NPASS Compound

Structure

CID133226 OpenBabel06191715492D 41 41 0 0 1 0 0 0 0 0999 V2000 16.4545 -10.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.5885 -11.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.7224 -10.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.7224 -9.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.8564 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.8564 -8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.9904 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.9904 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1244 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1244 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2583 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2583 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.7942 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9.5263 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 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 11.2583 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 0.0000 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 24 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 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 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 17 18 2 0 0 0 0 17 30 1 0 0 0 0 18 32 1 0 0 0 0 19 25 1 0 0 0 0 19 26 1 0 0 0 0 20 25 1 0 0 0 0 20 27 1 0 0 0 0 21 26 1 0 0 0 0 21 28 1 0 0 0 0 22 27 1 0 0 0 0 22 29 1 0 0 0 0 23 28 1 0 0 0 0 24 33 2 0 0 0 0 24 40 1 0 0 0 0 25 34 1 6 0 0 0 26 35 1 6 0 0 0 27 36 1 6 0 0 0 28 37 1 6 0 0 0 29 16 1 6 0 0 0 29 40 1 0 0 0 0 30 31 1 0 0 0 0 30 38 1 1 0 0 0 31 23 1 1 0 0 0 31 41 1 0 0 0 0 32 39 2 0 0 0 0 32 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	586.41
Volume:	624.674
LogP:	4.711
LogD:	2.997
LogS:	-5.452
# Rotatable Bonds:	26
TPSA:	150.59
# H-Bond Aceptor:	9
# H-Bond Donor:	4
# Rings:	1
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.085
Synthetic Accessibility Score:	4.498
Fsp3:	0.906
Lipinski Rule-of-5:	Accepted
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:	-5.076
MDCK Permeability:	3.036969792447053e-05
Pgp-inhibitor:	0.628
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.047
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.03
Plasma Protein Binding (PPB):	96.13286590576172%
Volume Distribution (VD):	1.029
Pgp-substrate:	2.968442916870117%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.1
CYP2C19-inhibitor:	0.063
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.332
CYP2C9-substrate:	0.931
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.018
CYP3A4-inhibitor:	0.61
CYP3A4-substrate:	0.074

ADMET: Excretion

Clearance (CL):	7.339
Half-life (T1/2):	0.827

ADMET: Toxicity

hERG Blockers:	0.071
Human Hepatotoxicity (H-HT):	0.874
Drug-inuced Liver Injury (DILI):	0.276
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.004
Maximum Recommended Daily Dose:	0.999
Skin Sensitization:	0.965
Carcinogencity:	0.157
Eye Corrosion:	0.093
Eye Irritation:	0.124
Respiratory Toxicity:	0.871

Download Data

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

Natural Product: NPC133226

Natural Product ID:	NPC133226
*Common Name:**	Cryptocaryol D
IUPAC Name:	[(2S,4S,6R,8R,10R)-2,4,6,8-tetrahydroxy-1-[(2S,3S)-3-hydroxy-6-oxo-2,3-dihydropyran-2-yl]pentacosan-10-yl] acetate
Synonyms:	Cryptocaryol D
Standard InCHIKey:	QTODHKJVJUSIHI-YEWNYCFTSA-N
Standard InCHI:	InChI=1S/C32H58O9/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-29(40-24(2)33)22-27(36)20-25(34)19-26(35)21-28(37)23-31-30(38)17-18-32(39)41-31/h17-18,25-31,34-38H,3-16,19-23H2,1-2H3/t25-,26+,27-,28+,29-,30+,31+/m1/s1
SMILES:	CCCCCCCCCCCCCCC[C@@H](OC(=O)C)C[C@@H](C[C@@H](C[C@@H](C[C@@H](C[C@@H]1OC(=O)C=C[C@@H]1O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1784375
PubChem CID:	54583047
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001722] Fatty alcohol esters

*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
NPO33207	cryptocarya sp.	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21539301]
NPO29906	Cryptocarya	Genus	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21539301]

