	High Similarity	NPC201395
0.9338	High Similarity	NPC174999
0.9323	High Similarity	NPC250057
0.9301	High Similarity	NPC188403
0.9296	High Similarity	NPC132592
0.9296	High Similarity	NPC321623
0.9296	High Similarity	NPC211811
0.9296	High Similarity	NPC161191
0.9296	High Similarity	NPC160821
0.9296	High Similarity	NPC189087
0.9291	High Similarity	NPC54577
0.9291	High Similarity	NPC111786
0.9291	High Similarity	NPC83357
0.9291	High Similarity	NPC470647
0.9291	High Similarity	NPC474161
0.9291	High Similarity	NPC67805
0.9291	High Similarity	NPC88964
0.9291	High Similarity	NPC246948
0.9291	High Similarity	NPC301276
0.9291	High Similarity	NPC476088
0.9291	High Similarity	NPC475052
0.9291	High Similarity	NPC195621
0.9291	High Similarity	NPC142405
0.9291	High Similarity	NPC214774
0.9291	High Similarity	NPC267375
0.9291	High Similarity	NPC176229
0.9291	High Similarity	NPC20488
0.9291	High Similarity	NPC312973
0.9286	High Similarity	NPC68104
0.9286	High Similarity	NPC166138
0.9286	High Similarity	NPC316816
0.9286	High Similarity	NPC18585
0.9286	High Similarity	NPC75049
0.9286	High Similarity	NPC149026
0.9286	High Similarity	NPC91560
0.9286	High Similarity	NPC214166
0.9286	High Similarity	NPC257097
0.9286	High Similarity	NPC169591
0.9286	High Similarity	NPC38219
0.9286	High Similarity	NPC39329
0.9286	High Similarity	NPC143896
0.9286	High Similarity	NPC175504
0.9286	High Similarity	NPC150408
0.9286	High Similarity	NPC310130
0.9286	High Similarity	NPC478086
0.9286	High Similarity	NPC221432
0.9286	High Similarity	NPC164980
0.9286	High Similarity	NPC106985
0.9281	High Similarity	NPC324386
0.9281	High Similarity	NPC4743
0.9281	High Similarity	NPC213322
0.9281	High Similarity	NPC282300
0.9281	High Similarity	NPC312391
0.9275	High Similarity	NPC139554
0.9275	High Similarity	NPC53181
0.9275	High Similarity	NPC217186
0.9275	High Similarity	NPC96565
0.9275	High Similarity	NPC216978
0.9275	High Similarity	NPC55018
0.9275	High Similarity	NPC471697
0.9275	High Similarity	NPC295384
0.9275	High Similarity	NPC301217
0.9275	High Similarity	NPC220062
0.9275	High Similarity	NPC303633
0.927	High Similarity	NPC266597
0.927	High Similarity	NPC250266
0.9265	High Similarity	NPC101752
0.9265	High Similarity	NPC46869
0.9259	High Similarity	NPC223457
0.9254	High Similarity	NPC31872
0.9254	High Similarity	NPC473584
0.9254	High Similarity	NPC475589
0.9231	High Similarity	NPC5173
0.9225	High Similarity	NPC283234
0.9225	High Similarity	NPC473077
0.9225	High Similarity	NPC296998
0.922	High Similarity	NPC236766
0.922	High Similarity	NPC131579
0.922	High Similarity	NPC197252
0.922	High Similarity	NPC473015
0.922	High Similarity	NPC469953
0.922	High Similarity	NPC131568
0.922	High Similarity	NPC473013
0.9214	High Similarity	NPC144499
0.9214	High Similarity	NPC166934
0.9214	High Similarity	NPC223500
0.9214	High Similarity	NPC324134
0.9214	High Similarity	NPC1089
0.9214	High Similarity	NPC37496
0.9214	High Similarity	NPC227579
0.9214	High Similarity	NPC32739
0.9214	High Similarity	NPC324436
0.9214	High Similarity	NPC328164
0.9214	High Similarity	NPC40833
0.9214	High Similarity	NPC306829
0.9214	High Similarity	NPC194432
0.9214	High Similarity	NPC265040
0.9214	High Similarity	NPC76338
0.9214	High Similarity	NPC125855
0.9214	High Similarity	NPC296917
0.9214	High Similarity	NPC228504
0.9214	High Similarity	NPC148757
0.9214	High Similarity	NPC78
0.9214	High Similarity	NPC66515
