NPASS Compound

Structure

CID63118 OpenBabel06191715402D 33 38 0 0 1 0 0 0 0 0999 V2000 -2.5062 -1.9021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7176 -1.9022 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1119 3.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8068 0.8179 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4078 0.7887 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7039 -1.1709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6830 -0.3943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0001 1.6257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7039 1.2193 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7040 -1.2192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8157 0.0001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1118 0.4065 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.8128 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1118 0.4063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4079 -0.0001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4079 2.4384 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8158 2.4384 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7040 1.2192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4079 1.6256 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4079 -0.8128 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7039 0.4064 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8158 -0.8127 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8158 1.6256 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9247 2.8448 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1119 -1.2192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1119 2.8448 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1119 1.2192 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4079 0.0001 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7040 0.4064 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 -3.4988 -1.2070 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3260 3.5398 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2222 2.3295 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 25 1 0 0 0 0 6 29 1 0 0 0 0 8 9 1 0 0 0 0 8 18 2 0 0 0 0 9 21 1 0 0 0 0 10 13 1 0 0 0 0 10 20 1 0 0 0 0 11 12 1 0 0 0 0 11 22 1 0 0 0 0 12 28 1 0 0 0 0 13 30 1 0 0 0 0 14 15 1 0 0 0 0 14 27 1 0 0 0 0 15 29 1 0 0 0 0 16 19 1 0 0 0 0 16 26 1 0 0 0 0 17 23 1 0 0 0 0 17 26 1 0 0 0 0 18 19 1 0 0 0 0 18 29 1 0 0 0 0 19 27 1 6 0 0 0 20 25 1 0 0 0 0 20 28 1 1 0 0 0 21 28 1 1 0 0 0 21 30 1 0 0 0 0 22 25 1 0 0 0 0 22 31 1 1 0 0 0 23 27 1 6 0 0 0 23 33 1 0 0 0 0 24 26 1 0 0 0 0 24 32 2 0 0 0 0 24 33 1 0 0 0 0 26 3 1 1 0 0 0 27 4 1 1 0 0 0 28 5 1 1 0 0 0 29 30 1 1 0 0 0 30 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	454.34
Volume:	497.195
LogP:	6.343
LogD:	4.973
LogS:	-5.968
# Rotatable Bonds:	0
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.328
Synthetic Accessibility Score:	5.78
Fsp3:	0.9
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:	-5.152
MDCK Permeability:	2.2274592993198894e-05
Pgp-inhibitor:	0.907
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.72
30% Bioavailability (F30%):	0.847

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.766
Plasma Protein Binding (PPB):	92.59904479980469%
Volume Distribution (VD):	0.896
Pgp-substrate:	6.646010398864746%

ADMET: Metabolism

CYP1A2-inhibitor:	0.028
CYP1A2-substrate:	0.153
CYP2C19-inhibitor:	0.061
CYP2C19-substrate:	0.9
CYP2C9-inhibitor:	0.263
CYP2C9-substrate:	0.065
CYP2D6-inhibitor:	0.05
CYP2D6-substrate:	0.061
CYP3A4-inhibitor:	0.826
CYP3A4-substrate:	0.665

ADMET: Excretion

Clearance (CL):	8.083
Half-life (T1/2):	0.045

ADMET: Toxicity

hERG Blockers:	0.145
Human Hepatotoxicity (H-HT):	0.244
Drug-inuced Liver Injury (DILI):	0.032
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.947
Maximum Recommended Daily Dose:	0.991
Skin Sensitization:	0.497
Carcinogencity:	0.189
Eye Corrosion:	0.358
Eye Irritation:	0.134
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC63118

