NPASS Compound

Structure

CID139418 OpenBabel06191715492D 46 47 0 0 1 0 0 0 0 0999 V2000 0.6088 -6.4012 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5962 -3.7281 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9456 -0.2045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5043 -5.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3133 -4.8189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2268 -5.2257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0358 -4.6379 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9494 -5.0446 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7584 -4.4568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6719 -4.8636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4810 -4.2758 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3945 -4.6825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6254 -1.9454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9344 -0.9943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6473 -2.1533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2035 -4.0947 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8689 -0.3706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8470 -0.1627 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9126 -0.7864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1998 0.3726 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3383 -3.1043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1171 -4.5015 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5162 -0.9058 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5647 -2.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1580 -1.3365 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -2.5691 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 -0.9271 -4.4712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2216 0.1647 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3601 -3.3122 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 9.9261 -3.9137 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.4943 -0.6979 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 9.8216 -2.9192 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 9.1634 -1.4410 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2361 -5.4223 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5525 0.9078 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.8396 -4.3204 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.8033 0.2532 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3578 0.6045 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0511 -4.2633 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.9555 -2.4192 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 4 1 0 0 0 0 2 28 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 16 1 0 0 0 0 13 14 1 0 0 0 0 13 15 1 0 0 0 0 14 19 1 0 0 0 0 15 21 1 0 0 0 0 16 22 1 0 0 0 0 17 18 1 0 0 0 0 17 20 1 0 0 0 0 18 23 1 0 0 0 0 19 30 1 0 0 0 0 20 30 1 0 0 0 0 22 32 1 0 0 0 0 23 33 1 0 0 0 0 24 25 1 0 0 0 0 24 34 1 0 0 0 0 25 35 1 0 0 0 0 26 29 1 0 0 0 0 26 31 1 0 0 0 0 27 29 2 0 0 0 0 27 37 1 0 0 0 0 28 38 2 0 0 0 0 28 44 1 0 0 0 0 29 36 1 0 0 0 0 30 39 1 1 0 0 0 31 21 1 1 0 0 0 31 44 1 0 0 0 0 32 40 1 6 0 0 0 33 41 1 1 0 0 0 34 32 1 6 0 0 0 34 45 1 0 0 0 0 35 33 1 1 0 0 0 35 45 1 0 0 0 0 36 42 2 0 0 0 0 36 46 1 0 0 0 0 37 3 1 1 0 0 0 37 43 1 0 0 0 0 37 46 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	386.25
Volume:	414.049
LogP:	3.902
LogD:	3.531
LogS:	-4.904
# Rotatable Bonds:	4
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.448
Synthetic Accessibility Score:	4.566
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.651
MDCK Permeability:	2.6564935978967696e-05
Pgp-inhibitor:	0.992
Pgp-substrate:	0.184
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.098
30% Bioavailability (F30%):	0.559

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.866
Plasma Protein Binding (PPB):	95.5240249633789%
Volume Distribution (VD):	1.422
Pgp-substrate:	3.5025722980499268%

ADMET: Metabolism

CYP1A2-inhibitor:	0.123
CYP1A2-substrate:	0.45
CYP2C19-inhibitor:	0.396
CYP2C19-substrate:	0.882
CYP2C9-inhibitor:	0.442
CYP2C9-substrate:	0.09
CYP2D6-inhibitor:	0.042
CYP2D6-substrate:	0.471
CYP3A4-inhibitor:	0.9
CYP3A4-substrate:	0.483

ADMET: Excretion

Clearance (CL):	9.849
Half-life (T1/2):	0.176

ADMET: Toxicity

hERG Blockers:	0.131
Human Hepatotoxicity (H-HT):	0.432
Drug-inuced Liver Injury (DILI):	0.049
AMES Toxicity:	0.025
Rat Oral Acute Toxicity:	0.438
Maximum Recommended Daily Dose:	0.946
Skin Sensitization:	0.909
Carcinogencity:	0.695
Eye Corrosion:	0.003
Eye Irritation:	0.022
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC139418

