NPASS Compound

Structure

NPC470576 OpenBabel07101718332D 25 28 0 0 1 0 0 0 0 0999 V2000 0.1293 5.3916 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7473 3.4895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5398 4.6485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9000 2.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5909 2.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.3090 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 2.6831 0.3090 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2308 3.6974 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.2709 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 -2.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 1.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 13 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 5 13 1 0 0 0 0 6 7 1 0 0 0 0 6 13 1 0 0 0 0 7 24 1 0 0 0 0 8 19 1 0 0 0 0 9 14 1 0 0 0 0 9 20 1 0 0 0 0 10 15 1 0 0 0 0 10 19 1 0 0 0 0 11 16 1 0 0 0 0 11 22 2 0 0 0 0 12 20 1 0 0 0 0 14 8 1 1 0 0 0 14 15 1 0 0 0 0 15 16 2 0 0 0 0 16 21 1 0 0 0 0 17 20 1 0 0 0 0 17 23 2 0 0 0 0 17 25 1 0 0 0 0 18 21 1 0 0 0 0 18 24 1 0 0 0 0 18 25 1 0 0 0 0 20 21 1 1 0 0 0 21 12 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	346.21
Volume:	364.798
LogP:	4.829
LogD:	4.141
LogS:	-5.6
# Rotatable Bonds:	6
TPSA:	52.6
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.538
Synthetic Accessibility Score:	5.082
Fsp3:	0.81
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.984
MDCK Permeability:	2.282730747538153e-05
Pgp-inhibitor:	0.336
Pgp-substrate:	0.175
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.046
30% Bioavailability (F30%):	0.096

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.459
Plasma Protein Binding (PPB):	75.94239044189453%
Volume Distribution (VD):	1.061
Pgp-substrate:	18.396684646606445%

ADMET: Metabolism

CYP1A2-inhibitor:	0.033
CYP1A2-substrate:	0.766
CYP2C19-inhibitor:	0.785
CYP2C19-substrate:	0.86
CYP2C9-inhibitor:	0.545
CYP2C9-substrate:	0.207
CYP2D6-inhibitor:	0.038
CYP2D6-substrate:	0.072
CYP3A4-inhibitor:	0.873
CYP3A4-substrate:	0.675

ADMET: Excretion

Clearance (CL):	6.774
Half-life (T1/2):	0.021

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.259
Drug-inuced Liver Injury (DILI):	0.103
AMES Toxicity:	0.937
Rat Oral Acute Toxicity:	0.411
Maximum Recommended Daily Dose:	0.907
Skin Sensitization:	0.427
Carcinogencity:	0.965
Eye Corrosion:	0.246
Eye Irritation:	0.075
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC470576

Natural Product ID:	NPC470576
*Common Name:**	Udalactarane A
IUPAC Name:	n.a.
Synonyms:	Udalactarane A
Standard InCHIKey:	CERWTWXWRVGAAK-PBGUIJGPSA-N
Standard InCHI:	InChI=1S/C21H30O4/c1-5-13(2)6-7-24-18-21-12-20(21,17(23)25-18)9-14-8-19(3,4)10-15(14)16(21)11-22/h11,13-14,18H,5-10,12H2,1-4H3/t13?,14-,18?,20+,21+/m0/s1
SMILES:	CCC(C)CCOC1C23CC2(CC4CC(CC4=C3C=O)(C)C)C(=O)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2071320
PubChem CID:	70693127
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001244] Delta valerolactones

*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
NPO33354	phlebia uda	Species	Meruliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22746380]

☑ 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
Others	4

Activity Type	# Activity
Cell Line	1
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	=	101000.0	nM	PMID[575283]
NPT1276	Organism	Gibberella zeae	Gibberella zeae	INH	=	10.0	ug ml-1	PMID[575283]
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	INH	=	10.0	ug ml-1	PMID[575283]
NPT825	Organism	Phytophthora infestans	Phytophthora infestans	INH	=	100.0	ug ml-1	PMID[575283]
NPT635	Organism	Botryotinia fuckeliana	Botryotinia fuckeliana	INH	>	100.0	ug ml-1	PMID[575283]