Natural Product ID:	NPC63118
*Common Name:**	3-Epiabruslactone A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	HHQJBWYXBWOFJY-YLXTXNMFSA-N
Standard InCHI:	InChI=1S/C30H46O3/c1-25(2)20-10-13-30(7)21(28(20,5)12-11-22(25)31)9-8-18-19-16-26(3)17-23(33-24(26)32)27(19,4)14-15-29(18,30)6/h8,19-23,31H,9-17H2,1-7H3/t19-,20-,21+,22-,23-,26-,27+,28-,29+,30+/m0/s1
SMILES:	CC1(C)[C@@H]2CC[C@]3(C)[C@H](CC=C4[C@@H]5C[C@@]6(C)C[C@@H]([C@]5(C)CC[C@@]34C)OC6=O)[C@@]2(C)CC[C@@H]1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL484424
PubChem CID:	158477
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO14242	Maytenus laevis	Species	Celastraceae	Eukaryota	bark	Leticia, Colombia	n.a.	PMID[15568791]
NPO29118	Euonymus alatus	Species	Celastraceae	Eukaryota	leaves and twigs	n.a.	n.a.	PMID[21435874]
NPO29118	Euonymus alatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29118	Euonymus alatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29118	Euonymus alatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29118	Euonymus alatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29118	Euonymus alatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14242	Maytenus laevis	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
Others	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT927	Cell Line	PBMC	Homo sapiens	Activity	=	308.4	pg/ml	PMID[541901]
NPT927	Cell Line	PBMC	Homo sapiens	Activity	<	7.8	pg/ml	PMID[541901]

