NPASS Compound

Structure

NPC301897 OpenBabel07101719142D 22 25 0 0 1 0 0 0 0 0999 V2000 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0029 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -0.3090 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 19 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 2 0 0 0 0 5 10 2 0 0 0 0 6 10 1 0 0 0 0 7 11 1 0 0 0 0 7 12 1 0 0 0 0 8 11 2 0 0 0 0 8 13 1 0 0 0 0 9 20 1 0 0 0 0 9 21 1 0 0 0 0 11 14 1 0 0 0 0 12 10 1 1 0 0 0 12 22 1 0 0 0 0 13 15 2 0 0 0 0 13 20 1 0 0 0 0 14 16 2 0 0 0 0 14 17 1 0 0 0 0 15 16 1 0 0 0 0 15 21 1 0 0 0 0 16 19 1 0 0 0 0 17 18 2 0 0 0 0 17 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	298.08
Volume:	293.858
LogP:	3.192
LogD:	3.145
LogS:	-4.521
# Rotatable Bonds:	2
TPSA:	53.99
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.798
Synthetic Accessibility Score:	2.896
Fsp3:	0.235
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:	-4.661
MDCK Permeability:	2.8028809538227506e-05
Pgp-inhibitor:	0.816
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.016

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.151
Plasma Protein Binding (PPB):	94.60779571533203%
Volume Distribution (VD):	0.606
Pgp-substrate:	4.029193878173828%

ADMET: Metabolism

CYP1A2-inhibitor:	0.862
CYP1A2-substrate:	0.75
CYP2C19-inhibitor:	0.97
CYP2C19-substrate:	0.296
CYP2C9-inhibitor:	0.868
CYP2C9-substrate:	0.9
CYP2D6-inhibitor:	0.903
CYP2D6-substrate:	0.739
CYP3A4-inhibitor:	0.932
CYP3A4-substrate:	0.276

ADMET: Excretion

Clearance (CL):	13.711
Half-life (T1/2):	0.098

ADMET: Toxicity

hERG Blockers:	0.051
Human Hepatotoxicity (H-HT):	0.281
Drug-inuced Liver Injury (DILI):	0.859
AMES Toxicity:	0.345
Rat Oral Acute Toxicity:	0.06
Maximum Recommended Daily Dose:	0.519
Skin Sensitization:	0.368
Carcinogencity:	0.871
Eye Corrosion:	0.021
Eye Irritation:	0.841
Respiratory Toxicity:	0.326

Download Data

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

Natural Product: NPC301897

Natural Product ID:	NPC301897
*Common Name:**	(S)-4-Methoxy-7-Phenyl-7,8-Dihydro[1,3]Dioxolo[4,5-G]Isochromen-5-One
IUPAC Name:	(7S)-4-methoxy-7-phenyl-7,8-dihydro-[1,3]dioxolo[4,5-g]isochromen-5-one
Synonyms:
Standard InCHIKey:	HIWRPYQCEDHZSU-LBPRGKRZSA-N
Standard InCHI:	InChI=1S/C17H14O5/c1-19-16-14-11(8-13-15(16)21-9-20-13)7-12(22-17(14)18)10-5-3-2-4-6-10/h2-6,8,12H,7,9H2,1H3/t12-/m0/s1
SMILES:	COc1c2c(C[C@@H](c3ccccc3)OC2=O)cc2c1OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1099259
PubChem CID:	46210741
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003411] 2-benzopyrans

*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
NPO23964	Haloxylon scoparium	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20210326]
NPO23964	Haloxylon scoparium	Species	Chenopodiaceae	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
EC50	1
Others	1

Activity Type	# Activity
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Activity	=	144.6	%	PMID[520988]
NPT2	Others	Unspecified		EC50	=	140200.0	nM	PMID[520988]