0.9214	High Similarity	NPC166482
0.9214	High Similarity	NPC147145
0.9214	High Similarity	NPC177354
0.9214	High Similarity	NPC10937
0.9214	High Similarity	NPC220998
0.9214	High Similarity	NPC76372
0.9214	High Similarity	NPC64915
0.9214	High Similarity	NPC182852
0.9214	High Similarity	NPC167624
0.9214	High Similarity	NPC107572
0.9214	High Similarity	NPC161506
0.9209	High Similarity	NPC48624
0.9209	High Similarity	NPC259166
0.9209	High Similarity	NPC144118
0.9209	High Similarity	NPC80962
0.9209	High Similarity	NPC326109
0.9209	High Similarity	NPC101366
0.9209	High Similarity	NPC215311
0.9209	High Similarity	NPC69769
0.9209	High Similarity	NPC172250
0.9209	High Similarity	NPC219917
0.9209	High Similarity	NPC204985
0.9209	High Similarity	NPC213659
0.9203	High Similarity	NPC472460
0.9203	High Similarity	NPC280284
0.9203	High Similarity	NPC188947
0.9203	High Similarity	NPC329225
0.9203	High Similarity	NPC272844
0.9203	High Similarity	NPC99333
0.9203	High Similarity	NPC254168
0.9203	High Similarity	NPC147686
0.9203	High Similarity	NPC124269
0.9203	High Similarity	NPC248995
0.9197	High Similarity	NPC231772
0.9197	High Similarity	NPC47815
0.9197	High Similarity	NPC29353
0.9197	High Similarity	NPC194281
0.9197	High Similarity	NPC124784
0.9197	High Similarity	NPC234133
0.9197	High Similarity	NPC156910
0.9197	High Similarity	NPC473887

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 NPC473076 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	356
0.1-0.2	1031
0.2-0.3	1658
0.3-0.4	2754
0.4-0.5	1831
0.5-0.6	1064
0.6-0.7	310
0.7-0.8	105
0.8-0.85	27
0.85-0.9	13
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9203	High Similarity	NPD1549	Phase 2
0.913	High Similarity	NPD1550	Clinical (unspecified phase)
0.913	High Similarity	NPD1552	Clinical (unspecified phase)
0.9124	High Similarity	NPD1510	Phase 2
0.9085	High Similarity	NPD4378	Clinical (unspecified phase)
0.9085	High Similarity	NPD7410	Clinical (unspecified phase)
0.8971	High Similarity	NPD1240	Approved
0.8841	High Similarity	NPD1607	Approved
0.8786	High Similarity	NPD2796	Approved
0.8716	High Similarity	NPD7411	Suspended
0.8658	High Similarity	NPD6801	Discontinued
0.8649	High Similarity	NPD4380	Phase 2
0.86	High Similarity	NPD2393	Clinical (unspecified phase)
0.8553	High Similarity	NPD7075	Discontinued
0.8543	High Similarity	NPD8443	Clinical (unspecified phase)
0.8493	Intermediate Similarity	NPD1511	Approved
0.8477	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8477	Intermediate Similarity	NPD7819	Suspended
0.8472	Intermediate Similarity	NPD2800	Approved
0.8446	Intermediate Similarity	NPD920	Approved
0.8411	Intermediate Similarity	NPD1934	Approved
0.8403	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8378	Intermediate Similarity	NPD1512	Approved
0.8367	Intermediate Similarity	NPD6799	Approved
0.8345	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8345	Intermediate Similarity	NPD1243	Approved
0.8312	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.831	Intermediate Similarity	NPD6651	Approved
0.8299	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8288	Intermediate Similarity	NPD3750	Approved
0.8264	Intermediate Similarity	NPD1551	Phase 2
0.8247	Intermediate Similarity	NPD7768	Phase 2
0.8235	Intermediate Similarity	NPD2801	Approved
0.8228	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD6599	Discontinued
0.8153	Intermediate Similarity	NPD6959	Discontinued
