NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	680.49
Volume:	734.553
LogP:	7.092
LogD:	4.481
LogS:	-5.488
# Rotatable Bonds:	30
TPSA:	146.66
# H-Bond Aceptor:	9
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.049
Synthetic Accessibility Score:	4.751
Fsp3:	0.846
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.181
MDCK Permeability:	1.2136410077800974e-05
Pgp-inhibitor:	0.42
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.026
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.974

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	96.31885528564453%
Volume Distribution (VD):	0.759
Pgp-substrate:	2.416299819946289%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.263
CYP2C19-inhibitor:	0.035
CYP2C19-substrate:	0.047
CYP2C9-inhibitor:	0.066
CYP2C9-substrate:	0.985
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.098
CYP3A4-inhibitor:	0.219
CYP3A4-substrate:	0.032

ADMET: Excretion

Clearance (CL):	4.084
Half-life (T1/2):	0.63

ADMET: Toxicity

hERG Blockers:	0.073
Human Hepatotoxicity (H-HT):	0.81
Drug-inuced Liver Injury (DILI):	0.275
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.074
Maximum Recommended Daily Dose:	0.921
Skin Sensitization:	0.959
Carcinogencity:	0.034
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.471

Download Data

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

Natural Product: NPC477016

Natural Product ID:	NPC477016
*Common Name:**	[(1R,13R)-1,13-dihydroxy-1-[(2R,5R)-5-[(1R)-1-hydroxytridecyl]oxolan-2-yl]-15-[(2S)-2-methyl-5-oxo-2H-furan-4-yl]-8-oxopentadecan-3-yl] acetate
IUPAC Name:	[(1R,13R)-1,13-dihydroxy-1-[(2R,5R)-5-[(1R)-1-hydroxytridecyl]oxolan-2-yl]-15-[(2S)-2-methyl-5-oxo-2H-furan-4-yl]-8-oxopentadecan-3-yl] acetate
Synonyms:	Plagioneurin D
Standard InCHIKey:	OJFDGOAJDAPKNG-QLPKJOPDSA-N
Standard InCHI:	InChI=1S/C39H68O9/c1-4-5-6-7-8-9-10-11-12-13-22-35(43)37-25-26-38(48-37)36(44)28-34(47-30(3)40)21-17-16-19-32(41)18-14-15-20-33(42)24-23-31-27-29(2)46-39(31)45/h27,29,33-38,42-44H,4-26,28H2,1-3H3/t29-,33+,34?,35+,36+,37+,38+/m0/s1
SMILES:	CCCCCCCCCCCC[C@H]([C@H]1CC[C@@H](O1)[C@@H](CC(CCCCC(=O)CCCC[C@H](CCC2=C[C@@H](OC2=O)C)O)OC(=O)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	16086536
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols [CHEMONTID:0002518] Annonaceous acetogenins

*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
NPO22123	Disepalum plagioneurum	Species	Annonaceae	Eukaryota	leaves	Tam Kim, Cao Bang Province, in North Vietnam	2000-JUN	PMID[16989521]
NPO22123	Disepalum plagioneurum	Species	Annonaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	2.8	nM	PMID[16989521]

