NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	166.06
Volume:	171.489
LogP:	1.316
LogD:	1.249
LogS:	-1.424
# Rotatable Bonds:	2
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.679
Synthetic Accessibility Score:	1.738
Fsp3:	0.222
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:	-4.524
MDCK Permeability:	1.7473355910624377e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.051
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.15

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.599
Plasma Protein Binding (PPB):	63.97504425048828%
Volume Distribution (VD):	0.874
Pgp-substrate:	35.36457824707031%

ADMET: Metabolism

CYP1A2-inhibitor:	0.951
CYP1A2-substrate:	0.907
CYP2C19-inhibitor:	0.545
CYP2C19-substrate:	0.307
CYP2C9-inhibitor:	0.116
CYP2C9-substrate:	0.927
CYP2D6-inhibitor:	0.237
CYP2D6-substrate:	0.872
CYP3A4-inhibitor:	0.123
CYP3A4-substrate:	0.296

ADMET: Excretion

Clearance (CL):	10.773
Half-life (T1/2):	0.886

ADMET: Toxicity

hERG Blockers:	0.042
Human Hepatotoxicity (H-HT):	0.042
Drug-inuced Liver Injury (DILI):	0.306
AMES Toxicity:	0.08
Rat Oral Acute Toxicity:	0.223
Maximum Recommended Daily Dose:	0.059
Skin Sensitization:	0.23
Carcinogencity:	0.294
Eye Corrosion:	0.69
Eye Irritation:	0.989
Respiratory Toxicity:	0.18

Download Data

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

Natural Product: NPC80694

Natural Product ID:	NPC80694
*Common Name:**	Isopeonol
IUPAC Name:	1-(4-hydroxy-2-methoxyphenyl)ethanone
Synonyms:
Standard InCHIKey:	XPHIPEXPAGCEBM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C9H10O3/c1-6(10)8-4-3-7(11)5-9(8)12-2/h3-5,11H,1-2H3
SMILES:	COc1cc(O)ccc1C(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3039008
PubChem CID:	529402
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0004296] Phenylketones [CHEMONTID:0004298] Alkyl-phenylketones

*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
NPO24694	Vincetoxicum pycnostelma	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24694	Vincetoxicum pycnostelma	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]

☑ 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	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	60.41	%	PMID[482303]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	84.87	%	PMID[482303]

☑ 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 NPC80694 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	371
0.1-0.2	1982
0.2-0.3	5205
0.3-0.4	11837
0.4-0.5	5347
0.5-0.6	4578
0.6-0.7	6166
0.7-0.8	5052
0.8-0.85	1387
0.85-0.9	634
0.9-0.95	106
0.95-1	32

