NPASS Compound

Structure

NPC473904 OpenBabel07101718322D 46 47 0 0 1 0 0 0 0 0999 V2000 -22.3057 5.7172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1499 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -21.9967 4.7661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -21.0185 4.5582 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -20.3494 5.3014 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -19.3713 5.0935 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -18.7021 5.8366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2837 -0.9463 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0927 -0.3585 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3701 -0.5395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -17.7240 5.6287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0062 -0.7652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5611 -1.1273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -17.0548 6.3718 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8152 -0.1774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6476 -0.7206 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -16.0767 6.1639 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.7288 -0.5842 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8385 -1.3084 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.4076 6.9071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.5378 0.0036 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.7895 5.0050 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.4805 4.0539 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.1934 1.2769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.7811 2.0859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1160 -1.4894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 -1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9250 -0.9016 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -14.4294 6.6992 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -14.1204 5.7481 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.4333 0.9981 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -13.5024 3.8460 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -12.2423 1.5859 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -13.1934 2.8949 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9945 -0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.8205 0.0929 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.7603 7.4423 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.1423 5.5402 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.5197 1.4049 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.8332 4.5891 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6637 0.6386 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 -12.2423 2.5859 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 3 1 0 0 0 0 2 37 1 0 0 0 0 3 4 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 11 1 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 9 12 1 0 0 0 0 10 13 1 0 0 0 0 11 14 1 0 0 0 0 12 15 1 0 0 0 0 13 16 1 0 0 0 0 14 17 1 0 0 0 0 15 18 1 0 0 0 0 16 19 1 0 0 0 0 17 20 1 0 0 0 0 18 21 1 0 0 0 0 19 29 1 0 0 0 0 20 30 1 0 0 0 0 21 32 1 0 0 0 0 22 23 1 0 0 0 0 22 31 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 28 1 0 0 0 0 26 29 1 0 0 0 0 27 28 2 0 0 0 0 27 37 1 0 0 0 0 28 36 1 0 0 0 0 29 38 1 0 0 0 0 30 31 1 0 0 0 0 30 39 1 1 0 0 0 31 40 1 1 0 0 0 32 41 1 1 0 0 0 33 42 1 6 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 43 2 0 0 0 0 36 46 1 0 0 0 0 37 44 1 0 0 0 0 37 46 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	656.49
Volume:	705.234
LogP:	6.51
LogD:	4.286
LogS:	-3.872
# Rotatable Bonds:	28
TPSA:	156.91
# H-Bond Aceptor:	9
# H-Bond Donor:	6
# Rings:	2
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.043
Synthetic Accessibility Score:	4.948
Fsp3:	0.919
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.142
MDCK Permeability:	1.0844979442481417e-05
Pgp-inhibitor:	0.192
Pgp-substrate:	0.878
Human Intestinal Absorption (HIA):	0.229
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.823

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.037
Plasma Protein Binding (PPB):	96.775634765625%
Volume Distribution (VD):	0.929
Pgp-substrate:	4.097662448883057%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.178
CYP2C19-inhibitor:	0.064
CYP2C19-substrate:	0.053
CYP2C9-inhibitor:	0.158
CYP2C9-substrate:	0.947
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.01
CYP3A4-inhibitor:	0.519
CYP3A4-substrate:	0.03

ADMET: Excretion

Clearance (CL):	8.432
Half-life (T1/2):	0.195

ADMET: Toxicity

hERG Blockers:	0.326
Human Hepatotoxicity (H-HT):	0.243
Drug-inuced Liver Injury (DILI):	0.017
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.001
Maximum Recommended Daily Dose:	0.824
Skin Sensitization:	0.971
Carcinogencity:	0.132
Eye Corrosion:	0.003
Eye Irritation:	0.089
Respiratory Toxicity:	0.951