☑ 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 NPC63118 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	184
0.1-0.2	1184
0.2-0.3	5002
0.3-0.4	14314
0.4-0.5	7943
0.5-0.6	5664
0.6-0.7	4504
0.7-0.8	3338
0.8-0.85	265
0.85-0.9	212
0.9-0.95	84
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474436
1.0	High Similarity	NPC49776
0.9535	High Similarity	NPC246708
0.9535	High Similarity	NPC40552
0.9451	High Similarity	NPC164349
0.9425	High Similarity	NPC470588
0.9419	High Similarity	NPC68160
0.9419	High Similarity	NPC242468
0.9419	High Similarity	NPC51700
0.9419	High Similarity	NPC88716
0.9419	High Similarity	NPC18064
0.9419	High Similarity	NPC307426
0.9419	High Similarity	NPC102683
0.9419	High Similarity	NPC130577
0.9419	High Similarity	NPC98442
0.9419	High Similarity	NPC171203
0.9419	High Similarity	NPC293564
0.9419	High Similarity	NPC142415
0.9326	High Similarity	NPC86368
0.9318	High Similarity	NPC227467
0.9318	High Similarity	NPC210037
0.9318	High Similarity	NPC291028
0.9318	High Similarity	NPC290614
0.9318	High Similarity	NPC120840
0.9318	High Similarity	NPC477872
0.9318	High Similarity	NPC474728
0.9318	High Similarity	NPC7260
0.9318	High Similarity	NPC18872
0.9318	High Similarity	NPC120968
0.9318	High Similarity	NPC113989
0.9318	High Similarity	NPC273621
0.931	High Similarity	NPC474512
0.931	High Similarity	NPC473242
0.931	High Similarity	NPC17733
0.931	High Similarity	NPC182797
0.931	High Similarity	NPC470629
0.931	High Similarity	NPC290690
0.931	High Similarity	NPC52169
0.931	High Similarity	NPC474845
0.931	High Similarity	NPC181225
0.9302	High Similarity	NPC72638
0.9239	High Similarity	NPC124703
0.9239	High Similarity	NPC234617
0.9231	High Similarity	NPC327179
0.9213	High Similarity	NPC60755
0.9213	High Similarity	NPC105189
0.9213	High Similarity	NPC77099
0.9213	High Similarity	NPC187722
0.9213	High Similarity	NPC285184
0.9213	High Similarity	NPC470590
0.9205	High Similarity	NPC290972
0.9205	High Similarity	NPC198664
0.9205	High Similarity	NPC95246
0.9205	High Similarity	NPC474972
0.9205	High Similarity	NPC293048
0.9205	High Similarity	NPC127689
0.9205	High Similarity	NPC274330
0.9205	High Similarity	NPC64872
0.9205	High Similarity	NPC25906
0.9205	High Similarity	NPC30522
0.9205	High Similarity	NPC143232
0.9205	High Similarity	NPC130520
0.9205	High Similarity	NPC270768
0.9205	High Similarity	NPC121798
0.9205	High Similarity	NPC263393
0.9205	High Similarity	NPC61543
0.9205	High Similarity	NPC59263
0.9205	High Similarity	NPC225585
0.9205	High Similarity	NPC161751
0.9205	High Similarity	NPC234346
0.9121	High Similarity	NPC474727
0.9111	High Similarity	NPC470224
0.9111	High Similarity	NPC118519
0.9111	High Similarity	NPC202728
0.9111	High Similarity	NPC214756
0.9111	High Similarity	NPC136313
0.9111	High Similarity	NPC272075
0.9111	High Similarity	NPC307335
0.9111	High Similarity	NPC295643
0.9111	High Similarity	NPC229281
0.9111	High Similarity	NPC158059
0.9111	High Similarity	NPC74855
0.9101	High Similarity	NPC470589
0.9101	High Similarity	NPC126369
0.9101	High Similarity	NPC193750
0.9101	High Similarity	NPC86372
0.9101	High Similarity	NPC130278
0.9101	High Similarity	NPC111110
0.9101	High Similarity	NPC172361
0.908	High Similarity	NPC10005
0.908	High Similarity	NPC74363
0.908	High Similarity	NPC329943
0.908	High Similarity	NPC325594
0.908	High Similarity	NPC91525
0.908	High Similarity	NPC9892
