NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	194.06
Volume:	189.018
LogP:	2.393
LogD:	1.896
LogS:	-2.142
# Rotatable Bonds:	0
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.609
Synthetic Accessibility Score:	2.934
Fsp3:	0.3
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.697
MDCK Permeability:	2.0688392396550626e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.544

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.144
Plasma Protein Binding (PPB):	81.11935424804688%
Volume Distribution (VD):	0.788
Pgp-substrate:	18.164981842041016%

ADMET: Metabolism

CYP1A2-inhibitor:	0.909
CYP1A2-substrate:	0.132
CYP2C19-inhibitor:	0.101
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.111
CYP2C9-substrate:	0.862
CYP2D6-inhibitor:	0.753
CYP2D6-substrate:	0.43
CYP3A4-inhibitor:	0.357
CYP3A4-substrate:	0.144

ADMET: Excretion

Clearance (CL):	15.81
Half-life (T1/2):	0.844

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.142
Drug-inuced Liver Injury (DILI):	0.544
AMES Toxicity:	0.055
Rat Oral Acute Toxicity:	0.054
Maximum Recommended Daily Dose:	0.721
Skin Sensitization:	0.592
Carcinogencity:	0.224
Eye Corrosion:	0.389
Eye Irritation:	0.969
Respiratory Toxicity:	0.629

Download Data

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

Natural Product: NPC235115

Natural Product ID:	NPC235115
*Common Name:**	(+)-6-Hydroxymellein
IUPAC Name:	(3S)-6,8-dihydroxy-3-methyl-3,4-dihydroisochromen-1-one
Synonyms:	(+)-6-Hydroxymellein
Standard InCHIKey:	DHLPMLVSBRRUGA-YFKPBYRVSA-N
Standard InCHI:	InChI=1S/C10H10O4/c1-5-2-6-3-7(11)4-8(12)9(6)10(13)14-5/h3-5,11-12H,2H2,1H3/t5-/m0/s1
SMILES:	C[C@@H]1OC(=O)c2c(C1)cc(cc2O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL446047
PubChem CID:	14353462
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001248] Hydroxybenzoic acid derivatives

*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
NPO25302	Viola philippica	Species	Violaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14519932]
NPO487	Tabebuia avellanedae	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17950604]
NPO487	Tabebuia avellanedae	Species	Bignoniaceae	Eukaryota	n.a.	bark	n.a.	PMID[17950604]
NPO487	Tabebuia avellanedae	Species	Bignoniaceae	Eukaryota	n.a.	Brazilian	n.a.	PMID[19674905]
NPO28287	Magnaporthe oryzae	Species	Magnaporthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26258762]
NPO487	Tabebuia avellanedae	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32044231]
NPO25302	Viola philippica	Species	Violaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25302	Viola philippica	Species	Violaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6773	Bryoria implexa	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25302	Viola philippica	Species	Violaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12083	Hydnellum zonatum	Species	Thelephoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO487	Tabebuia avellanedae	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28287	Magnaporthe oryzae	Species	Magnaporthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3641	Polyporus tuberaster	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3751	Orthantha lutea	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO16391	Protea neriifolia	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO318	Glycosmis trichanthera	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4567	Senecio chrysocoma	Species	Asteraceae	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
Others	12

Activity Type	# Activity
Organism	12

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2231	Organism	Cornus florida	Cornus florida	Activity	=	7.0	mm2	PMID[568662]
NPT2231	Organism	Cornus florida	Cornus florida	Activity	=	14.0	mm2	PMID[568662]
NPT2231	Organism	Cornus florida	Cornus florida	Activity	=	10.0	mm2	PMID[568662]
NPT2232	Organism	Senna obtusifolia	Senna obtusifolia	Activity	=	20.0	mm2	PMID[568662]
NPT2233	Organism	Sida spinosa	Sida spinosa	Activity	=	40.0	mm2	PMID[568662]
NPT2234	Organism	Convolvulaceae	Convolvulaceae	Activity	=	24.0	mm2	PMID[568662]
NPT2235	Organism	Datura stramonium	Datura stramonium	Activity	=	24.0	mm2	PMID[568662]
NPT2236	Organism	Sorghum halepense	Sorghum halepense	Activity	=	34.0	mm2	PMID[568662]
NPT2237	Organism	Sorghum	Sorghum	Activity	=	40.0	mm2	PMID[568662]
NPT125	Organism	Chenopodium album	Chenopodium album	Activity	=	14.0	mm2	PMID[568662]
NPT2238	Organism	Nasturtium officinale	Nasturtium officinale	Activity	=	36.0	mm2	PMID[568662]
NPT2239	Organism	Ambrosia artemisiifolia	Ambrosia artemisiifolia	Activity	=	60.0	mm2	PMID[568662]