Download Data

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

Natural Product: NPC473904

Natural Product ID:	NPC473904
*Common Name:**	Parisin
IUPAC Name:	3-[(13S)-2,13-dihydroxy-13-[(2S,5S)-5-[(1S,4S,5R)-1,4,5-trihydroxypentadecyl]oxolan-2-yl]tridecyl]-5-hydroxy-5-methylfuran-2-one
Synonyms:	Parisin
Standard InCHIKey:	USIUGLRYYKXESD-ZAAOCBMESA-N
Standard InCHI:	InChI=1S/C37H68O9/c1-3-4-5-6-7-11-14-17-20-30(39)31(40)22-23-33(42)35-25-24-34(45-35)32(41)21-18-15-12-9-8-10-13-16-19-29(38)26-28-27-37(2,44)46-36(28)43/h27,29-35,38-42,44H,3-26H2,1-2H3/t29?,30-,31+,32+,33+,34+,35+,37?/m1/s1
SMILES:	CCCCCCCCCC[C@H]([C@H](CC[C@@H]([C@@H]1CC[C@H](O1)[C@H](CCCCCCCCCCC(CC1=CC(OC1=O)(C)O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL454773
PubChem CID:	44566775
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
NPO33069	annona salzmanii	Species	Annonaceae	Eukaryota	roots	n.a.	n.a.	PMID[10346951]
NPO33069	annona salzmanii	Species	Annonaceae	Eukaryota	roots	n.a.	n.a.	PMID[12828457]

☑ 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
ED50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	1.0	10'-4 ug/ml	PMID[495893]
NPT189	Cell Line	Vero	Chlorocebus aethiops	ED50	=	1.0	10'-2 ug/ml	PMID[495893]

☑ 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 NPC473904 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	196
0.1-0.2	1480
0.2-0.3	5510
0.3-0.4	12523
0.4-0.5	12317
0.5-0.6	6921
0.6-0.7	3004
0.7-0.8	541
0.8-0.85	36
0.85-0.9	46
0.9-0.95	95
0.95-1	28

