NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	278.15
Volume:	298.714
LogP:	3.21
LogD:	3.371
LogS:	-2.871
# Rotatable Bonds:	6
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.664
Synthetic Accessibility Score:	3.361
Fsp3:	0.438
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:	-4.599
MDCK Permeability:	2.2360281946021132e-05
Pgp-inhibitor:	0.721
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.799
30% Bioavailability (F30%):	0.687

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.213
Plasma Protein Binding (PPB):	91.12610626220703%
Volume Distribution (VD):	1.145
Pgp-substrate:	10.48381233215332%

ADMET: Metabolism

CYP1A2-inhibitor:	0.838
CYP1A2-substrate:	0.861
CYP2C19-inhibitor:	0.912
CYP2C19-substrate:	0.888
CYP2C9-inhibitor:	0.7
CYP2C9-substrate:	0.618
CYP2D6-inhibitor:	0.877
CYP2D6-substrate:	0.503
CYP3A4-inhibitor:	0.869
CYP3A4-substrate:	0.733

ADMET: Excretion

Clearance (CL):	12.578
Half-life (T1/2):	0.817

ADMET: Toxicity

hERG Blockers:	0.047
Human Hepatotoxicity (H-HT):	0.073
Drug-inuced Liver Injury (DILI):	0.095
AMES Toxicity:	0.32
Rat Oral Acute Toxicity:	0.032
Maximum Recommended Daily Dose:	0.101
Skin Sensitization:	0.788
Carcinogencity:	0.215
Eye Corrosion:	0.036
Eye Irritation:	0.823
Respiratory Toxicity:	0.124

Download Data

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

Natural Product: NPC325301

Natural Product ID:	NPC325301
*Common Name:**	8-Methoxy-9-O-Angeloylthymol
IUPAC Name:	[2-(2-hydroxy-4-methylphenyl)-2-methoxypropyl] (Z)-2-methylbut-2-enoate
Synonyms:
Standard InCHIKey:	DLYGIKVZDGBGDN-SDQBBNPISA-N
Standard InCHI:	InChI=1S/C16H22O4/c1-6-12(3)15(18)20-10-16(4,19-5)13-8-7-11(2)9-14(13)17/h6-9,17H,10H2,1-5H3/b12-6-
SMILES:	C/C=C(C(=O)OCC(c1ccc(cc1O)C)(OC)C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1795996
PubChem CID:	21592275
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0002542] Benzylethers

*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
NPO6414	Eupatorium cannabinum	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21391659]
NPO6414	Eupatorium cannabinum	Species	Asteraceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[30653318]
NPO21343	Eupatorium fortunei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6414	Eupatorium cannabinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21343	Eupatorium fortunei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6414	Eupatorium cannabinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21343	Eupatorium fortunei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6414	Eupatorium cannabinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21343	Eupatorium fortunei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6414	Eupatorium cannabinum	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	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.	Inhibition	=	14.7	%	PMID[492495]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	13.6	%	PMID[492495]