☑ 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 NPC301897 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	421
0.1-0.2	1812
0.2-0.3	3965
0.3-0.4	9425
0.4-0.5	8969
0.5-0.6	3357
0.6-0.7	5797
0.7-0.8	7293
0.8-0.85	1463
0.85-0.9	184
0.9-0.95	10
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9221	High Similarity	NPC155063
0.9211	High Similarity	NPC473732
0.9172	High Similarity	NPC478199
0.9161	High Similarity	NPC258644
0.915	High Similarity	NPC153008
0.915	High Similarity	NPC148497
0.915	High Similarity	NPC475116
0.9128	High Similarity	NPC27106
0.9128	High Similarity	NPC470932
0.9103	High Similarity	NPC325122
0.9097	High Similarity	NPC227062
0.9091	High Similarity	NPC478213
0.9091	High Similarity	NPC244371
0.9067	High Similarity	NPC224687
0.9026	High Similarity	NPC68882
0.9026	High Similarity	NPC292460
0.8987	High Similarity	NPC34376
0.8981	High Similarity	NPC125713
0.8974	High Similarity	NPC150227
0.8968	High Similarity	NPC57211
0.8961	High Similarity	NPC279061
0.8961	High Similarity	NPC104353
0.8944	High Similarity	NPC471180
0.894	High Similarity	NPC296575
0.8938	High Similarity	NPC477884
0.8931	High Similarity	NPC61141
0.8931	High Similarity	NPC125991
0.8931	High Similarity	NPC469575
0.8924	High Similarity	NPC78944
0.8917	High Similarity	NPC84935
0.8917	High Similarity	NPC190020
0.8917	High Similarity	NPC77679
0.891	High Similarity	NPC199926
0.891	High Similarity	NPC478238
0.8903	High Similarity	NPC52623
0.8903	High Similarity	NPC295646
0.8882	High Similarity	NPC24257
0.8882	High Similarity	NPC153620
0.8875	High Similarity	NPC470178
0.8868	High Similarity	NPC209411
0.8868	High Similarity	NPC239890
0.8868	High Similarity	NPC15212
0.8868	High Similarity	NPC319749
0.8868	High Similarity	NPC258322
0.8868	High Similarity	NPC191352
0.8861	High Similarity	NPC215375
0.8861	High Similarity	NPC62518
0.8854	High Similarity	NPC477380
0.8851	High Similarity	NPC233780
0.8846	High Similarity	NPC273578
0.8846	High Similarity	NPC279930
0.8841	High Similarity	NPC477881
0.8839	High Similarity	NPC220577
0.8812	High Similarity	NPC280778
0.8812	High Similarity	NPC414831
0.8805	High Similarity	NPC474770
0.8797	High Similarity	NPC167595
0.8797	High Similarity	NPC310206
0.8797	High Similarity	NPC477885
0.879	High Similarity	NPC284353
0.879	High Similarity	NPC79998
0.879	High Similarity	NPC16082
0.879	High Similarity	NPC471746
0.879	High Similarity	NPC82592
0.8782	High Similarity	NPC308555
0.8782	High Similarity	NPC477961
0.8782	High Similarity	NPC35544
0.8782	High Similarity	NPC104728
0.8782	High Similarity	NPC477960
0.8782	High Similarity	NPC477962
0.8782	High Similarity	NPC474514
0.878	High Similarity	NPC471181
0.8774	High Similarity	NPC96501
0.8774	High Similarity	NPC234152
0.8766	High Similarity	NPC476342
0.8765	High Similarity	NPC113093
0.875	High Similarity	NPC184702
0.875	High Similarity	NPC260640
0.875	High Similarity	NPC295009
0.8742	High Similarity	NPC104459
0.8742	High Similarity	NPC474043
0.8742	High Similarity	NPC50430
0.8742	High Similarity	NPC113055
0.8742	High Similarity	NPC257914
0.8742	High Similarity	NPC279732
0.8742	High Similarity	NPC238405
0.8742	High Similarity	NPC297985
0.8734	High Similarity	NPC115123
0.8734	High Similarity	NPC239113
0.8734	High Similarity	NPC474983
0.8727	High Similarity	NPC474568
0.8726	High Similarity	NPC186507
0.8726	High Similarity	NPC281477
0.8726	High Similarity	NPC348849
0.8726	High Similarity	NPC178195