☑ 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 NPC470576 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	276
0.1-0.2	2303
0.2-0.3	9410
0.3-0.4	14719
0.4-0.5	7767
0.5-0.6	7064
0.6-0.7	1140
0.7-0.8	16
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8431	Intermediate Similarity	NPC470577
0.8242	Intermediate Similarity	NPC244174
0.7957	Intermediate Similarity	NPC265580
0.7812	Intermediate Similarity	NPC474631
0.7812	Intermediate Similarity	NPC65513
0.7634	Intermediate Similarity	NPC71626
0.7576	Intermediate Similarity	NPC473369
0.7475	Intermediate Similarity	NPC41649
0.7449	Intermediate Similarity	NPC179517
0.7449	Intermediate Similarity	NPC165904
0.7429	Intermediate Similarity	NPC127790
0.7426	Intermediate Similarity	NPC204054
0.7426	Intermediate Similarity	NPC257726
0.7391	Intermediate Similarity	NPC474956
0.7379	Intermediate Similarity	NPC473384
0.7374	Intermediate Similarity	NPC472225
0.7374	Intermediate Similarity	NPC471571
0.7374	Intermediate Similarity	NPC472226
0.7327	Intermediate Similarity	NPC112654
0.7282	Intermediate Similarity	NPC470906
0.7263	Intermediate Similarity	NPC100391
0.7245	Intermediate Similarity	NPC473039
0.7222	Intermediate Similarity	NPC112457
0.7216	Intermediate Similarity	NPC475773
0.72	Intermediate Similarity	NPC267266
0.72	Intermediate Similarity	NPC475657
0.72	Intermediate Similarity	NPC277721
0.72	Intermediate Similarity	NPC166346
0.7188	Intermediate Similarity	NPC300985
0.7157	Intermediate Similarity	NPC311166
0.7157	Intermediate Similarity	NPC470801
0.7143	Intermediate Similarity	NPC134077
0.7143	Intermediate Similarity	NPC190718
0.7143	Intermediate Similarity	NPC243981
0.713	Intermediate Similarity	NPC469844
0.7129	Intermediate Similarity	NPC56525
0.7129	Intermediate Similarity	NPC294266
0.7128	Intermediate Similarity	NPC149237
0.7115	Intermediate Similarity	NPC473219
0.7115	Intermediate Similarity	NPC470761
0.7103	Intermediate Similarity	NPC470309
0.7087	Intermediate Similarity	NPC226986
0.7087	Intermediate Similarity	NPC187159
0.7087	Intermediate Similarity	NPC23680
0.7083	Intermediate Similarity	NPC469407
0.7075	Intermediate Similarity	NPC132395
0.7075	Intermediate Similarity	NPC471365
0.7075	Intermediate Similarity	NPC471364
0.7075	Intermediate Similarity	NPC176883
0.7071	Intermediate Similarity	NPC174765
0.7048	Intermediate Similarity	NPC63249
0.7041	Intermediate Similarity	NPC167877
0.703	Intermediate Similarity	NPC470656
0.7027	Intermediate Similarity	NPC222834
0.7021	Intermediate Similarity	NPC473685
0.7019	Intermediate Similarity	NPC252295
0.701	Intermediate Similarity	NPC470223
0.7009	Intermediate Similarity	NPC119493
0.699	Remote Similarity	NPC307164
0.6979	Remote Similarity	NPC469561
0.6979	Remote Similarity	NPC271784
0.6979	Remote Similarity	NPC22611
0.6972	Remote Similarity	NPC470269
0.697	Remote Similarity	NPC226863
0.6964	Remote Similarity	NPC157441
0.6961	Remote Similarity	NPC472223
0.6961	Remote Similarity	NPC474554
0.6961	Remote Similarity	NPC88507
0.6961	Remote Similarity	NPC472224
0.6957	Remote Similarity	NPC161065
0.6957	Remote Similarity	NPC41017
0.6957	Remote Similarity	NPC474179
0.6957	Remote Similarity	NPC475834
0.6952	Remote Similarity	NPC241221
0.6944	Remote Similarity	NPC470267
0.6944	Remote Similarity	NPC103172
0.6944	Remote Similarity	NPC190867
0.6944	Remote Similarity	NPC164600
0.6939	Remote Similarity	NPC474062
0.6931	Remote Similarity	NPC150383
0.6931	Remote Similarity	NPC141831
0.6931	Remote Similarity	NPC476187
0.6923	Remote Similarity	NPC292133
0.6923	Remote Similarity	NPC216904
0.6923	Remote Similarity	NPC476768
0.6915	Remote Similarity	NPC170561
0.6909	Remote Similarity	NPC246205
0.6909	Remote Similarity	NPC23497
0.6907	Remote Similarity	NPC320801
0.6907	Remote Similarity	NPC82492
0.6907	Remote Similarity	NPC25802
