NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	280.2
Volume:	306.573
LogP:	3.327
LogD:	2.33
LogS:	-3.539
# Rotatable Bonds:	3
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.622
Synthetic Accessibility Score:	4.368
Fsp3:	0.824
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:	-4.636
MDCK Permeability:	1.8949776858789846e-05
Pgp-inhibitor:	0.694
Pgp-substrate:	0.192
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.737
30% Bioavailability (F30%):	0.411

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.273
Plasma Protein Binding (PPB):	89.58720397949219%
Volume Distribution (VD):	1.554
Pgp-substrate:	15.954669952392578%

ADMET: Metabolism

CYP1A2-inhibitor:	0.075
CYP1A2-substrate:	0.153
CYP2C19-inhibitor:	0.064
CYP2C19-substrate:	0.837
CYP2C9-inhibitor:	0.122
CYP2C9-substrate:	0.515
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.259
CYP3A4-inhibitor:	0.153
CYP3A4-substrate:	0.356

ADMET: Excretion

Clearance (CL):	5.968
Half-life (T1/2):	0.527

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.457
Drug-inuced Liver Injury (DILI):	0.121
AMES Toxicity:	0.051
Rat Oral Acute Toxicity:	0.958
Maximum Recommended Daily Dose:	0.903
Skin Sensitization:	0.263
Carcinogencity:	0.135
Eye Corrosion:	0.139
Eye Irritation:	0.693
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC283619

Natural Product ID:	NPC283619
*Common Name:**	Junceol A
IUPAC Name:	2-[(2R,4aR,5R,8S)-5-hydroxy-4a,8-dimethyl-3,4,5,6,7,8-hexahydro-2H-naphthalen-2-yl]propan-2-yl acetate
Synonyms:
Standard InCHIKey:	FORUHHDUOITCNL-BYMSMCERSA-N
Standard InCHI:	InChI=1S/C17H28O3/c1-11-6-7-15(19)17(5)9-8-13(10-14(11)17)16(3,4)20-12(2)18/h10-11,13,15,19H,6-9H2,1-5H3/t11-,13+,15+,17+/m0/s1
SMILES:	C[C@H]1CC[C@H]([C@]2(C)CC[C@H](C=C12)C(C)(C)OC(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL459235
PubChem CID:	10016534
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0000101] Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids

*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
NPO3452	Virgularia juncea	Species	Virgulariidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575967]
NPO1207	Microtropis triflora	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17972583]
NPO3452	Virgularia juncea	Species	Virgulariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20113	Tetraphis pellucida	Species	Tetraphidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7249	Euphorbia copiapina	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2897	Corbicula japonica	Species	Corbiculidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5505	Piptolepis ericoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1207	Microtropis triflora	Species	Celastraceae	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
ED50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	5.1	ug ml-1	PMID[485125]

☑ 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 NPC283619 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	161
0.1-0.2	1125
0.2-0.3	5025
0.3-0.4	14733
0.4-0.5	8648
0.5-0.6	6735
0.6-0.7	4880
0.7-0.8	1329
0.8-0.85	53
0.85-0.9	6
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9211	High Similarity	NPC142163
0.8947	High Similarity	NPC100906
0.8734	High Similarity	NPC470948
0.8718	High Similarity	NPC473420
0.8642	High Similarity	NPC474970
0.8533	High Similarity	NPC71152
