NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	208.07
Volume:	206.314
LogP:	2.688
LogD:	2.586
LogS:	-2.891
# Rotatable Bonds:	2
TPSA:	62.83
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.795
Synthetic Accessibility Score:	2.901
Fsp3:	0.273
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.743
MDCK Permeability:	1.4747465684195049e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.041
Plasma Protein Binding (PPB):	97.04935455322266%
Volume Distribution (VD):	0.633
Pgp-substrate:	8.250564575195312%

ADMET: Metabolism

CYP1A2-inhibitor:	0.945
CYP1A2-substrate:	0.943
CYP2C19-inhibitor:	0.05
CYP2C19-substrate:	0.39
CYP2C9-inhibitor:	0.415
CYP2C9-substrate:	0.792
CYP2D6-inhibitor:	0.466
CYP2D6-substrate:	0.709
CYP3A4-inhibitor:	0.08
CYP3A4-substrate:	0.184

ADMET: Excretion

Clearance (CL):	12.353
Half-life (T1/2):	0.789

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.612
Drug-inuced Liver Injury (DILI):	0.965
AMES Toxicity:	0.232
Rat Oral Acute Toxicity:	0.464
Maximum Recommended Daily Dose:	0.043
Skin Sensitization:	0.676
Carcinogencity:	0.673
Eye Corrosion:	0.009
Eye Irritation:	0.216
Respiratory Toxicity:	0.755

Download Data

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

Natural Product: NPC32058

Natural Product ID:	NPC32058
*Common Name:**	(R)-3-Ethyl-7-Hydroxy-6-Methoxyphthalide
IUPAC Name:	(3R)-3-ethyl-7-hydroxy-6-methoxy-3H-2-benzofuran-1-one
Synonyms:
Standard InCHIKey:	CJPMLOYFDLJAKU-SSDOTTSWSA-N
Standard InCHI:	InChI=1S/C11H12O4/c1-3-7-6-4-5-8(14-2)10(12)9(6)11(13)15-7/h4-5,7,12H,3H2,1-2H3/t7-/m1/s1
SMILES:	CC[C@@H]1c2ccc(c(c2C(=O)O1)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL490782
PubChem CID:	25135575
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans [CHEMONTID:0001578] Benzofuranones

*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
NPO9098.1	Pittosporum illicioides	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[18817445]
NPO1592	Citrullus colocynthis	Species	Cucurbitaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[30183289]
NPO1592	Citrullus colocynthis	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1592	Citrullus colocynthis	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1592	Citrullus colocynthis	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1592	Citrullus colocynthis	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9098	Pittosporum illicioides	Species	Pittosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10206	Anthemis fuscata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10606	Pteris japonica	Species	Pteridaceae	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	2

Activity Type	# Activity
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	21200.0	nM	PMID[481321]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[481321]