☑ 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 NPC235115 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	311
0.1-0.2	1438
0.2-0.3	3559
0.3-0.4	7923
0.4-0.5	10784
0.5-0.6	3739
0.6-0.7	6772
0.7-0.8	6594
0.8-0.85	1217
0.85-0.9	232
0.9-0.95	105
0.95-1	23

Similarity Score	Similarity Level	Natural Product ID
0.9767	High Similarity	NPC153783
0.9697	High Similarity	NPC472602
0.9627	High Similarity	NPC53649
0.9624	High Similarity	NPC88269
0.9624	High Similarity	NPC32360
0.9624	High Similarity	NPC268052
0.9621	High Similarity	NPC70380
0.9612	High Similarity	NPC219892
0.9612	High Similarity	NPC189823
0.9552	High Similarity	NPC472600
0.9552	High Similarity	NPC155205
0.9552	High Similarity	NPC472601
0.9549	High Similarity	NPC478200
0.9549	High Similarity	NPC33144
0.9549	High Similarity	NPC191835
0.9549	High Similarity	NPC212693
0.9549	High Similarity	NPC94248
0.9542	High Similarity	NPC175943
0.9485	High Similarity	NPC159721
0.9485	High Similarity	NPC469542
0.9481	High Similarity	NPC472603
0.9481	High Similarity	NPC472604
0.9481	High Similarity	NPC158634
0.9481	High Similarity	NPC472605
0.9478	High Similarity	NPC139634
0.9478	High Similarity	NPC105456
0.9474	High Similarity	NPC135837
0.9462	High Similarity	NPC470831
0.9462	High Similarity	NPC214702
0.9416	High Similarity	NPC42540
0.9416	High Similarity	NPC151607
0.9407	High Similarity	NPC158472
0.9398	High Similarity	NPC291454
0.9343	High Similarity	NPC478202
0.9343	High Similarity	NPC471731
0.9343	High Similarity	NPC472610
0.9338	High Similarity	NPC478217
0.9338	High Similarity	NPC313123
0.9338	High Similarity	NPC478201
0.9338	High Similarity	NPC1704
0.9338	High Similarity	NPC472035
0.9338	High Similarity	NPC244923
0.9338	High Similarity	NPC67650
0.9333	High Similarity	NPC52358
0.9333	High Similarity	NPC247409
0.9333	High Similarity	NPC92655
0.9328	High Similarity	NPC301915
0.9328	High Similarity	NPC261292
0.9328	High Similarity	NPC71256
0.9323	High Similarity	NPC180905
0.9323	High Similarity	NPC142027
0.9323	High Similarity	NPC27407
0.9323	High Similarity	NPC182496
0.9281	High Similarity	NPC473023
0.927	High Similarity	NPC471733
0.927	High Similarity	NPC469579
0.927	High Similarity	NPC474385
0.9259	High Similarity	NPC221104
0.9254	High Similarity	NPC50455
0.9254	High Similarity	NPC158481
0.9242	High Similarity	NPC476389
0.9203	High Similarity	NPC51106
0.9203	High Similarity	NPC472006
0.9197	High Similarity	NPC37530
0.9197	High Similarity	NPC470842
0.9197	High Similarity	NPC475730
0.9197	High Similarity	NPC90411
0.9191	High Similarity	NPC275356
0.9185	High Similarity	NPC178467
0.9185	High Similarity	NPC65837
0.9185	High Similarity	NPC194579
0.9185	High Similarity	NPC474771
0.9185	High Similarity	NPC149372
0.9185	High Similarity	NPC474849
0.9147	High Similarity	NPC201728
0.9147	High Similarity	NPC262671
0.9137	High Similarity	NPC277426
0.9137	High Similarity	NPC126882
0.9137	High Similarity	NPC478203
0.9137	High Similarity	NPC210425
0.9137	High Similarity	NPC210966
0.9137	High Similarity	NPC280404
0.9137	High Similarity	NPC86373
0.913	High Similarity	NPC82913
0.9124	High Similarity	NPC99441
0.9118	High Similarity	NPC9121
0.9118	High Similarity	NPC475974
0.9118	High Similarity	NPC177307
0.9118	High Similarity	NPC126739
0.9118	High Similarity	NPC197666
0.9118	High Similarity	NPC472403
0.9085	High Similarity	NPC270160
0.9085	High Similarity	NPC4423
0.9085	High Similarity	NPC237440
0.9085	High Similarity	NPC77325
