NPASS Compound

Structure

CID154517 OpenBabel06191715522D 27 28 0 0 0 0 0 0 0 0999 V2000 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 18 1 0 0 0 0 3 26 1 0 0 0 0 4 5 1 0 0 0 0 4 7 1 0 0 0 0 5 8 1 0 0 0 0 6 9 2 0 0 0 0 6 10 1 0 0 0 0 7 11 1 0 0 0 0 8 12 1 0 0 0 0 9 13 1 0 0 0 0 10 14 2 0 0 0 0 11 17 1 0 0 0 0 12 19 1 0 0 0 0 13 19 2 0 0 0 0 14 19 1 0 0 0 0 15 16 1 0 0 0 0 15 17 2 0 0 0 0 16 20 1 0 0 0 0 18 20 2 0 0 0 0 18 21 1 0 0 0 0 20 27 1 0 0 0 0 21 22 2 0 0 0 0 21 24 1 0 0 0 0 22 23 1 0 0 0 0 22 26 1 0 0 0 0 23 25 2 0 0 0 0 23 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	370.21
Volume:	405.957
LogP:	5.715
LogD:	4.877
LogS:	-5.235
# Rotatable Bonds:	10
TPSA:	59.67
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.561
Synthetic Accessibility Score:	3.11
Fsp3:	0.435
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.8
MDCK Permeability:	1.3109860447002575e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.023
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.158
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.093
Plasma Protein Binding (PPB):	100.54361724853516%
Volume Distribution (VD):	1.203
Pgp-substrate:	0.8109279870986938%

ADMET: Metabolism

CYP1A2-inhibitor:	0.913
CYP1A2-substrate:	0.884
CYP2C19-inhibitor:	0.956
CYP2C19-substrate:	0.489
CYP2C9-inhibitor:	0.947
CYP2C9-substrate:	0.951
CYP2D6-inhibitor:	0.573
CYP2D6-substrate:	0.711
CYP3A4-inhibitor:	0.889
CYP3A4-substrate:	0.383

ADMET: Excretion

Clearance (CL):	4.825
Half-life (T1/2):	0.304

ADMET: Toxicity

hERG Blockers:	0.087
Human Hepatotoxicity (H-HT):	0.936
Drug-inuced Liver Injury (DILI):	0.931
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.095
Maximum Recommended Daily Dose:	0.206
Skin Sensitization:	0.94
Carcinogencity:	0.147
Eye Corrosion:	0.004
Eye Irritation:	0.045
Respiratory Toxicity:	0.447

Download Data

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

Natural Product: NPC154517

Natural Product ID:	NPC154517
*Common Name:**	Lehualide F
IUPAC Name:	4-hydroxy-3-methoxy-5-methyl-6-[(E)-3-methyl-9-phenylnon-2-enyl]pyran-2-one
Synonyms:	Lehualide F
Standard InCHIKey:	RLHYLTRNTUTEBU-BMRADRMJSA-N
Standard InCHI:	InChI=1S/C23H30O4/c1-17(11-7-4-5-8-12-19-13-9-6-10-14-19)15-16-20-18(2)21(24)22(26-3)23(25)27-20/h6,9-10,13-15,24H,4-5,7-8,11-12,16H2,1-3H3/b17-15+
SMILES:	COc1c(=O)oc(c(c1O)C)C/C=C(/CCCCCCc1ccccc1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1773930
PubChem CID:	54728953
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000086] Pyrans [CHEMONTID:0000481] Pyranones and derivatives

*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
NPO31509	Plakortis	Genus	Plakinidae	Eukaryota	n.a.	Hawaiian	n.a.	PMID[16180823]
NPO31509	Plakortis	Genus	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21351759]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2
Others	2

Activity Type	# Activity
Cell Line	1
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	6200.0	nM	PMID[568685]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	GI	=	60.0	%	PMID[568685]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC50	=	44000.0	nM	PMID[568685]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	GI	=	48.0	%	PMID[568685]