☑ 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 NPC477016 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	193
0.1-0.2	1537
0.2-0.3	5710
0.3-0.4	11495
0.4-0.5	13048
0.5-0.6	6863
0.6-0.7	3051
0.7-0.8	599
0.8-0.85	40
0.85-0.9	60
0.9-0.95	86
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477017
0.988	High Similarity	NPC89001
0.9762	High Similarity	NPC280612
0.9639	High Similarity	NPC477010
0.9639	High Similarity	NPC477015
0.9529	High Similarity	NPC477011
0.9518	High Similarity	NPC329615
0.9518	High Similarity	NPC120398
0.9518	High Similarity	NPC477013
0.9518	High Similarity	NPC477014
0.9518	High Similarity	NPC471567
0.9518	High Similarity	NPC329838
0.9518	High Similarity	NPC477018
0.9518	High Similarity	NPC100921
0.9412	High Similarity	NPC21208
0.9412	High Similarity	NPC473905
0.9412	High Similarity	NPC320458
0.9412	High Similarity	NPC20339
0.9412	High Similarity	NPC48338
0.9412	High Similarity	NPC40376
0.9412	High Similarity	NPC233551
0.9412	High Similarity	NPC280621
0.9405	High Similarity	NPC309211
0.9398	High Similarity	NPC156804
0.9398	High Similarity	NPC163093
0.9294	High Similarity	NPC20533
0.9294	High Similarity	NPC178215
0.9294	High Similarity	NPC476583
0.9294	High Similarity	NPC477012
0.9294	High Similarity	NPC470401
0.9294	High Similarity	NPC159750
0.9294	High Similarity	NPC154097
0.9294	High Similarity	NPC258068
0.9294	High Similarity	NPC473649
0.9286	High Similarity	NPC322529
0.9277	High Similarity	NPC144415
0.9205	High Similarity	NPC11456
0.9195	High Similarity	NPC239517
0.9176	High Similarity	NPC103523
0.9176	High Similarity	NPC473840
0.9176	High Similarity	NPC62118
0.9176	High Similarity	NPC25703
0.9176	High Similarity	NPC282815
0.9176	High Similarity	NPC171174
0.9176	High Similarity	NPC473687
0.9176	High Similarity	NPC308412
0.9176	High Similarity	NPC114694
0.9176	High Similarity	NPC475581
0.9176	High Similarity	NPC107717
0.9176	High Similarity	NPC210218
0.9176	High Similarity	NPC241360
0.9176	High Similarity	NPC293136
0.9176	High Similarity	NPC134865
0.9176	High Similarity	NPC134807
0.9176	High Similarity	NPC204686
0.9176	High Similarity	NPC240695
0.9176	High Similarity	NPC232555
0.9176	High Similarity	NPC231096
0.9176	High Similarity	NPC219498
0.9176	High Similarity	NPC112685
0.9176	High Similarity	NPC132940
0.9176	High Similarity	NPC219652
0.9176	High Similarity	NPC134885
0.9176	High Similarity	NPC142117
0.9157	High Similarity	NPC473780
0.9157	High Similarity	NPC94875
0.9157	High Similarity	NPC475159
0.9157	High Similarity	NPC473529
0.9157	High Similarity	NPC11332
0.9157	High Similarity	NPC145914
0.9157	High Similarity	NPC131002
0.9157	High Similarity	NPC65930
0.9157	High Similarity	NPC73310
0.9157	High Similarity	NPC329829
0.9157	High Similarity	NPC473712
0.9157	High Similarity	NPC180363
0.908	High Similarity	NPC42598
0.908	High Similarity	NPC14901
0.908	High Similarity	NPC473504
0.908	High Similarity	NPC91067
0.908	High Similarity	NPC40066
0.908	High Similarity	NPC81778
0.908	High Similarity	NPC93794
0.908	High Similarity	NPC20621
0.908	High Similarity	NPC130359
0.908	High Similarity	NPC318963
0.9059	High Similarity	NPC9678
0.9059	High Similarity	NPC223871
0.9059	High Similarity	NPC475268
0.9059	High Similarity	NPC473669
0.9059	High Similarity	NPC82795
0.9059	High Similarity	NPC202055
0.9059	High Similarity	NPC25764
0.9059	High Similarity	NPC473156
0.9059	High Similarity	NPC66346
0.9059	High Similarity	NPC39167
0.9059	High Similarity	NPC132496
0.9059	High Similarity	NPC473671
0.9059	High Similarity	NPC283085
0.9059	High Similarity	NPC286338
0.9059	High Similarity	NPC39279
0.9059	High Similarity	NPC1083
0.9059	High Similarity	NPC235809