0.8129	Intermediate Similarity	NPD3882	Suspended
0.8079	Intermediate Similarity	NPD5403	Approved
0.8077	Intermediate Similarity	NPD3749	Approved
0.8075	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD5401	Approved
0.8028	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7971	Intermediate Similarity	NPD9717	Approved
0.7963	Intermediate Similarity	NPD7286	Phase 2
0.7949	Intermediate Similarity	NPD3817	Phase 2
0.7947	Intermediate Similarity	NPD2534	Approved
0.7947	Intermediate Similarity	NPD2532	Approved
0.7947	Intermediate Similarity	NPD2533	Approved
0.7945	Intermediate Similarity	NPD3748	Approved
0.7929	Intermediate Similarity	NPD1203	Approved
0.7911	Intermediate Similarity	NPD919	Approved
0.7902	Intermediate Similarity	NPD2313	Discontinued
0.7901	Intermediate Similarity	NPD3818	Discontinued
0.7899	Intermediate Similarity	NPD422	Phase 1
0.7899	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD2935	Discontinued
0.7888	Intermediate Similarity	NPD6166	Phase 2
0.7888	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7868	Intermediate Similarity	NPD1548	Phase 1
0.7866	Intermediate Similarity	NPD5953	Discontinued
0.7862	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD5494	Approved
0.7862	Intermediate Similarity	NPD5124	Phase 1
0.7838	Intermediate Similarity	NPD2344	Approved
0.7823	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD2799	Discontinued
0.7812	Intermediate Similarity	NPD1247	Approved
0.7744	Intermediate Similarity	NPD7054	Approved
0.7737	Intermediate Similarity	NPD9545	Approved
0.7722	Intermediate Similarity	NPD5402	Approved
0.7711	Intermediate Similarity	NPD6559	Discontinued
0.7703	Intermediate Similarity	NPD7033	Discontinued
0.7697	Intermediate Similarity	NPD7472	Approved
0.7697	Intermediate Similarity	NPD7074	Phase 3
0.7697	Intermediate Similarity	NPD1729	Discontinued
0.7682	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD943	Approved
0.7655	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD6232	Discontinued
0.7651	Intermediate Similarity	NPD6100	Approved
0.7651	Intermediate Similarity	NPD6099	Approved
0.7651	Intermediate Similarity	NPD6797	Phase 2
0.7643	Intermediate Similarity	NPD1610	Phase 2
0.7639	Intermediate Similarity	NPD6832	Phase 2
0.7632	Intermediate Similarity	NPD2309	Approved
0.763	Intermediate Similarity	NPD1241	Discontinued
0.7628	Intermediate Similarity	NPD3226	Approved
0.7622	Intermediate Similarity	NPD7473	Discontinued
0.7605	Intermediate Similarity	NPD7251	Discontinued
0.7591	Intermediate Similarity	NPD9493	Approved
0.7584	Intermediate Similarity	NPD4308	Phase 3
0.7566	Intermediate Similarity	NPD4628	Phase 3
0.756	Intermediate Similarity	NPD7808	Phase 3
0.7534	Intermediate Similarity	NPD1296	Phase 2
0.7534	Intermediate Similarity	NPD3268	Approved
0.753	Intermediate Similarity	NPD5844	Phase 1
0.7517	Intermediate Similarity	NPD4908	Phase 1
0.75	Intermediate Similarity	NPD1019	Discontinued
0.75	Intermediate Similarity	NPD2654	Approved
0.75	Intermediate Similarity	NPD2798	Approved
0.75	Intermediate Similarity	NPD230	Phase 1
0.7483	Intermediate Similarity	NPD3225	Approved
0.7483	Intermediate Similarity	NPD2346	Discontinued
0.7456	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD1465	Phase 2
0.7431	Intermediate Similarity	NPD2797	Approved
0.7429	Intermediate Similarity	NPD4360	Phase 2
0.7429	Intermediate Similarity	NPD4363	Phase 3
0.7415	Intermediate Similarity	NPD411	Approved