☑ 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 NPC154517 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	337
0.1-0.2	1528
0.2-0.3	4634
0.3-0.4	10350
0.4-0.5	8023
0.5-0.6	4760
0.6-0.7	6689
0.7-0.8	5919
0.8-0.85	414
0.85-0.9	40
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9891	High Similarity	NPC80115
0.9783	High Similarity	NPC135951
0.8478	Intermediate Similarity	NPC53299
0.8454	Intermediate Similarity	NPC473347
0.8352	Intermediate Similarity	NPC99240
0.835	Intermediate Similarity	NPC477251
0.8333	Intermediate Similarity	NPC472319
0.8302	Intermediate Similarity	NPC477250
0.8173	Intermediate Similarity	NPC136962
0.8163	Intermediate Similarity	NPC23453
0.8105	Intermediate Similarity	NPC96625
0.8105	Intermediate Similarity	NPC286608
0.8105	Intermediate Similarity	NPC169050
0.8043	Intermediate Similarity	NPC71795
0.8	Intermediate Similarity	NPC472316
0.8	Intermediate Similarity	NPC474376
0.8	Intermediate Similarity	NPC475203
0.8	Intermediate Similarity	NPC472315
0.7981	Intermediate Similarity	NPC242913
0.7981	Intermediate Similarity	NPC280616
0.7981	Intermediate Similarity	NPC171831
0.7872	Intermediate Similarity	NPC127491
0.7872	Intermediate Similarity	NPC308619
0.7872	Intermediate Similarity	NPC324835
0.787	Intermediate Similarity	NPC477247
0.7857	Intermediate Similarity	NPC108026
0.785	Intermediate Similarity	NPC281604
0.783	Intermediate Similarity	NPC37115
0.7798	Intermediate Similarity	NPC234376
0.7757	Intermediate Similarity	NPC156648
0.7736	Intermediate Similarity	NPC127676
0.7727	Intermediate Similarity	NPC265002
0.7714	Intermediate Similarity	NPC91820
0.7714	Intermediate Similarity	NPC82426
0.77	Intermediate Similarity	NPC77273
0.7684	Intermediate Similarity	NPC208183
0.7684	Intermediate Similarity	NPC243289
0.766	Intermediate Similarity	NPC303245
0.766	Intermediate Similarity	NPC89950
0.7647	Intermediate Similarity	NPC30361
0.7634	Intermediate Similarity	NPC78517
0.7634	Intermediate Similarity	NPC167577
0.7609	Intermediate Similarity	NPC287790
0.7609	Intermediate Similarity	NPC3672
0.7593	Intermediate Similarity	NPC277788
0.7547	Intermediate Similarity	NPC234305
0.7542	Intermediate Similarity	NPC14141
0.7542	Intermediate Similarity	NPC471466
0.7527	Intermediate Similarity	NPC176228
0.7523	Intermediate Similarity	NPC114741
0.7523	Intermediate Similarity	NPC182549
0.75	Intermediate Similarity	NPC240108
0.75	Intermediate Similarity	NPC213156
0.75	Intermediate Similarity	NPC175393
0.7477	Intermediate Similarity	NPC85977
0.7431	Intermediate Similarity	NPC20485
0.7431	Intermediate Similarity	NPC475465
0.7431	Intermediate Similarity	NPC472314
0.7429	Intermediate Similarity	NPC474308
0.7429	Intermediate Similarity	NPC98911
0.7429	Intermediate Similarity	NPC472318
0.7411	Intermediate Similarity	NPC477245
0.7411	Intermediate Similarity	NPC477246
0.7391	Intermediate Similarity	NPC32203
0.7391	Intermediate Similarity	NPC206800
0.7387	Intermediate Similarity	NPC323007
0.7387	Intermediate Similarity	NPC183700
0.7373	Intermediate Similarity	NPC475328
0.735	Intermediate Similarity	NPC243059
0.735	Intermediate Similarity	NPC280827
0.734	Intermediate Similarity	NPC50192
0.7333	Intermediate Similarity	NPC179411
0.7327	Intermediate Similarity	NPC110420
0.7327	Intermediate Similarity	NPC26224
0.7327	Intermediate Similarity	NPC303967
0.7327	Intermediate Similarity	NPC67585
0.7321	Intermediate Similarity	NPC474689
0.7321	Intermediate Similarity	NPC139946
0.7315	Intermediate Similarity	NPC269644
0.7304	Intermediate Similarity	NPC108532
0.7297	Intermediate Similarity	NPC273837
0.7297	Intermediate Similarity	NPC79543
0.7281	Intermediate Similarity	NPC469509
0.7273	Intermediate Similarity	NPC260952
0.7273	Intermediate Similarity	NPC47536
0.7265	Intermediate Similarity	NPC204784
0.7248	Intermediate Similarity	NPC472919
0.7245	Intermediate Similarity	NPC44546
0.7236	Intermediate Similarity	NPC217431
0.7222	Intermediate Similarity	NPC304638
0.7222	Intermediate Similarity	NPC160382
0.7217	Intermediate Similarity	NPC296526
0.7217	Intermediate Similarity	NPC476476
0.7212	Intermediate Similarity	NPC5472
0.7207	Intermediate Similarity	NPC184633