0.872	High Similarity	NPC212748
0.872	High Similarity	NPC477883
0.8718	High Similarity	NPC118332
0.8716	High Similarity	NPC160425
0.8712	High Similarity	NPC116745
0.8712	High Similarity	NPC298847
0.8712	High Similarity	NPC42892
0.871	High Similarity	NPC474648
0.871	High Similarity	NPC238366
0.8701	High Similarity	NPC474999
0.8701	High Similarity	NPC470511
0.8696	High Similarity	NPC273021
0.8696	High Similarity	NPC22324
0.8696	High Similarity	NPC18284
0.8693	High Similarity	NPC213482
0.8688	High Similarity	NPC200594
0.8688	High Similarity	NPC225624
0.8688	High Similarity	NPC285973
0.8688	High Similarity	NPC298093
0.8688	High Similarity	NPC131557
0.8683	High Similarity	NPC477880
0.8683	High Similarity	NPC477882
0.8679	High Similarity	NPC108456
0.8679	High Similarity	NPC19600
0.8671	High Similarity	NPC234730
0.8671	High Similarity	NPC254163
0.8667	High Similarity	NPC38438
0.8667	High Similarity	NPC475964
0.8667	High Similarity	NPC223375
0.8667	High Similarity	NPC472386
0.8667	High Similarity	NPC475825
0.8662	High Similarity	NPC38469
0.8659	High Similarity	NPC477165
0.8654	High Similarity	NPC303519
0.8654	High Similarity	NPC13985
0.8654	High Similarity	NPC210642
0.8654	High Similarity	NPC474975
0.865	High Similarity	NPC320471
0.865	High Similarity	NPC475214
0.865	High Similarity	NPC83049
0.865	High Similarity	NPC118162
0.865	High Similarity	NPC472452
0.8645	High Similarity	NPC10304
0.8645	High Similarity	NPC476058
0.8645	High Similarity	NPC63256
0.8645	High Similarity	NPC183236
0.8642	High Similarity	NPC475985
0.8636	High Similarity	NPC195919
0.8636	High Similarity	NPC216314
0.8636	High Similarity	NPC120924
0.8636	High Similarity	NPC231013
0.8634	High Similarity	NPC162668
0.8634	High Similarity	NPC182045
0.8631	High Similarity	NPC472725
0.8631	High Similarity	NPC472726
0.8627	High Similarity	NPC293201
0.8623	High Similarity	NPC156635
0.8623	High Similarity	NPC473713
0.8618	High Similarity	NPC185607
0.8616	High Similarity	NPC473900
0.8614	High Similarity	NPC72455
0.8599	High Similarity	NPC474663
0.8599	High Similarity	NPC200773
0.8599	High Similarity	NPC198615
0.8599	High Similarity	NPC215921
0.8599	High Similarity	NPC240768
0.8599	High Similarity	NPC228662
0.8599	High Similarity	NPC70016
0.8598	High Similarity	NPC79322
0.8598	High Similarity	NPC311912
0.8598	High Similarity	NPC135345
0.859	High Similarity	NPC149505
0.8589	High Similarity	NPC474301
0.8589	High Similarity	NPC475738
0.8589	High Similarity	NPC326520
0.8589	High Similarity	NPC7752
0.8589	High Similarity	NPC187923
0.8589	High Similarity	NPC165720
0.8581	High Similarity	NPC40654
0.8581	High Similarity	NPC262804
0.8581	High Similarity	NPC476463
0.858	High Similarity	NPC302741
0.858	High Similarity	NPC170203
0.858	High Similarity	NPC300537
0.858	High Similarity	NPC474763
0.858	High Similarity	NPC127782
0.8571	High Similarity	NPC110349
0.8571	High Similarity	NPC269906
0.8571	High Similarity	NPC74749
0.8571	High Similarity	NPC136278
0.8571	High Similarity	NPC87295
0.8571	High Similarity	NPC19554
0.8571	High Similarity	NPC43971
0.8571	High Similarity	NPC24627
0.8571	High Similarity	NPC299436
0.8571	High Similarity	NPC471590
0.8571	High Similarity	NPC477164
0.8571	High Similarity	NPC36217
0.8563	High Similarity	NPC66804
0.8563	High Similarity	NPC146803
0.8562	High Similarity	NPC18211
0.8562	High Similarity	NPC472860
0.8562	High Similarity	NPC19097
0.8562	High Similarity	NPC70853
0.8562	High Similarity	NPC474036