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC186098
0.9754	High Similarity	NPC305518
0.9754	High Similarity	NPC128428
0.968	High Similarity	NPC313618
0.968	High Similarity	NPC308037
0.968	High Similarity	NPC64359
0.9603	High Similarity	NPC129132
0.9603	High Similarity	NPC257756
0.9603	High Similarity	NPC205468
0.9603	High Similarity	NPC87231
0.9603	High Similarity	NPC212631
0.9597	High Similarity	NPC78662
0.9597	High Similarity	NPC212379
0.9597	High Similarity	NPC8005
0.9597	High Similarity	NPC69235
0.9597	High Similarity	NPC60558
0.9528	High Similarity	NPC192304
0.9528	High Similarity	NPC312318
0.9528	High Similarity	NPC337373
0.9528	High Similarity	NPC139813
0.9528	High Similarity	NPC472365
0.9528	High Similarity	NPC175098
0.9528	High Similarity	NPC188646
0.9528	High Similarity	NPC263670
0.9528	High Similarity	NPC56031
0.9528	High Similarity	NPC242294
0.9524	High Similarity	NPC262359
0.952	High Similarity	NPC185497
0.952	High Similarity	NPC307732
0.952	High Similarity	NPC42292
0.9453	High Similarity	NPC286336
0.9453	High Similarity	NPC164136
0.944	High Similarity	NPC230818
0.9431	High Similarity	NPC65041
0.9375	High Similarity	NPC20560
0.9375	High Similarity	NPC144051
0.9375	High Similarity	NPC159623
0.9375	High Similarity	NPC28753
0.9375	High Similarity	NPC294593
0.9375	High Similarity	NPC18877
0.9375	High Similarity	NPC82225
0.9375	High Similarity	NPC204960
0.937	High Similarity	NPC475589
0.937	High Similarity	NPC31872
0.937	High Similarity	NPC473584
0.9365	High Similarity	NPC247779
0.9365	High Similarity	NPC84772
0.936	High Similarity	NPC293453
0.9308	High Similarity	NPC66349
0.9308	High Similarity	NPC472364
0.9308	High Similarity	NPC472367
0.9308	High Similarity	NPC222633
0.9308	High Similarity	NPC476333
0.9308	High Similarity	NPC98115
0.9308	High Similarity	NPC150399
0.9308	High Similarity	NPC1486
0.9308	High Similarity	NPC12165
0.9308	High Similarity	NPC477242
0.9308	High Similarity	NPC240593
0.9308	High Similarity	NPC274109
0.9308	High Similarity	NPC41461
0.9308	High Similarity	NPC168105
0.9308	High Similarity	NPC477244
0.9308	High Similarity	NPC473391
0.9308	High Similarity	NPC25287
0.9308	High Similarity	NPC477243
0.9308	High Similarity	NPC249606
0.9308	High Similarity	NPC186838
0.9297	High Similarity	NPC203817
0.9297	High Similarity	NPC25937
0.9291	High Similarity	NPC270369
0.9291	High Similarity	NPC324482
0.9291	High Similarity	NPC5515
0.9237	High Similarity	NPC303644
0.9237	High Similarity	NPC162680
0.9237	High Similarity	NPC153979
0.9237	High Similarity	NPC317119
0.9237	High Similarity	NPC181124
0.9237	High Similarity	NPC472419
0.9237	High Similarity	NPC7013
0.9237	High Similarity	NPC116632
0.9237	High Similarity	NPC209560
0.9237	High Similarity	NPC294409
0.9237	High Similarity	NPC250266
0.9237	High Similarity	NPC266597
0.9237	High Similarity	NPC188879
0.9231	High Similarity	NPC13575
0.9231	High Similarity	NPC39426
0.9231	High Similarity	NPC234560
0.9231	High Similarity	NPC156092
0.9231	High Similarity	NPC151113
0.9231	High Similarity	NPC131039
0.9225	High Similarity	NPC223457
0.9225	High Similarity	NPC57601
0.9219	High Similarity	NPC475009
0.9219	High Similarity	NPC65060
0.9219	High Similarity	NPC66384
0.9219	High Similarity	NPC112192
0.9219	High Similarity	NPC27490