0.7207	Intermediate Similarity	NPC40178
0.7203	Intermediate Similarity	NPC474223
0.7203	Intermediate Similarity	NPC475827
0.7196	Intermediate Similarity	NPC253746
0.7182	Intermediate Similarity	NPC51174
0.7172	Intermediate Similarity	NPC475710
0.7172	Intermediate Similarity	NPC123476
0.717	Intermediate Similarity	NPC476120
0.717	Intermediate Similarity	NPC145052
0.7168	Intermediate Similarity	NPC470825
0.7168	Intermediate Similarity	NPC470355
0.7156	Intermediate Similarity	NPC109637
0.7155	Intermediate Similarity	NPC470820
0.7143	Intermediate Similarity	NPC75272
0.7143	Intermediate Similarity	NPC323379
0.7143	Intermediate Similarity	NPC471954
0.7143	Intermediate Similarity	NPC327204
0.713	Intermediate Similarity	NPC94343
0.7129	Intermediate Similarity	NPC304760
0.712	Intermediate Similarity	NPC289415
0.712	Intermediate Similarity	NPC17567
0.712	Intermediate Similarity	NPC319995
0.7105	Intermediate Similarity	NPC131530
0.7105	Intermediate Similarity	NPC272524
0.7103	Intermediate Similarity	NPC171843
0.7097	Intermediate Similarity	NPC110313
0.7094	Intermediate Similarity	NPC183154
0.7094	Intermediate Similarity	NPC263754
0.7094	Intermediate Similarity	NPC122117
0.7087	Intermediate Similarity	NPC477281
0.7087	Intermediate Similarity	NPC119631
0.7087	Intermediate Similarity	NPC477280
0.7087	Intermediate Similarity	NPC19719
0.7083	Intermediate Similarity	NPC469894
0.708	Intermediate Similarity	NPC43584
0.708	Intermediate Similarity	NPC63345
0.7075	Intermediate Similarity	NPC133135
0.7075	Intermediate Similarity	NPC278228
0.7075	Intermediate Similarity	NPC103048
0.7075	Intermediate Similarity	NPC251579
0.7071	Intermediate Similarity	NPC267704
0.7069	Intermediate Similarity	NPC471616
0.7069	Intermediate Similarity	NPC216387
0.7065	Intermediate Similarity	NPC155429
0.7059	Intermediate Similarity	NPC2058
0.7059	Intermediate Similarity	NPC193193
0.7059	Intermediate Similarity	NPC173443
0.7059	Intermediate Similarity	NPC31314
0.7054	Intermediate Similarity	NPC475282
0.7054	Intermediate Similarity	NPC206341
0.7054	Intermediate Similarity	NPC474364
0.7054	Intermediate Similarity	NPC469511
0.7043	Intermediate Similarity	NPC474641
0.7043	Intermediate Similarity	NPC87069
0.704	Intermediate Similarity	NPC253595
0.7034	Intermediate Similarity	NPC203124
0.7034	Intermediate Similarity	NPC471033
0.7034	Intermediate Similarity	NPC309434
0.7034	Intermediate Similarity	NPC311091
0.7025	Intermediate Similarity	NPC474159
0.7025	Intermediate Similarity	NPC327070
0.7025	Intermediate Similarity	NPC325301
0.7025	Intermediate Similarity	NPC474254
0.7018	Intermediate Similarity	NPC158282
0.7018	Intermediate Similarity	NPC474314
0.7018	Intermediate Similarity	NPC185840
0.7016	Intermediate Similarity	NPC473993
0.7009	Intermediate Similarity	NPC33717
0.7009	Intermediate Similarity	NPC281277
0.7008	Intermediate Similarity	NPC173034
0.7	Intermediate Similarity	NPC470849
0.7	Intermediate Similarity	NPC472221
0.7	Intermediate Similarity	NPC58616
0.7	Intermediate Similarity	NPC472222
0.7	Intermediate Similarity	NPC2518
0.7	Intermediate Similarity	NPC470848
0.6983	Remote Similarity	NPC33749
0.6983	Remote Similarity	NPC261453
0.6983	Remote Similarity	NPC328593
0.6983	Remote Similarity	NPC41851
0.6983	Remote Similarity	NPC210092
0.6975	Remote Similarity	NPC241634
0.6975	Remote Similarity	NPC141791
0.6975	Remote Similarity	NPC263386
0.6967	Remote Similarity	NPC472373
0.696	Remote Similarity	NPC93632
0.6957	Remote Similarity	NPC199462
0.6957	Remote Similarity	NPC266116
0.6957	Remote Similarity	NPC48525
0.6957	Remote Similarity	NPC161611
0.6953	Remote Similarity	NPC202743
0.6937	Remote Similarity	NPC243677
0.6937	Remote Similarity	NPC269457
0.6937	Remote Similarity	NPC288760
0.6937	Remote Similarity	NPC209632
0.6937	Remote Similarity	NPC227255
0.6935	Remote Similarity	NPC213552
0.6935	Remote Similarity	NPC276047
0.6935	Remote Similarity	NPC120225
0.6935	Remote Similarity	NPC267733
0.693	Remote Similarity	NPC476003
0.693	Remote Similarity	NPC133308
0.693	Remote Similarity	NPC474157
0.6929	Remote Similarity	NPC108553
0.6923	Remote Similarity	NPC64230