☑ 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
EC50	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4409	Individual Protein	Programmed cell death protein 4	Homo sapiens	EC50	=	1500.0	nM	PMID[554406]

☑ 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 NPC133226 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	1900
0.2-0.3	5676
0.3-0.4	15618
0.4-0.5	11758
0.5-0.6	5342
0.6-0.7	1750
0.7-0.8	412
0.8-0.85	36
0.85-0.9	7
0.9-0.95	7
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470147
0.9865	High Similarity	NPC180725
0.9865	High Similarity	NPC470148
0.9865	High Similarity	NPC470149
0.973	High Similarity	NPC248775
0.9595	High Similarity	NPC474026
0.9324	High Similarity	NPC285840
0.9324	High Similarity	NPC327041
0.9054	High Similarity	NPC185186
0.9054	High Similarity	NPC327383
0.8919	High Similarity	NPC475762
0.8846	High Similarity	NPC1180
0.8831	High Similarity	NPC475711
0.878	High Similarity	NPC208473
0.8625	High Similarity	NPC469469
0.859	High Similarity	NPC233071
0.8553	High Similarity	NPC329890
0.8553	High Similarity	NPC329914
0.8537	High Similarity	NPC473308
0.8514	High Similarity	NPC475760
0.8462	Intermediate Similarity	NPC188860
0.8415	Intermediate Similarity	NPC473315
0.8415	Intermediate Similarity	NPC142111
0.8375	Intermediate Similarity	NPC139712
0.8372	Intermediate Similarity	NPC177668
0.8372	Intermediate Similarity	NPC3952
0.8293	Intermediate Similarity	NPC251026
0.8289	Intermediate Similarity	NPC476012
0.8289	Intermediate Similarity	NPC476037
0.8256	Intermediate Similarity	NPC133450
0.8243	Intermediate Similarity	NPC201356
0.8182	Intermediate Similarity	NPC472196
0.8182	Intermediate Similarity	NPC238090
0.8182	Intermediate Similarity	NPC472195
0.8171	Intermediate Similarity	NPC8538
0.8171	Intermediate Similarity	NPC184208
0.8171	Intermediate Similarity	NPC315731
0.8148	Intermediate Similarity	NPC473947
0.814	Intermediate Similarity	NPC40376
0.814	Intermediate Similarity	NPC21208
0.814	Intermediate Similarity	NPC470137
0.814	Intermediate Similarity	NPC280621
0.814	Intermediate Similarity	NPC20339
0.814	Intermediate Similarity	NPC233551
0.814	Intermediate Similarity	NPC48338
0.8118	Intermediate Similarity	NPC47937
0.8108	Intermediate Similarity	NPC19769
0.8108	Intermediate Similarity	NPC96414
0.809	Intermediate Similarity	NPC159698
0.809	Intermediate Similarity	NPC256368
0.8025	Intermediate Similarity	NPC477314
0.8023	Intermediate Similarity	NPC178215
0.8022	Intermediate Similarity	NPC475332
0.8	Intermediate Similarity	NPC120398
0.8	Intermediate Similarity	NPC182383
0.8	Intermediate Similarity	NPC329615
0.8	Intermediate Similarity	NPC471494
0.8	Intermediate Similarity	NPC477014
0.8	Intermediate Similarity	NPC322529
0.8	Intermediate Similarity	NPC471567
0.8	Intermediate Similarity	NPC329838
0.8	Intermediate Similarity	NPC326661