0.6907	Remote Similarity	NPC469569
0.6907	Remote Similarity	NPC101138
0.6907	Remote Similarity	NPC51135
0.6903	Remote Similarity	NPC471398
0.69	Remote Similarity	NPC471222
0.6897	Remote Similarity	NPC241192
0.6882	Remote Similarity	NPC316500
0.6881	Remote Similarity	NPC293512
0.6875	Remote Similarity	NPC12046
0.6875	Remote Similarity	NPC327969
0.6875	Remote Similarity	NPC321289
0.6875	Remote Similarity	NPC194951
0.687	Remote Similarity	NPC471249
0.687	Remote Similarity	NPC475913
0.6869	Remote Similarity	NPC288952
0.6863	Remote Similarity	NPC109414
0.6863	Remote Similarity	NPC477615
0.6857	Remote Similarity	NPC153792
0.6857	Remote Similarity	NPC176845
0.6857	Remote Similarity	NPC112753
0.6857	Remote Similarity	NPC275439
0.6857	Remote Similarity	NPC271387
0.6852	Remote Similarity	NPC121566
0.6852	Remote Similarity	NPC228669
0.6852	Remote Similarity	NPC223741
0.6852	Remote Similarity	NPC164835
0.6852	Remote Similarity	NPC100955
0.6852	Remote Similarity	NPC244247
0.6847	Remote Similarity	NPC235014
0.6847	Remote Similarity	NPC101450
0.6847	Remote Similarity	NPC473036
0.6847	Remote Similarity	NPC272898
0.6842	Remote Similarity	NPC302471
0.6842	Remote Similarity	NPC195424
0.6842	Remote Similarity	NPC170038
0.6838	Remote Similarity	NPC204731
0.6837	Remote Similarity	NPC2709
0.6832	Remote Similarity	NPC232426
0.6832	Remote Similarity	NPC281942
0.6832	Remote Similarity	NPC469595
0.6832	Remote Similarity	NPC212679
0.6832	Remote Similarity	NPC220454
0.6827	Remote Similarity	NPC111684
0.6827	Remote Similarity	NPC125622
0.6827	Remote Similarity	NPC17578
0.6827	Remote Similarity	NPC58052
0.6827	Remote Similarity	NPC240673
0.6822	Remote Similarity	NPC271266
0.6822	Remote Similarity	NPC308351
0.6822	Remote Similarity	NPC475320
0.6818	Remote Similarity	NPC295389
0.6818	Remote Similarity	NPC94942
0.6818	Remote Similarity	NPC469845
0.6818	Remote Similarity	NPC325054
0.6818	Remote Similarity	NPC61411
0.6814	Remote Similarity	NPC471627
0.6814	Remote Similarity	NPC471173
0.681	Remote Similarity	NPC158963
0.6809	Remote Similarity	NPC35574
0.6804	Remote Similarity	NPC193198
0.6804	Remote Similarity	NPC472440
0.68	Remote Similarity	NPC80335
0.68	Remote Similarity	NPC28227
0.68	Remote Similarity	NPC477128
0.6796	Remote Similarity	NPC128488
0.6796	Remote Similarity	NPC477129
0.6796	Remote Similarity	NPC304968
0.6796	Remote Similarity	NPC96541
0.6796	Remote Similarity	NPC477130
0.6792	Remote Similarity	NPC469402
0.6792	Remote Similarity	NPC476303
0.6789	Remote Similarity	NPC95243
0.6789	Remote Similarity	NPC162033
0.6789	Remote Similarity	NPC96377
0.6789	Remote Similarity	NPC63023
0.6789	Remote Similarity	NPC181357
0.6789	Remote Similarity	NPC153095
0.6789	Remote Similarity	NPC469401
0.6786	Remote Similarity	NPC231589
0.6786	Remote Similarity	NPC118860
0.6786	Remote Similarity	NPC214797
0.6783	Remote Similarity	NPC477252
0.678	Remote Similarity	NPC470419
0.6771	Remote Similarity	NPC475665
0.6765	Remote Similarity	NPC470113
0.6762	Remote Similarity	NPC121339
0.6762	Remote Similarity	NPC472188
0.6759	Remote Similarity	NPC140723
0.6759	Remote Similarity	NPC159442
0.6759	Remote Similarity	NPC254202
0.6757	Remote Similarity	NPC241927
0.6757	Remote Similarity	NPC118225
0.6757	Remote Similarity	NPC477069
0.6757	Remote Similarity	NPC258543
0.6757	Remote Similarity	NPC477070
0.6754	Remote Similarity	NPC74727
0.675	Remote Similarity	NPC47113
0.675	Remote Similarity	NPC174367
0.6739	Remote Similarity	NPC469643
0.6739	Remote Similarity	NPC469641
0.6737	Remote Similarity	NPC118987
0.6735	Remote Similarity	NPC470011
0.6735	Remote Similarity	NPC109512
0.6733	Remote Similarity	NPC288699
0.6733	Remote Similarity	NPC168131
0.6733	Remote Similarity	NPC284561
0.6733	Remote Similarity	NPC469546
0.6731	Remote Similarity	NPC33473
0.6731	Remote Similarity	NPC241156