0.8519	High Similarity	NPC476602
0.8519	High Similarity	NPC191965
0.85	High Similarity	NPC52108
0.85	High Similarity	NPC474789
0.8481	Intermediate Similarity	NPC159148
0.8462	Intermediate Similarity	NPC242767
0.8415	Intermediate Similarity	NPC137306
0.8415	Intermediate Similarity	NPC73038
0.8415	Intermediate Similarity	NPC84121
0.8415	Intermediate Similarity	NPC6979
0.8415	Intermediate Similarity	NPC325594
0.8378	Intermediate Similarity	NPC92801
0.8375	Intermediate Similarity	NPC256112
0.8356	Intermediate Similarity	NPC208999
0.8354	Intermediate Similarity	NPC281880
0.8313	Intermediate Similarity	NPC245004
0.8312	Intermediate Similarity	NPC265588
0.8293	Intermediate Similarity	NPC35933
0.8289	Intermediate Similarity	NPC243342
0.8289	Intermediate Similarity	NPC477138
0.8272	Intermediate Similarity	NPC23748
0.8272	Intermediate Similarity	NPC476927
0.8267	Intermediate Similarity	NPC167706
0.8267	Intermediate Similarity	NPC164022
0.825	Intermediate Similarity	NPC170303
0.825	Intermediate Similarity	NPC327002
0.825	Intermediate Similarity	NPC108476
0.8235	Intermediate Similarity	NPC221111
0.8235	Intermediate Similarity	NPC280149
0.8228	Intermediate Similarity	NPC44083
0.8228	Intermediate Similarity	NPC153987
0.8193	Intermediate Similarity	NPC473226
0.8193	Intermediate Similarity	NPC329692
0.8193	Intermediate Similarity	NPC131813
0.8182	Intermediate Similarity	NPC477923
0.8182	Intermediate Similarity	NPC66566
0.8182	Intermediate Similarity	NPC291503
0.8171	Intermediate Similarity	NPC306951
0.8171	Intermediate Similarity	NPC102048
0.8158	Intermediate Similarity	NPC471799
0.8148	Intermediate Similarity	NPC2524
0.8148	Intermediate Similarity	NPC73882
0.8118	Intermediate Similarity	NPC246028
0.8118	Intermediate Similarity	NPC20946
0.8118	Intermediate Similarity	NPC470588
0.8118	Intermediate Similarity	NPC473647
0.8101	Intermediate Similarity	NPC321514
0.8101	Intermediate Similarity	NPC35574
0.8095	Intermediate Similarity	NPC473097
0.8095	Intermediate Similarity	NPC71507
0.8095	Intermediate Similarity	NPC166857
0.8095	Intermediate Similarity	NPC131329
0.8077	Intermediate Similarity	NPC1973
0.8077	Intermediate Similarity	NPC167873
0.8072	Intermediate Similarity	NPC109528
0.8072	Intermediate Similarity	NPC52628
0.8068	Intermediate Similarity	NPC134067
0.8056	Intermediate Similarity	NPC290367
0.8052	Intermediate Similarity	NPC91858
0.8052	Intermediate Similarity	NPC104644
0.8052	Intermediate Similarity	NPC471797
0.8049	Intermediate Similarity	NPC49208
0.8049	Intermediate Similarity	NPC79945
0.8049	Intermediate Similarity	NPC132386
0.8049	Intermediate Similarity	NPC57370
0.8049	Intermediate Similarity	NPC311070
0.8026	Intermediate Similarity	NPC242992
0.8026	Intermediate Similarity	NPC242001
0.8025	Intermediate Similarity	NPC195334
0.8025	Intermediate Similarity	NPC25554
0.8025	Intermediate Similarity	NPC290495
0.8023	Intermediate Similarity	NPC474728
0.8023	Intermediate Similarity	NPC310479
0.8023	Intermediate Similarity	NPC78973
0.8	Intermediate Similarity	NPC327674
0.8	Intermediate Similarity	NPC473242
0.8	Intermediate Similarity	NPC290690
0.8	Intermediate Similarity	NPC246708
0.8	Intermediate Similarity	NPC181225
0.8	Intermediate Similarity	NPC473229
0.8	Intermediate Similarity	NPC40552
0.8	Intermediate Similarity	NPC474512
0.8	Intermediate Similarity	NPC291379