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 NPC301897 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	368
0.1-0.2	945
0.2-0.3	1770
0.3-0.4	2720
0.4-0.5	1811
0.5-0.6	960
0.6-0.7	419
0.7-0.8	127
0.8-0.85	28
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8701	High Similarity	NPD6980	Clinical (unspecified phase)
0.8688	High Similarity	NPD5494	Approved
0.8598	High Similarity	NPD3818	Discontinued
0.8544	High Similarity	NPD1934	Approved
0.8466	Intermediate Similarity	NPD6232	Discontinued
0.8438	Intermediate Similarity	NPD3817	Phase 2
0.8428	Intermediate Similarity	NPD37	Approved
0.8385	Intermediate Similarity	NPD4967	Phase 2
0.8385	Intermediate Similarity	NPD4965	Approved
0.8385	Intermediate Similarity	NPD4966	Approved
0.8383	Intermediate Similarity	NPD7074	Phase 3
0.8343	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD7054	Approved
0.8313	Intermediate Similarity	NPD7473	Discontinued
0.8293	Intermediate Similarity	NPD7199	Phase 2
0.8282	Intermediate Similarity	NPD6234	Discontinued
0.8274	Intermediate Similarity	NPD7472	Approved
0.8261	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD7819	Suspended
0.8214	Intermediate Similarity	NPD5844	Phase 1
0.8193	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD919	Approved
0.816	Intermediate Similarity	NPD3882	Suspended
0.816	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD2801	Approved
0.8146	Intermediate Similarity	NPD1933	Approved
0.8129	Intermediate Similarity	NPD7808	Phase 3
0.8118	Intermediate Similarity	NPD6797	Phase 2
0.811	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD2533	Approved
0.8101	Intermediate Similarity	NPD2532	Approved
0.8101	Intermediate Similarity	NPD2534	Approved
0.807	Intermediate Similarity	NPD7251	Discontinued
0.8066	Intermediate Similarity	NPD5005	Approved
0.8066	Intermediate Similarity	NPD5006	Approved
0.8065	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD2796	Approved
0.8047	Intermediate Similarity	NPD7228	Approved
0.8037	Intermediate Similarity	NPD1465	Phase 2
0.8037	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD6166	Phase 2
0.7976	Intermediate Similarity	NPD3926	Phase 2
0.7965	Intermediate Similarity	NPD6559	Discontinued
0.7964	Intermediate Similarity	NPD1247	Approved
0.7944	Intermediate Similarity	NPD4420	Approved
0.7925	Intermediate Similarity	NPD6799	Approved
0.7925	Intermediate Similarity	NPD1511	Approved
0.7892	Intermediate Similarity	NPD3749	Approved
0.7892	Intermediate Similarity	NPD7075	Discontinued
0.7888	Intermediate Similarity	NPD920	Approved
0.7885	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD3748	Approved
0.7861	Intermediate Similarity	NPD7240	Approved
0.7853	Intermediate Similarity	NPD6599	Discontinued
0.7853	Intermediate Similarity	NPD4380	Phase 2
0.7834	Intermediate Similarity	NPD1549	Phase 2
0.7826	Intermediate Similarity	NPD1512	Approved
0.7791	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD5242	Approved
0.7764	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD6801	Discontinued
0.7756	Intermediate Similarity	NPD1510	Phase 2
0.7753	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD7411	Suspended
0.7673	Intermediate Similarity	NPD1243	Approved
0.7665	Intermediate Similarity	NPD5402	Approved
0.7665	Intermediate Similarity	NPD5353	Approved
0.7657	Intermediate Similarity	NPD7685	Pre-registration
0.7654	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD6959	Discontinued
0.764	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD3751	Discontinued
0.7625	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD3750	Approved
0.7613	Intermediate Similarity	NPD1240	Approved
0.7602	Intermediate Similarity	NPD5711	Approved
0.7602	Intermediate Similarity	NPD3787	Discontinued
0.7602	Intermediate Similarity	NPD5710	Approved
0.76	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD3705	Approved
0.7564	Intermediate Similarity	NPD230	Phase 1
0.7564	Intermediate Similarity	NPD447	Suspended
0.756	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD2346	Discontinued
0.7546	Intermediate Similarity	NPD5401	Approved
0.7516	Intermediate Similarity	NPD1607	Approved
0.7485	Intermediate Similarity	NPD6386	Approved
0.7485	Intermediate Similarity	NPD6385	Approved
0.7484	Intermediate Similarity	NPD2935	Discontinued
0.7484	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD8312	Approved