0.9078	High Similarity	NPC471734
0.9078	High Similarity	NPC476463
0.9071	High Similarity	NPC472034
0.9071	High Similarity	NPC473692
0.9071	High Similarity	NPC257558
0.9071	High Similarity	NPC83272
0.9058	High Similarity	NPC220106
0.9051	High Similarity	NPC474655
0.9051	High Similarity	NPC471819
0.9044	High Similarity	NPC245058
0.9014	High Similarity	NPC471641
0.9014	High Similarity	NPC471642
0.9014	High Similarity	NPC240253
0.9014	High Similarity	NPC240622
0.9014	High Similarity	NPC221352
0.9007	High Similarity	NPC267509
0.9007	High Similarity	NPC107625
0.9007	High Similarity	NPC472033
0.9007	High Similarity	NPC471735
0.9	High Similarity	NPC95123
0.9	High Similarity	NPC66404
0.8993	High Similarity	NPC322112
0.8993	High Similarity	NPC105648
0.8993	High Similarity	NPC250755
0.8986	High Similarity	NPC165172
0.8971	High Similarity	NPC472599
0.8971	High Similarity	NPC156967
0.8958	High Similarity	NPC70016
0.8958	High Similarity	NPC215921
0.8951	High Similarity	NPC476684
0.8944	High Similarity	NPC472036
0.8944	High Similarity	NPC166583
0.8944	High Similarity	NPC210320
0.8944	High Similarity	NPC53362
0.8939	High Similarity	NPC41263
0.8936	High Similarity	NPC32470
0.8936	High Similarity	NPC312789
0.8936	High Similarity	NPC134621
0.8931	High Similarity	NPC95309
0.8897	High Similarity	NPC167903
0.8889	High Similarity	NPC472891
0.8881	High Similarity	NPC215711
0.8881	High Similarity	NPC73411
0.8881	High Similarity	NPC153417
0.8873	High Similarity	NPC260946
0.8873	High Similarity	NPC237208
0.8849	High Similarity	NPC64664
0.8849	High Similarity	NPC156872
0.8836	High Similarity	NPC281477
0.8832	High Similarity	NPC242712
0.8824	High Similarity	NPC475645
0.8819	High Similarity	NPC84142
0.8811	High Similarity	NPC14098
0.8806	High Similarity	NPC247477
0.8806	High Similarity	NPC473271
0.8806	High Similarity	NPC296158
0.8806	High Similarity	NPC147757
0.8806	High Similarity	NPC17840
0.8803	High Similarity	NPC29577
0.8797	High Similarity	NPC293453
0.8794	High Similarity	NPC354984
0.8794	High Similarity	NPC471639
0.8794	High Similarity	NPC471643
0.8794	High Similarity	NPC310340
0.8786	High Similarity	NPC275734
0.8786	High Similarity	NPC130485
0.8786	High Similarity	NPC149533
0.8777	High Similarity	NPC57380
0.8776	High Similarity	NPC82592
0.8776	High Similarity	NPC16082
0.8776	High Similarity	NPC199926
0.8767	High Similarity	NPC115249
0.8767	High Similarity	NPC184284
0.8767	High Similarity	NPC76041
0.8767	High Similarity	NPC478224
0.8759	High Similarity	NPC469619
0.8759	High Similarity	NPC469670
0.8759	High Similarity	NPC470107
0.8759	High Similarity	NPC119929
0.8759	High Similarity	NPC96501
0.8759	High Similarity	NPC56204
0.8759	High Similarity	NPC164762
0.8759	High Similarity	NPC278375
0.8759	High Similarity	NPC470844
0.875	High Similarity	NPC43627
0.8741	High Similarity	NPC202112
0.8741	High Similarity	NPC138978
0.8741	High Similarity	NPC163846
0.8741	High Similarity	NPC51513
0.8741	High Similarity	NPC225173
0.8732	High Similarity	NPC257025
0.8723	High Similarity	NPC471644
0.8723	High Similarity	NPC471640
0.8716	High Similarity	NPC227062
0.8716	High Similarity	NPC150227
0.8714	High Similarity	NPC168471
0.8707	High Similarity	NPC472799
0.8707	High Similarity	NPC470102
0.8707	High Similarity	NPC478231
0.8707	High Similarity	NPC137301
0.8699	High Similarity	NPC91809
0.8699	High Similarity	NPC204350
0.8699	High Similarity	NPC200773
0.8699	High Similarity	NPC240768
0.8699	High Similarity	NPC227166