0.908	High Similarity	NPC475862
0.9043	High Similarity	NPC235142
0.9032	High Similarity	NPC471966
0.9022	High Similarity	NPC230151
0.9011	High Similarity	NPC191412
0.9011	High Similarity	NPC296164
0.9011	High Similarity	NPC74751
0.9011	High Similarity	NPC91010
0.9011	High Similarity	NPC78580
0.9011	High Similarity	NPC23621
0.9011	High Similarity	NPC184006
0.9011	High Similarity	NPC114159
0.9011	High Similarity	NPC6818
0.9	High Similarity	NPC324341
0.9	High Similarity	NPC4036
0.9	High Similarity	NPC84319
0.9	High Similarity	NPC966
0.9	High Similarity	NPC38754
0.9	High Similarity	NPC52021
0.9	High Similarity	NPC306541
0.9	High Similarity	NPC158030
0.9	High Similarity	NPC25299
0.9	High Similarity	NPC300351
0.9	High Similarity	NPC71074
0.9	High Similarity	NPC233455
0.9	High Similarity	NPC288833
0.9	High Similarity	NPC228784
0.9	High Similarity	NPC155120
0.9	High Similarity	NPC65120
0.9	High Similarity	NPC235884
0.9	High Similarity	NPC472149
0.9	High Similarity	NPC145067
0.9	High Similarity	NPC282616
0.9	High Similarity	NPC474525
0.8989	High Similarity	NPC474686
0.8977	High Similarity	NPC46912
0.8977	High Similarity	NPC162107
0.8977	High Similarity	NPC73064
0.8977	High Similarity	NPC71507
0.8966	High Similarity	NPC133954
0.8966	High Similarity	NPC191965
0.8925	High Similarity	NPC476878
0.8925	High Similarity	NPC259788
0.8925	High Similarity	NPC476879
0.8925	High Similarity	NPC255589
0.8913	High Similarity	NPC23241
0.8913	High Similarity	NPC195715
0.8913	High Similarity	NPC96916
0.8901	High Similarity	NPC118490
0.8901	High Similarity	NPC298554
0.8901	High Similarity	NPC275809
0.8889	High Similarity	NPC46441
0.8889	High Similarity	NPC49320
0.8876	High Similarity	NPC224145
0.8864	High Similarity	NPC137306
0.8864	High Similarity	NPC477579
0.8864	High Similarity	NPC235341
0.8864	High Similarity	NPC213412
0.8864	High Similarity	NPC6979
0.8864	High Similarity	NPC84121
0.8864	High Similarity	NPC95594
0.8864	High Similarity	NPC73038
0.8851	High Similarity	NPC171789
0.8842	High Similarity	NPC233012
0.8842	High Similarity	NPC54909
0.883	High Similarity	NPC260149
0.883	High Similarity	NPC188833
0.883	High Similarity	NPC58942
0.8817	High Similarity	NPC132824
0.8817	High Similarity	NPC98874
0.8817	High Similarity	NPC173744
0.8817	High Similarity	NPC62516
0.8817	High Similarity	NPC73004
0.8817	High Similarity	NPC116457
0.8817	High Similarity	NPC204961
0.8817	High Similarity	NPC157113
0.8817	High Similarity	NPC207922
0.8817	High Similarity	NPC158371
0.8817	High Similarity	NPC259733
0.8804	High Similarity	NPC263548
0.8804	High Similarity	NPC60692
0.8804	High Similarity	NPC209868
0.8804	High Similarity	NPC88116
0.8804	High Similarity	NPC159365
0.8804	High Similarity	NPC231063
0.8804	High Similarity	NPC222047
0.8804	High Similarity	NPC282395
0.8804	High Similarity	NPC20235
0.8804	High Similarity	NPC474529
0.8804	High Similarity	NPC299996
0.8804	High Similarity	NPC32407
0.8804	High Similarity	NPC145667
0.8791	High Similarity	NPC301244
0.8791	High Similarity	NPC6255
0.8791	High Similarity	NPC471588
0.8791	High Similarity	NPC475708
0.8778	High Similarity	NPC475049
0.8776	High Similarity	NPC301666
0.8764	High Similarity	NPC474684
0.8764	High Similarity	NPC142361
0.8736	High Similarity	NPC470948
0.8723	High Similarity	NPC43686
0.8723	High Similarity	NPC187933
0.8723	High Similarity	NPC261935
0.8723	High Similarity	NPC9613