Natural Product ID:	NPC139418
*Common Name:**	Donnaienin C
IUPAC Name:	[(2R,8R,13R)-8,13-dihydroxy-1-[(5S)-5-hydroxy-5-methyl-2-oxofuran-3-yl]-13-[(2R,5R)-5-[(1R)-1-hydroxytridecyl]oxolan-2-yl]tridecan-2-yl] acetate
Synonyms:	Donnaienin C
Standard InCHIKey:	MULMKVZTRRCCJX-VFHXHHDVSA-N
Standard InCHI:	InChI=1S/C37H66O9/c1-4-5-6-7-8-9-10-11-12-16-22-32(40)34-24-25-35(45-34)33(41)23-18-17-20-30(39)19-14-13-15-21-31(44-28(2)38)26-29-27-37(3,43)46-36(29)42/h27,30-35,39-41,43H,4-26H2,1-3H3/t30-,31-,32-,33-,34-,35-,37+/m1/s1
SMILES:	CCCCCCCCCCCC[C@H]([C@H]1CC[C@@H](O1)[C@@H](CCCC[C@@H](CCCCC[C@H](CC1=C[C@@](OC1=O)(C)O)OC(=O)C)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL500505
PubChem CID:	44559052
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
NPO9339	Beilschmiedia tsangii	Species	Lauraceae	Eukaryota	roots	Mudan, Pingtung County, Taiwan	2009-APR	PMID[21846089]
NPO9339	Beilschmiedia tsangii	Species	Lauraceae	Eukaryota	n.a.	root	n.a.	PMID[21846089]
NPO9339	Beilschmiedia tsangii	Species	Lauraceae	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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[462971]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[462971]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	=	7.1	ug.mL-1	PMID[462971]

☑ 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 NPC139418 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	188
0.1-0.2	1452
0.2-0.3	5506
0.3-0.4	13238
0.4-0.5	11783
0.5-0.6	6914
0.6-0.7	2891
0.7-0.8	526
0.8-0.85	34
0.85-0.9	60
0.9-0.95	80
0.95-1	25