0.9219	High Similarity	NPC189106
0.9219	High Similarity	NPC164236
0.9219	High Similarity	NPC128348
0.9219	High Similarity	NPC309717
0.9219	High Similarity	NPC475008
0.9219	High Similarity	NPC186097
0.92	High Similarity	NPC95309
0.9194	High Similarity	NPC255073
0.9174	High Similarity	NPC161617
0.9167	High Similarity	NPC21350
0.9167	High Similarity	NPC279668
0.9167	High Similarity	NPC278323
0.9167	High Similarity	NPC188947
0.9167	High Similarity	NPC99333
0.9167	High Similarity	NPC55162
0.9167	High Similarity	NPC309154
0.9167	High Similarity	NPC12175
0.9167	High Similarity	NPC124269
0.9167	High Similarity	NPC472368
0.9167	High Similarity	NPC280284
0.9167	High Similarity	NPC90665
0.916	High Similarity	NPC235428
0.916	High Similarity	NPC187826
0.916	High Similarity	NPC231772
0.916	High Similarity	NPC234133
0.916	High Similarity	NPC127447
0.916	High Similarity	NPC213603
0.916	High Similarity	NPC29353
0.916	High Similarity	NPC473887
0.916	High Similarity	NPC124784
0.916	High Similarity	NPC194281
0.916	High Similarity	NPC47815
0.916	High Similarity	NPC87545
0.9154	High Similarity	NPC103842
0.9154	High Similarity	NPC172262
0.9154	High Similarity	NPC125920
0.9154	High Similarity	NPC236974
0.9154	High Similarity	NPC144027
0.9147	High Similarity	NPC10971
0.9141	High Similarity	NPC250057
0.9134	High Similarity	NPC211120
0.9098	High Similarity	NPC137009
0.9098	High Similarity	NPC477956
0.9098	High Similarity	NPC472366
0.9098	High Similarity	NPC470211
0.9098	High Similarity	NPC49242
0.9098	High Similarity	NPC295384
0.9091	High Similarity	NPC212767
0.9091	High Similarity	NPC476480
0.9091	High Similarity	NPC290291
0.9091	High Similarity	NPC275055
0.9091	High Similarity	NPC84585
0.9091	High Similarity	NPC228661
0.9084	High Similarity	NPC239495
0.9084	High Similarity	NPC60667
0.9084	High Similarity	NPC9985
0.9084	High Similarity	NPC84699
0.9077	High Similarity	NPC50898
0.9077	High Similarity	NPC78540
0.9077	High Similarity	NPC213216
0.9077	High Similarity	NPC108113
0.9077	High Similarity	NPC93756
0.9077	High Similarity	NPC27643
0.9077	High Similarity	NPC274121
0.904	High Similarity	NPC6888
0.903	High Similarity	NPC219917
0.903	High Similarity	NPC101366
0.903	High Similarity	NPC80962
0.903	High Similarity	NPC172250
0.903	High Similarity	NPC281207
0.903	High Similarity	NPC326109
0.903	High Similarity	NPC269652
0.903	High Similarity	NPC259166
0.903	High Similarity	NPC11056
0.903	High Similarity	NPC48624
0.903	High Similarity	NPC213659
0.903	High Similarity	NPC144118
0.903	High Similarity	NPC215311
0.903	High Similarity	NPC204985
0.9023	High Similarity	NPC25427
0.9023	High Similarity	NPC472460
0.9023	High Similarity	NPC329225
0.9023	High Similarity	NPC251681
0.9023	High Similarity	NPC243528
0.9023	High Similarity	NPC147686
0.9023	High Similarity	NPC471620
0.9015	High Similarity	NPC470397
0.9015	High Similarity	NPC193792
0.9015	High Similarity	NPC156910
0.9015	High Similarity	NPC121243
0.9015	High Similarity	NPC470398
0.9015	High Similarity	NPC174999
0.9015	High Similarity	NPC240147
0.9015	High Similarity	NPC13408
0.9008	High Similarity	NPC182496
0.9008	High Similarity	NPC180905
0.8984	High Similarity	NPC187907
0.8976	High Similarity	NPC49852
0.8976	High Similarity	NPC475496
0.8963	High Similarity	NPC55832
0.8963	High Similarity	NPC301178