0.9059	High Similarity	NPC231009
0.9059	High Similarity	NPC110710
0.9059	High Similarity	NPC77871
0.9059	High Similarity	NPC107986
0.9059	High Similarity	NPC470400
0.9059	High Similarity	NPC473478
0.9059	High Similarity	NPC103284
0.9059	High Similarity	NPC292809
0.9059	High Similarity	NPC473651
0.9059	High Similarity	NPC319036
0.9048	High Similarity	NPC253801
0.8977	High Similarity	NPC473904
0.8966	High Similarity	NPC171135
0.8966	High Similarity	NPC169511
0.8966	High Similarity	NPC133730
0.8966	High Similarity	NPC234077
0.8966	High Similarity	NPC172821
0.8966	High Similarity	NPC151403
0.8966	High Similarity	NPC274446
0.8966	High Similarity	NPC100454
0.8966	High Similarity	NPC242364
0.8966	High Similarity	NPC61257
0.8966	High Similarity	NPC81045
0.8966	High Similarity	NPC39754
0.8966	High Similarity	NPC261952
0.8966	High Similarity	NPC287164
0.8966	High Similarity	NPC191929
0.8966	High Similarity	NPC320569
0.8953	High Similarity	NPC279267
0.8953	High Similarity	NPC69082
0.8864	High Similarity	NPC139418
0.8851	High Similarity	NPC473995
0.8736	High Similarity	NPC47937
0.8621	High Similarity	NPC182383
0.8571	High Similarity	NPC473723
0.8571	High Similarity	NPC473561
0.8571	High Similarity	NPC473663
0.8571	High Similarity	NPC475173
0.8571	High Similarity	NPC473520
0.8462	Intermediate Similarity	NPC473707
0.8387	Intermediate Similarity	NPC36954
0.837	Intermediate Similarity	NPC162205
0.837	Intermediate Similarity	NPC273579
0.837	Intermediate Similarity	NPC476300
0.837	Intermediate Similarity	NPC295204
0.837	Intermediate Similarity	NPC288240
0.8352	Intermediate Similarity	NPC473619
0.8261	Intermediate Similarity	NPC184463
0.8261	Intermediate Similarity	NPC30515
0.8261	Intermediate Similarity	NPC473321
0.8172	Intermediate Similarity	NPC475912
0.8172	Intermediate Similarity	NPC179746
0.8172	Intermediate Similarity	NPC81419
0.8152	Intermediate Similarity	NPC476004
0.8152	Intermediate Similarity	NPC474761
0.8152	Intermediate Similarity	NPC51004
0.8125	Intermediate Similarity	NPC473326
0.8105	Intermediate Similarity	NPC476315
0.8065	Intermediate Similarity	NPC12172
0.8065	Intermediate Similarity	NPC208886
0.8043	Intermediate Similarity	NPC295312
0.8043	Intermediate Similarity	NPC307411
0.8	Intermediate Similarity	NPC14961
0.8	Intermediate Similarity	NPC21469
0.8	Intermediate Similarity	NPC270013
0.8	Intermediate Similarity	NPC471142
0.798	Intermediate Similarity	NPC472755
0.798	Intermediate Similarity	NPC110989
0.7979	Intermediate Similarity	NPC212486
0.7957	Intermediate Similarity	NPC473448
0.7938	Intermediate Similarity	NPC471144
0.7935	Intermediate Similarity	NPC473715
0.7935	Intermediate Similarity	NPC202672
0.7917	Intermediate Similarity	NPC477921
0.7912	Intermediate Similarity	NPC469483
0.7912	Intermediate Similarity	NPC164393
0.79	Intermediate Similarity	NPC100487
0.79	Intermediate Similarity	NPC203659
0.7895	Intermediate Similarity	NPC81386
0.7895	Intermediate Similarity	NPC474035
0.7889	Intermediate Similarity	NPC474251
0.7889	Intermediate Similarity	NPC288471
0.7879	Intermediate Similarity	NPC225353
0.7879	Intermediate Similarity	NPC149371
0.7879	Intermediate Similarity	NPC320019
0.7879	Intermediate Similarity	NPC472754
0.7879	Intermediate Similarity	NPC324017
0.7849	Intermediate Similarity	NPC474032
0.7849	Intermediate Similarity	NPC92974
0.7841	Intermediate Similarity	NPC470147
0.7841	Intermediate Similarity	NPC133226
0.7841	Intermediate Similarity	NPC47653
0.7835	Intermediate Similarity	NPC40812
0.7826	Intermediate Similarity	NPC248602
0.7812	Intermediate Similarity	NPC477922
0.7802	Intermediate Similarity	NPC137033
0.78	Intermediate Similarity	NPC475871