☑ 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 NPC325301 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	230
0.1-0.2	1172
0.2-0.3	3183
0.3-0.4	7623
0.4-0.5	11234
0.5-0.6	4683
0.6-0.7	11288
0.7-0.8	3175
0.8-0.85	89
0.85-0.9	15
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9828	High Similarity	NPC327070
0.9569	High Similarity	NPC328485
0.9316	High Similarity	NPC160235
0.9217	High Similarity	NPC41851
0.8879	High Similarity	NPC26615
0.8871	High Similarity	NPC329272
0.8852	High Similarity	NPC477151
0.8852	High Similarity	NPC132518
0.8828	High Similarity	NPC472591
0.8803	High Similarity	NPC190212
0.876	High Similarity	NPC211164
0.875	High Similarity	NPC206205
0.8718	High Similarity	NPC228452
0.871	High Similarity	NPC469568
0.8629	High Similarity	NPC477152
0.856	High Similarity	NPC117794
0.8537	High Similarity	NPC165197
0.8537	High Similarity	NPC322569
0.8525	High Similarity	NPC98748
0.8525	High Similarity	NPC472593
0.8492	Intermediate Similarity	NPC170749
0.8492	Intermediate Similarity	NPC472592
0.8468	Intermediate Similarity	NPC25168
0.8417	Intermediate Similarity	NPC197513
0.84	Intermediate Similarity	NPC297193
0.8359	Intermediate Similarity	NPC257947
0.8359	Intermediate Similarity	NPC66331
0.8319	Intermediate Similarity	NPC228609
0.8293	Intermediate Similarity	NPC309434
0.8293	Intermediate Similarity	NPC203124
0.8291	Intermediate Similarity	NPC66834
0.8279	Intermediate Similarity	NPC123559
0.8271	Intermediate Similarity	NPC71108
0.8271	Intermediate Similarity	NPC267539
0.8271	Intermediate Similarity	NPC254832
0.8271	Intermediate Similarity	NPC204257
0.8271	Intermediate Similarity	NPC29317
0.8271	Intermediate Similarity	NPC229638
0.8271	Intermediate Similarity	NPC176102
0.8268	Intermediate Similarity	NPC10154
0.8268	Intermediate Similarity	NPC265413
0.8258	Intermediate Similarity	NPC200422
0.8258	Intermediate Similarity	NPC157478
0.8258	Intermediate Similarity	NPC289572
0.8258	Intermediate Similarity	NPC295406
0.8244	Intermediate Similarity	NPC7012
0.8235	Intermediate Similarity	NPC471535
0.8226	Intermediate Similarity	NPC38181
0.8226	Intermediate Similarity	NPC20230
0.8197	Intermediate Similarity	NPC232165
0.8189	Intermediate Similarity	NPC261992
0.8175	Intermediate Similarity	NPC469564
0.8174	Intermediate Similarity	NPC94343
0.8151	Intermediate Similarity	NPC75272
0.8151	Intermediate Similarity	NPC471954
0.8151	Intermediate Similarity	NPC98392
0.813	Intermediate Similarity	NPC281277
0.8125	Intermediate Similarity	NPC474532
0.8125	Intermediate Similarity	NPC20443
0.8125	Intermediate Similarity	NPC60517
0.8125	Intermediate Similarity	NPC146886
0.812	Intermediate Similarity	NPC43627
0.8115	Intermediate Similarity	NPC261453
0.8115	Intermediate Similarity	NPC328593
0.8115	Intermediate Similarity	NPC33749