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 NPC154517 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	315
0.1-0.2	917
0.2-0.3	1634
0.3-0.4	2724
0.4-0.5	1942
0.5-0.6	1134
0.6-0.7	360
0.7-0.8	116
0.8-0.85	7
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8105	Intermediate Similarity	NPD1282	Approved
0.7944	Intermediate Similarity	NPD2067	Discontinued
0.781	Intermediate Similarity	NPD5909	Discontinued
0.7684	Intermediate Similarity	NPD3971	Phase 1
0.7589	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD689	Discontinued
0.7526	Intermediate Similarity	NPD5734	Clinical (unspecified phase)
0.7522	Intermediate Similarity	NPD4198	Discontinued
0.7391	Intermediate Similarity	NPD9716	Approved
0.7222	Intermediate Similarity	NPD6647	Phase 2
0.717	Intermediate Similarity	NPD5926	Approved
0.7168	Intermediate Similarity	NPD969	Suspended
0.7155	Intermediate Similarity	NPD694	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD2629	Approved
0.7117	Intermediate Similarity	NPD1358	Approved
0.7115	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6049	Phase 2
0.7048	Intermediate Similarity	NPD6048	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD5048	Discontinued
0.6875	Remote Similarity	NPD4060	Phase 1
0.6875	Remote Similarity	NPD3134	Approved
0.6852	Remote Similarity	NPD9495	Approved
0.685	Remote Similarity	NPD6798	Discontinued
0.6822	Remote Similarity	NPD4340	Discontinued
0.6814	Remote Similarity	NPD5979	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD2066	Phase 3
0.6777	Remote Similarity	NPD5305	Approved
0.6777	Remote Similarity	NPD5306	Approved
0.6772	Remote Similarity	NPD7095	Approved
0.6754	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD4106	Approved
0.6721	Remote Similarity	NPD4135	Approved
0.6721	Remote Similarity	NPD4136	Approved
0.6721	Remote Similarity	NPD3496	Discontinued
0.672	Remote Similarity	NPD2797	Approved
0.6694	Remote Similarity	NPD4102	Approved
0.6694	Remote Similarity	NPD4105	Approved
0.6692	Remote Similarity	NPD6355	Discontinued
0.6667	Remote Similarity	NPD4807	Approved
0.6667	Remote Similarity	NPD4806	Approved
0.6667	Remote Similarity	NPD4062	Phase 3
0.6667	Remote Similarity	NPD6233	Phase 2
0.6667	Remote Similarity	NPD5535	Approved
0.6641	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD4626	Approved
0.6638	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.661	Remote Similarity	NPD6010	Discontinued
0.6609	Remote Similarity	NPD2182	Approved
0.6609	Remote Similarity	NPD2684	Approved
0.6607	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD3268	Approved
0.6585	Remote Similarity	NPD3847	Discontinued
0.6571	Remote Similarity	NPD5346	Phase 2
0.6571	Remote Similarity	NPD800	Approved
0.6571	Remote Similarity	NPD5347	Phase 2
0.6549	Remote Similarity	NPD1237	Approved
0.6538	Remote Similarity	NPD4793	Discontinued
0.6532	Remote Similarity	NPD422	Phase 1
0.6525	Remote Similarity	NPD7843	Approved
0.6514	Remote Similarity	NPD2860	Approved