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 NPC470576 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	263
0.1-0.2	3025
0.2-0.3	3956
0.3-0.4	1311
0.4-0.5	360
0.5-0.6	224
0.6-0.7	11
0.7-0.8	0
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
0.7264	Intermediate Similarity	NPD6008	Approved
0.7059	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5737	Approved
0.68	Remote Similarity	NPD6672	Approved
0.6796	Remote Similarity	NPD6001	Approved
0.6699	Remote Similarity	NPD6399	Phase 3
0.6667	Remote Similarity	NPD5207	Approved
0.6634	Remote Similarity	NPD6903	Approved
0.66	Remote Similarity	NPD7146	Approved
0.66	Remote Similarity	NPD6409	Approved
0.66	Remote Similarity	NPD7334	Approved
0.66	Remote Similarity	NPD7521	Approved
0.66	Remote Similarity	NPD5330	Approved
0.66	Remote Similarity	NPD6684	Approved
0.6577	Remote Similarity	NPD6412	Phase 2
0.6542	Remote Similarity	NPD5696	Approved
0.6531	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD7507	Approved
0.6471	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD8293	Discontinued
0.6415	Remote Similarity	NPD5695	Phase 3
0.6408	Remote Similarity	NPD6904	Approved
0.6408	Remote Similarity	NPD6080	Approved
0.6408	Remote Similarity	NPD6673	Approved
0.6372	Remote Similarity	NPD6686	Approved
0.6371	Remote Similarity	NPD7736	Approved
0.6364	Remote Similarity	NPD6370	Approved
0.6346	Remote Similarity	NPD5692	Phase 3
0.6337	Remote Similarity	NPD1694	Approved
0.6321	Remote Similarity	NPD7900	Approved
0.6321	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.632	Remote Similarity	NPD7319	Approved
0.6316	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD7122	Discontinued
0.6311	Remote Similarity	NPD5208	Approved
0.6296	Remote Similarity	NPD5959	Approved
0.6296	Remote Similarity	NPD6084	Phase 2
0.6296	Remote Similarity	NPD6083	Phase 2
0.6293	Remote Similarity	NPD6882	Approved
0.6286	Remote Similarity	NPD5281	Approved
0.6286	Remote Similarity	NPD5693	Phase 1
0.6286	Remote Similarity	NPD5694	Approved
0.6286	Remote Similarity	NPD5284	Approved
0.6286	Remote Similarity	NPD6050	Approved
0.6283	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.626	Remote Similarity	NPD7492	Approved
0.625	Remote Similarity	NPD1695	Approved
0.6228	Remote Similarity	NPD7320	Approved
0.6218	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD6009	Approved
0.621	Remote Similarity	NPD6616	Approved
0.6204	Remote Similarity	NPD4697	Phase 3
0.6198	Remote Similarity	NPD6059	Approved
0.6198	Remote Similarity	NPD6054	Approved
0.6195	Remote Similarity	NPD6675	Approved
0.6195	Remote Similarity	NPD7128	Approved
0.6195	Remote Similarity	NPD5739	Approved
0.6195	Remote Similarity	NPD6402	Approved
0.6174	Remote Similarity	NPD6373	Approved
0.6174	Remote Similarity	NPD6372	Approved
0.6168	Remote Similarity	NPD5282	Discontinued
0.6161	Remote Similarity	NPD6052	Approved
0.616	Remote Similarity	NPD7078	Approved