0.8115	Intermediate Similarity	NPC114918
0.811	Intermediate Similarity	NPC188997
0.811	Intermediate Similarity	NPC302211
0.8106	Intermediate Similarity	NPC191395
0.8095	Intermediate Similarity	NPC470848
0.8095	Intermediate Similarity	NPC470849
0.8083	Intermediate Similarity	NPC183700
0.808	Intermediate Similarity	NPC90522
0.808	Intermediate Similarity	NPC328459
0.808	Intermediate Similarity	NPC121866
0.808	Intermediate Similarity	NPC263386
0.808	Intermediate Similarity	NPC141791
0.8077	Intermediate Similarity	NPC95034
0.8077	Intermediate Similarity	NPC142087
0.8077	Intermediate Similarity	NPC473993
0.8074	Intermediate Similarity	NPC115861
0.8065	Intermediate Similarity	NPC320864
0.8065	Intermediate Similarity	NPC160199
0.8062	Intermediate Similarity	NPC287473
0.806	Intermediate Similarity	NPC474097
0.8049	Intermediate Similarity	NPC233669
0.8049	Intermediate Similarity	NPC474967
0.8047	Intermediate Similarity	NPC248786
0.8045	Intermediate Similarity	NPC329427
0.8045	Intermediate Similarity	NPC317601
0.8034	Intermediate Similarity	NPC93831
0.8034	Intermediate Similarity	NPC130817
0.8034	Intermediate Similarity	NPC475225
0.8033	Intermediate Similarity	NPC95381
0.8031	Intermediate Similarity	NPC476165
0.8017	Intermediate Similarity	NPC139946
0.8016	Intermediate Similarity	NPC72977
0.8016	Intermediate Similarity	NPC14177
0.8016	Intermediate Similarity	NPC193193
0.8016	Intermediate Similarity	NPC31314
0.8015	Intermediate Similarity	NPC81261
0.8	Intermediate Similarity	NPC213552
0.8	Intermediate Similarity	NPC94637
0.8	Intermediate Similarity	NPC275519
0.8	Intermediate Similarity	NPC120225
0.7985	Intermediate Similarity	NPC185777
0.7984	Intermediate Similarity	NPC147896
0.7969	Intermediate Similarity	NPC46634
0.7967	Intermediate Similarity	NPC81808
0.7967	Intermediate Similarity	NPC217472
0.7956	Intermediate Similarity	NPC132723
0.7956	Intermediate Similarity	NPC76032
0.7956	Intermediate Similarity	NPC151946
0.7955	Intermediate Similarity	NPC131684
0.7953	Intermediate Similarity	NPC204466
0.7951	Intermediate Similarity	NPC302371
0.7949	Intermediate Similarity	NPC235762
0.7949	Intermediate Similarity	NPC471228
0.7949	Intermediate Similarity	NPC304638
0.7931	Intermediate Similarity	NPC72729
0.7931	Intermediate Similarity	NPC174911
0.7923	Intermediate Similarity	NPC240744
0.7923	Intermediate Similarity	NPC289459
0.7923	Intermediate Similarity	NPC167055
0.792	Intermediate Similarity	NPC65791
0.792	Intermediate Similarity	NPC122117
0.7917	Intermediate Similarity	NPC169450
0.7917	Intermediate Similarity	NPC206341
0.7914	Intermediate Similarity	NPC257003
0.791	Intermediate Similarity	NPC302844
0.791	Intermediate Similarity	NPC470160
0.7899	Intermediate Similarity	NPC53740
0.7899	Intermediate Similarity	NPC86744