0.6514	Remote Similarity	NPD2859	Approved
0.6514	Remote Similarity	NPD1989	Approved
0.6509	Remote Similarity	NPD1089	Approved
0.6509	Remote Similarity	NPD1090	Approved
0.6509	Remote Similarity	NPD1086	Approved
0.6509	Remote Similarity	NPD3672	Approved
0.6509	Remote Similarity	NPD3673	Approved
0.6491	Remote Similarity	NPD9697	Approved
0.6486	Remote Similarity	NPD1238	Approved
0.6486	Remote Similarity	NPD7798	Approved
0.6471	Remote Similarity	NPD9491	Approved
0.6462	Remote Similarity	NPD1048	Approved
0.646	Remote Similarity	NPD1930	Approved
0.646	Remote Similarity	NPD1929	Approved
0.646	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD987	Approved
0.6444	Remote Similarity	NPD5762	Approved
0.6444	Remote Similarity	NPD5763	Approved
0.6436	Remote Similarity	NPD226	Approved
0.6435	Remote Similarity	NPD6685	Approved
0.6429	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD5691	Approved
0.6422	Remote Similarity	NPD1693	Approved
0.6422	Remote Similarity	NPD2933	Approved
0.6422	Remote Similarity	NPD2934	Approved
0.641	Remote Similarity	NPD5237	Approved
0.641	Remote Similarity	NPD5236	Approved
0.641	Remote Similarity	NPD5239	Approved
0.641	Remote Similarity	NPD5240	Approved
0.641	Remote Similarity	NPD5235	Approved
0.6406	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD164	Approved
0.6389	Remote Similarity	NPD1088	Approved
0.6378	Remote Similarity	NPD5667	Approved
0.6378	Remote Similarity	NPD3225	Approved
0.6364	Remote Similarity	NPD7157	Approved
0.6357	Remote Similarity	NPD5204	Approved
0.6356	Remote Similarity	NPD2201	Approved
0.6355	Remote Similarity	NPD9258	Approved
0.6355	Remote Similarity	NPD9256	Approved
0.6349	Remote Similarity	NPD1877	Discontinued
0.6341	Remote Similarity	NPD9545	Approved
0.6341	Remote Similarity	NPD1894	Discontinued
0.6339	Remote Similarity	NPD3020	Approved
0.6328	Remote Similarity	NPD2625	Approved
0.6328	Remote Similarity	NPD2626	Approved
0.6328	Remote Similarity	NPD2160	Approved
0.6328	Remote Similarity	NPD2628	Approved
0.6328	Remote Similarity	NPD2627	Approved
0.6328	Remote Similarity	NPD2159	Approved
0.6316	Remote Similarity	NPD5124	Phase 1
0.6316	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD9493	Approved
0.6308	Remote Similarity	NPD5201	Approved
0.6308	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD4617	Approved
0.6308	Remote Similarity	NPD5203	Approved
0.6308	Remote Similarity	NPD4620	Approved
0.6304	Remote Similarity	NPD4628	Phase 3
0.6303	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD1239	Approved
0.6288	Remote Similarity	NPD4248	Discontinued
0.6281	Remote Similarity	NPD5951	Approved
0.6279	Remote Similarity	NPD5647	Approved
0.6277	Remote Similarity	NPD4534	Discontinued
0.627	Remote Similarity	NPD6287	Discontinued
0.627	Remote Similarity	NPD4480	Approved
0.626	Remote Similarity	NPD5536	Phase 2
0.626	Remote Similarity	NPD5454	Clinical (unspecified phase)
0.6259	Remote Similarity	NPD2354	Approved