Similarity Score	Similarity Level	Natural Product ID
0.9881	High Similarity	NPC473904
0.9651	High Similarity	NPC11456
0.9639	High Similarity	NPC103523
0.9639	High Similarity	NPC134865
0.9524	High Similarity	NPC178215
0.9518	High Similarity	NPC110710
0.9518	High Similarity	NPC66346
0.9518	High Similarity	NPC132496
0.9518	High Similarity	NPC107986
0.9518	High Similarity	NPC82795
0.9518	High Similarity	NPC1083
0.9518	High Similarity	NPC473478
0.9518	High Similarity	NPC283085
0.9518	High Similarity	NPC103284
0.9518	High Similarity	NPC231009
0.9518	High Similarity	NPC473669
0.9518	High Similarity	NPC286338
0.9518	High Similarity	NPC473651
0.9518	High Similarity	NPC223871
0.9412	High Similarity	NPC21208
0.9412	High Similarity	NPC20339
0.9412	High Similarity	NPC48338
0.9412	High Similarity	NPC233551
0.9412	High Similarity	NPC40376
0.9412	High Similarity	NPC280621
0.9405	High Similarity	NPC308412
0.9405	High Similarity	NPC475581
0.9405	High Similarity	NPC219498
0.9405	High Similarity	NPC210218
0.9405	High Similarity	NPC204686
0.9405	High Similarity	NPC240695
0.9405	High Similarity	NPC107717
0.9405	High Similarity	NPC62118
0.9405	High Similarity	NPC171174
0.9405	High Similarity	NPC69082
0.9405	High Similarity	NPC279267
0.9405	High Similarity	NPC473687
0.9405	High Similarity	NPC114694
0.9405	High Similarity	NPC142117
0.9405	High Similarity	NPC134807
0.9405	High Similarity	NPC134885
0.9405	High Similarity	NPC232555
0.9405	High Similarity	NPC231096
0.9302	High Similarity	NPC477011
0.9302	High Similarity	NPC91067
0.9302	High Similarity	NPC473504
0.9302	High Similarity	NPC42598
0.9302	High Similarity	NPC130359
0.9302	High Similarity	NPC93794
0.9302	High Similarity	NPC40066
0.9302	High Similarity	NPC81778
0.9302	High Similarity	NPC20621
0.9302	High Similarity	NPC14901
0.9302	High Similarity	NPC318963
0.9286	High Similarity	NPC477014
0.9286	High Similarity	NPC329838
0.9286	High Similarity	NPC329615
0.9286	High Similarity	NPC477013
0.9205	High Similarity	NPC473561
0.9205	High Similarity	NPC473663
0.9205	High Similarity	NPC473723
0.9205	High Similarity	NPC475173
0.9195	High Similarity	NPC239517
0.9186	High Similarity	NPC81045
0.9186	High Similarity	NPC133730
0.9186	High Similarity	NPC61257
0.9186	High Similarity	NPC169511
0.9186	High Similarity	NPC39754
0.9186	High Similarity	NPC172821
0.9186	High Similarity	NPC261952
0.9186	High Similarity	NPC171135
0.9186	High Similarity	NPC242364
0.9186	High Similarity	NPC320569
0.9186	High Similarity	NPC274446
0.9186	High Similarity	NPC191929
0.9186	High Similarity	NPC151403
0.9186	High Similarity	NPC287164
0.9186	High Similarity	NPC100454
0.9186	High Similarity	NPC234077
0.9176	High Similarity	NPC477015
0.9176	High Similarity	NPC112685
0.9167	High Similarity	NPC163093
0.9167	High Similarity	NPC156804
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	NPC180363
0.9157	High Similarity	NPC73310
0.9157	High Similarity	NPC329829
0.9157	High Similarity	NPC473712
0.9091	High Similarity	NPC473707
0.908	High Similarity	NPC280612
0.907	High Similarity	NPC258068
0.907	High Similarity	NPC20533
0.907	High Similarity	NPC476583
0.9059	High Similarity	NPC471567
0.9059	High Similarity	NPC120398
0.9059	High Similarity	NPC182383
0.9059	High Similarity	NPC322529
0.9048	High Similarity	NPC144415
0.9048	High Similarity	NPC253801
0.8966	High Similarity	NPC89001
0.8966	High Similarity	NPC320458
0.8966	High Similarity	NPC473905
0.8953	High Similarity	NPC47937