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 NPC235115 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	265
0.1-0.2	932
0.2-0.3	1704
0.3-0.4	2634
0.4-0.5	1905
0.5-0.6	1151
0.6-0.7	402
0.7-0.8	135
0.8-0.85	18
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9333	High Similarity	NPD970	Clinical (unspecified phase)
0.8542	High Similarity	NPD2533	Approved
0.8542	High Similarity	NPD2534	Approved
0.8542	High Similarity	NPD2532	Approved
0.8478	Intermediate Similarity	NPD230	Phase 1
0.8456	Intermediate Similarity	NPD7819	Suspended
0.844	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.844	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.838	Intermediate Similarity	NPD1549	Phase 2
0.8298	Intermediate Similarity	NPD1510	Phase 2
0.8273	Intermediate Similarity	NPD1240	Approved
0.8244	Intermediate Similarity	NPD9545	Approved
0.8169	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8156	Intermediate Similarity	NPD1607	Approved
0.8146	Intermediate Similarity	NPD1934	Approved
0.8112	Intermediate Similarity	NPD1551	Phase 2
0.8092	Intermediate Similarity	NPD9493	Approved
0.8092	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD7075	Discontinued
0.8014	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD3750	Approved
0.8013	Intermediate Similarity	NPD6959	Discontinued
0.7974	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD6799	Approved
0.7973	Intermediate Similarity	NPD1511	Approved
0.7962	Intermediate Similarity	NPD5710	Approved
0.7962	Intermediate Similarity	NPD6232	Discontinued
0.7962	Intermediate Similarity	NPD5711	Approved
0.7961	Intermediate Similarity	NPD7411	Suspended
0.7935	Intermediate Similarity	NPD3749	Approved
0.7922	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD4380	Phase 2
0.7887	Intermediate Similarity	NPD943	Approved
0.7872	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD1512	Approved
0.7862	Intermediate Similarity	NPD2796	Approved
0.7862	Intermediate Similarity	NPD2935	Discontinued
0.7812	Intermediate Similarity	NPD7473	Discontinued
0.7806	Intermediate Similarity	NPD3817	Phase 2
0.7778	Intermediate Similarity	NPD6599	Discontinued
0.7756	Intermediate Similarity	NPD3882	Suspended
0.7756	Intermediate Similarity	NPD7768	Phase 2
0.775	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD3764	Approved
0.7742	Intermediate Similarity	NPD1465	Phase 2
0.7742	Intermediate Similarity	NPD2801	Approved
0.7733	Intermediate Similarity	NPD7390	Discontinued
0.7716	Intermediate Similarity	NPD5844	Phase 1
0.7707	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD2800	Approved
0.7703	Intermediate Similarity	NPD1243	Approved
0.7681	Intermediate Similarity	NPD9717	Approved
0.7681	Intermediate Similarity	NPD9269	Phase 2
0.7677	Intermediate Similarity	NPD6801	Discontinued
0.7671	Intermediate Similarity	NPD3748	Approved
0.7651	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD9268	Approved
0.7643	Intermediate Similarity	NPD1203	Approved
0.764	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD6166	Phase 2
0.764	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD5406	Approved
0.7619	Intermediate Similarity	NPD5408	Approved
0.7619	Intermediate Similarity	NPD5404	Approved
0.7619	Intermediate Similarity	NPD5405	Approved
0.7609	Intermediate Similarity	NPD422	Phase 1
0.7609	Intermediate Similarity	NPD1201	Approved
0.7607	Intermediate Similarity	NPD7054	Approved
0.7582	Intermediate Similarity	NPD920	Approved
0.7566	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD7472	Approved
0.7561	Intermediate Similarity	NPD7074	Phase 3
0.7556	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD6651	Approved
0.7533	Intermediate Similarity	NPD4628	Phase 3
0.753	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD1470	Approved
0.7518	Intermediate Similarity	NPD1164	Approved
0.7515	Intermediate Similarity	NPD6797	Phase 2
0.75	Intermediate Similarity	NPD6100	Approved
0.75	Intermediate Similarity	NPD411	Approved
0.75	Intermediate Similarity	NPD6099	Approved
0.7484	Intermediate Similarity	NPD3226	Approved
0.7481	Intermediate Similarity	NPD74	Approved
0.7481	Intermediate Similarity	NPD9266	Approved
0.747	Intermediate Similarity	NPD7251	Discontinued
0.7468	Intermediate Similarity	NPD5403	Approved
0.7468	Intermediate Similarity	NPD5402	Approved
0.7467	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD447	Suspended