0.7396	Intermediate Similarity	NPD6104	Discontinued
0.7386	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4361	Phase 2
0.7383	Intermediate Similarity	NPD447	Suspended
0.7333	Intermediate Similarity	NPD5710	Approved
0.7333	Intermediate Similarity	NPD5711	Approved
0.7315	Intermediate Similarity	NPD4307	Phase 2
0.7312	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD3267	Approved
0.731	Intermediate Similarity	NPD3266	Approved
0.7308	Intermediate Similarity	NPD7390	Discontinued
0.7289	Intermediate Similarity	NPD3926	Phase 2
0.7284	Intermediate Similarity	NPD4288	Approved
0.7267	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1933	Approved
0.7237	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD4625	Phase 3
0.7222	Intermediate Similarity	NPD3972	Approved
0.7222	Intermediate Similarity	NPD1608	Approved
0.7205	Intermediate Similarity	NPD5889	Approved
0.7205	Intermediate Similarity	NPD5890	Approved
0.72	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1613	Approved
0.7192	Intermediate Similarity	NPD1164	Approved
0.7192	Intermediate Similarity	NPD1470	Approved
0.7188	Intermediate Similarity	NPD7458	Discontinued
0.7181	Intermediate Similarity	NPD3764	Approved
0.7181	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD7584	Approved
0.7172	Intermediate Similarity	NPD4749	Approved
0.717	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD1652	Phase 2
0.7153	Intermediate Similarity	NPD1201	Approved
0.7143	Intermediate Similarity	NPD2403	Approved
0.7143	Intermediate Similarity	NPD1471	Phase 3
0.7143	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6585	Discontinued
0.7127	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD4287	Approved
0.7097	Intermediate Similarity	NPD2424	Discontinued
0.7095	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD9494	Approved
0.7086	Intermediate Similarity	NPD3142	Approved
0.7086	Intermediate Similarity	NPD3140	Approved
0.7081	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD2296	Approved
0.707	Intermediate Similarity	NPD2354	Approved
0.7067	Intermediate Similarity	NPD6798	Discontinued
0.7063	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3751	Discontinued
0.7044	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD7229	Phase 3
0.7014	Intermediate Similarity	NPD17	Approved
0.7012	Intermediate Similarity	NPD5761	Phase 2
0.7012	Intermediate Similarity	NPD5760	Phase 2
0.7007	Intermediate Similarity	NPD74	Approved
0.7007	Intermediate Similarity	NPD9266	Approved
0.7006	Intermediate Similarity	NPD7003	Approved
0.7	Intermediate Similarity	NPD5049	Phase 3
0.6986	Remote Similarity	NPD1481	Phase 2
0.6968	Remote Similarity	NPD5408	Approved
0.6968	Remote Similarity	NPD5406	Approved
0.6968	Remote Similarity	NPD5404	Approved
0.6968	Remote Similarity	NPD5405	Approved
0.6962	Remote Similarity	NPD3887	Approved
0.6959	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD7577	Discontinued
0.6951	Remote Similarity	NPD6844	Discontinued
0.6947	Remote Similarity	NPD4377	Discontinued
0.6937	Remote Similarity	NPD4662	Approved
0.6937	Remote Similarity	NPD4661	Approved
0.6934	Remote Similarity	NPD9263	Approved
0.6934	Remote Similarity	NPD9267	Approved
0.6934	Remote Similarity	NPD9264	Approved
0.6934	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6005	Phase 3
0.6923	Remote Similarity	NPD6002	Phase 3
0.6923	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2353	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