0.6154	Remote Similarity	NPD6053	Discontinued
0.6148	Remote Similarity	NPD6016	Approved
0.6148	Remote Similarity	NPD6015	Approved
0.6147	Remote Similarity	NPD7902	Approved
0.614	Remote Similarity	NPD5697	Approved
0.614	Remote Similarity	NPD5701	Approved
0.6121	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD6098	Approved
0.6111	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD5654	Approved
0.6111	Remote Similarity	NPD8336	Approved
0.6111	Remote Similarity	NPD8337	Approved
0.6098	Remote Similarity	NPD5988	Approved
0.6087	Remote Similarity	NPD6881	Approved
0.6087	Remote Similarity	NPD6011	Approved
0.6087	Remote Similarity	NPD6899	Approved
0.6068	Remote Similarity	NPD6650	Approved
0.6068	Remote Similarity	NPD6649	Approved
0.6058	Remote Similarity	NPD3573	Approved
0.6048	Remote Similarity	NPD6067	Discontinued
0.6048	Remote Similarity	NPD8328	Phase 3
0.6034	Remote Similarity	NPD6012	Approved
0.6034	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD6014	Approved
0.6034	Remote Similarity	NPD6013	Approved
0.6019	Remote Similarity	NPD7748	Approved
0.5983	Remote Similarity	NPD7102	Approved
0.5983	Remote Similarity	NPD7290	Approved
0.5983	Remote Similarity	NPD6883	Approved
0.5981	Remote Similarity	NPD8035	Phase 2
0.5981	Remote Similarity	NPD8034	Phase 2
0.5966	Remote Similarity	NPD4632	Approved
0.5963	Remote Similarity	NPD5210	Approved
0.5963	Remote Similarity	NPD4629	Approved
0.5962	Remote Similarity	NPD3618	Phase 1
0.596	Remote Similarity	NPD3617	Approved
0.5946	Remote Similarity	NPD7638	Approved
0.5943	Remote Similarity	NPD4753	Phase 2
0.5943	Remote Similarity	NPD5328	Approved
0.5941	Remote Similarity	NPD1780	Approved
0.5941	Remote Similarity	NPD1779	Approved
0.5932	Remote Similarity	NPD8130	Phase 1
0.5932	Remote Similarity	NPD6847	Approved
0.5932	Remote Similarity	NPD6869	Approved
0.5932	Remote Similarity	NPD6617	Approved
0.5932	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD3666	Approved
0.5922	Remote Similarity	NPD3665	Phase 1
0.5922	Remote Similarity	NPD4786	Approved
0.5922	Remote Similarity	NPD3668	Phase 3
0.5922	Remote Similarity	NPD3133	Approved
0.592	Remote Similarity	NPD7604	Phase 2
0.5909	Remote Similarity	NPD7732	Phase 3
0.5893	Remote Similarity	NPD7640	Approved
0.5893	Remote Similarity	NPD7639	Approved
0.5887	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD4221	Approved
0.5882	Remote Similarity	NPD8297	Approved
0.5882	Remote Similarity	NPD3667	Approved
0.5882	Remote Similarity	NPD4223	Phase 3
0.5865	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD6614	Approved
0.5859	Remote Similarity	NPD6033	Approved
0.5856	Remote Similarity	NPD4755	Approved
0.5847	Remote Similarity	NPD6371	Approved
0.5833	Remote Similarity	NPD8133	Approved
0.5833	Remote Similarity	NPD6079	Approved
0.5833	Remote Similarity	NPD6411	Approved
0.5833	Remote Similarity	NPD7515	Phase 2
0.582	Remote Similarity	NPD7115	Discovery