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 NPC63118 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	157
0.1-0.2	1468
0.2-0.3	4003
0.3-0.4	2375
0.4-0.5	649
0.5-0.6	188
0.6-0.7	189
0.7-0.8	109
0.8-0.85	7
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9011	High Similarity	NPD7748	Approved
0.9	High Similarity	NPD7515	Phase 2
0.8925	High Similarity	NPD7902	Approved
0.8602	High Similarity	NPD7900	Approved
0.8602	High Similarity	NPD7901	Clinical (unspecified phase)
0.8539	High Similarity	NPD7520	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD8035	Phase 2
0.8387	Intermediate Similarity	NPD8034	Phase 2
0.8298	Intermediate Similarity	NPD6399	Phase 3
0.8276	Intermediate Similarity	NPD7645	Phase 2
0.8242	Intermediate Similarity	NPD3618	Phase 1
0.8065	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.8022	Intermediate Similarity	NPD4786	Approved
0.8	Intermediate Similarity	NPD3667	Approved
0.7979	Intermediate Similarity	NPD5328	Approved
0.7879	Intermediate Similarity	NPD7638	Approved
0.7849	Intermediate Similarity	NPD6684	Approved
0.7849	Intermediate Similarity	NPD7146	Approved
0.7849	Intermediate Similarity	NPD7521	Approved
0.7849	Intermediate Similarity	NPD7334	Approved
0.7849	Intermediate Similarity	NPD6409	Approved
0.7849	Intermediate Similarity	NPD5330	Approved
0.7812	Intermediate Similarity	NPD6079	Approved
0.78	Intermediate Similarity	NPD7640	Approved
0.78	Intermediate Similarity	NPD7639	Approved
0.7767	Intermediate Similarity	NPD5739	Approved
0.7767	Intermediate Similarity	NPD6675	Approved
0.7767	Intermediate Similarity	NPD6402	Approved
0.7767	Intermediate Similarity	NPD7128	Approved
0.7714	Intermediate Similarity	NPD6372	Approved
0.7714	Intermediate Similarity	NPD6373	Approved
0.7684	Intermediate Similarity	NPD6903	Approved
0.7634	Intermediate Similarity	NPD3665	Phase 1
0.7634	Intermediate Similarity	NPD3133	Approved
0.7634	Intermediate Similarity	NPD3666	Approved
0.7619	Intermediate Similarity	NPD6881	Approved
0.7619	Intermediate Similarity	NPD6899	Approved
0.7619	Intermediate Similarity	NPD7320	Approved
0.76	Intermediate Similarity	NPD6083	Phase 2
0.76	Intermediate Similarity	NPD6084	Phase 2
0.7579	Intermediate Similarity	NPD3573	Approved
0.7576	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.757	Intermediate Similarity	NPD6650	Approved
0.757	Intermediate Similarity	NPD6649	Approved
0.7551	Intermediate Similarity	NPD4202	Approved
0.7524	Intermediate Similarity	NPD5701	Approved
0.7524	Intermediate Similarity	NPD5697	Approved
0.75	Intermediate Similarity	NPD6672	Approved
0.75	Intermediate Similarity	NPD5737	Approved
0.75	Intermediate Similarity	NPD4697	Phase 3
0.7477	Intermediate Similarity	NPD6883	Approved
0.7477	Intermediate Similarity	NPD7290	Approved
0.7477	Intermediate Similarity	NPD7102	Approved
0.7453	Intermediate Similarity	NPD6011	Approved
0.7449	Intermediate Similarity	NPD6411	Approved
0.7423	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD8130	Phase 1
0.7407	Intermediate Similarity	NPD6617	Approved
0.7407	Intermediate Similarity	NPD6847	Approved
0.7407	Intermediate Similarity	NPD6869	Approved
0.7407	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7525	Registered
0.7387	Intermediate Similarity	NPD7115	Discovery
0.7383	Intermediate Similarity	NPD6013	Approved
0.7383	Intermediate Similarity	NPD6012	Approved
0.7383	Intermediate Similarity	NPD6014	Approved
0.7383	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1694	Approved
0.7353	Intermediate Similarity	NPD5696	Approved
0.7353	Intermediate Similarity	NPD4225	Approved
0.7339	Intermediate Similarity	NPD6882	Approved
0.7339	Intermediate Similarity	NPD8297	Approved
0.7333	Intermediate Similarity	NPD6117	Approved
0.7327	Intermediate Similarity	NPD5222	Approved
0.7327	Intermediate Similarity	NPD5221	Approved
0.7327	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD8328	Phase 3
0.7303	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD6001	Approved
0.7292	Intermediate Similarity	NPD6098	Approved
0.7264	Intermediate Similarity	NPD6008	Approved
0.7263	Intermediate Similarity	NPD3668	Phase 3
0.7255	Intermediate Similarity	NPD5173	Approved
0.7255	Intermediate Similarity	NPD4755	Approved
0.7253	Intermediate Similarity	NPD6116	Phase 1
0.7245	Intermediate Similarity	NPD6101	Approved
0.7245	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD5695	Phase 3
0.7222	Intermediate Similarity	NPD6942	Approved
0.7222	Intermediate Similarity	NPD7339	Approved
0.7174	Intermediate Similarity	NPD6118	Approved