☑ 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 NPC32058 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	331
0.1-0.2	1473
0.2-0.3	3881
0.3-0.4	8523
0.4-0.5	9722
0.5-0.6	3306
0.6-0.7	5794
0.7-0.8	8248
0.8-0.85	1249
0.85-0.9	148
0.9-0.95	16
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC85734
0.9784	High Similarity	NPC258307
0.9583	High Similarity	NPC96501
0.9424	High Similarity	NPC233780
0.9324	High Similarity	NPC199926
0.9324	High Similarity	NPC79998
0.9281	High Similarity	NPC160425
0.9262	High Similarity	NPC150227
0.92	High Similarity	NPC84935
0.92	High Similarity	NPC77679
0.92	High Similarity	NPC190020
0.9189	High Similarity	NPC295646
0.9128	High Similarity	NPC281477
0.9067	High Similarity	NPC16082
0.9067	High Similarity	NPC82592
0.9034	High Similarity	NPC27106
0.9007	High Similarity	NPC227062
0.8993	High Similarity	NPC200773
0.8993	High Similarity	NPC240768
0.8958	High Similarity	NPC90411
0.8954	High Similarity	NPC200594
0.8944	High Similarity	NPC62907
0.8839	High Similarity	NPC22324
0.8824	High Similarity	NPC143328
0.8819	High Similarity	NPC471819
0.8819	High Similarity	NPC134969
0.88	High Similarity	NPC179178
0.8776	High Similarity	NPC210425
0.8776	High Similarity	NPC277426
0.8776	High Similarity	NPC280404
0.8776	High Similarity	NPC86373
0.8758	High Similarity	NPC54928
0.875	High Similarity	NPC197666
0.875	High Similarity	NPC126739
0.8742	High Similarity	NPC70016
0.8742	High Similarity	NPC215921
0.8742	High Similarity	NPC204350
0.8726	High Similarity	NPC191930
0.8718	High Similarity	NPC144843
0.8707	High Similarity	NPC27159
0.8699	High Similarity	NPC130485
0.8693	High Similarity	NPC16286
0.8693	High Similarity	NPC38898
0.869	High Similarity	NPC147379
0.8684	High Similarity	NPC199773
0.8684	High Similarity	NPC180388
0.8681	High Similarity	NPC135837
0.8675	High Similarity	NPC31132
0.8675	High Similarity	NPC469670
0.8675	High Similarity	NPC469619
0.8671	High Similarity	NPC470990
0.8662	High Similarity	NPC249181
0.8662	High Similarity	NPC159418
0.8662	High Similarity	NPC283823
0.8658	High Similarity	NPC138978
0.8649	High Similarity	NPC223185
0.8639	High Similarity	NPC474385
0.8639	High Similarity	NPC299154
0.8636	High Similarity	NPC197751
0.863	High Similarity	NPC50823
0.8627	High Similarity	NPC144801
0.8627	High Similarity	NPC116850
0.8627	High Similarity	NPC197188
0.8627	High Similarity	NPC238672
0.8627	High Similarity	NPC291510
0.8627	High Similarity	NPC43872
0.8618	High Similarity	NPC473732
0.8616	High Similarity	NPC283041
0.8611	High Similarity	NPC326847
0.86	High Similarity	NPC210320
0.86	High Similarity	NPC166583
0.86	High Similarity	NPC476463
0.86	High Similarity	NPC53362
0.8592	High Similarity	NPC111888
0.859	High Similarity	NPC47623
0.8581	High Similarity	NPC473395
0.8581	High Similarity	NPC51106
0.8581	High Similarity	NPC469615
0.8581	High Similarity	NPC302258
0.8581	High Similarity	NPC472006
0.8571	High Similarity	NPC1704
0.8571	High Similarity	NPC67650
0.8571	High Similarity	NPC475730
0.8571	High Similarity	NPC20541
0.8562	High Similarity	NPC475116
0.8553	High Similarity	NPC20237
0.8553	High Similarity	NPC472452
0.8552	High Similarity	NPC112068
0.8552	High Similarity	NPC110899
0.8552	High Similarity	NPC25305
0.8552	High Similarity	NPC95679
0.8552	High Similarity	NPC125417
0.8544	High Similarity	NPC223006
0.8544	High Similarity	NPC173729
0.8544	High Similarity	NPC272750
0.8544	High Similarity	NPC475985
0.8544	High Similarity	NPC477689
0.8544	High Similarity	NPC134047
0.8543	High Similarity	NPC55327
0.8543	High Similarity	NPC73411
0.8543	High Similarity	NPC215711
0.8542	High Similarity	NPC180905
0.8542	High Similarity	NPC182496
0.8533	High Similarity	NPC472033
0.8533	High Similarity	NPC226987