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 NPC477016 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	174
0.1-0.2	2305
0.2-0.3	3843
0.3-0.4	1916
0.4-0.5	604
0.5-0.6	257
0.6-0.7	46
0.7-0.8	5
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
0.7957	Intermediate Similarity	NPD46	Approved
0.7957	Intermediate Similarity	NPD6698	Approved
0.7684	Intermediate Similarity	NPD7983	Approved
0.7579	Intermediate Similarity	NPD7838	Discovery
0.7573	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6686	Approved
0.71	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6371	Approved
0.6893	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD6435	Approved
0.6735	Remote Similarity	NPD4250	Approved
0.6735	Remote Similarity	NPD4251	Approved
0.6639	Remote Similarity	NPD7507	Approved
0.6633	Remote Similarity	NPD4249	Approved
0.6607	Remote Similarity	NPD6053	Discontinued
0.6581	Remote Similarity	NPD8516	Approved
0.6581	Remote Similarity	NPD8515	Approved
0.6581	Remote Similarity	NPD8513	Phase 3
0.6581	Remote Similarity	NPD8517	Approved
0.6538	Remote Similarity	NPD7839	Suspended
0.6535	Remote Similarity	NPD5785	Approved
0.6526	Remote Similarity	NPD5368	Approved
0.6512	Remote Similarity	NPD3197	Phase 1
0.6495	Remote Similarity	NPD7154	Phase 3
0.6477	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD7319	Approved
0.6471	Remote Similarity	NPD7830	Approved
0.6471	Remote Similarity	NPD7829	Approved
0.6449	Remote Similarity	NPD5344	Discontinued
0.6436	Remote Similarity	NPD1695	Approved
0.6415	Remote Similarity	NPD4225	Approved
0.6408	Remote Similarity	NPD5778	Approved
0.6408	Remote Similarity	NPD5779	Approved
0.6383	Remote Similarity	NPD4756	Discovery
0.6364	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5363	Approved
0.6354	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD7642	Approved
0.6327	Remote Similarity	NPD5362	Discontinued
0.6327	Remote Similarity	NPD6110	Phase 1
0.6325	Remote Similarity	NPD7641	Discontinued
0.6316	Remote Similarity	NPD8297	Approved
0.6311	Remote Similarity	NPD8074	Phase 3
0.6303	Remote Similarity	NPD8444	Approved
0.63	Remote Similarity	NPD5786	Approved
0.6262	Remote Similarity	NPD7638	Approved
0.625	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD6319	Approved
0.6204	Remote Similarity	NPD7639	Approved
0.6204	Remote Similarity	NPD7640	Approved
0.619	Remote Similarity	NPD5282	Discontinued
0.6161	Remote Similarity	NPD6412	Phase 2
0.6148	Remote Similarity	NPD7492	Approved
0.6146	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD4268	Approved
0.6146	Remote Similarity	NPD4271	Approved
0.614	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD7736	Approved
0.6121	Remote Similarity	NPD4632	Approved
0.6102	Remote Similarity	NPD7115	Discovery
0.61	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD6616	Approved
0.6083	Remote Similarity	NPD8294	Approved
0.6083	Remote Similarity	NPD8377	Approved
0.6083	Remote Similarity	NPD6054	Approved
0.6066	Remote Similarity	NPD8328	Phase 3
0.6061	Remote Similarity	NPD5209	Approved
0.6061	Remote Similarity	NPD4269	Approved
0.6061	Remote Similarity	NPD4270	Approved
0.6055	Remote Similarity	NPD6648	Approved
0.605	Remote Similarity	NPD7328	Approved
0.605	Remote Similarity	NPD7327	Approved
0.6048	Remote Similarity	NPD7078	Approved
0.6048	Remote Similarity	NPD8293	Discontinued
0.604	Remote Similarity	NPD1694	Approved
0.6033	Remote Similarity	NPD8380	Approved
0.6033	Remote Similarity	NPD8378	Approved
0.6033	Remote Similarity	NPD8033	Approved
0.6033	Remote Similarity	NPD8296	Approved
0.6033	Remote Similarity	NPD8335	Approved
0.6033	Remote Similarity	NPD8379	Approved
0.6024	Remote Similarity	NPD3728	Approved
0.6024	Remote Similarity	NPD3730	Approved
0.602	Remote Similarity	NPD4822	Approved
0.602	Remote Similarity	NPD4821	Approved
0.602	Remote Similarity	NPD4819	Approved
0.602	Remote Similarity	NPD4252	Approved
0.602	Remote Similarity	NPD4820	Approved
0.6	Remote Similarity	NPD7516	Approved
0.6	Remote Similarity	NPD7331	Phase 2
0.6	Remote Similarity	NPD8039	Approved
0.5984	Remote Similarity	NPD8080	Discontinued
0.5984	Remote Similarity	NPD7260	Phase 2
0.5984	Remote Similarity	NPD6370	Approved