0.7174	Intermediate Similarity	NPD6115	Approved
0.7174	Intermediate Similarity	NPD6114	Approved
0.7174	Intermediate Similarity	NPD6697	Approved
0.7143	Intermediate Similarity	NPD7632	Discontinued
0.7143	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6868	Approved
0.7115	Intermediate Similarity	NPD5285	Approved
0.7115	Intermediate Similarity	NPD4696	Approved
0.7115	Intermediate Similarity	NPD4700	Approved
0.7115	Intermediate Similarity	NPD5286	Approved
0.7113	Intermediate Similarity	NPD5279	Phase 3
0.7113	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD4753	Phase 2
0.7071	Intermediate Similarity	NPD6904	Approved
0.7071	Intermediate Similarity	NPD6673	Approved
0.7071	Intermediate Similarity	NPD6080	Approved
0.7053	Intermediate Similarity	NPD4221	Approved
0.7053	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD4223	Phase 3
0.7048	Intermediate Similarity	NPD5223	Approved
0.7037	Intermediate Similarity	NPD6412	Phase 2
0.7018	Intermediate Similarity	NPD6335	Approved
0.701	Intermediate Similarity	NPD5329	Approved
0.7	Intermediate Similarity	NPD5207	Approved
0.6991	Remote Similarity	NPD6274	Approved
0.699	Remote Similarity	NPD7614	Phase 1
0.6983	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD5211	Phase 2
0.6981	Remote Similarity	NPD5225	Approved
0.6981	Remote Similarity	NPD5226	Approved
0.6981	Remote Similarity	NPD5224	Approved
0.6981	Remote Similarity	NPD4633	Approved
0.6979	Remote Similarity	NPD4788	Approved
0.697	Remote Similarity	NPD5208	Approved
0.6964	Remote Similarity	NPD4632	Approved
0.6957	Remote Similarity	NPD7100	Approved
0.6957	Remote Similarity	NPD7101	Approved
0.6931	Remote Similarity	NPD5281	Approved
0.6931	Remote Similarity	NPD5284	Approved
0.693	Remote Similarity	NPD6317	Approved
0.6917	Remote Similarity	NPD7736	Approved
0.6916	Remote Similarity	NPD5175	Approved
0.6916	Remote Similarity	NPD4754	Approved
0.6916	Remote Similarity	NPD5174	Approved
0.6909	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD4197	Approved
0.6893	Remote Similarity	NPD5210	Approved
0.6893	Remote Similarity	NPD4629	Approved
0.6889	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.687	Remote Similarity	NPD6313	Approved
0.687	Remote Similarity	NPD6314	Approved
0.6863	Remote Similarity	NPD5778	Approved
0.6863	Remote Similarity	NPD5779	Approved
0.6854	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD5141	Approved
0.6847	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4695	Discontinued
0.6838	Remote Similarity	NPD6909	Approved
0.6838	Remote Similarity	NPD6908	Approved
0.6827	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD7732	Phase 3
0.6818	Remote Similarity	NPD6686	Approved
0.6814	Remote Similarity	NPD8133	Approved
0.6809	Remote Similarity	NPD3617	Approved
0.6807	Remote Similarity	NPD7492	Approved
0.6789	Remote Similarity	NPD4768	Approved
0.6789	Remote Similarity	NPD4767	Approved
0.6783	Remote Similarity	NPD6009	Approved
0.6768	Remote Similarity	NPD4623	Approved
0.6768	Remote Similarity	NPD4690	Approved
0.6768	Remote Similarity	NPD4519	Discontinued
0.6768	Remote Similarity	NPD4689	Approved
0.6768	Remote Similarity	NPD5205	Approved
0.6768	Remote Similarity	NPD4693	Phase 3
0.6768	Remote Similarity	NPD4138	Approved
0.6768	Remote Similarity	NPD4688	Approved
0.6765	Remote Similarity	NPD6050	Approved
0.6765	Remote Similarity	NPD5693	Phase 1
0.6752	Remote Similarity	NPD6059	Approved
0.6752	Remote Similarity	NPD6319	Approved
0.6752	Remote Similarity	NPD6054	Approved
0.675	Remote Similarity	NPD6616	Approved
0.675	Remote Similarity	NPD7507	Approved
0.6733	Remote Similarity	NPD6051	Approved
0.6723	Remote Similarity	NPD7604	Phase 2
0.6703	Remote Similarity	NPD5777	Approved
0.6695	Remote Similarity	NPD5983	Phase 2
0.6694	Remote Similarity	NPD7078	Approved
0.6694	Remote Similarity	NPD8293	Discontinued
0.6667	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4729	Approved
0.6667	Remote Similarity	NPD4730	Approved
0.6667	Remote Similarity	NPD5128	Approved
0.6667	Remote Similarity	NPD3703	Phase 2
0.6667	Remote Similarity	NPD5692	Phase 3
0.6667	Remote Similarity	NPD5168	Approved
0.6639	Remote Similarity	NPD6370	Approved
0.6632	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD6336	Discontinued
0.6606	Remote Similarity	NPD6052	Approved
0.6602	Remote Similarity	NPD5694	Approved
0.6602	Remote Similarity	NPD7637	Suspended
0.66	Remote Similarity	NPD5280	Approved
0.66	Remote Similarity	NPD4694	Approved
0.66	Remote Similarity	NPD5690	Phase 2
0.6598	Remote Similarity	NPD5369	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