0.7891	Intermediate Similarity	NPC147654
0.7891	Intermediate Similarity	NPC70752
0.7887	Intermediate Similarity	NPC472937
0.7887	Intermediate Similarity	NPC472938
0.7887	Intermediate Similarity	NPC472936
0.7886	Intermediate Similarity	NPC28784
0.7886	Intermediate Similarity	NPC296144
0.7883	Intermediate Similarity	NPC155963
0.7883	Intermediate Similarity	NPC476171
0.7879	Intermediate Similarity	NPC217431
0.7879	Intermediate Similarity	NPC478215
0.7879	Intermediate Similarity	NPC219923
0.7874	Intermediate Similarity	NPC202474
0.7872	Intermediate Similarity	NPC103910
0.7869	Intermediate Similarity	NPC470355
0.7869	Intermediate Similarity	NPC226250
0.7868	Intermediate Similarity	NPC27407
0.7868	Intermediate Similarity	NPC281169
0.7868	Intermediate Similarity	NPC142027
0.7868	Intermediate Similarity	NPC291119
0.7863	Intermediate Similarity	NPC475695
0.7857	Intermediate Similarity	NPC86198
0.7857	Intermediate Similarity	NPC329980
0.7852	Intermediate Similarity	NPC475468
0.7846	Intermediate Similarity	NPC474237
0.7846	Intermediate Similarity	NPC276962
0.7846	Intermediate Similarity	NPC246704
0.7846	Intermediate Similarity	NPC91475
0.7846	Intermediate Similarity	NPC265910
0.7846	Intermediate Similarity	NPC190086
0.7842	Intermediate Similarity	NPC195357
0.7842	Intermediate Similarity	NPC152771
0.784	Intermediate Similarity	NPC128825
0.784	Intermediate Similarity	NPC33717
0.7836	Intermediate Similarity	NPC473777
0.7836	Intermediate Similarity	NPC108553
0.7833	Intermediate Similarity	NPC260952
0.7833	Intermediate Similarity	NPC474352
0.7832	Intermediate Similarity	NPC81835
0.7829	Intermediate Similarity	NPC478058
0.7829	Intermediate Similarity	NPC77789
0.7829	Intermediate Similarity	NPC217756
0.7829	Intermediate Similarity	NPC18128
0.7826	Intermediate Similarity	NPC126739
0.7826	Intermediate Similarity	NPC279573
0.7826	Intermediate Similarity	NPC211110
0.7826	Intermediate Similarity	NPC197666
0.7823	Intermediate Similarity	NPC473931
0.7823	Intermediate Similarity	NPC474114
0.7823	Intermediate Similarity	NPC474050
0.782	Intermediate Similarity	NPC271832
0.782	Intermediate Similarity	NPC83062
0.7815	Intermediate Similarity	NPC47284
0.7815	Intermediate Similarity	NPC303141
0.7815	Intermediate Similarity	NPC288760
0.7815	Intermediate Similarity	NPC227255
0.7815	Intermediate Similarity	NPC243677
0.7812	Intermediate Similarity	NPC178395
0.7812	Intermediate Similarity	NPC159760
0.7812	Intermediate Similarity	NPC244994
0.7812	Intermediate Similarity	NPC222876
0.7812	Intermediate Similarity	NPC272454
0.7812	Intermediate Similarity	NPC115188
0.7812	Intermediate Similarity	NPC179092
0.7812	Intermediate Similarity	NPC26433
0.7812	Intermediate Similarity	NPC301987
0.7812	Intermediate Similarity	NPC35856