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 NPC80694 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	375
0.1-0.2	1019
0.2-0.3	1678
0.3-0.4	2752
0.4-0.5	1717
0.5-0.6	1098
0.6-0.7	358
0.7-0.8	120
0.8-0.85	26
0.85-0.9	4
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.968	High Similarity	NPD1240	Approved
0.9528	High Similarity	NPD1607	Approved
0.9231	High Similarity	NPD1510	Phase 2
0.9023	High Similarity	NPD1549	Phase 2
0.8947	High Similarity	NPD1552	Clinical (unspecified phase)
0.8947	High Similarity	NPD1550	Clinical (unspecified phase)
0.8741	High Similarity	NPD970	Clinical (unspecified phase)
0.8633	High Similarity	NPD4378	Clinical (unspecified phase)
0.8593	High Similarity	NPD2796	Approved
0.85	High Similarity	NPD7410	Clinical (unspecified phase)
0.8478	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8468	Intermediate Similarity	NPD9493	Approved
0.8429	Intermediate Similarity	NPD1511	Approved
0.8429	Intermediate Similarity	NPD6799	Approved
0.837	Intermediate Similarity	NPD6651	Approved
0.8333	Intermediate Similarity	NPD4380	Phase 2
0.8333	Intermediate Similarity	NPD9545	Approved
0.8321	Intermediate Similarity	NPD1551	Phase 2
0.831	Intermediate Similarity	NPD1512	Approved
0.8295	Intermediate Similarity	NPD9717	Approved
0.8276	Intermediate Similarity	NPD7411	Suspended
0.8219	Intermediate Similarity	NPD1934	Approved
0.8176	Intermediate Similarity	NPD3882	Suspended
0.8163	Intermediate Similarity	NPD2801	Approved
0.8163	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8143	Intermediate Similarity	NPD2654	Approved
0.8143	Intermediate Similarity	NPD2800	Approved
0.8143	Intermediate Similarity	NPD1243	Approved
0.8121	Intermediate Similarity	NPD7075	Discontinued
0.8108	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8106	Intermediate Similarity	NPD1203	Approved
0.8088	Intermediate Similarity	NPD943	Approved
0.8085	Intermediate Similarity	NPD3750	Approved
0.8082	Intermediate Similarity	NPD6599	Discontinued
0.8077	Intermediate Similarity	NPD422	Phase 1
0.8074	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8058	Intermediate Similarity	NPD2935	Discontinued
0.8041	Intermediate Similarity	NPD7819	Suspended
0.8041	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2344	Approved
0.7986	Intermediate Similarity	NPD2533	Approved
0.7986	Intermediate Similarity	NPD2534	Approved
0.7986	Intermediate Similarity	NPD2532	Approved
0.7973	Intermediate Similarity	NPD6801	Discontinued
0.7972	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7899	Intermediate Similarity	NPD230	Phase 1
0.7887	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD3749	Approved
0.7877	Intermediate Similarity	NPD920	Approved
0.7862	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD74	Approved
0.7823	Intermediate Similarity	NPD9266	Approved
0.7815	Intermediate Similarity	NPD7768	Phase 2
0.7806	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7795	Intermediate Similarity	NPD1241	Discontinued
0.7778	Intermediate Similarity	NPD2309	Approved
0.7778	Intermediate Similarity	NPD2798	Approved
0.7769	Intermediate Similarity	NPD1548	Phase 1
0.7755	Intermediate Similarity	NPD5403	Approved
0.7748	Intermediate Similarity	NPD3817	Phase 2
0.7744	Intermediate Similarity	NPD3972	Approved
0.7742	Intermediate Similarity	NPD9267	Approved
0.7742	Intermediate Similarity	NPD9264	Approved
0.7742	Intermediate Similarity	NPD9263	Approved
0.7742	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD5401	Approved
0.773	Intermediate Similarity	NPD3748	Approved
0.7721	Intermediate Similarity	NPD9494	Approved
0.7692	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6166	Phase 2
0.7692	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7681	Intermediate Similarity	NPD411	Approved
0.7677	Intermediate Similarity	NPD6232	Discontinued
0.7664	Intermediate Similarity	NPD6832	Phase 2
0.7647	Intermediate Similarity	NPD1019	Discontinued
0.7643	Intermediate Similarity	NPD447	Suspended
0.7643	Intermediate Similarity	NPD7473	Discontinued
0.7613	Intermediate Similarity	NPD6959	Discontinued
0.7606	Intermediate Similarity	NPD2799	Discontinued
0.7595	Intermediate Similarity	NPD3818	Discontinued
0.7562	Intermediate Similarity	NPD5953	Discontinued
0.7552	Intermediate Similarity	NPD6100	Approved
0.7552	Intermediate Similarity	NPD6099	Approved
0.7547	Intermediate Similarity	NPD7286	Phase 2
0.7547	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD7054	Approved
0.7537	Intermediate Similarity	NPD1610	Phase 2
0.75	Intermediate Similarity	NPD1729	Discontinued