0.8	Intermediate Similarity	NPC17733
0.8	Intermediate Similarity	NPC470429
0.8	Intermediate Similarity	NPC470629
0.7978	Intermediate Similarity	NPC327179
0.7976	Intermediate Similarity	NPC82979
0.7976	Intermediate Similarity	NPC155011
0.7976	Intermediate Similarity	NPC471219
0.7976	Intermediate Similarity	NPC475069
0.7976	Intermediate Similarity	NPC175145
0.7975	Intermediate Similarity	NPC318495
0.7975	Intermediate Similarity	NPC471798
0.7975	Intermediate Similarity	NPC155986
0.7975	Intermediate Similarity	NPC477924
0.7975	Intermediate Similarity	NPC198968
0.7975	Intermediate Similarity	NPC470428
0.7955	Intermediate Similarity	NPC215700
0.7955	Intermediate Similarity	NPC474922
0.7952	Intermediate Similarity	NPC46320
0.7952	Intermediate Similarity	NPC302360
0.7949	Intermediate Similarity	NPC113639
0.7931	Intermediate Similarity	NPC285184
0.7931	Intermediate Similarity	NPC234335
0.7931	Intermediate Similarity	NPC177641
0.7931	Intermediate Similarity	NPC186363
0.7931	Intermediate Similarity	NPC472811
0.7931	Intermediate Similarity	NPC233345
0.7931	Intermediate Similarity	NPC470590
0.7931	Intermediate Similarity	NPC26888
0.7931	Intermediate Similarity	NPC77099
0.7931	Intermediate Similarity	NPC60755
0.7931	Intermediate Similarity	NPC477574
0.7931	Intermediate Similarity	NPC72845
0.7927	Intermediate Similarity	NPC286786
0.7922	Intermediate Similarity	NPC182717
0.7922	Intermediate Similarity	NPC220939
0.7922	Intermediate Similarity	NPC265485
0.7907	Intermediate Similarity	NPC261320
0.7907	Intermediate Similarity	NPC474396
0.7907	Intermediate Similarity	NPC314727
0.7907	Intermediate Similarity	NPC50488
0.7907	Intermediate Similarity	NPC16265
0.7907	Intermediate Similarity	NPC198664
0.7907	Intermediate Similarity	NPC274330
0.7907	Intermediate Similarity	NPC146554
0.7907	Intermediate Similarity	NPC143232
0.7901	Intermediate Similarity	NPC269791
0.7901	Intermediate Similarity	NPC206735
0.7901	Intermediate Similarity	NPC233332
0.7895	Intermediate Similarity	NPC34834
0.7895	Intermediate Similarity	NPC145498
0.7889	Intermediate Similarity	NPC285513
0.7889	Intermediate Similarity	NPC254496
0.7882	Intermediate Similarity	NPC187376
0.7882	Intermediate Similarity	NPC18064
0.7882	Intermediate Similarity	NPC293564
0.7882	Intermediate Similarity	NPC98442
0.7882	Intermediate Similarity	NPC142415
0.7882	Intermediate Similarity	NPC477926
0.7882	Intermediate Similarity	NPC102683
0.7882	Intermediate Similarity	NPC474684
0.7882	Intermediate Similarity	NPC88716
0.7882	Intermediate Similarity	NPC51700
0.7882	Intermediate Similarity	NPC171203
0.7882	Intermediate Similarity	NPC68160
0.7882	Intermediate Similarity	NPC142361
0.7882	Intermediate Similarity	NPC233836
0.7882	Intermediate Similarity	NPC242468
0.7882	Intermediate Similarity	NPC130577
0.7882	Intermediate Similarity	NPC307426
0.7882	Intermediate Similarity	NPC159046
0.7875	Intermediate Similarity	NPC474989
0.7875	Intermediate Similarity	NPC476949
0.7875	Intermediate Similarity	NPC22955
0.7875	Intermediate Similarity	NPC275910
0.7875	Intermediate Similarity	NPC476314
0.7875	Intermediate Similarity	NPC99168
0.7875	Intermediate Similarity	NPC470396
0.7865	Intermediate Similarity	NPC276110
0.7857	Intermediate Similarity	NPC164424
0.7857	Intermediate Similarity	NPC329738
0.7857	Intermediate Similarity	NPC471795
0.7857	Intermediate Similarity	NPC290731