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 NPC325301 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	219
0.1-0.2	800
0.2-0.3	1594
0.3-0.4	2524
0.4-0.5	2025
0.5-0.6	1243
0.6-0.7	665
0.7-0.8	78
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.816	Intermediate Similarity	NPD4626	Approved
0.8095	Intermediate Similarity	NPD3496	Discontinued
0.808	Intermediate Similarity	NPD5691	Approved
0.784	Intermediate Similarity	NPD9493	Approved
0.7786	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4060	Phase 1
0.7754	Intermediate Similarity	NPD2935	Discontinued
0.7739	Intermediate Similarity	NPD844	Approved
0.7734	Intermediate Similarity	NPD1778	Approved
0.7686	Intermediate Similarity	NPD1358	Approved
0.7672	Intermediate Similarity	NPD288	Approved
0.7652	Intermediate Similarity	NPD2797	Approved
0.7619	Intermediate Similarity	NPD6671	Approved
0.7619	Intermediate Similarity	NPD4198	Discontinued
0.7591	Intermediate Similarity	NPD447	Suspended
0.7561	Intermediate Similarity	NPD4750	Phase 3
0.7554	Intermediate Similarity	NPD4308	Phase 3
0.7536	Intermediate Similarity	NPD6653	Approved
0.75	Intermediate Similarity	NPD3268	Approved
0.75	Intermediate Similarity	NPD4749	Approved
0.75	Intermediate Similarity	NPD411	Approved
0.7479	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD230	Phase 1
0.7459	Intermediate Similarity	NPD3134	Approved
0.7447	Intermediate Similarity	NPD7266	Discontinued
0.7442	Intermediate Similarity	NPD9545	Approved
0.7426	Intermediate Similarity	NPD7095	Approved
0.7424	Intermediate Similarity	NPD9717	Approved
0.7413	Intermediate Similarity	NPD8166	Discontinued
0.7413	Intermediate Similarity	NPD4628	Phase 3
0.7376	Intermediate Similarity	NPD6032	Approved
0.7372	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD422	Phase 1
0.7348	Intermediate Similarity	NPD1611	Approved
0.7338	Intermediate Similarity	NPD6355	Discontinued
0.7329	Intermediate Similarity	NPD2534	Approved
0.7329	Intermediate Similarity	NPD2533	Approved
0.7329	Intermediate Similarity	NPD2532	Approved
0.7324	Intermediate Similarity	NPD2346	Discontinued
0.7324	Intermediate Similarity	NPD5763	Approved
0.7324	Intermediate Similarity	NPD5762	Approved
0.7299	Intermediate Similarity	NPD4625	Phase 3
0.7279	Intermediate Similarity	NPD5736	Approved
0.7279	Intermediate Similarity	NPD2237	Approved
0.7273	Intermediate Similarity	NPD2424	Discontinued
0.7266	Intermediate Similarity	NPD4307	Phase 2
0.7266	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD1203	Approved
0.7258	Intermediate Similarity	NPD290	Approved
0.7254	Intermediate Similarity	NPD1551	Phase 2
0.7252	Intermediate Similarity	NPD5585	Approved
0.7246	Intermediate Similarity	NPD6798	Discontinued
0.7246	Intermediate Similarity	NPD7985	Registered
0.7246	Intermediate Similarity	NPD3764	Approved
0.7244	Intermediate Similarity	NPD7635	Approved
0.7241	Intermediate Similarity	NPD6190	Approved
0.7226	Intermediate Similarity	NPD6832	Phase 2
0.7214	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD7157	Approved
0.7206	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD9266	Approved
0.72	Intermediate Similarity	NPD2684	Approved
0.72	Intermediate Similarity	NPD74	Approved
0.7185	Intermediate Similarity	NPD3225	Approved
0.7185	Intermediate Similarity	NPD6696	Suspended
0.7185	Intermediate Similarity	NPD1283	Approved
0.7174	Intermediate Similarity	NPD3027	Phase 3
0.7174	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD228	Approved
0.7153	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3022	Approved
0.7143	Intermediate Similarity	NPD3021	Approved
0.7143	Intermediate Similarity	NPD2979	Phase 3
0.7133	Intermediate Similarity	NPD5404	Approved
0.7133	Intermediate Similarity	NPD2438	Suspended
0.7133	Intermediate Similarity	NPD5405	Approved
0.7133	Intermediate Similarity	NPD6099	Approved
0.7133	Intermediate Similarity	NPD6100	Approved
0.7133	Intermediate Similarity	NPD5406	Approved
0.7133	Intermediate Similarity	NPD5408	Approved
0.7133	Intermediate Similarity	NPD7458	Discontinued
0.7132	Intermediate Similarity	NPD3266	Approved
0.7132	Intermediate Similarity	NPD3267	Approved
0.7131	Intermediate Similarity	NPD846	Approved
0.7131	Intermediate Similarity	NPD940	Approved
0.7122	Intermediate Similarity	NPD1048	Approved
0.7122	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD9263	Approved
0.712	Intermediate Similarity	NPD9264	Approved
0.712	Intermediate Similarity	NPD9267	Approved
0.7119	Intermediate Similarity	NPD845	Approved