Similarity Score	Similarity Level	Natural Product ID
0.9881	High Similarity	NPC139418
0.954	High Similarity	NPC11456
0.9529	High Similarity	NPC233551
0.9529	High Similarity	NPC21208
0.9529	High Similarity	NPC280621
0.9529	High Similarity	NPC48338
0.9529	High Similarity	NPC40376
0.9529	High Similarity	NPC20339
0.9524	High Similarity	NPC107717
0.9524	High Similarity	NPC171174
0.9524	High Similarity	NPC232555
0.9524	High Similarity	NPC134865
0.9524	High Similarity	NPC114694
0.9524	High Similarity	NPC240695
0.9524	High Similarity	NPC62118
0.9524	High Similarity	NPC231096
0.9524	High Similarity	NPC103523
0.9524	High Similarity	NPC142117
0.9524	High Similarity	NPC475581
0.9419	High Similarity	NPC477011
0.9419	High Similarity	NPC20621
0.9419	High Similarity	NPC473504
0.9419	High Similarity	NPC81778
0.9419	High Similarity	NPC93794
0.9419	High Similarity	NPC91067
0.9419	High Similarity	NPC42598
0.9419	High Similarity	NPC318963
0.9419	High Similarity	NPC40066
0.9412	High Similarity	NPC178215
0.9405	High Similarity	NPC82795
0.9405	High Similarity	NPC473478
0.9405	High Similarity	NPC286338
0.9405	High Similarity	NPC110710
0.9405	High Similarity	NPC329615
0.9405	High Similarity	NPC473669
0.9405	High Similarity	NPC329838
0.9405	High Similarity	NPC473651
0.9405	High Similarity	NPC223871
0.9405	High Similarity	NPC1083
0.9405	High Similarity	NPC66346
0.9405	High Similarity	NPC283085
0.9405	High Similarity	NPC132496
0.9405	High Similarity	NPC107986
0.9405	High Similarity	NPC103284
0.9405	High Similarity	NPC231009
0.9318	High Similarity	NPC473561
0.9318	High Similarity	NPC475173
0.9318	High Similarity	NPC473723
0.9318	High Similarity	NPC473663
0.931	High Similarity	NPC239517
0.9302	High Similarity	NPC39754
0.9302	High Similarity	NPC81045
0.9302	High Similarity	NPC191929
0.9302	High Similarity	NPC274446
0.9302	High Similarity	NPC242364
0.9302	High Similarity	NPC261952
0.9302	High Similarity	NPC320569
0.9302	High Similarity	NPC287164
0.9302	High Similarity	NPC234077
0.9302	High Similarity	NPC100454
0.9302	High Similarity	NPC169511
0.9302	High Similarity	NPC172821
0.9302	High Similarity	NPC133730
0.9302	High Similarity	NPC151403
0.9302	High Similarity	NPC171135
0.9302	High Similarity	NPC61257
0.9294	High Similarity	NPC204686
0.9294	High Similarity	NPC69082
0.9294	High Similarity	NPC134885
0.9294	High Similarity	NPC473687
0.9294	High Similarity	NPC210218
0.9294	High Similarity	NPC134807
0.9294	High Similarity	NPC219498
0.9294	High Similarity	NPC308412
0.9294	High Similarity	NPC279267
0.9286	High Similarity	NPC156804
0.9205	High Similarity	NPC473707
0.9195	High Similarity	NPC130359
0.9195	High Similarity	NPC14901
0.9186	High Similarity	NPC20533
0.9186	High Similarity	NPC476583
0.9186	High Similarity	NPC258068
0.9176	High Similarity	NPC477014
0.9176	High Similarity	NPC477013
0.9176	High Similarity	NPC322529
0.9176	High Similarity	NPC471567
0.9176	High Similarity	NPC120398
0.908	High Similarity	NPC320458
0.908	High Similarity	NPC89001
0.908	High Similarity	NPC473905
0.907	High Similarity	NPC112685
0.907	High Similarity	NPC47937
0.907	High Similarity	NPC241360
0.907	High Similarity	NPC132940
0.907	High Similarity	NPC473840
0.907	High Similarity	NPC282815
0.907	High Similarity	NPC219652
0.907	High Similarity	NPC477015
0.907	High Similarity	NPC25703
0.907	High Similarity	NPC293136
0.9059	High Similarity	NPC163093
0.9048	High Similarity	NPC329829
0.9048	High Similarity	NPC131002
0.9048	High Similarity	NPC65930
0.9048	High Similarity	NPC11332
0.9048	High Similarity	NPC475159