0.7848	Intermediate Similarity	NPC106364
0.7848	Intermediate Similarity	NPC300324
0.7848	Intermediate Similarity	NPC477925
0.7848	Intermediate Similarity	NPC96319
0.7848	Intermediate Similarity	NPC321016
0.7848	Intermediate Similarity	NPC274079
0.7848	Intermediate Similarity	NPC240604
0.7848	Intermediate Similarity	NPC321381
0.7848	Intermediate Similarity	NPC107059
0.7841	Intermediate Similarity	NPC202728
0.7841	Intermediate Similarity	NPC474436
0.7841	Intermediate Similarity	NPC49776
0.7841	Intermediate Similarity	NPC63118
0.7841	Intermediate Similarity	NPC162615
0.7841	Intermediate Similarity	NPC472812
0.7841	Intermediate Similarity	NPC53555
0.7841	Intermediate Similarity	NPC118519
0.7841	Intermediate Similarity	NPC470224
0.7841	Intermediate Similarity	NPC158059
0.7841	Intermediate Similarity	NPC152778
0.7841	Intermediate Similarity	NPC86368
0.7841	Intermediate Similarity	NPC205034
0.7831	Intermediate Similarity	NPC312480
0.7831	Intermediate Similarity	NPC473592
0.7831	Intermediate Similarity	NPC472377
0.7821	Intermediate Similarity	NPC201048
0.7821	Intermediate Similarity	NPC476366
0.7821	Intermediate Similarity	NPC78527
0.7821	Intermediate Similarity	NPC100334

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 NPC283619 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	147
0.1-0.2	1536
0.2-0.3	3925
0.3-0.4	2358
0.4-0.5	734
0.5-0.6	242
0.6-0.7	195
0.7-0.8	13
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7848	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7645	Phase 2
0.7722	Intermediate Similarity	NPD6942	Approved
0.7722	Intermediate Similarity	NPD7339	Approved
0.7711	Intermediate Similarity	NPD3667	Approved
0.764	Intermediate Similarity	NPD6399	Phase 3
0.7595	Intermediate Similarity	NPD6926	Approved
0.7595	Intermediate Similarity	NPD6924	Approved
0.7556	Intermediate Similarity	NPD7748	Approved
0.7529	Intermediate Similarity	NPD4786	Approved
0.7528	Intermediate Similarity	NPD7515	Phase 2
0.747	Intermediate Similarity	NPD7525	Registered
0.7419	Intermediate Similarity	NPD4225	Approved
0.7407	Intermediate Similarity	NPD6933	Approved
0.7356	Intermediate Similarity	NPD3618	Phase 1
0.7333	Intermediate Similarity	NPD6411	Approved
0.7312	Intermediate Similarity	NPD7902	Approved
0.7284	Intermediate Similarity	NPD8264	Approved
0.7234	Intermediate Similarity	NPD7638	Approved
0.7209	Intermediate Similarity	NPD6695	Phase 3
0.7159	Intermediate Similarity	NPD7146	Approved
0.7159	Intermediate Similarity	NPD7334	Approved
0.7159	Intermediate Similarity	NPD7521	Approved
0.7159	Intermediate Similarity	NPD6409	Approved
0.7159	Intermediate Similarity	NPD6684	Approved
0.7159	Intermediate Similarity	NPD5330	Approved
0.7158	Intermediate Similarity	NPD7640	Approved
0.7158	Intermediate Similarity	NPD7639	Approved
0.7143	Intermediate Similarity	NPD7128	Approved
0.7143	Intermediate Similarity	NPD5739	Approved
0.7143	Intermediate Similarity	NPD6402	Approved
0.7143	Intermediate Similarity	NPD6675	Approved
0.7128	Intermediate Similarity	NPD6084	Phase 2
0.7128	Intermediate Similarity	NPD6083	Phase 2
0.7126	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD3665	Phase 1
0.7126	Intermediate Similarity	NPD3666	Approved
0.7126	Intermediate Similarity	NPD3133	Approved
0.7125	Intermediate Similarity	NPD7150	Approved
0.7125	Intermediate Similarity	NPD7151	Approved