0.8	Intermediate Similarity	NPC477013
0.7973	Intermediate Similarity	NPC148233
0.7973	Intermediate Similarity	NPC25747
0.7955	Intermediate Similarity	NPC473311
0.7955	Intermediate Similarity	NPC239517
0.7955	Intermediate Similarity	NPC473904
0.7931	Intermediate Similarity	NPC320458
0.7931	Intermediate Similarity	NPC473905
0.7931	Intermediate Similarity	NPC89001
0.7907	Intermediate Similarity	NPC279267
0.7907	Intermediate Similarity	NPC103523
0.7907	Intermediate Similarity	NPC134865
0.7907	Intermediate Similarity	NPC62118
0.7907	Intermediate Similarity	NPC69082
0.7907	Intermediate Similarity	NPC231096
0.7907	Intermediate Similarity	NPC477015
0.7907	Intermediate Similarity	NPC114694
0.7907	Intermediate Similarity	NPC107717
0.7907	Intermediate Similarity	NPC171174
0.7907	Intermediate Similarity	NPC475581
0.7907	Intermediate Similarity	NPC142117
0.7907	Intermediate Similarity	NPC311163
0.7907	Intermediate Similarity	NPC240695
0.7907	Intermediate Similarity	NPC232555
0.7901	Intermediate Similarity	NPC477203
0.7882	Intermediate Similarity	NPC163093
0.7882	Intermediate Similarity	NPC156804
0.7882	Intermediate Similarity	NPC78673
0.7882	Intermediate Similarity	NPC160517
0.7882	Intermediate Similarity	NPC186155
0.7841	Intermediate Similarity	NPC477011
0.7841	Intermediate Similarity	NPC318963
0.7841	Intermediate Similarity	NPC477016
0.7841	Intermediate Similarity	NPC139418
0.7841	Intermediate Similarity	NPC40066
0.7841	Intermediate Similarity	NPC93794
0.7841	Intermediate Similarity	NPC81778
0.7841	Intermediate Similarity	NPC473504
0.7841	Intermediate Similarity	NPC20621
0.7841	Intermediate Similarity	NPC91067
0.7841	Intermediate Similarity	NPC42598
0.7841	Intermediate Similarity	NPC477017
0.7816	Intermediate Similarity	NPC118077
0.7816	Intermediate Similarity	NPC258068
0.7816	Intermediate Similarity	NPC475186
0.7816	Intermediate Similarity	NPC20533
0.7816	Intermediate Similarity	NPC476583
0.7791	Intermediate Similarity	NPC470124
0.7791	Intermediate Similarity	NPC103284
0.7791	Intermediate Similarity	NPC473651
0.7791	Intermediate Similarity	NPC107986
0.7791	Intermediate Similarity	NPC1083
0.7791	Intermediate Similarity	NPC223871
0.7791	Intermediate Similarity	NPC110710
0.7791	Intermediate Similarity	NPC132496
0.7791	Intermediate Similarity	NPC66346
0.7791	Intermediate Similarity	NPC82795
0.7791	Intermediate Similarity	NPC231009
0.7791	Intermediate Similarity	NPC283085
0.7791	Intermediate Similarity	NPC473669
0.7791	Intermediate Similarity	NPC473478
0.7791	Intermediate Similarity	NPC286338
0.7778	Intermediate Similarity	NPC109406
0.7778	Intermediate Similarity	NPC469880
0.7778	Intermediate Similarity	NPC477202
0.7765	Intermediate Similarity	NPC253801
0.7763	Intermediate Similarity	NPC146811
0.7763	Intermediate Similarity	NPC276299
0.7763	Intermediate Similarity	NPC124586