0.9048	High Similarity	NPC180363
0.9048	High Similarity	NPC473529
0.9048	High Similarity	NPC145914
0.9048	High Similarity	NPC473780
0.9048	High Similarity	NPC94875
0.9048	High Similarity	NPC73310
0.9048	High Similarity	NPC473712
0.8977	High Similarity	NPC477016
0.8977	High Similarity	NPC280612
0.8977	High Similarity	NPC477017
0.8953	High Similarity	NPC182383
0.8953	High Similarity	NPC25764
0.8953	High Similarity	NPC235809
0.8953	High Similarity	NPC77871
0.8953	High Similarity	NPC477018
0.8953	High Similarity	NPC470400
0.8953	High Similarity	NPC319036
0.8953	High Similarity	NPC202055
0.8953	High Similarity	NPC39279
0.8953	High Similarity	NPC473671
0.8953	High Similarity	NPC292809
0.8953	High Similarity	NPC475268
0.8953	High Similarity	NPC100921
0.8953	High Similarity	NPC39167
0.8953	High Similarity	NPC9678
0.8953	High Similarity	NPC473156
0.8941	High Similarity	NPC144415
0.8941	High Similarity	NPC253801
0.8889	High Similarity	NPC473520
0.8851	High Similarity	NPC309211
0.8851	High Similarity	NPC477010
0.875	High Similarity	NPC473995
0.875	High Similarity	NPC154097
0.875	High Similarity	NPC473649
0.875	High Similarity	NPC477012
0.875	High Similarity	NPC470401
0.875	High Similarity	NPC159750
0.8421	Intermediate Similarity	NPC187268
0.8298	Intermediate Similarity	NPC36954
0.8295	Intermediate Similarity	NPC286770
0.8295	Intermediate Similarity	NPC284472
0.8295	Intermediate Similarity	NPC229799
0.8182	Intermediate Similarity	NPC475046
0.8182	Intermediate Similarity	NPC474959
0.8182	Intermediate Similarity	NPC310450
0.8182	Intermediate Similarity	NPC11383
0.8172	Intermediate Similarity	NPC473321
0.8172	Intermediate Similarity	NPC30515
0.8152	Intermediate Similarity	NPC295312
0.8111	Intermediate Similarity	NPC21469
0.8105	Intermediate Similarity	NPC471141
0.8085	Intermediate Similarity	NPC475912
0.8085	Intermediate Similarity	NPC273579
0.8085	Intermediate Similarity	NPC295204
0.8085	Intermediate Similarity	NPC162205
0.8085	Intermediate Similarity	NPC81419
0.8085	Intermediate Similarity	NPC476300
0.8085	Intermediate Similarity	NPC288240
0.8085	Intermediate Similarity	NPC179746
0.8065	Intermediate Similarity	NPC476004
0.8065	Intermediate Similarity	NPC473619
0.8065	Intermediate Similarity	NPC474761
0.8065	Intermediate Similarity	NPC51004
0.8041	Intermediate Similarity	NPC203627
0.8021	Intermediate Similarity	NPC279621
0.8021	Intermediate Similarity	NPC306041
0.8021	Intermediate Similarity	NPC476315
0.8	Intermediate Similarity	NPC474338
0.8	Intermediate Similarity	NPC474035
0.8	Intermediate Similarity	NPC81386
0.8	Intermediate Similarity	NPC288471
0.7979	Intermediate Similarity	NPC12172
0.7979	Intermediate Similarity	NPC184463
0.7979	Intermediate Similarity	NPC208886
0.7957	Intermediate Similarity	NPC474032
0.7957	Intermediate Similarity	NPC307411
0.7955	Intermediate Similarity	NPC470147
0.7955	Intermediate Similarity	NPC133226
0.7938	Intermediate Similarity	NPC471462
0.7935	Intermediate Similarity	NPC160138
0.7917	Intermediate Similarity	NPC14961
0.7917	Intermediate Similarity	NPC270013
0.7917	Intermediate Similarity	NPC471142
0.7895	Intermediate Similarity	NPC238090
0.7895	Intermediate Similarity	NPC472196
0.7895	Intermediate Similarity	NPC472195
0.7889	Intermediate Similarity	NPC116543
0.7872	Intermediate Similarity	NPC118078
0.7872	Intermediate Similarity	NPC474232
0.7872	Intermediate Similarity	NPC80875
0.7872	Intermediate Similarity	NPC473448
0.7857	Intermediate Similarity	NPC473326
0.7849	Intermediate Similarity	NPC473715
0.7849	Intermediate Similarity	NPC202672