0.5816	Remote Similarity	NPD8039	Approved
0.581	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.581	Remote Similarity	NPD5279	Phase 3
0.5806	Remote Similarity	NPD6319	Approved
0.5802	Remote Similarity	NPD6845	Suspended
0.5794	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD7632	Discontinued
0.578	Remote Similarity	NPD4202	Approved
0.5772	Remote Similarity	NPD7328	Approved
0.5772	Remote Similarity	NPD7327	Approved
0.5769	Remote Similarity	NPD4197	Approved
0.5766	Remote Similarity	NPD5221	Approved
0.5766	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD5222	Approved
0.576	Remote Similarity	NPD5983	Phase 2
0.576	Remote Similarity	NPD8033	Approved
0.5752	Remote Similarity	NPD4700	Approved
0.5752	Remote Similarity	NPD5286	Approved
0.5752	Remote Similarity	NPD4696	Approved
0.5752	Remote Similarity	NPD5285	Approved
0.5741	Remote Similarity	NPD46	Approved
0.5741	Remote Similarity	NPD6698	Approved
0.5738	Remote Similarity	NPD6274	Approved
0.5729	Remote Similarity	NPD4747	Approved
0.5726	Remote Similarity	NPD7516	Approved
0.5714	Remote Similarity	NPD5329	Approved
0.5714	Remote Similarity	NPD5173	Approved
0.5702	Remote Similarity	NPD5223	Approved
0.5691	Remote Similarity	NPD6317	Approved
0.5686	Remote Similarity	NPD4695	Discontinued
0.568	Remote Similarity	NPD8294	Approved
0.568	Remote Similarity	NPD8377	Approved
0.5673	Remote Similarity	NPD5362	Discontinued
0.5664	Remote Similarity	NPD4225	Approved
0.566	Remote Similarity	NPD4689	Approved
0.566	Remote Similarity	NPD4694	Approved
0.566	Remote Similarity	NPD4138	Approved
0.566	Remote Similarity	NPD4693	Phase 3
0.566	Remote Similarity	NPD4690	Approved
0.566	Remote Similarity	NPD4688	Approved
0.566	Remote Similarity	NPD5280	Approved
0.566	Remote Similarity	NPD5690	Phase 2
0.566	Remote Similarity	NPD5205	Approved
0.5657	Remote Similarity	NPD3702	Approved
0.5652	Remote Similarity	NPD4633	Approved
0.5652	Remote Similarity	NPD5224	Approved
0.5652	Remote Similarity	NPD5225	Approved
0.5652	Remote Similarity	NPD5211	Phase 2
0.5652	Remote Similarity	NPD5226	Approved
0.5649	Remote Similarity	NPD5956	Approved
0.5648	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5648	Remote Similarity	NPD6101	Approved
0.5648	Remote Similarity	NPD6051	Approved
0.5645	Remote Similarity	NPD6335	Approved
0.5645	Remote Similarity	NPD6314	Approved
0.5645	Remote Similarity	NPD6313	Approved
0.5645	Remote Similarity	NPD7641	Discontinued
0.5636	Remote Similarity	NPD5133	Approved
0.5636	Remote Similarity	NPD5779	Approved
0.5636	Remote Similarity	NPD5778	Approved
0.5635	Remote Similarity	NPD8296	Approved
0.5635	Remote Similarity	NPD8379	Approved
0.5635	Remote Similarity	NPD7503	Approved
0.5635	Remote Similarity	NPD8515	Approved
0.5635	Remote Similarity	NPD8335	Approved
0.5635	Remote Similarity	NPD8380	Approved
0.5635	Remote Similarity	NPD8517	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