0.624	Remote Similarity	NPD5126	Approved
0.624	Remote Similarity	NPD5125	Phase 3
0.6239	Remote Similarity	NPD290	Approved
0.6231	Remote Similarity	NPD3664	Approved
0.6231	Remote Similarity	NPD3662	Phase 3
0.6231	Remote Similarity	NPD3663	Approved
0.6231	Remote Similarity	NPD3661	Approved
0.623	Remote Similarity	NPD6671	Approved
0.6228	Remote Similarity	NPD1932	Approved
0.6226	Remote Similarity	NPD1087	Approved
0.6222	Remote Similarity	NPD7097	Phase 1
0.622	Remote Similarity	NPD9717	Approved
0.622	Remote Similarity	NPD6637	Approved
0.6212	Remote Similarity	NPD4621	Approved
0.6212	Remote Similarity	NPD2313	Discontinued
0.6212	Remote Similarity	NPD4619	Approved
0.6204	Remote Similarity	NPD7266	Discontinued
0.6202	Remote Similarity	NPD3266	Approved
0.6202	Remote Similarity	NPD3267	Approved
0.62	Remote Similarity	NPD9294	Approved
0.6198	Remote Similarity	NPD5283	Phase 1
0.6197	Remote Similarity	NPD5049	Phase 3
0.6182	Remote Similarity	NPD1202	Approved
0.6182	Remote Similarity	NPD1066	Discontinued
0.6182	Remote Similarity	NPD845	Approved
0.6179	Remote Similarity	NPD4431	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD7033	Discontinued
0.6176	Remote Similarity	NPD4308	Phase 3
0.6176	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD5765	Approved
0.617	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.617	Remote Similarity	NPD6799	Approved
0.6167	Remote Similarity	NPD228	Approved
0.6161	Remote Similarity	NPD1566	Phase 3
0.6161	Remote Similarity	NPD1564	Approved
0.6161	Remote Similarity	NPD1565	Approved
0.6159	Remote Similarity	NPD5958	Discontinued
0.6154	Remote Similarity	NPD2788	Approved
0.6154	Remote Similarity	NPD5704	Approved
0.6154	Remote Similarity	NPD5705	Approved
0.6154	Remote Similarity	NPD968	Approved
0.6154	Remote Similarity	NPD5403	Approved
0.6154	Remote Similarity	NPD5706	Approved
0.6148	Remote Similarity	NPD6653	Approved
0.6147	Remote Similarity	NPD7609	Phase 3
0.6143	Remote Similarity	NPD3887	Approved
0.6143	Remote Similarity	NPD6190	Approved
0.6142	Remote Similarity	NPD1535	Discovery
0.614	Remote Similarity	NPD2555	Approved
0.614	Remote Similarity	NPD2552	Approved
0.614	Remote Similarity	NPD2553	Approved
0.614	Remote Similarity	NPD2550	Approved
0.614	Remote Similarity	NPD2549	Approved
0.614	Remote Similarity	NPD2558	Approved
0.6139	Remote Similarity	NPD227	Approved
0.6139	Remote Similarity	NPD225	Approved
0.6136	Remote Similarity	NPD7008	Discontinued
0.6134	Remote Similarity	NPD3022	Approved
0.6134	Remote Similarity	NPD3021	Approved
0.6131	Remote Similarity	NPD6032	Approved
0.6131	Remote Similarity	NPD2935	Discontinued
0.6129	Remote Similarity	NPD2347	Approved
0.6127	Remote Similarity	NPD3536	Discontinued
0.6126	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6119	Remote Similarity	NPD5121	Approved
0.6119	Remote Similarity	NPD5119	Approved
0.6119	Remote Similarity	NPD5120	Approved
0.6117	Remote Similarity	NPD942	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