0.7125	Intermediate Similarity	NPD7152	Approved
0.7111	Intermediate Similarity	NPD5328	Approved
0.7111	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD6051	Approved
0.7111	Intermediate Similarity	NPD6101	Approved
0.7097	Intermediate Similarity	NPD5695	Phase 3
0.7089	Intermediate Similarity	NPD6923	Approved
0.7089	Intermediate Similarity	NPD6922	Approved
0.7079	Intermediate Similarity	NPD3573	Approved
0.7079	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD5697	Approved
0.7071	Intermediate Similarity	NPD5701	Approved
0.7065	Intermediate Similarity	NPD4202	Approved
0.7059	Intermediate Similarity	NPD7509	Discontinued
0.7059	Intermediate Similarity	NPD6930	Phase 2
0.7059	Intermediate Similarity	NPD6931	Approved
0.7059	Intermediate Similarity	NPD4748	Discontinued
0.7045	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7144	Approved
0.7	Intermediate Similarity	NPD7143	Approved
0.7	Intermediate Similarity	NPD6899	Approved
0.7	Intermediate Similarity	NPD6903	Approved
0.7	Intermediate Similarity	NPD6011	Approved
0.7	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6881	Approved
0.7	Intermediate Similarity	NPD7320	Approved
0.6989	Remote Similarity	NPD7900	Approved
0.6989	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD5279	Phase 3
0.6957	Remote Similarity	NPD7637	Suspended
0.6957	Remote Similarity	NPD6079	Approved
0.6951	Remote Similarity	NPD4785	Approved
0.6951	Remote Similarity	NPD4784	Approved
0.6941	Remote Similarity	NPD6929	Approved
0.6941	Remote Similarity	NPD4195	Approved
0.6932	Remote Similarity	NPD3668	Phase 3
0.6932	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD6012	Approved
0.6931	Remote Similarity	NPD6373	Approved
0.6931	Remote Similarity	NPD6372	Approved
0.6931	Remote Similarity	NPD6013	Approved
0.6931	Remote Similarity	NPD6014	Approved
0.6914	Remote Similarity	NPD4243	Approved
0.6905	Remote Similarity	NPD6932	Approved
0.6897	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD7524	Approved
0.6889	Remote Similarity	NPD7750	Discontinued
0.6882	Remote Similarity	NPD5778	Approved
0.6882	Remote Similarity	NPD5779	Approved
0.6875	Remote Similarity	NPD5696	Approved
0.6863	Remote Similarity	NPD7102	Approved
0.6863	Remote Similarity	NPD7290	Approved
0.6863	Remote Similarity	NPD6883	Approved
0.686	Remote Similarity	NPD4695	Discontinued
0.6842	Remote Similarity	NPD368	Approved
0.6824	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6672	Approved
0.6813	Remote Similarity	NPD5737	Approved
0.6796	Remote Similarity	NPD6649	Approved
0.6796	Remote Similarity	NPD6847	Approved
0.6796	Remote Similarity	NPD6617	Approved
0.6796	Remote Similarity	NPD6650	Approved
0.6796	Remote Similarity	NPD6869	Approved
0.6796	Remote Similarity	NPD8130	Phase 1
0.6796	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD6098	Approved
0.6774	Remote Similarity	NPD8035	Phase 2
0.6774	Remote Similarity	NPD8034	Phase 2
0.6771	Remote Similarity	NPD4755	Approved
0.6744	Remote Similarity	NPD6683	Phase 2
0.6739	Remote Similarity	NPD4753	Phase 2
0.6735	Remote Similarity	NPD5344	Discontinued
0.6731	Remote Similarity	NPD8297	Approved
0.6731	Remote Similarity	NPD6882	Approved
0.6706	Remote Similarity	NPD6925	Approved
0.6706	Remote Similarity	NPD5776	Phase 2
0.6705	Remote Similarity	NPD4221	Approved
0.6705	Remote Similarity	NPD4223	Phase 3