0.75	Intermediate Similarity	NPD7074	Phase 3
0.75	Intermediate Similarity	NPD7472	Approved
0.7484	Intermediate Similarity	NPD919	Approved
0.7481	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD940	Approved
0.748	Intermediate Similarity	NPD846	Approved
0.7468	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD4628	Phase 3
0.7453	Intermediate Similarity	NPD6797	Phase 2
0.7445	Intermediate Similarity	NPD1164	Approved
0.7444	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD5494	Approved
0.7429	Intermediate Similarity	NPD2313	Discontinued
0.7429	Intermediate Similarity	NPD1296	Phase 2
0.7419	Intermediate Similarity	NPD9261	Approved
0.7407	Intermediate Similarity	NPD1201	Approved
0.7407	Intermediate Similarity	NPD7251	Discontinued
0.7403	Intermediate Similarity	NPD5402	Approved
0.74	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD1247	Approved
0.7372	Intermediate Similarity	NPD1876	Approved
0.7362	Intermediate Similarity	NPD7808	Phase 3
0.7362	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD9269	Phase 2
0.7353	Intermediate Similarity	NPD1608	Approved
0.7347	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD9281	Approved
0.7319	Intermediate Similarity	NPD1470	Approved
0.7319	Intermediate Similarity	NPD2797	Approved
0.7315	Intermediate Similarity	NPD7390	Discontinued
0.7313	Intermediate Similarity	NPD9268	Approved
0.7305	Intermediate Similarity	NPD3268	Approved
0.7303	Intermediate Similarity	NPD3226	Approved
0.7301	Intermediate Similarity	NPD6559	Discontinued
0.7296	Intermediate Similarity	NPD3926	Phase 2
0.7286	Intermediate Similarity	NPD4908	Phase 1
0.7273	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1933	Approved
0.7256	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD3225	Approved
0.7241	Intermediate Similarity	NPD7033	Discontinued
0.7241	Intermediate Similarity	NPD4308	Phase 3
0.7233	Intermediate Similarity	NPD5710	Approved
0.7233	Intermediate Similarity	NPD5711	Approved
0.7226	Intermediate Similarity	NPD1465	Phase 2
0.7203	Intermediate Similarity	NPD3140	Approved
0.7203	Intermediate Similarity	NPD3142	Approved
0.7195	Intermediate Similarity	NPD6104	Discontinued
0.7183	Intermediate Similarity	NPD3764	Approved
0.7183	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD2296	Approved
0.7163	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2346	Discontinued
0.7132	Intermediate Similarity	NPD17	Approved
0.7132	Intermediate Similarity	NPD1778	Approved
0.7117	Intermediate Similarity	NPD5844	Phase 1
0.7114	Intermediate Similarity	NPD7003	Approved
0.7101	Intermediate Similarity	NPD1481	Phase 2
0.7078	Intermediate Similarity	NPD7458	Discontinued
0.7071	Intermediate Similarity	NPD3266	Approved
0.7071	Intermediate Similarity	NPD3267	Approved
0.707	Intermediate Similarity	NPD4288	Approved
0.705	Intermediate Similarity	NPD4749	Approved
0.705	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD5124	Phase 1
0.7034	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD1535	Discovery
0.7027	Intermediate Similarity	NPD1471	Phase 3
0.7014	Intermediate Similarity	NPD520	Approved
0.7007	Intermediate Similarity	NPD4626	Approved
0.7	Intermediate Similarity	NPD1283	Approved
0.6993	Remote Similarity	NPD3027	Phase 3
0.6985	Remote Similarity	NPD1894	Discontinued
0.6977	Remote Similarity	NPD3134	Approved
0.6974	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.697	Remote Similarity	NPD228	Approved
0.6966	Remote Similarity	NPD1613	Approved
0.6966	Remote Similarity	NPD4307	Phase 2
0.6966	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD5405	Approved
0.6959	Remote Similarity	NPD5408	Approved
0.6959	Remote Similarity	NPD5404	Approved
0.6959	Remote Similarity	NPD5406	Approved
0.6954	Remote Similarity	NPD2354	Approved
0.6954	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD4363	Phase 3
0.6936	Remote Similarity	NPD4360	Phase 2
0.6934	Remote Similarity	NPD1651	Approved
0.6933	Remote Similarity	NPD2403	Approved
0.6933	Remote Similarity	NPD1652	Phase 2
0.6928	Remote Similarity	NPD4661	Approved
0.6928	Remote Similarity	NPD4662	Approved
0.6923	Remote Similarity	NPD290	Approved
0.6923	Remote Similarity	NPD1358	Approved
0.6913	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD4287	Approved
0.6901	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD4361	Phase 2
0.6897	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4625	Phase 3
0.685	Remote Similarity	NPD1242	Phase 1
0.6848	Remote Similarity	NPD3751	Discontinued
0.6842	Remote Similarity	NPD1609	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