0.8953	High Similarity	NPC241360
0.8953	High Similarity	NPC132940
0.8953	High Similarity	NPC282815
0.8953	High Similarity	NPC25703
0.8953	High Similarity	NPC293136
0.8953	High Similarity	NPC219652
0.8953	High Similarity	NPC473840
0.8864	High Similarity	NPC477017
0.8864	High Similarity	NPC477016
0.8851	High Similarity	NPC477012
0.8837	High Similarity	NPC477018
0.8837	High Similarity	NPC470400
0.8837	High Similarity	NPC473156
0.8837	High Similarity	NPC319036
0.8837	High Similarity	NPC77871
0.8837	High Similarity	NPC202055
0.8837	High Similarity	NPC39279
0.8837	High Similarity	NPC473671
0.8837	High Similarity	NPC100921
0.8837	High Similarity	NPC25764
0.8837	High Similarity	NPC292809
0.8837	High Similarity	NPC475268
0.8837	High Similarity	NPC39167
0.8837	High Similarity	NPC235809
0.8837	High Similarity	NPC9678
0.8778	High Similarity	NPC473520
0.8736	High Similarity	NPC477010
0.8736	High Similarity	NPC309211
0.8636	High Similarity	NPC470401
0.8636	High Similarity	NPC154097
0.8636	High Similarity	NPC159750
0.8636	High Similarity	NPC473649
0.8636	High Similarity	NPC473995
0.8391	Intermediate Similarity	NPC286770
0.8391	Intermediate Similarity	NPC284472
0.8391	Intermediate Similarity	NPC229799
0.8316	Intermediate Similarity	NPC187268
0.8276	Intermediate Similarity	NPC11383
0.8276	Intermediate Similarity	NPC474959
0.8276	Intermediate Similarity	NPC475046
0.8276	Intermediate Similarity	NPC310450
0.8202	Intermediate Similarity	NPC21469
0.8191	Intermediate Similarity	NPC36954
0.8172	Intermediate Similarity	NPC273579
0.8172	Intermediate Similarity	NPC295204
0.8172	Intermediate Similarity	NPC162205
0.8172	Intermediate Similarity	NPC288240
0.8065	Intermediate Similarity	NPC30515
0.8065	Intermediate Similarity	NPC473321
0.8043	Intermediate Similarity	NPC295312
0.8	Intermediate Similarity	NPC471141
0.7979	Intermediate Similarity	NPC475912
0.7979	Intermediate Similarity	NPC476300
0.7979	Intermediate Similarity	NPC81419
0.7979	Intermediate Similarity	NPC179746
0.7978	Intermediate Similarity	NPC116543
0.7957	Intermediate Similarity	NPC474232
0.7957	Intermediate Similarity	NPC474761
0.7957	Intermediate Similarity	NPC476004
0.7957	Intermediate Similarity	NPC51004
0.7957	Intermediate Similarity	NPC473619
0.7957	Intermediate Similarity	NPC473448
0.7938	Intermediate Similarity	NPC203627
0.7917	Intermediate Similarity	NPC306041
0.7917	Intermediate Similarity	NPC279621
0.7917	Intermediate Similarity	NPC476315
0.7912	Intermediate Similarity	NPC469483
0.7895	Intermediate Similarity	NPC81386
0.7895	Intermediate Similarity	NPC474035
0.7895	Intermediate Similarity	NPC474338
0.7889	Intermediate Similarity	NPC288471
0.7889	Intermediate Similarity	NPC41856
0.7872	Intermediate Similarity	NPC12172
0.7872	Intermediate Similarity	NPC208886
0.7872	Intermediate Similarity	NPC184463
0.7849	Intermediate Similarity	NPC307411
0.7849	Intermediate Similarity	NPC474032
0.7841	Intermediate Similarity	NPC470147
0.7841	Intermediate Similarity	NPC133226
0.7835	Intermediate Similarity	NPC471462
0.7826	Intermediate Similarity	NPC160138
0.7816	Intermediate Similarity	NPC279214
0.7816	Intermediate Similarity	NPC221095
0.7816	Intermediate Similarity	NPC108816
0.7816	Intermediate Similarity	NPC93763
0.7812	Intermediate Similarity	NPC14961
0.7812	Intermediate Similarity	NPC270013
0.7812	Intermediate Similarity	NPC471142
0.7789	Intermediate Similarity	NPC238090
0.7789	Intermediate Similarity	NPC472195