0.6667	Remote Similarity	NPD6893	Approved
0.6667	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7514	Phase 3
0.6667	Remote Similarity	NPD1694	Approved
0.6667	Remote Similarity	NPD4190	Phase 3
0.6667	Remote Similarity	NPD7332	Phase 2
0.6667	Remote Similarity	NPD4697	Phase 3
0.6667	Remote Similarity	NPD5275	Approved
0.6667	Remote Similarity	NPD5222	Approved
0.6667	Remote Similarity	NPD5221	Approved
0.6636	Remote Similarity	NPD7115	Discovery
0.6634	Remote Similarity	NPD6008	Approved
0.6633	Remote Similarity	NPD4696	Approved
0.6633	Remote Similarity	NPD5285	Approved
0.6633	Remote Similarity	NPD5286	Approved
0.6633	Remote Similarity	NPD4700	Approved
0.663	Remote Similarity	NPD5208	Approved
0.6628	Remote Similarity	NPD7145	Approved
0.6598	Remote Similarity	NPD5173	Approved
0.6596	Remote Similarity	NPD5284	Approved
0.6596	Remote Similarity	NPD7087	Discontinued
0.6596	Remote Similarity	NPD5281	Approved
0.6591	Remote Similarity	NPD6898	Phase 1
0.6591	Remote Similarity	NPD5369	Approved
0.6582	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD5223	Approved
0.6562	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD6904	Approved
0.6559	Remote Similarity	NPD6673	Approved
0.6559	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD6080	Approved
0.6556	Remote Similarity	NPD4197	Approved
0.6542	Remote Similarity	NPD6274	Approved
0.6531	Remote Similarity	NPD5290	Discontinued
0.6509	Remote Similarity	NPD4632	Approved
0.65	Remote Similarity	NPD5225	Approved
0.65	Remote Similarity	NPD5226	Approved
0.65	Remote Similarity	NPD7632	Discontinued
0.65	Remote Similarity	NPD4633	Approved
0.65	Remote Similarity	NPD5224	Approved
0.65	Remote Similarity	NPD5211	Phase 2
0.6489	Remote Similarity	NPD5207	Approved
0.6489	Remote Similarity	NPD5692	Phase 3
0.6484	Remote Similarity	NPD5329	Approved
0.6481	Remote Similarity	NPD6317	Approved
0.6477	Remote Similarity	NPD4819	Approved
0.6477	Remote Similarity	NPD4820	Approved
0.6477	Remote Similarity	NPD4822	Approved
0.6477	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD4821	Approved
0.6471	Remote Similarity	NPD8039	Approved
0.6465	Remote Similarity	NPD6648	Approved
0.6458	Remote Similarity	NPD5707	Approved
0.6458	Remote Similarity	NPD6001	Approved
0.6456	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD5362	Discontinued
0.6444	Remote Similarity	NPD7154	Phase 3
0.6442	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD4754	Approved
0.6436	Remote Similarity	NPD5174	Approved
0.6436	Remote Similarity	NPD5175	Approved
0.6422	Remote Similarity	NPD6335	Approved
0.6422	Remote Similarity	NPD6313	Approved
0.6422	Remote Similarity	NPD6314	Approved
0.6421	Remote Similarity	NPD5694	Approved
0.6421	Remote Similarity	NPD6050	Approved
0.6421	Remote Similarity	NPD5693	Phase 1
0.6413	Remote Similarity	NPD4138	Approved
0.6413	Remote Similarity	NPD4693	Phase 3
0.6413	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD4688	Approved
0.6413	Remote Similarity	NPD4623	Approved
0.6413	Remote Similarity	NPD4690	Approved
0.6413	Remote Similarity	NPD5280	Approved
0.6413	Remote Similarity	NPD4519	Discontinued
0.6413	Remote Similarity	NPD5690	Phase 2
0.6413	Remote Similarity	NPD5205	Approved
0.6413	Remote Similarity	NPD4689	Approved
0.6413	Remote Similarity	NPD6422	Discontinued
0.6413	Remote Similarity	NPD4694	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