0.5977	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5968	Remote Similarity	NPD8451	Approved
0.5965	Remote Similarity	NPD6899	Approved
0.5965	Remote Similarity	NPD6881	Approved
0.5965	Remote Similarity	NPD7320	Approved
0.5965	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD6101	Approved
0.5962	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.596	Remote Similarity	NPD5369	Approved
0.595	Remote Similarity	NPD6059	Approved
0.5948	Remote Similarity	NPD8130	Phase 1
0.5948	Remote Similarity	NPD6649	Approved
0.5948	Remote Similarity	NPD6650	Approved
0.5938	Remote Similarity	NPD6845	Suspended
0.5929	Remote Similarity	NPD5739	Approved
0.5929	Remote Similarity	NPD6675	Approved
0.5929	Remote Similarity	NPD7128	Approved
0.5929	Remote Similarity	NPD6402	Approved
0.592	Remote Similarity	NPD8448	Approved
0.5913	Remote Similarity	NPD6373	Approved
0.5913	Remote Similarity	NPD6372	Approved
0.5902	Remote Similarity	NPD6015	Approved
0.5902	Remote Similarity	NPD6016	Approved
0.5897	Remote Similarity	NPD6882	Approved
0.5889	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD5697	Approved
0.5862	Remote Similarity	NPD6883	Approved
0.5862	Remote Similarity	NPD7290	Approved
0.5862	Remote Similarity	NPD6421	Discontinued
0.5862	Remote Similarity	NPD7102	Approved
0.5854	Remote Similarity	NPD5988	Approved
0.5849	Remote Similarity	NPD6411	Approved
0.5847	Remote Similarity	NPD8133	Approved
0.5843	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD5331	Approved
0.5842	Remote Similarity	NPD5332	Approved
0.584	Remote Similarity	NPD8273	Phase 1
0.5833	Remote Similarity	NPD4266	Approved
0.5833	Remote Similarity	NPD3196	Approved
0.5833	Remote Similarity	NPD3194	Approved
0.5833	Remote Similarity	NPD6009	Approved
0.5833	Remote Similarity	NPD3195	Phase 2
0.5833	Remote Similarity	NPD7500	Approved
0.5833	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5824	Remote Similarity	NPD3704	Approved
0.5812	Remote Similarity	NPD2204	Approved
0.5812	Remote Similarity	NPD6847	Approved
0.5812	Remote Similarity	NPD6869	Approved
0.5812	Remote Similarity	NPD6617	Approved
0.5812	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD7604	Phase 2
0.5802	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.58	Remote Similarity	NPD4790	Discontinued
0.5789	Remote Similarity	NPD6008	Approved
0.5781	Remote Similarity	NPD8390	Approved
0.5781	Remote Similarity	NPD8391	Approved
0.5781	Remote Similarity	NPD8392	Approved
0.5776	Remote Similarity	NPD6013	Approved
0.5776	Remote Similarity	NPD6014	Approved
0.5776	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5776	Remote Similarity	NPD6012	Approved
0.5772	Remote Similarity	NPD8267	Approved
0.5772	Remote Similarity	NPD8266	Approved
0.5772	Remote Similarity	NPD8268	Approved
0.5772	Remote Similarity	NPD7503	Approved
0.5772	Remote Similarity	NPD8269	Approved
0.5772	Remote Similarity	NPD5983	Phase 2
0.5772	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.576	Remote Similarity	NPD8341	Approved
0.576	Remote Similarity	NPD8342	Approved
0.576	Remote Similarity	NPD8340	Approved
0.576	Remote Similarity	NPD8299	Approved
0.5747	Remote Similarity	NPD6109	Phase 1
0.5747	Remote Similarity	NPD69	Approved
0.5747	Remote Similarity	NPD9119	Approved
0.5741	Remote Similarity	NPD7748	Approved
0.5739	Remote Similarity	NPD5701	Approved
0.5727	Remote Similarity	NPD7902	Approved
0.5727	Remote Similarity	NPD6083	Phase 2
0.5727	Remote Similarity	NPD6084	Phase 2
0.5725	Remote Similarity	NPD8415	Approved
0.5714	Remote Similarity	NPD6336	Discontinued
0.5714	Remote Similarity	NPD3172	Approved
0.5702	Remote Similarity	NPD7505	Discontinued
0.5701	Remote Similarity	NPD7637	Suspended
0.569	Remote Similarity	NPD6011	Approved
0.5673	Remote Similarity	NPD6422	Discontinued
0.5664	Remote Similarity	NPD7632	Discontinued
0.5663	Remote Similarity	NPD6927	Phase 3
0.566	Remote Similarity	NPD5370	Suspended
0.5652	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5648	Remote Similarity	NPD6399	Phase 3
0.5632	Remote Similarity	NPD9118	Approved
0.5614	Remote Similarity	NPD6647	Phase 2
0.5607	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5604	Remote Similarity	NPD7909	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