0.8533	High Similarity	NPC260946
0.8533	High Similarity	NPC143903
0.8533	High Similarity	NPC107625
0.8531	High Similarity	NPC200422
0.8531	High Similarity	NPC157478
0.8531	High Similarity	NPC289572
0.8531	High Similarity	NPC295406
0.8526	High Similarity	NPC238381
0.8523	High Similarity	NPC469683
0.8523	High Similarity	NPC213900
0.8523	High Similarity	NPC257025
0.8521	High Similarity	NPC7012
0.8516	High Similarity	NPC301897
0.8514	High Similarity	NPC314271
0.8506	High Similarity	NPC298802
0.8506	High Similarity	NPC25127
0.8503	High Similarity	NPC187690
0.8503	High Similarity	NPC158472
0.8503	High Similarity	NPC100675
0.8503	High Similarity	NPC470991
0.85	High Similarity	NPC298847
0.8497	Intermediate Similarity	NPC267091
0.8493	Intermediate Similarity	NPC325625
0.8491	Intermediate Similarity	NPC474301
0.8491	Intermediate Similarity	NPC326520
0.8487	Intermediate Similarity	NPC270160
0.8487	Intermediate Similarity	NPC237440
0.8481	Intermediate Similarity	NPC144557
0.8477	Intermediate Similarity	NPC61871
0.8477	Intermediate Similarity	NPC472969
0.8477	Intermediate Similarity	NPC30647
0.8477	Intermediate Similarity	NPC55557
0.8477	Intermediate Similarity	NPC472036
0.8471	Intermediate Similarity	NPC24627
0.8471	Intermediate Similarity	NPC292415
0.8471	Intermediate Similarity	NPC36217
0.8467	Intermediate Similarity	NPC83272
0.8467	Intermediate Similarity	NPC472034
0.8457	Intermediate Similarity	NPC471181
0.8456	Intermediate Similarity	NPC469542
0.8452	Intermediate Similarity	NPC67396
0.8452	Intermediate Similarity	NPC99381
0.8452	Intermediate Similarity	NPC18954
0.8452	Intermediate Similarity	NPC286052
0.8452	Intermediate Similarity	NPC476642
0.8451	Intermediate Similarity	NPC285776
0.8446	Intermediate Similarity	NPC84273
0.8442	Intermediate Similarity	NPC271681
0.8442	Intermediate Similarity	NPC289968
0.8442	Intermediate Similarity	NPC236637
0.8442	Intermediate Similarity	NPC302950
0.8442	Intermediate Similarity	NPC219582
0.8442	Intermediate Similarity	NPC167903
0.8438	Intermediate Similarity	NPC170245
0.8435	Intermediate Similarity	NPC247409
0.8435	Intermediate Similarity	NPC275356
0.8435	Intermediate Similarity	NPC4796
0.8431	Intermediate Similarity	NPC151473
0.8431	Intermediate Similarity	NPC119929
0.8431	Intermediate Similarity	NPC103509
0.8431	Intermediate Similarity	NPC243891
0.8428	Intermediate Similarity	NPC147596
0.8421	Intermediate Similarity	NPC98809
0.8421	Intermediate Similarity	NPC125570
0.8421	Intermediate Similarity	NPC287395
0.8421	Intermediate Similarity	NPC183655
0.8421	Intermediate Similarity	NPC476394
0.8418	Intermediate Similarity	NPC349525
0.8418	Intermediate Similarity	NPC103201
0.8418	Intermediate Similarity	NPC201560
0.8418	Intermediate Similarity	NPC117985
0.8418	Intermediate Similarity	NPC473106
0.8418	Intermediate Similarity	NPC474779
0.8414	Intermediate Similarity	NPC254832
0.8414	Intermediate Similarity	NPC229638
0.8414	Intermediate Similarity	NPC71108
0.8414	Intermediate Similarity	NPC176102
0.8414	Intermediate Similarity	NPC267539
0.8414	Intermediate Similarity	NPC29317
0.8414	Intermediate Similarity	NPC204257
0.8408	Intermediate Similarity	NPC470339
0.8408	Intermediate Similarity	NPC45846
0.8403	Intermediate Similarity	NPC129889
0.8403	Intermediate Similarity	NPC153783
0.8403	Intermediate Similarity	NPC307006
0.84	Intermediate Similarity	NPC142165
0.84	Intermediate Similarity	NPC470932
0.84	Intermediate Similarity	NPC113397
0.8397	Intermediate Similarity	NPC24640
0.8397	Intermediate Similarity	NPC317383
0.8397	Intermediate Similarity	NPC235165
0.8397	Intermediate Similarity	NPC255106
0.8392	Intermediate Similarity	NPC469480
0.8392	Intermediate Similarity	NPC214702
0.8392	Intermediate Similarity	NPC470831