0.7451	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD5401	Approved
0.745	Intermediate Similarity	NPD2346	Discontinued
0.7439	Intermediate Similarity	NPD3818	Discontinued
0.7438	Intermediate Similarity	NPD919	Approved
0.7429	Intermediate Similarity	NPD1608	Approved
0.7425	Intermediate Similarity	NPD7808	Phase 3
0.7405	Intermediate Similarity	NPD9263	Approved
0.7405	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD9267	Approved
0.7405	Intermediate Similarity	NPD9264	Approved
0.7394	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD5494	Approved
0.7365	Intermediate Similarity	NPD6559	Discontinued
0.7361	Intermediate Similarity	NPD6832	Phase 2
0.7347	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD520	Approved
0.7315	Intermediate Similarity	NPD2799	Discontinued
0.7305	Intermediate Similarity	NPD5953	Discontinued
0.7305	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD6190	Approved
0.7251	Intermediate Similarity	NPD8150	Discontinued
0.7237	Intermediate Similarity	NPD2654	Approved
0.7234	Intermediate Similarity	NPD1610	Phase 2
0.7233	Intermediate Similarity	NPD37	Approved
0.7222	Intermediate Similarity	NPD6234	Discontinued
0.7222	Intermediate Similarity	NPD1019	Discontinued
0.7219	Intermediate Similarity	NPD2344	Approved
0.7214	Intermediate Similarity	NPD17	Approved
0.7205	Intermediate Similarity	NPD4965	Approved
0.7205	Intermediate Similarity	NPD4967	Phase 2
0.7205	Intermediate Similarity	NPD4966	Approved
0.7203	Intermediate Similarity	NPD1283	Approved
0.72	Intermediate Similarity	NPD7033	Discontinued
0.7186	Intermediate Similarity	NPD7286	Phase 2
0.7153	Intermediate Similarity	NPD9281	Approved
0.7143	Intermediate Similarity	NPD4288	Approved
0.7143	Intermediate Similarity	NPD5353	Approved
0.7143	Intermediate Similarity	NPD1296	Phase 2
0.7143	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7199	Phase 2
0.7134	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD3751	Discontinued
0.7123	Intermediate Similarity	NPD4908	Phase 1
0.7114	Intermediate Similarity	NPD5124	Phase 1
0.7114	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD9261	Approved
0.7092	Intermediate Similarity	NPD4626	Approved
0.7092	Intermediate Similarity	NPD1778	Approved
0.7091	Intermediate Similarity	NPD7229	Phase 3
0.7071	Intermediate Similarity	NPD1548	Phase 1
0.7055	Intermediate Similarity	NPD9494	Approved
0.7051	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD1613	Approved
0.7047	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD2797	Approved
0.7032	Intermediate Similarity	NPD2309	Approved
0.703	Intermediate Similarity	NPD1247	Approved
0.7027	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD2313	Discontinued
0.7027	Intermediate Similarity	NPD3268	Approved
0.7024	Intermediate Similarity	NPD7228	Approved
0.7021	Intermediate Similarity	NPD5691	Approved
0.7018	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD4749	Approved
0.7013	Intermediate Similarity	NPD1652	Phase 2
0.7006	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1933	Approved
0.6993	Remote Similarity	NPD1281	Approved
0.6988	Remote Similarity	NPD3787	Discontinued
0.6986	Remote Similarity	NPD2798	Approved
0.6981	Remote Similarity	NPD1653	Approved
0.698	Remote Similarity	NPD6663	Approved
0.6977	Remote Similarity	NPD8313	Approved
0.6977	Remote Similarity	NPD8312	Approved
0.6974	Remote Similarity	NPD4308	Phase 3
0.6973	Remote Similarity	NPD8151	Discontinued
0.6971	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD4287	Approved
0.6968	Remote Similarity	NPD7003	Approved
0.6966	Remote Similarity	NPD3225	Approved
0.6962	Remote Similarity	NPD6273	Approved
0.6959	Remote Similarity	NPD4625	Phase 3
0.6957	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD3926	Phase 2
0.6939	Remote Similarity	NPD5736	Approved
0.6939	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD4060	Phase 1
0.6913	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD4750	Phase 3
0.691	Remote Similarity	NPD6534	Approved
0.691	Remote Similarity	NPD6535	Approved
0.6901	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD940	Approved
0.6894	Remote Similarity	NPD846	Approved
0.6892	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6355	Discontinued
0.6885	Remote Similarity	NPD7435	Discontinued
0.6883	Remote Similarity	NPD7266	Discontinued
0.6871	Remote Similarity	NPD6917	Clinical (unspecified phase)

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