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 NPC473904 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	173
0.1-0.2	2233
0.2-0.3	3793
0.3-0.4	2032
0.4-0.5	665
0.5-0.6	203
0.6-0.7	46
0.7-0.8	5
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7872	Intermediate Similarity	NPD46	Approved
0.7872	Intermediate Similarity	NPD6698	Approved
0.7677	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7838	Discovery
0.7429	Intermediate Similarity	NPD6686	Approved
0.7423	Intermediate Similarity	NPD7983	Approved
0.7383	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD6371	Approved
0.6837	Remote Similarity	NPD4251	Approved
0.6837	Remote Similarity	NPD4250	Approved
0.681	Remote Similarity	NPD8516	Approved
0.681	Remote Similarity	NPD8517	Approved
0.681	Remote Similarity	NPD8513	Phase 3
0.681	Remote Similarity	NPD8515	Approved
0.6804	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5785	Approved
0.6735	Remote Similarity	NPD4249	Approved
0.6699	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4225	Approved
0.6635	Remote Similarity	NPD7839	Suspended
0.6633	Remote Similarity	NPD5363	Approved
0.6598	Remote Similarity	NPD7154	Phase 3
0.6598	Remote Similarity	NPD5362	Discontinued
0.6542	Remote Similarity	NPD5344	Discontinued
0.6535	Remote Similarity	NPD1695	Approved
0.6531	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD8074	Phase 3
0.6489	Remote Similarity	NPD4756	Discovery
0.6465	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD7507	Approved
0.6437	Remote Similarity	NPD3197	Phase 1
0.6417	Remote Similarity	NPD7830	Approved
0.6417	Remote Similarity	NPD7829	Approved
0.6404	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD4270	Approved
0.6327	Remote Similarity	NPD4269	Approved
0.6296	Remote Similarity	NPD7639	Approved
0.6296	Remote Similarity	NPD7640	Approved
0.629	Remote Similarity	NPD7319	Approved
0.6289	Remote Similarity	NPD4252	Approved
0.6281	Remote Similarity	NPD7642	Approved
0.6271	Remote Similarity	NPD7641	Discontinued
0.6263	Remote Similarity	NPD6110	Phase 1
0.6261	Remote Similarity	NPD6053	Discontinued
0.625	Remote Similarity	NPD8033	Approved
0.625	Remote Similarity	NPD4268	Approved
0.625	Remote Similarity	NPD4271	Approved
0.6238	Remote Similarity	NPD5786	Approved
0.6204	Remote Similarity	NPD7638	Approved
0.6202	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.619	Remote Similarity	NPD5779	Approved
0.619	Remote Similarity	NPD5778	Approved
0.6186	Remote Similarity	NPD7115	Discovery
0.6186	Remote Similarity	NPD7500	Approved
0.6174	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD8294	Approved
0.6167	Remote Similarity	NPD8377	Approved
0.6162	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD6648	Approved
0.614	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD7327	Approved
0.6134	Remote Similarity	NPD7328	Approved
0.6132	Remote Similarity	NPD5282	Discontinued
0.6122	Remote Similarity	NPD4820	Approved
0.6122	Remote Similarity	NPD4819	Approved
0.6122	Remote Similarity	NPD4821	Approved
0.6122	Remote Similarity	NPD4822	Approved
0.6116	Remote Similarity	NPD8378	Approved
0.6116	Remote Similarity	NPD8444	Approved
0.6116	Remote Similarity	NPD8296	Approved
0.6116	Remote Similarity	NPD8380	Approved
0.6116	Remote Similarity	NPD8335	Approved
0.6116	Remote Similarity	NPD8379	Approved
0.6106	Remote Similarity	NPD6412	Phase 2
0.61	Remote Similarity	NPD5331	Approved
0.61	Remote Similarity	NPD5332	Approved
0.6092	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD7516	Approved
0.6082	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD4790	Discontinued
0.6061	Remote Similarity	NPD5369	Approved
0.6048	Remote Similarity	NPD8451	Approved
0.6	Remote Similarity	NPD8448	Approved
0.6	Remote Similarity	NPD6435	Approved
0.598	Remote Similarity	NPD1694	Approved
0.5968	Remote Similarity	NPD8342	Approved
0.5968	Remote Similarity	NPD8341	Approved
0.5968	Remote Similarity	NPD8299	Approved
0.5968	Remote Similarity	NPD8340	Approved
0.5948	Remote Similarity	NPD6421	Discontinued
0.5938	Remote Similarity	NPD8039	Approved
0.5932	Remote Similarity	NPD8133	Approved
0.592	Remote Similarity	NPD8273	Phase 1
0.5905	Remote Similarity	NPD5370	Suspended
0.5887	Remote Similarity	NPD8328	Phase 3
0.5862	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD8390	Approved
0.5859	Remote Similarity	NPD8392	Approved
0.5859	Remote Similarity	NPD8391	Approved
0.5854	Remote Similarity	NPD7503	Approved
0.5849	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD5209	Approved
0.584	Remote Similarity	NPD7492	Approved
0.5827	Remote Similarity	NPD7736	Approved
0.5826	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5824	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD7260	Phase 2
0.5806	Remote Similarity	NPD8080	Discontinued
0.58	Remote Similarity	NPD5368	Approved
0.5794	Remote Similarity	NPD6616	Approved
0.5794	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD7637	Suspended
0.5785	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5785	Remote Similarity	NPD7505	Discontinued
0.5778	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5772	Remote Similarity	NPD6054	Approved
0.5769	Remote Similarity	NPD6845	Suspended
0.5765	Remote Similarity	NPD3196	Approved
0.5765	Remote Similarity	NPD3195	Phase 2
0.5765	Remote Similarity	NPD3194	Approved
0.5765	Remote Similarity	NPD4266	Approved
0.5765	Remote Similarity	NPD3730	Approved
0.5765	Remote Similarity	NPD3728	Approved
0.5763	Remote Similarity	NPD2204	Approved
0.5761	Remote Similarity	NPD3704	Approved
0.5752	Remote Similarity	NPD7632	Discontinued
0.5748	Remote Similarity	NPD7078	Approved
0.5748	Remote Similarity	NPD8293	Discontinued
0.5741	Remote Similarity	NPD6399	Phase 3
0.5727	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD8266	Approved
0.5726	Remote Similarity	NPD8268	Approved
0.5726	Remote Similarity	NPD8267	Approved
0.5726	Remote Similarity	NPD8269	Approved
0.5714	Remote Similarity	NPD8297	Approved
0.5682	Remote Similarity	NPD6109	Phase 1
0.5682	Remote Similarity	NPD9119	Approved
0.5682	Remote Similarity	NPD69	Approved
0.568	Remote Similarity	NPD7623	Phase 3
0.568	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.568	Remote Similarity	NPD6370	Approved
0.5678	Remote Similarity	NPD2067	Discontinued
0.5676	Remote Similarity	NPD7902	Approved
0.5667	Remote Similarity	NPD4632	Approved
0.5656	Remote Similarity	NPD6009	Approved
0.5656	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5647	Remote Similarity	NPD3172	Approved
0.5645	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.5645	Remote Similarity	NPD6319	Approved
0.5645	Remote Similarity	NPD6059	Approved
0.5639	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD7746	Phase 1
0.5625	Remote Similarity	NPD7747	Phase 1
0.5607	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5607	Remote Similarity	NPD6101	Approved
0.5603	Remote Similarity	NPD6008	Approved
0.56	Remote Similarity	NPD6016	Approved
0.56	Remote Similarity	NPD6015	Approved
0.56	Remote Similarity	NPD8274	Clinical (unspecified phase)

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