0.7113	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD7097	Phase 1
0.7111	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD7843	Approved
0.7107	Intermediate Similarity	NPD3020	Approved
0.7101	Intermediate Similarity	NPD4908	Phase 1
0.7099	Intermediate Similarity	NPD5536	Phase 2
0.7097	Intermediate Similarity	NPD9697	Approved
0.7095	Intermediate Similarity	NPD1578	Phase 2
0.7092	Intermediate Similarity	NPD5124	Phase 1
0.7092	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD1091	Approved
0.7086	Intermediate Similarity	NPD6599	Discontinued
0.7083	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6004	Phase 3
0.7083	Intermediate Similarity	NPD6002	Phase 3
0.7083	Intermediate Similarity	NPD6005	Phase 3
0.7083	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD1019	Discontinued
0.7078	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD6233	Phase 2
0.7071	Intermediate Similarity	NPD6663	Approved
0.707	Intermediate Similarity	NPD6232	Discontinued
0.7067	Intermediate Similarity	NPD1653	Approved
0.7063	Intermediate Similarity	NPD2182	Approved
0.7063	Intermediate Similarity	NPD7033	Discontinued
0.7063	Intermediate Similarity	NPD2799	Discontinued
0.7063	Intermediate Similarity	NPD5844	Phase 1
0.7059	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD4110	Phase 3
0.7055	Intermediate Similarity	NPD7003	Approved
0.7055	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD3750	Approved
0.7055	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD1398	Phase 1
0.7054	Intermediate Similarity	NPD5283	Phase 1
0.7037	Intermediate Similarity	NPD1608	Approved
0.7037	Intermediate Similarity	NPD2230	Approved
0.7037	Intermediate Similarity	NPD2233	Approved
0.7037	Intermediate Similarity	NPD2232	Approved
0.7031	Intermediate Similarity	NPD969	Suspended
0.7029	Intermediate Similarity	NPD2861	Phase 2
0.7023	Intermediate Similarity	NPD7340	Approved
0.7021	Intermediate Similarity	NPD1613	Approved
0.7021	Intermediate Similarity	NPD4140	Approved
0.7021	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD3226	Approved
0.7015	Intermediate Similarity	NPD3847	Discontinued
0.7008	Intermediate Similarity	NPD2067	Discontinued
0.7007	Intermediate Similarity	NPD1164	Approved
0.7007	Intermediate Similarity	NPD987	Approved
0.7007	Intermediate Similarity	NPD6362	Approved
0.7	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2860	Approved
0.7	Intermediate Similarity	NPD2313	Discontinued
0.7	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2859	Approved
0.6986	Remote Similarity	NPD1652	Phase 2
0.6986	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD4359	Approved
0.6984	Remote Similarity	NPD2342	Discontinued
0.6978	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD5535	Approved
0.697	Remote Similarity	NPD7644	Approved
0.6966	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD1281	Approved
0.6963	Remote Similarity	NPD1610	Phase 2
0.6957	Remote Similarity	NPD5647	Approved
0.6957	Remote Similarity	NPD2798	Approved
0.6953	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD7819	Suspended
0.6937	Remote Similarity	NPD7473	Discontinued
0.6935	Remote Similarity	NPD6647	Phase 2
0.6933	Remote Similarity	NPD2675	Approved
0.6933	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD2676	Approved
0.6928	Remote Similarity	NPD8150	Discontinued
0.6923	Remote Similarity	NPD1607	Approved
0.6923	Remote Similarity	NPD7075	Discontinued
0.6917	Remote Similarity	NPD1759	Phase 1
0.6917	Remote Similarity	NPD2934	Approved
0.6917	Remote Similarity	NPD2933	Approved
0.6913	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD6799	Approved
0.6908	Remote Similarity	NPD3455	Phase 2
0.6906	Remote Similarity	NPD9494	Approved
0.6906	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD968	Approved
0.6903	Remote Similarity	NPD5402	Approved
0.6901	Remote Similarity	NPD825	Approved
0.6901	Remote Similarity	NPD826	Approved
0.6901	Remote Similarity	NPD2203	Discontinued
0.6894	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD1470	Approved
0.6884	Remote Similarity	NPD3094	Phase 2
0.6883	Remote Similarity	NPD1934	Approved
0.6883	Remote Similarity	NPD37	Approved
0.6879	Remote Similarity	NPD6234	Discontinued
0.6871	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.687	Remote Similarity	NPD2629	Approved
0.687	Remote Similarity	NPD9281	Approved
0.6867	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD1651	Approved
0.6863	Remote Similarity	NPD4380	Phase 2

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