0.7472	Intermediate Similarity	NPD8313	Approved
0.747	Intermediate Similarity	NPD3226	Approved
0.7455	Intermediate Similarity	NPD5403	Approved
0.7452	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7435	Intermediate Similarity	NPD8151	Discontinued
0.7414	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD7768	Phase 2
0.741	Intermediate Similarity	NPD1653	Approved
0.7407	Intermediate Similarity	NPD4628	Phase 3
0.7399	Intermediate Similarity	NPD7229	Phase 3
0.7389	Intermediate Similarity	NPD943	Approved
0.7375	Intermediate Similarity	NPD1551	Phase 2
0.7355	Intermediate Similarity	NPD6832	Phase 2
0.7354	Intermediate Similarity	NPD7435	Discontinued
0.7346	Intermediate Similarity	NPD2800	Approved
0.7333	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD6780	Approved
0.7287	Intermediate Similarity	NPD6779	Approved
0.7287	Intermediate Similarity	NPD6778	Approved
0.7287	Intermediate Similarity	NPD6777	Approved
0.7287	Intermediate Similarity	NPD6776	Approved
0.7287	Intermediate Similarity	NPD6781	Approved
0.7287	Intermediate Similarity	NPD6782	Approved
0.7278	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD1613	Approved
0.7262	Intermediate Similarity	NPD7458	Discontinued
0.7261	Intermediate Similarity	NPD3764	Approved
0.7239	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD2798	Approved
0.7219	Intermediate Similarity	NPD17	Approved
0.7205	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD2799	Discontinued
0.7197	Intermediate Similarity	NPD3027	Phase 3
0.7196	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD8455	Phase 2
0.7186	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7783	Phase 2
0.7179	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD7697	Approved
0.7173	Intermediate Similarity	NPD7696	Phase 3
0.7173	Intermediate Similarity	NPD7698	Approved
0.7173	Intermediate Similarity	NPD7680	Approved
0.716	Intermediate Similarity	NPD2438	Suspended
0.7158	Intermediate Similarity	NPD8434	Phase 2
0.7152	Intermediate Similarity	NPD6190	Approved
0.7152	Intermediate Similarity	NPD2313	Discontinued
0.7135	Intermediate Similarity	NPD7870	Phase 2
0.7135	Intermediate Similarity	NPD7871	Phase 2
0.7134	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2654	Approved
0.7128	Intermediate Similarity	NPD7874	Approved
0.7128	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD2403	Approved
0.7117	Intermediate Similarity	NPD2344	Approved
0.7117	Intermediate Similarity	NPD1471	Phase 3
0.7117	Intermediate Similarity	NPD7266	Discontinued
0.7099	Intermediate Similarity	NPD7033	Discontinued
0.7078	Intermediate Similarity	NPD1608	Approved
0.7071	Intermediate Similarity	NPD7930	Approved
0.707	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD8150	Discontinued
0.7063	Intermediate Similarity	NPD2979	Phase 3
0.7059	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD4288	Approved
0.7052	Intermediate Similarity	NPD5977	Approved
0.7052	Intermediate Similarity	NPD5978	Approved
0.7051	Intermediate Similarity	NPD3267	Approved
0.7051	Intermediate Similarity	NPD3266	Approved
0.7045	Intermediate Similarity	NPD8127	Discontinued
0.7039	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD6823	Phase 2
0.703	Intermediate Similarity	NPD6674	Discontinued
0.7029	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD7701	Phase 2
0.7021	Intermediate Similarity	NPD6534	Approved
0.7021	Intermediate Similarity	NPD6535	Approved
0.7019	Intermediate Similarity	NPD6355	Discontinued
0.7018	Intermediate Similarity	NPD7028	Phase 2
0.7017	Intermediate Similarity	NPD5953	Discontinued
0.7013	Intermediate Similarity	NPD1281	Approved
0.7006	Intermediate Similarity	NPD6808	Phase 2
0.7006	Intermediate Similarity	NPD1019	Discontinued
0.7	Intermediate Similarity	NPD7286	Phase 2
0.6989	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD4287	Approved
0.6988	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD4110	Phase 3
0.6987	Remote Similarity	NPD1876	Approved
0.6982	Remote Similarity	NPD6273	Approved
0.6977	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD7390	Discontinued
0.6962	Remote Similarity	NPD3018	Phase 2
0.6962	Remote Similarity	NPD9494	Approved
0.6959	Remote Similarity	NPD8320	Phase 1
0.6959	Remote Similarity	NPD8319	Approved
0.6957	Remote Similarity	NPD4307	Phase 2
0.6951	Remote Similarity	NPD6100	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