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 NPC32058 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	292
0.1-0.2	879
0.2-0.3	1893
0.3-0.4	2552
0.4-0.5	1779
0.5-0.6	1047
0.6-0.7	541
0.7-0.8	151
0.8-0.85	14
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8531	High Similarity	NPD447	Suspended
0.8442	Intermediate Similarity	NPD1934	Approved
0.8435	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8397	Intermediate Similarity	NPD3882	Suspended
0.8344	Intermediate Similarity	NPD2533	Approved
0.8344	Intermediate Similarity	NPD2532	Approved
0.8344	Intermediate Similarity	NPD2534	Approved
0.8276	Intermediate Similarity	NPD230	Phase 1
0.8269	Intermediate Similarity	NPD2801	Approved
0.825	Intermediate Similarity	NPD6232	Discontinued
0.816	Intermediate Similarity	NPD3818	Discontinued
0.8158	Intermediate Similarity	NPD1511	Approved
0.8153	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD3817	Phase 2
0.8098	Intermediate Similarity	NPD7473	Discontinued
0.8063	Intermediate Similarity	NPD6234	Discontinued
0.8052	Intermediate Similarity	NPD1512	Approved
0.805	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD1465	Phase 2
0.7986	Intermediate Similarity	NPD9494	Approved
0.7933	Intermediate Similarity	NPD2935	Discontinued
0.7927	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD6166	Phase 2
0.7927	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD7054	Approved
0.7867	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD37	Approved
0.7849	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD7074	Phase 3
0.7844	Intermediate Similarity	NPD7472	Approved
0.7826	Intermediate Similarity	NPD4966	Approved
0.7826	Intermediate Similarity	NPD4967	Phase 2
0.7826	Intermediate Similarity	NPD4965	Approved
0.7791	Intermediate Similarity	NPD5494	Approved
0.7784	Intermediate Similarity	NPD5844	Phase 1
0.7762	Intermediate Similarity	NPD9717	Approved
0.773	Intermediate Similarity	NPD919	Approved
0.7727	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD7228	Approved
0.7702	Intermediate Similarity	NPD7819	Suspended
0.7697	Intermediate Similarity	NPD1551	Phase 2
0.7692	Intermediate Similarity	NPD6797	Phase 2
0.7692	Intermediate Similarity	NPD6799	Approved
0.7692	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD7075	Discontinued
0.7654	Intermediate Similarity	NPD5402	Approved
0.7647	Intermediate Similarity	NPD7251	Discontinued
0.7647	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD9493	Approved
0.7632	Intermediate Similarity	NPD1510	Phase 2
0.7625	Intermediate Similarity	NPD4380	Phase 2
0.7613	Intermediate Similarity	NPD3750	Approved
0.7613	Intermediate Similarity	NPD4628	Phase 3
0.7603	Intermediate Similarity	NPD1203	Approved
0.7602	Intermediate Similarity	NPD7808	Phase 3
0.76	Intermediate Similarity	NPD1240	Approved
0.76	Intermediate Similarity	NPD943	Approved
0.7597	Intermediate Similarity	NPD1549	Phase 2
0.7593	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD5711	Approved
0.759	Intermediate Similarity	NPD5710	Approved
0.7584	Intermediate Similarity	NPD411	Approved
0.7584	Intermediate Similarity	NPD3764	Approved
0.7572	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD3226	Approved
0.7561	Intermediate Similarity	NPD3749	Approved
0.755	Intermediate Similarity	NPD1933	Approved
0.7544	Intermediate Similarity	NPD7685	Pre-registration
0.7544	Intermediate Similarity	NPD6559	Discontinued
0.7535	Intermediate Similarity	NPD9545	Approved
0.7532	Intermediate Similarity	NPD2346	Discontinued
0.753	Intermediate Similarity	NPD1247	Approved
0.753	Intermediate Similarity	NPD7199	Phase 2
0.7517	Intermediate Similarity	NPD3027	Phase 3
0.7517	Intermediate Similarity	NPD9269	Phase 2
0.7516	Intermediate Similarity	NPD6599	Discontinued
0.75	Intermediate Similarity	NPD1607	Approved
0.75	Intermediate Similarity	NPD1653	Approved
0.7485	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1613	Approved
0.7483	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD6190	Approved
0.7448	Intermediate Similarity	NPD3705	Approved
0.744	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD5403	Approved
0.7438	Intermediate Similarity	NPD920	Approved
0.7436	Intermediate Similarity	NPD2800	Approved
0.7434	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD1019	Discontinued
0.7423	Intermediate Similarity	NPD6801	Discontinued
0.7421	Intermediate Similarity	NPD5401	Approved