0.7742	Intermediate Similarity	NPC475653
0.7727	Intermediate Similarity	NPC261952
0.7727	Intermediate Similarity	NPC39754
0.7727	Intermediate Similarity	NPC151403
0.7727	Intermediate Similarity	NPC61257
0.7727	Intermediate Similarity	NPC171135
0.7727	Intermediate Similarity	NPC191929
0.7727	Intermediate Similarity	NPC100454
0.7727	Intermediate Similarity	NPC274446
0.7727	Intermediate Similarity	NPC169511
0.7727	Intermediate Similarity	NPC81045
0.7727	Intermediate Similarity	NPC287164
0.7727	Intermediate Similarity	NPC320569
0.7727	Intermediate Similarity	NPC242364
0.7727	Intermediate Similarity	NPC234077
0.7727	Intermediate Similarity	NPC172821
0.7727	Intermediate Similarity	NPC133730
0.7717	Intermediate Similarity	NPC173329
0.7717	Intermediate Similarity	NPC255410
0.7717	Intermediate Similarity	NPC472995
0.7717	Intermediate Similarity	NPC288350
0.7703	Intermediate Similarity	NPC26810
0.7701	Intermediate Similarity	NPC219498
0.7701	Intermediate Similarity	NPC134885
0.7701	Intermediate Similarity	NPC308412
0.7701	Intermediate Similarity	NPC219652
0.7701	Intermediate Similarity	NPC293136
0.7701	Intermediate Similarity	NPC61527
0.7701	Intermediate Similarity	NPC25703
0.7701	Intermediate Similarity	NPC134807
0.7701	Intermediate Similarity	NPC132940
0.7701	Intermediate Similarity	NPC210218
0.7701	Intermediate Similarity	NPC241360
0.7701	Intermediate Similarity	NPC204686
0.7701	Intermediate Similarity	NPC473687
0.7701	Intermediate Similarity	NPC309211
0.7701	Intermediate Similarity	NPC473840
0.7701	Intermediate Similarity	NPC282815
0.7674	Intermediate Similarity	NPC266718
0.7674	Intermediate Similarity	NPC475035
0.7674	Intermediate Similarity	NPC474251
0.7667	Intermediate Similarity	NPC206679
0.7667	Intermediate Similarity	NPC476084
0.7667	Intermediate Similarity	NPC471324
0.7667	Intermediate Similarity	NPC469410
0.7667	Intermediate Similarity	NPC476075
0.7667	Intermediate Similarity	NPC114172
0.7647	Intermediate Similarity	NPC73310
0.7647	Intermediate Similarity	NPC145914
0.7647	Intermediate Similarity	NPC65930
0.7647	Intermediate Similarity	NPC94875
0.7647	Intermediate Similarity	NPC475159
0.7647	Intermediate Similarity	NPC473780
0.7647	Intermediate Similarity	NPC329829
0.7647	Intermediate Similarity	NPC473529
0.7647	Intermediate Similarity	NPC473712
0.7647	Intermediate Similarity	NPC180363
0.7647	Intermediate Similarity	NPC131002
0.7647	Intermediate Similarity	NPC11332
0.764	Intermediate Similarity	NPC280612
0.764	Intermediate Similarity	NPC130359
0.764	Intermediate Similarity	NPC14901
0.7634	Intermediate Similarity	NPC120299
0.7634	Intermediate Similarity	NPC40812
0.7625	Intermediate Similarity	NPC470435
0.7625	Intermediate Similarity	NPC477085
0.7625	Intermediate Similarity	NPC284006
0.7619	Intermediate Similarity	NPC127295
0.7619	Intermediate Similarity	NPC163362