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 NPC139418 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	167
0.1-0.2	2196
0.2-0.3	3808
0.3-0.4	2075
0.4-0.5	646
0.5-0.6	208
0.6-0.7	46
0.7-0.8	4
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
0.7766	Intermediate Similarity	NPD6698	Approved
0.7766	Intermediate Similarity	NPD46	Approved
0.7576	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7573	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7838	Discovery
0.7333	Intermediate Similarity	NPD6686	Approved
0.732	Intermediate Similarity	NPD7983	Approved
0.729	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6371	Approved
0.6869	Remote Similarity	NPD5785	Approved
0.6765	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD4250	Approved
0.6735	Remote Similarity	NPD4251	Approved
0.6731	Remote Similarity	NPD4225	Approved
0.6724	Remote Similarity	NPD8516	Approved
0.6724	Remote Similarity	NPD8517	Approved
0.6724	Remote Similarity	NPD8515	Approved
0.6724	Remote Similarity	NPD8513	Phase 3
0.6701	Remote Similarity	NPD5363	Approved
0.6701	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD7839	Suspended
0.6667	Remote Similarity	NPD7154	Phase 3
0.6667	Remote Similarity	NPD5362	Discontinued
0.6633	Remote Similarity	NPD4249	Approved
0.6598	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD4756	Discovery
0.6531	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD3197	Phase 1
0.6477	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD5344	Discontinued
0.6446	Remote Similarity	NPD8074	Phase 3
0.6436	Remote Similarity	NPD1695	Approved
0.6392	Remote Similarity	NPD4270	Approved
0.6392	Remote Similarity	NPD4269	Approved
0.6364	Remote Similarity	NPD7507	Approved
0.6354	Remote Similarity	NPD4252	Approved
0.6333	Remote Similarity	NPD7829	Approved
0.6333	Remote Similarity	NPD7830	Approved
0.6316	Remote Similarity	NPD4271	Approved
0.6316	Remote Similarity	NPD4268	Approved
0.63	Remote Similarity	NPD5786	Approved
0.625	Remote Similarity	NPD5778	Approved
0.625	Remote Similarity	NPD5779	Approved
0.6239	Remote Similarity	NPD7115	Discovery
0.6228	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.621	Remote Similarity	NPD7319	Approved
0.6204	Remote Similarity	NPD7640	Approved
0.6204	Remote Similarity	NPD7639	Approved
0.6198	Remote Similarity	NPD7642	Approved
0.6186	Remote Similarity	NPD4822	Approved
0.6186	Remote Similarity	NPD4819	Approved
0.6186	Remote Similarity	NPD4821	Approved
0.6186	Remote Similarity	NPD7641	Discontinued
0.6186	Remote Similarity	NPD4820	Approved
0.6174	Remote Similarity	NPD6053	Discontinued
0.6167	Remote Similarity	NPD8033	Approved
0.6163	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD6110	Phase 1
0.6162	Remote Similarity	NPD5331	Approved
0.6162	Remote Similarity	NPD5332	Approved
0.6146	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD5369	Approved
0.6122	Remote Similarity	NPD4790	Discontinued
0.6111	Remote Similarity	NPD7638	Approved
0.6102	Remote Similarity	NPD7500	Approved
0.6083	Remote Similarity	NPD8377	Approved
0.6083	Remote Similarity	NPD8294	Approved
0.6061	Remote Similarity	NPD6435	Approved
0.6055	Remote Similarity	NPD6648	Approved
0.6053	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.605	Remote Similarity	NPD7328	Approved
0.605	Remote Similarity	NPD7327	Approved
0.604	Remote Similarity	NPD1694	Approved
0.6038	Remote Similarity	NPD5282	Discontinued
0.6033	Remote Similarity	NPD8378	Approved
0.6033	Remote Similarity	NPD8296	Approved
0.6033	Remote Similarity	NPD8380	Approved
0.6033	Remote Similarity	NPD8444	Approved
0.6033	Remote Similarity	NPD8335	Approved
0.6033	Remote Similarity	NPD8379	Approved
0.6018	Remote Similarity	NPD6412	Phase 2
0.6	Remote Similarity	NPD7516	Approved
0.6	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6	Remote Similarity	NPD8039	Approved
0.5968	Remote Similarity	NPD8451	Approved
0.5962	Remote Similarity	NPD5370	Suspended
0.592	Remote Similarity	NPD8448	Approved
0.59	Remote Similarity	NPD5209	Approved
0.5889	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5887	Remote Similarity	NPD8341	Approved
0.5887	Remote Similarity	NPD8340	Approved
0.5887	Remote Similarity	NPD8342	Approved
0.5887	Remote Similarity	NPD8299	Approved
0.5862	Remote Similarity	NPD6421	Discontinued
0.5859	Remote Similarity	NPD5368	Approved
0.5849	Remote Similarity	NPD7637	Suspended
0.5849	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5847	Remote Similarity	NPD8133	Approved
0.5843	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.584	Remote Similarity	NPD8273	Phase 1
0.5833	Remote Similarity	NPD3730	Approved
0.5833	Remote Similarity	NPD4266	Approved
0.5833	Remote Similarity	NPD3196	Approved
0.5833	Remote Similarity	NPD3194	Approved
0.5833	Remote Similarity	NPD3728	Approved
0.5833	Remote Similarity	NPD7505	Discontinued
0.5833	Remote Similarity	NPD3195	Phase 2
0.5824	Remote Similarity	NPD3704	Approved
0.5806	Remote Similarity	NPD8328	Phase 3
0.5794	Remote Similarity	NPD6399	Phase 3
0.5781	Remote Similarity	NPD8390	Approved
0.5781	Remote Similarity	NPD8391	Approved
0.5781	Remote Similarity	NPD8392	Approved
0.578	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5776	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5772	Remote Similarity	NPD7503	Approved
0.5763	Remote Similarity	NPD8297	Approved
0.576	Remote Similarity	NPD7492	Approved
0.5755	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5748	Remote Similarity	NPD7736	Approved
0.5747	Remote Similarity	NPD6109	Phase 1
0.5747	Remote Similarity	NPD69	Approved
0.5747	Remote Similarity	NPD9119	Approved
0.5739	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5736	Remote Similarity	NPD7260	Phase 2
0.5727	Remote Similarity	NPD7902	Approved
0.5726	Remote Similarity	NPD2067	Discontinued
0.5726	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD7623	Phase 3
0.5726	Remote Similarity	NPD8080	Discontinued
0.5714	Remote Similarity	NPD3172	Approved
0.5714	Remote Similarity	NPD6616	Approved
0.5702	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5692	Remote Similarity	NPD6845	Suspended
0.5691	Remote Similarity	NPD6054	Approved
0.5691	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.5678	Remote Similarity	NPD2204	Approved
0.5669	Remote Similarity	NPD8293	Discontinued
0.5669	Remote Similarity	NPD7747	Phase 1
0.5669	Remote Similarity	NPD7078	Approved
0.5669	Remote Similarity	NPD7746	Phase 1
0.5664	Remote Similarity	NPD7632	Discontinued
0.5663	Remote Similarity	NPD6927	Phase 3
0.566	Remote Similarity	NPD6101	Approved
0.566	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5645	Remote Similarity	NPD8268	Approved
0.5645	Remote Similarity	NPD8269	Approved
0.5645	Remote Similarity	NPD8267	Approved
0.5645	Remote Similarity	NPD8266	Approved
0.5632	Remote Similarity	NPD9118	Approved
0.563	Remote Similarity	NPD6882	Approved
0.5614	Remote Similarity	NPD6647	Phase 2
0.56	Remote Similarity	NPD6370	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