0.7421	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD228	Approved
0.7403	Intermediate Similarity	NPD2799	Discontinued
0.7394	Intermediate Similarity	NPD7768	Phase 2
0.736	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD8312	Approved
0.7356	Intermediate Similarity	NPD8313	Approved
0.7347	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD3926	Phase 2
0.7333	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6832	Phase 2
0.7321	Intermediate Similarity	NPD6959	Discontinued
0.732	Intermediate Similarity	NPD6355	Discontinued
0.7312	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD2344	Approved
0.729	Intermediate Similarity	NPD3748	Approved
0.7278	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD4110	Phase 3
0.7267	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD6386	Approved
0.7256	Intermediate Similarity	NPD6385	Approved
0.7256	Intermediate Similarity	NPD7411	Suspended
0.7255	Intermediate Similarity	NPD4060	Phase 1
0.7253	Intermediate Similarity	NPD4420	Approved
0.7244	Intermediate Similarity	NPD2796	Approved
0.7241	Intermediate Similarity	NPD9268	Approved
0.7241	Intermediate Similarity	NPD7240	Approved
0.7237	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD2313	Discontinued
0.7229	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD5353	Approved
0.7219	Intermediate Similarity	NPD8127	Discontinued
0.7215	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD1243	Approved
0.7211	Intermediate Similarity	NPD422	Phase 1
0.7209	Intermediate Similarity	NPD3751	Discontinued
0.72	Intermediate Similarity	NPD5647	Approved
0.7197	Intermediate Similarity	NPD6004	Phase 3
0.7197	Intermediate Similarity	NPD6002	Phase 3
0.7197	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD7266	Discontinued
0.7197	Intermediate Similarity	NPD6005	Phase 3
0.7197	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD4626	Approved
0.7188	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD1283	Approved
0.7169	Intermediate Similarity	NPD1006	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD1608	Approved
0.7161	Intermediate Similarity	NPD6653	Approved
0.7153	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD8434	Phase 2
0.7135	Intermediate Similarity	NPD8150	Discontinued
0.7135	Intermediate Similarity	NPD5242	Approved
0.7134	Intermediate Similarity	NPD5408	Approved
0.7134	Intermediate Similarity	NPD3455	Phase 2
0.7134	Intermediate Similarity	NPD5406	Approved
0.7134	Intermediate Similarity	NPD5404	Approved
0.7134	Intermediate Similarity	NPD5405	Approved
0.7134	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1470	Approved
0.7125	Intermediate Similarity	NPD2309	Approved
0.7124	Intermediate Similarity	NPD6798	Discontinued
0.7123	Intermediate Similarity	NPD5691	Approved
0.7119	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD5005	Approved
0.7097	Intermediate Similarity	NPD5006	Approved
0.7095	Intermediate Similarity	NPD1201	Approved
0.7093	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6233	Phase 2
0.7076	Intermediate Similarity	NPD3787	Discontinued
0.7075	Intermediate Similarity	NPD1778	Approved
0.7071	Intermediate Similarity	NPD9266	Approved
0.7071	Intermediate Similarity	NPD74	Approved
0.707	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD7033	Discontinued
0.7063	Intermediate Similarity	NPD8166	Discontinued
0.7063	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6273	Approved
0.7027	Intermediate Similarity	NPD3496	Discontinued
0.7025	Intermediate Similarity	NPD2438	Suspended
0.7025	Intermediate Similarity	NPD9570	Approved
0.702	Intermediate Similarity	NPD1164	Approved
0.702	Intermediate Similarity	NPD2797	Approved
0.7007	Intermediate Similarity	NPD1357	Approved
0.7	Intermediate Similarity	NPD9267	Approved
0.7	Intermediate Similarity	NPD9263	Approved
0.7	Intermediate Similarity	NPD1652	Phase 2
0.7	Intermediate Similarity	NPD9264	Approved
0.6994	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD5762	Approved
0.6981	Remote Similarity	NPD5763	Approved
0.698	Remote Similarity	NPD1281	Approved
0.698	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD7229	Phase 3
0.6974	Remote Similarity	NPD2798	Approved
0.6968	Remote Similarity	NPD7435	Discontinued
0.6962	Remote Similarity	NPD4308	Phase 3
0.6959	Remote Similarity	NPD17	Approved
0.6957	Remote Similarity	NPD7003	Approved
0.6949	Remote Similarity	NPD7039	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