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 NPC133226 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	162
0.1-0.2	2504
0.2-0.3	3744
0.3-0.4	2050
0.4-0.5	522
0.5-0.6	136
0.6-0.7	28
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
0.8161	Intermediate Similarity	NPD7838	Discovery
0.7753	Intermediate Similarity	NPD6698	Approved
0.7753	Intermediate Similarity	NPD46	Approved
0.7553	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD5344	Discontinued
0.7283	Intermediate Similarity	NPD7983	Approved
0.6939	Remote Similarity	NPD6648	Approved
0.6762	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4250	Approved
0.6667	Remote Similarity	NPD4251	Approved
0.6635	Remote Similarity	NPD6686	Approved
0.6632	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD4249	Approved
0.6509	Remote Similarity	NPD6371	Approved
0.65	Remote Similarity	NPD4225	Approved
0.6456	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.642	Remote Similarity	NPD3197	Phase 1
0.641	Remote Similarity	NPD585	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD4271	Approved
0.6404	Remote Similarity	NPD4268	Approved
0.63	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.63	Remote Similarity	NPD7839	Suspended
0.6289	Remote Similarity	NPD5785	Approved
0.6264	Remote Similarity	NPD4821	Approved
0.6264	Remote Similarity	NPD4819	Approved
0.6264	Remote Similarity	NPD4822	Approved
0.6264	Remote Similarity	NPD4820	Approved
0.6261	Remote Similarity	NPD7829	Approved
0.6261	Remote Similarity	NPD7830	Approved
0.6237	Remote Similarity	NPD7154	Phase 3
0.6228	Remote Similarity	NPD7503	Approved
0.6228	Remote Similarity	NPD8513	Phase 3
0.6203	Remote Similarity	NPD6109	Phase 1
0.6203	Remote Similarity	NPD9119	Approved
0.6203	Remote Similarity	NPD69	Approved
0.6162	Remote Similarity	NPD5779	Approved
0.6162	Remote Similarity	NPD5778	Approved
0.6145	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD7639	Approved
0.6117	Remote Similarity	NPD7640	Approved
0.6111	Remote Similarity	NPD4756	Discovery
0.6105	Remote Similarity	NPD5363	Approved
0.6087	Remote Similarity	NPD8516	Approved
0.6087	Remote Similarity	NPD8515	Approved
0.6087	Remote Similarity	NPD8517	Approved
0.6087	Remote Similarity	NPD8033	Approved
0.6076	Remote Similarity	NPD9118	Approved
0.6064	Remote Similarity	NPD6110	Phase 1
0.6061	Remote Similarity	NPD7637	Suspended
0.6055	Remote Similarity	NPD6421	Discontinued
0.6019	Remote Similarity	NPD7638	Approved
0.6018	Remote Similarity	NPD7505	Discontinued
0.6018	Remote Similarity	NPD7115	Discovery
0.6	Remote Similarity	NPD8294	Approved
0.6	Remote Similarity	NPD8377	Approved
0.5983	Remote Similarity	NPD7642	Approved
0.5965	Remote Similarity	NPD7328	Approved
0.5965	Remote Similarity	NPD7327	Approved
0.5948	Remote Similarity	NPD8444	Approved
0.5948	Remote Similarity	NPD8296	Approved
0.5948	Remote Similarity	NPD8335	Approved
0.5948	Remote Similarity	NPD8380	Approved
0.5948	Remote Similarity	NPD8379	Approved
0.5948	Remote Similarity	NPD8378	Approved
0.5946	Remote Similarity	NPD6053	Discontinued
0.5943	Remote Similarity	NPD1407	Approved
0.5938	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD7516	Approved
0.5895	Remote Similarity	NPD5362	Discontinued
0.5882	Remote Similarity	NPD8273	Phase 1
0.5882	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD8074	Phase 3
0.5826	Remote Similarity	NPD7641	Discontinued
0.5816	Remote Similarity	NPD7524	Approved
0.5789	Remote Similarity	NPD6435	Approved
0.5789	Remote Similarity	NPD4269	Approved
0.5789	Remote Similarity	NPD4270	Approved
0.575	Remote Similarity	NPD8451	Approved
0.5745	Remote Similarity	NPD4252	Approved
0.5739	Remote Similarity	NPD7500	Approved
0.5729	Remote Similarity	NPD5332	Approved
0.5729	Remote Similarity	NPD5331	Approved
0.5714	Remote Similarity	NPD8039	Approved
0.5714	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD5786	Approved
0.5702	Remote Similarity	NPD8448	Approved
0.5699	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5696	Remote Similarity	NPD4266	Approved
0.5696	Remote Similarity	NPD3728	Approved
0.5696	Remote Similarity	NPD3730	Approved
0.5696	Remote Similarity	NPD3196	Approved
0.5696	Remote Similarity	NPD3194	Approved
0.5696	Remote Similarity	NPD3195	Phase 2
0.5684	Remote Similarity	NPD4790	Discontinued
0.5676	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.567	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD8342	Approved
0.5667	Remote Similarity	NPD8340	Approved
0.5667	Remote Similarity	NPD8299	Approved
0.5667	Remote Similarity	NPD8341	Approved
0.5625	Remote Similarity	NPD5209	Approved
0.562	Remote Similarity	NPD7507	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